# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_erk7638
_database_code_depnum_ccdc_archive 'CCDC 1411182'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H27 B F10 N'
_chemical_formula_weight         638.37

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                   8.35890(10)
_cell_length_b                   20.9131(3)
_cell_length_c                   17.1468(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5820(10)
_cell_angle_gamma                90.00
_cell_volume                     2971.23(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6953
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1308
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9875
_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            25543
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         28.29
_reflns_number_total             7262
_reflns_number_gt                5314
_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 C6F5 group and one C=CH2(Me) group are 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)+(0.0165P)²+2.0955P] 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         7262
_refine_ls_number_parameters     536
_refine_ls_number_restraints     328
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7848(2) 0.26666(9) 0.40339(12) 0.0355(4) Uani 1 1 d . . .
C2 C 0.7005(2) 0.29677(9) 0.46410(11) 0.0356(4) Uani 1 1 d . B .
H2A H 0.7244 0.3427 0.4655 0.043 Uiso 1 1 calc R . .
H2B H 0.7431 0.2789 0.5155 0.043 Uiso 1 1 calc R . .
C3 C 0.4634(2) 0.21150(9) 0.43810(11) 0.0319(4) Uani 1 1 d . B .
H3 H 0.4839 0.1944 0.3897 0.038 Uiso 1 1 calc R . .
C4 C 0.4103(2) 0.17021(9) 0.48764(11) 0.0350(4) Uani 1 1 d D . .
H4 H 0.3876 0.1866 0.5361 0.042 Uiso 1 1 calc R A 1
C5 C 0.3834(15) 0.1012(2) 0.4740(5) 0.033(2) Uani 0.72(5) 1 d PDU B 1
C6 C 0.363(2) 0.0634(5) 0.5346(7) 0.049(2) Uani 0.72(5) 1 d PDU B 1
H6A H 0.3651 0.0808 0.5853 0.058 Uiso 0.72(5) 1 calc PR B 1
H6B H 0.3454 0.0193 0.5266 0.058 Uiso 0.72(5) 1 calc PR B 1
C7 C 0.3963(16) 0.0732(4) 0.3946(4) 0.0395(18) Uani 0.72(5) 1 d PDU B 1
H7A H 0.3166 0.0929 0.3557 0.059 Uiso 0.72(5) 1 calc PR B 1
H7B H 0.3773 0.0275 0.3958 0.059 Uiso 0.72(5) 1 calc PR B 1
H7C H 0.5035 0.0811 0.3808 0.059 Uiso 0.72(5) 1 calc PR B 1
C5A C 0.389(4) 0.1009(7) 0.4816(15) 0.046(6) Uani 0.28(5) 1 d PDU B 2
C6A C 0.324(5) 0.0683(13) 0.5362(17) 0.048(5) Uani 0.28(5) 1 d PDU B 2
H601 H 0.2905 0.0898 0.5794 0.058 Uiso 0.28(5) 1 calc PR B 2
H602 H 0.3107 0.0238 0.5315 0.058 Uiso 0.28(5) 1 calc PR B 2
C7A C 0.376(5) 0.0747(13) 0.3994(14) 0.058(7) Uani 0.28(5) 1 d PDU B 2
H701 H 0.4831 0.0729 0.3830 0.087 Uiso 0.28(5) 1 calc PR B 2
H702 H 0.3076 0.1022 0.3640 0.087 Uiso 0.28(5) 1 calc PR B 2
H703 H 0.3307 0.0320 0.3982 0.087 Uiso 0.28(5) 1 calc PR B 2
N11 N 0.86713(19) 0.21364(8) 0.41349(10) 0.0376(4) Uani 1 1 d . . .
C12 C 0.8963(3) 0.17793(11) 0.48867(13) 0.0463(5) Uani 1 1 d . . .
H12A H 0.8348 0.1977 0.5271 0.056 Uiso 1 1 calc R . .
H12B H 1.0111 0.1804 0.5095 0.056 Uiso 1 1 calc R . .
C13 C 0.8473(3) 0.10841(11) 0.47774(14) 0.0478(5) Uani 1 1 d . . .
H13A H 0.7297 0.1058 0.4652 0.057 Uiso 1 1 calc R . .
H13B H 0.8786 0.0853 0.5272 0.057 Uiso 1 1 calc R . .
C14 C 0.9252(3) 0.07660(11) 0.41267(14) 0.0499(6) Uani 1 1 d . . .
H14A H 1.0413 0.0717 0.4295 0.060 Uiso 1 1 calc R . .
H14B H 0.8789 0.0339 0.4024 0.060 Uiso 1 1 calc R . .
C15 C 0.8989(3) 0.11598(11) 0.33801(14) 0.0495(5) Uani 1 1 d . . .
H15A H 0.7838 0.1161 0.3174 0.059 Uiso 1 1 calc R . .
H15B H 0.9578 0.0965 0.2983 0.059 Uiso 1 1 calc R . .
C16 C 0.9562(2) 0.18435(10) 0.35306(13) 0.0429(5) Uani 1 1 d . . .
H16A H 1.0723 0.1847 0.3714 0.051 Uiso 1 1 calc R . .
H16B H 0.9371 0.2091 0.3042 0.051 Uiso 1 1 calc R . .
C21 C 0.7695(2) 0.30025(10) 0.32633(12) 0.0395(5) Uani 1 1 d . . .
C22 C 0.6863(3) 0.27332(12) 0.25860(13) 0.0506(5) Uani 1 1 d . . .
H22 H 0.6471 0.2313 0.2599 0.061 Uiso 1 1 calc R . .
C23 C 0.6609(3) 0.30793(15) 0.18949(15) 0.0647(7) Uani 1 1 d . . .
H23 H 0.6042 0.2894 0.1441 0.078 Uiso 1 1 calc R . .
C24 C 0.7180(4) 0.36897(16) 0.18705(18) 0.0729(8) Uani 1 1 d . . .
H24 H 0.6994 0.3926 0.1401 0.087 Uiso 1 1 calc R . .
C25 C 0.8028(4) 0.39596(13) 0.25329(18) 0.0701(8) Uani 1 1 d . . .
H25 H 0.8441 0.4376 0.2510 0.084 Uiso 1 1 calc R . .
C26 C 0.8277(3) 0.36199(11) 0.32338(15) 0.0544(6) Uani 1 1 d . . .
H26 H 0.8839 0.3809 0.3687 0.065 Uiso 1 1 calc R . .
B1 B 0.4973(2) 0.28683(10) 0.44985(12) 0.0311(4) Uani 1 1 d D . .
C31 C 0.417(4) 0.3351(8) 0.3800(14) 0.035(5) Uani 0.28(2) 1 d PDU B 1
F32 F 0.525(3) 0.4247(13) 0.4528(12) 0.051(3) Uani 0.28(2) 1 d PDU B 1
C32 C 0.442(3) 0.4000(6) 0.3871(11) 0.027(3) Uani 0.28(2) 1 d PDU B 1
F33 F 0.412(3) 0.5064(7) 0.3420(11) 0.081(4) Uani 0.28(2) 1 d PDU B 1
C33 C 0.380(3) 0.4437(7) 0.3319(11) 0.046(4) Uani 0.28(2) 1 d PDU B 1
F34 F 0.226(3) 0.4645(7) 0.2091(8) 0.084(4) Uani 0.28(2) 1 d PDU B 1
C34 C 0.293(3) 0.4233(7) 0.2641(9) 0.047(4) Uani 0.28(2) 1 d PDU B 1
F35 F 0.175(3) 0.3378(9) 0.1865(10) 0.077(4) Uani 0.28(2) 1 d PDU B 1
C35 C 0.266(2) 0.3593(7) 0.2520(9) 0.040(3) Uani 0.28(2) 1 d PDU B 1
F36 F 0.284(4) 0.2551(9) 0.298(2) 0.052(4) Uani 0.28(2) 1 d PDU B 1
C36 C 0.323(5) 0.3180(9) 0.3113(14) 0.050(5) Uani 0.28(2) 1 d PDU B 1
C31A C 0.4122(18) 0.3293(3) 0.3726(6) 0.0349(17) Uani 0.72(2) 1 d PDU B 2
F32A F 0.5106(14) 0.4253(5) 0.4347(6) 0.0625(16) Uani 0.72(2) 1 d PDU B 2
C32A C 0.4184(14) 0.3955(4) 0.3731(6) 0.0484(19) Uani 0.72(2) 1 d PDU B 2
F33A F 0.3567(11) 0.4996(3) 0.3235(6) 0.0845(17) Uani 0.72(2) 1 d PDU B 2
C33A C 0.3398(13) 0.4352(3) 0.3166(6) 0.0540(17) Uani 0.72(2) 1 d PDU B 2
F34A F 0.1645(10) 0.4473(4) 0.1993(4) 0.0819(18) Uani 0.72(2) 1 d PDU B 2
C34A C 0.2444(10) 0.4090(4) 0.2546(4) 0.0524(16) Uani 0.72(2) 1 d PDU B 2
F35A F 0.1403(9) 0.3175(5) 0.1875(4) 0.0752(16) Uani 0.72(2) 1 d PDU B 2
C35A C 0.2308(10) 0.3438(4) 0.2494(4) 0.0491(15) Uani 0.72(2) 1 d PDU B 2
F36A F 0.2973(18) 0.2429(4) 0.2947(8) 0.0543(18) Uani 0.72(2) 1 d PDU B 2
C36A C 0.3167(16) 0.3066(4) 0.3072(5) 0.0369(14) Uani 0.72(2) 1 d PDU B 2
C41 C 0.4189(2) 0.31320(9) 0.52769(11) 0.0320(4) Uani 1 1 d . B .
F42 F 0.15964(13) 0.28700(6) 0.46192(7) 0.0476(3) Uani 1 1 d . B .
C42 C 0.2526(2) 0.30924(9) 0.52687(12) 0.0366(4) Uani 1 1 d . . .
F43 F 0.00993(14) 0.32014(8) 0.58291(9) 0.0645(4) Uani 1 1 d . . .
C43 C 0.1708(2) 0.32663(11) 0.58821(13) 0.0422(5) Uani 1 1 d . B .
F44 F 0.17754(16) 0.36944(7) 0.71558(8) 0.0593(4) Uani 1 1 d . B .
C44 C 0.2551(2) 0.35098(10) 0.65552(12) 0.0417(5) Uani 1 1 d . . .
F45 F 0.50332(15) 0.38113(7) 0.72584(7) 0.0542(3) Uani 1 1 d . . .
C45 C 0.4188(2) 0.35741(10) 0.66001(12) 0.0389(4) Uani 1 1 d . B .
F46 F 0.65800(13) 0.34797(7) 0.60856(7) 0.0510(3) Uani 1 1 d . B .
C46 C 0.4958(2) 0.33911(9) 0.59718(11) 0.0351(4) Uani 1 1 d . . .
C51 C 0.9846(5) 0.48133(16) 0.5748(2) 0.0886(10) Uani 1 1 d . . .
H51 H 0.9740 0.4684 0.6264 0.106 Uiso 1 1 calc R . .
C52 C 0.8499(4) 0.48826(15) 0.5207(2) 0.0820(9) Uani 1 1 d . . .
H52 H 0.7472 0.4802 0.5352 0.098 Uiso 1 1 calc R . .
C53 C 0.8644(4) 0.50684(15) 0.4459(2) 0.0852(10) Uani 1 1 d . . .
H53 H 0.7720 0.5116 0.4087 0.102 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N11 1.304(3) . ?
C1 C2 1.473(3) . ?
C1 C21 1.487(3) . ?
C2 B1 1.697(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.328(3) . ?
C3 B1 1.608(3) . ?
C3 H3 0.9400 . ?
C4 C5A 1.463(14) . ?
C4 C5 1.474(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.335(6) . ?
C5 C7 1.500(6) . ?
C6 H6A 0.9400 . ?
C6 H6B 0.9400 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C5A C6A 1.331(15) . ?
C5A C7A 1.502(15) . ?
C6A H601 0.9400 . ?
C6A H602 0.9400 . ?
C7A H701 0.9700 . ?
C7A H702 0.9700 . ?
C7A H703 0.9700 . ?
N11 C12 1.482(3) . ?
N11 C16 1.486(2) . ?
C12 C13 1.515(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.514(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C21 C26 1.383(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.365(4) . ?
C23 H23 0.9400 . ?
C24 C25 1.378(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.388(4) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
B1 C31 1.639(12) . ?
B1 C41 1.657(3) . ?
B1 C31A 1.674(5) . ?
C31 C32 1.375(12) . ?
C31 C36 1.375(13) . ?
F32 C32 1.346(12) . ?
C32 C33 1.366(11) . ?
F33 C33 1.343(12) . ?
C33 C34 1.359(11) . ?
F34 C34 1.342(11) . ?
C34 C35 1.369(11) . ?
F35 C35 1.347(12) . ?
C35 C36 1.371(12) . ?
F36 C36 1.366(13) . ?
C31A C36A 1.372(6) . ?
C31A C32A 1.386(7) . ?
F32A C32A 1.371(7) . ?
C32A C33A 1.375(7) . ?
F33A C33A 1.358(6) . ?
C33A C34A 1.359(7) . ?
F34A C34A 1.347(5) . ?
C34A C35A 1.371(7) . ?
F35A C35A 1.337(6) . ?
C35A C36A 1.383(6) . ?
F36A C36A 1.356(7) . ?
C41 C46 1.387(3) . ?
C41 C42 1.390(3) . ?
F42 C42 1.354(2) . ?
C42 C43 1.377(3) . ?
F43 C43 1.343(2) . ?
C43 C44 1.368(3) . ?
F44 C44 1.344(2) . ?
C44 C45 1.367(3) . ?
F45 C45 1.345(2) . ?
C45 C46 1.380(3) . ?
F46 C46 1.356(2) . ?
C51 C52 1.369(5) . ?
C51 C53 1.379(5) 3_766 ?
C51 H51 0.9400 . ?
C52 C53 1.360(5) . ?
C52 H52 0.9400 . ?
C53 C51 1.379(5) 3_766 ?
C53 H53 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 C1 C2 124.25(19) . . ?
N11 C1 C21 120.10(18) . . ?
C2 C1 C21 115.65(17) . . ?
C1 C2 B1 114.15(15) . . ?
C1 C2 H2A 108.7 . . ?
B1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
B1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 B1 128.68(18) . . ?
C4 C3 H3 115.7 . . ?
B1 C3 H3 115.7 . . ?
C3 C4 C5A 130.3(9) . . ?
C3 C4 C5 126.3(4) . . ?
C5A C4 C5 5.1(14) . . ?
C3 C4 H4 116.9 . . ?
C5A C4 H4 112.7 . . ?
C5 C4 H4 116.9 . . ?
C6 C5 C4 119.3(7) . . ?
C6 C5 C7 120.5(6) . . ?
C4 C5 C7 119.9(5) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
C6A C5A C4 121.0(18) . . ?
C6A C5A C7A 119(2) . . ?
C4 C5A C7A 114.9(17) . . ?
C5A C6A H601 120.0 . . ?
C5A C6A H602 120.0 . . ?
H601 C6A H602 120.0 . . ?
C5A C7A H701 109.5 . . ?
C5A C7A H702 109.5 . . ?
H701 C7A H702 109.5 . . ?
C5A C7A H703 109.5 . . ?
H701 C7A H703 109.5 . . ?
H702 C7A H703 109.5 . . ?
C1 N11 C12 124.57(17) . . ?
C1 N11 C16 124.21(18) . . ?
C12 N11 C16 111.01(16) . . ?
N11 C12 C13 111.42(18) . . ?
N11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 112.10(18) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 110.78(18) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 111.15(19) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N11 C16 C15 109.31(17) . . ?
N11 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N11 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C26 C21 C22 119.1(2) . . ?
C26 C21 C1 119.0(2) . . ?
C22 C21 C1 121.70(19) . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.8(3) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C3 B1 C31 117.6(6) . . ?
C3 B1 C41 110.18(15) . . ?
C31 B1 C41 102.5(14) . . ?
C3 B1 C31A 111.8(3) . . ?
C31 B1 C31A 6.0(9) . . ?
C41 B1 C31A 106.8(6) . . ?
C3 B1 C2 107.13(15) . . ?
C31 B1 C2 109.5(13) . . ?
C41 B1 C2 109.75(15) . . ?
C31A B1 C2 111.2(6) . . ?
C32 C31 C36 113.2(12) . . ?
C32 C31 B1 120.1(11) . . ?
C36 C31 B1 126.7(11) . . ?
F32 C32 C33 115.3(14) . . ?
F32 C32 C31 120.5(15) . . ?
C33 C32 C31 124.1(12) . . ?
F33 C33 C34 119.4(12) . . ?
F33 C33 C32 120.9(12) . . ?
C34 C33 C32 119.6(12) . . ?
F34 C34 C33 121.7(11) . . ?
F34 C34 C35 118.6(11) . . ?
C33 C34 C35 119.6(11) . . ?
F35 C35 C34 120.9(11) . . ?
F35 C35 C36 120.7(12) . . ?
C34 C35 C36 118.1(12) . . ?
F36 C36 C35 115.8(16) . . ?
F36 C36 C31 119.1(16) . . ?
C35 C36 C31 125.1(13) . . ?
C36A C31A C32A 111.6(5) . . ?
C36A C31A B1 127.2(5) . . ?
C32A C31A B1 120.9(5) . . ?
F32A C32A C33A 115.8(7) . . ?
F32A C32A C31A 118.4(6) . . ?
C33A C32A C31A 125.8(6) . . ?
F33A C33A C34A 120.7(5) . . ?
F33A C33A C32A 120.2(6) . . ?
C34A C33A C32A 119.0(5) . . ?
F34A C34A C33A 119.8(6) . . ?
F34A C34A C35A 121.1(6) . . ?
C33A C34A C35A 119.1(5) . . ?
F35A C35A C34A 119.5(5) . . ?
F35A C35A C36A 121.6(6) . . ?
C34A C35A C36A 118.8(6) . . ?
F36A C36A C31A 120.8(6) . . ?
F36A C36A C35A 113.5(6) . . ?
C31A C36A C35A 125.6(6) . . ?
C46 C41 C42 112.43(17) . . ?
C46 C41 B1 129.34(16) . . ?
C42 C41 B1 118.22(16) . . ?
F42 C42 C43 115.47(17) . . ?
F42 C42 C41 119.58(17) . . ?
C43 C42 C41 124.95(18) . . ?
F43 C43 C44 119.61(19) . . ?
F43 C43 C42 121.03(18) . . ?
C44 C43 C42 119.36(18) . . ?
F44 C44 C45 120.60(19) . . ?
F44 C44 C43 120.43(19) . . ?
C45 C44 C43 118.96(19) . . ?
F45 C45 C44 119.67(18) . . ?
F45 C45 C46 120.62(18) . . ?
C44 C45 C46 119.71(18) . . ?
F46 C46 C45 114.23(16) . . ?
F46 C46 C41 121.21(17) . . ?
C45 C46 C41 124.56(17) . . ?
C52 C51 C53 120.3(3) . 3_766 ?
C52 C51 H51 119.8 . . ?
C53 C51 H51 119.8 3_766 . ?
C53 C52 C51 120.2(3) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C52 C53 C51 119.5(3) . 3_766 ?
C52 C53 H53 120.2 . . ?
C51 C53 H53 120.2 3_766 . ?

