# Electronic Supplementary Material (ESI) for ChemComm.
# 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
#
#  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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 B F2 N3'
_chemical_formula_weight         289.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   8.3942(3)
_cell_length_b                   12.6829(4)
_cell_length_c                   14.0136(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.074(3)
_cell_angle_gamma                90.00
_cell_volume                     1486.08(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4780
_cell_measurement_theta_min      4.7072
_cell_measurement_theta_max      71.9176

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_min  0.8219
_exptl_absorpt_correction_T_max  0.9048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9691
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.71
_diffrn_reflns_theta_max         72.08
_reflns_number_total             2895
_reflns_number_gt                2493
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0848P)²+0.5016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2895
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
F1 F -0.0625(2) 0.69690(11) 0.74130(11) 0.0946(6) Uani 1 1 d . . .
F2 F 0.2010(2) 0.71151(14) 0.72503(11) 0.1031(6) Uani 1 1 d . . .
N1 N 0.06202(19) 0.86454(13) 0.77343(10) 0.0507(4) Uani 1 1 d . . .
N2 N 0.1157(2) 0.71625(12) 0.88399(11) 0.0523(4) Uani 1 1 d . . .
N3 N 0.34121(19) 1.13676(13) 1.05510(11) 0.0517(4) Uani 1 1 d . . .
B1 B 0.0796(3) 0.7446(2) 0.77799(17) 0.0607(6) Uani 1 1 d . . .
C1 C -0.0019(3) 0.92054(19) 0.69744(15) 0.0631(5) Uani 1 1 d . . .
H1 H -0.0369 0.8916 0.6366 0.076 Uiso 1 1 calc R . .
C2 C -0.0090(3) 1.02539(19) 0.72092(16) 0.0698(6) Uani 1 1 d . . .
H2 H -0.0490 1.0808 0.6800 0.084 Uiso 1 1 calc R . .
C3 C 0.0530(2) 1.03539(16) 0.81549(15) 0.0577(5) Uani 1 1 d . . .
H3 H 0.0624 1.0988 0.8516 0.069 Uiso 1 1 calc R . .
C4 C 0.0990(2) 0.93486(15) 0.84771(13) 0.0466(4) Uani 1 1 d . . .
C5 C 0.1646(2) 0.89765(14) 0.93967(12) 0.0449(4) Uani 1 1 d . . .
C6 C 0.1552(2) 0.78651(14) 0.95817(12) 0.0464(4) Uani 1 1 d . . .
C7 C 0.1876(2) 0.72851(16) 1.04195(15) 0.0553(5) Uani 1 1 d . . .
H7 H 0.2176 0.7562 1.1039 0.066 Uiso 1 1 calc R . .
C8 C 0.1679(3) 0.62250(17) 1.01810(16) 0.0648(6) Uani 1 1 d . . .
H8 H 0.1810 0.5643 1.0608 0.078 Uiso 1 1 calc R . .
C9 C 0.1261(3) 0.61784(17) 0.92131(16) 0.0641(6) Uani 1 1 d . . .
H9 H 0.1071 0.5547 0.8857 0.077 Uiso 1 1 calc R . .
C10 C 0.2349(2) 0.96415(15) 1.01091(13) 0.0500(4) Uani 1 1 d . . .
H10 H 0.2458 0.9395 1.0752 0.060 Uiso 1 1 calc R . .
C11 C 0.2896(2) 1.06499(15) 0.99193(13) 0.0499(4) Uani 1 1 d . . .
H11 H 0.2897 1.0840 0.9264 0.060 Uiso 1 1 calc R . .
C12 C 0.3290(3) 1.12489(18) 1.15831(14) 0.0587(5) Uani 1 1 d . . .
H12A H 0.2432 1.0737 1.1686 0.070 Uiso 1 1 calc R . .
H12B H 0.2985 1.1935 1.1850 0.070 Uiso 1 1 calc R . .
C13 C 0.4821(4) 1.0880(3) 1.21124(19) 0.0934(9) Uani 1 1 d . . .
H13A H 0.4672 1.0811 1.2795 0.140 Uiso 1 1 calc R . .
H13B H 0.5669 1.1394 1.2028 0.140 Uiso 1 1 calc R . .
H13C H 0.5120 1.0195 1.1859 0.140 Uiso 1 1 calc R . .
C14 C 0.4043(3) 1.23697(16) 1.02243(16) 0.0581(5) Uani 1 1 d . . .
H14A H 0.4522 1.2255 0.9612 0.070 Uiso 1 1 calc R . .
H14B H 0.4898 1.2621 1.0702 0.070 Uiso 1 1 calc R . .
C15 C 0.2763(3) 1.3201(2) 1.0084(2) 0.0782(7) Uani 1 1 d . . .
H15A H 0.3230 1.3856 0.9862 0.117 Uiso 1 1 calc R . .
H15B H 0.2304 1.3330 1.0692 0.117 Uiso 1 1 calc R . .
H15C H 0.1920 1.2959 0.9605 0.117 Uiso 1 1 calc R . .


_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
F1 B1 1.395(3) . ?
F2 B1 1.378(3) . ?
N1 C1 1.351(3) . ?
N1 C4 1.385(2) . ?
N1 B1 1.529(3) . ?
N2 C9 1.353(3) . ?
N2 C6 1.387(2) . ?
N2 B1 1.532(3) . ?
N3 C11 1.316(2) . ?
N3 C14 1.466(3) . ?
N3 C12 1.467(2) . ?
C1 C2 1.372(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.436(2) . ?
C5 C10 1.397(2) . ?
