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

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

data_2a
_database_code_depnum_ccdc_archive 'CCDC 1018403'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C69 H45 B3 F6 N6'
_chemical_formula_weight         1104.54

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   17.0474(6)
_cell_length_b                   13.3497(4)
_cell_length_c                   49.6003(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.859(3)
_cell_angle_gamma                90.00
_cell_volume                     11282.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6776
_cell_measurement_theta_min      3.0880
_cell_measurement_theta_max      30.6160

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4560
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38792
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9903
_reflns_number_gt                6424
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0414P)²+9.8819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9903
_refine_ls_number_parameters     758
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
B1 B 0.4503(2) 0.4348(3) 0.70422(8) 0.0583(10) Uani 1 1 d . . .
B2 B 0.8536(2) 0.4268(3) 0.62575(6) 0.0493(8) Uani 1 1 d . . .
B3 B 0.8712(2) 0.3806(3) 1.04120(7) 0.0565(9) Uani 1 1 d . . .
F1 F 0.43300(12) 0.51324(15) 0.72117(4) 0.0837(6) Uani 1 1 d . . .
F2 F 0.43231(12) 0.34480(15) 0.71672(4) 0.0858(6) Uani 1 1 d . . .
F3 F 0.77446(10) 0.43264(14) 0.61848(4) 0.0706(5) Uani 1 1 d . . .
F4 F 0.89551(12) 0.39525(14) 0.60426(3) 0.0769(6) Uani 1 1 d . . .
F5 F 0.94032(11) 0.37213(16) 1.05678(3) 0.0792(6) Uani 1 1 d . . .
F6 F 0.81227(11) 0.41566(15) 1.05699(4) 0.0798(6) Uani 1 1 d . . .
N1 N 0.53787(14) 0.43641(17) 0.69742(5) 0.0506(6) Uani 1 1 d . . .
N2 N 0.40303(15) 0.44499(18) 0.67736(5) 0.0558(6) Uani 1 1 d . . .
N3 N 0.88300(13) 0.53014(17) 0.63593(4) 0.0449(6) Uani 1 1 d . . .
N4 N 0.86465(14) 0.35468(17) 0.64994(5) 0.0504(6) Uani 1 1 d . . .
N5 N 0.84925(14) 0.27786(19) 1.02909(5) 0.0537(6) Uani 1 1 d . . .
N6 N 0.88448(14) 0.45116(19) 1.01712(5) 0.0534(6) Uani 1 1 d . . .
C1 C 0.5999(2) 0.4306(2) 0.71468(6) 0.0606(8) Uani 1 1 d . . .
H1 H 0.5967 0.4249 0.7337 0.073 Uiso 1 1 calc R . .
C2 C 0.6697(2) 0.4340(2) 0.70085(7) 0.0649(9) Uani 1 1 d . . .
H2 H 0.7213 0.4310 0.7086 0.078 Uiso 1 1 calc R . .
C3 C 0.65001(18) 0.4424(2) 0.67397(7) 0.0593(8) Uani 1 1 d . . .
H3 H 0.6854 0.4458 0.6596 0.071 Uiso 1 1 calc R . .
C4 C 0.56751(18) 0.4450(2) 0.67163(6) 0.0489(7) Uani 1 1 d . . .
C5 C 0.51646(18) 0.4541(2) 0.64925(6) 0.0527(8) Uani 1 1 d . . .
C6 C 0.43452(19) 0.4568(2) 0.65214(6) 0.0543(8) Uani 1 1 d . . .
C7 C 0.3727(2) 0.4665(3) 0.63313(8) 0.0730(10) Uani 1 1 d . . .
H7 H 0.3771 0.4755 0.6142 0.088 Uiso 1 1 calc R . .
C8 C 0.3042(2) 0.4605(3) 0.64696(9) 0.0869(12) Uani 1 1 d . . .
H8 H 0.2525 0.4647 0.6394 0.104 Uiso 1 1 calc R . .
C9 C 0.3246(2) 0.4473(3) 0.67392(8) 0.0751(10) Uani 1 1 d . . .
H9 H 0.2883 0.4409 0.6880 0.090 Uiso 1 1 calc R . .
C10 C 0.54525(19) 0.4561(2) 0.62269(6) 0.0593(8) Uani 1 1 d . . .
C11 C 0.56468(19) 0.4471(2) 0.59979(6) 0.0617(8) Uani 1 1 d . . .
C12 C 0.58250(19) 0.4296(2) 0.57217(6) 0.0566(8) Uani 1 1 d . . .
C13 C 0.65682(18) 0.4386(2) 0.56263(6) 0.0575(8) Uani 1 1 d . . .
H13 H 0.6988 0.4593 0.5744 0.069 Uiso 1 1 calc R . .
C14 C 0.67054(17) 0.4176(2) 0.53600(6) 0.0573(8) Uani 1 1 d . . .
H14 H 0.7224 0.4247 0.5298 0.069 Uiso 1 1 calc R . .
C15 C 0.61177(17) 0.3867(2) 0.51796(6) 0.0501(7) Uani 1 1 d . . .
C16 C 0.5376(2) 0.3772(3) 0.52802(7) 0.0865(12) Uani 1 1 d . . .
H16 H 0.4956 0.3559 0.5164 0.104 Uiso 1 1 calc R . .
C17 C 0.5232(2) 0.3982(3) 0.55460(7) 0.0956(14) Uani 1 1 d . . .
H17 H 0.4715 0.3908 0.5609 0.115 Uiso 1 1 calc R . .
C18 C 0.6264(2) 0.3638(2) 0.48939(6) 0.0574(8) Uani 1 1 d . . .
C19 C 0.7008(2) 0.3432(3) 0.48075(7) 0.0807(11) Uani 1 1 d . . .
H19 H 0.7434 0.3435 0.4936 0.097 Uiso 1 1 calc R . .
C20 C 0.7153(3) 0.3223(4) 0.45431(9) 0.1079(15) Uani 1 1 d . . .
H20 H 0.7673 0.3086 0.4491 0.129 Uiso 1 1 calc R . .
C21 C 0.6554(4) 0.3210(4) 0.43564(10) 0.130(2) Uani 1 1 d . . .
H21 H 0.6651 0.3045 0.4174 0.156 Uiso 1 1 calc R . .
C22 C 0.5808(3) 0.3436(5) 0.44331(9) 0.140(2) Uani 1 1 d . . .
H22 H 0.5389 0.3449 0.4302 0.167 Uiso 1 1 calc R . .
C23 C 0.5665(2) 0.3645(4) 0.46992(7) 0.0991(14) Uani 1 1 d . . .
H23 H 0.5145 0.3796 0.4750 0.119 Uiso 1 1 calc R . .
C24 C 0.8552(2) 0.2544(2) 0.65038(8) 0.0716(10) Uani 1 1 d . . .
H24 H 0.8453 0.2141 0.6348 0.086 Uiso 1 1 calc R . .
C25 C 0.8617(2) 0.2181(3) 0.67639(8) 0.0797(11) Uani 1 1 d . . .
H25 H 0.8575 0.1501 0.6818 0.096 Uiso 1 1 calc R . .
C26 C 0.8755(2) 0.2991(3) 0.69294(7) 0.0676(9) Uani 1 1 d . . .
H26 H 0.8829 0.2976 0.7120 0.081 Uiso 1 1 calc R . .
C27 C 0.87667(16) 0.3838(2) 0.67653(5) 0.0481(7) Uani 1 1 d . . .
C28 C 0.88973(15) 0.4856(2) 0.68305(5) 0.0451(7) Uani 1 1 d . . .
C29 C 0.89423(16) 0.5573(2) 0.66287(5) 0.0435(7) Uani 1 1 d . . .
C30 C 0.91435(17) 0.6600(2) 0.66368(6) 0.0558(8) Uani 1 1 d . . .
H30 H 0.9249 0.6990 0.6794 0.067 Uiso 1 1 calc R . .
C31 C 0.9158(2) 0.6927(2) 0.63758(7) 0.0662(9) Uani 1 1 d . . .
H31 H 0.9282 0.7585 0.6318 0.079 Uiso 1 1 calc R . .
C32 C 0.89588(18) 0.6114(2) 0.62094(6) 0.0600(8) Uani 1 1 d . . .
H32 H 0.8920 0.6136 0.6018 0.072 Uiso 1 1 calc R . .
C33 C 0.89673(18) 0.5127(2) 0.71069(6) 0.0541(8) Uani 1 1 d . . .
C34 C 0.89747(18) 0.5294(2) 0.73429(6) 0.0558(8) Uani 1 1 d . . .
C35 C 0.89563(17) 0.5488(2) 0.76264(5) 0.0508(7) Uani 1 1 d . . .
C36 C 0.90339(18) 0.6455(2) 0.77292(6) 0.0560(8) Uani 1 1 d . . .
H36 H 0.9116 0.7000 0.7611 0.067 Uiso 1 1 calc R . .
C37 C 0.89915(18) 0.6623(2) 0.80020(5) 0.0517(7) Uani 1 1 d . . .
H37 H 0.9039 0.7289 0.8068 0.062 Uiso 1 1 calc R . .
C38 C 0.88808(16) 0.5845(2) 0.81838(5) 0.0428(6) Uani 1 1 d . . .
C39 C 0.88164(18) 0.4879(2) 0.80792(6) 0.0535(8) Uani 1 1 d . . .
H39 H 0.8748 0.4331 0.8199 0.064 Uiso 1 1 calc R . .
C40 C 0.88507(18) 0.4701(2) 0.78058(6) 0.0563(8) Uani 1 1 d . . .
H40 H 0.8802 0.4036 0.7739 0.068 Uiso 1 1 calc R . .
C41 C 0.88466(16) 0.6038(2) 0.84769(5) 0.0446(7) Uani 1 1 d . . .
C42 C 0.84994(18) 0.6905(2) 0.85746(6) 0.0552(8) Uani 1 1 d . . .
H42 H 0.8265 0.7370 0.8451 0.066 Uiso 1 1 calc R . .
C43 C 0.8491(2) 0.7097(3) 0.88475(7) 0.0718(10) Uani 1 1 d . . .
H43 H 0.8244 0.7685 0.8911 0.086 Uiso 1 1 calc R . .
C44 C 0.8837(2) 0.6439(3) 0.90273(7) 0.0798(11) Uani 1 1 d . . .
H44 H 0.8849 0.6583 0.9215 0.096 Uiso 1 1 calc R . .
C45 C 0.9167(2) 0.5571(3) 0.89355(6) 0.0745(10) Uani 1 1 d . . .
H45 H 0.9397 0.5110 0.9061 0.089 Uiso 1 1 calc R . .
C46 C 0.91683(18) 0.5362(2) 0.86633(6) 0.0556(8) Uani 1 1 d . . .
H46 H 0.9390 0.4753 0.8603 0.067 Uiso 1 1 calc R . .
C47 C 0.82513(19) 0.1964(3) 1.04232(7) 0.0694(10) Uani 1 1 d . . .
H47 H 0.8166 0.1937 1.0611 0.083 Uiso 1 1 calc R . .
C48 C 0.8144(2) 0.1164(3) 1.02462(9) 0.0798(11) Uani 1 1 d . . .
H48 H 0.7980 0.0506 1.0291 0.096 Uiso 1 1 calc R . .
C49 C 0.83220(19) 0.1506(3) 0.99944(8) 0.0699(10) Uani 1 1 d . . .
H49 H 0.8300 0.1129 0.9832 0.084 Uiso 1 1 calc R . .
C50 C 0.85423(17) 0.2515(2) 1.00212(6) 0.0513(7) Uani 1 1 d . . .
C51 C 0.87550(16) 0.3226(2) 0.98303(6) 0.0514(8) Uani 1 1 d . . .
C52 C 0.89025(17) 0.4215(2) 0.99047(6) 0.0522(8) Uani 1 1 d . . .
C53 C 0.9087(2) 0.5064(3) 0.97510(7) 0.0690(9) Uani 1 1 d . . .
H53 H 0.9161 0.5079 0.9562 0.083 Uiso 1 1 calc R . .
C54 C 0.9141(2) 0.5862(3) 0.99237(9) 0.0796(11) Uani 1 1 d . . .
H54 H 0.9257 0.6535 0.9877 0.095 Uiso 1 1 calc R . .
C55 C 0.89940(19) 0.5505(3) 1.01804(8) 0.0699(9) Uani 1 1 d . . .
H55 H 0.8998 0.5903 1.0339 0.084 Uiso 1 1 calc R . .
C56 C 0.87968(18) 0.2935(3) 0.95540(6) 0.0626(9) Uani 1 1 d . . .
C57 C 0.88029(19) 0.2688(3) 0.93226(6) 0.0630(9) Uani 1 1 d . . .
C58 C 0.87706(18) 0.2441(2) 0.90418(6) 0.0551(8) Uani 1 1 d . . .
C59 C 0.93626(19) 0.2746(2) 0.88729(6) 0.0594(8) Uani 1 1 d . . .
H59 H 0.9818 0.3066 0.8947 0.071 Uiso 1 1 calc R . .
C60 C 0.92917(17) 0.2585(2) 0.85979(6) 0.0534(8) Uani 1 1 d . . .
H60 H 0.9706 0.2785 0.8486 0.064 Uiso 1 1 calc R . .
C61 C 0.86276(16) 0.2138(2) 0.84809(5) 0.0452(7) Uani 1 1 d . . .
C62 C 0.80543(18) 0.1796(2) 0.86548(6) 0.0581(8) Uani 1 1 d . . .
H62 H 0.7604 0.1461 0.8582 0.070 Uiso 1 1 calc R . .
C63 C 0.81293(19) 0.1935(3) 0.89295(6) 0.0653(9) Uani 1 1 d . . .
H63 H 0.7738 0.1682 0.9043 0.078 Uiso 1 1 calc R . .
C64 C 0.85113(17) 0.2049(2) 0.81841(5) 0.0463(7) Uani 1 1 d . . .
C65 C 0.91312(19) 0.1848(2) 0.80182(6) 0.0572(8) Uani 1 1 d . . .
H65 H 0.9648 0.1784 0.8093 0.069 Uiso 1 1 calc R . .
C66 C 0.8997(3) 0.1741(3) 0.77414(7) 0.0739(11) Uani 1 1 d . . .
H66 H 0.9423 0.1596 0.7629 0.089 Uiso 1 1 calc R . .
C67 C 0.8256(3) 0.1843(3) 0.76295(7) 0.0800(12) Uani 1 1 d . . .
H67 H 0.8167 0.1758 0.7441 0.096 Uiso 1 1 calc R . .
C68 C 0.7645(2) 0.2067(3) 0.77912(7) 0.0757(10) Uani 1 1 d . . .
H68 H 0.7132 0.2157 0.7714 0.091 Uiso 1 1 calc R . .
C69 C 0.77693(19) 0.2162(2) 0.80656(6) 0.0574(8) Uani 1 1 d . . .
H69 H 0.7338 0.2308 0.8176 0.069 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
B1 F1 1.380(4) . ?
B1 F2 1.391(4) . ?
B1 N2 1.540(5) . ?
B1 N1 1.541(4) . ?
B2 F4 1.369(3) . ?
B2 F3 1.388(4) . ?
B2 N4 1.545(4) . ?
B2 N3 1.546(4) . ?
B3 F6 1.376(4) . ?
B3 F5 1.393(4) . ?
B3 N5 1.538(4) . ?
B3 N6 1.544(4) . ?
N1 C1 1.341(4) . ?
N1 C4 1.395(3) . ?
N2 C9 1.343(4) . ?
N2 C6 1.386(4) . ?
N3 C32 1.337(4) . ?
N3 C29 1.392(3) . ?
N4 C24 1.349(4) . ?
N4 C27 1.384(3) . ?
N5 C47 1.342(4) . ?
N5 C50 1.389(3) . ?
N6 C55 1.351(4) . ?
N6 C52 1.386(3) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(4) . ?
C5 C6 1.409(4) . ?
C5 C10 1.421(4) . ?
C6 C7 1.397(4) . ?
C7 C8 1.375(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.200(4) . ?
C11 C12 1.432(4) . ?
C12 C13 1.372(4) . ?
C12 C17 1.378(4) . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 C18 1.479(4) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.379(4) . ?
C18 C23 1.383(5) . ?
C19 C20 1.371(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.355(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.379(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.394(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.413(4) . ?
C28 C29 1.389(4) . ?
C28 C33 1.419(4) . ?
C29 C30 1.414(4) . ?
C30 C31 1.367(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.398(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.191(4) . ?
C34 C35 1.431(4) . ?
C35 C36 1.392(4) . ?
C35 C40 1.392(4) . ?
C36 C37 1.376(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.393(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.393(4) . ?
C38 C41 1.479(4) . ?
C39 C40 1.380(4) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.394(4) . ?
C41 C46 1.392(4) . ?
C42 C43 1.378(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.372(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.371(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.379(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C48 1.391(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.373(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.403(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.397(4) . ?
C51 C52 1.392(4) . ?
C51 C56 1.428(4) . ?
C52 C53 1.407(4) . ?
C53 C54 1.369(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(5) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C57 1.194(4) . ?
C57 C58 1.431(4) . ?
C58 C63 1.386(4) . ?
C58 C59 1.393(4) . ?
C59 C60 1.382(4) . ?
C59 H59 0.9500 . ?
C60 C61 1.390(4) . ?
C60 H60 0.9500 . ?
C61 C62 1.401(4) . ?
C61 C64 1.484(4) . ?
C62 C63 1.377(4) . ?
C62 H62 0.9500 . ?
C63 H63 0.9500 . ?
C64 C65 1.387(4) . ?
C64 C69 1.386(4) . ?
C65 C66 1.392(4) . ?
C65 H65 0.9500 . ?
C66 C67 1.369(5) . ?
C66 H66 0.9500 . ?
C67 C68 1.369(5) . ?
C67 H67 0.9500 . ?
C68 C69 1.377(4) . ?
C68 H68 0.9500 . ?
C69 H69 0.9500 . ?

