# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 B F2 N3 O'
_chemical_formula_sum            'C12 H12 B F2 N3 O'
_chemical_formula_weight         263.06

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                   7.2978(8)
_cell_length_b                   8.1140(10)
_cell_length_c                   10.4990(13)
_cell_angle_alpha                93.34(2)
_cell_angle_beta                 107.60(2)
_cell_angle_gamma                94.49(3)
_cell_volume                     588.57(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2719
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      31.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8233
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         30.03
_reflns_number_total             3324
_reflns_number_gt                3079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.0834P)²+0.1530P] 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         3324
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.32138(9) 0.60150(7) 0.67046(6) 0.02060(16) Uani 1 1 d . . .
F2 F 0.26703(9) 0.61477(7) 0.87366(6) 0.02048(16) Uani 1 1 d . . .
O1 O 0.57827(11) 0.66088(9) 0.86353(8) 0.02028(18) Uani 1 1 d . . .
N1 N 0.69147(12) 0.94023(11) 0.90323(9) 0.01891(19) Uani 1 1 d . . .
N2 N 0.35315(12) 0.87442(10) 0.78949(8) 0.01514(18) Uani 1 1 d . . .
N3 N 0.02685(12) 0.80698(11) 0.67950(9) 0.01697(19) Uani 1 1 d . . .
C1 C 0.91064(15) 0.73022(14) 0.97229(11) 0.0216(2) Uani 1 1 d . . .
H1A H 0.9031 0.6455 1.0339 0.026 Uiso 1 1 calc R . .
H1B H 0.9982 0.8262 1.0220 0.026 Uiso 1 1 calc R . .
H1C H 0.9595 0.6842 0.9019 0.026 Uiso 1 1 calc R . .
C2 C 0.71473(14) 0.78298(13) 0.91012(10) 0.0174(2) Uani 1 1 d . . .
C3 C 0.51031(14) 0.98539(13) 0.84181(10) 0.0166(2) Uani 1 1 d . . .
C4 C 0.49378(15) 1.15830(13) 0.83515(10) 0.0195(2) Uani 1 1 d . . .
H4 H 0.6050 1.2354 0.8720 0.023 Uiso 1 1 calc R . .
C5 C 0.31981(15) 1.21384(12) 0.77643(10) 0.0191(2) Uani 1 1 d . . .
H5 H 0.3097 1.3296 0.7729 0.023 Uiso 1 1 calc R . .
C6 C 0.15260(14) 1.09919(12) 0.72022(10) 0.0163(2) Uani 1 1 d . . .
C7 C 0.17317(14) 0.92796(12) 0.72846(9) 0.01522(19) Uani 1 1 d . . .
C8 C -0.14668(15) 0.85292(13) 0.61878(10) 0.0180(2) Uani 1 1 d . . .
C9 C -0.18151(15) 1.02046(13) 0.60524(10) 0.0193(2) Uani 1 1 d . . .
H9 H -0.3083 1.0469 0.5605 0.023 Uiso 1 1 calc R . .
C10 C -0.03460(15) 1.14651(13) 0.65585(10) 0.0182(2) Uani 1 1 d . . .
C11 C -0.30792(15) 0.71631(13) 0.56354(11) 0.0228(2) Uani 1 1 d . . .
H11A H -0.2828 0.6489 0.4912 0.027 Uiso 1 1 calc R . .
H11B H -0.4303 0.7646 0.5283 0.027 Uiso 1 1 calc R . .
H11C H -0.3158 0.6463 0.6350 0.027 Uiso 1 1 calc R . .
C12 C -0.07162(16) 1.32478(13) 0.64202(11) 0.0236(2) Uani 1 1 d . . .
H12A H -0.0245 1.3869 0.7305 0.028 Uiso 1 1 calc R . .
H12B H -0.2107 1.3319 0.6036 0.028 Uiso 1 1 calc R . .
H12C H -0.0039 1.3720 0.5829 0.028 Uiso 1 1 calc R . .
B1 B 0.37280(16) 0.68174(14) 0.79738(11) 0.0166(2) 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 1.3780(12) . ?
F2 B1 1.3753(13) . ?
O1 C2 1.3066(13) . ?
O1 B1 1.4775(13) . ?
N1 C2 1.3035(14) . ?
N1 C3 1.3732(13) . ?
N2 C3 1.3519(13) . ?
N2 C7 1.3918(13) . ?
N2 B1 1.5858(14) . ?
N3 C8 1.3276(13) . ?
N3 C7 1.3466(13) . ?
C1 C2 1.4891(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.4215(14) . ?
C4 C5 1.3578(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4232(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4139(14) . ?
C6 C10 1.4228(14) . ?
C8 C9 1.4099(14) . ?
C8 C11 1.5026(15) . ?
C9 C10 1.3778(15) . ?
C9 H9 0.9500 . ?
C10 C12 1.4995(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C2 O1 B1 124.60(8) . . ?
C2 N1 C3 118.82(9) . . ?
C3 N2 C7 120.45(9) . . ?
C3 N2 B1 120.07(9) . . ?
C7 N2 B1 119.48(8) . . ?
C8 N3 C7 117.30(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 O1 125.46(9) . . ?
N1 C2 C1 119.99(10) . . ?
O1 C2 C1 114.54(9) . . ?
N2 C3 N1 123.14(9) . . ?
N2 C3 C4 120.39(9) . . ?
N1 C3 C4 116.47(9) . . ?
C5 C4 C3 120.35(10) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.22(9) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C10 117.86(9) . . ?
C7 C6 C5 118.24(9) . . ?
C10 C6 C5 123.90(9) . . ?
N3 C7 N2 115.48(9) . . ?
N3 C7 C6 124.16(9) . . ?
N2 C7 C6 120.36(9) . . ?
N3 C8 C9 122.71(10) . . ?
N3 C8 C11 116.62(9) . . ?
C9 C8 C11 120.67(9) . . ?
C10 C9 C8 121.05(10) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C6 116.90(9) . . ?
C9 C10 C12 121.10(10) . . ?
C6 C10 C12 121.99(10) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F2 B1 F1 112.04(9) . . ?
F2 B1 O1 107.97(8) . . ?
F1 B1 O1 107.44(8) . . ?
F2 B1 N2 110.87(8) . . ?
F1 B1 N2 110.47(8) . . ?
O1 B1 N2 107.87(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
C3 N1 C2 O1 -0.39(16) . . . . ?
C3 N1 C2 C1 178.06(8) . . . . ?
B1 O1 C2 N1 -1.36(16) . . . . ?
B1 O1 C2 C1 -179.89(8) . . . . ?
C7 N2 C3 N1 179.98(8) . . . . ?
B1 N2 C3 N1 0.00(14) . . . . ?
C7 N2 C3 C4 0.00(15) . . . . ?
B1 N2 C3 C4 -179.98(8) . . . . ?
C2 N1 C3 N2 1.02(15) . . . . ?
C2 N1 C3 C4 -179.00(9) . . . . ?
N2 C3 C4 C5 0.15(16) . . . . ?
N1 C3 C4 C5 -179.83(9) . . . . ?
C3 C4 C5 C6 -0.41(16) . . . . ?
C4 C5 C6 C7 0.51(15) . . . . ?
C4 C5 C6 C10 -179.40(9) . . . . ?
C8 N3 C7 N2 -179.05(8) . . . . ?
C8 N3 C7 C6 0.64(15) . . . . ?
C3 N2 C7 N3 179.82(8) . . . . ?
B1 N2 C7 N3 -0.20(13) . . . . ?
C3 N2 C7 C6 0.11(14) . . . . ?
B1 N2 C7 C6 -179.91(8) . . . . ?
C10 C6 C7 N3 -0.13(15) . . . . ?
C5 C6 C7 N3 179.96(9) . . . . ?
C10 C6 C7 N2 179.55(8) . . . . ?
C5 C6 C7 N2 -0.36(14) . . . . ?
C7 N3 C8 C9 -0.43(15) . . . . ?
C7 N3 C8 C11 179.42(8) . . . . ?
N3 C8 C9 C10 -0.30(16) . . . . ?
C11 C8 C9 C10 179.85(9) . . . . ?
C8 C9 C10 C6 0.80(15) . . . . ?
C8 C9 C10 C12 -179.75(9) . . . . ?
C7 C6 C10 C9 -0.59(14) . . . . ?
C5 C6 C10 C9 179.31(9) . . . . ?
C7 C6 C10 C12 179.96(9) . . . . ?
C5 C6 C10 C12 -0.13(16) . . . . ?
C2 O1 B1 F2 -117.79(10) . . . . ?
C2 O1 B1 F1 121.19(10) . . . . ?
C2 O1 B1 N2 2.08(13) . . . . ?
C3 N2 B1 F2 116.63(10) . . . . ?
C7 N2 B1 F2 -63.35(11) . . . . ?
C3 N2 B1 F1 -118.56(10) . . . . ?
C7 N2 B1 F1 61.47(11) . . . . ?
C3 N2 B1 O1 -1.40(12) . . . . ?
C7 N2 B1 O1 178.63(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 983345'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H20 B F2 N3 O2'
_chemical_formula_sum            'C10 H20 B F2 N3 O2'
_chemical_formula_weight         263.10

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   4.6470(8)
_cell_length_b                   19.055(3)
_cell_length_c                   11.3230(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.136(8)
_cell_angle_gamma                90.00
_cell_volume                     996.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3191
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.90

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10375
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.89
_reflns_number_total             2350
_reflns_number_gt                1737
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.0493P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2350
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.44476(17) 0.41803(4) 0.37036(7) 0.0207(2) Uani 1 1 d . . .
F2 F 0.00538(17) 0.36858(4) 0.38296(6) 0.0200(2) Uani 1 1 d . . .
O1 O 0.0437(2) 0.48961(5) 0.35127(8) 0.0192(2) Uani 1 1 d . . .
O2 O 0.8089(2) 0.23225(5) 0.22630(9) 0.0220(3) Uani 1 1 d . . .
N1 N -0.2472(3) 0.49714(6) 0.17234(10) 0.0171(3) Uani 1 1 d . . .
N2 N 0.1086(2) 0.40548(6) 0.19043(9) 0.0139(3) Uani 1 1 d . . .
N3 N 0.4642(2) 0.31692(6) 0.20323(10) 0.0153(3) Uani 1 1 d . . .
C1 C -0.2937(3) 0.58197(8) 0.32752(13) 0.0234(3) Uani 1 1 d . . .
H1A H -0.3930 0.5686 0.3963 0.028 Uiso 1 1 calc R . .
H1B H -0.4333 0.6028 0.2664 0.028 Uiso 1 1 calc R . .
H1C H -0.1418 0.6162 0.3521 0.028 Uiso 1 1 calc R . .
C2 C -0.1623(3) 0.51888(7) 0.27879(12) 0.0177(3) Uani 1 1 d . . .
C3 C -0.1082(3) 0.44168(7) 0.12517(11) 0.0150(3) Uani 1 1 d . . .
C4 C -0.1945(3) 0.42320(7) 0.00742(11) 0.0167(3) Uani 1 1 d . . .
H4 H -0.3428 0.4490 -0.0377 0.020 Uiso 1 1 calc R . .
C5 C -0.0650(3) 0.36789(7) -0.04274(11) 0.0165(3) Uani 1 1 d . . .
H5 H -0.1273 0.3546 -0.1222 0.020 Uiso 1 1 calc R . .
C6 C 0.1586(3) 0.33067(7) 0.02201(11) 0.0151(3) Uani 1 1 d . . .
C7 C 0.2430(3) 0.35174(7) 0.13863(11) 0.0142(3) Uani 1 1 d . . .
C8 C 0.6109(3) 0.25936(7) 0.16182(12) 0.0169(3) Uani 1 1 d . . .
C9 C 0.5120(3) 0.23671(7) 0.04238(12) 0.0184(3) Uani 1 1 d . . .
H9 H 0.5987 0.1969 0.0100 0.022 Uiso 1 1 calc R . .
C10 C 0.2989(3) 0.27113(7) -0.02357(12) 0.0177(3) Uani 1 1 d . . .
H10 H 0.2402 0.2556 -0.1022 0.021 Uiso 1 1 calc R . .
B1 B 0.1538(4) 0.42042(8) 0.32946(13) 0.0159(3) Uani 1 1 d . . .
H2 H 0.537(3) 0.3327(9) 0.2747(15) 0.030(5) 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 1.3823(18) . ?
F2 B1 1.3812(18) . ?
O1 C2 1.3167(16) . ?
O1 B1 1.4448(18) . ?
O2 C8 1.2256(16) . ?
N1 C2 1.2956(17) . ?
N1 C3 1.3760(18) . ?
N2 C7 1.3643(17) . ?
N2 C3 1.3703(17) . ?
N2 B1 1.5915(18) . ?
N3 C7 1.3678(17) . ?
N3 C8 1.3987(18) . ?
N3 H2 0.895(17) . ?
C1 C2 1.481(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.3958(17) . ?
C4 C5 1.3669(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3989(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3958(18) . ?
C6 C10 1.4320(19) . ?
C8 C9 1.4470(19) . ?
C9 C10 1.3453(19) . ?
C9 H9 0.9500 . ?
C10 H10 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
C2 O1 B1 121.81(11) . . ?
C2 N1 C3 119.85(12) . . ?
C7 N2 C3 119.34(11) . . ?
