# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_rmo78a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 B Cl F2 N2'
_chemical_formula_weight         226.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.6805(3)
_cell_length_b                   13.5584(4)
_cell_length_c                   9.0977(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.345(4)
_cell_angle_gamma                90.00
_cell_volume                     928.88(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7232
_cell_measurement_theta_min      3.1722
_cell_measurement_theta_max      32.3939

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_min  0.9132
_exptl_absorpt_correction_T_max  0.9533
_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            6552
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1632
_reflns_number_gt                1565
_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)+(0.0295P)²+0.4785P] 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         1632
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cl1 Cl -0.53047(5) 0.24377(2) -0.03642(4) 0.02706(13) Uani 1 1 d . . .
F1 F -0.26804(11) 0.47331(6) 0.47303(8) 0.0251(2) Uani 1 1 d . . .
F2 F -0.18584(11) 0.56536(6) 0.29126(9) 0.0263(2) Uani 1 1 d . . .
B1 B -0.2711(2) 0.47986(11) 0.32023(16) 0.0188(3) Uani 1 1 d . . .
N1 N -0.46590(15) 0.47852(8) 0.23130(12) 0.0185(3) Uani 1 1 d . . .
N2 N -0.17972(14) 0.38808(8) 0.26675(12) 0.0173(2) Uani 1 1 d . . .
C1 C -0.59332(19) 0.54451(11) 0.24094(15) 0.0239(3) Uani 1 1 d . . .
H1 H -0.5783 0.6004 0.3052 0.029 Uiso 1 1 calc R . .
C2 C -0.75136(19) 0.51948(11) 0.14312(16) 0.0267(3) Uani 1 1 d . . .
H2 H -0.8603 0.5547 0.1294 0.032 Uiso 1 1 calc R . .
C3 C -0.71962(18) 0.43434(11) 0.07046(15) 0.0228(3) Uani 1 1 d . . .
H3 H -0.8024 0.3997 -0.0028 0.027 Uiso 1 1 calc R . .
C4 C -0.54064(17) 0.40813(10) 0.12531(14) 0.0183(3) Uani 1 1 d . . .
C5 C -0.43677(18) 0.33033(10) 0.09396(14) 0.0184(3) Uani 1 1 d . . .
C6 C -0.25978(17) 0.31819(9) 0.16269(14) 0.0173(3) Uani 1 1 d . . .
C7 C -0.13294(19) 0.24552(10) 0.14832(15) 0.0202(3) Uani 1 1 d . . .
H7 H -0.1513 0.1891 0.0852 0.024 Uiso 1 1 calc R . .
C8 C 0.02280(19) 0.27184(10) 0.24330(16) 0.0228(3) Uani 1 1 d . . .
H8 H 0.1321 0.2370 0.2580 0.027 Uiso 1 1 calc R . .
C9 C -0.01021(18) 0.35978(10) 0.31425(15) 0.0215(3) Uani 1 1 d . . .
H9 H 0.0750 0.3944 0.3856 0.026 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
Cl1 C5 1.7223(13) . ?
F1 B1 1.3886(16) . ?
F2 B1 1.3820(17) . ?
B1 N2 1.5530(18) . ?
B1 N1 1.5548(19) . ?
N1 C1 1.3416(18) . ?
N1 C4 1.3973(17) . ?
N2 C9 1.3445(17) . ?
N2 C6 1.3940(16) . ?
C1 C2 1.398(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4125(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3856(19) . ?
C5 C6 1.3898(19) . ?
C6 C7 1.4096(19) . ?
C7 C8 1.378(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?

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 109.23(11) . . ?
F2 B1 N2 110.61(11) . . ?
F1 B1 N2 110.05(11) . . ?
F2 B1 N1 110.74(11) . . ?
F1 B1 N1 110.19(11) . . ?
N2 B1 N1 105.99(10) . . ?
C1 N1 C4 107.14(11) . . ?
C1 N1 B1 126.72(11) . . ?
C4 N1 B1 126.14(11) . . ?
C9 N2 C6 107.11(11) . . ?
C9 N2 B1 126.63(11) . . ?
C6 N2 B1 126.25(11) . . ?
N1 C1 C2 110.46(13) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 107.21(13) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.07(13) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
C5 C4 N1 119.15(12) . . ?
C5 C4 C3 132.73(13) . . ?
N1 C4 C3 108.12(12) . . ?
C4 C5 C6 123.32(12) . . ?
C4 C5 Cl1 118.75(10) . . ?
C6 C5 Cl1 117.93(10) . . ?
C5 C6 N2 119.13(12) . . ?
C5 C6 C7 132.35(12) . . ?
N2 C6 C7 108.51(11) . . ?
C8 C7 C6 106.94(12) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 C9 107.20(12) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 110.24(12) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?

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 -59.57(17) . . . . ?
F1 B1 N1 C1 61.38(17) . . . . ?
N2 B1 N1 C1 -179.58(11) . . . . ?
F2 B1 N1 C4 120.05(13) . . . . ?
F1 B1 N1 C4 -119.00(13) . . . . ?
N2 B1 N1 C4 0.04(16) . . . . ?
F2 B1 N2 C9 60.10(17) . . . . ?
F1 B1 N2 C9 -60.68(17) . . . . ?
N1 B1 N2 C9 -179.81(12) . . . . ?
F2 B1 N2 C6 -121.53(13) . . . . ?
F1 B1 N2 C6 117.69(13) . . . . ?
N1 B1 N2 C6 -1.44(16) . . . . ?
C4 N1 C1 C2 -0.12(15) . . . . ?
B1 N1 C1 C2 179.55(12) . . . . ?
N1 C1 C2 C3 0.10(16) . . . . ?
C1 C2 C3 C4 -0.03(16) . . . . ?
C1 N1 C4 C5 -179.64(12) . . . . ?
B1 N1 C4 C5 0.68(18) . . . . ?
C1 N1 C4 C3 0.11(14) . . . . ?
B1 N1 C4 C3 -179.58(11) . . . . ?
C2 C3 C4 C5 179.65(14) . . . . ?
C2 C3 C4 N1 -0.05(15) . . . . ?
N1 C4 C5 C6 -0.12(19) . . . . ?
C3 C4 C5 C6 -179.79(13) . . . . ?
N1 C4 C5 Cl1 179.78(9) . . . . ?
C3 C4 C5 Cl1 0.1(2) . . . . ?
C4 C5 C6 N2 -1.20(19) . . . . ?
Cl1 C5 C6 N2 178.90(9) . . . . ?
C4 C5 C6 C7 179.50(13) . . . . ?
Cl1 C5 C6 C7 -0.4(2) . . . . ?
C9 N2 C6 C5 -179.29(12) . . . . ?
B1 N2 C6 C5 2.08(19) . . . . ?