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
N11 C1 C2 B1 -104.2(2) . . . . ?
C21 C1 C2 B1 74.9(2) . . . . ?
B1 C3 C4 C5A -175(2) . . . . ?
B1 C3 C4 C5 -179.1(6) . . . . ?
C3 C4 C5 C6 166.0(10) . . . . ?
C5A C4 C5 C6 23(19) . . . . ?
C3 C4 C5 C7 -7.8(14) . . . . ?
C5A C4 C5 C7 -151(21) . . . . ?
C3 C4 C5A C6A -176(3) . . . . ?
C5 C4 C5A C6A -136(23) . . . . ?
C3 C4 C5A C7A -21(4) . . . . ?
C5 C4 C5A C7A 19(18) . . . . ?
C2 C1 N11 C12 -3.9(3) . . . . ?
C21 C1 N11 C12 177.06(18) . . . . ?
C2 C1 N11 C16 -178.07(17) . . . . ?
C21 C1 N11 C16 2.8(3) . . . . ?
C1 N11 C12 C13 127.1(2) . . . . ?
C16 N11 C12 C13 -58.0(2) . . . . ?
N11 C12 C13 C14 53.0(2) . . . . ?
C12 C13 C14 C15 -51.1(3) . . . . ?
C13 C14 C15 C16 54.3(2) . . . . ?
C1 N11 C16 C15 -124.5(2) . . . . ?
C12 N11 C16 C15 60.6(2) . . . . ?
C14 C15 C16 N11 -58.9(2) . . . . ?
N11 C1 C21 C26 -119.6(2) . . . . ?
C2 C1 C21 C26 61.2(2) . . . . ?
N11 C1 C21 C22 66.0(3) . . . . ?
C2 C1 C21 C22 -113.2(2) . . . . ?
C26 C21 C22 C23 -0.6(3) . . . . ?
C1 C21 C22 C23 173.9(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 0.8(4) . . . . ?
C23 C24 C25 C26 -1.5(4) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C1 C21 C26 C25 -174.8(2) . . . . ?
C24 C25 C26 C21 1.2(4) . . . . ?
C4 C3 B1 C31 -129.5(18) . . . . ?
C4 C3 B1 C41 -12.5(3) . . . . ?
C4 C3 B1 C31A -131.1(7) . . . . ?
C4 C3 B1 C2 106.8(2) . . . . ?
C1 C2 B1 C3 52.2(2) . . . . ?
C1 C2 B1 C31 -76.4(11) . . . . ?
C1 C2 B1 C41 171.80(16) . . . . ?
C1 C2 B1 C31A -70.2(5) . . . . ?
C3 B1 C31 C32 180(3) . . . . ?
C41 B1 C31 C32 59(3) . . . . ?
C31A B1 C31 C32 -166(23) . . . . ?
C2 B1 C31 C32 -58(4) . . . . ?
C3 B1 C31 C36 0(5) . . . . ?
C41 B1 C31 C36 -121(4) . . . . ?
C31A B1 C31 C36 14(17) . . . . ?
C2 B1 C31 C36 122(4) . . . . ?
C36 C31 C32 F32 177(3) . . . . ?
B1 C31 C32 F32 -3(5) . . . . ?
C36 C31 C32 C33 0(5) . . . . ?
B1 C31 C32 C33 180(2) . . . . ?
F32 C32 C33 F33 4(4) . . . . ?
C31 C32 C33 F33 -179(3) . . . . ?
F32 C32 C33 C34 -179(2) . . . . ?
C31 C32 C33 C34 -2(4) . . . . ?
F33 C33 C34 F34 -5(3) . . . . ?
C32 C33 C34 F34 178(2) . . . . ?
F33 C33 C34 C35 177.2(19) . . . . ?
C32 C33 C34 C35 0(3) . . . . ?
F34 C34 C35 F35 0(3) . . . . ?
C33 C34 C35 F35 178(2) . . . . ?
F34 C34 C35 C36 -175(3) . . . . ?
C33 C34 C35 C36 3(4) . . . . ?
F35 C35 C36 F36 1(5) . . . . ?
C34 C35 C36 F36 176(3) . . . . ?
F35 C35 C36 C31 180(4) . . . . ?
C34 C35 C36 C31 -6(6) . . . . ?
C32 C31 C36 F36 -177(4) . . . . ?
B1 C31 C36 F36 2(7) . . . . ?
C32 C31 C36 C35 4(6) . . . . ?
B1 C31 C36 C35 -176(3) . . . . ?
C3 B1 C31A C36A 3.3(19) . . . . ?
C31 B1 C31A C36A -163(21) . . . . ?
C41 B1 C31A C36A -117.3(16) . . . . ?
C2 B1 C31A C36A 123.0(15) . . . . ?
C3 B1 C31A C32A 175.9(12) . . . . ?
C31 B1 C31A C32A 10(19) . . . . ?
C41 B1 C31A C32A 55.3(15) . . . . ?
C2 B1 C31A C32A -64.4(15) . . . . ?
C36A C31A C32A F32A -179.5(13) . . . . ?
B1 C31A C32A F32A 7(2) . . . . ?
C36A C31A C32A C33A 0(2) . . . . ?
B1 C31A C32A C33A -173.2(11) . . . . ?
F32A C32A C33A F33A 0.4(16) . . . . ?
C31A C32A C33A F33A -179.5(13) . . . . ?
F32A C32A C33A C34A -179.0(10) . . . . ?
C31A C32A C33A C34A 1.1(19) . . . . ?
F33A C33A C34A F34A -0.4(13) . . . . ?
C32A C33A C34A F34A 179.0(9) . . . . ?
F33A C33A C34A C35A 179.7(8) . . . . ?
C32A C33A C34A C35A -0.8(13) . . . . ?
F34A C34A C35A F35A 1.8(11) . . . . ?
C33A C34A C35A F35A -178.4(8) . . . . ?
F34A C34A C35A C36A 179.3(9) . . . . ?
C33A C34A C35A C36A -0.9(13) . . . . ?
C32A C31A C36A F36A 178.7(15) . . . . ?
B1 C31A C36A F36A -8(3) . . . . ?
C32A C31A C36A C35A -2(2) . . . . ?
B1 C31A C36A C35A 170.8(12) . . . . ?
F35A C35A C36A F36A -0.9(17) . . . . ?
C34A C35A C36A F36A -178.3(11) . . . . ?
F35A C35A C36A C31A -179.9(14) . . . . ?
C34A C35A C36A C31A 3(2) . . . . ?
C3 B1 C41 C46 116.6(2) . . . . ?
C31 B1 C41 C46 -117.4(10) . . . . ?
C31A B1 C41 C46 -121.8(5) . . . . ?
C2 B1 C41 C46 -1.1(3) . . . . ?
C3 B1 C41 C42 -62.5(2) . . . . ?
C31 B1 C41 C42 63.5(10) . . . . ?
C31A B1 C41 C42 59.1(5) . . . . ?
C2 B1 C41 C42 179.78(17) . . . . ?
C46 C41 C42 F42 177.73(17) . . . . ?
B1 C41 C42 F42 -3.0(3) . . . . ?
C46 C41 C42 C43 -2.1(3) . . . . ?
B1 C41 C42 C43 177.14(19) . . . . ?
F42 C42 C43 F43 1.4(3) . . . . ?
C41 C42 C43 F43 -178.80(19) . . . . ?
F42 C42 C43 C44 -178.55(19) . . . . ?
C41 C42 C43 C44 1.3(3) . . . . ?
F43 C43 C44 F44 -1.2(3) . . . . ?
C42 C43 C44 F44 178.71(19) . . . . ?
F43 C43 C44 C45 -179.9(2) . . . . ?
C42 C43 C44 C45 0.0(3) . . . . ?
F44 C44 C45 F45 1.5(3) . . . . ?
C43 C44 C45 F45 -179.8(2) . . . . ?
F44 C44 C45 C46 -178.97(19) . . . . ?
C43 C44 C45 C46 -0.3(3) . . . . ?
F45 C45 C46 F46 -0.6(3) . . . . ?
C44 C45 C46 F46 179.81(19) . . . . ?
F45 C45 C46 C41 178.83(19) . . . . ?
C44 C45 C46 C41 -0.7(3) . . . . ?
C42 C41 C46 F46 -178.76(17) . . . . ?
B1 C41 C46 F46 2.1(3) . . . . ?
C42 C41 C46 C45 1.8(3) . . . . ?
B1 C41 C46 C45 -177.33(19) . . . . ?
C53 C51 C52 C53 0.1(6) 3_766 . . . ?
C51 C52 C53 C51 -0.1(5) . . . 3_766 ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_erk7639
_database_code_depnum_ccdc_archive 'CCDC 1411183'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 B F10 N O'
_chemical_formula_weight         579.28

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.9201(2)
_cell_length_b                   10.7594(3)
_cell_length_c                   25.6057(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.6190(10)
_cell_angle_gamma                90.00
_cell_volume                     2457.36(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4913
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_T_max  0.9826
_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            13001
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4976
_reflns_number_gt                3891
_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)+(0.0275P)²+1.6132P] 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         4976
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0877(2) 0.2702(2) 0.12644(10) 0.0327(5) Uani 1 1 d . . .
C2 C 0.0823(2) 0.32991(19) 0.06747(8) 0.0321(4) Uani 1 1 d . . .
H2 H 0.1018 0.4201 0.0709 0.039 Uiso 1 1 calc R . .
C3 C 0.1690(2) 0.2846(2) 0.02207(8) 0.0358(5) Uani 1 1 d . . .
H3 H 0.2709 0.3063 0.0205 0.043 Uiso 1 1 calc R . .
C4 C 0.1134(2) 0.2161(2) -0.01616(9) 0.0398(5) Uani 1 1 d . . .
C5 C -0.0480(2) 0.1743(2) -0.01540(9) 0.0428(5) Uani 1 1 d . . .
H5A H -0.0516 0.0867 -0.0257 0.051 Uiso 1 1 calc R . .
H5B H -0.1036 0.2217 -0.0419 0.051 Uiso 1 1 calc R . .
C6 C -0.1299(2) 0.1879(2) 0.03687(8) 0.0367(5) Uani 1 1 d . . .
H6 H -0.0965 0.1196 0.0601 0.044 Uiso 1 1 calc R . .
C7 C -0.2990(2) 0.1705(3) 0.02548(10) 0.0487(6) Uani 1 1 d . . .
H7A H -0.3128 0.0972 0.0032 0.058 Uiso 1 1 calc R . .
H7B H -0.3505 0.1546 0.0584 0.058 Uiso 1 1 calc R . .
C8 C -0.3713(3) 0.2823(3) -0.00119(11) 0.0611(8) Uani 1 1 d . . .
H8A H -0.3343 0.2887 -0.0370 0.073 Uiso 1 1 calc R . .
H8B H -0.4801 0.2700 -0.0030 0.073 Uiso 1 1 calc R . .
C9 C -0.3378(3) 0.4022(3) 0.02759(11) 0.0560(7) Uani 1 1 d . . .
H9A H -0.3866 0.4010 0.0617 0.067 Uiso 1 1 calc R . .
H9B H -0.3782 0.4726 0.0076 0.067 Uiso 1 1 calc R . .
C10 C -0.1690(2) 0.4183(2) 0.03516(10) 0.0437(5) Uani 1 1 d . . .
H10A H -0.1237 0.4287 0.0007 0.052 Uiso 1 1 calc R . .
H10B H -0.1513 0.4952 0.0548 0.052 Uiso 1 1 calc R . .
C1 C -0.0879(2) 0.3127(2) 0.06336(8) 0.0341(4) Uani 1 1 d . . .
C11 C 0.2001(3) 0.1811(3) -0.06397(10) 0.0553(7) Uani 1 1 d . . .
H11A H 0.3010 0.2143 -0.0612 0.083 Uiso 1 1 calc R . .
H11B H 0.1507 0.2151 -0.0947 0.083 Uiso 1 1 calc R . .
H11C H 0.2046 0.0913 -0.0668 0.083 Uiso 1 1 calc R . .
N1 N -0.10392(18) 0.30823(16) 0.12496(7) 0.0337(4) Uani 1 1 d . . .
C12 C -0.1270(2) 0.4375(2) 0.14640(10) 0.0422(5) Uani 1 1 d . . .
H12A H -0.2145 0.4749 0.1291 0.051 Uiso 1 1 calc R . .
H12B H -0.0394 0.4885 0.1381 0.051 Uiso 1 1 calc R . .
C13 C -0.1503(3) 0.4393(2) 0.20493(10) 0.0503(6) Uani 1 1 d . . .
H13A H -0.0597 0.4082 0.2225 0.060 Uiso 1 1 calc R . .
H13B H -0.1663 0.5252 0.2163 0.060 Uiso 1 1 calc R . .
O14 O -0.27440(19) 0.36586(17) 0.22000(7) 0.0540(4) Uani 1 1 d . . .
C15 C -0.2509(3) 0.2418(2) 0.20315(10) 0.0490(6) Uani 1 1 d . . .
H15A H -0.3356 0.1901 0.2139 0.059 Uiso 1 1 calc R . .
H15B H -0.1599 0.2088 0.2198 0.059 Uiso 1 1 calc R . .
C16 C -0.2354(2) 0.2352(2) 0.14470(9) 0.0397(5) Uani 1 1 d . . .
H16A H -0.2241 0.1481 0.1343 0.048 Uiso 1 1 calc R . .
H16B H -0.3274 0.2670 0.1282 0.048 Uiso 1 1 calc R . .
C31 C 0.1900(2) 0.3409(2) 0.17097(9) 0.0365(5) Uani 1 1 d . . .
F32 F 0.31088(16) 0.48085(14) 0.11232(6) 0.0619(4) Uani 1 1 d . . .
C32 C 0.2956(3) 0.4332(2) 0.16085(10) 0.0446(5) Uani 1 1 d . . .
F33 F 0.49287(17) 0.56891(14) 0.18490(8) 0.0739(5) Uani 1 1 d . . .
C33 C 0.3943(3) 0.4805(2) 0.19784(11) 0.0509(6) Uani 1 1 d . . .
F34 F 0.48430(18) 0.48320(17) 0.28434(7) 0.0754(5) Uani 1 1 d . . .
C34 C 0.3913(3) 0.4356(3) 0.24789(11) 0.0538(7) Uani 1 1 d . . .
F35 F 0.28939(18) 0.29667(18) 0.30919(6) 0.0715(5) Uani 1 1 d . . .
C35 C 0.2923(3) 0.3433(3) 0.26046(10) 0.0515(6) Uani 1 1 d . . .
F36 F 0.10221(15) 0.20672(13) 0.23687(5) 0.0517(4) Uani 1 1 d . . .
C36 C 0.1963(2) 0.2988(2) 0.22215(9) 0.0422(5) Uani 1 1 d . . .
C21 C 0.1380(2) 0.1233(2) 0.12966(8) 0.0333(4) Uani 1 1 d . . .
F22 F -0.06811(14) 0.02483(12) 0.17143(6) 0.0496(4) Uani 1 1 d . . .
C22 C 0.0706(2) 0.0183(2) 0.15057(9) 0.0374(5) Uani 1 1 d . . .
F23 F 0.06121(16) -0.19347(12) 0.17452(6) 0.0536(4) Uani 1 1 d . . .
C23 C 0.1360(2) -0.0976(2) 0.15359(9) 0.0391(5) Uani 1 1 d . . .
F24 F 0.34367(17) -0.22649(13) 0.13889(7) 0.0619(4) Uani 1 1 d . . .
C24 C 0.2784(3) -0.1151(2) 0.13570(9) 0.0423(5) Uani 1 1 d . . .
F25 F 0.49426(15) -0.02864(14) 0.09869(6) 0.0596(4) Uani 1 1 d . . .
C25 C 0.3529(2) -0.0152(2) 0.11535(9) 0.0408(5) Uani 1 1 d . . .
F26 F 0.37131(13) 0.19441(12) 0.09720(5) 0.0454(3) Uani 1 1 d . . .
C26 C 0.2847(2) 0.0993(2) 0.11363(9) 0.0369(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C31 1.640(3) . ?
B1 C2 1.641(3) . ?
B1 C21 1.645(3) . ?
B1 N1 1.758(3) . ?
C2 C3 1.486(3) . ?
C2 C1 1.532(3) . ?
C2 H2 0.9900 . ?
C3 C4 1.318(3) . ?
C3 H3 0.9400 . ?
C4 C11 1.503(3) . ?
C4 C5 1.508(3) . ?
C5 C6 1.539(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.545(3) . ?
C6 C1 1.548(3) . ?
C6 H6 0.9900 . ?
C7 C8 1.523(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.514(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C1 1.525(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C1 N1 1.586(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
N1 C16 1.504(3) . ?
N1 C12 1.510(3) . ?
C12 C13 1.515(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 O14 1.417(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
O14 C15 1.419(3) . ?
C15 C16 1.506(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C31 C36 1.387(3) . ?
C31 C32 1.395(3) . ?
F32 C32 1.353(3) . ?
C32 C33 1.383(3) . ?
F33 C33 1.340(3) . ?
C33 C34 1.370(4) . ?
F34 C34 1.343(3) . ?
C34 C35 1.370(4) . ?
F35 C35 1.345(3) . ?
C35 C36 1.381(3) . ?
F36 C36 1.354(3) . ?
C21 C22 1.389(3) . ?
C21 C26 1.400(3) . ?
F22 C22 1.355(2) . ?
C22 C23 1.379(3) . ?
F23 C23 1.343(2) . ?
C23 C24 1.368(3) . ?
F24 C24 1.335(2) . ?
C24 C25 1.370(3) . ?
F25 C25 1.343(2) . ?
C25 C26 1.374(3) . ?
F26 C26 1.352(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C31 B1 C2 117.96(17) . . ?
C31 B1 C21 105.18(16) . . ?
C2 B1 C21 115.33(18) . . ?
C31 B1 N1 116.13(16) . . ?
C2 B1 N1 82.51(13) . . ?
C21 B1 N1 119.30(16) . . ?
C3 C2 C1 115.49(17) . . ?
C3 C2 B1 125.50(17) . . ?
C1 C2 B1 92.03(15) . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
B1 C2 H2 107.4 . . ?
C4 C3 C2 124.71(18) . . ?
C4 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
C3 C4 C11 123.5(2) . . ?
C3 C4 C5 120.6(2) . . ?
C11 C4 C5 115.8(2) . . ?
C4 C5 C6 116.42(18) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
C5 C6 C7 107.22(18) . . ?
C5 C6 C1 110.42(17) . . ?
C7 C6 C1 114.80(18) . . ?
C5 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C1 C6 H6 108.1 . . ?
C8 C7 C6 113.3(2) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 112.0(2) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 110.3(2) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C1 C10 C9 116.0(2) . . ?
C1 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C1 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C1 C2 114.01(17) . . ?
C10 C1 C6 109.12(17) . . ?
C2 C1 C6 111.72(16) . . ?
C10 C1 N1 116.48(17) . . ?
C2 C1 N1 92.01(15) . . ?
C6 C1 N1 112.69(16) . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 N1 C12 104.42(16) . . ?
C16 N1 C1 115.40(16) . . ?
C12 N1 C1 110.37(16) . . ?
C16 N1 B1 129.27(16) . . ?
C12 N1 B1 110.06(15) . . ?
C1 N1 B1 86.00(13) . . ?
N1 C12 C13 113.07(19) . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O14 C13 C12 112.2(2) . . ?
O14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
O14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 O14 C15 108.87(17) . . ?
O14 C15 C16 111.2(2) . . ?
O14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
O14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N1 C16 C15 112.93(18) . . ?
N1 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
N1 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C36 C31 C32 112.8(2) . . ?
C36 C31 B1 121.5(2) . . ?
C32 C31 B1 125.0(2) . . ?
F32 C32 C33 114.8(2) . . ?
F32 C32 C31 121.04(19) . . ?
C33 C32 C31 124.1(2) . . ?
F33 C33 C34 120.1(2) . . ?
F33 C33 C32 120.4(3) . . ?
C34 C33 C32 119.5(2) . . ?
F34 C34 C35 120.5(3) . . ?
F34 C34 C33 119.8(3) . . ?
C35 C34 C33 119.6(2) . . ?
F35 C35 C34 120.5(2) . . ?
F35 C35 C36 120.8(3) . . ?
C34 C35 C36 118.7(2) . . ?
F36 C36 C35 115.9(2) . . ?
F36 C36 C31 118.9(2) . . ?
C35 C36 C31 125.2(2) . . ?
C22 C21 C26 111.88(19) . . ?
C22 C21 B1 132.99(18) . . ?
C26 C21 B1 114.69(17) . . ?
F22 C22 C23 114.34(18) . . ?
F22 C22 C21 120.70(18) . . ?
C23 C22 C21 124.94(19) . . ?
F23 C23 C24 119.7(2) . . ?
F23 C23 C22 120.4(2) . . ?
C24 C23 C22 119.9(2) . . ?
F24 C24 C23 120.6(2) . . ?
F24 C24 C25 121.0(2) . . ?
C23 C24 C25 118.4(2) . . ?
F25 C25 C24 119.8(2) . . ?
F25 C25 C26 120.2(2) . . ?
C24 C25 C26 119.92(19) . . ?
F26 C26 C25 115.72(18) . . ?
F26 C26 C21 119.39(18) . . ?
C25 C26 C21 124.8(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
C31 B1 C2 C3 100.7(2) . . . . ?
C21 B1 C2 C3 -24.7(3) . . . . ?
N1 B1 C2 C3 -143.61(19) . . . . ?
C31 B1 C2 C1 -135.61(18) . . . . ?
C21 B1 C2 C1 98.99(18) . . . . ?
N1 B1 C2 C1 -19.94(14) . . . . ?
C1 C2 C3 C4 -10.7(3) . . . . ?
B1 C2 C3 C4 102.2(3) . . . . ?
C2 C3 C4 C11 174.4(2) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C3 C4 C5 C6 -14.2(3) . . . . ?
C11 C4 C5 C6 169.2(2) . . . . ?
C4 C5 C6 C7 166.6(2) . . . . ?
C4 C5 C6 C1 40.9(3) . . . . ?
C5 C6 C7 C8 -74.9(3) . . . . ?
C1 C6 C7 C8 48.2(3) . . . . ?
C6 C7 C8 C9 -51.4(3) . . . . ?
C7 C8 C9 C10 54.1(3) . . . . ?
C8 C9 C10 C1 -56.4(3) . . . . ?
C9 C10 C1 C2 177.0(2) . . . . ?
C9 C10 C1 C6 51.3(3) . . . . ?
C9 C10 C1 N1 -77.7(3) . . . . ?
C3 C2 C1 C10 -86.3(2) . . . . ?
B1 C2 C1 C10 142.30(19) . . . . ?
C3 C2 C1 C6 37.9(2) . . . . ?
B1 C2 C1 C6 -93.40(18) . . . . ?
C3 C2 C1 N1 153.38(17) . . . . ?
B1 C2 C1 N1 22.03(15) . . . . ?
C5 C6 C1 C10 75.1(2) . . . . ?
C7 C6 C1 C10 -46.2(2) . . . . ?
C5 C6 C1 C2 -51.9(2) . . . . ?
C7 C6 C1 C2 -173.23(18) . . . . ?
C5 C6 C1 N1 -153.88(17) . . . . ?
C7 C6 C1 N1 84.8(2) . . . . ?
C10 C1 N1 C16 89.3(2) . . . . ?
C2 C1 N1 C16 -152.55(16) . . . . ?
C6 C1 N1 C16 -38.0(2) . . . . ?
C10 C1 N1 C12 -28.8(2) . . . . ?
C2 C1 N1 C12 89.40(17) . . . . ?
C6 C1 N1 C12 -156.01(16) . . . . ?
C10 C1 N1 B1 -138.72(18) . . . . ?
C2 C1 N1 B1 -20.54(14) . . . . ?
C6 C1 N1 B1 94.05(16) . . . . ?
C31 B1 N1 C16 -103.3(2) . . . . ?
C2 B1 N1 C16 139.2(2) . . . . ?
C21 B1 N1 C16 24.3(3) . . . . ?
C31 B1 N1 C12 26.6(2) . . . . ?
C2 B1 N1 C12 -90.97(17) . . . . ?
C21 B1 N1 C12 154.13(19) . . . . ?
C31 B1 N1 C1 136.80(18) . . . . ?
C2 B1 N1 C1 19.27(14) . . . . ?
C21 B1 N1 C1 -95.64(19) . . . . ?
C16 N1 C12 C13 52.8(2) . . . . ?
C1 N1 C12 C13 177.36(17) . . . . ?
B1 N1 C12 C13 -89.4(2) . . . . ?
N1 C12 C13 O14 -57.9(2) . . . . ?
C12 C13 O14 C15 58.5(3) . . . . ?
C13 O14 C15 C16 -59.9(3) . . . . ?
C12 N1 C16 C15 -54.7(2) . . . . ?
C1 N1 C16 C15 -175.98(17) . . . . ?
B1 N1 C16 C15 77.2(3) . . . . ?
O14 C15 C16 N1 61.3(2) . . . . ?
C2 B1 C31 C36 177.71(18) . . . . ?
C21 B1 C31 C36 -52.1(2) . . . . ?
N1 B1 C31 C36 82.2(2) . . . . ?
C2 B1 C31 C32 -13.2(3) . . . . ?
C21 B1 C31 C32 117.0(2) . . . . ?
N1 B1 C31 C32 -108.7(2) . . . . ?
C36 C31 C32 F32 176.6(2) . . . . ?
B1 C31 C32 F32 6.8(3) . . . . ?
C36 C31 C32 C33 -1.4(3) . . . . ?
B1 C31 C32 C33 -171.3(2) . . . . ?
F32 C32 C33 F33 1.6(3) . . . . ?
C31 C32 C33 F33 179.8(2) . . . . ?
F32 C32 C33 C34 -178.0(2) . . . . ?
C31 C32 C33 C34 0.2(4) . . . . ?
F33 C33 C34 F34 2.0(3) . . . . ?
C32 C33 C34 F34 -178.4(2) . . . . ?
F33 C33 C34 C35 -178.6(2) . . . . ?
C32 C33 C34 C35 1.0(4) . . . . ?
F34 C34 C35 F35 -1.7(3) . . . . ?
C33 C34 C35 F35 178.9(2) . . . . ?
F34 C34 C35 C36 178.5(2) . . . . ?
C33 C34 C35 C36 -0.8(4) . . . . ?
F35 C35 C36 F36 -0.4(3) . . . . ?
C34 C35 C36 F36 179.3(2) . . . . ?
F35 C35 C36 C31 179.7(2) . . . . ?
C34 C35 C36 C31 -0.6(4) . . . . ?
C32 C31 C36 F36 -178.31(19) . . . . ?
B1 C31 C36 F36 -8.0(3) . . . . ?
C32 C31 C36 C35 1.6(3) . . . . ?
B1 C31 C36 C35 171.9(2) . . . . ?
C31 B1 C21 C22 104.0(2) . . . . ?
C2 B1 C21 C22 -124.3(2) . . . . ?
N1 B1 C21 C22 -28.5(3) . . . . ?
C31 B1 C21 C26 -67.6(2) . . . . ?
C2 B1 C21 C26 64.2(2) . . . . ?
N1 B1 C21 C26 159.93(18) . . . . ?
C26 C21 C22 F22 175.66(19) . . . . ?
B1 C21 C22 F22 3.9(4) . . . . ?
C26 C21 C22 C23 -2.5(3) . . . . ?
B1 C21 C22 C23 -174.2(2) . . . . ?
F22 C22 C23 F23 1.8(3) . . . . ?
C21 C22 C23 F23 -179.9(2) . . . . ?
F22 C22 C23 C24 -177.5(2) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
F23 C23 C24 F24 0.0(3) . . . . ?
C22 C23 C24 F24 179.3(2) . . . . ?
F23 C23 C24 C25 -178.9(2) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
F24 C24 C25 F25 -0.6(3) . . . . ?
C23 C24 C25 F25 178.3(2) . . . . ?
F24 C24 C25 C26 -178.4(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
F25 C25 C26 F26 -3.5(3) . . . . ?
C24 C25 C26 F26 174.4(2) . . . . ?
F25 C25 C26 C21 179.6(2) . . . . ?
C24 C25 C26 C21 -2.6(4) . . . . ?
C22 C21 C26 F26 -173.45(19) . . . . ?
B1 C21 C26 F26 -0.1(3) . . . . ?
C22 C21 C26 C25 3.4(3) . . . . ?
B1 C21 C26 C25 176.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_erk7717
_database_code_depnum_ccdc_archive 'CCDC 1411184'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 B F10 N'
_chemical_formula_weight         563.28