C5 C6 1.437(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.500(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.507(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 C4 107.51(17) . . ?
C1 N1 B1 125.88(17) . . ?
C4 N1 B1 126.50(16) . . ?
C9 N2 C6 107.45(16) . . ?
C9 N2 B1 126.28(17) . . ?
C6 N2 B1 126.11(17) . . ?
C11 N3 C14 119.74(16) . . ?
C11 N3 C12 123.01(17) . . ?
C14 N3 C12 117.11(16) . . ?
F2 B1 F1 108.55(19) . . ?
F2 B1 N1 110.7(2) . . ?
F1 B1 N1 109.88(18) . . ?
F2 B1 N2 111.00(18) . . ?
F1 B1 N2 110.2(2) . . ?
N1 B1 N2 106.51(16) . . ?
N1 C1 C2 110.06(19) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C1 C2 C3 107.30(19) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.3 . . ?
C2 C3 C4 107.18(19) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C3 107.94(16) . . ?
N1 C4 C5 120.37(16) . . ?
C3 C4 C5 131.60(18) . . ?
C10 C5 C4 123.17(17) . . ?
C10 C5 C6 119.33(16) . . ?
C4 C5 C6 117.49(16) . . ?
N2 C6 C7 107.98(17) . . ?
N2 C6 C5 120.56(16) . . ?
C7 C6 C5 131.38(17) . . ?
C8 C7 C6 107.33(18) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C9 C8 C7 107.07(19) . . ?
C9 C8 H8 126.5 . . ?
C7 C8 H8 126.5 . . ?
N2 C9 C8 110.15(18) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
C11 C10 C5 122.91(17) . . ?
C11 C10 H10 118.5 . . ?
C5 C10 H10 118.5 . . ?
N3 C11 C10 126.95(18) . . ?
N3 C11 H11 116.5 . . ?
C10 C11 H11 116.5 . . ?
N3 C12 C13 112.83(19) . . ?
N3 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N3 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.00(18) . . ?
N3 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 F2 73.9(3) . . . . ?
C4 N1 B1 F2 -110.5(2) . . . . ?
C1 N1 B1 F1 -46.0(3) . . . . ?
C4 N1 B1 F1 129.6(2) . . . . ?
C1 N1 B1 N2 -165.35(19) . . . . ?
C4 N1 B1 N2 10.3(3) . . . . ?
C9 N2 B1 F2 -65.6(3) . . . . ?
C6 N2 B1 F2 109.3(2) . . . . ?
C9 N2 B1 F1 54.6(3) . . . . ?
C6 N2 B1 F1 -130.4(2) . . . . ?
C9 N2 B1 N1 173.7(2) . . . . ?
C6 N2 B1 N1 -11.3(3) . . . . ?
C4 N1 C1 C2 -0.7(2) . . . . ?
B1 N1 C1 C2 175.7(2) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 N1 C4 C3 1.1(2) . . . . ?
B1 N1 C4 C3 -175.2(2) . . . . ?
C1 N1 C4 C5 177.97(17) . . . . ?
B1 N1 C4 C5 1.7(3) . . . . ?
C2 C3 C4 N1 -1.1(2) . . . . ?
C2 C3 C4 C5 -177.5(2) . . . . ?
N1 C4 C5 C10 166.32(17) . . . . ?
C3 C4 C5 C10 -17.7(3) . . . . ?
N1 C4 C5 C6 -14.2(2) . . . . ?
C3 C4 C5 C6 161.8(2) . . . . ?
C9 N2 C6 C7 -0.9(2) . . . . ?
B1 N2 C6 C7 -176.59(19) . . . . ?
C9 N2 C6 C5 176.11(18) . . . . ?
B1 N2 C6 C5 0.4(3) . . . . ?
C10 C5 C6 N2 -167.28(17) . . . . ?
C4 C5 C6 N2 13.3(2) . . . . ?
C10 C5 C6 C7 8.9(3) . . . . ?
C4 C5 C6 C7 -170.58(19) . . . . ?
N2 C6 C7 C8 0.1(2) . . . . ?
C5 C6 C7 C8 -176.4(2) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C6 N2 C9 C8 1.3(3) . . . . ?
B1 N2 C9 C8 177.0(2) . . . . ?
C7 C8 C9 N2 -1.2(3) . . . . ?
C4 C5 C10 C11 -19.1(3) . . . . ?
C6 C5 C10 C11 161.45(18) . . . . ?
C14 N3 C11 C10 176.11(19) . . . . ?
C12 N3 C11 C10 -8.2(3) . . . . ?
C5 C10 C11 N3 172.19(19) . . . . ?
C11 N3 C12 C13 99.1(3) . . . . ?
C14 N3 C12 C13 -85.1(3) . . . . ?
C11 N3 C14 C15 91.5(2) . . . . ?
C12 N3 C14 C15 -84.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        72.08
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 1001550'
#######################################################################
#
#                 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_4a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 B F2 N3'
_chemical_formula_weight         317.19

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.2376(16)
_cell_length_b                   14.7140(12)
_cell_length_c                   15.929(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.73(3)
_cell_angle_gamma                90.00
_cell_volume                     1712.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5196
_cell_measurement_theta_min      3.5410
_cell_measurement_theta_max      29.4450

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3000
_reflns_number_gt                2405
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0429P)²+0.8433P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3000
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.5641(4) 0.18877(17) 0.2420(2) 0.0477(6) Uani 1 1 d . . .
F1 F 0.39753(19) 0.21129(10) 0.22166(12) 0.0745(5) Uani 1 1 d . . .
