# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_r131024g1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 B F2 N2'
_chemical_formula_weight         324.17

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   13.109(3)
_cell_length_b                   12.646(3)
_cell_length_c                   20.478(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3394.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5436
_cell_measurement_theta_min      1.8927
_cell_measurement_theta_max      30.4899

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26486
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2990
_reflns_number_gt                2119
_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  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1092P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2990
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.17804(12) 0.96147(13) 0.41188(6) 0.0861(6) Uani 1 1 d . . .
F2 F 0.06862(11) 0.82361(12) 0.40677(6) 0.0845(5) Uani 1 1 d . . .
N1 N 0.04980(13) 0.96267(13) 0.32731(8) 0.0510(5) Uani 1 1 d . . .
N2 N 0.19698(13) 0.83952(14) 0.32258(9) 0.0551(5) Uani 1 1 d . . .
B1 B 0.1232(2) 0.8963(2) 0.36983(12) 0.0572(7) Uani 1 1 d . . .
C1 C -0.0479(2) 1.0410(2) 0.42036(10) 0.0734(8) Uani 1 1 d . . .
H1A H -0.0696 0.9755 0.4396 0.110 Uiso 1 1 calc R . .
H1B H -0.1005 1.0931 0.4256 0.110 Uiso 1 1 calc R . .
H1C H 0.0132 1.0649 0.4415 0.110 Uiso 1 1 calc R . .
C2 C -0.02743(18) 1.02453(17) 0.34947(10) 0.0556(6) Uani 1 1 d . . .
C3 C -0.07997(18) 1.06585(18) 0.29570(10) 0.0575(6) Uani 1 1 d . . .
H3 H -0.1355 1.1115 0.2980 0.069 Uiso 1 1 calc R . .
C4 C -0.03671(17) 1.02849(17) 0.23884(10) 0.0518(6) Uani 1 1 d . . .
C5 C 0.04728(16) 0.96359(16) 0.25864(9) 0.0472(5) Uani 1 1 d . . .
C6 C 0.12161(15) 0.90893(15) 0.22273(10) 0.0484(6) Uani 1 1 d . . .
C7 C 0.19744(16) 0.84993(16) 0.25413(11) 0.0520(6) Uani 1 1 d . . .
C8 C 0.28201(18) 0.79136(17) 0.22921(11) 0.0593(6) Uani 1 1 d . . .
C9 C 0.32819(19) 0.7459(2) 0.28314(12) 0.0690(7) Uani 1 1 d . . .
H9 H 0.3852 0.7022 0.2820 0.083 Uiso 1 1 calc R . .
C10 C 0.27554(19) 0.77595(19) 0.33973(12) 0.0639(7) Uani 1 1 d . . .
C11 C 0.2980(2) 0.7469(2) 0.40907(12) 0.0852(9) Uani 1 1 d . . .
H11A H 0.3383 0.8015 0.4289 0.128 Uiso 1 1 calc R . .
H11B H 0.3348 0.6814 0.4102 0.128 Uiso 1 1 calc R . .
H11C H 0.2351 0.7393 0.4326 0.128 Uiso 1 1 calc R . .
C12 C -0.07535(19) 1.05263(19) 0.17135(11) 0.0667(7) Uani 1 1 d . . .
H12A H -0.1339 1.0980 0.1743 0.100 Uiso 1 1 calc R . .
H12B H -0.0941 0.9880 0.1499 0.100 Uiso 1 1 calc R . .
H12C H -0.0228 1.0873 0.1468 0.100 Uiso 1 1 calc R . .
C13 C 0.3197(2) 0.7825(2) 0.16005(13) 0.0757(8) Uani 1 1 d . . .
H13A H 0.3815 0.7418 0.1592 0.113 Uiso 1 1 calc R . .
H13B H 0.3327 0.8519 0.1430 0.113 Uiso 1 1 calc R . .
H13C H 0.2689 0.7482 0.1338 0.113 Uiso 1 1 calc R . .
C14 C 0.12069(16) 0.91480(16) 0.15011(10) 0.0514(6) Uani 1 1 d . . .
C15 C 0.1686(2) 0.9979(2) 0.11845(11) 0.0741(8) Uani 1 1 d . . .
H15 H 0.2003 1.0505 0.1428 0.089 Uiso 1 1 calc R . .
C16 C 0.1697(2) 1.0034(3) 0.05105(13) 0.0898(9) Uani 1 1 d . . .
H16 H 0.2029 1.0591 0.0304 0.108 Uiso 1 1 calc R . .
C17 C 0.1221(2) 0.9270(3) 0.01456(13) 0.0902(10) Uani 1 1 d . . .
H17 H 0.1218 0.9316 -0.0308 0.108 Uiso 1 1 calc R . .
C18 C 0.0748(2) 0.8439(2) 0.04514(12) 0.0833(8) Uani 1 1 d . . .
H18 H 0.0433 0.7915 0.0205 0.100 Uiso 1 1 calc R . .
C19 C 0.07377(19) 0.8379(2) 0.11297(11) 0.0665(7) Uani 1 1 d . . .
H19 H 0.0412 0.7816 0.1334 0.080 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 1.392(3) . ?
F2 B1 1.389(3) . ?
N1 C2 1.358(3) . ?
N1 C5 1.406(2) . ?
N1 B1 1.545(3) . ?
N2 C10 1.353(3) . ?
N2 C7 1.408(3) . ?
N2 B1 1.545(3) . ?
C1 C2 1.491(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.400(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.432(3) . ?
C4 C12 1.503(3) . ?
C5 C6 1.403(3) . ?
C6 C7 1.399(3) . ?
C6 C14 1.489(3) . ?
C7 C8 1.428(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.504(3) . ?
C9 C10 1.401(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.496(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.379(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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 N1 C5 108.17(17) . . ?
C2 N1 B1 126.07(18) . . ?
C5 N1 B1 125.63(18) . . ?
C10 N2 C7 108.10(18) . . ?
C10 N2 B1 126.18(19) . . ?
C7 N2 B1 125.64(17) . . ?
F2 B1 F1 108.73(19) . . ?
F2 B1 N2 110.82(19) . . ?
F1 B1 N2 109.84(19) . . ?
F2 B1 N1 110.20(19) . . ?
F1 B1 N1 110.43(19) . . ?
N2 B1 N1 106.81(18) . . ?
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 C3 108.61(18) . . ?
N1 C2 C1 122.7(2) . . ?
C3 C2 C1 128.7(2) . . ?
C4 C3 C2 109.5(2) . . ?
C4 C3 H3 125.2 . . ?
C2 C3 H3 125.2 . . ?
C3 C4 C5 105.87(17) . . ?
C3 C4 C12 124.6(2) . . ?
C5 C4 C12 129.49(19) . . ?
C6 C5 N1 120.24(18) . . ?
C6 C5 C4 131.91(17) . . ?
N1 C5 C4 107.82(17) . . ?
C7 C6 C5 121.01(19) . . ?
C7 C6 C14 119.42(18) . . ?
C5 C6 C14 119.57(18) . . ?
C6 C7 N2 120.28(19) . . ?
C6 C7 C8 131.6(2) . . ?
N2 C7 C8 108.11(18) . . ?