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
F1 B1 F2 109.2(3) . . ?
F1 B1 N2 110.1(3) . . ?
F2 B1 N2 110.2(3) . . ?
F1 B1 N1 110.5(3) . . ?
F2 B1 N1 109.8(3) . . ?
N2 B1 N1 107.0(2) . . ?
F4 B2 F3 110.0(2) . . ?
F4 B2 N4 111.0(3) . . ?
F3 B2 N4 109.2(3) . . ?
F4 B2 N3 110.9(3) . . ?
F3 B2 N3 109.7(2) . . ?
N4 B2 N3 105.8(2) . . ?
F6 B3 F5 109.4(3) . . ?
F6 B3 N5 110.7(3) . . ?
F5 B3 N5 109.6(3) . . ?
F6 B3 N6 111.2(3) . . ?
F5 B3 N6 109.6(3) . . ?
N5 B3 N6 106.4(2) . . ?
C1 N1 C4 106.8(2) . . ?
C1 N1 B1 127.5(3) . . ?
C4 N1 B1 125.7(3) . . ?
C9 N2 C6 107.2(3) . . ?
C9 N2 B1 127.1(3) . . ?
C6 N2 B1 125.7(3) . . ?
C32 N3 C29 107.6(2) . . ?
C32 N3 B2 126.8(3) . . ?
C29 N3 B2 125.4(2) . . ?
C24 N4 C27 106.1(3) . . ?
C24 N4 B2 128.3(3) . . ?
C27 N4 B2 125.1(2) . . ?
C47 N5 C50 107.1(3) . . ?
C47 N5 B3 127.3(3) . . ?
C50 N5 B3 125.5(3) . . ?
C55 N6 C52 107.1(3) . . ?
C55 N6 B3 127.3(3) . . ?
C52 N6 B3 125.5(3) . . ?
N1 C1 C2 110.6(3) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C3 C2 C1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.2(3) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 N1 120.1(3) . . ?
C5 C4 C3 131.6(3) . . ?
N1 C4 C3 108.2(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 C10 121.0(3) . . ?
C6 C5 C10 117.9(3) . . ?
N2 C6 C7 108.3(3) . . ?
N2 C6 C5 120.2(3) . . ?
C7 C6 C5 131.4(3) . . ?
C8 C7 C6 107.0(3) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 C9 107.5(4) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N2 C9 C8 110.1(3) . . ?
N2 C9 H9 125.0 . . ?
C8 C9 H9 125.0 . . ?
C11 C10 C5 172.0(3) . . ?
C10 C11 C12 174.9(3) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 122.9(3) . . ?
C17 C12 C11 118.7(3) . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 122.6(3) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 116.5(3) . . ?
C16 C15 C18 120.8(3) . . ?
C14 C15 C18 122.7(3) . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C19 C18 C23 116.7(3) . . ?
C19 C18 C15 121.6(3) . . ?
C23 C18 C15 121.6(3) . . ?
C20 C19 C18 122.3(4) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.4(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 120.3(5) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 121.1(4) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
N4 C24 C25 111.0(3) . . ?
N4 C24 H24 124.5 . . ?
C25 C24 H24 124.5 . . ?
C26 C25 C24 106.8(3) . . ?
C26 C25 H25 126.6 . . ?
C24 C25 H25 126.6 . . ?
C25 C26 C27 107.2(3) . . ?
C25 C26 H26 126.4 . . ?
C27 C26 H26 126.4 . . ?
N4 C27 C26 108.9(3) . . ?
N4 C27 C28 120.4(3) . . ?
C26 C27 C28 130.7(3) . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 C33 121.1(3) . . ?
C27 C28 C33 118.3(3) . . ?
C28 C29 N3 120.2(2) . . ?
C28 C29 C30 131.8(3) . . ?
N3 C29 C30 107.8(2) . . ?
C31 C30 C29 107.1(3) . . ?
C31 C30 H30 126.4 . . ?
C29 C30 H30 126.4 . . ?
C30 C31 C32 107.5(3) . . ?
C30 C31 H31 126.3 . . ?
C32 C31 H31 126.3 . . ?
N3 C32 C31 110.0(3) . . ?
N3 C32 H32 125.0 . . ?
C31 C32 H32 125.0 . . ?
C34 C33 C28 174.2(3) . . ?
C33 C34 C35 178.1(3) . . ?
C36 C35 C40 118.6(3) . . ?
C36 C35 C34 121.5(3) . . ?
C40 C35 C34 119.9(3) . . ?
C37 C36 C35 120.3(3) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C38 121.8(3) . . ?
C36 C37 H37 119.1 . . ?
C38 C37 H37 119.1 . . ?
C37 C38 C39 117.4(3) . . ?
C37 C38 C41 121.1(2) . . ?
C39 C38 C41 121.5(2) . . ?
C40 C39 C38 121.3(3) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C35 120.6(3) . . ?
C39 C40 H40 119.7 . . ?
C35 C40 H40 119.7 . . ?
C42 C41 C46 118.0(3) . . ?
C42 C41 C38 121.2(3) . . ?
C46 C41 C38 120.8(3) . . ?
C43 C42 C41 120.9(3) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 120.1(3) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 120.0 . . ?
C43 C44 C45 119.8(3) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C44 C45 C46 120.7(3) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C45 C46 C41 120.4(3) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
N5 C47 C48 110.5(3) . . ?
N5 C47 H47 124.8 . . ?
C48 C47 H47 124.8 . . ?
C49 C48 C47 106.9(3) . . ?
C49 C48 H48 126.6 . . ?
C47 C48 H48 126.6 . . ?
C48 C49 C50 107.4(3) . . ?
C48 C49 H49 126.3 . . ?
C50 C49 H49 126.3 . . ?
N5 C50 C51 120.4(3) . . ?
N5 C50 C49 108.1(3) . . ?
C51 C50 C49 131.5(3) . . ?
C52 C51 C50 120.9(3) . . ?
C52 C51 C56 119.9(3) . . ?
C50 C51 C56 119.2(3) . . ?
N6 C52 C51 120.4(3) . . ?
N6 C52 C53 108.1(3) . . ?
C51 C52 C53 131.4(3) . . ?
C54 C53 C52 107.4(3) . . ?
C54 C53 H53 126.3 . . ?
C52 C53 H53 126.3 . . ?
C53 C54 C55 107.2(3) . . ?
C53 C54 H54 126.4 . . ?
C55 C54 H54 126.4 . . ?
N6 C55 C54 110.2(3) . . ?
N6 C55 H55 124.9 . . ?
C54 C55 H55 124.9 . . ?
C57 C56 C51 177.6(3) . . ?
C56 C57 C58 176.2(4) . . ?
C63 C58 C59 118.6(3) . . ?
C63 C58 C57 120.5(3) . . ?
C59 C58 C57 120.8(3) . . ?
C60 C59 C58 120.4(3) . . ?
C60 C59 H59 119.8 . . ?
C58 C59 H59 119.8 . . ?
C59 C60 C61 121.5(3) . . ?
C59 C60 H60 119.2 . . ?
C61 C60 H60 119.2 . . ?
C60 C61 C62 117.3(3) . . ?
C60 C61 C64 122.0(3) . . ?
C62 C61 C64 120.8(3) . . ?
C63 C62 C61 121.4(3) . . ?
C63 C62 H62 119.3 . . ?
C61 C62 H62 119.3 . . ?
C62 C63 C58 120.7(3) . . ?
C62 C63 H63 119.7 . . ?
C58 C63 H63 119.7 . . ?
C65 C64 C69 118.2(3) . . ?
C65 C64 C61 121.6(3) . . ?
C69 C64 C61 120.2(3) . . ?
C64 C65 C66 120.1(3) . . ?
C64 C65 H65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C67 C66 C65 120.7(3) . . ?
C67 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C66 C67 C68 119.6(3) . . ?
C66 C67 H67 120.2 . . ?
C68 C67 H67 120.2 . . ?
C67 C68 C69 120.2(4) . . ?
C67 C68 H68 119.9 . . ?
C69 C68 H68 119.9 . . ?
C68 C69 C64 121.3(3) . . ?
C68 C69 H69 119.4 . . ?
C64 C69 H69 119.4 . . ?

