# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_erk8479
_database_code_depnum_ccdc_archive 'CCDC 1843575'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 B F10 N'
_chemical_formula_weight         525.24

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                   13.7333(3)
_cell_length_b                   13.9943(3)
_cell_length_c                   14.2142(5)
_cell_angle_alpha                75.8940(10)
_cell_angle_beta                 88.5530(10)
_cell_angle_gamma                64.471(2)
_cell_volume                     2380.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7381
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9889
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            24670
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8215
_reflns_number_gt                5157
_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+5.7882P] 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         8215
_refine_ls_number_parameters     659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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 1.0423(3) 0.1727(3) 0.0989(3) 0.0392(9) Uani 1 1 d . . .
B1A B 0.8632(4) 0.0341(4) 0.1903(4) 0.0391(13) Uani 1 1 d . . .
C1A C 0.9900(3) 0.1140(4) 0.1414(3) 0.0376(11) Uani 1 1 d . . .
H1A H 1.0165 0.0773 0.2076 0.045 Uiso 1 1 calc R . .
C2A C 0.9059(4) 0.0938(4) 0.1117(3) 0.0392(11) Uani 1 1 d . . .
C3A C 0.8671(4) 0.1177(4) 0.0048(3) 0.0497(13) Uani 1 1 d . . .
H301 H 0.8236 0.1968 -0.0213 0.075 Uiso 1 1 calc R . .
H302 H 0.8230 0.0793 0.0000 0.075 Uiso 1 1 calc R . .
H303 H 0.9300 0.0923 -0.0327 0.075 Uiso 1 1 calc R . .
C11A C 1.1547(4) 0.1381(4) 0.1475(4) 0.0467(13) Uani 1 1 d . . .
C12A C 1.2181(5) 0.1771(6) 0.0717(5) 0.0752(19) Uani 1 1 d . . .
H12A H 1.2915 0.1540 0.1020 0.090 Uiso 1 1 calc R . .
H12B H 1.2265 0.1402 0.0188 0.090 Uiso 1 1 calc R . .
C13A C 1.1676(6) 0.2994(7) 0.0275(5) 0.095(3) Uani 1 1 d . . .
H13A H 1.1850 0.3145 -0.0409 0.114 Uiso 1 1 calc R . .
H13B H 1.1989 0.3334 0.0636 0.114 Uiso 1 1 calc R . .
C14A C 1.0460(5) 0.3502(5) 0.0306(5) 0.0707(18) Uani 1 1 d . . .
H14A H 1.0139 0.4191 -0.0219 0.085 Uiso 1 1 calc R . .
H14B H 1.0292 0.3698 0.0934 0.085 Uiso 1 1 calc R . .
C15A C 0.9913(4) 0.2785(4) 0.0194(4) 0.0484(13) Uani 1 1 d . . .
C16A C 1.2134(4) 0.0126(5) 0.1803(5) 0.0699(18) Uani 1 1 d . . .
H16A H 1.2899 -0.0106 0.1994 0.105 Uiso 1 1 calc R . .
H16B H 1.2078 -0.0177 0.1265 0.105 Uiso 1 1 calc R . .
H16C H 1.1800 -0.0140 0.2359 0.105 Uiso 1 1 calc R . .
C17A C 1.1463(5) 0.1823(5) 0.2366(4) 0.0594(15) Uani 1 1 d . . .
H17A H 1.2185 0.1517 0.2710 0.089 Uiso 1 1 calc R . .
H17B H 1.0984 0.1614 0.2802 0.089 Uiso 1 1 calc R . .
H17C H 1.1167 0.2624 0.2161 0.089 Uiso 1 1 calc R . .
C18A C 1.0059(5) 0.2573(5) -0.0826(4) 0.0677(17) Uani 1 1 d . . .
H18A H 1.0833 0.2226 -0.0915 0.102 Uiso 1 1 calc R . .
H18B H 0.9702 0.3271 -0.1323 0.102 Uiso 1 1 calc R . .
H18C H 0.9734 0.2088 -0.0890 0.102 Uiso 1 1 calc R . .
C19A C 0.8729(4) 0.3409(4) 0.0358(4) 0.0637(16) Uani 1 1 d . . .
H19A H 0.8335 0.2986 0.0288 0.095 Uiso 1 1 calc R . .
H19B H 0.8409 0.4121 -0.0123 0.095 Uiso 1 1 calc R . .
H19C H 0.8680 0.3520 0.1015 0.095 Uiso 1 1 calc R . .
C21A C 0.9179(4) -0.0219(4) 0.2997(3) 0.0368(11) Uani 1 1 d . . .
F22A F 1.0804(2) -0.1484(2) 0.2556(2) 0.0558(8) Uani 1 1 d . . .
C22A C 1.0197(4) -0.1096(4) 0.3253(4) 0.0402(11) Uani 1 1 d . . .
F23A F 1.1628(2) -0.2431(2) 0.4417(2) 0.0633(9) Uani 1 1 d . . .
C23A C 1.0623(4) -0.1604(4) 0.4204(4) 0.0452(13) Uani 1 1 d . . .
F24A F 1.0446(2) -0.1740(2) 0.5875(2) 0.0613(8) Uani 1 1 d . . .
C24A C 1.0031(4) -0.1254(4) 0.4947(4) 0.0433(12) Uani 1 1 d . . .
F25A F 0.8444(2) -0.0022(2) 0.5449(2) 0.0577(8) Uani 1 1 d . . .
C25A C 0.9018(4) -0.0394(4) 0.4729(4) 0.0427(12) Uani 1 1 d . . .
F26A F 0.7618(2) 0.0949(2) 0.3589(2) 0.0509(7) Uani 1 1 d . . .
C26A C 0.8613(4) 0.0096(4) 0.3768(4) 0.0412(12) Uani 1 1 d . . .
C31A C 0.7596(4) 0.0170(4) 0.1696(3) 0.0430(12) Uani 1 1 d . . .
F32A F 0.8487(2) -0.1722(2) 0.2459(2) 0.0585(8) Uani 1 1 d . . .
C32A C 0.7599(4) -0.0855(4) 0.1972(4) 0.0488(13) Uani 1 1 d . . .
F33A F 0.6785(3) -0.2052(3) 0.2062(3) 0.0819(11) Uani 1 1 d . . .
C33A C 0.6731(5) -0.1045(5) 0.1768(4) 0.0534(14) Uani 1 1 d . . .
F34A F 0.4937(3) -0.0347(3) 0.1094(3) 0.0834(11) Uani 1 1 d . . .
C34A C 0.5804(5) -0.0185(5) 0.1284(4) 0.0600(16) Uani 1 1 d . . .
F35A F 0.4814(3) 0.1701(3) 0.0556(3) 0.0820(11) Uani 1 1 d . . .
C35A C 0.5737(4) 0.0850(5) 0.1014(4) 0.0553(15) Uani 1 1 d . . .
F36A F 0.6513(2) 0.2044(2) 0.0950(2) 0.0647(9) Uani 1 1 d . . .
C36A C 0.6623(4) 0.1006(4) 0.1217(4) 0.0492(13) Uani 1 1 d . . .
N1B N 0.5096(3) 0.5080(3) 0.2662(3) 0.0362(9) Uani 1 1 d . . .
B1B B 0.3348(5) 0.3727(5) 0.3750(4) 0.0430(14) Uani 1 1 d . . .
C1B C 0.4594(4) 0.4500(4) 0.3149(3) 0.0370(11) Uani 1 1 d . . .
H1B H 0.5087 0.3779 0.3492 0.044 Uiso 1 1 calc R . .
C2B C 0.3523(4) 0.4706(4) 0.3269(4) 0.0422(12) Uani 1 1 d . . .
C3B C 0.2596(4) 0.5851(4) 0.3069(4) 0.0537(14) Uani 1 1 d . . .
H311 H 0.2872 0.6367 0.3155 0.081 Uiso 1 1 calc R . .
H312 H 0.2048 0.5853 0.3525 0.081 Uiso 1 1 calc R . .
H313 H 0.2271 0.6072 0.2400 0.081 Uiso 1 1 calc R . .
C11B C 0.6257(4) 0.4700(4) 0.3056(4) 0.0430(12) Uani 1 1 d . . .
C12B C 0.6601(4) 0.5604(4) 0.2628(4) 0.0484(13) Uani 1 1 d . . .
H12C H 0.6138 0.6261 0.2853 0.058 Uiso 1 1 calc R . .
H12D H 0.7357 0.5360 0.2885 0.058 Uiso 1 1 calc R . .
C13B C 0.6532(4) 0.5926(4) 0.1521(4) 0.0531(14) Uani 1 1 d . . .
H13C H 0.6386 0.6707 0.1289 0.064 Uiso 1 1 calc R . .
H13D H 0.7235 0.5481 0.1301 0.064 Uiso 1 1 calc R . .
C14B C 0.5643(4) 0.5753(4) 0.1084(4) 0.0501(13) Uani 1 1 d . . .
H14C H 0.5961 0.5003 0.0991 0.060 Uiso 1 1 calc R . .
H14D H 0.5380 0.6273 0.0433 0.060 Uiso 1 1 calc R . .
C15B C 0.4671(4) 0.5900(4) 0.1681(3) 0.0418(12) Uani 1 1 d . . .
C16B C 0.6286(4) 0.4547(4) 0.4164(4) 0.0534(14) Uani 1 1 d . . .
H16D H 0.6993 0.4441 0.4415 0.080 Uiso 1 1 calc R . .
H16E H 0.6167 0.3903 0.4472 0.080 Uiso 1 1 calc R . .
H16F H 0.5715 0.5199 0.4312 0.080 Uiso 1 1 calc R . .
C17B C 0.7011(4) 0.3622(4) 0.2823(4) 0.0602(15) Uani 1 1 d . . .
H17D H 0.6989 0.3726 0.2116 0.090 Uiso 1 1 calc R . .
H17E H 0.6774 0.3057 0.3119 0.090 Uiso 1 1 calc R . .
H17F H 0.7753 0.3393 0.3087 0.090 Uiso 1 1 calc R . .
C18B C 0.3935(4) 0.5619(5) 0.1125(4) 0.0577(15) Uani 1 1 d . . .
H18D H 0.4315 0.4851 0.1103 0.086 Uiso 1 1 calc R . .
H18E H 0.3744 0.6094 0.0460 0.086 Uiso 1 1 calc R . .
H18F H 0.3274 0.5733 0.1455 0.086 Uiso 1 1 calc R . .
C19B C 0.4105(4) 0.7081(4) 0.1755(4) 0.0521(14) Uani 1 1 d . . .
H19D H 0.3455 0.7187 0.2102 0.078 Uiso 1 1 calc R . .
H19E H 0.3897 0.7578 0.1099 0.078 Uiso 1 1 calc R . .
H19F H 0.4598 0.7236 0.2111 0.078 Uiso 1 1 calc R . .
C21B C 0.4310(4) 0.2524(4) 0.4122(4) 0.0398(11) Uani 1 1 d . . .
F22B F 0.4763(2) 0.2840(2) 0.5570(2) 0.0627(9) Uani 1 1 d . . .
C22B C 0.4941(4) 0.2158(4) 0.4990(4) 0.0436(12) Uani 1 1 d . . .
F23B F 0.6326(3) 0.0795(3) 0.6185(2) 0.0738(10) Uani 1 1 d . . .
C23B C 0.5757(4) 0.1112(4) 0.5322(4) 0.0488(13) Uani 1 1 d . . .
F24B F 0.6769(2) -0.0637(2) 0.5065(3) 0.0736(10) Uani 1 1 d . . .
C24B C 0.5971(4) 0.0391(4) 0.4761(4) 0.0516(14) Uani 1 1 d . . .
F25B F 0.5587(3) -0.0006(3) 0.3353(3) 0.0787(10) Uani 1 1 d . . .
C25B C 0.5372(4) 0.0714(4) 0.3895(4) 0.0523(14) Uani 1 1 d . . .
F26B F 0.3986(3) 0.2042(3) 0.2729(2) 0.0660(9) Uani 1 1 d . . .
C26B C 0.4560(4) 0.1761(4) 0.3594(4) 0.0448(12) Uani 1 1 d . . .
C31B C 0.2157(4) 0.3825(4) 0.3885(4) 0.0430(12) Uani 1 1 d . . .
F32B F 0.2533(2) 0.3092(3) 0.5585(2) 0.0683(9) Uani 1 1 d . . .
C32B C 0.1825(4) 0.3510(4) 0.4787(4) 0.0510(14) Uani 1 1 d . . .
F33B F 0.0495(3) 0.3340(3) 0.5826(2) 0.0776(11) Uani 1 1 d . . .
C33B C 0.0786(4) 0.3625(4) 0.4935(4) 0.0528(14) Uani 1 1 d . . .
F34B F -0.0976(2) 0.4173(3) 0.4270(3) 0.0765(10) Uani 1 1 d . . .
C34B C 0.0037(4) 0.4057(4) 0.4140(4) 0.0541(14) Uani 1 1 d . . .
F35B F -0.0412(2) 0.4783(3) 0.2456(2) 0.0783(11) Uani 1 1 d . . .
C35B C 0.0323(4) 0.4366(4) 0.3234(4) 0.0532(14) Uani 1 1 d . . .
F36B F 0.1605(2) 0.4554(3) 0.2203(2) 0.0650(9) Uani 1 1 d . . .
C36B C 0.1359(4) 0.4256(4) 0.3117(4) 0.0475(13) 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
N1A C1A 1.341(6) . ?
N1A C15A 1.513(6) . ?
N1A C11A 1.530(5) . ?
B1A C2A 1.491(7) . ?
B1A C31A 1.586(7) . ?
B1A C21A 1.598(7) . ?
C1A C2A 1.399(6) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.531(6) . ?
C3A H301 0.9800 . ?
C3A H302 0.9800 . ?
C3A H303 0.9800 . ?
C11A C12A 1.514(7) . ?
C11A C17A 1.522(7) . ?
C11A C16A 1.533(7) . ?
C12A C13A 1.510(9) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.511(9) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.528(7) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C19A 1.523(7) . ?
C15A C18A 1.540(7) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C21A C26A 1.377(7) . ?
C21A C22A 1.386(6) . ?
F22A C22A 1.343(5) . ?
C22A C23A 1.374(6) . ?
F23A C23A 1.346(5) . ?
C23A C24A 1.371(7) . ?
F24A C24A 1.340(5) . ?
C24A C25A 1.370(7) . ?
F25A C25A 1.344(6) . ?
C25A C26A 1.377(6) . ?
F26A C26A 1.349(5) . ?
C31A C36A 1.389(6) . ?
C31A C32A 1.390(7) . ?
F32A C32A 1.341(5) . ?
C32A C33A 1.380(7) . ?
F33A C33A 1.338(6) . ?
C33A C34A 1.364(8) . ?
F34A C34A 1.350(5) . ?
C34A C35A 1.367(8) . ?
F35A C35A 1.346(6) . ?
C35A C36A 1.375(7) . ?
F36A C36A 1.349(6) . ?
N1B C1B 1.341(6) . ?
N1B C15B 1.512(6) . ?
N1B C11B 1.519(5) . ?
B1B C2B 1.491(7) . ?
B1B C31B 1.591(7) . ?
B1B C21B 1.595(7) . ?
C1B C2B 1.385(6) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.519(6) . ?
C3B H311 0.9800 . ?
C3B H312 0.9800 . ?
C3B H313 0.9800 . ?
C11B C12B 1.523(6) . ?
C11B C17B 1.528(7) . ?
C11B C16B 1.537(7) . ?
C12B C13B 1.521(7) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.517(7) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.528(7) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C19B 1.523(6) . ?
C15B C18B 1.528(6) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C21B C26B 1.372(7) . ?
C21B C22B 1.378(6) . ?
F22B C22B 1.351(5) . ?
C22B C23B 1.377(7) . ?
F23B C23B 1.341(6) . ?
C23B C24B 1.364(7) . ?
F24B C24B 1.349(6) . ?
C24B C25B 1.362(7) . ?
F25B C25B 1.344(6) . ?
C25B C26B 1.373(7) . ?
F26B C26B 1.354(5) . ?
C31B C32B 1.384(7) . ?
C31B C36B 1.389(6) . ?
F32B C32B 1.348(5) . ?
C32B C33B 1.381(7) . ?
F33B C33B 1.337(6) . ?
C33B C34B 1.375(7) . ?
F34B C34B 1.343(5) . ?
C34B C35B 1.360(7) . ?
F35B C35B 1.347(6) . ?
C35B C36B 1.374(7) . ?
F36B C36B 1.345(6) . ?

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
C1A N1A C15A 124.5(4) . . ?
C1A N1A C11A 115.7(4) . . ?
C15A N1A C11A 119.0(4) . . ?
C2A B1A C31A 121.5(4) . . ?
C2A B1A C21A 124.4(4) . . ?
C31A B1A C21A 114.0(4) . . ?
N1A C1A C2A 135.5(4) . . ?
N1A C1A H1A 112.3 . . ?
C2A C1A H1A 112.3 . . ?
C1A C2A B1A 116.0(4) . . ?
C1A C2A C3A 123.4(4) . . ?
B1A C2A C3A 120.2(4) . . ?
C2A C3A H301 109.5 . . ?
C2A C3A H302 109.5 . . ?
H301 C3A H302 109.5 . . ?
C2A C3A H303 109.5 . . ?
H301 C3A H303 109.5 . . ?
H302 C3A H303 109.5 . . ?
C12A C11A C17A 112.6(5) . . ?
C12A C11A N1A 107.8(4) . . ?
C17A C11A N1A 111.0(4) . . ?
C12A C11A C16A 108.0(5) . . ?
C17A C11A C16A 108.4(4) . . ?
N1A C11A C16A 109.0(4) . . ?
C13A C12A C11A 114.8(5) . . ?
C13A C12A H12A 108.6 . . ?
C11A C12A H12A 108.6 . . ?
C13A C12A H12B 108.6 . . ?
C11A C12A H12B 108.6 . . ?
H12A C12A H12B 107.6 . . ?
C12A C13A C14A 111.6(5) . . ?
C12A C13A H13A 109.3 . . ?
C14A C13A H13A 109.3 . . ?
C12A C13A H13B 109.3 . . ?
C14A C13A H13B 109.3 . . ?
H13A C13A H13B 108.0 . . ?
C13A C14A C15A 115.5(6) . . ?
C13A C14A H14A 108.4 . . ?
C15A C14A H14A 108.4 . . ?
C13A C14A H14B 108.4 . . ?
C15A C14A H14B 108.4 . . ?
H14A C14A H14B 107.5 . . ?
N1A C15A C19A 109.1(4) . . ?
N1A C15A C14A 107.9(4) . . ?
C19A C15A C14A 106.0(5) . . ?
N1A C15A C18A 111.6(4) . . ?
C19A C15A C18A 112.7(5) . . ?
C14A C15A C18A 109.4(5) . . ?
C11A C16A H16A 109.5 . . ?
C11A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C11A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C11A C17A H17A 109.5 . . ?
C11A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C11A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C15A C18A H18A 109.5 . . ?
C15A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C15A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C15A C19A H19A 109.5 . . ?
C15A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C15A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C26A C21A C22A 115.1(4) . . ?
C26A C21A B1A 120.8(4) . . ?
C22A C21A B1A 123.9(5) . . ?
F22A C22A C23A 117.5(4) . . ?
F22A C22A C21A 119.8(4) . . ?
C23A C22A C21A 122.7(5) . . ?
F23A C23A C24A 119.3(4) . . ?
F23A C23A C22A 120.7(5) . . ?
C24A C23A C22A 120.0(4) . . ?
F24A C24A C25A 120.4(5) . . ?
F24A C24A C23A 120.3(4) . . ?
C25A C24A C23A 119.3(4) . . ?
F25A C25A C24A 119.8(4) . . ?
F25A C25A C26A 120.9(4) . . ?
C24A C25A C26A 119.3(5) . . ?
F26A C26A C25A 117.1(5) . . ?
F26A C26A C21A 119.3(4) . . ?
C25A C26A C21A 123.6(4) . . ?
C36A C31A C32A 114.0(4) . . ?
C36A C31A B1A 124.0(4) . . ?
C32A C31A B1A 122.0(4) . . ?
F32A C32A C33A 116.9(5) . . ?
F32A C32A C31A 119.4(4) . . ?
C33A C32A C31A 123.7(5) . . ?
F33A C33A C34A 120.4(5) . . ?
F33A C33A C32A 120.6(5) . . ?
C34A C33A C32A 119.0(5) . . ?
F34A C34A C33A 120.1(5) . . ?
F34A C34A C35A 119.6(5) . . ?
C33A C34A C35A 120.3(5) . . ?
F35A C35A C34A 120.2(5) . . ?
F35A C35A C36A 120.7(5) . . ?
C34A C35A C36A 119.1(5) . . ?
F36A C36A C35A 116.9(5) . . ?
F36A C36A C31A 119.2(4) . . ?
C35A C36A C31A 123.8(5) . . ?
C1B N1B C15B 124.4(4) . . ?
C1B N1B C11B 115.1(4) . . ?
C15B N1B C11B 119.4(4) . . ?
C2B B1B C31B 120.9(4) . . ?
C2B B1B C21B 123.4(4) . . ?
C31B B1B C21B 115.8(4) . . ?
N1B C1B C2B 135.0(4) . . ?
N1B C1B H1B 112.5 . . ?
C2B C1B H1B 112.5 . . ?
C1B C2B B1B 115.1(4) . . ?
C1B C2B C3B 123.6(4) . . ?
B1B C2B C3B 120.7(4) . . ?
C2B C3B H311 109.5 . . ?
C2B C3B H312 109.5 . . ?
H311 C3B H312 109.5 . . ?
C2B C3B H313 109.5 . . ?
H311 C3B H313 109.5 . . ?
H312 C3B H313 109.5 . . ?
N1B C11B C12B 108.6(4) . . ?
N1B C11B C17B 111.0(4) . . ?
C12B C11B C17B 111.7(4) . . ?
N1B C11B C16B 108.2(4) . . ?
C12B C11B C16B 107.3(4) . . ?
C17B C11B C16B 109.9(4) . . ?
C13B C12B C11B 114.3(4) . . ?
C13B C12B H12C 108.7 . . ?
C11B C12B H12C 108.7 . . ?
C13B C12B H12D 108.7 . . ?
C11B C12B H12D 108.7 . . ?
H12C C12B H12D 107.6 . . ?
C14B C13B C12B 111.1(4) . . ?
C14B C13B H13C 109.4 . . ?
C12B C13B H13C 109.4 . . ?
C14B C13B H13D 109.4 . . ?
C12B C13B H13D 109.4 . . ?
H13C C13B H13D 108.0 . . ?
C13B C14B C15B 115.6(4) . . ?
C13B C14B H14C 108.4 . . ?
C15B C14B H14C 108.4 . . ?
C13B C14B H14D 108.4 . . ?
C15B C14B H14D 108.4 . . ?
H14C C14B H14D 107.4 . . ?
N1B C15B C19B 112.9(4) . . ?
N1B C15B C18B 110.3(4) . . ?
C19B C15B C18B 111.4(4) . . ?
N1B C15B C14B 107.0(4) . . ?
C19B C15B C14B 109.4(4) . . ?
C18B C15B C14B 105.4(4) . . ?
C11B C16B H16D 109.5 . . ?
C11B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C11B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C11B C17B H17D 109.5 . . ?
C11B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C11B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C15B C18B H18D 109.5 . . ?
C15B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C15B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C15B C19B H19D 109.5 . . ?
C15B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C15B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C26B C21B C22B 114.7(4) . . ?
C26B C21B B1B 121.6(4) . . ?
C22B C21B B1B 123.7(5) . . ?
F22B C22B C23B 116.6(4) . . ?
F22B C22B C21B 119.7(4) . . ?
C23B C22B C21B 123.8(5) . . ?
F23B C23B C24B 120.1(5) . . ?
F23B C23B C22B 121.0(5) . . ?
C24B C23B C22B 118.9(5) . . ?
F24B C24B C25B 120.1(5) . . ?
F24B C24B C23B 120.2(5) . . ?
C25B C24B C23B 119.6(5) . . ?
F25B C25B C24B 119.1(5) . . ?
F25B C25B C26B 121.2(5) . . ?
C24B C25B C26B 119.7(5) . . ?
F26B C26B C21B 119.2(4) . . ?
F26B C26B C25B 117.5(5) . . ?
C21B C26B C25B 123.3(5) . . ?
C32B C31B C36B 114.4(4) . . ?
C32B C31B B1B 122.5(4) . . ?
C36B C31B B1B 123.1(5) . . ?
F32B C32B C33B 116.8(5) . . ?
F32B C32B C31B 119.2(4) . . ?
C33B C32B C31B 124.0(5) . . ?
F33B C33B C34B 119.8(5) . . ?
F33B C33B C32B 121.7(5) . . ?
C34B C33B C32B 118.5(5) . . ?
F34B C34B C35B 120.6(5) . . ?
F34B C34B C33B 119.3(5) . . ?
C35B C34B C33B 120.1(5) . . ?
F35B C35B C34B 119.9(5) . . ?
F35B C35B C36B 120.3(5) . . ?
C34B C35B C36B 119.8(5) . . ?
F36B C36B C35B 117.4(4) . . ?
F36B C36B C31B 119.3(4) . . ?
C35B C36B C31B 123.3(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
C15A N1A C1A C2A 32.0(8) . . . . ?
C11A N1A C1A C2A -158.4(5) . . . . ?
N1A C1A C2A B1A -171.5(5) . . . . ?
N1A C1A C2A C3A 15.7(9) . . . . ?
C31A B1A C2A C1A 173.1(4) . . . . ?
C21A B1A C2A C1A -9.4(7) . . . . ?
C31A B1A C2A C3A -13.8(7) . . . . ?
C21A B1A C2A C3A 163.7(5) . . . . ?
C1A N1A C11A C12A 156.9(5) . . . . ?
C15A N1A C11A C12A -32.9(6) . . . . ?
C1A N1A C11A C17A -79.3(5) . . . . ?
C15A N1A C11A C17A 90.9(5) . . . . ?
C1A N1A C11A C16A 39.9(6) . . . . ?
C15A N1A C11A C16A -149.9(5) . . . . ?
C17A C11A C12A C13A -63.5(7) . . . . ?
N1A C11A C12A C13A 59.3(7) . . . . ?
C16A C11A C12A C13A 176.9(5) . . . . ?
C11A C12A C13A C14A -26.8(8) . . . . ?
C12A C13A C14A C15A -33.5(8) . . . . ?
C1A N1A C15A C19A 33.4(6) . . . . ?
C11A N1A C15A C19A -135.9(4) . . . . ?
C1A N1A C15A C14A 148.1(5) . . . . ?
C11A N1A C15A C14A -21.2(6) . . . . ?
C1A N1A C15A C18A -91.7(6) . . . . ?
C11A N1A C15A C18A 99.0(5) . . . . ?
C13A C14A C15A N1A 57.2(6) . . . . ?
C13A C14A C15A C19A 173.9(5) . . . . ?
C13A C14A C15A C18A -64.3(6) . . . . ?
C2A B1A C21A C26A 120.8(5) . . . . ?
C31A B1A C21A C26A -61.6(6) . . . . ?
C2A B1A C21A C22A -64.7(7) . . . . ?
C31A B1A C21A C22A 112.9(5) . . . . ?
C26A C21A C22A F22A 178.4(4) . . . . ?
B1A C21A C22A F22A 3.6(7) . . . . ?
C26A C21A C22A C23A -1.2(7) . . . . ?
B1A C21A C22A C23A -176.0(4) . . . . ?
F22A C22A C23A F23A 2.5(7) . . . . ?
C21A C22A C23A F23A -177.9(4) . . . . ?
F22A C22A C23A C24A -178.9(4) . . . . ?
C21A C22A C23A C24A 0.7(7) . . . . ?
F23A C23A C24A F24A -0.7(7) . . . . ?
C22A C23A C24A F24A -179.4(4) . . . . ?
F23A C23A C24A C25A 178.4(4) . . . . ?
C22A C23A C24A C25A -0.3(7) . . . . ?
F24A C24A C25A F25A 1.2(7) . . . . ?
C23A C24A C25A F25A -177.9(4) . . . . ?
F24A C24A C25A C26A 179.5(4) . . . . ?
C23A C24A C25A C26A 0.4(7) . . . . ?
F25A C25A C26A F26A -0.8(6) . . . . ?
C24A C25A C26A F26A -179.2(4) . . . . ?
F25A C25A C26A C21A 177.3(4) . . . . ?
C24A C25A C26A C21A -1.1(7) . . . . ?
C22A C21A C26A F26A 179.5(4) . . . . ?
B1A C21A C26A F26A -5.5(6) . . . . ?
C22A C21A C26A C25A 1.4(7) . . . . ?
B1A C21A C26A C25A 176.4(4) . . . . ?
C2A B1A C31A C36A -49.7(7) . . . . ?
C21A B1A C31A C36A 132.5(5) . . . . ?
C2A B1A C31A C32A 129.1(5) . . . . ?
C21A B1A C31A C32A -48.6(7) . . . . ?
C36A C31A C32A F32A -178.6(5) . . . . ?
B1A C31A C32A F32A 2.5(8) . . . . ?
C36A C31A C32A C33A 1.9(8) . . . . ?
B1A C31A C32A C33A -177.0(5) . . . . ?
F32A C32A C33A F33A 1.0(8) . . . . ?
C31A C32A C33A F33A -179.5(5) . . . . ?
F32A C32A C33A C34A 179.2(5) . . . . ?
C31A C32A C33A C34A -1.3(9) . . . . ?
F33A C33A C34A F34A -0.4(8) . . . . ?
C32A C33A C34A F34A -178.6(5) . . . . ?
F33A C33A C34A C35A 177.7(5) . . . . ?
C32A C33A C34A C35A -0.4(9) . . . . ?
F34A C34A C35A F35A -0.3(9) . . . . ?
C33A C34A C35A F35A -178.5(5) . . . . ?
F34A C34A C35A C36A 179.5(5) . . . . ?
C33A C34A C35A C36A 1.3(9) . . . . ?
F35A C35A C36A F36A 0.8(8) . . . . ?
C34A C35A C36A F36A -179.0(5) . . . . ?
F35A C35A C36A C31A 179.2(5) . . . . ?
C34A C35A C36A C31A -0.6(9) . . . . ?
C32A C31A C36A F36A 177.4(5) . . . . ?
B1A C31A C36A F36A -3.7(8) . . . . ?
C32A C31A C36A C35A -1.0(8) . . . . ?
B1A C31A C36A C35A 178.0(5) . . . . ?
C15B N1B C1B C2B -36.0(8) . . . . ?
C11B N1B C1B C2B 156.2(5) . . . . ?
N1B C1B C2B B1B 169.8(5) . . . . ?
N1B C1B C2B C3B -18.9(9) . . . . ?
C31B B1B C2B C1B -176.7(5) . . . . ?
C21B B1B C2B C1B 0.9(8) . . . . ?
C31B B1B C2B C3B 11.7(8) . . . . ?
C21B B1B C2B C3B -170.7(5) . . . . ?
C1B N1B C11B C12B -164.2(4) . . . . ?
C15B N1B C11B C12B 27.4(6) . . . . ?
C1B N1B C11B C17B 72.7(5) . . . . ?
C15B N1B C11B C17B -95.8(5) . . . . ?
C1B N1B C11B C16B -47.9(5) . . . . ?
C15B N1B C11B C16B 143.6(4) . . . . ?
N1B C11B C12B C13B -58.6(6) . . . . ?
C17B C11B C12B C13B 64.1(6) . . . . ?
C16B C11B C12B C13B -175.4(4) . . . . ?
C11B C12B C13B C14B 29.7(6) . . . . ?
C12B C13B C14B C15B 30.9(6) . . . . ?
C1B N1B C15B C19B 99.6(5) . . . . ?
C11B N1B C15B C19B -93.0(5) . . . . ?
C1B N1B C15B C18B -25.8(6) . . . . ?
C11B N1B C15B C18B 141.6(4) . . . . ?
C1B N1B C15B C14B -140.0(4) . . . . ?
C11B N1B C15B C14B 27.4(5) . . . . ?
C13B C14B C15B N1B -59.3(5) . . . . ?
C13B C14B C15B C19B 63.3(5) . . . . ?
C13B C14B C15B C18B -176.8(4) . . . . ?
C2B B1B C21B C26B -100.6(6) . . . . ?
C31B B1B C21B C26B 77.1(6) . . . . ?
C2B B1B C21B C22B 80.4(7) . . . . ?
C31B B1B C21B C22B -101.9(6) . . . . ?
C26B C21B C22B F22B -179.8(4) . . . . ?
B1B C21B C22B F22B -0.8(7) . . . . ?
C26B C21B C22B C23B -0.5(7) . . . . ?
B1B C21B C22B C23B 178.5(5) . . . . ?
F22B C22B C23B F23B 1.0(7) . . . . ?
C21B C22B C23B F23B -178.4(5) . . . . ?
F22B C22B C23B C24B -179.8(4) . . . . ?
C21B C22B C23B C24B 0.9(8) . . . . ?
F23B C23B C24B F24B -1.1(7) . . . . ?
C22B C23B C24B F24B 179.7(4) . . . . ?
F23B C23B C24B C25B 178.6(5) . . . . ?
C22B C23B C24B C25B -0.6(8) . . . . ?
F24B C24B C25B F25B 0.2(7) . . . . ?
C23B C24B C25B F25B -179.5(4) . . . . ?
F24B C24B C25B C26B 179.7(4) . . . . ?
C23B C24B C25B C26B 0.1(8) . . . . ?
C22B C21B C26B F26B -180.0(4) . . . . ?
B1B C21B C26B F26B 1.0(7) . . . . ?
C22B C21B C26B C25B -0.1(7) . . . . ?
B1B C21B C26B C25B -179.2(5) . . . . ?
F25B C25B C26B F26B -0.3(7) . . . . ?
C24B C25B C26B F26B -179.8(4) . . . . ?
F25B C25B C26B C21B 179.9(4) . . . . ?
C24B C25B C26B C21B 0.3(8) . . . . ?
C2B B1B C31B C32B -123.4(6) . . . . ?
C21B B1B C31B C32B 58.9(7) . . . . ?
C2B B1B C31B C36B 55.1(7) . . . . ?
C21B B1B C31B C36B -122.7(5) . . . . ?
C36B C31B C32B F32B -179.2(5) . . . . ?
B1B C31B C32B F32B -0.7(8) . . . . ?
C36B C31B C32B C33B -1.3(8) . . . . ?
B1B C31B C32B C33B 177.3(5) . . . . ?
F32B C32B C33B F33B 0.2(8) . . . . ?
C31B C32B C33B F33B -177.8(5) . . . . ?
F32B C32B C33B C34B 179.4(5) . . . . ?
C31B C32B C33B C34B 1.5(9) . . . . ?
F33B C33B C34B F34B -0.8(8) . . . . ?
C32B C33B C34B F34B 179.9(5) . . . . ?
F33B C33B C34B C35B 178.9(5) . . . . ?
C32B C33B C34B C35B -0.4(8) . . . . ?
F34B C34B C35B F35B -0.7(8) . . . . ?
C33B C34B C35B F35B 179.6(5) . . . . ?
F34B C34B C35B C36B 179.0(5) . . . . ?
C33B C34B C35B C36B -0.7(9) . . . . ?
F35B C35B C36B F36B -1.6(8) . . . . ?
C34B C35B C36B F36B 178.7(5) . . . . ?
F35B C35B C36B C31B -179.5(5) . . . . ?
C34B C35B C36B C31B 0.8(9) . . . . ?
C32B C31B C36B F36B -177.7(5) . . . . ?
B1B C31B C36B F36B 3.7(8) . . . . ?
C32B C31B C36B C35B 0.1(8) . . . . ?
B1B C31B C36B C35B -178.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_erk8875
_database_code_depnum_ccdc_archive 'CCDC 1843579'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 B F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         629.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   10.5438(16)
_cell_length_b                   14.550(2)
_cell_length_c                   19.382(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.141(11)
_cell_angle_gamma                90
_cell_volume                     2917.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2387
_cell_measurement_theta_min      3.8252
_cell_measurement_theta_max      64.2740
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296

