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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_erk6293
_audit_block_doi                 10.5517/cc148pgk
_database_code_depnum_ccdc_archive 'CCDC 1051038'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5CP00306G 2015
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H26 B F10 N3'
_chemical_formula_weight         665.38

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           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.4308(2)
_cell_length_b                   18.9125(2)
_cell_length_c                   15.1079(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.7900(10)
_cell_angle_gamma                90.00
_cell_volume                     3547.62(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5959
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8310
_exptl_absorpt_correction_T_max  0.9100
_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            29690
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         67.01
_reflns_number_total             6109
_reflns_number_gt                4294
_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. 
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 220 48 ' '
2 0.101 0.582 0.294 17 0 ' '
3 0.502 0.500 0.501 219 48 ' '
4 0.407 0.084 0.210 16 0 ' '
5 0.593 0.916 0.790 15 0 ' '
6 0.907 0.416 0.710 16 0 ' '
_platon_squeeze_details          
;
 A badly disordered half hexane molecule was found in the 
 asymmetrical unit and could not be satisfactorily refined. The program 
 SQUEEZE (A. L. Spek J. Appl. Cryst., 2003, 36, 7-13) was therefore used
 to remove mathematically the effect of the solvent.
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule. 
;

_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)+(0.0644P)²+1.1709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'at N and B from difmap, others geom'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6109
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
N37 N 0.2729(2) -0.21725(12) 0.94564(15) 0.0705(6) Uani 1 1 d . . .
C37 C 0.2657(2) -0.16930(13) 0.89923(16) 0.0555(6) Uani 1 1 d . . .
C34 C 0.25660(19) -0.10919(12) 0.84145(14) 0.0469(5) Uani 1 1 d . . .
C33 C 0.3340(2) -0.09588(13) 0.78092(15) 0.0556(6) Uani 1 1 d . . .
H33 H 0.3924 -0.1270 0.7763 0.067 Uiso 1 1 calc R . .
C32 C 0.32559(19) -0.03684(13) 0.72724(15) 0.0516(6) Uani 1 1 d . . .
H32 H 0.3782 -0.0279 0.6860 0.062 Uiso 1 1 calc R . .
C31 C 0.24042(17) 0.00895(11) 0.73394(13) 0.0399(5) Uani 1 1 d . . .
C36 C 0.1638(2) -0.00416(13) 0.79492(16) 0.0556(6) Uani 1 1 d . . .
H36 H 0.1062 0.0275 0.8004 0.067 Uiso 1 1 calc R . .
C35 C 0.1712(2) -0.06357(14) 0.84779(17) 0.0612(7) Uani 1 1 d . . .
H35 H 0.1178 -0.0729 0.8882 0.073 Uiso 1 1 calc R . .
N2 N 0.23317(13) 0.07222(9) 0.68143(10) 0.0395(4) Uani 1 1 d . . .
C1 C 0.15366(17) 0.07732(11) 0.62041(13) 0.0406(5) Uani 1 1 d . . .
C2 C 0.0836(2) 0.01618(13) 0.59635(17) 0.0589(7) Uani 1 1 d . . .
H2A H 0.1256 -0.0197 0.5678 0.088 Uiso 1 1 calc R . .
H2B H 0.0251 0.0316 0.5561 0.088 Uiso 1 1 calc R . .
H2C H 0.0544 -0.0033 0.6495 0.088 Uiso 1 1 calc R . .
N1 N 0.13973(15) 0.13704(10) 0.57501(11) 0.0435(4) Uani 1 1 d . . .
H1A H 0.181(2) 0.1732(15) 0.5847(16) 0.057(8) Uiso 1 1 d . . .
C11 C 0.05038(18) 0.15156(12) 0.51239(14) 0.0458(5) Uani 1 1 d . . .
C12 C 0.0701(2) 0.15386(13) 0.42248(15) 0.0536(6) Uani 1 1 d . . .
C13 C -0.0177(2) 0.16956(14) 0.36414(17) 0.0644(7) Uani 1 1 d . . .
H13 H -0.0075 0.1709 0.3029 0.077 Uiso 1 1 calc R . .
C14 C -0.1170(2) 0.18290(15) 0.39383(19) 0.0693(8) Uani 1 1 d . . .
H14 H -0.1743 0.1937 0.3531 0.083 Uiso 1 1 calc R . .
C15 C -0.1345(2) 0.18067(14) 0.48291(19) 0.0645(7) Uani 1 1 d . . .
H15 H -0.2040 0.1897 0.5022 0.077 Uiso 1 1 calc R . .
C16 C -0.05160(19) 0.16538(13) 0.54499(16) 0.0529(6) Uani 1 1 d . . .
C17 C 0.1799(2) 0.13994(17) 0.38718(17) 0.0699(8) Uani 1 1 d . . .
H17 H 0.2310 0.1345 0.4390 0.084 Uiso 1 1 calc R . .
C18 C 0.1827(3) 0.0728(2) 0.3355(3) 0.1167(14) Uani 1 1 d . . .
H18A H 0.1612 0.0337 0.3723 0.175 Uiso 1 1 calc R . .
H18B H 0.2552 0.0647 0.3167 0.175 Uiso 1 1 calc R . .
H18C H 0.1336 0.0763 0.2838 0.175 Uiso 1 1 calc R . .
C19 C 0.2186(4) 0.2027(2) 0.3334(3) 0.1154(14) Uani 1 1 d . . .
H19A H 0.2943 0.1968 0.3225 0.173 Uiso 1 1 calc R . .
H19B H 0.2086 0.2461 0.3662 0.173 Uiso 1 1 calc R . .
H19C H 0.1774 0.2050 0.2772 0.173 Uiso 1 1 calc R . .
C20 C -0.0695(2) 0.16738(15) 0.64341(17) 0.0621(7) Uani 1 1 d . . .
H20 H -0.0243 0.1297 0.6716 0.075 Uiso 1 1 calc R . .
C21 C -0.1865(3) 0.1527(2) 0.6663(2) 0.0956(11) Uani 1 1 d . . .
H21A H -0.2320 0.1914 0.6451 0.143 Uiso 1 1 calc R . .
H21B H -0.1904 0.1484 0.7301 0.143 Uiso 1 1 calc R . .
H21C H -0.2108 0.1091 0.6382 0.143 Uiso 1 1 calc R . .
C22 C -0.0319(3) 0.23717(19) 0.6837(2) 0.0890(10) Uani 1 1 d . . .
H22A H 0.0431 0.2448 0.6715 0.134 Uiso 1 1 calc R . .
H22B H -0.0396 0.2360 0.7473 0.134 Uiso 1 1 calc R . .
H22C H -0.0753 0.2753 0.6581 0.134 Uiso 1 1 calc R . .
B1 B 0.3200(2) 0.13317(14) 0.69764(16) 0.0429(6) Uani 1 1 d . . .
H1B H 0.2762(17) 0.1849(12) 0.6995(13) 0.042(5) Uiso 1 1 d . . .
C51 C 0.38056(18) 0.12130(12) 0.79432(14) 0.0478(6) Uani 1 1 d . . .
C52 C 0.3260(2) 0.13715(13) 0.86976(15) 0.0535(6) Uani 1 1 d . . .
F52 F 0.22434(12) 0.16155(9) 0.86175(9) 0.0684(4) Uani 1 1 d . . .
C53 C 0.3684(2) 0.12767(16) 0.95475(16) 0.0673(8) Uani 1 1 d . . .
F53 F 0.31026(17) 0.14329(11) 1.02532(10) 0.0969(6) Uani 1 1 d . . .
C54 C 0.4696(3) 0.10266(19) 0.96748(19) 0.0803(9) Uani 1 1 d . . .
F54 F 0.51262(18) 0.09194(14) 1.05007(12) 0.1213(8) Uani 1 1 d . . .
C55 C 0.5285(2) 0.0869(2) 0.8967(2) 0.0859(10) Uani 1 1 d . . .
F55 F 0.62866(16) 0.06129(16) 0.90812(15) 0.1358(9) Uani 1 1 d . . .
C56 C 0.4830(2) 0.09609(17) 0.81127(18) 0.0682(7) Uani 1 1 d . . .
F56 F 0.54417(13) 0.07731(12) 0.74393(12) 0.0988(6) Uani 1 1 d . . .
C41 C 0.39902(17) 0.13903(12) 0.61470(14) 0.0468(5) Uani 1 1 d . . .
C42 C 0.4653(2) 0.19789(14) 0.60989(16) 0.0576(6) Uani 1 1 d . . .
F42 F 0.46602(14) 0.24552(9) 0.67650(11) 0.0790(5) Uani 1 1 d . . .
C43 C 0.5312(2) 0.21170(16) 0.54128(19) 0.0677(7) Uani 1 1 d . . .
F43 F 0.59487(15) 0.26926(11) 0.54296(14) 0.1023(6) Uani 1 1 d . . .
C44 C 0.5317(2) 0.16608(18) 0.47145(18) 0.0684(8) Uani 1 1 d . . .
F44 F 0.59388(14) 0.17945(12) 0.40255(12) 0.1012(6) Uani 1 1 d . . .