C9 N2 C6 C7 0.17(14) . . . . ?
B1 N2 C6 C7 -178.46(11) . . . . ?
C5 C6 C7 C8 179.26(14) . . . . ?
N2 C6 C7 C8 -0.09(15) . . . . ?
C6 C7 C8 C9 -0.02(16) . . . . ?
C6 N2 C9 C8 -0.18(15) . . . . ?
B1 N2 C9 C8 178.44(12) . . . . ?
C7 C8 C9 N2 0.13(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 964025'
#######################################################################
#
#                 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_rm099

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 B2 F4 N6 O'
_chemical_formula_weight         546.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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/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                   14.2703(2)
_cell_length_b                   8.20790(10)
_cell_length_c                   22.8846(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.5780(10)
_cell_angle_gamma                90.00
_cell_volume                     2594.16(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10258
_cell_measurement_theta_min      3.1972
_cell_measurement_theta_max      72.0942

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_min  0.7547
_exptl_absorpt_correction_T_max  0.8543
_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            17912
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         72.24
_reflns_number_total             5056
_reflns_number_gt                4559
_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)+(0.0505P)²+1.2973P] 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         5056
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.30550(7) 0.11449(12) 0.20069(4) 0.0371(2) Uani 1 1 d . . .
F2 F 0.25012(7) 0.36045(12) 0.16197(4) 0.0391(2) Uani 1 1 d . . .
F3 F 0.06706(9) 0.90267(13) -0.11540(5) 0.0565(3) Uani 1 1 d . . .
F4 F -0.06773(7) 0.80692(14) -0.18050(4) 0.0448(3) Uani 1 1 d . . .
B1 B 0.30279(12) 0.2239(2) 0.15353(7) 0.0263(3) Uani 1 1 d . . .
B2 B 0.03056(13) 0.7805(2) -0.15636(8) 0.0314(4) Uani 1 1 d . . .
N1 N 0.40539(8) 0.27479(15) 0.15199(5) 0.0250(3) Uani 1 1 d . . .
N2 N 0.25683(8) 0.14330(14) 0.09246(5) 0.0231(2) Uani 1 1 d . . .
N3 N 0.42146(8) 0.23297(14) -0.00329(5) 0.0230(2) Uani 1 1 d . . .
H3 H 0.4813 0.2690 0.0037 0.028 Uiso 1 1 calc R . .
N4 N 0.21289(8) 0.39217(15) -0.19787(5) 0.0249(3) Uani 1 1 d . . .
H4 H 0.2155 0.3893 -0.2359 0.030 Uiso 1 1 calc R . .
N5 N 0.04651(8) 0.61145(16) -0.12578(5) 0.0287(3) Uani 1 1 d . . .
N6 N 0.08305(8) 0.77668(15) -0.20741(5) 0.0268(3) Uani 1 1 d . . .
C1 C 0.47235(11) 0.34491(19) 0.19769(6) 0.0315(3) Uani 1 1 d . . .
H1 H 0.4670 0.3551 0.2381 0.038 Uiso 1 1 calc R . .
C2 C 0.54970(11) 0.39935(19) 0.17684(7) 0.0318(3) Uani 1 1 d . . .
H2 H 0.6062 0.4520 0.2000 0.038 Uiso 1 1 calc R . .
C3 C 0.52903(10) 0.36239(18) 0.11537(6) 0.0271(3) Uani 1 1 d . . .
H3A H 0.5687 0.3856 0.0887 0.033 Uiso 1 1 calc R . .
C4 C 0.43931(9) 0.28498(16) 0.10057(6) 0.0218(3) Uani 1 1 d . . .
C5 C 0.38384(9) 0.21972(16) 0.04428(6) 0.0204(3) Uani 1 1 d . . .
C6 C 0.29305(10) 0.14314(16) 0.04138(6) 0.0213(3) Uani 1 1 d . . .
C7 C 0.22634(10) 0.05897(17) -0.00440(6) 0.0245(3) Uani 1 1 d . . .
H7 H 0.2322 0.0390 -0.0442 0.029 Uiso 1 1 calc R . .
C8 C 0.15038(10) 0.01055(18) 0.01941(6) 0.0282(3) Uani 1 1 d . . .
H8 H 0.0945 -0.0485 -0.0011 0.034 Uiso 1 1 calc R . .
C9 C 0.17120(10) 0.06442(18) 0.07878(6) 0.0276(3) Uani 1 1 d . . .
H9 H 0.1311 0.0481 0.1057 0.033 Uiso 1 1 calc R . .
C10 C 0.37370(9) 0.19403(17) -0.06491(6) 0.0222(3) Uani 1 1 d . . .
C11 C 0.39327(12) 0.04769(19) -0.08941(7) 0.0329(3) Uani 1 1 d . . .
H11 H 0.4351 -0.0301 -0.0653 0.039 Uiso 1 1 calc R . .
C12 C 0.35068(13) 0.01637(19) -0.15002(7) 0.0360(4) Uani 1 1 d . . .
H12 H 0.3637 -0.0834 -0.1675 0.043 Uiso 1 1 calc R . .
C13 C 0.28957(11) 0.12930(17) -0.18504(6) 0.0276(3) Uani 1 1 d . . .
H13 H 0.2610 0.1074 -0.2265 0.033 Uiso 1 1 calc R . .
C14 C 0.27002(9) 0.27476(16) -0.15957(6) 0.0215(3) Uani 1 1 d . . .
C15 C 0.31330(9) 0.30922(16) -0.09913(6) 0.0205(3) Uani 1 1 d . . .
H15 H 0.3015 0.4099 -0.0818 0.025 Uiso 1 1 calc R . .
C16 C 0.15486(9) 0.50807(17) -0.18396(6) 0.0227(3) Uani 1 1 d . . .
C17 C 0.14124(9) 0.65190(17) -0.21908(6) 0.0238(3) Uani 1 1 d . . .
C18 C 0.17990(10) 0.70040(19) -0.26701(6) 0.0288(3) Uani 1 1 d . . .
H18 H 0.2225 0.6390 -0.2844 0.035 Uiso 1 1 calc R . .
C19 C 0.14429(11) 0.85445(19) -0.28414(7) 0.0333(3) Uani 1 1 d . . .
H19 H 0.1572 0.9184 -0.3158 0.040 Uiso 1 1 calc R . .
C20 C 0.08608(11) 0.89836(19) -0.24639(7) 0.0323(3) Uani 1 1 d . . .
H20 H 0.0532 0.9995 -0.2478 0.039 Uiso 1 1 calc R . .
C21 C 0.10444(9) 0.48591(18) -0.13808(6) 0.0252(3) Uani 1 1 d . . .
C22 C 0.08933(10) 0.3480(2) -0.10566(7) 0.0312(3) Uani 1 1 d . . .
