# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_Compound1a
_database_code_depnum_ccdc_archive 'CCDC 1435988'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 B F2 I2 N2, C H2 Cl2'
_chemical_formula_sum            'C24 H23 B Cl2 F2 I2 N2'
_chemical_formula_weight         712.95

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab '
_symmetry_space_group_name_H-M   'P 21 21 21 '

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

_cell_length_a                   8.2966(4)
_cell_length_b                   23.4782(12)
_cell_length_c                   25.1750(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4903.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.80

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2752
_exptl_absorpt_coefficient_mu    2.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3706
_exptl_absorpt_correction_T_max  0.9458
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            64679
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         26.80
_reflns_number_total             10489
_reflns_number_gt                10111
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0405P)²+54.45P] 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     SHELXL
_refine_ls_extinction_coef       0.00063(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack (1983) '
_refine_ls_abs_structure_Flack   0.47(3)
_refine_ls_number_reflns         10489
_refine_ls_number_parameters     597
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_restrained_S_all      1.217
_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
I1 I 0.07599(7) 0.87340(3) 0.60042(2) 0.01907(14) Uani 1 1 d . . .
I2 I 0.75583(8) 0.97467(3) 0.51692(2) 0.02107(14) Uani 1 1 d . . .
F1 F 0.4689(6) 0.8695(2) 0.5398(2) 0.0187(11) Uani 1 1 d . . .
F2 F 0.3492(6) 0.9570(2) 0.5348(2) 0.0201(11) Uani 1 1 d . . .
N1 N 0.2242(8) 0.8776(3) 0.4894(3) 0.0119(14) Uani 1 1 d . . .
N2 N 0.4800(8) 0.9198(3) 0.4564(3) 0.0097(14) Uani 1 1 d . . .
C1 C 0.0979(10) 0.8603(4) 0.5195(4) 0.0165(17) Uani 1 1 d . . .
C2 C -0.0184(11) 0.8312(4) 0.4895(4) 0.0145(18) Uani 1 1 d . . .
C3 C -0.1720(11) 0.8051(4) 0.5070(4) 0.0160(18) Uani 1 1 d U . .
H3A H -0.2281 0.8313 0.5316 0.019 Uiso 1 1 calc R . .
H3B H -0.1491 0.7693 0.5264 0.019 Uiso 1 1 calc R . .
C4 C -0.2816(11) 0.7922(4) 0.4594(4) 0.024(2) Uani 1 1 d . . .
H4A H -0.3694 0.7664 0.4707 0.029 Uiso 1 1 calc R . .
H4B H -0.3311 0.8281 0.4466 0.029 Uiso 1 1 calc R . .
C5 C -0.1871(12) 0.7648(4) 0.4147(4) 0.022(2) Uani 1 1 d U . .
H5A H -0.2617 0.7559 0.3852 0.027 Uiso 1 1 calc R . .
H5B H -0.1410 0.7284 0.4276 0.027 Uiso 1 1 calc R . .
C6 C -0.0516(11) 0.8020(4) 0.3937(4) 0.0159(17) Uani 1 1 d U . .
H6A H 0.0233 0.7785 0.3723 0.019 Uiso 1 1 calc R . .
H6B H -0.0968 0.8319 0.3704 0.019 Uiso 1 1 calc R . .
C7 C 0.0376(10) 0.8289(3) 0.4384(3) 0.0099(16) Uani 1 1 d U . .
C8 C 0.1911(10) 0.8587(4) 0.4376(3) 0.0115(16) Uani 1 1 d . . .
C9 C 0.2983(9) 0.8702(4) 0.3969(4) 0.0163(17) Uani 1 1 d . . .
C10 C 0.4380(11) 0.9026(4) 0.4053(3) 0.0150(17) Uani 1 1 d U . .
C11 C 0.5617(10) 0.9197(3) 0.3698(3) 0.0094(15) Uani 1 1 d U . .
C12 C 0.5764(11) 0.9138(4) 0.3106(3) 0.0149(16) Uani 1 1 d U . .
H12A H 0.5020 0.9408 0.2929 0.018 Uiso 1 1 calc R . .
H12B H 0.5456 0.8747 0.2999 0.018 Uiso 1 1 calc R . .
C13 C 0.7523(12) 0.9262(4) 0.2926(3) 0.0176(16) Uani 1 1 d . . .
H13A H 0.8215 0.8933 0.3019 0.021 Uiso 1 1 calc R . .
H13B H 0.7550 0.9309 0.2536 0.021 Uiso 1 1 calc R . .
C14 C 0.8191(11) 0.9798(4) 0.3190(3) 0.0177(19) Uani 1 1 d . . .
H14A H 0.7475 1.0125 0.3113 0.021 Uiso 1 1 calc R . .
H14B H 0.9271 0.9885 0.3044 0.021 Uiso 1 1 calc R . .
C15 C 0.8309(10) 0.9712(4) 0.3791(3) 0.0146(17) Uani 1 1 d . . .
H15A H 0.9218 0.9452 0.3871 0.017 Uiso 1 1 calc R . .
H15B H 0.8526 1.0082 0.3965 0.017 Uiso 1 1 calc R . .
C16 C 0.6774(10) 0.9464(3) 0.4007(4) 0.0123(16) Uani 1 1 d . . .
C17 C 0.6269(10) 0.9452(4) 0.4523(3) 0.0125(17) Uani 1 1 d . . .
C18 C 0.2671(11) 0.8483(3) 0.3425(3) 0.0116(15) Uani 1 1 d U . .
C19 C 0.3279(11) 0.7955(4) 0.3274(4) 0.0167(18) Uani 1 1 d . . .
H19 H 0.3830 0.7727 0.3528 0.020 Uiso 1 1 calc R . .
C20 C 0.3093(12) 0.7757(4) 0.2762(4) 0.024(2) Uani 1 1 d . . .
H20 H 0.3531 0.7399 0.2663 0.029 Uiso 1 1 calc R . .
C21 C 0.2267(12) 0.8082(4) 0.2392(4) 0.023(2) Uani 1 1 d . . .
H21 H 0.2134 0.7945 0.2040 0.027 Uiso 1 1 calc R . .
C22 C 0.1632(10) 0.8608(4) 0.2537(3) 0.0190(19) Uani 1 1 d . . .
H22 H 0.1052 0.8827 0.2284 0.023 Uiso 1 1 calc R . .
C23 C 0.1842(11) 0.8814(4) 0.3050(3) 0.0154(17) Uani 1 1 d . . .
H23 H 0.1427 0.9176 0.3146 0.018 Uiso 1 1 calc R . .
B1 B 0.3827(11) 0.9065(4) 0.5080(4) 0.015(2) Uani 1 1 d . . .
I3 I 1.24652(7) 0.96003(2) 0.74052(2) 0.01431(12) Uani 1 1 d . . .
I4 I 0.57782(7) 0.86365(2) 0.65106(2) 0.01455(12) Uani 1 1 d . . .
F3 F 0.8435(6) 0.9454(2) 0.7215(2) 0.0174(11) Uani 1 1 d . . .
F4 F 0.9588(6) 0.8575(2) 0.71384(19) 0.0143(10) Uani 1 1 d . . .
N3 N 0.9689(9) 0.9036(3) 0.7987(3) 0.0137(15) Uani 1 1 d U . .
N4 N 0.7108(8) 0.8645(3) 0.7633(3) 0.0124(14) Uani 1 1 d . . .
C24 C 1.1117(10) 0.9302(4) 0.8040(3) 0.0147(18) Uani 1 1 d U . .
C25 C 1.1641(10) 0.9296(3) 0.8570(3) 0.0122(16) Uani 1 1 d . . .
C26 C 1.3159(10) 0.9536(4) 0.8791(3) 0.0128(16) Uani 1 1 d . . .
H26A H 1.3359 0.9918 0.8639 0.015 Uiso 1 1 calc R . .
H26B H 1.4079 0.9287 0.8698 0.015 Uiso 1 1 calc R . .
C27 C 1.3008(10) 0.9580(4) 0.9400(3) 0.0133(17) Uani 1 1 d U . .
H27A H 1.4083 0.9652 0.9556 0.016 Uiso 1 1 calc R . .
H27B H 1.2300 0.9904 0.9492 0.016 Uiso 1 1 calc R . .
C28 C 1.2317(11) 0.9037(3) 0.9630(3) 0.0135(16) Uani 1 1 d . . .
H28A H 1.3007 0.8712 0.9525 0.016 Uiso 1 1 calc R . .
H28B H 1.2334 0.9063 1.0023 0.016 Uiso 1 1 calc R . .
C29 C 1.0611(11) 0.8926(4) 0.9448(3) 0.0173(18) Uani 1 1 d . . .
H29A H 1.0307 0.8529 0.9535 0.021 Uiso 1 1 calc R . .
H29B H 0.9864 0.9184 0.9638 0.021 Uiso 1 1 calc R . .
C30 C 1.0461(9) 0.9019(3) 0.8859(3) 0.0098(16) Uani 1 1 d U . .
C31 C 0.9238(10) 0.8850(3) 0.8496(3) 0.0108(14) Uani 1 1 d U . .
C32 C 0.7810(10) 0.8539(3) 0.8568(3) 0.0140(17) Uani 1 1 d . . .
C33 C 0.6745(10) 0.8442(3) 0.8144(3) 0.0101(16) Uani 1 1 d U . .
C34 C 0.5247(10) 0.8153(3) 0.8116(3) 0.0098(16) Uani 1 1 d U . .
C35 C 0.4289(11) 0.7856(4) 0.8544(3) 0.0176(17) Uani 1 1 d . . .
H35A H 0.4211 0.8106 0.8860 0.021 Uiso 1 1 calc R . .
H35B H 0.4846 0.7501 0.8650 0.021 Uiso 1 1 calc R . .
C36 C 0.2566(14) 0.7712(4) 0.8338(4) 0.025(2) Uani 1 1 d . . .
H36A H 0.2048 0.7439 0.8584 0.030 Uiso 1 1 calc R . .
H36B H 0.1907 0.8064 0.8333 0.030 Uiso 1 1 calc R . .
C37 C 0.2612(14) 0.7462(4) 0.7793(4) 0.026(2) Uani 1 1 d . . .
H37A H 0.1512 0.7342 0.7690 0.031 Uiso 1 1 calc R . .
H37B H 0.3308 0.7119 0.7795 0.031 Uiso 1 1 calc R . .
C38 C 0.3251(10) 0.7883(4) 0.7388(4) 0.0143(17) Uani 1 1 d . . .
H38A H 0.3499 0.7683 0.7051 0.017 Uiso 1 1 calc R . .
H38B H 0.2426 0.8177 0.7314 0.017 Uiso 1 1 calc R . .
C39 C 0.4744(9) 0.8157(3) 0.7602(3) 0.0096(15) Uani 1 1 d U . .
C40 C 0.5940(10) 0.8482(3) 0.7308(3) 0.0113(15) Uani 1 1 d U . .
C41 C 0.7429(12) 0.8303(3) 0.9104(3) 0.0138(15) Uani 1 1 d U . .
C42 C 0.6731(10) 0.8636(4) 0.9495(4) 0.0166(17) Uani 1 1 d . . .
H42 H 0.6446 0.9020 0.9424 0.020 Uiso 1 1 calc R . .
C43 C 0.6455(12) 0.8403(5) 0.9989(4) 0.025(2) Uani 1 1 d . . .
H43 H 0.5980 0.8630 1.0260 0.030 Uiso 1 1 calc R . .
C44 C 0.6850(13) 0.7858(5) 1.0094(4) 0.033(3) Uani 1 1 d . . .
H44 H 0.6625 0.7703 1.0435 0.040 Uiso 1 1 calc R . .
C45 C 0.7580(16) 0.7518(4) 0.9712(4) 0.031(2) Uani 1 1 d U . .
H45 H 0.7877 0.7138 0.9796 0.037 Uiso 1 1 calc R . .
C46 C 0.7880(11) 0.7735(4) 0.9204(4) 0.019(2) Uani 1 1 d U . .
H46 H 0.8370 0.7508 0.8937 0.023 Uiso 1 1 calc R . .
B2 B 0.8726(12) 0.8944(4) 0.7472(4) 0.0118(18) Uani 1 1 d . . .
C47 C 0.5038(18) 0.0705(5) 0.5958(6) 0.045(3) Uani 1 1 d . . .
H47A H 0.6045 0.0774 0.5758 0.055 Uiso 1 1 calc R . .
H47B H 0.4321 0.0470 0.5734 0.055 Uiso 1 1 calc R . .
Cl1 Cl 0.4096(5) 0.13594(13) 0.60876(13) 0.0496(8) Uani 1 1 d . . .
Cl2 Cl 0.5497(4) 0.03272(13) 0.65507(13) 0.0462(8) Uani 1 1 d . . .
C48 C 1.0083(17) 0.0684(5) 0.6584(6) 0.043(3) Uani 1 1 d . . .
H48A H 0.9380 0.0415 0.6779 0.051 Uiso 1 1 calc R . .
H48B H 1.1051 0.0755 0.6804 0.051 Uiso 1 1 calc R . .
Cl3 Cl 0.9053(5) 0.13259(16) 0.64922(15) 0.0591(9) Uani 1 1 d . . .
Cl4 Cl 1.0672(4) 0.03732(14) 0.59815(14) 0.0484(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.069(9) . ?
I2 C17 2.066(8) . ?
F1 B1 1.381(11) . ?
F2 B1 1.393(12) . ?
N1 C1 1.356(11) . ?
N1 C8 1.405(10) . ?
N1 B1 1.551(11) . ?
N2 C17 1.361(11) . ?
N2 C10 1.391(11) . ?
N2 B1 1.561(12) . ?
C1 C2 1.403(13) . ?
C2 C7 1.369(12) . ?
C2 C3 1.480(12) . ?
C3 C4 1.533(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.488(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.453(11) . ?
C8 C9 1.384(12) . ?
C9 C10 1.403(12) . ?
C9 C18 1.484(12) . ?
C10 C11 1.419(12) . ?
C11 C16 1.385(12) . ?
C11 C12 1.503(11) . ?
C12 C13 1.555(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.528(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.528(12) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.502(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.365(12) . ?
C18 C19 1.392(11) . ?
C18 C23 1.402(12) . ?
C19 C20 1.379(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(13) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
I3 C24 2.073(9) . ?
I4 C40 2.045(8) . ?
F3 B2 1.383(10) . ?
F4 B2 1.403(10) . ?
N3 C24 1.347(11) . ?
N3 C31 1.403(11) . ?
N3 B2 1.536(12) . ?
N4 C40 1.326(11) . ?
N4 C33 1.403(10) . ?
N4 B2 1.568(12) . ?
C24 C25 1.401(12) . ?
C25 C30 1.383(12) . ?
C25 C26 1.488(12) . ?
C26 C27 1.540(11) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.513(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.510(12) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.505(11) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.422(11) . ?
C31 C32 1.404(12) . ?
C32 C33 1.405(12) . ?
C32 C41 1.493(11) . ?
C33 C34 1.418(11) . ?
C34 C39 1.359(11) . ?
C34 C35 1.510(12) . ?
C35 C36 1.558(14) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.493(13) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.516(13) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.496(11) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.453(11) . ?
C41 C42 1.384(12) . ?
C41 C46 1.408(12) . ?
C42 C43 1.378(13) . ?
C42 H42 0.9500 . ?
C43 C44 1.348(16) . ?
C43 H43 0.9500 . ?
C44 C45 1.389(16) . ?
C44 H44 0.9500 . ?
C45 C46 1.399(13) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 Cl1 1.753(13) . ?
C47 Cl2 1.777(14) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 Cl3 1.747(12) . ?
C48 Cl4 1.753(15) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 105.8(7) . . ?
C1 N1 B1 128.1(7) . . ?
C8 N1 B1 125.8(7) . . ?
C17 N2 C10 106.4(7) . . ?
C17 N2 B1 127.8(7) . . ?
C10 N2 B1 125.6(7) . . ?
N1 C1 C2 112.2(8) . . ?
N1 C1 I1 125.0(6) . . ?
C2 C1 I1 122.8(6) . . ?
C7 C2 C1 106.9(8) . . ?
C7 C2 C3 123.7(8) . . ?
C1 C2 C3 129.4(8) . . ?
C2 C3 C4 111.1(8) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.9(8) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 113.5(8) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 110.4(7) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C2 C7 C8 107.0(7) . . ?
C2 C7 C6 123.9(8) . . ?
C8 C7 C6 129.0(8) . . ?
C9 C8 N1 120.0(8) . . ?
C9 C8 C7 131.9(8) . . ?
N1 C8 C7 108.1(7) . . ?
C8 C9 C10 121.6(8) . . ?
C8 C9 C18 120.2(7) . . ?
C10 C9 C18 118.2(8) . . ?
N2 C10 C9 120.3(8) . . ?
N2 C10 C11 108.6(7) . . ?
C9 C10 C11 130.9(8) . . ?
C16 C11 C10 106.0(7) . . ?
C16 C11 C12 122.9(8) . . ?
C10 C11 C12 131.1(8) . . ?
C11 C12 C13 110.3(7) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.6(7) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.1(7) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 110.8(7) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C11 108.2(7) . . ?
C17 C16 C15 127.8(8) . . ?
C11 C16 C15 124.0(8) . . ?
N2 C17 C16 110.8(7) . . ?
N2 C17 I2 123.5(6) . . ?
C16 C17 I2 125.7(6) . . ?
C19 C18 C23 119.1(8) . . ?
C19 C18 C9 119.8(8) . . ?
C23 C18 C9 121.0(7) . . ?
C20 C19 C18 120.9(9) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.9(9) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.0(9) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.3(9) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 119.7(8) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?
F1 B1 F2 110.9(8) . . ?
F1 B1 N1 109.8(7) . . ?
F2 B1 N1 110.5(7) . . ?
F1 B1 N2 109.9(7) . . ?
F2 B1 N2 109.7(7) . . ?
N1 B1 N2 105.9(7) . . ?
C24 N3 C31 106.7(7) . . ?
C24 N3 B2 127.4(7) . . ?
C31 N3 B2 126.0(7) . . ?
C40 N4 C33 108.1(7) . . ?
C40 N4 B2 126.6(7) . . ?
C33 N4 B2 124.9(7) . . ?
N3 C24 C25 111.4(8) . . ?
N3 C24 I3 123.7(6) . . ?
C25 C24 I3 124.7(6) . . ?
C30 C25 C24 106.6(8) . . ?
C30 C25 C26 125.4(8) . . ?
C24 C25 C26 128.0(8) . . ?
C25 C26 C27 109.2(7) . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
C27 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C28 C27 C26 110.9(7) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.0 . . ?
C29 C28 C27 112.6(7) . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C30 C29 C28 110.6(7) . . ?
C30 C29 H29A 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C25 C30 C31 107.3(7) . . ?
C25 C30 C29 121.9(7) . . ?
C31 C30 C29 130.8(7) . . ?
N3 C31 C32 120.3(7) . . ?
N3 C31 C30 108.1(7) . . ?
C32 C31 C30 131.6(8) . . ?
C31 C32 C33 121.1(8) . . ?
C31 C32 C41 119.3(7) . . ?
C33 C32 C41 119.6(8) . . ?
N4 C33 C32 120.4(7) . . ?
N4 C33 C34 107.8(7) . . ?
C32 C33 C34 131.8(8) . . ?
C39 C34 C33 108.3(7) . . ?
C39 C34 C35 121.4(8) . . ?
C33 C34 C35 130.3(8) . . ?
C34 C35 C36 110.2(7) . . ?
C34 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
C34 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C37 C36 C35 111.6(9) . . ?
C37 C36 H36A 109.3 . . ?
C35 C36 H36A 109.3 . . ?
C37 C36 H36B 109.3 . . ?
C35 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
C36 C37 C38 111.7(8) . . ?
C36 C37 H37A 109.3 . . ?
C38 C37 H37A 109.3 . . ?
C36 C37 H37B 109.3 . . ?
C38 C37 H37B 109.3 . . ?
H37A C37 H37B 107.9 . . ?
C39 C38 C37 109.1(8) . . ?
C39 C38 H38A 109.9 . . ?
C37 C38 H38A 109.9 . . ?
C39 C38 H38B 109.9 . . ?
C37 C38 H38B 109.9 . . ?
H38A C38 H38B 108.3 . . ?
C34 C39 C40 106.1(7) . . ?
C34 C39 C38 126.4(8) . . ?
C40 C39 C38 127.4(8) . . ?
N4 C40 C39 109.7(7) . . ?
N4 C40 I4 127.1(6) . . ?
C39 C40 I4 123.2(6) . . ?
C42 C41 C46 121.2(8) . . ?
C42 C41 C32 121.5(7) . . ?
C46 C41 C32 117.2(8) . . ?
C43 C42 C41 119.2(9) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C44 C43 C42 120.9(10) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 121.0(10) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C45 C46 120.2(10) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C45 C46 C41 117.5(9) . . ?
C45 C46 H46 121.3 . . ?
C41 C46 H46 121.3 . . ?
F3 B2 F4 110.1(7) . . ?
F3 B2 N3 111.3(7) . . ?
F4 B2 N3 109.1(7) . . ?
F3 B2 N4 111.0(7) . . ?
F4 B2 N4 108.4(7) . . ?
N3 B2 N4 106.9(7) . . ?
Cl1 C47 Cl2 112.2(8) . . ?
Cl1 C47 H47A 109.2 . . ?
Cl2 C47 H47A 109.2 . . ?
Cl1 C47 H47B 109.2 . . ?
Cl2 C47 H47B 109.2 . . ?
H47A C47 H47B 107.9 . . ?
Cl3 C48 Cl4 112.4(8) . . ?
Cl3 C48 H48A 109.1 . . ?
Cl4 C48 H48A 109.1 . . ?
Cl3 C48 H48B 109.1 . . ?
Cl4 C48 H48B 109.1 . . ?
H48A C48 H48B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -0.7(9) . . . . ?
B1 N1 C1 C2 -174.5(8) . . . . ?
C8 N1 C1 I1 178.5(6) . . . . ?
B1 N1 C1 I1 4.7(12) . . . . ?
N1 C1 C2 C7 1.3(10) . . . . ?
I1 C1 C2 C7 -178.0(6) . . . . ?
N1 C1 C2 C3 179.4(8) . . . . ?
I1 C1 C2 C3 0.1(13) . . . . ?
C7 C2 C3 C4 -17.6(11) . . . . ?
C1 C2 C3 C4 164.6(9) . . . . ?
C2 C3 C4 C5 44.8(11) . . . . ?
C3 C4 C5 C6 -60.5(11) . . . . ?
C4 C5 C6 C7 43.5(11) . . . . ?
C1 C2 C7 C8 -1.2(9) . . . . ?
C3 C2 C7 C8 -179.4(7) . . . . ?
C1 C2 C7 C6 -179.2(8) . . . . ?
C3 C2 C7 C6 2.5(13) . . . . ?
C5 C6 C7 C2 -14.9(12) . . . . ?
C5 C6 C7 C8 167.5(8) . . . . ?
C1 N1 C8 C9 179.5(8) . . . . ?
B1 N1 C8 C9 -6.5(12) . . . . ?
C1 N1 C8 C7 0.0(9) . . . . ?
B1 N1 C8 C7 174.0(7) . . . . ?
C2 C7 C8 C9 -178.7(9) . . . . ?
C6 C7 C8 C9 -0.8(15) . . . . ?
C2 C7 C8 N1 0.8(9) . . . . ?
C6 C7 C8 N1 178.7(8) . . . . ?
N1 C8 C9 C10 -2.5(13) . . . . ?
C7 C8 C9 C10 176.9(8) . . . . ?
N1 C8 C9 C18 177.6(7) . . . . ?
C7 C8 C9 C18 -3.0(14) . . . . ?
C17 N2 C10 C9 174.2(8) . . . . ?
B1 N2 C10 C9 -0.4(12) . . . . ?
C17 N2 C10 C11 -1.5(9) . . . . ?
B1 N2 C10 C11 -176.2(7) . . . . ?
C8 C9 C10 N2 5.8(13) . . . . ?
C18 C9 C10 N2 -174.3(7) . . . . ?
C8 C9 C10 C11 -179.5(8) . . . . ?
C18 C9 C10 C11 0.5(14) . . . . ?
N2 C10 C11 C16 0.8(9) . . . . ?
C9 C10 C11 C16 -174.4(9) . . . . ?
N2 C10 C11 C12 -178.0(8) . . . . ?
C9 C10 C11 C12 6.8(15) . . . . ?
C16 C11 C12 C13 15.2(11) . . . . ?
C10 C11 C12 C13 -166.3(8) . . . . ?
C11 C12 C13 C14 -46.0(9) . . . . ?
C12 C13 C14 C15 64.3(9) . . . . ?
C13 C14 C15 C16 -47.7(10) . . . . ?
C10 C11 C16 C17 0.3(9) . . . . ?
C12 C11 C16 C17 179.2(8) . . . . ?
C10 C11 C16 C15 179.8(7) . . . . ?
C12 C11 C16 C15 -1.3(13) . . . . ?
C14 C15 C16 C17 -163.0(9) . . . . ?
C14 C15 C16 C11 17.6(12) . . . . ?
C10 N2 C17 C16 1.8(9) . . . . ?
B1 N2 C17 C16 176.3(8) . . . . ?
C10 N2 C17 I2 -176.0(6) . . . . ?
B1 N2 C17 I2 -1.5(11) . . . . ?
C11 C16 C17 N2 -1.3(10) . . . . ?
C15 C16 C17 N2 179.2(8) . . . . ?
C11 C16 C17 I2 176.4(6) . . . . ?
C15 C16 C17 I2 -3.1(13) . . . . ?
C8 C9 C18 C19 -90.7(11) . . . . ?
C10 C9 C18 C19 89.3(10) . . . . ?
C8 C9 C18 C23 92.6(11) . . . . ?
C10 C9 C18 C23 -87.3(11) . . . . ?
C23 C18 C19 C20 0.8(13) . . . . ?
C9 C18 C19 C20 -175.9(8) . . . . ?
C18 C19 C20 C21 -1.2(14) . . . . ?
C19 C20 C21 C22 0.3(14) . . . . ?
C20 C21 C22 C23 0.9(14) . . . . ?
C21 C22 C23 C18 -1.3(13) . . . . ?
C19 C18 C23 C22 0.4(13) . . . . ?
C9 C18 C23 C22 177.1(8) . . . . ?
C1 N1 B1 F1 64.2(11) . . . . ?
C8 N1 B1 F1 -108.5(9) . . . . ?
C1 N1 B1 F2 -58.5(11) . . . . ?
C8 N1 B1 F2 128.9(8) . . . . ?
C1 N1 B1 N2 -177.2(8) . . . . ?
C8 N1 B1 N2 10.1(11) . . . . ?
C17 N2 B1 F1 -61.6(11) . . . . ?
C10 N2 B1 F1 111.9(9) . . . . ?
C17 N2 B1 F2 60.6(10) . . . . ?
C10 N2 B1 F2 -125.9(8) . . . . ?
C17 N2 B1 N1 179.8(7) . . . . ?
C10 N2 B1 N1 -6.7(11) . . . . ?
C31 N3 C24 C25 0.4(9) . . . . ?
B2 N3 C24 C25 -179.1(8) . . . . ?
C31 N3 C24 I3 174.3(6) . . . . ?
B2 N3 C24 I3 -5.3(12) . . . . ?
N3 C24 C25 C30 -0.9(10) . . . . ?
I3 C24 C25 C30 -174.7(6) . . . . ?
N3 C24 C25 C26 179.1(8) . . . . ?
I3 C24 C25 C26 5.3(12) . . . . ?
C30 C25 C26 C27 -15.6(11) . . . . ?
C24 C25 C26 C27 164.4(8) . . . . ?
C25 C26 C27 C28 46.0(9) . . . . ?
C26 C27 C28 C29 -64.3(9) . . . . ?
C27 C28 C29 C30 45.6(10) . . . . ?
C24 C25 C30 C31 1.0(9) . . . . ?
C26 C25 C30 C31 -179.0(7) . . . . ?
C24 C25 C30 C29 179.4(8) . . . . ?
C26 C25 C30 C29 -0.5(13) . . . . ?
C28 C29 C30 C25 -13.9(11) . . . . ?
C28 C29 C30 C31 164.1(8) . . . . ?
C24 N3 C31 C32 -178.0(7) . . . . ?
B2 N3 C31 C32 1.6(12) . . . . ?
C24 N3 C31 C30 0.2(9) . . . . ?
B2 N3 C31 C30 179.8(7) . . . . ?
C25 C30 C31 N3 -0.7(9) . . . . ?
C29 C30 C31 N3 -179.0(8) . . . . ?
C25 C30 C31 C32 177.2(8) . . . . ?
C29 C30 C31 C32 -1.1(15) . . . . ?
N3 C31 C32 C33 -4.6(12) . . . . ?
C30 C31 C32 C33 177.6(8) . . . . ?
N3 C31 C32 C41 174.6(7) . . . . ?
C30 C31 C32 C41 -3.1(13) . . . . ?
C40 N4 C33 C32 178.1(7) . . . . ?
B2 N4 C33 C32 5.2(12) . . . . ?
C40 N4 C33 C34 -1.5(9) . . . . ?
B2 N4 C33 C34 -174.4(7) . . . . ?
C31 C32 C33 N4 1.3(12) . . . . ?
C41 C32 C33 N4 -177.9(7) . . . . ?
C31 C32 C33 C34 -179.2(8) . . . . ?
C41 C32 C33 C34 1.6(13) . . . . ?
N4 C33 C34 C39 2.6(9) . . . . ?
C32 C33 C34 C39 -176.9(9) . . . . ?
N4 C33 C34 C35 -179.7(8) . . . . ?
C32 C33 C34 C35 0.7(15) . . . . ?
C39 C34 C35 C36 -14.0(11) . . . . ?
C33 C34 C35 C36 168.5(8) . . . . ?
C34 C35 C36 C37 45.2(10) . . . . ?
C35 C36 C37 C38 -64.3(11) . . . . ?
C36 C37 C38 C39 46.9(11) . . . . ?
C33 C34 C39 C40 -2.6(9) . . . . ?
C35 C34 C39 C40 179.5(7) . . . . ?
C33 C34 C39 C38 177.8(8) . . . . ?
C35 C34 C39 C38 -0.1(13) . . . . ?
C37 C38 C39 C34 -15.7(12) . . . . ?
C37 C38 C39 C40 164.7(8) . . . . ?
C33 N4 C40 C39 -0.1(9) . . . . ?
B2 N4 C40 C39 172.7(7) . . . . ?
C33 N4 C40 I4 -179.3(6) . . . . ?
B2 N4 C40 I4 -6.5(12) . . . . ?
C34 C39 C40 N4 1.7(9) . . . . ?
C38 C39 C40 N4 -178.6(8) . . . . ?
C34 C39 C40 I4 -179.0(6) . . . . ?
C38 C39 C40 I4 0.6(12) . . . . ?
C31 C32 C41 C42 82.0(11) . . . . ?
C33 C32 C41 C42 -98.7(10) . . . . ?
C31 C32 C41 C46 -95.0(10) . . . . ?
C33 C32 C41 C46 84.3(11) . . . . ?
C46 C41 C42 C43 -0.9(14) . . . . ?
C32 C41 C42 C43 -177.8(8) . . . . ?
C41 C42 C43 C44 -0.2(15) . . . . ?
C42 C43 C44 C45 1.5(17) . . . . ?
C43 C44 C45 C46 -1.7(18) . . . . ?
C44 C45 C46 C41 0.5(16) . . . . ?
C42 C41 C46 C45 0.7(15) . . . . ?
C32 C41 C46 C45 177.7(9) . . . . ?
C24 N3 B2 F3 -55.3(11) . . . . ?
C31 N3 B2 F3 125.2(8) . . . . ?
C24 N3 B2 F4 66.4(10) . . . . ?
C31 N3 B2 F4 -113.1(9) . . . . ?
C24 N3 B2 N4 -176.6(8) . . . . ?
C31 N3 B2 N4 3.9(11) . . . . ?
C40 N4 B2 F3 59.6(11) . . . . ?
C33 N4 B2 F3 -128.8(8) . . . . ?
C40 N4 B2 F4 -61.5(10) . . . . ?
C33 N4 B2 F4 110.2(8) . . . . ?
C40 N4 B2 N3 -178.9(7) . . . . ?
C33 N4 B2 N3 -7.2(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         3.467
_refine_diff_density_min         -1.350
_refine_diff_density_rms         0.213
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound5a
_database_code_depnum_ccdc_archive 'CCDC 1435989'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H31 B F2 N2'
_chemical_formula_sum            'C35 H31 B F2 N2'
_chemical_formula_weight         528.43