_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            36674
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_full        66.79
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5166
_reflns_number_gt                3527
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1620
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_number_reflns         5166
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4090(2) 0.91863(15) 0.72564(12) 0.0325(5) Uani d . . . 1 . .
C C1 0.5258(3) 0.89983(17) 0.72342(14) 0.0328(6) Uani d . . . 1 . .
C C2 0.6437(3) 0.88044(18) 0.72245(14) 0.0326(6) Uani d . . . 1 . .
C C3 0.7465(3) 0.95140(19) 0.74885(17) 0.0399(7) Uani d . . . 1 . .
H H3A 0.7059 1.0119 0.7499 0.06 Uiso calc U . R 1 . .
H H3B 0.8089 0.9534 0.7174 0.06 Uiso calc U . R 1 . .
H H3C 0.7911 0.9349 0.7964 0.06 Uiso calc U . R 1 . .
C C11 0.3229(3) 0.9628(2) 0.66092(16) 0.0380(7) Uani d . . . 1 . .
C C12 0.2456(3) 1.0404(2) 0.68621(17) 0.0471(8) Uani d . . . 1 . .
H H12A 0.3045 1.0927 0.7013 0.057 Uiso calc U . R 1 . .
H H12B 0.179 1.0615 0.6461 0.057 Uiso calc U . R 1 . .
C C13 0.1800(4) 1.0146(3) 0.74606(19) 0.0611(10) Uani d . . . 1 . .
H H13A 0.1171 0.9645 0.7312 0.073 Uiso calc U . R 1 . .
H H13B 0.1326 1.0682 0.7597 0.073 Uiso calc U . R 1 . .
C C14 0.2815(4) 0.9831(3) 0.80830(18) 0.0579(9) Uani d . . . 1 . .
H H14A 0.2383 0.9689 0.8481 0.069 Uiso calc U . R 1 . .
H H14B 0.3425 1.0344 0.8231 0.069 Uiso calc U . R 1 . .
C C15 0.3580(3) 0.8992(2) 0.79335(17) 0.0443(7) Uani d . . . 1 . .
C C16 0.4120(3) 1.0010(2) 0.61506(17) 0.0456(7) Uani d . . . 1 . .
H H16A 0.3608 1.0342 0.5752 0.068 Uiso calc U . R 1 . .
H H16B 0.4584 0.9504 0.5976 0.068 Uiso calc U . R 1 . .
H H16C 0.4743 1.0432 0.6428 0.068 Uiso calc U . R 1 . .
C C17 0.2356(3) 0.8894(2) 0.62029(18) 0.0473(8) Uani d . . . 1 . .
H H17A 0.1964 0.9131 0.5737 0.071 Uiso calc U . R 1 . .
H H17B 0.1674 0.8733 0.6461 0.071 Uiso calc U . R 1 . .
H H17C 0.2869 0.8346 0.615 0.071 Uiso calc U . R 1 . .
C C18 0.4740(3) 0.8876(2) 0.85318(17) 0.0485(8) Uani d . . . 1 . .
H H18A 0.532 0.9404 0.8541 0.073 Uiso calc U . R 1 . .
H H18B 0.5204 0.8311 0.8459 0.073 Uiso calc U . R 1 . .
H H18C 0.4443 0.8837 0.898 0.073 Uiso calc U . R 1 . .
C C19 0.2795(3) 0.8108(3) 0.7843(2) 0.0576(9) Uani d . . . 1 . .
H H19A 0.2566 0.7938 0.8292 0.086 Uiso calc U . R 1 . .
H H19B 0.331 0.7616 0.7688 0.086 Uiso calc U . R 1 . .
H H19C 0.2005 0.8201 0.749 0.086 Uiso calc U . R 1 . .
B B1 0.6810(3) 0.7747(2) 0.69937(18) 0.0341(7) Uani d . . . 1 . .
C C21 0.4511(3) 0.58072(19) 0.58626(15) 0.0357(6) Uani d . . . 1 . .
C C22 0.3520(3) 0.6318(2) 0.54706(17) 0.0431(7) Uani d . . . 1 . .
H H22 0.3521 0.6968 0.5523 0.052 Uiso calc U . R 1 . .
C C23 0.2526(3) 0.5903(2) 0.50048(18) 0.0483(8) Uani d . . . 1 . .
H H23 0.1859 0.6269 0.474 0.058 Uiso calc U . R 1 . .
C C24 0.2497(3) 0.4962(2) 0.49209(17) 0.0451(7) Uani d . . . 1 . .
H H24 0.1812 0.4678 0.4602 0.054 Uiso calc U . R 1 . .
C C25 0.3474(3) 0.4440(2) 0.53050(17) 0.0438(7) Uani d . . . 1 . .
H H25 0.3467 0.3791 0.5249 0.053 Uiso calc U . R 1 . .
C C26 0.4464(3) 0.4857(2) 0.57714(16) 0.0389(7) Uani d . . . 1 . .
H H26 0.5127 0.4487 0.6036 0.047 Uiso calc U . R 1 . .
C C4 0.5512(3) 0.72454(18) 0.65562(15) 0.0341(6) Uani d . . . 1 . .
H H4A 0.4827 0.7287 0.684 0.041 Uiso calc U . R 1 . .
H H4B 0.5211 0.7597 0.6118 0.041 Uiso calc U . R 1 . .
C C5 0.5648(3) 0.62386(19) 0.63588(15) 0.0363(6) Uani d . . . 1 . .
H H5A 0.642 0.6183 0.6141 0.044 Uiso calc U . R 1 . .
H H5B 0.5815 0.5873 0.6798 0.044 Uiso calc U . R 1 . .
C C31 0.7836(3) 0.77910(18) 0.64481(15) 0.0335(6) Uani d . . . 1 . .
F F32 0.69235(17) 0.91589(11) 0.58971(9) 0.0443(4) Uani d . . . 1 . .
C C32 0.7784(3) 0.84601(19) 0.59370(15) 0.0369(6) Uani d . . . 1 . .
F F33 0.84734(19) 0.91600(12) 0.49617(10) 0.0514(5) Uani d . . . 1 . .
C C33 0.8559(3) 0.84742(19) 0.54324(15) 0.0391(7) Uani d . . . 1 . .
F F34 1.01763(18) 0.77662(12) 0.49257(10) 0.0509(5) Uani d . . . 1 . .
C C34 0.9427(3) 0.7776(2) 0.54116(16) 0.0403(7) Uani d . . . 1 . .
F F35 1.03538(18) 0.63908(12) 0.58883(11) 0.0535(5) Uani d . . . 1 . .
C C35 0.9509(3) 0.70869(19) 0.59045(17) 0.0412(7) Uani d . . . 1 . .
F F36 0.88963(16) 0.63951(10) 0.68602(9) 0.0432(4) Uani d . . . 1 . .
C C36 0.8743(3) 0.71071(18) 0.64017(16) 0.0368(6) Uani d . . . 1 . .
C C41 0.7467(3) 0.73004(18) 0.77699(15) 0.0338(6) Uani d . . . 1 . .
F F42 0.55262(16) 0.65904(11) 0.79537(9) 0.0424(4) Uani d . . . 1 . .
C C42 0.6787(3) 0.67940(19) 0.81877(15) 0.0357(6) Uani d . . . 1 . .
F F43 0.65714(19) 0.59610(12) 0.92070(10) 0.0517(5) Uani d . . . 1 . .
C C43 0.7298(3) 0.64675(19) 0.88502(16) 0.0399(7) Uani d . . . 1 . .
F F44 0.9090(2) 0.63511(13) 0.97893(10) 0.0586(5) Uani d . . . 1 . .
C C44 0.8559(3) 0.6661(2) 0.91498(16) 0.0439(7) Uani d . . . 1 . .
F F45 1.05342(18) 0.73577(13) 0.90450(10) 0.0537(5) Uani d . . . 1 . .
C C45 0.9290(3) 0.7173(2) 0.87672(17) 0.0420(7) Uani d . . . 1 . .
F F46 0.95342(16) 0.79720(11) 0.77718(9) 0.0439(4) Uani d . . . 1 . .
C C46 0.8735(3) 0.74731(19) 0.81036(16) 0.0383(7) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.270(4) ?
N1 C15 . 1.538(4) ?
N1 C11 . 1.539(4) ?
C1 C2 . 1.279(4) ?
C2 C3 . 1.512(4) ?
C2 B1 . 1.670(4) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C11 C16 . 1.518(5) ?
C11 C17 . 1.526(4) ?
C11 C12 . 1.528(4) ?
C12 C13 . 1.508(5) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.520(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.521(5) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C19 . 1.521(5) ?
C15 C18 . 1.524(4) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
B1 C4 . 1.636(4) ?
B1 C31 . 1.654(4) ?
B1 C41 . 1.662(4) ?
C21 C22 . 1.384(4) ?
C21 C26 . 1.394(4) ?
C21 C5 . 1.520(4) ?
C22 C23 . 1.383(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.378(5) ?
C23 H23 . 0.95 ?
C24 C25 . 1.377(5) ?
C24 H24 . 0.95 ?
C25 C26 . 1.382(4) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C4 C5 . 1.528(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C31 C32 . 1.382(4) ?
C31 C36 . 1.395(4) ?
F32 C32 . 1.355(3) ?
C32 C33 . 1.390(4) ?
F33 C33 . 1.343(3) ?
C33 C34 . 1.373(4) ?
F34 C34 . 1.341(4) ?
C34 C35 . 1.377(4) ?
F35 C35 . 1.353(3) ?
C35 C36 . 1.372(4) ?
F36 C36 . 1.354(3) ?
C41 C42 . 1.391(4) ?
C41 C46 . 1.391(4) ?
F42 C42 . 1.352(3) ?
C42 C43 . 1.377(4) ?
F43 C43 . 1.346(4) ?
C43 C44 . 1.374(5) ?
F44 C44 . 1.336(4) ?
C44 C45 . 1.386(5) ?
F45 C45 . 1.345(4) ?
C45 C46 . 1.377(4) ?
F46 C46 . 1.364(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C15 . . 119.4(2) ?
C1 N1 C11 . . 119.0(2) ?
C15 N1 C11 . . 121.6(2) ?
N1 C1 C2 . . 178.9(3) ?
C1 C2 C3 . . 118.6(2) ?
C1 C2 B1 . . 119.1(2) ?
C3 C2 B1 . . 122.0(2) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C16 C11 C17 . . 109.5(3) ?
C16 C11 C12 . . 110.2(3) ?
C17 C11 C12 . . 112.1(3) ?
C16 C11 N1 . . 107.2(2) ?
C17 C11 N1 . . 109.3(2) ?
C12 C11 N1 . . 108.3(2) ?
C13 C12 C11 . . 114.5(3) ?
C13 C12 H12A . . 108.6 ?
C11 C12 H12A . . 108.6 ?
C13 C12 H12B . . 108.6 ?
C11 C12 H12B . . 108.6 ?
H12A C12 H12B . . 107.6 ?
C12 C13 C14 . . 109.1(3) ?
C12 C13 H13A . . 109.9 ?
C14 C13 H13A . . 109.9 ?
C12 C13 H13B . . 109.9 ?
C14 C13 H13B . . 109.9 ?
H13A C13 H13B . . 108.3 ?
C13 C14 C15 . . 114.1(3) ?
C13 C14 H14A . . 108.7 ?
C15 C14 H14A . . 108.7 ?
C13 C14 H14B . . 108.7 ?
C15 C14 H14B . . 108.7 ?
H14A C14 H14B . . 107.6 ?
C19 C15 C14 . . 113.9(3) ?
C19 C15 C18 . . 109.4(3) ?
C14 C15 C18 . . 108.7(3) ?
C19 C15 N1 . . 109.2(3) ?
C14 C15 N1 . . 107.5(2) ?
C18 C15 N1 . . 107.9(2) ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C11 C17 H17A . . 109.5 ?
C11 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C11 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C15 C19 H19A . . 109.5 ?
C15 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C15 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C4 B1 C31 . . 105.7(2) ?
C4 B1 C41 . . 117.1(2) ?
C31 B1 C41 . . 112.6(2) ?
C4 B1 C2 . . 109.5(2) ?
C31 B1 C2 . . 110.6(2) ?
C41 B1 C2 . . 101.3(2) ?
C22 C21 C26 . . 117.3(3) ?
C22 C21 C5 . . 123.0(2) ?
C26 C21 C5 . . 119.6(3) ?
C23 C22 C21 . . 121.3(3) ?
C23 C22 H22 . . 119.3 ?
C21 C22 H22 . . 119.3 ?
C24 C23 C22 . . 120.5(3) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C25 C24 C23 . . 119.2(3) ?
C25 C24 H24 . . 120.4 ?
C23 C24 H24 . . 120.4 ?
C24 C25 C26 . . 120.2(3) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C25 C26 C21 . . 121.5(3) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
C5 C4 B1 . . 116.6(2) ?
C5 C4 H4A . . 108.1 ?
B1 C4 H4A . . 108.1 ?
C5 C4 H4B . . 108.1 ?
B1 C4 H4B . . 108.1 ?
H4A C4 H4B . . 107.3 ?
C21 C5 C4 . . 117.0(2) ?
C21 C5 H5A . . 108.0 ?
C4 C5 H5A . . 108.0 ?
C21 C5 H5B . . 108.0 ?
C4 C5 H5B . . 108.0 ?
H5A C5 H5B . . 107.3 ?
C32 C31 C36 . . 112.8(3) ?
C32 C31 B1 . . 123.1(2) ?
C36 C31 B1 . . 123.7(2) ?
F32 C32 C31 . . 120.1(3) ?
F32 C32 C33 . . 115.3(2) ?
C31 C32 C33 . . 124.6(3) ?
F33 C33 C34 . . 119.2(3) ?
F33 C33 C32 . . 121.1(3) ?
C34 C33 C32 . . 119.7(3) ?
F34 C34 C33 . . 121.0(3) ?
F34 C34 C35 . . 120.9(3) ?
C33 C34 C35 . . 118.1(3) ?
F35 C35 C36 . . 120.8(3) ?
F35 C35 C34 . . 118.8(3) ?
C36 C35 C34 . . 120.4(3) ?
F36 C36 C35 . . 115.7(2) ?
F36 C36 C31 . . 120.0(3) ?
C35 C36 C31 . . 124.4(3) ?
C42 C41 C46 . . 112.4(3) ?
C42 C41 B1 . . 124.2(2) ?
C46 C41 B1 . . 123.0(3) ?
F42 C42 C43 . . 114.8(3) ?
F42 C42 C41 . . 120.3(3) ?
C43 C42 C41 . . 125.0(3) ?
F43 C43 C44 . . 119.7(3) ?
F43 C43 C42 . . 120.6(3) ?
C44 C43 C42 . . 119.7(3) ?
F44 C44 C43 . . 121.4(3) ?
F44 C44 C45 . . 120.1(3) ?
C43 C44 C45 . . 118.5(3) ?
F45 C45 C46 . . 121.1(3) ?
F45 C45 C44 . . 119.6(3) ?
C46 C45 C44 . . 119.3(3) ?
F46 C46 C45 . . 114.8(3) ?
F46 C46 C41 . . 120.2(3) ?
C45 C46 C41 . . 125.0(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C11 C16 . . . . -17.2(3) ?
C15 N1 C11 C16 . . . . 161.2(2) ?
C1 N1 C11 C17 . . . . 101.5(3) ?
C15 N1 C11 C17 . . . . -80.2(3) ?
C1 N1 C11 C12 . . . . -136.1(3) ?
C15 N1 C11 C12 . . . . 42.2(3) ?
C16 C11 C12 C13 . . . . -165.3(3) ?
C17 C11 C12 C13 . . . . 72.4(4) ?
N1 C11 C12 C13 . . . . -48.2(4) ?
C11 C12 C13 C14 . . . . 59.1(4) ?
C12 C13 C14 C15 . . . . -60.9(4) ?
C13 C14 C15 C19 . . . . -70.0(4) ?
C13 C14 C15 C18 . . . . 167.8(3) ?
C13 C14 C15 N1 . . . . 51.1(4) ?
C1 N1 C15 C19 . . . . -101.3(3) ?
C11 N1 C15 C19 . . . . 80.3(3) ?
C1 N1 C15 C14 . . . . 134.7(3) ?
C11 N1 C15 C14 . . . . -43.7(4) ?
C1 N1 C15 C18 . . . . 17.5(4) ?
C11 N1 C15 C18 . . . . -160.8(2) ?
C1 C2 B1 C4 . . . . 19.8(4) ?
C3 C2 B1 C4 . . . . -166.1(3) ?
C1 C2 B1 C31 . . . . 135.9(3) ?
C3 C2 B1 C31 . . . . -50.0(3) ?
C1 C2 B1 C41 . . . . -104.5(3) ?
C3 C2 B1 C41 . . . . 69.6(3) ?
C26 C21 C22 C23 . . . . -0.3(5) ?
C5 C21 C22 C23 . . . . 177.5(3) ?
C21 C22 C23 C24 . . . . 0.2(5) ?
C22 C23 C24 C25 . . . . -0.3(5) ?
C23 C24 C25 C26 . . . . 0.4(5) ?
C24 C25 C26 C21 . . . . -0.5(5) ?
C22 C21 C26 C25 . . . . 0.5(4) ?
C5 C21 C26 C25 . . . . -177.5(3) ?
C31 B1 C4 C5 . . . . 66.1(3) ?
C41 B1 C4 C5 . . . . -60.2(3) ?
C2 B1 C4 C5 . . . . -174.7(2) ?
C22 C21 C5 C4 . . . . 14.8(4) ?
C26 C21 C5 C4 . . . . -167.4(3) ?
B1 C4 C5 C21 . . . . -171.2(2) ?
C4 B1 C31 C32 . . . . 81.6(3) ?
C41 B1 C31 C32 . . . . -149.4(3) ?
C2 B1 C31 C32 . . . . -36.8(4) ?
C4 B1 C31 C36 . . . . -91.0(3) ?
C41 B1 C31 C36 . . . . 38.1(4) ?
C2 B1 C31 C36 . . . . 150.6(3) ?
C36 C31 C32 F32 . . . . 178.0(2) ?
B1 C31 C32 F32 . . . . 4.7(4) ?
C36 C31 C32 C33 . . . . -1.0(4) ?
B1 C31 C32 C33 . . . . -174.3(3) ?
F32 C32 C33 F33 . . . . 2.4(4) ?
C31 C32 C33 F33 . . . . -178.5(3) ?
F32 C32 C33 C34 . . . . -177.5(3) ?
C31 C32 C33 C34 . . . . 1.6(5) ?
F33 C33 C34 F34 . . . . -0.7(4) ?
C32 C33 C34 F34 . . . . 179.2(3) ?
F33 C33 C34 C35 . . . . 179.2(3) ?
C32 C33 C34 C35 . . . . -0.9(4) ?
F34 C34 C35 F35 . . . . -0.5(4) ?
C33 C34 C35 F35 . . . . 179.6(3) ?
F34 C34 C35 C36 . . . . 179.6(3) ?
C33 C34 C35 C36 . . . . -0.3(5) ?
F35 C35 C36 F36 . . . . -0.1(4) ?
C34 C35 C36 F36 . . . . 179.8(3) ?
F35 C35 C36 C31 . . . . -179.0(3) ?
C34 C35 C36 C31 . . . . 0.9(5) ?
C32 C31 C36 F36 . . . . -179.1(2) ?
B1 C31 C36 F36 . . . . -5.9(4) ?
C32 C31 C36 C35 . . . . -0.2(4) ?
B1 C31 C36 C35 . . . . 173.0(3) ?
C4 B1 C41 C42 . . . . -25.6(4) ?
C31 B1 C41 C42 . . . . -148.5(3) ?
C2 B1 C41 C42 . . . . 93.4(3) ?
C4 B1 C41 C46 . . . . 161.1(3) ?
C31 B1 C41 C46 . . . . 38.2(4) ?
C2 B1 C41 C46 . . . . -80.0(3) ?
C46 C41 C42 F42 . . . . 177.8(2) ?
B1 C41 C42 F42 . . . . 3.9(4) ?
C46 C41 C42 C43 . . . . -1.8(4) ?
B1 C41 C42 C43 . . . . -175.8(3) ?
F42 C42 C43 F43 . . . . 2.2(4) ?
C41 C42 C43 F43 . . . . -178.2(3) ?
F42 C42 C43 C44 . . . . -177.8(2) ?
C41 C42 C43 C44 . . . . 1.9(4) ?
F43 C43 C44 F44 . . . . 0.5(4) ?
C42 C43 C44 F44 . . . . -179.5(3) ?
F43 C43 C44 C45 . . . . 179.2(3) ?
C42 C43 C44 C45 . . . . -0.9(4) ?
F44 C44 C45 F45 . . . . -0.2(4) ?
C43 C44 C45 F45 . . . . -178.9(3) ?
F44 C44 C45 C46 . . . . 178.8(3) ?
C43 C44 C45 C46 . . . . 0.1(4) ?
F45 C45 C46 F46 . . . . -1.1(4) ?
C44 C45 C46 F46 . . . . 179.9(3) ?
F45 C45 C46 C41 . . . . 178.7(3) ?
C44 C45 C46 C41 . . . . -0.2(5) ?
C42 C41 C46 F46 . . . . -179.2(2) ?
B1 C41 C46 F46 . . . . -5.1(4) ?
C42 C41 C46 C45 . . . . 1.0(4) ?
B1 C41 C46 C45 . . . . 175.1(3) ?

####################################################################### 
# 
# 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_erk8286
_database_code_depnum_ccdc_archive 'CCDC 1843584'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H38 B F10 N3 Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         669.53

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   13.5304(5)
_cell_length_b                   17.4187(6)
_cell_length_c                   14.8740(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.5560(10)
_cell_angle_gamma                90
_cell_volume                     3360.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      4.2500
_cell_measurement_theta_max      67.4000
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392