C9 C8 C7 105.7(2) . . ?
C9 C8 C13 125.2(2) . . ?
C7 C8 C13 129.1(2) . . ?
C8 C9 C10 109.4(2) . . ?
C8 C9 H9 125.3 . . ?
C10 C9 H9 125.3 . . ?
N2 C10 C9 108.8(2) . . ?
N2 C10 C11 122.8(2) . . ?
C9 C10 C11 128.4(2) . . ?
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 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.6(2) . . ?
C19 C14 C6 121.27(19) . . ?
C15 C14 C6 120.11(19) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.5(2) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 B1 F2 -62.2(3) . . . . ?
C7 N2 B1 F2 121.7(2) . . . . ?
C10 N2 B1 F1 58.0(3) . . . . ?
C7 N2 B1 F1 -118.2(2) . . . . ?
C10 N2 B1 N1 177.78(19) . . . . ?
C7 N2 B1 N1 1.6(3) . . . . ?
C2 N1 B1 F2 59.2(3) . . . . ?
C5 N1 B1 F2 -116.2(2) . . . . ?
C2 N1 B1 F1 -60.9(3) . . . . ?
C5 N1 B1 F1 123.7(2) . . . . ?
C2 N1 B1 N2 179.69(19) . . . . ?
C5 N1 B1 N2 4.3(3) . . . . ?
C5 N1 C2 C3 -0.1(2) . . . . ?
B1 N1 C2 C3 -176.22(19) . . . . ?
C5 N1 C2 C1 179.5(2) . . . . ?
B1 N1 C2 C1 3.5(3) . . . . ?
N1 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C4 -178.7(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C2 C3 C4 C12 177.6(2) . . . . ?
C2 N1 C5 C6 177.57(18) . . . . ?
B1 N1 C5 C6 -6.3(3) . . . . ?
C2 N1 C5 C4 -0.7(2) . . . . ?
B1 N1 C5 C4 175.39(18) . . . . ?
C3 C4 C5 C6 -176.7(2) . . . . ?
C12 C4 C5 C6 4.4(4) . . . . ?
C3 C4 C5 N1 1.3(2) . . . . ?
C12 C4 C5 N1 -177.6(2) . . . . ?
N1 C5 C6 C7 2.0(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
N1 C5 C6 C14 -177.17(18) . . . . ?
C4 C5 C6 C14 0.6(3) . . . . ?
C5 C6 C7 N2 3.6(3) . . . . ?
C14 C6 C7 N2 -177.17(17) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C14 C6 C7 C8 1.6(3) . . . . ?
C10 N2 C7 C6 177.75(18) . . . . ?
B1 N2 C7 C6 -5.5(3) . . . . ?
C10 N2 C7 C8 -1.3(2) . . . . ?
B1 N2 C7 C8 175.44(19) . . . . ?
C6 C7 C8 C9 -177.6(2) . . . . ?
N2 C7 C8 C9 1.3(2) . . . . ?
C6 C7 C8 C13 5.2(4) . . . . ?
N2 C7 C8 C13 -175.9(2) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C13 C8 C9 C10 176.5(2) . . . . ?
C7 N2 C10 C9 0.8(2) . . . . ?
B1 N2 C10 C9 -175.9(2) . . . . ?
C7 N2 C10 C11 -179.7(2) . . . . ?
B1 N2 C10 C11 3.6(3) . . . . ?
C8 C9 C10 N2 0.0(3) . . . . ?
C8 C9 C10 C11 -179.5(2) . . . . ?
C7 C6 C14 C19 85.3(3) . . . . ?
C5 C6 C14 C19 -95.5(2) . . . . ?
C7 C6 C14 C15 -93.9(3) . . . . ?
C5 C6 C14 C15 85.3(3) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?
C6 C14 C15 C16 179.0(2) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C15 C14 C19 C18 0.0(4) . . . . ?
C6 C14 C19 C18 -179.2(2) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 989184'
#######################################################################
#
#                 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_r130721f1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 B F2 N2 O'
_chemical_formula_weight         368.22

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

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

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

_cell_length_a                   8.0768(16)
_cell_length_b                   9.6024(19)
_cell_length_c                   24.077(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1867.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6849
_cell_measurement_theta_min      1.6916
_cell_measurement_theta_max      27.8984

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_T_max  0.9815
_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  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18813
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.89
_reflns_number_total             4462
_reflns_number_gt                3908
_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  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.050(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_number_reflns         4462
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_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 0.73910(9) -0.09713(7) 0.25059(3) 0.02355(18) Uani 1 1 d . . .
F2 F 0.83810(9) -0.16682(7) 0.16691(3) 0.02495(18) Uani 1 1 d . . .
O1 O 0.24014(11) 0.54277(8) -0.00954(4) 0.0232(2) Uani 1 1 d . . .
N1 N 0.55408(12) -0.08810(10) 0.17189(4) 0.0179(2) Uani 1 1 d . . .
N2 N 0.78733(12) 0.07892(10) 0.18092(4) 0.0175(2) Uani 1 1 d . . .
B1 B 0.73354(17) -0.07265(14) 0.19338(6) 0.0183(3) Uani 1 1 d . . .
C1 C 0.17669(16) 0.01587(13) 0.09066(5) 0.0244(3) Uani 1 1 d . . .
H1A H 0.2112 0.0154 0.0516 0.037 Uiso 1 1 calc R . .
H1B H 0.1554 0.1119 0.1025 0.037 Uiso 1 1 calc R . .
H1C H 0.0755 -0.0394 0.0949 0.037 Uiso 1 1 calc R . .
C2 C 0.50072(18) -0.32130(13) 0.21404(6) 0.0263(3) Uani 1 1 d . . .
H2A H 0.6079 -0.3565 0.2011 0.039 Uiso 1 1 calc R . .
H2B H 0.4167 -0.3943 0.2100 0.039 Uiso 1 1 calc R . .
H2C H 0.5094 -0.2944 0.2532 0.039 Uiso 1 1 calc R . .
C3 C 0.45230(16) -0.19793(12) 0.18036(5) 0.0201(3) Uani 1 1 d . . .
C4 C 0.30219(16) -0.17340(13) 0.15268(5) 0.0214(3) Uani 1 1 d . . .
H4 H 0.2094 -0.2342 0.1524 0.026 Uiso 1 1 calc R . .
C5 C 0.31141(15) -0.04566(12) 0.12587(5) 0.0200(3) Uani 1 1 d . . .
C6 C 0.47140(16) 0.00918(12) 0.13825(5) 0.0179(3) Uani 1 1 d . . .
C7 C 0.54557(15) 0.13743(11) 0.12582(5) 0.0172(2) Uani 1 1 d . . .
C8 C 0.70108(15) 0.17236(12) 0.14655(5) 0.0179(2) Uani 1 1 d . . .
C9 C 0.76622(17) 0.42620(12) 0.10849(6) 0.0257(3) Uani 1 1 d . . .
H9A H 0.8638 0.4868 0.1099 0.039 Uiso 1 1 calc R . .
H9B H 0.6708 0.4755 0.1241 0.039 Uiso 1 1 calc R . .
H9C H 0.7429 0.4009 0.0698 0.039 Uiso 1 1 calc R . .