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

_symmetry_space_group_name_H-M   'P 21 21 21    '
_symmetry_space_group_name_Hall  'P 2ac 2ab '
_symmetry_cell_setting           Orthorhombic

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

_cell_length_a                   11.0477(15)
_cell_length_b                   14.069(2)
_cell_length_c                   17.029(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2646.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.36

_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            79037
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         26.48
_reflns_number_total             5446
_reflns_number_gt                4897
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0365P)²+0.7227P] 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     SHELXL
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_number_reflns         5446
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.48638(8) 0.39372(7) 0.33124(6) 0.0284(2) Uani 1 1 d . . .
F2 F 0.52232(9) 0.24235(7) 0.37268(6) 0.0307(3) Uani 1 1 d . . .
N1 N 0.65833(11) 0.36844(9) 0.41261(7) 0.0139(3) Uani 1 1 d . . .
N2 N 0.65479(11) 0.30560(8) 0.27500(7) 0.0141(3) Uani 1 1 d . . .
C1 C 0.62323(14) 0.40309(11) 0.48346(9) 0.0150(3) Uani 1 1 d . . .
C2 C 0.72504(14) 0.44031(11) 0.52296(9) 0.0166(3) Uani 1 1 d . . .
C3 C 0.73060(15) 0.47835(13) 0.60548(9) 0.0216(4) Uani 1 1 d . . .
H3A H 0.6865 0.4350 0.6413 0.026 Uiso 1 1 calc R . .
H3B H 0.6910 0.5414 0.6077 0.026 Uiso 1 1 calc R . .
C4 C 0.86267(14) 0.48722(12) 0.63209(9) 0.0226(4) Uani 1 1 d . . .
H4A H 0.8670 0.5266 0.6802 0.027 Uiso 1 1 calc R . .
H4B H 0.8953 0.4235 0.6446 0.027 Uiso 1 1 calc R . .
C5 C 0.93782(14) 0.53247(12) 0.56764(10) 0.0209(4) Uani 1 1 d . . .
H5A H 1.0200 0.5461 0.5879 0.025 Uiso 1 1 calc R . .
H5B H 0.9004 0.5935 0.5519 0.025 Uiso 1 1 calc R . .
C6 C 0.94729(14) 0.46754(11) 0.49605(9) 0.0187(3) Uani 1 1 d . . .
H6A H 0.9834 0.5029 0.4516 0.022 Uiso 1 1 calc R . .
H6B H 1.0005 0.4129 0.5083 0.022 Uiso 1 1 calc R . .
C7 C 0.82369(13) 0.43235(11) 0.47354(9) 0.0151(3) Uani 1 1 d . . .
C8 C 0.78232(13) 0.38706(11) 0.40374(9) 0.0140(3) Uani 1 1 d . . .
C9 C 0.84022(13) 0.36594(10) 0.33310(9) 0.0149(3) Uani 1 1 d . . .
C10 C 0.77934(13) 0.32305(11) 0.27082(9) 0.0142(3) Uani 1 1 d . . .
C11 C 0.82242(13) 0.28515(11) 0.19868(9) 0.0160(3) Uani 1 1 d . . .
C12 C 0.94836(13) 0.28461(12) 0.16523(9) 0.0179(3) Uani 1 1 d . . .
H12A H 1.0053 0.2592 0.2049 0.021 Uiso 1 1 calc R . .
H12B H 0.9730 0.3506 0.1528 0.021 Uiso 1 1 calc R . .
C13 C 0.95570(14) 0.22394(12) 0.09074(9) 0.0214(4) Uani 1 1 d . . .
H13A H 1.0289 0.2421 0.0607 0.026 Uiso 1 1 calc R . .
H13B H 0.9640 0.1563 0.1058 0.026 Uiso 1 1 calc R . .
C14 C 0.84497(14) 0.23528(13) 0.03838(10) 0.0235(4) Uani 1 1 d . . .
H14A H 0.8565 0.1980 -0.0104 0.028 Uiso 1 1 calc R . .
H14B H 0.8357 0.3030 0.0236 0.028 Uiso 1 1 calc R . .
C15 C 0.73061(14) 0.20137(12) 0.08033(9) 0.0187(3) Uani 1 1 d . . .
H15A H 0.6583 0.2198 0.0496 0.022 Uiso 1 1 calc R . .
H15B H 0.7317 0.1312 0.0849 0.022 Uiso 1 1 calc R . .
C16 C 0.72443(13) 0.24510(11) 0.16061(9) 0.0156(3) Uani 1 1 d . . .
C17 C 0.62204(13) 0.25890(10) 0.20889(9) 0.0150(3) Uani 1 1 d . . .
C18 C 0.49656(14) 0.40997(11) 0.51073(9) 0.0167(3) Uani 1 1 d . . .
C19 C 0.41775(14) 0.33343(12) 0.51497(9) 0.0197(3) Uani 1 1 d . . .
H19 H 0.4433 0.2724 0.4977 0.024 Uiso 1 1 calc R . .
C20 C 0.30149(14) 0.34578(13) 0.54435(10) 0.0244(4) Uani 1 1 d . . .
H20 H 0.2479 0.2931 0.5471 0.029 Uiso 1 1 calc R . .
C21 C 0.26342(15) 0.43394(13) 0.56951(10) 0.0254(4) Uani 1 1 d . . .
H21 H 0.1845 0.4415 0.5907 0.030 Uiso 1 1 calc R . .
C22 C 0.33943(15) 0.51091(13) 0.56393(10) 0.0246(4) Uani 1 1 d . . .
H22 H 0.3124 0.5720 0.5799 0.030 Uiso 1 1 calc R . .
C23 C 0.45585(14) 0.49925(12) 0.53484(10) 0.0212(4) Uani 1 1 d . . .
H23 H 0.5084 0.5526 0.5313 0.025 Uiso 1 1 calc R . .
C24 C 0.96936(13) 0.39507(11) 0.32266(9) 0.0166(3) Uani 1 1 d . . .
C25 C 1.06474(14) 0.34227(13) 0.35288(10) 0.0212(4) Uani 1 1 d . . .
H25 H 1.0493 0.2843 0.3797 0.025 Uiso 1 1 calc R . .
C26 C 1.18326(14) 0.37460(14) 0.34368(10) 0.0273(4) Uani 1 1 d . . .
H26 H 1.2487 0.3388 0.3646 0.033 Uiso 1 1 calc R . .
C27 C 1.20569(15) 0.45879(14) 0.30410(11) 0.0305(4) Uani 1 1 d . . .
H27 H 1.2865 0.4807 0.2982 0.037 Uiso 1 1 calc R . .
C28 C 1.11163(15) 0.51086(13) 0.27322(11) 0.0276(4) Uani 1 1 d . . .
H28 H 1.1274 0.5684 0.2458 0.033 Uiso 1 1 calc R . .
C29 C 0.99328(14) 0.47897(11) 0.28227(9) 0.0205(3) Uani 1 1 d . . .
H29 H 0.9283 0.5147 0.2607 0.025 Uiso 1 1 calc R . .
C30 C 0.49681(13) 0.22758(11) 0.19106(9) 0.0158(3) Uani 1 1 d . . .
C31 C 0.39841(14) 0.28869(12) 0.19474(9) 0.0178(3) Uani 1 1 d . . .
H31 H 0.4101 0.3532 0.2093 0.021 Uiso 1 1 calc R . .
C32 C 0.28303(14) 0.25589(12) 0.17730(9) 0.0206(3) Uani 1 1 d . . .
H32 H 0.2159 0.2979 0.1805 0.025 Uiso 1 1 calc R . .
C33 C 0.26524(14) 0.16228(12) 0.15531(10) 0.0225(4) Uani 1 1 d . . .
H33 H 0.1861 0.1399 0.1437 0.027 Uiso 1 1 calc R . .
C34 C 0.36298(15) 0.10157(12) 0.15028(10) 0.0247(4) Uani 1 1 d . . .
H34 H 0.3511 0.0372 0.1352 0.030 Uiso 1 1 calc R . .
C35 C 0.47887(14) 0.13428(11) 0.16727(10) 0.0212(3) Uani 1 1 d . . .
H35 H 0.5461 0.0926 0.1626 0.025 Uiso 1 1 calc R . .
B1 B 0.57464(15) 0.32658(13) 0.34799(11) 0.0167(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
F1 B1 1.387(2) . ?
F2 B1 1.384(2) . ?
N1 C1 1.358(2) . ?
N1 C8 1.4028(18) . ?
N1 B1 1.553(2) . ?
N2 C17 1.353(2) . ?
N2 C10 1.3995(19) . ?
N2 B1 1.554(2) . ?
C1 C2 1.411(2) . ?
C1 C18 1.478(2) . ?
C2 C7 1.381(2) . ?
C2 C3 1.505(2) . ?
C3 C4 1.533(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.424(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.393(2) . ?
C9 C24 1.495(2) . ?
C10 C11 1.421(2) . ?
C11 C16 1.382(2) . ?
C11 C12 1.504(2) . ?
C12 C13 1.531(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.522(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.528(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.501(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.412(2) . ?
C17 C30 1.483(2) . ?
C18 C19 1.387(2) . ?
C18 C23 1.396(2) . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.388(2) . ?
C24 C29 1.391(2) . ?
C25 C26 1.395(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.391(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.387(2) . ?
C30 C35 1.388(2) . ?
C31 C32 1.388(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.383(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(2) . ?
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
C1 N1 C8 107.91(12) . . ?
C1 N1 B1 126.56(12) . . ?
C8 N1 B1 125.15(13) . . ?
C17 N2 C10 107.81(13) . . ?
C17 N2 B1 127.25(12) . . ?
C10 N2 B1 124.57(13) . . ?
N1 C1 C2 109.21(13) . . ?
N1 C1 C18 124.98(13) . . ?
C2 C1 C18 125.50(14) . . ?
C7 C2 C1 107.96(13) . . ?
C7 C2 C3 124.43(14) . . ?
C1 C2 C3 127.55(14) . . ?
C2 C3 C4 110.11(13) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 109.96(13) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C6 111.36(13) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 109.79(13) . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C2 C7 C8 106.95(13) . . ?
C2 C7 C6 122.35(14) . . ?
C8 C7 C6 130.70(14) . . ?
C9 C8 N1 120.07(13) . . ?
C9 C8 C7 131.93(14) . . ?
N1 C8 C7 107.88(13) . . ?
C10 C9 C8 121.84(13) . . ?
C10 C9 C24 119.26(14) . . ?
C8 C9 C24 118.81(13) . . ?
C9 C10 N2 120.79(14) . . ?
C9 C10 C11 131.20(14) . . ?
N2 C10 C11 107.91(13) . . ?
C16 C11 C10 107.22(13) . . ?
C16 C11 C12 123.03(13) . . ?
C10 C11 C12 129.75(14) . . ?
C11 C12 C13 111.45(13) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 112.60(13) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 110.97(13) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 109.60(13) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C11 C16 C17 107.36(13) . . ?
C11 C16 C15 123.98(14) . . ?
C17 C16 C15 128.55(14) . . ?
N2 C17 C16 109.70(13) . . ?
N2 C17 C30 124.34(13) . . ?
C16 C17 C30 125.97(14) . . ?
C19 C18 C23 118.76(15) . . ?
C19 C18 C1 124.06(14) . . ?
C23 C18 C1 117.16(14) . . ?
C18 C19 C20 120.14(16) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.44(16) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.10(15) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.87(16) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C18 120.66(16) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C25 C24 C29 119.54(14) . . ?
C25 C24 C9 122.24(14) . . ?
C29 C24 C9 118.20(14) . . ?
C24 C25 C26 119.76(16) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.10(16) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.40(15) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.73(17) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C24 120.46(16) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C31 C30 C35 119.17(14) . . ?
C31 C30 C17 122.51(14) . . ?
C35 C30 C17 118.28(14) . . ?
C30 C31 C32 120.26(15) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 120.33(15) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 119.68(15) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.18(16) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C30 C35 C34 120.34(15) . . ?
C30 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
F2 B1 F1 110.61(13) . . ?
F2 B1 N1 110.98(14) . . ?
F1 B1 N1 107.81(13) . . ?
F2 B1 N2 108.56(13) . . ?
F1 B1 N2 111.42(13) . . ?
N1 B1 N2 107.42(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -2.87(16) . . . . ?
B1 N1 C1 C2 -176.06(14) . . . . ?
C8 N1 C1 C18 171.02(14) . . . . ?
B1 N1 C1 C18 -2.2(2) . . . . ?
N1 C1 C2 C7 2.89(17) . . . . ?
C18 C1 C2 C7 -170.97(14) . . . . ?
N1 C1 C2 C3 -174.45(15) . . . . ?
C18 C1 C2 C3 11.7(3) . . . . ?
C7 C2 C3 C4 -11.6(2) . . . . ?
C1 C2 C3 C4 165.31(15) . . . . ?
C2 C3 C4 C5 45.23(18) . . . . ?
C3 C4 C5 C6 -66.87(17) . . . . ?
C4 C5 C6 C7 49.01(18) . . . . ?
C1 C2 C7 C8 -1.70(17) . . . . ?
C3 C2 C7 C8 175.74(14) . . . . ?
C1 C2 C7 C6 178.40(14) . . . . ?
C3 C2 C7 C6 -4.2(2) . . . . ?
C5 C6 C7 C2 -14.4(2) . . . . ?
C5 C6 C7 C8 165.74(15) . . . . ?
C1 N1 C8 C9 -174.68(13) . . . . ?
B1 N1 C8 C9 -1.4(2) . . . . ?
C1 N1 C8 C7 1.80(16) . . . . ?
B1 N1 C8 C7 175.11(13) . . . . ?
C2 C7 C8 C9 175.89(15) . . . . ?
C6 C7 C8 C9 -4.2(3) . . . . ?
C2 C7 C8 N1 -0.02(17) . . . . ?
C6 C7 C8 N1 179.87(15) . . . . ?
N1 C8 C9 C10 -2.4(2) . . . . ?
C7 C8 C9 C10 -177.92(15) . . . . ?
N1 C8 C9 C24 174.20(13) . . . . ?
C7 C8 C9 C24 -1.3(2) . . . . ?
C8 C9 C10 N2 4.6(2) . . . . ?
C24 C9 C10 N2 -172.02(13) . . . . ?
C8 C9 C10 C11 -171.23(15) . . . . ?
C24 C9 C10 C11 12.2(2) . . . . ?
C17 N2 C10 C9 -176.51(14) . . . . ?
B1 N2 C10 C9 -3.0(2) . . . . ?
C17 N2 C10 C11 0.19(16) . . . . ?
B1 N2 C10 C11 173.66(13) . . . . ?
C9 C10 C11 C16 175.89(15) . . . . ?
N2 C10 C11 C16 -0.33(17) . . . . ?
C9 C10 C11 C12 -3.8(3) . . . . ?
N2 C10 C11 C12 -179.99(15) . . . . ?
C16 C11 C12 C13 -7.3(2) . . . . ?
C10 C11 C12 C13 172.27(15) . . . . ?
C11 C12 C13 C14 39.52(19) . . . . ?
C12 C13 C14 C15 -62.76(19) . . . . ?
C13 C14 C15 C16 49.25(18) . . . . ?
C10 C11 C16 C17 0.34(17) . . . . ?
C12 C11 C16 C17 -179.97(14) . . . . ?
C10 C11 C16 C15 176.95(14) . . . . ?
C12 C11 C16 C15 -3.4(2) . . . . ?
C14 C15 C16 C11 -17.9(2) . . . . ?
C14 C15 C16 C17 157.95(15) . . . . ?
C10 N2 C17 C16 0.03(16) . . . . ?
B1 N2 C17 C16 -173.22(14) . . . . ?
C10 N2 C17 C30 -179.99(14) . . . . ?
B1 N2 C17 C30 6.8(2) . . . . ?
C11 C16 C17 N2 -0.24(17) . . . . ?
C15 C16 C17 N2 -176.64(14) . . . . ?
C11 C16 C17 C30 179.78(14) . . . . ?
C15 C16 C17 C30 3.4(3) . . . . ?
N1 C1 C18 C19 56.5(2) . . . . ?
C2 C1 C18 C19 -130.56(17) . . . . ?
N1 C1 C18 C23 -124.68(16) . . . . ?
C2 C1 C18 C23 48.2(2) . . . . ?
C23 C18 C19 C20 -1.4(2) . . . . ?
C1 C18 C19 C20 177.41(15) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C22 1.6(3) . . . . ?
C20 C21 C22 C23 -1.7(3) . . . . ?
C21 C22 C23 C18 0.3(2) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C1 C18 C23 C22 -177.65(14) . . . . ?
C10 C9 C24 C25 -102.21(18) . . . . ?
C8 C9 C24 C25 81.09(19) . . . . ?
C10 C9 C24 C29 78.89(19) . . . . ?
C8 C9 C24 C29 -97.82(18) . . . . ?
C29 C24 C25 C26 1.1(2) . . . . ?
C9 C24 C25 C26 -177.79(15) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C28 -0.4(3) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C27 C28 C29 C24 0.3(2) . . . . ?
C25 C24 C29 C28 -1.1(2) . . . . ?
C9 C24 C29 C28 177.85(15) . . . . ?
N2 C17 C30 C31 51.6(2) . . . . ?
C16 C17 C30 C31 -128.38(17) . . . . ?
N2 C17 C30 C35 -130.59(16) . . . . ?
C16 C17 C30 C35 49.4(2) . . . . ?
C35 C30 C31 C32 2.1(2) . . . . ?
C17 C30 C31 C32 179.84(14) . . . . ?
C30 C31 C32 C33 -0.7(2) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C31 C30 C35 C34 -2.5(2) . . . . ?
C17 C30 C35 C34 179.69(15) . . . . ?
C33 C34 C35 C30 1.4(3) . . . . ?
C1 N1 B1 F2 -66.84(19) . . . . ?
C8 N1 B1 F2 121.10(15) . . . . ?
C1 N1 B1 F1 54.44(19) . . . . ?
C8 N1 B1 F1 -117.62(15) . . . . ?
C1 N1 B1 N2 174.64(13) . . . . ?
C8 N1 B1 N2 2.6(2) . . . . ?
C17 N2 B1 F2 51.7(2) . . . . ?
C10 N2 B1 F2 -120.46(15) . . . . ?
C17 N2 B1 F1 -70.32(19) . . . . ?
C10 N2 B1 F1 117.50(15) . . . . ?
C17 N2 B1 N1 171.81(13) . . . . ?
C10 N2 B1 N1 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound5c
_database_code_depnum_ccdc_archive 'CCDC 1435990'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 B F2 N4 O4'
_chemical_formula_sum            'C35 H29 B F2 N4 O4'
_chemical_formula_weight         618.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_Hall  '-C 2yc '
_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                   15.7880(6)
_cell_length_b                   12.5007(6)
_cell_length_c                   15.9397(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.931(4)
_cell_angle_gamma                90
_cell_volume                     2804.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7746
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      33.10