_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            58309
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5922
_reflns_number_gt                4690
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0895
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         5922
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+1.1580P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.67696(15) 0.36940(11) 0.33124(15) 0.0193(4) Uani d . . . 1 . .
C C2 0.60141(13) 0.22552(10) 0.46362(12) 0.0192(4) Uani d . . . 1 . .
N N2 0.57941(11) 0.34430(8) 0.36181(10) 0.0184(3) Uani d . . . 1 . .
Si Si1 0.60618(4) 0.12100(3) 0.43328(4) 0.02138(13) Uani d . . . 1 . .
C C1 0.57100(13) 0.26389(10) 0.53220(13) 0.0212(4) Uani d . . . 1 . .
H H1 0.5733 0.3181 0.526 0.025 Uiso calc U . R 1 . .
N N3 0.71941(11) 0.28914(8) 0.37907(10) 0.0179(3) Uani d . . . 1 . .
C C6 0.63142(13) 0.28170(10) 0.40270(12) 0.0184(4) Uani d . . . 1 . .
N N1 0.53878(12) 0.24214(8) 0.60599(11) 0.0235(3) Uani d . . . 1 . .
C C21 0.46690(13) 0.35307(10) 0.32882(13) 0.0225(4) Uani d . . . 1 . .
H H21 0.4376 0.3336 0.3791 0.027 Uiso calc U . R 1 . .
C C22 0.43813(15) 0.43724(11) 0.31252(16) 0.0320(5) Uani d . . . 1 . .
H H22A 0.4676 0.4661 0.3705 0.048 Uiso calc U . R 1 . .
H H22B 0.3629 0.4425 0.2936 0.048 Uiso calc U . R 1 . .
H H22C 0.4654 0.4575 0.2629 0.048 Uiso calc U . R 1 . .
C C23 0.42101(16) 0.30584(13) 0.24082(16) 0.0380(5) Uani d . . . 1 . .
H H23A 0.4446 0.3264 0.1891 0.057 Uiso calc U . R 1 . .
H H23B 0.3456 0.3084 0.2242 0.057 Uiso calc U . R 1 . .
H H23C 0.4433 0.2523 0.2524 0.057 Uiso calc U . R 1 . .
C C24 0.81843(13) 0.25506(10) 0.43132(13) 0.0204(4) Uani d . . . 1 . .
H H24 0.8037 0.2024 0.4509 0.024 Uiso calc U . R 1 . .
C C25 0.87149(15) 0.29964(11) 0.52026(13) 0.0268(4) Uani d . . . 1 . .
H H25A 0.8912 0.3506 0.5033 0.04 Uiso calc U . R 1 . .
H H25B 0.9332 0.2718 0.5557 0.04 Uiso calc U . R 1 . .
H H25C 0.8241 0.3052 0.5589 0.04 Uiso calc U . R 1 . .
C C26 0.88744(14) 0.24618(11) 0.36722(14) 0.0264(4) Uani d . . . 1 . .
H H26A 0.8522 0.2148 0.3128 0.04 Uiso calc U . R 1 . .
H H26B 0.952 0.2211 0.4016 0.04 Uiso calc U . R 1 . .
H H26C 0.9026 0.2969 0.3459 0.04 Uiso calc U . R 1 . .
C C11 0.51608(17) 0.30329(11) 0.66723(14) 0.0319(5) Uani d . . . 1 . .
H H11 0.4934 0.277 0.7178 0.038 Uiso calc U . R 1 . .
C C12 0.6126(2) 0.34938(13) 0.71540(15) 0.0426(6) Uani d . . . 1 . .
H H12A 0.6666 0.3145 0.7508 0.064 Uiso calc U . R 1 . .
H H12B 0.5962 0.3867 0.7584 0.064 Uiso calc U . R 1 . .
H H12C 0.6369 0.3765 0.668 0.064 Uiso calc U . R 1 . .
C C13 0.4271(2) 0.35424(13) 0.61382(17) 0.0422(6) Uani d . . . 1 . .
H H13A 0.4479 0.3834 0.5658 0.063 Uiso calc U . R 1 . .
H H13B 0.4089 0.3899 0.6576 0.063 Uiso calc U . R 1 . .
H H13C 0.3673 0.3222 0.5837 0.063 Uiso calc U . R 1 . .
C C14 0.52086(14) 0.16223(10) 0.62838(13) 0.0228(4) Uani d . . . 1 . .
H H14 0.5412 0.129 0.5818 0.027 Uiso calc U . R 1 . .
C C15 0.40678(15) 0.14774(12) 0.61670(15) 0.0299(5) Uani d . . . 1 . .
H H15A 0.3844 0.1785 0.6625 0.045 Uiso calc U . R 1 . .
H H15B 0.396 0.0932 0.6269 0.045 Uiso calc U . R 1 . .
H H15C 0.3666 0.1622 0.5532 0.045 Uiso calc U . R 1 . .
C C16 0.58832(16) 0.13906(12) 0.72560(14) 0.0309(5) Uani d . . . 1 . .
H H16A 0.6609 0.1485 0.7298 0.046 Uiso calc U . R 1 . .
H H16B 0.5784 0.0844 0.7359 0.046 Uiso calc U . R 1 . .
H H16C 0.5689 0.1694 0.7734 0.046 Uiso calc U . R 1 . .
C C3 0.64703(16) 0.11028(11) 0.32408(14) 0.0294(4) Uani d . . . 1 . .
H H3A 0.6031 0.1423 0.2744 0.044 Uiso calc U . R 1 . .
H H3B 0.6404 0.0564 0.3042 0.044 Uiso calc U . R 1 . .
H H3C 0.719 0.1265 0.3364 0.044 Uiso calc U . R 1 . .
C C4 0.69925(15) 0.06498(11) 0.52829(14) 0.0284(4) Uani d . . . 1 . .
H H4A 0.7679 0.0882 0.5419 0.043 Uiso calc U . R 1 . .
H H4B 0.7023 0.0119 0.5076 0.043 Uiso calc U . R 1 . .
H H4C 0.6762 0.0656 0.5851 0.043 Uiso calc U . R 1 . .
C C5 0.47340(15) 0.07786(11) 0.40239(15) 0.0303(5) Uani d . . . 1 . .
H H5A 0.4461 0.0812 0.4566 0.045 Uiso calc U . R 1 . .
H H5B 0.4769 0.0239 0.3849 0.045 Uiso calc U . R 1 . .
H H5C 0.428 0.106 0.3495 0.045 Uiso calc U . R 1 . .
C C31 0.74252(13) 0.44105(10) 0.39036(12) 0.0190(4) Uani d . . . 1 . .
C C32 0.82976(14) 0.46863(10) 0.36910(12) 0.0196(4) Uani d . . . 1 . .
F F32 0.86054(8) 0.43556(6) 0.29881(7) 0.0235(2) Uani d . . . 1 . .
C C33 0.89065(13) 0.52813(10) 0.41553(13) 0.0213(4) Uani d . . . 1 . .
F F33 0.97477(8) 0.55051(6) 0.39121(8) 0.0277(3) Uani d . . . 1 . .
C C34 0.86600(14) 0.56297(10) 0.48946(13) 0.0247(4) Uani d . . . 1 . .
F F34 0.92559(9) 0.61941(6) 0.53767(8) 0.0331(3) Uani d . . . 1 . .
C C35 0.78109(15) 0.53786(11) 0.51409(13) 0.0247(4) Uani d . . . 1 . .
F F35 0.75618(9) 0.57164(7) 0.58635(8) 0.0363(3) Uani d . . . 1 . .
C C36 0.72211(14) 0.47816(10) 0.46555(13) 0.0222(4) Uani d . . . 1 . .
F F36 0.64108(8) 0.45743(6) 0.49669(8) 0.0302(3) Uani d . . . 1 . .
C C41 0.65685(13) 0.37987(10) 0.21835(12) 0.0186(4) Uani d . . . 1 . .
C C42 0.63417(13) 0.45138(10) 0.17568(12) 0.0198(4) Uani d . . . 1 . .
F F42 0.62538(8) 0.51382(6) 0.22760(7) 0.0247(2) Uani d . . . 1 . .
C C43 0.61887(13) 0.46524(10) 0.08153(13) 0.0222(4) Uani d . . . 1 . .
F F43 0.59729(8) 0.53644(6) 0.04632(7) 0.0280(3) Uani d . . . 1 . .
C C44 0.62553(14) 0.40518(11) 0.02348(13) 0.0239(4) Uani d . . . 1 . .
F F44 0.61088(9) 0.41706(7) -0.06874(7) 0.0335(3) Uani d . . . 1 . .
C C45 0.64671(14) 0.33276(11) 0.06097(13) 0.0231(4) Uani d . . . 1 . .
F F45 0.65539(9) 0.27378(6) 0.00509(8) 0.0325(3) Uani d . . . 1 . .
C C46 0.66092(13) 0.32134(10) 0.15580(13) 0.0213(4) Uani d . . . 1 . .
F F46 0.68115(8) 0.24829(6) 0.18588(7) 0.0285(3) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N2 . 1.576(2) ?
B1 N3 . 1.599(2) ?
B1 C41 . 1.633(3) ?
B1 C31 . 1.635(3) ?
B1 C6 . 2.053(3) ?
C2 C1 . 1.377(3) ?
C2 C6 . 1.467(2) ?
C2 Si1 . 1.8812(18) ?
N2 C6 . 1.345(2) ?
N2 C21 . 1.468(2) ?
Si1 C3 . 1.868(2) ?
Si1 C4 . 1.876(2) ?
Si1 C5 . 1.880(2) ?
C1 N1 . 1.346(2) ?
C1 H1 . 0.95 ?
N3 C6 . 1.340(2) ?
N3 C24 . 1.469(2) ?
N1 C14 . 1.467(2) ?
N1 C11 . 1.489(2) ?
C21 C22 . 1.519(3) ?
C21 C23 . 1.521(3) ?
C21 H21 . 1.0 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C24 C26 . 1.521(3) ?
C24 C25 . 1.526(3) ?
C24 H24 . 1.0 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C11 C13 . 1.524(3) ?
C11 C12 . 1.526(3) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C15 . 1.524(3) ?
C14 C16 . 1.528(3) ?
C14 H14 . 1.0 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C31 C36 . 1.386(3) ?
C31 C32 . 1.392(3) ?
C32 F32 . 1.359(2) ?
C32 C33 . 1.380(3) ?
C33 F33 . 1.347(2) ?
C33 C34 . 1.378(3) ?
C34 F34 . 1.342(2) ?
C34 C35 . 1.373(3) ?
C35 F35 . 1.350(2) ?
C35 C36 . 1.382(3) ?
C36 F36 . 1.355(2) ?
C41 C46 . 1.392(3) ?
C41 C42 . 1.392(3) ?
C42 F42 . 1.359(2) ?
C42 C43 . 1.377(3) ?
C43 F43 . 1.345(2) ?
C43 C44 . 1.376(3) ?
C44 F44 . 1.345(2) ?
C44 C45 . 1.376(3) ?
C45 F45 . 1.347(2) ?
C45 C46 . 1.382(3) ?
C46 F46 . 1.351(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 B1 N3 . . 81.56(12) ?
N2 B1 C41 . . 114.83(15) ?
N3 B1 C41 . . 119.25(15) ?
N2 B1 C31 . . 115.30(15) ?
N3 B1 C31 . . 110.92(14) ?
C41 B1 C31 . . 111.94(14) ?
N2 B1 C6 . . 40.93(9) ?
N3 B1 C6 . . 40.72(8) ?
C41 B1 C6 . . 128.95(14) ?
C31 B1 C6 . . 119.10(14) ?
C1 C2 C6 . . 109.12(15) ?
C1 C2 Si1 . . 133.27(14) ?
C6 C2 Si1 . . 117.57(12) ?
C6 N2 C21 . . 126.46(15) ?
C6 N2 B1 . . 88.97(13) ?
C21 N2 B1 . . 138.49(15) ?
C3 Si1 C4 . . 107.54(9) ?
C3 Si1 C5 . . 104.27(9) ?
C4 Si1 C5 . . 111.46(9) ?
C3 Si1 C2 . . 110.13(8) ?
C4 Si1 C2 . . 112.59(8) ?
C5 Si1 C2 . . 110.48(8) ?
N1 C1 C2 . . 134.61(17) ?
N1 C1 H1 . . 112.7 ?
C2 C1 H1 . . 112.7 ?
C6 N3 C24 . . 124.52(15) ?
C6 N3 B1 . . 88.16(13) ?
C24 N3 B1 . . 138.28(14) ?
N3 C6 N2 . . 101.09(14) ?
N3 C6 C2 . . 130.48(16) ?
N2 C6 C2 . . 128.20(16) ?
N3 C6 B1 . . 51.12(10) ?
N2 C6 B1 . . 50.10(10) ?
C2 C6 B1 . . 172.94(14) ?
C1 N1 C14 . . 124.40(15) ?
C1 N1 C11 . . 117.95(15) ?
C14 N1 C11 . . 117.61(14) ?
N2 C21 C22 . . 110.36(15) ?
N2 C21 C23 . . 111.19(15) ?
C22 C21 C23 . . 111.20(17) ?
N2 C21 H21 . . 108.0 ?
C22 C21 H21 . . 108.0 ?
C23 C21 H21 . . 108.0 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
N3 C24 C26 . . 109.87(14) ?
N3 C24 C25 . . 112.70(15) ?
C26 C24 C25 . . 111.98(15) ?
N3 C24 H24 . . 107.3 ?
C26 C24 H24 . . 107.3 ?
C25 C24 H24 . . 107.3 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C24 C26 H26A . . 109.5 ?
C24 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C24 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
N1 C11 C13 . . 111.57(17) ?
N1 C11 C12 . . 111.44(17) ?
C13 C11 C12 . . 112.42(18) ?
N1 C11 H11 . . 107.0 ?
C13 C11 H11 . . 107.0 ?
C12 C11 H11 . . 107.0 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 C15 . . 111.02(15) ?
N1 C14 C16 . . 111.87(15) ?
C15 C14 C16 . . 112.12(16) ?
N1 C14 H14 . . 107.2 ?
C15 C14 H14 . . 107.2 ?
C16 C14 H14 . . 107.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
Si1 C3 H3A . . 109.5 ?
Si1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Si1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Si1 C4 H4A . . 109.5 ?
Si1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Si1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C36 C31 C32 . . 113.54(16) ?
C36 C31 B1 . . 125.99(16) ?
C32 C31 B1 . . 120.44(15) ?
F32 C32 C33 . . 115.67(16) ?
F32 C32 C31 . . 119.62(15) ?
C33 C32 C31 . . 124.71(17) ?
F33 C33 C34 . . 120.16(16) ?
F33 C33 C32 . . 120.84(16) ?
C34 C33 C32 . . 118.97(17) ?
F34 C34 C35 . . 120.77(17) ?
F34 C34 C33 . . 120.27(17) ?
C35 C34 C33 . . 118.95(16) ?
F35 C35 C34 . . 119.44(16) ?
F35 C35 C36 . . 120.39(17) ?
C34 C35 C36 . . 120.18(17) ?
F36 C36 C35 . . 115.14(16) ?
F36 C36 C31 . . 121.21(16) ?
C35 C36 C31 . . 123.65(17) ?
C46 C41 C42 . . 113.34(16) ?
C46 C41 B1 . . 125.37(16) ?
C42 C41 B1 . . 121.29(15) ?
F42 C42 C43 . . 115.18(15) ?
F42 C42 C41 . . 120.06(15) ?
C43 C42 C41 . . 124.77(17) ?
F43 C43 C44 . . 120.16(16) ?
F43 C43 C42 . . 120.69(16) ?
C44 C43 C42 . . 119.15(17) ?
F44 C44 C43 . . 120.41(17) ?
F44 C44 C45 . . 120.50(17) ?
C43 C44 C45 . . 119.09(17) ?
F45 C45 C44 . . 119.58(16) ?
F45 C45 C46 . . 120.56(17) ?
C44 C45 C46 . . 119.85(17) ?
F46 C46 C45 . . 115.44(15) ?
F46 C46 C41 . . 120.76(16) ?
C45 C46 C41 . . 123.79(17) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 B1 N2 C6 . . . . 3.18(12) ?
C41 B1 N2 C6 . . . . 121.59(16) ?
C31 B1 N2 C6 . . . . -106.03(16) ?
N3 B1 N2 C21 . . . . -148.03(19) ?
C41 B1 N2 C21 . . . . -29.6(3) ?
C31 B1 N2 C21 . . . . 102.8(2) ?
C6 B1 N2 C21 . . . . -151.2(2) ?
C1 C2 Si1 C3 . . . . 175.61(18) ?
C6 C2 Si1 C3 . . . . -1.59(16) ?
C1 C2 Si1 C4 . . . . -64.4(2) ?
C6 C2 Si1 C4 . . . . 118.43(14) ?
C1 C2 Si1 C5 . . . . 61.0(2) ?
C6 C2 Si1 C5 . . . . -116.24(14) ?
C6 C2 C1 N1 . . . . -178.3(2) ?
Si1 C2 C1 N1 . . . . 4.3(3) ?
N2 B1 N3 C6 . . . . -3.20(12) ?
C41 B1 N3 C6 . . . . -117.00(16) ?
C31 B1 N3 C6 . . . . 110.74(15) ?
N2 B1 N3 C24 . . . . -147.88(19) ?
C41 B1 N3 C24 . . . . 98.3(2) ?
C31 B1 N3 C24 . . . . -33.9(3) ?
C6 B1 N3 C24 . . . . -144.7(2) ?
C24 N3 C6 N2 . . . . 155.94(15) ?
B1 N3 C6 N2 . . . . 3.78(14) ?
C24 N3 C6 C2 . . . . -18.9(3) ?
B1 N3 C6 C2 . . . . -171.07(19) ?
C24 N3 C6 B1 . . . . 152.2(2) ?
C21 N2 C6 N3 . . . . 152.79(16) ?
B1 N2 C6 N3 . . . . -3.83(15) ?
C21 N2 C6 C2 . . . . -32.2(3) ?
B1 N2 C6 C2 . . . . 171.18(18) ?
C21 N2 C6 B1 . . . . 156.6(2) ?
C1 C2 C6 N3 . . . . 124.8(2) ?
Si1 C2 C6 N3 . . . . -57.4(2) ?
C1 C2 C6 N2 . . . . -48.8(2) ?
Si1 C2 C6 N2 . . . . 129.07(17) ?
C2 C1 N1 C14 . . . . -4.6(3) ?
C2 C1 N1 C11 . . . . 177.8(2) ?
C6 N2 C21 C22 . . . . 164.10(17) ?
B1 N2 C21 C22 . . . . -52.7(3) ?
C6 N2 C21 C23 . . . . -72.0(2) ?
B1 N2 C21 C23 . . . . 71.2(3) ?
C6 N3 C24 C26 . . . . 156.77(16) ?
B1 N3 C24 C26 . . . . -67.8(3) ?
C6 N3 C24 C25 . . . . -77.6(2) ?
B1 N3 C24 C25 . . . . 57.9(3) ?
C1 N1 C11 C13 . . . . 63.2(2) ?
C14 N1 C11 C13 . . . . -114.61(19) ?
C1 N1 C11 C12 . . . . -63.3(2) ?
C14 N1 C11 C12 . . . . 118.83(19) ?
C1 N1 C14 C15 . . . . -113.2(2) ?
C11 N1 C14 C15 . . . . 64.5(2) ?
C1 N1 C14 C16 . . . . 120.68(19) ?
C11 N1 C14 C16 . . . . -61.6(2) ?
N2 B1 C31 C36 . . . . 2.8(3) ?
N3 B1 C31 C36 . . . . -87.6(2) ?
C41 B1 C31 C36 . . . . 136.56(18) ?
C6 B1 C31 C36 . . . . -43.3(2) ?
N2 B1 C31 C32 . . . . -179.50(15) ?
N3 B1 C31 C32 . . . . 90.11(19) ?
C41 B1 C31 C32 . . . . -45.8(2) ?
C6 B1 C31 C32 . . . . 134.40(16) ?
C36 C31 C32 F32 . . . . 177.83(15) ?
B1 C31 C32 F32 . . . . -0.1(2) ?
C36 C31 C32 C33 . . . . -1.3(3) ?
B1 C31 C32 C33 . . . . -179.26(16) ?
F32 C32 C33 F33 . . . . -0.1(2) ?
C31 C32 C33 F33 . . . . 179.05(16) ?
F32 C32 C33 C34 . . . . -178.10(15) ?
C31 C32 C33 C34 . . . . 1.1(3) ?
F33 C33 C34 F34 . . . . 0.0(3) ?
C32 C33 C34 F34 . . . . 178.00(16) ?
F33 C33 C34 C35 . . . . -178.56(16) ?
C32 C33 C34 C35 . . . . -0.6(3) ?
F34 C34 C35 F35 . . . . 1.5(3) ?
C33 C34 C35 F35 . . . . -179.93(16) ?
F34 C34 C35 C36 . . . . -178.11(16) ?
C33 C34 C35 C36 . . . . 0.5(3) ?
F35 C35 C36 F36 . . . . -0.5(3) ?
C34 C35 C36 F36 . . . . 179.11(17) ?
F35 C35 C36 C31 . . . . 179.57(17) ?
C34 C35 C36 C31 . . . . -0.8(3) ?
C32 C31 C36 F36 . . . . -178.74(16) ?
B1 C31 C36 F36 . . . . -0.9(3) ?
C32 C31 C36 C35 . . . . 1.2(3) ?
B1 C31 C36 C35 . . . . 178.98(17) ?
N2 B1 C41 C46 . . . . -85.6(2) ?
N3 B1 C41 C46 . . . . 8.7(3) ?
C31 B1 C41 C46 . . . . 140.49(17) ?
C6 B1 C41 C46 . . . . -39.7(3) ?
N2 B1 C41 C42 . . . . 95.02(19) ?
N3 B1 C41 C42 . . . . -170.75(15) ?
C31 B1 C41 C42 . . . . -38.9(2) ?
C6 B1 C41 C42 . . . . 140.88(17) ?
C46 C41 C42 F42 . . . . 178.56(15) ?
B1 C41 C42 F42 . . . . -2.0(2) ?
C46 C41 C42 C43 . . . . -1.2(2) ?
B1 C41 C42 C43 . . . . 178.25(16) ?
F42 C42 C43 F43 . . . . 0.2(2) ?
C41 C42 C43 F43 . . . . -179.96(16) ?
F42 C42 C43 C44 . . . . -179.52(15) ?
C41 C42 C43 C44 . . . . 0.3(3) ?
F43 C43 C44 F44 . . . . 0.2(3) ?
C42 C43 C44 F44 . . . . 179.96(16) ?
F43 C43 C44 C45 . . . . -179.38(16) ?
C42 C43 C44 C45 . . . . 0.4(3) ?
F44 C44 C45 F45 . . . . 1.7(3) ?
C43 C44 C45 F45 . . . . -178.72(16) ?
F44 C44 C45 C46 . . . . -179.58(16) ?
C43 C44 C45 C46 . . . . 0.0(3) ?
F45 C45 C46 F46 . . . . -1.4(2) ?
C44 C45 C46 F46 . . . . 179.88(15) ?
F45 C45 C46 C41 . . . . 177.61(16) ?
C44 C45 C46 C41 . . . . -1.1(3) ?
C42 C41 C46 F46 . . . . -179.39(15) ?
B1 C41 C46 F46 . . . . 1.1(3) ?
C42 C41 C46 C45 . . . . 1.6(3) ?
B1 C41 C46 C45 . . . . -177.83(17) ?

####################################################################### 
# 
# 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_erk8359
_database_code_depnum_ccdc_archive 'CCDC 1843576'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 B F10 N'
_chemical_formula_weight         527.25

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                   12.8034(2)
_cell_length_b                   11.3378(2)
_cell_length_c                   18.2647(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.982(1)
_cell_angle_gamma                90.00
_cell_volume                     2548.87(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5768
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_T_max  0.9961
_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            17860
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_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         4.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4421
_reflns_number_gt                2961
_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. 

 The hydrogens at B1 and N1 atoms were refined freely.

 A disordered solvent molecule (probably a mixture of dichloromethane and 
 pentane) 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.
;
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 0.500 0.000 0.500 109 42 ' '
2 0.500 0.500 0.000 109 42 ' '

_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)+(0.0219P)²+2.8694P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4421
_refine_ls_number_parameters     438
_refine_ls_number_restraints     298
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.027
_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 0.81100(17) 0.0677(2) 0.15392(13) 0.0376(6) Uani 1 1 d . . .
H2 H 0.770(2) 0.014(2) 0.1720(15) 0.033(7) Uiso 1 1 d . . .
C1 C 0.9280(2) 0.0166(3) 0.18456(18) 0.0487(8) Uani 1 1 d . . .
C2 C 0.9344(2) -0.1014(3) 0.14626(18) 0.0528(8) Uani 1 1 d . . .
H2A H 1.0101 -0.1280 0.1607 0.063 Uiso 1 1 calc R . .
H2B H 0.8918 -0.1595 0.1655 0.063 Uiso 1 1 calc R . .
C3 C 0.8935(3) -0.0979(3) 0.06039(19) 0.0629(10) Uani 1 1 d . . .
H3A H 0.9377 -0.0432 0.0400 0.076 Uiso 1 1 calc R . .
H3B H 0.8991 -0.1765 0.0394 0.076 Uiso 1 1 calc R . .
C4 C 0.7767(3) -0.0579(3) 0.03799(18) 0.0571(9) Uani 1 1 d . . .
H4A H 0.7337 -0.1145 0.0582 0.069 Uiso 1 1 calc R . .
H4B H 0.7494 -0.0595 -0.0177 0.069 Uiso 1 1 calc R . .
C5 C 0.7585(2) 0.0646(3) 0.06574(16) 0.0459(8) Uani 1 1 d . . .
C6 C 1.0138(2) 0.1026(4) 0.1728(2) 0.0720(11) Uani 1 1 d . . .
H6A H 1.0856 0.0739 0.1995 0.108 Uiso 1 1 calc R . .
H6B H 1.0024 0.1795 0.1927 0.108 Uiso 1 1 calc R . .
H6C H 1.0079 0.1091 0.1189 0.108 Uiso 1 1 calc R . .
C7 C 0.9450(3) -0.0037(4) 0.26954(19) 0.0698(11) Uani 1 1 d . . .
H7A H 0.8864 -0.0520 0.2772 0.105 Uiso 1 1 calc R . .
H7B H 0.9457 0.0716 0.2949 0.105 Uiso 1 1 calc R . .
H7C H 1.0137 -0.0436 0.2906 0.105 Uiso 1 1 calc R . .
C8 C 0.8047(3) 0.1595(4) 0.0246(2) 0.0718(11) Uani 1 1 d . . .
H8A H 0.7727 0.1520 -0.0299 0.108 Uiso 1 1 calc R . .
H8B H 0.8828 0.1503 0.0362 0.108 Uiso 1 1 calc R . .
H8C H 0.7878 0.2367 0.0412 0.108 Uiso 1 1 calc R . .
C9 C 0.6370(2) 0.0861(3) 0.05326(18) 0.0565(9) Uani 1 1 d . . .
H9A H 0.6259 0.1644 0.0710 0.085 Uiso 1 1 calc R . .
H9B H 0.6081 0.0279 0.0814 0.085 Uiso 1 1 calc R . .
H9C H 0.5999 0.0794 -0.0006 0.085 Uiso 1 1 calc R . .
C11 C 0.7969(2) 0.1827(3) 0.18722(18) 0.0439(7) Uani 1 1 d . . .
H11 H 0.8310 0.2488 0.1729 0.053 Uiso 1 1 calc R . .
C12 C 0.7388(2) 0.1983(3) 0.23615(18) 0.0443(7) Uani 1 1 d . A .
C13 C 0.7272(3) 0.3257(3) 0.2585(2) 0.0617(10) Uani 1 1 d . . .
H13A H 0.7715 0.3760 0.2362 0.093 Uiso 1 1 calc R . .
H13B H 0.7509 0.3330 0.3135 0.093 Uiso 1 1 calc R . .
H13C H 0.6517 0.3495 0.2401 0.093 Uiso 1 1 calc R . .
B1 B 0.6754(2) 0.0938(3) 0.26761(19) 0.0389(8) Uani 1 1 d D . .
H1 H 0.6686(19) 0.017(2) 0.2272(14) 0.034(7) Uiso 1 1 d . . .
C21 C 0.724(2) 0.034(2) 0.3530(10) 0.038(5) Uani 0.36(2) 1 d PDU A 1
F22 F 0.5849(15) -0.110(2) 0.3228(11) 0.056(3) Uani 0.36(2) 1 d PDU A 1
C22 C 0.6728(18) -0.0621(18) 0.3736(9) 0.040(4) Uani 0.36(2) 1 d PDU A 1
F23 F 0.6508(14) -0.2114(13) 0.4598(9) 0.086(4) Uani 0.36(2) 1 d PDU A 1
C23 C 0.7039(14) -0.1165(15) 0.4438(8) 0.054(4) Uani 0.36(2) 1 d PDU A 1
F24 F 0.8218(15) -0.1194(14) 0.5710(7) 0.090(4) Uani 0.36(2) 1 d PDU A 1
C24 C 0.7900(15) -0.0741(15) 0.4998(7) 0.053(4) Uani 0.36(2) 1 d PDU A 1
F25 F 0.9287(12) 0.0716(15) 0.5374(7) 0.074(3) Uani 0.36(2) 1 d PDU A 1
C25 C 0.8456(13) 0.0215(17) 0.4840(7) 0.048(4) Uani 0.36(2) 1 d PDU A 1
F26 F 0.8687(16) 0.1677(15) 0.4012(9) 0.049(3) Uani 0.36(2) 1 d PDU A 1
C26 C 0.8106(17) 0.0730(19) 0.4130(8) 0.037(4) Uani 0.36(2) 1 d PDU A 1
C21A C 0.7393(14) 0.0514(15) 0.3539(6) 0.043(3) Uani 0.64(2) 1 d PDU A 2
F22A F 0.6134(9) -0.1073(11) 0.3357(7) 0.059(2) Uani 0.64(2) 1 d PDU A 2
C22A C 0.7022(11) -0.0492(12) 0.3805(6) 0.051(3) Uani 0.64(2) 1 d PDU A 2
F23A F 0.6985(10) -0.1939(7) 0.4733(5) 0.093(2) Uani 0.64(2) 1 d PDU A 2
C23A C 0.7422(10) -0.0957(9) 0.4525(5) 0.064(2) Uani 0.64(2) 1 d PDU A 2
F24A F 0.8696(9) -0.0851(9) 0.5718(4) 0.103(3) Uani 0.64(2) 1 d PDU A 2
C24A C 0.8287(9) -0.0400(10) 0.5010(4) 0.056(3) Uani 0.64(2) 1 d PDU A 2
F25A F 0.9554(7) 0.1124(10) 0.5274(5) 0.079(2) Uani 0.64(2) 1 d PDU A 2
C25A C 0.8709(8) 0.0597(10) 0.4782(5) 0.053(2) Uani 0.64(2) 1 d PDU A 2
F26A F 0.8740(9) 0.2016(10) 0.3871(7) 0.061(2) Uani 0.64(2) 1 d PDU A 2
C26A C 0.8281(9) 0.1025(11) 0.4060(5) 0.044(2) Uani 0.64(2) 1 d PDU A 2
C31 C 0.5514(2) 0.1340(3) 0.26568(15) 0.0372(7) Uani 1 1 d . A .
F32 F 0.46720(12) 0.02600(17) 0.15368(9) 0.0540(5) Uani 1 1 d . A .
C32 C 0.4591(2) 0.0971(3) 0.21142(16) 0.0396(7) Uani 1 1 d . . .
F33 F 0.26835(13) 0.08864(19) 0.15620(10) 0.0640(6) Uani 1 1 d . . .
C33 C 0.3552(2) 0.1268(3) 0.21173(17) 0.0438(7) Uani 1 1 d . A .
F34 F 0.23807(13) 0.22895(19) 0.26942(12) 0.0705(6) Uani 1 1 d . A .
C34 C 0.3391(2) 0.1971(3) 0.26874(18) 0.0462(8) Uani 1 1 d . . .
F35 F 0.41208(14) 0.30352(17) 0.38129(10) 0.0606(5) Uani 1 1 d . . .
C35 C 0.4269(2) 0.2366(3) 0.32432(17) 0.0424(7) Uani 1 1 d . A .
F36 F 0.61219(13) 0.24614(17) 0.37909(10) 0.0562(5) Uani 1 1 d . A .
C36 C 0.5294(2) 0.2047(3) 0.32132(16) 0.0401(7) 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
N1 C11 1.471(4) . ?
N1 C1 1.559(4) . ?
N1 C5 1.565(4) . ?
N1 H2 0.92(3) . ?
C1 C2 1.522(4) . ?
C1 C7 1.524(4) . ?
C1 C6 1.528(4) . ?
C2 C3 1.511(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.508(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.519(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C8 1.523(4) . ?
C5 C9 1.528(4) . ?
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 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C11 C12 1.322(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.520(4) . ?
C12 B1 1.628(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
B1 C21A 1.635(8) . ?
B1 C31 1.643(4) . ?
B1 C21 1.657(11) . ?
B1 H1 1.13(3) . ?
C21 C22 1.376(12) . ?
C21 C26 1.398(12) . ?
F22 C22 1.360(12) . ?
C22 C23 1.379(11) . ?
F23 C23 1.347(12) . ?
C23 C24 1.367(11) . ?
F24 C24 1.352(11) . ?
C24 C25 1.371(11) . ?
F25 C25 1.354(11) . ?
C25 C26 1.380(13) . ?
F26 C26 1.356(11) . ?
C21A C22A 1.374(9) . ?
C21A C26A 1.392(9) . ?
F22A C22A 1.373(9) . ?
C22A C23A 1.378(9) . ?
F23A C23A 1.346(9) . ?
C23A C24A 1.368(9) . ?
F24A C24A 1.356(8) . ?
C24A C25A 1.366(9) . ?
F25A C25A 1.341(8) . ?
C25A C26A 1.370(9) . ?
F26A C26A 1.356(9) . ?
C31 C32 1.382(4) . ?
C31 C36 1.383(4) . ?
F32 C32 1.354(3) . ?
C32 C33 1.374(4) . ?
F33 C33 1.353(3) . ?
C33 C34 1.371(4) . ?
F34 C34 1.347(3) . ?
C34 C35 1.366(4) . ?
F35 C35 1.342(3) . ?
C35 C36 1.377(4) . ?
F36 C36 1.358(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
C11 N1 C1 113.4(2) . . ?
C11 N1 C5 112.2(2) . . ?
C1 N1 C5 117.3(2) . . ?
C11 N1 H2 106.9(16) . . ?
C1 N1 H2 102.2(16) . . ?
C5 N1 H2 103.3(16) . . ?
C2 C1 C7 109.0(3) . . ?
C2 C1 C6 111.4(3) . . ?
C7 C1 C6 109.4(3) . . ?
C2 C1 N1 109.2(2) . . ?
C7 C1 N1 106.0(2) . . ?
C6 C1 N1 111.7(3) . . ?
C3 C2 C1 114.0(3) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 108.9(3) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 C5 114.6(3) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C8 111.5(3) . . ?
C4 C5 C9 109.8(3) . . ?
C8 C5 C9 109.4(3) . . ?
C4 C5 N1 107.6(3) . . ?
C8 C5 N1 112.2(3) . . ?
C9 C5 N1 106.3(2) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C11 N1 123.6(3) . . ?
C12 C11 H11 118.2 . . ?
N1 C11 H11 118.2 . . ?
C11 C12 C13 115.1(3) . . ?
C11 C12 B1 124.7(3) . . ?
C13 C12 B1 120.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 B1 C21A 112.9(5) . . ?
C12 B1 C31 111.3(2) . . ?
C21A B1 C31 109.0(8) . . ?
C12 B1 C21 122.4(6) . . ?
C21A B1 C21 9.6(7) . . ?
C31 B1 C21 104.2(12) . . ?
C12 B1 H1 106.7(13) . . ?
C21A B1 H1 109.4(15) . . ?
C31 B1 H1 107.4(12) . . ?
C21 B1 H1 103.9(17) . . ?
C22 C21 C26 111.8(11) . . ?
C22 C21 B1 119.8(10) . . ?
C26 C21 B1 128.2(11) . . ?
F22 C22 C21 119.8(13) . . ?
F22 C22 C23 115.3(13) . . ?
C21 C22 C23 124.8(12) . . ?
F23 C23 C24 118.0(10) . . ?
F23 C23 C22 121.7(11) . . ?
C24 C23 C22 120.3(11) . . ?
F24 C24 C23 123.6(11) . . ?
F24 C24 C25 117.7(11) . . ?
C23 C24 C25 118.6(10) . . ?
F25 C25 C24 122.1(11) . . ?
F25 C25 C26 119.1(12) . . ?
C24 C25 C26 118.6(10) . . ?
F26 C26 C25 115.7(11) . . ?
F26 C26 C21 118.5(12) . . ?
C25 C26 C21 125.7(11) . . ?
C22A C21A C26A 113.6(7) . . ?
C22A C21A B1 117.1(7) . . ?
C26A C21A B1 129.3(7) . . ?
F22A C22A C21A 119.9(8) . . ?
F22A C22A C23A 114.4(9) . . ?
C21A C22A C23A 125.6(9) . . ?
F23A C23A C24A 121.7(8) . . ?
F23A C23A C22A 120.8(8) . . ?
C24A C23A C22A 117.5(8) . . ?
F24A C24A C25A 121.4(8) . . ?
F24A C24A C23A 118.3(8) . . ?
C25A C24A C23A 120.2(7) . . ?
F25A C25A C24A 118.5(7) . . ?
F25A C25A C26A 121.5(8) . . ?
C24A C25A C26A 119.9(7) . . ?
F26A C26A C25A 116.9(8) . . ?
F26A C26A C21A 120.1(8) . . ?
C25A C26A C21A 123.0(8) . . ?
C32 C31 C36 113.2(2) . . ?
C32 C31 B1 124.2(3) . . ?
C36 C31 B1 122.5(2) . . ?
F32 C32 C33 115.5(2) . . ?
F32 C32 C31 120.3(2) . . ?
C33 C32 C31 124.2(3) . . ?
F33 C33 C34 119.4(2) . . ?
F33 C33 C32 121.0(3) . . ?
C34 C33 C32 119.6(3) . . ?
F34 C34 C35 120.0(3) . . ?
F34 C34 C33 120.5(3) . . ?
C35 C34 C33 119.4(2) . . ?
F35 C35 C34 119.9(2) . . ?
F35 C35 C36 121.2(3) . . ?
C34 C35 C36 118.8(3) . . ?
F36 C36 C35 115.3(2) . . ?
F36 C36 C31 119.9(2) . . ?
C35 C36 C31 124.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 -179.5(2) . . . . ?
C5 N1 C1 C2 -46.1(3) . . . . ?
C11 N1 C1 C7 63.3(3) . . . . ?
C5 N1 C1 C7 -163.3(3) . . . . ?
C11 N1 C1 C6 -55.8(3) . . . . ?
C5 N1 C1 C6 77.6(3) . . . . ?
C7 C1 C2 C3 166.6(3) . . . . ?
C6 C1 C2 C3 -72.6(4) . . . . ?
N1 C1 C2 C3 51.2(3) . . . . ?
C1 C2 C3 C4 -59.0(4) . . . . ?
C2 C3 C4 C5 61.1(4) . . . . ?
C3 C4 C5 C8 69.5(4) . . . . ?
C3 C4 C5 C9 -169.2(3) . . . . ?
C3 C4 C5 N1 -53.9(3) . . . . ?
C11 N1 C5 C4 -179.3(2) . . . . ?
C1 N1 C5 C4 46.9(3) . . . . ?
C11 N1 C5 C8 57.8(3) . . . . ?
C1 N1 C5 C8 -76.0(4) . . . . ?
C11 N1 C5 C9 -61.7(3) . . . . ?
C1 N1 C5 C9 164.5(3) . . . . ?
C1 N1 C11 C12 -109.2(3) . . . . ?
C5 N1 C11 C12 115.1(3) . . . . ?
N1 C11 C12 C13 -175.2(3) . . . . ?
N1 C11 C12 B1 0.6(5) . . . . ?
C11 C12 B1 C21A 102.7(10) . . . . ?
C13 C12 B1 C21A -81.7(10) . . . . ?
C11 C12 B1 C31 -134.4(3) . . . . ?
C13 C12 B1 C31 41.2(4) . . . . ?
C11 C12 B1 C21 101.7(16) . . . . ?
C13 C12 B1 C21 -82.7(16) . . . . ?
C12 B1 C21 C22 -174(2) . . . . ?
C21A B1 C21 C22 -179(16) . . . . ?
C31 B1 C21 C22 59(3) . . . . ?
C12 B1 C21 C26 12(4) . . . . ?
C21A B1 C21 C26 6(10) . . . . ?
C31 B1 C21 C26 -116(3) . . . . ?
C26 C21 C22 F22 178(3) . . . . ?
B1 C21 C22 F22 3(4) . . . . ?
C26 C21 C22 C23 -2(5) . . . . ?
B1 C21 C22 C23 -178(2) . . . . ?
F22 C22 C23 F23 1(3) . . . . ?
C21 C22 C23 F23 -179(3) . . . . ?
F22 C22 C23 C24 -179(2) . . . . ?
C21 C22 C23 C24 2(4) . . . . ?
F23 C23 C24 F24 -3(3) . . . . ?
C22 C23 C24 F24 176.8(19) . . . . ?
F23 C23 C24 C25 179.2(17) . . . . ?
C22 C23 C24 C25 -1(3) . . . . ?
F24 C24 C25 F25 -1(3) . . . . ?
C23 C24 C25 F25 177.1(17) . . . . ?
F24 C24 C25 C26 -176.5(18) . . . . ?
C23 C24 C25 C26 2(3) . . . . ?
F25 C25 C26 F26 4(3) . . . . ?
C24 C25 C26 F26 180(2) . . . . ?
F25 C25 C26 C21 -178(3) . . . . ?
C24 C25 C26 C21 -3(4) . . . . ?
C22 C21 C26 F26 -180(3) . . . . ?
B1 C21 C26 F26 -4(5) . . . . ?
C22 C21 C26 C25 3(5) . . . . ?
B1 C21 C26 C25 178(2) . . . . ?
C12 B1 C21A C22A -169.4(15) . . . . ?
C31 B1 C21A C22A 66.4(19) . . . . ?
C21 B1 C21A C22A 5(12) . . . . ?
C12 B1 C21A C26A 10(3) . . . . ?
C31 B1 C21A C26A -114(2) . . . . ?
C21 B1 C21A C26A -175(15) . . . . ?
C26A C21A C22A F22A 178.6(17) . . . . ?
B1 C21A C22A F22A -2(3) . . . . ?
C26A C21A C22A C23A 3(3) . . . . ?
B1 C21A C22A C23A -177.0(14) . . . . ?
F22A C22A C23A F23A 3(2) . . . . ?
C21A C22A C23A F23A 178.8(17) . . . . ?
F22A C22A C23A C24A -178.2(12) . . . . ?
C21A C22A C23A C24A -3(2) . . . . ?
F23A C23A C24A F24A -0.9(16) . . . . ?
C22A C23A C24A F24A -179.5(11) . . . . ?
F23A C23A C24A C25A -179.8(10) . . . . ?
C22A C23A C24A C25A 1.6(17) . . . . ?
F24A C24A C25A F25A 0.7(15) . . . . ?
C23A C24A C25A F25A 179.6(9) . . . . ?
F24A C24A C25A C26A 179.6(10) . . . . ?
C23A C24A C25A C26A -1.6(16) . . . . ?
F25A C25A C26A F26A -1.0(18) . . . . ?
C24A C25A C26A F26A -179.9(12) . . . . ?
F25A C25A C26A C21A -178.8(16) . . . . ?
C24A C25A C26A C21A 2(2) . . . . ?
C22A C21A C26A F26A 179.3(16) . . . . ?
B1 C21A C26A F26A 0(3) . . . . ?
C22A C21A C26A C25A -3(3) . . . . ?
B1 C21A C26A C25A 177.2(15) . . . . ?
C12 B1 C31 C32 103.0(3) . . . . ?
C21A B1 C31 C32 -131.8(6) . . . . ?
C21 B1 C31 C32 -123.2(9) . . . . ?
C12 B1 C31 C36 -80.1(3) . . . . ?
C21A B1 C31 C36 45.0(6) . . . . ?
C21 B1 C31 C36 53.6(9) . . . . ?
C36 C31 C32 F32 -179.1(3) . . . . ?
B1 C31 C32 F32 -2.0(4) . . . . ?
C36 C31 C32 C33 0.0(4) . . . . ?
B1 C31 C32 C33 177.1(3) . . . . ?
F32 C32 C33 F33 -1.6(4) . . . . ?
C31 C32 C33 F33 179.2(3) . . . . ?
F32 C32 C33 C34 179.0(3) . . . . ?
C31 C32 C33 C34 -0.1(5) . . . . ?
F33 C33 C34 F34 -0.6(5) . . . . ?
C32 C33 C34 F34 178.8(3) . . . . ?
F33 C33 C34 C35 -179.3(3) . . . . ?
C32 C33 C34 C35 0.1(5) . . . . ?
F34 C34 C35 F35 2.6(4) . . . . ?
C33 C34 C35 F35 -178.6(3) . . . . ?
F34 C34 C35 C36 -178.6(3) . . . . ?
C33 C34 C35 C36 0.1(5) . . . . ?
F35 C35 C36 F36 -0.4(4) . . . . ?
C34 C35 C36 F36 -179.1(3) . . . . ?
F35 C35 C36 C31 178.5(3) . . . . ?
C34 C35 C36 C31 -0.3(5) . . . . ?
C32 C31 C36 F36 179.0(3) . . . . ?
B1 C31 C36 F36 1.9(4) . . . . ?
C32 C31 C36 C35 0.2(4) . . . . ?
B1 C31 C36 C35 -177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_erk8313
_database_code_depnum_ccdc_archive 'CCDC 1843580'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H23 B F15 N Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         709.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   12.6697(4)
_cell_length_b                   17.9299(6)
_cell_length_c                   13.6897(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.9250(10)
_cell_angle_gamma                90
_cell_volume                     3053.48(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9561
_cell_measurement_theta_min      4.1105
_cell_measurement_theta_max      67.9030
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432