C7 N2 B1 122.78(11) . . ?
C3 N2 B1 117.07(11) . . ?
C7 N3 C8 124.51(12) . . ?
C7 N3 H2 120.7(10) . . ?
C8 N3 H2 114.5(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 O1 124.99(13) . . ?
N1 C2 C1 120.62(12) . . ?
O1 C2 C1 114.39(12) . . ?
N2 C3 N1 121.73(12) . . ?
N2 C3 C4 120.51(12) . . ?
N1 C3 C4 117.76(12) . . ?
C5 C4 C3 119.81(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.56(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 117.90(13) . . ?
C7 C6 C10 118.43(12) . . ?
C5 C6 C10 123.65(12) . . ?
N2 C7 N3 119.12(12) . . ?
N2 C7 C6 121.83(12) . . ?
N3 C7 C6 119.05(13) . . ?
O2 C8 N3 119.51(12) . . ?
O2 C8 C9 125.06(13) . . ?
N3 C8 C9 115.43(12) . . ?
C10 C9 C8 121.00(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C6 121.51(12) . . ?
C9 C10 H10 119.2 . . ?
C6 C10 H10 119.2 . . ?
F2 B1 F1 110.24(11) . . ?
F2 B1 O1 112.03(13) . . ?
F1 B1 O1 108.92(12) . . ?
F2 B1 N2 106.65(11) . . ?
F1 B1 N2 110.27(12) . . ?
O1 B1 N2 108.70(11) . . ?

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
C3 N1 C2 O1 -3.6(2) . . . . ?
C3 N1 C2 C1 175.11(13) . . . . ?
B1 O1 C2 N1 -14.2(2) . . . . ?
B1 O1 C2 C1 166.95(13) . . . . ?
C7 N2 C3 N1 -178.77(12) . . . . ?
B1 N2 C3 N1 11.20(19) . . . . ?
C7 N2 C3 C4 1.0(2) . . . . ?
B1 N2 C3 C4 -169.00(12) . . . . ?
C2 N1 C3 N2 4.1(2) . . . . ?
C2 N1 C3 C4 -175.75(13) . . . . ?
N2 C3 C4 C5 1.0(2) . . . . ?
N1 C3 C4 C5 -179.18(13) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C4 C5 C6 C10 178.30(14) . . . . ?
C3 N2 C7 N3 178.38(12) . . . . ?
B1 N2 C7 N3 -12.2(2) . . . . ?
C3 N2 C7 C6 -2.5(2) . . . . ?
B1 N2 C7 C6 166.93(12) . . . . ?
C8 N3 C7 N2 177.37(12) . . . . ?
C8 N3 C7 C6 -1.8(2) . . . . ?
C5 C6 C7 N2 1.9(2) . . . . ?
C10 C6 C7 N2 -176.31(12) . . . . ?
C5 C6 C7 N3 -178.98(12) . . . . ?
C10 C6 C7 N3 2.8(2) . . . . ?
C7 N3 C8 O2 179.15(13) . . . . ?
C7 N3 C8 C9 -0.6(2) . . . . ?
O2 C8 C9 C10 -177.76(14) . . . . ?
N3 C8 C9 C10 2.0(2) . . . . ?
C8 C9 C10 C6 -1.0(2) . . . . ?
C7 C6 C10 C9 -1.5(2) . . . . ?
C5 C6 C10 C9 -179.58(14) . . . . ?
C2 O1 B1 F2 -91.07(15) . . . . ?
C2 O1 B1 F1 146.71(12) . . . . ?
C2 O1 B1 N2 26.53(18) . . . . ?
C7 N2 B1 F2 -73.38(16) . . . . ?
C3 N2 B1 F2 96.28(13) . . . . ?
C7 N2 B1 F1 46.32(17) . . . . ?
C3 N2 B1 F1 -144.03(12) . . . . ?
C7 N2 B1 O1 165.65(12) . . . . ?
C3 N2 B1 O1 -24.69(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H2 F2 0.895(17) 2.477(16) 3.2159(14) 140.1(14) 1_655
N3 H2 F1 0.895(17) 2.025(17) 2.7089(14) 132.2(14) .

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 983346'
#######################################################################
#
#                 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_m110831g1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 B F2 N3 O3.50'
_chemical_formula_weight         356.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   20.167(6)
_cell_length_b                   17.717(5)
_cell_length_c                   9.387(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.038(4)
_cell_angle_gamma                90.00
_cell_volume                     3312.2(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    10613
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33243
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         27.88
_reflns_number_total             7848
_reflns_number_gt                5857
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_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)+(0.0400P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7848
_refine_ls_number_parameters     481
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.34425(5) 0.39190(5) 0.60771(9) 0.0331(2) Uani 1 1 d . . .
F2 F 0.29191(5) 0.36727(5) 0.37910(10) 0.0321(2) Uani 1 1 d . . .
F3 F 0.16831(5) 0.52444(5) 0.74299(9) 0.0278(2) Uani 1 1 d . . .
F4 F 0.19415(5) 0.64075(5) 0.66607(9) 0.0287(2) Uani 1 1 d . . .
O1 O 0.37052(7) 0.72185(7) 0.28130(14) 0.0432(3) Uani 1 1 d . . .
O2 O 0.34138(6) 0.26935(6) 0.51847(12) 0.0304(3) Uani 1 1 d . . .
O3 O 0.54362(7) 0.41592(8) 0.03261(12) 0.0439(4) Uani 1 1 d . . .
O4 O 0.08855(6) 0.47005(7) 0.03691(12) 0.0396(3) Uani 1 1 d . . .
O5 O 0.16141(6) 0.62870(6) 0.89014(11) 0.0292(3) Uani 1 1 d . . .
O6 O -0.11857(7) 0.76471(7) 0.41169(14) 0.0440(3) Uani 1 1 d . . .
N1 N 0.34020(7) 0.60981(8) 0.37351(14) 0.0234(3) Uani 1 1 d D . .
N2 N 0.38152(6) 0.49062(7) 0.39220(13) 0.0215(3) Uani 1 1 d . . .
N3 N 0.41478(7) 0.36567(7) 0.42365(13) 0.0212(3) Uani 1 1 d . . .
N4 N 0.13912(7) 0.50606(8) 0.26275(14) 0.0239(3) Uani 1 1 d D . .
N5 N 0.10304(6) 0.55997(7) 0.45781(13) 0.0219(3) Uani 1 1 d . . .
N6 N 0.07526(7) 0.61243(7) 0.66772(13) 0.0228(3) Uani 1 1 d . . .
B1 B 0.34673(10) 0.34931(10) 0.4831(2) 0.0249(4) Uani 1 1 d . . .
B2 B 0.15109(10) 0.60095(11) 0.74119(19) 0.0243(4) Uani 1 1 d . . .
C1 C 0.27652(9) 0.72150(9) 0.40922(18) 0.0315(4) Uani 1 1 d . . .
H1A H 0.2940 0.7448 0.5022 0.047 Uiso 1 1 calc R . .
H1B H 0.2434 0.6828 0.4232 0.047 Uiso 1 1 calc R . .
H1C H 0.2551 0.7602 0.3428 0.047 Uiso 1 1 calc R . .
C2 C 0.33331(9) 0.68582(9) 0.34702(17) 0.0270(4) Uani 1 1 d . . .
C3 C 0.39267(8) 0.56121(9) 0.35297(15) 0.0216(3) Uani 1 1 d . . .
C4 C 0.45114(8) 0.58420(9) 0.29988(15) 0.0227(4) Uani 1 1 d . . .
H4A H 0.4571 0.6351 0.2724 0.027 Uiso 1 1 calc R . .
C5 C 0.49892(8) 0.53075(9) 0.28932(15) 0.0227(4) Uani 1 1 d . . .
H5 H 0.5389 0.5447 0.2543 0.027 Uiso 1 1 calc R . .
C6 C 0.48982(8) 0.45491(9) 0.32968(15) 0.0200(3) Uani 1 1 d . . .
C7 C 0.53734(8) 0.39570(9) 0.32280(15) 0.0215(4) Uani 1 1 d . . .
C8 C 0.52121(8) 0.32499(9) 0.36382(15) 0.0246(4) Uani 1 1 d . . .
H8 H 0.5519 0.2848 0.3581 0.030 Uiso 1 1 calc R . .
C9 C 0.46010(8) 0.30968(9) 0.41472(16) 0.0228(4) Uani 1 1 d . . .
C10 C 0.44485(9) 0.23485(9) 0.45533(17) 0.0278(4) Uani 1 1 d . . .
H10 H 0.4766 0.1959 0.4487 0.033 Uiso 1 1 calc R . .
C11 C 0.38700(9) 0.21738(9) 0.50280(17) 0.0262(4) Uani 1 1 d . . .
C12 C 0.42926(8) 0.43852(9) 0.38091(15) 0.0201(3) Uani 1 1 d . . .
C13 C 0.36726(9) 0.13923(9) 0.53740(19) 0.0331(4) Uani 1 1 d . . .
H13A H 0.3489 0.1396 0.6280 0.050 Uiso 1 1 calc R . .
H13B H 0.4068 0.1063 0.5474 0.050 Uiso 1 1 calc R . .
H13C H 0.3332 0.1204 0.4595 0.050 Uiso 1 1 calc R . .
C14 C 0.60347(8) 0.41023(9) 0.27199(16) 0.0245(4) Uani 1 1 d . . .
H14A H 0.6342 0.3677 0.3028 0.029 Uiso 1 1 calc R . .
H14B H 0.6237 0.4565 0.3193 0.029 Uiso 1 1 calc R . .
C15 C 0.59754(9) 0.41950(9) 0.11029(17) 0.0277(4) Uani 1 1 d . . .
C16 C 0.66226(9) 0.43223(11) 0.05323(19) 0.0389(5) Uani 1 1 d . . .
H16A H 0.6894 0.3876 0.0679 0.058 Uiso 1 1 d R . .
H16B H 0.6860 0.4738 0.1033 0.058 Uiso 1 1 d R . .
H16C H 0.6527 0.4434 -0.0480 0.058 Uiso 1 1 d R . .
C17 C 0.20599(9) 0.44699(10) 0.09989(17) 0.0317(4) Uani 1 1 d . . .
H17A H 0.2063 0.3917 0.1007 0.047 Uiso 1 1 calc R . .
H17B H 0.2412 0.4659 0.1755 0.047 Uiso 1 1 calc R . .
H17C H 0.2144 0.4652 0.0057 0.047 Uiso 1 1 calc R . .
C18 C 0.13877(9) 0.47502(9) 0.12723(17) 0.0266(4) Uani 1 1 d . . .
C19 C 0.08591(8) 0.53810(9) 0.32026(16) 0.0230(4) Uani 1 1 d . . .
C20 C 0.02096(8) 0.54750(9) 0.24054(17) 0.0261(4) Uani 1 1 d . . .
H20 H 0.0113 0.5331 0.1420 0.031 Uiso 1 1 calc R . .
C21 C -0.02751(8) 0.57800(9) 0.30979(17) 0.0265(4) Uani 1 1 d . . .
H21 H -0.0717 0.5845 0.2589 0.032 Uiso 1 1 calc R . .
C22 C -0.01261(8) 0.60006(9) 0.45642(17) 0.0234(4) Uani 1 1 d . . .
C23 C -0.06069(8) 0.62927(9) 0.53860(17) 0.0247(4) Uani 1 1 d . . .
C24 C -0.03894(8) 0.65005(9) 0.67837(18) 0.0275(4) Uani 1 1 d . . .
H24 H -0.0703 0.6703 0.7339 0.033 Uiso 1 1 calc R . .
C25 C 0.02931(9) 0.64218(9) 0.74251(17) 0.0258(4) Uani 1 1 d . . .
C26 C 0.04976(9) 0.66587(10) 0.88875(17) 0.0302(4) Uani 1 1 d . . .
H26 H 0.0173 0.6869 0.9404 0.036 Uiso 1 1 calc R . .
C27 C 0.11354(9) 0.65920(9) 0.95496(17) 0.0277(4) Uani 1 1 d . . .
C28 C 0.05482(8) 0.59070(8) 0.52362(16) 0.0224(4) Uani 1 1 d . . .
C29 C 0.13866(9) 0.68533(10) 1.10551(17) 0.0347(4) Uani 1 1 d . . .
H29A H 0.1650 0.6450 1.1589 0.052 Uiso 1 1 calc R . .
H29B H 0.1004 0.6980 1.1538 0.052 Uiso 1 1 calc R . .
H29C H 0.1670 0.7301 1.1023 0.052 Uiso 1 1 calc R . .
C30 C -0.13394(8) 0.63583(9) 0.47250(18) 0.0265(4) Uani 1 1 d . . .
H30A H -0.1616 0.6349 0.5508 0.032 Uiso 1 1 calc R . .
H30B H -0.1464 0.5913 0.4104 0.032 Uiso 1 1 calc R . .
C31 C -0.15052(9) 0.70692(10) 0.38309(18) 0.0290(4) Uani 1 1 d . . .
C32 C -0.20849(9) 0.70210(11) 0.2619(2) 0.0445(5) Uani 1 1 d . . .
H32A H -0.2218 0.7531 0.2283 0.067 Uiso 1 1 calc R . .
H32B H -0.2464 0.6771 0.2960 0.067 Uiso 1 1 calc R . .