H22 H 0.1186 0.2441 -0.1060 0.037 Uiso 1 1 calc R . .
C23 C 0.02330(11) 0.3919(2) -0.07295(7) 0.0381(4) Uani 1 1 d . . .
H23 H -0.0003 0.3239 -0.0462 0.046 Uiso 1 1 calc R . .
C24 C -0.00171(11) 0.5529(2) -0.08654(7) 0.0361(4) Uani 1 1 d . . .
H24 H -0.0463 0.6134 -0.0706 0.043 Uiso 1 1 calc R . .
C111 C 0.33766(12) 0.65875(19) 0.04369(7) 0.0350(3) Uani 1 1 d . . .
C222 C 0.23567(13) 0.5937(2) 0.02789(9) 0.0441(4) Uani 1 1 d . . .
H22A H 0.2119 0.5861 -0.0161 0.066 Uiso 1 1 calc R . .
H22B H 0.1939 0.6674 0.0437 0.066 Uiso 1 1 calc R . .
H22C H 0.2349 0.4854 0.0458 0.066 Uiso 1 1 calc R . .
C333 C 0.37576(15) 0.7286(2) 0.10506(8) 0.0470(4) Uani 1 1 d . . .
H33A H 0.4437 0.7599 0.1104 0.071 Uiso 1 1 calc R . .
H33B H 0.3711 0.6470 0.1355 0.071 Uiso 1 1 calc R . .
H33C H 0.3377 0.8248 0.1098 0.071 Uiso 1 1 calc R . .
O111 O 0.38685(8) 0.65275(16) 0.00685(5) 0.0425(3) 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
F1 B1 1.3967(18) . ?
F2 B1 1.3900(19) . ?
F3 B2 1.382(2) . ?
F4 B2 1.3891(19) . ?
B1 N1 1.532(2) . ?
B1 N2 1.5360(19) . ?
B2 N6 1.539(2) . ?
B2 N5 1.545(2) . ?
N1 C1 1.3547(18) . ?
N1 C4 1.3829(17) . ?
N2 C9 1.3482(18) . ?
N2 C6 1.3920(17) . ?
N3 C5 1.3341(17) . ?
N3 C10 1.4391(16) . ?
N3 H3 0.8800 . ?
N4 C16 1.3509(18) . ?
N4 C14 1.4148(17) . ?
N4 H4 0.8800 . ?
N5 C24 1.3497(19) . ?
N5 C21 1.3934(18) . ?
N6 C20 1.3470(19) . ?
N6 C17 1.3861(18) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.3926(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4351(18) . ?
C5 C6 1.4264(19) . ?
C6 C7 1.4069(19) . ?
C7 C8 1.388(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.3822(18) . ?
C10 C11 1.383(2) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3874(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3944(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.4138(19) . ?
C16 C21 1.4261(19) . ?
C17 C18 1.404(2) . ?
C18 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.400(2) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C111 O111 1.2264(19) . ?
C111 C333 1.487(2) . ?
C111 C222 1.506(2) . ?
C222 H22A 0.9800 . ?
C222 H22B 0.9800 . ?
C222 H22C 0.9800 . ?
C333 H33A 0.9800 . ?
C333 H33B 0.9800 . ?
C333 H33C 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 108.78(12) . . ?
F2 B1 N1 109.67(12) . . ?
F1 B1 N1 110.65(12) . . ?
F2 B1 N2 110.59(12) . . ?
F1 B1 N2 110.41(12) . . ?
N1 B1 N2 106.75(11) . . ?
F3 B2 F4 109.08(14) . . ?
F3 B2 N6 110.94(14) . . ?
F4 B2 N6 109.69(12) . . ?
F3 B2 N5 110.92(13) . . ?
F4 B2 N5 109.83(14) . . ?
N6 B2 N5 106.35(12) . . ?
C1 N1 C4 107.53(12) . . ?
C1 N1 B1 126.21(12) . . ?
C4 N1 B1 125.28(11) . . ?
C9 N2 C6 108.12(11) . . ?
C9 N2 B1 124.92(12) . . ?
C6 N2 B1 126.92(12) . . ?
C5 N3 C10 126.36(11) . . ?
C5 N3 H3 116.8 . . ?
C10 N3 H3 116.8 . . ?
C16 N4 C14 128.71(11) . . ?
C16 N4 H4 115.6 . . ?
C14 N4 H4 115.6 . . ?
C24 N5 C21 107.38(13) . . ?
C24 N5 B2 125.43(13) . . ?
C21 N5 B2 126.86(12) . . ?
C20 N6 C17 107.44(12) . . ?
C20 N6 B2 126.20(13) . . ?
C17 N6 B2 126.22(12) . . ?
N1 C1 C2 109.89(13) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C1 C2 C3 107.04(13) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C4 C3 C2 107.00(12) . . ?
C4 C3 H3A 126.5 . . ?
C2 C3 H3A 126.5 . . ?
N1 C4 C3 108.54(12) . . ?
N1 C4 C5 120.59(12) . . ?
C3 C4 C5 130.86(12) . . ?
N3 C5 C6 123.05(12) . . ?
N3 C5 C4 117.24(12) . . ?
C6 C5 C4 119.71(11) . . ?
N2 C6 C7 107.53(12) . . ?
N2 C6 C5 119.04(11) . . ?
C7 C6 C5 133.43(12) . . ?
C8 C7 C6 107.28(12) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C9 C8 C7 107.29(12) . . ?
C9 C8 H8 126.4 . . ?
C7 C8 H8 126.4 . . ?
N2 C9 C8 109.78(12) . . ?
N2 C9 H9 125.1 . . ?
C8 C9 H9 125.1 . . ?
C15 C10 C11 121.67(12) . . ?
C15 C10 N3 118.51(12) . . ?
C11 C10 N3 119.72(12) . . ?
C10 C11 C12 118.84(13) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.52(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.86(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.36(12) . . ?
C13 C14 N4 118.12(12) . . ?
C15 C14 N4 121.24(12) . . ?
C10 C15 C14 118.73(12) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N4 C16 C17 117.31(12) . . ?
N4 C16 C21 122.45(12) . . ?
C17 C16 C21 120.16(12) . . ?
N6 C17 C18 108.26(12) . . ?
N6 C17 C16 120.72(12) . . ?
C18 C17 C16 131.00(13) . . ?
C19 C18 C17 106.99(14) . . ?
C19 C18 H18 126.5 . . ?
C17 C18 H18 126.5 . . ?
C18 C19 C20 107.21(13) . . ?
C18 C19 H19 126.4 . . ?
C20 C19 H19 126.4 . . ?
N6 C20 C19 110.09(13) . . ?
N6 C20 H20 125.0 . . ?
C19 C20 H20 125.0 . . ?