C45 C 0.4686(2) 0.10732(16) 0.47164(16) 0.0607(7) Uani 1 1 d . . .
F45 F 0.46711(13) 0.06195(10) 0.40260(10) 0.0822(5) Uani 1 1 d . . .
C46 C 0.40553(18) 0.09448(13) 0.54251(15) 0.0489(6) Uani 1 1 d . . .
F46 F 0.34644(11) 0.03438(7) 0.53658(8) 0.0595(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N37 C37 1.147(3) . ?
C37 C34 1.434(3) . ?
C34 C35 1.375(3) . ?
C34 C33 1.382(3) . ?
C33 C32 1.381(3) . ?
C33 H33 0.9400 . ?
C32 C31 1.375(3) . ?
C32 H32 0.9400 . ?
C31 C36 1.380(3) . ?
C31 N2 1.436(3) . ?
C36 C35 1.379(3) . ?
C36 H36 0.9400 . ?
C35 H35 0.9400 . ?
N2 C1 1.322(3) . ?
N2 B1 1.590(3) . ?
C1 N1 1.328(3) . ?
C1 C2 1.482(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
N1 C11 1.450(3) . ?
N1 H1A 0.86(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.407(3) . ?
C12 C13 1.400(3) . ?
C12 C17 1.513(4) . ?
C13 C14 1.358(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9400 . ?
C16 C20 1.515(4) . ?
C17 C18 1.493(5) . ?
C17 C19 1.530(4) . ?
C17 H17 0.9900 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 C22 1.518(4) . ?
C20 C21 1.536(4) . ?
C20 H20 0.9900 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
B1 C51 1.626(3) . ?
B1 C41 1.633(3) . ?
B1 H1B 1.12(2) . ?
C51 C56 1.372(3) . ?
C51 C52 1.387(3) . ?
C52 F52 1.345(3) . ?
C52 C53 1.376(3) . ?
C53 C54 1.349(4) . ?
C53 F53 1.350(3) . ?
C54 F54 1.349(3) . ?
C54 C55 1.357(5) . ?
C55 F55 1.340(4) . ?
C55 C56 1.395(4) . ?
C56 F56 1.347(3) . ?
C41 C46 1.384(3) . ?
C41 C42 1.389(3) . ?
C42 F42 1.350(3) . ?
C42 C43 1.377(4) . ?
C43 F43 1.345(3) . ?
C43 C44 1.363(4) . ?
C44 F44 1.350(3) . ?
C44 C45 1.360(4) . ?
C45 F45 1.350(3) . ?
C45 C46 1.379(3) . ?
C46 F46 1.354(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N37 C37 C34 179.8(3) . . ?
C35 C34 C33 119.8(2) . . ?
C35 C34 C37 119.6(2) . . ?
C33 C34 C37 120.7(2) . . ?
C32 C33 C34 120.0(2) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C31 C32 C33 120.2(2) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C31 C36 119.7(2) . . ?
C32 C31 N2 120.79(19) . . ?
C36 C31 N2 119.46(19) . . ?
C35 C36 C31 120.3(2) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C34 C35 C36 120.1(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C1 N2 C31 118.08(17) . . ?
C1 N2 B1 122.24(18) . . ?
C31 N2 B1 119.68(16) . . ?
N2 C1 N1 119.77(19) . . ?
N2 C1 C2 121.63(19) . . ?
N1 C1 C2 118.45(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N1 C11 125.07(19) . . ?
C1 N1 H1A 121.7(17) . . ?
C11 N1 H1A 113.0(17) . . ?
C12 C11 C16 122.7(2) . . ?
C12 C11 N1 118.5(2) . . ?
C16 C11 N1 118.8(2) . . ?
C11 C12 C13 116.9(2) . . ?
C11 C12 C17 122.9(2) . . ?
C13 C12 C17 120.2(2) . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 117.0(2) . . ?
C15 C16 C20 121.2(2) . . ?
C11 C16 C20 121.7(2) . . ?
C18 C17 C12 112.2(3) . . ?
C18 C17 C19 111.5(3) . . ?
C12 C17 C19 111.4(3) . . ?
C18 C17 H17 107.2 . . ?
C12 C17 H17 107.2 . . ?
C19 C17 H17 107.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 C22 111.0(2) . . ?
C16 C20 C21 113.7(2) . . ?
C22 C20 C21 110.0(3) . . ?
C16 C20 H20 107.3 . . ?
C22 C20 H20 107.3 . . ?
C21 C20 H20 107.3 . . ?
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 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 B1 C51 108.64(18) . . ?
N2 B1 C41 111.11(17) . . ?
C51 B1 C41 115.40(19) . . ?
N2 B1 H1B 108.0(11) . . ?
C51 B1 H1B 107.6(10) . . ?
C41 B1 H1B 105.7(11) . . ?
C56 C51 C52 114.1(2) . . ?
C56 C51 B1 126.9(2) . . ?
C52 C51 B1 119.0(2) . . ?
F52 C52 C53 116.4(2) . . ?
F52 C52 C51 119.67(19) . . ?
C53 C52 C51 123.9(3) . . ?
C54 C53 F53 119.7(2) . . ?
C54 C53 C52 119.4(3) . . ?
F53 C53 C52 120.8(3) . . ?
C53 C54 F54 120.6(3) . . ?
C53 C54 C55 120.0(2) . . ?
F54 C54 C55 119.4(3) . . ?
F55 C55 C54 120.8(3) . . ?
F55 C55 C56 119.7(3) . . ?
C54 C55 C56 119.4(3) . . ?
F56 C56 C51 120.2(2) . . ?
F56 C56 C55 116.6(3) . . ?
C51 C56 C55 123.1(3) . . ?
C46 C41 C42 112.9(2) . . ?
C46 C41 B1 128.6(2) . . ?
C42 C41 B1 118.4(2) . . ?
F42 C42 C43 116.9(2) . . ?
F42 C42 C41 118.6(2) . . ?
C43 C42 C41 124.6(2) . . ?
F43 C43 C44 120.1(3) . . ?
F43 C43 C42 120.7(3) . . ?
C44 C43 C42 119.2(3) . . ?
F44 C44 C45 120.4(3) . . ?
F44 C44 C43 120.2(3) . . ?
C45 C44 C43 119.4(2) . . ?
F45 C45 C44 120.3(2) . . ?
F45 C45 C46 120.1(3) . . ?
C44 C45 C46 119.7(2) . . ?
F46 C46 C45 115.1(2) . . ?
F46 C46 C41 120.7(2) . . ?
C45 C46 C41 124.2(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
N37 C37 C34 C35 -50(100) . . . . ?
N37 C37 C34 C33 129(100) . . . . ?
C35 C34 C33 C32 0.2(4) . . . . ?
C37 C34 C33 C32 -178.4(2) . . . . ?
C34 C33 C32 C31 0.1(4) . . . . ?
C33 C32 C31 C36 0.4(3) . . . . ?
C33 C32 C31 N2 177.2(2) . . . . ?
C32 C31 C36 C35 -1.2(4) . . . . ?
N2 C31 C36 C35 -178.1(2) . . . . ?
C33 C34 C35 C36 -1.0(4) . . . . ?
C37 C34 C35 C36 177.5(2) . . . . ?
C31 C36 C35 C34 1.6(4) . . . . ?
C32 C31 N2 C1 113.8(2) . . . . ?
C36 C31 N2 C1 -69.4(3) . . . . ?
C32 C31 N2 B1 -65.9(3) . . . . ?
C36 C31 N2 B1 110.9(2) . . . . ?
C31 N2 C1 N1 175.13(19) . . . . ?
B1 N2 C1 N1 -5.2(3) . . . . ?
C31 N2 C1 C2 -9.3(3) . . . . ?
B1 N2 C1 C2 170.3(2) . . . . ?
N2 C1 N1 C11 -174.1(2) . . . . ?
C2 C1 N1 C11 10.2(3) . . . . ?
C1 N1 C11 C12 -108.8(3) . . . . ?
C1 N1 C11 C16 73.6(3) . . . . ?
C16 C11 C12 C13 -1.1(4) . . . . ?
N1 C11 C12 C13 -178.6(2) . . . . ?
C16 C11 C12 C17 179.2(2) . . . . ?
N1 C11 C12 C17 1.7(3) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C17 C12 C13 C14 -179.4(3) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C14 C15 C16 C20 176.2(3) . . . . ?
C12 C11 C16 C15 1.0(4) . . . . ?
N1 C11 C16 C15 178.5(2) . . . . ?
C12 C11 C16 C20 -175.8(2) . . . . ?
N1 C11 C16 C20 1.7(3) . . . . ?
C11 C12 C17 C18 111.8(3) . . . . ?
C13 C12 C17 C18 -67.9(4) . . . . ?
C11 C12 C17 C19 -122.4(3) . . . . ?
C13 C12 C17 C19 57.9(4) . . . . ?
C15 C16 C20 C22 -97.7(3) . . . . ?
C11 C16 C20 C22 79.0(3) . . . . ?
C15 C16 C20 C21 27.0(4) . . . . ?
C11 C16 C20 C21 -156.3(3) . . . . ?