H32C H -0.1951 0.6730 0.1823 0.067 Uiso 1 1 calc R . .
O7 O 0.25012(6) 0.51779(7) 0.49894(13) 0.0291(3) Uani 1 1 d . . .
H7A H 0.2733(11) 0.4762(13) 0.521(2) 0.067(8) Uiso 1 1 d . . .
H7B H 0.2236(11) 0.5271(12) 0.561(2) 0.060(8) Uiso 1 1 d . . .
H1 H 0.3080(7) 0.5881(9) 0.4157(17) 0.039(5) Uiso 1 1 d D . .
H4 H 0.1776(6) 0.5050(9) 0.3263(15) 0.033(5) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.400(2) . ?
F2 B1 1.392(2) . ?
F3 B2 1.399(2) . ?
F4 B2 1.393(2) . ?
O1 C2 1.223(2) . ?
O2 C11 1.3261(19) . ?
O2 B1 1.463(2) . ?
O3 C15 1.212(2) . ?
O4 C18 1.2176(19) . ?
O5 C27 1.334(2) . ?
O5 B2 1.466(2) . ?
O6 C31 1.217(2) . ?
N1 C2 1.372(2) . ?
N1 C3 1.401(2) . ?
N1 H1 0.899(9) . ?
N2 C3 1.3328(19) . ?
N2 C12 1.3500(19) . ?
N3 C9 1.3603(19) . ?
N3 C12 1.3959(19) . ?
N3 B1 1.587(2) . ?
N4 C18 1.385(2) . ?
N4 C19 1.395(2) . ?
N4 H4 0.902(9) . ?
N5 C19 1.3402(19) . ?
N5 C28 1.3464(19) . ?
N6 C25 1.354(2) . ?
N6 C28 1.4045(19) . ?
N6 B2 1.589(2) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.410(2) . ?
C4 C5 1.366(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.416(2) . ?
C5 H5 0.9500 . ?
C6 C12 1.411(2) . ?
C6 C7 1.429(2) . ?
C7 C8 1.365(2) . ?
C7 C14 1.508(2) . ?
C8 C9 1.416(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.426(2) . ?
C10 C11 1.349(2) . ?
C10 H10 0.9500 . ?
C11 C13 1.491(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.513(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.504(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.503(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.413(2) . ?
C20 C21 1.367(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.417(2) . ?
C21 H21 0.9500 . ?
C22 C28 1.416(2) . ?
C22 C23 1.428(2) . ?
C23 C24 1.367(2) . ?
C23 C30 1.514(2) . ?
C24 C25 1.420(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.433(2) . ?
C26 C27 1.343(2) . ?
C26 H26 0.9500 . ?
C27 C29 1.498(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.521(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.500(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O7 H7A 0.88(2) . ?
O7 H7B 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 B1 124.74(14) . . ?
C27 O5 B2 124.51(13) . . ?
C2 N1 C3 129.45(15) . . ?
C2 N1 H1 116.2(12) . . ?
C3 N1 H1 114.3(12) . . ?
C3 N2 C12 117.81(14) . . ?
C9 N3 C12 118.93(14) . . ?
C9 N3 B1 120.98(13) . . ?
C12 N3 B1 120.09(13) . . ?
C18 N4 C19 128.58(14) . . ?
C18 N4 H4 118.6(11) . . ?
C19 N4 H4 112.8(11) . . ?
C19 N5 C28 117.61(13) . . ?
C25 N6 C28 119.00(14) . . ?
C25 N6 B2 121.01(13) . . ?
C28 N6 B2 119.99(13) . . ?
F2 B1 F1 109.52(14) . . ?
F2 B1 O2 107.57(14) . . ?
F1 B1 O2 108.58(14) . . ?
F2 B1 N3 110.32(14) . . ?
F1 B1 N3 109.98(13) . . ?
O2 B1 N3 110.82(14) . . ?
F4 B2 F3 108.87(14) . . ?
F4 B2 O5 107.86(14) . . ?
F3 B2 O5 108.40(13) . . ?
F4 B2 N6 110.46(13) . . ?
F3 B2 N6 110.45(13) . . ?
O5 B2 N6 110.72(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 123.41(16) . . ?
O1 C2 C1 122.76(16) . . ?
N1 C2 C1 113.81(14) . . ?
N2 C3 N1 112.02(14) . . ?
N2 C3 C4 123.74(15) . . ?
N1 C3 C4 124.23(15) . . ?
C5 C4 C3 117.64(15) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
C4 C5 C6 121.07(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C12 C6 C5 116.22(14) . . ?
C12 C6 C7 119.12(14) . . ?
C5 C6 C7 124.65(15) . . ?
C8 C7 C6 118.02(15) . . ?
C8 C7 C14 120.53(15) . . ?
C6 C7 C14 121.45(15) . . ?
C7 C8 C9 121.98(15) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
N3 C9 C8 120.64(15) . . ?
N3 C9 C10 119.10(15) . . ?
C8 C9 C10 120.25(15) . . ?
C11 C10 C9 122.39(16) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
O2 C11 C10 121.91(15) . . ?
O2 C11 C13 114.01(16) . . ?
C10 C11 C13 124.04(16) . . ?
N2 C12 N3 115.19(14) . . ?
N2 C12 C6 123.51(14) . . ?
N3 C12 C6 121.30(14) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 C15 113.67(13) . . ?
C7 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C7 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
O3 C15 C16 122.71(15) . . ?
O3 C15 C14 121.35(16) . . ?
C16 C15 C14 115.94(15) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 N4 123.49(16) . . ?
O4 C18 C17 122.08(15) . . ?
N4 C18 C17 114.42(14) . . ?
N5 C19 N4 113.12(14) . . ?
N5 C19 C20 123.61(15) . . ?
N4 C19 C20 123.26(14) . . ?
C21 C20 C19 117.86(14) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 120.83(15) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C28 C22 C21 116.27(14) . . ?
C28 C22 C23 119.21(14) . . ?
C21 C22 C23 124.51(15) . . ?
C24 C23 C22 118.26(15) . . ?
C24 C23 C30 121.20(15) . . ?
C22 C23 C30 120.54(14) . . ?
C23 C24 C25 121.61(15) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
N6 C25 C24 121.00(14) . . ?
N6 C25 C26 119.55(15) . . ?
C24 C25 C26 119.44(15) . . ?
C27 C26 C25 121.89(16) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
O5 C27 C26 122.27(15) . . ?
O5 C27 C29 113.20(15) . . ?
C26 C27 C29 124.53(16) . . ?
N5 C28 N6 115.40(14) . . ?
N5 C28 C22 123.73(14) . . ?
N6 C28 C22 120.86(14) . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C30 C31 113.91(13) . . ?
C23 C30 H30A 108.8 . . ?
C31 C30 H30A 108.8 . . ?
C23 C30 H30B 108.8 . . ?
C31 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
O6 C31 C32 122.52(16) . . ?
O6 C31 C30 120.79(16) . . ?
C32 C31 C30 116.67(15) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H7A O7 H7B 111.4(18) . . ?

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
C11 O2 B1 F2 120.49(16) . . . . ?
C11 O2 B1 F1 -121.08(16) . . . . ?
C11 O2 B1 N3 -0.2(2) . . . . ?
C9 N3 B1 F2 -120.84(15) . . . . ?
C12 N3 B1 F2 59.81(18) . . . . ?
C9 N3 B1 F1 118.25(15) . . . . ?
C12 N3 B1 F1 -61.10(17) . . . . ?
C9 N3 B1 O2 -1.82(19) . . . . ?
C12 N3 B1 O2 178.83(12) . . . . ?
C27 O5 B2 F4 121.14(16) . . . . ?
C27 O5 B2 F3 -121.13(16) . . . . ?
C27 O5 B2 N6 0.2(2) . . . . ?
C25 N6 B2 F4 -121.29(15) . . . . ?
C28 N6 B2 F4 59.54(18) . . . . ?
C25 N6 B2 F3 118.21(15) . . . . ?
C28 N6 B2 F3 -60.96(18) . . . . ?
C25 N6 B2 O5 -1.9(2) . . . . ?
C28 N6 B2 O5 178.95(13) . . . . ?
C3 N1 C2 O1 9.9(3) . . . . ?
C3 N1 C2 C1 -168.76(14) . . . . ?
C12 N2 C3 N1 -178.44(12) . . . . ?
C12 N2 C3 C4 0.4(2) . . . . ?
C2 N1 C3 N2 179.64(14) . . . . ?
C2 N1 C3 C4 0.8(2) . . . . ?
N2 C3 C4 C5 -0.4(2) . . . . ?
N1 C3 C4 C5 178.24(14) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C12 -0.1(2) . . . . ?
C4 C5 C6 C7 -179.63(14) . . . . ?
C12 C6 C7 C8 1.3(2) . . . . ?
C5 C6 C7 C8 -179.22(13) . . . . ?
C12 C6 C7 C14 -178.69(12) . . . . ?
C5 C6 C7 C14 0.8(2) . . . . ?
C6 C7 C8 C9 -1.2(2) . . . . ?
C14 C7 C8 C9 178.75(13) . . . . ?
C12 N3 C9 C8 0.4(2) . . . . ?
B1 N3 C9 C8 -178.95(13) . . . . ?
C12 N3 C9 C10 -178.66(13) . . . . ?
B1 N3 C9 C10 2.0(2) . . . . ?
C7 C8 C9 N3 0.4(2) . . . . ?
C7 C8 C9 C10 179.44(14) . . . . ?
N3 C9 C10 C11 -0.1(2) . . . . ?
C8 C9 C10 C11 -179.22(14) . . . . ?
B1 O2 C11 C10 2.0(2) . . . . ?
B1 O2 C11 C13 -176.08(14) . . . . ?
C9 C10 C11 O2 -1.9(2) . . . . ?
C9 C10 C11 C13 175.97(15) . . . . ?
C3 N2 C12 N3 179.96(12) . . . . ?
C3 N2 C12 C6 -0.2(2) . . . . ?
C9 N3 C12 N2 179.56(12) . . . . ?
B1 N3 C12 N2 -1.08(19) . . . . ?
C9 N3 C12 C6 -0.3(2) . . . . ?
B1 N3 C12 C6 179.05(13) . . . . ?
C5 C6 C12 N2 0.1(2) . . . . ?
C7 C6 C12 N2 179.60(13) . . . . ?
C5 C6 C12 N3 179.92(12) . . . . ?
C7 C6 C12 N3 -0.5(2) . . . . ?
C8 C7 C14 C15 104.23(16) . . . . ?
C6 C7 C14 C15 -75.80(18) . . . . ?
C7 C14 C15 O3 0.7(2) . . . . ?
C7 C14 C15 C16 -178.55(15) . . . . ?
C19 N4 C18 O4 -1.7(3) . . . . ?
C19 N4 C18 C17 178.65(15) . . . . ?
C28 N5 C19 N4 -179.14(13) . . . . ?
C28 N5 C19 C20 1.8(2) . . . . ?
C18 N4 C19 N5 177.26(15) . . . . ?
C18 N4 C19 C20 -3.7(3) . . . . ?
N5 C19 C20 C21 -2.6(2) . . . . ?
N4 C19 C20 C21 178.46(15) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C28 1.8(2) . . . . ?
C20 C21 C22 C23 -177.18(15) . . . . ?
C28 C22 C23 C24 2.6(2) . . . . ?
C21 C22 C23 C24 -178.43(15) . . . . ?
C28 C22 C23 C30 -176.52(13) . . . . ?
C21 C22 C23 C30 2.4(2) . . . . ?
C22 C23 C24 C25 -0.9(2) . . . . ?
C30 C23 C24 C25 178.25(14) . . . . ?
C28 N6 C25 C24 1.4(2) . . . . ?
B2 N6 C25 C24 -177.83(14) . . . . ?
C28 N6 C25 C26 -178.85(14) . . . . ?
B2 N6 C25 C26 2.0(2) . . . . ?
C23 C24 C25 N6 -1.1(2) . . . . ?
C23 C24 C25 C26 179.06(15) . . . . ?
N6 C25 C26 C27 -0.3(2) . . . . ?
C24 C25 C26 C27 179.51(16) . . . . ?
B2 O5 C27 C26 1.5(2) . . . . ?
B2 O5 C27 C29 -177.82(14) . . . . ?
C25 C26 C27 O5 -1.5(3) . . . . ?
C25 C26 C27 C29 177.71(16) . . . . ?
C19 N5 C28 N6 179.80(13) . . . . ?
C19 N5 C28 C22 0.9(2) . . . . ?
C25 N6 C28 N5 -178.46(14) . . . . ?
B2 N6 C28 N5 0.7(2) . . . . ?
C25 N6 C28 C22 0.5(2) . . . . ?
B2 N6 C28 C22 179.64(14) . . . . ?
C21 C22 C28 N5 -2.7(2) . . . . ?
C23 C22 C28 N5 176.36(14) . . . . ?
C21 C22 C28 N6 178.51(14) . . . . ?
C23 C22 C28 N6 -2.5(2) . . . . ?
C24 C23 C30 C31 97.80(19) . . . . ?
C22 C23 C30 C31 -83.09(18) . . . . ?
C23 C30 C31 O6 -29.7(2) . . . . ?
C23 C30 C31 C32 151.57(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A F1 0.88(2) 2.14(2) 3.0020(17) 166.6(19) .