N5 C21 C22 108.22(12) . . ?
N5 C21 C16 119.30(13) . . ?
C22 C21 C16 131.83(14) . . ?
C23 C22 C21 106.94(14) . . ?
C23 C22 H22 126.5 . . ?
C21 C22 H22 126.5 . . ?
C24 C23 C22 107.33(14) . . ?
C24 C23 H23 126.3 . . ?
C22 C23 H23 126.3 . . ?
N5 C24 C23 110.12(14) . . ?
N5 C24 H24 124.9 . . ?
C23 C24 H24 124.9 . . ?
O111 C111 C333 121.88(16) . . ?
O111 C111 C222 120.43(16) . . ?
C333 C111 C222 117.69(15) . . ?
C111 C222 H22A 109.5 . . ?
C111 C222 H22B 109.5 . . ?
H22A C222 H22B 109.5 . . ?
C111 C222 H22C 109.5 . . ?
H22A C222 H22C 109.5 . . ?
H22B C222 H22C 109.5 . . ?
C111 C333 H33A 109.5 . . ?
C111 C333 H33B 109.5 . . ?
H33A C333 H33B 109.5 . . ?
C111 C333 H33C 109.5 . . ?
H33A C333 H33C 109.5 . . ?
H33B C333 H33C 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 62.76(18) . . . . ?
F1 B1 N1 C1 -57.23(19) . . . . ?
N2 B1 N1 C1 -177.40(13) . . . . ?
F2 B1 N1 C4 -104.49(15) . . . . ?
F1 B1 N1 C4 135.52(13) . . . . ?
N2 B1 N1 C4 15.35(19) . . . . ?
F2 B1 N2 C9 -69.26(18) . . . . ?
F1 B1 N2 C9 51.18(18) . . . . ?
N1 B1 N2 C9 171.50(13) . . . . ?
F2 B1 N2 C6 108.24(15) . . . . ?
F1 B1 N2 C6 -131.32(13) . . . . ?
N1 B1 N2 C6 -11.00(19) . . . . ?
F3 B2 N5 C24 72.30(19) . . . . ?
F4 B2 N5 C24 -48.36(19) . . . . ?
N6 B2 N5 C24 -166.98(13) . . . . ?
F3 B2 N5 C21 -115.18(16) . . . . ?
F4 B2 N5 C21 124.16(15) . . . . ?
N6 B2 N5 C21 5.54(19) . . . . ?
F3 B2 N6 C20 -60.65(19) . . . . ?
F4 B2 N6 C20 59.93(19) . . . . ?
N5 B2 N6 C20 178.65(13) . . . . ?
F3 B2 N6 C17 114.61(15) . . . . ?
F4 B2 N6 C17 -124.81(15) . . . . ?
N5 B2 N6 C17 -6.10(19) . . . . ?
C4 N1 C1 C2 -0.49(17) . . . . ?
B1 N1 C1 C2 -169.60(14) . . . . ?
N1 C1 C2 C3 0.55(18) . . . . ?
C1 C2 C3 C4 -0.38(17) . . . . ?
C1 N1 C4 C3 0.24(16) . . . . ?
B1 N1 C4 C3 169.48(13) . . . . ?
C1 N1 C4 C5 179.69(12) . . . . ?
B1 N1 C4 C5 -11.1(2) . . . . ?
C2 C3 C4 N1 0.09(16) . . . . ?
C2 C3 C4 C5 -179.28(14) . . . . ?
C10 N3 C5 C6 8.6(2) . . . . ?
C10 N3 C5 C4 -172.09(12) . . . . ?
N1 C4 C5 N3 -179.54(12) . . . . ?
C3 C4 C5 N3 -0.2(2) . . . . ?
N1 C4 C5 C6 -0.22(19) . . . . ?
C3 C4 C5 C6 179.09(14) . . . . ?
C9 N2 C6 C7 -0.61(15) . . . . ?
B1 N2 C6 C7 -178.44(13) . . . . ?
C9 N2 C6 C5 -179.93(12) . . . . ?
B1 N2 C6 C5 2.2(2) . . . . ?
N3 C5 C6 N2 -176.30(12) . . . . ?
C4 C5 C6 N2 4.43(18) . . . . ?
N3 C5 C6 C7 4.6(2) . . . . ?
C4 C5 C6 C7 -174.68(14) . . . . ?
N2 C6 C7 C8 0.47(15) . . . . ?
C5 C6 C7 C8 179.66(14) . . . . ?
C6 C7 C8 C9 -0.17(16) . . . . ?
C6 N2 C9 C8 0.51(16) . . . . ?
B1 N2 C9 C8 178.40(13) . . . . ?
C7 C8 C9 N2 -0.21(17) . . . . ?
C5 N3 C10 C15 82.98(17) . . . . ?
C5 N3 C10 C11 -100.70(17) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
N3 C10 C11 C12 -176.33(14) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C12 C13 C14 N4 175.43(14) . . . . ?
C16 N4 C14 C13 152.48(14) . . . . ?
C16 N4 C14 C15 -33.5(2) . . . . ?
C11 C10 C15 C14 1.1(2) . . . . ?
N3 C10 C15 C14 177.36(11) . . . . ?
C13 C14 C15 C10 -1.73(19) . . . . ?
N4 C14 C15 C10 -175.61(12) . . . . ?
C14 N4 C16 C17 151.50(13) . . . . ?
C14 N4 C16 C21 -31.8(2) . . . . ?
C20 N6 C17 C18 -0.40(15) . . . . ?
B2 N6 C17 C18 -176.39(13) . . . . ?
C20 N6 C17 C16 178.20(12) . . . . ?
B2 N6 C17 C16 2.2(2) . . . . ?
N4 C16 C17 N6 -179.74(12) . . . . ?
C21 C16 C17 N6 3.45(19) . . . . ?
N4 C16 C17 C18 -1.5(2) . . . . ?
C21 C16 C17 C18 -178.32(14) . . . . ?
N6 C17 C18 C19 -0.23(16) . . . . ?
C16 C17 C18 C19 -178.63(14) . . . . ?
C17 C18 C19 C20 0.76(16) . . . . ?
C17 N6 C20 C19 0.89(16) . . . . ?
B2 N6 C20 C19 176.88(13) . . . . ?
C18 C19 C20 N6 -1.04(17) . . . . ?
C24 N5 C21 C22 0.67(16) . . . . ?
B2 N5 C21 C22 -172.95(13) . . . . ?
C24 N5 C21 C16 172.55(12) . . . . ?
B2 N5 C21 C16 -1.1(2) . . . . ?
N4 C16 C21 N5 179.40(12) . . . . ?
C17 C16 C21 N5 -3.95(19) . . . . ?
N4 C16 C21 C22 -11.0(2) . . . . ?
