# 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_erk7178

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 B N'
_chemical_formula_weight         233.11

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   8.7384(3)
_cell_length_b                   16.7458(6)
_cell_length_c                   18.9805(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.163(2)
_cell_angle_gamma                90.00
_cell_volume                     2761.39(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4739
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8849
_exptl_absorpt_correction_T_max  0.9670
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24587
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         67.35
_reflns_number_total             4809
_reflns_number_gt                3697
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_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)+(0.0531P)²+0.4778P] 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         4809
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
N1A N 0.43067(13) 0.55317(7) 0.36564(6) 0.0473(3) Uani 1 1 d . . .
B1A B 0.2865(2) 0.53235(11) 0.38814(8) 0.0492(4) Uani 1 1 d . . .
C1A C 0.24914(17) 0.44310(10) 0.40236(8) 0.0546(4) Uani 1 1 d . . .
H1A H 0.2985 0.4040 0.3774 0.066 Uiso 1 1 calc R . .
C2A C 0.1534(2) 0.41851(11) 0.44686(10) 0.0670(5) Uani 1 1 d . . .
H2A1 H 0.1019 0.4559 0.4728 0.080 Uiso 1 1 calc R . .
H2A2 H 0.1365 0.3636 0.4527 0.080 Uiso 1 1 calc R . .
C3A C 0.16800(18) 0.60037(10) 0.39710(8) 0.0551(4) Uani 1 1 d . . .
H3A H 0.2080 0.6511 0.4097 0.066 Uiso 1 1 calc R . .
C4A C 0.0165(2) 0.59303(12) 0.38862(9) 0.0663(5) Uani 1 1 d . . .
H4A1 H -0.0286 0.5434 0.3761 0.080 Uiso 1 1 calc R . .
H4A2 H -0.0461 0.6375 0.3952 0.080 Uiso 1 1 calc R . .
C11A C 0.55433(16) 0.49769(8) 0.35901(8) 0.0464(3) Uani 1 1 d . . .
C12A C 0.61903(18) 0.49281(9) 0.29563(8) 0.0546(4) Uani 1 1 d . . .
H12A H 0.5811 0.5251 0.2572 0.066 Uiso 1 1 calc R . .
C13A C 0.73900(19) 0.44067(10) 0.28861(9) 0.0603(4) Uani 1 1 d . . .
H13A H 0.7820 0.4375 0.2454 0.072 Uiso 1 1 calc R . .
C14A C 0.79587(19) 0.39327(10) 0.34468(9) 0.0586(4) Uani 1 1 d . . .
H14A H 0.8777 0.3579 0.3399 0.070 Uiso 1 1 calc R . .
C15A C 0.73225(19) 0.39796(10) 0.40774(9) 0.0591(4) Uani 1 1 d . . .
H15A H 0.7706 0.3656 0.4461 0.071 Uiso 1 1 calc R . .
C16A C 0.61195(18) 0.45016(9) 0.41500(8) 0.0541(4) Uani 1 1 d . . .
H16A H 0.5694 0.4532 0.4583 0.065 Uiso 1 1 calc R . .
C21A C 0.46445(16) 0.63393(9) 0.34581(8) 0.0475(3) Uani 1 1 d . . .
C22A C 0.57728(19) 0.67704(10) 0.38579(9) 0.0585(4) Uani 1 1 d . . .
H22A H 0.6337 0.6533 0.4253 0.070 Uiso 1 1 calc R . .
C23A C 0.6073(2) 0.75502(11) 0.36774(10) 0.0690(5) Uani 1 1 d . . .
H23A H 0.6842 0.7841 0.3950 0.083 Uiso 1 1 calc R . .
C24A C 0.5252(2) 0.79031(10) 0.31004(10) 0.0669(5) Uani 1 1 d . . .
H24A H 0.5443 0.8437 0.2984 0.080 Uiso 1 1 calc R . .
C25A C 0.4149(2) 0.74686(11) 0.26954(10) 0.0668(5) Uani 1 1 d . . .
H25A H 0.3597 0.7704 0.2296 0.080 Uiso 1 1 calc R . .
C26A C 0.38466(19) 0.66866(10) 0.28710(9) 0.0587(4) Uani 1 1 d . . .
H26A H 0.3096 0.6392 0.2590 0.070 Uiso 1 1 calc R . .
N1B N 0.08172(14) 0.54821(7) 0.12080(6) 0.0491(3) Uani 1 1 d . . .
B1B B 0.2253(2) 0.56867(11) 0.09717(9) 0.0515(4) Uani 1 1 d . . .
C1B C 0.34360(19) 0.50070(10) 0.08852(9) 0.0594(4) Uani 1 1 d . . .
H1B H 0.3040 0.4502 0.0749 0.071 Uiso 1 1 calc R . .
C2B C 0.4948(2) 0.50805(12) 0.09869(10) 0.0693(5) Uani 1 1 d . . .
H2B1 H 0.5393 0.5576 0.1124 0.083 Uiso 1 1 calc R . .
H2B2 H 0.5580 0.4638 0.0923 0.083 Uiso 1 1 calc R . .
C3B C 0.26032(18) 0.65764(10) 0.08069(9) 0.0594(4) Uani 1 1 d . . .
H3B H 0.2070 0.6973 0.1033 0.071 Uiso 1 1 calc R . .
C4B C 0.3599(2) 0.68118(12) 0.03715(10) 0.0708(5) Uani 1 1 d . . .
H4B1 H 0.4152 0.6432 0.0137 0.085 Uiso 1 1 calc R . .
H4B2 H 0.3753 0.7360 0.0297 0.085 Uiso 1 1 calc R . .
C11B C 0.04750(16) 0.46840(9) 0.14315(7) 0.0470(3) Uani 1 1 d . . .
C12B C -0.06957(18) 0.42492(10) 0.10594(8) 0.0546(4) Uani 1 1 d . . .
H12B H -0.1273 0.4476 0.0663 0.066 Uiso 1 1 calc R . .
C13B C -0.1017(2) 0.34834(10) 0.12701(9) 0.0617(4) Uani 1 1 d . . .
H13B H -0.1811 0.3191 0.1015 0.074 Uiso 1 1 calc R . .
C14B C -0.01799(19) 0.31452(10) 0.18510(9) 0.0599(4) Uani 1 1 d . . .
H14B H -0.0392 0.2621 0.1990 0.072 Uiso 1 1 calc R . .
C15B C 0.0968(2) 0.35807(10) 0.22262(9) 0.0605(4) Uani 1 1 d . . .
H15B H 0.1532 0.3355 0.2627 0.073 Uiso 1 1 calc R . .
C16B C 0.13007(18) 0.43482(9) 0.20194(8) 0.0548(4) Uani 1 1 d . . .
H16B H 0.2088 0.4641 0.2279 0.066 Uiso 1 1 calc R . .
C21B C -0.04223(17) 0.60395(9) 0.12633(8) 0.0483(3) Uani 1 1 d . . .
C22B C -0.09969(18) 0.61462(9) 0.19104(8) 0.0547(4) Uani 1 1 d . . .
H22B H -0.0569 0.5860 0.2310 0.066 Uiso 1 1 calc R . .
C23B C -0.21955(19) 0.66709(10) 0.19706(9) 0.0605(4) Uani 1 1 d . . .
H23B H -0.2577 0.6741 0.2411 0.073 Uiso 1 1 calc R . .
C24B C -0.28324(19) 0.70915(10) 0.13898(10) 0.0617(4) Uani 1 1 d . . .
H24B H -0.3648 0.7449 0.1431 0.074 Uiso 1 1 calc R . .
C25B C -0.22654(19) 0.69848(10) 0.07462(10) 0.0637(4) Uani 1 1 d . . .
H25B H -0.2697 0.7273 0.0348 0.076 Uiso 1 1 calc R . .
C26B C -0.10669(18) 0.64582(10) 0.06793(8) 0.0570(4) Uani 1 1 d . . .
H26B H -0.0694 0.6386 0.0237 0.068 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
N1A B1A 1.416(2) . ?
N1A C11A 1.4408(18) . ?
N1A C21A 1.4427(18) . ?
B1A C1A 1.559(2) . ?
B1A C3A 1.561(2) . ?
C1A C2A 1.317(2) . ?
C1A H1A 0.9400 . ?
C2A H2A1 0.9400 . ?
C2A H2A2 0.9400 . ?
C3A C4A 1.322(2) . ?
C3A H3A 0.9400 . ?
C4A H4A1 0.9400 . ?
C4A H4A2 0.9400 . ?
C11A C16A 1.379(2) . ?
C11A C12A 1.385(2) . ?
C12A C13A 1.382(2) . ?
C12A H12A 0.9400 . ?
C13A C14A 1.377(2) . ?
C13A H13A 0.9400 . ?
C14A C15A 1.375(2) . ?
C14A H14A 0.9400 . ?
C15A C16A 1.385(2) . ?
C15A H15A 0.9400 . ?
C16A H16A 0.9400 . ?
C21A C26A 1.378(2) . ?
C21A C22A 1.382(2) . ?
C22A C23A 1.382(2) . ?
C22A H22A 0.9400 . ?
C23A C24A 1.376(3) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.375(3) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.384(2) . ?
C25A H25A 0.9400 . ?
C26A H26A 0.9400 . ?
N1B B1B 1.419(2) . ?
N1B C21B 1.4422(18) . ?
N1B C11B 1.4433(19) . ?
B1B C1B 1.558(2) . ?
B1B C3B 1.559(2) . ?
C1B C2B 1.321(2) . ?
C1B H1B 0.9400 . ?
C2B H2B1 0.9400 . ?
C2B H2B2 0.9400 . ?
C3B C4B 1.323(2) . ?
C3B H3B 0.9400 . ?
C4B H4B1 0.9400 . ?
C4B H4B2 0.9400 . ?
C11B C16B 1.382(2) . ?
C11B C12B 1.386(2) . ?
C12B C13B 1.381(2) . ?
C12B H12B 0.9400 . ?
C13B C14B 1.378(2) . ?
C13B H13B 0.9400 . ?
C14B C15B 1.375(2) . ?
C14B H14B 0.9400 . ?
C15B C16B 1.384(2) . ?
C15B H15B 0.9400 . ?
C16B H16B 0.9400 . ?
C21B C26B 1.380(2) . ?