O7 H7A F2 0.88(2) 2.41(2) 3.0636(18) 131.8(17) .
O7 H7B F3 0.87(2) 2.18(2) 3.0284(18) 165.3(19) .
O7 H7B F4 0.87(2) 2.36(2) 3.0061(18) 131.8(18) .
O7 H7B N5 0.87(2) 2.54(2) 3.024(2) 116.4(16) .
N1 H1 O7 0.899(9) 1.952(10) 2.831(2) 165.7(17) .
N4 H4 O7 0.902(9) 2.018(10) 2.9000(19) 165.7(15) .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 983347'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C37H41B3Cl2F6N9O3
_chemical_formula_sum            'C37 H41 B3 Cl2 F6 N9 O3'
_chemical_formula_weight         877.12

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'
Cl Cl 0.1484 0.1585 '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                   11.461(3)
_cell_length_b                   12.130(3)
_cell_length_c                   14.451(4)
_cell_angle_alpha                83.107(7)
_cell_angle_beta                 82.118(7)
_cell_angle_gamma                73.049(6)
_cell_volume                     1896.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             906
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation,
Tokyo, Japan. 
;

_diffrn_ambient_temperature      113(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16390
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6688
_reflns_number_gt                4203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1457P)²+0.6742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6688
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2227
_refine_ls_wR_factor_gt          0.2047
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 -0.0512(2) 0.64592(18) 0.90680(14) 0.0233(5) Uani 1 1 d . . .
F2 F -0.17251(18) 0.82809(18) 0.87020(14) 0.0203(5) Uani 1 1 d . . .
F3 F 0.75293(19) -0.18116(17) 0.45217(15) 0.0210(5) Uani 1 1 d . . .
F4 F 0.84146(18) -0.06675(18) 0.34774(13) 0.0189(5) Uani 1 1 d . . .
F5 F 0.43284(18) 0.59151(17) 0.25489(13) 0.0177(5) Uani 1 1 d . . .
F6 F 0.32000(18) 0.77735(16) 0.22031(13) 0.0152(5) Uani 1 1 d . . .
O1 O -0.0353(2) 0.7298(2) 0.75582(17) 0.0210(6) Uani 1 1 d . . .
O2 O 0.8266(2) -0.0490(2) 0.50709(18) 0.0224(6) Uani 1 1 d . . .
O3 O 0.2228(2) 0.6476(2) 0.29740(16) 0.0189(6) Uani 1 1 d . . .
N1 N -0.1497(3) 0.8013(3) 1.1842(2) 0.0164(7) Uani 1 1 d . . .
H1A H -0.2018 0.7712 1.1642 0.020 Uiso 1 1 calc R . .
H1B H -0.1571 0.8149 1.2435 0.020 Uiso 1 1 calc R . .
N2 N -0.0514(3) 0.8046(2) 1.03562(19) 0.0122(6) Uani 1 1 d . . .
N3 N 0.0436(3) 0.8049(2) 0.88272(19) 0.0121(6) Uani 1 1 d . . .
N4 N 0.5655(3) -0.2014(3) 0.2147(2) 0.0188(7) Uani 1 1 d . . .
H4A H 0.6328 -0.2539 0.2299 0.023 Uiso 1 1 calc R . .
H4B H 0.5220 -0.2155 0.1742 0.023 Uiso 1 1 calc R . .
N5 N 0.5993(3) -0.0837(3) 0.31447(19) 0.0146(7) Uani 1 1 d . . .
N6 N 0.6398(3) 0.0246(2) 0.42068(19) 0.0127(6) Uani 1 1 d . . .
N7 N 0.6360(3) 0.7589(3) 0.0035(2) 0.0199(7) Uani 1 1 d . . .
H7A H 0.6377 0.7799 0.0594 0.024 Uiso 1 1 calc R . .
H7B H 0.6899 0.7714 -0.0431 0.024 Uiso 1 1 calc R . .
N8 N 0.4722(3) 0.6913(2) 0.0623(2) 0.0123(6) Uani 1 1 d . . .
N9 N 0.3044(3) 0.6275(2) 0.12776(19) 0.0107(6) Uani 1 1 d . . .
B1 B -0.0563(4) 0.7502(4) 0.8554(3) 0.0147(9) Uani 1 1 d . . .
B2 B 0.7676(4) -0.0720(3) 0.4318(3) 0.0135(8) Uani 1 1 d . . .
B3 B 0.3214(4) 0.6617(4) 0.2268(3) 0.0142(8) Uani 1 1 d . . .
C1 C -0.0585(3) 0.8267(3) 1.1240(2) 0.0120(7) Uani 1 1 d . . .
C2 C 0.0254(3) 0.8756(3) 1.1574(2) 0.0150(8) Uani 1 1 d . . .
H2B H 0.0184 0.8894 1.2215 0.018 Uiso 1 1 calc R . .
C3 C 0.1147(3) 0.9017(3) 1.0957(2) 0.0128(7) Uani 1 1 d . . .
H3A H 0.1705 0.9357 1.1162 0.015 Uiso 1 1 calc R . .
C4 C 0.1262(3) 0.8789(3) 1.0000(2) 0.0126(7) Uani 1 1 d . . .
C5 C 0.2173(3) 0.9041(3) 0.9315(2) 0.0130(7) Uani 1 1 d . . .
C6 C 0.2180(3) 0.8787(3) 0.8417(2) 0.0146(8) Uani 1 1 d . . .
H6A H 0.2785 0.8950 0.7945 0.018 Uiso 1 1 calc R . .
C7 C 0.1302(3) 0.8287(3) 0.8176(2) 0.0129(7) Uani 1 1 d . . .
C8 C 0.0392(3) 0.8293(3) 0.9752(2) 0.0123(7) Uani 1 1 d . . .
C9 C 0.3099(3) 0.9585(3) 0.9564(3) 0.0170(8) Uani 1 1 d . . .
H9A H 0.3655 0.9694 0.9004 0.026 Uiso 1 1 calc R . .
H9B H 0.3572 0.9079 1.0045 0.026 Uiso 1 1 calc R . .
H9C H 0.2674 1.0336 0.9805 0.026 Uiso 1 1 calc R . .
C10 C 0.1344(3) 0.8039(3) 0.7225(2) 0.0150(8) Uani 1 1 d . . .
H10A H 0.1963 0.8212 0.6772 0.018 Uiso 1 1 calc R . .
C11 C 0.0524(3) 0.7563(3) 0.6957(2) 0.0159(8) Uani 1 1 d . . .
C12 C 0.0505(4) 0.7302(3) 0.5975(2) 0.0235(9) Uani 1 1 d . . .
H12A H -0.0169 0.6964 0.5953 0.035 Uiso 1 1 calc R . .
H12B H 0.1286 0.6752 0.5769 0.035 Uiso 1 1 calc R . .
H12C H 0.0386 0.8018 0.5561 0.035 Uiso 1 1 calc R . .
C13 C 0.5287(3) -0.0983(3) 0.2540(2) 0.0155(8) Uani 1 1 d . . .
C14 C 0.4219(3) -0.0115(3) 0.2285(2) 0.0179(8) Uani 1 1 d . . .
H14A H 0.3755 -0.0235 0.1829 0.021 Uiso 1 1 calc R . .
C15 C 0.3876(3) 0.0888(3) 0.2707(2) 0.0170(8) Uani 1 1 d . . .
H15A H 0.3157 0.1472 0.2555 0.020 Uiso 1 1 calc R . .
C16 C 0.4587(3) 0.1069(3) 0.3378(2) 0.0131(7) Uani 1 1 d . . .
C17 C 0.4285(3) 0.2084(3) 0.3865(2) 0.0161(8) Uani 1 1 d . . .
C18 C 0.5032(3) 0.2116(3) 0.4507(2) 0.0169(8) Uani 1 1 d . . .
H18A H 0.4837 0.2779 0.4849 0.020 Uiso 1 1 calc R . .
C19 C 0.6085(3) 0.1204(3) 0.4685(2) 0.0126(7) Uani 1 1 d . . .
C20 C 0.5642(3) 0.0156(3) 0.3564(2) 0.0120(7) Uani 1 1 d . . .
C21 C 0.3183(4) 0.3084(3) 0.3679(3) 0.0229(9) Uani 1 1 d . . .
H21A H 0.3131 0.3698 0.4080 0.034 Uiso 1 1 calc R . .
H21B H 0.2439 0.2825 0.3818 0.034 Uiso 1 1 calc R . .
H21C H 0.3261 0.3382 0.3019 0.034 Uiso 1 1 calc R . .
C22 C 0.6845(3) 0.1284(3) 0.5362(2) 0.0163(8) Uani 1 1 d . . .
H22A H 0.6606 0.1948 0.5707 0.020 Uiso 1 1 calc R . .
C23 C 0.7879(3) 0.0466(3) 0.5534(2) 0.0158(8) Uani 1 1 d . . .
C24 C 0.8697(4) 0.0488(4) 0.6242(3) 0.0235(9) Uani 1 1 d . . .
H24A H 0.8370 0.1204 0.6557 0.035 Uiso 1 1 calc R . .
H24B H 0.9521 0.0452 0.5930 0.035 Uiso 1 1 calc R . .
H24C H 0.8739 -0.0178 0.6706 0.035 Uiso 1 1 calc R . .
C25 C 0.5506(3) 0.7076(3) -0.0107(2) 0.0146(8) Uani 1 1 d . . .
C26 C 0.5480(3) 0.6733(3) -0.1008(2) 0.0168(8) Uani 1 1 d . . .
H26A H 0.6070 0.6843 -0.1514 0.020 Uiso 1 1 calc R . .
C27 C 0.4598(3) 0.6247(3) -0.1130(2) 0.0152(8) Uani 1 1 d . . .
H27A H 0.4564 0.6018 -0.1730 0.018 Uiso 1 1 calc R . .
C28 C 0.3733(3) 0.6076(3) -0.0383(2) 0.0138(8) Uani 1 1 d . . .
C29 C 0.2766(3) 0.5567(3) -0.0449(2) 0.0143(8) Uani 1 1 d . . .
C30 C 0.1998(3) 0.5451(3) 0.0332(2) 0.0155(8) Uani 1 1 d . . .
H30A H 0.1344 0.5131 0.0292 0.019 Uiso 1 1 calc R . .
C31 C 0.2132(3) 0.5786(3) 0.1206(2) 0.0127(7) Uani 1 1 d . . .
C32 C 0.3843(3) 0.6429(3) 0.0491(2) 0.0115(7) Uani 1 1 d . . .
C33 C 0.2636(3) 0.5168(3) -0.1363(2) 0.0195(8) Uani 1 1 d . . .
H33A H 0.1934 0.4847 -0.1286 0.029 Uiso 1 1 calc R . .
H33B H 0.3385 0.4573 -0.1560 0.029 Uiso 1 1 calc R . .
H33C H 0.2505 0.5825 -0.1841 0.029 Uiso 1 1 calc R . .
C34 C 0.1330(3) 0.5617(3) 0.2013(2) 0.0155(8) Uani 1 1 d . . .
H34A H 0.0733 0.5230 0.1963 0.019 Uiso 1 1 calc R . .
C35 C 0.1376(3) 0.5978(3) 0.2846(3) 0.0159(8) Uani 1 1 d . . .
C36 C 0.0509(4) 0.5890(4) 0.3711(3) 0.0250(9) Uani 1 1 d . . .
H36A H 0.0743 0.6214 0.4224 0.037 Uiso 1 1 calc R . .
H36B H 0.0547 0.5076 0.3889 0.037 Uiso 1 1 calc R . .
H36C H -0.0328 0.6322 0.3586 0.037 Uiso 1 1 calc R . .
Cl1 Cl 0.34615(13) 0.56450(11) 0.48704(8) 0.0481(4) Uani 1 1 d . . .
Cl2 Cl 0.26812(12) 0.41541(12) 0.63723(9) 0.0490(4) Uani 1 1 d . . .
C37 C 0.3449(5) 0.5242(4) 0.6086(3) 0.0419(12) Uani 1 1 d . . .
H37A H 0.3021 0.5921 0.6441 0.050 Uiso 1 1 calc R . .
H37B H 0.4300 0.4946 0.6255 0.050 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.378(5) . ?
F2 B1 1.396(5) . ?
F3 B2 1.375(4) . ?
F4 B2 1.388(4) . ?
F5 B3 1.395(5) . ?
F6 B3 1.390(4) . ?
O1 C11 1.322(4) . ?
O1 B1 1.464(4) . ?
O2 C23 1.340(4) . ?
O2 B2 1.451(4) . ?
O3 C35 1.331(4) . ?
O3 B3 1.450(5) . ?
N1 C1 1.347(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.324(4) . ?
N2 C8 1.342(4) . ?
N3 C7 1.341(4) . ?
N3 C8 1.394(4) . ?
N3 B1 1.593(5) . ?
N4 C13 1.365(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C13 1.328(4) . ?
N5 C20 1.344(4) . ?
N6 C19 1.355(4) . ?
N6 C20 1.387(4) . ?
N6 B2 1.602(5) . ?
N7 C25 1.353(4) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N8 C25 1.324(4) . ?
N8 C32 1.349(4) . ?
N9 C31 1.365(4) . ?
N9 C32 1.389(4) . ?
N9 B3 1.589(4) . ?
C1 C2 1.428(5) . ?