C10 C 0.79882(16) 0.29607(12) 0.14179(5) 0.0209(3) Uani 1 1 d . . .
C11 C 0.93822(16) 0.27435(13) 0.17348(5) 0.0225(3) Uani 1 1 d . . .
H11 H 1.0261 0.3389 0.1785 0.027 Uiso 1 1 calc R . .
C12 C 0.92911(16) 0.14067(12) 0.19726(5) 0.0212(3) Uani 1 1 d . . .
C13 C 1.05214(18) 0.07474(14) 0.23486(6) 0.0285(3) Uani 1 1 d . . .
H13A H 1.0239 0.0962 0.2735 0.043 Uiso 1 1 calc R . .
H13B H 1.1628 0.1109 0.2265 0.043 Uiso 1 1 calc R . .
H13C H 1.0508 -0.0264 0.2294 0.043 Uiso 1 1 calc R . .
C14 C 0.45549(15) 0.24121(11) 0.09107(5) 0.0173(2) Uani 1 1 d . . .
C15 C 0.46092(15) 0.23385(12) 0.03326(5) 0.0197(3) Uani 1 1 d . . .
H15 H 0.5158 0.1581 0.0158 0.024 Uiso 1 1 calc R . .
C16 C 0.38718(15) 0.33574(12) 0.00111(5) 0.0193(3) Uani 1 1 d . . .
H16 H 0.3923 0.3301 -0.0382 0.023 Uiso 1 1 calc R . .
C17 C 0.30535(15) 0.44676(11) 0.02641(5) 0.0185(3) Uani 1 1 d . . .
C18 C 0.29541(15) 0.45360(12) 0.08365(5) 0.0227(3) Uani 1 1 d . . .
H18 H 0.2373 0.5278 0.1010 0.027 Uiso 1 1 calc R . .
C19 C 0.37141(17) 0.35064(12) 0.11576(5) 0.0219(3) Uani 1 1 d . . .
H19 H 0.3653 0.3558 0.1551 0.026 Uiso 1 1 calc R . .
C20 C 0.16082(17) 0.66354(12) 0.01340(6) 0.0251(3) Uani 1 1 d . . .
H20A H 0.2356 0.7110 0.0399 0.030 Uiso 1 1 calc R . .
H20B H 0.0583 0.6366 0.0332 0.030 Uiso 1 1 calc R . .
C21 C 0.12067(19) 0.75836(14) -0.03448(6) 0.0322(3) Uani 1 1 d . . .
H21A H 0.2229 0.7827 -0.0542 0.048 Uiso 1 1 calc R . .
H21B H 0.0681 0.8434 -0.0204 0.048 Uiso 1 1 calc R . .
H21C H 0.0449 0.7108 -0.0600 0.048 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 1.3982(16) . ?
F2 B1 1.3917(16) . ?
O1 C17 1.3699(14) . ?
O1 C20 1.4354(15) . ?
N1 C3 1.3526(15) . ?
N1 C6 1.4053(15) . ?
N1 B1 1.5461(17) . ?
N2 C12 1.3481(15) . ?
N2 C8 1.4055(15) . ?
N2 B1 1.5483(16) . ?
C1 C5 1.5005(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4880(17) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.4033(19) . ?
C4 C5 1.3881(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4269(18) . ?
C6 C7 1.4018(16) . ?
C7 C8 1.3926(17) . ?
C7 C14 1.4907(16) . ?
C8 C10 1.4309(16) . ?
C9 C10 1.5078(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3759(19) . ?
C11 C12 1.4075(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4859(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.3852(16) . ?
C14 C15 1.3945(17) . ?
C15 C16 1.3823(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3944(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3820(17) . ?
C18 C19 1.3972(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5044(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C17 O1 C20 118.17(10) . . ?
C3 N1 C6 108.44(10) . . ?
C3 N1 B1 126.45(10) . . ?
C6 N1 B1 125.07(10) . . ?
C12 N2 C8 108.18(10) . . ?
C12 N2 B1 126.53(10) . . ?
C8 N2 B1 125.11(10) . . ?
F2 B1 F1 108.81(10) . . ?
F2 B1 N1 110.69(10) . . ?
F1 B1 N1 110.10(10) . . ?
F2 B1 N2 110.59(10) . . ?
F1 B1 N2 109.87(10) . . ?
N1 B1 N2 106.76(9) . . ?
C5 C1 H1A 109.5 . . ?
C5 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C5 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 108.82(11) . . ?
N1 C3 C2 122.90(12) . . ?
C4 C3 C2 128.28(12) . . ?
C5 C4 C3 108.83(11) . . ?
C5 C4 H4 125.6 . . ?
C3 C4 H4 125.6 . . ?
C4 C5 C6 106.11(11) . . ?
C4 C5 C1 124.88(11) . . ?
C6 C5 C1 129.00(11) . . ?
C7 C6 N1 120.26(11) . . ?
C7 C6 C5 131.81(11) . . ?
N1 C6 C5 107.79(10) . . ?
C8 C7 C6 121.37(11) . . ?
C8 C7 C14 118.70(10) . . ?
C6 C7 C14 119.90(11) . . ?
C7 C8 N2 120.29(10) . . ?
C7 C8 C10 131.98(11) . . ?
N2 C8 C10 107.68(10) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 106.33(11) . . ?
C11 C10 C9 124.29(11) . . ?
C8 C10 C9 129.36(11) . . ?
C10 C11 C12 108.72(11) . . ?
C10 C11 H11 125.6 . . ?
C12 C11 H11 125.6 . . ?
N2 C12 C11 109.08(11) . . ?
N2 C12 C13 123.94(12) . . ?
C11 C12 C13 126.98(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.83(11) . . ?
C19 C14 C7 120.37(11) . . ?
C15 C14 C7 120.73(11) . . ?
C16 C15 C14 120.63(11) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.06(11) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
O1 C17 C18 125.15(11) . . ?
O1 C17 C16 114.89(11) . . ?
C18 C17 C16 119.96(11) . . ?
C17 C18 C19 119.52(11) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.98(11) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
O1 C20 C21 106.87(11) . . ?
O1 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O1 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 B1 F2 68.26(15) . . . . ?
C6 N1 B1 F2 -109.31(12) . . . . ?
C3 N1 B1 F1 -52.09(15) . . . . ?
C6 N1 B1 F1 130.34(11) . . . . ?
C3 N1 B1 N2 -171.31(11) . . . . ?
C6 N1 B1 N2 11.12(15) . . . . ?
C12 N2 B1 F2 -66.04(16) . . . . ?
C8 N2 B1 F2 108.55(12) . . . . ?
C12 N2 B1 F1 54.10(15) . . . . ?
C8 N2 B1 F1 -131.31(12) . . . . ?
C12 N2 B1 N1 173.47(10) . . . . ?
C8 N2 B1 N1 -11.94(15) . . . . ?
C6 N1 C3 C4 -0.32(14) . . . . ?
B1 N1 C3 C4 -178.22(11) . . . . ?
C6 N1 C3 C2 179.60(11) . . . . ?
B1 N1 C3 C2 1.69(19) . . . . ?
N1 C3 C4 C5 0.60(14) . . . . ?