_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            72474
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         68.07
_diffrn_reflns_theta_full        68.07
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5523
_reflns_number_gt                4965
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0746
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         5523
_refine_ls_number_parameters     431
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²+1.8541P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.11515(10) 0.19388(7) 0.50803(9) 0.0200(3) Uani d . . . 1 . .
C C2 0.20995(11) 0.24319(8) 0.37307(11) 0.0170(3) Uani d . . . 1 . .
C C1 0.16240(11) 0.21963(8) 0.44092(11) 0.0176(3) Uani d . . . 1 . .
C C11 -0.00417(12) 0.20407(9) 0.50045(12) 0.0245(3) Uani d . . . 1 . .
H H11 -0.0265 0.1764 0.5566 0.029 Uiso calc U . R 1 . .
C C12 -0.06516(14) 0.17217(12) 0.40384(14) 0.0386(4) Uani d . . . 1 . .
H H12A -0.0469 0.2001 0.3478 0.058 Uiso calc U . R 1 . .
H H12B -0.1426 0.1761 0.4025 0.058 Uiso calc U . R 1 . .
H H12C -0.0456 0.1197 0.3986 0.058 Uiso calc U . R 1 . .
C C13 -0.02843(14) 0.28602(10) 0.51139(14) 0.0317(4) Uani d . . . 1 . .
H H13A 0.0112 0.3043 0.5754 0.048 Uiso calc U . R 1 . .
H H13B -0.1057 0.2926 0.5086 0.048 Uiso calc U . R 1 . .
H H13C -0.0064 0.3142 0.4572 0.048 Uiso calc U . R 1 . .
C C14 0.17816(14) 0.15296(10) 0.59643(12) 0.0307(4) Uani d . . . 1 . .
H H14 0.2555 0.1531 0.5902 0.037 Uiso calc U . R 1 . .
C C15 0.14100(17) 0.07230(11) 0.59543(15) 0.0438(5) Uani d . . . 1 . .
H H15A 0.0669 0.0705 0.6065 0.066 Uiso calc U . R 1 . .
H H15B 0.1878 0.0445 0.6483 0.066 Uiso calc U . R 1 . .
H H15C 0.1443 0.0498 0.5308 0.066 Uiso calc U . R 1 . .
C C16 0.16918(16) 0.19224(12) 0.69267(13) 0.0410(5) Uani d . . . 1 . .
H H16A 0.191 0.2445 0.6892 0.061 Uiso calc U . R 1 . .
H H16B 0.2161 0.1676 0.7485 0.061 Uiso calc U . R 1 . .
H H16C 0.0946 0.19 0.7025 0.061 Uiso calc U . R 1 . .
Si Si1 0.21592(3) 0.16727(2) 0.27453(3) 0.02110(10) Uani d . . . 1 . .
C C3 0.08463(16) 0.16493(11) 0.18605(13) 0.0401(4) Uani d . . . 1 . .
H H3A 0.0709 0.2137 0.1537 0.06 Uiso calc U . R 1 . .
H H3B 0.0271 0.1533 0.2224 0.06 Uiso calc U . R 1 . .
H H3C 0.0869 0.1266 0.1355 0.06 Uiso calc U . R 1 . .
C C4 0.24125(16) 0.07664(9) 0.34040(13) 0.0328(4) Uani d . . . 1 . .
H H4A 0.2578 0.0386 0.2941 0.049 Uiso calc U . R 1 . .
H H4B 0.1771 0.0617 0.3659 0.049 Uiso calc U . R 1 . .
H H4C 0.3022 0.0818 0.396 0.049 Uiso calc U . R 1 . .
C C5 0.32404(18) 0.18580(11) 0.20374(17) 0.0475(5) Uani d . . . 1 . .
H H5A 0.3935 0.1876 0.2497 0.071 Uiso calc U . R 1 . .
H H5B 0.3107 0.2337 0.1691 0.071 Uiso calc U . R 1 . .
H H5C 0.3252 0.1459 0.155 0.071 Uiso calc U . R 1 . .
B B1 0.25307(13) 0.33131(9) 0.36558(13) 0.0182(3) Uani d . . . 1 . .
C C21 0.38512(11) 0.33826(8) 0.38739(10) 0.0178(3) Uani d . . . 1 . .
F F22 0.42843(7) 0.21157(5) 0.42882(7) 0.0286(2) Uani d . . . 1 . .
C C22 0.46030(12) 0.28226(8) 0.41541(11) 0.0201(3) Uani d . . . 1 . .
F F23 0.63914(7) 0.23663(5) 0.45716(8) 0.0315(2) Uani d . . . 1 . .
C C23 0.57020(12) 0.29372(8) 0.43257(11) 0.0209(3) Uani d . . . 1 . .
F F24 0.71695(7) 0.37588(5) 0.44292(7) 0.0294(2) Uani d . . . 1 . .
C C24 0.61038(11) 0.36443(9) 0.42567(11) 0.0214(3) Uani d . . . 1 . .
F F25 0.57720(7) 0.49235(5) 0.39538(8) 0.0323(2) Uani d . . . 1 . .
C C25 0.53957(12) 0.42278(8) 0.40185(11) 0.0214(3) Uani d . . . 1 . .
F F26 0.36591(7) 0.46818(5) 0.35799(7) 0.0256(2) Uani d . . . 1 . .
C C26 0.43102(12) 0.40855(8) 0.38358(11) 0.0201(3) Uani d . . . 1 . .
C C31 0.21787(11) 0.38275(8) 0.45439(11) 0.0192(3) Uani d . . . 1 . .
F F32 0.31477(7) 0.30050(5) 0.57544(6) 0.0256(2) Uani d . . . 1 . .
C C32 0.25347(11) 0.36274(9) 0.55339(12) 0.0221(3) Uani d . . . 1 . .
F F33 0.27180(9) 0.37955(7) 0.72755(7) 0.0418(3) Uani d . . . 1 . .
C C33 0.23325(13) 0.40271(10) 0.63406(12) 0.0289(4) Uani d . . . 1 . .
F F34 0.15437(9) 0.50801(7) 0.69516(9) 0.0464(3) Uani d . . . 1 . .
C C34 0.17483(13) 0.46777(10) 0.61801(14) 0.0315(4) Uani d . . . 1 . .
F F35 0.08430(7) 0.55544(5) 0.50522(8) 0.0362(2) Uani d . . . 1 . .
C C35 0.13993(12) 0.49138(9) 0.52247(14) 0.0272(4) Uani d . . . 1 . .
F F36 0.12747(7) 0.48065(5) 0.35301(7) 0.0280(2) Uani d . . . 1 . .
C C36 0.16217(11) 0.45006(8) 0.44372(12) 0.0229(3) Uani d . . . 1 . .
C C41 0.19833(11) 0.35860(8) 0.25174(11) 0.0184(3) Uani d . . . 1 . .
F F42 0.02428(7) 0.34770(5) 0.29040(7) 0.0258(2) Uani d . . . 1 . .
C C42 0.08696(12) 0.36498(8) 0.22366(12) 0.0206(3) Uani d . . . 1 . .
F F43 -0.07417(7) 0.39577(5) 0.11255(7) 0.0317(2) Uani d . . . 1 . .
C C43 0.03371(12) 0.38910(8) 0.13198(12) 0.0230(3) Uani d . . . 1 . .
F F44 0.04179(8) 0.43039(5) -0.03057(7) 0.0308(2) Uani d . . . 1 . .
C C44 0.09142(13) 0.40727(8) 0.05953(11) 0.0231(3) Uani d . . . 1 . .
F F45 0.25984(8) 0.41660(5) 0.01179(7) 0.0295(2) Uani d . . . 1 . .
C C45 0.20127(12) 0.40012(8) 0.08137(11) 0.0219(3) Uani d . . . 1 . .
F F46 0.36050(7) 0.37154(5) 0.18686(6) 0.02403(19) Uani d . . . 1 . .
C C46 0.25165(11) 0.37645(8) 0.17494(11) 0.0192(3) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.2744(19) ?
N1 C11 . 1.5067(19) ?
N1 C14 . 1.508(2) ?
C2 C1 . 1.271(2) ?
C2 B1 . 1.681(2) ?
C2 Si1 . 1.9281(15) ?
C11 C12 . 1.512(2) ?
C11 C13 . 1.515(2) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C16 . 1.517(3) ?
C14 C15 . 1.520(3) ?
C14 H14 . 1.0 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
Si1 C5 . 1.8518(19) ?
Si1 C4 . 1.8565(17) ?
Si1 C3 . 1.8634(19) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
B1 C21 . 1.647(2) ?
B1 C31 . 1.653(2) ?
B1 C41 . 1.655(2) ?
C21 C22 . 1.387(2) ?
C21 C26 . 1.393(2) ?
F22 C22 . 1.3532(17) ?
C22 C23 . 1.383(2) ?
F23 C23 . 1.3462(17) ?
C23 C24 . 1.376(2) ?
F24 C24 . 1.3417(17) ?
C24 C25 . 1.377(2) ?
F25 C25 . 1.3443(17) ?
C25 C26 . 1.374(2) ?
F26 C26 . 1.3553(17) ?
C31 C36 . 1.392(2) ?
C31 C32 . 1.392(2) ?
F32 C32 . 1.3603(17) ?
C32 C33 . 1.381(2) ?
F33 C33 . 1.346(2) ?
C33 C34 . 1.377(3) ?
F34 C34 . 1.3442(19) ?
C34 C35 . 1.366(3) ?
F35 C35 . 1.3449(18) ?
C35 C36 . 1.380(2) ?
F36 C36 . 1.3524(19) ?
C41 C46 . 1.390(2) ?
C41 C42 . 1.395(2) ?
F42 C42 . 1.3552(17) ?
C42 C43 . 1.377(2) ?
F43 C43 . 1.3474(17) ?
C43 C44 . 1.378(2) ?
F44 C44 . 1.3396(18) ?
C44 C45 . 1.373(2) ?
F45 C45 . 1.3466(18) ?
C45 C46 . 1.385(2) ?
F46 C46 . 1.3606(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C11 . . 120.58(12) ?
C1 N1 C14 . . 120.35(12) ?
C11 N1 C14 . . 119.07(12) ?
C1 C2 B1 . . 124.15(13) ?
C1 C2 Si1 . . 111.31(11) ?
B1 C2 Si1 . . 124.37(10) ?
C2 C1 N1 . . 178.17(15) ?
N1 C11 C12 . . 110.74(13) ?
N1 C11 C13 . . 109.30(13) ?
C12 C11 C13 . . 111.95(15) ?
N1 C11 H11 . . 108.2 ?
C12 C11 H11 . . 108.2 ?
C13 C11 H11 . . 108.2 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 C16 . . 110.83(14) ?
N1 C14 C15 . . 109.86(15) ?
C16 C14 C15 . . 112.05(15) ?
N1 C14 H14 . . 108.0 ?
C16 C14 H14 . . 108.0 ?
C15 C14 H14 . . 108.0 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C5 Si1 C4 . . 109.53(9) ?
C5 Si1 C3 . . 108.76(10) ?
C4 Si1 C3 . . 110.29(9) ?
C5 Si1 C2 . . 111.74(8) ?
C4 Si1 C2 . . 107.72(7) ?
C3 Si1 C2 . . 108.79(7) ?
Si1 C3 H3A . . 109.5 ?
Si1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Si1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Si1 C4 H4A . . 109.5 ?
Si1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Si1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C21 B1 C31 . . 103.34(11) ?
C21 B1 C41 . . 112.22(12) ?
C31 B1 C41 . . 113.84(12) ?
C21 B1 C2 . . 112.99(11) ?
C31 B1 C2 . . 110.08(12) ?
C41 B1 C2 . . 104.60(11) ?
C22 C21 C26 . . 113.30(13) ?
C22 C21 B1 . . 128.02(13) ?
C26 C21 B1 . . 118.58(12) ?
F22 C22 C23 . . 115.65(13) ?
F22 C22 C21 . . 120.57(13) ?
C23 C22 C21 . . 123.78(14) ?
F23 C23 C24 . . 119.13(13) ?
F23 C23 C22 . . 120.94(13) ?
C24 C23 C22 . . 119.92(13) ?
F24 C24 C23 . . 120.12(13) ?
F24 C24 C25 . . 120.95(13) ?
C23 C24 C25 . . 118.92(13) ?
F25 C25 C26 . . 121.03(13) ?
F25 C25 C24 . . 119.83(13) ?
C26 C25 C24 . . 119.13(14) ?
F26 C26 C25 . . 116.08(13) ?
F26 C26 C21 . . 119.04(12) ?
C25 C26 C21 . . 124.87(13) ?
C36 C31 C32 . . 112.96(14) ?
C36 C31 B1 . . 127.50(14) ?
C32 C31 B1 . . 119.31(13) ?
F32 C32 C33 . . 115.66(14) ?
F32 C32 C31 . . 119.57(13) ?
C33 C32 C31 . . 124.75(15) ?
F33 C33 C34 . . 120.03(15) ?
F33 C33 C32 . . 120.76(15) ?
C34 C33 C32 . . 119.20(16) ?
F34 C34 C35 . . 120.69(16) ?
F34 C34 C33 . . 120.48(17) ?
C35 C34 C33 . . 118.82(15) ?
F35 C35 C34 . . 119.76(15) ?
F35 C35 C36 . . 119.93(16) ?
C34 C35 C36 . . 120.30(15) ?
F36 C36 C35 . . 114.86(13) ?
F36 C36 C31 . . 121.21(14) ?
C35 C36 C31 . . 123.91(15) ?
C46 C41 C42 . . 112.57(13) ?
C46 C41 B1 . . 127.09(13) ?
C42 C41 B1 . . 120.34(13) ?
F42 C42 C43 . . 115.97(13) ?
F42 C42 C41 . . 119.13(13) ?
C43 C42 C41 . . 124.89(14) ?
F43 C43 C42 . . 120.74(14) ?
F43 C43 C44 . . 119.58(14) ?
C42 C43 C44 . . 119.67(14) ?
F44 C44 C45 . . 120.58(14) ?
F44 C44 C43 . . 121.02(14) ?
C45 C44 C43 . . 118.39(14) ?
F45 C45 C44 . . 119.82(14) ?
F45 C45 C46 . . 120.15(14) ?
C44 C45 C46 . . 120.03(14) ?
F46 C46 C45 . . 114.19(13) ?
F46 C46 C41 . . 121.41(13) ?
C45 C46 C41 . . 124.40(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C11 C12 . . . . 56.72(19) ?
C14 N1 C11 C12 . . . . -123.49(16) ?
C1 N1 C11 C13 . . . . -67.07(18) ?
C14 N1 C11 C13 . . . . 112.72(15) ?
C1 N1 C14 C16 . . . . 119.81(16) ?
C11 N1 C14 C16 . . . . -59.98(19) ?
C1 N1 C14 C15 . . . . -115.82(16) ?
C11 N1 C14 C15 . . . . 64.39(18) ?
C1 C2 B1 C21 . . . . 111.49(16) ?
Si1 C2 B1 C21 . . . . -73.68(15) ?
C1 C2 B1 C31 . . . . -3.48(19) ?
Si1 C2 B1 C31 . . . . 171.36(9) ?
C1 C2 B1 C41 . . . . -126.16(15) ?
Si1 C2 B1 C41 . . . . 48.67(14) ?
C31 B1 C21 C22 . . . . 115.09(16) ?
C41 B1 C21 C22 . . . . -121.83(16) ?
C2 B1 C21 C22 . . . . -3.8(2) ?
C31 B1 C21 C26 . . . . -60.95(16) ?
C41 B1 C21 C26 . . . . 62.12(17) ?
C2 B1 C21 C26 . . . . -179.90(13) ?
C26 C21 C22 F22 . . . . 175.75(13) ?
B1 C21 C22 F22 . . . . -0.5(2) ?
C26 C21 C22 C23 . . . . -3.5(2) ?
B1 C21 C22 C23 . . . . -179.67(14) ?
F22 C22 C23 F23 . . . . 2.5(2) ?
C21 C22 C23 F23 . . . . -178.29(14) ?
F22 C22 C23 C24 . . . . -176.79(13) ?
C21 C22 C23 C24 . . . . 2.5(2) ?
F23 C23 C24 F24 . . . . 0.3(2) ?
C22 C23 C24 F24 . . . . 179.55(13) ?
F23 C23 C24 C25 . . . . -179.11(13) ?
C22 C23 C24 C25 . . . . 0.2(2) ?
F24 C24 C25 F25 . . . . 0.2(2) ?
C23 C24 C25 F25 . . . . 179.56(14) ?
F24 C24 C25 C26 . . . . 179.23(14) ?
C23 C24 C25 C26 . . . . -1.4(2) ?
F25 C25 C26 F26 . . . . 0.7(2) ?
C24 C25 C26 F26 . . . . -178.32(13) ?
F25 C25 C26 C21 . . . . 179.19(14) ?
C24 C25 C26 C21 . . . . 0.2(2) ?
C22 C21 C26 F26 . . . . -179.40(13) ?
B1 C21 C26 F26 . . . . -2.8(2) ?
C22 C21 C26 C25 . . . . 2.2(2) ?
B1 C21 C26 C25 . . . . 178.78(14) ?
C21 B1 C31 C36 . . . . 112.09(15) ?
C41 B1 C31 C36 . . . . -9.9(2) ?
C2 B1 C31 C36 . . . . -126.97(15) ?
C21 B1 C31 C32 . . . . -61.84(16) ?
C41 B1 C31 C32 . . . . 176.16(12) ?
C2 B1 C31 C32 . . . . 59.09(17) ?
C36 C31 C32 F32 . . . . -176.05(12) ?
B1 C31 C32 F32 . . . . -1.3(2) ?
C36 C31 C32 C33 . . . . 2.5(2) ?
B1 C31 C32 C33 . . . . 177.24(14) ?
F32 C32 C33 F33 . . . . -0.8(2) ?
C31 C32 C33 F33 . . . . -179.35(14) ?
F32 C32 C33 C34 . . . . 177.84(14) ?
C31 C32 C33 C34 . . . . -0.7(2) ?
F33 C33 C34 F34 . . . . -1.1(2) ?
C32 C33 C34 F34 . . . . -179.69(14) ?
F33 C33 C34 C35 . . . . 177.68(15) ?
C32 C33 C34 C35 . . . . -1.0(2) ?
F34 C34 C35 F35 . . . . -0.1(2) ?
C33 C34 C35 F35 . . . . -178.88(14) ?
F34 C34 C35 C36 . . . . 179.40(14) ?
C33 C34 C35 C36 . . . . 0.7(2) ?
F35 C35 C36 F36 . . . . 2.2(2) ?
C34 C35 C36 F36 . . . . -177.30(14) ?
F35 C35 C36 C31 . . . . -179.12(13) ?
C34 C35 C36 C31 . . . . 1.3(2) ?
C32 C31 C36 F36 . . . . 175.80(13) ?
B1 C31 C36 F36 . . . . 1.5(2) ?
C32 C31 C36 C35 . . . . -2.8(2) ?
B1 C31 C36 C35 . . . . -177.01(14) ?
C21 B1 C41 C46 . . . . 8.3(2) ?
C31 B1 C41 C46 . . . . 125.27(15) ?
C2 B1 C41 C46 . . . . -114.53(15) ?
C21 B1 C41 C42 . . . . -172.45(12) ?
C31 B1 C41 C42 . . . . -55.50(18) ?
C2 B1 C41 C42 . . . . 64.70(16) ?
C46 C41 C42 F42 . . . . 178.55(12) ?
B1 C41 C42 F42 . . . . -0.8(2) ?
C46 C41 C42 C43 . . . . -2.6(2) ?
B1 C41 C42 C43 . . . . 178.11(14) ?
F42 C42 C43 F43 . . . . 1.1(2) ?
C41 C42 C43 F43 . . . . -177.84(13) ?
F42 C42 C43 C44 . . . . -179.50(13) ?
C41 C42 C43 C44 . . . . 1.6(2) ?
F43 C43 C44 F44 . . . . -1.0(2) ?
C42 C43 C44 F44 . . . . 179.52(13) ?
F43 C43 C44 C45 . . . . 179.85(13) ?
C42 C43 C44 C45 . . . . 0.4(2) ?
F44 C44 C45 F45 . . . . 0.1(2) ?
C43 C44 C45 F45 . . . . 179.24(13) ?
F44 C44 C45 C46 . . . . 179.74(13) ?
C43 C44 C45 C46 . . . . -1.2(2) ?
F45 C45 C46 F46 . . . . -0.55(19) ?
C44 C45 C46 F46 . . . . 179.85(13) ?
F45 C45 C46 C41 . . . . 179.59(13) ?
C44 C45 C46 C41 . . . . 0.0(2) ?
C42 C41 C46 F46 . . . . -178.09(12) ?
B1 C41 C46 F46 . . . . 1.2(2) ?
C42 C41 C46 C45 . . . . 1.8(2) ?
B1 C41 C46 C45 . . . . -178.96(14) ?