C1 N2 B1 C51 162.40(19) . . . . ?
C31 N2 B1 C51 -17.9(3) . . . . ?
C1 N2 B1 C41 -69.6(3) . . . . ?
C31 N2 B1 C41 110.1(2) . . . . ?
N2 B1 C51 C56 105.4(3) . . . . ?
C41 B1 C51 C56 -20.1(4) . . . . ?
N2 B1 C51 C52 -74.1(3) . . . . ?
C41 B1 C51 C52 160.4(2) . . . . ?
C56 C51 C52 F52 -179.2(2) . . . . ?
B1 C51 C52 F52 0.3(3) . . . . ?
C56 C51 C52 C53 -1.1(4) . . . . ?
B1 C51 C52 C53 178.5(2) . . . . ?
F52 C52 C53 C54 179.3(3) . . . . ?
C51 C52 C53 C54 1.1(4) . . . . ?
F52 C52 C53 F53 -0.9(4) . . . . ?
C51 C52 C53 F53 -179.1(2) . . . . ?
F53 C53 C54 F54 1.1(5) . . . . ?
C52 C53 C54 F54 -179.1(3) . . . . ?
F53 C53 C54 C55 -179.9(3) . . . . ?
C52 C53 C54 C55 -0.1(5) . . . . ?
C53 C54 C55 F55 -179.2(3) . . . . ?
F54 C54 C55 F55 -0.3(5) . . . . ?
C53 C54 C55 C56 -0.8(5) . . . . ?
F54 C54 C55 C56 178.2(3) . . . . ?
C52 C51 C56 F56 178.7(3) . . . . ?
B1 C51 C56 F56 -0.9(4) . . . . ?
C52 C51 C56 C55 0.2(4) . . . . ?
B1 C51 C56 C55 -179.4(3) . . . . ?
F55 C55 C56 F56 0.7(5) . . . . ?
C54 C55 C56 F56 -177.8(3) . . . . ?
F55 C55 C56 C51 179.3(3) . . . . ?
C54 C55 C56 C51 0.8(5) . . . . ?
N2 B1 C41 C46 -7.8(3) . . . . ?
C51 B1 C41 C46 116.4(3) . . . . ?
N2 B1 C41 C42 167.65(19) . . . . ?
C51 B1 C41 C42 -68.1(3) . . . . ?
C46 C41 C42 F42 179.9(2) . . . . ?
B1 C41 C42 F42 3.8(3) . . . . ?
C46 C41 C42 C43 0.0(4) . . . . ?
B1 C41 C42 C43 -176.1(2) . . . . ?
F42 C42 C43 F43 1.7(4) . . . . ?
C41 C42 C43 F43 -178.4(2) . . . . ?
F42 C42 C43 C44 -178.5(2) . . . . ?
C41 C42 C43 C44 1.3(4) . . . . ?
F43 C43 C44 F44 -1.8(4) . . . . ?
C42 C43 C44 F44 178.5(2) . . . . ?
F43 C43 C44 C45 178.6(2) . . . . ?
C42 C43 C44 C45 -1.1(4) . . . . ?
F44 C44 C45 F45 -0.4(4) . . . . ?
C43 C44 C45 F45 179.3(2) . . . . ?
F44 C44 C45 C46 -180.0(2) . . . . ?
C43 C44 C45 C46 -0.3(4) . . . . ?
F45 C45 C46 F46 0.9(3) . . . . ?
C44 C45 C46 F46 -179.5(2) . . . . ?
F45 C45 C46 C41 -177.8(2) . . . . ?
C44 C45 C46 C41 1.8(4) . . . . ?
C42 C41 C46 F46 179.8(2) . . . . ?
B1 C41 C46 F46 -4.5(4) . . . . ?
C42 C41 C46 C45 -1.6(3) . . . . ?
B1 C41 C46 C45 174.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        67.01
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_erk6469
_audit_block_doi                 10.5517/cc148phl
_database_code_depnum_ccdc_archive 'CCDC 1051039'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5CP00306G 2015
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35.50 H26 B F15 N2'
_chemical_formula_weight         776.39

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.9877(2)
_cell_length_b                   11.1552(2)
_cell_length_c                   18.1937(3)
_cell_angle_alpha                72.6580(10)
_cell_angle_beta                 82.8280(10)
_cell_angle_gamma                66.7880(10)
_cell_volume                     1778.22(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4565
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             786
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_T_max  0.9632
_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            16889
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6108
_reflns_number_gt                5226
_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)+(0.0407P)²+1.1574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'at N and B from difmap, others geom'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6108
_refine_ls_number_parameters     516
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.101
_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 1.2213(2) 0.34914(18) 0.30340(11) 0.0420(4) Uani 1 1 d . . .
H1B H 1.156(2) 0.374(2) 0.3335(13) 0.037(6) Uiso 1 1 d . . .
C1 C 1.2057(2) 0.4300(2) 0.23261(12) 0.0386(5) Uani 1 1 d . . .
N2 N 1.09688(18) 0.55033(16) 0.21778(9) 0.0382(4) Uani 1 1 d . . .
C2 C 1.3114(3) 0.3855(2) 0.17179(14) 0.0550(6) Uani 1 1 d . . .
H2A H 1.3818 0.2951 0.1934 0.082 Uiso 1 1 calc R . .
H2B H 1.3614 0.4477 0.1520 0.082 Uiso 1 1 calc R . .
H2C H 1.2598 0.3847 0.1303 0.082 Uiso 1 1 calc R . .
B1 B 0.9739(3) 0.5946(2) 0.28043(14) 0.0404(5) Uani 1 1 d . . .
H1A H 0.941(2) 0.505(2) 0.3063(13) 0.046(6) Uiso 1 1 d . . .
C11 C 1.3276(2) 0.2120(2) 0.32814(12) 0.0458(5) Uani 1 1 d . . .
C12 C 1.2817(3) 0.1058(2) 0.33717(14) 0.0531(6) Uani 1 1 d . . .
C13 C 1.3861(3) -0.0253(3) 0.36109(18) 0.0705(8) Uani 1 1 d . . .
H13 H 1.3598 -0.0999 0.3670 0.085 Uiso 1 1 calc R . .
C14 C 1.5262(3) -0.0473(3) 0.3761(2) 0.0806(9) Uani 1 1 d . . .
H14 H 1.5949 -0.1365 0.3916 0.097 Uiso 1 1 calc R . .
C15 C 1.5672(3) 0.0587(3) 0.36890(19) 0.0741(8) Uani 1 1 d . . .
H15 H 1.6634 0.0414 0.3804 0.089 Uiso 1 1 calc R . .
C16 C 1.4688(3) 0.1926(3) 0.34471(15) 0.0572(6) Uani 1 1 d . . .
C17 C 1.1259(3) 0.1284(3) 0.32222(17) 0.0638(7) Uani 1 1 d . . .
H17 H 1.0641 0.2208 0.3262 0.077 Uiso 1 1 calc R . .
C18 C 1.1091(5) 0.1258(7) 0.2416(3) 0.141(2) Uani 1 1 d . . .
H18A H 1.1673 0.0362 0.2355 0.212 Uiso 1 1 calc R . .
H18B H 1.1417 0.1921 0.2049 0.212 Uiso 1 1 calc R . .
H18C H 1.0075 0.1474 0.2325 0.212 Uiso 1 1 calc R . .
C19 C 1.0698(4) 0.0320(4) 0.3813(3) 0.1131(15) Uani 1 1 d U . .
H19A H 0.9651 0.0632 0.3762 0.170 Uiso 1 1 calc R . .
H19B H 1.0924 0.0281 0.4324 0.170 Uiso 1 1 calc R . .
H19C H 1.1157 -0.0577 0.3732 0.170 Uiso 1 1 calc R . .
C20 C 1.5150(3) 0.3079(3) 0.34104(19) 0.0702(8) Uani 1 1 d . . .
H20 H 1.4438 0.3916 0.3085 0.084 Uiso 1 1 calc R . .
C21 C 1.5079(5) 0.3273(4) 0.4211(2) 0.1054(12) Uani 1 1 d . . .
H21A H 1.4096 0.3451 0.4415 0.158 Uiso 1 1 calc R . .
H21B H 1.5347 0.4034 0.4179 0.158 Uiso 1 1 calc R . .
H21C H 1.5749 0.2459 0.4548 0.158 Uiso 1 1 calc R . .
C22 C 1.6652(4) 0.2902(4) 0.3046(3) 0.1131(14) Uani 1 1 d . . .
H22A H 1.7380 0.2102 0.3361 0.170 Uiso 1 1 calc R . .
H22B H 1.6865 0.3694 0.3010 0.170 Uiso 1 1 calc R . .
H22C H 1.6665 0.2797 0.2534 0.170 Uiso 1 1 calc R . .
C31 C 1.0755(2) 0.6309(2) 0.13930(12) 0.0419(5) Uani 1 1 d . . .
C32 C 0.9882(3) 0.6168(3) 0.09229(14) 0.0540(6) Uani 1 1 d . . .
F32 F 0.93038(19) 0.52188(18) 0.11991(9) 0.0759(5) Uani 1 1 d . . .