_exptl_crystal_description       fragment
_exptl_crystal_colour            red-brown
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31542
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         33.20
_reflns_number_total             5374
_reflns_number_gt                4112
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0699P)²+1.8012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
F1 F 0.43808(9) 0.47371(9) 0.17680(8) 0.0517(4) Uani 1 1 d . . .
O1 O 0.27986(7) 0.09319(7) 0.33551(7) 0.0233(2) Uani 1 1 d . . .
O2 O 0.30789(8) 0.13403(8) 0.47816(7) 0.0255(2) Uani 1 1 d . . .
N1 N 0.44741(6) 0.60962(7) 0.29151(6) 0.00913(16) Uani 1 1 d . . .
N2 N 0.30291(7) 0.15692(8) 0.40093(7) 0.01612(19) Uani 1 1 d . . .
C1 C 0.40939(7) 0.57976(8) 0.35009(7) 0.00905(17) Uani 1 1 d . . .
C2 C 0.39821(7) 0.67157(8) 0.39669(7) 0.00957(18) Uani 1 1 d . . .
C3 C 0.36384(8) 0.67952(8) 0.47048(8) 0.01183(19) Uani 1 1 d . . .
H3A H 0.4133 0.6516 0.5310 0.014 Uiso 1 1 calc R . .
H3B H 0.3061 0.6352 0.4516 0.014 Uiso 1 1 calc R . .
C4 C 0.34135(8) 0.79566(9) 0.48318(8) 0.01304(19) Uani 1 1 d . . .
H4A H 0.2816 0.8176 0.4286 0.016 Uiso 1 1 calc R . .
H4B H 0.3321 0.8016 0.5404 0.016 Uiso 1 1 calc R . .
C5 C 0.42158(8) 0.86997(9) 0.49194(8) 0.0135(2) Uani 1 1 d . . .
H5A H 0.4822 0.8452 0.5439 0.016 Uiso 1 1 calc R . .
H5B H 0.4089 0.9432 0.5070 0.016 Uiso 1 1 calc R . .
C6 C 0.43009(8) 0.87166(8) 0.40008(7) 0.01207(19) Uani 1 1 d . . .
H6A H 0.3770 0.9136 0.3522 0.014 Uiso 1 1 calc R . .
H6B H 0.4903 0.9069 0.4109 0.014 Uiso 1 1 calc R . .
C7 C 0.42791(7) 0.75985(8) 0.36426(7) 0.00946(18) Uani 1 1 d . . .
C8 C 0.45839(7) 0.72084(8) 0.29844(7) 0.00953(18) Uani 1 1 d . . .
C9 C 0.5000 0.77566(11) 0.2500 0.0098(2) Uani 1 2 d S . .
C10 C 0.38147(7) 0.47041(8) 0.36049(7) 0.00993(18) Uani 1 1 d . . .
C11 C 0.34277(7) 0.39788(8) 0.28486(7) 0.01133(18) Uani 1 1 d . . .
H11 H 0.3346 0.4191 0.2244 0.014 Uiso 1 1 calc R . .
C12 C 0.31652(8) 0.29568(8) 0.29785(8) 0.01232(19) Uani 1 1 d . . .
H12 H 0.2912 0.2465 0.2469 0.015 Uiso 1 1 calc R . .
C13 C 0.32784(7) 0.26627(8) 0.38645(8) 0.01237(19) Uani 1 1 d . . .
C14 C 0.36276(8) 0.33634(8) 0.46179(8) 0.01268(19) Uani 1 1 d . . .
H14 H 0.3684 0.3153 0.5214 0.015 Uiso 1 1 calc R . .
C15 C 0.38940(8) 0.43814(8) 0.44824(7) 0.01159(19) Uani 1 1 d . . .
H15 H 0.4135 0.4871 0.4994 0.014 Uiso 1 1 calc R . .
C16 C 0.5000 0.89459(11) 0.2500 0.0109(2) Uani 1 2 d S . .
C17 C 0.41429(8) 0.95056(9) 0.20771(8) 0.0139(2) Uani 1 1 d . . .
H17 H 0.3558 0.9128 0.1785 0.017 Uiso 1 1 calc R . .
C18 C 0.41482(10) 1.06177(9) 0.20855(8) 0.0187(2) Uani 1 1 d . . .
H18 H 0.3564 1.0998 0.1805 0.022 Uiso 1 1 calc R . .
C19 C 0.5000 1.11761(13) 0.2500 0.0211(3) Uani 1 2 d S . .
H19 H 0.5000 1.1936 0.2500 0.025 Uiso 1 2 calc SR . .
B1 B 0.5000 0.53652(14) 0.2500 0.0164(3) Uani 1 2 d S . .


_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 1.3785(13) . ?
O1 N2 1.2291(14) . ?
O2 N2 1.2312(14) . ?
N1 C1 1.3708(13) . ?
N1 C8 1.3993(13) . ?
N1 B1 1.5684(13) . ?
N2 C13 1.4694(14) . ?
C1 C2 1.4208(14) . ?
C1 C10 1.4685(14) . ?
C2 C7 1.3873(14) . ?
C2 C3 1.5054(14) . ?
C3 C4 1.5298(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5254(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5298(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5043(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.4239(14) . ?
C8 C9 1.3989(12) . ?
C9 C8 1.3989(12) 2_655 ?
C9 C16 1.487(2) . ?
C10 C15 1.4058(14) . ?
C10 C11 1.4076(14) . ?
C11 C12 1.3872(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3903(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3833(15) . ?
C14 C15 1.3875(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3960(13) 2_655 ?
C16 C17 1.3960(13) . ?
C17 C18 1.3902(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3884(16) . ?
C18 H18 0.9500 . ?
C19 C18 1.3884(16) 2_655 ?
C19 H19 0.9500 . ?
B1 F1 1.3785(13) 2_655 ?
B1 N1 1.5685(13) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 107.07(8) . . ?
C1 N1 B1 127.41(9) . . ?
C8 N1 B1 122.81(9) . . ?
O1 N2 O2 123.91(10) . . ?
O1 N2 C13 117.85(10) . . ?
O2 N2 C13 118.23(10) . . ?
N1 C1 C2 109.42(9) . . ?
N1 C1 C10 125.22(9) . . ?
C2 C1 C10 125.32(9) . . ?
C7 C2 C1 107.75(9) . . ?
C7 C2 C3 122.74(9) . . ?
C1 C2 C3 129.49(9) . . ?
C2 C3 C4 110.70(8) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 110.92(9) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 110.49(9) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 110.71(9) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C2 C7 C8 106.62(9) . . ?
C2 C7 C6 123.45(9) . . ?
C8 C7 C6 129.84(9) . . ?
C9 C8 N1 121.04(9) . . ?
C9 C8 C7 129.70(9) . . ?
N1 C8 C7 109.11(8) . . ?
C8 C9 C8 121.33(13) . 2_655 ?
C8 C9 C16 119.34(6) . . ?
C8 C9 C16 119.34(6) 2_655 . ?
C15 C10 C11 118.41(9) . . ?
C15 C10 C1 118.91(9) . . ?
C11 C10 C1 122.61(9) . . ?
C12 C11 C10 120.57(10) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.04(10) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 122.12(10) . . ?
C14 C13 N2 118.85(10) . . ?
C12 C13 N2 119.03(10) . . ?
C13 C14 C15 118.38(10) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C10 121.42(10) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C17 C16 C17 119.84(14) 2_655 . ?
C17 C16 C9 120.08(7) 2_655 . ?
C17 C16 C9 120.08(7) . . ?
C18 C17 C16 119.76(12) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.50(12) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C18 119.63(15) 2_655 . ?
C18 C19 H19 120.2 2_655 . ?
C18 C19 H19 120.2 . . ?
F1 B1 F1 110.56(17) . 2_655 ?
F1 B1 N1 112.39(6) . . ?
F1 B1 N1 106.43(5) 2_655 . ?
F1 B1 N1 106.43(5) . 2_655 ?
F1 B1 N1 112.39(6) 2_655 2_655 ?
N1 B1 N1 108.73(12) . 2_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -1.53(11) . . . . ?
B1 N1 C1 C2 160.01(8) . . . . ?
C8 N1 C1 C10 176.50(10) . . . . ?
B1 N1 C1 C10 -21.96(15) . . . . ?
N1 C1 C2 C7 1.43(12) . . . . ?
C10 C1 C2 C7 -176.60(10) . . . . ?
N1 C1 C2 C3 -176.94(10) . . . . ?
C10 C1 C2 C3 5.03(17) . . . . ?
C7 C2 C3 C4 15.26(14) . . . . ?
C1 C2 C3 C4 -166.59(10) . . . . ?
C2 C3 C4 C5 -47.27(12) . . . . ?
C3 C4 C5 C6 65.35(12) . . . . ?
C4 C5 C6 C7 -46.82(12) . . . . ?
C1 C2 C7 C8 -0.73(12) . . . . ?
C3 C2 C7 C8 177.78(9) . . . . ?
C1 C2 C7 C6 -177.66(9) . . . . ?
C3 C2 C7 C6 0.84(16) . . . . ?
C5 C6 C7 C2 15.10(14) . . . . ?
C5 C6 C7 C8 -161.07(11) . . . . ?
C1 N1 C8 C9 177.00(8) . . . . ?
B1 N1 C8 C9 14.41(13) . . . . ?
C1 N1 C8 C7 1.07(11) . . . . ?
B1 N1 C8 C7 -161.51(7) . . . . ?
C2 C7 C8 C9 -175.65(9) . . . . ?
C6 C7 C8 C9 1.01(18) . . . . ?
C2 C7 C8 N1 -0.20(12) . . . . ?
C6 C7 C8 N1 176.47(10) . . . . ?
N1 C8 C9 C8 -7.23(7) . . . 2_655 ?
C7 C8 C9 C8 167.76(13) . . . 2_655 ?
N1 C8 C9 C16 172.77(7) . . . . ?
C7 C8 C9 C16 -12.24(13) . . . . ?
N1 C1 C10 C15 148.22(10) . . . . ?
C2 C1 C10 C15 -34.06(15) . . . . ?
N1 C1 C10 C11 -34.86(15) . . . . ?
C2 C1 C10 C11 142.86(11) . . . . ?
C15 C10 C11 C12 -2.40(15) . . . . ?
C1 C10 C11 C12 -179.33(10) . . . . ?
C10 C11 C12 C13 0.83(16) . . . . ?
C11 C12 C13 C14 1.27(16) . . . . ?
C11 C12 C13 N2 -178.06(9) . . . . ?
O1 N2 C13 C14 -173.82(10) . . . . ?
O2 N2 C13 C14 4.95(15) . . . . ?
O1 N2 C13 C12 5.53(15) . . . . ?
O2 N2 C13 C12 -175.71(11) . . . . ?
C12 C13 C14 C15 -1.68(16) . . . . ?
N2 C13 C14 C15 177.65(9) . . . . ?
C13 C14 C15 C10 0.01(16) . . . . ?
C11 C10 C15 C14 1.99(16) . . . . ?
C1 C10 C15 C14 179.04(10) . . . . ?
C8 C9 C16 C17 115.79(7) . . . 2_655 ?
C8 C9 C16 C17 -64.21(7) 2_655 . . 2_655 ?
C8 C9 C16 C17 -64.20(7) . . . . ?
C8 C9 C16 C17 115.80(7) 2_655 . . . ?
C17 C16 C17 C18 -0.44(7) 2_655 . . . ?
C9 C16 C17 C18 179.56(7) . . . . ?
C16 C17 C18 C19 0.89(15) . . . . ?
C17 C18 C19 C18 -0.44(7) . . . 2_655 ?
C1 N1 B1 F1 76.50(13) . . . . ?
C8 N1 B1 F1 -124.61(12) . . . . ?
C1 N1 B1 F1 -44.66(13) . . . 2_655 ?
C8 N1 B1 F1 114.23(12) . . . 2_655 ?
C1 N1 B1 N1 -165.94(11) . . . 2_655 ?
C8 N1 B1 N1 -7.05(6) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.066
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound5d
_database_code_depnum_ccdc_archive 'CCDC 1435991'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H29 B F2 N4, C H2 Cl2'
_chemical_formula_sum            'C38 H31 B Cl2 F2 N4'
_chemical_formula_weight         663.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P -1          '
_symmetry_space_group_name_Hall  '-P 1 '
_symmetry_cell_setting           Triclinic

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

_cell_length_a                   9.7694(8)
_cell_length_b                   13.1321(10)
_cell_length_c                   13.2027(8)
_cell_angle_alpha                93.757(5)
_cell_angle_beta                 104.793(4)
_cell_angle_gamma                102.323(4)
_cell_volume                     1587.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7487
_cell_measurement_theta_min      2.546
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9338
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   'Denzo & Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius KappaCCD '
_diffrn_measurement_method       'φ and ω scans '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24995
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         28.77
_reflns_number_total             8128
_reflns_number_gt                5008
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_cell_refinement       
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'Direct_methods (SIR, Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_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)+(0.0596P)²+0.8176P] 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         8128
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.59841(16) 0.58315(10) 0.36535(10) 0.0183(3) Uani 1 1 d . . .
F2 F 0.83989(15) 0.58523(10) 0.40414(10) 0.0187(3) Uani 1 1 d . . .
N1 N 0.6843(2) 0.49236(14) 0.23753(14) 0.0132(4) Uani 1 1 d . . .
N2 N 0.6675(2) 0.42391(14) 0.40670(14) 0.0123(4) Uani 1 1 d . . .
N3 N 1.0835(3) 1.07457(18) 0.27219(19) 0.0321(6) Uani 1 1 d . . .
N4 N 1.0489(3) 0.78472(18) 0.93804(18) 0.0288(5) Uani 1 1 d . . .
C1 C 0.7362(3) 0.55119(18) 0.16777(17) 0.0130(5) Uani 1 1 d . . .
C2 C 0.7068(3) 0.48777(18) 0.07083(17) 0.0141(5) Uani 1 1 d . . .
C3 C 0.7445(3) 0.51791(18) -0.02841(18) 0.0174(5) Uani 1 1 d . . .
H3A H 0.8496 0.5234 -0.0198 0.021 Uiso 1 1 calc R . .
H3B H 0.7246 0.5874 -0.0418 0.021 Uiso 1 1 calc R . .
C4 C 0.6540(3) 0.43531(18) -0.12241(17) 0.0170(5) Uani 1 1 d . . .
H4A H 0.6932 0.4474 -0.1839 0.020 Uiso 1 1 calc R . .
H4B H 0.5518 0.4420 -0.1421 0.020 Uiso 1 1 calc R . .
C5 C 0.6587(3) 0.32446(19) -0.09391(18) 0.0182(5) Uani 1 1 d . . .
H5A H 0.6095 0.2726 -0.1576 0.022 Uiso 1 1 calc R . .
H5B H 0.7614 0.3196 -0.0698 0.022 Uiso 1 1 calc R . .
C6 C 0.5839(3) 0.29775(18) -0.00686(18) 0.0167(5) Uani 1 1 d . . .
H6A H 0.4769 0.2830 -0.0368 0.020 Uiso 1 1 calc R . .
H6B H 0.6083 0.2339 0.0214 0.020 Uiso 1 1 calc R . .
C7 C 0.6327(3) 0.38753(18) 0.08080(18) 0.0145(5) Uani 1 1 d . . .
C8 C 0.6191(3) 0.39073(17) 0.18557(17) 0.0127(5) Uani 1 1 d . . .
C9 C 0.5658(2) 0.30929(18) 0.24090(17) 0.0129(5) Uani 1 1 d . . .
C10 C 0.5886(3) 0.32569(17) 0.34953(17) 0.0131(5) Uani 1 1 d . . .
C11 C 0.5589(3) 0.25489(18) 0.42417(18) 0.0135(5) Uani 1 1 d . . .
C12 C 0.4696(3) 0.14437(18) 0.40810(18) 0.0167(5) Uani 1 1 d . . .
H12A H 0.5273 0.0950 0.3924 0.020 Uiso 1 1 calc R . .
H12B H 0.3820 0.1351 0.3475 0.020 Uiso 1 1 calc R . .
C13 C 0.4237(3) 0.12101(19) 0.50862(19) 0.0215(6) Uani 1 1 d . . .
H13A H 0.3518 0.1616 0.5166 0.026 Uiso 1 1 calc R . .
H13B H 0.3761 0.0454 0.5019 0.026 Uiso 1 1 calc R . .
C14 C 0.5539(3) 0.14920(19) 0.60682(19) 0.0219(6) Uani 1 1 d . . .
H14A H 0.6274 0.1105 0.5980 0.026 Uiso 1 1 calc R . .
H14B H 0.5215 0.1276 0.6690 0.026 Uiso 1 1 calc R . .
C15 C 0.6228(3) 0.26711(18) 0.62570(18) 0.0164(5) Uani 1 1 d . . .
H15A H 0.5662 0.3038 0.6616 0.020 Uiso 1 1 calc R . .
H15B H 0.7234 0.2805 0.6725 0.020 Uiso 1 1 calc R . .
C16 C 0.6263(3) 0.30984(18) 0.52328(18) 0.0137(5) Uani 1 1 d . . .
C17 C 0.6904(3) 0.41375(18) 0.51074(17) 0.0127(5) Uani 1 1 d . . .
C18 C 0.8081(3) 0.66447(18) 0.19142(17) 0.0145(5) Uani 1 1 d . . .
C19 C 0.7518(3) 0.73627(18) 0.24216(18) 0.0174(5) Uani 1 1 d . . .
H19 H 0.6660 0.7121 0.2636 0.021 Uiso 1 1 calc R . .
C20 C 0.8201(3) 0.84184(19) 0.26108(19) 0.0192(5) Uani 1 1 d . . .
H20 H 0.7808 0.8901 0.2950 0.023 Uiso 1 1 calc R . .
C21 C 0.9471(3) 0.87803(19) 0.23044(19) 0.0198(5) Uani 1 1 d . . .
C22 C 1.0040(3) 0.80757(19) 0.17911(19) 0.0216(6) Uani 1 1 d . . .
H22 H 1.0898 0.8318 0.1578 0.026 Uiso 1 1 calc R . .
C23 C 0.9337(3) 0.70191(19) 0.15976(19) 0.0184(5) Uani 1 1 d . . .
H23 H 0.9716 0.6540 0.1243 0.022 Uiso 1 1 calc R . .
C24 C 1.0228(3) 0.9879(2) 0.2530(2) 0.0244(6) Uani 1 1 d . . .
C25 C 0.4897(3) 0.20279(18) 0.18223(17) 0.0149(5) Uani 1 1 d . . .
C26 C 0.3470(3) 0.18458(19) 0.11840(18) 0.0182(5) Uani 1 1 d . . .
H26 H 0.2992 0.2406 0.1105 0.022 Uiso 1 1 calc R . .
C27 C 0.2745(3) 0.0847(2) 0.06629(19) 0.0240(6) Uani 1 1 d . . .
H27 H 0.1764 0.0722 0.0243 0.029 Uiso 1 1 calc R . .
C28 C 0.3454(3) 0.0033(2) 0.0756(2) 0.0259(6) Uani 1 1 d . . .
H28 H 0.2962 -0.0650 0.0398 0.031 Uiso 1 1 calc R . .
C29 C 0.4879(3) 0.0220(2) 0.1372(2) 0.0231(6) Uani 1 1 d . . .
H29 H 0.5369 -0.0335 0.1424 0.028 Uiso 1 1 calc R . .
C30 C 0.5604(3) 0.12076(18) 0.19138(18) 0.0174(5) Uani 1 1 d . . .
H30 H 0.6577 0.1325 0.2346 0.021 Uiso 1 1 calc R . .
C31 C 0.7689(3) 0.49918(18) 0.59813(17) 0.0130(5) Uani 1 1 d . . .
C32 C 0.7174(3) 0.58889(17) 0.61190(18) 0.0146(5) Uani 1 1 d . . .
H32 H 0.6344 0.5990 0.5613 0.018 Uiso 1 1 calc R . .
C33 C 0.7878(3) 0.66338(18) 0.69970(18) 0.0151(5) Uani 1 1 d . . .
H33 H 0.7530 0.7246 0.7093 0.018 Uiso 1 1 calc R . .
C34 C 0.9091(3) 0.64809(18) 0.77352(18) 0.0161(5) Uani 1 1 d . . .
C35 C 0.9622(3) 0.55893(19) 0.75999(18) 0.0174(5) Uani 1 1 d . . .
H35 H 1.0458 0.5492 0.8102 0.021 Uiso 1 1 calc R . .
C36 C 0.8915(3) 0.48489(18) 0.67234(18) 0.0161(5) Uani 1 1 d . . .
H36 H 0.9266 0.4239 0.6627 0.019 Uiso 1 1 calc R . .
C37 C 0.9860(3) 0.72544(19) 0.86457(19) 0.0189(5) Uani 1 1 d . . .
B1 B 0.7001(3) 0.5261(2) 0.3557(2) 0.0131(5) Uani 1 1 d . . .
Cl1 Cl 0.90841(7) 0.28254(5) 0.40122(5) 0.02823(17) Uani 1 1 d . . .
Cl2 Cl 0.87261(9) 0.08320(6) 0.48596(6) 0.0399(2) Uani 1 1 d . . .
C38 C 0.9985(3) 0.1959(2) 0.4709(2) 0.0265(6) Uani 1 1 d . . .
H38A H 1.0585 0.2321 0.5414 0.032 Uiso 1 1 calc R . .
H38B H 1.0646 0.1743 0.4325 0.032 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 1.391(3) . ?
F2 B1 1.383(3) . ?
N1 C1 1.366(3) . ?
N1 C8 1.397(3) . ?
N1 B1 1.553(3) . ?
N2 C17 1.354(3) . ?
N2 C10 1.406(3) . ?
N2 B1 1.549(3) . ?
N3 C24 1.145(3) . ?
N4 C37 1.148(3) . ?
C1 C2 1.409(3) . ?
C1 C18 1.478(3) . ?
C2 C7 1.392(3) . ?
C2 C3 1.504(3) . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.534(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.533(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.422(3) . ?
C8 C9 1.417(3) . ?
C9 C10 1.389(3) . ?
C9 C25 1.493(3) . ?
C10 C11 1.439(3) . ?
C11 C16 1.378(3) . ?
C11 C12 1.496(3) . ?
C12 C13 1.535(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.527(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.503(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.414(3) . ?
C17 C31 1.480(3) . ?
C18 C23 1.398(3) . ?
C18 C19 1.403(3) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(3) . ?
C21 C24 1.446(4) . ?
C22 C23 1.385(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C26 1.394(3) . ?
C25 C30 1.394(3) . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.395(3) . ?
C31 C36 1.396(3) . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.397(3) . ?
C34 C37 1.447(3) . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
Cl1 C38 1.751(3) . ?
Cl2 C38 1.769(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 107.68(18) . . ?
C1 N1 B1 128.06(19) . . ?
C8 N1 B1 124.16(19) . . ?
C17 N2 C10 107.56(18) . . ?
C17 N2 B1 127.83(19) . . ?
C10 N2 B1 124.11(18) . . ?
N1 C1 C2 109.43(19) . . ?
N1 C1 C18 124.4(2) . . ?
C2 C1 C18 126.2(2) . . ?
C7 C2 C1 107.7(2) . . ?
C7 C2 C3 123.8(2) . . ?
C1 C2 C3 128.5(2) . . ?
C2 C3 C4 110.06(19) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 110.27(19) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 111.48(19) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 110.37(19) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C2 C7 C8 106.77(19) . . ?
C2 C7 C6 123.1(2) . . ?
C8 C7 C6 130.1(2) . . ?
N1 C8 C9 120.6(2) . . ?
N1 C8 C7 108.42(19) . . ?
C9 C8 C7 130.7(2) . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 C25 119.4(2) . . ?
C8 C9 C25 119.5(2) . . ?
C9 C10 N2 120.1(2) . . ?
C9 C10 C11 131.7(2) . . ?
N2 C10 C11 107.89(19) . . ?
C16 C11 C10 106.6(2) . . ?
C16 C11 C12 122.2(2) . . ?
C10 C11 C12 131.1(2) . . ?
C11 C12 C13 109.13(19) . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 111.7(2) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 111.1(2) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 110.96(19) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C11 C16 C17 108.0(2) . . ?
C11 C16 C15 125.2(2) . . ?
C17 C16 C15 126.7(2) . . ?
N2 C17 C16 109.87(19) . . ?
N2 C17 C31 125.0(2) . . ?
C16 C17 C31 125.1(2) . . ?
C23 C18 C19 118.8(2) . . ?
C23 C18 C1 119.2(2) . . ?
C19 C18 C1 122.0(2) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 C24 119.1(2) . . ?
C20 C21 C24 120.8(2) . . ?
C23 C22 C21 119.2(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C18 121.3(2) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
N3 C24 C21 179.1(3) . . ?
C26 C25 C30 119.5(2) . . ?
C26 C25 C9 120.1(2) . . ?
C30 C25 C9 120.3(2) . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 119.7(2) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
C32 C31 C36 119.9(2) . . ?
C32 C31 C17 121.7(2) . . ?
C36 C31 C17 118.3(2) . . ?
C33 C32 C31 119.9(2) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 119.8(2) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C35 120.7(2) . . ?
C33 C34 C37 120.9(2) . . ?
C35 C34 C37 118.3(2) . . ?
C36 C35 C34 119.2(2) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C35 C36 C31 120.6(2) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
N4 C37 C34 178.1(3) . . ?
F2 B1 F1 110.30(19) . . ?
F2 B1 N2 110.9(2) . . ?
F1 B1 N2 108.32(19) . . ?
F2 B1 N1 109.9(2) . . ?
F1 B1 N1 110.48(19) . . ?
N2 B1 N1 106.89(18) . . ?
Cl1 C38 Cl2 111.02(15) . . ?
Cl1 C38 H38A 109.4 . . ?
Cl2 C38 H38A 109.4 . . ?
Cl1 C38 H38B 109.4 . . ?
Cl2 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -0.8(3) . . . . ?
B1 N1 C1 C2 175.7(2) . . . . ?
C8 N1 C1 C18 177.7(2) . . . . ?
B1 N1 C1 C18 -5.8(4) . . . . ?
N1 C1 C2 C7 0.9(3) . . . . ?
C18 C1 C2 C7 -177.5(2) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
C18 C1 C2 C3 2.1(4) . . . . ?
C7 C2 C3 C4 16.3(3) . . . . ?
C1 C2 C3 C4 -163.3(2) . . . . ?
C2 C3 C4 C5 -47.6(3) . . . . ?
C3 C4 C5 C6 65.4(3) . . . . ?
C4 C5 C6 C7 -46.1(3) . . . . ?
C1 C2 C7 C8 -0.6(3) . . . . ?
C3 C2 C7 C8 179.7(2) . . . . ?
C1 C2 C7 C6 -179.5(2) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
C5 C6 C7 C2 14.0(3) . . . . ?
C5 C6 C7 C8 -164.6(2) . . . . ?
C1 N1 C8 C9 174.7(2) . . . . ?
B1 N1 C8 C9 -2.0(3) . . . . ?
C1 N1 C8 C7 0.4(3) . . . . ?
B1 N1 C8 C7 -176.2(2) . . . . ?
C2 C7 C8 N1 0.1(3) . . . . ?
C6 C7 C8 N1 178.9(2) . . . . ?
C2 C7 C8 C9 -173.4(2) . . . . ?
C6 C7 C8 C9 5.4(4) . . . . ?
N1 C8 C9 C10 -5.9(3) . . . . ?
C7 C8 C9 C10 166.9(2) . . . . ?
N1 C8 C9 C25 176.9(2) . . . . ?
C7 C8 C9 C25 -10.3(4) . . . . ?
C8 C9 C10 N2 -0.9(3) . . . . ?
C25 C9 C10 N2 176.3(2) . . . . ?
C8 C9 C10 C11 -173.2(2) . . . . ?
C25 C9 C10 C11 4.1(4) . . . . ?
C17 N2 C10 C9 -171.7(2) . . . . ?
B1 N2 C10 C9 15.9(3) . . . . ?
C17 N2 C10 C11 2.2(3) . . . . ?
B1 N2 C10 C11 -170.1(2) . . . . ?
C9 C10 C11 C16 169.9(2) . . . . ?
N2 C10 C11 C16 -3.1(3) . . . . ?
C9 C10 C11 C12 -12.7(4) . . . . ?
N2 C10 C11 C12 174.3(2) . . . . ?
C16 C11 C12 C13 19.6(3) . . . . ?
C10 C11 C12 C13 -157.4(2) . . . . ?
C11 C12 C13 C14 -51.4(3) . . . . ?
C12 C13 C14 C15 63.8(3) . . . . ?
C13 C14 C15 C16 -39.6(3) . . . . ?
C10 C11 C16 C17 2.7(3) . . . . ?
C12 C11 C16 C17 -175.0(2) . . . . ?
C10 C11 C16 C15 179.3(2) . . . . ?
C12 C11 C16 C15 1.6(4) . . . . ?
C14 C15 C16 C11 8.5(3) . . . . ?
C14 C15 C16 C17 -175.6(2) . . . . ?
C10 N2 C17 C16 -0.6(3) . . . . ?
B1 N2 C17 C16 171.4(2) . . . . ?
C10 N2 C17 C31 -179.7(2) . . . . ?
B1 N2 C17 C31 -7.7(4) . . . . ?
C11 C16 C17 N2 -1.4(3) . . . . ?
C15 C16 C17 N2 -177.9(2) . . . . ?
C11 C16 C17 C31 177.7(2) . . . . ?
C15 C16 C17 C31 1.2(4) . . . . ?
N1 C1 C18 C23 136.5(2) . . . . ?
C2 C1 C18 C23 -45.2(3) . . . . ?
N1 C1 C18 C19 -45.3(3) . . . . ?
C2 C1 C18 C19 133.0(3) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
C1 C18 C19 C20 -178.7(2) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C19 C20 C21 C24 -177.8(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C24 C21 C22 C23 178.4(2) . . . . ?
C21 C22 C23 C18 -0.6(4) . . . . ?
C19 C18 C23 C22 1.1(4) . . . . ?
C1 C18 C23 C22 179.3(2) . . . . ?
C10 C9 C25 C26 107.0(3) . . . . ?
C8 C9 C25 C26 -75.8(3) . . . . ?
C10 C9 C25 C30 -72.6(3) . . . . ?
C8 C9 C25 C30 104.7(3) . . . . ?
C30 C25 C26 C27 1.6(4) . . . . ?
C9 C25 C26 C27 -178.0(2) . . . . ?
C25 C26 C27 C28 -1.6(4) . . . . ?
C26 C27 C28 C29 0.3(4) . . . . ?
C27 C28 C29 C30 1.1(4) . . . . ?
C28 C29 C30 C25 -1.2(4) . . . . ?
C26 C25 C30 C29 -0.2(3) . . . . ?
C9 C25 C30 C29 179.4(2) . . . . ?
N2 C17 C31 C32 63.0(3) . . . . ?
C16 C17 C31 C32 -116.0(3) . . . . ?
N2 C17 C31 C36 -121.8(3) . . . . ?
C16 C17 C31 C36 59.3(3) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
C17 C31 C32 C33 174.8(2) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C35 0.6(4) . . . . ?
C32 C33 C34 C37 178.8(2) . . . . ?
C33 C34 C35 C36 -0.7(4) . . . . ?
C37 C34 C35 C36 -178.9(2) . . . . ?
C34 C35 C36 C31 0.2(4) . . . . ?
C32 C31 C36 C35 0.3(4) . . . . ?
C17 C31 C36 C35 -175.1(2) . . . . ?
C17 N2 B1 F2 48.7(3) . . . . ?
C10 N2 B1 F2 -140.6(2) . . . . ?
C17 N2 B1 F1 -72.5(3) . . . . ?
C10 N2 B1 F1 98.3(2) . . . . ?
C17 N2 B1 N1 168.4(2) . . . . ?
C10 N2 B1 N1 -20.8(3) . . . . ?
C1 N1 B1 F2 -41.8(3) . . . . ?
C8 N1 B1 F2 134.2(2) . . . . ?
C1 N1 B1 F1 80.1(3) . . . . ?
C8 N1 B1 F1 -103.9(2) . . . . ?
C1 N1 B1 N2 -162.2(2) . . . . ?
C8 N1 B1 N2 13.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.077
# END OF CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound5e
_database_code_depnum_ccdc_archive 'CCDC 1435992'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H29 B F8 N2'
_chemical_formula_sum            'C37 H29 B F8 N2'
_chemical_formula_weight         664.43