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.0839(3)
_cell_length_b                   10.3125(3)
_cell_length_c                   11.7098(3)
_cell_angle_alpha                93.7870(13)
_cell_angle_beta                 92.7690(12)
_cell_angle_gamma                102.9490(12)
_cell_volume                     1181.65(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7800
_cell_measurement_theta_min      3.791
_cell_measurement_theta_max      68.274

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc.,
Madison, Wisconsin, USA.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro focus tube'
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13126
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         68.25
_reflns_number_total             4285
_reflns_number_gt                3710
_reflns_threshold_expression     >2sigma(I)

_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)'

_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)+(0.0508P)²+0.6970P] 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         4285
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.72910(19) 0.71948(18) 0.23152(16) 0.0157(4) Uani 1 1 d . . .
N1 N 0.57320(14) 0.74277(13) 0.19328(11) 0.0155(3) Uani 1 1 d . . .
C2 C 0.72205(16) 0.82325(16) 0.34215(14) 0.0168(3) Uani 1 1 d . . .
H2 H 0.7592 0.9161 0.3207 0.020 Uiso 1 1 calc R . .
C3 C 0.77762(17) 0.81251(17) 0.46041(14) 0.0190(4) Uani 1 1 d . . .
H3 H 0.8721 0.8485 0.4788 0.023 Uiso 1 1 calc R . .
C4 C 0.70287(18) 0.75556(17) 0.54175(14) 0.0195(4) Uani 1 1 d . . .
C5 C 0.55268(17) 0.69916(17) 0.51956(14) 0.0199(4) Uani 1 1 d . . .
H5A H 0.5042 0.7596 0.5608 0.024 Uiso 1 1 calc R . .
H5B H 0.5298 0.6123 0.5538 0.024 Uiso 1 1 calc R . .
C6 C 0.49562(17) 0.67728(16) 0.39313(14) 0.0174(3) Uani 1 1 d . . .
H6 H 0.5168 0.5932 0.3592 0.021 Uiso 1 1 calc R . .
C7 C 0.33943(17) 0.65562(17) 0.39231(15) 0.0206(4) Uani 1 1 d . . .
H7A H 0.2993 0.6218 0.3142 0.025 Uiso 1 1 calc R . .
H7B H 0.3043 0.5868 0.4453 0.025 Uiso 1 1 calc R . .
C8 C 0.29367(18) 0.78311(18) 0.42792(15) 0.0226(4) Uani 1 1 d . . .
H8A H 0.1928 0.7650 0.4222 0.027 Uiso 1 1 calc R . .
H8B H 0.3256 0.8125 0.5087 0.027 Uiso 1 1 calc R . .
C9 C 0.35087(18) 0.89346(18) 0.35132(15) 0.0222(4) Uani 1 1 d . . .
H9A H 0.3276 0.9774 0.3803 0.027 Uiso 1 1 calc R . .
H9B H 0.3084 0.8693 0.2725 0.027 Uiso 1 1 calc R . .
C10 C 0.50612(17) 0.91555(16) 0.34828(15) 0.0187(3) Uani 1 1 d . . .
H10A H 0.5474 0.9600 0.4233 0.022 Uiso 1 1 calc R . .
H10B H 0.5360 0.9786 0.2894 0.022 Uiso 1 1 calc R . .
C1 C 0.56543(16) 0.79282(16) 0.32352(13) 0.0153(3) Uani 1 1 d . . .
C11 C 0.75813(19) 0.74988(19) 0.66223(15) 0.0253(4) Uani 1 1 d . . .
H11A H 0.8550 0.7948 0.6701 0.038 Uiso 1 1 calc R . .
H11B H 0.7474 0.6565 0.6794 0.038 Uiso 1 1 calc R . .
H11C H 0.7080 0.7947 0.7159 0.038 Uiso 1 1 calc R . .
C12 C 0.45692(17) 0.64113(16) 0.13214(14) 0.0174(3) Uani 1 1 d . . .
H12A H 0.4119 0.5781 0.1862 0.021 Uiso 1 1 calc R . .
H12B H 0.4904 0.5898 0.0698 0.021 Uiso 1 1 calc R . .
C13 C 0.35659(18) 0.71783(17) 0.08283(15) 0.0217(4) Uani 1 1 d . . .
H13A H 0.2829 0.7207 0.1352 0.026 Uiso 1 1 calc R . .
H13B H 0.3153 0.6755 0.0072 0.026 Uiso 1 1 calc R . .
C14 C 0.44279(18) 0.85901(18) 0.07110(15) 0.0230(4) Uani 1 1 d . . .
H14A H 0.4397 0.8818 -0.0097 0.028 Uiso 1 1 calc R . .
H14B H 0.4096 0.9262 0.1192 0.028 Uiso 1 1 calc R . .
C15 C 0.58737(18) 0.85312(17) 0.11253(14) 0.0190(4) Uani 1 1 d . . .
H15A H 0.6398 0.8336 0.0467 0.023 Uiso 1 1 calc R . .
H15B H 0.6355 0.9394 0.1529 0.023 Uiso 1 1 calc R . .
C21 C 0.74850(16) 0.57070(17) 0.26288(13) 0.0164(3) Uani 1 1 d . . .
C22 C 0.87493(17) 0.57083(17) 0.31735(14) 0.0197(4) Uani 1 1 d . . .
F22 F 0.96607(10) 0.68828(10) 0.34259(9) 0.0242(2) Uani 1 1 d . . .
C23 C 0.91921(17) 0.45864(19) 0.34400(14) 0.0208(4) Uani 1 1 d . . .
F23 F 1.04450(10) 0.46927(11) 0.39327(9) 0.0282(3) Uani 1 1 d . . .
C24 C 0.83543(18) 0.33423(18) 0.31670(14) 0.0211(4) Uani 1 1 d . . .
F24 F 0.87611(11) 0.22337(11) 0.33996(9) 0.0277(3) Uani 1 1 d . . .
C25 C 0.70949(18) 0.32660(17) 0.26226(14) 0.0189(3) Uani 1 1 d . . .
F25 F 0.62553(11) 0.20660(10) 0.23191(9) 0.0250(2) Uani 1 1 d . . .
C26 C 0.66958(17) 0.44191(17) 0.23646(14) 0.0173(3) Uani 1 1 d . . .
F26 F 0.54505(10) 0.41989(9) 0.18037(9) 0.0216(2) Uani 1 1 d . . .
C31 C 0.84271(16) 0.76609(16) 0.13773(14) 0.0168(3) Uani 1 1 d . . .
C32 C 0.95800(17) 0.87023(17) 0.15744(14) 0.0181(3) Uani 1 1 d . . .
F32 F 0.97819(10) 0.95046(10) 0.25514(9) 0.0250(2) Uani 1 1 d . . .
C33 C 1.05938(17) 0.89735(17) 0.08147(15) 0.0190(4) Uani 1 1 d . . .
F33 F 1.16778(10) 1.00013(10) 0.10467(9) 0.0248(2) Uani 1 1 d . . .
C34 C 1.05073(17) 0.81849(17) -0.01959(14) 0.0194(4) Uani 1 1 d . . .
F34 F 1.14894(10) 0.84412(11) -0.09324(9) 0.0271(2) Uani 1 1 d . . .
C35 C 0.93889(18) 0.71309(17) -0.04363(14) 0.0196(4) Uani 1 1 d . . .
F35 F 0.92881(11) 0.63343(11) -0.14075(9) 0.0277(3) Uani 1 1 d . . .
C36 C 0.83881(17) 0.69094(16) 0.03395(14) 0.0182(3) Uani 1 1 d . . .
F36 F 0.73070(10) 0.58744(10) 0.00561(8) 0.0235(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C2 1.640(2) . ?
B1 C31 1.641(2) . ?
B1 C21 1.652(2) . ?
B1 N1 1.687(2) . ?
N1 C12 1.502(2) . ?
N1 C15 1.514(2) . ?
N1 C1 1.589(2) . ?
C2 C3 1.489(2) . ?
C2 C1 1.541(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.329(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.499(2) . ?
C4 C11 1.501(2) . ?
C5 C6 1.546(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.540(2) . ?
C6 C1 1.545(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.533(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C1 1.533(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.531(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.530(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 C26 1.393(2) . ?
C21 C22 1.397(2) . ?
C22 F22 1.3515(19) . ?
C22 C23 1.379(3) . ?
C23 F23 1.3417(19) . ?
C23 C24 1.377(3) . ?
C24 F24 1.338(2) . ?
C24 C25 1.377(2) . ?
C25 F25 1.3483(19) . ?
C25 C26 1.385(2) . ?
C26 F26 1.3538(19) . ?
C31 C36 1.391(2) . ?
C31 C32 1.393(2) . ?
C32 F32 1.3461(19) . ?
C32 C33 1.381(2) . ?
C33 F33 1.3439(19) . ?
C33 C34 1.379(2) . ?
C34 F34 1.338(2) . ?
C34 C35 1.383(2) . ?
C35 F35 1.3441(19) . ?
C35 C36 1.382(2) . ?
C36 F36 1.3545(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 B1 C31 118.79(13) . . ?
C2 B1 C21 115.29(13) . . ?
C31 B1 C21 104.45(13) . . ?
C2 B1 N1 84.24(11) . . ?
C31 B1 N1 113.71(13) . . ?
C21 B1 N1 120.42(13) . . ?
C12 N1 C15 100.42(12) . . ?
C12 N1 C1 120.48(12) . . ?
C15 N1 C1 113.50(12) . . ?
C12 N1 B1 126.50(12) . . ?
C15 N1 B1 109.33(12) . . ?
C1 N1 B1 86.91(11) . . ?
C3 C2 C1 116.20(14) . . ?
C3 C2 B1 124.44(14) . . ?
C1 C2 B1 90.18(12) . . ?
C3 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
B1 C2 H2 108.1 . . ?
C4 C3 C2 123.86(16) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 C4 C5 120.97(15) . . ?
C3 C4 C11 123.67(16) . . ?
C5 C4 C11 115.26(15) . . ?
C4 C5 C6 117.21(14) . . ?
C4 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C4 C5 H5B 108.0 . . ?
C6 C5 H5B 108.0 . . ?
H5A C5 H5B 107.2 . . ?
C7 C6 C1 114.43(14) . . ?
C7 C6 C5 107.80(14) . . ?
C1 C6 C5 110.95(13) . . ?
C7 C6 H6 107.8 . . ?
C1 C6 H6 107.8 . . ?
C5 C6 H6 107.8 . . ?
C8 C7 C6 112.72(14) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 110.59(14) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.34(14) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C1 117.79(14) . . ?
C9 C10 H10A 107.9 . . ?
C1 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C1 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
C10 C1 C2 113.18(13) . . ?
C10 C1 C6 110.32(13) . . ?
C2 C1 C6 111.97(13) . . ?
C10 C1 N1 117.94(13) . . ?
C2 C1 N1 90.92(11) . . ?
C6 C1 N1 111.28(12) . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 106.95(13) . . ?
N1 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
N1 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 C14 104.96(14) . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C14 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C15 C14 C13 104.54(14) . . ?
C15 C14 H14A 110.8 . . ?
C13 C14 H14A 110.8 . . ?
C15 C14 H14B 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
N1 C15 C14 106.72(13) . . ?
N1 C15 H15A 110.4 . . ?
C14 C15 H15A 110.4 . . ?
N1 C15 H15B 110.4 . . ?
C14 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C26 C21 C22 112.16(15) . . ?
C26 C21 B1 133.04(14) . . ?
C22 C21 B1 114.46(14) . . ?
F22 C22 C23 115.57(15) . . ?
F22 C22 C21 119.08(15) . . ?
C23 C22 C21 125.28(16) . . ?
F23 C23 C24 119.66(16) . . ?
F23 C23 C22 120.69(16) . . ?
C24 C23 C22 119.62(16) . . ?
F24 C24 C25 120.69(16) . . ?
F24 C24 C23 121.08(16) . . ?
C25 C24 C23 118.22(16) . . ?
F25 C25 C24 120.07(15) . . ?
F25 C25 C26 119.72(15) . . ?
C24 C25 C26 120.20(16) . . ?
F26 C26 C25 114.05(14) . . ?
F26 C26 C21 121.44(14) . . ?
C25 C26 C21 124.51(16) . . ?
C36 C31 C32 113.74(15) . . ?
C36 C31 B1 120.75(14) . . ?
C32 C31 B1 125.05(14) . . ?
F32 C32 C33 115.52(15) . . ?
F32 C32 C31 120.96(15) . . ?
C33 C32 C31 123.51(15) . . ?
F33 C33 C34 118.99(15) . . ?
F33 C33 C32 120.85(15) . . ?
C34 C33 C32 120.16(15) . . ?
F34 C34 C33 120.36(15) . . ?
F34 C34 C35 120.68(15) . . ?
C33 C34 C35 118.96(15) . . ?
F35 C35 C36 120.87(15) . . ?
F35 C35 C34 120.21(15) . . ?
C36 C35 C34 118.92(15) . . ?
F36 C36 C35 116.54(15) . . ?
F36 C36 C31 118.77(15) . . ?
C35 C36 C31 124.68(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 B1 N1 C12 -146.23(15) . . . . ?
C31 B1 N1 C12 94.80(17) . . . . ?
C21 B1 N1 C12 -30.2(2) . . . . ?
C2 B1 N1 C15 93.90(13) . . . . ?
C31 B1 N1 C15 -25.06(17) . . . . ?
C21 B1 N1 C15 -150.08(14) . . . . ?
C2 B1 N1 C1 -19.94(11) . . . . ?
C31 B1 N1 C1 -138.91(13) . . . . ?
C21 B1 N1 C1 96.08(15) . . . . ?
C31 B1 C2 C3 -103.00(19) . . . . ?
C21 B1 C2 C3 22.1(2) . . . . ?
N1 B1 C2 C3 143.07(16) . . . . ?
C31 B1 C2 C1 134.48(15) . . . . ?
C21 B1 C2 C1 -100.46(15) . . . . ?
N1 B1 C2 C1 20.55(11) . . . . ?
C1 C2 C3 C4 13.2(2) . . . . ?
B1 C2 C3 C4 -96.8(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C11 -177.41(15) . . . . ?
C3 C4 C5 C6 15.1(2) . . . . ?
C11 C4 C5 C6 -168.40(15) . . . . ?
C4 C5 C6 C7 -165.18(14) . . . . ?
C4 C5 C6 C1 -39.2(2) . . . . ?
C1 C6 C7 C8 -52.73(19) . . . . ?
C5 C6 C7 C8 71.21(18) . . . . ?
C6 C7 C8 C9 56.36(19) . . . . ?
C7 C8 C9 C10 -53.65(19) . . . . ?
C8 C9 C10 C1 49.9(2) . . . . ?
C9 C10 C1 C2 -170.49(14) . . . . ?
C9 C10 C1 C6 -44.15(19) . . . . ?
C9 C10 C1 N1 85.22(18) . . . . ?
C3 C2 C1 C10 87.94(17) . . . . ?
B1 C2 C1 C10 -142.87(14) . . . . ?
C3 C2 C1 C6 -37.51(19) . . . . ?
B1 C2 C1 C6 91.68(14) . . . . ?
C3 C2 C1 N1 -150.96(14) . . . . ?
B1 C2 C1 N1 -21.76(12) . . . . ?
C7 C6 C1 C10 44.44(18) . . . . ?
C5 C6 C1 C10 -77.80(17) . . . . ?
C7 C6 C1 C2 171.45(13) . . . . ?
C5 C6 C1 C2 49.21(18) . . . . ?
C7 C6 C1 N1 -88.43(16) . . . . ?
C5 C6 C1 N1 149.33(13) . . . . ?
C12 N1 C1 C10 -90.59(17) . . . . ?
C15 N1 C1 C10 28.41(19) . . . . ?
B1 N1 C1 C10 138.16(14) . . . . ?
C12 N1 C1 C2 152.41(13) . . . . ?
C15 N1 C1 C2 -88.60(14) . . . . ?
B1 N1 C1 C2 21.16(11) . . . . ?
C12 N1 C1 C6 38.34(18) . . . . ?
C15 N1 C1 C6 157.34(13) . . . . ?
B1 N1 C1 C6 -92.91(13) . . . . ?
C15 N1 C12 C13 -38.49(16) . . . . ?
C1 N1 C12 C13 86.86(17) . . . . ?
B1 N1 C12 C13 -162.18(14) . . . . ?
N1 C12 C13 C14 23.82(17) . . . . ?
C12 C13 C14 C15 0.96(18) . . . . ?
C12 N1 C15 C14 39.16(16) . . . . ?
C1 N1 C15 C14 -90.80(15) . . . . ?
B1 N1 C15 C14 174.02(12) . . . . ?
C13 C14 C15 N1 -25.21(17) . . . . ?
C2 B1 C21 C26 119.60(19) . . . . ?
C31 B1 C21 C26 -108.20(19) . . . . ?
N1 B1 C21 C26 21.0(3) . . . . ?
C2 B1 C21 C22 -67.76(19) . . . . ?
C31 B1 C21 C22 64.44(17) . . . . ?
N1 B1 C21 C22 -166.31(14) . . . . ?
C26 C21 C22 F22 176.32(14) . . . . ?
B1 C21 C22 F22 2.1(2) . . . . ?
C26 C21 C22 C23 -0.5(2) . . . . ?
B1 C21 C22 C23 -174.73(16) . . . . ?
F22 C22 C23 F23 0.9(2) . . . . ?
C21 C22 C23 F23 177.88(15) . . . . ?
F22 C22 C23 C24 -177.15(14) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
F23 C23 C24 F24 1.0(2) . . . . ?
C22 C23 C24 F24 179.06(15) . . . . ?
F23 C23 C24 C25 -177.56(14) . . . . ?
C22 C23 C24 C25 0.5(2) . . . . ?
F24 C24 C25 F25 0.1(2) . . . . ?
C23 C24 C25 F25 178.62(15) . . . . ?
F24 C24 C25 C26 -178.65(15) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
F25 C25 C26 F26 -0.4(2) . . . . ?
C24 C25 C26 F26 178.37(14) . . . . ?
F25 C25 C26 C21 -179.44(15) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C22 C21 C26 F26 -178.03(14) . . . . ?
B1 C21 C26 F26 -5.3(3) . . . . ?
C22 C21 C26 C25 1.0(2) . . . . ?
B1 C21 C26 C25 173.75(16) . . . . ?
C2 B1 C31 C36 -169.85(15) . . . . ?
C21 B1 C31 C36 59.99(19) . . . . ?
N1 B1 C31 C36 -73.17(19) . . . . ?
C2 B1 C31 C32 18.3(2) . . . . ?
C21 B1 C31 C32 -111.84(17) . . . . ?
N1 B1 C31 C32 114.99(17) . . . . ?
C36 C31 C32 F32 -178.63(15) . . . . ?
B1 C31 C32 F32 -6.3(3) . . . . ?
C36 C31 C32 C33 0.1(2) . . . . ?
B1 C31 C32 C33 172.48(16) . . . . ?
F32 C32 C33 F33 -1.8(2) . . . . ?
C31 C32 C33 F33 179.36(15) . . . . ?
F32 C32 C33 C34 177.97(14) . . . . ?
C31 C32 C33 C34 -0.9(3) . . . . ?
F33 C33 C34 F34 0.0(2) . . . . ?
C32 C33 C34 F34 -179.77(15) . . . . ?
F33 C33 C34 C35 -179.73(15) . . . . ?
C32 C33 C34 C35 0.5(2) . . . . ?
F34 C34 C35 F35 1.2(2) . . . . ?
C33 C34 C35 F35 -179.05(15) . . . . ?
F34 C34 C35 C36 -179.18(15) . . . . ?
C33 C34 C35 C36 0.6(2) . . . . ?
F35 C35 C36 F36 -1.2(2) . . . . ?
C34 C35 C36 F36 179.22(15) . . . . ?
F35 C35 C36 C31 178.24(15) . . . . ?
C34 C35 C36 C31 -1.4(3) . . . . ?
C32 C31 C36 F36 -179.61(14) . . . . ?
B1 C31 C36 F36 7.7(2) . . . . ?
C32 C31 C36 C35 1.0(2) . . . . ?
B1 C31 C36 C35 -171.72(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_erk7724
_database_code_depnum_ccdc_archive 'CCDC 1411185'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 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 H26 B F10 N'
_chemical_formula_weight         577.31