C2 C3 C4 C5 -179.31(12) . . . . ?
C3 C4 C5 C6 -0.62(14) . . . . ?
C3 C4 C5 C1 178.49(12) . . . . ?
C3 N1 C6 C7 176.08(11) . . . . ?
B1 N1 C6 C7 -5.99(17) . . . . ?
C3 N1 C6 C5 -0.07(13) . . . . ?
B1 N1 C6 C5 177.87(11) . . . . ?
C4 C5 C6 C7 -175.11(13) . . . . ?
C1 C5 C6 C7 5.8(2) . . . . ?
C4 C5 C6 N1 0.43(13) . . . . ?
C1 C5 C6 N1 -178.63(12) . . . . ?
N1 C6 C7 C8 -0.50(17) . . . . ?
C5 C6 C7 C8 174.58(13) . . . . ?
N1 C6 C7 C14 -178.72(11) . . . . ?
C5 C6 C7 C14 -3.6(2) . . . . ?
C6 C7 C8 N2 -0.28(17) . . . . ?
C14 C7 C8 N2 177.96(11) . . . . ?
C6 C7 C8 C10 -177.32(13) . . . . ?
C14 C7 C8 C10 0.9(2) . . . . ?
C12 N2 C8 C7 -176.97(11) . . . . ?
B1 N2 C8 C7 7.60(17) . . . . ?
C12 N2 C8 C10 0.72(13) . . . . ?
B1 N2 C8 C10 -174.71(11) . . . . ?
C7 C8 C10 C11 176.68(13) . . . . ?
N2 C8 C10 C11 -0.63(14) . . . . ?
C7 C8 C10 C9 -4.8(2) . . . . ?
N2 C8 C10 C9 177.86(12) . . . . ?
C8 C10 C11 C12 0.32(14) . . . . ?
C9 C10 C11 C12 -178.27(12) . . . . ?
C8 N2 C12 C11 -0.53(13) . . . . ?
B1 N2 C12 C11 174.82(11) . . . . ?
C8 N2 C12 C13 178.98(12) . . . . ?
B1 N2 C12 C13 -5.67(19) . . . . ?
C10 C11 C12 N2 0.13(14) . . . . ?
C10 C11 C12 C13 -179.36(13) . . . . ?
C8 C7 C14 C19 -79.56(15) . . . . ?
C6 C7 C14 C19 98.71(14) . . . . ?
C8 C7 C14 C15 97.34(14) . . . . ?
C6 C7 C14 C15 -84.40(15) . . . . ?
C19 C14 C15 C16 1.56(18) . . . . ?
C7 C14 C15 C16 -175.38(11) . . . . ?
C14 C15 C16 C17 -0.46(18) . . . . ?
C20 O1 C17 C18 2.74(17) . . . . ?
C20 O1 C17 C16 -177.10(10) . . . . ?
C15 C16 C17 O1 178.69(10) . . . . ?
C15 C16 C17 C18 -1.16(18) . . . . ?
O1 C17 C18 C19 -178.21(11) . . . . ?
C16 C17 C18 C19 1.63(18) . . . . ?
C15 C14 C19 C18 -1.09(18) . . . . ?
C7 C14 C19 C18 175.87(11) . . . . ?
C17 C18 C19 C14 -0.50(19) . . . . ?
C17 O1 C20 C21 173.04(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 989185'
#######################################################################
#
#                 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         ?
_chemical_formula_sum            'C23 H27 B F2 N2 O2'
_chemical_formula_weight         412.28

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

_symmetry_cell_setting           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                   13.111(3)
_cell_length_b                   10.490(2)
_cell_length_c                   16.055(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.21(3)
_cell_angle_gamma                90.00
_cell_volume                     2058.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5624
_cell_measurement_theta_min      1.6661
_cell_measurement_theta_max      27.9664

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9867
_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  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20684
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.89
_reflns_number_total             4901
_reflns_number_gt                2867
_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  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4901
_refine_ls_number_parameters     290
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1860
_refine_ls_wR_factor_gt          0.1711
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.19944(10) 0.46679(12) 0.49592(8) 0.0201(3) Uani 1 1 d . . .
F2 F 0.16128(10) 0.66968(12) 0.52467(8) 0.0216(3) Uani 1 1 d . . .
O1 O 0.84718(12) 0.55550(14) 1.00755(10) 0.0217(4) Uani 1 1 d . A .
O2 O 1.01461(13) 0.54863(16) 1.17940(10) 0.0258(4) Uani 1 1 d D . .
N1 N 0.34937(14) 0.61525(18) 0.55263(11) 0.0171(4) Uani 1 1 d . . .
N2 N 0.25465(14) 0.53234(17) 0.64981(11) 0.0155(4) Uani 1 1 d . . .
B1 B 0.23719(19) 0.5710(2) 0.55288(15) 0.0158(5) Uani 1 1 d . . .
C1 C 0.2825(2) 0.6799(2) 0.39238(15) 0.0296(6) Uani 1 1 d . . .
H1A H 0.2114 0.6595 0.3962 0.044 Uiso 1 1 calc R . .
H1B H 0.2943 0.6264 0.3466 0.044 Uiso 1 1 calc R . .
H1C H 0.2839 0.7699 0.3765 0.044 Uiso 1 1 calc R . .
C2 C 0.37101(19) 0.6551(2) 0.48062(14) 0.0212(5) Uani 1 1 d . . .
C3 C 0.48379(18) 0.6714(2) 0.50497(15) 0.0228(5) Uani 1 1 d . . .
H3A H 0.5197 0.6983 0.4661 0.027 Uiso 1 1 calc R . .
C4 C 0.53484(17) 0.6425(2) 0.59428(15) 0.0198(5) Uani 1 1 d . . .
C5 C 0.65592(17) 0.6487(2) 0.64463(16) 0.0258(5) Uani 1 1 d . . .
H5A H 0.6926 0.6768 0.6044 0.039 Uiso 1 1 calc R . .
H5B H 0.6829 0.5641 0.6683 0.039 Uiso 1 1 calc R . .
H5C H 0.6714 0.7093 0.6942 0.039 Uiso 1 1 calc R . .
C6 C 0.44928(16) 0.6076(2) 0.62553(14) 0.0166(4) Uani 1 1 d . . .
C7 C 0.45041(16) 0.5720(2) 0.70983(14) 0.0163(5) Uani 1 1 d . . .
C8 C 0.35430(16) 0.5387(2) 0.72251(13) 0.0151(4) Uani 1 1 d . . .
C9 C 0.40879(18) 0.4996(2) 0.89608(14) 0.0221(5) Uani 1 1 d . . .
H9A H 0.3684 0.4742 0.9342 0.033 Uiso 1 1 calc R . .
H9B H 0.4419 0.5836 0.9148 0.033 Uiso 1 1 calc R . .
H9C H 0.4664 0.4371 0.9016 0.033 Uiso 1 1 calc R . .
C10 C 0.33226(17) 0.5058(2) 0.80120(13) 0.0165(4) Uani 1 1 d . . .
C11 C 0.22154(17) 0.4810(2) 0.77280(14) 0.0183(5) Uani 1 1 d . . .
H11A H 0.1829 0.4568 0.8102 0.022 Uiso 1 1 calc R . .