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
F1 B1 N1 C1 59.4(4) . . . . ?
F2 B1 N1 C1 -61.2(4) . . . . ?
N2 B1 N1 C1 179.3(3) . . . . ?
F1 B1 N1 C4 -120.2(3) . . . . ?
F2 B1 N1 C4 119.3(3) . . . . ?
N2 B1 N1 C4 -0.3(4) . . . . ?
F1 B1 N2 C9 -59.6(4) . . . . ?
F2 B1 N2 C9 60.9(4) . . . . ?
N1 B1 N2 C9 -179.8(3) . . . . ?
F1 B1 N2 C6 118.1(3) . . . . ?
F2 B1 N2 C6 -121.3(3) . . . . ?
N1 B1 N2 C6 -2.0(4) . . . . ?
F4 B2 N3 C32 48.4(4) . . . . ?
F3 B2 N3 C32 -73.3(4) . . . . ?
N4 B2 N3 C32 168.9(3) . . . . ?
F4 B2 N3 C29 -137.6(3) . . . . ?
F3 B2 N3 C29 100.7(3) . . . . ?
N4 B2 N3 C29 -17.1(4) . . . . ?
F4 B2 N4 C24 -52.1(4) . . . . ?
F3 B2 N4 C24 69.4(4) . . . . ?
N3 B2 N4 C24 -172.5(3) . . . . ?
F4 B2 N4 C27 136.9(3) . . . . ?
F3 B2 N4 C27 -101.6(3) . . . . ?
N3 B2 N4 C27 16.4(4) . . . . ?
F6 B3 N5 C47 -52.0(4) . . . . ?
F5 B3 N5 C47 68.7(4) . . . . ?
N6 B3 N5 C47 -172.9(3) . . . . ?
F6 B3 N5 C50 130.9(3) . . . . ?
F5 B3 N5 C50 -108.4(3) . . . . ?
N6 B3 N5 C50 10.0(4) . . . . ?
F6 B3 N6 C55 54.4(4) . . . . ?
F5 B3 N6 C55 -66.6(4) . . . . ?
N5 B3 N6 C55 175.0(3) . . . . ?
F6 B3 N6 C52 -131.8(3) . . . . ?
F5 B3 N6 C52 107.2(3) . . . . ?
N5 B3 N6 C52 -11.2(4) . . . . ?
C4 N1 C1 C2 -0.7(3) . . . . ?
B1 N1 C1 C2 179.7(3) . . . . ?
N1 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 N1 C4 C5 -179.0(3) . . . . ?
B1 N1 C4 C5 0.6(4) . . . . ?
C1 N1 C4 C3 1.0(3) . . . . ?
B1 N1 C4 C3 -179.4(3) . . . . ?
C2 C3 C4 C5 179.0(3) . . . . ?
C2 C3 C4 N1 -1.0(3) . . . . ?
N1 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
N1 C4 C5 C10 -175.7(3) . . . . ?
C3 C4 C5 C10 4.3(5) . . . . ?
C9 N2 C6 C7 0.1(3) . . . . ?
B1 N2 C6 C7 -178.1(3) . . . . ?
C9 N2 C6 C5 -178.0(3) . . . . ?
B1 N2 C6 C5 3.9(4) . . . . ?
C4 C5 C6 N2 -3.4(4) . . . . ?
C10 C5 C6 N2 173.6(3) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C10 C5 C6 C7 -3.9(5) . . . . ?
N2 C6 C7 C8 0.0(4) . . . . ?
C5 C6 C7 C8 177.7(3) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 N2 C9 C8 -0.1(4) . . . . ?
B1 N2 C9 C8 178.0(3) . . . . ?
C7 C8 C9 N2 0.1(4) . . . . ?
C4 C5 C10 C11 116(3) . . . . ?
C6 C5 C10 C11 -61(3) . . . . ?
C5 C10 C11 C12 14(6) . . . . ?
C10 C11 C12 C13 -148(4) . . . . ?
C10 C11 C12 C17 29(4) . . . . ?
C17 C12 C13 C14 0.8(5) . . . . ?
C11 C12 C13 C14 178.0(3) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C13 C14 C15 C18 -179.8(3) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C18 C15 C16 C17 179.9(4) . . . . ?
C15 C16 C17 C12 0.1(7) . . . . ?
C13 C12 C17 C16 -0.7(6) . . . . ?
C11 C12 C17 C16 -178.0(4) . . . . ?
C16 C15 C18 C19 -160.1(4) . . . . ?
C14 C15 C18 C19 19.4(5) . . . . ?
C16 C15 C18 C23 21.5(5) . . . . ?
C14 C15 C18 C23 -159.0(4) . . . . ?
C23 C18 C19 C20 -1.3(6) . . . . ?
C15 C18 C19 C20 -179.7(4) . . . . ?
C18 C19 C20 C21 -0.2(7) . . . . ?
C19 C20 C21 C22 1.9(9) . . . . ?
C20 C21 C22 C23 -2.0(9) . . . . ?
C21 C22 C23 C18 0.4(8) . . . . ?
C19 C18 C23 C22 1.2(6) . . . . ?
C15 C18 C23 C22 179.6(4) . . . . ?
C27 N4 C24 C25 -0.7(4) . . . . ?
B2 N4 C24 C25 -173.1(3) . . . . ?
N4 C24 C25 C26 0.3(4) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C24 N4 C27 C26 0.9(3) . . . . ?
B2 N4 C27 C26 173.6(3) . . . . ?
C24 N4 C27 C28 179.2(3) . . . . ?
B2 N4 C27 C28 -8.1(4) . . . . ?
C25 C26 C27 N4 -0.8(4) . . . . ?
C25 C26 C27 C28 -178.8(3) . . . . ?
N4 C27 C28 C29 -2.9(4) . . . . ?
C26 C27 C28 C29 174.9(3) . . . . ?
N4 C27 C28 C33 176.0(3) . . . . ?
C26 C27 C28 C33 -6.2(5) . . . . ?
C27 C28 C29 N3 2.4(4) . . . . ?
C33 C28 C29 N3 -176.5(2) . . . . ?
C27 C28 C29 C30 -172.6(3) . . . . ?
C33 C28 C29 C30 8.5(5) . . . . ?
C32 N3 C29 C28 -175.8(3) . . . . ?
B2 N3 C29 C28 9.3(4) . . . . ?
C32 N3 C29 C30 0.3(3) . . . . ?
B2 N3 C29 C30 -174.7(2) . . . . ?
C28 C29 C30 C31 174.8(3) . . . . ?
N3 C29 C30 C31 -0.7(3) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C29 N3 C32 C31 0.2(3) . . . . ?
B2 N3 C32 C31 175.0(3) . . . . ?
C30 C31 C32 N3 -0.6(4) . . . . ?
C29 C28 C33 C34 140(3) . . . . ?
C27 C28 C33 C34 -39(3) . . . . ?
C28 C33 C34 C35 -31(12) . . . . ?
C33 C34 C35 C36 -109(10) . . . . ?
C33 C34 C35 C40 70(10) . . . . ?
C40 C35 C36 C37 -1.2(5) . . . . ?
C34 C35 C36 C37 178.1(3) . . . . ?
C35 C36 C37 C38 0.8(5) . . . . ?
C36 C37 C38 C39 0.2(4) . . . . ?
C36 C37 C38 C41 179.2(3) . . . . ?
C37 C38 C39 C40 -0.8(4) . . . . ?
C41 C38 C39 C40 -179.8(3) . . . . ?
C38 C39 C40 C35 0.4(5) . . . . ?
C36 C35 C40 C39 0.6(5) . . . . ?
C34 C35 C40 C39 -178.7(3) . . . . ?
C37 C38 C41 C42 35.9(4) . . . . ?
C39 C38 C41 C42 -145.1(3) . . . . ?
C37 C38 C41 C46 -143.4(3) . . . . ?
C39 C38 C41 C46 35.5(4) . . . . ?
C46 C41 C42 C43 1.4(4) . . . . ?
C38 C41 C42 C43 -178.0(3) . . . . ?
C41 C42 C43 C44 1.0(5) . . . . ?
C42 C43 C44 C45 -2.4(6) . . . . ?
C43 C44 C45 C46 1.3(6) . . . . ?
C44 C45 C46 C41 1.1(5) . . . . ?
C42 C41 C46 C45 -2.5(4) . . . . ?
C38 C41 C46 C45 176.9(3) . . . . ?
C50 N5 C47 C48 0.3(4) . . . . ?
B3 N5 C47 C48 -177.2(3) . . . . ?
N5 C47 C48 C49 -0.5(4) . . . . ?
C47 C48 C49 C50 0.4(4) . . . . ?
C47 N5 C50 C51 177.8(3) . . . . ?
B3 N5 C50 C51 -4.6(4) . . . . ?
C47 N5 C50 C49 0.0(3) . . . . ?
B3 N5 C50 C49 177.5(3) . . . . ?
C48 C49 C50 N5 -0.3(4) . . . . ?
C48 C49 C50 C51 -177.7(3) . . . . ?
N5 C50 C51 C52 -1.5(4) . . . . ?
C49 C50 C51 C52 175.7(3) . . . . ?
N5 C50 C51 C56 -179.6(3) . . . . ?
C49 C50 C51 C56 -2.4(5) . . . . ?
C55 N6 C52 C51 -178.1(3) . . . . ?
B3 N6 C52 C51 7.1(4) . . . . ?
C55 N6 C52 C53 -0.4(3) . . . . ?
B3 N6 C52 C53 -175.2(3) . . . . ?
C50 C51 C52 N6 0.4(4) . . . . ?
C56 C51 C52 N6 178.4(3) . . . . ?
C50 C51 C52 C53 -176.7(3) . . . . ?
C56 C51 C52 C53 1.3(5) . . . . ?
N6 C52 C53 C54 0.1(4) . . . . ?
C51 C52 C53 C54 177.4(3) . . . . ?
C52 C53 C54 C55 0.2(4) . . . . ?
C52 N6 C55 C54 0.5(4) . . . . ?
B3 N6 C55 C54 175.2(3) . . . . ?
C53 C54 C55 N6 -0.5(4) . . . . ?
C52 C51 C56 C57 -111(9) . . . . ?
C50 C51 C56 C57 67(9) . . . . ?
C51 C56 C57 C58 52(13) . . . . ?
C56 C57 C58 C63 -72(6) . . . . ?
C56 C57 C58 C59 105(6) . . . . ?
C63 C58 C59 C60 2.8(5) . . . . ?
C57 C58 C59 C60 -174.0(3) . . . . ?
C58 C59 C60 C61 1.4(5) . . . . ?
C59 C60 C61 C62 -4.1(4) . . . . ?
C59 C60 C61 C64 174.1(3) . . . . ?
C60 C61 C62 C63 2.7(5) . . . . ?
C64 C61 C62 C63 -175.5(3) . . . . ?
C61 C62 C63 C58 1.4(5) . . . . ?
C59 C58 C63 C62 -4.2(5) . . . . ?
C57 C58 C63 C62 172.6(3) . . . . ?
C60 C61 C64 C65 37.5(4) . . . . ?
C62 C61 C64 C65 -144.4(3) . . . . ?
C60 C61 C64 C69 -142.8(3) . . . . ?
C62 C61 C64 C69 35.3(4) . . . . ?
C69 C64 C65 C66 -1.5(4) . . . . ?
C61 C64 C65 C66 178.1(3) . . . . ?
C64 C65 C66 C67 0.7(5) . . . . ?
C65 C66 C67 C68 1.0(5) . . . . ?
C66 C67 C68 C69 -1.8(5) . . . . ?
C67 C68 C69 C64 0.9(5) . . . . ?
C65 C64 C69 C68 0.7(5) . . . . ?
C61 C64 C69 C68 -179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3b
_database_code_depnum_ccdc_archive 'CCDC 1018404'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-03-13 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 H21 B F2 N2'
_chemical_formula_weight         494.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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                   9.3787(5)
_cell_length_b                   9.6798(8)
_cell_length_c                   14.6648(8)
_cell_angle_alpha                97.430(5)
_cell_angle_beta                 90.537(4)
_cell_angle_gamma                107.816(6)
_cell_volume                     1255.15(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2371
_cell_measurement_theta_min      3.7250
_cell_measurement_theta_max      29.4300