####################################################################### 
# 
# 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_erk8383
_database_code_depnum_ccdc_archive 'CCDC 1843578'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H21 B F15 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         691.29

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.0404(3)
_cell_length_b                   16.5379(6)
_cell_length_c                   19.3560(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.7720(10)
_cell_angle_gamma                90
_cell_volume                     2851.91(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.3531
_cell_measurement_theta_max      27.5665
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392

_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            77832
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             6574
_reflns_number_gt                5555
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0882
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         6574
_refine_ls_number_parameters     429
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+1.6218P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.50857(16) 0.30083(8) 0.35221(7) 0.0109(3) Uani d . . . 1 . .
N N1 0.73926(12) 0.26443(7) 0.20709(6) 0.0146(2) Uani d . . . 1 . .
C C1 0.62877(14) 0.27552(8) 0.23833(6) 0.0125(2) Uani d . . . 1 . .
C C2 0.51288(14) 0.27895(7) 0.26865(6) 0.0110(2) Uani d . . . 1 . .
C C3 0.36273(15) 0.25646(8) 0.22384(7) 0.0162(3) Uani d . . . 1 . .
H H3A 0.3667 0.2673 0.1744 0.024 Uiso calc U . R 1 . .
H H3B 0.2825 0.2888 0.2384 0.024 Uiso calc U . R 1 . .
H H3C 0.3426 0.1989 0.2299 0.024 Uiso calc U . R 1 . .
C C11 0.80563(16) 0.33578(10) 0.17084(7) 0.0218(3) Uani d . . . 1 . .
C C12 0.86331(19) 0.30304(11) 0.10626(8) 0.0319(4) Uani d . . . 1 . .
H H12A 0.7764 0.2875 0.0704 0.038 Uiso calc U . R 1 . .
H H12B 0.9179 0.3467 0.0862 0.038 Uiso calc U . R 1 . .
C C13 0.96644(18) 0.23069(12) 0.12205(9) 0.0366(4) Uani d . . . 1 . .
H H13A 1.008 0.2153 0.0798 0.044 Uiso calc U . R 1 . .
H H13B 1.051 0.2441 0.1599 0.044 Uiso calc U . R 1 . .
C C14 0.87661(17) 0.16172(11) 0.14455(8) 0.0291(4) Uani d . . . 1 . .
H H14A 0.9425 0.1137 0.1532 0.035 Uiso calc U . R 1 . .
H H14B 0.7947 0.1483 0.1054 0.035 Uiso calc U . R 1 . .
C C15 0.80759(16) 0.17799(9) 0.21036(7) 0.0210(3) Uani d . . . 1 . .
C C16 0.68190(19) 0.39720(10) 0.14912(8) 0.0278(3) Uani d . . . 1 . .
H H16A 0.7203 0.4416 0.1237 0.042 Uiso calc U . R 1 . .
H H16B 0.6478 0.4186 0.1909 0.042 Uiso calc U . R 1 . .
H H16C 0.5977 0.3711 0.1187 0.042 Uiso calc U . R 1 . .
C C17 0.93463(17) 0.37327(10) 0.22275(8) 0.0262(3) Uani d . . . 1 . .
H H17A 0.9814 0.4166 0.1995 0.039 Uiso calc U . R 1 . .
H H17B 1.0096 0.3316 0.239 0.039 Uiso calc U . R 1 . .
H H17C 0.8953 0.3955 0.2629 0.039 Uiso calc U . R 1 . .
C C18 0.68068(18) 0.11772(9) 0.21186(8) 0.0252(3) Uani d . . . 1 . .
H H18A 0.7189 0.0626 0.2088 0.038 Uiso calc U . R 1 . .
H H18B 0.6003 0.1278 0.172 0.038 Uiso calc U . R 1 . .
H H18C 0.6412 0.124 0.2557 0.038 Uiso calc U . R 1 . .
C C19 0.92327(19) 0.17214(11) 0.27767(8) 0.0324(4) Uani d . . . 1 . .
H H19A 0.878 0.1906 0.3174 0.049 Uiso calc U . R 1 . .
H H19B 1.01 0.2062 0.2734 0.049 Uiso calc U . R 1 . .
H H19C 0.9559 0.1159 0.2853 0.049 Uiso calc U . R 1 . .
C C21 0.41641(14) 0.38639(7) 0.35689(7) 0.0113(2) Uani d . . . 1 . .
C C22 0.36658(15) 0.44066(8) 0.30321(7) 0.0135(3) Uani d . . . 1 . .
F F22 0.38623(10) 0.42635(5) 0.23649(4) 0.02057(18) Uani d . . . 1 . .
C C23 0.29649(15) 0.51329(8) 0.31252(7) 0.0155(3) Uani d . . . 1 . .
F F23 0.24905(11) 0.56176(5) 0.25727(4) 0.0259(2) Uani d . . . 1 . .
C C24 0.27730(15) 0.53682(8) 0.37873(7) 0.0151(3) Uani d . . . 1 . .
F F24 0.21052(10) 0.60709(5) 0.38854(4) 0.02302(19) Uani d . . . 1 . .
C C25 0.32833(14) 0.48645(8) 0.43446(7) 0.0132(2) Uani d . . . 1 . .
F F25 0.31218(9) 0.50856(5) 0.49961(4) 0.01897(17) Uani d . . . 1 . .
C C26 0.39390(14) 0.41385(8) 0.42241(7) 0.0118(2) Uani d . . . 1 . .
F F26 0.43904(9) 0.36688(5) 0.47928(4) 0.01639(17) Uani d . . . 1 . .
C C31 0.42274(15) 0.22179(8) 0.38020(7) 0.0136(3) Uani d . . . 1 . .
C C32 0.27836(15) 0.22009(8) 0.39617(7) 0.0151(3) Uani d . . . 1 . .
F F32 0.19026(9) 0.28683(5) 0.38856(4) 0.01927(18) Uani d . . . 1 . .
C C33 0.21277(16) 0.15231(9) 0.42041(7) 0.0187(3) Uani d . . . 1 . .
F F33 0.07452(9) 0.15683(6) 0.43714(5) 0.0259(2) Uani d . . . 1 . .
C C34 0.28939(18) 0.08013(9) 0.42754(8) 0.0218(3) Uani d . . . 1 . .
F F34 0.22732(12) 0.01392(6) 0.45024(5) 0.0351(2) Uani d . . . 1 . .
C C35 0.43128(18) 0.07737(8) 0.41040(8) 0.0211(3) Uani d . . . 1 . .
F F35 0.50847(11) 0.00726(5) 0.41659(5) 0.0315(2) Uani d . . . 1 . .
C C36 0.49291(16) 0.14654(8) 0.38744(7) 0.0164(3) Uani d . . . 1 . .
F F36 0.63330(9) 0.13887(5) 0.37265(4) 0.02122(18) Uani d . . . 1 . .
C C41 0.67675(14) 0.31782(8) 0.39821(6) 0.0120(2) Uani d . . . 1 . .
C C42 0.74584(15) 0.28033(8) 0.45995(7) 0.0140(3) Uani d . . . 1 . .
F F42 0.67597(9) 0.22212(5) 0.49106(4) 0.02033(18) Uani d . . . 1 . .
C C43 0.88724(15) 0.30088(9) 0.49527(7) 0.0172(3) Uani d . . . 1 . .
F F43 0.94822(9) 0.26142(6) 0.55397(4) 0.02408(19) Uani d . . . 1 . .
C C44 0.96497(15) 0.36359(9) 0.47151(7) 0.0175(3) Uani d . . . 1 . .
F F44 1.10058(9) 0.38486(6) 0.50601(4) 0.0267(2) Uani d . . . 1 . .
C C45 0.90020(15) 0.40503(8) 0.41252(7) 0.0156(3) Uani d . . . 1 . .
F F45 0.97196(9) 0.46840(5) 0.38965(4) 0.02281(19) Uani d . . . 1 . .
C C46 0.76023(14) 0.38163(8) 0.37837(6) 0.0125(2) Uani d . . . 1 . .
F F46 0.70075(8) 0.42747(4) 0.32213(4) 0.01479(16) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C41 . 1.6504(18) ?
B1 C21 . 1.6524(18) ?
B1 C31 . 1.6574(19) ?
B1 C2 . 1.6642(18) ?
N1 C1 . 1.2657(17) ?
N1 C11 . 1.5451(18) ?
N1 C15 . 1.5543(18) ?
C1 C2 . 1.2861(19) ?
C2 C3 . 1.5276(17) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C11 C16 . 1.517(2) ?
C11 C12 . 1.532(2) ?
C11 C17 . 1.5351(19) ?
C12 C13 . 1.516(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.507(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.534(2) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C18 . 1.524(2) ?
C15 C19 . 1.529(2) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C21 C22 . 1.3890(18) ?
C21 C26 . 1.3942(18) ?
C22 F22 . 1.3540(15) ?
C22 C23 . 1.3839(18) ?
C23 F23 . 1.3469(15) ?
C23 C24 . 1.3782(19) ?
C24 F24 . 1.3380(15) ?
C24 C25 . 1.3790(19) ?
C25 F25 . 1.3444(14) ?
C25 C26 . 1.3763(18) ?
C26 F26 . 1.3524(14) ?
C31 C32 . 1.3917(19) ?
C31 C36 . 1.3931(19) ?
C32 F32 . 1.3544(15) ?
C32 C33 . 1.3866(19) ?
C33 F33 . 1.3453(16) ?
C33 C34 . 1.375(2) ?
C34 F34 . 1.3381(16) ?
C34 C35 . 1.379(2) ?
C35 F35 . 1.3481(16) ?
C35 C36 . 1.379(2) ?
C36 F36 . 1.3535(16) ?
C41 C46 . 1.3889(18) ?
C41 C42 . 1.3961(18) ?
C42 F42 . 1.3481(15) ?
C42 C43 . 1.3858(19) ?
C43 F43 . 1.3446(15) ?
C43 C44 . 1.375(2) ?
C44 F44 . 1.3398(15) ?
C44 C45 . 1.3744(19) ?
C45 F45 . 1.3463(16) ?
C45 C46 . 1.3798(18) ?
C46 F46 . 1.3603(14) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C41 B1 C21 . . 104.57(10) ?
C41 B1 C31 . . 113.41(10) ?
C21 B1 C31 . . 112.89(10) ?
C41 B1 C2 . . 112.95(10) ?
C21 B1 C2 . . 109.55(10) ?
C31 B1 C2 . . 103.64(10) ?
C1 N1 C11 . . 120.34(12) ?
C1 N1 C15 . . 117.01(11) ?
C11 N1 C15 . . 122.58(11) ?
N1 C1 C2 . . 173.97(13) ?
C1 C2 C3 . . 116.39(11) ?
C1 C2 B1 . . 127.46(11) ?
C3 C2 B1 . . 116.08(10) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C16 C11 C12 . . 110.34(13) ?
C16 C11 C17 . . 110.71(13) ?
C12 C11 C17 . . 110.53(12) ?
C16 C11 N1 . . 108.20(11) ?
C12 C11 N1 . . 108.22(12) ?
C17 C11 N1 . . 108.76(11) ?
C13 C12 C11 . . 113.41(14) ?
C13 C12 H12A . . 108.9 ?
C11 C12 H12A . . 108.9 ?
C13 C12 H12B . . 108.9 ?
C11 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.7 ?
C14 C13 C12 . . 108.22(13) ?
C14 C13 H13A . . 110.1 ?
C12 C13 H13A . . 110.1 ?
C14 C13 H13B . . 110.1 ?
C12 C13 H13B . . 110.1 ?
H13A C13 H13B . . 108.4 ?
C13 C14 C15 . . 114.98(13) ?
C13 C14 H14A . . 108.5 ?
C15 C14 H14A . . 108.5 ?
C13 C14 H14B . . 108.5 ?
C15 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
C18 C15 C19 . . 110.52(14) ?
C18 C15 C14 . . 108.34(12) ?
C19 C15 C14 . . 112.37(12) ?
C18 C15 N1 . . 107.88(11) ?
C19 C15 N1 . . 107.61(11) ?
C14 C15 N1 . . 110.02(12) ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C11 C17 H17A . . 109.5 ?
C11 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C11 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C15 C19 H19A . . 109.5 ?
C15 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C15 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C22 C21 C26 . . 113.02(11) ?
C22 C21 B1 . . 127.95(11) ?
C26 C21 B1 . . 118.80(11) ?
F22 C22 C23 . . 114.39(11) ?
F22 C22 C21 . . 121.47(11) ?
C23 C22 C21 . . 124.13(12) ?
F23 C23 C24 . . 119.79(12) ?
F23 C23 C22 . . 120.29(12) ?
C24 C23 C22 . . 119.92(12) ?
F24 C24 C23 . . 120.55(12) ?
F24 C24 C25 . . 120.85(12) ?
C23 C24 C25 . . 118.60(12) ?
F25 C25 C26 . . 120.98(11) ?
F25 C25 C24 . . 119.62(11) ?
C26 C25 C24 . . 119.40(12) ?
F26 C26 C25 . . 116.25(11) ?
F26 C26 C21 . . 118.86(11) ?
C25 C26 C21 . . 124.89(12) ?
C32 C31 C36 . . 112.83(12) ?
C32 C31 B1 . . 126.68(11) ?
C36 C31 B1 . . 120.46(12) ?
F32 C32 C33 . . 114.72(12) ?
F32 C32 C31 . . 121.05(11) ?
C33 C32 C31 . . 124.23(13) ?
F33 C33 C34 . . 119.78(12) ?
F33 C33 C32 . . 120.31(13) ?
C34 C33 C32 . . 119.91(13) ?
F34 C34 C33 . . 120.74(14) ?
F34 C34 C35 . . 120.72(13) ?
C33 C34 C35 . . 118.54(13) ?
F35 C35 C36 . . 120.72(13) ?
F35 C35 C34 . . 119.72(13) ?
C36 C35 C34 . . 119.56(13) ?
F36 C36 C35 . . 115.80(12) ?
F36 C36 C31 . . 119.33(12) ?
C35 C36 C31 . . 124.86(13) ?
C46 C41 C42 . . 112.89(11) ?
C46 C41 B1 . . 118.31(11) ?
C42 C41 B1 . . 128.57(12) ?
F42 C42 C43 . . 114.69(11) ?
F42 C42 C41 . . 121.60(12) ?
C43 C42 C41 . . 123.68(12) ?
F43 C43 C44 . . 119.28(12) ?
F43 C43 C42 . . 120.63(13) ?
C44 C43 C42 . . 120.06(12) ?
F44 C44 C45 . . 120.53(13) ?
F44 C44 C43 . . 120.51(12) ?
C45 C44 C43 . . 118.95(12) ?
F45 C45 C44 . . 120.01(12) ?
F45 C45 C46 . . 120.97(12) ?
C44 C45 C46 . . 119.00(13) ?
F46 C46 C45 . . 115.65(11) ?
F46 C46 C41 . . 119.03(11) ?
C45 C46 C41 . . 125.30(12) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C41 B1 C2 C1 . . . . -1.07(18) ?
C21 B1 C2 C1 . . . . 115.05(14) ?
C31 B1 C2 C1 . . . . -124.22(14) ?
C41 B1 C2 C3 . . . . 175.74(10) ?
C21 B1 C2 C3 . . . . -68.14(13) ?
C31 B1 C2 C3 . . . . 52.59(13) ?
C1 N1 C11 C16 . . . . -27.53(16) ?
C15 N1 C11 C16 . . . . 155.51(12) ?
C1 N1 C11 C12 . . . . -147.10(13) ?
C15 N1 C11 C12 . . . . 35.94(16) ?
C1 N1 C11 C17 . . . . 92.78(15) ?
C15 N1 C11 C17 . . . . -84.18(15) ?
C16 C11 C12 C13 . . . . -169.46(13) ?
C17 C11 C12 C13 . . . . 67.76(17) ?
N1 C11 C12 C13 . . . . -51.25(16) ?
C11 C12 C13 C14 . . . . 65.08(16) ?
C12 C13 C14 C15 . . . . -60.34(17) ?
C13 C14 C15 C18 . . . . 160.75(13) ?
C13 C14 C15 C19 . . . . -76.85(18) ?
C13 C14 C15 N1 . . . . 43.03(17) ?
C1 N1 C15 C18 . . . . 32.94(15) ?
C11 N1 C15 C18 . . . . -150.00(12) ?
C1 N1 C15 C19 . . . . -86.33(15) ?
C11 N1 C15 C19 . . . . 90.73(15) ?
C1 N1 C15 C14 . . . . 150.94(12) ?
C11 N1 C15 C14 . . . . -32.00(16) ?
C41 B1 C21 C22 . . . . 112.42(14) ?
C31 B1 C21 C22 . . . . -123.84(13) ?
C2 B1 C21 C22 . . . . -8.91(17) ?
C41 B1 C21 C26 . . . . -61.55(14) ?
C31 B1 C21 C26 . . . . 62.19(15) ?
C2 B1 C21 C26 . . . . 177.13(11) ?
C26 C21 C22 F22 . . . . 176.45(11) ?
B1 C21 C22 F22 . . . . 2.2(2) ?
C26 C21 C22 C23 . . . . -2.32(19) ?
B1 C21 C22 C23 . . . . -176.58(12) ?
F22 C22 C23 F23 . . . . 2.41(18) ?
C21 C22 C23 F23 . . . . -178.74(12) ?
F22 C22 C23 C24 . . . . -176.52(12) ?
C21 C22 C23 C24 . . . . 2.3(2) ?
F23 C23 C24 F24 . . . . 0.7(2) ?
C22 C23 C24 F24 . . . . 179.61(12) ?
F23 C23 C24 C25 . . . . -179.32(12) ?
C22 C23 C24 C25 . . . . -0.4(2) ?
F24 C24 C25 F25 . . . . -0.67(19) ?
C23 C24 C25 F25 . . . . 179.32(12) ?
F24 C24 C25 C26 . . . . 178.74(12) ?
C23 C24 C25 C26 . . . . -1.27(19) ?
F25 C25 C26 F26 . . . . 0.50(18) ?
C24 C25 C26 F26 . . . . -178.91(11) ?
F25 C25 C26 C21 . . . . -179.40(12) ?
C24 C25 C26 C21 . . . . 1.2(2) ?
C22 C21 C26 F26 . . . . -179.34(11) ?
B1 C21 C26 F26 . . . . -4.51(17) ?
C22 C21 C26 C25 . . . . 0.56(19) ?
B1 C21 C26 C25 . . . . 175.39(12) ?
C41 B1 C31 C32 . . . . 128.60(13) ?
C21 B1 C31 C32 . . . . 9.89(18) ?
C2 B1 C31 C32 . . . . -108.56(14) ?
C41 B1 C31 C36 . . . . -53.94(16) ?
C21 B1 C31 C36 . . . . -172.65(11) ?
C2 B1 C31 C36 . . . . 68.91(14) ?
C36 C31 C32 F32 . . . . -176.54(11) ?
B1 C31 C32 F32 . . . . 1.1(2) ?
C36 C31 C32 C33 . . . . 3.32(19) ?
B1 C31 C32 C33 . . . . -179.05(12) ?
F32 C32 C33 F33 . . . . -2.69(18) ?
C31 C32 C33 F33 . . . . 177.44(12) ?
F32 C32 C33 C34 . . . . 177.44(12) ?
C31 C32 C33 C34 . . . . -2.4(2) ?
F33 C33 C34 F34 . . . . 0.7(2) ?
C32 C33 C34 F34 . . . . -179.38(13) ?
F33 C33 C34 C35 . . . . -179.62(13) ?
C32 C33 C34 C35 . . . . 0.3(2) ?
F34 C34 C35 F35 . . . . 0.0(2) ?
C33 C34 C35 F35 . . . . -179.67(13) ?
F34 C34 C35 C36 . . . . -179.71(13) ?
C33 C34 C35 C36 . . . . 0.6(2) ?
F35 C35 C36 F36 . . . . -0.6(2) ?
C34 C35 C36 F36 . . . . 179.12(12) ?
F35 C35 C36 C31 . . . . -179.17(13) ?
C34 C35 C36 C31 . . . . 0.5(2) ?
C32 C31 C36 F36 . . . . 179.06(11) ?
B1 C31 C36 F36 . . . . 1.27(18) ?
C32 C31 C36 C35 . . . . -2.4(2) ?
B1 C31 C36 C35 . . . . 179.84(12) ?
C21 B1 C41 C46 . . . . -57.96(14) ?
C31 B1 C41 C46 . . . . 178.64(11) ?
C2 B1 C41 C46 . . . . 61.09(14) ?
C21 B1 C41 C42 . . . . 116.11(14) ?
C31 B1 C41 C42 . . . . -7.30(18) ?
C2 B1 C41 C42 . . . . -124.84(13) ?
C46 C41 C42 F42 . . . . 173.78(11) ?
B1 C41 C42 F42 . . . . -0.6(2) ?
C46 C41 C42 C43 . . . . -4.09(18) ?
B1 C41 C42 C43 . . . . -178.42(12) ?
F42 C42 C43 F43 . . . . 3.03(18) ?
C41 C42 C43 F43 . . . . -178.97(12) ?
F42 C42 C43 C44 . . . . -175.17(12) ?
C41 C42 C43 C44 . . . . 2.8(2) ?
F43 C43 C44 F44 . . . . 0.6(2) ?
C42 C43 C44 F44 . . . . 178.79(12) ?
F43 C43 C44 C45 . . . . -178.28(12) ?
C42 C43 C44 C45 . . . . -0.1(2) ?
F44 C44 C45 F45 . . . . -1.1(2) ?
C43 C44 C45 F45 . . . . 177.73(12) ?
F44 C44 C45 C46 . . . . -179.84(12) ?
C43 C44 C45 C46 . . . . -1.0(2) ?
F45 C45 C46 F46 . . . . -1.28(18) ?
C44 C45 C46 F46 . . . . 177.44(11) ?
F45 C45 C46 C41 . . . . -179.33(12) ?
C44 C45 C46 C41 . . . . -0.6(2) ?
C42 C41 C46 F46 . . . . -174.98(11) ?
B1 C41 C46 F46 . . . . -0.01(17) ?
C42 C41 C46 C45 . . . . 3.02(19) ?
B1 C41 C46 C45 . . . . 177.99(12) ?

####################################################################### 
# 
# 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_erk8204
_database_code_depnum_ccdc_archive 'CCDC 1843582'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H36 B F20 N Si Zr'
_chemical_formula_iupac          ?
_chemical_formula_weight         1112.88

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1163(6)
_cell_length_b                   13.9216(8)
_cell_length_c                   14.4781(8)
_cell_angle_alpha                88.616(3)
_cell_angle_beta                 88.273(3)
_cell_angle_gamma                84.773(2)
_cell_volume                     2229.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      3.0544
_cell_measurement_theta_max      66.5745
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1116