C17 C16 C21 C22 165.67(14) . . . . ?
N5 C21 C22 C23 -1.03(17) . . . . ?
C16 C21 C22 C23 -171.51(14) . . . . ?
C21 C22 C23 C24 0.99(18) . . . . ?
C21 N5 C24 C23 -0.05(17) . . . . ?
B2 N5 C24 C23 173.69(14) . . . . ?
C22 C23 C24 N5 -0.60(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        72.24
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 964026'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_3e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 B2 F4 N4 O2'
_chemical_formula_weight         490.03

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'
O O 0.0492 0.0322 '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'
B B 0.0090 0.0039 '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                   9.9907(7)
_cell_length_b                   10.7791(9)
_cell_length_c                   11.2843(9)
_cell_angle_alpha                81.573(7)
_cell_angle_beta                 66.188(8)
_cell_angle_gamma                83.531(7)
_cell_volume                     1097.84(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3057
_cell_measurement_theta_min      4.1499
_cell_measurement_theta_max      71.9285

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_T_min  0.8010
_exptl_absorpt_correction_T_max  0.8799
_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            7319
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         72.07
_reflns_number_total             4205
_reflns_number_gt                3426
_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)+(0.0575P)²+0.1700P] 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         4205
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.2013(3) 0.6673(2) 1.7030(2) 0.0613(5) Uani 1 1 d . . .
B2 B 0.3485(2) 0.13239(18) 0.89946(16) 0.0457(4) Uani 1 1 d . . .
F1 F 0.17610(18) 0.79465(11) 1.68803(15) 0.1076(5) Uani 1 1 d . . .
F2 F 0.28192(15) 0.63435(16) 1.77841(13) 0.1014(5) Uani 1 1 d . . .
F3 F 0.45951(11) 0.09884(10) 0.78612(9) 0.0646(3) Uani 1 1 d . . .
F4 F 0.26104(11) 0.23108(9) 0.86790(9) 0.0586(3) Uani 1 1 d . . .
N1 N 0.05382(15) 0.60351(12) 1.76761(13) 0.0504(3) Uani 1 1 d . . .
N2 N 0.28223(15) 0.61662(13) 1.56920(14) 0.0524(3) Uani 1 1 d . . .
N3 N 0.25441(14) 0.02187(12) 0.97781(12) 0.0461(3) Uani 1 1 d . . .
N4 N 0.41136(13) 0.17554(12) 0.99082(12) 0.0448(3) Uani 1 1 d . . .
O1 O 0.05816(12) 0.37408(11) 1.56300(13) 0.0603(3) Uani 1 1 d . . .
O2 O 0.18388(14) 0.02925(10) 1.31377(10) 0.0567(3) Uani 1 1 d . . .
C1 C -0.0564(2) 0.62384(19) 1.88133(18) 0.0666(5) Uani 1 1 d . . .
H1 H -0.0587 0.6855 1.9344 0.080 Uiso 1 1 calc R . .
C2 C -0.1666(2) 0.5428(2) 1.9111(2) 0.0724(5) Uani 1 1 d . . .
H2 H -0.2558 0.5394 1.9863 0.087 Uiso 1 1 calc R . .
C3 C -0.12261(19) 0.46834(17) 1.81151(18) 0.0596(4) Uani 1 1 d . . .
H3 H -0.1754 0.4036 1.8048 0.072 Uiso 1 1 calc R . .
C4 C 0.01561(17) 0.50626(14) 1.72141(15) 0.0462(3) Uani 1 1 d . . .
C5 C 0.10851(17) 0.46510(15) 1.60332(15) 0.0464(3) Uani 1 1 d . . .
C6 C 0.24096(17) 0.51883(15) 1.52562(15) 0.0497(4) Uani 1 1 d . . .
C7 C 0.3461(2) 0.50058(19) 1.40055(17) 0.0626(5) Uani 1 1 d . . .
H7 H 0.3455 0.4402 1.3474 0.075 Uiso 1 1 calc R . .
C8 C 0.4500(2) 0.5863(2) 1.36958(19) 0.0699(5) Uani 1 1 d . . .
H8 H 0.5349 0.5962 1.2910 0.084 Uiso 1 1 calc R . .
C9 C 0.4080(2) 0.65594(18) 1.4745(2) 0.0659(5) Uani 1 1 d . . .
H9 H 0.4608 0.7220 1.4787 0.079 Uiso 1 1 calc R . .
C10 C 0.14449(16) 0.26410(14) 1.52823(14) 0.0432(3) Uani 1 1 d . . .
C11 C 0.23312(17) 0.21037(16) 1.59172(14) 0.0486(4) Uani 1 1 d . . .
H11 H 0.2438 0.2517 1.6559 0.058 Uiso 1 1 calc R . .
C12 C 0.30580(19) 0.09570(17) 1.56019(16) 0.0555(4) Uani 1 1 d . . .
H12 H 0.3667 0.0576 1.6035 0.067 Uiso 1 1 calc R . .
C13 C 0.29127(19) 0.03538(16) 1.46638(16) 0.0545(4) Uani 1 1 d . . .
H13 H 0.3411 -0.0438 1.4449 0.065 Uiso 1 1 calc R . .
C14 C 0.20296(18) 0.09290(14) 1.40501(13) 0.0459(3) Uani 1 1 d . . .
C15 C 0.12623(17) 0.20606(14) 1.43491(14) 0.0461(3) Uani 1 1 d . . .
H15 H 0.0633 0.2428 1.3931 0.055 Uiso 1 1 calc R . .
C16 C 0.1952(2) -0.05940(17) 0.93607(18) 0.0601(4) Uani 1 1 d . . .
H16 H 0.2133 -0.0641 0.8474 0.072 Uiso 1 1 calc R . .
C17 C 0.1038(2) -0.13557(19) 1.0413(2) 0.0667(5) Uani 1 1 d . . .
H17 H 0.0496 -0.2007 1.0373 0.080 Uiso 1 1 calc R . .
C18 C 0.10601(19) -0.09940(16) 1.15214(18) 0.0570(4) Uani 1 1 d . . .
H18 H 0.0535 -0.1343 1.2392 0.068 Uiso 1 1 calc R . .
C19 C 0.20047(16) -0.00132(14) 1.11231(14) 0.0440(3) Uani 1 1 d . . .
C20 C 0.24820(16) 0.06401(13) 1.18515(13) 0.0420(3) Uani 1 1 d . . .
C21 C 0.35621(16) 0.15136(14) 1.12629(14) 0.0417(3) Uani 1 1 d . . .
C22 C 0.43729(18) 0.21819(15) 1.16998(16) 0.0512(4) Uani 1 1 d . . .
H22 H 0.4241 0.2194 1.2580 0.061 Uiso 1 1 calc R . .