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9380
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0613
_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       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4415
_reflns_number_gt                2726
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0410P)²+0.0596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4415
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
F1 F 0.98314(13) 0.18881(17) 0.53690(10) 0.0702(5) Uani 1 1 d . . .
F2 F 0.84601(16) 0.08125(18) 0.40451(10) 0.0784(5) Uani 1 1 d . . .
B1 B 0.8402(3) 0.1428(4) 0.4939(2) 0.0509(8) Uani 1 1 d . . .
N1 N 0.77883(19) 0.2739(2) 0.49667(13) 0.0494(5) Uani 1 1 d . . .
N2 N 0.73180(18) 0.0317(2) 0.54818(13) 0.0459(5) Uani 1 1 d . . .
C1 C 0.7391(3) -0.1006(3) 0.56244(18) 0.0588(7) Uani 1 1 d . . .
H1 H 0.8100 -0.1446 0.5367 0.071 Uiso 1 1 calc R . .
C2 C 0.6280(3) -0.1641(3) 0.62033(18) 0.0614(7) Uani 1 1 d . . .
H2 H 0.6099 -0.2569 0.6407 0.074 Uiso 1 1 calc R . .
C3 C 0.5497(3) -0.0664(3) 0.64209(16) 0.0515(7) Uani 1 1 d . . .
H3 H 0.4665 -0.0800 0.6802 0.062 Uiso 1 1 calc R . .
C4 C 0.6142(2) 0.0572(3) 0.59821(15) 0.0405(6) Uani 1 1 d . . .
C5 C 0.5850(2) 0.1909(3) 0.60331(15) 0.0408(6) Uani 1 1 d . . .
C6 C 0.6656(2) 0.2981(3) 0.55143(15) 0.0432(6) Uani 1 1 d . . .
C7 C 0.6468(3) 0.4311(3) 0.53470(18) 0.0576(7) Uani 1 1 d . . .
H7 H 0.5772 0.4749 0.5626 0.069 Uiso 1 1 calc R . .
C8 C 0.7471(3) 0.4869(3) 0.4707(2) 0.0718(8) Uani 1 1 d . . .
H8 H 0.7597 0.5756 0.4459 0.086 Uiso 1 1 calc R . .
C9 C 0.8264(3) 0.3879(3) 0.44946(19) 0.0672(8) Uani 1 1 d . . .
H9 H 0.9040 0.3994 0.4072 0.081 Uiso 1 1 calc R . .
C10 C 0.4659(2) 0.2113(3) 0.66271(15) 0.0423(6) Uani 1 1 d . . .
H10 H 0.3729 0.1348 0.6550 0.051 Uiso 1 1 calc R . .
C11 C 0.4743(2) 0.3269(3) 0.72701(15) 0.0406(6) Uani 1 1 d . . .
C12 C 0.6098(2) 0.4468(3) 0.74928(15) 0.0444(6) Uani 1 1 d . . .
C13 C 0.7226(2) 0.5451(3) 0.77186(16) 0.0478(6) Uani 1 1 d . . .
C14 C 0.8620(2) 0.6587(3) 0.79833(16) 0.0466(6) Uani 1 1 d . . .
C15 C 0.8621(3) 0.7996(3) 0.83867(19) 0.0607(7) Uani 1 1 d . . .
H15 H 0.7700 0.8208 0.8452 0.073 Uiso 1 1 calc R . .
C16 C 0.9929(3) 0.9049(3) 0.86814(19) 0.0661(8) Uani 1 1 d . . .
H16 H 0.9909 0.9987 0.8954 0.079 Uiso 1 1 calc R . .
C17 C 1.1319(3) 0.8776(3) 0.85900(18) 0.0572(7) Uani 1 1 d . . .
C18 C 1.2699(3) 0.9834(3) 0.8914(2) 0.0793(10) Uani 1 1 d . . .
H18 H 1.2714 1.0789 0.9176 0.095 Uiso 1 1 calc R . .
C19 C 1.4002(3) 0.9499(5) 0.8854(2) 0.0944(13) Uani 1 1 d . . .
H19 H 1.4920 1.0222 0.9075 0.113 Uiso 1 1 calc R . .
C20 C 1.4003(3) 0.8102(5) 0.8472(2) 0.0927(12) Uani 1 1 d . . .
H20 H 1.4920 0.7875 0.8450 0.111 Uiso 1 1 calc R . .
C21 C 1.2703(3) 0.7057(4) 0.81311(19) 0.0692(8) Uani 1 1 d . . .
H21 H 1.2723 0.6120 0.7855 0.083 Uiso 1 1 calc R . .
C22 C 1.1330(2) 0.7367(3) 0.81876(16) 0.0492(6) Uani 1 1 d . . .
C23 C 0.9956(2) 0.6291(3) 0.78835(15) 0.0466(6) Uani 1 1 d . . .
H23 H 0.9955 0.5348 0.7606 0.056 Uiso 1 1 calc R . .
C24 C 0.3456(2) 0.3290(2) 0.78499(15) 0.0399(6) Uani 1 1 d . . .
C25 C 0.3719(2) 0.3934(3) 0.87872(15) 0.0477(6) Uani 1 1 d . . .
H25 H 0.4720 0.4383 0.9032 0.057 Uiso 1 1 calc R . .
C26 C 0.2553(2) 0.3918(3) 0.93418(16) 0.0511(7) Uani 1 1 d . . .
H26 H 0.2757 0.4338 0.9970 0.061 Uiso 1 1 calc R . .
C27 C 0.1049(2) 0.3287(3) 0.89974(15) 0.0422(6) Uani 1 1 d . . .
C28 C -0.0184(3) 0.3243(3) 0.95539(16) 0.0520(7) Uani 1 1 d . . .
H28 H -0.0013 0.3651 1.0185 0.062 Uiso 1 1 calc R . .
C29 C -0.1616(3) 0.2622(3) 0.91921(18) 0.0574(7) Uani 1 1 d . . .
H29 H -0.2433 0.2596 0.9574 0.069 Uiso 1 1 calc R . .
C30 C -0.1892(2) 0.2024(3) 0.82654(18) 0.0566(7) Uani 1 1 d . . .
H30 H -0.2896 0.1605 0.8020 0.068 Uiso 1 1 calc R . .
C31 C -0.0731(2) 0.2037(3) 0.77077(16) 0.0503(7) Uani 1 1 d . . .
H31 H -0.0935 0.1622 0.7079 0.060 Uiso 1 1 calc R . .
C32 C 0.0767(2) 0.2660(2) 0.80573(15) 0.0394(6) Uani 1 1 d . . .
C33 C 0.2000(2) 0.2675(3) 0.75022(15) 0.0425(6) Uani 1 1 d . . .
H33 H 0.1816 0.2249 0.6875 0.051 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.393(3) . ?
F2 B1 1.377(3) . ?
B1 N1 1.541(4) . ?
B1 N2 1.546(4) . ?
N1 C9 1.341(3) . ?
N1 C6 1.396(3) . ?
N2 C1 1.346(3) . ?
N2 C4 1.396(3) . ?
C1 C2 1.394(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.401(3) . ?
C5 C10 1.468(3) . ?
C6 C7 1.403(3) . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.349(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.435(3) . ?
C11 C24 1.487(3) . ?
C12 C13 1.196(3) . ?
C13 C14 1.439(3) . ?
C14 C23 1.373(3) . ?
C14 C15 1.415(3) . ?
C15 C16 1.357(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.415(3) . ?
C17 C22 1.418(4) . ?
C18 C19 1.358(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.365(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.409(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.412(3) . ?
C23 H23 0.9500 . ?
C24 C33 1.375(3) . ?
C24 C25 1.420(3) . ?
C25 C26 1.367(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.413(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.415(3) . ?
C27 C32 1.420(3) . ?
C28 C29 1.362(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.366(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.411(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.418(3) . ?
C33 H33 0.9500 . ?

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
F2 B1 F1 109.52(19) . . ?
F2 B1 N1 110.8(2) . . ?
F1 B1 N1 109.8(2) . . ?
F2 B1 N2 110.9(2) . . ?
F1 B1 N2 109.6(2) . . ?
N1 B1 N2 106.14(18) . . ?
C9 N1 C6 107.1(2) . . ?
C9 N1 B1 126.9(2) . . ?
C6 N1 B1 126.0(2) . . ?
C1 N2 C4 107.3(2) . . ?
C1 N2 B1 127.3(2) . . ?
C4 N2 B1 125.2(2) . . ?
N2 C1 C2 110.5(2) . . ?
N2 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C3 C2 C1 106.6(2) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 108.1(2) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
C5 C4 N2 121.3(2) . . ?
C5 C4 C3 131.1(2) . . ?
N2 C4 C3 107.5(2) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 C10 117.3(2) . . ?
C6 C5 C10 122.5(2) . . ?
N1 C6 C5 120.3(2) . . ?
N1 C6 C7 107.7(2) . . ?
C5 C6 C7 131.7(2) . . ?
C8 C7 C6 107.9(2) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C7 C8 C9 106.4(3) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N1 C9 C8 110.9(2) . . ?
N1 C9 H9 124.5 . . ?
C8 C9 H9 124.5 . . ?
C11 C10 C5 126.98(19) . . ?
C11 C10 H10 116.5 . . ?
C5 C10 H10 116.5 . . ?
C10 C11 C12 122.62(19) . . ?
C10 C11 C24 120.80(19) . . ?
C12 C11 C24 116.34(19) . . ?
C13 C12 C11 177.0(3) . . ?
C12 C13 C14 177.4(3) . . ?
C23 C14 C15 119.6(2) . . ?
C23 C14 C13 120.1(2) . . ?
C15 C14 C13 120.3(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 122.7(3) . . ?
C16 C17 C22 118.7(2) . . ?
C18 C17 C22 118.5(3) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 121.6(3) . . ?
C21 C22 C17 119.4(2) . . ?
C23 C22 C17 119.0(2) . . ?
C14 C23 C22 121.0(2) . . ?
C14 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C33 C24 C25 118.73(18) . . ?
C33 C24 C11 121.34(19) . . ?
C25 C24 C11 119.93(18) . . ?
C26 C25 C24 120.9(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 121.2(2) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 122.6(2) . . ?
C26 C27 C32 118.60(19) . . ?
C28 C27 C32 118.78(19) . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C33 122.2(2) . . ?
C31 C32 C27 118.89(19) . . ?
C33 C32 C27 118.95(18) . . ?
C24 C33 C32 121.6(2) . . ?
C24 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?