C12 C 0.17545(16) 0.4971(2) 0.68052(14) 0.0167(5) Uani 1 1 d . . .
C13 C 0.05962(17) 0.4769(2) 0.62117(15) 0.0211(5) Uani 1 1 d . . .
H13A H 0.0514 0.4956 0.5593 0.032 Uiso 1 1 calc R . .
H13B H 0.0122 0.5338 0.6394 0.032 Uiso 1 1 calc R . .
H13C H 0.0389 0.3882 0.6257 0.032 Uiso 1 1 calc R . .
C14 C 0.55575(16) 0.5712(2) 0.78823(14) 0.0165(5) Uani 1 1 d . . .
C15 C 0.60432(16) 0.6834(2) 0.82901(14) 0.0182(5) Uani 1 1 d . . .
H15A H 0.5709 0.7624 0.8053 0.022 Uiso 1 1 calc R . .
C16 C 0.70079(17) 0.6839(2) 0.90377(14) 0.0184(5) Uani 1 1 d . . .
H16A H 0.7320 0.7618 0.9315 0.022 Uiso 1 1 calc R . .
C17 C 0.75071(16) 0.5680(2) 0.93718(14) 0.0170(5) Uani 1 1 d . . .
C18 C 0.70304(17) 0.4537(2) 0.89713(15) 0.0202(5) Uani 1 1 d . . .
H18A H 0.7366 0.3747 0.9204 0.024 Uiso 1 1 calc R . .
C19 C 0.60694(16) 0.4562(2) 0.82350(15) 0.0204(5) Uani 1 1 d . . .
H19A H 0.5751 0.3782 0.7963 0.024 Uiso 1 1 calc R . .
C20 C 0.90432(16) 0.6690(2) 1.04911(14) 0.0201(5) Uani 1 1 d . . .
H20A H 0.8654 0.7113 1.0841 0.024 Uiso 1 1 calc R A .
H20B H 0.9087 0.7294 1.0032 0.024 Uiso 1 1 calc R . .
C21 C 1.01732(17) 0.6298(2) 1.10948(14) 0.0210(5) Uani 1 1 d . A .
H21A H 1.0541 0.5851 1.0738 0.025 Uiso 1 1 calc R . .
H21B H 1.0606 0.7069 1.1356 0.025 Uiso 1 1 calc R . .
C22 C 1.0402(3) 0.4176(3) 1.16344(19) 0.0273(8) Uani 0.821(5) 1 d PDU A 1
H22A H 1.1134 0.4136 1.1588 0.033 Uiso 0.821(5) 1 calc PR A 1
H22B H 0.9855 0.3856 1.1068 0.033 Uiso 0.821(5) 1 calc PR A 1
C23 C 1.0382(3) 0.3371(3) 1.2407(2) 0.0298(8) Uani 0.821(5) 1 d PDU A 1
H23A H 1.0550 0.2484 1.2314 0.045 Uiso 0.821(5) 1 calc PR A 1
H23B H 0.9655 0.3416 1.2447 0.045 Uiso 0.821(5) 1 calc PR A 1
H23C H 1.0929 0.3690 1.2964 0.045 Uiso 0.821(5) 1 calc PR A 1
C22' C 1.0943(9) 0.4631(11) 1.2287(9) 0.031(3) Uani 0.179(5) 1 d PDU A 2
H22C H 1.1057 0.4647 1.2931 0.037 Uiso 0.179(5) 1 calc PR A 2
H22D H 1.1648 0.4758 1.2204 0.037 Uiso 0.179(5) 1 calc PR A 2
C23' C 1.0351(14) 0.3437(15) 1.1825(13) 0.041(4) Uani 0.179(5) 1 d PDU A 2
H23D H 1.0798 0.2686 1.2084 0.062 Uiso 0.179(5) 1 calc PR A 2
H23E H 1.0225 0.3483 1.1186 0.062 Uiso 0.179(5) 1 calc PR A 2
H23F H 0.9647 0.3370 1.1906 0.062 Uiso 0.179(5) 1 calc PR A 2


_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 1.396(3) . ?
F2 B1 1.393(3) . ?
O1 C17 1.363(2) . ?
O1 C20 1.436(3) . ?
O2 C22' 1.388(8) . ?
O2 C21 1.420(3) . ?
O2 C22 1.460(3) . ?
N1 C2 1.353(3) . ?
N1 C6 1.408(3) . ?
N1 B1 1.544(3) . ?
N2 C12 1.352(3) . ?
N2 C8 1.404(3) . ?
N2 B1 1.543(3) . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.396(3) . ?
C3 C4 1.379(3) . ?
C3 H3A 0.9500 . ?
C4 C6 1.432(3) . ?
C4 C5 1.500(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.399(3) . ?
C7 C8 1.392(3) . ?
C7 C14 1.495(3) . ?
C8 C10 1.436(3) . ?
C9 C10 1.492(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.380(3) . ?
C11 C12 1.393(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.487(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.385(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.394(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.393(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.396(3) . ?
C18 C19 1.381(3) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.505(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.509(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C22' C23' 1.518(10) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 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
C17 O1 C20 118.49(16) . . ?
C22' O2 C21 127.6(6) . . ?
C22' O2 C22 47.0(6) . . ?
C21 O2 C22 110.68(18) . . ?
C2 N1 C6 107.96(17) . . ?
C2 N1 B1 126.15(17) . . ?
C6 N1 B1 125.54(17) . . ?
C12 N2 C8 108.44(17) . . ?
C12 N2 B1 125.89(18) . . ?
C8 N2 B1 125.45(17) . . ?
F2 B1 F1 109.07(17) . . ?
F2 B1 N2 110.55(18) . . ?
F1 B1 N2 110.06(18) . . ?
F2 B1 N1 110.18(18) . . ?
F1 B1 N1 110.25(18) . . ?
N2 B1 N1 106.73(17) . . ?
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 C3 109.08(19) . . ?
N1 C2 C1 122.2(2) . . ?
C3 C2 C1 128.6(2) . . ?
C4 C3 C2 109.3(2) . . ?
C4 C3 H3A 125.4 . . ?
C2 C3 H3A 125.4 . . ?
C3 C4 C6 105.87(19) . . ?
C3 C4 C5 124.9(2) . . ?
C6 C4 C5 129.3(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 120.03(18) . . ?
C7 C6 C4 132.2(2) . . ?
N1 C6 C4 107.77(18) . . ?
C8 C7 C6 121.02(19) . . ?
C8 C7 C14 119.01(18) . . ?
C6 C7 C14 119.97(18) . . ?
C7 C8 N2 120.65(18) . . ?
C7 C8 C10 132.07(19) . . ?
N2 C8 C10 107.28(17) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 106.09(18) . . ?
C11 C10 C9 124.59(19) . . ?
C8 C10 C9 129.31(19) . . ?
C10 C11 C12 109.2(2) . . ?
C10 C11 H11A 125.4 . . ?
C12 C11 H11A 125.4 . . ?
N2 C12 C11 109.03(18) . . ?
N2 C12 C13 123.10(18) . . ?
C11 C12 C13 127.8(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.11(19) . . ?
C15 C14 C7 121.30(19) . . ?