C21B C22B 1.387(2) . ?
C22B C23B 1.381(2) . ?
C22B H22B 0.9400 . ?
C23B C24B 1.375(2) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.378(2) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.385(2) . ?
C25B H25B 0.9400 . ?
C26B H26B 0.9400 . ?

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
B1A N1A C11A 124.56(13) . . ?
B1A N1A C21A 121.53(12) . . ?
C11A N1A C21A 113.90(11) . . ?
N1A B1A C1A 119.85(14) . . ?
N1A B1A C3A 118.37(14) . . ?
C1A B1A C3A 121.78(14) . . ?
C2A C1A B1A 124.74(16) . . ?
C2A C1A H1A 117.6 . . ?
B1A C1A H1A 117.6 . . ?
C1A C2A H2A1 120.0 . . ?
C1A C2A H2A2 120.0 . . ?
H2A1 C2A H2A2 120.0 . . ?
C4A C3A B1A 125.89(16) . . ?
C4A C3A H3A 117.1 . . ?
B1A C3A H3A 117.1 . . ?
C3A C4A H4A1 120.0 . . ?
C3A C4A H4A2 120.0 . . ?
H4A1 C4A H4A2 120.0 . . ?
C16A C11A C12A 119.07(14) . . ?
C16A C11A N1A 121.34(13) . . ?
C12A C11A N1A 119.59(13) . . ?
C13A C12A C11A 120.37(15) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C14A C13A C12A 120.28(15) . . ?
C14A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
C15A C14A C13A 119.59(15) . . ?
C15A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
C14A C15A C16A 120.31(16) . . ?
C14A C15A H15A 119.8 . . ?
C16A C15A H15A 119.8 . . ?
C11A C16A C15A 120.38(15) . . ?
C11A C16A H16A 119.8 . . ?
C15A C16A H16A 119.8 . . ?
C26A C21A C22A 119.53(15) . . ?
C26A C21A N1A 120.43(13) . . ?
C22A C21A N1A 120.04(13) . . ?
C21A C22A C23A 120.05(16) . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C24A C23A C22A 120.42(17) . . ?
C24A C23A H23A 119.8 . . ?
C22A C23A H23A 119.8 . . ?
C25A C24A C23A 119.47(16) . . ?
C25A C24A H24A 120.3 . . ?
C23A C24A H24A 120.3 . . ?
C24A C25A C26A 120.46(16) . . ?
C24A C25A H25A 119.8 . . ?
C26A C25A H25A 119.8 . . ?
C21A C26A C25A 120.06(16) . . ?
C21A C26A H26A 120.0 . . ?
C25A C26A H26A 120.0 . . ?
B1B N1B C21B 124.27(13) . . ?
B1B N1B C11B 122.32(12) . . ?
C21B N1B C11B 113.39(11) . . ?
N1B B1B C1B 118.44(15) . . ?
N1B B1B C3B 119.58(15) . . ?
C1B B1B C3B 121.98(14) . . ?
C2B C1B B1B 125.55(16) . . ?
C2B C1B H1B 117.2 . . ?
B1B C1B H1B 117.2 . . ?
C1B C2B H2B1 120.0 . . ?
C1B C2B H2B2 120.0 . . ?
H2B1 C2B H2B2 120.0 . . ?
C4B C3B B1B 124.52(17) . . ?
C4B C3B H3B 117.7 . . ?
B1B C3B H3B 117.7 . . ?
C3B C4B H4B1 120.0 . . ?
C3B C4B H4B2 120.0 . . ?
H4B1 C4B H4B2 120.0 . . ?
C16B C11B C12B 119.39(14) . . ?
C16B C11B N1B 120.50(13) . . ?
C12B C11B N1B 120.12(13) . . ?
C13B C12B C11B 120.14(15) . . ?
C13B C12B H12B 119.9 . . ?
C11B C12B H12B 119.9 . . ?
C14B C13B C12B 120.44(16) . . ?
C14B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
C15B C14B C13B 119.43(16) . . ?
C15B C14B H14B 120.3 . . ?
C13B C14B H14B 120.3 . . ?
C14B C15B C16B 120.62(16) . . ?
C14B C15B H15B 119.7 . . ?
C16B C15B H15B 119.7 . . ?
C11B C16B C15B 119.97(15) . . ?
C11B C16B H16B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C26B C21B C22B 119.38(14) . . ?
C26B C21B N1B 121.02(13) . . ?
C22B C21B N1B 119.59(13) . . ?
C23B C22B C21B 120.32(15) . . ?
C23B C22B H22B 119.8 . . ?
C21B C22B H22B 119.8 . . ?
C24B C23B C22B 120.33(16) . . ?
C24B C23B H23B 119.8 . . ?
C22B C23B H23B 119.8 . . ?
C23B C24B C25B 119.43(16) . . ?
C23B C24B H24B 120.3 . . ?
C25B C24B H24B 120.3 . . ?
C24B C25B C26B 120.73(16) . . ?
C24B C25B H25B 119.6 . . ?
C26B C25B H25B 119.6 . . ?
C21B C26B C25B 119.81(15) . . ?
C21B C26B H26B 120.1 . . ?
C25B C26B H26B 120.1 . . ?

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
C11A N1A B1A C1A -4.5(2) . . . . ?
C21A N1A B1A C1A 174.34(13) . . . . ?
C11A N1A B1A C3A 176.25(13) . . . . ?
C21A N1A B1A C3A -4.9(2) . . . . ?
N1A B1A C1A C2A 152.72(16) . . . . ?
C3A B1A C1A C2A -28.0(2) . . . . ?
N1A B1A C3A C4A 150.26(16) . . . . ?
C1A B1A C3A C4A -29.0(2) . . . . ?
B1A N1A C11A C16A -54.7(2) . . . . ?
C21A N1A C11A C16A 126.40(15) . . . . ?
B1A N1A C11A C12A 126.52(16) . . . . ?
C21A N1A C11A C12A -52.39(17) . . . . ?
C16A C11A C12A C13A 0.4(2) . . . . ?
N1A C11A C12A C13A 179.18(14) . . . . ?
C11A C12A C13A C14A -0.3(2) . . . . ?
C12A C13A C14A C15A 0.2(2) . . . . ?
C13A C14A C15A C16A -0.2(2) . . . . ?
C12A C11A C16A C15A -0.4(2) . . . . ?
N1A C11A C16A C15A -179.16(14) . . . . ?
C14A C15A C16A C11A 0.3(2) . . . . ?
B1A N1A C21A C26A -65.37(19) . . . . ?
C11A N1A C21A C26A 113.58(15) . . . . ?
B1A N1A C21A C22A 114.55(16) . . . . ?
C11A N1A C21A C22A -66.50(17) . . . . ?
C26A C21A C22A C23A 1.4(2) . . . . ?
N1A C21A C22A C23A -178.54(14) . . . . ?
C21A C22A C23A C24A 0.1(3) . . . . ?
C22A C23A C24A C25A -1.3(3) . . . . ?
C23A C24A C25A C26A 1.0(3) . . . . ?
C22A C21A C26A C25A -1.6(2) . . . . ?
N1A C21A C26A C25A 178.27(14) . . . . ?
C24A C25A C26A C21A 0.4(3) . . . . ?
C21B N1B B1B C1B -175.42(13) . . . . ?
C11B N1B B1B C1B 5.8(2) . . . . ?
C21B N1B B1B C3B 4.6(2) . . . . ?
C11B N1B B1B C3B -174.18(13) . . . . ?
N1B B1B C1B C2B -147.63(17) . . . . ?
C3B B1B C1B C2B 32.4(2) . . . . ?
N1B B1B C3B C4B -155.66(16) . . . . ?
C1B B1B C3B C4B 24.3(2) . . . . ?
B1B N1B C11B C16B 63.89(19) . . . . ?
C21B N1B C11B C16B -115.00(15) . . . . ?
B1B N1B C11B C12B -116.57(16) . . . . ?
C21B N1B C11B C12B 64.55(17) . . . . ?
C16B C11B C12B C13B -0.9(2) . . . . ?
N1B C11B C12B C13B 179.55(13) . . . . ?
C11B C12B C13B C14B 0.1(2) . . . . ?
C12B C13B C14B C15B 0.8(2) . . . . ?
C13B C14B C15B C16B -0.9(2) . . . . ?
C12B C11B C16B C15B 0.8(2) . . . . ?
N1B C11B C16B C15B -179.62(14) . . . . ?
C14B C15B C16B C11B 0.1(2) . . . . ?
B1B N1B C21B C26B 58.6(2) . . . . ?
C11B N1B C21B C26B -122.49(15) . . . . ?
B1B N1B C21B C22B -122.58(16) . . . . ?
C11B N1B C21B C22B 56.28(18) . . . . ?
C26B C21B C22B C23B -0.5(2) . . . . ?
N1B C21B C22B C23B -179.26(14) . . . . ?
C21B C22B C23B C24B 0.1(2) . . . . ?
C22B C23B C24B C25B 0.0(2) . . . . ?
C23B C24B C25B C26B 0.2(3) . . . . ?
C22B C21B C26B C25B 0.7(2) . . . . ?
N1B C21B C26B C25B 179.44(14) . . . . ?
C24B C25B C26B C21B -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        67.35
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 982551'
#######################################################################
#
#                 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_erk7175

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H18 B3 F20 N'
_chemical_formula_weight         924.98

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           monoclinic
_symmetry_space_group_name_H-M   P21/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                   19.6734(4)
_cell_length_b                   6.2270(2)
_cell_length_c                   31.1173(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.093(2)
_cell_angle_gamma                90.00
_cell_volume                     3802.34(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7842
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22625
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6453
_reflns_number_gt                3882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_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)+(0.0000P)²+7.1508P] 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         6453
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2728(2) 0.2856(10) 0.55782(15) 0.0508(14) Uani 1 1 d . . .
B2 B 0.2183(3) 0.2177(10) 0.67500(16) 0.0541(14) Uani 1 1 d . . .
B3 B 0.1588(3) 0.3847(10) 0.45458(16) 0.0581(15) Uani 1 1 d . . .
N1 N 0.34334(16) 0.3093(6) 0.55428(9) 0.0457(9) Uani 1 1 d . . .
C1 C 0.2405(2) 0.3362(9) 0.60216(12) 0.0577(13) Uani 1 1 d . . .