C33 C 0.9581(3) 0.6976(3) 0.01766(15) 0.0700(8) Uani 1 1 d . . .
F33 F 0.8726(2) 0.6800(3) -0.02610(10) 0.1069(7) Uani 1 1 d . . .
C34 C 1.0166(3) 0.7949(3) -0.01073(14) 0.0682(8) Uani 1 1 d . . .
F34 F 0.9884(2) 0.8738(2) -0.08290(9) 0.1059(7) Uani 1 1 d . . .
C35 C 1.1039(3) 0.8107(3) 0.03387(15) 0.0603(7) Uani 1 1 d . . .
F35 F 1.1631(2) 0.90445(17) 0.00544(10) 0.0834(5) Uani 1 1 d . . .
C36 C 1.1349(3) 0.7286(2) 0.10857(13) 0.0489(5) Uani 1 1 d . . .
F36 F 1.22410(17) 0.74467(16) 0.14954(9) 0.0659(4) Uani 1 1 d . . .
C41 C 0.8348(2) 0.7261(2) 0.23937(12) 0.0433(5) Uani 1 1 d . . .
C42 C 0.8320(3) 0.8567(2) 0.21794(13) 0.0478(5) Uani 1 1 d . . .
F42 F 0.95226(17) 0.87734(14) 0.22644(10) 0.0677(4) Uani 1 1 d . . .
C43 C 0.7124(3) 0.9706(2) 0.18682(15) 0.0621(7) Uani 1 1 d . . .
F43 F 0.7175(2) 1.09457(15) 0.16813(12) 0.0929(6) Uani 1 1 d . . .
C44 C 0.5877(3) 0.9561(3) 0.17595(18) 0.0744(8) Uani 1 1 d . . .
F44 F 0.4705(2) 1.0660(2) 0.14613(14) 0.1164(8) Uani 1 1 d . . .
C45 C 0.5830(3) 0.8300(4) 0.1966(2) 0.0790(9) Uani 1 1 d . . .
F45 F 0.4595(2) 0.8150(3) 0.18756(18) 0.1330(10) Uani 1 1 d . . .
C46 C 0.7054(3) 0.7180(3) 0.22745(17) 0.0607(7) Uani 1 1 d . . .
F46 F 0.6923(2) 0.59706(18) 0.24656(14) 0.0937(6) Uani 1 1 d . . .
C51 C 1.0315(2) 0.6251(2) 0.35087(12) 0.0438(5) Uani 1 1 d . . .
C52 C 1.1615(3) 0.6362(2) 0.35793(13) 0.0485(5) Uani 1 1 d . . .
F52 F 1.26300(16) 0.62296(15) 0.30113(8) 0.0607(4) Uani 1 1 d . . .
C53 C 1.1997(3) 0.6602(2) 0.42125(15) 0.0592(7) Uani 1 1 d . . .
F53 F 1.3291(2) 0.66799(18) 0.42415(10) 0.0821(5) Uani 1 1 d . . .
C54 C 1.1018(4) 0.6791(3) 0.48043(15) 0.0668(8) Uani 1 1 d . . .
F54 F 1.1343(3) 0.7044(2) 0.54211(10) 0.0975(6) Uani 1 1 d . . .
C55 C 0.9694(3) 0.6724(2) 0.47612(13) 0.0617(7) Uani 1 1 d . . .
F55 F 0.8704(2) 0.69237(17) 0.53351(9) 0.0863(6) Uani 1 1 d . . .
C56 C 0.9376(3) 0.6440(2) 0.41317(13) 0.0495(6) Uani 1 1 d . . .
F56 F 0.80706(16) 0.63387(15) 0.41361(8) 0.0635(4) Uani 1 1 d . . .
C101 C 0.5302(6) 0.5307(6) 0.0250(3) 0.0849(17) Uani 0.50 1 d PGDU A -1
C102 C 0.5749(5) 0.3927(6) 0.0329(3) 0.087(3) Uani 0.50 1 d PGDU A -1
H102 H 0.6482 0.3300 0.0682 0.104 Uiso 0.50 1 calc PR A -1
C103 C 0.5112(6) 0.3473(5) -0.0113(3) 0.101(2) Uani 0.50 1 d PGDU A -1
H103 H 0.5415 0.2540 -0.0059 0.121 Uiso 0.50 1 calc PR A -1
C104 C 0.4028(6) 0.4400(7) -0.0635(3) 0.106(3) Uani 0.50 1 d PGDU A -1
H104 H 0.3597 0.4093 -0.0934 0.127 Uiso 0.50 1 calc PR A -1
C105 C 0.3581(5) 0.5780(6) -0.0715(3) 0.097(2) Uani 0.50 1 d PGDU A -1
H105 H 0.2847 0.6407 -0.1068 0.117 Uiso 0.50 1 calc PR A -1
C106 C 0.4218(6) 0.6233(5) -0.0272(3) 0.083(3) Uani 0.50 1 d PGDU A -1
H106 H 0.3915 0.7167 -0.0326 0.100 Uiso 0.50 1 calc PR A -1
C107 C 0.5951(11) 0.5798(12) 0.0708(6) 0.194(6) Uani 0.50 1 d PDU A -1
H10A H 0.5474 0.5754 0.1208 0.291 Uiso 0.50 1 calc PR A -1
H10B H 0.5833 0.6729 0.0448 0.291 Uiso 0.50 1 calc PR A -1
H10C H 0.6980 0.5238 0.0774 0.291 Uiso 0.50 1 calc PR A -1


_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 C1 1.320(3) . ?
N1 C11 1.449(3) . ?
N1 H1B 0.81(2) . ?
C1 N2 1.328(3) . ?
C1 C2 1.486(3) . ?
N2 C31 1.433(3) . ?
N2 B1 1.600(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
B1 C41 1.625(3) . ?
B1 C51 1.639(3) . ?
B1 H1A 1.12(2) . ?
C11 C12 1.390(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.522(4) . ?
C13 C14 1.371(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.363(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.396(4) . ?
C15 H15 0.9400 . ?
C16 C20 1.510(4) . ?
C17 C19 1.504(4) . ?
C17 C18 1.507(5) . ?
C17 H17 0.9900 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 C21 1.524(5) . ?
C20 C22 1.525(5) . ?
C20 H20 0.9900 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C31 C32 1.376(3) . ?
C31 C36 1.383(3) . ?
C32 F32 1.341(3) . ?
C32 C33 1.380(4) . ?
C33 F33 1.341(3) . ?
C33 C34 1.369(4) . ?
C34 F34 1.337(3) . ?
C34 C35 1.354(4) . ?
C35 F35 1.341(3) . ?
C35 C36 1.386(3) . ?
C36 F36 1.324(3) . ?
C41 C46 1.378(3) . ?
C41 C42 1.381(3) . ?
C42 F42 1.344(3) . ?
C42 C43 1.380(3) . ?
C43 F43 1.342(3) . ?
C43 C44 1.363(4) . ?
C44 F44 1.341(3) . ?
C44 C45 1.361(5) . ?
C45 F45 1.344(3) . ?
C45 C46 1.386(4) . ?
C46 F46 1.343(3) . ?
C51 C52 1.378(3) . ?
C51 C56 1.389(3) . ?
C52 F52 1.352(3) . ?
C52 C53 1.385(3) . ?
C53 F53 1.337(3) . ?
C53 C54 1.367(4) . ?
C54 F54 1.341(3) . ?
C54 C55 1.367(4) . ?
C55 F55 1.351(3) . ?
C55 C56 1.378(4) . ?
C56 F56 1.351(3) . ?
C101 C102 1.3900 . ?
C101 C106 1.3900 . ?
C101 C107 1.450(9) . ?
C102 C103 1.3900 . ?
C102 H102 0.9400 . ?
C103 C104 1.3900 . ?
C103 H103 0.9400 . ?
C104 C105 1.3900 . ?
C104 H104 0.9400 . ?
C105 C106 1.3900 . ?
C105 H105 0.9400 . ?
C106 H106 0.9400 . ?
C107 H10A 0.9700 . ?
C107 H10B 0.9700 . ?
C107 H10C 0.9700 . ?

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
C1 N1 C11 126.02(19) . . ?
C1 N1 H1B 115.8(16) . . ?
C11 N1 H1B 117.1(16) . . ?
N1 C1 N2 119.04(18) . . ?
N1 C1 C2 119.42(19) . . ?
N2 C1 C2 121.53(19) . . ?
C1 N2 C31 117.68(17) . . ?
C1 N2 B1 122.19(17) . . ?
C31 N2 B1 119.09(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 B1 C41 110.35(17) . . ?
N2 B1 C51 113.83(18) . . ?
C41 B1 C51 109.82(17) . . ?
N2 B1 H1A 105.4(11) . . ?
C41 B1 H1A 110.0(12) . . ?
C51 B1 H1A 107.2(12) . . ?
C12 C11 C16 123.2(2) . . ?
C12 C11 N1 117.9(2) . . ?
C16 C11 N1 118.8(2) . . ?
C11 C12 C13 116.8(2) . . ?
C11 C12 C17 122.7(2) . . ?