C2 C3 1.347(5) . ?
C2 H2B 0.9500 . ?
C3 C4 1.424(5) . ?
C3 H3A 0.9500 . ?
C4 C8 1.409(5) . ?
C4 C5 1.412(5) . ?
C5 C6 1.368(5) . ?
C5 C9 1.504(5) . ?
C6 C7 1.416(5) . ?
C6 H6A 0.9500 . ?
C7 C10 1.433(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.356(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.494(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.422(5) . ?
C14 C15 1.357(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.422(5) . ?
C15 H15A 0.9500 . ?
C16 C20 1.414(5) . ?
C16 C17 1.423(5) . ?
C17 C18 1.357(5) . ?
C17 C21 1.503(5) . ?
C18 C19 1.409(5) . ?
C18 H18A 0.9500 . ?
C19 C22 1.426(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.336(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.487(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.421(5) . ?
C26 C27 1.349(5) . ?
C26 H26A 0.9500 . ?
C27 C28 1.402(5) . ?
C27 H27A 0.9500 . ?
C28 C32 1.414(5) . ?
C28 C29 1.435(5) . ?
C29 C30 1.353(5) . ?
C29 C33 1.500(4) . ?
C30 C31 1.413(5) . ?
C30 H30A 0.9500 . ?
C31 C34 1.416(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.342(5) . ?
C34 H34A 0.9500 . ?
C35 C36 1.500(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Cl1 C37 1.766(5) . ?
Cl2 C37 1.770(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 B1 124.8(3) . . ?
C23 O2 B2 125.0(3) . . ?
C35 O3 B3 124.3(3) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C8 118.1(3) . . ?
C7 N3 C8 120.2(3) . . ?
C7 N3 B1 120.6(3) . . ?
C8 N3 B1 119.2(3) . . ?
C13 N4 H4A 120.0 . . ?
C13 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C13 N5 C20 118.1(3) . . ?
C19 N6 C20 119.1(3) . . ?
C19 N6 B2 120.5(3) . . ?
C20 N6 B2 120.2(3) . . ?
C25 N7 H7A 120.0 . . ?
C25 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C25 N8 C32 118.1(3) . . ?
C31 N9 C32 119.6(3) . . ?
C31 N9 B3 119.7(3) . . ?
C32 N9 B3 120.7(3) . . ?
F1 B1 F2 111.0(3) . . ?
F1 B1 O1 108.1(3) . . ?
F2 B1 O1 107.1(3) . . ?
F1 B1 N3 110.5(3) . . ?
F2 B1 N3 109.2(3) . . ?
O1 B1 N3 110.9(3) . . ?
F3 B2 F4 110.2(3) . . ?
F3 B2 O2 107.5(3) . . ?
F4 B2 O2 109.4(3) . . ?
F3 B2 N6 112.2(3) . . ?
F4 B2 N6 107.1(3) . . ?
O2 B2 N6 110.5(3) . . ?
F6 B3 F5 110.1(3) . . ?
F6 B3 O3 107.1(3) . . ?
F5 B3 O3 109.1(3) . . ?
F6 B3 N9 109.9(3) . . ?
F5 B3 N9 108.9(3) . . ?
O3 B3 N9 111.6(3) . . ?
N2 C1 N1 117.6(3) . . ?
N2 C1 C2 122.9(3) . . ?
N1 C1 C2 119.4(3) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2B 120.8 . . ?
C1 C2 H2B 120.8 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C8 C4 C5 120.2(3) . . ?
C8 C4 C3 116.1(3) . . ?
C5 C4 C3 123.6(3) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C9 121.0(3) . . ?
C4 C5 C9 121.0(3) . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
N3 C7 C6 120.6(3) . . ?
N3 C7 C10 120.1(3) . . ?
C6 C7 C10 119.3(3) . . ?
N2 C8 N3 116.4(3) . . ?
N2 C8 C4 123.9(3) . . ?
N3 C8 C4 119.7(3) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 121.6(3) . . ?
C11 C10 H10A 119.2 . . ?
C7 C10 H10A 119.2 . . ?
O1 C11 C10 121.8(3) . . ?
O1 C11 C12 113.9(3) . . ?
C10 C11 C12 124.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 N4 116.4(3) . . ?
N5 C13 C14 122.9(3) . . ?
N4 C13 C14 120.7(3) . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C20 C16 C15 116.2(3) . . ?
C20 C16 C17 119.7(3) . . ?
C15 C16 C17 124.1(3) . . ?
C18 C17 C16 117.4(3) . . ?
C18 C17 C21 121.0(3) . . ?
C16 C17 C21 121.6(3) . . ?
C17 C18 C19 122.5(3) . . ?
C17 C18 H18A 118.7 . . ?
C19 C18 H18A 118.7 . . ?
N6 C19 C18 120.5(3) . . ?
N6 C19 C22 119.1(3) . . ?
C18 C19 C22 120.3(3) . . ?
N5 C20 N6 115.4(3) . . ?
N5 C20 C16 123.8(3) . . ?
N6 C20 C16 120.7(3) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C19 122.9(3) . . ?
C23 C22 H22A 118.6 . . ?
C19 C22 H22A 118.6 . . ?
C22 C23 O2 121.4(3) . . ?
C22 C23 C24 125.5(3) . . ?
O2 C23 C24 113.1(3) . . ?
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 . . ?
N8 C25 N7 117.1(3) . . ?
N8 C25 C26 122.8(3) . . ?
N7 C25 C26 120.1(3) . . ?
C27 C26 C25 118.5(3) . . ?
C27 C26 H26A 120.7 . . ?
C25 C26 H26A 120.7 . . ?
C26 C27 C28 120.8(3) . . ?
C26 C27 H27A 119.6 . . ?
C28 C27 H27A 119.6 . . ?
C27 C28 C32 116.7(3) . . ?
C27 C28 C29 124.5(3) . . ?
C32 C28 C29 118.8(3) . . ?
C30 C29 C28 118.2(3) . . ?
C30 C29 C33 121.8(3) . . ?
C28 C29 C33 120.0(3) . . ?
C29 C30 C31 122.5(3) . . ?
C29 C30 H30A 118.7 . . ?
C31 C30 H30A 118.7 . . ?
N9 C31 C30 119.9(3) . . ?
N9 C31 C34 119.4(3) . . ?
C30 C31 C34 120.7(3) . . ?
N8 C32 N9 115.9(3) . . ?
N8 C32 C28 123.1(3) . . ?
N9 C32 C28 121.0(3) . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C31 122.9(3) . . ?
C35 C34 H34A 118.5 . . ?
C31 C34 H34A 118.5 . . ?
O3 C35 C34 121.5(3) . . ?
O3 C35 C36 112.9(3) . . ?
C34 C35 C36 125.6(3) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl1 C37 Cl2 108.7(2) . . ?
Cl1 C37 H37A 110.0 . . ?
Cl2 C37 H37A 110.0 . . ?
Cl1 C37 H37B 110.0 . . ?
Cl2 C37 H37B 110.0 . . ?
H37A C37 H37B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 B1 F1 -123.3(3) . . . . ?
C11 O1 B1 F2 117.1(3) . . . . ?
C11 O1 B1 N3 -2.0(5) . . . . ?
C7 N3 B1 F1 121.4(3) . . . . ?
C8 N3 B1 F1 -59.5(4) . . . . ?
C7 N3 B1 F2 -116.3(3) . . . . ?
C8 N3 B1 F2 62.9(4) . . . . ?
C7 N3 B1 O1 1.5(5) . . . . ?
C8 N3 B1 O1 -179.3(3) . . . . ?
C23 O2 B2 F3 -130.3(3) . . . . ?
C23 O2 B2 F4 110.1(4) . . . . ?
C23 O2 B2 N6 -7.6(5) . . . . ?
C19 N6 B2 F3 128.9(3) . . . . ?
C20 N6 B2 F3 -56.2(4) . . . . ?
C19 N6 B2 F4 -110.1(3) . . . . ?
C20 N6 B2 F4 64.9(4) . . . . ?
C19 N6 B2 O2 9.0(4) . . . . ?
C20 N6 B2 O2 -176.1(3) . . . . ?
C35 O3 B3 F6 128.7(3) . . . . ?
C35 O3 B3 F5 -112.1(3) . . . . ?
C35 O3 B3 N9 8.4(5) . . . . ?
C31 N9 B3 F6 -125.8(3) . . . . ?
C32 N9 B3 F6 56.6(4) . . . . ?
C31 N9 B3 F5 113.4(3) . . . . ?
C32 N9 B3 F5 -64.1(4) . . . . ?
C31 N9 B3 O3 -7.1(4) . . . . ?
C32 N9 B3 O3 175.3(3) . . . . ?
C8 N2 C1 N1 -179.9(3) . . . . ?
C8 N2 C1 C2 0.2(5) . . . . ?
N2 C1 C2 C3 0.9(5) . . . . ?
N1 C1 C2 C3 -179.1(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C2 C3 C4 C8 0.5(5) . . . . ?
C2 C3 C4 C5 179.9(3) . . . . ?
C8 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
C8 C4 C5 C9 179.2(3) . . . . ?
C3 C4 C5 C9 -0.2(5) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C9 C5 C6 C7 -179.3(3) . . . . ?
C8 N3 C7 C6 0.0(5) . . . . ?
B1 N3 C7 C6 179.2(3) . . . . ?
C8 N3 C7 C10 -179.8(3) . . . . ?
B1 N3 C7 C10 -0.7(5) . . . . ?
C5 C6 C7 N3 0.0(5) . . . . ?
C5 C6 C7 C10 179.9(3) . . . . ?
C1 N2 C8 N3 -180.0(3) . . . . ?
C1 N2 C8 C4 -0.9(5) . . . . ?
C7 N3 C8 N2 178.9(3) . . . . ?
B1 N3 C8 N2 -0.2(4) . . . . ?
C7 N3 C8 C4 -0.1(5) . . . . ?
B1 N3 C8 C4 -179.3(3) . . . . ?
C5 C4 C8 N2 -178.8(3) . . . . ?
C3 C4 C8 N2 0.6(5) . . . . ?
C5 C4 C8 N3 0.2(5) . . . . ?
C3 C4 C8 N3 179.6(3) . . . . ?
N3 C7 C10 C11 0.0(5) . . . . ?
C6 C7 C10 C11 -179.8(3) . . . . ?
B1 O1 C11 C10 1.5(6) . . . . ?
B1 O1 C11 C12 -177.9(3) . . . . ?
C7 C10 C11 O1 -0.4(6) . . . . ?
C7 C10 C11 C12 178.9(3) . . . . ?
C20 N5 C13 N4 -178.3(3) . . . . ?
C20 N5 C13 C14 3.3(5) . . . . ?
N5 C13 C14 C15 -2.9(5) . . . . ?
N4 C13 C14 C15 178.8(3) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C14 C15 C16 C20 0.0(5) . . . . ?
C14 C15 C16 C17 -178.9(3) . . . . ?
C20 C16 C17 C18 -0.9(5) . . . . ?
C15 C16 C17 C18 177.9(3) . . . . ?
C20 C16 C17 C21 179.1(3) . . . . ?
C15 C16 C17 C21 -2.1(5) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C21 C17 C18 C19 -178.7(3) . . . . ?
C20 N6 C19 C18 -2.4(5) . . . . ?
B2 N6 C19 C18 172.5(3) . . . . ?
C20 N6 C19 C22 178.5(3) . . . . ?
B2 N6 C19 C22 -6.6(5) . . . . ?
C17 C18 C19 N6 0.4(5) . . . . ?
C17 C18 C19 C22 179.5(3) . . . . ?
C13 N5 C20 N6 178.4(3) . . . . ?
C13 N5 C20 C16 -2.1(5) . . . . ?
C19 N6 C20 N5 -177.7(3) . . . . ?
B2 N6 C20 N5 7.3(4) . . . . ?
C19 N6 C20 C16 2.7(5) . . . . ?
B2 N6 C20 C16 -172.3(3) . . . . ?
C15 C16 C20 N5 0.5(5) . . . . ?
C17 C16 C20 N5 179.4(3) . . . . ?
C15 C16 C20 N6 -180.0(3) . . . . ?
C17 C16 C20 N6 -1.0(5) . . . . ?
N6 C19 C22 C23 1.8(5) . . . . ?
C18 C19 C22 C23 -177.3(3) . . . . ?
C19 C22 C23 O2 0.1(6) . . . . ?
C19 C22 C23 C24 -178.7(3) . . . . ?
B2 O2 C23 C22 3.6(5) . . . . ?
B2 O2 C23 C24 -177.4(3) . . . . ?
C32 N8 C25 N7 178.4(3) . . . . ?
C32 N8 C25 C26 -1.9(5) . . . . ?
N8 C25 C26 C27 1.7(5) . . . . ?
N7 C25 C26 C27 -178.5(3) . . . . ?
C25 C26 C27 C28 -0.5(5) . . . . ?
C26 C27 C28 C32 -0.4(5) . . . . ?
C26 C27 C28 C29 180.0(3) . . . . ?
C27 C28 C29 C30 179.7(3) . . . . ?
C32 C28 C29 C30 0.1(5) . . . . ?
C27 C28 C29 C33 0.5(5) . . . . ?
C32 C28 C29 C33 -179.1(3) . . . . ?
C28 C29 C30 C31 -1.4(5) . . . . ?
