# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

#######################################################################
#
#                 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_ch14596

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 B F2 N2 O'
_chemical_formula_sum            'C19 H13 B F2 N2 O'
_chemical_formula_weight         334.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.6771(16)
_cell_length_b                   10.1854(17)
_cell_length_c                   20.076(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.451(9)
_cell_angle_gamma                90.00
_cell_volume                     1548.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10317
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_sigmaI/netI    0.1265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2713
_reflns_number_gt                1135
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0919P)²+0.0000P] 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         2713
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1768
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1957
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3299(6) -0.1304(4) 0.9043(2) 0.0520(12) Uani 1 1 d . . .
C2 C 0.3582(6) -0.1972(4) 0.8471(3) 0.0653(14) Uani 1 1 d . . .
H2 H 0.3246 -0.1625 0.8041 0.078 Uiso 1 1 calc R . .
C3 C 0.4390(7) -0.3180(5) 0.8573(3) 0.0808(17) Uani 1 1 d . . .
H3 H 0.4600 -0.3664 0.8201 0.097 Uiso 1 1 calc R . .
C4 C 0.4894(7) -0.3688(5) 0.9211(4) 0.0835(18) Uani 1 1 d . . .
H4 H 0.5458 -0.4498 0.9256 0.100 Uiso 1 1 calc R . .
C5 C 0.4597(6) -0.3046(5) 0.9785(3) 0.0760(16) Uani 1 1 d . . .
H5 H 0.4925 -0.3394 1.0216 0.091 Uiso 1 1 calc R . .
C6 C 0.3775(6) -0.1850(4) 0.9670(3) 0.0584(13) Uani 1 1 d . . .
C7 C 0.2521(5) 0.0041(4) 0.9793(2) 0.0487(11) Uani 1 1 d . . .
C8 C 0.1789(5) 0.1105(4) 1.0099(2) 0.0471(11) Uani 1 1 d . . .
C9 C 0.1834(6) 0.1179(4) 1.0802(2) 0.0601(13) Uani 1 1 d . . .
H9 H 0.2374 0.0513 1.1078 0.072 Uiso 1 1 calc R . .
C10 C 0.1104(7) 0.2202(5) 1.1078(2) 0.0683(15) Uani 1 1 d . . .
H10 H 0.1154 0.2251 1.1543 0.082 Uiso 1 1 calc R . .
C11 C 0.0274(6) 0.3184(4) 1.0661(2) 0.0622(14) Uani 1 1 d . . .
H11 H -0.0226 0.3890 1.0854 0.075 Uiso 1 1 calc R . .
C12 C 0.0172(6) 0.3141(4) 0.9973(2) 0.0538(12) Uani 1 1 d . . .
H12 H -0.0407 0.3807 0.9707 0.065 Uiso 1 1 calc R . .
C13 C 0.0938(5) 0.2095(4) 0.9668(2) 0.0470(11) Uani 1 1 d . . .
C14 C -0.0115(6) 0.2969(4) 0.8556(2) 0.0506(12) Uani 1 1 d . . .
C15 C 0.0726(7) 0.3945(4) 0.8251(2) 0.0629(14) Uani 1 1 d . . .
H15 H 0.1952 0.3999 0.8329 0.075 Uiso 1 1 calc R . .
C16 C -0.0275(9) 0.4851(5) 0.7825(3) 0.0721(15) Uani 1 1 d . . .
H16 H 0.0283 0.5508 0.7617 0.086 Uiso 1 1 calc R . .
C17 C -0.2072(9) 0.4764(5) 0.7716(2) 0.0758(16) Uani 1 1 d . . .
H17 H -0.2735 0.5366 0.7432 0.091 Uiso 1 1 calc R . .
C18 C -0.2908(7) 0.3808(5) 0.8019(3) 0.0721(15) Uani 1 1 d . . .
H18 H -0.4135 0.3766 0.7945 0.087 Uiso 1 1 calc R . .
C19 C -0.1936(7) 0.2906(4) 0.8433(2) 0.0590(13) Uani 1 1 d . . .
H19 H -0.2511 0.2246 0.8632 0.071 Uiso 1 1 calc R . .
B1 B 0.1983(7) 0.1062(5) 0.8635(3) 0.0550(14) Uani 1 1 d . . .
N1 N 0.2539(4) -0.0085(3) 0.91395(18) 0.0506(10) Uani 1 1 d . . .
N2 N 0.0903(5) 0.2015(3) 0.89824(17) 0.0491(9) Uani 1 1 d . . .
O1 O 0.3277(4) -0.0998(3) 1.01500(15) 0.0587(9) Uani 1 1 d . . .
F1 F 0.1038(4) 0.0539(3) 0.80543(13) 0.0867(10) Uani 1 1 d . . .
F2 F 0.3512(4) 0.1625(2) 0.84849(14) 0.0821(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.370(6) . ?
C1 C2 1.383(6) . ?
C1 N1 1.399(5) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9300 . ?
C6 O1 1.395(5) . ?
C7 N1 1.320(5) . ?
C7 O1 1.355(4) . ?
C7 C8 1.407(5) . ?
C8 C9 1.408(6) . ?
C8 C13 1.416(6) . ?
C9 C10 1.345(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(5) . ?
C12 H12 0.9300 . ?
C13 N2 1.374(5) . ?
C14 C19 1.381(6) . ?
C14 C15 1.382(6) . ?
C14 N2 1.438(5) . ?
C15 C16 1.400(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
B1 F1 1.376(6) . ?
B1 F2 1.383(6) . ?
B1 N2 1.519(6) . ?
B1 N1 1.558(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.6(4) . . ?
C6 C1 N1 106.8(4) . . ?
C2 C1 N1 132.7(4) . . ?
C3 C2 C1 116.4(5) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 C4 121.6(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 122.8(5) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 114.5(5) . . ?
C4 C5 H5 122.7 . . ?
C6 C5 H5 122.7 . . ?
C1 C6 C5 124.1(5) . . ?
C1 C6 O1 108.6(4) . . ?
C5 C6 O1 127.3(5) . . ?
N1 C7 O1 112.1(4) . . ?
N1 C7 C8 125.3(4) . . ?
O1 C7 C8 122.6(4) . . ?
C9 C8 C7 122.2(4) . . ?
C9 C8 C13 120.5(4) . . ?
C7 C8 C13 117.3(4) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.3(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.9(4) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N2 C13 C12 122.7(4) . . ?
N2 C13 C8 120.1(4) . . ?
C12 C13 C8 117.2(4) . . ?
C19 C14 C15 119.1(4) . . ?
C19 C14 N2 120.7(4) . . ?
C15 C14 N2 120.1(4) . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.6(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 120.9(5) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.9(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.7(5) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
F1 B1 F2 108.9(4) . . ?
F1 B1 N2 112.6(4) . . ?
F2 B1 N2 112.4(4) . . ?
F1 B1 N1 108.1(4) . . ?
F2 B1 N1 107.5(4) . . ?
N2 B1 N1 107.0(4) . . ?
C7 N1 C1 107.2(4) . . ?
C7 N1 B1 121.8(4) . . ?
C1 N1 B1 130.6(4) . . ?
C13 N2 C14 118.4(3) . . ?
C13 N2 B1 125.1(4) . . ?
C14 N2 B1 116.3(3) . . ?