H1A H 0.2654 0.4549 0.6168 0.069 Uiso 1 1 calc R . .
H1B H 0.1929 0.3804 0.5965 0.069 Uiso 1 1 calc R . .
C2 C 0.2440(2) 0.1344(8) 0.63181(13) 0.0559(12) Uani 1 1 d . . .
H2A H 0.2907 0.0802 0.6360 0.067 Uiso 1 1 calc R . .
H2B H 0.2144 0.0198 0.6196 0.067 Uiso 1 1 calc R . .
C3 C 0.2238(2) 0.2225(9) 0.51785(13) 0.0582(13) Uani 1 1 d . . .
H3A H 0.1873 0.1285 0.5265 0.070 Uiso 1 1 calc R . .
H3B H 0.2489 0.1479 0.4962 0.070 Uiso 1 1 calc R . .
C4 C 0.1939(2) 0.4402(9) 0.49941(13) 0.0627(14) Uani 1 1 d . . .
H4A H 0.1608 0.4993 0.5183 0.075 Uiso 1 1 calc R . .
H4B H 0.2303 0.5457 0.4967 0.075 Uiso 1 1 calc R . .
C11 C 0.3903(2) 0.3898(9) 0.58859(12) 0.0504(12) Uani 1 1 d . . .
C12 C 0.4410(2) 0.2554(9) 0.60613(13) 0.0603(13) Uani 1 1 d . . .
H12 H 0.4451 0.1154 0.5953 0.072 Uiso 1 1 calc R . .
C13 C 0.4853(3) 0.3244(13) 0.63903(16) 0.0798(18) Uani 1 1 d . . .
H13 H 0.5198 0.2322 0.6505 0.096 Uiso 1 1 calc R . .
C14 C 0.4797(3) 0.5255(14) 0.65528(17) 0.085(2) Uani 1 1 d . . .
H14 H 0.5099 0.5709 0.6782 0.102 Uiso 1 1 calc R . .
C15 C 0.4301(3) 0.6634(11) 0.63840(16) 0.0791(18) Uani 1 1 d . . .
H15 H 0.4267 0.8026 0.6498 0.095 Uiso 1 1 calc R . .
C16 C 0.3845(3) 0.5965(9) 0.60416(14) 0.0641(14) Uani 1 1 d . . .
H16 H 0.3508 0.6901 0.5921 0.077 Uiso 1 1 calc R . .
C21 C 0.3762(2) 0.2584(8) 0.51528(13) 0.0483(11) Uani 1 1 d . . .
C22 C 0.4075(2) 0.4152(9) 0.49354(14) 0.0608(13) Uani 1 1 d . . .
H22 H 0.4097 0.5551 0.5049 0.073 Uiso 1 1 calc R . .
C23 C 0.4361(2) 0.3727(10) 0.45496(14) 0.0654(14) Uani 1 1 d . . .
H23 H 0.4562 0.4841 0.4399 0.079 Uiso 1 1 calc R . .
C24 C 0.4349(2) 0.1705(11) 0.43905(16) 0.0714(16) Uani 1 1 d . . .
H24 H 0.4556 0.1410 0.4134 0.086 Uiso 1 1 calc R . .
C25 C 0.4037(3) 0.0073(10) 0.46022(17) 0.0830(17) Uani 1 1 d . . .
H25 H 0.4016 -0.1323 0.4487 0.100 Uiso 1 1 calc R . .
C26 C 0.3752(3) 0.0530(9) 0.49909(15) 0.0702(15) Uani 1 1 d . . .
H26 H 0.3552 -0.0580 0.5143 0.084 Uiso 1 1 calc R . .
C31 C 0.2690(2) 0.3586(8) 0.70452(12) 0.0509(12) Uani 1 1 d . . .
F32 F 0.35925(14) 0.1074(6) 0.70325(9) 0.0792(9) Uani 1 1 d . . .
C32 C 0.3360(2) 0.3015(10) 0.71552(14) 0.0604(13) Uani 1 1 d . . .
F33 F 0.44439(14) 0.3589(7) 0.75116(9) 0.1032(13) Uani 1 1 d . . .
C33 C 0.3812(3) 0.4284(12) 0.74034(15) 0.0708(17) Uani 1 1 d . . .
F34 F 0.40272(17) 0.7489(7) 0.77775(10) 0.1160(14) Uani 1 1 d . . .
C34 C 0.3593(3) 0.6223(12) 0.75385(15) 0.0759(17) Uani 1 1 d . . .
F35 F 0.27330(18) 0.8806(6) 0.75774(10) 0.0985(11) Uani 1 1 d . . .
C35 C 0.2941(3) 0.6894(10) 0.74373(16) 0.0693(14) Uani 1 1 d . . .
F36 F 0.18717(14) 0.6326(5) 0.71016(9) 0.0801(9) Uani 1 1 d . . .
C36 C 0.2508(2) 0.5579(9) 0.71938(14) 0.0575(13) Uani 1 1 d . . .
C41 C 0.1429(2) 0.1902(8) 0.68822(14) 0.0554(12) Uani 1 1 d . . .
F42 F 0.17392(15) 0.2135(6) 0.76279(8) 0.0881(10) Uani 1 1 d . . .
C42 C 0.1256(3) 0.1913(9) 0.73106(15) 0.0652(14) Uani 1 1 d . . .
F43 F 0.04643(18) 0.1679(7) 0.78417(10) 0.1140(13) Uani 1 1 d . . .
C43 C 0.0601(3) 0.1661(10) 0.74254(18) 0.0752(16) Uani 1 1 d . . .
F44 F -0.05720(16) 0.1354(6) 0.72260(13) 0.1154(13) Uani 1 1 d . . .
C44 C 0.0087(3) 0.1488(10) 0.7122(2) 0.0796(17) Uani 1 1 d . . .
F45 F -0.02955(15) 0.1275(6) 0.63835(11) 0.1058(12) Uani 1 1 d . . .
C45 C 0.0208(2) 0.1465(10) 0.66951(19) 0.0736(15) Uani 1 1 d . . .
F46 F 0.09631(13) 0.1650(6) 0.61582(9) 0.0845(10) Uani 1 1 d . . .
C46 C 0.0876(2) 0.1647(9) 0.65870(15) 0.0629(13) Uani 1 1 d . . .
C51 C 0.2062(2) 0.3531(10) 0.41643(14) 0.0608(13) Uani 1 1 d . . .
F52 F 0.26208(15) 0.6893(6) 0.42905(9) 0.0861(9) Uani 1 1 d . . .
C52 C 0.2557(3) 0.5008(10) 0.40762(15) 0.0687(15) Uani 1 1 d . . .
F53 F 0.34832(18) 0.6212(8) 0.36870(10) 0.1140(13) Uani 1 1 d . . .
C53 C 0.3009(3) 0.4715(12) 0.37589(17) 0.0782(17) Uani 1 1 d . . .
F54 F 0.34248(18) 0.2534(8) 0.32290(10) 0.1304(16) Uani 1 1 d . . .
C54 C 0.2977(3) 0.2874(14) 0.35290(16) 0.090(2) Uani 1 1 d . . .
F55 F 0.2461(2) -0.0481(7) 0.33694(10) 0.1203(14) Uani 1 1 d . . .
C55 C 0.2498(3) 0.1359(12) 0.35979(17) 0.0847(19) Uani 1 1 d . . .
F56 F 0.15903(17) 0.0175(6) 0.39787(10) 0.0924(10) Uani 1 1 d . . .
C56 C 0.2055(3) 0.1710(11) 0.39144(16) 0.0720(15) Uani 1 1 d . . .
C61 C 0.0800(2) 0.3400(8) 0.44678(13) 0.0564(12) Uani 1 1 d . . .
F62 F 0.06500(13) 0.2583(5) 0.52027(8) 0.0727(8) Uani 1 1 d . . .
C62 C 0.0386(2) 0.2844(9) 0.47935(15) 0.0615(13) Uani 1 1 d . . .
F63 F -0.06712(14) 0.1900(5) 0.50564(10) 0.0826(9) Uani 1 1 d . . .
C63 C -0.0299(3) 0.2463(9) 0.47262(16) 0.0648(14) Uani 1 1 d . . .
F64 F -0.12826(14) 0.2324(5) 0.42503(10) 0.0897(10) Uani 1 1 d . . .
C64 C -0.0611(2) 0.2665(9) 0.43232(19) 0.0695(15) Uani 1 1 d . . .
F65 F -0.05421(15) 0.3503(6) 0.35908(9) 0.0929(10) Uani 1 1 d . . .
C65 C -0.0237(3) 0.3262(10) 0.39905(16) 0.0698(15) Uani 1 1 d . . .
F66 F 0.07876(14) 0.4197(6) 0.37238(8) 0.0832(10) Uani 1 1 d . . .
C66 C 0.0446(3) 0.3603(9) 0.40658(14) 0.0659(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.407(6) . ?
B1 C3 1.568(6) . ?
B1 C1 1.591(6) . ?
B2 C2 1.558(6) . ?
B2 C31 1.574(7) . ?
B2 C41 1.577(6) . ?
B3 C4 1.551(6) . ?
B3 C51 1.573(7) . ?
B3 C61 1.577(7) . ?
N1 C21 1.450(5) . ?
N1 C11 1.451(5) . ?
C1 C2 1.557(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.571(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C11 C16 1.383(7) . ?
C11 C12 1.384(6) . ?
C12 C13 1.365(7) . ?
C12 H12 0.9400 . ?
C13 C14 1.358(9) . ?
C13 H13 0.9400 . ?
C14 C15 1.375(8) . ?
C14 H14 0.9400 . ?
C15 C16 1.406(6) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C22 1.360(6) . ?
C21 C26 1.374(7) . ?
C22 C23 1.387(6) . ?
C22 H22 0.9400 . ?
C23 C24 1.353(7) . ?
C23 H23 0.9400 . ?
C24 C25 1.379(7) . ?
C24 H24 0.9400 . ?
C25 C26 1.398(6) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C36 1.380(7) . ?
C31 C32 1.384(6) . ?
F32 C32 1.357(6) . ?
C32 C33 1.383(7) . ?
F33 C33 1.337(6) . ?
C33 C34 1.359(8) . ?
F34 C34 1.346(6) . ?