C33 C29 C30 C31 177.9(3) . . . . ?
C32 N9 C31 C30 -0.6(5) . . . . ?
B3 N9 C31 C30 -178.2(3) . . . . ?
C32 N9 C31 C34 179.1(3) . . . . ?
B3 N9 C31 C34 1.5(5) . . . . ?
C29 C30 C31 N9 1.7(5) . . . . ?
C29 C30 C31 C34 -178.1(3) . . . . ?
C25 N8 C32 N9 179.9(3) . . . . ?
C25 N8 C32 C28 0.9(5) . . . . ?
C31 N9 C32 N8 -179.7(3) . . . . ?
B3 N9 C32 N8 -2.1(4) . . . . ?
C31 N9 C32 C28 -0.6(5) . . . . ?
B3 N9 C32 C28 176.9(3) . . . . ?
C27 C28 C32 N8 0.2(5) . . . . ?
C29 C28 C32 N8 179.9(3) . . . . ?
C27 C28 C32 N9 -178.7(3) . . . . ?
C29 C28 C32 N9 0.9(5) . . . . ?
N9 C31 C34 C35 4.1(5) . . . . ?
C30 C31 C34 C35 -176.2(3) . . . . ?
B3 O3 C35 C34 -3.7(5) . . . . ?
B3 O3 C35 C36 176.8(3) . . . . ?
C31 C34 C35 O3 -3.3(6) . . . . ?
C31 C34 C35 C36 176.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N4 0.88 2.60 3.243(4) 130.6 1_466
N1 H1B F4 0.88 2.20 2.984(3) 148.6 1_466
N1 H1B N5 0.88 2.81 3.252(4) 112.9 1_466
N4 H4B N7 0.88 2.64 3.106(4) 114.5 1_545
N4 H4B F6 0.88 2.34 2.889(4) 120.3 1_545
N4 H4B N8 0.88 2.30 3.136(4) 158.8 1_545
N4 H4B F5 0.88 2.88 3.255(4) 107.4 1_545
N4 H4A Cl2 0.88 2.69 3.442(4) 144.8 2_656
N7 H7B F2 0.88 2.10 2.959(4) 164.9 1_654
N7 H7A N4 0.88 2.30 3.106(4) 152.9 1_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.959
_refine_diff_density_min         -1.578
_refine_diff_density_rms         0.101
_database_code_depnum_ccdc_archive 'CCDC 983348'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 B2 Cl2 F4 N6 O4'
_chemical_formula_sum            'C28 H26 B2 Cl2 F4 N6 O4'
_chemical_formula_weight         679.07

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.6450(15)
_cell_length_b                   12.310(3)
_cell_length_c                   16.339(3)
_cell_angle_alpha                94.37(3)
_cell_angle_beta                 99.76(3)
_cell_angle_gamma                95.76(3)
_cell_volume                     1500.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9447
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11969
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5758
_reflns_number_gt                4493
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 1990)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'

_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)+(0.1067P)²+0.4672P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5758
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
Cl2 Cl 0.10392(12) 0.35371(6) 0.34060(4) 0.0526(3) Uani 1 1 d . . .
F4 F -0.0042(3) 0.28881(14) 0.09279(10) 0.0505(5) Uani 1 1 d . . .
N3A N 0.1494(3) 0.35554(16) -0.01849(12) 0.0292(5) Uani 1 1 d . . .
N2A N 0.2406(3) 0.47665(17) 0.10210(12) 0.0312(5) Uani 1 1 d . . .
C6A C 0.2823(3) 0.5416(2) -0.03162(15) 0.0290(5) Uani 1 1 d . . .
O2A O 0.0057(3) 0.16216(16) -0.01465(12) 0.0485(5) Uani 1 1 d . . .
F3 F 0.2652(3) 0.23211(15) 0.07986(12) 0.0579(5) Uani 1 1 d . . .
C5A C 0.2616(3) 0.5174(2) -0.12061(15) 0.0312(5) Uani 1 1 d . . .
C10A C 0.2255(3) 0.45969(19) 0.01761(14) 0.0275(5) Uani 1 1 d . . .
N1A N 0.3215(4) 0.59594(19) 0.22537(13) 0.0442(6) Uani 1 1 d . . .
H1AA H 0.3761 0.6592 0.2457 0.053 Uiso 1 1 calc R . .
C3A C 0.1274(4) 0.3334(2) -0.10318(15) 0.0330(6) Uani 1 1 d . . .
C11A C 0.3226(4) 0.6027(2) -0.17429(16) 0.0423(7) Uani 1 1 d . . .
H11A H 0.2990 0.5727 -0.2316 0.063 Uiso 1 1 calc R . .
H11B H 0.4485 0.6243 -0.1570 0.063 Uiso 1 1 calc R . .
H11C H 0.2592 0.6656 -0.1685 0.063 Uiso 1 1 calc R . .
C4A C 0.1840(4) 0.4154(2) -0.15351(15) 0.0373(6) Uani 1 1 d . . .
H4AA H 0.1672 0.3985 -0.2110 0.045 Uiso 1 1 calc R . .
C9A C 0.3095(4) 0.5750(2) 0.13862(15) 0.0336(6) Uani 1 1 d . . .
O1A O 0.2743(4) 0.57529(19) 0.35518(12) 0.0663(8) Uani 1 1 d . . .
C12A C 0.2616(4) 0.5333(2) 0.28353(16) 0.0391(6) Uani 1 1 d . . .
C7A C 0.3598(4) 0.6445(2) 0.01139(16) 0.0362(6) Uani 1 1 d . . .
H7AA H 0.4014 0.7002 -0.0183 0.043 Uiso 1 1 calc R . .
C1A C -0.0143(4) 0.1480(2) -0.09687(16) 0.0371(6) Uani 1 1 d . . .
C13A C 0.1855(4) 0.4158(2) 0.25723(16) 0.0370(6) Uani 1 1 d . . .
H13A H 0.2773 0.3751 0.2399 0.044 Uiso 1 1 calc R . .
H13B H 0.0888 0.4131 0.2100 0.044 Uiso 1 1 calc R . .
B2 B 0.1055(4) 0.2584(2) 0.03812(18) 0.0339(6) Uani 1 1 d . . .
C2A C 0.0451(4) 0.2277(2) -0.14138(17) 0.0429(7) Uani 1 1 d . . .
H2AB H 0.0322 0.2134 -0.1989 0.051 Uiso 1 1 calc R . .
C8A C 0.3738(4) 0.6625(2) 0.09583(16) 0.0384(6) Uani 1 1 d . . .
H8AA H 0.4237 0.7297 0.1243 0.046 Uiso 1 1 calc R . .
Cl1 Cl 0.74328(15) 0.56658(6) 0.39036(5) 0.0645(3) Uani 1 1 d . . .
F2 F 0.3387(3) 0.22008(13) 0.72146(10) 0.0471(4) Uani 1 1 d . . .
F1 F 0.6062(2) 0.15456(13) 0.71829(10) 0.0445(4) Uani 1 1 d . . .
N2 N 0.4323(3) 0.17495(16) 0.55604(12) 0.0293(5) Uani 1 1 d . . .
N3 N 0.3326(3) 0.04554(16) 0.63941(12) 0.0285(5) Uani 1 1 d . . .
O2 O 0.4148(3) 0.07293(16) 0.79589(12) 0.0461(5) Uani 1 1 d . . .
C10 C 0.3403(3) 0.07590(19) 0.55922(15) 0.0274(5) Uani 1 1 d . . .
O1 O 0.5629(3) 0.33356(18) 0.34995(11) 0.0530(6) Uani 1 1 d . . .
C8 C 0.3705(4) 0.1442(2) 0.40490(16) 0.0349(6) Uani 1 1 d . . .
H8A H 0.3826 0.1698 0.3538 0.042 Uiso 1 1 calc R . .
C3 C 0.2425(4) -0.0531(2) 0.64822(17) 0.0337(6) Uani 1 1 d . . .
C6 C 0.2589(3) 0.00545(19) 0.48701(15) 0.0302(5) Uani 1 1 d . . .
N1 N 0.5508(3) 0.30911(17) 0.48672(12) 0.0328(5) Uani 1 1 d . . .
H1A H 0.5831 0.3422 0.5361 0.039 Uiso 1 1 calc R . .
C4 C 0.1571(4) -0.1242(2) 0.57597(17) 0.0367(6) Uani 1 1 d . . .
H4A H 0.0942 -0.1903 0.5833 0.044 Uiso 1 1 calc R . .
C7 C 0.2783(4) 0.0446(2) 0.40920(16) 0.0333(6) Uani 1 1 d . . .
H7A H 0.2271 0.0015 0.3601 0.040 Uiso 1 1 calc R . .
C5 C 0.1649(3) -0.0984(2) 0.49690(17) 0.0333(6) Uani 1 1 d . . .
C12 C 0.6076(4) 0.3634(2) 0.42377(16) 0.0348(6) Uani 1 1 d . . .
C2 C 0.2353(4) -0.0857(2) 0.72995(18) 0.0434(7) Uani 1 1 d . . .
H2B H 0.1676 -0.1509 0.7354 0.052 Uiso 1 1 calc R . .
C9 C 0.4475(3) 0.20744(19) 0.48141(15) 0.0296(5) Uani 1 1 d . . .
C1 C 0.3248(4) -0.0237(2) 0.79983(18) 0.0415(7) Uani 1 1 d . . .
B1 B 0.4253(4) 0.1262(2) 0.71938(18) 0.0339(6) Uani 1 1 d . . .
C11 C 0.0795(4) -0.1768(2) 0.42162(19) 0.0455(7) Uani 1 1 d . . .
H11D H 0.0227 -0.2416 0.4397 0.068 Uiso 1 1 calc R . .
H11E H 0.1696 -0.1965 0.3907 0.068 Uiso 1 1 calc R . .
H11F H -0.0080 -0.1420 0.3867 0.068 Uiso 1 1 calc R . .
C13 C 0.7445(5) 0.4616(3) 0.45747(18) 0.0515(8) Uani 1 1 d . . .
H13C H 0.8626 0.4374 0.4669 0.062 Uiso 1 1 calc R . .
H13D H 0.7210 0.4908 0.5108 0.062 Uiso 1 1 calc R . .
C14A C -0.1151(5) 0.0393(2) -0.1344(2) 0.0518(8) Uani 1 1 d . . .
H14A H -0.1433 -0.0035 -0.0907 0.078 Uiso 1 1 calc R . .
H14B H -0.0427 0.0007 -0.1666 0.078 Uiso 1 1 calc R . .
H14C H -0.2237 0.0513 -0.1699 0.078 Uiso 1 1 calc R . .
C14 C 0.3368(5) -0.0572(3) 0.8871(2) 0.0597(9) Uani 1 1 d . . .
H14D H 0.4063 0.0000 0.9258 0.090 Uiso 1 1 calc R . .
H14E H 0.3929 -0.1234 0.8912 0.090 Uiso 1 1 calc R . .
H14F H 0.2189 -0.0696 0.9000 0.090 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
Cl2 C13A 1.783(3) . ?
F4 B2 1.382(4) . ?
N3A C3A 1.368(3) . ?
N3A C10A 1.396(3) . ?
N3A B2 1.610(3) . ?
N2A C9A 1.325(3) . ?
N2A C10A 1.364(3) . ?
C6A C10A 1.416(3) . ?
C6A C7A 1.423(4) . ?
C6A C5A 1.440(3) . ?
O2A C1A 1.322(3) . ?
O2A B2 1.473(3) . ?
F3 B2 1.375(4) . ?
C5A C4A 1.363(4) . ?
C5A C11A 1.507(3) . ?
N1A C12A 1.377(3) . ?
N1A C9A 1.407(3) . ?
C3A C4A 1.428(4) . ?
C3A C2A 1.434(4) . ?
C9A C8A 1.420(3) . ?
O1A C12A 1.228(3) . ?
C12A C13A 1.505(4) . ?
C7A C8A 1.365(4) . ?
C1A C2A 1.353(4) . ?
C1A C14A 1.507(4) . ?
Cl1 C13 1.757(3) . ?
F2 B1 1.389(4) . ?
F1 B1 1.396(4) . ?
N2 C9 1.332(3) . ?
N2 C10 1.354(3) . ?
N3 C3 1.365(3) . ?
N3 C10 1.399(3) . ?
N3 B1 1.594(4) . ?
O2 C1 1.325(3) . ?
O2 B1 1.465(3) . ?
C10 C6 1.421(3) . ?
O1 C12 1.214(3) . ?
C8 C7 1.364(4) . ?
C8 C9 1.423(4) . ?
C3 C2 1.431(4) . ?
C3 C4 1.432(4) . ?
C6 C7 1.419(3) . ?
C6 C5 1.436(3) . ?
N1 C12 1.375(3) . ?
N1 C9 1.400(3) . ?
C4 C5 1.363(4) . ?
C5 C11 1.514(4) . ?
C12 C13 1.520(4) . ?
C2 C1 1.360(4) . ?
C1 C14 1.505(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
C3A N3A C10A 119.0(2) . . ?
C3A N3A B2 119.5(2) . . ?
C10A N3A B2 121.22(19) . . ?
C9A N2A C10A 117.7(2) . . ?
C10A C6A C7A 116.8(2) . . ?
C10A C6A C5A 119.6(2) . . ?