C19 C14 C7 120.57(19) . . ?
C14 C15 C16 121.9(2) . . ?
C14 C15 H15A 119.0 . . ?
C16 C15 H15A 119.0 . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
O1 C17 C16 124.64(19) . . ?
O1 C17 C18 115.21(19) . . ?
C16 C17 C18 120.14(19) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19A 119.4 . . ?
C14 C19 H19A 119.4 . . ?
O1 C20 C21 107.41(18) . . ?
O1 C20 H20A 110.2 . . ?
C21 C20 H20A 110.2 . . ?
O1 C20 H20B 110.2 . . ?
C21 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
O2 C21 C20 111.88(17) . . ?
O2 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
O2 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
O2 C22 C23 108.0(2) . . ?
O2 C22 H22A 110.1 . . ?
C23 C22 H22A 110.1 . . ?
O2 C22 H22B 110.1 . . ?
C23 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C22' C23' 96.2(10) . . ?
O2 C22' H22C 112.5 . . ?
C23' C22' H22C 112.5 . . ?
O2 C22' H22D 112.5 . . ?
C23' C22' H22D 112.5 . . ?
H22C C22' H22D 110.0 . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 B1 F2 54.9(3) . . . . ?
C8 N2 B1 F2 -119.2(2) . . . . ?
C12 N2 B1 F1 -65.7(3) . . . . ?
C8 N2 B1 F1 120.3(2) . . . . ?
C12 N2 B1 N1 174.67(19) . . . . ?
C8 N2 B1 N1 0.6(3) . . . . ?
C2 N1 B1 F2 -61.2(3) . . . . ?
C6 N1 B1 F2 126.3(2) . . . . ?
C2 N1 B1 F1 59.2(3) . . . . ?
C6 N1 B1 F1 -113.2(2) . . . . ?
C2 N1 B1 N2 178.7(2) . . . . ?
C6 N1 B1 N2 6.3(3) . . . . ?
C6 N1 C2 C3 1.1(2) . . . . ?
B1 N1 C2 C3 -172.5(2) . . . . ?
C6 N1 C2 C1 -177.0(2) . . . . ?
B1 N1 C2 C1 9.5(3) . . . . ?
N1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 177.3(2) . . . . ?
C2 C3 C4 C6 -0.2(3) . . . . ?
C2 C3 C4 C5 180.0(2) . . . . ?
C2 N1 C6 C7 178.1(2) . . . . ?
B1 N1 C6 C7 -8.3(3) . . . . ?
C2 N1 C6 C4 -1.2(2) . . . . ?
B1 N1 C6 C4 172.43(19) . . . . ?
C3 C4 C6 C7 -178.3(2) . . . . ?
C5 C4 C6 C7 1.5(4) . . . . ?
C3 C4 C6 N1 0.8(2) . . . . ?
C5 C4 C6 N1 -179.3(2) . . . . ?
N1 C6 C7 C8 2.7(3) . . . . ?
C4 C6 C7 C8 -178.2(2) . . . . ?
N1 C6 C7 C14 -176.48(19) . . . . ?
C4 C6 C7 C14 2.6(4) . . . . ?
C6 C7 C8 N2 3.9(3) . . . . ?
C14 C7 C8 N2 -176.87(18) . . . . ?
C6 C7 C8 C10 -176.2(2) . . . . ?
C14 C7 C8 C10 3.0(4) . . . . ?
C12 N2 C8 C7 179.5(2) . . . . ?
B1 N2 C8 C7 -5.6(3) . . . . ?
C12 N2 C8 C10 -0.4(2) . . . . ?
B1 N2 C8 C10 174.55(19) . . . . ?
C7 C8 C10 C11 -179.7(2) . . . . ?
N2 C8 C10 C11 0.2(2) . . . . ?
C7 C8 C10 C9 1.1(4) . . . . ?
N2 C8 C10 C9 -179.0(2) . . . . ?
C8 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
C8 N2 C12 C11 0.4(2) . . . . ?
B1 N2 C12 C11 -174.46(19) . . . . ?
C8 N2 C12 C13 -178.0(2) . . . . ?
B1 N2 C12 C13 7.1(3) . . . . ?
C10 C11 C12 N2 -0.3(3) . . . . ?
C10 C11 C12 C13 178.0(2) . . . . ?
C8 C7 C14 C15 -103.8(3) . . . . ?
C6 C7 C14 C15 75.4(3) . . . . ?
C8 C7 C14 C19 75.0(3) . . . . ?
C6 C7 C14 C19 -105.8(2) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?
C7 C14 C15 C16 178.05(18) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C20 O1 C17 C16 -2.2(3) . . . . ?
C20 O1 C17 C18 176.59(19) . . . . ?
C15 C16 C17 O1 177.37(19) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
O1 C17 C18 C19 -177.95(19) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
C7 C14 C19 C18 -178.55(19) . . . . ?
C17 O1 C20 C21 -167.61(17) . . . . ?
C22' O2 C21 C20 157.5(7) . . . . ?
C22 O2 C21 C20 106.6(2) . . . . ?
O1 C20 C21 O2 -63.2(2) . . . . ?
C22' O2 C22 C23 56.2(8) . . . . ?
C21 O2 C22 C23 178.9(2) . . . . ?
C21 O2 C22' C23' -104.5(10) . . . . ?
C22 O2 C22' C23' -20.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 989186'
#######################################################################
#
#                 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         ?
_chemical_formula_sum            'C25 H31 B F2 N2 O3'
_chemical_formula_weight         456.33

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9161(16)
_cell_length_b                   12.051(2)
_cell_length_c                   12.960(3)
_cell_angle_alpha                73.25(3)
_cell_angle_beta                 77.85(3)
_cell_angle_gamma                85.14(3)
_cell_volume                     1157.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3597
_cell_measurement_theta_min      1.6731
_cell_measurement_theta_max      27.8704

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9867
_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  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12020
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.89
_reflns_number_total             5428
_reflns_number_gt                2957
_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  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5428
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.002
_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 0.33503(11) 0.53872(7) 0.66282(7) 0.0203(2) Uani 1 1 d . . .
F2 F 0.48319(11) 0.68722(7) 0.53493(7) 0.0188(2) Uani 1 1 d . . .
O1 O 0.76348(14) 0.81308(9) 1.17270(9) 0.0194(3) Uani 1 1 d . . .
O2 O 0.99566(14) 0.77304(9) 1.34213(9) 0.0207(3) Uani 1 1 d . . .
O3 O 1.23203(13) 0.95126(9) 1.32132(9) 0.0185(3) Uani 1 1 d . . .
N1 N 0.60232(16) 0.59110(10) 0.69495(10) 0.0139(3) Uani 1 1 d . . .
N2 N 0.33999(16) 0.71771(11) 0.70821(10) 0.0140(3) Uani 1 1 d . . .
B1 B 0.4387(2) 0.63255(15) 0.64695(15) 0.0141(4) Uani 1 1 d . . .
C1 C 0.7320(2) 0.47539(14) 0.56496(14) 0.0245(4) Uani 1 1 d . . .
H1A H 0.6173 0.4472 0.5697 0.037 Uiso 1 1 calc R . .
H1B H 0.8176 0.4116 0.5655 0.037 Uiso 1 1 calc R . .