C13 C12 C17 120.5(2) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 116.8(3) . . ?
C15 C16 C20 120.0(3) . . ?
C11 C16 C20 123.1(2) . . ?
C19 C17 C18 111.5(3) . . ?
C19 C17 C12 112.9(3) . . ?
C18 C17 C12 111.4(3) . . ?
C19 C17 H17 106.9 . . ?
C18 C17 H17 106.9 . . ?
C12 C17 H17 106.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 C21 110.1(3) . . ?
C16 C20 C22 113.2(3) . . ?
C21 C20 C22 111.0(3) . . ?
C16 C20 H20 107.4 . . ?
C21 C20 H20 107.4 . . ?
C22 C20 H20 107.4 . . ?
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 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C32 C31 C36 117.4(2) . . ?
C32 C31 N2 120.0(2) . . ?
C36 C31 N2 122.5(2) . . ?
F32 C32 C31 119.0(2) . . ?
F32 C32 C33 119.1(2) . . ?
C31 C32 C33 121.9(3) . . ?
F33 C33 C34 120.8(3) . . ?
F33 C33 C32 119.8(3) . . ?
C34 C33 C32 119.3(3) . . ?
F34 C34 C35 119.8(3) . . ?
F34 C34 C33 120.0(3) . . ?
C35 C34 C33 120.2(2) . . ?
F35 C35 C34 120.1(2) . . ?
F35 C35 C36 119.6(3) . . ?
C34 C35 C36 120.3(3) . . ?
F36 C36 C31 120.8(2) . . ?
F36 C36 C35 118.4(2) . . ?
C31 C36 C35 120.8(2) . . ?
C46 C41 C42 113.9(2) . . ?
C46 C41 B1 122.7(2) . . ?
C42 C41 B1 123.2(2) . . ?
F42 C42 C43 116.4(2) . . ?
F42 C42 C41 119.4(2) . . ?
C43 C42 C41 124.2(2) . . ?
F43 C43 C44 120.1(2) . . ?
F43 C43 C42 120.8(3) . . ?
C44 C43 C42 119.1(2) . . ?
F44 C44 C45 120.8(3) . . ?
F44 C44 C43 119.7(3) . . ?
C45 C44 C43 119.5(2) . . ?
F45 C45 C44 119.9(3) . . ?
F45 C45 C46 120.3(3) . . ?
C44 C45 C46 119.7(3) . . ?
F46 C46 C41 120.2(2) . . ?
F46 C46 C45 116.3(2) . . ?
C41 C46 C45 123.5(3) . . ?
C52 C51 C56 113.6(2) . . ?
C52 C51 B1 129.41(19) . . ?
C56 C51 B1 117.0(2) . . ?
F52 C52 C51 120.5(2) . . ?
F52 C52 C53 115.1(2) . . ?
C51 C52 C53 124.4(2) . . ?
F53 C53 C54 120.1(2) . . ?
F53 C53 C52 120.8(2) . . ?
C54 C53 C52 119.1(3) . . ?
F54 C54 C55 120.0(3) . . ?
F54 C54 C53 120.7(3) . . ?
C55 C54 C53 119.3(2) . . ?
F55 C55 C54 120.3(2) . . ?
F55 C55 C56 120.0(3) . . ?
C54 C55 C56 119.7(2) . . ?
F56 C56 C55 116.8(2) . . ?
F56 C56 C51 119.3(2) . . ?
C55 C56 C51 123.9(3) . . ?
C102 C101 C106 120.0 . . ?
C102 C101 C107 120.7(4) . . ?
C106 C101 C107 119.3(4) . . ?
C101 C102 C103 120.0 . . ?
C101 C102 H102 120.0 . . ?
C103 C102 H102 120.0 . . ?
C102 C103 C104 120.0 . . ?
C102 C103 H103 120.0 . . ?
C104 C103 H103 120.0 . . ?
C105 C104 C103 120.0 . . ?
C105 C104 H104 120.0 . . ?
C103 C104 H104 120.0 . . ?
C106 C105 C104 120.0 . . ?
C106 C105 H105 120.0 . . ?
C104 C105 H105 120.0 . . ?
C105 C106 C101 120.0 . . ?
C105 C106 H106 120.0 . . ?
C101 C106 H106 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 N2 175.7(2) . . . . ?
C11 N1 C1 C2 -5.3(3) . . . . ?
N1 C1 N2 C31 -174.92(19) . . . . ?
C2 C1 N2 C31 6.2(3) . . . . ?
N1 C1 N2 B1 -6.7(3) . . . . ?
C2 C1 N2 B1 174.4(2) . . . . ?
C1 N2 B1 C41 -164.40(19) . . . . ?
C31 N2 B1 C41 3.7(3) . . . . ?
C1 N2 B1 C51 71.6(2) . . . . ?
C31 N2 B1 C51 -120.3(2) . . . . ?
C1 N1 C11 C12 -99.8(3) . . . . ?
C1 N1 C11 C16 82.7(3) . . . . ?
C16 C11 C12 C13 -2.6(4) . . . . ?
N1 C11 C12 C13 -180.0(2) . . . . ?
C16 C11 C12 C17 177.3(2) . . . . ?
N1 C11 C12 C17 0.0(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C17 C12 C13 C14 -178.8(3) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?
C14 C15 C16 C20 176.9(3) . . . . ?
C12 C11 C16 C15 2.2(4) . . . . ?
N1 C11 C16 C15 179.5(2) . . . . ?
C12 C11 C16 C20 -174.9(2) . . . . ?
N1 C11 C16 C20 2.4(4) . . . . ?
C11 C12 C17 C19 -138.8(3) . . . . ?
C13 C12 C17 C19 41.2(4) . . . . ?
C11 C12 C17 C18 94.8(4) . . . . ?
C13 C12 C17 C18 -85.3(4) . . . . ?
C15 C16 C20 C21 -80.3(4) . . . . ?
C11 C16 C20 C21 96.8(3) . . . . ?
C15 C16 C20 C22 44.6(4) . . . . ?
C11 C16 C20 C22 -138.4(3) . . . . ?
C1 N2 C31 C32 88.5(3) . . . . ?
B1 N2 C31 C32 -80.1(3) . . . . ?
C1 N2 C31 C36 -94.2(2) . . . . ?
B1 N2 C31 C36 97.2(2) . . . . ?
C36 C31 C32 F32 179.1(2) . . . . ?
N2 C31 C32 F32 -3.5(3) . . . . ?
C36 C31 C32 C33 -1.0(4) . . . . ?
N2 C31 C32 C33 176.3(2) . . . . ?
F32 C32 C33 F33 -0.3(4) . . . . ?
C31 C32 C33 F33 179.9(2) . . . . ?
F32 C32 C33 C34 179.8(2) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
F33 C33 C34 F34 0.1(4) . . . . ?
C32 C33 C34 F34 180.0(3) . . . . ?
F33 C33 C34 C35 -179.4(3) . . . . ?
C32 C33 C34 C35 0.5(4) . . . . ?
F34 C34 C35 F35 -0.7(4) . . . . ?
C33 C34 C35 F35 178.8(2) . . . . ?
F34 C34 C35 C36 -179.4(2) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C32 C31 C36 F36 -177.6(2) . . . . ?
N2 C31 C36 F36 5.1(3) . . . . ?
C32 C31 C36 C35 1.6(3) . . . . ?
N2 C31 C36 C35 -175.7(2) . . . . ?
F35 C35 C36 F36 -0.7(3) . . . . ?
C34 C35 C36 F36 178.1(2) . . . . ?
F35 C35 C36 C31 -179.9(2) . . . . ?
C34 C35 C36 C31 -1.1(4) . . . . ?
N2 B1 C41 C46 105.3(2) . . . . ?
C51 B1 C41 C46 -128.4(2) . . . . ?
N2 B1 C41 C42 -79.1(3) . . . . ?
C51 B1 C41 C42 47.2(3) . . . . ?
C46 C41 C42 F42 -179.6(2) . . . . ?
B1 C41 C42 F42 4.4(3) . . . . ?
C46 C41 C42 C43 -0.4(4) . . . . ?
B1 C41 C42 C43 -176.3(2) . . . . ?
F42 C42 C43 F43 -1.5(4) . . . . ?
C41 C42 C43 F43 179.3(2) . . . . ?
F42 C42 C43 C44 179.2(2) . . . . ?
C41 C42 C43 C44 0.0(4) . . . . ?
F43 C43 C44 F44 0.4(4) . . . . ?
C42 C43 C44 F44 179.7(3) . . . . ?
F43 C43 C44 C45 -178.7(3) . . . . ?
C42 C43 C44 C45 0.6(4) . . . . ?
F44 C44 C45 F45 -0.5(5) . . . . ?
C43 C44 C45 F45 178.6(3) . . . . ?
F44 C44 C45 C46 -179.8(3) . . . . ?
C43 C44 C45 C46 -0.8(5) . . . . ?
C42 C41 C46 F46 -179.2(2) . . . . ?
B1 C41 C46 F46 -3.3(4) . . . . ?
C42 C41 C46 C45 0.2(4) . . . . ?
B1 C41 C46 C45 176.2(3) . . . . ?