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1   '

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

_cell_length_a                   8.1559(9)
_cell_length_b                   13.0389(14)
_cell_length_c                   15.7981(18)
_cell_angle_alpha                114.011(4)
_cell_angle_beta                 91.649(5)
_cell_angle_gamma                102.179(5)
_cell_volume                     1487.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      33.69

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9242
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35888
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         33.71
_reflns_number_total             11819
_reflns_number_gt                9928
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0667P)²+0.3526P] 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         11819
_refine_ls_number_parameters     442
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.035
_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
F1 F 0.83106(7) 0.37448(6) 0.20432(5) 0.02560(13) Uani 1 1 d . A .
F2 F 0.67382(7) 0.39242(5) 0.32331(5) 0.03068(16) Uani 1 1 d . A .
F3 F 1.13421(9) 0.90373(5) 0.44336(5) 0.02848(14) Uani 1 1 d . . .
F4 F 1.23740(11) 0.84026(6) 0.31358(5) 0.03541(17) Uani 1 1 d . . .
F5 F 1.39420(9) 0.89604(6) 0.44354(6) 0.03512(17) Uani 1 1 d . . .
F6 F 0.09862(9) 0.56771(6) 0.13836(5) 0.02904(14) Uani 1 1 d . A .
F7 F 0.19327(8) 0.52227(6) 0.00560(5) 0.02644(13) Uani 1 1 d . A .
F8 F 0.35490(10) 0.64614(5) 0.13142(6) 0.0396(2) Uani 1 1 d . A .
N1 N 0.90099(9) 0.29333(6) 0.30623(5) 0.01164(11) Uani 1 1 d . A .
N2 N 0.62713(8) 0.20456(6) 0.19793(5) 0.01044(11) Uani 1 1 d . A .
C1 C 1.05294(10) 0.36623(7) 0.35114(5) 0.01235(13) Uani 1 1 d . . .
C2 C 1.15765(10) 0.30440(7) 0.37315(5) 0.01307(13) Uani 1 1 d . A .
C3 C 1.33403(11) 0.35053(8) 0.42375(6) 0.01687(15) Uani 1 1 d D . .
H3A H 1.3417 0.4249 0.4784 0.020 Uiso 0.924(3) 1 calc PR A 1
H3B H 1.4143 0.3651 0.3817 0.020 Uiso 0.924(3) 1 calc PR A 1
H3C H 1.3308 0.3905 0.4918 0.020 Uiso 0.076(3) 1 calc PR A 2
H4C H 1.3999 0.4071 0.4030 0.020 Uiso 0.076(3) 1 calc PR A 2
C4 C 1.38176(12) 0.26431(9) 0.45622(7) 0.0179(2) Uani 0.924(3) 1 d PD A 1
H4A H 1.3251 0.2671 0.5114 0.021 Uiso 0.924(3) 1 calc PR A 1
H4B H 1.5055 0.2859 0.4750 0.021 Uiso 0.924(3) 1 calc PR A 1
C5 C 1.32971(12) 0.14151(8) 0.37861(8) 0.0175(2) Uani 0.924(3) 1 d PD A 1
H5A H 1.3717 0.0886 0.3994 0.021 Uiso 0.924(3) 1 calc PR A 1
H5B H 1.3831 0.1398 0.3227 0.021 Uiso 0.924(3) 1 calc PR A 1
C4A C 1.4246(17) 0.2426(11) 0.4016(10) 0.027(3) Uiso 0.076(3) 1 d PD A 2
H4A1 H 1.4493 0.2136 0.3361 0.032 Uiso 0.076(3) 1 calc PR A 2
H4A2 H 1.5332 0.2705 0.4429 0.032 Uiso 0.076(3) 1 calc PR A 2
C5A C 1.3109(15) 0.1431(11) 0.4169(11) 0.023(3) Uiso 0.076(3) 1 d PD A 2
H5A1 H 1.2908 0.1704 0.4831 0.028 Uiso 0.076(3) 1 calc PR A 2
H5A2 H 1.3676 0.0789 0.4022 0.028 Uiso 0.076(3) 1 calc PR A 2
C6 C 1.13757(10) 0.09865(7) 0.35234(6) 0.01590(14) Uani 1 1 d D . .
H6A H 1.1102 0.0273 0.2933 0.019 Uiso 0.924(3) 1 calc PR A 1
H6B H 1.0859 0.0799 0.4019 0.019 Uiso 0.924(3) 1 calc PR A 1
H6C H 1.1521 0.0427 0.2898 0.019 Uiso 0.076(3) 1 calc PR A 2
H6D H 1.0536 0.0562 0.3781 0.019 Uiso 0.076(3) 1 calc PR A 2
C7 C 1.06624(10) 0.18990(7) 0.34070(5) 0.01215(13) Uani 1 1 d . A .
C8 C 0.90514(10) 0.18297(6) 0.29749(5) 0.01145(13) Uani 1 1 d . . .
C9 C 0.77126(9) 0.08724(6) 0.24555(5) 0.01041(12) Uani 1 1 d . A .
C10 C 0.63388(9) 0.09780(6) 0.19686(5) 0.01037(12) Uani 1 1 d . . .
C11 C 0.48104(9) 0.01484(6) 0.14582(5) 0.01027(12) Uani 1 1 d . A .
C12 C 0.42397(10) -0.11193(6) 0.12250(6) 0.01299(13) Uani 1 1 d . . .
H12A H 0.4473 -0.1247 0.1788 0.016 Uiso 1 1 calc R A .
H12B H 0.4883 -0.1554 0.0739 0.016 Uiso 1 1 calc R . .
C13 C 0.23439(10) -0.15714(7) 0.08709(6) 0.01468(14) Uani 1 1 d . A .
H13A H 0.2052 -0.2428 0.0579 0.018 Uiso 1 1 calc R . .
H13B H 0.1693 -0.1312 0.1406 0.018 Uiso 1 1 calc R . .
C14 C 0.18450(11) -0.11399(7) 0.01581(6) 0.01478(14) Uani 1 1 d . . .
H14A H 0.0643 -0.1509 -0.0104 0.018 Uiso 1 1 calc R A .
H14B H 0.2540 -0.1358 -0.0361 0.018 Uiso 1 1 calc R . .
C15 C 0.21089(10) 0.01763(7) 0.06214(6) 0.01356(13) Uani 1 1 d . A .
H15A H 0.2003 0.0464 0.0136 0.016 Uiso 1 1 calc R . .
H15B H 0.1228 0.0383 0.1035 0.016 Uiso 1 1 calc R . .
C16 C 0.38261(10) 0.07359(6) 0.11825(5) 0.01082(12) Uani 1 1 d . . .
C17 C 0.47514(9) 0.19012(6) 0.15082(5) 0.01059(12) Uani 1 1 d . A .
C18 C 1.10054(10) 0.48971(7) 0.36991(5) 0.01338(13) Uani 1 1 d . . .
C19 C 1.25605(11) 0.53352(7) 0.34610(6) 0.01500(14) Uani 1 1 d . . .
H19 H 1.3320 0.4852 0.3234 0.018 Uiso 1 1 calc R . .
C20 C 1.29964(11) 0.64672(7) 0.35548(6) 0.01640(15) Uani 1 1 d . . .
H20 H 1.4033 0.6751 0.3373 0.020 Uiso 1 1 calc R . .
C21 C 1.19082(11) 0.71851(7) 0.39161(6) 0.01579(14) Uani 1 1 d . . .
C22 C 1.04103(12) 0.67840(7) 0.42053(6) 0.01768(15) Uani 1 1 d . . .
H22 H 0.9698 0.7289 0.4479 0.021 Uiso 1 1 calc R . .
C23 C 0.99559(11) 0.56410(7) 0.40937(6) 0.01642(15) Uani 1 1 d . . .
H23 H 0.8927 0.5366 0.4287 0.020 Uiso 1 1 calc R . .
C24 C 1.23839(13) 0.83903(7) 0.39797(6) 0.02002(16) Uani 1 1 d . . .
C25 C 0.77386(9) -0.02741(7) 0.24377(5) 0.01182(13) Uani 1 1 d . . .
C26 C 0.81143(11) -0.11496(7) 0.16546(6) 0.01577(14) Uani 1 1 d . A .
H26 H 0.8349 -0.1022 0.1115 0.019 Uiso 1 1 calc R . .
C27 C 0.81463(12) -0.22099(8) 0.16614(8) 0.02197(18) Uani 1 1 d . . .
H27 H 0.8410 -0.2801 0.1128 0.026 Uiso 1 1 calc R A .
C28 C 0.77935(13) -0.24046(8) 0.24458(8) 0.0257(2) Uani 1 1 d . A .
H28 H 0.7821 -0.3127 0.2451 0.031 Uiso 1 1 calc R . .
C29 C 0.74011(13) -0.15414(9) 0.32220(8) 0.02377(18) Uani 1 1 d . . .
H29 H 0.7150 -0.1677 0.3756 0.029 Uiso 1 1 calc R A .
C30 C 0.73739(11) -0.04766(8) 0.32223(6) 0.01700(15) Uani 1 1 d . A .
H30 H 0.7107 0.0112 0.3757 0.020 Uiso 1 1 calc R . .
C31 C 0.41715(10) 0.28116(6) 0.13496(5) 0.01161(13) Uani 1 1 d . . .
C32 C 0.52240(10) 0.35977(7) 0.10807(6) 0.01483(14) Uani 1 1 d . A .
H32 H 0.6352 0.3543 0.0982 0.018 Uiso 1 1 calc R . .
C33 C 0.46243(11) 0.44548(7) 0.09578(6) 0.01711(15) Uani 1 1 d . . .
H33 H 0.5353 0.5001 0.0797 0.021 Uiso 1 1 calc R A .
C34 C 0.29553(11) 0.45131(7) 0.10707(6) 0.01530(14) Uani 1 1 d . A .
C35 C 0.18696(11) 0.37070(7) 0.12902(6) 0.01527(14) Uani 1 1 d . . .
H35 H 0.0719 0.3730 0.1340 0.018 Uiso 1 1 calc R A .
C36 C 0.24835(10) 0.28675(7) 0.14360(6) 0.01353(13) Uani 1 1 d . A .
H36 H 0.1748 0.2324 0.1597 0.016 Uiso 1 1 calc R . .
C37 C 0.23516(12) 0.54687(8) 0.09623(7) 0.02011(17) Uani 1 1 d . . .
B1 B 0.75730(11) 0.32092(7) 0.25856(7) 0.01285(15) 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
F1 B1 1.3869(11) . ?
F2 B1 1.3824(11) . ?
F3 C24 1.3390(12) . ?
F4 C24 1.3397(11) . ?
F5 C24 1.3413(11) . ?
F6 C37 1.3343(12) . ?
F7 C37 1.3497(11) . ?
F8 C37 1.3371(11) . ?
N1 C1 1.3588(10) . ?
N1 C8 1.3964(10) . ?
N1 B1 1.5548(11) . ?
N2 C17 1.3640(10) . ?
N2 C10 1.3980(10) . ?
N2 B1 1.5574(11) . ?
C1 C2 1.4148(12) . ?
C1 C18 1.4737(11) . ?
C2 C7 1.3904(11) . ?
C2 C3 1.4992(11) . ?
C3 C4 1.5236(13) . ?
C3 C4A 1.644(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C3 H4C 0.9900 . ?
C4 C5 1.5273(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5312(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4A C5A 1.537(15) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6 1.570(12) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6 C7 1.5007(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 C8 1.4313(11) . ?
C8 C9 1.4012(10) . ?
C9 C10 1.4027(11) . ?
C9 C25 1.4884(11) . ?
C10 C11 1.4274(10) . ?
C11 C16 1.3899(10) . ?
C11 C12 1.5015(11) . ?
C12 C13 1.5324(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5284(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5298(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5002(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.4144(10) . ?
C17 C31 1.4722(11) . ?
C18 C23 1.3968(12) . ?
C18 C19 1.4047(11) . ?
C19 C20 1.3872(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.3909(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.3899(12) . ?
C21 C24 1.4974(12) . ?
C22 C23 1.3924(12) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C26 1.3956(12) . ?
C25 C30 1.3961(11) . ?
C26 C27 1.3926(12) . ?
C26 H26 0.9500 . ?
C27 C28 1.3887(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.3873(16) . ?
C28 H28 0.9500 . ?
C29 C30 1.3930(13) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.4016(11) . ?
C31 C32 1.4043(11) . ?
C32 C33 1.3884(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.3918(13) . ?
C33 H33 0.9500 . ?
C34 C35 1.3894(12) . ?
C34 C37 1.5007(12) . ?
C35 C36 1.3899(11) . ?
C35 H35 0.9500 . ?
C36 H36 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
C1 N1 C8 107.84(7) . . ?
C1 N1 B1 126.80(7) . . ?
C8 N1 B1 124.71(6) . . ?
C17 N2 C10 107.64(6) . . ?
C17 N2 B1 127.25(6) . . ?
C10 N2 B1 124.19(6) . . ?
N1 C1 C2 109.66(7) . . ?
N1 C1 C18 124.18(7) . . ?
C2 C1 C18 126.12(7) . . ?
C7 C2 C1 107.58(7) . . ?
C7 C2 C3 124.58(8) . . ?
C1 C2 C3 127.83(7) . . ?
C2 C3 C4 110.38(7) . . ?
C2 C3 C4A 109.2(5) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C2 C3 H3C 109.8 . . ?
C4A C3 H3C 109.8 . . ?
C2 C3 H4C 109.8 . . ?
C4A C3 H4C 109.8 . . ?
H3C C3 H4C 108.3 . . ?
C3 C4 C5 110.89(8) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 112.10(8) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5A C4A C3 111.4(10) . . ?
C5A C4A H4A1 109.3 . . ?
C3 C4A H4A1 109.3 . . ?
C5A C4A H4A2 109.3 . . ?
C3 C4A H4A2 109.3 . . ?
H4A1 C4A H4A2 108.0 . . ?
C4A C5A C6 109.8(10) . . ?
C4A C5A H5A1 109.7 . . ?
C6 C5A H5A1 109.7 . . ?
C4A C5A H5A2 109.7 . . ?
C6 C5A H5A2 109.7 . . ?
H5A1 C5A H5A2 108.2 . . ?
C7 C6 C5 110.15(7) . . ?
C7 C6 C5A 115.9(5) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5A C6 H6A 123.2 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6C 108.3 . . ?
C5A C6 H6C 108.3 . . ?
C7 C6 H6D 108.3 . . ?
C5A C6 H6D 108.3 . . ?
H6C C6 H6D 107.4 . . ?
C2 C7 C8 106.61(7) . . ?
C2 C7 C6 122.48(7) . . ?
C8 C7 C6 130.91(7) . . ?
N1 C8 C9 120.59(7) . . ?
N1 C8 C7 108.31(6) . . ?
C9 C8 C7 130.84(7) . . ?
C8 C9 C10 121.40(7) . . ?
C8 C9 C25 119.07(7) . . ?
C10 C9 C25 119.52(7) . . ?
N2 C10 C9 120.83(7) . . ?
N2 C10 C11 108.52(6) . . ?
C9 C10 C11 130.55(7) . . ?
C16 C11 C10 106.61(6) . . ?
C16 C11 C12 122.76(7) . . ?
C10 C11 C12 130.64(7) . . ?
C11 C12 C13 110.74(6) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.58(7) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.27(7) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.16(6) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C17 107.76(7) . . ?
C11 C16 C15 123.90(7) . . ?
C17 C16 C15 128.33(7) . . ?
N2 C17 C16 109.47(7) . . ?
N2 C17 C31 125.36(7) . . ?
C16 C17 C31 125.16(7) . . ?
C23 C18 C19 118.99(7) . . ?
C23 C18 C1 122.32(7) . . ?
C19 C18 C1 118.69(7) . . ?
C20 C19 C18 120.55(8) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.68(8) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.39(8) . . ?
C22 C21 C24 121.08(8) . . ?
C20 C21 C24 118.53(8) . . ?
C21 C22 C23 119.90(8) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.31(8) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
F3 C24 F4 106.54(8) . . ?
F3 C24 F5 106.23(8) . . ?
F4 C24 F5 106.61(8) . . ?
F3 C24 C21 112.96(8) . . ?
F4 C24 C21 112.15(7) . . ?
F5 C24 C21 111.89(8) . . ?
C26 C25 C30 119.40(7) . . ?
C26 C25 C9 121.49(7) . . ?
C30 C25 C9 119.11(7) . . ?
C27 C26 C25 120.23(8) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.16(9) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 119.82(8) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.37(9) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.02(9) . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?
C36 C31 C32 118.69(7) . . ?
C36 C31 C17 118.64(7) . . ?
C32 C31 C17 122.62(7) . . ?
C33 C32 C31 120.33(8) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 119.94(8) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.57(7) . . ?
C35 C34 C37 120.49(8) . . ?
C33 C34 C37 118.94(8) . . ?
C34 C35 C36 119.38(8) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 120.96(7) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
F6 C37 F8 107.30(8) . . ?
F6 C37 F7 106.44(7) . . ?
F8 C37 F7 106.52(8) . . ?
F6 C37 C34 112.90(8) . . ?
F8 C37 C34 111.51(7) . . ?
F7 C37 C34 111.79(8) . . ?
F2 B1 F1 109.92(7) . . ?
F2 B1 N1 111.88(7) . . ?
F1 B1 N1 107.33(6) . . ?
F2 B1 N2 108.22(6) . . ?
F1 B1 N2 111.59(7) . . ?
N1 B1 N2 107.92(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
C8 N1 C1 C2 -0.61(9) . . . . ?
B1 N1 C1 C2 -171.66(7) . . . . ?
C8 N1 C1 C18 177.21(7) . . . . ?
B1 N1 C1 C18 6.16(12) . . . . ?
N1 C1 C2 C7 -0.12(9) . . . . ?
C18 C1 C2 C7 -177.89(7) . . . . ?
N1 C1 C2 C3 -178.95(8) . . . . ?
C18 C1 C2 C3 3.28(13) . . . . ?
C7 C2 C3 C4 -14.35(12) . . . . ?
C1 C2 C3 C4 164.30(8) . . . . ?
C7 C2 C3 C4A 20.4(5) . . . . ?
C1 C2 C3 C4A -160.9(5) . . . . ?
C2 C3 C4 C5 45.03(10) . . . . ?
C4A C3 C4 C5 -49.0(9) . . . . ?
C3 C4 C5 C6 -64.20(11) . . . . ?
C2 C3 C4A C5A -49.6(11) . . . . ?
C4 C3 C4A C5A 48.5(8) . . . . ?
C3 C4A C5A C6 58.6(14) . . . . ?
C4 C5 C6 C7 46.65(11) . . . . ?
C4 C5 C6 C5A -62.4(13) . . . . ?
C4A C5A C6 C7 -38.3(12) . . . . ?
C4A C5A C6 C5 42.3(10) . . . . ?
C1 C2 C7 C8 0.78(9) . . . . ?
C3 C2 C7 C8 179.66(7) . . . . ?
C1 C2 C7 C6 -179.68(7) . . . . ?
C3 C2 C7 C6 -0.80(12) . . . . ?
C5 C6 C7 C2 -15.17(11) . . . . ?
C5A C6 C7 C2 9.2(7) . . . . ?
C5 C6 C7 C8 164.25(9) . . . . ?
C5A C6 C7 C8 -171.4(7) . . . . ?
C1 N1 C8 C9 -173.59(7) . . . . ?
B1 N1 C8 C9 -2.30(11) . . . . ?
C1 N1 C8 C7 1.09(9) . . . . ?
B1 N1 C8 C7 172.38(7) . . . . ?
C2 C7 C8 N1 -1.16(9) . . . . ?
C6 C7 C8 N1 179.36(8) . . . . ?
C2 C7 C8 C9 172.79(8) . . . . ?
C6 C7 C8 C9 -6.70(15) . . . . ?
N1 C8 C9 C10 3.42(11) . . . . ?
C7 C8 C9 C10 -169.91(8) . . . . ?
N1 C8 C9 C25 -175.36(7) . . . . ?
C7 C8 C9 C25 11.32(12) . . . . ?
C17 N2 C10 C9 -175.68(7) . . . . ?
B1 N2 C10 C9 -5.97(11) . . . . ?
C17 N2 C10 C11 0.94(8) . . . . ?
B1 N2 C10 C11 170.64(7) . . . . ?
C8 C9 C10 N2 0.65(11) . . . . ?
C25 C9 C10 N2 179.42(7) . . . . ?
C8 C9 C10 C11 -175.13(8) . . . . ?
C25 C9 C10 C11 3.64(12) . . . . ?
N2 C10 C11 C16 -1.10(8) . . . . ?
C9 C10 C11 C16 175.08(8) . . . . ?
N2 C10 C11 C12 179.07(8) . . . . ?
C9 C10 C11 C12 -4.75(14) . . . . ?
C16 C11 C12 C13 -13.50(11) . . . . ?
C10 C11 C12 C13 166.31(8) . . . . ?
C11 C12 C13 C14 45.31(9) . . . . ?
C12 C13 C14 C15 -65.01(9) . . . . ?
C13 C14 C15 C16 48.13(9) . . . . ?
C10 C11 C16 C17 0.83(8) . . . . ?
C12 C11 C16 C17 -179.32(7) . . . . ?
C10 C11 C16 C15 179.68(7) . . . . ?
C12 C11 C16 C15 -0.47(12) . . . . ?
C14 C15 C16 C11 -17.11(11) . . . . ?
C14 C15 C16 C17 161.50(8) . . . . ?
C10 N2 C17 C16 -0.42(8) . . . . ?
B1 N2 C17 C16 -169.71(7) . . . . ?
C10 N2 C17 C31 -179.54(7) . . . . ?
B1 N2 C17 C31 11.16(12) . . . . ?
C11 C16 C17 N2 -0.27(9) . . . . ?
C15 C16 C17 N2 -179.06(7) . . . . ?
C11 C16 C17 C31 178.85(7) . . . . ?
C15 C16 C17 C31 0.07(13) . . . . ?
N1 C1 C18 C23 48.77(12) . . . . ?
C2 C1 C18 C23 -133.77(9) . . . . ?
N1 C1 C18 C19 -130.39(8) . . . . ?
C2 C1 C18 C19 47.07(11) . . . . ?
C23 C18 C19 C20 -4.47(12) . . . . ?
C1 C18 C19 C20 174.72(7) . . . . ?
C18 C19 C20 C21 2.09(12) . . . . ?
C19 C20 C21 C22 1.66(13) . . . . ?
C19 C20 C21 C24 -177.99(8) . . . . ?
C20 C21 C22 C23 -2.97(13) . . . . ?
C24 C21 C22 C23 176.67(8) . . . . ?
C21 C22 C23 C18 0.52(13) . . . . ?
C19 C18 C23 C22 3.15(12) . . . . ?
C1 C18 C23 C22 -176.01(8) . . . . ?
C22 C21 C24 F3 7.48(12) . . . . ?
C20 C21 C24 F3 -172.87(8) . . . . ?
C22 C21 C24 F4 -112.94(10) . . . . ?
C20 C21 C24 F4 66.71(11) . . . . ?
C22 C21 C24 F5 127.32(9) . . . . ?
C20 C21 C24 F5 -53.04(11) . . . . ?
C8 C9 C25 C26 -105.35(9) . . . . ?
C10 C9 C25 C26 75.85(10) . . . . ?
C8 C9 C25 C30 74.83(10) . . . . ?
C10 C9 C25 C30 -103.97(9) . . . . ?
C30 C25 C26 C27 -0.84(12) . . . . ?
C9 C25 C26 C27 179.34(8) . . . . ?
C25 C26 C27 C28 0.42(14) . . . . ?
C26 C27 C28 C29 0.29(15) . . . . ?
C27 C28 C29 C30 -0.58(15) . . . . ?
C28 C29 C30 C25 0.16(14) . . . . ?
C26 C25 C30 C29 0.55(12) . . . . ?
C9 C25 C30 C29 -179.63(8) . . . . ?
N2 C17 C31 C36 -139.04(8) . . . . ?
C16 C17 C31 C36 41.97(11) . . . . ?
N2 C17 C31 C32 43.45(12) . . . . ?
C16 C17 C31 C32 -135.54(8) . . . . ?
C36 C31 C32 C33 3.75(12) . . . . ?
C17 C31 C32 C33 -178.74(8) . . . . ?
C31 C32 C33 C34 -2.16(13) . . . . ?
C32 C33 C34 C35 -1.13(13) . . . . ?
C32 C33 C34 C37 178.19(8) . . . . ?
C33 C34 C35 C36 2.73(13) . . . . ?
C37 C34 C35 C36 -176.58(8) . . . . ?
C34 C35 C36 C31 -1.06(12) . . . . ?
C32 C31 C36 C35 -2.15(12) . . . . ?
C17 C31 C36 C35 -179.75(7) . . . . ?
C35 C34 C37 F6 20.80(12) . . . . ?
C33 C34 C37 F6 -158.51(8) . . . . ?
C35 C34 C37 F8 141.70(9) . . . . ?
C33 C34 C37 F8 -37.62(12) . . . . ?
C35 C34 C37 F7 -99.18(10) . . . . ?
C33 C34 C37 F7 81.50(10) . . . . ?
C1 N1 B1 F2 -73.66(10) . . . . ?
C8 N1 B1 F2 116.72(8) . . . . ?
C1 N1 B1 F1 46.99(11) . . . . ?
C8 N1 B1 F1 -122.63(8) . . . . ?
C1 N1 B1 N2 167.39(7) . . . . ?
C8 N1 B1 N2 -2.23(10) . . . . ?
C17 N2 B1 F2 52.72(11) . . . . ?
C10 N2 B1 F2 -114.92(8) . . . . ?
C17 N2 B1 F1 -68.35(10) . . . . ?
C10 N2 B1 F1 124.01(8) . . . . ?
C17 N2 B1 N1 173.97(7) . . . . ?
C10 N2 B1 N1 6.33(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.061
# END OF CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound5f
_database_code_depnum_ccdc_archive 'CCDC 1435993'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H45 B Cl2 F2 N2 O4'
_chemical_formula_sum            'C52 H45 B Cl2 F2 N2 O4'
_chemical_formula_weight         881.61