F2 F 0.5911(3) 0.24614(10) 0.18469(12) 0.0839(6) Uani 1 1 d . . .
N1 N 0.5594(2) 0.08897(12) 0.21277(13) 0.0427(4) Uani 1 1 d . . .
N2 N 0.7232(2) 0.19625(11) 0.36100(14) 0.0416(4) Uani 1 1 d . . .
N3 N 0.8226(2) -0.09390(12) 0.62531(14) 0.0438(4) Uani 1 1 d . . .
C1 C 0.4681(3) 0.05281(16) 0.11421(18) 0.0538(6) Uani 1 1 d . . .
H1 H 0.4066 0.0869 0.0503 0.065 Uiso 1 1 calc R . .
C2 C 0.4777(3) -0.04057(16) 0.12045(19) 0.0563(6) Uani 1 1 d . . .
H2 H 0.4271 -0.0817 0.0628 0.068 Uiso 1 1 calc R . .
C3 C 0.5754(3) -0.06327(15) 0.22689(18) 0.0477(5) Uani 1 1 d . . .
H3 H 0.6029 -0.1230 0.2555 0.057 Uiso 1 1 calc R . .
C4 C 0.6257(3) 0.01759(13) 0.28407(16) 0.0383(5) Uani 1 1 d . . .
C5 C 0.7263(3) 0.03441(13) 0.39603(16) 0.0364(5) Uani 1 1 d . . .
C6 C 0.7948(3) 0.12495(13) 0.43340(16) 0.0372(5) Uani 1 1 d . . .
C7 C 0.9374(3) 0.16054(15) 0.53271(17) 0.0463(5) Uani 1 1 d . . .
H7 H 1.0120 0.1274 0.5972 0.056 Uiso 1 1 calc R . .
C8 C 0.9506(3) 0.25266(16) 0.52028(19) 0.0542(6) Uani 1 1 d . . .
H8 H 1.0360 0.2941 0.5743 0.065 Uiso 1 1 calc R . .
C9 C 0.8164(3) 0.27288(15) 0.41468(19) 0.0518(6) Uani 1 1 d . . .
H9 H 0.7926 0.3317 0.3841 0.062 Uiso 1 1 calc R . .
C10 C 0.7459(3) -0.03792(14) 0.45881(17) 0.0422(5) Uani 1 1 d . . .
H10 H 0.7129 -0.0968 0.4279 0.051 Uiso 1 1 calc R . .
C11 C 0.8101(3) -0.02993(14) 0.56317(17) 0.0423(5) Uani 1 1 d . . .
H11 H 0.8499 0.0289 0.5937 0.051 Uiso 1 1 calc R . .
C12 C 0.7606(4) -0.18872(15) 0.58670(19) 0.0537(6) Uani 1 1 d . . .
H12 H 0.7610 -0.1978 0.5246 0.064 Uiso 1 1 calc R . .
C13 C 0.5653(4) -0.1997(2) 0.5473(2) 0.0743(8) Uani 1 1 d . . .
H13A H 0.5606 -0.1920 0.6067 0.111 Uiso 1 1 calc R . .
H13B H 0.5209 -0.2604 0.5167 0.111 Uiso 1 1 calc R . .
H13C H 0.4879 -0.1537 0.4929 0.111 Uiso 1 1 calc R . .
C14 C 0.8895(5) -0.25889(19) 0.6704(3) 0.0855(10) Uani 1 1 d . . .
H14A H 1.0156 -0.2452 0.6983 0.128 Uiso 1 1 calc R . .
H14B H 0.8559 -0.3196 0.6384 0.128 Uiso 1 1 calc R . .
H14C H 0.8801 -0.2570 0.7284 0.128 Uiso 1 1 calc R . .
C15 C 0.8757(3) -0.06848(16) 0.73124(17) 0.0498(6) Uani 1 1 d . . .
H15 H 0.8438 -0.1212 0.7568 0.060 Uiso 1 1 calc R . .
C16 C 1.0804(4) -0.0550(2) 0.8106(2) 0.0814(9) Uani 1 1 d . . .
H16A H 1.1433 -0.1106 0.8153 0.122 Uiso 1 1 calc R . .
H16B H 1.1129 -0.0410 0.8804 0.122 Uiso 1 1 calc R . .
H16C H 1.1178 -0.0045 0.7875 0.122 Uiso 1 1 calc R . .
C17 C 0.7698(4) 0.0127(2) 0.7262(2) 0.0719(8) Uani 1 1 d . . .
H17A H 0.8133 0.0680 0.7136 0.108 Uiso 1 1 calc R . .
H17B H 0.7885 0.0184 0.7935 0.108 Uiso 1 1 calc R . .
H17C H 0.6392 0.0044 0.6682 0.108 Uiso 1 1 calc R . .


_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 1.373(3) . ?
B1 F1 1.405(3) . ?
B1 N1 1.533(3) . ?
B1 N2 1.535(3) . ?
N1 C1 1.356(3) . ?
N1 C4 1.384(3) . ?
N2 C9 1.357(3) . ?
N2 C6 1.391(2) . ?
N3 C11 1.319(3) . ?
N3 C15 1.488(3) . ?
N3 C12 1.491(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.441(3) . ?
C5 C10 1.394(3) . ?
C5 C6 1.438(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.513(4) . ?
C12 C14 1.523(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.512(4) . ?
C15 C17 1.515(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 108.7(2) . . ?
F2 B1 N1 111.7(2) . . ?
F1 B1 N1 109.41(19) . . ?
F2 B1 N2 110.5(2) . . ?
F1 B1 N2 110.7(2) . . ?
N1 B1 N2 105.76(17) . . ?