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.0475(2)
_cell_length_b                   10.2558(2)
_cell_length_c                   14.7499(5)
_cell_angle_alpha                84.788(1)
_cell_angle_beta                 79.791(1)
_cell_angle_gamma                76.629(2)
_cell_volume                     1308.68(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3171
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9946
_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            11743
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4426
_reflns_number_gt                3246
_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)+(0.0212P)²+2.3843P] 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         4426
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.4681(3) 0.7424(3) 0.25953(19) 0.0326(7) Uani 1 1 d . . .
C1 C 0.4668(4) 0.7868(3) 0.1537(2) 0.0315(8) Uani 1 1 d . . .
C2 C 0.2925(4) 0.8050(3) 0.1653(2) 0.0330(8) Uani 1 1 d . . .
H2 H 0.2461 0.8978 0.1840 0.040 Uiso 1 1 calc R . .
C3 C 0.2298(4) 0.7858(4) 0.0823(2) 0.0372(9) Uani 1 1 d . . .
H3 H 0.1225 0.8106 0.0843 0.045 Uiso 1 1 calc R . .
C4 C 0.3156(5) 0.7358(4) 0.0053(3) 0.0389(9) Uani 1 1 d . . .
C5 C 0.4866(4) 0.6930(4) -0.0023(3) 0.0425(9) Uani 1 1 d . . .
H5A H 0.5325 0.7602 -0.0419 0.051 Uiso 1 1 calc R . .
H5B H 0.5203 0.6083 -0.0335 0.051 Uiso 1 1 calc R . .
C6 C 0.5520(4) 0.6733(4) 0.0891(2) 0.0373(9) Uani 1 1 d . . .
H6 H 0.5331 0.5875 0.1199 0.045 Uiso 1 1 calc R . .
C7 C 0.7277(5) 0.6592(4) 0.0644(3) 0.0478(10) Uani 1 1 d . . .
H7A H 0.7751 0.6210 0.1185 0.057 Uiso 1 1 calc R . .
H7B H 0.7679 0.5962 0.0152 0.057 Uiso 1 1 calc R . .
C8 C 0.7747(5) 0.7920(5) 0.0330(3) 0.0556(12) Uani 1 1 d . . .
H8A H 0.8868 0.7785 0.0266 0.067 Uiso 1 1 calc R . .
H8B H 0.7451 0.8220 -0.0275 0.067 Uiso 1 1 calc R . .
C9 C 0.6993(5) 0.8988(5) 0.1009(3) 0.0577(12) Uani 1 1 d . . .
H9A H 0.7242 0.9846 0.0763 0.069 Uiso 1 1 calc R . .
H9B H 0.7399 0.8747 0.1589 0.069 Uiso 1 1 calc R . .
C10 C 0.5239(4) 0.9146(4) 0.1196(3) 0.0409(9) Uani 1 1 d . . .
H10A H 0.4802 0.9821 0.1656 0.049 Uiso 1 1 calc R . .
H10B H 0.4837 0.9493 0.0626 0.049 Uiso 1 1 calc R . .
C11 C 0.2505(5) 0.7255(4) -0.0806(3) 0.0520(11) Uani 1 1 d . . .
H11A H 0.1399 0.7600 -0.0697 0.078 Uiso 1 1 calc R . .
H11B H 0.2726 0.6322 -0.0961 0.078 Uiso 1 1 calc R . .
H11C H 0.2970 0.7775 -0.1313 0.078 Uiso 1 1 calc R . .
C12 C 0.6127(4) 0.6493(4) 0.2806(3) 0.0380(9) Uani 1 1 d . . .
H12A H 0.6993 0.6924 0.2585 0.046 Uiso 1 1 calc R . .
H12B H 0.6300 0.5679 0.2466 0.046 Uiso 1 1 calc R . .
C13 C 0.6109(5) 0.6096(4) 0.3819(3) 0.0493(10) Uani 1 1 d . . .
H13A H 0.7069 0.5455 0.3904 0.059 Uiso 1 1 calc R . .
H13B H 0.5251 0.5657 0.4049 0.059 Uiso 1 1 calc R . .
C14 C 0.5939(5) 0.7323(5) 0.4362(3) 0.0576(12) Uani 1 1 d . . .
H14A H 0.6845 0.7714 0.4179 0.069 Uiso 1 1 calc R . .
H14B H 0.5851 0.7070 0.5023 0.069 Uiso 1 1 calc R . .
C15 C 0.4499(5) 0.8344(4) 0.4169(3) 0.0471(10) Uani 1 1 d . . .
H15A H 0.3587 0.7996 0.4441 0.056 Uiso 1 1 calc R . .
H15B H 0.4440 0.9177 0.4464 0.056 Uiso 1 1 calc R . .
C16 C 0.4489(5) 0.8649(4) 0.3142(2) 0.0402(9) Uani 1 1 d . . .
H16A H 0.3514 0.9266 0.3057 0.048 Uiso 1 1 calc R . .
H16B H 0.5321 0.9110 0.2891 0.048 Uiso 1 1 calc R . .
B1 B 0.2901(4) 0.7064(4) 0.2595(3) 0.0299(9) Uani 1 1 d . . .
C21 C 0.2773(4) 0.5524(3) 0.2438(2) 0.0334(8) Uani 1 1 d . . .
F22 F 0.5070(3) 0.4150(2) 0.28732(17) 0.0537(6) Uani 1 1 d . . .
C22 C 0.3710(4) 0.4281(4) 0.2575(3) 0.0376(9) Uani 1 1 d . . .
F23 F 0.4340(3) 0.1908(2) 0.26340(18) 0.0611(7) Uani 1 1 d . . .
C23 C 0.3357(5) 0.3069(4) 0.2471(3) 0.0432(10) Uani 1 1 d . . .
F24 F 0.1606(3) 0.1887(2) 0.21173(18) 0.0681(8) Uani 1 1 d . . .
C24 C 0.1977(5) 0.3056(4) 0.2217(3) 0.0460(10) Uani 1 1 d . . .
F25 F -0.0407(3) 0.4257(3) 0.1864(2) 0.0719(8) Uani 1 1 d . . .
C25 C 0.0978(5) 0.4250(4) 0.2075(3) 0.0453(10) Uani 1 1 d . . .
F26 F 0.0275(2) 0.6561(2) 0.21026(16) 0.0480(6) Uani 1 1 d . . .
C26 C 0.1375(4) 0.5436(4) 0.2188(2) 0.0359(8) Uani 1 1 d . . .
C31 C 0.1601(4) 0.7546(3) 0.3500(2) 0.0328(8) Uani 1 1 d . . .
F32 F 0.2536(3) 0.5567(2) 0.43799(15) 0.0579(7) Uani 1 1 d . . .
C32 C 0.1487(4) 0.6728(4) 0.4312(3) 0.0393(9) Uani 1 1 d . . .
F33 F 0.0337(3) 0.6177(3) 0.58182(17) 0.0819(10) Uani 1 1 d . . .
C33 C 0.0357(5) 0.7034(5) 0.5068(3) 0.0492(11) Uani 1 1 d . . .
F34 F -0.1838(3) 0.8515(3) 0.57859(17) 0.0705(8) Uani 1 1 d . . .
C34 C -0.0741(5) 0.8199(4) 0.5059(3) 0.0463(10) Uani 1 1 d . . .
F35 F -0.1791(3) 1.0156(3) 0.4245(2) 0.0756(9) Uani 1 1 d . . .
C35 C -0.0697(5) 0.9027(4) 0.4280(3) 0.0448(10) Uani 1 1 d . . .
F36 F 0.0313(3) 0.9560(2) 0.27919(18) 0.0676(8) Uani 1 1 d . . .
C36 C 0.0439(4) 0.8690(4) 0.3529(3) 0.0395(9) 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 C12 1.494(4) . ?
N1 C16 1.514(4) . ?
N1 C1 1.588(4) . ?
N1 B1 1.733(5) . ?
C1 C2 1.525(5) . ?
C1 C10 1.529(4) . ?
C1 C6 1.543(5) . ?
C2 C3 1.483(5) . ?
C2 B1 1.643(5) . ?
C2 H2 0.9900 . ?
C3 C4 1.329(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.494(5) . ?
C4 C11 1.511(5) . ?
C5 C6 1.545(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.542(5) . ?
C6 H6 0.9900 . ?
C7 C8 1.528(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.510(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.535(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.511(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.516(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.524(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.520(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
B1 C31 1.644(5) . ?
B1 C21 1.650(5) . ?
C21 C22 1.378(5) . ?
C21 C26 1.403(5) . ?
F22 C22 1.353(4) . ?
C22 C23 1.380(5) . ?
F23 C23 1.342(4) . ?
C23 C24 1.369(6) . ?
F24 C24 1.345(4) . ?
C24 C25 1.367(6) . ?
F25 C25 1.342(5) . ?
C25 C26 1.377(5) . ?
F26 C26 1.351(4) . ?
C31 C36 1.381(5) . ?
C31 C32 1.401(5) . ?
F32 C32 1.348(4) . ?
C32 C33 1.377(5) . ?
F33 C33 1.350(4) . ?
C33 C34 1.366(6) . ?
F34 C34 1.334(4) . ?
C34 C35 1.366(6) . ?
F35 C35 1.342(5) . ?
C35 C36 1.379(5) . ?
F36 C36 1.346(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C16 105.8(3) . . ?
C12 N1 C1 115.2(3) . . ?
C16 N1 C1 109.6(2) . . ?
C12 N1 B1 128.4(3) . . ?
C16 N1 B1 109.9(3) . . ?
C1 N1 B1 86.2(2) . . ?
C2 C1 C10 113.9(3) . . ?
C2 C1 C6 112.0(3) . . ?
C10 C1 C6 109.0(3) . . ?
C2 C1 N1 92.0(2) . . ?
C10 C1 N1 116.4(3) . . ?
C6 C1 N1 112.7(3) . . ?
C3 C2 C1 116.2(3) . . ?
C3 C2 B1 125.2(3) . . ?
C1 C2 B1 91.6(3) . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
B1 C2 H2 107.4 . . ?
C4 C3 C2 124.1(3) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 C11 123.2(4) . . ?
C5 C4 C11 115.9(3) . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
C7 C6 C1 115.4(3) . . ?
C7 C6 C5 107.5(3) . . ?
C1 C6 C5 110.3(3) . . ?
C7 C6 H6 107.8 . . ?
C1 C6 H6 107.8 . . ?
C5 C6 H6 107.8 . . ?
C8 C7 C6 113.4(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 111.3(3) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 111.1(4) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C1 C10 C9 115.6(3) . . ?
C1 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C1 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 114.0(3) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 110.3(3) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 108.7(3) . . ?
C13 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 C14 112.2(3) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N1 C16 C15 114.3(3) . . ?
N1 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
N1 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C2 B1 C31 118.7(3) . . ?
C2 B1 C21 114.0(3) . . ?
C31 B1 C21 105.3(3) . . ?
C2 B1 N1 83.1(2) . . ?
C31 B1 N1 115.0(3) . . ?
C21 B1 N1 120.3(3) . . ?
C22 C21 C26 112.4(3) . . ?
C22 C21 B1 133.0(3) . . ?
C26 C21 B1 114.3(3) . . ?
F22 C22 C21 121.4(3) . . ?
F22 C22 C23 113.5(3) . . ?
C21 C22 C23 125.1(4) . . ?
F23 C23 C24 119.9(3) . . ?
F23 C23 C22 120.6(4) . . ?
C24 C23 C22 119.5(4) . . ?
F24 C24 C25 120.6(4) . . ?
F24 C24 C23 120.5(4) . . ?
C25 C24 C23 118.9(3) . . ?
F25 C25 C24 119.8(3) . . ?
F25 C25 C26 120.4(4) . . ?
C24 C25 C26 119.7(4) . . ?
F26 C26 C25 115.7(3) . . ?
F26 C26 C21 119.8(3) . . ?
C25 C26 C21 124.4(4) . . ?
C36 C31 C32 112.8(3) . . ?
C36 C31 B1 125.6(3) . . ?
C32 C31 B1 121.4(3) . . ?
F32 C32 C33 116.5(3) . . ?
F32 C32 C31 119.4(3) . . ?
C33 C32 C31 124.0(4) . . ?
F33 C33 C34 120.1(4) . . ?
F33 C33 C32 119.7(4) . . ?
C34 C33 C32 120.2(4) . . ?
F34 C34 C35 120.7(4) . . ?
F34 C34 C33 121.1(4) . . ?
C35 C34 C33 118.2(3) . . ?
F35 C35 C34 119.2(4) . . ?
F35 C35 C36 120.4(4) . . ?
C34 C35 C36 120.3(4) . . ?
F36 C36 C35 114.4(3) . . ?
F36 C36 C31 121.1(3) . . ?
C35 C36 C31 124.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 151.2(3) . . . . ?
C16 N1 C1 C2 -89.7(3) . . . . ?
B1 N1 C1 C2 20.1(2) . . . . ?
C12 N1 C1 C10 -90.8(4) . . . . ?
C16 N1 C1 C10 28.3(4) . . . . ?
B1 N1 C1 C10 138.1(3) . . . . ?
C12 N1 C1 C6 36.3(4) . . . . ?
C16 N1 C1 C6 155.3(3) . . . . ?
B1 N1 C1 C6 -94.9(3) . . . . ?
C10 C1 C2 C3 87.7(4) . . . . ?
C6 C1 C2 C3 -36.6(4) . . . . ?
N1 C1 C2 C3 -152.2(3) . . . . ?
C10 C1 C2 B1 -141.3(3) . . . . ?
C6 C1 C2 B1 94.4(3) . . . . ?
N1 C1 C2 B1 -21.2(3) . . . . ?
C1 C2 C3 C4 10.2(5) . . . . ?
B1 C2 C3 C4 -102.3(4) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C3 C4 C11 -175.9(3) . . . . ?
C3 C4 C5 C6 16.1(5) . . . . ?
C11 C4 C5 C6 -167.1(3) . . . . ?
C2 C1 C6 C7 173.1(3) . . . . ?
C10 C1 C6 C7 46.1(4) . . . . ?
N1 C1 C6 C7 -84.7(4) . . . . ?
C2 C1 C6 C5 51.0(4) . . . . ?
C10 C1 C6 C5 -75.9(4) . . . . ?
N1 C1 C6 C5 153.2(3) . . . . ?
C4 C5 C6 C7 -168.3(3) . . . . ?
C4 C5 C6 C1 -41.7(4) . . . . ?
C1 C6 C7 C8 -48.6(4) . . . . ?
C5 C6 C7 C8 75.0(4) . . . . ?
C6 C7 C8 C9 51.4(5) . . . . ?
C7 C8 C9 C10 -54.0(5) . . . . ?
C2 C1 C10 C9 -176.2(3) . . . . ?
C6 C1 C10 C9 -50.3(4) . . . . ?
N1 C1 C10 C9 78.6(4) . . . . ?
C8 C9 C10 C1 56.0(5) . . . . ?
C16 N1 C12 C13 58.4(4) . . . . ?
C1 N1 C12 C13 179.6(3) . . . . ?
B1 N1 C12 C13 -74.1(4) . . . . ?
N1 C12 C13 C14 -61.9(4) . . . . ?
C12 C13 C14 C15 55.4(4) . . . . ?
C13 C14 C15 C16 -52.9(5) . . . . ?
C12 N1 C16 C15 -54.7(4) . . . . ?
C1 N1 C16 C15 -179.5(3) . . . . ?
B1 N1 C16 C15 87.4(4) . . . . ?
C14 C15 C16 N1 55.0(4) . . . . ?
C3 C2 B1 C31 -101.7(4) . . . . ?
C1 C2 B1 C31 134.3(3) . . . . ?
C3 C2 B1 C21 23.4(5) . . . . ?
C1 C2 B1 C21 -100.6(3) . . . . ?
C3 C2 B1 N1 143.5(3) . . . . ?
C1 C2 B1 N1 19.5(2) . . . . ?
C12 N1 B1 C2 -138.3(3) . . . . ?
C16 N1 B1 C2 90.7(3) . . . . ?
C1 N1 B1 C2 -18.7(2) . . . . ?
C12 N1 B1 C31 103.2(4) . . . . ?
C16 N1 B1 C31 -27.8(4) . . . . ?
C1 N1 B1 C31 -137.3(3) . . . . ?
C12 N1 B1 C21 -24.4(5) . . . . ?
C16 N1 B1 C21 -155.4(3) . . . . ?
C1 N1 B1 C21 95.1(3) . . . . ?
C2 B1 C21 C22 120.2(4) . . . . ?
C31 B1 C21 C22 -107.9(4) . . . . ?
N1 B1 C21 C22 24.0(5) . . . . ?
C2 B1 C21 C26 -66.3(4) . . . . ?
C31 B1 C21 C26 65.7(4) . . . . ?
N1 B1 C21 C26 -162.4(3) . . . . ?
C26 C21 C22 F22 -176.0(3) . . . . ?
B1 C21 C22 F22 -2.3(6) . . . . ?
C26 C21 C22 C23 0.9(5) . . . . ?
B1 C21 C22 C23 174.6(4) . . . . ?
F22 C22 C23 F23 -1.9(5) . . . . ?
C21 C22 C23 F23 -179.0(3) . . . . ?
F22 C22 C23 C24 176.8(3) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
F23 C23 C24 F24 -0.9(6) . . . . ?
C22 C23 C24 F24 -179.6(3) . . . . ?
F23 C23 C24 C25 178.5(3) . . . . ?
C22 C23 C24 C25 -0.3(6) . . . . ?
F24 C24 C25 F25 2.2(6) . . . . ?
C23 C24 C25 F25 -177.1(4) . . . . ?
F24 C24 C25 C26 179.5(3) . . . . ?
C23 C24 C25 C26 0.1(6) . . . . ?
F25 C25 C26 F26 2.1(5) . . . . ?
C24 C25 C26 F26 -175.2(3) . . . . ?
F25 C25 C26 C21 177.8(3) . . . . ?
C24 C25 C26 C21 0.5(6) . . . . ?
C22 C21 C26 F26 174.6(3) . . . . ?
B1 C21 C26 F26 -0.4(5) . . . . ?
C22 C21 C26 C25 -1.0(5) . . . . ?
B1 C21 C26 C25 -176.0(3) . . . . ?
C2 B1 C31 C36 4.1(5) . . . . ?
C21 B1 C31 C36 -125.1(4) . . . . ?
N1 B1 C31 C36 100.1(4) . . . . ?
C2 B1 C31 C32 177.7(3) . . . . ?
C21 B1 C31 C32 48.5(4) . . . . ?
N1 B1 C31 C32 -86.3(4) . . . . ?
C36 C31 C32 F32 179.3(3) . . . . ?
B1 C31 C32 F32 5.0(5) . . . . ?
C36 C31 C32 C33 -0.9(6) . . . . ?
B1 C31 C32 C33 -175.3(4) . . . . ?
F32 C32 C33 F33 -0.7(6) . . . . ?
C31 C32 C33 F33 179.5(4) . . . . ?
F32 C32 C33 C34 179.3(4) . . . . ?
C31 C32 C33 C34 -0.4(7) . . . . ?
F33 C33 C34 F34 0.4(6) . . . . ?
C32 C33 C34 F34 -179.6(4) . . . . ?
F33 C33 C34 C35 -178.8(4) . . . . ?
C32 C33 C34 C35 1.2(6) . . . . ?
F34 C34 C35 F35 -1.3(6) . . . . ?
C33 C34 C35 F35 178.0(4) . . . . ?
F34 C34 C35 C36 -179.7(4) . . . . ?
C33 C34 C35 C36 -0.5(6) . . . . ?
F35 C35 C36 F36 -1.2(6) . . . . ?
C34 C35 C36 F36 177.2(4) . . . . ?
F35 C35 C36 C31 -179.4(4) . . . . ?
C34 C35 C36 C31 -1.0(6) . . . . ?
C32 C31 C36 F36 -176.5(3) . . . . ?
B1 C31 C36 F36 -2.4(6) . . . . ?
C32 C31 C36 C35 1.6(5) . . . . ?
B1 C31 C36 C35 175.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_erk7890
_database_code_depnum_ccdc_archive 'CCDC 1411186'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 B F10 N'
_chemical_formula_weight         587.30