C7 O1 C6 105.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.202
_database_code_depnum_ccdc_archive 'CCDC 966878'
#######################################################################
#
#                 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_a14978

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 B F2 N2 O'
_chemical_formula_sum            'C21 H17 B F2 N2 O'
_chemical_formula_weight         362.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
B B 0.0013 0.0007 '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                   7.9845(12)
_cell_length_b                   14.683(2)
_cell_length_c                   15.599(2)
_cell_angle_alpha                102.511(4)
_cell_angle_beta                 92.422(7)
_cell_angle_gamma                92.278(5)
_cell_volume                     1781.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14810
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_sigmaI/netI    0.1535
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6254
_reflns_number_gt                3142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0927P)²+0.0000P] 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         6254
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2202
_refine_ls_wR_factor_gt          0.1694
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4311(6) 0.7787(2) 0.5887(2) 0.0299(10) Uani 1 1 d . . .
C2 C 0.5905(6) 0.7576(3) 0.6173(3) 0.0358(11) Uani 1 1 d . . .
C3 C 0.7049(6) 0.6982(3) 0.5568(3) 0.0529(13) Uani 1 1 d . . .
H3A H 0.8096 0.6914 0.5894 0.079 Uiso 1 1 calc R . .
H3B H 0.7299 0.7281 0.5080 0.079 Uiso 1 1 calc R . .
H3C H 0.6498 0.6364 0.5334 0.079 Uiso 1 1 calc R . .
C4 C 0.6396(7) 0.7946(3) 0.7063(3) 0.0548(14) Uani 1 1 d . . .
H4 H 0.7473 0.7821 0.7280 0.066 Uiso 1 1 calc R . .
C5 C 0.5365(8) 0.8481(3) 0.7625(3) 0.0614(17) Uani 1 1 d . . .
H5 H 0.5718 0.8710 0.8225 0.074 Uiso 1 1 calc R . .
C6 C 0.3822(8) 0.8685(3) 0.7319(3) 0.0530(15) Uani 1 1 d . . .
H6 H 0.3121 0.9063 0.7711 0.064 Uiso 1 1 calc R . .
C7 C 0.3253(6) 0.8348(2) 0.6440(2) 0.0329(11) Uani 1 1 d . . .
C8 C 0.1564(6) 0.8598(3) 0.6132(3) 0.0482(13) Uani 1 1 d . . .
H8A H 0.1036 0.8999 0.6622 0.072 Uiso 1 1 calc R . .
H8B H 0.0856 0.8027 0.5915 0.072 Uiso 1 1 calc R . .
H8C H 0.1695 0.8932 0.5656 0.072 Uiso 1 1 calc R . .
C9 C 0.4342(5) 0.7867(2) 0.4350(2) 0.0260(9) Uani 1 1 d . . .
C10 C 0.5329(5) 0.8714(2) 0.4581(2) 0.0321(10) Uani 1 1 d . . .
H10 H 0.5617 0.8984 0.5182 0.039 Uiso 1 1 calc R . .
C11 C 0.5877(6) 0.9151(3) 0.3933(3) 0.0399(12) Uani 1 1 d . . .
H11 H 0.6525 0.9723 0.4104 0.048 Uiso 1 1 calc R . .
C12 C 0.5512(6) 0.8783(3) 0.3038(3) 0.0412(12) Uani 1 1 d . . .
H12 H 0.5899 0.9098 0.2608 0.049 Uiso 1 1 calc R . .
C13 C 0.4587(6) 0.7958(3) 0.2799(3) 0.0370(11) Uani 1 1 d . . .
H13 H 0.4358 0.7688 0.2192 0.044 Uiso 1 1 calc R . .
C14 C 0.3963(5) 0.7497(2) 0.3435(2) 0.0278(10) Uani 1 1 d . . .
C15 C 0.2953(5) 0.6659(3) 0.3201(2) 0.0287(10) Uani 1 1 d . . .
C16 C 0.1515(6) 0.5443(3) 0.2398(3) 0.0375(11) Uani 1 1 d . . .
C17 C 0.0794(7) 0.4768(3) 0.1701(3) 0.0522(14) Uani 1 1 d . . .
H17 H 0.0886 0.4804 0.1104 0.063 Uiso 1 1 calc R . .
C18 C -0.0067(7) 0.4040(3) 0.1949(3) 0.0559(14) Uani 1 1 d . . .
H18 H -0.0574 0.3550 0.1501 0.067 Uiso 1 1 calc R . .
C19 C -0.0229(6) 0.3988(3) 0.2823(3) 0.0507(13) Uani 1 1 d . . .
H19 H -0.0855 0.3474 0.2952 0.061 Uiso 1 1 calc R . .
C20 C 0.0507(6) 0.4673(3) 0.3516(3) 0.0401(11) Uani 1 1 d . . .
H20 H 0.0409 0.4643 0.4114 0.048 Uiso 1 1 calc R . .
C21 C 0.1394(5) 0.5403(2) 0.3268(2) 0.0294(10) Uani 1 1 d . . .
C22 C 0.9509(6) 0.8128(3) 0.0396(2) 0.0334(11) Uani 1 1 d . . .
C23 C 0.8396(6) 0.8714(3) 0.0101(2) 0.0366(11) Uani 1 1 d . . .
C24 C 0.6800(6) 0.8996(3) 0.0564(3) 0.0521(13) Uani 1 1 d . . .
H24A H 0.6702 0.8689 0.1059 0.078 Uiso 1 1 calc R . .
H24B H 0.5828 0.8806 0.0150 0.078 Uiso 1 1 calc R . .
H24C H 0.6842 0.9675 0.0781 0.078 Uiso 1 1 calc R . .
C25 C 0.8801(6) 0.9070(3) -0.0627(3) 0.0440(12) Uani 1 1 d . . .
H25 H 0.8059 0.9473 -0.0835 0.053 Uiso 1 1 calc R . .
C26 C 1.0251(7) 0.8849(3) -0.1048(3) 0.0475(13) Uani 1 1 d . . .
H26 H 1.0485 0.9081 -0.1556 0.057 Uiso 1 1 calc R . .
C27 C 1.1371(6) 0.8288(3) -0.0737(3) 0.0448(12) Uani 1 1 d . . .
H27 H 1.2391 0.8156 -0.1021 0.054 Uiso 1 1 calc R . .
C28 C 1.1019(6) 0.7915(3) -0.0011(2) 0.0368(11) Uani 1 1 d . . .
C29 C 1.2259(6) 0.7304(3) 0.0321(3) 0.0567(14) Uani 1 1 d . . .
H29A H 1.1821 0.7103 0.0832 0.085 Uiso 1 1 calc R . .
H29B H 1.3331 0.7659 0.0493 0.085 Uiso 1 1 calc R . .
H29C H 1.2428 0.6755 -0.0145 0.085 Uiso 1 1 calc R . .
C30 C 0.9681(5) 0.8175(3) 0.1962(2) 0.0308(10) Uani 1 1 d . . .
C31 C 1.0671(6) 0.9026(3) 0.2118(2) 0.0358(11) Uani 1 1 d . . .
H31 H 1.0954 0.9291 0.1635 0.043 Uiso 1 1 calc R . .
C32 C 1.1229(6) 0.9473(3) 0.2958(3) 0.0392(11) Uani 1 1 d . . .
H32 H 1.1890 1.0041 0.3042 0.047 Uiso 1 1 calc R . .
C33 C 1.0843(6) 0.9111(3) 0.3690(3) 0.0400(11) Uani 1 1 d . . .
H33 H 1.1227 0.9432 0.4265 0.048 Uiso 1 1 calc R . .
C34 C 0.9903(5) 0.8287(3) 0.3566(2) 0.0348(11) Uani 1 1 d . . .