H1C H 0.7624 0.5375 0.4967 0.037 Uiso 1 1 calc R . .
C2 C 0.7300(2) 0.52058(13) 0.66025(13) 0.0174(4) Uani 1 1 d . . .
C3 C 0.8521(2) 0.50074(14) 0.72710(13) 0.0201(4) Uani 1 1 d . . .
H3 H 0.9536 0.4533 0.7202 0.024 Uiso 1 1 calc R . .
C4 C 0.8028(2) 0.56063(13) 0.80459(13) 0.0180(4) Uani 1 1 d . . .
C5 C 0.9023(2) 0.55928(16) 0.89157(14) 0.0269(4) Uani 1 1 d . . .
H5A H 1.0125 0.5170 0.8789 0.040 Uiso 1 1 calc R . .
H5B H 0.8350 0.5209 0.9640 0.040 Uiso 1 1 calc R . .
H5C H 0.9245 0.6390 0.8886 0.040 Uiso 1 1 calc R . .
C6 C 0.6428(2) 0.61873(13) 0.78517(12) 0.0146(3) Uani 1 1 d . . .
C7 C 0.5342(2) 0.69318(13) 0.83584(12) 0.0149(3) Uani 1 1 d . . .
C8 C 0.3850(2) 0.74242(13) 0.79840(12) 0.0146(3) Uani 1 1 d . . .
C9 C 0.2465(2) 0.87564(16) 0.92502(14) 0.0282(4) Uani 1 1 d . . .
H9A H 0.1409 0.9240 0.9307 0.042 Uiso 1 1 calc R . .
H9B H 0.3473 0.9233 0.9119 0.042 Uiso 1 1 calc R . .
H9C H 0.2431 0.8135 0.9936 0.042 Uiso 1 1 calc R . .
C10 C 0.2591(2) 0.82361(14) 0.83133(13) 0.0187(4) Uani 1 1 d . . .
C11 C 0.1452(2) 0.84585(14) 0.76032(13) 0.0200(4) Uani 1 1 d . . .
H11 H 0.0479 0.8977 0.7618 0.024 Uiso 1 1 calc R . .
C12 C 0.1959(2) 0.77971(13) 0.68573(13) 0.0179(4) Uani 1 1 d . . .
C13 C 0.1086(2) 0.77279(15) 0.59685(13) 0.0227(4) Uani 1 1 d . . .
H13A H 0.1957 0.7643 0.5334 0.034 Uiso 1 1 calc R . .
H13B H 0.0390 0.8437 0.5751 0.034 Uiso 1 1 calc R . .
H13C H 0.0334 0.7058 0.6235 0.034 Uiso 1 1 calc R . .
C14 C 0.5854(2) 0.72383(13) 0.92847(13) 0.0155(3) Uani 1 1 d . . .
C15 C 0.5441(2) 0.65624(14) 1.03562(13) 0.0205(4) Uani 1 1 d . . .
H15 H 0.4757 0.5901 1.0519 0.025 Uiso 1 1 calc R . .
C16 C 0.5999(2) 0.68225(14) 1.12028(13) 0.0198(4) Uani 1 1 d . . .
H16 H 0.5700 0.6344 1.1935 0.024 Uiso 1 1 calc R . .
C17 C 0.6996(2) 0.77866(13) 1.09708(13) 0.0155(3) Uani 1 1 d . . .
C18 C 0.7398(2) 0.84893(13) 0.98974(13) 0.0187(4) Uani 1 1 d . . .
H18 H 0.8059 0.9161 0.9739 0.022 Uiso 1 1 calc R . .
C19 C 0.6843(2) 0.82191(13) 0.90593(13) 0.0180(4) Uani 1 1 d . . .
H19 H 0.7134 0.8701 0.8328 0.022 Uiso 1 1 calc R . .
C20 C 0.7300(2) 0.74269(13) 1.28467(12) 0.0158(3) Uani 1 1 d . . .
H20A H 0.7773 0.6631 1.2890 0.019 Uiso 1 1 calc R . .
H20B H 0.6039 0.7383 1.3136 0.019 Uiso 1 1 calc R . .
C21 C 0.81438(19) 0.79635(14) 1.35133(13) 0.0179(4) Uani 1 1 d . . .
H21A H 0.7942 0.8813 1.3282 0.022 Uiso 1 1 calc R . .
H21B H 0.7578 0.7678 1.4295 0.022 Uiso 1 1 calc R . .
C22 C 1.1000(2) 0.83522(14) 1.24164(13) 0.0213(4) Uani 1 1 d . . .
H22A H 1.0384 0.9073 1.2082 0.026 Uiso 1 1 calc R . .
H22B H 1.1245 0.7874 1.1894 0.026 Uiso 1 1 calc R . .
C23 C 1.2661(2) 0.86412(14) 1.26552(14) 0.0208(4) Uani 1 1 d . . .
H23A H 1.3162 0.7940 1.3116 0.025 Uiso 1 1 calc R . .
H23B H 1.3503 0.8920 1.1960 0.025 Uiso 1 1 calc R . .
C24 C 1.3813(2) 0.97398(14) 1.35678(14) 0.0221(4) Uani 1 1 d . . .
H24A H 1.4757 1.0012 1.2927 0.027 Uiso 1 1 calc R . .
H24B H 1.4218 0.9023 1.4062 0.027 Uiso 1 1 calc R . .
C25 C 1.3326(2) 1.06553(14) 1.41646(14) 0.0254(4) Uani 1 1 d . . .
H25A H 1.2871 1.1347 1.3681 0.038 Uiso 1 1 calc R . .
H25B H 1.4350 1.0856 1.4380 0.038 Uiso 1 1 calc R . .
H25C H 1.2441 1.0360 1.4822 0.038 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 1.3952(19) . ?
F2 B1 1.392(2) . ?
O1 C17 1.3665(17) . ?
O1 C20 1.4360(18) . ?
O2 C22 1.424(2) . ?
O2 C21 1.4253(18) . ?
O3 C23 1.4164(17) . ?
O3 C24 1.4275(17) . ?
N1 C2 1.3527(19) . ?
N1 C6 1.4074(18) . ?
N1 B1 1.538(2) . ?
N2 C12 1.3471(19) . ?
N2 C8 1.4056(18) . ?
N2 B1 1.538(2) . ?
C1 C2 1.483(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.391(2) . ?
C3 C4 1.374(2) . ?
C3 H3 0.9500 . ?
C4 C6 1.428(2) . ?
C4 C5 1.501(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.395(2) . ?
C7 C8 1.393(2) . ?
C7 C14 1.493(2) . ?
C8 C10 1.424(2) . ?
C9 C10 1.502(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.378(2) . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.487(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.379(2) . ?
C14 C19 1.399(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(2) . ?
C18 C19 1.381(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.500(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.502(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.503(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C17 O1 C20 118.10(12) . . ?
C22 O2 C21 115.27(12) . . ?
C23 O3 C24 111.78(11) . . ?
C2 N1 C6 108.06(13) . . ?
C2 N1 B1 126.60(12) . . ?
C6 N1 B1 125.33(12) . . ?
C12 N2 C8 108.68(12) . . ?