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                   8.3829(2)
_cell_length_b                   18.0928(5)
_cell_length_c                   18.0057(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8140(10)
_cell_angle_gamma                90.00
_cell_volume                     2716.88(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4998
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9845
_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            15978
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4665
_reflns_number_gt                3183
_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 C=CH2(Me) 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)+(0.0185P)²+3.9763P] 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         4665
_refine_ls_number_parameters     402
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.130
_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
N11 N 0.5537(4) 0.71263(16) 0.15079(17) 0.0416(7) Uani 1 1 d . . .
C4 C 0.0858(4) 0.7754(2) 0.1246(2) 0.0409(9) Uani 1 1 d D . .
H4 H 0.0554 0.8208 0.1444 0.049 Uiso 1 1 calc R A 1
C5 C 0.047(2) 0.7663(10) 0.0437(6) 0.037(3) Uani 0.59(6) 1 d PDU B 1
C6 C -0.019(2) 0.8194(13) 0.0011(7) 0.049(3) Uani 0.59(6) 1 d PDU B 1
H6A H -0.0433 0.8651 0.0223 0.058 Uiso 0.59(6) 1 calc PR B 1
H6B H -0.0426 0.8117 -0.0504 0.058 Uiso 0.59(6) 1 calc PR B 1
C7 C 0.085(2) 0.6920(11) 0.0122(8) 0.051(4) Uani 0.59(6) 1 d PDU B 1
H7A H 0.0463 0.6903 -0.0404 0.076 Uiso 0.59(6) 1 calc PR B 1
H7B H 0.0333 0.6535 0.0386 0.076 Uiso 0.59(6) 1 calc PR B 1
H7C H 0.2002 0.6843 0.0181 0.076 Uiso 0.59(6) 1 calc PR B 1
C5A C 0.031(4) 0.7512(14) 0.0473(8) 0.038(5) Uani 0.41(6) 1 d PDU B 2
C6A C -0.047(3) 0.7983(17) 0.0003(10) 0.047(5) Uani 0.41(6) 1 d PDU B 2
H601 H -0.0675 0.8467 0.0159 0.057 Uiso 0.41(6) 1 calc PR B 2
H602 H -0.0824 0.7833 -0.0486 0.057 Uiso 0.41(6) 1 calc PR B 2
C7A C 0.058(3) 0.6740(15) 0.0207(14) 0.062(6) Uani 0.41(6) 1 d PDU B 2
H701 H 0.0107 0.6687 -0.0304 0.093 Uiso 0.41(6) 1 calc PR B 2
H702 H 0.0088 0.6390 0.0522 0.093 Uiso 0.41(6) 1 calc PR B 2
H703 H 0.1723 0.6644 0.0232 0.093 Uiso 0.41(6) 1 calc PR B 2
C3 C 0.1581(4) 0.7282(2) 0.17380(19) 0.0384(9) Uani 1 1 d . B .
H3 H 0.1714 0.6800 0.1558 0.046 Uiso 1 1 calc R . .
C2 C 0.4235(4) 0.7596(2) 0.2568(2) 0.0393(9) Uani 1 1 d . B .
H2A H 0.4344 0.8075 0.2324 0.047 Uiso 1 1 calc R . .
H2B H 0.4737 0.7639 0.3082 0.047 Uiso 1 1 calc R . .
C1 C 0.5119(4) 0.70397(19) 0.2178(2) 0.0382(9) Uani 1 1 d . . .
C12 C 0.6581(5) 0.6606(2) 0.1144(2) 0.0545(11) Uani 1 1 d . . .
H12A H 0.7001 0.6234 0.1509 0.065 Uiso 1 1 calc R . .
H12B H 0.7495 0.6878 0.0981 0.065 Uiso 1 1 calc R . .
C13 C 0.5704(7) 0.6217(3) 0.0474(3) 0.0827(17) Uani 1 1 d . . .
H13A H 0.4861 0.5908 0.0639 0.124 Uiso 1 1 calc R . .
H13B H 0.6453 0.5912 0.0234 0.124 Uiso 1 1 calc R . .
H13C H 0.5237 0.6582 0.0123 0.124 Uiso 1 1 calc R . .
C14 C 0.5187(5) 0.7812(2) 0.1077(2) 0.0465(10) Uani 1 1 d . . .
H14A H 0.4157 0.8013 0.1196 0.056 Uiso 1 1 calc R . .
H14B H 0.5091 0.7697 0.0542 0.056 Uiso 1 1 calc R . .
C15 C 0.6475(5) 0.8388(2) 0.1243(3) 0.0585(12) Uani 1 1 d . . .
H15A H 0.6522 0.8530 0.1765 0.088 Uiso 1 1 calc R . .
H15B H 0.6228 0.8819 0.0931 0.088 Uiso 1 1 calc R . .
H15C H 0.7502 0.8187 0.1141 0.088 Uiso 1 1 calc R . .
C21 C 0.5500(4) 0.6337(2) 0.2586(2) 0.0414(9) Uani 1 1 d . . .
C22 C 0.6471(5) 0.6347(2) 0.3262(2) 0.0502(10) Uani 1 1 d . . .
H22 H 0.6915 0.6796 0.3447 0.060 Uiso 1 1 calc R . .
C23 C 0.6782(5) 0.5708(3) 0.3656(3) 0.0652(13) Uani 1 1 d . . .
H23 H 0.7446 0.5720 0.4109 0.078 Uiso 1 1 calc R . .
C24 C 0.6133(6) 0.5046(3) 0.3396(3) 0.0685(13) Uani 1 1 d . . .
H24 H 0.6363 0.4608 0.3667 0.082 Uiso 1 1 calc R . .
C25 C 0.5149(6) 0.5031(2) 0.2740(3) 0.0629(13) Uani 1 1 d . . .
H25 H 0.4681 0.4582 0.2568 0.075 Uiso 1 1 calc R . .
C26 C 0.4838(5) 0.5672(2) 0.2328(2) 0.0512(10) Uani 1 1 d . . .
H26 H 0.4178 0.5656 0.1874 0.061 Uiso 1 1 calc R . .
B1 B 0.2258(5) 0.7417(2) 0.2593(2) 0.0356(9) Uani 1 1 d . . .
C31 C 0.1376(4) 0.81236(19) 0.29620(19) 0.0369(8) Uani 1 1 d . B .
F32 F 0.3682(3) 0.88268(12) 0.34024(14) 0.0606(7) Uani 1 1 d . B .
C32 C 0.2059(5) 0.8747(2) 0.3307(2) 0.0417(9) Uani 1 1 d . . .
F33 F 0.1990(3) 0.99046(13) 0.39129(16) 0.0759(8) Uani 1 1 d . . .
C33 C 0.1222(5) 0.9320(2) 0.3587(2) 0.0484(10) Uani 1 1 d . B .
F34 F -0.1259(3) 0.98258(13) 0.38489(15) 0.0729(8) Uani 1 1 d . B .
C34 C -0.0417(5) 0.9285(2) 0.3556(2) 0.0497(10) Uani 1 1 d . . .
F35 F -0.2779(3) 0.86158(14) 0.32375(14) 0.0664(7) Uani 1 1 d . . .
C35 C -0.1185(5) 0.8680(2) 0.3246(2) 0.0459(10) Uani 1 1 d . B .
F36 F -0.1140(2) 0.75367(12) 0.26649(12) 0.0513(6) Uani 1 1 d . B .
C36 C -0.0298(4) 0.8127(2) 0.29546(19) 0.0404(9) Uani 1 1 d . . .
C41 C 0.2007(4) 0.66954(19) 0.31307(19) 0.0368(8) Uani 1 1 d . B .
F42 F 0.0224(3) 0.60233(13) 0.22629(12) 0.0605(7) Uani 1 1 d . B .
C42 C 0.1097(4) 0.6068(2) 0.2943(2) 0.0410(9) Uani 1 1 d . . .
F43 F 0.0087(3) 0.48721(12) 0.31576(14) 0.0682(7) Uani 1 1 d . . .
C43 C 0.0970(5) 0.54608(19) 0.3393(2) 0.0455(10) Uani 1 1 d . B .
F44 F 0.1682(3) 0.48729(12) 0.45459(14) 0.0713(8) Uani 1 1 d . B .
C44 C 0.1791(5) 0.5456(2) 0.4092(2) 0.0497(10) Uani 1 1 d . . .
F45 F 0.3491(3) 0.60590(14) 0.50100(13) 0.0738(8) Uani 1 1 d . . .
C45 C 0.2689(5) 0.6054(2) 0.4322(2) 0.0479(10) Uani 1 1 d . B .
F46 F 0.3653(3) 0.72324(12) 0.41402(12) 0.0559(6) Uani 1 1 d . B .
C46 C 0.2767(4) 0.66483(19) 0.3857(2) 0.0400(9) 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
N11 C1 1.299(4) . ?
N11 C14 1.477(4) . ?
N11 C12 1.483(5) . ?
C4 C3 1.331(5) . ?
C4 C5 1.469(9) . ?
C4 C5A 1.488(12) . ?
C4 H4 0.9400 . ?
C5 C6 1.317(10) . ?
C5 C7 1.506(10) . ?
C6 H6A 0.9400 . ?
C6 H6B 0.9400 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C5A C6A 1.326(13) . ?
C5A C7A 1.502(13) . ?
C6A H601 0.9400 . ?
C6A H602 0.9400 . ?
C7A H701 0.9700 . ?
C7A H702 0.9700 . ?
C7A H703 0.9700 . ?
C3 B1 1.605(5) . ?
C3 H3 0.9400 . ?
C2 C1 1.470(5) . ?
C2 B1 1.694(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C1 C21 1.488(5) . ?
C12 C13 1.519(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.509(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C21 C26 1.385(5) . ?
C21 C22 1.393(5) . ?
C22 C23 1.369(5) . ?
C22 H22 0.9400 . ?
C23 C24 1.378(6) . ?
C23 H23 0.9400 . ?
C24 C25 1.370(6) . ?
C24 H24 0.9400 . ?
C25 C26 1.388(5) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
B1 C31 1.650(5) . ?
B1 C41 1.651(5) . ?
C31 C32 1.383(5) . ?
C31 C36 1.402(5) . ?
F32 C32 1.362(4) . ?
C32 C33 1.376(5) . ?
F33 C33 1.341(4) . ?
C33 C34 1.371(6) . ?
F34 C34 1.345(4) . ?
C34 C35 1.361(6) . ?
F35 C35 1.340(4) . ?
C35 C36 1.380(5) . ?
F36 C36 1.356(4) . ?
C41 C42 1.390(5) . ?
C41 C46 1.398(5) . ?
F42 C42 1.364(4) . ?
C42 C43 1.377(5) . ?
F43 C43 1.341(4) . ?
C43 C44 1.372(5) . ?
F44 C44 1.343(4) . ?
C44 C45 1.359(5) . ?
F45 C45 1.348(4) . ?
C45 C46 1.369(5) . ?
F46 C46 1.361(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N11 C14 122.1(3) . . ?
C1 N11 C12 124.1(3) . . ?
C14 N11 C12 113.3(3) . . ?
C3 C4 C5 128.8(7) . . ?
C3 C4 C5A 120.7(9) . . ?
C5 C4 C5A 12.2(15) . . ?
C3 C4 H4 115.6 . . ?
C5 C4 H4 115.6 . . ?
C5A C4 H4 122.7 . . ?
C6 C5 C4 122.2(10) . . ?
C6 C5 C7 121.7(10) . . ?
C4 C5 C7 116.1(9) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
C6A C5A C4 119.6(13) . . ?
C6A C5A C7A 118.4(13) . . ?
C4 C5A C7A 122.0(13) . . ?
C5A C6A H601 120.0 . . ?
C5A C6A H602 120.0 . . ?
H601 C6A H602 120.0 . . ?
C5A C7A H701 109.5 . . ?
C5A C7A H702 109.5 . . ?
H701 C7A H702 109.5 . . ?
C5A C7A H703 109.5 . . ?
H701 C7A H703 109.5 . . ?
H702 C7A H703 109.5 . . ?
C4 C3 B1 129.3(3) . . ?
C4 C3 H3 115.4 . . ?
B1 C3 H3 115.4 . . ?
C1 C2 B1 115.1(3) . . ?
C1 C2 H2A 108.5 . . ?
B1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
B1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
N11 C1 C2 123.9(3) . . ?
N11 C1 C21 119.8(3) . . ?
C2 C1 C21 116.2(3) . . ?
N11 C12 C13 112.6(4) . . ?
N11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
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 . . ?
N11 C14 C15 112.1(3) . . ?
N11 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N11 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
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 . . ?
C26 C21 C22 118.9(4) . . ?
C26 C21 C1 121.2(3) . . ?
C22 C21 C1 119.8(3) . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.7(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.0(4) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C3 B1 C31 112.0(3) . . ?
C3 B1 C41 112.9(3) . . ?
C31 B1 C41 106.7(3) . . ?
C3 B1 C2 104.8(3) . . ?
C31 B1 C2 110.0(3) . . ?
C41 B1 C2 110.5(3) . . ?
C32 C31 C36 111.6(3) . . ?
C32 C31 B1 129.1(3) . . ?
C36 C31 B1 119.2(3) . . ?
F32 C32 C33 114.5(3) . . ?
F32 C32 C31 120.4(3) . . ?
C33 C32 C31 125.1(4) . . ?
F33 C33 C34 119.3(4) . . ?
F33 C33 C32 120.9(4) . . ?
C34 C33 C32 119.7(4) . . ?
F34 C34 C35 120.1(4) . . ?
F34 C34 C33 120.9(4) . . ?
C35 C34 C33 119.0(4) . . ?
F35 C35 C34 120.2(4) . . ?
F35 C35 C36 120.6(4) . . ?
C34 C35 C36 119.2(4) . . ?
F36 C36 C35 115.9(3) . . ?
F36 C36 C31 118.8(3) . . ?
C35 C36 C31 125.2(3) . . ?
C42 C41 C46 111.4(3) . . ?
C42 C41 B1 127.0(3) . . ?
C46 C41 B1 121.6(3) . . ?
F42 C42 C43 114.5(3) . . ?
F42 C42 C41 119.9(3) . . ?
C43 C42 C41 125.6(3) . . ?
F43 C43 C44 119.6(3) . . ?
F43 C43 C42 121.4(4) . . ?
C44 C43 C42 119.0(3) . . ?
F44 C44 C45 120.6(4) . . ?
F44 C44 C43 120.3(4) . . ?
C45 C44 C43 119.1(4) . . ?
F45 C45 C44 119.7(3) . . ?
F45 C45 C46 120.5(3) . . ?
C44 C45 C46 119.9(3) . . ?
F46 C46 C45 116.0(3) . . ?
F46 C46 C41 118.9(3) . . ?
C45 C46 C41 125.1(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
C3 C4 C5 C6 -177.0(12) . . . . ?
C5A C4 C5 C6 132(9) . . . . ?
C3 C4 C5 C7 4(2) . . . . ?
C5A C4 C5 C7 -47(6) . . . . ?
C3 C4 C5A C6A 177.1(18) . . . . ?
C5 C4 C5A C6A -48(6) . . . . ?
C3 C4 C5A C7A -2(3) . . . . ?
C5 C4 C5A C7A 133(9) . . . . ?
C5 C4 C3 B1 169.4(12) . . . . ?
C5A C4 C3 B1 -179.6(16) . . . . ?
C14 N11 C1 C2 1.5(5) . . . . ?
C12 N11 C1 C2 172.9(4) . . . . ?
C14 N11 C1 C21 179.9(3) . . . . ?
C12 N11 C1 C21 -8.6(5) . . . . ?
B1 C2 C1 N11 103.0(4) . . . . ?
B1 C2 C1 C21 -75.6(4) . . . . ?
C1 N11 C12 C13 113.9(4) . . . . ?
C14 N11 C12 C13 -74.0(5) . . . . ?
C1 N11 C14 C15 86.6(4) . . . . ?
C12 N11 C14 C15 -85.7(4) . . . . ?
N11 C1 C21 C26 -63.8(5) . . . . ?
C2 C1 C21 C26 114.8(4) . . . . ?
N11 C1 C21 C22 119.7(4) . . . . ?
C2 C1 C21 C22 -61.7(5) . . . . ?
C26 C21 C22 C23 1.0(6) . . . . ?
C1 C21 C22 C23 177.6(4) . . . . ?
C21 C22 C23 C24 -0.5(7) . . . . ?
C22 C23 C24 C25 -0.8(8) . . . . ?
C23 C24 C25 C26 1.7(7) . . . . ?
C22 C21 C26 C25 -0.2(6) . . . . ?
C1 C21 C26 C25 -176.7(4) . . . . ?
C24 C25 C26 C21 -1.2(7) . . . . ?
C4 C3 B1 C31 23.2(5) . . . . ?
C4 C3 B1 C41 143.7(4) . . . . ?
C4 C3 B1 C2 -96.0(4) . . . . ?
C1 C2 B1 C3 -53.2(4) . . . . ?
C1 C2 B1 C31 -173.8(3) . . . . ?
C1 C2 B1 C41 68.6(4) . . . . ?
C3 B1 C31 C32 -124.6(4) . . . . ?
C41 B1 C31 C32 111.4(4) . . . . ?
C2 B1 C31 C32 -8.5(5) . . . . ?
C3 B1 C31 C36 56.4(4) . . . . ?
C41 B1 C31 C36 -67.6(4) . . . . ?
C2 B1 C31 C36 172.5(3) . . . . ?
C36 C31 C32 F32 176.7(3) . . . . ?
B1 C31 C32 F32 -2.4(6) . . . . ?
C36 C31 C32 C33 -2.3(5) . . . . ?
B1 C31 C32 C33 178.6(4) . . . . ?
F32 C32 C33 F33 1.0(5) . . . . ?
C31 C32 C33 F33 -179.9(3) . . . . ?
F32 C32 C33 C34 -176.8(3) . . . . ?
C31 C32 C33 C34 2.3(6) . . . . ?
F33 C33 C34 F34 -0.1(6) . . . . ?
C32 C33 C34 F34 177.7(4) . . . . ?
F33 C33 C34 C35 -178.0(4) . . . . ?
C32 C33 C34 C35 -0.2(6) . . . . ?
F34 C34 C35 F35 -0.8(6) . . . . ?
C33 C34 C35 F35 177.1(4) . . . . ?
F34 C34 C35 C36 -179.4(3) . . . . ?
C33 C34 C35 C36 -1.5(6) . . . . ?
F35 C35 C36 F36 0.4(5) . . . . ?
C34 C35 C36 F36 179.0(3) . . . . ?
F35 C35 C36 C31 -177.2(3) . . . . ?
C34 C35 C36 C31 1.3(6) . . . . ?
C32 C31 C36 F36 -177.1(3) . . . . ?
B1 C31 C36 F36 2.1(5) . . . . ?
C32 C31 C36 C35 0.5(5) . . . . ?
B1 C31 C36 C35 179.7(3) . . . . ?
C3 B1 C41 C42 -10.4(5) . . . . ?
C31 B1 C41 C42 113.1(4) . . . . ?
C2 B1 C41 C42 -127.3(4) . . . . ?
C3 B1 C41 C46 168.1(3) . . . . ?
C31 B1 C41 C46 -68.4(4) . . . . ?
C2 B1 C41 C46 51.1(4) . . . . ?
C46 C41 C42 F42 177.9(3) . . . . ?
B1 C41 C42 F42 -3.6(6) . . . . ?
C46 C41 C42 C43 -1.7(6) . . . . ?
B1 C41 C42 C43 176.9(4) . . . . ?
F42 C42 C43 F43 1.9(5) . . . . ?
C41 C42 C43 F43 -178.5(4) . . . . ?
F42 C42 C43 C44 -179.4(4) . . . . ?
C41 C42 C43 C44 0.2(6) . . . . ?
F43 C43 C44 F44 -1.7(6) . . . . ?
C42 C43 C44 F44 179.6(4) . . . . ?
F43 C43 C44 C45 179.6(4) . . . . ?
C42 C43 C44 C45 0.8(6) . . . . ?
F44 C44 C45 F45 0.7(6) . . . . ?
C43 C44 C45 F45 179.4(4) . . . . ?
F44 C44 C45 C46 -179.0(4) . . . . ?
C43 C44 C45 C46 -0.2(6) . . . . ?
F45 C45 C46 F46 -1.6(6) . . . . ?
C44 C45 C46 F46 178.1(4) . . . . ?
F45 C45 C46 C41 178.9(4) . . . . ?
C44 C45 C46 C41 -1.5(6) . . . . ?
C42 C41 C46 F46 -177.2(3) . . . . ?
B1 C41 C46 F46 4.1(5) . . . . ?
C42 C41 C46 C45 2.3(6) . . . . ?
B1 C41 C46 C45 -176.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_erk7693
_database_code_depnum_ccdc_archive 'CCDC 1411187'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 B F10 N O'
_chemical_formula_weight         431.04