H34 H 0.9643 0.8031 0.4057 0.042 Uiso 1 1 calc R . .
C35 C 0.9319(5) 0.7815(3) 0.2712(2) 0.0306(10) Uani 1 1 d . . .
C36 C 0.8309(5) 0.6967(3) 0.2566(2) 0.0320(10) Uani 1 1 d . . .
C37 C 0.6849(6) 0.5760(3) 0.2812(3) 0.0353(11) Uani 1 1 d . . .
C38 C 0.6088(6) 0.5109(3) 0.3207(3) 0.0454(12) Uani 1 1 d . . .
H38 H 0.6147 0.5160 0.3825 0.054 Uiso 1 1 calc R . .
C39 C 0.5225(6) 0.4370(3) 0.2623(3) 0.0496(13) Uani 1 1 d . . .
H39 H 0.4667 0.3898 0.2853 0.060 Uiso 1 1 calc R . .
C40 C 0.5148(6) 0.4295(3) 0.1715(3) 0.0496(13) Uani 1 1 d . . .
H40 H 0.4558 0.3770 0.1346 0.059 Uiso 1 1 calc R . .
C41 C 0.5905(6) 0.4963(3) 0.1339(3) 0.0395(12) Uani 1 1 d . . .
H41 H 0.5839 0.4918 0.0722 0.047 Uiso 1 1 calc R . .
C42 C 0.6775(6) 0.5709(3) 0.1915(3) 0.0340(11) Uani 1 1 d . . .
N1 N 0.3753(4) 0.74088(19) 0.49720(18) 0.0251(8) Uani 1 1 d . . .
N2 N 0.2339(4) 0.61988(19) 0.37626(19) 0.0272(8) Uani 1 1 d . . .
N3 N 0.9087(4) 0.7718(2) 0.11284(19) 0.0326(9) Uani 1 1 d . . .
N4 N 0.7716(4) 0.6494(2) 0.17794(19) 0.0320(9) Uani 1 1 d . . .
O1 O 0.2510(4) 0.62426(18) 0.23514(15) 0.0382(8) Uani 1 1 d . . .
O2 O 0.7826(4) 0.65654(17) 0.32236(16) 0.0366(8) Uani 1 1 d . . .
F1 F 0.1158(3) 0.65703(16) 0.51798(15) 0.0523(8) Uani 1 1 d . . .
F2 F 0.3525(4) 0.57766(15) 0.50520(14) 0.0507(8) Uani 1 1 d . . .
F3 F 0.8928(4) 0.60821(16) 0.03805(15) 0.0621(9) Uani 1 1 d . . .
F4 F 0.6526(4) 0.68445(17) 0.04644(16) 0.0625(8) Uani 1 1 d . . .
B1 B 0.2697(6) 0.6490(3) 0.4783(3) 0.0284(11) Uani 1 1 d . . .
B2 B 0.8084(7) 0.6784(3) 0.0896(3) 0.0380(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C7 1.395(5) . ?
C1 C2 1.399(6) . ?
C1 N1 1.458(4) . ?
C2 C4 1.410(6) . ?
C2 C3 1.505(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.499(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.383(4) . ?
C9 C10 1.414(5) . ?
C9 C14 1.427(5) . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.365(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.413(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.413(5) . ?
C15 N2 1.316(4) . ?
C15 O1 1.359(4) . ?
C16 C21 1.378(5) . ?
C16 C17 1.390(6) . ?
C16 O1 1.408(5) . ?
C17 C18 1.381(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(5) . ?
C20 H20 0.9500 . ?
C21 N2 1.422(5) . ?
C22 C23 1.393(6) . ?
C22 C28 1.402(6) . ?
C22 N3 1.447(5) . ?
C23 C25 1.393(5) . ?
C23 C24 1.518(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.371(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.381(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.395(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.510(6) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N3 1.382(5) . ?
C30 C35 1.420(5) . ?
C30 C31 1.420(5) . ?
C31 C32 1.379(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.401(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.370(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.412(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.427(5) . ?
C36 N4 1.330(5) . ?
C36 O2 1.351(4) . ?
C37 C38 1.380(5) . ?
C37 C42 1.383(5) . ?
C37 O2 1.405(5) . ?
C38 C39 1.393(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.396(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.380(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.396(6) . ?
C41 H41 0.9500 . ?
C42 N4 1.410(5) . ?
N1 B1 1.528(5) . ?
N2 B1 1.568(5) . ?
N3 B2 1.526(6) . ?
N4 B2 1.564(5) . ?
F1 B1 1.397(5) . ?
F2 B1 1.389(5) . ?
F3 B2 1.380(5) . ?
F4 B2 1.404(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 122.5(4) . . ?
C7 C1 N1 119.2(4) . . ?
C2 C1 N1 118.3(3) . . ?
C1 C2 C4 116.7(4) . . ?
C1 C2 C3 122.2(4) . . ?
C4 C2 C3 121.1(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 121.9(5) . . ?
C5 C4 H4 119.0 . . ?
C2 C4 H4 119.0 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C1 C7 C6 117.5(4) . . ?
C1 C7 C8 122.8(4) . . ?
C6 C7 C8 119.7(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 122.3(3) . . ?
N1 C9 C14 120.6(3) . . ?
C10 C9 C14 117.1(3) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 122.6(4) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C13 C12 C11 118.2(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C14 121.3(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 122.1(3) . . ?
C15 C14 C9 117.3(3) . . ?
C13 C14 C9 120.6(4) . . ?
N2 C15 O1 112.6(3) . . ?
N2 C15 C14 124.9(3) . . ?
O1 C15 C14 122.5(3) . . ?
C21 C16 C17 123.6(4) . . ?
C21 C16 O1 109.0(3) . . ?
C17 C16 O1 127.4(4) . . ?
C18 C17 C16 114.4(4) . . ?
C18 C17 H17 122.8 . . ?
C16 C17 H17 122.8 . . ?
C17 C18 C19 123.2(4) . . ?
C17 C18 H18 118.4 . . ?
C19 C18 H18 118.4 . . ?
C18 C19 C20 121.6(5) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 115.3(4) . . ?
C21 C20 H20 122.3 . . ?
C19 C20 H20 122.3 . . ?
C16 C21 C20 121.9(4) . . ?
C16 C21 N2 105.9(3) . . ?
C20 C21 N2 132.2(4) . . ?
C23 C22 C28 121.3(4) . . ?
C23 C22 N3 119.4(4) . . ?
C28 C22 N3 119.3(4) . . ?
C25 C23 C22 118.3(4) . . ?
C25 C23 C24 119.6(4) . . ?
C22 C23 C24 122.1(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C23 121.3(4) . . ?
C26 C25 H25 119.4 . . ?
C23 C25 H25 119.4 . . ?
C25 C26 C27 120.2(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C22 118.3(4) . . ?
C27 C28 C29 120.0(4) . . ?
C22 C28 C29 121.7(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 C35 121.2(4) . . ?
N3 C30 C31 122.3(3) . . ?
C35 C30 C31 116.4(3) . . ?
C32 C31 C30 121.1(4) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 121.6(4) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C34 C33 C32 119.1(4) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 120.4(4) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C34 C35 C30 121.4(4) . . ?
C34 C35 C36 121.5(4) . . ?
C30 C35 C36 117.1(3) . . ?
N4 C36 O2 112.6(3) . . ?
N4 C36 C35 124.3(3) . . ?
O2 C36 C35 123.1(3) . . ?
C38 C37 C42 124.2(4) . . ?