C7A C6A C5A 123.6(2) . . ?
C1A O2A B2 125.2(2) . . ?
C4A C5A C6A 117.3(2) . . ?
C4A C5A C11A 122.1(2) . . ?
C6A C5A C11A 120.7(2) . . ?
N2A C10A N3A 115.8(2) . . ?
N2A C10A C6A 122.9(2) . . ?
N3A C10A C6A 121.2(2) . . ?
C12A N1A C9A 131.5(2) . . ?
N3A C3A C4A 120.3(2) . . ?
N3A C3A C2A 119.6(2) . . ?
C4A C3A C2A 120.1(2) . . ?
C5A C4A C3A 122.5(2) . . ?
N2A C9A N1A 119.0(2) . . ?
N2A C9A C8A 124.2(2) . . ?
N1A C9A C8A 116.8(2) . . ?
O1A C12A N1A 118.5(3) . . ?
O1A C12A C13A 122.6(2) . . ?
N1A C12A C13A 118.9(2) . . ?
C8A C7A C6A 120.7(2) . . ?
O2A C1A C2A 121.5(2) . . ?
O2A C1A C14A 113.8(2) . . ?
C2A C1A C14A 124.6(3) . . ?
C12A C13A Cl2 111.01(18) . . ?
F3 B2 F4 111.5(2) . . ?
F3 B2 O2A 110.5(2) . . ?
F4 B2 O2A 105.6(2) . . ?
F3 B2 N3A 107.8(2) . . ?
F4 B2 N3A 111.3(2) . . ?
O2A B2 N3A 110.2(2) . . ?
C1A C2A C3A 122.5(2) . . ?
C7A C8A C9A 117.7(2) . . ?
C9 N2 C10 118.2(2) . . ?
C3 N3 C10 119.2(2) . . ?
C3 N3 B1 120.5(2) . . ?
C10 N3 B1 120.30(19) . . ?
C1 O2 B1 125.4(2) . . ?
N2 C10 N3 115.4(2) . . ?
N2 C10 C6 123.3(2) . . ?
N3 C10 C6 121.4(2) . . ?
C7 C8 C9 117.6(2) . . ?
N3 C3 C2 119.7(2) . . ?
N3 C3 C4 120.1(2) . . ?
C2 C3 C4 120.2(2) . . ?
C7 C6 C10 116.1(2) . . ?
C7 C6 C5 124.8(2) . . ?
C10 C6 C5 119.1(2) . . ?
C12 N1 C9 128.8(2) . . ?
C5 C4 C3 122.4(2) . . ?
C8 C7 C6 121.4(2) . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 C11 121.4(2) . . ?
C6 C5 C11 120.7(2) . . ?
O1 C12 N1 124.6(2) . . ?
O1 C12 C13 123.3(2) . . ?
N1 C12 C13 112.0(2) . . ?
C1 C2 C3 121.8(2) . . ?
N2 C9 N1 112.6(2) . . ?
N2 C9 C8 123.5(2) . . ?
N1 C9 C8 123.9(2) . . ?
O2 C1 C2 121.6(2) . . ?
O2 C1 C14 113.6(3) . . ?
C2 C1 C14 124.8(3) . . ?
F2 B1 F1 109.9(2) . . ?
F2 B1 O2 109.0(2) . . ?
F1 B1 O2 106.9(2) . . ?
F2 B1 N3 109.3(2) . . ?
F1 B1 N3 111.1(2) . . ?
O2 B1 N3 110.5(2) . . ?
C12 C13 Cl1 113.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A C6A C5A C4A 1.2(4) . . . . ?
C7A C6A C5A C4A -179.6(3) . . . . ?
C10A C6A C5A C11A -179.4(2) . . . . ?
C7A C6A C5A C11A -0.2(4) . . . . ?
C9A N2A C10A N3A -179.0(2) . . . . ?
C9A N2A C10A C6A 0.9(4) . . . . ?
C3A N3A C10A N2A 178.9(2) . . . . ?
B2 N3A C10A N2A -7.2(3) . . . . ?
C3A N3A C10A C6A -1.0(4) . . . . ?
B2 N3A C10A C6A 173.0(2) . . . . ?
C7A C6A C10A N2A 0.8(4) . . . . ?
C5A C6A C10A N2A -179.9(2) . . . . ?
C7A C6A C10A N3A -179.3(2) . . . . ?
C5A C6A C10A N3A -0.1(4) . . . . ?
C10A N3A C3A C4A 0.9(4) . . . . ?
B2 N3A C3A C4A -173.1(2) . . . . ?
C10A N3A C3A C2A -178.4(2) . . . . ?
B2 N3A C3A C2A 7.6(4) . . . . ?
C6A C5A C4A C3A -1.2(4) . . . . ?
C11A C5A C4A C3A 179.3(3) . . . . ?
N3A C3A C4A C5A 0.2(4) . . . . ?
C2A C3A C4A C5A 179.5(3) . . . . ?
C10A N2A C9A N1A 178.0(2) . . . . ?
C10A N2A C9A C8A -2.1(4) . . . . ?
C12A N1A C9A N2A -5.3(5) . . . . ?
C12A N1A C9A C8A 174.9(3) . . . . ?
C9A N1A C12A O1A -173.0(3) . . . . ?
C9A N1A C12A C13A 7.8(5) . . . . ?
C10A C6A C7A C8A -1.4(4) . . . . ?
C5A C6A C7A C8A 179.3(3) . . . . ?
B2 O2A C1A C2A -5.7(5) . . . . ?
B2 O2A C1A C14A 177.0(3) . . . . ?
O1A C12A C13A Cl2 4.5(4) . . . . ?
N1A C12A C13A Cl2 -176.3(2) . . . . ?
C1A O2A B2 F3 -106.3(3) . . . . ?
C1A O2A B2 F4 133.0(3) . . . . ?
C1A O2A B2 N3A 12.7(4) . . . . ?
C3A N3A B2 F3 107.3(3) . . . . ?
C10A N3A B2 F3 -66.5(3) . . . . ?
C3A N3A B2 F4 -130.2(2) . . . . ?
C10A N3A B2 F4 56.0(3) . . . . ?
C3A N3A B2 O2A -13.4(3) . . . . ?
C10A N3A B2 O2A 172.7(2) . . . . ?
O2A C1A C2A C3A -2.3(5) . . . . ?
C14A C1A C2A C3A 174.7(3) . . . . ?
N3A C3A C2A C1A 0.7(5) . . . . ?
C4A C3A C2A C1A -178.5(3) . . . . ?
C6A C7A C8A C9A 0.4(4) . . . . ?
N2A C9A C8A C7A 1.5(5) . . . . ?
N1A C9A C8A C7A -178.6(3) . . . . ?
C9 N2 C10 N3 178.6(2) . . . . ?
C9 N2 C10 C6 -0.3(4) . . . . ?
C3 N3 C10 N2 -180.0(2) . . . . ?
B1 N3 C10 N2 1.0(3) . . . . ?
C3 N3 C10 C6 -1.0(4) . . . . ?
B1 N3 C10 C6 180.0(2) . . . . ?
C10 N3 C3 C2 179.3(2) . . . . ?
B1 N3 C3 C2 -1.7(4) . . . . ?
C10 N3 C3 C4 -0.1(4) . . . . ?
B1 N3 C3 C4 178.9(2) . . . . ?
N2 C10 C6 C7 -0.2(4) . . . . ?
N3 C10 C6 C7 -179.0(2) . . . . ?
N2 C10 C6 C5 179.7(2) . . . . ?
N3 C10 C6 C5 0.8(4) . . . . ?
N3 C3 C4 C5 1.4(4) . . . . ?
C2 C3 C4 C5 -178.0(3) . . . . ?
C9 C8 C7 C6 0.3(4) . . . . ?
C10 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
C3 C4 C5 C11 177.6(3) . . . . ?
C7 C6 C5 C4 -179.7(2) . . . . ?
C10 C6 C5 C4 0.5(4) . . . . ?
C7 C6 C5 C11 1.1(4) . . . . ?
C10 C6 C5 C11 -178.7(2) . . . . ?
C9 N1 C12 O1 6.3(5) . . . . ?
C9 N1 C12 C13 -169.6(3) . . . . ?
N3 C3 C2 C1 -3.9(4) . . . . ?
C4 C3 C2 C1 175.5(3) . . . . ?
C10 N2 C9 N1 -177.8(2) . . . . ?
C10 N2 C9 C8 0.7(4) . . . . ?
C12 N1 C9 N2 173.8(2) . . . . ?
C12 N1 C9 C8 -4.7(4) . . . . ?
C7 C8 C9 N2 -0.7(4) . . . . ?
C7 C8 C9 N1 177.7(2) . . . . ?
B1 O2 C1 C2 2.1(5) . . . . ?
B1 O2 C1 C14 -179.4(3) . . . . ?
C3 C2 C1 O2 4.0(5) . . . . ?
C3 C2 C1 C14 -174.3(3) . . . . ?
C1 O2 B1 F2 113.3(3) . . . . ?
C1 O2 B1 F1 -128.0(3) . . . . ?
C1 O2 B1 N3 -6.9(4) . . . . ?
C3 N3 B1 F2 -113.5(3) . . . . ?
C10 N3 B1 F2 65.5(3) . . . . ?
C3 N3 B1 F1 125.1(2) . . . . ?
C10 N3 B1 F1 -56.0(3) . . . . ?
C3 N3 B1 O2 6.5(3) . . . . ?
C10 N3 B1 O2 -174.5(2) . . . . ?
O1 C12 C13 Cl1 32.5(4) . . . . ?
N1 C12 C13 Cl1 -151.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.098
_database_code_depnum_ccdc_archive 'CCDC 983349'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 B F2 N6 O2'
_chemical_formula_sum            'C26 H25 B F2 N6 O2'
_chemical_formula_weight         502.33

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'
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'

_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                   8.5060(10)
_cell_length_b                   8.8100(11)
_cell_length_c                   17.414(2)
_cell_angle_alpha                96.487(5)
_cell_angle_beta                 103.927(3)
_cell_angle_gamma                105.669(4)
_cell_volume                     1197.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15576
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         27.93
_reflns_number_total             5705
_reflns_number_gt                3333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.0506P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5705
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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 0.44350(11) 0.70040(10) 0.21027(5) 0.0343(2) Uani 1 1 d . . .
F2 F 0.62899(10) 0.94961(10) 0.22222(5) 0.0353(2) Uani 1 1 d . . .
O1 O 0.34090(12) 0.91352(11) 0.18989(6) 0.0274(2) Uani 1 1 d . . .
O2 O 1.03387(12) 0.43585(12) 0.12110(6) 0.0293(2) Uani 1 1 d . . .
N1 N 0.46551(13) 0.80214(12) 0.08795(6) 0.0184(2) Uani 1 1 d . . .
N2 N 0.69160(13) 0.70293(12) 0.12590(6) 0.0192(2) Uani 1 1 d . . .
N3 N 0.90841(14) 0.60599(14) 0.17436(7) 0.0221(3) Uani 1 1 d . . .
N4 N 1.06904(14) 0.60479(13) 0.32475(7) 0.0223(3) Uani 1 1 d . . .
N6 N 0.79475(16) 0.32151(15) 0.39664(8) 0.0362(3) Uani 1 1 d . . .
C1 C 0.34765(16) 0.83410(15) 0.03025(8) 0.0215(3) Uani 1 1 d . . .
C2 C 0.34506(17) 0.80336(16) -0.05172(8) 0.0238(3) Uani 1 1 d . . .
H2 H 0.2625 0.8294 -0.0909 0.029 Uiso 1 1 calc R . .
C3 C 0.45615(17) 0.73812(15) -0.07627(8) 0.0221(3) Uani 1 1 d . . .
C4 C 0.58004(16) 0.70214(15) -0.01597(8) 0.0201(3) Uani 1 1 d . . .
C5 C 0.58187(15) 0.73507(15) 0.06558(8) 0.0187(3) Uani 1 1 d . . .
C6 C 0.80282(16) 0.63631(16) 0.10718(8) 0.0202(3) Uani 1 1 d . . .
C7 C 0.81559(17) 0.60026(16) 0.02851(8) 0.0233(3) Uani 1 1 d . . .
H7 H 0.8996 0.5549 0.0182 0.028 Uiso 1 1 calc R . .
C8 C 0.70241(17) 0.63308(16) -0.03223(8) 0.0232(3) Uani 1 1 d . . .
H8 H 0.7062 0.6090 -0.0862 0.028 Uiso 1 1 calc R . .
C9 C 0.22709(17) 0.90072(17) 0.05282(9) 0.0268(3) Uani 1 1 d . . .
H9 H 0.1422 0.9194 0.0117 0.032 Uiso 1 1 calc R . .
C10 C 0.22817(17) 0.93844(16) 0.12990(9) 0.0246(3) Uani 1 1 d . . .
C11 C 0.10812(19) 1.01470(18) 0.15637(10) 0.0333(4) Uani 1 1 d . . .
H11A H 0.0507 0.9492 0.1894 0.040 Uiso 1 1 calc R . .
H11B H 0.0232 1.0224 0.1089 0.040 Uiso 1 1 calc R . .
H11C H 0.1718 1.1225 0.1881 0.040 Uiso 1 1 calc R . .
C12 C 0.44898(18) 0.70080(17) -0.16329(8) 0.0289(3) Uani 1 1 d . . .