C34 C35 1.366(7) . ?
F35 C35 1.342(6) . ?
C35 C36 1.370(7) . ?
F36 C36 1.347(5) . ?
C41 C46 1.382(6) . ?
C41 C42 1.399(6) . ?
F42 C42 1.327(5) . ?
C42 C43 1.370(7) . ?
F43 C43 1.342(5) . ?
C43 C44 1.339(7) . ?
F44 C44 1.362(5) . ?
C44 C45 1.365(7) . ?
F45 C45 1.341(6) . ?
C45 C46 1.384(6) . ?
F46 C46 1.358(5) . ?
C51 C56 1.375(7) . ?
C51 C52 1.381(7) . ?
F52 C52 1.352(6) . ?
C52 C53 1.388(7) . ?
F53 C53 1.348(7) . ?
C53 C54 1.351(9) . ?
F54 C54 1.345(6) . ?
C54 C55 1.361(9) . ?
F55 C55 1.347(7) . ?
C55 C56 1.378(7) . ?
F56 C56 1.348(6) . ?
C61 C62 1.388(6) . ?
C61 C66 1.394(6) . ?
F62 C62 1.350(5) . ?
C62 C63 1.370(6) . ?
F63 C63 1.350(5) . ?
C63 C64 1.362(7) . ?
F64 C64 1.342(5) . ?
C64 C65 1.364(7) . ?
F65 C65 1.350(5) . ?
C65 C66 1.363(6) . ?
F66 C66 1.350(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 B1 C3 121.2(4) . . ?
N1 B1 C1 120.3(4) . . ?
C3 B1 C1 118.5(4) . . ?
C2 B2 C31 117.3(4) . . ?
C2 B2 C41 123.9(4) . . ?
C31 B2 C41 118.5(4) . . ?
C4 B3 C51 117.2(4) . . ?
C4 B3 C61 123.2(4) . . ?
C51 B3 C61 119.4(4) . . ?
B1 N1 C21 122.9(3) . . ?
B1 N1 C11 124.0(3) . . ?
C21 N1 C11 113.1(3) . . ?
C2 C1 B1 110.5(4) . . ?
C2 C1 H1A 109.5 . . ?
B1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
B1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 B2 103.9(4) . . ?
C1 C2 H2A 111.0 . . ?
B2 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
B2 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
B1 C3 C4 105.5(4) . . ?
B1 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
B1 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
B3 C4 C3 105.5(4) . . ?
B3 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
B3 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C16 C11 C12 120.0(4) . . ?
C16 C11 N1 121.0(4) . . ?
C12 C11 N1 119.0(5) . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.4(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 120.1(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 118.5(5) . . ?
C11 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C22 C21 C26 118.8(4) . . ?
C22 C21 N1 120.3(4) . . ?
C26 C21 N1 121.0(4) . . ?
C21 C22 C23 121.3(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 119.8(5) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.5(5) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 118.9(5) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C21 C26 C25 120.7(5) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C36 C31 C32 114.4(5) . . ?
C36 C31 B2 121.9(4) . . ?
C32 C31 B2 123.6(5) . . ?
F32 C32 C33 116.7(5) . . ?
F32 C32 C31 119.5(5) . . ?
C33 C32 C31 123.7(6) . . ?
F33 C33 C34 121.3(6) . . ?
F33 C33 C32 120.3(6) . . ?
C34 C33 C32 118.4(5) . . ?
F34 C34 C33 119.3(6) . . ?
F34 C34 C35 119.8(7) . . ?
C33 C34 C35 120.9(5) . . ?
F35 C35 C34 120.0(6) . . ?
F35 C35 C36 121.3(5) . . ?
C34 C35 C36 118.8(6) . . ?
F36 C36 C35 116.3(5) . . ?
F36 C36 C31 119.9(4) . . ?
C35 C36 C31 123.9(5) . . ?
C46 C41 C42 113.6(4) . . ?
C46 C41 B2 123.4(4) . . ?
C42 C41 B2 123.0(4) . . ?
F42 C42 C43 117.0(4) . . ?
F42 C42 C41 120.0(4) . . ?
C43 C42 C41 123.0(5) . . ?
C44 C43 F43 119.2(5) . . ?
C44 C43 C42 120.2(5) . . ?
F43 C43 C42 120.5(5) . . ?
C43 C44 F44 121.4(5) . . ?
C43 C44 C45 120.8(5) . . ?
F44 C44 C45 117.8(6) . . ?
F45 C45 C44 122.2(5) . . ?
F45 C45 C46 119.8(5) . . ?
C44 C45 C46 118.0(5) . . ?
F46 C46 C41 120.3(4) . . ?
F46 C46 C45 115.3(4) . . ?
C41 C46 C45 124.3(5) . . ?
C56 C51 C52 114.5(5) . . ?
C56 C51 B3 123.2(5) . . ?
C52 C51 B3 122.1(5) . . ?
F52 C52 C51 121.5(5) . . ?
F52 C52 C53 115.0(6) . . ?
C51 C52 C53 123.4(6) . . ?
F53 C53 C54 120.4(6) . . ?
F53 C53 C52 120.9(6) . . ?
C54 C53 C52 118.7(6) . . ?
F54 C54 C53 119.5(7) . . ?
F54 C54 C55 119.7(7) . . ?
C53 C54 C55 120.8(5) . . ?
F55 C55 C54 121.2(6) . . ?
F55 C55 C56 119.9(7) . . ?
C54 C55 C56 118.8(6) . . ?
F56 C56 C51 118.7(5) . . ?
F56 C56 C55 117.6(6) . . ?
C51 C56 C55 123.7(6) . . ?
C62 C61 C66 113.4(4) . . ?
C62 C61 B3 123.6(4) . . ?
C66 C61 B3 123.0(4) . . ?
F62 C62 C63 115.5(4) . . ?
F62 C62 C61 120.9(4) . . ?
C63 C62 C61 123.6(4) . . ?
F63 C63 C64 119.4(5) . . ?
F63 C63 C62 120.7(4) . . ?
C64 C63 C62 119.9(5) . . ?
F64 C64 C63 121.0(5) . . ?
F64 C64 C65 119.6(5) . . ?
C63 C64 C65 119.5(5) . . ?
F65 C65 C66 120.6(5) . . ?
F65 C65 C64 120.1(5) . . ?
C66 C65 C64 119.4(4) . . ?
F66 C66 C65 116.6(4) . . ?
F66 C66 C61 119.1(4) . . ?
C65 C66 C61 124.3(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 B1 N1 C21 -6.0(7) . . . . ?
C1 B1 N1 C21 177.7(4) . . . . ?
C3 B1 N1 C11 173.0(4) . . . . ?
C1 B1 N1 C11 -3.4(7) . . . . ?
N1 B1 C1 C2 -86.7(6) . . . . ?
C3 B1 C1 C2 96.9(5) . . . . ?
B1 C1 C2 B2 173.9(4) . . . . ?
C31 B2 C2 C1 -75.6(5) . . . . ?
C41 B2 C2 C1 97.6(5) . . . . ?
N1 B1 C3 C4 -96.2(5) . . . . ?
C1 B1 C3 C4 80.2(5) . . . . ?
C51 B3 C4 C3 -77.8(6) . . . . ?
C61 B3 C4 C3 96.9(6) . . . . ?
B1 C3 C4 B3 167.6(4) . . . . ?
B1 N1 C11 C16 -62.8(6) . . . . ?
C21 N1 C11 C16 116.2(5) . . . . ?
B1 N1 C11 C12 116.3(5) . . . . ?
C21 N1 C11 C12 -64.7(5) . . . . ?
C16 C11 C12 C13 0.5(7) . . . . ?
N1 C11 C12 C13 -178.7(4) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C12 C13 C14 C15 -1.0(9) . . . . ?
C13 C14 C15 C16 0.2(8) . . . . ?
C12 C11 C16 C15 -1.2(7) . . . . ?
N1 C11 C16 C15 177.9(4) . . . . ?
C14 C15 C16 C11 0.9(7) . . . . ?
B1 N1 C21 C22 116.5(5) . . . . ?
C11 N1 C21 C22 -62.5(5) . . . . ?
B1 N1 C21 C26 -62.1(6) . . . . ?
C11 N1 C21 C26 118.9(5) . . . . ?
C26 C21 C22 C23 2.1(7) . . . . ?
N1 C21 C22 C23 -176.5(4) . . . . ?
C21 C22 C23 C24 -2.0(8) . . . . ?
C22 C23 C24 C25 2.0(8) . . . . ?
C23 C24 C25 C26 -2.1(8) . . . . ?
C22 C21 C26 C25 -2.2(8) . . . . ?
N1 C21 C26 C25 176.4(4) . . . . ?
C24 C25 C26 C21 2.2(8) . . . . ?
C2 B2 C31 C36 127.0(5) . . . . ?
C41 B2 C31 C36 -46.6(6) . . . . ?
C2 B2 C31 C32 -48.8(6) . . . . ?
C41 B2 C31 C32 137.6(5) . . . . ?
C36 C31 C32 F32 178.9(4) . . . . ?
B2 C31 C32 F32 -5.1(6) . . . . ?
C36 C31 C32 C33 1.8(6) . . . . ?
B2 C31 C32 C33 177.9(4) . . . . ?
F32 C32 C33 F33 0.1(6) . . . . ?
C31 C32 C33 F33 177.2(4) . . . . ?
F32 C32 C33 C34 -178.9(4) . . . . ?
C31 C32 C33 C34 -1.7(7) . . . . ?
F33 C33 C34 F34 1.6(7) . . . . ?
C32 C33 C34 F34 -179.5(4) . . . . ?
F33 C33 C34 C35 -178.0(4) . . . . ?
C32 C33 C34 C35 0.9(8) . . . . ?
F34 C34 C35 F35 -0.2(7) . . . . ?
C33 C34 C35 F35 179.4(5) . . . . ?
F34 C34 C35 C36 180.0(4) . . . . ?
C33 C34 C35 C36 -0.4(8) . . . . ?
F35 C35 C36 F36 0.6(7) . . . . ?
C34 C35 C36 F36 -179.6(4) . . . . ?
F35 C35 C36 C31 -179.2(4) . . . . ?
C34 C35 C36 C31 0.6(7) . . . . ?
C32 C31 C36 F36 179.0(4) . . . . ?