C38 C37 O2 127.5(4) . . ?
C42 C37 O2 108.3(3) . . ?
C37 C38 C39 114.4(4) . . ?
C37 C38 H38 122.8 . . ?
C39 C38 H38 122.8 . . ?
C38 C39 C40 122.6(4) . . ?
C38 C39 H39 118.7 . . ?
C40 C39 H39 118.7 . . ?
C41 C40 C39 121.7(4) . . ?
C41 C40 H40 119.1 . . ?
C39 C40 H40 119.1 . . ?
C40 C41 C42 116.4(4) . . ?
C40 C41 H41 121.8 . . ?
C42 C41 H41 121.8 . . ?
C37 C42 C41 120.7(4) . . ?
C37 C42 N4 106.7(4) . . ?
C41 C42 N4 132.7(4) . . ?
C9 N1 C1 117.3(3) . . ?
C9 N1 B1 126.0(3) . . ?
C1 N1 B1 116.4(3) . . ?
C15 N2 C21 107.5(3) . . ?
C15 N2 B1 124.1(3) . . ?
C21 N2 B1 128.4(3) . . ?
C30 N3 C22 118.1(3) . . ?
C30 N3 B2 125.8(3) . . ?
C22 N3 B2 116.0(3) . . ?
C36 N4 C42 106.9(3) . . ?
C36 N4 B2 124.1(3) . . ?
C42 N4 B2 129.0(3) . . ?
C15 O1 C16 105.0(3) . . ?
C36 O2 C37 105.5(3) . . ?
F2 B1 F1 107.9(3) . . ?
F2 B1 N1 112.5(4) . . ?
F1 B1 N1 112.8(3) . . ?
F2 B1 N2 108.3(3) . . ?
F1 B1 N2 108.1(3) . . ?
N1 B1 N2 107.1(3) . . ?
F3 B2 F4 108.0(4) . . ?
F3 B2 N3 113.3(4) . . ?
F4 B2 N3 112.5(4) . . ?
F3 B2 N4 108.4(3) . . ?
F4 B2 N4 107.1(4) . . ?
N3 B2 N4 107.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 966879'
#######################################################################
#
#                 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_ch14962

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 B F2 N2 O'
_chemical_formula_sum            'C23 H21 B F2 N2 O'
_chemical_formula_weight         390.23

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   'P b c a'

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'
'-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                   9.9254(4)
_cell_length_b                   15.5842(5)
_cell_length_c                   24.9184(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3854.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow-green
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9294
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22055
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3412
_reflns_number_gt                2620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0905P)²+1.1481P] 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         3412
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.9184(3) 0.57661(15) 0.09681(9) 0.0296(5) Uani 1 1 d . . .
C1 C 0.7428(2) 0.69225(13) 0.09186(8) 0.0285(5) Uani 1 1 d . . .
C2 C 0.7994(2) 0.77459(14) 0.09323(9) 0.0338(5) Uani 1 1 d . . .
C3 C 0.9155(3) 0.79741(16) 0.12921(11) 0.0496(7) Uani 1 1 d . . .
H3A H 0.9363 0.7471 0.1520 0.060 Uiso 1 1 calc R . .
H3B H 0.9954 0.8085 0.1065 0.060 Uiso 1 1 calc R . .
C4 C 0.8945(4) 0.8717(2) 0.16410(14) 0.0877(12) Uani 1 1 d . . .
H4A H 0.9754 0.8813 0.1858 0.132 Uiso 1 1 calc R . .
H4B H 0.8174 0.8610 0.1877 0.132 Uiso 1 1 calc R . .
H4C H 0.8766 0.9226 0.1421 0.132 Uiso 1 1 calc R . .
C5 C 0.7445(3) 0.83657(15) 0.05979(10) 0.0422(6) Uani 1 1 d . . .
H5 H 0.7819 0.8927 0.0598 0.051 Uiso 1 1 calc R . .
C6 C 0.6378(3) 0.81893(16) 0.02678(10) 0.0457(6) Uani 1 1 d . . .
H6 H 0.6026 0.8624 0.0040 0.055 Uiso 1 1 calc R . .
C7 C 0.5817(3) 0.73839(17) 0.02656(9) 0.0449(6) Uani 1 1 d . . .
H7 H 0.5067 0.7270 0.0039 0.054 Uiso 1 1 calc R . .
C8 C 0.6324(2) 0.67320(15) 0.05886(9) 0.0362(5) Uani 1 1 d . . .
C9 C 0.5679(3) 0.58549(17) 0.05732(12) 0.0535(7) Uani 1 1 d . . .
H9A H 0.5548 0.5685 0.0194 0.064 Uiso 1 1 calc R . .
H9B H 0.6302 0.5435 0.0739 0.064 Uiso 1 1 calc R . .
C10 C 0.4347(3) 0.5811(2) 0.08577(17) 0.0839(11) Uani 1 1 d . . .
H10A H 0.3988 0.5227 0.0833 0.126 Uiso 1 1 calc R . .
H10B H 0.3715 0.6213 0.0690 0.126 Uiso 1 1 calc R . .
H10C H 0.4470 0.5966 0.1236 0.126 Uiso 1 1 calc R . .
C11 C 0.7640(2) 0.61511(12) 0.17628(8) 0.0283(5) Uani 1 1 d . . .
C12 C 0.6681(2) 0.66947(14) 0.20068(9) 0.0351(5) Uani 1 1 d . . .
H12 H 0.6257 0.7130 0.1800 0.042 Uiso 1 1 calc R . .
C13 C 0.6354(2) 0.66015(14) 0.25392(9) 0.0387(6) Uani 1 1 d . . .
H13 H 0.5705 0.6977 0.2692 0.046 Uiso 1 1 calc R . .
C14 C 0.6946(2) 0.59717(15) 0.28635(9) 0.0382(6) Uani 1 1 d . . .
H14 H 0.6728 0.5931 0.3234 0.046 Uiso 1 1 calc R . .
C15 C 0.7845(2) 0.54163(14) 0.26350(8) 0.0354(5) Uani 1 1 d . . .
H15 H 0.8235 0.4974 0.2846 0.042 Uiso 1 1 calc R . .
C16 C 0.8199(2) 0.54935(13) 0.20886(8) 0.0297(5) Uani 1 1 d . . .
C17 C 0.9117(2) 0.49258(12) 0.18423(8) 0.0284(5) Uani 1 1 d . . .
C18 C 1.0536(2) 0.38662(13) 0.17274(9) 0.0320(5) Uani 1 1 d . . .
C19 C 1.1340(2) 0.31550(14) 0.17966(10) 0.0407(6) Uani 1 1 d . . .
H19 H 1.1364 0.2839 0.2123 0.049 Uiso 1 1 calc R . .
C20 C 1.2113(2) 0.29352(15) 0.13540(11) 0.0441(6) Uani 1 1 d . . .
H20 H 1.2682 0.2446 0.1376 0.053 Uiso 1 1 calc R . .
C21 C 1.2085(2) 0.34029(15) 0.08817(10) 0.0401(6) Uani 1 1 d . . .
H21 H 1.2640 0.3227 0.0591 0.048 Uiso 1 1 calc R . .
C22 C 1.1273(2) 0.41187(14) 0.08196(9) 0.0344(5) Uani 1 1 d . . .
H22 H 1.1254 0.4441 0.0496 0.041 Uiso 1 1 calc R . .
C23 C 1.0490(2) 0.43345(13) 0.12588(8) 0.0290(5) Uani 1 1 d . . .