H12A H 0.3616 0.7389 -0.1958 0.035 Uiso 1 1 calc R . .
H12B H 0.4207 0.5845 -0.1805 0.035 Uiso 1 1 calc R . .
H12C H 0.5599 0.7546 -0.1706 0.035 Uiso 1 1 calc R . .
C13 C 1.00652(16) 0.50579(16) 0.17835(8) 0.0215(3) Uani 1 1 d . . .
C14 C 1.07197(17) 0.48040(16) 0.26343(8) 0.0242(3) Uani 1 1 d . . .
H14A H 1.0016 0.3752 0.2694 0.029 Uiso 1 1 calc R . .
H14B H 1.1903 0.4770 0.2722 0.029 Uiso 1 1 calc R . .
C15 C 1.21846(17) 0.74720(17) 0.34494(9) 0.0267(3) Uani 1 1 d . A .
H15A H 1.2513 0.7686 0.2955 0.032 Uiso 1 1 calc R . .
H15B H 1.3151 0.7277 0.3828 0.032 Uiso 1 1 calc R . .
C16 C 1.18170(17) 0.89089(16) 0.38284(8) 0.0233(3) Uani 1 1 d . . .
N5 N 1.03931(17) 0.92302(17) 0.34455(8) 0.0340(4) Uani 0.497(11) 1 d P A 1
C17 C 1.29078(16) 0.98223(15) 0.45325(8) 0.0257(3) Uani 0.497(11) 1 d P A 1
H17A H 1.3906 0.9575 0.4784 0.031 Uiso 0.497(11) 1 calc PR A 1
C17' C 1.03931(17) 0.92302(17) 0.34455(8) 0.0340(4) Uani 0.503(11) 1 d P A -1
H17B H 0.9659 0.8578 0.2949 0.041 Uiso 0.503(11) 1 calc PR A -1
N5' N 1.29078(16) 0.98223(15) 0.45325(8) 0.0257(3) Uani 0.503(11) 1 d P A -1
C18 C 1.25332(19) 1.11014(17) 0.48684(9) 0.0320(4) Uani 1 1 d . . .
H18 H 1.3286 1.1756 0.5361 0.038 Uiso 1 1 calc R A 1
C19 C 1.1095(2) 1.14686(18) 0.45126(10) 0.0344(4) Uani 1 1 d . A .
H19 H 1.0833 1.2354 0.4756 0.041 Uiso 1 1 calc R . .
C20 C 1.0044(2) 1.0518(2) 0.37949(10) 0.0396(4) Uani 1 1 d . . .
H20 H 0.9051 1.0764 0.3535 0.048 Uiso 1 1 calc R A 1
C21 C 1.03274(17) 0.54631(17) 0.39625(8) 0.0255(3) Uani 1 1 d . . .
H21A H 1.0761 0.6372 0.4426 0.031 Uiso 1 1 calc R . .
H21B H 1.0929 0.4667 0.4096 0.031 Uiso 1 1 calc R . .
C22 C 0.84422(17) 0.46967(17) 0.38251(8) 0.0222(3) Uani 1 1 d . . .
C23 C 0.73137(18) 0.55385(18) 0.35829(9) 0.0285(3) Uani 1 1 d . . .
H23 H 0.7711 0.6590 0.3480 0.034 Uiso 1 1 calc R . .
C24 C 0.56112(19) 0.48389(19) 0.34931(9) 0.0334(4) Uani 1 1 d . . .
H24 H 0.4816 0.5400 0.3331 0.040 Uiso 1 1 calc R . .
C25 C 0.5080(2) 0.3309(2) 0.36430(9) 0.0389(4) Uani 1 1 d . . .
H25 H 0.3913 0.2794 0.3590 0.047 Uiso 1 1 calc R . .
C26 C 0.6279(2) 0.2551(2) 0.38700(11) 0.0468(5) Uani 1 1 d . . .
H26 H 0.5906 0.1489 0.3965 0.056 Uiso 1 1 calc R . .
B1 B 0.4740(2) 0.84056(19) 0.18078(9) 0.0227(3) Uani 1 1 d . . .
H1 H 0.903(2) 0.6499(19) 0.2240(10) 0.050(5) 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 1.3749(18) . ?
F2 B1 1.3723(18) . ?
O1 C10 1.3200(16) . ?
O1 B1 1.4752(18) . ?
O2 C13 1.2158(15) . ?
N1 C1 1.3511(16) . ?
N1 C5 1.3892(16) . ?
N1 B1 1.5938(18) . ?
N2 C6 1.3233(16) . ?
N2 C5 1.3389(16) . ?
N3 C13 1.3655(17) . ?
N3 C6 1.3933(17) . ?
N3 H1 0.924(16) . ?
N4 C14 1.4508(16) . ?
N4 C15 1.4618(17) . ?
N4 C21 1.4681(17) . ?
N6 C22 1.3294(18) . ?
N6 C26 1.342(2) . ?
C1 C2 1.4162(19) . ?
C1 C9 1.4204(19) . ?
C2 C3 1.3559(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4271(18) . ?
C3 C12 1.4966(18) . ?
C4 C8 1.4067(18) . ?
C4 C5 1.4124(17) . ?
C6 C7 1.4075(17) . ?
C7 C8 1.3633(19) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.3431(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4945(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5167(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5034(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N5 1.3530(19) . ?
C16 C17 1.3558(18) . ?
N5 C20 1.363(2) . ?
C17 C18 1.3595(18) . ?
C17 H17A 0.9500 . ?
C18 C19 1.371(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.372(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.5094(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.3819(19) . ?
C23 C24 1.374(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.370(2) . ?
C25 H25 0.9500 . ?
C26 H26 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
C10 O1 B1 125.06(11) . . ?
C1 N1 C5 119.06(12) . . ?
C1 N1 B1 121.36(11) . . ?
C5 N1 B1 119.58(11) . . ?
C6 N2 C5 117.58(11) . . ?
C13 N3 C6 129.48(12) . . ?
C13 N3 H1 113.7(11) . . ?
C6 N3 H1 116.4(11) . . ?
C14 N4 C15 113.08(11) . . ?
C14 N4 C21 113.68(11) . . ?
C15 N4 C21 112.76(11) . . ?
C22 N6 C26 117.07(14) . . ?
N1 C1 C2 120.58(13) . . ?
N1 C1 C9 119.20(13) . . ?
C2 C1 C9 120.22(13) . . ?
C3 C2 C1 122.35(13) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 117.58(12) . . ?
C2 C3 C12 122.08(13) . . ?
C4 C3 C12 120.33(13) . . ?
C8 C4 C5 116.59(12) . . ?
C8 C4 C3 124.10(12) . . ?
C5 C4 C3 119.32(12) . . ?
N2 C5 N1 115.52(12) . . ?
N2 C5 C4 123.37(12) . . ?
N1 C5 C4 121.10(12) . . ?
N2 C6 N3 112.56(11) . . ?
N2 C6 C7 124.39(13) . . ?
N3 C6 C7 123.04(12) . . ?
C8 C7 C6 117.25(13) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C4 120.80(12) . . ?
C7 C8 H8 119.6 . . ?
C4 C8 H8 119.6 . . ?
C10 C9 C1 122.69(14) . . ?
C10 C9 H9 118.7 . . ?
C1 C9 H9 118.7 . . ?
O1 C10 C9 121.81(13) . . ?
O1 C10 C11 113.83(13) . . ?
C9 C10 C11 124.34(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N3 125.54(13) . . ?
O2 C13 C14 121.91(12) . . ?
N3 C13 C14 112.44(11) . . ?
N4 C14 C13 113.18(11) . . ?
N4 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N4 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
N4 C15 C16 110.65(11) . . ?
N4 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N5 C16 C17 122.79(13) . . ?
N5 C16 C15 117.89(12) . . ?
C17 C16 C15 119.31(13) . . ?
C16 N5 C20 117.95(13) . . ?
C16 C17 C18 118.14(13) . . ?
C16 C17 H17A 120.9 . . ?
C18 C17 H17A 120.9 . . ?
C17 C18 C19 121.52(14) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C20 118.02(14) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
N5 C20 C19 121.56(15) . . ?
N5 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
N4 C21 C22 111.42(11) . . ?
N4 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N4 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
N6 C22 C23 122.63(13) . . ?
N6 C22 C21 116.95(12) . . ?
C23 C22 C21 120.40(13) . . ?
C24 C23 C22 119.32(14) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 118.77(15) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 118.19(15) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
N6 C26 C25 124.01(16) . . ?
N6 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?
F2 B1 F1 112.55(12) . . ?
F2 B1 O1 107.81(11) . . ?
F1 B1 O1 107.69(12) . . ?
F2 B1 N1 109.19(11) . . ?
F1 B1 N1 109.71(11) . . ?
O1 B1 N1 109.83(11) . . ?

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
C5 N1 C1 C2 -1.50(18) . . . . ?
B1 N1 C1 C2 178.20(11) . . . . ?
C5 N1 C1 C9 179.18(12) . . . . ?
B1 N1 C1 C9 -1.11(18) . . . . ?
N1 C1 C2 C3 1.5(2) . . . . ?
C9 C1 C2 C3 -179.18(13) . . . . ?
C1 C2 C3 C4 -0.77(19) . . . . ?
C1 C2 C3 C12 177.89(12) . . . . ?
C2 C3 C4 C8 179.43(12) . . . . ?
C12 C3 C4 C8 0.74(19) . . . . ?
C2 C3 C4 C5 0.12(18) . . . . ?
C12 C3 C4 C5 -178.57(11) . . . . ?
C6 N2 C5 N1 178.84(11) . . . . ?
C6 N2 C5 C4 -0.28(18) . . . . ?
C1 N1 C5 N2 -178.27(11) . . . . ?
B1 N1 C5 N2 2.02(16) . . . . ?
C1 N1 C5 C4 0.87(18) . . . . ?
B1 N1 C5 C4 -178.85(11) . . . . ?
C8 C4 C5 N2 -0.46(18) . . . . ?
C3 C4 C5 N2 178.90(11) . . . . ?
C8 C4 C5 N1 -179.52(11) . . . . ?
C3 C4 C5 N1 -0.16(18) . . . . ?
C5 N2 C6 N3 -179.02(11) . . . . ?
C5 N2 C6 C7 1.39(19) . . . . ?
C13 N3 C6 N2 161.86(13) . . . . ?
C13 N3 C6 C7 -18.5(2) . . . . ?
N2 C6 C7 C8 -1.7(2) . . . . ?
N3 C6 C7 C8 178.77(12) . . . . ?
C6 C7 C8 C4 0.83(19) . . . . ?
C5 C4 C8 C7 0.14(19) . . . . ?
C3 C4 C8 C7 -179.19(13) . . . . ?
N1 C1 C9 C10 2.2(2) . . . . ?
C2 C1 C9 C10 -177.16(13) . . . . ?
B1 O1 C10 C9 -1.3(2) . . . . ?
B1 O1 C10 C11 -179.86(12) . . . . ?
C1 C9 C10 O1 -1.0(2) . . . . ?
C1 C9 C10 C11 177.44(13) . . . . ?
C6 N3 C13 O2 8.7(2) . . . . ?
C6 N3 C13 C14 -167.54(12) . . . . ?
C15 N4 C14 C13 -83.64(14) . . . . ?
C21 N4 C14 C13 146.11(12) . . . . ?
O2 C13 C14 N4 163.48(12) . . . . ?
N3 C13 C14 N4 -20.08(16) . . . . ?
C14 N4 C15 C16 158.68(11) . . . . ?
C21 N4 C15 C16 -70.62(15) . . . . ?
N4 C15 C16 N5 -50.43(17) . . . . ?
N4 C15 C16 C17 129.47(13) . . . . ?
C17 C16 N5 C20 -0.9(2) . . . . ?
C15 C16 N5 C20 179.00(13) . . . . ?
N5 C16 C17 C18 0.8(2) . . . . ?
C15 C16 C17 C18 -179.07(12) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C16 N5 C20 C19 0.0(2) . . . . ?
C18 C19 C20 N5 0.9(2) . . . . ?
C14 N4 C21 C22 -81.23(14) . . . . ?
C15 N4 C21 C22 148.37(11) . . . . ?
C26 N6 C22 C23 -0.5(2) . . . . ?
C26 N6 C22 C21 177.89(13) . . . . ?
N4 C21 C22 N6 126.39(13) . . . . ?
N4 C21 C22 C23 -55.18(17) . . . . ?
N6 C22 C23 C24 0.9(2) . . . . ?
C21 C22 C23 C24 -177.39(13) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C22 N6 C26 C25 -0.5(3) . . . . ?
C24 C25 C26 N6 0.9(3) . . . . ?
C10 O1 B1 F2 120.89(13) . . . . ?
C10 O1 B1 F1 -117.42(14) . . . . ?
C10 O1 B1 N1 2.02(18) . . . . ?
C1 N1 B1 F2 -118.79(13) . . . . ?
C5 N1 B1 F2 60.91(15) . . . . ?
C1 N1 B1 F1 117.41(13) . . . . ?
C5 N1 B1 F1 -62.88(15) . . . . ?
C1 N1 B1 O1 -0.78(16) . . . . ?
C5 N1 B1 O1 178.93(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H1 N4 0.924(16) 2.120(17) 2.6489(16) 115.2(13) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 983350'