_exptl_absorpt_coefficient_mu    3.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            35784
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         66.72
_diffrn_reflns_theta_full        66.72
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             7704
_reflns_number_gt                6445
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0991
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_number_reflns         7704
_refine_ls_number_parameters     639
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+5.4112P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.573
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -0.1862 2.2449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr Zr1 0.34593(3) 0.46693(2) 0.74858(2) 0.01977(9) Uani d . . . 1 . .
B B1 0.2015(4) 0.2285(3) 0.3022(3) 0.0213(9) Uani d . . . 1 . .
Si Si1 0.19297(9) 0.25783(7) 0.86147(7) 0.0253(2) Uani d . . . 1 . .
N N1 0.5233(3) 0.1936(2) 0.8033(2) 0.0218(7) Uani d . . . 1 . .
C C21 0.2480(4) 0.5606(3) 0.6200(3) 0.0383(11) Uani d . . . 1 . .
H H21 0.2654 0.6258 0.6115 0.046 Uiso calc U . R 1 . .
C C22 0.1546(3) 0.5270(3) 0.6758(3) 0.0281(9) Uani d . . . 1 . .
H H22 0.0975 0.5658 0.7122 0.034 Uiso calc U . R 1 . .
C C23 0.1598(4) 0.4276(3) 0.6688(3) 0.0336(10) Uani d . . . 1 . .
H H23 0.1059 0.3868 0.6986 0.04 Uiso calc U . R 1 . .
C C24 0.2565(4) 0.3978(3) 0.6111(3) 0.0404(11) Uani d . . . 1 . .
H H24 0.2811 0.3328 0.5961 0.048 Uiso calc U . R 1 . .
C C25 0.3123(5) 0.4779(4) 0.5783(3) 0.0459(12) Uani d . . . 1 . .
H H25 0.3798 0.4778 0.5365 0.055 Uiso calc U . R 1 . .
C C26 0.3107(3) 0.6272(3) 0.8237(3) 0.0252(8) Uani d . . . 1 . .
H H26 0.2678 0.6782 0.7903 0.03 Uiso calc U . R 1 . .
C C27 0.2599(4) 0.5597(3) 0.8837(3) 0.0241(8) Uani d . . . 1 . .
H H27 0.1762 0.557 0.8976 0.029 Uiso calc U . R 1 . .
C C28 0.3540(4) 0.4973(3) 0.9194(2) 0.0237(8) Uani d . . . 1 . .
H H28 0.3454 0.4456 0.9625 0.028 Uiso calc U . R 1 . .
C C29 0.4628(4) 0.5243(3) 0.8807(3) 0.0250(8) Uani d . . . 1 . .
H H29 0.541 0.4936 0.8919 0.03 Uiso calc U . R 1 . .
C C30 0.4363(4) 0.6051(3) 0.8223(3) 0.0275(9) Uani d . . . 1 . .
H H30 0.4936 0.6389 0.7878 0.033 Uiso calc U . R 1 . .
C C6 0.5359(3) 0.4407(3) 0.6840(3) 0.0284(9) Uani d . . . 1 . .
H H6A 0.5926 0.4176 0.7319 0.043 Uiso calc U . R 1 . .
H H6B 0.5604 0.5011 0.6564 0.043 Uiso calc U . R 1 . .
H H6C 0.536 0.3921 0.6361 0.043 Uiso calc U . R 1 . .
C C2 0.3336(3) 0.3098(2) 0.8111(2) 0.0202(8) Uani d . . . 1 . .
C C1 0.4283(3) 0.2530(3) 0.8074(2) 0.0220(8) Uani d . . . 1 . .
C C14 0.5495(4) 0.1289(3) 0.7225(3) 0.0269(8) Uani d . . . 1 . .
H H14 0.5844 0.0651 0.7474 0.032 Uiso calc U . R 1 . .
C C15 0.4373(4) 0.1114(3) 0.6728(3) 0.0434(11) Uani d . . . 1 . .
H H15A 0.3781 0.0869 0.7168 0.065 Uiso calc U . R 1 . .
H H15B 0.4574 0.0637 0.6247 0.065 Uiso calc U . R 1 . .
H H15C 0.403 0.1719 0.6443 0.065 Uiso calc U . R 1 . .
C C16 0.6447(4) 0.1679(3) 0.6589(3) 0.0403(11) Uani d . . . 1 . .
H H16A 0.6146 0.2317 0.6347 0.06 Uiso calc U . R 1 . .
H H16B 0.663 0.124 0.6074 0.06 Uiso calc U . R 1 . .
H H16C 0.7183 0.1735 0.6933 0.06 Uiso calc U . R 1 . .
C C11 0.6129(4) 0.1843(3) 0.8796(3) 0.0267(8) Uani d . . . 1 . .
H H11 0.6958 0.1775 0.8502 0.032 Uiso calc U . R 1 . .
C C12 0.6031(5) 0.2736(3) 0.9375(3) 0.0433(12) Uani d . . . 1 . .
H H12A 0.6146 0.3302 0.8978 0.065 Uiso calc U . R 1 . .
H H12B 0.6654 0.2671 0.9843 0.065 Uiso calc U . R 1 . .
H H12C 0.5231 0.2815 0.9681 0.065 Uiso calc U . R 1 . .
C C13 0.5983(5) 0.0948(3) 0.9380(3) 0.0405(11) Uani d . . . 1 . .
H H13A 0.5194 0.101 0.9704 0.061 Uiso calc U . R 1 . .
H H13B 0.6624 0.0867 0.9833 0.061 Uiso calc U . R 1 . .
H H13C 0.6037 0.0384 0.8983 0.061 Uiso calc U . R 1 . .
C C3 0.1230(4) 0.1965(3) 0.7657(3) 0.0362(10) Uani d . . . 1 . .
H H3A 0.1622 0.131 0.7595 0.054 Uiso calc U . R 1 . .
H H3B 0.1334 0.233 0.7077 0.054 Uiso calc U . R 1 . .
H H3C 0.0366 0.1935 0.7797 0.054 Uiso calc U . R 1 . .
C C4 0.0869(4) 0.3546(3) 0.9129(3) 0.0330(9) Uani d . . . 1 . .
H H4A 0.0654 0.4042 0.8657 0.05 Uiso calc U . R 1 . .
H H4B 0.1257 0.3835 0.964 0.05 Uiso calc U . R 1 . .
H H4C 0.0136 0.3269 0.9362 0.05 Uiso calc U . R 1 . .
C C5 0.2412(4) 0.1684(3) 0.9541(3) 0.0347(10) Uani d . . . 1 . .
H H5A 0.1699 0.1421 0.9828 0.052 Uiso calc U . R 1 . .
H H5B 0.2844 0.2002 1.001 0.052 Uiso calc U . R 1 . .
H H5C 0.2947 0.1159 0.9272 0.052 Uiso calc U . R 1 . .
C C31 0.1830(3) 0.3478(2) 0.2953(2) 0.0195(7) Uani d . . . 1 . .
C C32 0.2119(3) 0.3941(3) 0.2127(2) 0.0208(8) Uani d . . . 1 . .
F F32 0.25157(19) 0.34095(14) 0.13866(13) 0.0243(5) Uani d . . . 1 . .
C C33 0.2001(3) 0.4928(3) 0.1981(3) 0.0226(8) Uani d . . . 1 . .
F F33 0.2260(2) 0.53234(15) 0.11491(15) 0.0302(5) Uani d . . . 1 . .
C C34 0.1626(3) 0.5520(3) 0.2708(3) 0.0246(8) Uani d . . . 1 . .
F F34 0.1525(2) 0.64829(15) 0.25831(17) 0.0334(5) Uani d . . . 1 . .
C C35 0.1369(3) 0.5108(3) 0.3552(3) 0.0251(8) Uani d . . . 1 . .
F F35 0.1006(2) 0.56765(16) 0.42650(16) 0.0337(5) Uani d . . . 1 . .
C C36 0.1472(3) 0.4111(3) 0.3654(2) 0.0214(8) Uani d . . . 1 . .
F F36 0.1159(2) 0.37798(16) 0.45029(14) 0.0283(5) Uani d . . . 1 . .
C C41 0.1431(3) 0.1822(3) 0.3981(2) 0.0217(8) Uani d . . . 1 . .
C C42 0.0213(3) 0.2055(3) 0.4191(2) 0.0229(8) Uani d . . . 1 . .
F F42 -0.04440(18) 0.26754(15) 0.36355(14) 0.0265(5) Uani d . . . 1 . .
C C43 -0.0403(3) 0.1684(3) 0.4944(3) 0.0266(8) Uani d . . . 1 . .
F F43 -0.1574(2) 0.19730(18) 0.50991(16) 0.0358(6) Uani d . . . 1 . .
C C44 0.0199(4) 0.1035(3) 0.5530(3) 0.0271(9) Uani d . . . 1 . .
F F44 -0.0378(2) 0.06637(18) 0.62672(15) 0.0375(6) Uani d . . . 1 . .
C C45 0.1390(4) 0.0758(3) 0.5349(3) 0.0262(8) Uani d . . . 1 . .
F F45 0.1991(2) 0.00944(17) 0.59034(15) 0.0359(6) Uani d . . . 1 . .
C C46 0.1975(3) 0.1141(3) 0.4588(3) 0.0233(8) Uani d . . . 1 . .
F F46 0.31449(19) 0.07939(16) 0.44621(15) 0.0298(5) Uani d . . . 1 . .
C C51 0.3495(3) 0.2052(2) 0.2966(2) 0.0211(8) Uani d . . . 1 . .
C C52 0.4202(3) 0.1611(3) 0.2259(2) 0.0222(8) Uani d . . . 1 . .
F F52 0.36910(19) 0.13247(15) 0.14893(14) 0.0266(5) Uani d . . . 1 . .
C C53 0.5445(3) 0.1438(3) 0.2285(3) 0.0249(8) Uani d . . . 1 . .
F F53 0.6063(2) 0.09873(17) 0.15797(17) 0.0375(6) Uani d . . . 1 . .
C C54 0.6055(3) 0.1729(3) 0.3018(3) 0.0284(9) Uani d . . . 1 . .
F F54 0.7265(2) 0.15863(18) 0.30369(17) 0.0385(6) Uani d . . . 1 . .
C C55 0.5408(3) 0.2199(3) 0.3730(3) 0.0273(9) Uani d . . . 1 . .
F F55 0.5984(2) 0.25028(19) 0.44557(16) 0.0390(6) Uani d . . . 1 . .
C C56 0.4179(3) 0.2340(3) 0.3680(2) 0.0233(8) Uani d . . . 1 . .
F F56 0.36042(19) 0.28000(17) 0.44096(14) 0.0303(5) Uani d . . . 1 . .
C C61 0.1260(3) 0.1775(2) 0.2225(2) 0.0190(7) Uani d . . . 1 . .
C C62 0.0320(3) 0.2208(2) 0.1704(2) 0.0210(8) Uani d . . . 1 . .
F F62 0.00236(19) 0.31686(14) 0.17057(14) 0.0249(5) Uani d . . . 1 . .
C C63 -0.0409(3) 0.1699(3) 0.1172(3) 0.0230(8) Uani d . . . 1 . .
F F63 -0.1313(2) 0.21668(16) 0.06919(16) 0.0325(5) Uani d . . . 1 . .
C C64 -0.0213(3) 0.0708(3) 0.1129(3) 0.0242(8) Uani d . . . 1 . .
F F64 -0.0941(2) 0.02169(16) 0.06292(16) 0.0339(5) Uani d . . . 1 . .
C C65 0.0723(3) 0.0248(3) 0.1609(3) 0.0242(8) Uani d . . . 1 . .
F F65 0.0955(2) -0.07195(15) 0.15575(16) 0.0331(5) Uani d . . . 1 . .
C C66 0.1414(3) 0.0776(3) 0.2140(2) 0.0212(8) Uani d . . . 1 . .
F F66 0.22769(19) 0.02640(14) 0.26310(15) 0.0269(5) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 C6 . 2.285(4) ?
Zr1 C2 . 2.361(3) ?
Zr1 C21 . 2.469(4) ?
Zr1 C22 . 2.470(4) ?
Zr1 C27 . 2.489(4) ?
Zr1 C26 . 2.499(4) ?
Zr1 C24 . 2.503(4) ?
Zr1 C25 . 2.504(4) ?
Zr1 C23 . 2.510(4) ?
Zr1 C30 . 2.522(4) ?
Zr1 C28 . 2.525(3) ?
Zr1 C29 . 2.530(3) ?
B1 C51 . 1.648(6) ?
B1 C41 . 1.656(5) ?
B1 C31 . 1.656(5) ?
B1 C61 . 1.658(5) ?
Si1 C4 . 1.862(4) ?
Si1 C5 . 1.865(4) ?
Si1 C3 . 1.871(4) ?
Si1 C2 . 1.900(4) ?
N1 C1 . 1.282(5) ?
N1 C14 . 1.499(5) ?
N1 C11 . 1.505(5) ?
C21 C22 . 1.403(6) ?
C21 C25 . 1.435(7) ?
C21 H21 . 0.95 ?
C22 C23 . 1.386(6) ?
C22 H22 . 0.95 ?
C23 C24 . 1.381(6) ?
C23 H23 . 0.95 ?
C24 C25 . 1.391(7) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?
C26 C30 . 1.401(6) ?
C26 C27 . 1.409(5) ?
C26 H26 . 0.95 ?
C27 C28 . 1.401(5) ?
C27 H27 . 0.95 ?
C28 C29 . 1.397(6) ?
C28 H28 . 0.95 ?
C29 C30 . 1.405(5) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C2 C1 . 1.259(5) ?
C14 C15 . 1.501(6) ?
C14 C16 . 1.512(6) ?
C14 H14 . 1.0 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C11 C13 . 1.507(5) ?
C11 C12 . 1.511(6) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C31 C36 . 1.385(5) ?
C31 C32 . 1.388(5) ?
C32 F32 . 1.357(4) ?
C32 C33 . 1.380(5) ?
C33 F33 . 1.347(4) ?
C33 C34 . 1.383(5) ?
C34 F34 . 1.344(4) ?
C34 C35 . 1.370(6) ?
C35 F35 . 1.346(4) ?
C35 C36 . 1.387(5) ?
C36 F36 . 1.350(4) ?
C41 C46 . 1.388(5) ?
C41 C42 . 1.389(5) ?
C42 F42 . 1.347(4) ?
C42 C43 . 1.385(5) ?
C43 F43 . 1.340(5) ?
C43 C44 . 1.368(6) ?
C44 F44 . 1.346(4) ?
C44 C45 . 1.364(6) ?
C45 F45 . 1.352(4) ?
C45 C46 . 1.383(5) ?
C46 F46 . 1.353(4) ?
C51 C56 . 1.390(5) ?
C51 C52 . 1.391(5) ?
C52 F52 . 1.351(4) ?
C52 C53 . 1.382(5) ?
C53 F53 . 1.349(5) ?
C53 C54 . 1.366(6) ?
C54 F54 . 1.343(4) ?
C54 C55 . 1.382(6) ?
C55 F55 . 1.343(4) ?
C55 C56 . 1.366(5) ?
C56 F56 . 1.361(4) ?
C61 C62 . 1.390(5) ?
C61 C66 . 1.395(5) ?
C62 F62 . 1.348(4) ?
C62 C63 . 1.386(5) ?
C63 F63 . 1.348(4) ?
C63 C64 . 1.379(5) ?
C64 F64 . 1.345(4) ?
C64 C65 . 1.370(5) ?
C65 F65 . 1.352(4) ?
C65 C66 . 1.373(5) ?
C66 F66 . 1.351(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 Zr1 C2 . . 96.92(13) ?
C6 Zr1 C21 . . 98.67(15) ?
C2 Zr1 C21 . . 134.44(14) ?
C6 Zr1 C22 . . 129.60(14) ?
C2 Zr1 C22 . . 110.65(13) ?
C21 Zr1 C22 . . 33.01(15) ?
C6 Zr1 C27 . . 133.77(14) ?
C2 Zr1 C27 . . 98.39(12) ?
C21 Zr1 C27 . . 100.94(14) ?
C22 Zr1 C27 . . 84.01(13) ?
C6 Zr1 C26 . . 112.61(14) ?
C2 Zr1 C26 . . 130.31(12) ?
C21 Zr1 C26 . . 81.01(14) ?
C22 Zr1 C26 . . 80.68(13) ?
C27 Zr1 C26 . . 32.83(13) ?
C6 Zr1 C24 . . 90.99(15) ?
C2 Zr1 C24 . . 83.04(14) ?
C21 Zr1 C24 . . 54.23(16) ?
C22 Zr1 C24 . . 53.69(14) ?
C27 Zr1 C24 . . 134.02(14) ?
C26 Zr1 C24 . . 132.58(14) ?
C6 Zr1 C25 . . 76.13(15) ?
C2 Zr1 C25 . . 112.96(15) ?
C21 Zr1 C25 . . 33.54(16) ?
C22 Zr1 C25 . . 54.65(15) ?
C27 Zr1 C25 . . 134.24(15) ?
C26 Zr1 C25 . . 112.43(15) ?
C24 Zr1 C25 . . 32.26(17) ?
C6 Zr1 C23 . . 122.94(15) ?
C2 Zr1 C23 . . 81.72(13) ?
C21 Zr1 C23 . . 54.02(15) ?
C22 Zr1 C23 . . 32.31(13) ?
C27 Zr1 C23 . . 102.35(14) ?
C26 Zr1 C23 . . 110.54(13) ?
C24 Zr1 C23 . . 31.98(15) ?
C25 Zr1 C23 . . 53.64(16) ?
C6 Zr1 C30 . . 82.59(14) ?
C2 Zr1 C30 . . 127.14(12) ?
C21 Zr1 C30 . . 97.26(14) ?
C22 Zr1 C30 . . 109.45(13) ?
C27 Zr1 C30 . . 53.72(13) ?
C26 Zr1 C30 . . 32.40(13) ?
C24 Zr1 C30 . . 149.61(15) ?
C25 Zr1 C30 . . 117.98(16) ?
C23 Zr1 C30 . . 141.39(13) ?
C6 Zr1 C28 . . 111.07(14) ?
C2 Zr1 C28 . . 78.88(12) ?
C21 Zr1 C28 . . 132.47(14) ?
C22 Zr1 C28 . . 115.04(13) ?
C27 Zr1 C28 . . 32.43(12) ?
C26 Zr1 C28 . . 53.91(12) ?
C24 Zr1 C28 . . 152.85(15) ?
C25 Zr1 C28 . . 165.90(15) ?
C23 Zr1 C28 . . 124.20(14) ?
C30 Zr1 C28 . . 53.37(12) ?
C6 Zr1 C29 . . 81.80(14) ?
C2 Zr1 C29 . . 95.00(12) ?
C21 Zr1 C29 . . 129.46(14) ?
C22 Zr1 C29 . . 133.63(13) ?
C27 Zr1 C29 . . 53.62(13) ?
C26 Zr1 C29 . . 53.80(12) ?
C24 Zr1 C29 . . 172.26(14) ?
C25 Zr1 C29 . . 145.97(16) ?
C23 Zr1 C29 . . 155.23(14) ?
C30 Zr1 C29 . . 32.30(12) ?
C28 Zr1 C29 . . 32.09(13) ?
C51 B1 C41 . . 111.2(3) ?
C51 B1 C31 . . 103.1(3) ?
C41 B1 C31 . . 113.9(3) ?
C51 B1 C61 . . 115.6(3) ?
C41 B1 C61 . . 101.1(3) ?
C31 B1 C61 . . 112.3(3) ?
C4 Si1 C5 . . 108.9(2) ?
C4 Si1 C3 . . 111.9(2) ?
C5 Si1 C3 . . 110.3(2) ?
C4 Si1 C2 . . 110.66(17) ?
C5 Si1 C2 . . 107.86(17) ?
C3 Si1 C2 . . 107.22(18) ?
C1 N1 C14 . . 121.4(3) ?
C1 N1 C11 . . 121.9(3) ?
C14 N1 C11 . . 116.7(3) ?
C22 C21 C25 . . 107.1(4) ?
C22 C21 Zr1 . . 73.5(2) ?
C25 C21 Zr1 . . 74.5(2) ?
C22 C21 H21 . . 126.4 ?
C25 C21 H21 . . 126.4 ?
Zr1 C21 H21 . . 117.6 ?
C23 C22 C21 . . 108.3(4) ?
C23 C22 Zr1 . . 75.4(2) ?
C21 C22 Zr1 . . 73.4(2) ?
C23 C22 H22 . . 125.8 ?
C21 C22 H22 . . 125.8 ?
Zr1 C22 H22 . . 117.3 ?
C24 C23 C22 . . 108.5(4) ?
C24 C23 Zr1 . . 73.7(2) ?
C22 C23 Zr1 . . 72.3(2) ?
C24 C23 H23 . . 125.7 ?
C22 C23 H23 . . 125.7 ?
Zr1 C23 H23 . . 120.0 ?
C23 C24 C25 . . 109.4(4) ?
C23 C24 Zr1 . . 74.3(2) ?
C25 C24 Zr1 . . 73.9(3) ?
C23 C24 H24 . . 125.3 ?
C25 C24 H24 . . 125.3 ?
Zr1 C24 H24 . . 118.3 ?
C24 C25 C21 . . 106.6(4) ?
C24 C25 Zr1 . . 73.9(2) ?
C21 C25 Zr1 . . 71.9(2) ?
C24 C25 H25 . . 126.7 ?
C21 C25 H25 . . 126.7 ?
Zr1 C25 H25 . . 119.5 ?
C30 C26 C27 . . 107.4(3) ?
C30 C26 Zr1 . . 74.7(2) ?
C27 C26 Zr1 . . 73.2(2) ?
C30 C26 H26 . . 126.3 ?
C27 C26 H26 . . 126.3 ?
Zr1 C26 H26 . . 117.8 ?
C28 C27 C26 . . 108.3(3) ?
C28 C27 Zr1 . . 75.2(2) ?
C26 C27 Zr1 . . 74.0(2) ?
C28 C27 H27 . . 125.9 ?
C26 C27 H27 . . 125.9 ?
Zr1 C27 H27 . . 117.0 ?
C29 C28 C27 . . 108.0(3) ?
C29 C28 Zr1 . . 74.1(2) ?
C27 C28 Zr1 . . 72.4(2) ?
C29 C28 H28 . . 126.0 ?
C27 C28 H28 . . 126.0 ?
Zr1 C28 H28 . . 119.4 ?
C28 C29 C30 . . 108.0(3) ?
C28 C29 Zr1 . . 73.8(2) ?
C30 C29 Zr1 . . 73.6(2) ?
C28 C29 H29 . . 126.0 ?
C30 C29 H29 . . 126.0 ?
Zr1 C29 H29 . . 118.6 ?
C26 C30 C29 . . 108.3(3) ?
C26 C30 Zr1 . . 72.9(2) ?
C29 C30 Zr1 . . 74.1(2) ?
C26 C30 H30 . . 125.8 ?
C29 C30 H30 . . 125.8 ?
Zr1 C30 H30 . . 119.0 ?
Zr1 C6 H6A . . 109.5 ?
Zr1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
Zr1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C1 C2 Si1 . . 116.2(3) ?
C1 C2 Zr1 . . 117.1(3) ?
Si1 C2 Zr1 . . 126.67(18) ?
C2 C1 N1 . . 178.7(4) ?
N1 C14 C15 . . 112.3(3) ?
N1 C14 C16 . . 110.2(3) ?
C15 C14 C16 . . 112.5(4) ?
N1 C14 H14 . . 107.2 ?
C15 C14 H14 . . 107.2 ?
C16 C14 H14 . . 107.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N1 C11 C13 . . 110.9(3) ?
N1 C11 C12 . . 111.2(3) ?
C13 C11 C12 . . 111.5(4) ?
N1 C11 H11 . . 107.7 ?
C13 C11 H11 . . 107.7 ?
C12 C11 H11 . . 107.7 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
Si1 C3 H3A . . 109.5 ?
Si1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Si1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Si1 C4 H4A . . 109.5 ?
Si1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Si1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C36 C31 C32 . . 113.2(3) ?
C36 C31 B1 . . 127.6(3) ?
C32 C31 B1 . . 119.1(3) ?
F32 C32 C33 . . 115.8(3) ?
F32 C32 C31 . . 119.5(3) ?
C33 C32 C31 . . 124.6(3) ?
F33 C33 C32 . . 121.2(3) ?
F33 C33 C34 . . 119.6(3) ?
C32 C33 C34 . . 119.2(3) ?
F34 C34 C35 . . 121.0(3) ?
F34 C34 C33 . . 120.0(3) ?
C35 C34 C33 . . 119.0(3) ?
F35 C35 C34 . . 119.5(3) ?
F35 C35 C36 . . 121.1(3) ?
C34 C35 C36 . . 119.4(3) ?
F36 C36 C31 . . 120.9(3) ?
F36 C36 C35 . . 114.6(3) ?
C31 C36 C35 . . 124.5(3) ?
C46 C41 C42 . . 113.0(3) ?
C46 C41 B1 . . 128.3(3) ?
C42 C41 B1 . . 118.4(3) ?
F42 C42 C43 . . 115.9(3) ?
F42 C42 C41 . . 119.5(3) ?
C43 C42 C41 . . 124.5(3) ?
F43 C43 C44 . . 120.8(3) ?
F43 C43 C42 . . 119.9(3) ?
C44 C43 C42 . . 119.3(4) ?
F44 C44 C45 . . 120.3(3) ?
F44 C44 C43 . . 120.5(4) ?
C45 C44 C43 . . 119.1(3) ?
F45 C45 C44 . . 120.0(3) ?
F45 C45 C46 . . 120.0(4) ?
C44 C45 C46 . . 120.0(3) ?
F46 C46 C45 . . 114.9(3) ?
F46 C46 C41 . . 121.1(3) ?
C45 C46 C41 . . 124.0(4) ?
C56 C51 C52 . . 112.6(3) ?
C56 C51 B1 . . 119.2(3) ?
C52 C51 B1 . . 128.2(3) ?
F52 C52 C53 . . 115.7(3) ?
F52 C52 C51 . . 120.7(3) ?
C53 C52 C51 . . 123.7(3) ?
F53 C53 C54 . . 119.6(3) ?
F53 C53 C52 . . 120.0(3) ?
C54 C53 C52 . . 120.4(4) ?
F54 C54 C53 . . 120.7(4) ?
F54 C54 C55 . . 120.4(4) ?
C53 C54 C55 . . 118.8(3) ?
F55 C55 C56 . . 121.2(4) ?
F55 C55 C54 . . 120.2(3) ?
C56 C55 C54 . . 118.6(3) ?
F56 C56 C55 . . 115.3(3) ?
F56 C56 C51 . . 118.9(3) ?
C55 C56 C51 . . 125.9(4) ?
C62 C61 C66 . . 113.0(3) ?
C62 C61 B1 . . 127.2(3) ?
C66 C61 B1 . . 119.0(3) ?
F62 C62 C63 . . 114.6(3) ?
F62 C62 C61 . . 121.7(3) ?
C63 C62 C61 . . 123.7(3) ?
F63 C63 C64 . . 119.5(3) ?
F63 C63 C62 . . 120.4(3) ?
C64 C63 C62 . . 120.1(3) ?
F64 C64 C65 . . 121.6(3) ?
F64 C64 C63 . . 119.8(3) ?
C65 C64 C63 . . 118.6(3) ?
F65 C65 C64 . . 119.7(3) ?
F65 C65 C66 . . 120.7(3) ?
C64 C65 C66 . . 119.5(3) ?
F66 C66 C65 . . 116.0(3) ?
F66 C66 C61 . . 119.0(3) ?
C65 C66 C61 . . 125.0(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C25 C21 C22 C23 . . . . -0.4(4) ?
Zr1 C21 C22 C23 . . . . -68.0(3) ?
C25 C21 C22 Zr1 . . . . 67.6(3) ?
C21 C22 C23 C24 . . . . 1.3(4) ?
Zr1 C22 C23 C24 . . . . -65.4(3) ?
C21 C22 C23 Zr1 . . . . 66.6(3) ?
C22 C23 C24 C25 . . . . -1.7(5) ?
Zr1 C23 C24 C25 . . . . -66.1(3) ?
C22 C23 C24 Zr1 . . . . 64.4(3) ?
C23 C24 C25 C21 . . . . 1.5(5) ?
Zr1 C24 C25 C21 . . . . -64.9(3) ?
C23 C24 C25 Zr1 . . . . 66.4(3) ?
C22 C21 C25 C24 . . . . -0.6(5) ?
Zr1 C21 C25 C24 . . . . 66.2(3) ?
C22 C21 C25 Zr1 . . . . -66.9(3) ?
C30 C26 C27 C28 . . . . 0.5(4) ?
Zr1 C26 C27 C28 . . . . 68.0(2) ?
C30 C26 C27 Zr1 . . . . -67.5(3) ?
C26 C27 C28 C29 . . . . -1.1(4) ?
Zr1 C27 C28 C29 . . . . 66.1(2) ?
C26 C27 C28 Zr1 . . . . -67.2(3) ?
C27 C28 C29 C30 . . . . 1.2(4) ?
Zr1 C28 C29 C30 . . . . 66.2(2) ?
C27 C28 C29 Zr1 . . . . -64.9(2) ?
C27 C26 C30 C29 . . . . 0.3(4) ?
Zr1 C26 C30 C29 . . . . -66.2(3) ?
C27 C26 C30 Zr1 . . . . 66.5(3) ?
C28 C29 C30 C26 . . . . -0.9(4) ?
Zr1 C29 C30 C26 . . . . 65.4(3) ?
C28 C29 C30 Zr1 . . . . -66.3(2) ?
C1 N1 C14 C15 . . . . -23.8(5) ?
C11 N1 C14 C15 . . . . 155.3(4) ?
C1 N1 C14 C16 . . . . 102.4(4) ?
C11 N1 C14 C16 . . . . -78.5(4) ?
C1 N1 C11 C13 . . . . 103.2(4) ?
C14 N1 C11 C13 . . . . -75.9(4) ?
C1 N1 C11 C12 . . . . -21.5(5) ?
C14 N1 C11 C12 . . . . 159.4(4) ?
C51 B1 C31 C36 . . . . -107.3(4) ?
C41 B1 C31 C36 . . . . 13.4(5) ?
C61 B1 C31 C36 . . . . 127.6(4) ?
C51 B1 C31 C32 . . . . 68.8(4) ?
C41 B1 C31 C32 . . . . -170.6(3) ?
C61 B1 C31 C32 . . . . -56.4(4) ?
C36 C31 C32 F32 . . . . 178.3(3) ?
B1 C31 C32 F32 . . . . 1.7(5) ?
C36 C31 C32 C33 . . . . -3.7(5) ?
B1 C31 C32 C33 . . . . 179.7(3) ?
F32 C32 C33 F33 . . . . 0.4(5) ?
C31 C32 C33 F33 . . . . -177.6(3) ?
F32 C32 C33 C34 . . . . -178.7(3) ?
C31 C32 C33 C34 . . . . 3.3(6) ?
F33 C33 C34 F34 . . . . -0.2(5) ?
C32 C33 C34 F34 . . . . 178.9(3) ?
F33 C33 C34 C35 . . . . -179.8(3) ?
C32 C33 C34 C35 . . . . -0.7(5) ?
F34 C34 C35 F35 . . . . 0.3(5) ?
C33 C34 C35 F35 . . . . 179.8(3) ?
F34 C34 C35 C36 . . . . 179.4(3) ?
C33 C34 C35 C36 . . . . -1.1(5) ?
C32 C31 C36 F36 . . . . 180.0(3) ?
B1 C31 C36 F36 . . . . -3.8(6) ?
C32 C31 C36 C35 . . . . 1.9(5) ?
B1 C31 C36 C35 . . . . 178.1(3) ?
F35 C35 C36 F36 . . . . 1.3(5) ?
C34 C35 C36 F36 . . . . -177.8(3) ?
F35 C35 C36 C31 . . . . 179.5(3) ?
C34 C35 C36 C31 . . . . 0.4(6) ?
C51 B1 C41 C46 . . . . -14.4(5) ?
C31 B1 C41 C46 . . . . -130.5(4) ?
C61 B1 C41 C46 . . . . 108.9(4) ?
C51 B1 C41 C42 . . . . 172.1(3) ?
C31 B1 C41 C42 . . . . 56.1(4) ?
C61 B1 C41 C42 . . . . -64.6(4) ?
C46 C41 C42 F42 . . . . -177.1(3) ?
B1 C41 C42 F42 . . . . -2.6(5) ?
C46 C41 C42 C43 . . . . 2.3(5) ?
B1 C41 C42 C43 . . . . 176.8(3) ?
F42 C42 C43 F43 . . . . -2.2(5) ?
C41 C42 C43 F43 . . . . 178.4(3) ?
F42 C42 C43 C44 . . . . 178.7(3) ?
C41 C42 C43 C44 . . . . -0.7(6) ?
F43 C43 C44 F44 . . . . 0.8(6) ?
C42 C43 C44 F44 . . . . 179.9(3) ?
F43 C43 C44 C45 . . . . 180.0(3) ?
C42 C43 C44 C45 . . . . -0.9(6) ?
F44 C44 C45 F45 . . . . 1.2(6) ?
C43 C44 C45 F45 . . . . -178.0(3) ?
F44 C44 C45 C46 . . . . 179.8(3) ?
C43 C44 C45 C46 . . . . 0.7(6) ?
F45 C45 C46 F46 . . . . 0.5(5) ?
C44 C45 C46 F46 . . . . -178.2(3) ?
F45 C45 C46 C41 . . . . 179.9(3) ?
C44 C45 C46 C41 . . . . 1.2(6) ?
C42 C41 C46 F46 . . . . 176.8(3) ?
B1 C41 C46 F46 . . . . 3.0(6) ?
C42 C41 C46 C45 . . . . -2.6(5) ?
B1 C41 C46 C45 . . . . -176.4(4) ?
C41 B1 C51 C56 . . . . -56.7(4) ?
C31 B1 C51 C56 . . . . 65.8(4) ?
C61 B1 C51 C56 . . . . -171.2(3) ?
C41 B1 C51 C52 . . . . 125.5(4) ?
C31 B1 C51 C52 . . . . -112.0(4) ?
C61 B1 C51 C52 . . . . 10.9(5) ?
C56 C51 C52 F52 . . . . -177.0(3) ?
B1 C51 C52 F52 . . . . 1.0(5) ?
C56 C51 C52 C53 . . . . 2.9(5) ?
B1 C51 C52 C53 . . . . -179.2(3) ?
F52 C52 C53 F53 . . . . -1.6(5) ?
C51 C52 C53 F53 . . . . 178.6(3) ?
F52 C52 C53 C54 . . . . 177.8(3) ?
C51 C52 C53 C54 . . . . -2.1(6) ?
F53 C53 C54 F54 . . . . 1.1(5) ?
C52 C53 C54 F54 . . . . -178.2(3) ?
F53 C53 C54 C55 . . . . 179.3(3) ?
C52 C53 C54 C55 . . . . -0.1(6) ?
F54 C54 C55 F55 . . . . -1.2(5) ?
C53 C54 C55 F55 . . . . -179.3(3) ?
F54 C54 C55 C56 . . . . 179.2(3) ?
C53 C54 C55 C56 . . . . 1.1(6) ?
F55 C55 C56 F56 . . . . -0.2(5) ?
C54 C55 C56 F56 . . . . 179.4(3) ?
F55 C55 C56 C51 . . . . -179.7(3) ?
C54 C55 C56 C51 . . . . -0.1(6) ?
C52 C51 C56 F56 . . . . 178.7(3) ?
B1 C51 C56 F56 . . . . 0.6(5) ?
C52 C51 C56 C55 . . . . -1.8(5) ?
B1 C51 C56 C55 . . . . -180.0(3) ?
C51 B1 C61 C62 . . . . -134.9(4) ?
C41 B1 C61 C62 . . . . 104.9(4) ?
C31 B1 C61 C62 . . . . -17.0(5) ?
C51 B1 C61 C66 . . . . 56.2(4) ?
C41 B1 C61 C66 . . . . -64.0(4) ?
C31 B1 C61 C66 . . . . 174.1(3) ?
C66 C61 C62 F62 . . . . 179.2(3) ?
B1 C61 C62 F62 . . . . 9.7(6) ?
C66 C61 C62 C63 . . . . 1.5(5) ?
B1 C61 C62 C63 . . . . -167.9(4) ?
F62 C62 C63 F63 . . . . 1.5(5) ?
C61 C62 C63 F63 . . . . 179.3(3) ?
F62 C62 C63 C64 . . . . -178.7(3) ?
C61 C62 C63 C64 . . . . -0.9(6) ?
F63 C63 C64 F64 . . . . -1.7(5) ?
C62 C63 C64 F64 . . . . 178.5(3) ?
F63 C63 C64 C65 . . . . 178.9(3) ?
C62 C63 C64 C65 . . . . -1.0(6) ?
F64 C64 C65 F65 . . . . 2.4(6) ?
C63 C64 C65 F65 . . . . -178.1(3) ?
F64 C64 C65 C66 . . . . -177.5(3) ?
C63 C64 C65 C66 . . . . 2.0(6) ?
F65 C65 C66 F66 . . . . -3.4(5) ?
C64 C65 C66 F66 . . . . 176.5(3) ?
F65 C65 C66 C61 . . . . 178.8(3) ?
C64 C65 C66 C61 . . . . -1.3(6) ?
C62 C61 C66 F66 . . . . -178.2(3) ?
B1 C61 C66 F66 . . . . -7.8(5) ?
C62 C61 C66 C65 . . . . -0.5(5) ?
B1 C61 C66 C65 . . . . 169.9(3) ?