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.6260(5)
_cell_length_b                   18.2872(12)
_cell_length_c                   21.3911(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.102(2)
_cell_angle_gamma                90.00
_cell_volume                     3373.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5163
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      25.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_T_max  0.9964
_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            17034
_diffrn_reflns_av_R_equivalents  0.128
_diffrn_reflns_av_sigmaI/netI    0.1694
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5714
_reflns_number_gt                2608
_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 morpholino group at B1b atom 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+32.8256P] 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         5714
_refine_ls_number_parameters     578
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.3246
_refine_ls_R_factor_gt           0.1902
_refine_ls_wR_factor_ref         0.3268
_refine_ls_wR_factor_gt          0.2615
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_restrained_S_all      1.247
_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
O1A O -0.5463(11) -0.2038(6) 0.4348(5) 0.075(3) Uani 1 1 d . . .
B1A B -0.1275(17) -0.1316(8) 0.3656(7) 0.043(4) Uani 1 1 d . . .
N1A N -0.2808(11) -0.1488(6) 0.3722(5) 0.047(3) Uani 1 1 d . . .
C1A C -0.3464(17) -0.2221(7) 0.3589(7) 0.064(4) Uani 1 1 d . . .
H1A1 H -0.2637 -0.2558 0.3470 0.077 Uiso 1 1 calc R . .
H1A2 H -0.4218 -0.2191 0.3241 0.077 Uiso 1 1 calc R . .
C2A C -0.4243(16) -0.2499(8) 0.4164(7) 0.067(4) Uani 1 1 d . . .
H2A1 H -0.4652 -0.2990 0.4082 0.080 Uiso 1 1 calc R . .
H2A2 H -0.3476 -0.2535 0.4507 0.080 Uiso 1 1 calc R . .
C3A C -0.4802(17) -0.1347(9) 0.4497(7) 0.077(5) Uani 1 1 d . . .
H3A1 H -0.4041 -0.1407 0.4839 0.092 Uiso 1 1 calc R . .
H3A2 H -0.5618 -0.1019 0.4643 0.092 Uiso 1 1 calc R . .
C4A C -0.4022(16) -0.1001(7) 0.3948(7) 0.065(4) Uani 1 1 d . . .
H4A1 H -0.4787 -0.0910 0.3613 0.077 Uiso 1 1 calc R . .
H4A2 H -0.3566 -0.0532 0.4074 0.077 Uiso 1 1 calc R . .
C11A C -0.0018(15) -0.1865(6) 0.3418(6) 0.044(3) Uani 1 1 d . . .
F12A F -0.0070(10) -0.2543(4) 0.4361(4) 0.075(2) Uani 1 1 d . . .
C12A C 0.0496(18) -0.2418(7) 0.3780(7) 0.062(4) Uani 1 1 d . . .
F13A F 0.2245(10) -0.3412(4) 0.4007(5) 0.097(3) Uani 1 1 d . . .
C13A C 0.169(2) -0.2883(8) 0.3614(9) 0.074(5) Uani 1 1 d . . .
F14A F 0.3499(10) -0.3244(5) 0.2875(5) 0.106(3) Uani 1 1 d . . .
C14A C 0.2361(19) -0.2787(9) 0.3035(9) 0.075(5) Uani 1 1 d . . .
F15A F 0.2423(10) -0.2176(5) 0.2091(4) 0.095(3) Uani 1 1 d . . .
C15A C 0.1811(18) -0.2258(8) 0.2657(7) 0.064(4) Uani 1 1 d . . .
F16A F 0.0166(10) -0.1272(4) 0.2459(3) 0.072(2) Uani 1 1 d . . .
C16A C 0.0637(16) -0.1800(7) 0.2842(6) 0.052(4) Uani 1 1 d . . .
C21A C -0.0677(15) -0.0493(7) 0.3753(6) 0.043(3) Uani 1 1 d . . .
F22A F -0.2254(11) 0.0023(4) 0.2949(4) 0.081(3) Uani 1 1 d . . .
C22A C -0.1153(18) 0.0111(8) 0.3398(7) 0.059(4) Uani 1 1 d . . .
F23A F -0.1050(12) 0.1357(5) 0.3163(5) 0.106(3) Uani 1 1 d . . .
C23A C -0.053(2) 0.0795(8) 0.3503(8) 0.072(5) Uani 1 1 d . . .
F24A F 0.1142(11) 0.1575(5) 0.4058(5) 0.104(3) Uani 1 1 d U . .
C24A C 0.0567(19) 0.0884(9) 0.3959(9) 0.067(5) Uani 1 1 d . . .
F25A F 0.2219(11) 0.0411(5) 0.4745(5) 0.104(3) Uani 1 1 d . . .
C25A C 0.1118(18) 0.0319(9) 0.4303(8) 0.064(4) Uani 1 1 d . . .
F26A F 0.1005(10) -0.0922(5) 0.4546(4) 0.077(2) Uani 1 1 d . . .
C26A C 0.0453(16) -0.0369(7) 0.4185(7) 0.054(4) Uani 1 1 d . . .
B1B B 0.401(2) 0.3932(9) 0.3805(8) 0.074(6) Uani 1 1 d D . .
N1B N 0.2826(19) 0.4190(8) 0.4178(8) 0.035(5) Uani 0.521(14) 1 d PDU A 1
C1B C 0.169(2) 0.3727(12) 0.4491(11) 0.052(7) Uani 0.521(14) 1 d PDU A 1
H1B1 H 0.1564 0.3894 0.4922 0.062 Uiso 0.521(14) 1 calc PR A 1
H1B2 H 0.2060 0.3221 0.4503 0.062 Uiso 0.521(14) 1 calc PR A 1
C2B C 0.014(3) 0.3755(12) 0.4151(13) 0.061(8) Uani 0.521(14) 1 d PDU A 1
H2B1 H 0.0254 0.3571 0.3724 0.073 Uiso 0.521(14) 1 calc PR A 1
H2B2 H -0.0601 0.3441 0.4365 0.073 Uiso 0.521(14) 1 calc PR A 1
O1B O -0.044(2) 0.4491(11) 0.4130(12) 0.084(7) Uani 0.521(14) 1 d PDU A 1
C3B C 0.064(3) 0.4968(14) 0.3832(13) 0.066(9) Uani 0.521(14) 1 d PDU A 1
H3B1 H 0.0243 0.5471 0.3845 0.080 Uiso 0.521(14) 1 calc PR A 1
H3B2 H 0.0724 0.4828 0.3392 0.080 Uiso 0.521(14) 1 calc PR A 1
C4B C 0.222(2) 0.4942(10) 0.4142(12) 0.058(8) Uani 0.521(14) 1 d PDU A 1
H4B1 H 0.2940 0.5246 0.3905 0.070 Uiso 0.521(14) 1 calc PR A 1
H4B2 H 0.2162 0.5145 0.4565 0.070 Uiso 0.521(14) 1 calc PR A 1
N1C N 0.2398(19) 0.4095(9) 0.3833(10) 0.036(5) Uani 0.479(14) 1 d PDU A 2
C1C C 0.122(3) 0.3606(13) 0.4094(14) 0.071(10) Uani 0.479(14) 1 d PDU A 2
H1C1 H 0.1732 0.3156 0.4236 0.085 Uiso 0.479(14) 1 calc PR A 2
H1C2 H 0.0482 0.3473 0.3759 0.085 Uiso 0.479(14) 1 calc PR A 2
C2C C 0.033(4) 0.3912(14) 0.4626(13) 0.079(11) Uani 0.479(14) 1 d PDU A 2
H2C1 H -0.0530 0.3582 0.4719 0.095 Uiso 0.479(14) 1 calc PR A 2
H2C2 H 0.1011 0.3936 0.4997 0.095 Uiso 0.479(14) 1 calc PR A 2
O1C O -0.027(2) 0.4624(11) 0.4495(12) 0.082(7) Uani 0.479(14) 1 d PDU A 2
C3C C 0.092(3) 0.5112(14) 0.4300(14) 0.073(10) Uani 0.479(14) 1 d PDU A 2
H3C1 H 0.1688 0.5173 0.4641 0.088 Uiso 0.479(14) 1 calc PR A 2
H3C2 H 0.0471 0.5592 0.4206 0.088 Uiso 0.479(14) 1 calc PR A 2
C4C C 0.172(3) 0.4822(13) 0.3728(12) 0.065(9) Uani 0.479(14) 1 d PDU A 2
H4C1 H 0.0961 0.4795 0.3381 0.078 Uiso 0.479(14) 1 calc PR A 2
H4C2 H 0.2535 0.5163 0.3609 0.078 Uiso 0.479(14) 1 calc PR A 2
C11B C 0.4582(16) 0.3099(7) 0.3863(6) 0.052(4) Uani 1 1 d . A .
F12B F 0.2691(11) 0.2681(5) 0.3117(5) 0.094(3) Uani 1 1 d . A .
C12B C 0.3894(19) 0.2542(8) 0.3506(7) 0.059(4) Uani 1 1 d . . .
F13B F 0.3775(12) 0.1309(5) 0.3193(5) 0.114(4) Uani 1 1 d . . .
C13B C 0.445(2) 0.1820(9) 0.3536(8) 0.073(5) Uani 1 1 d . A .
F14B F 0.6208(12) 0.0990(5) 0.3955(5) 0.111(3) Uani 1 1 d U A .
C14B C 0.569(2) 0.1695(9) 0.3921(9) 0.075(5) Uani 1 1 d . . .
F15B F 0.7656(11) 0.2052(5) 0.4599(5) 0.105(3) Uani 1 1 d U . .
C15B C 0.6381(18) 0.2218(9) 0.4238(7) 0.061(4) Uani 1 1 d . A .
F16B F 0.6529(11) 0.3428(5) 0.4568(4) 0.091(3) Uani 1 1 d . A .
C16B C 0.5829(18) 0.2896(8) 0.4223(7) 0.058(4) Uani 1 1 d . . .
C21B C 0.5201(16) 0.4495(7) 0.3503(6) 0.055(4) Uani 1 1 d . A .
F22B F 0.5510(12) 0.5212(4) 0.4421(4) 0.097(3) Uani 1 1 d . A .
C22B C 0.5866(18) 0.5074(8) 0.3823(7) 0.064(4) Uani 1 1 d . . .
F23B F 0.7626(11) 0.6060(4) 0.3891(4) 0.088(3) Uani 1 1 d . . .
C23B C 0.6973(18) 0.5507(8) 0.3548(7) 0.066(4) Uani 1 1 d . A .
F24B F 0.8550(10) 0.5805(5) 0.2713(4) 0.083(3) Uani 1 1 d . A .
C24B C 0.7442(16) 0.5382(8) 0.2968(7) 0.060(4) Uani 1 1 d . . .
F25B F 0.7231(10) 0.4699(4) 0.2039(4) 0.080(3) Uani 1 1 d . . .
C25B C 0.6775(17) 0.4818(8) 0.2630(6) 0.058(4) Uani 1 1 d . A .
F26B F 0.5072(9) 0.3839(4) 0.2560(4) 0.069(2) Uani 1 1 d . A .
C26B C 0.5700(16) 0.4387(7) 0.2909(6) 0.054(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C2A 1.409(15) . ?
O1A C3A 1.421(17) . ?
B1A N1A 1.369(16) . ?
B1A C11A 1.570(18) . ?
B1A C21A 1.603(18) . ?
N1A C4A 1.464(15) . ?
N1A C1A 1.481(16) . ?
C1A C2A 1.501(17) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C3A C4A 1.503(18) . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C11A C12A 1.344(17) . ?
C11A C16A 1.369(16) . ?
F12A C12A 1.364(14) . ?
C12A C13A 1.39(2) . ?
F13A C13A 1.362(16) . ?
C13A C14A 1.39(2) . ?
F14A C14A 1.338(16) . ?
C14A C15A 1.34(2) . ?
F15A C15A 1.338(15) . ?
C15A C16A 1.379(18) . ?
F16A C16A 1.325(14) . ?
C21A C26A 1.349(17) . ?
C21A C22A 1.399(17) . ?
F22A C22A 1.347(16) . ?
C22A C23A 1.38(2) . ?
F23A C23A 1.333(16) . ?
C23A C24A 1.35(2) . ?
F24A C24A 1.371(15) . ?
C24A C25A 1.35(2) . ?
F25A C25A 1.339(17) . ?
C25A C26A 1.404(19) . ?
F26A C26A 1.352(14) . ?
B1B N1B 1.39(2) . ?
B1B N1C 1.42(2) . ?
B1B C21B 1.60(2) . ?
B1B C11B 1.60(2) . ?
N1B C1B 1.468(17) . ?
N1B C4B 1.473(17) . ?
C1B C2B 1.506(19) . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C2B O1B 1.435(18) . ?
C2B H2B1 0.9800 . ?
C2B H2B2 0.9800 . ?
O1B C3B 1.433(19) . ?
C3B C4B 1.508(19) . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
N1C C4C 1.469(18) . ?
N1C C1C 1.472(18) . ?
C1C C2C 1.49(2) . ?
C1C H1C1 0.9800 . ?
C1C H1C2 0.9800 . ?
C2C O1C 1.428(19) . ?
C2C H2C1 0.9800 . ?
C2C H2C2 0.9800 . ?
O1C C3C 1.431(19) . ?
C3C C4C 1.509(19) . ?
C3C H3C1 0.9800 . ?
C3C H3C2 0.9800 . ?
C4C H4C1 0.9800 . ?
C4C H4C2 0.9800 . ?
C11B C16B 1.363(18) . ?
C11B C12B 1.399(18) . ?
F12B C12B 1.342(16) . ?
C12B C13B 1.41(2) . ?
F13B C13B 1.319(18) . ?
C13B C14B 1.36(2) . ?
F14B C14B 1.366(17) . ?
C14B C15B 1.31(2) . ?
F15B C15B 1.367(16) . ?
C15B C16B 1.329(18) . ?
F16B C16B 1.355(16) . ?
C21B C26B 1.365(16) . ?
C21B C22B 1.380(18) . ?
F22B C22B 1.347(14) . ?
C22B C23B 1.380(19) . ?
F23B C23B 1.365(16) . ?
C23B C24B 1.332(18) . ?
F24B C24B 1.352(14) . ?
C24B C25B 1.378(18) . ?
F25B C25B 1.348(13) . ?
C25B C26B 1.363(17) . ?
F26B C26B 1.356(14) . ?