F1 F 1.03460(13) 0.62639(8) 0.09163(5) 0.0412(4) Uani 1 1 d . . .
F2 F 0.88325(14) 0.54443(8) 0.04721(5) 0.0433(4) Uani 1 1 d . . .
N1 N 0.80310(17) 0.62446(11) 0.12384(7) 0.0293(4) Uani 1 1 d . . .
N2 N 0.95554(17) 0.49998(11) 0.13469(7) 0.0280(4) Uani 1 1 d . . .
O1 O 0.96604(15) 0.42403(9) 0.20982(6) 0.0347(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 1.379(3) . ?
B1 F1 1.396(3) . ?
B1 N1 1.523(3) . ?
B1 N2 1.566(3) . ?
C1 C2 1.401(3) . ?
C1 C8 1.401(3) . ?
C1 N1 1.452(3) . ?
C2 C5 1.387(3) . ?
C2 C3 1.503(3) . ?
C3 C4 1.463(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.368(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.510(3) . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.371(3) . ?
C11 C12 1.412(3) . ?
C11 C16 1.420(3) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(3) . ?
C17 N2 1.314(3) . ?
C17 O1 1.356(2) . ?
C18 C23 1.378(3) . ?
C18 C19 1.377(3) . ?
C18 O1 1.396(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 N2 1.408(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 B1 F1 109.17(18) . . ?
F2 B1 N1 112.60(18) . . ?
F1 B1 N1 112.94(18) . . ?
F2 B1 N2 108.81(17) . . ?
F1 B1 N2 106.57(17) . . ?
N1 B1 N2 106.47(17) . . ?
C2 C1 C8 121.43(19) . . ?
C2 C1 N1 119.18(18) . . ?
C8 C1 N1 119.34(18) . . ?
C5 C2 C1 117.8(2) . . ?
C5 C2 C3 119.7(2) . . ?
C1 C2 C3 122.6(2) . . ?
C4 C3 C2 115.6(2) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C2 C5 H5 119.2 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C1 117.9(2) . . ?
C7 C8 C9 119.5(2) . . ?
C1 C8 C9 122.6(2) . . ?
C10 C9 C8 113.7(2) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 122.51(19) . . ?
N1 C11 C16 120.74(18) . . ?
C12 C11 C16 116.74(19) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 122.2(2) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 121.82(19) . . ?
C17 C16 C11 117.13(18) . . ?
C15 C16 C11 121.1(2) . . ?
N2 C17 O1 112.30(18) . . ?
N2 C17 C16 124.59(18) . . ?
O1 C17 C16 123.11(18) . . ?
C23 C18 C19 123.5(2) . . ?
C23 C18 O1 108.61(17) . . ?
C19 C18 O1 127.9(2) . . ?
C18 C19 C20 114.8(2) . . ?
C18 C19 H19 122.6 . . ?
C20 C19 H19 122.6 . . ?
C21 C20 C19 122.3(2) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C22 C21 C20 122.0(2) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 115.7(2) . . ?
C21 C22 H22 122.1 . . ?
C23 C22 H22 122.1 . . ?
C18 C23 C22 121.5(2) . . ?
C18 C23 N2 106.25(18) . . ?
C22 C23 N2 132.22(19) . . ?
C11 N1 C1 118.93(16) . . ?
C11 N1 B1 125.60(17) . . ?
C1 N1 B1 115.04(16) . . ?
C17 N2 C23 107.45(16) . . ?
C17 N2 B1 123.73(17) . . ?
C23 N2 B1 128.49(17) . . ?
C17 O1 C18 105.37(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.123
_database_code_depnum_ccdc_archive 'CCDC 966880'
#######################################################################
#
#                 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_a15120

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 B F2 N2 O'
_chemical_formula_sum            'C25 H25 B F2 N2 O'
_chemical_formula_weight         418.28

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   'P b c a'

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'
'-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                   9.6279(19)
_cell_length_b                   18.412(3)
_cell_length_c                   24.120(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4275.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18153
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_sigmaI/netI    0.1213
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3774
_reflns_number_gt                1798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0705P)²+0.0000P] 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         3774
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7734(4) 0.28439(17) 0.26342(13) 0.0312(9) Uani 1 1 d . . .
C2 C 0.8728(4) 0.33547(18) 0.27605(14) 0.0392(10) Uani 1 1 d . . .
H2 H 0.9038 0.3434 0.3130 0.047 Uiso 1 1 calc R . .
C3 C 0.9250(4) 0.37480(19) 0.23153(17) 0.0490(11) Uani 1 1 d . . .
H3 H 0.9941 0.4106 0.2382 0.059 Uiso 1 1 calc R . .
C4 C 0.8798(4) 0.3634(2) 0.17801(17) 0.0509(11) Uani 1 1 d . . .
H4 H 0.9201 0.3909 0.1488 0.061 Uiso 1 1 calc R . .
C5 C 0.7772(4) 0.31300(18) 0.16545(14) 0.0432(10) Uani 1 1 d . . .
H5 H 0.7434 0.3060 0.1288 0.052 Uiso 1 1 calc R . .
C6 C 0.7286(4) 0.27424(18) 0.20958(14) 0.0374(9) Uani 1 1 d . . .
C7 C 0.6158(4) 0.19764(17) 0.26236(13) 0.0308(9) Uani 1 1 d . . .
C8 C 0.5257(3) 0.14153(17) 0.27897(12) 0.0278(8) Uani 1 1 d . . .
C9 C 0.4385(4) 0.10626(18) 0.24065(13) 0.0354(9) Uani 1 1 d . . .
H9 H 0.4403 0.1204 0.2028 0.042 Uiso 1 1 calc R . .
C10 C 0.3517(4) 0.05218(18) 0.25728(14) 0.0429(10) Uani 1 1 d . . .
H10 H 0.2920 0.0287 0.2315 0.051 Uiso 1 1 calc R . .
C11 C 0.3523(4) 0.03189(18) 0.31329(15) 0.0438(10) Uani 1 1 d . . .
H11 H 0.2914 -0.0055 0.3253 0.053 Uiso 1 1 calc R . .
C12 C 0.4385(4) 0.06455(17) 0.35130(14) 0.0379(9) Uani 1 1 d . . .
H12 H 0.4374 0.0486 0.3888 0.046 Uiso 1 1 calc R . .
C13 C 0.5284(3) 0.12136(16) 0.33551(13) 0.0276(8) Uani 1 1 d . . .
C14 C 0.6158(3) 0.12915(16) 0.42893(12) 0.0259(8) Uani 1 1 d . . .
C15 C 0.5219(3) 0.15885(17) 0.46719(13) 0.0304(9) Uani 1 1 d . . .
C16 C 0.4095(4) 0.21207(18) 0.45064(14) 0.0366(9) Uani 1 1 d . . .
H16 H 0.4214 0.2227 0.4103 0.044 Uiso 1 1 calc R . .
C17 C 0.4189(4) 0.28366(18) 0.48158(14) 0.0515(11) Uani 1 1 d . . .
H17A H 0.3451 0.3162 0.4688 0.077 Uiso 1 1 calc R . .
H17B H 0.5095 0.3061 0.4745 0.077 Uiso 1 1 calc R . .
H17C H 0.4083 0.2749 0.5214 0.077 Uiso 1 1 calc R . .
C18 C 0.2650(4) 0.1778(2) 0.45834(16) 0.0604(12) Uani 1 1 d . . .
H18A H 0.1935 0.2125 0.4466 0.091 Uiso 1 1 calc R . .