####################################################################### 
# 
# 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_erk8302
_database_code_depnum_ccdc_archive 'CCDC 1843583'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 B F10 N Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         543.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3272(5)
_cell_length_b                   12.2348(5)
_cell_length_c                   15.6178(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.650(2)
_cell_angle_gamma                90
_cell_volume                     2517.60(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3491
_cell_measurement_theta_min      3.3543
_cell_measurement_theta_max      66.0102
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    1.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            36240
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_full        66.61
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             4428
_reflns_number_gt                3082
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1196
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.5396P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Si Si 0.2541 0.3302 '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'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.7233(2) 0.6100(2) 0.4419(2) 0.0229(7) Uani d . . . 1 . .
C C2 0.7657(2) 0.5532(2) 0.37389(18) 0.0231(6) Uani d . . . 1 . .
N N1 0.78502(17) 0.35790(17) 0.41578(14) 0.0209(5) Uani d . . . 1 . .
Si Si1 0.78403(6) 0.61916(6) 0.26833(5) 0.0237(2) Uani d . . . 1 . .
C C1 0.8175(2) 0.4510(2) 0.38750(17) 0.0224(6) Uani d . . . 1 . .
H H1 0.8848 0.45 0.3743 0.027 Uiso calc U . R 1 . .
C C11 0.8531(2) 0.2599(2) 0.4273(2) 0.0269(7) Uani d . . . 1 . .
H H11 0.8087 0.1942 0.4286 0.032 Uiso calc U . R 1 . .
C C12 0.9128(2) 0.2445(2) 0.3526(2) 0.0343(8) Uani d . . . 1 . .
H H12A 0.8674 0.2533 0.2976 0.051 Uiso calc U . R 1 . .
H H12B 0.9425 0.171 0.3555 0.051 Uiso calc U . R 1 . .
H H12C 0.9671 0.2991 0.3566 0.051 Uiso calc U . R 1 . .
C C13 0.9221(2) 0.2655(2) 0.5143(2) 0.0327(7) Uani d . . . 1 . .
H H13A 0.9673 0.3288 0.515 0.049 Uiso calc U . R 1 . .
H H13B 0.9626 0.1985 0.5232 0.049 Uiso calc U . R 1 . .
H H13C 0.8806 0.273 0.5608 0.049 Uiso calc U . R 1 . .
C C14 0.6768(2) 0.3401(2) 0.42548(18) 0.0231(6) Uani d . . . 1 . .
H H14 0.6433 0.4134 0.4235 0.028 Uiso calc U . R 1 . .
C C15 0.6255(2) 0.2747(2) 0.3480(2) 0.0327(7) Uani d . . . 1 . .
H H15A 0.6333 0.3132 0.2944 0.049 Uiso calc U . R 1 . .
H H15B 0.5531 0.2665 0.3519 0.049 Uiso calc U . R 1 . .
H H15C 0.657 0.2023 0.348 0.049 Uiso calc U . R 1 . .
C C16 0.6648(2) 0.2877(2) 0.51141(19) 0.0270(7) Uani d . . . 1 . .
H H16A 0.6937 0.2139 0.514 0.041 Uiso calc U . R 1 . .
H H16B 0.5926 0.2835 0.5168 0.041 Uiso calc U . R 1 . .
H H16C 0.7003 0.3318 0.5589 0.041 Uiso calc U . R 1 . .
C C3 0.8755(2) 0.7358(2) 0.2835(2) 0.0335(7) Uani d . . . 1 . .
H H3A 0.8793 0.77 0.2274 0.05 Uiso calc U . R 1 . .
H H3B 0.9428 0.7087 0.3085 0.05 Uiso calc U . R 1 . .
H H3C 0.8524 0.7897 0.3227 0.05 Uiso calc U . R 1 . .
C C4 0.6608(2) 0.6699(3) 0.2089(2) 0.0337(7) Uani d . . . 1 . .
H H4A 0.641 0.7368 0.2367 0.051 Uiso calc U . R 1 . .
H H4B 0.6084 0.614 0.2102 0.051 Uiso calc U . R 1 . .
H H4C 0.6683 0.6857 0.1487 0.051 Uiso calc U . R 1 . .
C C5 0.8332(2) 0.5149(2) 0.19705(19) 0.0315(7) Uani d . . . 1 . .
H H5A 0.8474 0.5501 0.1438 0.047 Uiso calc U . R 1 . .
H H5B 0.7822 0.4575 0.1825 0.047 Uiso calc U . R 1 . .
H H5C 0.8958 0.4825 0.2276 0.047 Uiso calc U . R 1 . .
C C21 0.6748(2) 0.7303(2) 0.43076(17) 0.0211(6) Uani d . . . 1 . .
C C22 0.7306(2) 0.8210(2) 0.46284(18) 0.0214(6) Uani d . . . 1 . .
F F22 0.82842(12) 0.80771(13) 0.49988(10) 0.0296(4) Uani d . . . 1 . .
C C23 0.6915(2) 0.9259(2) 0.45971(18) 0.0255(7) Uani d . . . 1 . .
F F23 0.75007(14) 1.01144(12) 0.48926(11) 0.0330(4) Uani d . . . 1 . .
C C24 0.5916(2) 0.9421(2) 0.42540(19) 0.0264(7) Uani d . . . 1 . .
F F24 0.55149(14) 1.04300(12) 0.42323(11) 0.0350(4) Uani d . . . 1 . .
C C25 0.5327(2) 0.8551(2) 0.39253(18) 0.0252(6) Uani d . . . 1 . .
F F25 0.43492(12) 0.87212(13) 0.35892(11) 0.0321(4) Uani d . . . 1 . .
C C26 0.5754(2) 0.7518(2) 0.39527(18) 0.0229(6) Uani d . . . 1 . .
F F26 0.51440(12) 0.66870(12) 0.36171(11) 0.0288(4) Uani d . . . 1 . .
C C31 0.7328(2) 0.5671(2) 0.53985(18) 0.0215(6) Uani d . . . 1 . .
C C32 0.6506(2) 0.5644(2) 0.58522(19) 0.0238(6) Uani d . . . 1 . .
F F32 0.55768(12) 0.59442(13) 0.54389(10) 0.0299(4) Uani d . . . 1 . .
C C33 0.6558(2) 0.5317(2) 0.67025(19) 0.0259(7) Uani d . . . 1 . .
F F33 0.57353(13) 0.53289(14) 0.71060(11) 0.0328(4) Uani d . . . 1 . .
C C34 0.7480(2) 0.4997(2) 0.71442(18) 0.0266(7) Uani d . . . 1 . .
F F34 0.75687(14) 0.47008(14) 0.79840(10) 0.0353(4) Uani d . . . 1 . .
C C35 0.8327(2) 0.5010(2) 0.67333(18) 0.0249(7) Uani d . . . 1 . .
F F35 0.92343(13) 0.47170(14) 0.71742(11) 0.0362(4) Uani d . . . 1 . .
C C36 0.8237(2) 0.5341(2) 0.58845(18) 0.0222(6) Uani d . . . 1 . .
F F36 0.91061(12) 0.53577(13) 0.55338(10) 0.0280(4) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C2 . 1.453(4) ?
B1 C31 . 1.604(4) ?
B1 C21 . 1.608(4) ?
C2 C1 . 1.428(4) ?
C2 Si1 . 1.884(3) ?
N1 C1 . 1.318(3) ?
N1 C14 . 1.488(3) ?
N1 C11 . 1.498(3) ?
Si1 C4 . 1.867(3) ?
Si1 C3 . 1.868(3) ?
Si1 C5 . 1.875(3) ?
C1 H1 . 0.95 ?
C11 C12 . 1.519(4) ?
C11 C13 . 1.524(4) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C16 . 1.518(4) ?
C14 C15 . 1.524(4) ?
C14 H14 . 1.0 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C21 C26 . 1.382(4) ?
C21 C22 . 1.387(4) ?
C22 F22 . 1.354(3) ?
C22 C23 . 1.383(4) ?
C23 F23 . 1.345(3) ?
C23 C24 . 1.373(4) ?
C24 F24 . 1.344(3) ?
C24 C25 . 1.374(4) ?
C25 F25 . 1.346(3) ?
C25 C26 . 1.384(4) ?
C26 F26 . 1.357(3) ?
C31 C36 . 1.390(4) ?
C31 C32 . 1.392(4) ?
C32 F32 . 1.358(3) ?
C32 C33 . 1.378(4) ?
C33 F33 . 1.345(3) ?
C33 C34 . 1.373(4) ?
C34 F34 . 1.349(3) ?
C34 C35 . 1.379(4) ?
C35 F35 . 1.347(3) ?
C35 C36 . 1.374(4) ?
C36 F36 . 1.353(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 B1 C31 . . 123.9(3) ?
C2 B1 C21 . . 123.6(3) ?
C31 B1 C21 . . 112.1(2) ?
C1 C2 B1 . . 122.8(3) ?
C1 C2 Si1 . . 112.5(2) ?
B1 C2 Si1 . . 123.4(2) ?
C1 N1 C14 . . 122.2(2) ?
C1 N1 C11 . . 120.6(2) ?
C14 N1 C11 . . 116.7(2) ?
C4 Si1 C3 . . 108.51(15) ?
C4 Si1 C5 . . 106.94(14) ?
C3 Si1 C5 . . 108.38(15) ?
C4 Si1 C2 . . 110.94(13) ?
C3 Si1 C2 . . 112.57(13) ?
C5 Si1 C2 . . 109.30(13) ?
N1 C1 C2 . . 129.1(3) ?
N1 C1 H1 . . 115.5 ?
C2 C1 H1 . . 115.5 ?
N1 C11 C12 . . 112.7(2) ?
N1 C11 C13 . . 110.1(2) ?
C12 C11 C13 . . 112.0(3) ?
N1 C11 H11 . . 107.3 ?
C12 C11 H11 . . 107.3 ?
C13 C11 H11 . . 107.3 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 C16 . . 112.6(2) ?
N1 C14 C15 . . 108.8(2) ?
C16 C14 C15 . . 112.7(2) ?
N1 C14 H14 . . 107.5 ?
C16 C14 H14 . . 107.5 ?
C15 C14 H14 . . 107.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
Si1 C3 H3A . . 109.5 ?
Si1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Si1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Si1 C4 H4A . . 109.5 ?
Si1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Si1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C26 C21 C22 . . 115.0(2) ?
C26 C21 B1 . . 124.3(2) ?
C22 C21 B1 . . 120.6(2) ?
F22 C22 C23 . . 117.4(2) ?
F22 C22 C21 . . 119.2(2) ?
C23 C22 C21 . . 123.4(3) ?
F23 C23 C24 . . 120.0(2) ?
F23 C23 C22 . . 120.9(3) ?
C24 C23 C22 . . 119.0(3) ?
F24 C24 C23 . . 120.1(3) ?
F24 C24 C25 . . 119.9(3) ?
C23 C24 C25 . . 120.0(3) ?
F25 C25 C24 . . 119.4(2) ?
F25 C25 C26 . . 121.5(3) ?
C24 C25 C26 . . 119.1(3) ?
F26 C26 C21 . . 119.7(2) ?
F26 C26 C25 . . 116.9(3) ?
C21 C26 C25 . . 123.4(3) ?
C36 C31 C32 . . 113.8(3) ?
C36 C31 B1 . . 123.6(2) ?
C32 C31 B1 . . 122.5(3) ?
F32 C32 C33 . . 116.6(3) ?
F32 C32 C31 . . 118.9(2) ?
C33 C32 C31 . . 124.6(3) ?
F33 C33 C34 . . 119.9(3) ?
F33 C33 C32 . . 121.4(3) ?
C34 C33 C32 . . 118.6(3) ?
F34 C34 C33 . . 120.4(3) ?
F34 C34 C35 . . 119.8(3) ?
C33 C34 C35 . . 119.7(3) ?
F35 C35 C36 . . 120.8(3) ?
F35 C35 C34 . . 119.6(3) ?
C36 C35 C34 . . 119.6(3) ?
F36 C36 C35 . . 116.1(2) ?
F36 C36 C31 . . 120.2(2) ?
C35 C36 C31 . . 123.7(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C31 B1 C2 C1 . . . . 2.1(5) ?
C21 B1 C2 C1 . . . . 173.6(3) ?
C31 B1 C2 Si1 . . . . -163.8(2) ?
C21 B1 C2 Si1 . . . . 7.7(4) ?
C1 C2 Si1 C4 . . . . 133.9(2) ?
B1 C2 Si1 C4 . . . . -58.9(3) ?
C1 C2 Si1 C3 . . . . -104.3(2) ?
B1 C2 Si1 C3 . . . . 62.9(3) ?
C1 C2 Si1 C5 . . . . 16.2(2) ?
B1 C2 Si1 C5 . . . . -176.6(2) ?
C14 N1 C1 C2 . . . . 10.3(4) ?
C11 N1 C1 C2 . . . . -178.7(3) ?
B1 C2 C1 N1 . . . . 56.9(4) ?
Si1 C2 C1 N1 . . . . -135.9(3) ?
C1 N1 C11 C12 . . . . -42.9(4) ?
C14 N1 C11 C12 . . . . 128.6(3) ?
C1 N1 C11 C13 . . . . 82.9(3) ?
C14 N1 C11 C13 . . . . -105.6(3) ?
C1 N1 C14 C16 . . . . -133.8(3) ?
C11 N1 C14 C16 . . . . 54.9(3) ?
C1 N1 C14 C15 . . . . 100.6(3) ?
C11 N1 C14 C15 . . . . -70.8(3) ?
C2 B1 C21 C26 . . . . 85.0(4) ?
C31 B1 C21 C26 . . . . -102.6(3) ?
C2 B1 C21 C22 . . . . -99.5(4) ?
C31 B1 C21 C22 . . . . 72.9(3) ?
C26 C21 C22 F22 . . . . 179.2(2) ?
B1 C21 C22 F22 . . . . 3.3(4) ?
C26 C21 C22 C23 . . . . -0.4(4) ?
B1 C21 C22 C23 . . . . -176.3(3) ?
F22 C22 C23 F23 . . . . 2.6(4) ?
C21 C22 C23 F23 . . . . -177.8(3) ?
F22 C22 C23 C24 . . . . -177.7(2) ?
C21 C22 C23 C24 . . . . 1.8(4) ?
F23 C23 C24 F24 . . . . -1.6(4) ?
C22 C23 C24 F24 . . . . 178.7(2) ?
F23 C23 C24 C25 . . . . 177.8(3) ?
C22 C23 C24 C25 . . . . -1.9(4) ?
F24 C24 C25 F25 . . . . -0.4(4) ?
C23 C24 C25 F25 . . . . -179.9(3) ?
F24 C24 C25 C26 . . . . 179.9(3) ?
C23 C24 C25 C26 . . . . 0.5(4) ?
C22 C21 C26 F26 . . . . 179.7(2) ?
B1 C21 C26 F26 . . . . -4.6(4) ?
C22 C21 C26 C25 . . . . -1.0(4) ?
B1 C21 C26 C25 . . . . 174.7(3) ?
F25 C25 C26 F26 . . . . 0.7(4) ?
C24 C25 C26 F26 . . . . -179.7(2) ?
F25 C25 C26 C21 . . . . -178.6(2) ?
C24 C25 C26 C21 . . . . 1.0(4) ?
C2 B1 C31 C36 . . . . 49.4(4) ?
C21 B1 C31 C36 . . . . -123.0(3) ?
C2 B1 C31 C32 . . . . -133.7(3) ?
C21 B1 C31 C32 . . . . 53.9(3) ?
C36 C31 C32 F32 . . . . -179.7(2) ?
B1 C31 C32 F32 . . . . 3.1(4) ?
C36 C31 C32 C33 . . . . -0.5(4) ?
B1 C31 C32 C33 . . . . -177.7(3) ?
F32 C32 C33 F33 . . . . -1.9(4) ?
C31 C32 C33 F33 . . . . 178.9(2) ?
F32 C32 C33 C34 . . . . 179.4(2) ?
C31 C32 C33 C34 . . . . 0.3(4) ?
F33 C33 C34 F34 . . . . -0.5(4) ?
C32 C33 C34 F34 . . . . 178.2(2) ?
F33 C33 C34 C35 . . . . -178.6(2) ?
C32 C33 C34 C35 . . . . 0.1(4) ?
F34 C34 C35 F35 . . . . 0.5(4) ?
C33 C34 C35 F35 . . . . 178.6(2) ?
F34 C34 C35 C36 . . . . -178.2(2) ?
C33 C34 C35 C36 . . . . -0.1(4) ?
F35 C35 C36 F36 . . . . -0.4(4) ?
C34 C35 C36 F36 . . . . 178.3(2) ?
F35 C35 C36 C31 . . . . -178.9(2) ?
C34 C35 C36 C31 . . . . -0.2(4) ?
C32 C31 C36 F36 . . . . -178.0(2) ?
B1 C31 C36 F36 . . . . -0.8(4) ?
C32 C31 C36 C35 . . . . 0.4(4) ?
B1 C31 C36 C35 . . . . 177.6(3) ?

####################################################################### 
# 
# 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_erk8404
_database_code_depnum_ccdc_archive 'CCDC 1843581'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 B F10 N Si'
_chemical_formula_weight         609.43

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'
Si Si 0.0817 0.0704 '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                   10.0190(2)
_cell_length_b                   19.0596(3)
_cell_length_c                   15.5129(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4220(10)
_cell_angle_gamma                90.00
_cell_volume                     2953.50(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6501
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.9746
_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            20730
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         28.32
_reflns_number_total             7211
_reflns_number_gt                5743
_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. 
 
 One N(iPr)2 group is disordered over two positions. Several restraints (SADI,
 SAME, ISOR and SIMU) were used in order to improve refinement stability
;

_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)+(0.0395P)²+1.4919P] 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         7211
_refine_ls_number_parameters     437
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.074
_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
C2 C -0.13078(17) 0.25420(9) 0.68102(11) 0.0387(4) Uani 1 1 d . . .
C1 C -0.12478(17) 0.31791(10) 0.70457(12) 0.0406(4) Uani 1 1 d . A .
N1 N -0.11480(16) 0.38200(8) 0.72645(11) 0.0468(4) Uani 1 1 d DU . .
C11 C -0.0779(8) 0.4377(5) 0.6643(5) 0.058(3) Uani 0.697(16) 1 d PDU A 1
H11 H -0.0279 0.4748 0.6979 0.069 Uiso 0.697(16) 1 calc PR A 1
C12 C 0.0126(9) 0.4088(3) 0.5998(5) 0.084(2) Uani 0.697(16) 1 d PDU A 1
H12A H 0.0902 0.3872 0.6303 0.125 Uiso 0.697(16) 1 calc PR A 1
H12B H 0.0415 0.4466 0.5637 0.125 Uiso 0.697(16) 1 calc PR A 1
H12C H -0.0355 0.3740 0.5639 0.125 Uiso 0.697(16) 1 calc PR A 1
C13 C -0.2038(7) 0.4705(4) 0.6219(6) 0.093(2) Uani 0.697(16) 1 d PDU A 1
H13A H -0.2535 0.4356 0.5872 0.139 Uiso 0.697(16) 1 calc PR A 1
H13B H -0.1799 0.5090 0.5852 0.139 Uiso 0.697(16) 1 calc PR A 1
H13C H -0.2586 0.4880 0.6661 0.139 Uiso 0.697(16) 1 calc PR A 1
C14 C -0.1430(9) 0.4060(6) 0.8156(5) 0.062(3) Uani 0.697(16) 1 d PDU A 1
H14 H -0.1982 0.4489 0.8081 0.074 Uiso 0.697(16) 1 calc PR A 1
C15 C -0.0130(7) 0.4276(3) 0.8660(5) 0.0651(14) Uani 0.697(16) 1 d PDU A 1
H15A H 0.0414 0.3863 0.8790 0.098 Uiso 0.697(16) 1 calc PR A 1
H15B H -0.0331 0.4502 0.9194 0.098 Uiso 0.697(16) 1 calc PR A 1
H15C H 0.0354 0.4599 0.8315 0.098 Uiso 0.697(16) 1 calc PR A 1
C16 C -0.2209(7) 0.3555(4) 0.8651(4) 0.0748(17) Uani 0.697(16) 1 d PDU A 1
H16A H -0.2994 0.3403 0.8294 0.112 Uiso 0.697(16) 1 calc PR A 1
H16B H -0.2486 0.3781 0.9168 0.112 Uiso 0.697(16) 1 calc PR A 1
H16C H -0.1655 0.3151 0.8813 0.112 Uiso 0.697(16) 1 calc PR A 1
C11A C -0.0702(17) 0.4341(13) 0.6610(12) 0.058(6) Uani 0.303(16) 1 d PDU A 2
H11A H -0.0534 0.4794 0.6913 0.070 Uiso 0.303(16) 1 calc PR A 2
C12A C 0.0596(17) 0.4107(11) 0.6281(13) 0.096(5) Uani 0.303(16) 1 d PDU A 2
H121 H 0.1257 0.4040 0.6765 0.144 Uiso 0.303(16) 1 calc PR A 2
H122 H 0.0910 0.4461 0.5896 0.144 Uiso 0.303(16) 1 calc PR A 2
H123 H 0.0460 0.3668 0.5970 0.144 Uiso 0.303(16) 1 calc PR A 2
C13A C -0.1797(17) 0.4462(9) 0.5897(10) 0.085(4) Uani 0.303(16) 1 d PDU A 2
H131 H -0.1836 0.4065 0.5504 0.127 Uiso 0.303(16) 1 calc PR A 2
H132 H -0.1606 0.4886 0.5583 0.127 Uiso 0.303(16) 1 calc PR A 2
H133 H -0.2650 0.4512 0.6147 0.127 Uiso 0.303(16) 1 calc PR A 2
C14A C -0.1467(17) 0.4139(13) 0.8114(9) 0.049(4) Uani 0.303(16) 1 d PDU A 2
H14A H -0.1656 0.4645 0.8026 0.059 Uiso 0.303(16) 1 calc PR A 2
C15A C -0.025(2) 0.4058(13) 0.8742(13) 0.099(6) Uani 0.303(16) 1 d PDU A 2
H151 H -0.0152 0.3570 0.8915 0.148 Uiso 0.303(16) 1 calc PR A 2
H152 H -0.0348 0.4347 0.9247 0.148 Uiso 0.303(16) 1 calc PR A 2
H153 H 0.0544 0.4205 0.8466 0.148 Uiso 0.303(16) 1 calc PR A 2
C16A C -0.2714(18) 0.3779(10) 0.8369(12) 0.092(5) Uani 0.303(16) 1 d PDU A 2
H161 H -0.3418 0.3827 0.7908 0.138 Uiso 0.303(16) 1 calc PR A 2
H162 H -0.2999 0.3992 0.8892 0.138 Uiso 0.303(16) 1 calc PR A 2
H163 H -0.2529 0.3285 0.8473 0.138 Uiso 0.303(16) 1 calc PR A 2
Si1 Si 0.03451(5) 0.20403(3) 0.70387(4) 0.04659(15) Uani 1 1 d . . .
C3 C 0.1333(3) 0.24731(14) 0.79530(18) 0.0739(7) Uani 1 1 d . . .
H3A H 0.2161 0.2217 0.8084 0.111 Uiso 1 1 calc R . .
H3B H 0.0818 0.2476 0.8457 0.111 Uiso 1 1 calc R . .
H3C H 0.1535 0.2952 0.7795 0.111 Uiso 1 1 calc R . .
C4 C 0.1293(2) 0.20810(16) 0.60559(17) 0.0729(7) Uani 1 1 d . . .
H4A H 0.2240 0.2019 0.6218 0.109 Uiso 1 1 calc R . .
H4B H 0.1149 0.2534 0.5778 0.109 Uiso 1 1 calc R . .
H4C H 0.0985 0.1712 0.5659 0.109 Uiso 1 1 calc R . .
C5 C 0.0001(2) 0.11190(11) 0.73462(16) 0.0625(6) Uani 1 1 d . . .
H5A H -0.0313 0.0856 0.6835 0.094 Uiso 1 1 calc R . .
H5B H -0.0680 0.1113 0.7758 0.094 Uiso 1 1 calc R . .
H5C H 0.0815 0.0907 0.7606 0.094 Uiso 1 1 calc R . .
C6 C -0.36503(18) 0.28083(10) 0.58761(12) 0.0423(4) Uani 1 1 d . . .
H6 H -0.3583 0.2894 0.5284 0.051 Uiso 1 1 calc R . .
C7 C -0.4502(2) 0.32063(11) 0.62636(13) 0.0490(4) Uani 1 1 d . . .
H7 H -0.4605 0.3108 0.6849 0.059 Uiso 1 1 calc R . .
C8 C -0.5305(2) 0.37868(11) 0.58777(15) 0.0550(5) Uani 1 1 d . . .
C9 C -0.5997(3) 0.41989(17) 0.6365(2) 0.0944(10) Uani 1 1 d . . .
H9A H -0.5978 0.4121 0.6964 0.113 Uiso 1 1 calc R . .
H9B H -0.6509 0.4569 0.6112 0.113 Uiso 1 1 calc R . .
C10 C -0.5294(3) 0.39112(15) 0.49288(17) 0.0814(8) Uani 1 1 d . . .
H10A H -0.5833 0.4320 0.4769 0.122 Uiso 1 1 calc R . .
H10B H -0.5660 0.3505 0.4617 0.122 Uiso 1 1 calc R . .
H10C H -0.4381 0.3989 0.4783 0.122 Uiso 1 1 calc R . .
B1 B -0.2709(2) 0.21897(10) 0.63015(13) 0.0376(4) Uani 1 1 d . . .
C21 C -0.21777(17) 0.16810(9) 0.55340(11) 0.0382(4) Uani 1 1 d . . .
F22 F -0.27369(13) 0.05795(6) 0.61267(8) 0.0590(3) Uani 1 1 d . . .
C22 C -0.2213(2) 0.09570(10) 0.54947(12) 0.0449(4) Uani 1 1 d . . .
F23 F -0.17804(18) -0.01434(7) 0.48688(10) 0.0824(5) Uani 1 1 d . . .
C23 C -0.1719(2) 0.05603(10) 0.48469(14) 0.0551(5) Uani 1 1 d . . .
F24 F -0.06546(19) 0.05083(8) 0.35513(10) 0.0907(5) Uani 1 1 d . . .
C24 C -0.1152(2) 0.08854(12) 0.41821(14) 0.0590(6) Uani 1 1 d . . .
F25 F -0.05186(14) 0.19378(8) 0.35318(8) 0.0690(4) Uani 1 1 d . . .
C25 C -0.1087(2) 0.16046(11) 0.41773(13) 0.0502(5) Uani 1 1 d . . .
F26 F -0.14140(12) 0.26816(6) 0.47982(7) 0.0510(3) Uani 1 1 d . . .
C26 C -0.15822(18) 0.19794(9) 0.48384(12) 0.0415(4) Uani 1 1 d . . .
C31 C -0.35801(19) 0.17665(9) 0.69928(12) 0.0432(4) Uani 1 1 d . . .
F32 F -0.21999(14) 0.19898(7) 0.82819(8) 0.0650(3) Uani 1 1 d . . .
C32 C -0.3343(2) 0.17317(11) 0.78799(13) 0.0502(5) Uani 1 1 d . . .
F33 F -0.38998(19) 0.14418(9) 0.92893(10) 0.0919(5) Uani 1 1 d . . .
C33 C -0.4214(3) 0.14397(12) 0.84306(15) 0.0633(6) Uani 1 1 d . . .
F34 F -0.62254(17) 0.08472(9) 0.86183(13) 0.1006(6) Uani 1 1 d . . .
C34 C -0.5370(3) 0.11433(12) 0.81004(19) 0.0683(7) Uani 1 1 d . . .
F35 F -0.67659(14) 0.08148(8) 0.68762(13) 0.0903(5) Uani 1 1 d . . .
C35 C -0.5651(2) 0.11365(12) 0.72204(19) 0.0637(6) Uani 1 1 d . . .
F36 F -0.51209(13) 0.14290(7) 0.58341(9) 0.0656(3) Uani 1 1 d . . .
C36 C -0.4780(2) 0.14502(11) 0.66934(15) 0.0515(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
C2 C1 1.268(2) . ?
C2 B1 1.695(3) . ?
C2 Si1 1.9215(18) . ?
C1 N1 1.270(2) . ?
N1 C11 1.500(7) . ?
N1 C14 1.504(7) . ?
N1 C14A 1.507(12) . ?
N1 C11A 1.512(13) . ?
C11 C12 1.505(8) . ?
C11 C13 1.512(7) . ?
C11 H11 0.9900 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C16 1.489(8) . ?
C14 C15 1.522(7) . ?
C14 H14 0.9900 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C11A C12A 1.501(14) . ?
C11A C13A 1.515(14) . ?
C11A H11A 0.9900 . ?
C12A H121 0.9700 . ?
C12A H122 0.9700 . ?
C12A H123 0.9700 . ?
C13A H131 0.9700 . ?
C13A H132 0.9700 . ?
C13A H133 0.9700 . ?
C14A C16A 1.506(13) . ?
C14A C15A 1.512(14) . ?
C14A H14A 0.9900 . ?
C15A H151 0.9700 . ?
C15A H152 0.9700 . ?
C15A H153 0.9700 . ?
C16A H161 0.9700 . ?
C16A H162 0.9700 . ?
C16A H163 0.9700 . ?
Si1 C5 1.859(2) . ?
Si1 C3 1.859(2) . ?
Si1 C4 1.859(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.320(3) . ?
C6 B1 1.618(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.468(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.323(3) . ?
C8 C10 1.492(3) . ?
C9 H9A 0.9400 . ?
C9 H9B 0.9400 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
B1 C31 1.645(3) . ?
B1 C21 1.655(3) . ?
C21 C22 1.382(2) . ?
C21 C26 1.394(2) . ?
F22 C22 1.354(2) . ?
C22 C23 1.379(3) . ?
F23 C23 1.343(2) . ?
C23 C24 1.364(3) . ?
F24 C24 1.341(2) . ?
C24 C25 1.372(3) . ?
F25 C25 1.348(2) . ?
C25 C26 1.374(3) . ?
F26 C26 1.351(2) . ?
C31 C32 1.380(3) . ?
C31 C36 1.392(3) . ?
F32 C32 1.353(3) . ?
C32 C33 1.385(3) . ?
F33 C33 1.345(3) . ?
C33 C34 1.353(4) . ?
F34 C34 1.343(2) . ?
C34 C35 1.372(4) . ?
F35 C35 1.348(3) . ?
C35 C36 1.378(3) . ?
F36 C36 1.351(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
C1 C2 B1 122.18(16) . . ?
C1 C2 Si1 113.73(14) . . ?
B1 C2 Si1 124.03(12) . . ?
C2 C1 N1 177.8(2) . . ?
C1 N1 C11 121.8(5) . . ?
C1 N1 C14 121.5(4) . . ?
C11 N1 C14 116.7(6) . . ?
C1 N1 C14A 127.2(9) . . ?
C11 N1 C14A 110.8(10) . . ?
C14 N1 C14A 6.4(14) . . ?
C1 N1 C11A 118.3(10) . . ?
C11 N1 C11A 4.4(12) . . ?
C14 N1 C11A 120.2(11) . . ?
C14A N1 C11A 114.5(13) . . ?
N1 C11 C12 111.0(6) . . ?
N1 C11 C13 109.5(5) . . ?
C12 C11 C13 112.8(6) . . ?
N1 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C13 C11 H11 107.8 . . ?
C16 C14 N1 114.9(6) . . ?
C16 C14 C15 111.8(6) . . ?
N1 C14 C15 109.9(6) . . ?
C16 C14 H14 106.6 . . ?
N1 C14 H14 106.6 . . ?
C15 C14 H14 106.6 . . ?
C12A C11A N1 110.0(13) . . ?
C12A C11A C13A 113.2(15) . . ?
N1 C11A C13A 110.8(13) . . ?
C12A C11A H11A 107.5 . . ?
N1 C11A H11A 107.5 . . ?
C13A C11A H11A 107.5 . . ?
C11A C12A H121 109.5 . . ?
C11A C12A H122 109.5 . . ?
H121 C12A H122 109.5 . . ?
C11A C12A H123 109.5 . . ?
H121 C12A H123 109.5 . . ?
H122 C12A H123 109.5 . . ?
C11A C13A H131 109.5 . . ?
C11A C13A H132 109.5 . . ?
H131 C13A H132 109.5 . . ?
C11A C13A H133 109.5 . . ?
H131 C13A H133 109.5 . . ?
H132 C13A H133 109.5 . . ?
C16A C14A N1 106.4(11) . . ?
C16A C14A C15A 115.5(16) . . ?
N1 C14A C15A 107.9(14) . . ?
C16A C14A H14A 109.0 . . ?
N1 C14A H14A 109.0 . . ?
C15A C14A H14A 109.0 . . ?
C14A C15A H151 109.5 . . ?
C14A C15A H152 109.5 . . ?
H151 C15A H152 109.5 . . ?
C14A C15A H153 109.5 . . ?
H151 C15A H153 109.5 . . ?
H152 C15A H153 109.5 . . ?
C14A C16A H161 109.5 . . ?
C14A C16A H162 109.5 . . ?
H161 C16A H162 109.5 . . ?
C14A C16A H163 109.5 . . ?
H161 C16A H163 109.5 . . ?
H162 C16A H163 109.5 . . ?
C5 Si1 C3 108.77(12) . . ?
C5 Si1 C4 111.51(12) . . ?
C3 Si1 C4 109.36(14) . . ?
C5 Si1 C2 110.07(10) . . ?
C3 Si1 C2 108.69(10) . . ?
C4 Si1 C2 108.40(9) . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 B1 127.56(17) . . ?
C7 C6 H6 116.2 . . ?
B1 C6 H6 116.2 . . ?
C6 C7 C8 126.89(19) . . ?
C6 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 C10 120.9(2) . . ?
C7 C8 C10 118.45(19) . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
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 . . ?
C6 B1 C31 107.52(14) . . ?
C6 B1 C21 110.07(14) . . ?
C31 B1 C21 113.45(14) . . ?
C6 B1 C2 109.69(14) . . ?
C31 B1 C2 110.65(14) . . ?
C21 B1 C2 105.45(14) . . ?
C22 C21 C26 112.60(16) . . ?
C22 C21 B1 127.48(16) . . ?
C26 C21 B1 119.90(15) . . ?
F22 C22 C23 114.65(17) . . ?
F22 C22 C21 120.57(17) . . ?
C23 C22 C21 124.76(18) . . ?
F23 C23 C24 119.69(19) . . ?
F23 C23 C22 120.6(2) . . ?
C24 C23 C22 119.71(19) . . ?
F24 C24 C23 120.5(2) . . ?
F24 C24 C25 120.8(2) . . ?
C23 C24 C25 118.71(18) . . ?
F25 C25 C24 119.81(18) . . ?
F25 C25 C26 120.47(19) . . ?
C24 C25 C26 119.71(19) . . ?
F26 C26 C25 115.30(17) . . ?
F26 C26 C21 120.15(16) . . ?
C25 C26 C21 124.51(17) . . ?
C32 C31 C36 112.94(18) . . ?
C32 C31 B1 127.90(18) . . ?
C36 C31 B1 118.87(17) . . ?
F32 C32 C31 121.10(18) . . ?
F32 C32 C33 114.4(2) . . ?
C31 C32 C33 124.5(2) . . ?
F33 C33 C34 120.3(2) . . ?
F33 C33 C32 119.9(3) . . ?
C34 C33 C32 119.8(2) . . ?
F34 C34 C33 121.0(3) . . ?
F34 C34 C35 120.0(3) . . ?
C33 C34 C35 119.0(2) . . ?
F35 C35 C34 119.9(2) . . ?
F35 C35 C36 120.4(2) . . ?
C34 C35 C36 119.7(2) . . ?
F36 C36 C35 116.7(2) . . ?
F36 C36 C31 119.24(18) . . ?
C35 C36 C31 124.1(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
B1 C2 C1 N1 -124(5) . . . . ?
Si1 C2 C1 N1 53(5) . . . . ?
C2 C1 N1 C11 39(5) . . . . ?
C2 C1 N1 C14 -143(5) . . . . ?
C2 C1 N1 C14A -146(5) . . . . ?
C2 C1 N1 C11A 36(5) . . . . ?
C1 N1 C11 C12 -30.9(8) . . . . ?
C14 N1 C11 C12 150.6(7) . . . . ?
C14A N1 C11 C12 153.4(10) . . . . ?
C11A N1 C11 C12 7(16) . . . . ?
C1 N1 C11 C13 94.3(7) . . . . ?
C14 N1 C11 C13 -84.2(9) . . . . ?
C14A N1 C11 C13 -81.4(10) . . . . ?
C11A N1 C11 C13 132(17) . . . . ?
C1 N1 C14 C16 -17.7(10) . . . . ?
C11 N1 C14 C16 160.8(7) . . . . ?
C14A N1 C14 C16 137(8) . . . . ?
C11A N1 C14 C16 163.8(9) . . . . ?
C1 N1 C14 C15 109.4(6) . . . . ?
C11 N1 C14 C15 -72.2(9) . . . . ?
C14A N1 C14 C15 -96(8) . . . . ?
C11A N1 C14 C15 -69.1(11) . . . . ?
C1 N1 C11A C12A -54.0(19) . . . . ?
C11 N1 C11A C12A 162(18) . . . . ?
C14 N1 C11A C12A 124.6(16) . . . . ?
C14A N1 C11A C12A 127.7(17) . . . . ?
C1 N1 C11A C13A 71.9(17) . . . . ?
C11 N1 C11A C13A -72(16) . . . . ?
C14 N1 C11A C13A -109.5(17) . . . . ?
C14A N1 C11A C13A -106.4(18) . . . . ?
C1 N1 C14A C16A -40(2) . . . . ?
C11 N1 C14A C16A 135.8(15) . . . . ?
C14 N1 C14A C16A -67(8) . . . . ?
C11A N1 C14A C16A 138.5(15) . . . . ?
C1 N1 C14A C15A 84.8(15) . . . . ?
C11 N1 C14A C15A -99.7(17) . . . . ?
C14 N1 C14A C15A 58(8) . . . . ?
C11A N1 C14A C15A -97.0(19) . . . . ?
C1 C2 Si1 C5 144.28(16) . . . . ?
B1 C2 Si1 C5 -38.38(17) . . . . ?
C1 C2 Si1 C3 25.25(19) . . . . ?
B1 C2 Si1 C3 -157.41(16) . . . . ?
C1 C2 Si1 C4 -93.52(18) . . . . ?
B1 C2 Si1 C4 83.81(17) . . . . ?
B1 C6 C7 C8 177.04(19) . . . . ?
C6 C7 C8 C9 -171.6(3) . . . . ?
C6 C7 C8 C10 6.8(4) . . . . ?
C7 C6 B1 C31 38.4(3) . . . . ?
C7 C6 B1 C21 162.42(19) . . . . ?
C7 C6 B1 C2 -82.0(2) . . . . ?
C1 C2 B1 C6 20.5(2) . . . . ?
Si1 C2 B1 C6 -156.61(13) . . . . ?
C1 C2 B1 C31 -98.0(2) . . . . ?
Si1 C2 B1 C31 84.93(17) . . . . ?
C1 C2 B1 C21 139.00(18) . . . . ?
Si1 C2 B1 C21 -38.12(18) . . . . ?
C6 B1 C21 C22 -130.97(19) . . . . ?
C31 B1 C21 C22 -10.5(3) . . . . ?
C2 B1 C21 C22 110.8(2) . . . . ?
C6 B1 C21 C26 50.9(2) . . . . ?
C31 B1 C21 C26 171.45(16) . . . . ?
C2 B1 C21 C26 -67.30(19) . . . . ?
C26 C21 C22 F22 178.87(16) . . . . ?
B1 C21 C22 F22 0.7(3) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
B1 C21 C22 C23 -178.11(19) . . . . ?
F22 C22 C23 F23 0.2(3) . . . . ?
C21 C22 C23 F23 179.06(19) . . . . ?
F22 C22 C23 C24 -179.2(2) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
F23 C23 C24 F24 0.0(4) . . . . ?
C22 C23 C24 F24 179.4(2) . . . . ?
F23 C23 C24 C25 -179.3(2) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
F24 C24 C25 F25 0.0(3) . . . . ?
C23 C24 C25 F25 179.3(2) . . . . ?
F24 C24 C25 C26 -178.9(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
F25 C25 C26 F26 -2.0(3) . . . . ?
C24 C25 C26 F26 176.90(18) . . . . ?
F25 C25 C26 C21 -179.59(17) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C22 C21 C26 F26 -177.06(16) . . . . ?
B1 C21 C26 F26 1.3(3) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
B1 C21 C26 C25 178.77(17) . . . . ?
C6 B1 C31 C32 -114.1(2) . . . . ?
C21 B1 C31 C32 124.0(2) . . . . ?
C2 B1 C31 C32 5.7(3) . . . . ?
C6 B1 C31 C36 59.3(2) . . . . ?
C21 B1 C31 C36 -62.7(2) . . . . ?
C2 B1 C31 C36 179.03(16) . . . . ?
C36 C31 C32 F32 177.57(17) . . . . ?
B1 C31 C32 F32 -8.8(3) . . . . ?
C36 C31 C32 C33 -2.3(3) . . . . ?
B1 C31 C32 C33 171.32(18) . . . . ?
F32 C32 C33 F33 1.2(3) . . . . ?
C31 C32 C33 F33 -178.90(19) . . . . ?
F32 C32 C33 C34 -177.76(19) . . . . ?
C31 C32 C33 C34 2.1(3) . . . . ?
F33 C33 C34 F34 0.1(3) . . . . ?
C32 C33 C34 F34 179.05(19) . . . . ?
F33 C33 C34 C35 -178.69(19) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
F34 C34 C35 F35 -1.9(3) . . . . ?
C33 C34 C35 F35 176.9(2) . . . . ?
F34 C34 C35 C36 179.04(19) . . . . ?
C33 C34 C35 C36 -2.2(3) . . . . ?
F35 C35 C36 F36 1.4(3) . . . . ?
C34 C35 C36 F36 -179.55(19) . . . . ?
F35 C35 C36 C31 -177.12(18) . . . . ?
C34 C35 C36 C31 1.9(3) . . . . ?
C32 C31 C36 F36 -178.21(17) . . . . ?
B1 C31 C36 F36 7.5(3) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
B1 C31 C36 C35 -173.98(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_erk8394
_database_code_depnum_ccdc_archive 'CCDC 1843577'
_audit_update_record             
;
2018-05-16 deposited with the CCDC.
2018-06-20 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 H28 B F10 N'
_chemical_formula_weight         627.36