B2 C31 C36 F36 2.9(6) . . . . ?
C32 C31 C36 C35 -1.3(7) . . . . ?
B2 C31 C36 C35 -177.4(4) . . . . ?
C2 B2 C41 C46 -24.6(8) . . . . ?
C31 B2 C41 C46 148.5(5) . . . . ?
C2 B2 C41 C42 155.9(5) . . . . ?
C31 B2 C41 C42 -31.0(7) . . . . ?
C46 C41 C42 F42 179.7(5) . . . . ?
B2 C41 C42 F42 -0.8(8) . . . . ?
C46 C41 C42 C43 0.9(8) . . . . ?
B2 C41 C42 C43 -179.6(5) . . . . ?
F42 C42 C43 C44 178.1(5) . . . . ?
C41 C42 C43 C44 -3.1(10) . . . . ?
F42 C42 C43 F43 1.1(9) . . . . ?
C41 C42 C43 F43 179.9(5) . . . . ?
F43 C43 C44 F44 0.8(9) . . . . ?
C42 C43 C44 F44 -176.4(5) . . . . ?
F43 C43 C44 C45 180.0(6) . . . . ?
C42 C43 C44 C45 2.9(10) . . . . ?
C43 C44 C45 F45 179.4(6) . . . . ?
F44 C44 C45 F45 -1.3(9) . . . . ?
C43 C44 C45 C46 -0.6(9) . . . . ?
F44 C44 C45 C46 178.6(5) . . . . ?
C42 C41 C46 F46 178.6(5) . . . . ?
B2 C41 C46 F46 -0.9(8) . . . . ?
C42 C41 C46 C45 1.4(8) . . . . ?
B2 C41 C46 C45 -178.1(5) . . . . ?
F45 C45 C46 F46 1.0(8) . . . . ?
C44 C45 C46 F46 -178.9(5) . . . . ?
F45 C45 C46 C41 178.3(5) . . . . ?
C44 C45 C46 C41 -1.6(9) . . . . ?
C4 B3 C51 C56 125.1(5) . . . . ?
C61 B3 C51 C56 -49.7(7) . . . . ?
C4 B3 C51 C52 -49.7(7) . . . . ?
C61 B3 C51 C52 135.4(5) . . . . ?
C56 C51 C52 F52 179.0(4) . . . . ?
B3 C51 C52 F52 -5.7(7) . . . . ?
C56 C51 C52 C53 0.7(7) . . . . ?
B3 C51 C52 C53 176.0(5) . . . . ?
F52 C52 C53 F53 1.7(7) . . . . ?
C51 C52 C53 F53 -179.9(5) . . . . ?
F52 C52 C53 C54 -179.8(5) . . . . ?
C51 C52 C53 C54 -1.5(8) . . . . ?
F53 C53 C54 F54 0.5(8) . . . . ?
C52 C53 C54 F54 -178.0(5) . . . . ?
F53 C53 C54 C55 -179.6(5) . . . . ?
C52 C53 C54 C55 1.9(9) . . . . ?
F54 C54 C55 F55 -0.3(9) . . . . ?
C53 C54 C55 F55 179.8(5) . . . . ?
F54 C54 C55 C56 178.3(5) . . . . ?
C53 C54 C55 C56 -1.6(9) . . . . ?
C52 C51 C56 F56 179.8(4) . . . . ?
B3 C51 C56 F56 4.6(7) . . . . ?
C52 C51 C56 C55 -0.4(8) . . . . ?
B3 C51 C56 C55 -175.6(5) . . . . ?
F55 C55 C56 F56 -0.8(8) . . . . ?
C54 C55 C56 F56 -179.4(5) . . . . ?
F55 C55 C56 C51 179.5(5) . . . . ?
C54 C55 C56 C51 0.9(9) . . . . ?
C4 B3 C61 C62 -19.5(8) . . . . ?
C51 B3 C61 C62 155.1(5) . . . . ?
C4 B3 C61 C66 158.1(5) . . . . ?
C51 B3 C61 C66 -27.4(8) . . . . ?
C66 C61 C62 F62 -180.0(5) . . . . ?
B3 C61 C62 F62 -2.2(8) . . . . ?
C66 C61 C62 C63 2.0(8) . . . . ?
B3 C61 C62 C63 179.7(5) . . . . ?
F62 C62 C63 F63 1.0(7) . . . . ?
C61 C62 C63 F63 179.1(5) . . . . ?
F62 C62 C63 C64 -179.4(5) . . . . ?
C61 C62 C63 C64 -1.3(9) . . . . ?
F63 C63 C64 F64 0.4(8) . . . . ?
C62 C63 C64 F64 -179.2(5) . . . . ?
F63 C63 C64 C65 179.1(5) . . . . ?
C62 C63 C64 C65 -0.5(8) . . . . ?
F64 C64 C65 F65 -0.1(8) . . . . ?
C63 C64 C65 F65 -178.9(5) . . . . ?
F64 C64 C65 C66 -179.9(5) . . . . ?
C63 C64 C65 C66 1.4(9) . . . . ?
F65 C65 C66 F66 0.4(8) . . . . ?
C64 C65 C66 F66 -179.8(5) . . . . ?
F65 C65 C66 C61 179.7(5) . . . . ?
C64 C65 C66 C61 -0.5(9) . . . . ?
C62 C61 C66 F66 178.2(5) . . . . ?
B3 C61 C66 F66 0.4(8) . . . . ?
C62 C61 C66 C65 -1.1(8) . . . . ?
B3 C61 C66 C65 -178.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 982552'
#######################################################################
#
#                 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_erk7147

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H35 B2 F10 N2'
_chemical_formula_weight         707.28

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.0640(4)
_cell_length_b                   12.5390(5)
_cell_length_c                   14.4570(6)
_cell_angle_alpha                95.573(2)
_cell_angle_beta                 101.176(2)
_cell_angle_gamma                104.130(2)
_cell_volume                     1715.50(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4963
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             730
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7720
_exptl_absorpt_correction_T_max  0.9057
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18481
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         67.20
_reflns_number_total             5829
_reflns_number_gt                5364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_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)+(0.0492P)²+0.4911P] 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         5829
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
N1 N 0.81153(12) 0.58217(9) 0.34120(8) 0.0383(3) Uani 1 1 d . . .
C1 C 0.73631(14) 0.35907(11) 0.33843(9) 0.0355(3) Uani 1 1 d . . .
H1 H 0.8327 0.3550 0.3365 0.043 Uiso 1 1 calc R . .
B1 B 0.74544(16) 0.48691(13) 0.37554(11) 0.0368(3) Uani 1 1 d . . .
C2 C 0.69444(16) 0.30039(12) 0.42393(10) 0.0426(3) Uani 1 1 d . . .
H2A H 0.6364 0.2240 0.4004 0.051 Uiso 1 1 calc R . .
H2B H 0.7791 0.2976 0.4694 0.051 Uiso 1 1 calc R . .
B2 B 0.63116(16) 0.28991(12) 0.23745(11) 0.0348(3) Uani 1 1 d . . .
C3 C 0.61221(17) 0.36719(13) 0.47277(10) 0.0465(3) Uani 1 1 d . . .
H3A H 0.5130 0.3460 0.4393 0.056 Uiso 1 1 calc R . .
H3B H 0.6182 0.3546 0.5391 0.056 Uiso 1 1 calc R . .
C4 C 0.68110(17) 0.48867(13) 0.46837(11) 0.0467(3) Uani 1 1 d . . .
H4A H 0.7554 0.5217 0.5257 0.056 Uiso 1 1 calc R . .
H4B H 0.6114 0.5317 0.4630 0.056 Uiso 1 1 calc R . .
C5 C 0.81590(17) 0.69823(12) 0.37796(11) 0.0463(3) Uani 1 1 d . . .
H5 H 0.8732 0.7470 0.3421 0.056 Uiso 1 1 calc R . .
C6 C 0.8885(2) 0.73460(15) 0.48319(13) 0.0643(5) Uani 1 1 d . . .
H6A H 0.8266 0.7003 0.5221 0.096 Uiso 1 1 calc R . .
H6B H 0.9102 0.8149 0.4983 0.096 Uiso 1 1 calc R . .
H6C H 0.9748 0.7117 0.4961 0.096 Uiso 1 1 calc R . .
C7 C 0.6703(2) 0.71784(15) 0.35594(15) 0.0617(4) Uani 1 1 d . . .
H7A H 0.6314 0.7005 0.2877 0.093 Uiso 1 1 calc R . .
H7B H 0.6774 0.7951 0.3776 0.093 Uiso 1 1 calc R . .
H7C H 0.6094 0.6704 0.3885 0.093 Uiso 1 1 calc R . .
C8 C 0.89650(15) 0.57448(12) 0.26903(10) 0.0408(3) Uani 1 1 d . . .
H8 H 0.8794 0.4943 0.2461 0.049 Uiso 1 1 calc R . .
C9 C 1.05318(17) 0.61869(15) 0.31360(12) 0.0537(4) Uani 1 1 d . . .
H9A H 1.0752 0.6976 0.3367 0.080 Uiso 1 1 calc R . .
H9B H 1.1063 0.6069 0.2661 0.080 Uiso 1 1 calc R . .
H9C H 1.0779 0.5797 0.3664 0.080 Uiso 1 1 calc R . .
C10 C 0.85346(19) 0.62771(15) 0.18169(11) 0.0547(4) Uani 1 1 d . . .
H10A H 0.7533 0.5979 0.1554 0.082 Uiso 1 1 calc R . .
H10B H 0.9046 0.6115 0.1341 0.082 Uiso 1 1 calc R . .
H10C H 0.8751 0.7076 0.2000 0.082 Uiso 1 1 calc R . .
N11 N 0.47636(12) 0.30291(9) 0.24706(8) 0.0364(3) Uani 1 1 d . . .
C12 C 0.45719(15) 0.40598(12) 0.24735(10) 0.0410(3) Uani 1 1 d . . .
H12 H 0.5287 0.4634 0.2356 0.049 Uiso 1 1 calc R . .
C13 C 0.33714(17) 0.42982(14) 0.26413(11) 0.0493(4) Uani 1 1 d . . .
H13 H 0.3271 0.5024 0.2642 0.059 Uiso 1 1 calc R . .