C23 C 0.5391(2) 0.28138(17) 1.06236(18) 0.0598(4) Uani 1 1 d . . .
H23 H 0.6091 0.3344 1.0621 0.072 Uiso 1 1 calc R . .
C24 C 0.52030(18) 0.25311(17) 0.95424(17) 0.0559(4) Uani 1 1 d . . .
H24 H 0.5766 0.2843 0.8667 0.067 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 1.365(3) . ?
B1 F2 1.378(3) . ?
B1 N2 1.546(3) . ?
B1 N1 1.546(3) . ?
B2 F3 1.377(2) . ?
B2 F4 1.397(2) . ?
B2 N3 1.535(2) . ?
B2 N4 1.550(2) . ?
N1 C1 1.340(2) . ?
N1 C4 1.3883(19) . ?
N2 C9 1.343(2) . ?
N2 C6 1.392(2) . ?
N3 C16 1.342(2) . ?
N3 C19 1.3839(19) . ?
N4 C24 1.340(2) . ?
N4 C21 1.3943(18) . ?
O1 C5 1.3599(18) . ?
O1 C10 1.3915(18) . ?
O2 C20 1.3422(17) . ?
O2 C14 1.4008(17) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.404(2) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.3811(19) . ?
C10 C11 1.381(2) . ?
C11 C12 1.378(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(2) . ?
C20 C21 1.400(2) . ?
C21 C22 1.406(2) . ?
C22 C23 1.375(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 110.59(17) . . ?
F1 B1 N2 110.82(17) . . ?
F2 B1 N2 109.87(17) . . ?
F1 B1 N1 109.79(18) . . ?
F2 B1 N1 109.70(17) . . ?
N2 B1 N1 105.97(13) . . ?
F3 B2 F4 108.75(13) . . ?
F3 B2 N3 112.10(14) . . ?
F4 B2 N3 109.97(13) . . ?
F3 B2 N4 110.93(14) . . ?
F4 B2 N4 109.11(13) . . ?
N3 B2 N4 105.93(12) . . ?
C1 N1 C4 106.81(15) . . ?
C1 N1 B1 127.57(15) . . ?
C4 N1 B1 125.48(14) . . ?
C9 N2 C6 106.97(16) . . ?
C9 N2 B1 126.54(16) . . ?
C6 N2 B1 126.47(14) . . ?
C16 N3 C19 107.05(14) . . ?
C16 N3 B2 128.81(14) . . ?
C19 N3 B2 123.72(12) . . ?
C24 N4 C21 107.63(13) . . ?
C24 N4 B2 125.62(13) . . ?
C21 N4 B2 126.47(12) . . ?
C5 O1 C10 119.66(12) . . ?
C20 O2 C14 121.81(12) . . ?
N1 C1 C2 110.83(16) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C3 C2 C1 107.09(17) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 106.91(17) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
C5 C4 N1 120.10(14) . . ?
C5 C4 C3 131.54(15) . . ?
N1 C4 C3 108.36(14) . . ?
O1 C5 C4 115.78(14) . . ?
O1 C5 C6 121.55(14) . . ?
C4 C5 C6 122.54(14) . . ?
N2 C6 C5 118.72(14) . . ?
N2 C6 C7 108.22(15) . . ?
C5 C6 C7 132.92(16) . . ?
C8 C7 C6 107.14(17) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 107.27(17) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 110.41(18) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C15 C10 C11 121.96(14) . . ?
C15 C10 O1 115.99(13) . . ?
C11 C10 O1 121.80(13) . . ?
C12 C11 C10 118.78(14) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.88(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 118.29(15) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 122.88(14) . . ?
C13 C14 O2 118.12(14) . . ?
C15 C14 O2 118.89(14) . . ?
C14 C15 C10 117.19(14) . . ?
C14 C15 H15 121.4 . . ?
C10 C15 H15 121.4 . . ?
N3 C16 C17 110.10(15) . . ?
N3 C16 H16 125.0 . . ?
C17 C16 H16 125.0 . . ?
C18 C17 C16 107.37(15) . . ?
C18 C17 H17 126.3 . . ?
C16 C17 H17 126.3 . . ?
C17 C18 C19 106.84(16) . . ?
C17 C18 H18 126.6 . . ?
C19 C18 H18 126.6 . . ?
N3 C19 C18 108.64(13) . . ?
N3 C19 C20 121.00(13) . . ?
C18 C19 C20 130.24(14) . . ?
O2 C20 C21 125.19(13) . . ?
O2 C20 C19 112.60(13) . . ?
C21 C20 C19 122.15(13) . . ?
N4 C21 C20 117.31(12) . . ?
N4 C21 C22 107.33(13) . . ?
C20 C21 C22 135.11(14) . . ?
C23 C22 C21 107.69(14) . . ?
C23 C22 H22 126.2 . . ?
C21 C22 H22 126.2 . . ?
C22 C23 C24 106.97(15) . . ?
C22 C23 H23 126.5 . . ?
C24 C23 H23 126.5 . . ?
N4 C24 C23 110.37(15) . . ?
N4 C24 H24 124.8 . . ?
C23 C24 H24 124.8 . . ?

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 -56.2(3) . . . . ?
F2 B1 N1 C1 65.6(2) . . . . ?
N2 B1 N1 C1 -175.89(16) . . . . ?
F1 B1 N1 C4 128.85(18) . . . . ?
F2 B1 N1 C4 -109.43(19) . . . . ?
N2 B1 N1 C4 9.1(2) . . . . ?
F1 B1 N2 C9 53.8(3) . . . . ?
F2 B1 N2 C9 -68.7(2) . . . . ?
N1 B1 N2 C9 172.83(15) . . . . ?
F1 B1 N2 C6 -128.38(18) . . . . ?
F2 B1 N2 C6 109.11(19) . . . . ?
N1 B1 N2 C6 -9.3(2) . . . . ?
F3 B2 N3 C16 -47.7(2) . . . . ?
F4 B2 N3 C16 73.4(2) . . . . ?
N4 B2 N3 C16 -168.86(15) . . . . ?
F3 B2 N3 C19 140.64(14) . . . . ?
F4 B2 N3 C19 -98.25(16) . . . . ?
N4 B2 N3 C19 19.5(2) . . . . ?
F3 B2 N4 C24 44.8(2) . . . . ?
F4 B2 N4 C24 -75.0(2) . . . . ?
N3 B2 N4 C24 166.63(15) . . . . ?
F3 B2 N4 C21 -142.08(15) . . . . ?
F4 B2 N4 C21 98.13(17) . . . . ?
N3 B2 N4 C21 -20.2(2) . . . . ?
C4 N1 C1 C2 -0.2(2) . . . . ?
B1 N1 C1 C2 -175.96(17) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 N1 C4 C5 179.15(15) . . . . ?