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                   8.6741(3)
_cell_length_b                   11.6278(4)
_cell_length_c                   14.9181(5)
_cell_angle_alpha                83.1550(10)
_cell_angle_beta                 85.9390(10)
_cell_angle_gamma                77.6090(10)
_cell_volume                     1457.54(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3648
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_correction_T_max  0.9937
_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            13670
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5035
_reflns_number_gt                3685
_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. 

 The hydrogen at N1 atom was refined freely.

 One phenyl group is disordered over two positions. Several restraints (SADI,
 SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

_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+2.7236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5035
_refine_ls_number_parameters     461
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.115
_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 0.2997(4) 0.0799(2) 0.2457(2) 0.0390(7) Uani 1 1 d . . .
H1A H 0.402(4) 0.066(3) 0.243(2) 0.035(10) Uiso 1 1 d . . .
C11 C 0.2515(4) 0.0046(3) 0.3325(3) 0.0446(9) Uani 1 1 d . . .
C12 C 0.3128(5) -0.1254(3) 0.3189(3) 0.0582(11) Uani 1 1 d . . .
H12A H 0.4284 -0.1427 0.3194 0.070 Uiso 1 1 calc R . .
H12B H 0.2740 -0.1742 0.3701 0.070 Uiso 1 1 calc R . .
C13 C 0.2650(6) -0.1610(4) 0.2323(3) 0.0685(13) Uani 1 1 d . . .
H13A H 0.3077 -0.2455 0.2285 0.082 Uiso 1 1 calc R . .
H13B H 0.1496 -0.1471 0.2316 0.082 Uiso 1 1 calc R . .
C14 C 0.3283(6) -0.0888(3) 0.1530(3) 0.0615(12) Uani 1 1 d . . .
H14A H 0.2997 -0.1137 0.0971 0.074 Uiso 1 1 calc R . .
H14B H 0.4439 -0.1059 0.1537 0.074 Uiso 1 1 calc R . .
C15 C 0.2676(5) 0.0443(3) 0.1521(3) 0.0462(9) Uani 1 1 d . . .
C16 C 0.0736(5) 0.0324(4) 0.3534(3) 0.0597(11) Uani 1 1 d . . .
H16A H 0.0496 -0.0113 0.4104 0.090 Uiso 1 1 calc R . .
H16B H 0.0202 0.0094 0.3056 0.090 Uiso 1 1 calc R . .
H16C H 0.0379 0.1166 0.3576 0.090 Uiso 1 1 calc R . .
C17 C 0.3348(5) 0.0346(4) 0.4100(3) 0.0599(11) Uani 1 1 d . . .
H17A H 0.2932 0.1165 0.4205 0.090 Uiso 1 1 calc R . .
H17B H 0.4472 0.0235 0.3948 0.090 Uiso 1 1 calc R . .
H17C H 0.3172 -0.0168 0.4642 0.090 Uiso 1 1 calc R . .
C18 C 0.0924(5) 0.0816(4) 0.1314(3) 0.0629(12) Uani 1 1 d . . .
H18A H 0.0782 0.0644 0.0709 0.094 Uiso 1 1 calc R . .
H18B H 0.0568 0.1659 0.1355 0.094 Uiso 1 1 calc R . .
H18C H 0.0314 0.0382 0.1747 0.094 Uiso 1 1 calc R . .
C19 C 0.3633(5) 0.1091(4) 0.0825(3) 0.0557(11) Uani 1 1 d . . .
H19A H 0.4735 0.0891 0.0976 0.084 Uiso 1 1 calc R . .
H19B H 0.3243 0.1938 0.0822 0.084 Uiso 1 1 calc R . .
H19C H 0.3534 0.0859 0.0232 0.084 Uiso 1 1 calc R . .
C1 C 0.2465(4) 0.2075(3) 0.2513(2) 0.0405(9) Uani 1 1 d . . .
H1 H 0.1368 0.2369 0.2516 0.049 Uiso 1 1 calc R . .
C2 C 0.3355(4) 0.2863(3) 0.2562(2) 0.0373(8) Uani 1 1 d . . .
C3 C 0.2377(5) 0.4112(3) 0.2573(3) 0.0484(10) Uani 1 1 d . . .
H3A H 0.1263 0.4089 0.2610 0.073 Uiso 1 1 calc R . .
H3B H 0.2615 0.4589 0.2023 0.073 Uiso 1 1 calc R . .
H3C H 0.2629 0.4455 0.3091 0.073 Uiso 1 1 calc R . .
C4 C 0.6182(4) 0.1336(3) 0.2556(2) 0.0383(8) Uani 1 1 d . A .
B1 B 0.5268(5) 0.2682(3) 0.2578(3) 0.0371(9) Uani 1 1 d . . .
C21 C 0.5861(4) 0.3072(3) 0.3518(2) 0.0400(9) Uani 1 1 d . . .
F22 F 0.3478(3) 0.3088(2) 0.44076(14) 0.0531(6) Uani 1 1 d . . .
C22 C 0.4994(4) 0.3224(3) 0.4315(2) 0.0402(9) Uani 1 1 d . . .
F23 F 0.4623(3) 0.3687(2) 0.58317(15) 0.0599(6) Uani 1 1 d . . .
C23 C 0.5552(5) 0.3537(3) 0.5076(2) 0.0457(9) Uani 1 1 d . . .
F24 F 0.7637(3) 0.4000(2) 0.57955(16) 0.0711(7) Uani 1 1 d . . .
C24 C 0.7061(5) 0.3700(3) 0.5062(3) 0.0496(10) Uani 1 1 d . . .
F25 F 0.9516(3) 0.3664(3) 0.42685(18) 0.0767(8) Uani 1 1 d . . .
C25 C 0.8012(5) 0.3530(4) 0.4296(3) 0.0512(10) Uani 1 1 d . . .
F26 F 0.8408(3) 0.3066(2) 0.28216(15) 0.0577(6) Uani 1 1 d . . .
C26 C 0.7395(5) 0.3221(3) 0.3554(2) 0.0436(9) Uani 1 1 d . . .
C31 C 0.5880(4) 0.3542(3) 0.1705(2) 0.0382(8) Uani 1 1 d . . .
F32 F 0.5080(3) 0.52742(18) 0.24682(15) 0.0553(6) Uani 1 1 d . . .
C32 C 0.5723(4) 0.4754(3) 0.1729(3) 0.0430(9) Uani 1 1 d . . .
F33 F 0.6001(3) 0.66750(19) 0.11098(18) 0.0701(7) Uani 1 1 d . . .
C33 C 0.6245(5) 0.5502(3) 0.1043(3) 0.0493(10) Uani 1 1 d . . .
F34 F 0.7537(4) 0.5772(2) -0.03778(18) 0.0821(8) Uani 1 1 d . . .
C34 C 0.6991(5) 0.5066(4) 0.0287(3) 0.0529(10) Uani 1 1 d . . .
F35 F 0.7878(3) 0.3423(2) -0.05301(17) 0.0787(8) Uani 1 1 d . . .
C35 C 0.7168(5) 0.3873(4) 0.0219(3) 0.0515(10) Uani 1 1 d . . .
F36 F 0.6857(3) 0.20059(19) 0.07665(15) 0.0586(6) Uani 1 1 d . . .
C36 C 0.6610(4) 0.3157(3) 0.0911(3) 0.0437(9) Uani 1 1 d . . .
C5 C 0.6847(4) 0.0315(3) 0.2591(3) 0.0412(9) Uani 1 1 d D . .
C41 C 0.766(6) -0.0917(14) 0.2674(10) 0.043(5) Uani 0.57(2) 1 d PDU A 1
C42 C 0.785(3) -0.1585(12) 0.3503(9) 0.046(3) Uani 0.57(2) 1 d PDU A 1
H42 H 0.7522 -0.1228 0.4036 0.056 Uiso 0.57(2) 1 calc PR A 1
C43 C 0.853(2) -0.2783(11) 0.3550(11) 0.067(4) Uani 0.57(2) 1 d PDU A 1
H43 H 0.8618 -0.3248 0.4112 0.081 Uiso 0.57(2) 1 calc PR A 1
C44 C 0.9063(16) -0.3283(10) 0.2772(12) 0.067(4) Uani 0.57(2) 1 d PDU A 1
H44 H 0.9584 -0.4083 0.2812 0.081 Uiso 0.57(2) 1 calc PR A 1
C45 C 0.887(2) -0.2656(12) 0.1938(11) 0.072(5) Uani 0.57(2) 1 d PDU A 1
H45 H 0.9214 -0.3022 0.1410 0.086 Uiso 0.57(2) 1 calc PR A 1
C46 C 0.815(3) -0.1473(12) 0.1892(10) 0.047(3) Uani 0.57(2) 1 d PDU A 1
H46 H 0.7986 -0.1032 0.1323 0.057 Uiso 0.57(2) 1 calc PR A 1
C41A C 0.758(7) -0.0901(17) 0.2484(14) 0.035(5) Uani 0.43(2) 1 d PDU A 2
C42A C 0.793(4) -0.1741(15) 0.3212(13) 0.056(5) Uani 0.43(2) 1 d PDU A 2
H42A H 0.7631 -0.1528 0.3798 0.067 Uiso 0.43(2) 1 calc PR A 2
C43A C 0.871(2) -0.2890(13) 0.3109(16) 0.066(5) Uani 0.43(2) 1 d PDU A 2
H43A H 0.8923 -0.3456 0.3613 0.079 Uiso 0.43(2) 1 calc PR A 2
C44A C 0.916(3) -0.3184(14) 0.2250(16) 0.073(5) Uani 0.43(2) 1 d PDU A 2
H44A H 0.9671 -0.3964 0.2165 0.087 Uiso 0.43(2) 1 calc PR A 2
C45A C 0.886(3) -0.2349(15) 0.1512(14) 0.067(5) Uani 0.43(2) 1 d PDU A 2
H45A H 0.9195 -0.2562 0.0929 0.080 Uiso 0.43(2) 1 calc PR A 2
C46A C 0.810(5) -0.1213(17) 0.1621(13) 0.051(5) Uani 0.43(2) 1 d PDU A 2
H46A H 0.7917 -0.0644 0.1116 0.062 Uiso 0.43(2) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.466(4) . ?
N1 C11 1.559(4) . ?
N1 C15 1.561(5) . ?
N1 H1A 0.87(4) . ?
C11 C17 1.518(5) . ?
C11 C12 1.523(5) . ?
C11 C16 1.524(5) . ?
C12 C13 1.513(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.508(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.523(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C19 1.515(5) . ?
C15 C18 1.531(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C1 C2 1.329(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.517(5) . ?
C2 B1 1.629(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 C5 1.200(5) . ?
C4 B1 1.599(5) . ?
B1 C21 1.671(5) . ?
B1 C31 1.673(5) . ?
C21 C22 1.370(5) . ?
C21 C26 1.383(5) . ?
F22 C22 1.353(4) . ?
C22 C23 1.381(5) . ?
F23 C23 1.345(4) . ?
C23 C24 1.361(6) . ?
F24 C24 1.346(4) . ?
C24 C25 1.370(6) . ?
F25 C25 1.344(5) . ?
C25 C26 1.380(5) . ?
F26 C26 1.356(4) . ?
C31 C36 1.380(5) . ?
C31 C32 1.391(5) . ?
F32 C32 1.349(4) . ?
C32 C33 1.378(5) . ?
F33 C33 1.350(4) . ?
C33 C34 1.357(6) . ?
F34 C34 1.337(4) . ?
C34 C35 1.377(6) . ?
F35 C35 1.344(4) . ?
C35 C36 1.374(5) . ?
F36 C36 1.351(4) . ?
C5 C41A 1.443(12) . ?
C5 C41 1.448(10) . ?
C41 C42 1.381(11) . ?
C41 C46 1.397(11) . ?
C42 C43 1.386(11) . ?
C42 H42 0.9400 . ?
C43 C44 1.367(11) . ?
C43 H43 0.9400 . ?
C44 C45 1.368(11) . ?
C44 H44 0.9400 . ?
C45 C46 1.379(11) . ?
C45 H45 0.9400 . ?
C46 H46 0.9400 . ?
C41A C42A 1.377(12) . ?
C41A C46A 1.396(14) . ?
C42A C43A 1.382(12) . ?
C42A H42A 0.9400 . ?
C43A C44A 1.373(13) . ?
C43A H43A 0.9400 . ?
C44A C45A 1.378(13) . ?
C44A H44A 0.9400 . ?
C45A C46A 1.369(12) . ?
C45A H45A 0.9400 . ?
C46A H46A 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
C1 N1 C11 112.3(3) . . ?
C1 N1 C15 112.0(3) . . ?
C11 N1 C15 117.9(3) . . ?
C1 N1 H1A 107(2) . . ?
C11 N1 H1A 106(2) . . ?
C15 N1 H1A 100(2) . . ?
C17 C11 C12 109.1(3) . . ?
C17 C11 C16 109.2(3) . . ?
C12 C11 C16 111.9(3) . . ?
C17 C11 N1 106.9(3) . . ?
C12 C11 N1 107.6(3) . . ?
C16 C11 N1 112.1(3) . . ?
C13 C12 C11 114.5(3) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 109.0(4) . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C15 114.1(4) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C19 C15 C14 109.7(4) . . ?
C19 C15 C18 109.4(3) . . ?
C14 C15 C18 112.1(3) . . ?
C19 C15 N1 106.0(3) . . ?
C14 C15 N1 107.8(3) . . ?
C18 C15 N1 111.7(3) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 N1 127.6(3) . . ?
C2 C1 H1 116.2 . . ?
N1 C1 H1 116.2 . . ?
C1 C2 C3 112.2(3) . . ?
C1 C2 B1 130.0(3) . . ?
C3 C2 B1 117.8(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 B1 176.2(4) . . ?
C4 B1 C2 113.7(3) . . ?
C4 B1 C21 103.7(3) . . ?
C2 B1 C21 113.0(3) . . ?
C4 B1 C31 110.7(3) . . ?
C2 B1 C31 108.2(3) . . ?
C21 B1 C31 107.4(3) . . ?
C22 C21 C26 113.3(3) . . ?
C22 C21 B1 126.7(3) . . ?
C26 C21 B1 119.9(3) . . ?
F22 C22 C21 121.3(3) . . ?
F22 C22 C23 114.4(3) . . ?
C21 C22 C23 124.3(4) . . ?
F23 C23 C24 119.4(3) . . ?
F23 C23 C22 120.9(4) . . ?
C24 C23 C22 119.7(4) . . ?
F24 C24 C23 120.9(4) . . ?
F24 C24 C25 119.8(4) . . ?
C23 C24 C25 119.3(4) . . ?
F25 C25 C24 120.6(4) . . ?
F25 C25 C26 120.7(4) . . ?
C24 C25 C26 118.7(4) . . ?
F26 C26 C25 115.3(4) . . ?
F26 C26 C21 120.0(3) . . ?
C25 C26 C21 124.7(4) . . ?
C36 C31 C32 112.8(3) . . ?
C36 C31 B1 125.5(3) . . ?
C32 C31 B1 121.7(3) . . ?
F32 C32 C33 115.0(3) . . ?
F32 C32 C31 120.7(3) . . ?
C33 C32 C31 124.3(4) . . ?
F33 C33 C34 119.3(4) . . ?
F33 C33 C32 120.5(4) . . ?
C34 C33 C32 120.2(4) . . ?
F34 C34 C33 121.1(4) . . ?
F34 C34 C35 120.7(4) . . ?
C33 C34 C35 118.1(4) . . ?
F35 C35 C36 120.7(4) . . ?
F35 C35 C34 119.3(4) . . ?
C36 C35 C34 120.0(4) . . ?
F36 C36 C35 114.4(3) . . ?
F36 C36 C31 121.1(3) . . ?
C35 C36 C31 124.5(4) . . ?
C4 C5 C41A 170.7(12) . . ?
C4 C5 C41 177.6(9) . . ?
C41A C5 C41 11.6(19) . . ?
C42 C41 C46 118.7(9) . . ?
C42 C41 C5 121.8(11) . . ?
C46 C41 C5 119.3(10) . . ?
C41 C42 C43 120.1(10) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C44 C43 C42 119.4(10) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 122.1(10) . . ?
C43 C44 H44 118.9 . . ?
C45 C44 H44 118.9 . . ?
C44 C45 C46 118.2(11) . . ?
C44 C45 H45 120.9 . . ?
C46 C45 H45 120.9 . . ?
C45 C46 C41 121.3(10) . . ?
C45 C46 H46 119.4 . . ?
C41 C46 H46 119.4 . . ?
C42A C41A C46A 118.5(11) . . ?
C42A C41A C5 122.1(13) . . ?
C46A C41A C5 119.1(13) . . ?
C41A C42A C43A 122.0(12) . . ?
C41A C42A H42A 119.0 . . ?
C43A C42A H42A 119.0 . . ?
C44A C43A C42A 118.3(13) . . ?
C44A C43A H43A 120.8 . . ?
C42A C43A H43A 120.8 . . ?
C43A C44A C45A 120.8(14) . . ?
C43A C44A H44A 119.6 . . ?
C45A C44A H44A 119.6 . . ?
C46A C45A C44A 120.4(14) . . ?
C46A C45A H45A 119.8 . . ?
C44A C45A H45A 119.8 . . ?
C45A C46A C41A 119.9(13) . . ?
C45A C46A H46A 120.1 . . ?
C41A C46A H46A 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
C1 N1 C11 C17 -62.9(4) . . . . ?
C15 N1 C11 C17 164.6(3) . . . . ?
C1 N1 C11 C12 -179.9(3) . . . . ?
C15 N1 C11 C12 47.5(4) . . . . ?
C1 N1 C11 C16 56.7(4) . . . . ?
C15 N1 C11 C16 -75.9(4) . . . . ?
C17 C11 C12 C13 -168.1(4) . . . . ?
C16 C11 C12 C13 71.0(5) . . . . ?
N1 C11 C12 C13 -52.5(5) . . . . ?
C11 C12 C13 C14 60.0(5) . . . . ?
C12 C13 C14 C15 -60.1(5) . . . . ?
C13 C14 C15 C19 168.0(4) . . . . ?
C13 C14 C15 C18 -70.3(5) . . . . ?
C13 C14 C15 N1 53.0(5) . . . . ?
C1 N1 C15 C19 62.1(4) . . . . ?
C11 N1 C15 C19 -165.3(3) . . . . ?
C1 N1 C15 C14 179.5(3) . . . . ?
C11 N1 C15 C14 -47.9(4) . . . . ?
C1 N1 C15 C18 -57.0(4) . . . . ?
C11 N1 C15 C18 75.7(4) . . . . ?
C11 N1 C1 C2 112.3(4) . . . . ?
C15 N1 C1 C2 -112.3(4) . . . . ?
N1 C1 C2 C3 177.6(3) . . . . ?
N1 C1 C2 B1 -0.3(6) . . . . ?
C5 C4 B1 C2 -80(6) . . . . ?
C5 C4 B1 C21 43(6) . . . . ?
C5 C4 B1 C31 158(5) . . . . ?
C1 C2 B1 C4 -1.6(5) . . . . ?
C3 C2 B1 C4 -179.5(3) . . . . ?
C1 C2 B1 C21 -119.4(4) . . . . ?
C3 C2 B1 C21 62.8(4) . . . . ?
C1 C2 B1 C31 121.8(4) . . . . ?
C3 C2 B1 C31 -56.0(4) . . . . ?
C4 B1 C21 C22 -106.2(4) . . . . ?
C2 B1 C21 C22 17.3(5) . . . . ?
C31 B1 C21 C22 136.6(3) . . . . ?
C4 B1 C21 C26 70.7(4) . . . . ?
C2 B1 C21 C26 -165.8(3) . . . . ?
C31 B1 C21 C26 -46.5(4) . . . . ?
C26 C21 C22 F22 -178.6(3) . . . . ?
B1 C21 C22 F22 -1.6(5) . . . . ?
C26 C21 C22 C23 2.3(5) . . . . ?
B1 C21 C22 C23 179.3(3) . . . . ?
F22 C22 C23 F23 -0.1(5) . . . . ?
C21 C22 C23 F23 179.1(3) . . . . ?
F22 C22 C23 C24 -180.0(3) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
F23 C23 C24 F24 0.4(5) . . . . ?
C22 C23 C24 F24 -179.7(3) . . . . ?
F23 C23 C24 C25 179.1(3) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
F24 C24 C25 F25 -0.2(6) . . . . ?
C23 C24 C25 F25 -178.8(3) . . . . ?
F24 C24 C25 C26 179.9(3) . . . . ?
C23 C24 C25 C26 1.2(6) . . . . ?
F25 C25 C26 F26 0.2(5) . . . . ?
C24 C25 C26 F26 -179.9(3) . . . . ?
F25 C25 C26 C21 -179.5(3) . . . . ?
C24 C25 C26 C21 0.4(6) . . . . ?
C22 C21 C26 F26 178.2(3) . . . . ?
B1 C21 C26 F26 0.9(5) . . . . ?
C22 C21 C26 C25 -2.1(5) . . . . ?
B1 C21 C26 C25 -179.4(3) . . . . ?
C4 B1 C31 C36 21.5(5) . . . . ?
C2 B1 C31 C36 -103.7(4) . . . . ?
C21 B1 C31 C36 134.1(4) . . . . ?
C4 B1 C31 C32 -156.7(3) . . . . ?
C2 B1 C31 C32 78.1(4) . . . . ?
C21 B1 C31 C32 -44.2(4) . . . . ?
C36 C31 C32 F32 -177.9(3) . . . . ?
B1 C31 C32 F32 0.6(5) . . . . ?
C36 C31 C32 C33 -0.5(5) . . . . ?
B1 C31 C32 C33 178.0(3) . . . . ?
F32 C32 C33 F33 -4.5(5) . . . . ?
C31 C32 C33 F33 177.9(3) . . . . ?
F32 C32 C33 C34 176.4(3) . . . . ?
C31 C32 C33 C34 -1.1(6) . . . . ?
F33 C33 C34 F34 2.4(6) . . . . ?
C32 C33 C34 F34 -178.5(4) . . . . ?
F33 C33 C34 C35 -177.4(4) . . . . ?
C32 C33 C34 C35 1.7(6) . . . . ?
F34 C34 C35 F35 -1.0(6) . . . . ?
C33 C34 C35 F35 178.8(4) . . . . ?
F34 C34 C35 C36 179.5(4) . . . . ?
C33 C34 C35 C36 -0.7(6) . . . . ?
F35 C35 C36 F36 0.6(6) . . . . ?
C34 C35 C36 F36 -179.9(4) . . . . ?
F35 C35 C36 C31 179.5(4) . . . . ?
C34 C35 C36 C31 -1.0(6) . . . . ?
C32 C31 C36 F36 -179.7(3) . . . . ?
B1 C31 C36 F36 1.9(6) . . . . ?
C32 C31 C36 C35 1.5(5) . . . . ?
B1 C31 C36 C35 -176.9(4) . . . . ?
B1 C4 C5 C41A 151(15) . . . . ?
B1 C4 C5 C41 -24(53) . . . . ?
C4 C5 C41 C42 17(56) . . . . ?
C41A C5 C41 C42 -159(26) . . . . ?
C4 C5 C41 C46 -168(48) . . . . ?
C41A C5 C41 C46 16(18) . . . . ?
C46 C41 C42 C43 0(6) . . . . ?
C5 C41 C42 C43 175(3) . . . . ?
C41 C42 C43 C44 3(4) . . . . ?
C42 C43 C44 C45 -4(3) . . . . ?
C43 C44 C45 C46 2(3) . . . . ?
C44 C45 C46 C41 1(4) . . . . ?
C42 C41 C46 C45 -2(6) . . . . ?
C5 C41 C46 C45 -177(3) . . . . ?
C4 C5 C41A C42A -161(10) . . . . ?
C41 C5 C41A C42A 18(17) . . . . ?
C4 C5 C41A C46A 25(19) . . . . ?
C41 C5 C41A C46A -156(26) . . . . ?
C46A C41A C42A C43A -3(8) . . . . ?
C5 C41A C42A C43A -176(4) . . . . ?
C41A C42A C43A C44A 1(6) . . . . ?
C42A C43A C44A C45A 1(4) . . . . ?
C43A C44A C45A C46A -1(5) . . . . ?
C44A C45A C46A C41A -1(6) . . . . ?
C42A C41A C46A C45A 3(8) . . . . ?
C5 C41A C46A C45A 177(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