C14 C 0.23105(17) 0.34555(16) 0.28091(12) 0.0553(4) Uani 1 1 d . . .
H14 H 0.1474 0.3597 0.2918 0.066 Uiso 1 1 calc R . .
C15 C 0.25022(17) 0.24064(15) 0.28139(12) 0.0542(4) Uani 1 1 d . . .
H15 H 0.1796 0.1822 0.2927 0.065 Uiso 1 1 calc R . .
C16 C 0.37383(15) 0.22188(13) 0.26508(10) 0.0440(3) Uani 1 1 d . . .
H16 H 0.3868 0.1503 0.2666 0.053 Uiso 1 1 calc R . .
C21 C 0.62515(15) 0.15531(11) 0.21930(9) 0.0373(3) Uani 1 1 d . . .
F22 F 0.42231(9) 0.12069(7) 0.09460(6) 0.0477(2) Uani 1 1 d . . .
C22 C 0.52267(15) 0.08247(11) 0.14632(10) 0.0391(3) Uani 1 1 d . . .
F23 F 0.40984(10) -0.09302(7) 0.05108(6) 0.0573(2) Uani 1 1 d . . .
C23 C 0.51481(17) -0.02800(12) 0.12090(10) 0.0448(3) Uani 1 1 d . . .
F24 F 0.61270(13) -0.17875(7) 0.14341(8) 0.0695(3) Uani 1 1 d . . .
C24 C 0.61638(18) -0.07194(12) 0.16743(11) 0.0487(4) Uani 1 1 d . . .
F25 F 0.82435(12) -0.04524(8) 0.28400(8) 0.0688(3) Uani 1 1 d . . .
C25 C 0.72231(17) -0.00424(13) 0.23888(11) 0.0482(4) Uani 1 1 d . . .
F26 F 0.83723(9) 0.16424(7) 0.33215(6) 0.0533(2) Uani 1 1 d . . .
C26 C 0.72537(16) 0.10597(12) 0.26294(10) 0.0421(3) Uani 1 1 d . . .
C31 C 0.66498(14) 0.33095(10) 0.13623(9) 0.0345(3) Uani 1 1 d . . .
F32 F 0.43892(9) 0.34773(7) 0.06155(6) 0.0465(2) Uani 1 1 d . . .
C32 C 0.57449(15) 0.35451(11) 0.06018(10) 0.0371(3) Uani 1 1 d . . .
F33 F 0.51943(11) 0.40792(7) -0.09244(6) 0.0560(2) Uani 1 1 d . . .
C33 C 0.61267(17) 0.38446(11) -0.02292(10) 0.0430(3) Uani 1 1 d . . .
F34 F 0.78391(13) 0.41698(9) -0.11486(7) 0.0704(3) Uani 1 1 d . . .
C34 C 0.74588(18) 0.38876(13) -0.03466(10) 0.0484(4) Uani 1 1 d . . .
F35 F 0.96977(11) 0.36663(9) 0.02635(7) 0.0659(3) Uani 1 1 d . . .
C35 C 0.83881(16) 0.36286(13) 0.03638(11) 0.0460(3) Uani 1 1 d . . .
F36 F 0.89395(9) 0.30624(7) 0.18332(6) 0.0470(2) Uani 1 1 d . . .
C36 C 0.79704(15) 0.33385(11) 0.11801(9) 0.0378(3) Uani 1 1 d . . .
C41 C 0.3464(3) 0.8616(3) 0.2968(3) 0.1069(10) Uani 1 1 d . . .
H41 H 0.4087 0.8274 0.2728 0.128 Uiso 1 1 calc R . .
C42 C 0.3645(3) 0.8893(3) 0.3925(3) 0.1098(11) Uani 1 1 d . . .
H42 H 0.4393 0.8747 0.4348 0.132 Uiso 1 1 calc R . .
C43 C 0.2730(4) 0.9388(2) 0.4269(2) 0.1088(10) Uani 1 1 d . . .
H43 H 0.2853 0.9586 0.4930 0.131 Uiso 1 1 calc R . .
C44 C 0.1628(3) 0.9595(2) 0.3647(2) 0.0948(7) Uani 1 1 d . . .
H44 H 0.0993 0.9926 0.3883 0.114 Uiso 1 1 calc R . .
C45 C 0.1467(3) 0.9318(2) 0.2691(2) 0.0859(7) Uani 1 1 d . . .
H45 H 0.0723 0.9463 0.2264 0.103 Uiso 1 1 calc R . .
C46 C 0.2382(3) 0.8831(2) 0.2353(2) 0.0958(8) Uani 1 1 d . . .
H46 H 0.2269 0.8642 0.1692 0.115 Uiso 1 1 calc R . .
C51 C 0.1141(3) 0.0649(3) -0.0232(2) 0.1056(9) Uani 1 1 d . . .
H51 H 0.1928 0.1102 -0.0395 0.127 Uiso 1 1 calc R . .
C52 C 0.0797(4) -0.0458(4) -0.0476(2) 0.1154(11) Uani 1 1 d . . .
H52 H 0.1354 -0.0782 -0.0805 0.139 Uiso 1 1 calc R . .
C53 C -0.0336(4) -0.1113(2) -0.0255(2) 0.1063(9) Uani 1 1 d . . .
H53 H -0.0573 -0.1888 -0.0436 0.128 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
N1 B1 1.404(2) . ?
N1 C8 1.4818(17) . ?
N1 C5 1.4872(18) . ?
C1 C2 1.5729(18) . ?
C1 B1 1.615(2) . ?
C1 B2 1.646(2) . ?
C1 H1 0.9900 . ?
B1 C4 1.600(2) . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
B2 N11 1.6361(18) . ?
B2 C31 1.6661(19) . ?
B2 C21 1.667(2) . ?
C3 C4 1.525(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C7 1.523(2) . ?
C5 C6 1.526(2) . ?
C5 H5 0.9900 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C9 1.523(2) . ?
C8 C10 1.523(2) . ?
C8 H8 0.9900 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
N11 C16 1.3448(19) . ?
N11 C12 1.3522(18) . ?
C12 C13 1.372(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C26 1.390(2) . ?
C21 C22 1.394(2) . ?
F22 C22 1.3499(16) . ?
C22 C23 1.377(2) . ?
F23 C23 1.3438(18) . ?
C23 C24 1.372(2) . ?
F24 C24 1.3402(17) . ?
C24 C25 1.373(2) . ?
F25 C25 1.3446(18) . ?
C25 C26 1.383(2) . ?
F26 C26 1.3498(17) . ?
C31 C32 1.3898(19) . ?
C31 C36 1.3968(19) . ?
F32 C32 1.3502(16) . ?
C32 C33 1.389(2) . ?
F33 C33 1.3431(17) . ?
C33 C34 1.373(2) . ?
F34 C34 1.3422(17) . ?
C34 C35 1.370(2) . ?
F35 C35 1.3437(18) . ?
C35 C36 1.379(2) . ?
F36 C36 1.3542(16) . ?
C41 C42 1.359(5) . ?
C41 C46 1.365(4) . ?
C41 H41 0.9400 . ?
C42 C43 1.370(5) . ?
C42 H42 0.9400 . ?
C43 C44 1.381(4) . ?
C43 H43 0.9400 . ?
C44 C45 1.360(4) . ?
C44 H44 0.9400 . ?
C45 C46 1.361(4) . ?
C45 H45 0.9400 . ?
C46 H46 0.9400 . ?
C51 C52 1.340(5) . ?
C51 C53 1.364(4) 2 ?
C51 H51 0.9400 . ?
C52 C53 1.346(5) . ?
C52 H52 0.9400 . ?
C53 C51 1.364(4) 2 ?
C53 H53 0.9400 . ?

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
B1 N1 C8 120.99(11) . . ?
B1 N1 C5 125.04(12) . . ?
C8 N1 C5 113.72(11) . . ?
C2 C1 B1 101.49(10) . . ?
C2 C1 B2 109.53(11) . . ?
B1 C1 B2 122.50(11) . . ?
C2 C1 H1 107.5 . . ?
B1 C1 H1 107.5 . . ?
B2 C1 H1 107.5 . . ?
N1 B1 C4 124.60(13) . . ?
N1 B1 C1 127.40(12) . . ?
C4 B1 C1 107.62(12) . . ?
C3 C2 C1 108.15(11) . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N11 B2 C1 103.73(10) . . ?
N11 B2 C31 109.33(10) . . ?
C1 B2 C31 117.84(11) . . ?
N11 B2 C21 109.44(11) . . ?
C1 B2 C21 114.30(11) . . ?
C31 B2 C21 102.14(10) . . ?
C4 C3 C2 105.40(12) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C3 C4 B1 105.47(12) . . ?
C3 C4 H4A 110.6 . . ?
B1 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
B1 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C7 111.44(13) . . ?
N1 C5 C6 113.73(13) . . ?
C7 C5 C6 111.94(14) . . ?
N1 C5 H5 106.4 . . ?
C7 C5 H5 106.4 . . ?
C6 C5 H5 106.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 111.27(12) . . ?
N1 C8 C10 113.79(12) . . ?
C9 C8 C10 111.73(13) . . ?
N1 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C10 C8 H8 106.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 N11 C12 118.12(12) . . ?
C16 N11 B2 124.58(11) . . ?
C12 N11 B2 116.87(11) . . ?
N11 C12 C13 122.42(14) . . ?
N11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C14 119.12(15) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 118.78(15) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.52(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N11 C16 C15 122.02(15) . . ?
N11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C26 C21 C22 112.67(12) . . ?
C26 C21 B2 126.26(12) . . ?
C22 C21 B2 120.56(12) . . ?
F22 C22 C23 115.77(12) . . ?
F22 C22 C21 119.11(12) . . ?
C23 C22 C21 125.12(13) . . ?
F23 C23 C24 119.63(13) . . ?
F23 C23 C22 121.08(14) . . ?
C24 C23 C22 119.29(14) . . ?
F24 C24 C23 120.69(14) . . ?
F24 C24 C25 120.60(14) . . ?
C23 C24 C25 118.71(13) . . ?
F25 C25 C24 119.56(13) . . ?
F25 C25 C26 120.28(14) . . ?
C24 C25 C26 120.16(14) . . ?
F26 C26 C25 114.24(13) . . ?