C12 N2 B1 126.08(13) . . ?
C8 N2 B1 125.24(12) . . ?
F2 B1 F1 109.04(13) . . ?
F2 B1 N1 110.26(13) . . ?
F1 B1 N1 110.28(13) . . ?
F2 B1 N2 110.37(13) . . ?
F1 B1 N2 109.64(13) . . ?
N1 B1 N2 107.25(12) . . ?
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 C3 108.98(13) . . ?
N1 C2 C1 123.07(14) . . ?
C3 C2 C1 127.94(14) . . ?
C4 C3 C2 109.28(14) . . ?
C4 C3 H3 125.4 . . ?
C2 C3 H3 125.4 . . ?
C3 C4 C6 106.28(13) . . ?
C3 C4 C5 124.39(14) . . ?
C6 C4 C5 129.32(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 120.24(13) . . ?
C7 C6 C4 132.35(14) . . ?
N1 C6 C4 107.39(13) . . ?
C8 C7 C6 121.24(14) . . ?
C8 C7 C14 120.19(14) . . ?
C6 C7 C14 118.51(14) . . ?
C7 C8 N2 120.44(13) . . ?
C7 C8 C10 132.27(14) . . ?
N2 C8 C10 107.23(13) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 106.46(13) . . ?
C11 C10 C9 125.23(14) . . ?
C8 C10 C9 128.30(15) . . ?
C10 C11 C12 108.97(14) . . ?
C10 C11 H11 125.5 . . ?
C12 C11 H11 125.5 . . ?
N2 C12 C11 108.66(13) . . ?
N2 C12 C13 123.44(14) . . ?
C11 C12 C13 127.87(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.51(14) . . ?
C15 C14 C7 122.22(14) . . ?
C19 C14 C7 119.22(14) . . ?
C14 C15 C16 121.76(15) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 119.37(16) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
O1 C17 C16 125.06(15) . . ?
O1 C17 C18 115.35(14) . . ?
C16 C17 C18 119.59(14) . . ?
C19 C18 C17 120.57(15) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 120.18(15) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O1 C20 C21 108.42(13) . . ?
O1 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
O1 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
O2 C21 C20 114.58(13) . . ?
O2 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
O2 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
O2 C22 C23 108.56(13) . . ?
O2 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
O2 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
O3 C23 C22 109.01(12) . . ?
O3 C23 H23A 109.9 . . ?
C22 C23 H23A 109.9 . . ?
O3 C23 H23B 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
O3 C24 C25 108.10(13) . . ?
O3 C24 H24A 110.1 . . ?
C25 C24 H24A 110.1 . . ?
O3 C24 H24B 110.1 . . ?
C25 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 B1 F2 -55.82(19) . . . . ?
C6 N1 B1 F2 125.62(15) . . . . ?
C2 N1 B1 F1 64.65(19) . . . . ?
C6 N1 B1 F1 -113.90(16) . . . . ?
C2 N1 B1 N2 -176.02(14) . . . . ?
C6 N1 B1 N2 5.4(2) . . . . ?
C12 N2 B1 F2 55.0(2) . . . . ?
C8 N2 B1 F2 -125.89(15) . . . . ?
C12 N2 B1 F1 -65.16(19) . . . . ?
C8 N2 B1 F1 113.98(15) . . . . ?
C12 N2 B1 N1 175.10(14) . . . . ?
C8 N2 B1 N1 -5.8(2) . . . . ?
C6 N1 C2 C3 0.66(17) . . . . ?
B1 N1 C2 C3 -178.10(15) . . . . ?
C6 N1 C2 C1 -178.98(15) . . . . ?
B1 N1 C2 C1 2.3(2) . . . . ?
N1 C2 C3 C4 -0.80(19) . . . . ?
C1 C2 C3 C4 178.82(16) . . . . ?
C2 C3 C4 C6 0.59(19) . . . . ?
C2 C3 C4 C5 179.52(16) . . . . ?
C2 N1 C6 C7 178.41(14) . . . . ?
B1 N1 C6 C7 -2.8(2) . . . . ?
C2 N1 C6 C4 -0.29(17) . . . . ?
B1 N1 C6 C4 178.49(14) . . . . ?
C3 C4 C6 C7 -178.67(17) . . . . ?
C5 C4 C6 C7 2.5(3) . . . . ?
C3 C4 C6 N1 -0.19(17) . . . . ?
C5 C4 C6 N1 -179.05(16) . . . . ?
N1 C6 C7 C8 -0.5(2) . . . . ?
C4 C6 C7 C8 177.82(17) . . . . ?
N1 C6 C7 C14 -177.66(14) . . . . ?
C4 C6 C7 C14 0.7(3) . . . . ?
C6 C7 C8 N2 0.2(2) . . . . ?
C14 C7 C8 N2 177.29(14) . . . . ?
C6 C7 C8 C10 -176.61(16) . . . . ?
C14 C7 C8 C10 0.5(3) . . . . ?
C12 N2 C8 C7 -177.25(14) . . . . ?
B1 N2 C8 C7 3.5(2) . . . . ?
C12 N2 C8 C10 0.26(17) . . . . ?
B1 N2 C8 C10 -179.01(14) . . . . ?
C7 C8 C10 C11 176.47(17) . . . . ?
N2 C8 C10 C11 -0.62(18) . . . . ?
C7 C8 C10 C9 -4.3(3) . . . . ?
N2 C8 C10 C9 178.59(16) . . . . ?
C8 C10 C11 C12 0.75(19) . . . . ?
C9 C10 C11 C12 -178.49(16) . . . . ?
C8 N2 C12 C11 0.20(17) . . . . ?
B1 N2 C12 C11 179.46(14) . . . . ?
C8 N2 C12 C13 -178.35(15) . . . . ?
B1 N2 C12 C13 0.9(2) . . . . ?
C10 C11 C12 N2 -0.61(19) . . . . ?
C10 C11 C12 C13 177.86(16) . . . . ?
C8 C7 C14 C15 96.20(19) . . . . ?
C6 C7 C14 C15 -86.6(2) . . . . ?
C8 C7 C14 C19 -86.29(19) . . . . ?
C6 C7 C14 C19 90.91(18) . . . . ?
C19 C14 C15 C16 -0.9(2) . . . . ?
C7 C14 C15 C16 176.64(15) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C20 O1 C17 C16 2.0(2) . . . . ?
C20 O1 C17 C18 -178.57(13) . . . . ?
C15 C16 C17 O1 -179.48(14) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
O1 C17 C18 C19 179.08(13) . . . . ?
C16 C17 C18 C19 -1.4(2) . . . . ?
C17 C18 C19 C14 0.6(2) . . . . ?
C15 C14 C19 C18 0.5(2) . . . . ?
C7 C14 C19 C18 -177.06(14) . . . . ?
C17 O1 C20 C21 179.15(12) . . . . ?
C22 O2 C21 C20 74.49(17) . . . . ?
O1 C20 C21 O2 -79.42(16) . . . . ?
C21 O2 C22 C23 144.58(13) . . . . ?
C24 O3 C23 C22 173.79(13) . . . . ?
O2 C22 C23 O3 -71.68(16) . . . . ?
C23 O3 C24 C25 -179.06(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 989187'