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_space_group_name_Hall           '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n  '

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

_cell_length_a                   9.5919(2)
_cell_length_b                   34.4320(6)
_cell_length_c                   13.4607(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.8990(10)
_cell_angle_gamma                90
_cell_volume                     4230.47(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      36.22


_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50441
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         36.35
_reflns_number_total             20106
_reflns_number_gt                14388
_reflns_threshold_expression     I>2σ(I)

_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0662P)²+1.4432P] 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         20106
_refine_ls_number_parameters     568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
F1 F 0.56820(8) 0.24097(2) 0.44221(5) 0.01800(15) Uani 1 1 d . . .
F2 F 0.81713(9) 0.23747(2) 0.50005(6) 0.01696(14) Uani 1 1 d . . .
O1 O 0.55853(10) 0.07222(2) 0.64245(7) 0.01794(17) Uani 1 1 d . . .
O2 O 0.75147(11) 0.06724(3) 0.78816(7) 0.02214(19) Uani 1 1 d . . .
O3 O 0.59896(10) 0.15032(3) 0.02346(7) 0.01591(16) Uani 1 1 d . . .
O4 O 0.82457(10) 0.16682(3) 0.01792(7) 0.01707(16) Uani 1 1 d . . .
N1 N 0.69612(10) 0.27522(3) 0.60108(7) 0.00909(14) Uani 1 1 d . . .
N2 N 0.70234(10) 0.29778(3) 0.42542(7) 0.01008(15) Uani 1 1 d . . .
C1 C 0.70557(11) 0.25311(3) 0.68708(8) 0.00951(16) Uani 1 1 d . . .
C2 C 0.70483(11) 0.27737(3) 0.77133(8) 0.01007(17) Uani 1 1 d . . .
C3 C 0.70245(13) 0.26557(3) 0.87843(8) 0.01265(18) Uani 1 1 d . . .
H3A H 0.8031 0.2594 0.9229 0.015 Uiso 1 1 calc R . .
H3B H 0.6415 0.2420 0.8734 0.015 Uiso 1 1 calc R . .
C4 C 0.63966(14) 0.29873(3) 0.92727(8) 0.01472(19) Uani 1 1 d . . .
H4A H 0.6552 0.2932 1.0021 0.018 Uiso 1 1 calc R . .
H4B H 0.5329 0.3009 0.8921 0.018 Uiso 1 1 calc R . .
C5 C 0.71459(13) 0.33707(3) 0.91634(8) 0.01429(19) Uani 1 1 d . . .
H5A H 0.8220 0.3341 0.9467 0.017 Uiso 1 1 calc R . .
H5B H 0.6824 0.3576 0.9559 0.017 Uiso 1 1 calc R . .
C6 C 0.67805(12) 0.34943(3) 0.80163(8) 0.01210(18) Uani 1 1 d . . .
H6A H 0.5764 0.3594 0.7765 0.015 Uiso 1 1 calc R . .
H6B H 0.7449 0.3705 0.7953 0.015 Uiso 1 1 calc R . .
C7 C 0.69383(11) 0.31548(3) 0.73586(8) 0.00969(16) Uani 1 1 d . . .
C8 C 0.69060(11) 0.31416(3) 0.62907(8) 0.00937(16) Uani 1 1 d . . .
C9 C 0.68803(11) 0.34407(3) 0.55802(8) 0.00947(16) Uani 1 1 d . . .
C10 C 0.69184(12) 0.33598(3) 0.45702(8) 0.01017(17) Uani 1 1 d . . .
C11 C 0.68979(12) 0.36128(3) 0.37237(8) 0.01118(17) Uani 1 1 d . . .
C12 C 0.66214(14) 0.40418(3) 0.35821(9) 0.01483(19) Uani 1 1 d . . .
H12A H 0.7539 0.4186 0.3913 0.018 Uiso 1 1 calc R . .
H12B H 0.5886 0.4122 0.3921 0.018 Uiso 1 1 calc R . .
C13 C 0.60593(15) 0.41356(4) 0.24093(9) 0.0182(2) Uani 1 1 d . . .
H13A H 0.5057 0.4030 0.2109 0.022 Uiso 1 1 calc R . .
H13B H 0.6011 0.4421 0.2311 0.022 Uiso 1 1 calc R . .
C14 C 0.70557(16) 0.39623(4) 0.18368(10) 0.0197(2) Uani 1 1 d . . .
H14A H 0.8073 0.4052 0.2170 0.024 Uiso 1 1 calc R . .
H14B H 0.6741 0.4053 0.1104 0.024 Uiso 1 1 calc R . .
C15 C 0.70073(14) 0.35182(4) 0.18583(8) 0.0163(2) Uani 1 1 d . . .
H15A H 0.6101 0.3425 0.1333 0.020 Uiso 1 1 calc R . .
H15B H 0.7855 0.3411 0.1676 0.020 Uiso 1 1 calc R . .
C16 C 0.70458(12) 0.33774(3) 0.29225(8) 0.01203(18) Uani 1 1 d . . .
C17 C 0.70957(12) 0.29881(3) 0.32653(8) 0.01079(17) Uani 1 1 d . . .
C18 C 0.70330(11) 0.21036(3) 0.68942(8) 0.00983(16) Uani 1 1 d . . .
C19 C 0.59090(12) 0.18943(3) 0.61831(8) 0.01321(18) Uani 1 1 d . . .
H19 H 0.5204 0.2028 0.5637 0.016 Uiso 1 1 calc R . .
C20 C 0.58164(13) 0.14942(3) 0.62687(8) 0.01385(19) Uani 1 1 d . . .
H20 H 0.5044 0.1356 0.5785 0.017 Uiso 1 1 calc R . .
C21 C 0.68530(12) 0.12932(3) 0.70630(8) 0.01118(17) Uani 1 1 d . . .
C22 C 0.79714(12) 0.14995(3) 0.77756(8) 0.01211(18) Uani 1 1 d . . .
H22 H 0.8679 0.1365 0.8318 0.015 Uiso 1 1 calc R . .
C23 C 0.80575(12) 0.19008(3) 0.76978(8) 0.01174(17) Uani 1 1 d . . .
H23 H 0.8817 0.2039 0.8193 0.014 Uiso 1 1 calc R . .
C24 C 0.67292(12) 0.08661(3) 0.71842(8) 0.01283(18) Uani 1 1 d . . .
C25 C 0.52538(14) 0.03171(3) 0.64644(9) 0.0165(2) Uani 1 1 d . . .
H25A H 0.5124 0.0253 0.7147 0.020 Uiso 1 1 calc R . .
H25B H 0.6063 0.0157 0.6373 0.020 Uiso 1 1 calc R . .
C26 C 0.38580(13) 0.02370(3) 0.55945(9) 0.01512(19) Uani 1 1 d . . .
C27 C 0.32156(14) 0.05113(4) 0.48292(9) 0.0183(2) Uani 1 1 d . . .
H27 H 0.3669 0.0757 0.4840 0.022 Uiso 1 1 calc R . .
C28 C 0.19131(16) 0.04273(4) 0.40478(10) 0.0229(2) Uani 1 1 d . . .
H28 H 0.1478 0.0617 0.3533 0.027 Uiso 1 1 calc R . .
C29 C 0.12503(17) 0.00682(5) 0.40197(12) 0.0281(3) Uani 1 1 d . . .
H29 H 0.0358 0.0012 0.3491 0.034 Uiso 1 1 calc R . .
C30 C 0.18957(18) -0.02084(5) 0.47673(12) 0.0303(3) Uani 1 1 d . . .
H30 H 0.1450 -0.0456 0.4745 0.036 Uiso 1 1 calc R . .
C31 C 0.31941(16) -0.01255(4) 0.55512(10) 0.0226(2) Uani 1 1 d . . .
H31 H 0.3630 -0.0317 0.6060 0.027 Uiso 1 1 calc R . .
C32 C 0.69042(11) 0.38557(3) 0.58989(8) 0.00949(16) Uani 1 1 d . . .
C33 C 0.56200(12) 0.40550(3) 0.58536(9) 0.01404(19) Uani 1 1 d . . .
H33 H 0.4707 0.3922 0.5658 0.017 Uiso 1 1 calc R . .
C34 C 0.56810(14) 0.44492(4) 0.60969(10) 0.0172(2) Uani 1 1 d . . .
H34 H 0.4804 0.4586 0.6054 0.021 Uiso 1 1 calc R . .
C35 C 0.70143(14) 0.46450(3) 0.64021(10) 0.0175(2) Uani 1 1 d . . .
H35 H 0.7049 0.4914 0.6569 0.021 Uiso 1 1 calc R . .
C36 C 0.82978(13) 0.44440(4) 0.64618(9) 0.0162(2) Uani 1 1 d . . .
H36 H 0.9214 0.4575 0.6680 0.019 Uiso 1 1 calc R . .
C37 C 0.82414(12) 0.40520(3) 0.62021(8) 0.01253(18) Uani 1 1 d . . .
H37 H 0.9117 0.3917 0.6231 0.015 Uiso 1 1 calc R . .
C38 C 0.71279(12) 0.26467(3) 0.26069(8) 0.01075(17) Uani 1 1 d . . .
C39 C 0.59476(12) 0.23882(3) 0.22945(9) 0.01374(19) Uani 1 1 d . . .
H39 H 0.5147 0.2415 0.2564 0.016 Uiso 1 1 calc R . .
C40 C 0.59407(12) 0.20919(3) 0.15912(9) 0.01355(19) Uani 1 1 d . . .
H40 H 0.5131 0.1919 0.1374 0.016 Uiso 1 1 calc R . .
C41 C 0.71257(12) 0.20488(3) 0.12043(8) 0.01072(17) Uani 1 1 d . . .
C42 C 0.83058(12) 0.23045(3) 0.15128(8) 0.01244(18) Uani 1 1 d . . .
H42 H 0.9113 0.2274 0.1251 0.015 Uiso 1 1 calc R . .
C43 C 0.83012(12) 0.26038(3) 0.22034(8) 0.01263(18) Uani 1 1 d . . .
H43 H 0.9100 0.2781 0.2403 0.015 Uiso 1 1 calc R . .
C44 C 0.72047(12) 0.17277(3) 0.04860(8) 0.01198(18) Uani 1 1 d . . .
C45 C 0.60618(14) 0.11456(4) -0.03038(9) 0.0165(2) Uani 1 1 d . . .
H45A H 0.6752 0.1177 -0.0714 0.020 Uiso 1 1 calc R . .
H45B H 0.5083 0.1086 -0.0796 0.020 Uiso 1 1 calc R . .
C46 C 0.65588(13) 0.08136(4) 0.04520(9) 0.01452(19) Uani 1 1 d . . .
C47 C 0.71269(14) 0.08705(4) 0.15273(9) 0.0172(2) Uani 1 1 d . . .
H47 H 0.7239 0.1127 0.1802 0.021 Uiso 1 1 calc R . .
C48 C 0.75306(15) 0.05551(4) 0.21994(10) 0.0210(2) Uani 1 1 d . . .
H48 H 0.7924 0.0597 0.2930 0.025 Uiso 1 1 calc R . .
C49 C 0.73610(15) 0.01788(4) 0.18075(11) 0.0222(2) Uani 1 1 d . . .
H49 H 0.7609 -0.0037 0.2269 0.027 Uiso 1 1 calc R . .
C50 C 0.68273(15) 0.01197(4) 0.07364(11) 0.0226(2) Uani 1 1 d . . .
H50 H 0.6734 -0.0137 0.0463 0.027 Uiso 1 1 calc R . .
C51 C 0.64296(15) 0.04347(4) 0.00640(10) 0.0196(2) Uani 1 1 d . . .
H51 H 0.6066 0.0392 -0.0668 0.023 Uiso 1 1 calc R . .
B1 B 0.69754(13) 0.26116(3) 0.49161(9) 0.01042(19) Uani 1 1 d . . .
C52 C 0.73167(16) 0.15615(4) 0.41065(13) 0.0263(3) Uani 1 1 d . . .
H52A H 0.7475 0.1752 0.3601 0.032 Uiso 1 1 calc R . .
H52B H 0.7267 0.1706 0.4731 0.032 Uiso 1 1 calc R . .
Cl1 Cl 0.56446(4) 0.131873(13) 0.35414(3) 0.03226(9) Uani 1 1 d . . .
Cl2 Cl 0.88028(5) 0.123736(13) 0.44697(4) 0.04399(12) 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
F1 B1 1.3992(14) . ?
F2 B1 1.3834(14) . ?
O1 C24 1.3436(14) . ?
O1 C25 1.4353(15) . ?
O2 C24 1.2078(14) . ?
O3 C44 1.3521(14) . ?
O3 C45 1.4412(14) . ?
O4 C44 1.2095(14) . ?
N1 C1 1.3652(13) . ?
N1 C8 1.3980(14) . ?
N1 B1 1.5550(14) . ?
N2 C17 1.3546(13) . ?
N2 C10 1.3953(14) . ?
N2 B1 1.5528(15) . ?
C1 C2 1.4105(14) . ?
C1 C18 1.4725(15) . ?
C2 C7 1.3892(15) . ?
C2 C3 1.5047(14) . ?
C3 C4 1.5304(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5318(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5348(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5017(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.4289(14) . ?
C8 C9 1.4004(14) . ?
C9 C10 1.3993(14) . ?
C9 C32 1.4902(15) . ?
C10 C11 1.4296(14) . ?
C11 C16 1.3908(15) . ?
C11 C12 1.5024(16) . ?
C12 C13 1.5376(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5218(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5305(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5019(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.4137(16) . ?
C17 C38 1.4782(15) . ?
C18 C19 1.4013(15) . ?
C18 C23 1.4036(15) . ?
C19 C20 1.3875(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.3991(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.3938(15) . ?
C21 C24 1.4884(16) . ?
C22 C23 1.3901(16) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C26 1.5087(17) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.3939(17) . ?
C26 C31 1.3945(18) . ?
C27 C28 1.3940(18) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.3949(15) . ?
C32 C37 1.3951(15) . ?
C33 C34 1.3932(17) . ?
C33 H33 0.9500 . ?
C34 C35 1.3914(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3931(18) . ?
C35 H35 0.9500 . ?
C36 C37 1.3912(17) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.3994(16) . ?
C38 C43 1.3997(15) . ?
C39 C40 1.3902(15) . ?
C39 H39 0.9500 . ?
C40 C41 1.3961(15) . ?
C40 H40 0.9500 . ?
C41 C42 1.3929(16) . ?
C41 C44 1.4859(15) . ?
C42 C43 1.3888(15) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C45 C46 1.5068(17) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.3949(16) . ?
C46 C51 1.3967(17) . ?
C47 C48 1.3901(19) . ?
C47 H47 0.9500 . ?
C48 C49 1.389(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.389(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.3889(19) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 Cl2 1.7574(16) . ?
C52 Cl1 1.7606(15) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?