C1 N1 C4 107.54(18) . . ?
C1 N1 B1 127.55(18) . . ?
C4 N1 B1 124.17(17) . . ?
C9 N2 C6 107.93(18) . . ?
C9 N2 B1 126.61(18) . . ?
C6 N2 B1 125.45(17) . . ?
C11 N3 C15 119.23(18) . . ?
C11 N3 C12 121.57(18) . . ?
C15 N3 C12 118.67(17) . . ?
N1 C1 C2 110.0(2) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C1 C2 C3 107.1(2) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C2 C3 C4 107.5(2) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.96(18) . . ?
N1 C4 C5 120.75(18) . . ?
C3 C4 C5 131.29(19) . . ?
C10 C5 C6 125.39(19) . . ?
C10 C5 C4 117.31(19) . . ?
C6 C5 C4 117.28(17) . . ?
N2 C6 C7 107.21(18) . . ?
N2 C6 C5 119.34(18) . . ?
C7 C6 C5 133.26(19) . . ?
C8 C7 C6 108.0(2) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
C9 C8 C7 107.0(2) . . ?
C9 C8 H8 126.5 . . ?
C7 C8 H8 126.5 . . ?
N2 C9 C8 109.8(2) . . ?
N2 C9 H9 125.1 . . ?
C8 C9 H9 125.1 . . ?
C11 C10 C5 124.6(2) . . ?
C11 C10 H10 117.7 . . ?
C5 C10 H10 117.7 . . ?
N3 C11 C10 128.0(2) . . ?
N3 C11 H11 116.0 . . ?
C10 C11 H11 116.0 . . ?
N3 C12 C13 109.32(19) . . ?
N3 C12 C14 112.1(2) . . ?
C13 C12 C14 112.7(2) . . ?
N3 C12 H12 107.5 . . ?
C13 C12 H12 107.5 . . ?
C14 C12 H12 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 110.9(2) . . ?
N3 C15 C17 112.58(19) . . ?
C16 C15 C17 112.2(2) . . ?
N3 C15 H15 106.9 . . ?
C16 C15 H15 106.9 . . ?
C17 C15 H15 106.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 B1 N1 C1 -45.4(3) . . . . ?
F1 B1 N1 C1 75.0(3) . . . . ?
N2 B1 N1 C1 -165.8(2) . . . . ?
F2 B1 N1 C4 145.6(2) . . . . ?
F1 B1 N1 C4 -94.0(2) . . . . ?
N2 B1 N1 C4 25.3(3) . . . . ?
F2 B1 N2 C9 36.5(3) . . . . ?
F1 B1 N2 C9 -83.9(3) . . . . ?
N1 B1 N2 C9 157.6(2) . . . . ?
F2 B1 N2 C6 -144.8(2) . . . . ?
F1 B1 N2 C6 94.7(2) . . . . ?
N1 B1 N2 C6 -23.8(3) . . . . ?
C4 N1 C1 C2 -1.4(3) . . . . ?
B1 N1 C1 C2 -171.8(2) . . . . ?
N1 C1 C2 C3 1.3(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 N1 C4 C3 1.0(2) . . . . ?
B1 N1 C4 C3 171.8(2) . . . . ?
C1 N1 C4 C5 -178.67(19) . . . . ?
B1 N1 C4 C5 -7.9(3) . . . . ?
C2 C3 C4 N1 -0.2(2) . . . . ?
C2 C3 C4 C5 179.4(2) . . . . ?
N1 C4 C5 C10 163.16(18) . . . . ?
C3 C4 C5 C10 -16.4(3) . . . . ?
N1 C4 C5 C6 -15.5(3) . . . . ?
C3 C4 C5 C6 164.9(2) . . . . ?
C9 N2 C6 C7 -1.2(2) . . . . ?
B1 N2 C6 C7 180.0(2) . . . . ?
C9 N2 C6 C5 -176.81(18) . . . . ?
B1 N2 C6 C5 4.4(3) . . . . ?
C10 C5 C6 N2 -161.45(19) . . . . ?
C4 C5 C6 N2 17.1(3) . . . . ?
C10 C5 C6 C7 24.3(4) . . . . ?
C4 C5 C6 C7 -157.1(2) . . . . ?
N2 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C8 175.2(2) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C6 N2 C9 C8 1.5(3) . . . . ?
B1 N2 C9 C8 -179.6(2) . . . . ?
C7 C8 C9 N2 -1.3(3) . . . . ?
C6 C5 C10 C11 10.2(3) . . . . ?
C4 C5 C10 C11 -168.41(19) . . . . ?
C15 N3 C11 C10 -173.0(2) . . . . ?
C12 N3 C11 C10 -1.5(3) . . . . ?
C5 C10 C11 N3 175.9(2) . . . . ?
C11 N3 C12 C13 -94.0(2) . . . . ?
C15 N3 C12 C13 77.5(3) . . . . ?
C11 N3 C12 C14 140.2(2) . . . . ?
C15 N3 C12 C14 -48.3(3) . . . . ?
C11 N3 C15 C16 -79.4(3) . . . . ?
C12 N3 C15 C16 108.9(2) . . . . ?
C11 N3 C15 C17 47.2(3) . . . . ?
C12 N3 C15 C17 -124.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1001551'
#######################################################################
#
#                 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_4b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 B F2 N3'
_chemical_formula_weight         317.19

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   11.1777(8)
_cell_length_b                   11.3773(5)
_cell_length_c                   14.4649(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.830(8)
_cell_angle_gamma                90.00
_cell_volume                     1730.45(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2012
_cell_measurement_theta_min      3.8630
_cell_measurement_theta_max      22.8800

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9413
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3022
_reflns_number_gt                1866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0492P)²+0.1640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.5065(3) 0.2173(2) 0.2732(2) 0.0401(8) Uani 1 1 d . . .