B1 N1 C4 C5 -5.0(2) . . . . ?
C1 N1 C4 C3 0.14(19) . . . . ?
B1 N1 C4 C3 175.99(16) . . . . ?
C2 C3 C4 C5 -178.86(18) . . . . ?
C2 C3 C4 N1 0.0(2) . . . . ?
C10 O1 C5 C4 -127.33(16) . . . . ?
C10 O1 C5 C6 56.9(2) . . . . ?
N1 C4 C5 O1 -176.64(13) . . . . ?
C3 C4 C5 O1 2.1(3) . . . . ?
N1 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 C5 C6 177.84(17) . . . . ?
C9 N2 C6 C5 -176.56(15) . . . . ?
B1 N2 C6 C5 5.3(2) . . . . ?
C9 N2 C6 C7 -0.25(18) . . . . ?
B1 N2 C6 C7 -178.43(16) . . . . ?
O1 C5 C6 N2 176.30(13) . . . . ?
C4 C5 C6 N2 0.8(2) . . . . ?
O1 C5 C6 C7 1.1(3) . . . . ?
C4 C5 C6 C7 -174.40(18) . . . . ?
N2 C6 C7 C8 0.3(2) . . . . ?
C5 C6 C7 C8 175.84(18) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C6 N2 C9 C8 0.1(2) . . . . ?
B1 N2 C9 C8 178.32(17) . . . . ?
C7 C8 C9 N2 0.0(2) . . . . ?
C5 O1 C10 C15 -150.23(15) . . . . ?
C5 O1 C10 C11 35.4(2) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
O1 C10 C11 C12 174.33(14) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -1.5(2) . . . . ?
C12 C13 C14 O2 -177.51(14) . . . . ?
C20 O2 C14 C13 -106.29(17) . . . . ?
C20 O2 C14 C15 77.5(2) . . . . ?
C13 C14 C15 C10 2.1(2) . . . . ?
O2 C14 C15 C10 178.06(13) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
O1 C10 C15 C14 -175.80(13) . . . . ?
C19 N3 C16 C17 -0.2(2) . . . . ?
B2 N3 C16 C17 -172.90(16) . . . . ?
N3 C16 C17 C18 0.4(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C16 N3 C19 C18 -0.05(18) . . . . ?
B2 N3 C19 C18 173.13(14) . . . . ?
C16 N3 C19 C20 176.46(15) . . . . ?
B2 N3 C19 C20 -10.4(2) . . . . ?
C17 C18 C19 N3 0.3(2) . . . . ?
C17 C18 C19 C20 -175.81(17) . . . . ?
C14 O2 C20 C21 10.3(2) . . . . ?
C14 O2 C20 C19 -172.41(14) . . . . ?
N3 C19 C20 O2 179.91(14) . . . . ?
C18 C19 C20 O2 -4.4(2) . . . . ?
N3 C19 C20 C21 -2.7(2) . . . . ?
C18 C19 C20 C21 172.95(16) . . . . ?
C24 N4 C21 C20 -175.16(14) . . . . ?
B2 N4 C21 C20 10.7(2) . . . . ?
C24 N4 C21 C22 -0.02(18) . . . . ?
B2 N4 C21 C22 -174.19(14) . . . . ?
O2 C20 C21 N4 179.67(14) . . . . ?
C19 C20 C21 N4 2.6(2) . . . . ?
O2 C20 C21 C22 6.3(3) . . . . ?
C19 C20 C21 C22 -170.78(17) . . . . ?
N4 C21 C22 C23 0.07(19) . . . . ?
C20 C21 C22 C23 173.94(18) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C21 N4 C24 C23 0.0(2) . . . . ?
B2 N4 C24 C23 174.20(15) . . . . ?
C22 C23 C24 N4 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        72.07
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 964027'
#######################################################################
#
#                 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_2c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 B2 Cl2 F4 N6'
_chemical_formula_weight         572.99

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   10.7934(2)
_cell_length_b                   15.9368(2)
_cell_length_c                   14.8791(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.658(2)
_cell_angle_gamma                90.00
_cell_volume                     2464.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4715
_cell_measurement_theta_min      3.0820
_cell_measurement_theta_max      71.9856

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    2.898
_exptl_absorpt_correction_T_min  0.5554
_exptl_absorpt_correction_T_max  0.7045
_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            7702
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.08
_diffrn_reflns_theta_max         72.13
_reflns_number_total             2408
_reflns_number_gt                2204
_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)+(0.0588P)²+4.8050P] 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     SHELXL
_refine_ls_extinction_coef       0.00060(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2408
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.23895(17) 0.12424(11) 0.43290(12) 0.0696(5) Uani 1 1 d . . .
F2 F 0.19519(17) 0.13687(11) 0.57114(15) 0.0756(6) Uani 1 1 d . . .
B1 B 0.2738(3) 0.09707(18) 0.5250(2) 0.0447(6) Uani 1 1 d . . .
N1 N 0.25800(18) 0.00158(13) 0.52909(13) 0.0421(5) Uani 1 1 d . . .
N2 N 0.4155(2) 0.11620(12) 0.57186(14) 0.0439(5) Uani 1 1 d . . .
N3 N 0.56225(18) -0.07791(12) 0.67944(14) 0.0413(5) Uani 1 1 d . . .
H3 H 0.6433 -0.0624 0.6908 0.050 Uiso 1 1 calc R . .
C1 C 0.1534(2) -0.04202(17) 0.48346(19) 0.0517(6) Uani 1 1 d . . .
H1 H 0.0780 -0.0181 0.4432 0.062 Uiso 1 1 calc R . .
C2 C 0.1709(3) -0.12640(18) 0.5034(2) 0.0561(7) Uani 1 1 d . . .
H2 H 0.1107 -0.1700 0.4802 0.067 Uiso 1 1 calc R . .
C3 C 0.2924(2) -0.13558(15) 0.56354(18) 0.0474(6) Uani 1 1 d . . .
H3A H 0.3315 -0.1868 0.5891 0.057 Uiso 1 1 calc R . .
C4 C 0.3474(2) -0.05549(14) 0.57990(16) 0.0380(5) Uani 1 1 d . . .
C5 C 0.4721(2) -0.02629(14) 0.62816(15) 0.0361(5) Uani 1 1 d . . .
C6 C 0.5048(2) 0.05948(14) 0.62217(16) 0.0404(5) Uani 1 1 d . . .
C7 C 0.6167(3) 0.10328(17) 0.6646(2) 0.0553(7) Uani 1 1 d . . .
H7 H 0.6938 0.0802 0.7036 0.066 Uiso 1 1 calc R . .
C8 C 0.5950(3) 0.18658(18) 0.6394(2) 0.0649(8) Uani 1 1 d . . .