H18B H 0.2512 0.1656 0.4975 0.091 Uiso 1 1 calc R . .
H18C H 0.2582 0.1337 0.4358 0.091 Uiso 1 1 calc R . .
C19 C 0.5284(4) 0.13367(19) 0.52193(13) 0.0367(9) Uani 1 1 d . . .
H19 H 0.4672 0.1534 0.5489 0.044 Uiso 1 1 calc R . .
C20 C 0.6218(4) 0.08097(18) 0.53719(14) 0.0401(10) Uani 1 1 d . . .
H20 H 0.6256 0.0652 0.5747 0.048 Uiso 1 1 calc R . .
C21 C 0.7099(4) 0.05079(17) 0.49874(13) 0.0359(9) Uani 1 1 d . . .
H21 H 0.7720 0.0134 0.5097 0.043 Uiso 1 1 calc R . .
C22 C 0.7094(3) 0.07428(16) 0.44390(12) 0.0283(8) Uani 1 1 d . . .
C23 C 0.8067(4) 0.03924(17) 0.40178(14) 0.0358(9) Uani 1 1 d . . .
H23 H 0.7947 0.0656 0.3659 0.043 Uiso 1 1 calc R . .
C24 C 0.7675(4) -0.03982(17) 0.39197(16) 0.0609(12) Uani 1 1 d . . .
H24A H 0.8310 -0.0612 0.3647 0.091 Uiso 1 1 calc R . .
H24B H 0.6721 -0.0424 0.3779 0.091 Uiso 1 1 calc R . .
H24C H 0.7740 -0.0667 0.4269 0.091 Uiso 1 1 calc R . .
C25 C 0.9599(4) 0.0457(2) 0.41838(15) 0.0585(12) Uani 1 1 d . . .
H25A H 1.0180 0.0229 0.3899 0.088 Uiso 1 1 calc R . .
H25B H 0.9747 0.0213 0.4540 0.088 Uiso 1 1 calc R . .
H25C H 0.9849 0.0971 0.4218 0.088 Uiso 1 1 calc R . .
B1 B 0.7070(4) 0.2202(2) 0.36016(15) 0.0309(10) Uani 1 1 d . . .
N1 N 0.6986(3) 0.23430(13) 0.29609(10) 0.0261(7) Uani 1 1 d . . .
N2 N 0.6145(3) 0.15531(13) 0.37230(9) 0.0252(7) Uani 1 1 d . . .
O1 O 0.6293(2) 0.21909(12) 0.20900(8) 0.0361(6) Uani 1 1 d . . .
F1 F 0.84603(19) 0.20729(10) 0.37273(7) 0.0405(5) Uani 1 1 d . . .
F2 F 0.6659(2) 0.28315(9) 0.38722(7) 0.0444(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(4) . ?
C1 C6 1.381(4) . ?
C1 N1 1.411(4) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.364(4) . ?
C5 H5 0.9500 . ?
C6 O1 1.395(4) . ?
C7 N1 1.324(4) . ?
C7 O1 1.353(3) . ?
C7 C8 1.407(4) . ?
C8 C9 1.407(4) . ?
C8 C13 1.414(4) . ?
C9 C10 1.361(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(4) . ?
C12 H12 0.9500 . ?
C13 N2 1.366(4) . ?
C14 C22 1.401(4) . ?
C14 C15 1.403(4) . ?
C14 N2 1.448(3) . ?
C15 C19 1.401(4) . ?
C15 C16 1.513(4) . ?
C16 C17 1.517(4) . ?
C16 C18 1.539(5) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.373(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.525(4) . ?
C23 C24 1.522(4) . ?
C23 C25 1.532(5) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
B1 F2 1.388(4) . ?
B1 F1 1.393(4) . ?
B1 N2 1.519(4) . ?
B1 N1 1.569(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(3) . . ?
C2 C1 N1 132.7(3) . . ?
C6 C1 N1 106.1(3) . . ?
C1 C2 C3 115.9(3) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 115.1(4) . . ?
C6 C5 H5 122.5 . . ?
C4 C5 H5 122.5 . . ?
C5 C6 C1 123.8(4) . . ?
C5 C6 O1 127.5(3) . . ?
C1 C6 O1 108.8(3) . . ?
N1 C7 O1 112.2(3) . . ?
N1 C7 C8 124.8(3) . . ?
O1 C7 C8 123.0(3) . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 C13 117.1(3) . . ?
C9 C8 C13 121.6(3) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 118.5(3) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N2 C13 C12 122.5(3) . . ?
N2 C13 C8 121.2(3) . . ?
C12 C13 C8 116.4(3) . . ?
C22 C14 C15 121.7(3) . . ?
C22 C14 N2 119.2(3) . . ?
C15 C14 N2 119.0(3) . . ?
C19 C15 C14 117.5(3) . . ?
C19 C15 C16 119.7(3) . . ?
C14 C15 C16 122.7(3) . . ?
C15 C16 C17 113.0(3) . . ?
C15 C16 C18 110.4(3) . . ?
C17 C16 C18 110.5(3) . . ?
C15 C16 H16 107.6 . . ?
C17 C16 H16 107.6 . . ?
C18 C16 H16 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C15 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C15 C19 H19 119.5 . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C14 118.1(3) . . ?
C21 C22 C23 120.0(3) . . ?
C14 C22 C23 121.9(3) . . ?
C24 C23 C22 110.8(3) . . ?
C24 C23 C25 110.7(3) . . ?
C22 C23 C25 112.6(3) . . ?
C24 C23 H23 107.5 . . ?
C22 C23 H23 107.5 . . ?
C25 C23 H23 107.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F2 B1 F1 108.3(3) . . ?
F2 B1 N2 113.5(3) . . ?
F1 B1 N2 112.8(3) . . ?
F2 B1 N1 108.1(3) . . ?
F1 B1 N1 107.0(3) . . ?
N2 B1 N1 106.9(3) . . ?
C7 N1 C1 107.3(3) . . ?
C7 N1 B1 123.5(3) . . ?
C1 N1 B1 129.2(3) . . ?
C13 N2 C14 117.7(2) . . ?
C13 N2 B1 126.2(3) . . ?
C14 N2 B1 116.0(2) . . ?
C7 O1 C6 105.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 966881'
#######################################################################
#
#                 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_a14989

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 B Cl2 F2 N2 O'
_chemical_formula_sum            'C19 H11 B Cl2 F2 N2 O'
_chemical_formula_weight         403.01

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'
Cl Cl 0.1484 0.1585 '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                   11.8174(18)
_cell_length_b                   10.0040(15)
_cell_length_c                   15.2107(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.682(7)
_cell_angle_gamma                90.00
_cell_volume                     1777.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8203
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11531
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3130
_reflns_number_gt                2258
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0826P)²+0.3479P] 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         3130
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.7101(3) 0.4237(4) 0.43347(19) 0.0235(8) Uani 1 1 d . . .
C1 C 0.7556(3) 0.5737(3) 0.58123(17) 0.0249(7) Uani 1 1 d . . .
C2 C 0.6646(3) 0.6597(3) 0.5784(2) 0.0323(8) Uani 1 1 d . . .
H2 H 0.6037 0.6604 0.5300 0.039 Uiso 1 1 calc R . .
C3 C 0.6667(3) 0.7457(4) 0.6505(2) 0.0432(9) Uani 1 1 d . . .
H3 H 0.6057 0.8073 0.6513 0.052 Uiso 1 1 calc R . .