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
F2 B1 N1 C9 -50.9(3) . . . . ?
F1 B1 N1 C9 70.3(3) . . . . ?
N2 B1 N1 C9 -171.4(2) . . . . ?
F2 B1 N1 C6 131.3(2) . . . . ?
F1 B1 N1 C6 -107.6(2) . . . . ?
N2 B1 N1 C6 10.8(3) . . . . ?
F2 B1 N2 C1 58.1(3) . . . . ?
F1 B1 N2 C1 -62.9(3) . . . . ?
N1 B1 N2 C1 178.6(2) . . . . ?
F2 B1 N2 C4 -127.5(2) . . . . ?
F1 B1 N2 C4 111.4(2) . . . . ?
N1 B1 N2 C4 -7.1(3) . . . . ?
C4 N2 C1 C2 0.5(3) . . . . ?
B1 N2 C1 C2 175.6(2) . . . . ?
N2 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 N2 C4 C5 175.05(19) . . . . ?
B1 N2 C4 C5 -0.2(3) . . . . ?
C1 N2 C4 C3 -0.8(2) . . . . ?
B1 N2 C4 C3 -176.1(2) . . . . ?
C2 C3 C4 C5 -174.4(2) . . . . ?
C2 C3 C4 N2 0.9(3) . . . . ?
N2 C4 C5 C6 5.6(3) . . . . ?
C3 C4 C5 C6 -179.6(2) . . . . ?
N2 C4 C5 C10 -175.82(19) . . . . ?
C3 C4 C5 C10 -1.0(3) . . . . ?
C9 N1 C6 C5 174.7(2) . . . . ?
B1 N1 C6 C5 -7.1(3) . . . . ?
C9 N1 C6 C7 0.3(3) . . . . ?
B1 N1 C6 C7 178.5(2) . . . . ?
C4 C5 C6 N1 -2.1(3) . . . . ?
C10 C5 C6 N1 179.38(19) . . . . ?
C4 C5 C6 C7 170.8(2) . . . . ?
C10 C5 C6 C7 -7.8(4) . . . . ?
N1 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 -173.5(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C6 N1 C9 C8 -0.5(3) . . . . ?
B1 N1 C9 C8 -178.7(2) . . . . ?
C7 C8 C9 N1 0.5(3) . . . . ?
C4 C5 C10 C11 130.8(3) . . . . ?
C6 C5 C10 C11 -50.6(4) . . . . ?
C5 C10 C11 C12 -3.2(4) . . . . ?
C5 C10 C11 C24 -177.3(2) . . . . ?
C10 C11 C12 C13 -118(5) . . . . ?
C24 C11 C12 C13 56(5) . . . . ?
C11 C12 C13 C14 83(7) . . . . ?
C12 C13 C14 C23 7(6) . . . . ?
C12 C13 C14 C15 -170(6) . . . . ?
C23 C14 C15 C16 -0.6(4) . . . . ?
C13 C14 C15 C16 176.5(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 -178.1(3) . . . . ?
C15 C16 C17 C22 -0.5(4) . . . . ?
C16 C17 C18 C19 176.5(3) . . . . ?
C22 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C21 1.6(5) . . . . ?
C19 C20 C21 C22 -2.0(5) . . . . ?
C20 C21 C22 C23 -176.8(2) . . . . ?
C20 C21 C22 C17 0.9(4) . . . . ?
C16 C17 C22 C21 -177.0(2) . . . . ?
C18 C17 C22 C21 0.7(4) . . . . ?
C16 C17 C22 C23 0.7(4) . . . . ?
C18 C17 C22 C23 178.4(2) . . . . ?
C15 C14 C23 C22 0.8(4) . . . . ?
C13 C14 C23 C22 -176.3(2) . . . . ?
C21 C22 C23 C14 176.8(2) . . . . ?
C17 C22 C23 C14 -0.8(4) . . . . ?
C10 C11 C24 C33 -35.5(4) . . . . ?
C12 C11 C24 C33 150.1(2) . . . . ?
C10 C11 C24 C25 143.5(2) . . . . ?
C12 C11 C24 C25 -31.0(3) . . . . ?
C33 C24 C25 C26 1.4(4) . . . . ?
C11 C24 C25 C26 -177.6(2) . . . . ?
C24 C25 C26 C27 -1.3(4) . . . . ?
C25 C26 C27 C28 179.6(3) . . . . ?
C25 C26 C27 C32 0.2(4) . . . . ?
C26 C27 C28 C29 -179.9(2) . . . . ?
C32 C27 C28 C29 -0.6(4) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C28 C29 C30 C31 0.8(4) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C30 C31 C32 C33 179.1(2) . . . . ?
C30 C31 C32 C27 -0.6(4) . . . . ?
C26 C27 C32 C31 -179.6(2) . . . . ?
C28 C27 C32 C31 1.0(3) . . . . ?
C26 C27 C32 C33 0.7(3) . . . . ?
C28 C27 C32 C33 -178.7(2) . . . . ?
C25 C24 C33 C32 -0.5(3) . . . . ?
C11 C24 C33 C32 178.5(2) . . . . ?
C31 C32 C33 C24 179.8(2) . . . . ?
C27 C32 C33 C24 -0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1018405'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H25 B F2 Fe N2'
_chemical_formula_weight         578.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.0180(3)
_cell_length_b                   9.7850(4)
_cell_length_c                   17.3902(7)
_cell_angle_alpha                75.968(4)
_cell_angle_beta                 86.559(3)
_cell_angle_gamma                70.319(4)
_cell_volume                     1401.38(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7140
_cell_measurement_theta_min      3.8050
_cell_measurement_theta_max      32.0490

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_min  0.8319
_exptl_absorpt_correction_T_max  0.8881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9666
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4930
_reflns_number_gt                4531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0388P)²+0.6115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4930
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
B1 B 0.6619(3) 0.1391(3) 0.02509(14) 0.0374(5) Uani 1 1 d . . .
Fe1 Fe 0.54978(3) 0.43952(3) 0.303233(16) 0.03564(11) Uani 1 1 d . . .
F1 F 0.52043(14) 0.17443(15) 0.06322(8) 0.0551(3) Uani 1 1 d . . .
F2 F 0.63233(15) 0.14662(16) -0.05343(7) 0.0542(3) Uani 1 1 d . . .
N1 N 0.74915(18) 0.24836(19) 0.03034(10) 0.0358(4) Uani 1 1 d . . .
N2 N 0.77301(18) -0.01820(19) 0.06532(10) 0.0381(4) Uani 1 1 d . . .
C1 C 0.7064(3) 0.3943(2) -0.00510(13) 0.0451(5) Uani 1 1 d . . .
H1 H 0.6194 0.4465 -0.0411 0.054 Uiso 1 1 calc R . .
C2 C 0.8069(3) 0.4584(3) 0.01816(14) 0.0525(6) Uani 1 1 d . . .
H2 H 0.8007 0.5602 0.0016 0.063 Uiso 1 1 calc R . .
C3 C 0.9168(3) 0.3469(3) 0.06963(13) 0.0463(5) Uani 1 1 d . . .
H3 H 1.0012 0.3573 0.0952 0.056 Uiso 1 1 calc R . .
C4 C 0.8825(2) 0.2143(2) 0.07788(12) 0.0358(4) Uani 1 1 d . . .
C5 C 0.9631(2) 0.0669(2) 0.11653(11) 0.0348(4) Uani 1 1 d . . .
C6 C 0.9110(2) -0.0483(2) 0.10823(12) 0.0370(4) Uani 1 1 d . . .
C7 C 0.9729(3) -0.2038(2) 0.13847(14) 0.0476(5) Uani 1 1 d . . .
H7 H 1.0667 -0.2564 0.1698 0.057 Uiso 1 1 calc R . .
C8 C 0.8726(3) -0.2658(3) 0.11432(16) 0.0556(6) Uani 1 1 d . . .
H8 H 0.8840 -0.3688 0.1260 0.067 Uiso 1 1 calc R . .
C9 C 0.7516(3) -0.1488(3) 0.06966(14) 0.0501(6) Uani 1 1 d . . .
H9 H 0.6659 -0.1600 0.0456 0.060 Uiso 1 1 calc R . .
C10 C 1.1098(2) 0.0256(2) 0.16298(12) 0.0390(5) Uani 1 1 d . . .
H10 H 1.2002 -0.0446 0.1470 0.047 Uiso 1 1 calc R . .
C11 C 1.1295(2) 0.0766(2) 0.22550(12) 0.0360(4) Uani 1 1 d . . .
C12 C 1.0003(2) 0.1733(2) 0.26006(12) 0.0411(5) Uani 1 1 d . . .
C13 C 0.8993(2) 0.2454(3) 0.29575(13) 0.0429(5) Uani 1 1 d . . .
C14 C 1.2860(2) 0.0230(2) 0.26709(12) 0.0352(4) Uani 1 1 d . . .
C15 C 1.4255(2) -0.0244(2) 0.22707(12) 0.0376(4) Uani 1 1 d . . .
H15 H 1.4214 -0.0195 0.1720 0.045 Uiso 1 1 calc R . .
C16 C 1.5695(2) -0.0784(2) 0.26653(12) 0.0387(5) Uani 1 1 d . . .
H16 H 1.6628 -0.1105 0.2379 0.046 Uiso 1 1 calc R . .
C17 C 1.5817(2) -0.0871(2) 0.34707(12) 0.0356(4) Uani 1 1 d . . .
C18 C 1.4420(2) -0.0383(3) 0.38663(13) 0.0448(5) Uani 1 1 d . . .
H18 H 1.4461 -0.0427 0.4417 0.054 Uiso 1 1 calc R . .
C19 C 1.2970(2) 0.0167(3) 0.34727(13) 0.0449(5) Uani 1 1 d . . .
H19 H 1.2037 0.0507 0.3756 0.054 Uiso 1 1 calc R . .
C20 C 1.7381(2) -0.1495(2) 0.38931(12) 0.0386(5) Uani 1 1 d . . .
C21 C 1.8736(3) -0.1433(3) 0.34879(15) 0.0542(6) Uani 1 1 d . . .
H21 H 1.8666 -0.0953 0.2940 0.065 Uiso 1 1 calc R . .
C22 C 2.0198(3) -0.2067(4) 0.38769(18) 0.0706(8) Uani 1 1 d . . .
H22 H 2.1118 -0.2026 0.3590 0.085 Uiso 1 1 calc R . .
C23 C 2.0329(3) -0.2746(4) 0.46650(18) 0.0755(9) Uani 1 1 d . . .
H23 H 2.1333 -0.3177 0.4926 0.091 Uiso 1 1 calc R . .
C24 C 1.8993(3) -0.2800(4) 0.50781(17) 0.0754(9) Uani 1 1 d . . .
H24 H 1.9074 -0.3269 0.5628 0.090 Uiso 1 1 calc R . .
C25 C 1.7532(3) -0.2175(3) 0.46973(14) 0.0565(6) Uani 1 1 d . . .
H25 H 1.6617 -0.2212 0.4991 0.068 Uiso 1 1 calc R . .
C26 C 0.7778(2) 0.3284(2) 0.33989(12) 0.0390(5) Uani 1 1 d . . .
C27 C 0.7371(3) 0.4831(3) 0.33822(13) 0.0441(5) Uani 1 1 d . . .
H27 H 0.7865 0.5496 0.3078 0.053 Uiso 1 1 calc R . .
C28 C 0.6104(3) 0.5199(3) 0.38989(13) 0.0487(5) Uani 1 1 d . . .
H28 H 0.5596 0.6158 0.4001 0.058 Uiso 1 1 calc R . .
C29 C 0.5726(3) 0.3902(3) 0.42350(13) 0.0499(6) Uani 1 1 d . . .
H29 H 0.4921 0.3835 0.4606 0.060 Uiso 1 1 calc R . .
C30 C 0.6746(3) 0.2712(3) 0.39291(12) 0.0459(5) Uani 1 1 d . . .
H30 H 0.6742 0.1713 0.4055 0.055 Uiso 1 1 calc R . .
C31 C 0.4173(4) 0.3629(4) 0.2454(2) 0.0885(12) Uani 1 1 d . . .
H31 H 0.4108 0.2651 0.2591 0.106 Uiso 1 1 calc R . .
C32 C 0.3203(3) 0.4887(4) 0.2726(2) 0.0793(9) Uani 1 1 d . . .
H32 H 0.2356 0.4910 0.3080 0.095 Uiso 1 1 calc R . .
C33 C 0.3713(3) 0.6067(3) 0.2382(2) 0.0753(9) Uani 1 1 d . . .
H33 H 0.3275 0.7050 0.2461 0.090 Uiso 1 1 calc R . .
C34 C 0.4951(4) 0.5596(4) 0.19092(18) 0.0815(10) Uani 1 1 d . . .
H34 H 0.5515 0.6198 0.1607 0.098 Uiso 1 1 calc R . .
C35 C 0.5246(4) 0.4120(5) 0.19411(19) 0.0837(11) Uani 1 1 d . . .
H35 H 0.6045 0.3526 0.1663 0.100 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
B1 F1 1.378(3) . ?
B1 F2 1.387(3) . ?
B1 N2 1.544(3) . ?
B1 N1 1.547(3) . ?
Fe1 C34 2.013(3) . ?
Fe1 C35 2.016(3) . ?
Fe1 C33 2.023(3) . ?
Fe1 C31 2.028(3) . ?
Fe1 C30 2.032(2) . ?
Fe1 C26 2.0326(19) . ?
Fe1 C27 2.035(2) . ?
Fe1 C32 2.033(3) . ?
Fe1 C29 2.036(2) . ?
Fe1 C28 2.038(2) . ?
N1 C1 1.341(3) . ?
N1 C4 1.399(2) . ?
N2 C9 1.339(3) . ?
N2 C6 1.396(2) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C5 C6 1.399(3) . ?
C5 C10 1.475(2) . ?
C6 C7 1.406(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.344(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.437(3) . ?
C11 C14 1.493(2) . ?
C12 C13 1.193(3) . ?
C13 C26 1.432(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(3) . ?
C17 C20 1.493(3) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 C25 1.389(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.363(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C30 1.424(3) . ?
C26 C27 1.426(3) . ?
C27 C28 1.414(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.406(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.416(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C35 1.401(5) . ?
C31 C32 1.418(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.376(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.364(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.366(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?