F26 C26 C21 121.73(12) . . ?
C25 C26 C21 124.02(14) . . ?
C32 C31 C36 112.72(12) . . ?
C32 C31 B2 128.83(12) . . ?
C36 C31 B2 118.18(11) . . ?
F32 C32 C33 114.48(12) . . ?
F32 C32 C31 121.42(12) . . ?
C33 C32 C31 124.10(13) . . ?
F33 C33 C34 119.76(13) . . ?
F33 C33 C32 120.38(14) . . ?
C34 C33 C32 119.86(13) . . ?
F34 C34 C35 120.62(15) . . ?
F34 C34 C33 120.46(14) . . ?
C35 C34 C33 118.92(13) . . ?
F35 C35 C34 119.88(13) . . ?
F35 C35 C36 120.63(14) . . ?
C34 C35 C36 119.49(14) . . ?
F36 C36 C35 115.64(12) . . ?
F36 C36 C31 119.56(12) . . ?
C35 C36 C31 124.81(13) . . ?
C42 C41 C46 120.4(3) . . ?
C42 C41 H41 119.8 . . ?
C46 C41 H41 119.8 . . ?
C41 C42 C43 119.4(3) . . ?
C41 C42 H42 120.3 . . ?
C43 C42 H42 120.3 . . ?
C42 C43 C44 120.2(3) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C45 C44 C43 119.6(3) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 120.0(2) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.4(3) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C52 C51 C53 119.3(3) . 2 ?
C52 C51 H51 120.4 . . ?
C53 C51 H51 120.4 2 . ?
C51 C52 C53 120.8(3) . . ?
C51 C52 H52 119.6 . . ?
C53 C52 H52 119.6 . . ?
C52 C53 C51 119.9(3) . 2 ?
C52 C53 H53 120.1 . . ?
C51 C53 H53 120.1 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
C8 N1 B1 C4 165.79(13) . . . . ?
C5 N1 B1 C4 -8.2(2) . . . . ?
C8 N1 B1 C1 -6.4(2) . . . . ?
C5 N1 B1 C1 179.65(13) . . . . ?
C2 C1 B1 N1 162.80(14) . . . . ?
B2 C1 B1 N1 -74.92(19) . . . . ?
C2 C1 B1 C4 -10.42(14) . . . . ?
B2 C1 B1 C4 111.85(14) . . . . ?
B1 C1 C2 C3 28.29(14) . . . . ?
B2 C1 C2 C3 -102.55(13) . . . . ?
C2 C1 B2 N11 64.22(13) . . . . ?
B1 C1 B2 N11 -54.24(15) . . . . ?
C2 C1 B2 C31 -174.82(11) . . . . ?
B1 C1 B2 C31 66.72(17) . . . . ?
C2 C1 B2 C21 -54.86(15) . . . . ?
B1 C1 B2 C21 -173.32(11) . . . . ?
C1 C2 C3 C4 -36.45(15) . . . . ?
C2 C3 C4 B1 28.02(15) . . . . ?
N1 B1 C4 C3 176.06(14) . . . . ?
C1 B1 C4 C3 -10.48(16) . . . . ?
B1 N1 C5 C7 -67.04(19) . . . . ?
C8 N1 C5 C7 118.59(14) . . . . ?
B1 N1 C5 C6 60.63(19) . . . . ?
C8 N1 C5 C6 -113.74(15) . . . . ?
B1 N1 C8 C9 -105.72(15) . . . . ?
C5 N1 C8 C9 68.91(16) . . . . ?
B1 N1 C8 C10 127.00(14) . . . . ?
C5 N1 C8 C10 -58.38(16) . . . . ?
C1 B2 N11 C16 -104.82(14) . . . . ?
C31 B2 N11 C16 128.66(13) . . . . ?
C21 B2 N11 C16 17.55(17) . . . . ?
C1 B2 N11 C12 67.49(13) . . . . ?
C31 B2 N11 C12 -59.03(14) . . . . ?
C21 B2 N11 C12 -170.13(11) . . . . ?
C16 N11 C12 C13 -0.8(2) . . . . ?
B2 N11 C12 C13 -173.60(13) . . . . ?
N11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C12 N11 C16 C15 1.5(2) . . . . ?
B2 N11 C16 C15 173.73(13) . . . . ?
C14 C15 C16 N11 -1.1(2) . . . . ?
N11 B2 C21 C26 -136.33(13) . . . . ?
C1 B2 C21 C26 -20.52(19) . . . . ?
C31 B2 C21 C26 107.89(14) . . . . ?
N11 B2 C21 C22 52.43(16) . . . . ?
C1 B2 C21 C22 168.24(12) . . . . ?
C31 B2 C21 C22 -63.35(15) . . . . ?
C26 C21 C22 F22 -176.86(12) . . . . ?
B2 C21 C22 F22 -4.51(19) . . . . ?
C26 C21 C22 C23 2.6(2) . . . . ?
B2 C21 C22 C23 174.94(13) . . . . ?
F22 C22 C23 F23 -2.4(2) . . . . ?
C21 C22 C23 F23 178.17(13) . . . . ?
F22 C22 C23 C24 177.30(13) . . . . ?
C21 C22 C23 C24 -2.2(2) . . . . ?
F23 C23 C24 F24 0.6(2) . . . . ?
C22 C23 C24 F24 -179.07(13) . . . . ?
F23 C23 C24 C25 -179.67(13) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
F24 C24 C25 F25 1.1(2) . . . . ?
C23 C24 C25 F25 -178.67(14) . . . . ?
F24 C24 C25 C26 179.81(14) . . . . ?
C23 C24 C25 C26 0.1(2) . . . . ?
F25 C25 C26 F26 0.7(2) . . . . ?
C24 C25 C26 F26 -178.02(14) . . . . ?
F25 C25 C26 C21 179.29(14) . . . . ?
C24 C25 C26 C21 0.5(2) . . . . ?
C22 C21 C26 F26 176.70(12) . . . . ?
B2 C21 C26 F26 4.9(2) . . . . ?
C22 C21 C26 C25 -1.8(2) . . . . ?
B2 C21 C26 C25 -173.58(13) . . . . ?
N11 B2 C31 C32 -11.00(18) . . . . ?
C1 B2 C31 C32 -129.01(14) . . . . ?
C21 B2 C31 C32 104.85(14) . . . . ?
N11 B2 C31 C36 175.44(11) . . . . ?
C1 B2 C31 C36 57.43(16) . . . . ?
C21 B2 C31 C36 -68.70(14) . . . . ?
C36 C31 C32 F32 175.09(11) . . . . ?
B2 C31 C32 F32 1.2(2) . . . . ?
C36 C31 C32 C33 -3.71(19) . . . . ?
B2 C31 C32 C33 -177.55(13) . . . . ?
F32 C32 C33 F33 2.37(18) . . . . ?
C31 C32 C33 F33 -178.76(12) . . . . ?
F32 C32 C33 C34 -176.80(12) . . . . ?
C31 C32 C33 C34 2.1(2) . . . . ?
F33 C33 C34 F34 0.5(2) . . . . ?
C32 C33 C34 F34 179.63(13) . . . . ?
F33 C33 C34 C35 -178.98(13) . . . . ?
C32 C33 C34 C35 0.2(2) . . . . ?
F34 C34 C35 F35 0.6(2) . . . . ?
C33 C34 C35 F35 -179.95(13) . . . . ?
F34 C34 C35 C36 -179.84(13) . . . . ?
C33 C34 C35 C36 -0.4(2) . . . . ?
F35 C35 C36 F36 -2.4(2) . . . . ?
C34 C35 C36 F36 178.06(13) . . . . ?
F35 C35 C36 C31 177.92(13) . . . . ?
C34 C35 C36 C31 -1.6(2) . . . . ?
C32 C31 C36 F36 -176.17(11) . . . . ?
B2 C31 C36 F36 -1.61(18) . . . . ?
C32 C31 C36 C35 3.5(2) . . . . ?
B2 C31 C36 C35 178.07(13) . . . . ?
C46 C41 C42 C43 0.2(4) . . . . ?
C41 C42 C43 C44 0.4(4) . . . . ?
C42 C43 C44 C45 -0.8(4) . . . . ?
C43 C44 C45 C46 0.5(4) . . . . ?
C44 C45 C46 C41 0.1(4) . . . . ?
C42 C41 C46 C45 -0.5(4) . . . . ?
C53 C51 C52 C53 0.7(5) 2 . . . ?
C51 C52 C53 C51 -0.7(5) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        67.20
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.030
#=============================================================================
#  end of cif data for "erk7147" (compound 11)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
_database_code_depnum_ccdc_archive 'CCDC 982553'
#######################################################################
#
#                 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_erk6640

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H7 B F10 O'
_chemical_formula_weight         452.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.5636(2)
_cell_length_b                   11.1442(5)
_cell_length_c                   11.3520(6)
_cell_angle_alpha                117.035(3)
_cell_angle_beta                 93.834(3)
_cell_angle_gamma                95.053(2)
_cell_volume                     842.81(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2528
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6170
_exptl_absorpt_correction_T_max  0.8508
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9196
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         66.75
_reflns_number_total             2852
_reflns_number_gt                2721
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_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)+(0.0571P)²+0.2892P] 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         2852
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.33477(14) 0.58009(10) 0.49632(10) 0.0332(2) Uani 1 1 d . . .
B1 B 0.2499(2) 0.58615(17) 0.39279(16) 0.0302(3) Uani 1 1 d . . .
C1 C 0.4443(2) 0.69415(15) 0.60510(15) 0.0363(3) Uani 1 1 d . . .
H1A H 0.4004 0.7786 0.6169 0.044 Uiso 1 1 calc R . .
H1B H 0.5676 0.6974 0.5839 0.044 Uiso 1 1 calc R . .
C2 C 0.44145(19) 0.68362(15) 0.73268(15) 0.0324(3) Uani 1 1 d . . .
C3 C 0.3648(2) 0.56871(16) 0.73747(16) 0.0366(3) Uani 1 1 d . . .
H3 H 0.3086 0.4936 0.6590 0.044 Uiso 1 1 calc R . .
C4 C 0.3707(2) 0.56411(18) 0.85822(17) 0.0446(4) Uani 1 1 d . . .
H4 H 0.3181 0.4860 0.8610 0.054 Uiso 1 1 calc R . .