C4 C 0.7575(3) 0.7436(4) 0.7225(2) 0.0451(10) Uani 1 1 d . . .
H4 H 0.7549 0.8024 0.7713 0.054 Uiso 1 1 calc R . .
C5 C 0.8497(3) 0.6589(4) 0.7241(2) 0.0398(9) Uani 1 1 d . . .
H5 H 0.9116 0.6580 0.7718 0.048 Uiso 1 1 calc R . .
C6 C 0.8458(3) 0.5755(3) 0.65151(18) 0.0283(8) Uani 1 1 d . . .
C7 C 0.8833(3) 0.4239(3) 0.55630(16) 0.0223(7) Uani 1 1 d . . .
C8 C 0.9421(2) 0.3223(3) 0.51655(17) 0.0230(7) Uani 1 1 d . . .
C9 C 1.0538(3) 0.2815(3) 0.55251(18) 0.0285(8) Uani 1 1 d . . .
H9 H 1.0924 0.3246 0.6042 0.034 Uiso 1 1 calc R . .
C10 C 1.1075(3) 0.1805(4) 0.5139(2) 0.0357(9) Uani 1 1 d . . .
H10 H 1.1828 0.1532 0.5380 0.043 Uiso 1 1 calc R . .
C11 C 1.0484(3) 0.1185(3) 0.4379(2) 0.0356(9) Uani 1 1 d . . .
H11 H 1.0845 0.0474 0.4114 0.043 Uiso 1 1 calc R . .
C12 C 0.9406(3) 0.1566(3) 0.40043(18) 0.0307(8) Uani 1 1 d . . .
H12 H 0.9041 0.1123 0.3485 0.037 Uiso 1 1 calc R . .
C13 C 0.8826(3) 0.2608(3) 0.43763(16) 0.0222(7) Uani 1 1 d . . .
C14 C 0.7133(3) 0.2332(3) 0.32846(18) 0.0269(8) Uani 1 1 d . . .
C15 C 0.6413(3) 0.1271(4) 0.3395(2) 0.0370(9) Uani 1 1 d . . .
C16 C 0.5731(3) 0.0659(4) 0.2663(3) 0.0530(11) Uani 1 1 d . . .
H16 H 0.5242 -0.0069 0.2749 0.064 Uiso 1 1 calc R . .
C17 C 0.5788(3) 0.1143(5) 0.1815(2) 0.0551(12) Uani 1 1 d . . .
H17 H 0.5313 0.0758 0.1320 0.066 Uiso 1 1 calc R . .
C18 C 0.6506(3) 0.2153(4) 0.1678(2) 0.0510(11) Uani 1 1 d . . .
H18 H 0.6543 0.2462 0.1093 0.061 Uiso 1 1 calc R . .
C19 C 0.7190(3) 0.2731(4) 0.24047(19) 0.0369(9) Uani 1 1 d . . .
Cl1 Cl 0.63512(10) 0.06677(10) 0.44566(7) 0.0563(4) Uani 1 1 d . . .
Cl2 Cl 0.81567(10) 0.39583(11) 0.22082(6) 0.0586(4) Uani 1 1 d . . .
F1 F 0.69904(16) 0.52950(19) 0.37308(10) 0.0352(5) Uani 1 1 d . . .
F2 F 0.60222(15) 0.38969(18) 0.45115(10) 0.0317(5) Uani 1 1 d . . .
N1 N 0.7835(2) 0.4745(2) 0.52237(13) 0.0213(6) Uani 1 1 d . . .
N2 N 0.7745(2) 0.3042(3) 0.40219(14) 0.0237(6) Uani 1 1 d . . .
O1 O 0.92679(17) 0.4805(2) 0.63524(11) 0.0281(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 F2 1.385(4) . ?
B1 F1 1.395(4) . ?
B1 N2 1.531(4) . ?
B1 N1 1.576(4) . ?
C1 C2 1.373(4) . ?
C1 C6 1.391(4) . ?
C1 N1 1.408(4) . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 O1 1.397(4) . ?
C7 N1 1.316(4) . ?
C7 O1 1.356(3) . ?
C7 C8 1.417(4) . ?
C8 C9 1.411(4) . ?
C8 C13 1.435(4) . ?
C9 C10 1.372(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.369(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(4) . ?
C12 H12 0.9500 . ?
C13 N2 1.380(4) . ?
C14 C15 1.386(5) . ?
C14 C19 1.408(4) . ?
C14 N2 1.428(4) . ?
C15 C16 1.412(5) . ?
C15 Cl1 1.736(4) . ?
C16 C17 1.389(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.355(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(5) . ?
C18 H18 0.9500 . ?
C19 Cl2 1.733(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 B1 F1 108.5(3) . . ?
F2 B1 N2 112.6(3) . . ?
F1 B1 N2 112.9(2) . . ?
F2 B1 N1 108.4(2) . . ?
F1 B1 N1 107.7(3) . . ?
N2 B1 N1 106.5(2) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 N1 132.7(3) . . ?
C6 C1 N1 105.8(3) . . ?
C1 C2 C3 116.3(3) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 115.3(3) . . ?
C4 C5 H5 122.3 . . ?
C6 C5 H5 122.3 . . ?
C5 C6 C1 123.5(3) . . ?
C5 C6 O1 127.8(3) . . ?
C1 C6 O1 108.7(2) . . ?
N1 C7 O1 112.6(2) . . ?
N1 C7 C8 125.2(2) . . ?
O1 C7 C8 122.2(3) . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 C13 120.8(3) . . ?
C7 C8 C13 117.1(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N2 C13 C12 123.5(3) . . ?
N2 C13 C8 120.0(3) . . ?
C12 C13 C8 116.5(3) . . ?
C15 C14 C19 116.8(3) . . ?
C15 C14 N2 122.2(3) . . ?
C19 C14 N2 120.9(3) . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 Cl1 119.4(2) . . ?
C16 C15 Cl1 118.9(3) . . ?
C17 C16 C15 118.6(4) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C14 122.1(4) . . ?
C18 C19 Cl2 118.4(3) . . ?
C14 C19 Cl2 119.5(2) . . ?
C7 N1 C1 107.7(2) . . ?
C7 N1 B1 123.8(2) . . ?
C1 N1 B1 128.4(2) . . ?
C13 N2 C14 118.7(2) . . ?
C13 N2 B1 126.8(2) . . ?
C14 N2 B1 114.6(2) . . ?
C7 O1 C6 105.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.109
_database_code_depnum_ccdc_archive 'CCDC 966882'
#######################################################################
#
#                 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_a15002

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 B Br2 F2 N2 O'
_chemical_formula_sum            'C19 H11 B Br2 F2 N2 O'
_chemical_formula_weight         491.93

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   '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                   12.050(3)
_cell_length_b                   9.965(3)
_cell_length_c                   15.290(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.226(5)
_cell_angle_gamma                90.00
_cell_volume                     1806.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    4.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1246
_exptl_absorpt_correction_T_max  0.2857
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9438
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3190
_reflns_number_gt                1905
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0436P)²+0.0000P] 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         3190
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7510(4) 0.5751(6) 1.0793(3) 0.0222(14) Uani 1 1 d . . .
C2 C 0.6588(4) 0.6592(6) 1.0751(4) 0.0296(15) Uani 1 1 d . . .
H2 H 0.5985 0.6589 1.0258 0.035 Uiso 1 1 calc R . .
C3 C 0.6599(5) 0.7439(6) 1.1472(4) 0.0377(17) Uani 1 1 d . . .