F1 F 0.56016(16) 0.32765(12) 0.29885(11) 0.0605(5) Uani 1 1 d . . .
F2 F 0.46507(16) 0.17564(13) 0.34847(10) 0.0567(5) Uani 1 1 d . . .
N1 N 0.6009(2) 0.13074(16) 0.25421(14) 0.0375(5) Uani 1 1 d . . .
N2 N 0.3938(2) 0.22347(16) 0.17609(14) 0.0382(5) Uani 1 1 d . . .
N3 N 0.2344(2) -0.21468(16) -0.01918(14) 0.0393(6) Uani 1 1 d . . .
C1 C 0.7280(3) 0.1215(2) 0.30291(19) 0.0458(7) Uani 1 1 d . . .
H1 H 0.7771 0.1738 0.3525 0.055 Uiso 1 1 calc R . .
C2 C 0.7748(3) 0.0246(2) 0.2692(2) 0.0519(8) Uani 1 1 d . . .
H2 H 0.8609 -0.0009 0.2903 0.062 Uiso 1 1 calc R . .
C3 C 0.6726(3) -0.0288(2) 0.1987(2) 0.0468(7) Uani 1 1 d . . .
H3 H 0.6761 -0.0979 0.1629 0.056 Uiso 1 1 calc R . .
C4 C 0.5642(3) 0.03641(19) 0.18962(18) 0.0378(6) Uani 1 1 d . . .
C5 C 0.4322(2) 0.0247(2) 0.12709(17) 0.0369(6) Uani 1 1 d . . .
C6 C 0.3557(2) 0.1302(2) 0.11104(17) 0.0369(6) Uani 1 1 d . . .
C7 C 0.2531(3) 0.1667(2) 0.03098(18) 0.0450(7) Uani 1 1 d . . .
H7 H 0.2092 0.1212 -0.0254 0.054 Uiso 1 1 calc R . .
C8 C 0.2263(3) 0.2826(2) 0.04866(19) 0.0502(8) Uani 1 1 d . . .
H8 H 0.1603 0.3305 0.0071 0.060 Uiso 1 1 calc R . .
C9 C 0.3139(3) 0.3144(2) 0.1379(2) 0.0490(8) Uani 1 1 d . . .
H9 H 0.3177 0.3891 0.1682 0.059 Uiso 1 1 calc R . .
C10 C 0.3905(3) -0.0819(2) 0.08061(18) 0.0435(7) Uani 1 1 d . . .
H10 H 0.4544 -0.1322 0.0731 0.052 Uiso 1 1 calc R . .
C11 C 0.2643(3) -0.1247(2) 0.04309(18) 0.0397(7) Uani 1 1 d . . .
C12 C 0.1636(3) -0.0809(2) 0.0833(2) 0.0600(9) Uani 1 1 d . . .
H12A H 0.0898 -0.0525 0.0291 0.090 Uiso 1 1 calc R . .
H12B H 0.1985 -0.0165 0.1297 0.090 Uiso 1 1 calc R . .
H12C H 0.1373 -0.1452 0.1172 0.090 Uiso 1 1 calc R . .
C13 C 0.3290(3) -0.2600(2) -0.06124(19) 0.0478(7) Uani 1 1 d . . .
H13A H 0.3803 -0.1933 -0.0711 0.057 Uiso 1 1 calc R . .
H13B H 0.2833 -0.2945 -0.1265 0.057 Uiso 1 1 calc R . .
C14 C 0.4180(3) -0.3520(2) 0.0020(2) 0.0698(10) Uani 1 1 d . . .
H14A H 0.4524 -0.3239 0.0700 0.105 Uiso 1 1 calc R . .
H14B H 0.4880 -0.3661 -0.0230 0.105 Uiso 1 1 calc R . .
H14C H 0.3712 -0.4253 -0.0002 0.105 Uiso 1 1 calc R . .
C15 C 0.1034(3) -0.2657(2) -0.0584(2) 0.0518(8) Uani 1 1 d . . .
H15 H 0.0562 -0.2383 -0.0147 0.062 Uiso 1 1 calc R . .
C16 C 0.1057(3) -0.3990(2) -0.0549(2) 0.0733(10) Uani 1 1 d . . .
H16A H 0.1478 -0.4290 -0.0996 0.110 Uiso 1 1 calc R . .
H16B H 0.0184 -0.4289 -0.0752 0.110 Uiso 1 1 calc R . .
H16C H 0.1525 -0.4251 0.0122 0.110 Uiso 1 1 calc R . .
C17 C 0.0340(3) -0.2179(3) -0.1606(2) 0.0836(11) Uani 1 1 d . . .
H17A H 0.0360 -0.1318 -0.1589 0.125 Uiso 1 1 calc R . .
H17B H -0.0545 -0.2449 -0.1828 0.125 Uiso 1 1 calc R . .
H17C H 0.0756 -0.2463 -0.2061 0.125 Uiso 1 1 calc R . .


_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 1.387(3) . ?
B1 F2 1.402(3) . ?
B1 N1 1.534(4) . ?
B1 N2 1.538(3) . ?
N1 C1 1.360(3) . ?
N1 C4 1.390(3) . ?
N2 C9 1.356(3) . ?
N2 C6 1.386(3) . ?
N3 C11 1.329(3) . ?
N3 C13 1.479(3) . ?