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
F1 B1 F2 108.66(16) . . ?
F1 B1 N2 111.25(18) . . ?
F2 B1 N2 110.34(18) . . ?
F1 B1 N1 110.22(17) . . ?
F2 B1 N1 110.46(18) . . ?
N2 B1 N1 105.89(15) . . ?
C34 Fe1 C35 39.62(14) . . ?
C34 Fe1 C33 39.50(14) . . ?
C35 Fe1 C33 66.74(13) . . ?
C34 Fe1 C31 67.48(14) . . ?
C35 Fe1 C31 40.53(15) . . ?
C33 Fe1 C31 67.56(13) . . ?
C34 Fe1 C30 157.26(13) . . ?
C35 Fe1 C30 123.16(13) . . ?
C33 Fe1 C30 162.19(13) . . ?
C31 Fe1 C30 109.31(11) . . ?
C34 Fe1 C26 120.99(12) . . ?
C35 Fe1 C26 108.05(11) . . ?
C33 Fe1 C26 155.32(12) . . ?
C31 Fe1 C26 125.32(12) . . ?
C30 Fe1 C26 41.00(9) . . ?
C34 Fe1 C27 106.57(12) . . ?
C35 Fe1 C27 123.67(13) . . ?
C33 Fe1 C27 120.01(11) . . ?
C31 Fe1 C27 161.23(14) . . ?
C30 Fe1 C27 68.86(9) . . ?
C26 Fe1 C27 41.04(9) . . ?
C34 Fe1 C32 66.88(13) . . ?
C35 Fe1 C32 67.66(14) . . ?
C33 Fe1 C32 39.65(13) . . ?
C31 Fe1 C32 40.87(14) . . ?
C30 Fe1 C32 126.51(12) . . ?
C26 Fe1 C32 163.19(13) . . ?
C27 Fe1 C32 155.08(13) . . ?
C34 Fe1 C29 160.11(14) . . ?
C35 Fe1 C29 159.06(15) . . ?
C33 Fe1 C29 125.04(12) . . ?
C31 Fe1 C29 123.38(14) . . ?
C30 Fe1 C29 40.74(9) . . ?
C26 Fe1 C29 68.57(9) . . ?
C27 Fe1 C29 68.26(9) . . ?
C32 Fe1 C29 109.24(12) . . ?
C34 Fe1 C28 123.34(13) . . ?
C35 Fe1 C28 159.50(15) . . ?
C33 Fe1 C28 107.25(11) . . ?
C31 Fe1 C28 157.57(15) . . ?
C30 Fe1 C28 68.56(9) . . ?
C26 Fe1 C28 68.70(9) . . ?
C27 Fe1 C28 40.64(9) . . ?
C32 Fe1 C28 121.20(12) . . ?
C29 Fe1 C28 40.37(9) . . ?
C1 N1 C4 107.21(17) . . ?
C1 N1 B1 126.95(17) . . ?
C4 N1 B1 125.71(17) . . ?
C9 N2 C6 107.52(18) . . ?
C9 N2 B1 127.05(17) . . ?
C6 N2 B1 125.34(17) . . ?
N1 C1 C2 110.59(19) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C3 C2 C1 106.9(2) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.87(19) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 N1 120.37(18) . . ?
C5 C4 C3 131.87(18) . . ?
N1 C4 C3 107.45(18) . . ?
C4 C5 C6 120.20(17) . . ?
C4 C5 C10 121.90(18) . . ?
C6 C5 C10 117.80(18) . . ?
N2 C6 C5 121.19(18) . . ?
N2 C6 C7 107.66(18) . . ?
C5 C6 C7 131.14(18) . . ?
C8 C7 C6 107.40(19) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.0(2) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.43(19) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C11 C10 C5 127.06(18) . . ?
C11 C10 H10 116.5 . . ?
C5 C10 H10 116.5 . . ?
C10 C11 C12 122.32(17) . . ?
C10 C11 C14 120.86(17) . . ?
C12 C11 C14 116.58(17) . . ?
C13 C12 C11 173.6(2) . . ?
C12 C13 C26 178.5(3) . . ?
C19 C14 C15 117.87(17) . . ?
C19 C14 C11 121.00(17) . . ?
C15 C14 C11 121.12(17) . . ?
C16 C15 C14 120.77(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.80(18) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 117.19(17) . . ?
C16 C17 C20 121.14(18) . . ?
C18 C17 C20 121.66(18) . . ?
C19 C18 C17 121.29(19) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 121.05(19) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 C25 117.88(19) . . ?
C21 C20 C17 120.70(19) . . ?
C25 C20 C17 121.41(19) . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.3(2) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
C30 C26 C27 107.60(19) . . ?
C30 C26 C13 126.0(2) . . ?
C27 C26 C13 126.4(2) . . ?
C30 C26 Fe1 69.47(12) . . ?
C27 C26 Fe1 69.55(12) . . ?
C13 C26 Fe1 125.91(14) . . ?
C28 C27 C26 108.0(2) . . ?
C28 C27 Fe1 69.80(13) . . ?
C26 C27 Fe1 69.41(12) . . ?
C28 C27 H27 126.0 . . ?
C26 C27 H27 126.0 . . ?
Fe1 C27 H27 126.3 . . ?
C29 C28 C27 108.2(2) . . ?
C29 C28 Fe1 69.74(13) . . ?
C27 C28 Fe1 69.56(12) . . ?
C29 C28 H28 125.9 . . ?
C27 C28 H28 125.9 . . ?
Fe1 C28 H28 126.4 . . ?
C28 C29 C30 108.6(2) . . ?
C28 C29 Fe1 69.88(13) . . ?
C30 C29 Fe1 69.47(12) . . ?
C28 C29 H29 125.7 . . ?
C30 C29 H29 125.7 . . ?
Fe1 C29 H29 126.5 . . ?
C29 C30 C26 107.6(2) . . ?
C29 C30 Fe1 69.79(13) . . ?
C26 C30 Fe1 69.53(12) . . ?
C29 C30 H30 126.2 . . ?
C26 C30 H30 126.2 . . ?
Fe1 C30 H30 126.1 . . ?
C35 C31 C32 106.2(3) . . ?
C35 C31 Fe1 69.27(16) . . ?
C32 C31 Fe1 69.75(16) . . ?
C35 C31 H31 126.9 . . ?
C32 C31 H31 126.9 . . ?
Fe1 C31 H31 125.7 . . ?
C33 C32 C31 107.4(3) . . ?
C33 C32 Fe1 69.77(15) . . ?
C31 C32 Fe1 69.38(16) . . ?
C33 C32 H32 126.3 . . ?
C31 C32 H32 126.3 . . ?
Fe1 C32 H32 126.2 . . ?
C34 C33 C32 108.9(3) . . ?
C34 C33 Fe1 69.84(16) . . ?
C32 C33 Fe1 70.58(16) . . ?
C34 C33 H33 125.5 . . ?
C32 C33 H33 125.5 . . ?
Fe1 C33 H33 125.6 . . ?
C33 C34 C35 109.0(3) . . ?
C33 C34 Fe1 70.65(17) . . ?
C35 C34 Fe1 70.33(17) . . ?
C33 C34 H34 125.5 . . ?
C35 C34 H34 125.5 . . ?
Fe1 C34 H34 125.1 . . ?
C34 C35 C31 108.4(3) . . ?
C34 C35 Fe1 70.05(17) . . ?
C31 C35 Fe1 70.19(17) . . ?
C34 C35 H35 125.8 . . ?
C31 C35 H35 125.8 . . ?
Fe1 C35 H35 125.6 . . ?