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
C24 O1 C25 117.92(9) . . ?
C44 O3 C45 116.32(9) . . ?
C1 N1 C8 107.73(8) . . ?
C1 N1 B1 127.75(9) . . ?
C8 N1 B1 124.48(9) . . ?
C17 N2 C10 107.77(9) . . ?
C17 N2 B1 127.20(9) . . ?
C10 N2 B1 124.95(8) . . ?
N1 C1 C2 109.63(9) . . ?
N1 C1 C18 125.32(9) . . ?
C2 C1 C18 124.83(9) . . ?
C7 C2 C1 107.56(9) . . ?
C7 C2 C3 124.24(9) . . ?
C1 C2 C3 127.99(10) . . ?
C2 C3 C4 109.50(9) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 110.10(9) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C6 111.51(9) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 110.13(9) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C2 C7 C8 106.96(9) . . ?
C2 C7 C6 122.91(9) . . ?
C8 C7 C6 130.00(10) . . ?
N1 C8 C9 121.02(9) . . ?
N1 C8 C7 108.10(9) . . ?
C9 C8 C7 130.84(10) . . ?
C10 C9 C8 121.12(10) . . ?
C10 C9 C32 117.90(9) . . ?
C8 C9 C32 120.87(9) . . ?
N2 C10 C9 120.64(9) . . ?
N2 C10 C11 108.43(9) . . ?
C9 C10 C11 130.92(10) . . ?
C16 C11 C10 106.45(9) . . ?
C16 C11 C12 122.05(9) . . ?
C10 C11 C12 131.21(10) . . ?
C11 C12 C13 109.23(9) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 111.16(10) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.78(10) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.39(9) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C17 107.50(9) . . ?
C11 C16 C15 124.97(10) . . ?
C17 C16 C15 127.28(10) . . ?
N2 C17 C16 109.80(9) . . ?
N2 C17 C38 125.82(10) . . ?
C16 C17 C38 124.28(9) . . ?
C19 C18 C23 118.68(10) . . ?
C19 C18 C1 120.85(9) . . ?
C23 C18 C1 120.15(9) . . ?
C20 C19 C18 120.62(10) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.40(10) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.33(10) . . ?
C22 C21 C24 119.90(10) . . ?
C20 C21 C24 120.71(10) . . ?
C23 C22 C21 120.37(10) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.59(10) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
O2 C24 O1 123.82(11) . . ?
O2 C24 C21 125.37(10) . . ?
O1 C24 C21 110.78(9) . . ?
O1 C25 C26 107.61(9) . . ?
O1 C25 H25A 110.2 . . ?
C26 C25 H25A 110.2 . . ?
O1 C25 H25B 110.2 . . ?
C26 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C27 C26 C31 118.90(12) . . ?
C27 C26 C25 122.34(11) . . ?
C31 C26 C25 118.75(11) . . ?
C26 C27 C28 120.47(12) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 120.21(13) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 119.65(13) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 120.38(13) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 120.38(13) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
C33 C32 C37 119.65(10) . . ?
C33 C32 C9 121.59(9) . . ?
C37 C32 C9 118.69(9) . . ?
C34 C33 C32 119.75(11) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 120.66(11) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 119.47(11) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C37 C36 C35 120.14(11) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C32 120.31(11) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?
C39 C38 C43 119.27(10) . . ?
C39 C38 C17 121.47(10) . . ?
C43 C38 C17 118.95(10) . . ?
C40 C39 C38 120.36(10) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 119.87(10) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C42 C41 C40 120.12(10) . . ?
C42 C41 C44 117.71(9) . . ?
C40 C41 C44 122.14(10) . . ?
C43 C42 C41 119.94(10) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C38 120.43(10) . . ?
C42 C43 H43 119.8 . . ?
C38 C43 H43 119.8 . . ?
O4 C44 O3 123.80(10) . . ?
O4 C44 C41 124.11(10) . . ?
O3 C44 C41 112.08(9) . . ?
O3 C45 C46 111.27(9) . . ?
O3 C45 H45A 109.4 . . ?
C46 C45 H45A 109.4 . . ?
O3 C45 H45B 109.4 . . ?
C46 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
C47 C46 C51 118.72(12) . . ?
C47 C46 C45 122.40(11) . . ?
C51 C46 C45 118.87(10) . . ?
C48 C47 C46 120.50(12) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C49 C48 C47 120.31(12) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C50 C49 C48 119.59(13) . . ?
C50 C49 H49 120.2 . . ?
C48 C49 H49 120.2 . . ?
C49 C50 C51 120.12(13) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C50 C51 C46 120.72(12) . . ?
C50 C51 H51 119.6 . . ?
C46 C51 H51 119.6 . . ?
F2 B1 F1 109.74(9) . . ?
F2 B1 N2 110.84(9) . . ?
F1 B1 N2 108.01(9) . . ?
F2 B1 N1 110.75(9) . . ?
F1 B1 N1 109.90(9) . . ?
N2 B1 N1 107.54(8) . . ?
Cl2 C52 Cl1 111.84(8) . . ?
Cl2 C52 H52A 109.2 . . ?
Cl1 C52 H52A 109.2 . . ?
Cl2 C52 H52B 109.2 . . ?
Cl1 C52 H52B 109.2 . . ?
H52A C52 H52B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 0.57(11) . . . . ?
B1 N1 C1 C2 178.17(10) . . . . ?
C8 N1 C1 C18 175.42(10) . . . . ?
B1 N1 C1 C18 -6.98(17) . . . . ?
N1 C1 C2 C7 0.32(12) . . . . ?
C18 C1 C2 C7 -174.56(10) . . . . ?
N1 C1 C2 C3 175.22(10) . . . . ?
C18 C1 C2 C3 0.34(17) . . . . ?
C7 C2 C3 C4 17.51(15) . . . . ?
C1 C2 C3 C4 -156.61(11) . . . . ?
C2 C3 C4 C5 -48.61(12) . . . . ?
C3 C4 C5 C6 66.16(12) . . . . ?
C4 C5 C6 C7 -46.14(13) . . . . ?
C1 C2 C7 C8 -1.05(12) . . . . ?
C3 C2 C7 C8 -176.20(10) . . . . ?
C1 C2 C7 C6 175.10(10) . . . . ?
C3 C2 C7 C6 -0.05(17) . . . . ?
C5 C6 C7 C2 14.15(15) . . . . ?
C5 C6 C7 C8 -170.66(11) . . . . ?
C1 N1 C8 C9 176.73(9) . . . . ?
B1 N1 C8 C9 -0.96(15) . . . . ?
C1 N1 C8 C7 -1.22(11) . . . . ?
B1 N1 C8 C7 -178.92(9) . . . . ?
C2 C7 C8 N1 1.41(12) . . . . ?
C6 C7 C8 N1 -174.37(10) . . . . ?
C2 C7 C8 C9 -176.27(11) . . . . ?
C6 C7 C8 C9 7.95(19) . . . . ?
N1 C8 C9 C10 -0.41(16) . . . . ?
C7 C8 C9 C10 177.02(11) . . . . ?
N1 C8 C9 C32 -176.61(9) . . . . ?
C7 C8 C9 C32 0.82(17) . . . . ?
C17 N2 C10 C9 -177.65(10) . . . . ?
B1 N2 C10 C9 5.41(16) . . . . ?
C17 N2 C10 C11 1.16(12) . . . . ?
B1 N2 C10 C11 -175.78(9) . . . . ?
C8 C9 C10 N2 -1.75(16) . . . . ?
C32 C9 C10 N2 174.56(9) . . . . ?
C8 C9 C10 C11 179.75(11) . . . . ?
C32 C9 C10 C11 -3.94(17) . . . . ?
N2 C10 C11 C16 -2.14(12) . . . . ?
C9 C10 C11 C16 176.51(11) . . . . ?
N2 C10 C11 C12 171.67(11) . . . . ?
C9 C10 C11 C12 -9.7(2) . . . . ?
C16 C11 C12 C13 17.95(15) . . . . ?
C10 C11 C12 C13 -155.04(12) . . . . ?
C11 C12 C13 C14 -51.03(14) . . . . ?
C12 C13 C14 C15 66.03(14) . . . . ?
C13 C14 C15 C16 -42.62(14) . . . . ?
C10 C11 C16 C17 2.26(12) . . . . ?
C12 C11 C16 C17 -172.25(10) . . . . ?
C10 C11 C16 C15 176.87(11) . . . . ?
C12 C11 C16 C15 2.37(18) . . . . ?
C14 C15 C16 C11 10.02(17) . . . . ?
C14 C15 C16 C17 -176.44(11) . . . . ?
C10 N2 C17 C16 0.27(12) . . . . ?
B1 N2 C17 C16 177.12(10) . . . . ?
C10 N2 C17 C38 -176.14(10) . . . . ?
B1 N2 C17 C38 0.71(17) . . . . ?
C11 C16 C17 N2 -1.62(13) . . . . ?
C15 C16 C17 N2 -176.08(11) . . . . ?
C11 C16 C17 C38 174.86(10) . . . . ?
C15 C16 C17 C38 0.40(18) . . . . ?
N1 C1 C18 C19 -52.60(15) . . . . ?
C2 C1 C18 C19 121.48(12) . . . . ?
N1 C1 C18 C23 133.87(11) . . . . ?
C2 C1 C18 C23 -52.05(15) . . . . ?
C23 C18 C19 C20 -0.37(16) . . . . ?
C1 C18 C19 C20 -173.99(10) . . . . ?
C18 C19 C20 C21 -0.50(18) . . . . ?
C19 C20 C21 C22 0.72(17) . . . . ?
C19 C20 C21 C24 177.69(11) . . . . ?
C20 C21 C22 C23 -0.06(16) . . . . ?
C24 C21 C22 C23 -177.05(10) . . . . ?
C21 C22 C23 C18 -0.82(16) . . . . ?
C19 C18 C23 C22 1.03(16) . . . . ?
C1 C18 C23 C22 174.70(10) . . . . ?
C25 O1 C24 O2 1.98(18) . . . . ?
C25 O1 C24 C21 -176.13(10) . . . . ?
C22 C21 C24 O2 1.81(18) . . . . ?
C20 C21 C24 O2 -175.13(12) . . . . ?
C22 C21 C24 O1 179.89(10) . . . . ?
C20 C21 C24 O1 2.94(15) . . . . ?
C24 O1 C25 C26 174.83(10) . . . . ?
O1 C25 C26 C27 8.98(16) . . . . ?
O1 C25 C26 C31 -171.52(11) . . . . ?
C31 C26 C27 C28 1.46(19) . . . . ?
C25 C26 C27 C28 -179.04(12) . . . . ?
C26 C27 C28 C29 -0.6(2) . . . . ?
C27 C28 C29 C30 -0.6(2) . . . . ?
C28 C29 C30 C31 0.7(3) . . . . ?
C29 C30 C31 C26 0.2(2) . . . . ?
C27 C26 C31 C30 -1.3(2) . . . . ?
C25 C26 C31 C30 179.22(13) . . . . ?
C10 C9 C32 C33 97.39(13) . . . . ?
C8 C9 C32 C33 -86.29(13) . . . . ?
C10 C9 C32 C37 -79.58(13) . . . . ?
C8 C9 C32 C37 96.74(12) . . . . ?
C37 C32 C33 C34 0.91(16) . . . . ?
C9 C32 C33 C34 -176.03(10) . . . . ?
C32 C33 C34 C35 -1.10(18) . . . . ?
C33 C34 C35 C36 0.14(19) . . . . ?
C34 C35 C36 C37 1.00(18) . . . . ?
C35 C36 C37 C32 -1.18(17) . . . . ?
C33 C32 C37 C36 0.22(16) . . . . ?
C9 C32 C37 C36 177.24(10) . . . . ?
N2 C17 C38 C39 63.56(15) . . . . ?
C16 C17 C38 C39 -112.35(13) . . . . ?
N2 C17 C38 C43 -122.90(12) . . . . ?
C16 C17 C38 C43 61.18(15) . . . . ?
C43 C38 C39 C40 0.00(17) . . . . ?
C17 C38 C39 C40 173.52(10) . . . . ?
C38 C39 C40 C41 0.83(17) . . . . ?
C39 C40 C41 C42 -0.72(17) . . . . ?
C39 C40 C41 C44 177.40(10) . . . . ?
C40 C41 C42 C43 -0.24(16) . . . . ?
C44 C41 C42 C43 -178.43(10) . . . . ?
C41 C42 C43 C38 1.08(17) . . . . ?
C39 C38 C43 C42 -0.96(16) . . . . ?
C17 C38 C43 C42 -174.64(10) . . . . ?
C45 O3 C44 O4 9.16(16) . . . . ?
C45 O3 C44 C41 -169.31(9) . . . . ?
C42 C41 C44 O4 2.32(17) . . . . ?
C40 C41 C44 O4 -175.84(11) . . . . ?
C42 C41 C44 O3 -179.22(10) . . . . ?
C40 C41 C44 O3 2.63(15) . . . . ?
C44 O3 C45 C46 92.36(12) . . . . ?
O3 C45 C46 C47 -11.06(16) . . . . ?
O3 C45 C46 C51 168.12(11) . . . . ?
C51 C46 C47 C48 -1.17(18) . . . . ?
C45 C46 C47 C48 178.02(12) . . . . ?
C46 C47 C48 C49 -0.54(19) . . . . ?
C47 C48 C49 C50 2.0(2) . . . . ?
C48 C49 C50 C51 -1.7(2) . . . . ?
C49 C50 C51 C46 0.0(2) . . . . ?
C47 C46 C51 C50 1.45(19) . . . . ?
C45 C46 C51 C50 -177.76(12) . . . . ?
C17 N2 B1 F2 56.52(14) . . . . ?
C10 N2 B1 F2 -127.14(10) . . . . ?
C17 N2 B1 F1 -63.73(14) . . . . ?
C10 N2 B1 F1 112.61(11) . . . . ?
C17 N2 B1 N1 177.71(10) . . . . ?
C10 N2 B1 N1 -5.95(14) . . . . ?
C1 N1 B1 F2 -52.25(14) . . . . ?
C8 N1 B1 F2 124.97(10) . . . . ?
C1 N1 B1 F1 69.17(13) . . . . ?
C8 N1 B1 F1 -113.61(11) . . . . ?
C1 N1 B1 N2 -173.50(9) . . . . ?
C8 N1 B1 N2 3.72(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.580
_refine_diff_density_min         -1.786
_refine_diff_density_rms         0.076
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound6a
_database_code_depnum_ccdc_archive 'CCDC 1435994'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H23 B F2 N2'
_chemical_formula_sum            'C35 H23 B F2 N2'
_chemical_formula_weight         520.36

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

_symmetry_space_group_name_H-M   'P -1          '
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_cell_setting           Triclinic

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

_cell_length_a                   8.9607(14)
_cell_length_b                   10.4013(15)
_cell_length_c                   14.964(3)
_cell_angle_alpha                98.262(9)
_cell_angle_beta                 106.170(6)
_cell_angle_gamma                107.413(9)
_cell_volume                     1238.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    5549
_cell_measurement_theta_min      2.546
_cell_measurement_theta_max      27.878

_exptl_crystal_description       prism
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius KappaCCD '
_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            22864
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         27.87
_reflns_number_total             5881
_reflns_number_gt                4349
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_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)+(0.0516P)²+0.3483P] 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         5881
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.42835(11) 0.23459(10) 0.31533(7) 0.0333(2) Uani 1 1 d . . .
F2 F 0.44227(11) 0.13762(9) 0.17273(7) 0.0342(3) Uani 1 1 d . . .
N1 N 0.69693(14) 0.29807(12) 0.29843(8) 0.0167(3) Uani 1 1 d . . .
N2 N 0.47407(14) 0.37699(12) 0.20288(8) 0.0168(3) Uani 1 1 d . . .
C1 C 0.77144(17) 0.22983(14) 0.35628(10) 0.0168(3) Uani 1 1 d . . .
C2 C 0.94353(17) 0.31294(15) 0.40119(10) 0.0179(3) Uani 1 1 d . . .
C3 C 0.97190(17) 0.43597(14) 0.36799(10) 0.0170(3) Uani 1 1 d . . .
C4 C 0.81485(17) 0.42499(14) 0.30269(10) 0.0170(3) Uani 1 1 d . . .
C5 C 0.76777(17) 0.51722(14) 0.25224(10) 0.0170(3) Uani 1 1 d . . .
C6 C 0.60195(17) 0.49205(14) 0.20024(10) 0.0170(3) Uani 1 1 d . . .
C7 C 0.52806(17) 0.56241(14) 0.13501(10) 0.0166(3) Uani 1 1 d . . .
C8 C 0.35454(17) 0.48740(14) 0.10168(10) 0.0167(3) Uani 1 1 d . . .
C9 C 0.32609(17) 0.37339(14) 0.14489(10) 0.0162(3) Uani 1 1 d . . .
C10 C 1.07463(18) 0.28901(16) 0.46572(11) 0.0206(3) Uani 1 1 d . . .
H10 H 1.0563 0.2045 0.4855 0.025 Uiso 1 1 calc R . .
C11 C 1.22941(18) 0.39112(16) 0.49911(11) 0.0233(3) Uani 1 1 d . . .
H11 H 1.3190 0.3777 0.5436 0.028 Uiso 1 1 calc R . .
C12 C 1.25788(18) 0.51542(16) 0.46858(11) 0.0212(3) Uani 1 1 d . . .
H12 H 1.3659 0.5851 0.4941 0.025 Uiso 1 1 calc R . .
C13 C 1.13272(17) 0.53849(15) 0.40252(11) 0.0192(3) Uani 1 1 d . . .
H13 H 1.1544 0.6214 0.3808 0.023 Uiso 1 1 calc R . .
C14 C 0.59034(18) 0.67766(14) 0.09860(10) 0.0181(3) Uani 1 1 d . . .
H14 H 0.7063 0.7290 0.1192 0.022 Uiso 1 1 calc R . .
C15 C 0.47880(18) 0.71355(15) 0.03255(10) 0.0204(3) Uani 1 1 d . . .
H15 H 0.5196 0.7898 0.0069 0.024 Uiso 1 1 calc R . .
C16 C 0.30575(19) 0.64057(15) 0.00170(11) 0.0212(3) Uani 1 1 d . . .
H16 H 0.2323 0.6693 -0.0432 0.025 Uiso 1 1 calc R . .
C17 C 0.24277(18) 0.52858(15) 0.03597(10) 0.0191(3) Uani 1 1 d . . .
H17 H 0.1262 0.4798 0.0158 0.023 Uiso 1 1 calc R . .
C18 C 0.68990(17) 0.09082(15) 0.36775(11) 0.0184(3) Uani 1 1 d . . .
C19 C 0.71224(18) 0.06930(16) 0.45969(11) 0.0225(3) Uani 1 1 d . . .
H19 H 0.7780 0.1451 0.5141 0.027 Uiso 1 1 calc R . .
C20 C 0.63963(19) -0.06150(17) 0.47276(12) 0.0262(3) Uani 1 1 d . . .
H20 H 0.6546 -0.0747 0.5357 0.031 Uiso 1 1 calc R . .
C21 C 0.54490(19) -0.17308(16) 0.39324(12) 0.0254(3) Uani 1 1 d . . .
H21 H 0.4925 -0.2622 0.4018 0.031 Uiso 1 1 calc R . .
C22 C 0.52709(18) -0.15417(15) 0.30164(12) 0.0237(3) Uani 1 1 d . . .
H22 H 0.4655 -0.2312 0.2475 0.028 Uiso 1 1 calc R . .
C23 C 0.59841(17) -0.02377(15) 0.28829(11) 0.0200(3) Uani 1 1 d . . .
H23 H 0.5854 -0.0118 0.2252 0.024 Uiso 1 1 calc R . .
C24 C 0.89647(17) 0.64742(15) 0.25343(10) 0.0177(3) Uani 1 1 d . . .
C25 C 1.00677(17) 0.64324(15) 0.20435(10) 0.0197(3) Uani 1 1 d . . .
H25 H 1.0044 0.5562 0.1728 0.024 Uiso 1 1 calc R . .
C26 C 1.12010(18) 0.76569(16) 0.20143(11) 0.0239(3) Uani 1 1 d . . .
H26 H 1.1926 0.7623 0.1661 0.029 Uiso 1 1 calc R . .
C27 C 1.12814(19) 0.89323(16) 0.24980(12) 0.0265(4) Uani 1 1 d . . .
H27 H 1.2069 0.9769 0.2483 0.032 Uiso 1 1 calc R . .
C28 C 1.02067(19) 0.89815(16) 0.30038(11) 0.0244(3) Uani 1 1 d . . .
H28 H 1.0268 0.9852 0.3343 0.029 Uiso 1 1 calc R . .
C29 C 0.90431(18) 0.77585(15) 0.30141(10) 0.0197(3) Uani 1 1 d . . .
H29 H 0.8295 0.7797 0.3350 0.024 Uiso 1 1 calc R . .
C30 C 0.16102(17) 0.26896(14) 0.12757(10) 0.0178(3) Uani 1 1 d . . .
C31 C 0.10013(18) 0.24191(15) 0.20213(11) 0.0205(3) Uani 1 1 d . . .
H31 H 0.1683 0.2863 0.2671 0.025 Uiso 1 1 calc R . .
C32 C -0.06102(18) 0.14945(15) 0.18025(12) 0.0232(3) Uani 1 1 d . . .
H32 H -0.1027 0.1315 0.2308 0.028 Uiso 1 1 calc R . .
C33 C -0.16172(18) 0.08315(15) 0.08604(12) 0.0230(3) Uani 1 1 d . . .
H33 H -0.2714 0.0199 0.0723 0.028 Uiso 1 1 calc R . .
C34 C -0.10202(18) 0.10931(15) 0.01160(11) 0.0218(3) Uani 1 1 d . . .
H34 H -0.1702 0.0635 -0.0531 0.026 Uiso 1 1 calc R . .
C35 C 0.05808(17) 0.20289(15) 0.03262(11) 0.0196(3) Uani 1 1 d . . .
H35 H 0.0981 0.2222 -0.0183 0.023 Uiso 1 1 calc R . .
B1 B 0.5043(2) 0.25547(17) 0.24746(13) 0.0209(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
F1 B1 1.379(2) . ?
F2 B1 1.3836(19) . ?
N1 C1 1.3555(18) . ?
N1 C4 1.4024(18) . ?
N1 B1 1.571(2) . ?
N2 C9 1.3538(17) . ?
N2 C6 1.4018(18) . ?
N2 B1 1.569(2) . ?
C1 C2 1.426(2) . ?
C1 C18 1.471(2) . ?
C2 C10 1.410(2) . ?
C2 C3 1.417(2) . ?
C3 C13 1.410(2) . ?
C3 C4 1.4332(19) . ?
C4 C5 1.393(2) . ?
C5 C6 1.395(2) . ?
C5 C24 1.4870(19) . ?
C6 C7 1.436(2) . ?
C7 C14 1.415(2) . ?
C7 C8 1.4160(19) . ?
C8 C17 1.4082(19) . ?
C8 C9 1.421(2) . ?
C9 C30 1.4761(19) . ?
C10 C11 1.372(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.376(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.395(2) . ?
C18 C23 1.404(2) . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.392(2) . ?
C24 C29 1.395(2) . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.388(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C35 1.397(2) . ?
C30 C31 1.400(2) . ?
C31 C32 1.390(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.385(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(2) . ?
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
C1 N1 C4 109.67(11) . . ?
C1 N1 B1 125.64(12) . . ?
C4 N1 B1 123.98(12) . . ?
C9 N2 C6 109.42(12) . . ?
C9 N2 B1 125.44(12) . . ?
C6 N2 B1 123.80(12) . . ?
N1 C1 C2 108.61(12) . . ?
N1 C1 C18 125.67(13) . . ?
C2 C1 C18 125.68(13) . . ?
C10 C2 C3 121.11(13) . . ?
C10 C2 C1 131.25(14) . . ?
C3 C2 C1 107.62(12) . . ?
C13 C3 C2 119.55(13) . . ?
C13 C3 C4 133.98(13) . . ?
C2 C3 C4 106.46(12) . . ?
C5 C4 N1 120.78(12) . . ?
C5 C4 C3 131.50(13) . . ?
N1 C4 C3 107.64(12) . . ?
C4 C5 C6 122.06(13) . . ?
C4 C5 C24 119.75(12) . . ?
C6 C5 C24 118.19(12) . . ?
C5 C6 N2 120.72(13) . . ?
C5 C6 C7 131.33(13) . . ?
N2 C6 C7 107.88(12) . . ?
C14 C7 C8 119.18(13) . . ?
C14 C7 C6 134.79(13) . . ?
C8 C7 C6 105.97(12) . . ?
C17 C8 C7 121.25(13) . . ?
C17 C8 C9 130.80(13) . . ?
C7 C8 C9 107.94(12) . . ?
N2 C9 C8 108.77(12) . . ?
N2 C9 C30 126.52(13) . . ?
C8 C9 C30 124.70(12) . . ?
C11 C10 C2 118.12(14) . . ?
C11 C10 H10 120.9 . . ?
C2 C10 H10 120.9 . . ?
C10 C11 C12 121.15(14) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 121.61(14) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C3 118.38(14) . . ?
C12 C13 H13 120.8 . . ?
C3 C13 H13 120.8 . . ?
C15 C14 C7 118.39(13) . . ?
C15 C14 H14 120.8 . . ?
C7 C14 H14 120.8 . . ?
C14 C15 C16 122.06(14) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 120.51(14) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C8 118.56(13) . . ?
C16 C17 H17 120.7 . . ?
C8 C17 H17 120.7 . . ?
C19 C18 C23 118.65(14) . . ?
C19 C18 C1 119.60(13) . . ?
C23 C18 C1 121.62(13) . . ?
C20 C19 C18 120.90(15) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.70(15) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 119.94(14) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.51(15) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 120.22(14) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C25 C24 C29 119.22(13) . . ?
C25 C24 C5 120.67(13) . . ?
C29 C24 C5 120.08(13) . . ?
C26 C25 C24 120.19(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.36(15) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 119.77(14) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 119.96(14) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C24 120.46(14) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C35 C30 C31 119.23(13) . . ?
C35 C30 C9 118.25(13) . . ?
C31 C30 C9 122.34(13) . . ?
C32 C31 C30 119.37(14) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C33 C32 C31 121.08(14) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 119.87(14) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C35 C34 C33 119.50(14) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C30 120.92(14) . . ?
C34 C35 H35 119.5 . . ?
C30 C35 H35 119.5 . . ?
F1 B1 F2 111.12(13) . . ?
F1 B1 N2 111.19(13) . . ?
F2 B1 N2 107.25(13) . . ?
F1 B1 N1 108.25(13) . . ?
F2 B1 N1 111.25(13) . . ?
N2 B1 N1 107.74(11) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.053
# END OF CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound6c
_database_code_depnum_ccdc_archive 'CCDC 1435995'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H21 B F2 N4 O4'
_chemical_formula_sum            'C35 H21 B F2 N4 O4'
_chemical_formula_weight         610.37

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'
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_Hall  '-P 2ybc'
_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                   12.2985(6)
_cell_length_b                   12.9578(6)
_cell_length_c                   18.4622(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.407(2)
_cell_angle_gamma                90
_cell_volume                     2791.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    8340
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.12

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8677
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27177
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.25
_reflns_number_total             26528
_reflns_number_gt                20508
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
 Refinement of F² against ALL reflections. The crystal was a nonmerohedral
twin by 180 deg rotation about reciprocal 1 0 0. Refinement was vs. an 
HKLF 5 file, and the BASF parameter refined to 0.1557(9).