F45 C45 C46 F46 0.5(5) . . . . ?
C44 C45 C46 F46 179.8(3) . . . . ?
F45 C45 C46 C41 -179.0(3) . . . . ?
C44 C45 C46 C41 0.4(5) . . . . ?
N2 B1 C51 C52 10.0(3) . . . . ?
C41 B1 C51 C52 -114.3(2) . . . . ?
N2 B1 C51 C56 -170.56(18) . . . . ?
C41 B1 C51 C56 65.2(2) . . . . ?
C56 C51 C52 F52 -178.71(19) . . . . ?
B1 C51 C52 F52 0.7(3) . . . . ?
C56 C51 C52 C53 1.7(3) . . . . ?
B1 C51 C52 C53 -178.9(2) . . . . ?
F52 C52 C53 F53 -0.5(3) . . . . ?
C51 C52 C53 F53 179.1(2) . . . . ?
F52 C52 C53 C54 178.0(2) . . . . ?
C51 C52 C53 C54 -2.3(4) . . . . ?
F53 C53 C54 F54 -0.5(4) . . . . ?
C52 C53 C54 F54 -179.1(2) . . . . ?
F53 C53 C54 C55 179.2(2) . . . . ?
C52 C53 C54 C55 0.7(4) . . . . ?
F54 C54 C55 F55 0.6(4) . . . . ?
C53 C54 C55 F55 -179.2(2) . . . . ?
F54 C54 C55 C56 -178.9(2) . . . . ?
C53 C54 C55 C56 1.4(4) . . . . ?
F55 C55 C56 F56 -1.8(3) . . . . ?
C54 C55 C56 F56 177.7(2) . . . . ?
F55 C55 C56 C51 178.5(2) . . . . ?
C54 C55 C56 C51 -2.0(4) . . . . ?
C52 C51 C56 F56 -179.17(18) . . . . ?
B1 C51 C56 F56 1.3(3) . . . . ?
C52 C51 C56 C55 0.5(3) . . . . ?
B1 C51 C56 C55 -179.0(2) . . . . ?
C106 C101 C102 C103 0.0 . . . . ?
C107 C101 C102 C103 179.8(3) . . . . ?
C101 C102 C103 C104 0.0 . . . . ?
C102 C103 C104 C105 0.0 . . . . ?
C103 C104 C105 C106 0.0 . . . . ?
C104 C105 C106 C101 0.0 . . . . ?
C102 C101 C106 C105 0.0 . . . . ?
C107 C101 C106 C105 -179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.035
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_erk6506
_audit_block_doi                 10.5517/cc148pjm
_database_code_depnum_ccdc_archive 'CCDC 1051040'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5CP00306G 2015
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 B F15 N2'
_chemical_formula_weight         728.31

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.8429(2)
_cell_length_b                   11.1654(3)
_cell_length_c                   14.1978(3)
_cell_angle_alpha                83.369(2)
_cell_angle_beta                 71.919(2)
_cell_angle_gamma                71.5990(10)
_cell_volume                     1550.15(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4014
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_T_max  0.9893
_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            14899
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5374
_reflns_number_gt                4254
_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)+(0.0226P)²+1.9888P] 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         5374
_refine_ls_number_parameters     456
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.092
_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 0.3867(3) 0.1629(3) 0.1933(2) 0.0346(7) Uani 1 1 d . . .
N1 N 0.2915(2) 0.2575(2) 0.28354(16) 0.0325(5) Uani 1 1 d . . .
N2 N 0.3138(2) 0.2800(2) 0.13320(17) 0.0350(5) Uani 1 1 d . . .
C1 C 0.2446(3) 0.3394(3) 0.2189(2) 0.0347(6) Uani 1 1 d . . .
C2 C 0.1478(3) 0.4679(3) 0.2351(2) 0.0460(7) Uani 1 1 d . . .
H2A H 0.1851 0.5263 0.1874 0.069 Uiso 1 1 calc R . .
H2B H 0.1327 0.4938 0.3017 0.069 Uiso 1 1 calc R . .
H2C H 0.0624 0.4679 0.2268 0.069 Uiso 1 1 calc R . .
C11 C 0.2310(3) 0.2554(3) 0.3890(2) 0.0380(7) Uani 1 1 d . . .
C12 C 0.0993(3) 0.2441(3) 0.4282(2) 0.0436(7) Uani 1 1 d . . .
C13 C 0.0481(4) 0.2386(4) 0.5308(3) 0.0641(10) Uani 1 1 d . . .
H13 H -0.0405 0.2324 0.5590 0.077 Uiso 1 1 calc R . .
C14 C 0.1230(4) 0.2419(5) 0.5923(3) 0.0767(12) Uani 1 1 d . . .
H14 H 0.0863 0.2370 0.6614 0.092 Uiso 1 1 calc R . .
C15 C 0.2523(4) 0.2525(4) 0.5520(3) 0.0652(10) Uani 1 1 d . . .
H15 H 0.3034 0.2540 0.5943 0.078 Uiso 1 1 calc R . .
C16 C 0.3086(3) 0.2609(3) 0.4503(2) 0.0466(8) Uani 1 1 d . . .
C17 C 0.0106(3) 0.2374(3) 0.3655(2) 0.0480(8) Uani 1 1 d . . .
H17 H 0.0621 0.2425 0.2949 0.058 Uiso 1 1 calc R . .
C18 C -0.1202(4) 0.3481(4) 0.3861(3) 0.0702(11) Uani 1 1 d . . .
H18A H -0.1782 0.3383 0.4522 0.105 Uiso 1 1 calc R . .
H18B H -0.1673 0.3495 0.3378 0.105 Uiso 1 1 calc R . .
H18C H -0.0980 0.4266 0.3814 0.105 Uiso 1 1 calc R . .
C19 C -0.0254(4) 0.1130(4) 0.3830(3) 0.0596(9) Uani 1 1 d . . .
H19A H -0.0786 0.1073 0.4514 0.089 Uiso 1 1 calc R . .
H19B H 0.0574 0.0427 0.3693 0.089 Uiso 1 1 calc R . .
H19C H -0.0778 0.1100 0.3395 0.089 Uiso 1 1 calc R . .
C20 C 0.4489(3) 0.2771(3) 0.4086(3) 0.0531(8) Uani 1 1 d . . .
H20 H 0.4682 0.2818 0.3356 0.064 Uiso 1 1 calc R . .
C21 C 0.4558(6) 0.3997(5) 0.4390(5) 0.122(2) Uani 1 1 d U . .
H21A H 0.3879 0.4698 0.4197 0.182 Uiso 1 1 calc R . .
H21B H 0.5453 0.4090 0.4066 0.182 Uiso 1 1 calc R . .
H21C H 0.4384 0.3990 0.5103 0.182 Uiso 1 1 calc R . .
C22 C 0.5588(5) 0.1648(6) 0.4316(5) 0.115(2) Uani 1 1 d . . .
H22A H 0.6474 0.1734 0.3946 0.173 Uiso 1 1 calc R . .
H22B H 0.5500 0.0877 0.4129 0.173 Uiso 1 1 calc R . .
H22C H 0.5494 0.1615 0.5020 0.173 Uiso 1 1 calc R . .
C31 C 0.2958(3) 0.3194(3) 0.0397(2) 0.0359(6) Uani 1 1 d . . .
C32 C 0.1703(3) 0.3382(3) 0.0242(2) 0.0430(7) Uani 1 1 d . . .
F32 F 0.06666(19) 0.32093(19) 0.09972(15) 0.0579(5) Uani 1 1 d . . .
C33 C 0.1506(4) 0.3698(3) -0.0675(3) 0.0547(9) Uani 1 1 d . . .
F33 F 0.0279(2) 0.3851(2) -0.07921(18) 0.0786(7) Uani 1 1 d . . .
C34 C 0.2551(4) 0.3849(3) -0.1465(3) 0.0592(10) Uani 1 1 d . . .
F34 F 0.2367(3) 0.4156(2) -0.23614(16) 0.0922(9) Uani 1 1 d . . .
C35 C 0.3793(4) 0.3688(3) -0.1338(2) 0.0557(9) Uani 1 1 d . . .
F35 F 0.4827(3) 0.3853(2) -0.21083(15) 0.0806(7) Uani 1 1 d . . .
C36 C 0.3991(3) 0.3364(3) -0.0417(2) 0.0444(7) Uani 1 1 d . . .
F36 F 0.52319(19) 0.31972(19) -0.03218(14) 0.0595(5) Uani 1 1 d . . .
C41 C 0.5488(3) 0.1408(3) 0.1693(2) 0.0362(6) Uani 1 1 d . . .
C42 C 0.6019(3) 0.2416(3) 0.1567(2) 0.0408(7) Uani 1 1 d . . .
F42 F 0.51937(17) 0.36139(15) 0.16227(14) 0.0490(5) Uani 1 1 d . . .
C43 C 0.7376(3) 0.2294(3) 0.1411(3) 0.0485(8) Uani 1 1 d . . .
F43 F 0.7802(2) 0.3315(2) 0.13048(19) 0.0744(7) Uani 1 1 d . . .