N3 C15 1.496(3) . ?
C1 C2 1.379(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.451(3) . ?
C5 C10 1.388(3) . ?
C5 C6 1.447(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.415(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.516(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.519(4) . ?
C15 C16 1.517(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 109.0(2) . . ?
F1 B1 N1 111.6(2) . . ?
F2 B1 N1 110.5(2) . . ?
F1 B1 N2 110.4(2) . . ?
F2 B1 N2 109.9(2) . . ?
N1 B1 N2 105.4(2) . . ?
C1 N1 C4 107.9(2) . . ?
C1 N1 B1 128.2(2) . . ?
C4 N1 B1 123.5(2) . . ?
C9 N2 C6 107.4(2) . . ?
C9 N2 B1 129.0(2) . . ?
C6 N2 B1 123.59(19) . . ?
C11 N3 C13 119.8(2) . . ?
C11 N3 C15 123.0(2) . . ?
C13 N3 C15 116.9(2) . . ?
N1 C1 C2 109.5(2) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 H1 125.2 . . ?
C1 C2 C3 107.1(2) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C2 C3 C4 108.1(2) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
N1 C4 C3 107.4(2) . . ?
N1 C4 C5 119.7(2) . . ?
C3 C4 C5 132.8(2) . . ?
C10 C5 C6 124.3(2) . . ?
C10 C5 C4 119.1(2) . . ?
C6 C5 C4 116.4(2) . . ?
N2 C6 C7 108.3(2) . . ?
N2 C6 C5 119.8(2) . . ?
C7 C6 C5 131.2(2) . . ?
C6 C7 C8 107.3(2) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
C9 C8 C7 107.0(2) . . ?
C9 C8 H8 126.5 . . ?
C7 C8 H8 126.5 . . ?
N2 C9 C8 110.0(2) . . ?
N2 C9 H9 125.0 . . ?
C8 C9 H9 125.0 . . ?
C5 C10 C11 127.9(3) . . ?
C5 C10 H10 116.1 . . ?
C11 C10 H10 116.1 . . ?
N3 C11 C10 120.9(2) . . ?
N3 C11 C12 117.7(2) . . ?
C10 C11 C12 120.8(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 114.0(2) . . ?
N3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C17 109.9(2) . . ?
N3 C15 C16 111.8(2) . . ?
C17 C15 C16 112.8(2) . . ?
N3 C15 H15 107.3 . . ?
C17 C15 H15 107.3 . . ?
C16 C15 H15 107.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
F1 B1 N1 C1 37.8(4) . . . . ?
F2 B1 N1 C1 -83.6(3) . . . . ?
N2 B1 N1 C1 157.7(2) . . . . ?
F1 B1 N1 C4 -150.9(2) . . . . ?
F2 B1 N1 C4 87.6(3) . . . . ?
N2 B1 N1 C4 -31.1(3) . . . . ?
F1 B1 N2 C9 -29.1(4) . . . . ?
F2 B1 N2 C9 91.1(3) . . . . ?
N1 B1 N2 C9 -149.8(3) . . . . ?
F1 B1 N2 C6 151.7(2) . . . . ?
F2 B1 N2 C6 -88.1(3) . . . . ?
N1 B1 N2 C6 31.1(3) . . . . ?
C4 N1 C1 C2 1.5(3) . . . . ?
B1 N1 C1 C2 173.8(2) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 N1 C4 C3 -1.3(3) . . . . ?
B1 N1 C4 C3 -174.1(2) . . . . ?
C1 N1 C4 C5 -179.5(2) . . . . ?
B1 N1 C4 C5 7.7(4) . . . . ?
C2 C3 C4 N1 0.6(3) . . . . ?
C2 C3 C4 C5 178.5(3) . . . . ?
N1 C4 C5 C10 -164.9(2) . . . . ?
C3 C4 C5 C10 17.4(4) . . . . ?
N1 C4 C5 C6 20.4(3) . . . . ?
C3 C4 C5 C6 -157.3(3) . . . . ?
C9 N2 C6 C7 1.6(3) . . . . ?
B1 N2 C6 C7 -179.1(2) . . . . ?
C9 N2 C6 C5 173.2(2) . . . . ?
B1 N2 C6 C5 -7.5(4) . . . . ?
C10 C5 C6 N2 165.1(2) . . . . ?
C4 C5 C6 N2 -20.5(3) . . . . ?
C10 C5 C6 C7 -25.5(5) . . . . ?
C4 C5 C6 C7 148.9(3) . . . . ?
N2 C6 C7 C8 -1.5(3) . . . . ?
C5 C6 C7 C8 -171.8(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C6 N2 C9 C8 -1.1(3) . . . . ?
B1 N2 C9 C8 179.6(3) . . . . ?
C7 C8 C9 N2 0.2(3) . . . . ?
C6 C5 C10 C11 -27.1(4) . . . . ?
C4 C5 C10 C11 158.6(3) . . . . ?
C13 N3 C11 C10 -8.9(4) . . . . ?
C15 N3 C11 C10 177.9(2) . . . . ?
C13 N3 C11 C12 179.4(2) . . . . ?
C15 N3 C11 C12 6.3(4) . . . . ?
C5 C10 C11 N3 164.1(2) . . . . ?
C5 C10 C11 C12 -24.5(4) . . . . ?
C11 N3 C13 C14 87.0(3) . . . . ?
C15 N3 C13 C14 -99.5(3) . . . . ?
C11 N3 C15 C17 99.2(3) . . . . ?
C13 N3 C15 C17 -74.1(3) . . . . ?
C11 N3 C15 C16 -134.7(3) . . . . ?