;

_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)+(0.0617P)²+2.1349P] 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         26528
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
F1 F 0.51822(5) 0.38869(5) 0.54358(3) 0.01931(15) Uani 1 1 d . . .
F2 F 0.49297(5) 0.34372(5) 0.65582(4) 0.01947(15) Uani 1 1 d . . .
O1 O 0.07651(9) 0.02228(7) 0.43919(5) 0.0424(3) Uani 1 1 d . . .
O2 O 0.18265(8) -0.01115(6) 0.55429(5) 0.0351(2) Uani 1 1 d . . .
O3 O 0.87006(9) 0.00571(7) 0.82768(5) 0.0402(3) Uani 1 1 d . . .
O4 O 0.82804(8) -0.02256(6) 0.70621(5) 0.0290(2) Uani 1 1 d . . .
N1 N 0.39547(7) 0.49634(6) 0.58801(5) 0.01189(19) Uani 1 1 d . . .
N2 N 0.60886(7) 0.49162(6) 0.65579(5) 0.01194(19) Uani 1 1 d . . .
N3 N 0.14272(9) 0.04848(7) 0.50074(6) 0.0227(2) Uani 1 1 d . . .
N4 N 0.83640(8) 0.03467(7) 0.76074(6) 0.0227(2) Uani 1 1 d . . .
C1 C 0.28880(9) 0.46692(8) 0.54567(6) 0.0129(2) Uani 1 1 d . . .
C2 C 0.22100(9) 0.55593(8) 0.51769(6) 0.0129(2) Uani 1 1 d . . .
C3 C 0.10590(9) 0.56697(8) 0.47326(6) 0.0161(2) Uani 1 1 d . . .
H3A H 0.0596 0.5082 0.4541 0.019 Uiso 1 1 calc R . .
C4 C 0.06170(10) 0.66480(9) 0.45809(6) 0.0176(2) Uani 1 1 d . . .
H4A H -0.0162 0.6739 0.4283 0.021 Uiso 1 1 calc R . .
C5 C 0.13046(9) 0.75169(8) 0.48617(6) 0.0156(2) Uani 1 1 d . . .
H5 H 0.0976 0.8185 0.4750 0.019 Uiso 1 1 calc R . .
C6 C 0.24425(9) 0.74303(8) 0.52941(6) 0.0142(2) Uani 1 1 d . . .
H6 H 0.2896 0.8027 0.5476 0.017 Uiso 1 1 calc R . .
C7 C 0.29159(9) 0.64315(8) 0.54588(6) 0.0128(2) Uani 1 1 d . . .
C8 C 0.40221(9) 0.60380(8) 0.58905(6) 0.0124(2) Uani 1 1 d . . .
C9 C 0.50582(9) 0.65356(8) 0.62229(6) 0.0121(2) Uani 1 1 d . . .
C10 C 0.60756(9) 0.59897(8) 0.65653(6) 0.0121(2) Uani 1 1 d . . .
C11 C 0.71848(9) 0.63342(8) 0.70283(6) 0.0127(2) Uani 1 1 d . . .
C12 C 0.77024(9) 0.73106(8) 0.72223(6) 0.0148(2) Uani 1 1 d . . .
H12 H 0.7286 0.7926 0.7039 0.018 Uiso 1 1 calc R . .
C13 C 0.88259(9) 0.73494(8) 0.76840(6) 0.0164(2) Uani 1 1 d . . .
H13 H 0.9187 0.8002 0.7815 0.020 Uiso 1 1 calc R . .
C14 C 0.94543(10) 0.64453(8) 0.79668(6) 0.0175(2) Uani 1 1 d . . .
H14 H 1.0224 0.6503 0.8291 0.021 Uiso 1 1 calc R . .
C15 C 0.89805(9) 0.54859(9) 0.77849(6) 0.0164(2) Uani 1 1 d . . .
H15 H 0.9412 0.4879 0.7971 0.020 Uiso 1 1 calc R . .
C16 C 0.78311(9) 0.54274(8) 0.73119(6) 0.0138(2) Uani 1 1 d . . .
C17 C 0.71218(9) 0.45684(8) 0.70043(6) 0.0133(2) Uani 1 1 d . . .
C18 C 0.24992(9) 0.35918(8) 0.53430(6) 0.0128(2) Uani 1 1 d . . .
C19 C 0.19195(9) 0.32300(8) 0.46066(6) 0.0152(2) Uani 1 1 d . . .
H19 H 0.1781 0.3684 0.4183 0.018 Uiso 1 1 calc R . .
C20 C 0.15471(9) 0.22167(8) 0.44904(6) 0.0171(2) Uani 1 1 d . . .
H20 H 0.1150 0.1969 0.3993 0.021 Uiso 1 1 calc R . .
C21 C 0.17699(10) 0.15760(8) 0.51199(6) 0.0161(2) Uani 1 1 d . . .
C22 C 0.23113(9) 0.19093(8) 0.58568(6) 0.0153(2) Uani 1 1 d . . .
H22 H 0.2440 0.1451 0.6277 0.018 Uiso 1 1 calc R . .
C23 C 0.26607(9) 0.29292(8) 0.59656(6) 0.0143(2) Uani 1 1 d . . .
H23 H 0.3014 0.3181 0.6469 0.017 Uiso 1 1 calc R . .
C24 C 0.51169(9) 0.76838(8) 0.62204(6) 0.0130(2) Uani 1 1 d . . .
C25 C 0.55703(9) 0.81853(8) 0.57109(6) 0.0162(2) Uani 1 1 d . . .
H25 H 0.5809 0.7797 0.5352 0.019 Uiso 1 1 calc R . .
C26 C 0.56700(10) 0.92497(9) 0.57313(6) 0.0192(2) Uani 1 1 d . . .
H26 H 0.5991 0.9591 0.5391 0.023 Uiso 1 1 calc R . .
C27 C 0.53024(10) 0.98222(9) 0.62470(7) 0.0225(3) Uani 1 1 d . . .
H27 H 0.5359 1.0553 0.6252 0.027 Uiso 1 1 calc R . .
C28 C 0.48542(10) 0.93265(9) 0.67519(7) 0.0224(3) Uani 1 1 d . . .
H28 H 0.4606 0.9716 0.7106 0.027 Uiso 1 1 calc R . .
C29 C 0.47669(10) 0.82550(8) 0.67408(6) 0.0174(2) Uani 1 1 d . . .
H29 H 0.4466 0.7914 0.7092 0.021 Uiso 1 1 calc R . .
C30 C 0.74415(9) 0.34712(8) 0.71472(6) 0.0133(2) Uani 1 1 d . . .
C31 C 0.79747(9) 0.31432(9) 0.78986(6) 0.0172(2) Uani 1 1 d . . .
H31 H 0.8134 0.3628 0.8305 0.021 Uiso 1 1 calc R . .
C32 C 0.82717(10) 0.21178(9) 0.80535(6) 0.0182(2) Uani 1 1 d . . .
H32 H 0.8623 0.1889 0.8563 0.022 Uiso 1 1 calc R . .
C33 C 0.80452(10) 0.14371(8) 0.74503(7) 0.0175(2) Uani 1 1 d . . .
C34 C 0.75491(9) 0.17449(8) 0.66996(6) 0.0175(2) Uani 1 1 d . . .
H34 H 0.7422 0.1261 0.6295 0.021 Uiso 1 1 calc R . .
C35 C 0.72434(9) 0.27627(8) 0.65499(6) 0.0164(2) Uani 1 1 d . . .
H35 H 0.6896 0.2984 0.6038 0.020 Uiso 1 1 calc R . .
B1 B 0.50393(10) 0.42447(9) 0.61051(7) 0.0129(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3820(13) . ?
F2 B1 1.3726(13) . ?
O1 N3 1.2187(12) . ?
O2 N3 1.2285(12) . ?
O3 N4 1.2314(13) . ?
O4 N4 1.2283(12) . ?
N1 C1 1.3527(13) . ?
N1 C8 1.3947(12) . ?
N1 B1 1.5714(15) . ?
N2 C17 1.3549(13) . ?
N2 C10 1.3912(12) . ?
N2 B1 1.5620(15) . ?
N3 C21 1.4713(13) . ?
N4 C33 1.4704(13) . ?
C1 C2 1.4214(15) . ?
C1 C18 1.4691(14) . ?
C2 C3 1.4014(15) . ?
C2 C7 1.4200(14) . ?
C3 C4 1.3729(15) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4053(15) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3793(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4122(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.4358(15) . ?
C8 C9 1.3864(15) . ?
C9 C10 1.4022(15) . ?
C9 C24 1.4897(14) . ?
C10 C11 1.4333(15) . ?
C11 C12 1.4108(14) . ?
C11 C16 1.4226(14) . ?
C12 C13 1.3764(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.4098(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3690(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.4095(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.4175(15) . ?
C17 C30 1.4765(14) . ?
C18 C23 1.3977(14) . ?
C18 C19 1.4016(15) . ?
C19 C20 1.3849(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.3834(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.3814(15) . ?
C22 C23 1.3846(14) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.3848(14) . ?
C24 C25 1.3961(14) . ?
C25 C26 1.3841(15) . ?
C25 H25 0.9500 . ?
C26 C27 1.3903(16) . ?
C26 H26 0.9500 . ?
C27 C28 1.3820(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.3922(15) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C35 1.3959(15) . ?
C30 C31 1.4002(15) . ?
C31 C32 1.3836(15) . ?
C31 H31 0.9500 . ?
C32 C33 1.3785(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.3849(15) . ?
C34 C35 1.3754(15) . ?
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
C1 N1 C8 109.39(8) . . ?
C1 N1 B1 124.97(9) . . ?
C8 N1 B1 123.11(8) . . ?
C17 N2 C10 109.76(8) . . ?
C17 N2 B1 126.72(9) . . ?
C10 N2 B1 123.51(8) . . ?
O1 N3 O2 123.70(10) . . ?
O1 N3 C21 118.47(10) . . ?
O2 N3 C21 117.83(9) . . ?
O4 N4 O3 123.58(10) . . ?
O4 N4 C33 118.06(9) . . ?
O3 N4 C33 118.36(10) . . ?
N1 C1 C2 109.38(9) . . ?
N1 C1 C18 124.25(9) . . ?
C2 C1 C18 126.31(10) . . ?
C3 C2 C7 121.39(10) . . ?
C3 C2 C1 131.59(10) . . ?
C7 C2 C1 106.98(10) . . ?
C4 C3 C2 118.39(10) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C5 120.74(11) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 122.06(10) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 118.23(10) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C2 119.19(10) . . ?
C6 C7 C8 134.34(10) . . ?
C2 C7 C8 106.45(9) . . ?
C9 C8 N1 120.85(9) . . ?
C9 C8 C7 131.14(9) . . ?
N1 C8 C7 107.77(9) . . ?
C8 C9 C10 121.98(9) . . ?
C8 C9 C24 120.12(9) . . ?
C10 C9 C24 117.90(9) . . ?
N2 C10 C9 120.75(9) . . ?
N2 C10 C11 107.79(9) . . ?
C9 C10 C11 131.11(10) . . ?
C12 C11 C16 119.50(10) . . ?
C12 C11 C10 134.34(10) . . ?
C16 C11 C10 106.15(9) . . ?
C13 C12 C11 118.31(10) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 121.65(10) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 121.51(11) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 117.82(10) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C15 C16 C17 131.32(10) . . ?
C15 C16 C11 121.20(10) . . ?
C17 C16 C11 107.42(10) . . ?
N2 C17 C16 108.84(9) . . ?
N2 C17 C30 125.07(9) . . ?
C16 C17 C30 126.09(10) . . ?
C23 C18 C19 119.28(10) . . ?
C23 C18 C1 120.73(9) . . ?
C19 C18 C1 119.95(9) . . ?
C20 C19 C18 120.62(10) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 118.09(10) . . ?
C21 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C22 C21 C20 123.07(10) . . ?
C22 C21 N3 117.84(10) . . ?
C20 C21 N3 119.08(10) . . ?
C21 C22 C23 118.19(10) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C18 120.66(10) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C29 C24 C25 119.77(10) . . ?
C29 C24 C9 120.37(9) . . ?
C25 C24 C9 119.81(9) . . ?
C26 C25 C24 119.75(10) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.34(10) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 119.94(10) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.93(10) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 120.25(10) . . ?
C24 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C35 C30 C31 119.56(10) . . ?
C35 C30 C17 121.46(9) . . ?
C31 C30 C17 118.97(9) . . ?
C32 C31 C30 120.45(10) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 118.34(10) . . ?
C33 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C32 C33 C34 122.48(10) . . ?
C32 C33 N4 118.83(10) . . ?
C34 C33 N4 118.68(10) . . ?
C35 C34 C33 118.91(10) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C30 120.23(10) . . ?
C34 C35 H35 119.9 . . ?
C30 C35 H35 119.9 . . ?
F2 B1 F1 110.73(9) . . ?
F2 B1 N2 108.78(9) . . ?
F1 B1 N2 110.40(9) . . ?
F2 B1 N1 111.98(9) . . ?
F1 B1 N1 107.43(8) . . ?
N2 B1 N1 107.47(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -0.46(11) . . . . ?
B1 N1 C1 C2 -162.78(9) . . . . ?
C8 N1 C1 C18 -177.86(9) . . . . ?
B1 N1 C1 C18 19.82(15) . . . . ?
N1 C1 C2 C3 -178.38(10) . . . . ?
C18 C1 C2 C3 -1.05(18) . . . . ?
N1 C1 C2 C7 -0.62(11) . . . . ?
C18 C1 C2 C7 176.71(9) . . . . ?
C7 C2 C3 C4 -0.82(15) . . . . ?
C1 C2 C3 C4 176.68(11) . . . . ?
C2 C3 C4 C5 0.30(16) . . . . ?
C3 C4 C5 C6 0.33(16) . . . . ?
C4 C5 C6 C7 -0.43(15) . . . . ?
C5 C6 C7 C2 -0.08(14) . . . . ?
C5 C6 C7 C8 -178.38(11) . . . . ?
C3 C2 C7 C6 0.72(15) . . . . ?
C1 C2 C7 C6 -177.33(9) . . . . ?
C3 C2 C7 C8 179.45(9) . . . . ?
C1 C2 C7 C8 1.41(11) . . . . ?
C1 N1 C8 C9 -173.56(9) . . . . ?
B1 N1 C8 C9 -10.85(14) . . . . ?
C1 N1 C8 C7 1.35(11) . . . . ?
B1 N1 C8 C7 164.06(9) . . . . ?
C6 C7 C8 C9 -9.0(2) . . . . ?
C2 C7 C8 C9 172.50(10) . . . . ?
C6 C7 C8 N1 176.76(11) . . . . ?
C2 C7 C8 N1 -1.69(11) . . . . ?
N1 C8 C9 C10 -0.41(15) . . . . ?
C7 C8 C9 C10 -173.97(10) . . . . ?
N1 C8 C9 C24 179.24(8) . . . . ?
C7 C8 C9 C24 5.68(17) . . . . ?
C17 N2 C10 C9 -172.14(9) . . . . ?
B1 N2 C10 C9 6.87(14) . . . . ?
C17 N2 C10 C11 1.82(11) . . . . ?
B1 N2 C10 C11 -179.18(9) . . . . ?
C8 C9 C10 N2 2.44(15) . . . . ?
C24 C9 C10 N2 -177.22(8) . . . . ?
C8 C9 C10 C11 -169.91(10) . . . . ?
C24 C9 C10 C11 10.43(16) . . . . ?
N2 C10 C11 C12 176.83(10) . . . . ?
C9 C10 C11 C12 -10.1(2) . . . . ?
N2 C10 C11 C16 -1.98(11) . . . . ?
C9 C10 C11 C16 171.12(10) . . . . ?
C16 C11 C12 C13 -0.02(14) . . . . ?
C10 C11 C12 C13 -178.70(11) . . . . ?
C11 C12 C13 C14 -0.54(15) . . . . ?
C12 C13 C14 C15 1.05(16) . . . . ?
C13 C14 C15 C16 -0.93(16) . . . . ?
C14 C15 C16 C17 177.43(10) . . . . ?
C14 C15 C16 C11 0.37(15) . . . . ?
C12 C11 C16 C15 0.10(15) . . . . ?
C10 C11 C16 C15 179.12(9) . . . . ?
C12 C11 C16 C17 -177.59(9) . . . . ?
C10 C11 C16 C17 1.43(11) . . . . ?
C10 N2 C17 C16 -0.91(11) . . . . ?
B1 N2 C17 C16 -179.88(9) . . . . ?
C10 N2 C17 C30 178.62(9) . . . . ?
B1 N2 C17 C30 -0.35(16) . . . . ?
C15 C16 C17 N2 -177.73(11) . . . . ?
C11 C16 C17 N2 -0.36(11) . . . . ?
C15 C16 C17 C30 2.75(18) . . . . ?
C11 C16 C17 C30 -179.89(9) . . . . ?
N1 C1 C18 C23 50.73(14) . . . . ?
C2 C1 C18 C23 -126.23(12) . . . . ?
N1 C1 C18 C19 -131.79(11) . . . . ?
C2 C1 C18 C19 51.25(15) . . . . ?
C23 C18 C19 C20 -2.43(15) . . . . ?
C1 C18 C19 C20 -179.95(10) . . . . ?
C18 C19 C20 C21 -0.36(16) . . . . ?
C19 C20 C21 C22 2.14(17) . . . . ?
C19 C20 C21 N3 -177.37(10) . . . . ?
O1 N3 C21 C22 166.25(11) . . . . ?
O2 N3 C21 C22 -13.66(15) . . . . ?
O1 N3 C21 C20 -14.22(16) . . . . ?
O2 N3 C21 C20 165.87(10) . . . . ?
C20 C21 C22 C23 -1.00(17) . . . . ?
N3 C21 C22 C23 178.51(10) . . . . ?
C21 C22 C23 C18 -1.92(16) . . . . ?
C19 C18 C23 C22 3.60(15) . . . . ?
C1 C18 C23 C22 -178.90(10) . . . . ?
C8 C9 C24 C29 79.06(13) . . . . ?
C10 C9 C24 C29 -101.27(12) . . . . ?
C8 C9 C24 C25 -103.52(12) . . . . ?
C10 C9 C24 C25 76.15(13) . . . . ?
C29 C24 C25 C26 0.21(16) . . . . ?
C9 C24 C25 C26 -177.22(10) . . . . ?
C24 C25 C26 C27 -1.15(16) . . . . ?
C25 C26 C27 C28 1.19(17) . . . . ?
C26 C27 C28 C29 -0.28(18) . . . . ?
C25 C24 C29 C28 0.70(16) . . . . ?
C9 C24 C29 C28 178.11(10) . . . . ?
C27 C28 C29 C24 -0.66(17) . . . . ?
N2 C17 C30 C35 49.00(15) . . . . ?
C16 C17 C30 C35 -131.55(11) . . . . ?
N2 C17 C30 C31 -132.23(11) . . . . ?
C16 C17 C30 C31 47.22(15) . . . . ?
C35 C30 C31 C32 -2.08(16) . . . . ?
C17 C30 C31 C32 179.14(10) . . . . ?
C30 C31 C32 C33 0.98(16) . . . . ?
C31 C32 C33 C34 0.91(17) . . . . ?
C31 C32 C33 N4 179.60(10) . . . . ?
O4 N4 C33 C32 -171.71(10) . . . . ?
O3 N4 C33 C32 8.22(15) . . . . ?
O4 N4 C33 C34 7.02(15) . . . . ?
O3 N4 C33 C34 -173.05(11) . . . . ?
C32 C33 C34 C35 -1.67(17) . . . . ?
N4 C33 C34 C35 179.64(10) . . . . ?
C33 C34 C35 C30 0.53(16) . . . . ?
C31 C30 C35 C34 1.30(16) . . . . ?
C17 C30 C35 C34 -179.94(10) . . . . ?
C17 N2 B1 F2 42.10(13) . . . . ?
C10 N2 B1 F2 -136.73(9) . . . . ?
C17 N2 B1 F1 -79.60(12) . . . . ?
C10 N2 B1 F1 101.58(10) . . . . ?
C17 N2 B1 N1 163.53(9) . . . . ?
C10 N2 B1 N1 -15.30(12) . . . . ?
C1 N1 B1 F2 -63.33(13) . . . . ?
C8 N1 B1 F2 136.68(9) . . . . ?
C1 N1 B1 F1 58.46(13) . . . . ?
C8 N1 B1 F1 -101.54(10) . . . . ?
C1 N1 B1 N2 177.26(9) . . . . ?
C8 N1 B1 N2 17.26(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.063
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_Compound6d
_database_code_depnum_ccdc_archive 'CCDC 1435996'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H20.95 B Cl0.05 F2 N4'
_chemical_formula_sum            'C37 H20.95 B Cl0.05 F2 N4'
_chemical_formula_weight         572.02

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb '
_symmetry_space_group_name_H-M   'P 21   '

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

_cell_length_a                   13.2913(16)
_cell_length_b                   16.431(2)
_cell_length_c                   13.4762(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.238(2)
_cell_angle_gamma                90
_cell_volume                     2810.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    8656
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      29.15