H3 H 0.5991 0.8046 1.1473 0.045 Uiso 1 1 calc R . .
C4 C 0.7495(5) 0.7418(7) 1.2204(4) 0.0428(18) Uani 1 1 d . . .
H4 H 0.7457 0.7994 1.2693 0.051 Uiso 1 1 calc R . .
C5 C 0.8428(5) 0.6593(6) 1.2240(4) 0.0354(17) Uani 1 1 d . . .
H5 H 0.9037 0.6591 1.2728 0.042 Uiso 1 1 calc R . .
C6 C 0.8399(4) 0.5784(6) 1.1514(4) 0.0244(14) Uani 1 1 d . . .
C7 C 0.8802(4) 0.4282(6) 1.0572(3) 0.0206(14) Uani 1 1 d . . .
C8 C 0.9386(4) 0.3280(5) 1.0183(3) 0.0168(13) Uani 1 1 d . . .
C9 C 1.0501(4) 0.2929(6) 1.0558(3) 0.0240(14) Uani 1 1 d . . .
H9 H 1.0876 0.3388 1.1070 0.029 Uiso 1 1 calc R . .
C10 C 1.1051(4) 0.1926(6) 1.0189(4) 0.0290(15) Uani 1 1 d . . .
H10 H 1.1803 0.1687 1.0440 0.035 Uiso 1 1 calc R . .
C11 C 1.0480(4) 0.1269(6) 0.9440(4) 0.0331(16) Uani 1 1 d . . .
H11 H 1.0851 0.0563 0.9190 0.040 Uiso 1 1 calc R . .
C12 C 0.9396(4) 0.1605(6) 0.9047(3) 0.0266(15) Uani 1 1 d . . .
H12 H 0.9037 0.1135 0.8533 0.032 Uiso 1 1 calc R . .
C13 C 0.8819(4) 0.2636(5) 0.9403(3) 0.0169(13) Uani 1 1 d . . .
C14 C 0.7134(4) 0.2296(6) 0.8296(3) 0.0225(14) Uani 1 1 d . . .
C15 C 0.6422(4) 0.1227(6) 0.8414(4) 0.0272(15) Uani 1 1 d . . .
C16 C 0.5750(5) 0.0620(7) 0.7698(5) 0.0430(19) Uani 1 1 d . . .
H16 H 0.5271 -0.0104 0.7789 0.052 Uiso 1 1 calc R . .
C17 C 0.5778(5) 0.1069(7) 0.6849(4) 0.0449(19) Uani 1 1 d . . .
H17 H 0.5296 0.0669 0.6359 0.054 Uiso 1 1 calc R . .
C18 C 0.6482(5) 0.2074(7) 0.6702(4) 0.0394(18) Uani 1 1 d . . .
H18 H 0.6506 0.2366 0.6114 0.047 Uiso 1 1 calc R . .
C19 C 0.7168(4) 0.2670(6) 0.7424(4) 0.0293(15) Uani 1 1 d . . .
B1 B 0.7091(5) 0.4243(7) 0.9325(4) 0.0222(17) Uani 1 1 d . . .
O1 O 0.9214(3) 0.4856(4) 1.1360(2) 0.0253(10) Uani 1 1 d . . .
F1 F 0.6968(2) 0.5279(3) 0.87113(19) 0.0328(9) Uani 1 1 d . . .
F2 F 0.6028(2) 0.3879(3) 0.94775(19) 0.0298(8) Uani 1 1 d . . .
Br1 Br 0.63958(5) 0.05738(7) 0.95711(5) 0.0462(2) Uani 1 1 d . . .
Br2 Br 0.82237(6) 0.39802(8) 0.71916(4) 0.0490(3) Uani 1 1 d . . .
N1 N 0.7799(3) 0.4762(4) 1.0213(3) 0.0165(10) Uani 1 1 d . . .
N2 N 0.7733(3) 0.3034(5) 0.9038(3) 0.0192(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(7) . ?
C1 C6 1.394(7) . ?
C1 N1 1.411(6) . ?
C2 C3 1.387(7) . ?
C3 C4 1.410(8) . ?
C4 C5 1.386(8) . ?
C5 C6 1.368(7) . ?
C6 O1 1.398(6) . ?
C7 N1 1.325(6) . ?
C7 O1 1.347(6) . ?
C7 C8 1.412(7) . ?
C8 C9 1.408(7) . ?
C8 C13 1.418(7) . ?
C9 C10 1.374(7) . ?
C10 C11 1.390(7) . ?
C11 C12 1.379(7) . ?
C12 C13 1.403(7) . ?
C13 N2 1.386(6) . ?
C14 C19 1.392(7) . ?
C14 C15 1.400(7) . ?
C14 N2 1.434(6) . ?
C15 C16 1.381(8) . ?
C15 Br1 1.890(6) . ?
C16 C17 1.379(9) . ?
C17 C18 1.357(8) . ?
C18 C19 1.389(8) . ?
C19 Br2 1.900(6) . ?
B1 F1 1.385(7) . ?
B1 F2 1.389(6) . ?
B1 N2 1.538(7) . ?
B1 N1 1.558(7) . ?

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
C2 C1 C6 121.4(5) . . ?
C2 C1 N1 132.8(5) . . ?
C6 C1 N1 105.8(4) . . ?
C1 C2 C3 115.9(5) . . ?
C2 C3 C4 121.3(6) . . ?
C5 C4 C3 122.8(6) . . ?
C6 C5 C4 114.5(6) . . ?
C5 C6 C1 124.1(5) . . ?
C5 C6 O1 127.5(5) . . ?
C1 C6 O1 108.5(4) . . ?
N1 C7 O1 112.4(4) . . ?
N1 C7 C8 124.5(5) . . ?
O1 C7 C8 123.1(5) . . ?
C9 C8 C7 121.0(5) . . ?
C9 C8 C13 120.8(5) . . ?
C7 C8 C13 118.2(5) . . ?
C10 C9 C8 120.6(5) . . ?
C9 C10 C11 118.4(5) . . ?
C12 C11 C10 122.5(5) . . ?
C11 C12 C13 120.3(5) . . ?
N2 C13 C12 123.4(5) . . ?
N2 C13 C8 119.2(5) . . ?
C12 C13 C8 117.4(5) . . ?
C19 C14 C15 116.8(5) . . ?
C19 C14 N2 121.6(5) . . ?
C15 C14 N2 121.5(5) . . ?
C16 C15 C14 121.2(5) . . ?
C16 C15 Br1 119.1(5) . . ?
C14 C15 Br1 119.7(4) . . ?
C17 C16 C15 119.7(6) . . ?
C18 C17 C16 121.0(6) . . ?
C17 C18 C19 119.1(6) . . ?
C18 C19 C14 122.1(6) . . ?
C18 C19 Br2 118.0(5) . . ?
C14 C19 Br2 119.8(4) . . ?
F1 B1 F2 108.5(4) . . ?
F1 B1 N2 112.9(4) . . ?
F2 B1 N2 111.6(5) . . ?
F1 B1 N1 108.6(5) . . ?
F2 B1 N1 108.6(4) . . ?
N2 B1 N1 106.4(4) . . ?
C7 O1 C6 105.8(4) . . ?
C7 N1 C1 107.5(4) . . ?
C7 N1 B1 124.1(4) . . ?
C1 N1 B1 128.4(4) . . ?
C13 N2 C14 118.6(4) . . ?
C13 N2 B1 126.6(4) . . ?
C14 N2 B1 114.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.123
_database_code_depnum_ccdc_archive 'CCDC 966883'