C44 C 0.8279(3) 0.1114(3) 0.1361(3) 0.0547(9) Uani 1 1 d . . .
F44 F 0.9609(2) 0.0969(2) 0.1198(2) 0.0860(8) Uani 1 1 d . . .
C45 C 0.7830(3) 0.0071(3) 0.1466(3) 0.0506(8) Uani 1 1 d . . .
F45 F 0.8709(2) -0.10941(19) 0.14111(19) 0.0739(7) Uani 1 1 d . . .
C46 C 0.6468(3) 0.0239(3) 0.1621(2) 0.0397(7) Uani 1 1 d . . .
F46 F 0.61243(18) -0.08391(16) 0.17074(15) 0.0532(5) Uani 1 1 d . . .
C51 C 0.3372(3) 0.0394(3) 0.2023(2) 0.0359(6) Uani 1 1 d . . .
C52 C 0.2884(3) 0.0022(3) 0.1347(2) 0.0406(7) Uani 1 1 d . . .
F52 F 0.2860(2) 0.06855(17) 0.04920(14) 0.0577(5) Uani 1 1 d . . .
C53 C 0.2433(3) -0.1026(3) 0.1483(2) 0.0459(8) Uani 1 1 d . . .
F53 F 0.1964(2) -0.13391(19) 0.08006(16) 0.0657(6) Uani 1 1 d . . .
C54 C 0.2479(3) -0.1761(3) 0.2316(3) 0.0503(8) Uani 1 1 d . . .
F54 F 0.2045(2) -0.2785(2) 0.24607(17) 0.0757(7) Uani 1 1 d . . .
C55 C 0.2984(3) -0.1458(3) 0.3000(2) 0.0488(8) Uani 1 1 d . . .
F55 F 0.3054(2) -0.21973(19) 0.38097(15) 0.0694(6) Uani 1 1 d . . .
C56 C 0.3408(3) -0.0401(3) 0.2843(2) 0.0400(7) Uani 1 1 d . . .
F56 F 0.3921(2) -0.01443(17) 0.35231(14) 0.0550(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N2 1.603(4) . ?
B1 C51 1.609(4) . ?
B1 N1 1.621(4) . ?
B1 C41 1.625(4) . ?
B1 C1 2.071(4) . ?
N1 C1 1.318(3) . ?
N1 C11 1.438(4) . ?
N2 C1 1.338(4) . ?
N2 C31 1.402(4) . ?
C1 C2 1.480(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C11 C12 1.403(4) . ?
C11 C16 1.403(4) . ?
C12 C13 1.390(5) . ?
C12 C17 1.522(4) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9400 . ?
C16 C20 1.512(5) . ?
C17 C18 1.531(5) . ?
C17 C19 1.532(5) . ?
C17 H17 0.9900 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 C21 1.513(6) . ?
C20 C22 1.518(6) . ?
C20 H20 0.9900 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C31 C36 1.381(4) . ?
C31 C32 1.393(4) . ?
C32 F32 1.339(4) . ?
C32 C33 1.373(5) . ?
C33 F33 1.347(4) . ?
C33 C34 1.364(5) . ?
C34 F34 1.338(4) . ?
C34 C35 1.366(5) . ?
C35 F35 1.346(4) . ?
C35 C36 1.379(5) . ?
C36 F36 1.346(4) . ?
C41 C42 1.388(4) . ?
C41 C46 1.389(4) . ?
C42 F42 1.350(3) . ?
C42 C43 1.382(4) . ?
C43 F43 1.336(4) . ?
C43 C44 1.365(5) . ?
C44 F44 1.346(4) . ?
C44 C45 1.375(5) . ?
C45 F45 1.342(4) . ?
C45 C46 1.377(4) . ?
C46 F46 1.351(3) . ?
C51 C56 1.383(4) . ?
C51 C52 1.386(4) . ?
C52 F52 1.350(3) . ?
C52 C53 1.378(4) . ?
C53 F53 1.347(3) . ?
C53 C54 1.365(5) . ?
C54 F54 1.340(3) . ?
C54 C55 1.371(5) . ?
C55 F55 1.344(4) . ?
C55 C56 1.368(4) . ?
C56 F56 1.349(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 B1 C51 115.3(2) . . ?
N2 B1 N1 79.73(19) . . ?
C51 B1 N1 110.5(2) . . ?
N2 B1 C41 113.6(2) . . ?
C51 B1 C41 117.1(2) . . ?
N1 B1 C41 115.0(2) . . ?
N2 B1 C1 40.23(14) . . ?
C51 B1 C1 119.8(2) . . ?
N1 B1 C1 39.51(13) . . ?
C41 B1 C1 123.0(2) . . ?
C1 N1 C11 126.9(2) . . ?
C1 N1 B1 89.0(2) . . ?
C11 N1 B1 140.5(2) . . ?
C1 N2 C31 127.0(2) . . ?
C1 N2 B1 89.1(2) . . ?
C31 N2 B1 143.4(2) . . ?
N1 C1 N2 102.2(2) . . ?
N1 C1 C2 129.3(3) . . ?
N2 C1 C2 128.3(3) . . ?
N1 C1 B1 51.48(16) . . ?
N2 C1 B1 50.72(16) . . ?
C2 C1 B1 177.5(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 C11 C16 121.7(3) . . ?
C12 C11 N1 120.0(2) . . ?
C16 C11 N1 118.2(3) . . ?
C13 C12 C11 117.3(3) . . ?
C13 C12 C17 118.7(3) . . ?
C11 C12 C17 124.0(3) . . ?
C14 C13 C12 122.0(3) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 118.0(3) . . ?
C15 C16 C20 120.1(3) . . ?
C11 C16 C20 121.9(3) . . ?
C12 C17 C18 111.2(3) . . ?
C12 C17 C19 111.7(3) . . ?
C18 C17 C19 109.3(3) . . ?
C12 C17 H17 108.1 . . ?
C18 C17 H17 108.1 . . ?
C19 C17 H17 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 C21 112.4(3) . . ?
C16 C20 C22 112.7(3) . . ?
C21 C20 C22 111.6(4) . . ?
C16 C20 H20 106.6 . . ?
C21 C20 H20 106.6 . . ?
C22 C20 H20 106.6 . . ?
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 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C36 C31 C32 116.5(3) . . ?
C36 C31 N2 123.4(3) . . ?
C32 C31 N2 120.1(3) . . ?
F32 C32 C33 118.6(3) . . ?
F32 C32 C31 119.4(3) . . ?
C33 C32 C31 121.9(3) . . ?
F33 C33 C34 120.2(3) . . ?
F33 C33 C32 119.7(4) . . ?
C34 C33 C32 120.1(3) . . ?
F34 C34 C33 120.4(4) . . ?
F34 C34 C35 120.0(4) . . ?
C33 C34 C35 119.6(3) . . ?
F35 C35 C34 120.2(3) . . ?
F35 C35 C36 119.5(4) . . ?
C34 C35 C36 120.2(3) . . ?
F36 C36 C35 118.6(3) . . ?
F36 C36 C31 119.7(3) . . ?
C35 C36 C31 121.7(3) . . ?
C42 C41 C46 113.2(3) . . ?
C42 C41 B1 121.5(3) . . ?
C46 C41 B1 125.3(3) . . ?
F42 C42 C43 115.2(3) . . ?
F42 C42 C41 120.4(3) . . ?
C43 C42 C41 124.4(3) . . ?
F43 C43 C44 120.3(3) . . ?
F43 C43 C42 120.6(3) . . ?
C44 C43 C42 119.1(3) . . ?
F44 C44 C43 120.3(3) . . ?
F44 C44 C45 120.0(3) . . ?
C43 C44 C45 119.7(3) . . ?
F45 C45 C44 120.4(3) . . ?
F45 C45 C46 120.6(3) . . ?
C44 C45 C46 119.1(3) . . ?
F46 C46 C45 114.8(3) . . ?
F46 C46 C41 120.8(3) . . ?
C45 C46 C41 124.4(3) . . ?
C56 C51 C52 114.2(3) . . ?
C56 C51 B1 119.5(2) . . ?
C52 C51 B1 126.3(3) . . ?
F52 C52 C53 116.5(3) . . ?
F52 C52 C51 120.0(3) . . ?
C53 C52 C51 123.5(3) . . ?
F53 C53 C54 119.9(3) . . ?
F53 C53 C52 120.9(3) . . ?
C54 C53 C52 119.2(3) . . ?
F54 C54 C53 120.1(3) . . ?
F54 C54 C55 120.1(3) . . ?
C53 C54 C55 119.9(3) . . ?
F55 C55 C56 121.1(3) . . ?
F55 C55 C54 119.8(3) . . ?
C56 C55 C54 119.2(3) . . ?
F56 C56 C55 117.5(3) . . ?
F56 C56 C51 118.5(3) . . ?
C55 C56 C51 124.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 B1 N1 C1 0.81(19) . . . . ?
C51 B1 N1 C1 -112.5(2) . . . . ?
C41 B1 N1 C1 112.2(3) . . . . ?
N2 B1 N1 C11 158.1(3) . . . . ?
C51 B1 N1 C11 44.9(4) . . . . ?