C5 C 0.4532(3) 0.6735(2) 0.97350(18) 0.0504(4) Uani 1 1 d . . .
H5 H 0.4574 0.6699 1.0547 0.060 Uiso 1 1 calc R . .
C6 C 0.5297(3) 0.78851(19) 0.96965(17) 0.0493(4) Uani 1 1 d . . .
H6 H 0.5858 0.8632 1.0484 0.059 Uiso 1 1 calc R . .
C7 C 0.5240(2) 0.79438(17) 0.85004(16) 0.0408(4) Uani 1 1 d . . .
H7 H 0.5759 0.8731 0.8480 0.049 Uiso 1 1 calc R . .
C11 C 0.14250(19) 0.44944(15) 0.27970(14) 0.0318(3) Uani 1 1 d . . .
F12 F 0.06979(14) 0.36231(10) 0.42833(10) 0.0470(3) Uani 1 1 d . . .
C12 C 0.0634(2) 0.34610(16) 0.30308(16) 0.0349(3) Uani 1 1 d . . .
F13 F -0.10515(14) 0.13142(10) 0.23344(13) 0.0591(3) Uani 1 1 d . . .
C13 C -0.0274(2) 0.22559(16) 0.20431(19) 0.0420(4) Uani 1 1 d . . .
F14 F -0.12601(17) 0.08692(11) -0.02339(12) 0.0700(4) Uani 1 1 d . . .
C14 C -0.0395(2) 0.20337(17) 0.07410(18) 0.0481(4) Uani 1 1 d . . .
F15 F 0.0288(2) 0.28072(13) -0.08076(11) 0.0765(4) Uani 1 1 d . . .
C15 C 0.0373(3) 0.30177(18) 0.04573(17) 0.0484(4) Uani 1 1 d . . .
F16 F 0.19770(16) 0.51339(10) 0.11137(10) 0.0531(3) Uani 1 1 d . . .
C16 C 0.1245(2) 0.42182(16) 0.14688(16) 0.0385(4) Uani 1 1 d . . .
C21 C 0.25346(19) 0.72231(14) 0.37843(14) 0.0306(3) Uani 1 1 d . . .
F22 F -0.05916(12) 0.71419(10) 0.37746(11) 0.0460(3) Uani 1 1 d . . .
C22 C 0.0981(2) 0.77586(15) 0.37028(14) 0.0324(3) Uani 1 1 d . . .
F23 F -0.06036(13) 0.93955(10) 0.34888(10) 0.0477(3) Uani 1 1 d . . .
C23 C 0.0933(2) 0.89069(15) 0.35363(14) 0.0337(3) Uani 1 1 d . . .
F24 F 0.24779(14) 1.06369(9) 0.32105(11) 0.0493(3) Uani 1 1 d . . .
C24 C 0.2496(2) 0.95346(14) 0.33964(15) 0.0348(3) Uani 1 1 d . . .
F25 F 0.55973(13) 0.96220(10) 0.32778(10) 0.0476(3) Uani 1 1 d . . .
C25 C 0.4075(2) 0.90233(15) 0.34406(14) 0.0338(3) Uani 1 1 d . . .
F26 F 0.56563(12) 0.74469(10) 0.37115(11) 0.0457(3) Uani 1 1 d . . .
C26 C 0.4078(2) 0.78992(15) 0.36529(14) 0.0325(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.333(2) . ?
O1 C1 1.4415(18) . ?
B1 C11 1.579(2) . ?
B1 C21 1.596(2) . ?
C1 C2 1.507(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.384(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.393(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C11 C16 1.389(2) . ?
C11 C12 1.390(2) . ?
F12 C12 1.3461(18) . ?
C12 C13 1.377(2) . ?
F13 C13 1.338(2) . ?
C13 C14 1.378(3) . ?
F14 C14 1.3360(19) . ?
C14 C15 1.370(3) . ?
F15 C15 1.342(2) . ?
C15 C16 1.375(2) . ?
F16 C16 1.3471(19) . ?
C21 C22 1.380(2) . ?
C21 C26 1.387(2) . ?
F22 C22 1.3465(17) . ?
C22 C23 1.379(2) . ?
F23 C23 1.3344(17) . ?
C23 C24 1.376(2) . ?
F24 C24 1.3386(17) . ?
C24 C25 1.375(2) . ?
F25 C25 1.3456(17) . ?
C25 C26 1.379(2) . ?
F26 C26 1.3451(17) . ?

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
B1 O1 C1 123.88(12) . . ?
O1 B1 C11 116.91(13) . . ?
O1 B1 C21 123.47(13) . . ?
C11 B1 C21 119.62(12) . . ?
O1 C1 C2 111.13(12) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C7 119.22(14) . . ?
C3 C2 C1 122.99(13) . . ?
C7 C2 C1 117.78(13) . . ?
C2 C3 C4 120.17(15) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.28(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.92(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.28(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.12(16) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C16 C11 C12 114.62(14) . . ?
C16 C11 B1 121.84(13) . . ?
C12 C11 B1 123.51(13) . . ?
F12 C12 C13 116.41(14) . . ?
F12 C12 C11 119.91(13) . . ?
C13 C12 C11 123.67(15) . . ?
F13 C13 C12 120.94(16) . . ?
F13 C13 C14 119.93(15) . . ?
C12 C13 C14 119.13(15) . . ?
F14 C14 C15 120.40(17) . . ?
F14 C14 C13 120.15(17) . . ?
C15 C14 C13 119.45(15) . . ?
F15 C15 C14 120.11(16) . . ?
F15 C15 C16 119.90(17) . . ?
C14 C15 C16 119.99(16) . . ?
F16 C16 C15 116.65(15) . . ?
F16 C16 C11 120.19(14) . . ?
C15 C16 C11 123.14(16) . . ?
C22 C21 C26 115.51(13) . . ?
C22 C21 B1 121.17(13) . . ?
C26 C21 B1 123.22(13) . . ?
F22 C22 C23 116.96(13) . . ?
F22 C22 C21 119.65(13) . . ?
C23 C22 C21 123.39(14) . . ?
F23 C23 C24 120.13(13) . . ?
F23 C23 C22 120.89(14) . . ?
C24 C23 C22 118.97(14) . . ?
F24 C24 C25 120.08(14) . . ?
F24 C24 C23 120.04(14) . . ?
C25 C24 C23 119.88(13) . . ?
F25 C25 C24 119.85(13) . . ?
F25 C25 C26 120.71(14) . . ?
C24 C25 C26 119.44(14) . . ?
F26 C26 C25 117.47(13) . . ?
F26 C26 C21 119.77(13) . . ?
C25 C26 C21 122.75(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 B1 C11 177.44(13) . . . . ?
C1 O1 B1 C21 -2.2(2) . . . . ?
B1 O1 C1 C2 149.92(14) . . . . ?
O1 C1 C2 C3 9.0(2) . . . . ?
O1 C1 C2 C7 -172.57(13) . . . . ?
C7 C2 C3 C4 -0.1(2) . . . . ?
C1 C2 C3 C4 178.32(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C1 C2 C7 C6 -178.17(15) . . . . ?
O1 B1 C11 C16 -147.74(15) . . . . ?
C21 B1 C11 C16 31.9(2) . . . . ?
O1 B1 C11 C12 30.3(2) . . . . ?
C21 B1 C11 C12 -150.06(14) . . . . ?
C16 C11 C12 F12 -178.98(13) . . . . ?
B1 C11 C12 F12 2.8(2) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
B1 C11 C12 C13 -178.64(14) . . . . ?
F12 C12 C13 F13 0.5(2) . . . . ?
C11 C12 C13 F13 -178.08(14) . . . . ?
F12 C12 C13 C14 179.60(14) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
F13 C13 C14 F14 -1.3(2) . . . . ?
C12 C13 C14 F14 179.62(14) . . . . ?
F13 C13 C14 C15 178.57(15) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
F14 C14 C15 F15 -1.2(3) . . . . ?
C13 C14 C15 F15 178.99(15) . . . . ?
F14 C14 C15 C16 179.39(15) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
F15 C15 C16 F16 0.2(2) . . . . ?
C14 C15 C16 F16 179.59(15) . . . . ?
F15 C15 C16 C11 -178.38(15) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C12 C11 C16 F16 -179.09(13) . . . . ?
B1 C11 C16 F16 -0.9(2) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
B1 C11 C16 C15 177.63(15) . . . . ?
O1 B1 C21 C22 -119.38(16) . . . . ?
C11 B1 C21 C22 61.03(19) . . . . ?
O1 B1 C21 C26 64.6(2) . . . . ?
C11 B1 C21 C26 -114.99(16) . . . . ?
C26 C21 C22 F22 177.79(12) . . . . ?
B1 C21 C22 F22 1.5(2) . . . . ?
C26 C21 C22 C23 -1.6(2) . . . . ?
B1 C21 C22 C23 -177.91(13) . . . . ?
F22 C22 C23 F23 1.9(2) . . . . ?
C21 C22 C23 F23 -178.74(13) . . . . ?
F22 C22 C23 C24 -177.04(13) . . . . ?
C21 C22 C23 C24 2.4(2) . . . . ?
F23 C23 C24 F24 -0.1(2) . . . . ?
C22 C23 C24 F24 178.84(13) . . . . ?
F23 C23 C24 C25 -179.73(13) . . . . ?
C22 C23 C24 C25 -0.8(2) . . . . ?
F24 C24 C25 F25 -0.9(2) . . . . ?
C23 C24 C25 F25 178.71(13) . . . . ?
F24 C24 C25 C26 179.03(13) . . . . ?
C23 C24 C25 C26 -1.3(2) . . . . ?
F25 C25 C26 F26 1.1(2) . . . . ?
C24 C25 C26 F26 -178.89(13) . . . . ?
F25 C25 C26 C21 -177.92(13) . . . . ?
C24 C25 C26 C21 2.1(2) . . . . ?
C22 C21 C26 F26 -179.64(12) . . . . ?
B1 C21 C26 F26 -3.4(2) . . . . ?
C22 C21 C26 C25 -0.7(2) . . . . ?
B1 C21 C26 C25 175.56(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        66.75
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
#=============================================================================
#  end of cif data for "erk6640" (compound 12)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
_database_code_depnum_ccdc_archive 'CCDC 983316'