C13 N3 C15 C16 52.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1001552'
#######################################################################
#
#                 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_5a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 B F2 N3'
_chemical_formula_weight         301.14

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   7.8218(4)
_cell_length_b                   23.1144(9)
_cell_length_c                   8.5337(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.867(6)
_cell_angle_gamma                90.00
_cell_volume                     1441.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5862
_cell_measurement_theta_min      3.6700
_cell_measurement_theta_max      31.7600

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11087
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2523
_reflns_number_gt                2188
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0288P)²+0.5953P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2523
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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 1.1287(2) 0.14193(8) 0.5223(2) 0.0219(4) Uani 1 1 d . . .
F1 F 1.20068(14) 0.18550(4) 0.64018(12) 0.0336(3) Uani 1 1 d . . .
F2 F 0.93931(13) 0.15058(4) 0.44628(13) 0.0310(3) Uani 1 1 d . . .
N1 N 1.16831(17) 0.08233(5) 0.60770(16) 0.0189(3) Uani 1 1 d . . .
N2 N 1.22045(17) 0.14173(5) 0.39095(16) 0.0211(3) Uani 1 1 d . . .
N3 N 1.33994(17) -0.11327(6) 0.27065(16) 0.0212(3) Uani 1 1 d . . .
C1 C 1.1459(2) 0.06905(7) 0.75375(19) 0.0220(4) Uani 1 1 d . . .
H1 H 1.1058 0.0953 0.8192 0.026 Uiso 1 1 calc R . .
C2 C 1.1898(2) 0.01190(7) 0.7931(2) 0.0228(4) Uani 1 1 d . . .
H2 H 1.1853 -0.0081 0.8888 0.027 Uiso 1 1 calc R . .
C3 C 1.2420(2) -0.01099(7) 0.66601(19) 0.0212(4) Uani 1 1 d . . .
H3 H 1.2808 -0.0496 0.6598 0.025 Uiso 1 1 calc R . .
C4 C 1.22735(19) 0.03289(6) 0.54905(19) 0.0174(3) Uani 1 1 d . . .
C5 C 1.26765(19) 0.03584(6) 0.39694(19) 0.0171(3) Uani 1 1 d . . .
C6 C 1.2744(2) 0.09253(7) 0.32761(19) 0.0196(3) Uani 1 1 d . . .
C7 C 1.3350(2) 0.11006(7) 0.1997(2) 0.0252(4) Uani 1 1 d . . .
H7 H 1.3799 0.0855 0.1337 0.030 Uiso 1 1 calc R . .
C8 C 1.3179(2) 0.17005(8) 0.1863(2) 0.0308(4) Uani 1 1 d . . .
H8 H 1.3496 0.1940 0.1103 0.037 Uiso 1 1 calc R . .
C9 C 1.2461(2) 0.18812(7) 0.3042(2) 0.0270(4) Uani 1 1 d . . .
H9 H 1.2187 0.2271 0.3220 0.032 Uiso 1 1 calc R . .
C10 C 1.30661(19) -0.01098(7) 0.31145(19) 0.0192(3) Uani 1 1 d . . .
H10 H 1.3424 -0.0021 0.2189 0.023 Uiso 1 1 calc R . .
C11 C 1.2982(2) -0.06921(7) 0.34813(19) 0.0199(3) Uani 1 1 d . . .
H11 H 1.2583 -0.0782 0.4382 0.024 Uiso 1 1 calc R . .
C12 C 1.3150(2) -0.17335(7) 0.3148(2) 0.0274(4) Uani 1 1 d . . .
H12A H 1.2740 -0.1738 0.4120 0.033 Uiso 1 1 calc R . .
H12B H 1.4329 -0.1943 0.3468 0.033 Uiso 1 1 calc R . .
C13 C 1.1733(2) -0.20352(7) 0.1661(2) 0.0297(4) Uani 1 1 d . . .
H13A H 1.1668 -0.2449 0.1930 0.036 Uiso 1 1 calc R . .
H13B H 1.0515 -0.1861 0.1453 0.036 Uiso 1 1 calc R . .
C14 C 1.2205(2) -0.19829(7) 0.0088(2) 0.0285(4) Uani 1 1 d . . .
H14A H 1.1196 -0.2146 -0.0876 0.034 Uiso 1 1 calc R . .
H14B H 1.3324 -0.2210 0.0232 0.034 Uiso 1 1 calc R . .
C15 C 1.2513(2) -0.13558(7) -0.0275(2) 0.0281(4) Uani 1 1 d . . .
H15A H 1.1355 -0.1137 -0.0550 0.034 Uiso 1 1 calc R . .
H15B H 1.2910 -0.1336 -0.1254 0.034 Uiso 1 1 calc R . .
C16 C 1.3973(2) -0.10864(7) 0.1251(2) 0.0234(4) Uani 1 1 d . . .
H16A H 1.5152 -0.1289 0.1485 0.028 Uiso 1 1 calc R . .
H16B H 1.4145 -0.0675 0.1025 0.028 Uiso 1 1 calc R . .


_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 1.393(2) . ?
B1 F2 1.404(2) . ?
B1 N2 1.531(2) . ?
B1 N1 1.538(2) . ?
N1 C1 1.354(2) . ?
N1 C4 1.3907(19) . ?
N2 C9 1.358(2) . ?
N2 C6 1.388(2) . ?
N3 C11 1.317(2) . ?
N3 C16 1.467(2) . ?
N3 C12 1.470(2) . ?
C1 C2 1.376(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.442(2) . ?
C5 C10 1.398(2) . ?