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
F1 B1 N1 C1 -68.3(3) . . . . ?
F2 B1 N1 C1 51.8(3) . . . . ?
N2 B1 N1 C1 171.28(18) . . . . ?
F1 B1 N1 C4 107.0(2) . . . . ?
F2 B1 N1 C4 -132.95(19) . . . . ?
N2 B1 N1 C4 -13.5(3) . . . . ?
F1 B1 N2 C9 65.4(3) . . . . ?
F2 B1 N2 C9 -55.3(3) . . . . ?
N1 B1 N2 C9 -174.81(19) . . . . ?
F1 B1 N2 C6 -110.5(2) . . . . ?
F2 B1 N2 C6 128.8(2) . . . . ?
N1 B1 N2 C6 9.3(3) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
B1 N1 C1 C2 175.43(19) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 N1 C4 C5 -173.90(18) . . . . ?
B1 N1 C4 C5 10.1(3) . . . . ?
C1 N1 C4 C3 0.4(2) . . . . ?
B1 N1 C4 C3 -175.64(18) . . . . ?
C2 C3 C4 C5 173.3(2) . . . . ?
C2 C3 C4 N1 -0.1(2) . . . . ?
N1 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 C6 -172.9(2) . . . . ?
N1 C4 C5 C10 176.02(17) . . . . ?
C3 C4 C5 C10 3.4(3) . . . . ?
C9 N2 C6 C5 -178.35(19) . . . . ?
B1 N2 C6 C5 -1.8(3) . . . . ?
C9 N2 C6 C7 0.4(2) . . . . ?
B1 N2 C6 C7 176.93(19) . . . . ?
C4 C5 C6 N2 -3.8(3) . . . . ?
C10 C5 C6 N2 179.85(17) . . . . ?
C4 C5 C6 C7 177.9(2) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
N2 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 178.2(2) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 N2 C9 C8 -0.2(3) . . . . ?
B1 N2 C9 C8 -176.7(2) . . . . ?
C7 C8 C9 N2 0.0(3) . . . . ?
C4 C5 C10 C11 58.4(3) . . . . ?
C6 C5 C10 C11 -125.3(2) . . . . ?
C5 C10 C11 C12 5.3(4) . . . . ?
C5 C10 C11 C14 179.5(2) . . . . ?
C10 C11 C12 C13 137(2) . . . . ?
C14 C11 C12 C13 -38(2) . . . . ?
C11 C12 C13 C26 -45(10) . . . . ?
C10 C11 C14 C19 -150.5(2) . . . . ?
C12 C11 C14 C19 24.0(3) . . . . ?
C10 C11 C14 C15 28.5(3) . . . . ?
C12 C11 C14 C15 -157.0(2) . . . . ?
C19 C14 C15 C16 1.2(3) . . . . ?
C11 C14 C15 C16 -177.84(19) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C15 C16 C17 C20 178.39(19) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C20 C17 C18 C19 -178.7(2) . . . . ?
C17 C18 C19 C14 0.9(4) . . . . ?
C15 C14 C19 C18 -1.5(3) . . . . ?
C11 C14 C19 C18 177.5(2) . . . . ?
C16 C17 C20 C21 26.8(3) . . . . ?
C18 C17 C20 C21 -154.5(2) . . . . ?
C16 C17 C20 C25 -152.1(2) . . . . ?
C18 C17 C20 C25 26.5(3) . . . . ?
C25 C20 C21 C22 1.5(4) . . . . ?
C17 C20 C21 C22 -177.5(2) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
C23 C24 C25 C20 0.6(5) . . . . ?
C21 C20 C25 C24 -1.4(4) . . . . ?
C17 C20 C25 C24 177.6(3) . . . . ?
C12 C13 C26 C30 -16(9) . . . . ?
C12 C13 C26 C27 165(9) . . . . ?
C12 C13 C26 Fe1 -105(9) . . . . ?
C34 Fe1 C26 C30 -161.60(17) . . . . ?
C35 Fe1 C26 C30 -120.13(18) . . . . ?
C33 Fe1 C26 C30 166.5(3) . . . . ?
C31 Fe1 C26 C30 -78.6(2) . . . . ?
C27 Fe1 C26 C30 118.96(18) . . . . ?
C32 Fe1 C26 C30 -47.8(4) . . . . ?
C29 Fe1 C26 C30 37.90(13) . . . . ?
C28 Fe1 C26 C30 81.39(14) . . . . ?
C34 Fe1 C26 C27 79.44(18) . . . . ?
C35 Fe1 C26 C27 120.91(18) . . . . ?
C33 Fe1 C26 C27 47.5(3) . . . . ?
C31 Fe1 C26 C27 162.43(18) . . . . ?
C30 Fe1 C26 C27 -118.96(18) . . . . ?
C32 Fe1 C26 C27 -166.8(4) . . . . ?
C29 Fe1 C26 C27 -81.07(14) . . . . ?
C28 Fe1 C26 C27 -37.57(13) . . . . ?
C34 Fe1 C26 C13 -41.3(3) . . . . ?
C35 Fe1 C26 C13 0.2(3) . . . . ?
C33 Fe1 C26 C13 -73.3(3) . . . . ?
C31 Fe1 C26 C13 41.7(3) . . . . ?
C30 Fe1 C26 C13 120.3(3) . . . . ?
C27 Fe1 C26 C13 -120.8(2) . . . . ?
C32 Fe1 C26 C13 72.5(4) . . . . ?
C29 Fe1 C26 C13 158.2(2) . . . . ?
C28 Fe1 C26 C13 -158.3(2) . . . . ?
C30 C26 C27 C28 0.1(2) . . . . ?
C13 C26 C27 C28 179.56(19) . . . . ?
Fe1 C26 C27 C28 59.37(15) . . . . ?
C30 C26 C27 Fe1 -59.27(14) . . . . ?
C13 C26 C27 Fe1 120.2(2) . . . . ?
C34 Fe1 C27 C28 122.27(18) . . . . ?
C35 Fe1 C27 C28 162.15(17) . . . . ?
C33 Fe1 C27 C28 81.54(18) . . . . ?
C31 Fe1 C27 C28 -169.2(3) . . . . ?
C30 Fe1 C27 C28 -81.30(14) . . . . ?
C26 Fe1 C27 C28 -119.28(19) . . . . ?
C32 Fe1 C27 C28 51.7(3) . . . . ?
C29 Fe1 C27 C28 -37.38(14) . . . . ?
C34 Fe1 C27 C26 -118.45(17) . . . . ?
C35 Fe1 C27 C26 -78.57(19) . . . . ?
C33 Fe1 C27 C26 -159.18(16) . . . . ?
C31 Fe1 C27 C26 -49.9(4) . . . . ?
C30 Fe1 C27 C26 37.99(12) . . . . ?
C32 Fe1 C27 C26 171.0(3) . . . . ?
C29 Fe1 C27 C26 81.90(14) . . . . ?
C28 Fe1 C27 C26 119.28(19) . . . . ?
C26 C27 C28 C29 0.1(3) . . . . ?
Fe1 C27 C28 C29 59.26(16) . . . . ?
C26 C27 C28 Fe1 -59.12(14) . . . . ?
C34 Fe1 C28 C29 164.55(16) . . . . ?
C35 Fe1 C28 C29 -166.2(3) . . . . ?
C33 Fe1 C28 C29 124.27(17) . . . . ?
C31 Fe1 C28 C29 51.5(3) . . . . ?
C30 Fe1 C28 C29 -37.37(14) . . . . ?
C26 Fe1 C28 C29 -81.56(15) . . . . ?
C27 Fe1 C28 C29 -119.5(2) . . . . ?
C32 Fe1 C28 C29 83.25(18) . . . . ?
C34 Fe1 C28 C27 -75.96(19) . . . . ?
C35 Fe1 C28 C27 -46.8(4) . . . . ?
C33 Fe1 C28 C27 -116.25(16) . . . . ?
C31 Fe1 C28 C27 170.9(3) . . . . ?
C30 Fe1 C28 C27 82.11(14) . . . . ?
C26 Fe1 C28 C27 37.93(13) . . . . ?
C32 Fe1 C28 C27 -157.27(16) . . . . ?
C29 Fe1 C28 C27 119.5(2) . . . . ?
C27 C28 C29 C30 -0.3(3) . . . . ?
Fe1 C28 C29 C30 58.82(16) . . . . ?
C27 C28 C29 Fe1 -59.14(16) . . . . ?
C34 Fe1 C29 C28 -40.8(4) . . . . ?
C35 Fe1 C29 C28 166.5(3) . . . . ?
C33 Fe1 C29 C28 -74.59(18) . . . . ?
C31 Fe1 C29 C28 -159.06(17) . . . . ?
C30 Fe1 C29 C28 120.0(2) . . . . ?
C26 Fe1 C29 C28 81.91(15) . . . . ?
C27 Fe1 C29 C28 37.62(13) . . . . ?
C32 Fe1 C29 C28 -115.88(17) . . . . ?
C34 Fe1 C29 C30 -160.9(3) . . . . ?
C35 Fe1 C29 C30 46.5(4) . . . . ?
C33 Fe1 C29 C30 165.37(16) . . . . ?
C31 Fe1 C29 C30 80.90(19) . . . . ?
C26 Fe1 C29 C30 -38.13(14) . . . . ?
C27 Fe1 C29 C30 -82.42(15) . . . . ?
C32 Fe1 C29 C30 124.08(17) . . . . ?
C28 Fe1 C29 C30 -120.0(2) . . . . ?
C28 C29 C30 C26 0.4(3) . . . . ?
Fe1 C29 C30 C26 59.46(15) . . . . ?
C28 C29 C30 Fe1 -59.08(17) . . . . ?
C27 C26 C30 C29 -0.3(2) . . . . ?
C13 C26 C30 C29 -179.8(2) . . . . ?
Fe1 C26 C30 C29 -59.62(16) . . . . ?
C27 C26 C30 Fe1 59.33(14) . . . . ?
C13 C26 C30 Fe1 -120.1(2) . . . . ?
C34 Fe1 C30 C29 163.2(3) . . . . ?
C35 Fe1 C30 C29 -161.97(18) . . . . ?
C33 Fe1 C30 C29 -42.5(4) . . . . ?
C31 Fe1 C30 C29 -119.11(19) . . . . ?
C26 Fe1 C30 C29 118.83(19) . . . . ?
C27 Fe1 C30 C29 80.81(15) . . . . ?
C32 Fe1 C30 C29 -76.6(2) . . . . ?
C28 Fe1 C30 C29 37.05(14) . . . . ?
C34 Fe1 C30 C26 44.4(4) . . . . ?
C35 Fe1 C30 C26 79.21(19) . . . . ?
C33 Fe1 C30 C26 -161.4(3) . . . . ?
C31 Fe1 C30 C26 122.06(18) . . . . ?
C27 Fe1 C30 C26 -38.02(12) . . . . ?
C32 Fe1 C30 C26 164.54(16) . . . . ?
C29 Fe1 C30 C26 -118.83(19) . . . . ?
C28 Fe1 C30 C26 -81.78(14) . . . . ?
C34 Fe1 C31 C35 37.0(2) . . . . ?
C33 Fe1 C31 C35 80.0(2) . . . . ?
C30 Fe1 C31 C35 -118.8(2) . . . . ?
C26 Fe1 C31 C35 -75.9(2) . . . . ?
C27 Fe1 C31 C35 -37.8(4) . . . . ?
C32 Fe1 C31 C35 117.2(3) . . . . ?
C29 Fe1 C31 C35 -161.89(18) . . . . ?
C28 Fe1 C31 C35 160.8(3) . . . . ?
C34 Fe1 C31 C32 -80.2(2) . . . . ?
C35 Fe1 C31 C32 -117.2(3) . . . . ?
C33 Fe1 C31 C32 -37.3(2) . . . . ?
C30 Fe1 C31 C32 124.0(2) . . . . ?
C26 Fe1 C31 C32 166.91(18) . . . . ?
C27 Fe1 C31 C32 -155.1(3) . . . . ?
C29 Fe1 C31 C32 80.9(2) . . . . ?
C28 Fe1 C31 C32 43.5(4) . . . . ?
C35 C31 C32 C33 -0.4(3) . . . . ?
Fe1 C31 C32 C33 59.6(2) . . . . ?
C35 C31 C32 Fe1 -60.00(19) . . . . ?
C34 Fe1 C32 C33 -36.9(2) . . . . ?
C35 Fe1 C32 C33 -80.0(2) . . . . ?
C31 Fe1 C32 C33 -118.7(3) . . . . ?
C30 Fe1 C32 C33 164.41(18) . . . . ?
C26 Fe1 C32 C33 -158.4(3) . . . . ?
C27 Fe1 C32 C33 42.5(4) . . . . ?
C29 Fe1 C32 C33 122.1(2) . . . . ?
C28 Fe1 C32 C33 79.2(2) . . . . ?
C34 Fe1 C32 C31 81.8(2) . . . . ?
C35 Fe1 C32 C31 38.7(2) . . . . ?
C33 Fe1 C32 C31 118.7(3) . . . . ?
C30 Fe1 C32 C31 -76.9(2) . . . . ?
C26 Fe1 C32 C31 -39.7(5) . . . . ?
C27 Fe1 C32 C31 161.2(3) . . . . ?
C29 Fe1 C32 C31 -119.2(2) . . . . ?
C28 Fe1 C32 C31 -162.1(2) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
Fe1 C32 C33 C34 59.5(2) . . . . ?
C31 C32 C33 Fe1 -59.4(2) . . . . ?
C35 Fe1 C33 C34 -37.2(2) . . . . ?
C31 Fe1 C33 C34 -81.3(2) . . . . ?
C30 Fe1 C33 C34 -164.7(3) . . . . ?
C26 Fe1 C33 C34 45.5(4) . . . . ?
C27 Fe1 C33 C34 79.5(2) . . . . ?
C32 Fe1 C33 C34 -119.7(3) . . . . ?
C29 Fe1 C33 C34 162.72(19) . . . . ?
C28 Fe1 C33 C34 121.9(2) . . . . ?
C34 Fe1 C33 C32 119.7(3) . . . . ?
C35 Fe1 C33 C32 82.5(2) . . . . ?
C31 Fe1 C33 C32 38.4(2) . . . . ?
C30 Fe1 C33 C32 -44.9(5) . . . . ?
C26 Fe1 C33 C32 165.2(2) . . . . ?
C27 Fe1 C33 C32 -160.80(19) . . . . ?
C29 Fe1 C33 C32 -77.5(2) . . . . ?
C28 Fe1 C33 C32 -118.4(2) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
Fe1 C33 C34 C35 60.1(2) . . . . ?
C32 C33 C34 Fe1 -60.0(2) . . . . ?
C35 Fe1 C34 C33 119.4(3) . . . . ?
C31 Fe1 C34 C33 81.6(2) . . . . ?
C30 Fe1 C34 C33 167.9(2) . . . . ?
C26 Fe1 C34 C33 -159.68(17) . . . . ?
C27 Fe1 C34 C33 -117.35(19) . . . . ?
C32 Fe1 C34 C33 37.0(2) . . . . ?
C29 Fe1 C34 C33 -45.6(4) . . . . ?
C28 Fe1 C34 C33 -76.1(2) . . . . ?
C33 Fe1 C34 C35 -119.4(3) . . . . ?
C31 Fe1 C34 C35 -37.9(2) . . . . ?
C30 Fe1 C34 C35 48.5(4) . . . . ?
C26 Fe1 C34 C35 80.9(2) . . . . ?
C27 Fe1 C34 C35 123.2(2) . . . . ?
C32 Fe1 C34 C35 -82.4(2) . . . . ?
C29 Fe1 C34 C35 -165.1(3) . . . . ?
C28 Fe1 C34 C35 164.45(19) . . . . ?
C33 C34 C35 C31 -0.4(3) . . . . ?
Fe1 C34 C35 C31 59.9(2) . . . . ?
C33 C34 C35 Fe1 -60.3(2) . . . . ?
C32 C31 C35 C34 0.5(3) . . . . ?
Fe1 C31 C35 C34 -59.8(2) . . . . ?
C32 C31 C35 Fe1 60.3(2) . . . . ?
C33 Fe1 C35 C34 37.1(2) . . . . ?
C31 Fe1 C35 C34 119.2(3) . . . . ?
C30 Fe1 C35 C34 -159.77(18) . . . . ?
C26 Fe1 C35 C34 -117.1(2) . . . . ?
C27 Fe1 C35 C34 -74.5(2) . . . . ?
C32 Fe1 C35 C34 80.2(2) . . . . ?
C29 Fe1 C35 C34 165.8(3) . . . . ?
C28 Fe1 C35 C34 -39.7(4) . . . . ?
C34 Fe1 C35 C31 -119.2(3) . . . . ?
C33 Fe1 C35 C31 -82.1(2) . . . . ?
C30 Fe1 C35 C31 81.0(2) . . . . ?
C26 Fe1 C35 C31 123.68(19) . . . . ?
C27 Fe1 C35 C31 166.28(17) . . . . ?
C32 Fe1 C35 C31 -38.98(19) . . . . ?
C29 Fe1 C35 C31 46.6(4) . . . . ?
C28 Fe1 C35 C31 -159.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.043