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
C2A O1A C3A 107.2(10) . . ?
N1A B1A C11A 124.1(12) . . ?
N1A B1A C21A 120.7(12) . . ?
C11A B1A C21A 114.8(11) . . ?
B1A N1A C4A 126.4(11) . . ?
B1A N1A C1A 123.7(11) . . ?
C4A N1A C1A 109.9(10) . . ?
N1A C1A C2A 108.9(11) . . ?
N1A C1A H1A1 109.9 . . ?
C2A C1A H1A1 109.9 . . ?
N1A C1A H1A2 109.9 . . ?
C2A C1A H1A2 109.9 . . ?
H1A1 C1A H1A2 108.3 . . ?
O1A C2A C1A 112.0(12) . . ?
O1A C2A H2A1 109.2 . . ?
C1A C2A H2A1 109.2 . . ?
O1A C2A H2A2 109.2 . . ?
C1A C2A H2A2 109.2 . . ?
H2A1 C2A H2A2 107.9 . . ?
O1A C3A C4A 112.5(12) . . ?
O1A C3A H3A1 109.1 . . ?
C4A C3A H3A1 109.1 . . ?
O1A C3A H3A2 109.1 . . ?
C4A C3A H3A2 109.1 . . ?
H3A1 C3A H3A2 107.8 . . ?
N1A C4A C3A 109.7(12) . . ?
N1A C4A H4A1 109.7 . . ?
C3A C4A H4A1 109.7 . . ?
N1A C4A H4A2 109.7 . . ?
C3A C4A H4A2 109.7 . . ?
H4A1 C4A H4A2 108.2 . . ?
C12A C11A C16A 116.5(12) . . ?
C12A C11A B1A 121.1(12) . . ?
C16A C11A B1A 122.4(12) . . ?
C11A C12A F12A 122.1(12) . . ?
C11A C12A C13A 123.5(14) . . ?
F12A C12A C13A 114.3(13) . . ?
F13A C13A C12A 122.1(16) . . ?
F13A C13A C14A 119.5(17) . . ?
C12A C13A C14A 118.4(14) . . ?
F14A C14A C15A 123.2(17) . . ?
F14A C14A C13A 118.1(17) . . ?
C15A C14A C13A 118.7(15) . . ?
F15A C15A C14A 119.1(15) . . ?
F15A C15A C16A 119.8(15) . . ?
C14A C15A C16A 121.2(15) . . ?
F16A C16A C11A 119.5(12) . . ?
F16A C16A C15A 118.8(13) . . ?
C11A C16A C15A 121.6(13) . . ?
C26A C21A C22A 116.1(13) . . ?
C26A C21A B1A 118.2(12) . . ?
C22A C21A B1A 125.5(13) . . ?
F22A C22A C23A 119.6(14) . . ?
F22A C22A C21A 119.2(13) . . ?
C23A C22A C21A 121.2(16) . . ?
F23A C23A C24A 121.6(17) . . ?
F23A C23A C22A 118.9(18) . . ?
C24A C23A C22A 119.5(15) . . ?
C25A C24A C23A 122.2(15) . . ?
C25A C24A F24A 119.9(17) . . ?
C23A C24A F24A 117.8(17) . . ?
F25A C25A C24A 121.8(16) . . ?
F25A C25A C26A 121.4(16) . . ?
C24A C25A C26A 116.8(16) . . ?
C21A C26A F26A 120.5(13) . . ?
C21A C26A C25A 124.1(14) . . ?
F26A C26A C25A 115.4(14) . . ?
N1B B1B N1C 34.6(10) . . ?
N1B B1B C21B 119.8(14) . . ?
N1C B1B C21B 121.2(14) . . ?
N1B B1B C11B 120.4(14) . . ?
N1C B1B C11B 119.7(15) . . ?
C21B B1B C11B 116.3(13) . . ?
B1B N1B C1B 124.8(16) . . ?
B1B N1B C4B 123.4(15) . . ?
C1B N1B C4B 108.9(15) . . ?
N1B C1B C2B 110.8(17) . . ?
N1B C1B H1B1 109.5 . . ?
C2B C1B H1B1 109.5 . . ?
N1B C1B H1B2 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 108.1 . . ?
O1B C2B C1B 110.6(18) . . ?
O1B C2B H2B1 109.5 . . ?
C1B C2B H2B1 109.5 . . ?
O1B C2B H2B2 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 108.1 . . ?
C3B O1B C2B 110.9(19) . . ?
O1B C3B C4B 112.0(19) . . ?
O1B C3B H3B1 109.2 . . ?
C4B C3B H3B1 109.2 . . ?
O1B C3B H3B2 109.2 . . ?
C4B C3B H3B2 109.2 . . ?
H3B1 C3B H3B2 107.9 . . ?
N1B C4B C3B 111.6(18) . . ?
N1B C4B H4B1 109.3 . . ?
C3B C4B H4B1 109.3 . . ?
N1B C4B H4B2 109.3 . . ?
C3B C4B H4B2 109.3 . . ?
H4B1 C4B H4B2 108.0 . . ?
B1B N1C C4C 124.9(17) . . ?
B1B N1C C1C 124.8(17) . . ?
C4C N1C C1C 109.2(17) . . ?
N1C C1C C2C 116(2) . . ?
N1C C1C H1C1 108.4 . . ?
C2C C1C H1C1 108.4 . . ?
N1C C1C H1C2 108.4 . . ?
C2C C1C H1C2 108.4 . . ?
H1C1 C1C H1C2 107.5 . . ?
O1C C2C C1C 113(2) . . ?
O1C C2C H2C1 109.1 . . ?
C1C C2C H2C1 109.1 . . ?
O1C C2C H2C2 109.1 . . ?
C1C C2C H2C2 109.1 . . ?
H2C1 C2C H2C2 107.8 . . ?
C2C O1C C3C 111(2) . . ?
O1C C3C C4C 111(2) . . ?
O1C C3C H3C1 109.5 . . ?
C4C C3C H3C1 109.5 . . ?
O1C C3C H3C2 109.5 . . ?
C4C C3C H3C2 109.5 . . ?
H3C1 C3C H3C2 108.0 . . ?
N1C C4C C3C 112.4(19) . . ?
N1C C4C H4C1 109.1 . . ?
C3C C4C H4C1 109.1 . . ?
N1C C4C H4C2 109.1 . . ?
C3C C4C H4C2 109.1 . . ?
H4C1 C4C H4C2 107.8 . . ?
C16B C11B C12B 115.6(14) . . ?
C16B C11B B1B 122.7(14) . . ?
C12B C11B B1B 121.5(15) . . ?
F12B C12B C11B 121.0(14) . . ?
F12B C12B C13B 117.8(15) . . ?
C11B C12B C13B 121.2(16) . . ?
F13B C13B C14B 123.6(17) . . ?
F13B C13B C12B 119.6(18) . . ?
C14B C13B C12B 116.8(16) . . ?
C15B C14B C13B 122.4(16) . . ?
C15B C14B F14B 121.2(19) . . ?
C13B C14B F14B 116.3(18) . . ?
C14B C15B C16B 120.8(17) . . ?
C14B C15B F15B 118.9(16) . . ?
C16B C15B F15B 120.3(17) . . ?
C15B C16B F16B 120.1(16) . . ?
C15B C16B C11B 123.1(16) . . ?
F16B C16B C11B 116.8(13) . . ?
C26B C21B C22B 115.9(12) . . ?
C26B C21B B1B 120.0(13) . . ?
C22B C21B B1B 124.0(13) . . ?
F22B C22B C23B 118.0(14) . . ?
F22B C22B C21B 121.0(14) . . ?
C23B C22B C21B 120.9(13) . . ?
C24B C23B F23B 119.9(14) . . ?
C24B C23B C22B 121.5(15) . . ?
F23B C23B C22B 118.6(13) . . ?
C23B C24B F24B 120.5(14) . . ?
C23B C24B C25B 119.1(13) . . ?
F24B C24B C25B 120.5(13) . . ?
F25B C25B C26B 121.9(13) . . ?
F25B C25B C24B 119.1(13) . . ?
C26B C25B C24B 118.9(12) . . ?
F26B C26B C25B 117.0(12) . . ?
F26B C26B C21B 119.3(12) . . ?
C25B C26B C21B 123.6(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11A B1A N1A C4A 179.2(12) . . . . ?
C21A B1A N1A C4A -7(2) . . . . ?
C11A B1A N1A C1A 1(2) . . . . ?
C21A B1A N1A C1A 174.8(11) . . . . ?
B1A N1A C1A C2A 123.1(13) . . . . ?
C4A N1A C1A C2A -55.0(15) . . . . ?
C3A O1A C2A C1A -62.3(15) . . . . ?
N1A C1A C2A O1A 60.6(15) . . . . ?
C2A O1A C3A C4A 61.0(16) . . . . ?
B1A N1A C4A C3A -124.1(14) . . . . ?
C1A N1A C4A C3A 54.0(14) . . . . ?
O1A C3A C4A N1A -58.3(16) . . . . ?
N1A B1A C11A C12A -72.5(18) . . . . ?
C21A B1A C11A C12A 113.7(15) . . . . ?
N1A B1A C11A C16A 109.0(16) . . . . ?
C21A B1A C11A C16A -64.7(17) . . . . ?
C16A C11A C12A F12A -179.7(12) . . . . ?
B1A C11A C12A F12A 2(2) . . . . ?
C16A C11A C12A C13A 4(2) . . . . ?
B1A C11A C12A C13A -174.7(14) . . . . ?
C11A C12A C13A F13A 176.0(14) . . . . ?
F12A C12A C13A F13A -1(2) . . . . ?
C11A C12A C13A C14A -2(2) . . . . ?
F12A C12A C13A C14A -178.6(13) . . . . ?
F13A C13A C14A F14A 3(2) . . . . ?
C12A C13A C14A F14A -179.2(13) . . . . ?
F13A C13A C14A C15A -179.2(14) . . . . ?
C12A C13A C14A C15A -1(2) . . . . ?
F14A C14A C15A F15A 0(2) . . . . ?
C13A C14A C15A F15A -178.1(13) . . . . ?
F14A C14A C15A C16A -179.9(13) . . . . ?
C13A C14A C15A C16A 2(2) . . . . ?
C12A C11A C16A F16A 179.0(12) . . . . ?
B1A C11A C16A F16A -2(2) . . . . ?
C12A C11A C16A C15A -3(2) . . . . ?
B1A C11A C16A C15A 175.7(12) . . . . ?
F15A C15A C16A F16A -2(2) . . . . ?
C14A C15A C16A F16A 178.0(13) . . . . ?
F15A C15A C16A C11A -179.9(12) . . . . ?
C14A C15A C16A C11A 0(2) . . . . ?
N1A B1A C21A C26A 123.0(14) . . . . ?
C11A B1A C21A C26A -63.0(16) . . . . ?
N1A B1A C21A C22A -61.5(18) . . . . ?
C11A B1A C21A C22A 112.5(14) . . . . ?
C26A C21A C22A F22A 178.6(12) . . . . ?
B1A C21A C22A F22A 3.1(19) . . . . ?
C26A C21A C22A C23A -1.9(19) . . . . ?
B1A C21A C22A C23A -177.5(13) . . . . ?
F22A C22A C23A F23A 1(2) . . . . ?
C21A C22A C23A F23A -178.1(12) . . . . ?
F22A C22A C23A C24A 179.2(13) . . . . ?
C21A C22A C23A C24A 0(2) . . . . ?
F23A C23A C24A C25A -179.4(13) . . . . ?
C22A C23A C24A C25A 3(2) . . . . ?
F23A C23A C24A F24A -1(2) . . . . ?
C22A C23A C24A F24A -178.7(12) . . . . ?
C23A C24A C25A F25A 178.7(14) . . . . ?
F24A C24A C25A F25A 0(2) . . . . ?
C23A C24A C25A C26A -3(2) . . . . ?
F24A C24A C25A C26A 178.7(12) . . . . ?
C22A C21A C26A F26A -179.1(11) . . . . ?
B1A C21A C26A F26A -3.2(18) . . . . ?
C22A C21A C26A C25A 2(2) . . . . ?
B1A C21A C26A C25A 177.7(12) . . . . ?
F25A C25A C26A C21A 178.9(12) . . . . ?
C24A C25A C26A C21A 0(2) . . . . ?
F25A C25A C26A F26A -0.2(19) . . . . ?
C24A C25A C26A F26A -178.6(12) . . . . ?
N1C B1B N1B C1B 79(2) . . . . ?
C21B B1B N1B C1B -178.6(17) . . . . ?
C11B B1B N1B C1B -20(3) . . . . ?
N1C B1B N1B C4B -80(2) . . . . ?
C21B B1B N1B C4B 23(3) . . . . ?
C11B B1B N1B C4B -178.9(18) . . . . ?
B1B N1B C1B C2B -104(2) . . . . ?
C4B N1B C1B C2B 57(2) . . . . ?
N1B C1B C2B O1B -60(3) . . . . ?
C1B C2B O1B C3B 58(3) . . . . ?
C2B O1B C3B C4B -56(3) . . . . ?
B1B N1B C4B C3B 107(2) . . . . ?
C1B N1B C4B C3B -55(2) . . . . ?
O1B C3B C4B N1B 55(3) . . . . ?
N1B B1B N1C C4C 84(2) . . . . ?
C21B B1B N1C C4C -14(3) . . . . ?
C11B B1B N1C C4C -174.1(19) . . . . ?
N1B B1B N1C C1C -82(2) . . . . ?
C21B B1B N1C C1C 179(2) . . . . ?
C11B B1B N1C C1C 19(3) . . . . ?
B1B N1C C1C C2C 121(3) . . . . ?
C4C N1C C1C C2C -47(3) . . . . ?
N1C C1C C2C O1C 49(4) . . . . ?
C1C C2C O1C C3C -54(3) . . . . ?
C2C O1C C3C C4C 58(3) . . . . ?
B1B N1C C4C C3C -117(3) . . . . ?
C1C N1C C4C C3C 51(3) . . . . ?
O1C C3C C4C N1C -58(3) . . . . ?
N1B B1B C11B C16B -96(2) . . . . ?
N1C B1B C11B C16B -136.0(17) . . . . ?
C21B B1B C11B C16B 63.0(19) . . . . ?
N1B B1B C11B C12B 89(2) . . . . ?
N1C B1B C11B C12B 49(2) . . . . ?
C21B B1B C11B C12B -112.1(16) . . . . ?
C16B C11B C12B F12B -177.7(12) . . . . ?
B1B C11B C12B F12B -2(2) . . . . ?
C16B C11B C12B C13B 1.3(19) . . . . ?
B1B C11B C12B C13B 176.8(13) . . . . ?
F12B C12B C13B F13B -1(2) . . . . ?
C11B C12B C13B F13B -180.0(12) . . . . ?
F12B C12B C13B C14B 178.4(13) . . . . ?
C11B C12B C13B C14B -1(2) . . . . ?
F13B C13B C14B C15B 177.2(14) . . . . ?
C12B C13B C14B C15B -2(2) . . . . ?
F13B C13B C14B F14B -2(2) . . . . ?
C12B C13B C14B F14B 178.9(12) . . . . ?
C13B C14B C15B C16B 4(2) . . . . ?
F14B C14B C15B C16B -177.0(13) . . . . ?
C13B C14B C15B F15B -177.8(13) . . . . ?
F14B C14B C15B F15B 1(2) . . . . ?
C14B C15B C16B F16B 178.2(13) . . . . ?
F15B C15B C16B F16B 0(2) . . . . ?
C14B C15B C16B C11B -3(2) . . . . ?
F15B C15B C16B C11B 178.6(12) . . . . ?
C12B C11B C16B C15B 1(2) . . . . ?
B1B C11B C16B C15B -174.8(13) . . . . ?
C12B C11B C16B F16B 179.2(11) . . . . ?
B1B C11B C16B F16B 3.9(19) . . . . ?
N1B B1B C21B C26B -141.0(17) . . . . ?
N1C B1B C21B C26B -100.6(19) . . . . ?
C11B B1B C21B C26B 60(2) . . . . ?
N1B B1B C21B C22B 44(2) . . . . ?
N1C B1B C21B C22B 84(2) . . . . ?
C11B B1B C21B C22B -115.3(17) . . . . ?
C26B C21B C22B F22B -177.2(13) . . . . ?
B1B C21B C22B F22B -2(2) . . . . ?
C26B C21B C22B C23B 0(2) . . . . ?
B1B C21B C22B C23B 175.2(14) . . . . ?
F22B C22B C23B C24B 176.7(14) . . . . ?
C21B C22B C23B C24B 0(2) . . . . ?
F22B C22B C23B F23B -1(2) . . . . ?
C21B C22B C23B F23B -178.2(13) . . . . ?
F23B C23B C24B F24B -1(2) . . . . ?
C22B C23B C24B F24B -178.7(13) . . . . ?
F23B C23B C24B C25B 179.7(13) . . . . ?
C22B C23B C24B C25B 2(2) . . . . ?
C23B C24B C25B F25B 179.0(13) . . . . ?
F24B C24B C25B F25B -1(2) . . . . ?
C23B C24B C25B C26B -3(2) . . . . ?
F24B C24B C25B C26B 177.7(12) . . . . ?
F25B C25B C26B F26B -2(2) . . . . ?
C24B C25B C26B F26B 179.9(12) . . . . ?
F25B C25B C26B C21B -179.5(13) . . . . ?
C24B C25B C26B C21B 2(2) . . . . ?
C22B C21B C26B F26B -178.4(12) . . . . ?
B1B C21B C26B F26B 6(2) . . . . ?
C22B C21B C26B C25B -1(2) . . . . ?
B1B C21B C26B C25B -176.5(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_erk7821
_database_code_depnum_ccdc_archive 'CCDC 1411188'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 B F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         563.28

_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                   8.0677(3)
_cell_length_b                   9.7095(4)
_cell_length_c                   18.3172(7)
_cell_angle_alpha                81.567(2)
_cell_angle_beta                 85.1470(10)
_cell_angle_gamma                70.6080(10)
_cell_volume                     1337.82(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8498
_cell_measurement_theta_min      4.8851
_cell_measurement_theta_max      68.3732
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.083
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576

_exptl_absorpt_coefficient_mu    1.142
_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  0.71
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_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            14889
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_theta_min         4.88
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_full        68.40
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
A half badly disordered dichloromethane molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program
SQUEEZE (A. L. Spek J. Appl. Cryst., 2003, 36, 7-13) was therefore used
to remove mathematically the effect of the solvent. 
The quoted formula and derived parameters are not included the squeezed
solvent molecule.
;

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
1 0.000 0.000 0.000 144.2 27.7

_reflns_number_total             4869
_reflns_number_gt                4089
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1190
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         4869
_refine_ls_number_parameters     353
_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)+(0.0674P)²+0.5165P] 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         0.374
_refine_diff_density_min         -0.201
_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       
;
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 0.4111(2) 0.4676(2) 0.26080(10) 0.0180(4) Uani d . . . 1 . .
C C1 0.5175(2) 0.29301(18) 0.26939(9) 0.0197(3) Uani d . . . 1 . .
H H1 0.5333 0.2473 0.2257 0.024 Uiso calc U . R 1 . .
N N1 0.14731(18) 0.24723(15) 0.28438(8) 0.0187(3) Uani d . . . 1 . .
C C2 0.5860(2) 0.20499(18) 0.33002(10) 0.0213(3) Uani d . . . 1 . .
H H2 0.5859 0.2511 0.3723 0.026 Uiso calc U . R 1 . .
C C3 0.6618(2) 0.04345(19) 0.33781(11) 0.0266(4) Uani d . . . 1 . .
C C4 0.7136(3) -0.0320(2) 0.40365(13) 0.0384(5) Uani d . . . 1 . .
H H4A 0.7015 0.0186 0.4454 0.046 Uiso calc U . R 1 . .
H H4B 0.7624 -0.1363 0.4087 0.046 Uiso calc U . R 1 . .
C C5 0.6782(3) -0.0338(2) 0.27115(13) 0.0372(5) Uani d . . . 1 . .
H H5A 0.7289 -0.1402 0.285 0.056 Uiso calc U . R 1 . .
H H5B 0.7548 -0.0003 0.2334 0.056 Uiso calc U . R 1 . .
H H5C 0.5616 -0.0112 0.2514 0.056 Uiso calc U . R 1 . .
C C6 0.1922(2) 0.48486(18) 0.26301(9) 0.0197(3) Uani d . . . 1 . .
H H6 0.1538 0.4817 0.3164 0.024 Uiso calc U . R 1 . .
C C7 0.1658(2) 0.35591(18) 0.23801(9) 0.0189(3) Uani d . . . 1 . .
C C8 0.1563(2) 0.3552(2) 0.15673(9) 0.0260(4) Uani d . . . 1 . .
H H8A 0.1281 0.2675 0.1478 0.031 Uiso calc U . R 1 . .
H H8B 0.2713 0.3511 0.1318 0.031 Uiso calc U . R 1 . .
C C9 0.0132(2) 0.4957(2) 0.12554(10) 0.0312(4) Uani d . . . 1 . .
H H9A 0.0083 0.4974 0.0716 0.037 Uiso calc U . R 1 . .
H H9B -0.1026 0.4961 0.1484 0.037 Uiso calc U . R 1 . .
C C10 0.0514(2) 0.6318(2) 0.14106(11) 0.0320(4) Uani d . . . 1 . .
H H10A -0.0436 0.7213 0.1218 0.038 Uiso calc U . R 1 . .
H H10B 0.1633 0.635 0.1153 0.038 Uiso calc U . R 1 . .
C C11 0.0646(2) 0.62982(19) 0.22413(10) 0.0273(4) Uani d . . . 1 . .
H H11A -0.0541 0.6463 0.2479 0.033 Uiso calc U . R 1 . .
H H11B 0.1038 0.7128 0.232 0.033 Uiso calc U . R 1 . .
C C12 0.1439(2) 0.23927(19) 0.36615(9) 0.0224(4) Uani d . . . 1 . .
H H12A 0.0653 0.3324 0.3828 0.027 Uiso calc U . R 1 . .
H H12B 0.2633 0.2189 0.3839 0.027 Uiso calc U . R 1 . .
C C13 0.0743(3) 0.1131(2) 0.39368(10) 0.0288(4) Uani d . . . 1 . .
H H13A -0.0558 0.147 0.3957 0.035 Uiso calc U . R 1 . .
H H13B 0.1173 0.066 0.4433 0.035 Uiso calc U . R 1 . .
C C14 0.1487(3) 0.0081(2) 0.33588(11) 0.0322(4) Uani d . . . 1 . .
H H14A 0.2744 -0.0481 0.3435 0.039 Uiso calc U . R 1 . .
H H14B 0.0825 -0.0617 0.337 0.039 Uiso calc U . R 1 . .
C C15 0.1250(2) 0.11070(19) 0.26406(10) 0.0262(4) Uani d . . . 1 . .
H H15A 0.2148 0.0679 0.2261 0.031 Uiso calc U . R 1 . .
H H15B 0.0067 0.1317 0.2451 0.031 Uiso calc U . R 1 . .
C C21 0.4548(2) 0.53869(17) 0.33155(9) 0.0181(3) Uani d . . . 1 . .
C C22 0.3396(2) 0.61446(18) 0.38415(9) 0.0206(3) Uani d . . . 1 . .
F F22 0.16346(13) 0.64591(12) 0.38193(6) 0.0279(2) Uani d . . . 1 . .
C C23 0.3894(2) 0.66844(18) 0.44151(9) 0.0228(4) Uani d . . . 1 . .
F F23 0.26862(14) 0.74028(12) 0.49006(6) 0.0307(3) Uani d . . . 1 . .
C C24 0.5640(2) 0.64958(19) 0.44896(9) 0.0230(4) Uani d . . . 1 . .
F F24 0.61641(15) 0.69848(12) 0.50497(6) 0.0308(3) Uani d . . . 1 . .
C C25 0.6858(2) 0.57740(19) 0.39790(10) 0.0226(4) Uani d . . . 1 . .
F F25 0.85654(14) 0.55993(12) 0.40381(6) 0.0308(3) Uani d . . . 1 . .
C C26 0.6296(2) 0.52465(17) 0.34169(9) 0.0200(3) Uani d . . . 1 . .
F F26 0.75790(13) 0.45683(11) 0.29392(5) 0.0248(2) Uani d . . . 1 . .
C C31 0.4698(2) 0.55893(18) 0.18423(9) 0.0200(3) Uani d . . . 1 . .
C C32 0.4419(2) 0.7101(2) 0.17764(9) 0.0245(4) Uani d . . . 1 . .
F F32 0.35882(15) 0.78877(11) 0.23322(6) 0.0312(3) Uani d . . . 1 . .
C C33 0.4920(3) 0.7921(2) 0.11698(11) 0.0308(4) Uani d . . . 1 . .
F F33 0.4598(2) 0.93709(13) 0.11632(7) 0.0456(3) Uani d . . . 1 . .
C C34 0.5750(3) 0.7236(2) 0.05686(10) 0.0320(4) Uani d . . . 1 . .
F F34 0.62715(19) 0.79991(16) -0.00231(6) 0.0471(3) Uani d . . . 1 . .
C C35 0.6050(2) 0.5760(2) 0.05934(9) 0.0267(4) Uani d . . . 1 . .
F F35 0.68875(15) 0.50526(14) 0.00185(6) 0.0360(3) Uani d . . . 1 . .
C C36 0.5540(2) 0.49740(19) 0.12145(9) 0.0224(3) Uani d . . . 1 . .
F F36 0.59088(14) 0.35251(11) 0.11635(6) 0.0292(2) 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 C1 . 1.616(2) ?
B1 C31 . 1.668(2) ?
B1 C21 . 1.668(2) ?
B1 C6 . 1.715(2) ?
C1 C2 . 1.335(2) ?
C1 H1 . 0.95 ?
N1 C7 . 1.295(2) ?
N1 C12 . 1.487(2) ?
N1 C15 . 1.498(2) ?
C2 C3 . 1.472(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.337(3) ?
C3 C5 . 1.499(3) ?
C4 H4A . 0.95 ?
C4 H4B . 0.95 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 C7 . 1.478(2) ?
C6 C11 . 1.554(2) ?
C6 H6 . 1.0 ?
C7 C8 . 1.498(2) ?
C8 C9 . 1.535(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.523(3) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.531(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.516(2) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.524(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.514(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C21 C22 . 1.391(2) ?
C21 C26 . 1.397(2) ?
C22 F22 . 1.354(2) ?
C22 C23 . 1.383(2) ?
C23 F23 . 1.3456(19) ?
C23 C24 . 1.375(3) ?
C24 F24 . 1.3440(19) ?
C24 C25 . 1.383(2) ?
C25 F25 . 1.342(2) ?
C25 C26 . 1.384(2) ?
C26 F26 . 1.3542(19) ?
C31 C36 . 1.393(2) ?
C31 C32 . 1.397(2) ?
C32 F32 . 1.357(2) ?
C32 C33 . 1.382(3) ?
C33 F33 . 1.343(2) ?
C33 C34 . 1.378(3) ?
C34 F34 . 1.340(2) ?
C34 C35 . 1.366(3) ?
C35 F35 . 1.349(2) ?
C35 C36 . 1.386(3) ?
C36 F36 . 1.354(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
C1 B1 C31 . . 113.10(13) ?
C1 B1 C21 . . 108.89(13) ?
C31 B1 C21 . . 106.46(13) ?
C1 B1 C6 . . 106.34(13) ?
C31 B1 C6 . . 111.69(13) ?
C21 B1 C6 . . 110.37(12) ?
C2 C1 B1 . . 128.25(15) ?
C2 C1 H1 . . 115.9 ?
B1 C1 H1 . . 115.9 ?
C7 N1 C12 . . 125.16(14) ?
C7 N1 C15 . . 125.36(14) ?
C12 N1 C15 . . 109.48(13) ?
C1 C2 C3 . . 126.42(16) ?
C1 C2 H2 . . 116.8 ?
C3 C2 H2 . . 116.8 ?
C4 C3 C2 . . 120.02(18) ?
C4 C3 C5 . . 121.10(18) ?
C2 C3 C5 . . 118.88(16) ?
C3 C4 H4A . . 120.0 ?
C3 C4 H4B . . 120.0 ?
H4A C4 H4B . . 120.0 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C11 . . 110.36(14) ?
C7 C6 B1 . . 111.24(13) ?
C11 C6 B1 . . 117.65(13) ?
C7 C6 H6 . . 105.5 ?
C11 C6 H6 . . 105.5 ?
B1 C6 H6 . . 105.5 ?
N1 C7 C6 . . 121.71(15) ?
N1 C7 C8 . . 120.20(15) ?
C6 C7 C8 . . 118.08(15) ?
C7 C8 C9 . . 109.02(15) ?
C7 C8 H8A . . 109.9 ?
C9 C8 H8A . . 109.9 ?
C7 C8 H8B . . 109.9 ?
C9 C8 H8B . . 109.9 ?
H8A C8 H8B . . 108.3 ?
C10 C9 C8 . . 110.56(15) ?
C10 C9 H9A . . 109.5 ?
C8 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
C9 C10 C11 . . 110.61(15) ?
C9 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C10 C11 C6 . . 114.50(15) ?
C10 C11 H11A . . 108.6 ?
C6 C11 H11A . . 108.6 ?
C10 C11 H11B . . 108.6 ?
C6 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
N1 C12 C13 . . 103.95(14) ?
N1 C12 H12A . . 111.0 ?
C13 C12 H12A . . 111.0 ?
N1 C12 H12B . . 111.0 ?
C13 C12 H12B . . 111.0 ?
H12A C12 H12B . . 109.0 ?
C12 C13 C14 . . 102.87(14) ?
C12 C13 H13A . . 111.2 ?
C14 C13 H13A . . 111.2 ?
C12 C13 H13B . . 111.2 ?
C14 C13 H13B . . 111.2 ?
H13A C13 H13B . . 109.1 ?
C15 C14 C13 . . 102.98(15) ?
C15 C14 H14A . . 111.2 ?
C13 C14 H14A . . 111.2 ?
C15 C14 H14B . . 111.2 ?
C13 C14 H14B . . 111.2 ?
H14A C14 H14B . . 109.1 ?
N1 C15 C14 . . 103.90(14) ?
N1 C15 H15A . . 111.0 ?
C14 C15 H15A . . 111.0 ?
N1 C15 H15B . . 111.0 ?
C14 C15 H15B . . 111.0 ?
H15A C15 H15B . . 109.0 ?
C22 C21 C26 . . 112.51(15) ?
C22 C21 B1 . . 129.20(15) ?
C26 C21 B1 . . 118.29(14) ?
F22 C22 C23 . . 113.39(14) ?
F22 C22 C21 . . 121.74(15) ?
C23 C22 C21 . . 124.84(16) ?
F23 C23 C24 . . 119.41(15) ?
F23 C23 C22 . . 120.77(16) ?
C24 C23 C22 . . 119.82(15) ?
F24 C24 C23 . . 121.09(15) ?
F24 C24 C25 . . 120.34(16) ?
C23 C24 C25 . . 118.57(15) ?
F25 C25 C24 . . 119.28(15) ?
F25 C25 C26 . . 121.29(15) ?
C24 C25 C26 . . 119.43(16) ?
F26 C26 C25 . . 115.26(15) ?
F26 C26 C21 . . 119.92(14) ?
C25 C26 C21 . . 124.82(15) ?
C36 C31 C32 . . 112.26(15) ?
C36 C31 B1 . . 125.75(15) ?
C32 C31 B1 . . 121.97(14) ?
F32 C32 C33 . . 114.46(16) ?
F32 C32 C31 . . 120.35(15) ?
C33 C32 C31 . . 125.18(17) ?
F33 C33 C34 . . 120.18(17) ?
F33 C33 C32 . . 120.54(17) ?
C34 C33 C32 . . 119.29(18) ?
F34 C34 C35 . . 120.82(18) ?
F34 C34 C33 . . 120.58(19) ?
C35 C34 C33 . . 118.59(17) ?
F35 C35 C34 . . 120.00(16) ?
F35 C35 C36 . . 119.59(17) ?
C34 C35 C36 . . 120.39(17) ?
F36 C36 C35 . . 114.23(15) ?
F36 C36 C31 . . 121.48(15) ?
C35 C36 C31 . . 124.28(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
C31 B1 C1 C2 . . . . 137.51(17) ?
C21 B1 C1 C2 . . . . 19.4(2) ?
C6 B1 C1 C2 . . . . -99.55(19) ?
B1 C1 C2 C3 . . . . 171.44(16) ?
C1 C2 C3 C4 . . . . -174.78(18) ?
C1 C2 C3 C5 . . . . 4.8(3) ?
C1 B1 C6 C7 . . . . -25.89(17) ?
C31 B1 C6 C7 . . . . 97.93(16) ?
C21 B1 C6 C7 . . . . -143.84(14) ?
C1 B1 C6 C11 . . . . -154.57(14) ?
C31 B1 C6 C11 . . . . -30.75(19) ?
C21 B1 C6 C11 . . . . 87.48(17) ?
C12 N1 C7 C6 . . . . 2.2(2) ?
C15 N1 C7 C6 . . . . -178.22(15) ?
C12 N1 C7 C8 . . . . -176.32(15) ?
C15 N1 C7 C8 . . . . 3.3(2) ?
C11 C6 C7 N1 . . . . -131.16(16) ?
B1 C6 C7 N1 . . . . 96.37(17) ?
C11 C6 C7 C8 . . . . 47.34(19) ?
B1 C6 C7 C8 . . . . -85.13(17) ?
N1 C7 C8 C9 . . . . 123.93(17) ?
C6 C7 C8 C9 . . . . -54.60(19) ?
C7 C8 C9 C10 . . . . 57.65(19) ?
C8 C9 C10 C11 . . . . -57.7(2) ?
C9 C10 C11 C6 . . . . 51.5(2) ?
C7 C6 C11 C10 . . . . -44.6(2) ?
B1 C6 C11 C10 . . . . 84.47(19) ?
C7 N1 C12 C13 . . . . 166.10(15) ?
C15 N1 C12 C13 . . . . -13.57(18) ?
N1 C12 C13 C14 . . . . 33.66(18) ?
C12 C13 C14 C15 . . . . -41.42(19) ?
C7 N1 C15 C14 . . . . 168.23(16) ?
C12 N1 C15 C14 . . . . -12.09(18) ?
C13 C14 C15 N1 . . . . 32.75(18) ?
C1 B1 C21 C22 . . . . -121.66(18) ?
C31 B1 C21 C22 . . . . 116.10(17) ?
C6 B1 C21 C22 . . . . -5.3(2) ?
C1 B1 C21 C26 . . . . 59.03(18) ?
C31 B1 C21 C26 . . . . -63.21(18) ?
C6 B1 C21 C26 . . . . 175.40(14) ?
C26 C21 C22 F22 . . . . 176.80(14) ?
B1 C21 C22 F22 . . . . -2.5(3) ?
C26 C21 C22 C23 . . . . -1.2(2) ?
B1 C21 C22 C23 . . . . 179.42(16) ?
F22 C22 C23 F23 . . . . 2.0(2) ?
C21 C22 C23 F23 . . . . -179.82(15) ?
F22 C22 C23 C24 . . . . -177.57(15) ?
C21 C22 C23 C24 . . . . 0.6(3) ?
F23 C23 C24 F24 . . . . 1.7(2) ?
C22 C23 C24 F24 . . . . -178.75(15) ?
F23 C23 C24 C25 . . . . -179.05(15) ?
C22 C23 C24 C25 . . . . 0.5(3) ?
F24 C24 C25 F25 . . . . -1.6(2) ?
C23 C24 C25 F25 . . . . 179.07(15) ?
F24 C24 C25 C26 . . . . 178.40(15) ?
C23 C24 C25 C26 . . . . -0.9(3) ?
F25 C25 C26 F26 . . . . -0.6(2) ?
C24 C25 C26 F26 . . . . 179.38(14) ?
F25 C25 C26 C21 . . . . -179.78(15) ?
C24 C25 C26 C21 . . . . 0.2(3) ?
C22 C21 C26 F26 . . . . -178.32(14) ?
B1 C21 C26 F26 . . . . 1.1(2) ?
C22 C21 C26 C25 . . . . 0.8(2) ?
B1 C21 C26 C25 . . . . -179.74(15) ?
C1 B1 C31 C36 . . . . 20.3(2) ?
C21 B1 C31 C36 . . . . 139.87(16) ?
C6 B1 C31 C36 . . . . -99.59(18) ?
C1 B1 C31 C32 . . . . -157.93(15) ?
C21 B1 C31 C32 . . . . -38.4(2) ?
C6 B1 C31 C32 . . . . 82.14(19) ?
C36 C31 C32 F32 . . . . 178.94(15) ?
B1 C31 C32 F32 . . . . -2.6(3) ?
C36 C31 C32 C33 . . . . -0.6(3) ?
B1 C31 C32 C33 . . . . 177.84(17) ?
F32 C32 C33 F33 . . . . 0.8(3) ?
C31 C32 C33 F33 . . . . -179.62(17) ?
F32 C32 C33 C34 . . . . -178.98(17) ?
C31 C32 C33 C34 . . . . 0.6(3) ?
F33 C33 C34 F34 . . . . 1.1(3) ?
C32 C33 C34 F34 . . . . -179.09(18) ?
F33 C33 C34 C35 . . . . -179.77(17) ?
C32 C33 C34 C35 . . . . 0.0(3) ?
F34 C34 C35 F35 . . . . 0.2(3) ?
C33 C34 C35 F35 . . . . -178.85(16) ?
F34 C34 C35 C36 . . . . 178.57(17) ?
C33 C34 C35 C36 . . . . -0.5(3) ?
F35 C35 C36 F36 . . . . -2.0(2) ?
C34 C35 C36 F36 . . . . 179.66(16) ?
F35 C35 C36 C31 . . . . 178.82(15) ?
C34 C35 C36 C31 . . . . 0.5(3) ?
C32 C31 C36 F36 . . . . -179.04(15) ?
B1 C31 C36 F36 . . . . 2.5(3) ?
C32 C31 C36 C35 . . . . 0.1(2) ?
B1 C31 C36 C35 . . . . -178.33(16) ?