C5 C6 1.446(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.524(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
F1 B1 F2 108.63(13) . . ?
F1 B1 N2 110.89(14) . . ?
F2 B1 N2 110.79(13) . . ?
F1 B1 N1 110.12(13) . . ?
F2 B1 N1 110.36(13) . . ?
N2 B1 N1 106.04(13) . . ?
C1 N1 C4 108.27(13) . . ?
C1 N1 B1 124.67(13) . . ?
C4 N1 B1 127.03(13) . . ?
C9 N2 C6 108.10(14) . . ?
C9 N2 B1 126.53(14) . . ?
C6 N2 B1 125.05(13) . . ?
C11 N3 C16 125.03(14) . . ?
C11 N3 C12 121.50(14) . . ?
C16 N3 C12 113.22(12) . . ?
N1 C1 C2 109.82(14) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C1 C2 C3 106.96(14) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C2 C3 C4 107.94(14) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
N1 C4 C3 107.00(13) . . ?
N1 C4 C5 119.47(13) . . ?
C3 C4 C5 133.45(14) . . ?
C10 C5 C4 126.23(14) . . ?
C10 C5 C6 116.19(14) . . ?
C4 C5 C6 117.55(13) . . ?
N2 C6 C7 107.55(14) . . ?
N2 C6 C5 121.51(14) . . ?
C7 C6 C5 130.90(15) . . ?
C8 C7 C6 107.68(15) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C9 C8 C7 107.04(15) . . ?
C9 C8 H8 126.5 . . ?
C7 C8 H8 126.5 . . ?
N2 C9 C8 109.62(15) . . ?
N2 C9 H9 125.2 . . ?
C8 C9 H9 125.2 . . ?
C11 C10 C5 126.59(15) . . ?
C11 C10 H10 116.7 . . ?
C5 C10 H10 116.7 . . ?
N3 C11 C10 126.60(15) . . ?
N3 C11 H11 116.7 . . ?
C10 C11 H11 116.7 . . ?
N3 C12 C13 110.03(13) . . ?
N3 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 111.47(14) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.26(14) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 109.89(14) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 C15 109.36(13) . . ?
N3 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?

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
F1 B1 N1 C1 45.1(2) . . . . ?
F2 B1 N1 C1 -74.82(18) . . . . ?
N2 B1 N1 C1 165.13(13) . . . . ?
F1 B1 N1 C4 -136.77(14) . . . . ?
F2 B1 N1 C4 103.31(17) . . . . ?
N2 B1 N1 C4 -16.7(2) . . . . ?
F1 B1 N2 C9 -49.3(2) . . . . ?
F2 B1 N2 C9 71.43(19) . . . . ?
N1 B1 N2 C9 -168.81(14) . . . . ?
F1 B1 N2 C6 137.99(14) . . . . ?
F2 B1 N2 C6 -101.30(16) . . . . ?
N1 B1 N2 C6 18.46(19) . . . . ?
C4 N1 C1 C2 0.30(17) . . . . ?
B1 N1 C1 C2 178.72(14) . . . . ?
N1 C1 C2 C3 0.16(17) . . . . ?
C1 C2 C3 C4 -0.55(17) . . . . ?
C1 N1 C4 C3 -0.63(16) . . . . ?
B1 N1 C4 C3 -179.01(14) . . . . ?
C1 N1 C4 C5 -177.95(13) . . . . ?
B1 N1 C4 C5 3.7(2) . . . . ?
C2 C3 C4 N1 0.72(16) . . . . ?
C2 C3 C4 C5 177.51(15) . . . . ?
N1 C4 C5 C10 -171.78(13) . . . . ?
C3 C4 C5 C10 11.8(3) . . . . ?
N1 C4 C5 C6 10.3(2) . . . . ?
C3 C4 C5 C6 -166.20(15) . . . . ?
C9 N2 C6 C7 0.32(17) . . . . ?
B1 N2 C6 C7 174.18(14) . . . . ?
C9 N2 C6 C5 178.53(13) . . . . ?
B1 N2 C6 C5 -7.6(2) . . . . ?
C10 C5 C6 N2 173.37(13) . . . . ?
C4 C5 C6 N2 -8.5(2) . . . . ?
C10 C5 C6 C7 -8.9(2) . . . . ?
C4 C5 C6 C7 169.28(15) . . . . ?
N2 C6 C7 C8 0.12(18) . . . . ?
C5 C6 C7 C8 -177.86(15) . . . . ?
C6 C7 C8 C9 -0.51(19) . . . . ?
C6 N2 C9 C8 -0.65(18) . . . . ?
B1 N2 C9 C8 -174.40(14) . . . . ?
C7 C8 C9 N2 0.72(19) . . . . ?
C4 C5 C10 C11 6.1(2) . . . . ?
C6 C5 C10 C11 -175.95(14) . . . . ?
C16 N3 C11 C10 -2.4(2) . . . . ?
C12 N3 C11 C10 -176.30(14) . . . . ?
C5 C10 C11 N3 -177.90(15) . . . . ?
C11 N3 C12 C13 116.40(16) . . . . ?
C16 N3 C12 C13 -58.14(18) . . . . ?
N3 C12 C13 C14 53.24(19) . . . . ?
C12 C13 C14 C15 -53.11(19) . . . . ?
C13 C14 C15 C16 55.07(19) . . . . ?
C11 N3 C16 C15 -113.65(16) . . . . ?
C12 N3 C16 C15 60.65(17) . . . . ?
C14 C15 C16 N3 -57.72(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.060

#===END
_database_code_depnum_ccdc_archive 'CCDC 1001553'