C41 B1 N1 C11 -90.5(4) . . . . ?
C1 B1 N1 C11 157.3(4) . . . . ?
C51 B1 N2 C1 107.1(3) . . . . ?
N1 B1 N2 C1 -0.79(19) . . . . ?
C41 B1 N2 C1 -113.8(3) . . . . ?
C51 B1 N2 C31 -63.5(5) . . . . ?
N1 B1 N2 C31 -171.4(4) . . . . ?
C41 B1 N2 C31 75.6(4) . . . . ?
C1 B1 N2 C31 -170.6(5) . . . . ?
C11 N1 C1 N2 -163.1(2) . . . . ?
B1 N1 C1 N2 -1.0(2) . . . . ?
C11 N1 C1 C2 20.8(5) . . . . ?
B1 N1 C1 C2 -177.0(3) . . . . ?
C11 N1 C1 B1 -162.2(3) . . . . ?
C31 N2 C1 N1 174.0(2) . . . . ?
B1 N2 C1 N1 1.0(2) . . . . ?
C31 N2 C1 C2 -9.9(5) . . . . ?
B1 N2 C1 C2 177.1(3) . . . . ?
C31 N2 C1 B1 173.0(3) . . . . ?
N2 B1 C1 N1 -178.8(3) . . . . ?
C51 B1 C1 N1 86.4(3) . . . . ?
C41 B1 C1 N1 -90.4(3) . . . . ?
C51 B1 C1 N2 -94.8(3) . . . . ?
N1 B1 C1 N2 178.8(3) . . . . ?
C41 B1 C1 N2 88.4(3) . . . . ?
N2 B1 C1 C2 -68(6) . . . . ?
C51 B1 C1 C2 -163(6) . . . . ?
N1 B1 C1 C2 110(6) . . . . ?
C41 B1 C1 C2 20(6) . . . . ?
C1 N1 C11 C12 59.2(4) . . . . ?
B1 N1 C11 C12 -92.0(4) . . . . ?
C1 N1 C11 C16 -122.7(3) . . . . ?
B1 N1 C11 C16 86.1(4) . . . . ?
C16 C11 C12 C13 0.0(5) . . . . ?
N1 C11 C12 C13 178.0(3) . . . . ?
C16 C11 C12 C17 -179.9(3) . . . . ?
N1 C11 C12 C17 -1.8(5) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C17 C12 C13 C14 178.9(4) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C14 C15 C16 C11 -1.5(6) . . . . ?
C14 C15 C16 C20 177.8(4) . . . . ?
C12 C11 C16 C15 1.2(5) . . . . ?
N1 C11 C16 C15 -176.9(3) . . . . ?
C12 C11 C16 C20 -178.1(3) . . . . ?
N1 C11 C16 C20 3.8(5) . . . . ?
C13 C12 C17 C18 61.4(4) . . . . ?
C11 C12 C17 C18 -118.7(3) . . . . ?
C13 C12 C17 C19 -61.1(4) . . . . ?
C11 C12 C17 C19 118.8(3) . . . . ?
C15 C16 C20 C21 -63.1(5) . . . . ?
C11 C16 C20 C21 116.2(4) . . . . ?
C15 C16 C20 C22 64.0(5) . . . . ?
C11 C16 C20 C22 -116.7(4) . . . . ?
C1 N2 C31 C36 124.1(3) . . . . ?
B1 N2 C31 C36 -67.6(5) . . . . ?
C1 N2 C31 C32 -58.7(4) . . . . ?
B1 N2 C31 C32 109.5(4) . . . . ?
C36 C31 C32 F32 178.8(3) . . . . ?
N2 C31 C32 F32 1.4(4) . . . . ?
C36 C31 C32 C33 1.1(4) . . . . ?
N2 C31 C32 C33 -176.3(3) . . . . ?
F32 C32 C33 F33 1.3(4) . . . . ?
C31 C32 C33 F33 179.0(3) . . . . ?
F32 C32 C33 C34 -178.3(3) . . . . ?
C31 C32 C33 C34 -0.6(5) . . . . ?
F33 C33 C34 F34 0.4(5) . . . . ?
C32 C33 C34 F34 180.0(3) . . . . ?
F33 C33 C34 C35 -179.8(3) . . . . ?
C32 C33 C34 C35 -0.2(5) . . . . ?
F34 C34 C35 F35 0.9(5) . . . . ?
C33 C34 C35 F35 -179.0(3) . . . . ?
F34 C34 C35 C36 -179.7(3) . . . . ?
C33 C34 C35 C36 0.5(5) . . . . ?
F35 C35 C36 F36 -1.3(5) . . . . ?
C34 C35 C36 F36 179.2(3) . . . . ?
F35 C35 C36 C31 179.5(3) . . . . ?
C34 C35 C36 C31 0.0(5) . . . . ?
C32 C31 C36 F36 -179.9(3) . . . . ?
N2 C31 C36 F36 -2.7(4) . . . . ?
C32 C31 C36 C35 -0.8(4) . . . . ?
N2 C31 C36 C35 176.5(3) . . . . ?
N2 B1 C41 C42 39.4(4) . . . . ?
C51 B1 C41 C42 177.7(3) . . . . ?
N1 B1 C41 C42 -50.0(4) . . . . ?
C1 B1 C41 C42 -5.4(4) . . . . ?
N2 B1 C41 C46 -142.5(3) . . . . ?
C51 B1 C41 C46 -4.2(4) . . . . ?
N1 B1 C41 C46 128.1(3) . . . . ?
C1 B1 C41 C46 172.7(3) . . . . ?
C46 C41 C42 F42 -179.6(3) . . . . ?
B1 C41 C42 F42 -1.3(4) . . . . ?
C46 C41 C42 C43 -1.6(5) . . . . ?
B1 C41 C42 C43 176.7(3) . . . . ?
F42 C42 C43 F43 -1.4(5) . . . . ?
C41 C42 C43 F43 -179.5(3) . . . . ?
F42 C42 C43 C44 179.0(3) . . . . ?
C41 C42 C43 C44 0.9(5) . . . . ?
F43 C43 C44 F44 -0.4(6) . . . . ?
C42 C43 C44 F44 179.2(3) . . . . ?
F43 C43 C44 C45 -179.6(3) . . . . ?
C42 C43 C44 C45 0.0(6) . . . . ?
F44 C44 C45 F45 0.3(6) . . . . ?
C43 C44 C45 F45 179.5(3) . . . . ?
F44 C44 C45 C46 -179.2(3) . . . . ?
C43 C44 C45 C46 -0.1(6) . . . . ?
F45 C45 C46 F46 -0.1(5) . . . . ?
C44 C45 C46 F46 179.5(3) . . . . ?
F45 C45 C46 C41 179.6(3) . . . . ?
C44 C45 C46 C41 -0.8(5) . . . . ?
C42 C41 C46 F46 -178.8(3) . . . . ?
B1 C41 C46 F46 3.1(5) . . . . ?
C42 C41 C46 C45 1.6(5) . . . . ?
B1 C41 C46 C45 -176.6(3) . . . . ?
N2 B1 C51 C56 -150.2(3) . . . . ?
N1 B1 C51 C56 -62.1(3) . . . . ?
C41 B1 C51 C56 72.2(4) . . . . ?
C1 B1 C51 C56 -104.8(3) . . . . ?
N2 B1 C51 C52 29.4(4) . . . . ?
N1 B1 C51 C52 117.4(3) . . . . ?
C41 B1 C51 C52 -108.3(3) . . . . ?
C1 B1 C51 C52 74.7(4) . . . . ?
C56 C51 C52 F52 -176.8(3) . . . . ?
B1 C51 C52 F52 3.7(5) . . . . ?
C56 C51 C52 C53 1.7(4) . . . . ?
B1 C51 C52 C53 -177.8(3) . . . . ?
F52 C52 C53 F53 -1.6(4) . . . . ?
C51 C52 C53 F53 179.7(3) . . . . ?
F52 C52 C53 C54 177.6(3) . . . . ?
C51 C52 C53 C54 -1.0(5) . . . . ?
F53 C53 C54 F54 -0.7(5) . . . . ?
C52 C53 C54 F54 180.0(3) . . . . ?
F53 C53 C54 C55 178.6(3) . . . . ?
C52 C53 C54 C55 -0.7(5) . . . . ?
F54 C54 C55 F55 0.7(5) . . . . ?
C53 C54 C55 F55 -178.6(3) . . . . ?
F54 C54 C55 C56 -179.3(3) . . . . ?
C53 C54 C55 C56 1.4(5) . . . . ?
F55 C55 C56 F56 1.2(5) . . . . ?
C54 C55 C56 F56 -178.8(3) . . . . ?
F55 C55 C56 C51 179.5(3) . . . . ?
C54 C55 C56 C51 -0.5(5) . . . . ?
C52 C51 C56 F56 177.3(3) . . . . ?
B1 C51 C56 F56 -3.1(4) . . . . ?
C52 C51 C56 C55 -1.0(4) . . . . ?
B1 C51 C56 C55 178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.047
#=============================================================================
#  end of cif data for "erk6506"
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