####################################################################### 
# 
# 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_erk7963
_database_code_depnum_ccdc_archive 'CCDC 1411189'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 B F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         429.07

_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                   9.0935(5)
_cell_length_b                   9.5304(5)
_cell_length_c                   11.4509(7)
_cell_angle_alpha                70.278(2)
_cell_angle_beta                 74.540(2)
_cell_angle_gamma                65.394(2)
_cell_volume                     840.08(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6710
_cell_measurement_theta_min      2.4906
_cell_measurement_theta_max      26.4180
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.173
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428

_exptl_absorpt_coefficient_mu    0.177
_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  0.91
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(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            14380
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3450
_reflns_number_gt                2806
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0920
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_number_reflns         3450
_refine_ls_number_parameters     262
_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)+(0.0379P)²+0.4930P] 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         0.264
_refine_diff_density_min         -0.252
_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 0.5616(2) 0.7321(2) 0.78067(16) 0.0170(4) Uani d . . . 1 . .
C C1 0.8505(2) 0.5912(2) 0.82758(16) 0.0215(4) Uani d . . . 1 . .
H H1A 0.8365 0.4986 0.8174 0.026 Uiso calc U . R 1 . .
H H1B 0.8758 0.5636 0.9133 0.026 Uiso calc U . R 1 . .
N N1 0.69768(16) 0.73102(16) 0.81170(12) 0.0175(3) Uani d . . . 1 . .
C C2 0.9917(2) 0.6254(2) 0.73186(17) 0.0239(4) Uani d . . . 1 . .
H H2A 0.971 0.6434 0.6464 0.029 Uiso calc U . R 1 . .
H H2B 1.0939 0.5318 0.7466 0.029 Uiso calc U . R 1 . .
C C3 1.0123(2) 0.7726(2) 0.74097(19) 0.0284(4) Uani d . . . 1 . .
H H3A 1.051 0.7483 0.8211 0.034 Uiso calc U . R 1 . .
H H3B 1.0956 0.8003 0.6715 0.034 Uiso calc U . R 1 . .
C C4 0.8502(2) 0.9145(2) 0.73412(17) 0.0251(4) Uani d . . . 1 . .
H H4A 0.8626 1.0043 0.7504 0.03 Uiso calc U . R 1 . .
H H4B 0.8213 0.9501 0.6487 0.03 Uiso calc U . R 1 . .
C C5 0.7129(2) 0.8707(2) 0.82934(16) 0.0194(3) Uani d . . . 1 . .
H H5A 0.7359 0.8459 0.9153 0.023 Uiso calc U . R 1 . .
H H5B 0.6085 0.9627 0.8193 0.023 Uiso calc U . R 1 . .
C C11 0.55744(19) 0.58337(18) 0.74880(15) 0.0172(3) Uani d . . . 1 . .
C C12 0.64552(19) 0.5322(2) 0.64242(15) 0.0193(3) Uani d . . . 1 . .
F F12 0.74989(12) 0.60220(13) 0.56443(10) 0.0283(2) Uani d . . . 1 . .
C C13 0.6306(2) 0.4121(2) 0.60962(16) 0.0216(4) Uani d . . . 1 . .
F F13 0.71786(13) 0.36749(13) 0.50506(10) 0.0314(3) Uani d . . . 1 . .
C C14 0.5224(2) 0.33973(19) 0.68522(16) 0.0219(4) Uani d . . . 1 . .
F F14 0.50273(14) 0.22586(12) 0.65355(10) 0.0323(3) Uani d . . . 1 . .
C C15 0.4336(2) 0.3849(2) 0.79261(16) 0.0213(4) Uani d . . . 1 . .
F F15 0.32907(13) 0.31314(12) 0.86654(10) 0.0305(3) Uani d . . . 1 . .
C C16 0.4513(2) 0.50598(19) 0.82179(15) 0.0186(3) Uani d . . . 1 . .
F F16 0.35972(12) 0.54957(12) 0.92667(9) 0.0255(2) Uani d . . . 1 . .
C C21 0.39485(19) 0.88318(19) 0.77435(15) 0.0167(3) Uani d . . . 1 . .
C C22 0.3224(2) 0.95499(19) 0.66622(15) 0.0184(3) Uani d . . . 1 . .
F F22 0.39870(12) 0.90160(12) 0.56290(9) 0.0261(2) Uani d . . . 1 . .
C C23 0.1729(2) 1.0782(2) 0.65918(16) 0.0228(4) Uani d . . . 1 . .
F F23 0.10491(14) 1.14171(13) 0.55376(10) 0.0353(3) Uani d . . . 1 . .
C C24 0.0900(2) 1.1334(2) 0.76353(18) 0.0250(4) Uani d . . . 1 . .
F F24 -0.05808(13) 1.25059(13) 0.75916(12) 0.0400(3) Uani d . . . 1 . .
C C25 0.1564(2) 1.0665(2) 0.87325(17) 0.0236(4) Uani d . . . 1 . .
F F25 0.07318(13) 1.12024(14) 0.97528(11) 0.0360(3) Uani d . . . 1 . .
C C26 0.3062(2) 0.9432(2) 0.87690(15) 0.0198(3) Uani d . . . 1 . .
F F26 0.36512(13) 0.87822(13) 0.98742(9) 0.0289(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 N1 . 1.371(2) ?
B1 C11 . 1.595(2) ?
B1 C21 . 1.596(2) ?
C1 N1 . 1.473(2) ?
C1 C2 . 1.521(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
N1 C5 . 1.477(2) ?
C2 C3 . 1.530(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.529(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.524(2) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C11 C12 . 1.385(2) ?
C11 C16 . 1.386(2) ?
C12 F12 . 1.3481(19) ?
C12 C13 . 1.384(2) ?
C13 F13 . 1.341(2) ?
C13 C14 . 1.379(2) ?
C14 F14 . 1.3427(19) ?
C14 C15 . 1.374(3) ?
C15 F15 . 1.3450(19) ?
C15 C16 . 1.383(2) ?
C16 F16 . 1.3507(19) ?
C21 C26 . 1.386(2) ?
C21 C22 . 1.387(2) ?
C22 F22 . 1.3472(18) ?
C22 C23 . 1.378(2) ?
C23 F23 . 1.3412(19) ?
C23 C24 . 1.373(3) ?
C24 F24 . 1.3447(19) ?
C24 C25 . 1.376(3) ?
C25 F25 . 1.3452(19) ?
C25 C26 . 1.379(2) ?
C26 F26 . 1.3523(19) ?

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
N1 B1 C11 . . 122.80(15) ?
N1 B1 C21 . . 122.09(15) ?
C11 B1 C21 . . 115.11(13) ?
N1 C1 C2 . . 110.83(14) ?
N1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
B1 N1 C1 . . 124.27(14) ?
B1 N1 C5 . . 124.73(14) ?
C1 N1 C5 . . 110.97(13) ?
C1 C2 C3 . . 110.95(14) ?
C1 C2 H2A . . 109.5 ?
C3 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.0 ?
C4 C3 C2 . . 110.59(14) ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 111.40(14) ?
C5 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
C5 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
N1 C5 C4 . . 110.53(13) ?
N1 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C12 C11 C16 . . 115.40(15) ?
C12 C11 B1 . . 123.46(14) ?
C16 C11 B1 . . 120.87(14) ?
F12 C12 C13 . . 117.09(14) ?
F12 C12 C11 . . 119.72(14) ?
C13 C12 C11 . . 123.19(15) ?
F13 C13 C14 . . 120.06(15) ?
F13 C13 C12 . . 120.93(16) ?
C14 C13 C12 . . 119.00(15) ?
F14 C14 C15 . . 119.89(16) ?
F14 C14 C13 . . 120.05(15) ?
C15 C14 C13 . . 120.05(15) ?
F15 C15 C14 . . 119.82(15) ?
F15 C15 C16 . . 121.00(15) ?
C14 C15 C16 . . 119.17(15) ?
F16 C16 C15 . . 117.61(14) ?
F16 C16 C11 . . 119.22(14) ?
C15 C16 C11 . . 123.17(15) ?
C26 C21 C22 . . 115.44(15) ?
C26 C21 B1 . . 123.30(14) ?
C22 C21 B1 . . 121.05(14) ?
F22 C22 C23 . . 117.59(14) ?
F22 C22 C21 . . 119.32(14) ?
C23 C22 C21 . . 123.09(15) ?
F23 C23 C24 . . 119.54(16) ?
F23 C23 C22 . . 121.26(16) ?
C24 C23 C22 . . 119.17(15) ?
F24 C24 C23 . . 119.88(16) ?
F24 C24 C25 . . 119.97(16) ?
C23 C24 C25 . . 120.14(16) ?
F25 C25 C24 . . 119.62(15) ?
F25 C25 C26 . . 121.27(16) ?
C24 C25 C26 . . 119.10(15) ?
F26 C26 C25 . . 117.19(15) ?
F26 C26 C21 . . 119.74(14) ?
C25 C26 C21 . . 123.06(15) ?

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
C11 B1 N1 C1 . . . . -4.3(2) ?
C21 B1 N1 C1 . . . . 175.50(14) ?
C11 B1 N1 C5 . . . . 173.47(14) ?
C21 B1 N1 C5 . . . . -6.7(2) ?
C2 C1 N1 B1 . . . . 117.52(17) ?
C2 C1 N1 C5 . . . . -60.52(17) ?
N1 C1 C2 C3 . . . . 56.66(19) ?
C1 C2 C3 C4 . . . . -52.4(2) ?
C2 C3 C4 C5 . . . . 52.2(2) ?
B1 N1 C5 C4 . . . . -118.13(17) ?
C1 N1 C5 C4 . . . . 59.90(17) ?
C3 C4 C5 N1 . . . . -55.87(18) ?
N1 B1 C11 C12 . . . . -68.2(2) ?
C21 B1 C11 C12 . . . . 112.03(17) ?
N1 B1 C11 C16 . . . . 118.06(18) ?
C21 B1 C11 C16 . . . . -61.8(2) ?
C16 C11 C12 F12 . . . . 178.90(14) ?
B1 C11 C12 F12 . . . . 4.8(2) ?
C16 C11 C12 C13 . . . . -0.1(2) ?
B1 C11 C12 C13 . . . . -174.17(15) ?
F12 C12 C13 F13 . . . . 0.5(2) ?
C11 C12 C13 F13 . . . . 179.52(15) ?
F12 C12 C13 C14 . . . . -178.51(14) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
F13 C13 C14 F14 . . . . -0.8(2) ?
C12 C13 C14 F14 . . . . 178.26(15) ?
F13 C13 C14 C15 . . . . 179.71(15) ?
C12 C13 C14 C15 . . . . -1.3(2) ?
F14 C14 C15 F15 . . . . 1.0(2) ?
C13 C14 C15 F15 . . . . -179.49(15) ?
F14 C14 C15 C16 . . . . -177.92(14) ?
C13 C14 C15 C16 . . . . 1.6(2) ?
F15 C15 C16 F16 . . . . -0.2(2) ?
C14 C15 C16 F16 . . . . 178.68(14) ?
F15 C15 C16 C11 . . . . 179.90(15) ?
C14 C15 C16 C11 . . . . -1.2(3) ?
C12 C11 C16 F16 . . . . -179.45(14) ?
B1 C11 C16 F16 . . . . -5.2(2) ?
C12 C11 C16 C15 . . . . 0.4(2) ?
B1 C11 C16 C15 . . . . 174.69(15) ?
N1 B1 C21 C26 . . . . -61.5(2) ?
C11 B1 C21 C26 . . . . 118.27(17) ?
N1 B1 C21 C22 . . . . 123.95(17) ?
C11 B1 C21 C22 . . . . -56.2(2) ?
C26 C21 C22 F22 . . . . -178.58(14) ?
B1 C21 C22 F22 . . . . -3.7(2) ?
C26 C21 C22 C23 . . . . 0.3(2) ?
B1 C21 C22 C23 . . . . 175.23(15) ?
F22 C22 C23 F23 . . . . 0.7(2) ?
C21 C22 C23 F23 . . . . -178.23(15) ?
F22 C22 C23 C24 . . . . 178.61(14) ?
C21 C22 C23 C24 . . . . -0.3(3) ?
F23 C23 C24 F24 . . . . -0.2(2) ?
C22 C23 C24 F24 . . . . -178.17(15) ?
F23 C23 C24 C25 . . . . 178.31(16) ?
C22 C23 C24 C25 . . . . 0.3(3) ?
F24 C24 C25 F25 . . . . -0.7(3) ?
C23 C24 C25 F25 . . . . -179.23(15) ?
F24 C24 C25 C26 . . . . 178.09(15) ?
C23 C24 C25 C26 . . . . -0.4(3) ?
F25 C25 C26 F26 . . . . 0.4(2) ?
C24 C25 C26 F26 . . . . -178.39(15) ?
F25 C25 C26 C21 . . . . 179.25(15) ?
C24 C25 C26 C21 . . . . 0.5(3) ?
C22 C21 C26 F26 . . . . 178.43(14) ?
B1 C21 C26 F26 . . . . 3.6(2) ?
C22 C21 C26 C25 . . . . -0.4(2) ?
B1 C21 C26 C25 . . . . -175.18(16) ?