H8 H 0.6546 0.2314 0.6576 0.078 Uiso 1 1 calc R . .
C9 C 0.4713(3) 0.19271(16) 0.5831(2) 0.0569(7) Uani 1 1 d . . .
H9 H 0.4311 0.2432 0.5562 0.068 Uiso 1 1 calc R . .
C10 C 0.5351(2) -0.15610(14) 0.71656(15) 0.0371(5) Uani 1 1 d . . .
C11 C 0.5752(2) -0.23093(15) 0.68736(17) 0.0441(5) Uani 1 1 d . . .
H11 H 0.6272 -0.2311 0.6450 0.053 Uiso 1 1 calc R . .
C12 C 0.5393(3) -0.30584(15) 0.72010(18) 0.0502(6) Uani 1 1 d . . .
H12 H 0.5687 -0.3575 0.7015 0.060 Uiso 1 1 calc R . .
C111 C 0.0000 0.8828(3) 0.7500 0.0768(14) Uani 1 2 d S . .
Cl1 Cl 0.10728(9) 0.94525(9) 0.71073(7) 0.1061(5) Uani 1 1 d . . .
H101 H 0.053(5) 0.851(3) 0.797(4) 0.137(19) Uiso 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
F1 B1 1.389(3) . ?
F2 B1 1.381(3) . ?
B1 N2 1.531(4) . ?
B1 N1 1.534(3) . ?
N1 C1 1.344(3) . ?
N1 C4 1.391(3) . ?
N2 C9 1.350(3) . ?
N2 C6 1.385(3) . ?
N3 C5 1.343(3) . ?
N3 C10 1.425(3) . ?
N3 H3 0.8800 . ?
C1 C2 1.379(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.422(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.378(3) . ?
C10 C10 1.404(5) 2_656 ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C12 1.386(6) 2_656 ?
C12 H12 0.9500 . ?
C111 Cl1 1.743(3) . ?
C111 Cl1 1.743(3) 2_556 ?
C111 H101 0.92(5) . ?

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 108.0(2) . . ?
F2 B1 N2 110.7(2) . . ?
F1 B1 N2 111.0(2) . . ?
F2 B1 N1 110.2(2) . . ?
F1 B1 N1 110.2(2) . . ?
N2 B1 N1 106.70(19) . . ?
C1 N1 C4 107.5(2) . . ?
C1 N1 B1 125.5(2) . . ?
C4 N1 B1 127.0(2) . . ?
C9 N2 C6 107.5(2) . . ?
C9 N2 B1 126.4(2) . . ?
C6 N2 B1 125.5(2) . . ?
C5 N3 C10 124.22(19) . . ?
C5 N3 H3 117.9 . . ?
C10 N3 H3 117.9 . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C1 C2 C3 107.1(2) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C2 C3 C4 107.4(2) . . ?
C2 C3 H3A 126.3 . . ?
C4 C3 H3A 126.3 . . ?
N1 C4 C3 107.6(2) . . ?
N1 C4 C5 118.9(2) . . ?
C3 C4 C5 133.2(2) . . ?
N3 C5 C6 118.1(2) . . ?
N3 C5 C4 121.9(2) . . ?
C6 C5 C4 120.0(2) . . ?
N2 C6 C7 108.1(2) . . ?
N2 C6 C5 120.9(2) . . ?
C7 C6 C5 130.9(2) . . ?
C8 C7 C6 107.2(2) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C9 C8 C7 107.4(2) . . ?
C9 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
N2 C9 C8 109.8(2) . . ?
N2 C9 H9 125.1 . . ?
C8 C9 H9 125.1 . . ?
C11 C10 C10 119.93(14) . 2_656 ?
C11 C10 N3 121.3(2) . . ?
C10 C10 N3 118.78(12) 2_656 . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C12 120.29(15) . 2_656 ?
C11 C12 H12 119.9 . . ?
C12 C12 H12 119.9 2_656 . ?
Cl1 C111 Cl1 110.4(3) . 2_556 ?
Cl1 C111 H101 104(3) . . ?
Cl1 C111 H101 113(3) 2_556 . ?

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 70.3(3) . . . . ?
F1 B1 N1 C1 -48.7(3) . . . . ?
N2 B1 N1 C1 -169.3(2) . . . . ?
F2 B1 N1 C4 -109.5(3) . . . . ?
F1 B1 N1 C4 131.4(2) . . . . ?
N2 B1 N1 C4 10.8(3) . . . . ?
F2 B1 N2 C9 -60.2(3) . . . . ?
F1 B1 N2 C9 59.7(3) . . . . ?
N1 B1 N2 C9 179.8(2) . . . . ?
F2 B1 N2 C6 109.7(3) . . . . ?
F1 B1 N2 C6 -130.4(2) . . . . ?
N1 B1 N2 C6 -10.3(3) . . . . ?
C4 N1 C1 C2 0.5(3) . . . . ?
B1 N1 C1 C2 -179.4(2) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 N1 C4 C3 -0.3(3) . . . . ?
B1 N1 C4 C3 179.6(2) . . . . ?
C1 N1 C4 C5 174.3(2) . . . . ?
B1 N1 C4 C5 -5.8(3) . . . . ?
C2 C3 C4 N1 -0.1(3) . . . . ?
C2 C3 C4 C5 -173.6(3) . . . . ?
C10 N3 C5 C6 159.1(2) . . . . ?
C10 N3 C5 C4 -21.5(3) . . . . ?
N1 C4 C5 N3 179.1(2) . . . . ?
C3 C4 C5 N3 -8.0(4) . . . . ?
N1 C4 C5 C6 -1.5(3) . . . . ?
C3 C4 C5 C6 171.4(3) . . . . ?
C9 N2 C6 C7 0.0(3) . . . . ?
B1 N2 C6 C7 -171.5(2) . . . . ?
C9 N2 C6 C5 176.6(2) . . . . ?
B1 N2 C6 C5 5.1(4) . . . . ?
N3 C5 C6 N2 -178.8(2) . . . . ?
C4 C5 C6 N2 1.8(3) . . . . ?
N3 C5 C6 C7 -3.1(4) . . . . ?
C4 C5 C6 C7 177.5(3) . . . . ?
N2 C6 C7 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 -176.4(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C6 N2 C9 C8 0.2(3) . . . . ?
B1 N2 C9 C8 171.7(3) . . . . ?
C7 C8 C9 N2 -0.4(4) . . . . ?
C5 N3 C10 C11 115.1(3) . . . . ?
C5 N3 C10 C10 -64.3(3) . . . 2_656 ?
C10 C10 C11 C12 3.9(4) 2_656 . . . ?
N3 C10 C11 C12 -175.5(2) . . . . ?
C10 C11 C12 C12 1.7(4) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        72.13
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.619
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 966965'