#===END
####################################################################### 
# 
# 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_rm151
_audit_block_doi                 10.5517/cc13yx87
_database_code_depnum_ccdc_archive 'CCDC 1041639'
_audit_update_record             
;
2014-12-31 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 B F2 N2'
_chemical_formula_weight         292.09

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.9615(3)
_cell_length_b                   10.2059(2)
_cell_length_c                   15.7879(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.796(3)
_cell_angle_gamma                90.00
_cell_volume                     1389.44(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4586
_cell_measurement_theta_min      5.1130
_cell_measurement_theta_max      71.1310

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_min  0.7689
_exptl_absorpt_correction_T_max  0.8433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8592
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         71.34
_reflns_number_total             2672
_reflns_number_gt                2535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0504P)²+0.4631P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2672
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
F1 F 0.59810(8) 0.20941(8) 0.05185(5) 0.0327(2) Uani 1 1 d . . .
F2 F 0.75798(9) 0.06102(8) 0.13720(5) 0.0329(2) Uani 1 1 d . . .
B1 B 0.74338(15) 0.15229(13) 0.07044(9) 0.0220(3) Uani 1 1 d . . .
N2 N 0.87102(11) 0.25808(10) 0.09867(6) 0.0222(2) Uani 1 1 d . . .
N1 N 0.77007(11) 0.08618(9) -0.01288(6) 0.0209(2) Uani 1 1 d . . .
C1 C 0.69329(14) -0.01667(12) -0.05666(8) 0.0266(3) Uani 1 1 d . . .
H1 H 0.6112 -0.0591 -0.0428 0.032 Uiso 1 1 calc R . .
C2 C 0.75436(15) -0.05129(13) -0.12645(8) 0.0291(3) Uani 1 1 d . . .
H2 H 0.7205 -0.1192 -0.1664 0.035 Uiso 1 1 calc R . .
C3 C 0.87362(14) 0.03413(12) -0.12466(8) 0.0258(3) Uani 1 1 d . . .
H3 H 0.9364 0.0344 -0.1628 0.031 Uiso 1 1 calc R . .
C4 C 0.88303(13) 0.12125(11) -0.05412(7) 0.0210(2) Uani 1 1 d . . .
C5 C 0.98263(13) 0.22628(11) -0.02341(7) 0.0214(2) Uani 1 1 d . . .
C6 C 0.97416(13) 0.29612(11) 0.05198(8) 0.0213(2) Uani 1 1 d . . .
C7 C 1.06560(14) 0.39855(13) 0.09772(9) 0.0283(3) Uani 1 1 d . . .
H7 H 1.1432 0.4431 0.0806 0.034 Uiso 1 1 calc R . .
C8 C 1.01889(16) 0.42101(14) 0.17290(9) 0.0349(3) Uani 1 1 d . . .
H8 H 1.0593 0.4831 0.2162 0.042 Uiso 1 1 calc R . .
C9 C 0.89934(15) 0.33252(14) 0.17138(9) 0.0312(3) Uani 1 1 d . . .
H9 H 0.8469 0.3261 0.2146 0.037 Uiso 1 1 calc R . .
C10 C 1.10004(14) 0.25976(12) -0.06476(8) 0.0255(3) Uani 1 1 d . . .
C11 C 1.20648(15) 0.28700(12) -0.09407(8) 0.0264(3) Uani 1 1 d . . .
C12 C 1.33664(13) 0.32110(12) -0.12571(8) 0.0238(3) Uani 1 1 d . . .
C13 C 1.40097(14) 0.44646(13) -0.10942(8) 0.0281(3) Uani 1 1 d . . .
H13 H 1.3584 0.5075 -0.0789 0.034 Uiso 1 1 calc R . .
C14 C 1.52810(15) 0.47937(13) -0.13877(9) 0.0315(3) Uani 1 1 d . . .
H14 H 1.5703 0.5630 -0.1285 0.038 Uiso 1 1 calc R . .
C15 C 1.59290(14) 0.38835(14) -0.18341(9) 0.0327(3) Uani 1 1 d . . .
H15 H 1.6780 0.4112 -0.2033 0.039 Uiso 1 1 calc R . .
C16 C 1.53108(14) 0.26360(14) -0.19846(9) 0.0300(3) Uani 1 1 d . . .
H16 H 1.5760 0.2024 -0.2276 0.036 Uiso 1 1 calc R . .
C17 C 1.40279(14) 0.22909(12) -0.17043(8) 0.0259(3) Uani 1 1 d . . .
H17 H 1.3609 0.1454 -0.1812 0.031 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3831(15) . ?
F2 B1 1.3858(15) . ?
B1 N2 1.5476(16) . ?
B1 N1 1.5538(16) . ?
N2 C9 1.3420(16) . ?
N2 C6 1.3854(14) . ?
N1 C1 1.3394(16) . ?
N1 C4 1.3913(14) . ?
C1 C2 1.4024(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.3735(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.4095(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3947(17) . ?
C5 C6 1.4070(17) . ?
C5 C10 1.4226(16) . ?
C6 C7 1.4013(17) . ?
C7 C8 1.3810(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.3964(18) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.2007(18) . ?
C11 C12 1.4312(16) . ?
C12 C13 1.3981(18) . ?
C12 C17 1.3998(18) . ?
C13 C14 1.3831(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3851(17) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 109.47(10) . . ?
F1 B1 N2 110.26(10) . . ?
F2 B1 N2 109.91(10) . . ?
F1 B1 N1 110.87(10) . . ?
F2 B1 N1 110.34(10) . . ?
N2 B1 N1 105.94(9) . . ?
C9 N2 C6 107.35(10) . . ?
C9 N2 B1 126.45(10) . . ?
C6 N2 B1 126.17(10) . . ?
C1 N1 C4 107.28(10) . . ?
C1 N1 B1 126.97(10) . . ?
C4 N1 B1 125.72(9) . . ?
N1 C1 C2 110.33(11) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 106.97(11) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 107.19(11) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C5 120.89(10) . . ?
N1 C4 C3 108.23(10) . . ?
C5 C4 C3 130.88(11) . . ?
C4 C5 C6 120.44(10) . . ?
C4 C5 C10 120.56(11) . . ?
C6 C5 C10 118.91(11) . . ?
N2 C6 C7 108.43(10) . . ?
N2 C6 C5 120.37(10) . . ?
C7 C6 C5 130.94(11) . . ?
C8 C7 C6 107.17(11) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 106.77(11) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
N2 C9 C8 110.27(11) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
C11 C10 C5 175.46(13) . . ?
C10 C11 C12 177.79(13) . . ?
C13 C12 C17 119.78(11) . . ?
C13 C12 C11 119.52(11) . . ?
C17 C12 C11 120.68(11) . . ?
C14 C13 C12 119.77(12) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.34(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.06(11) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.51(12) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 119.53(12) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?

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
F1 B1 N2 C9 65.33(16) . . . . ?
F2 B1 N2 C9 -55.43(16) . . . . ?
N1 B1 N2 C9 -174.64(11) . . . . ?
F1 B1 N2 C6 -112.54(12) . . . . ?
F2 B1 N2 C6 126.69(12) . . . . ?
N1 B1 N2 C6 7.48(15) . . . . ?
F1 B1 N1 C1 -65.03(15) . . . . ?
F2 B1 N1 C1 56.41(15) . . . . ?
N2 B1 N1 C1 175.34(10) . . . . ?
F1 B1 N1 C4 117.23(12) . . . . ?
F2 B1 N1 C4 -121.33(11) . . . . ?
N2 B1 N1 C4 -2.40(15) . . . . ?
C4 N1 C1 C2 0.37(13) . . . . ?
B1 N1 C1 C2 -177.71(11) . . . . ?
N1 C1 C2 C3 0.18(14) . . . . ?
C1 C2 C3 C4 -0.64(14) . . . . ?
C1 N1 C4 C5 179.91(10) . . . . ?
B1 N1 C4 C5 -1.98(17) . . . . ?
C1 N1 C4 C3 -0.76(13) . . . . ?
B1 N1 C4 C3 177.35(10) . . . . ?
C2 C3 C4 N1 0.87(13) . . . . ?
C2 C3 C4 C5 -179.89(12) . . . . ?
N1 C4 C5 C6 2.22(17) . . . . ?
C3 C4 C5 C6 -176.95(11) . . . . ?
N1 C4 C5 C10 178.63(10) . . . . ?
C3 C4 C5 C10 -0.54(19) . . . . ?
C9 N2 C6 C7 -1.04(14) . . . . ?
B1 N2 C6 C7 177.17(11) . . . . ?
C9 N2 C6 C5 173.66(11) . . . . ?
B1 N2 C6 C5 -8.13(17) . . . . ?
C4 C5 C6 N2 2.61(17) . . . . ?
C10 C5 C6 N2 -173.85(10) . . . . ?
C4 C5 C6 C7 175.95(12) . . . . ?
C10 C5 C6 C7 -0.5(2) . . . . ?
N2 C6 C7 C8 0.86(15) . . . . ?
C5 C6 C7 C8 -173.08(13) . . . . ?
C6 C7 C8 C9 -0.35(16) . . . . ?
C6 N2 C9 C8 0.83(15) . . . . ?
B1 N2 C9 C8 -177.37(12) . . . . ?
C7 C8 C9 N2 -0.30(17) . . . . ?
C4 C5 C10 C11 -123.4(17) . . . . ?
C6 C5 C10 C11 53.0(17) . . . . ?
C5 C10 C11 C12 -25(5) . . . . ?
C10 C11 C12 C13 -53(4) . . . . ?
C10 C11 C12 C17 126(4) . . . . ?
C17 C12 C13 C14 0.98(18) . . . . ?
C11 C12 C13 C14 179.10(12) . . . . ?
C12 C13 C14 C15 -0.66(19) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C15 C16 C17 C12 -0.69(19) . . . . ?
C13 C12 C17 C16 -0.31(18) . . . . ?
C11 C12 C17 C16 -178.41(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        71.34
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