_exptl_crystal_description       plate
_exptl_crystal_colour            'blue (reflects bronze)'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1179
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9387
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21435
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         29.20
_reflns_number_total             12494
_reflns_number_gt                10966
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0527P)²+0.4103P] 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_abs_structure_details 
;
 Flack x determined using 3923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_number_reflns         12494
_refine_ls_number_parameters     803
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
F1 F 0.22897(8) 0.44953(7) 0.66605(8) 0.0175(2) Uani 1 1 d . A .
F2 F 0.28953(8) 0.31884(7) 0.67653(8) 0.0171(2) Uani 1 1 d . A .
N1 N 0.41263(11) 0.42361(10) 0.75322(11) 0.0135(3) Uani 1 1 d . A .
N2 N 0.33789(11) 0.40896(10) 0.55846(11) 0.0136(3) Uani 1 1 d . A .
N3 N 0.02111(13) 0.46913(12) 1.07608(13) 0.0239(4) Uani 1 1 d . . .
N4 N -0.26639(13) 0.43697(12) 0.32272(14) 0.0279(4) Uani 1 1 d . . .
C1 C 0.42004(14) 0.43753(12) 0.85380(14) 0.0147(4) Uani 1 1 d . . .
C2 C 0.52775(14) 0.44800(12) 0.91072(14) 0.0157(4) Uani 1 1 d . . .
C3 C 0.57763(14) 0.45922(12) 1.01750(14) 0.0184(4) Uani 1 1 d . A .
H3 H 0.5378 0.4617 1.0655 0.022 Uiso 1 1 calc R . .
C4 C 0.68521(15) 0.46647(13) 1.05049(15) 0.0205(4) Uani 1 1 d . . .
H4 H 0.7202 0.4747 1.1222 0.025 Uiso 0.970(2) 1 calc PR A 1
Cl1 Cl 0.7540(12) 0.4380(10) 1.1712(12) 0.019(5) Uiso 0.030(2) 1 d P . 2
C5 C 0.74474(15) 0.46192(13) 0.97967(15) 0.0215(4) Uani 1 1 d . A .
H5 H 0.8190 0.4684 1.0044 0.026 Uiso 1 1 calc R . .
C6 C 0.69730(14) 0.44831(13) 0.87515(15) 0.0189(4) Uani 1 1 d . . .
H6 H 0.7383 0.4444 0.8283 0.023 Uiso 1 1 calc R A .
C7 C 0.58753(14) 0.44035(12) 0.83963(14) 0.0151(4) Uani 1 1 d . A .
C8 C 0.51303(13) 0.42496(12) 0.73995(14) 0.0148(4) Uani 1 1 d . . .
C9 C 0.52611(13) 0.41621(11) 0.64179(14) 0.0134(3) Uani 1 1 d . A .
C10 C 0.44149(13) 0.40850(11) 0.55277(14) 0.0134(3) Uani 1 1 d . . .
C11 C 0.43650(13) 0.40430(11) 0.44546(13) 0.0135(3) Uani 1 1 d . A .
C12 C 0.51360(13) 0.39829(12) 0.39281(14) 0.0144(4) Uani 1 1 d . . .
H12 H 0.5866 0.3995 0.4297 0.017 Uiso 1 1 calc R A .
C13 C 0.47970(14) 0.39062(12) 0.28629(14) 0.0158(4) Uani 1 1 d . A .
H13 H 0.5307 0.3862 0.2498 0.019 Uiso 1 1 calc R . .
C14 C 0.37234(14) 0.38916(12) 0.22964(14) 0.0164(4) Uani 1 1 d . . .
H14 H 0.3521 0.3834 0.1562 0.020 Uiso 1 1 calc R A .
C15 C 0.29614(13) 0.39602(12) 0.27971(14) 0.0151(4) Uani 1 1 d . A .
H15 H 0.2235 0.3953 0.2417 0.018 Uiso 1 1 calc R . .
C16 C 0.32875(13) 0.40404(12) 0.38855(14) 0.0138(3) Uani 1 1 d . . .
C17 C 0.27024(13) 0.40651(12) 0.46172(14) 0.0141(3) Uani 1 1 d . A .
C18 C 0.33105(14) 0.44286(12) 0.89791(14) 0.0145(4) Uani 1 1 d . . .
C19 C 0.32882(14) 0.50837(12) 0.96373(14) 0.0160(4) Uani 1 1 d . . .
H19 H 0.3829 0.5483 0.9775 0.019 Uiso 1 1 calc R . .
C20 C 0.24831(14) 0.51518(12) 1.00876(14) 0.0167(4) Uani 1 1 d . . .
H20 H 0.2467 0.5599 1.0529 0.020 Uiso 1 1 calc R . .
C21 C 0.16966(14) 0.45624(12) 0.98927(14) 0.0152(4) Uani 1 1 d . . .
C22 C 0.17149(14) 0.39063(12) 0.92476(14) 0.0176(4) Uani 1 1 d . . .
H22 H 0.1178 0.3504 0.9121 0.021 Uiso 1 1 calc R . .
C23 C 0.25185(14) 0.38385(12) 0.87878(14) 0.0164(4) Uani 1 1 d . . .
H23 H 0.2530 0.3392 0.8344 0.020 Uiso 1 1 calc R . .
C24 C 0.08605(14) 0.46358(13) 1.03738(14) 0.0178(4) Uani 1 1 d . . .
C25 C 0.63619(13) 0.41563(12) 0.63392(13) 0.0137(4) Uani 1 1 d . . .
C26 C 0.68293(14) 0.48655(13) 0.61304(15) 0.0185(4) Uani 1 1 d . A .
H26 H 0.6431 0.5354 0.5978 0.022 Uiso 1 1 calc R . .
C27 C 0.78770(15) 0.48626(13) 0.61436(16) 0.0221(4) Uani 1 1 d . . .
H27 H 0.8197 0.5349 0.6004 0.027 Uiso 1 1 calc R A .
C28 C 0.84565(14) 0.41469(14) 0.63611(16) 0.0235(4) Uani 1 1 d . A .
H28 H 0.9180 0.4148 0.6393 0.028 Uiso 1 1 calc R . .
C29 C 0.79855(15) 0.34362(14) 0.65307(17) 0.0249(5) Uani 1 1 d . . .
H29 H 0.8377 0.2944 0.6653 0.030 Uiso 1 1 calc R A .
C30 C 0.69350(15) 0.34375(13) 0.65233(15) 0.0192(4) Uani 1 1 d . A .
H30 H 0.6612 0.2947 0.6644 0.023 Uiso 1 1 calc R . .
C31 C 0.15442(13) 0.40834(12) 0.43457(14) 0.0149(4) Uani 1 1 d . . .
C32 C 0.10031(14) 0.45818(12) 0.35209(14) 0.0175(4) Uani 1 1 d . A .
H32 H 0.1389 0.4894 0.3164 0.021 Uiso 1 1 calc R . .
C33 C -0.00833(14) 0.46286(13) 0.32149(15) 0.0183(4) Uani 1 1 d . . .
H33 H -0.0444 0.4962 0.2644 0.022 Uiso 1 1 calc R A .
C34 C -0.06451(14) 0.41812(13) 0.37534(15) 0.0173(4) Uani 1 1 d . A .
C35 C -0.01190(14) 0.36619(12) 0.45616(14) 0.0173(4) Uani 1 1 d . . .
H35 H -0.0507 0.3344 0.4909 0.021 Uiso 1 1 calc R A .
C36 C 0.09650(13) 0.36125(12) 0.48535(14) 0.0157(4) Uani 1 1 d . A .
H36 H 0.1322 0.3258 0.5402 0.019 Uiso 1 1 calc R . .
C37 C -0.17713(15) 0.42747(13) 0.34696(15) 0.0200(4) Uani 1 1 d . . .
B1 B 0.31159(15) 0.40020(14) 0.66437(16) 0.0145(4) Uani 1 1 d . . .
F3 F 0.48674(8) 0.27905(7) 0.09229(8) 0.0182(2) Uani 1 1 d . B .
F4 F 0.53371(8) 0.14516(7) 0.09600(8) 0.0191(2) Uani 1 1 d . B .
N5 N 0.35417(11) 0.18291(10) 0.00796(11) 0.0151(3) Uani 1 1 d . B .
N6 N 0.42696(11) 0.18884(10) 0.20319(12) 0.0145(3) Uani 1 1 d . B .
N7 N 0.75424(14) 0.12824(12) -0.30381(15) 0.0279(4) Uani 1 1 d . . .
N8 N 1.02785(14) 0.13902(14) 0.43331(14) 0.0324(5) Uani 1 1 d . . .
C38 C 0.34806(14) 0.17302(12) -0.09360(14) 0.0152(4) Uani 1 1 d . . .
C39 C 0.24025(14) 0.16677(11) -0.15232(14) 0.0161(4) Uani 1 1 d . . .
C40 C 0.19134(16) 0.16162(12) -0.26031(15) 0.0206(4) Uani 1 1 d . B .
H40 H 0.2320 0.1581 -0.3075 0.025 Uiso 1 1 calc R . .
C41 C 0.08387(16) 0.16191(13) -0.29519(15) 0.0226(4) Uani 1 1 d . . .
H41 H 0.0493 0.1599 -0.3678 0.027 Uiso 0.934(3) 1 calc PR B 1
Cl2 Cl 0.0193(9) 0.1598(7) -0.4241(9) 0.049(4) Uiso 0.066(3) 1 d P . 2
C42 C 0.02322(16) 0.16511(13) -0.22521(16) 0.0226(4) Uani 1 1 d . B .
H42 H -0.0514 0.1639 -0.2519 0.027 Uiso 1 1 calc R . .
C43 C 0.06909(14) 0.16988(12) -0.11954(15) 0.0192(4) Uani 1 1 d . . .
H43 H 0.0272 0.1712 -0.0734 0.023 Uiso 1 1 calc R B .
C44 C 0.17986(14) 0.17278(12) -0.08158(14) 0.0163(4) Uani 1 1 d . B .
C45 C 0.25350(14) 0.18256(12) 0.01918(14) 0.0156(4) Uani 1 1 d . . .
C46 C 0.23917(14) 0.18677(12) 0.11773(14) 0.0151(3) Uani 1 1 d . B .
C47 C 0.32335(13) 0.19053(12) 0.20754(14) 0.0150(4) Uani 1 1 d . . .
C48 C 0.32701(14) 0.19295(12) 0.31515(14) 0.0143(3) Uani 1 1 d . B .
C49 C 0.25022(14) 0.19820(12) 0.36750(14) 0.0163(4) Uani 1 1 d . . .
H49 H 0.1773 0.1989 0.3302 0.020 Uiso 1 1 calc R B .
C50 C 0.28325(14) 0.20233(12) 0.47405(15) 0.0174(4) Uani 1 1 d . B .
H50 H 0.2320 0.2050 0.5104 0.021 Uiso 1 1 calc R . .
C51 C 0.39053(15) 0.20273(12) 0.53092(14) 0.0182(4) Uani 1 1 d . . .
H51 H 0.4105 0.2074 0.6045 0.022 Uiso 1 1 calc R B .
C52 C 0.46696(14) 0.19638(12) 0.48141(14) 0.0169(4) Uani 1 1 d . B .
H52 H 0.5395 0.1959 0.5198 0.020 Uiso 1 1 calc R . .
C53 C 0.43495(14) 0.19061(12) 0.37277(14) 0.0150(4) Uani 1 1 d . . .
C54 C 0.49398(14) 0.18752(12) 0.29970(14) 0.0143(3) Uani 1 1 d . B .
C55 C 0.43803(15) 0.16701(12) -0.13557(14) 0.0161(4) Uani 1 1 d . . .
C56 C 0.43727(15) 0.10426(12) -0.20575(14) 0.0172(4) Uani 1 1 d . . .
H56 H 0.3796 0.0674 -0.2244 0.021 Uiso 1 1 calc R . .
C57 C 0.51930(15) 0.09507(12) -0.24835(14) 0.0174(4) Uani 1 1 d . . .
H57 H 0.5186 0.0519 -0.2954 0.021 Uiso 1 1 calc R . .
C58 C 0.60285(15) 0.14969(12) -0.22156(14) 0.0170(4) Uani 1 1 d . . .
C59 C 0.60405(15) 0.21374(13) -0.15364(15) 0.0190(4) Uani 1 1 d . . .
H59 H 0.6610 0.2513 -0.1366 0.023 Uiso 1 1 calc R . .
C60 C 0.52169(15) 0.22249(12) -0.11095(15) 0.0179(4) Uani 1 1 d . . .
H60 H 0.5221 0.2663 -0.0648 0.021 Uiso 1 1 calc R . .
C61 C 0.68823(14) 0.13832(13) -0.26627(15) 0.0187(4) Uani 1 1 d . . .
C62 C 0.12985(14) 0.18534(13) 0.12599(14) 0.0172(4) Uani 1 1 d . . .
C63 C 0.06998(15) 0.25539(14) 0.11073(15) 0.0221(4) Uani 1 1 d . B .
H63 H 0.0996 0.3054 0.0977 0.027 Uiso 1 1 calc R . .
C64 C -0.03331(17) 0.25317(16) 0.11425(18) 0.0311(5) Uani 1 1 d . . .
H64 H -0.0746 0.3014 0.1028 0.037 Uiso 1 1 calc R B .
C65 C -0.07609(16) 0.18031(17) 0.13456(17) 0.0328(6) Uani 1 1 d . B .
H65 H -0.1473 0.1784 0.1353 0.039 Uiso 1 1 calc R . .
C66 C -0.01567(17) 0.11068(15) 0.15363(16) 0.0285(5) Uani 1 1 d . . .
H66 H -0.0444 0.0614 0.1703 0.034 Uiso 1 1 calc R B .
C67 C 0.08722(15) 0.11244(13) 0.14853(15) 0.0210(4) Uani 1 1 d . B .
H67 H 0.1284 0.0642 0.1604 0.025 Uiso 1 1 calc R . .
C68 C 0.60925(14) 0.18088(12) 0.32763(14) 0.0152(4) Uani 1 1 d . . .
C69 C 0.67055(14) 0.22963(12) 0.28307(14) 0.0172(4) Uani 1 1 d . B .
H69 H 0.6378 0.2693 0.2325 0.021 Uiso 1 1 calc R . .
C70 C 0.77876(14) 0.22013(13) 0.31260(15) 0.0193(4) Uani 1 1 d . . .
H70 H 0.8203 0.2535 0.2825 0.023 Uiso 1 1 calc R B .
C71 C 0.82680(15) 0.16187(13) 0.38620(15) 0.0192(4) Uani 1 1 d . B .
C72 C 0.76710(15) 0.11428(13) 0.43277(15) 0.0197(4) Uani 1 1 d . . .
H72 H 0.8002 0.0752 0.4840 0.024 Uiso 1 1 calc R B .
C73 C 0.65911(14) 0.12431(12) 0.40389(15) 0.0181(4) Uani 1 1 d . B .
H73 H 0.6182 0.0924 0.4363 0.022 Uiso 1 1 calc R . .
C74 C 0.93951(16) 0.14924(14) 0.41261(15) 0.0228(4) Uani 1 1 d . . .
B2 B 0.45569(16) 0.19890(14) 0.09918(16) 0.0159(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
F1 B1 1.371(2) . ?
F2 B1 1.389(2) . ?
N1 C1 1.349(2) . ?
N1 C8 1.398(2) . ?
N1 B1 1.560(3) . ?
N2 C17 1.347(2) . ?
N2 C10 1.402(2) . ?
N2 B1 1.573(2) . ?
N3 C24 1.137(2) . ?
N4 C37 1.144(2) . ?
C1 C2 1.420(3) . ?
C1 C18 1.475(2) . ?
C2 C3 1.407(3) . ?
C2 C7 1.420(2) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C4 Cl1 1.680(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.435(3) . ?
C8 C9 1.392(2) . ?
C9 C10 1.386(2) . ?
C9 C25 1.498(2) . ?
C10 C11 1.430(2) . ?
C11 C16 1.410(2) . ?
C11 C12 1.412(2) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.407(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.426(2) . ?
C17 C31 1.473(2) . ?
C18 C23 1.398(3) . ?
C18 C19 1.401(3) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(3) . ?
C21 C24 1.448(2) . ?
C22 C23 1.389(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C30 1.387(3) . ?
C25 C26 1.388(3) . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.396(3) . ?
C31 C36 1.404(2) . ?
C32 C33 1.381(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.395(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.397(3) . ?
C34 C37 1.439(3) . ?
C35 C36 1.379(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
F3 B2 1.391(3) . ?
F4 B2 1.372(2) . ?
N5 C38 1.357(2) . ?
N5 C45 1.390(2) . ?
N5 B2 1.555(3) . ?
N6 C54 1.341(2) . ?
N6 C47 1.396(2) . ?
N6 B2 1.567(2) . ?
N7 C61 1.147(2) . ?
N8 C74 1.136(3) . ?
C38 C39 1.421(3) . ?
C38 C55 1.470(2) . ?
C39 C40 1.410(3) . ?
C39 C44 1.420(2) . ?
C40 C41 1.365(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.412(3) . ?
C41 Cl2 1.695(11) . ?
C41 H41 0.9500 . ?
C42 C43 1.375(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.409(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.428(3) . ?
C45 C46 1.398(2) . ?
C46 C47 1.385(3) . ?
C46 C62 1.490(2) . ?
C47 C48 1.437(2) . ?
C48 C49 1.405(2) . ?
C48 C53 1.415(2) . ?
C49 C50 1.373(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.405(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.375(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.402(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.430(2) . ?
C54 C68 1.469(2) . ?
C55 C56 1.397(3) . ?
C55 C60 1.400(3) . ?
C56 C57 1.383(2) . ?
C56 H56 0.9500 . ?
C57 C58 1.390(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.392(3) . ?
C58 C61 1.446(2) . ?
C59 C60 1.387(2) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
C62 C63 1.380(3) . ?
C62 C67 1.396(3) . ?
C63 C64 1.388(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.387(4) . ?
C64 H64 0.9500 . ?
C65 C66 1.378(4) . ?
C65 H65 0.9500 . ?
C66 C67 1.390(3) . ?
C66 H66 0.9500 . ?
C67 H67 0.9500 . ?
C68 C73 1.398(3) . ?
C68 C69 1.399(3) . ?
C69 C70 1.383(3) . ?
C69 H69 0.9500 . ?
C70 C71 1.390(3) . ?
C70 H70 0.9500 . ?
C71 C72 1.389(3) . ?
C71 C74 1.448(3) . ?
C72 C73 1.381(3) . ?
C72 H72 0.9500 . ?
C73 H73 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
C1 N1 C8 109.73(14) . . ?
C1 N1 B1 127.08(14) . . ?
C8 N1 B1 122.90(14) . . ?
C17 N2 C10 109.38(14) . . ?
C17 N2 B1 127.66(14) . . ?
C10 N2 B1 122.35(14) . . ?
N1 C1 C2 108.96(15) . . ?
N1 C1 C18 125.90(16) . . ?
C2 C1 C18 125.13(16) . . ?
C3 C2 C7 120.90(16) . . ?
C3 C2 C1 131.48(16) . . ?
C7 C2 C1 107.52(16) . . ?
C4 C3 C2 118.24(16) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.08(17) . . ?
C3 C4 Cl1 120.4(5) . . ?
C5 C4 Cl1 112.8(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.39(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 118.59(17) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C2 119.72(17) . . ?
C6 C7 C8 134.12(17) . . ?
C2 C7 C8 106.16(15) . . ?
C9 C8 N1 120.84(16) . . ?
C9 C8 C7 131.44(16) . . ?
N1 C8 C7 107.63(15) . . ?
C10 C9 C8 122.30(15) . . ?
C10 C9 C25 119.83(15) . . ?
C8 C9 C25 117.88(15) . . ?
C9 C10 N2 120.71(15) . . ?
C9 C10 C11 131.49(15) . . ?
N2 C10 C11 107.68(15) . . ?
C16 C11 C12 119.85(16) . . ?
C16 C11 C10 106.59(14) . . ?
C12 C11 C10 133.52(16) . . ?
C13 C12 C11 117.92(16) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 122.26(16) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 120.54(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 118.30(16) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 121.11(15) . . ?
C15 C16 C17 131.37(16) . . ?
C11 C16 C17 107.33(15) . . ?
N2 C17 C16 109.00(14) . . ?
N2 C17 C31 126.04(15) . . ?
C16 C17 C31 124.93(16) . . ?
C23 C18 C19 119.59(16) . . ?
C23 C18 C1 122.30(17) . . ?
C19 C18 C1 118.08(16) . . ?
C20 C19 C18 120.30(17) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.79(18) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.43(16) . . ?
C22 C21 C24 120.18(17) . . ?
C20 C21 C24 119.39(17) . . ?
C23 C22 C21 119.97(17) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 119.91(18) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
N3 C24 C21 179.3(2) . . ?
C30 C25 C26 119.73(16) . . ?
C30 C25 C9 119.27(16) . . ?
C26 C25 C9 120.94(16) . . ?
C27 C26 C25 120.16(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.83(19) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 120.18(17) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 120.13(19) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 119.90(18) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C31 C36 118.93(16) . . ?
C32 C31 C17 117.61(16) . . ?
C36 C31 C17 123.44(17) . . ?
C33 C32 C31 121.10(17) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 119.25(18) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C33 C34 C35 120.40(16) . . ?
C33 C34 C37 118.71(18) . . ?
C35 C34 C37 120.88(17) . . ?
C36 C35 C34 119.85(17) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C31 120.39(18) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
N4 C37 C34 177.9(2) . . ?
F1 B1 F2 111.67(14) . . ?
F1 B1 N1 110.69(16) . . ?
F2 B1 N1 108.11(16) . . ?
F1 B1 N2 110.81(16) . . ?
F2 B1 N2 107.85(15) . . ?
N1 B1 N2 107.55(13) . . ?
C38 N5 C45 109.72(15) . . ?
C38 N5 B2 126.60(15) . . ?
C45 N5 B2 123.53(15) . . ?
C54 N6 C47 109.85(14) . . ?
C54 N6 B2 126.97(15) . . ?
C47 N6 B2 122.71(15) . . ?
N5 C38 C39 108.64(15) . . ?
N5 C38 C55 125.73(17) . . ?
C39 C38 C55 125.60(16) . . ?
C40 C39 C44 121.18(17) . . ?
C40 C39 C38 131.29(17) . . ?
C44 C39 C38 107.37(16) . . ?
C41 C40 C39 118.07(17) . . ?
C41 C40 H40 121.0 . . ?
C39 C40 H40 121.0 . . ?
C40 C41 C42 121.11(18) . . ?
C40 C41 Cl2 120.9(4) . . ?
C42 C41 Cl2 118.0(4) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 H41 119.4 . . ?
C43 C42 C41 121.88(18) . . ?
C43 C42 H42 119.1 . . ?
C41 C42 H42 119.1 . . ?
C42 C43 C44 118.21(17) . . ?
C42 C43 H43 120.9 . . ?
C44 C43 H43 120.9 . . ?
C43 C44 C39 119.45(17) . . ?
C43 C44 C45 134.18(17) . . ?
C39 C44 C45 106.36(15) . . ?
N5 C45 C46 120.63(16) . . ?
N5 C45 C44 107.91(15) . . ?
C46 C45 C44 131.35(16) . . ?
C47 C46 C45 122.02(16) . . ?
C47 C46 C62 119.25(16) . . ?
C45 C46 C62 118.73(16) . . ?
C46 C47 N6 120.93(16) . . ?
C46 C47 C48 131.31(16) . . ?
N6 C47 C48 107.71(15) . . ?
C49 C48 C53 119.70(16) . . ?
C49 C48 C47 134.11(17) . . ?
C53 C48 C47 106.17(14) . . ?
C50 C49 C48 118.26(16) . . ?
C50 C49 H49 120.9 . . ?
C48 C49 H49 120.9 . . ?
C49 C50 C51 121.94(16) . . ?
C49 C50 H50 119.0 . . ?
C51 C50 H50 119.0 . . ?
C52 C51 C50 120.77(17) . . ?
C52 C51 H51 119.6 . . ?
C50 C51 H51 119.6 . . ?
C51 C52 C53 118.22(17) . . ?
C51 C52 H52 120.9 . . ?
C53 C52 H52 120.9 . . ?
C52 C53 C48 121.05(15) . . ?
C52 C53 C54 131.52(17) . . ?
C48 C53 C54 107.28(15) . . ?
N6 C54 C53 108.96(15) . . ?
N6 C54 C68 126.30(16) . . ?
C53 C54 C68 124.71(16) . . ?
C56 C55 C60 119.15(17) . . ?
C56 C55 C38 117.81(17) . . ?
C60 C55 C38 123.01(17) . . ?
C57 C56 C55 120.88(18) . . ?
C57 C56 H56 119.6 . . ?
C55 C56 H56 119.6 . . ?
C56 C57 C58 119.29(18) . . ?
C56 C57 H57 120.4 . . ?
C58 C57 H57 120.4 . . ?
C57 C58 C59 120.78(17) . . ?
C57 C58 C61 118.27(18) . . ?
C59 C58 C61 120.95(18) . . ?
C60 C59 C58 119.65(18) . . ?
C60 C59 H59 120.2 . . ?
C58 C59 H59 120.2 . . ?
C59 C60 C55 120.22(18) . . ?
C59 C60 H60 119.9 . . ?
C55 C60 H60 119.9 . . ?
N7 C61 C58 178.3(2) . . ?
C63 C62 C67 119.66(17) . . ?
C63 C62 C46 120.52(18) . . ?
C67 C62 C46 119.82(18) . . ?
C62 C63 C64 120.4(2) . . ?
C62 C63 H63 119.8 . . ?
C64 C63 H63 119.8 . . ?
C65 C64 C63 119.8(2) . . ?
C65 C64 H64 120.1 . . ?
C63 C64 H64 120.1 . . ?
C66 C65 C64 120.22(19) . . ?
C66 C65 H65 119.9 . . ?
C64 C65 H65 119.9 . . ?
C65 C66 C67 120.1(2) . . ?
C65 C66 H66 120.0 . . ?
C67 C66 H66 120.0 . . ?
C66 C67 C62 119.8(2) . . ?
C66 C67 H67 120.1 . . ?
C62 C67 H67 120.1 . . ?
C73 C68 C69 119.12(16) . . ?
C73 C68 C54 117.95(16) . . ?
C69 C68 C54 122.92(17) . . ?
C70 C69 C68 120.03(18) . . ?
C70 C69 H69 120.0 . . ?
C68 C69 H69 120.0 . . ?
C69 C70 C71 120.12(18) . . ?
C69 C70 H70 119.9 . . ?
C71 C70 H70 119.9 . . ?
C72 C71 C70 120.45(17) . . ?
C72 C71 C74 119.73(19) . . ?
C70 C71 C74 119.80(18) . . ?
C73 C72 C71 119.37(18) . . ?
C73 C72 H72 120.3 . . ?
C71 C72 H72 120.3 . . ?
C72 C73 C68 120.86(17) . . ?
C72 C73 H73 119.6 . . ?
C68 C73 H73 119.6 . . ?
N8 C74 C71 179.7(3) . . ?
N8 C74 Cl2 66.4(3) . 1_656 ?
C71 C74 Cl2 113.6(3) . 1_656 ?
F4 B2 F3 111.41(15) . . ?
F4 B2 N5 110.69(16) . . ?
F3 B2 N5 108.20(16) . . ?
F4 B2 N6 110.29(16) . . ?
F3 B2 N6 108.38(15) . . ?
N5 B2 N6 107.76(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -0.5(2) . . . . ?
B1 N1 C1 C2 173.47(17) . . . . ?
C8 N1 C1 C18 178.36(18) . . . . ?
B1 N1 C1 C18 -7.7(3) . . . . ?
N1 C1 C2 C3 -175.9(2) . . . . ?
C18 C1 C2 C3 5.2(3) . . . . ?
N1 C1 C2 C7 0.4(2) . . . . ?
C18 C1 C2 C7 -178.44(18) . . . . ?
C7 C2 C3 C4 3.1(3) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C3 C4 Cl1 -152.1(7) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
Cl1 C4 C5 C6 152.0(6) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C2 1.3(3) . . . . ?
C5 C6 C7 C8 -178.8(2) . . . . ?
C3 C2 C7 C6 -3.4(3) . . . . ?
C1 C2 C7 C6 179.82(18) . . . . ?
C3 C2 C7 C8 176.63(18) . . . . ?
C1 C2 C7 C8 -0.2(2) . . . . ?
C1 N1 C8 C9 -176.74(18) . . . . ?
B1 N1 C8 C9 9.0(3) . . . . ?
C1 N1 C8 C7 0.3(2) . . . . ?
B1 N1 C8 C7 -173.89(17) . . . . ?
C6 C7 C8 C9 -3.4(4) . . . . ?
C2 C7 C8 C9 176.6(2) . . . . ?
C6 C7 C8 N1 179.9(2) . . . . ?
C2 C7 C8 N1 -0.1(2) . . . . ?
N1 C8 C9 C10 2.1(3) . . . . ?
C7 C8 C9 C10 -174.2(2) . . . . ?
N1 C8 C9 C25 -178.11(16) . . . . ?
C7 C8 C9 C25 5.6(3) . . . . ?
C8 C9 C10 N2 -0.2(3) . . . . ?
C25 C9 C10 N2 -179.96(17) . . . . ?
C8 C9 C10 C11 175.3(2) . . . . ?
C25 C9 C10 C11 -4.4(3) . . . . ?
C17 N2 C10 C9 175.62(17) . . . . ?
B1 N2 C10 C9 -12.7(3) . . . . ?
C17 N2 C10 C11 -0.9(2) . . . . ?
B1 N2 C10 C11 170.79(17) . . . . ?
C9 C10 C11 C16 -174.8(2) . . . . ?
N2 C10 C11 C16 1.2(2) . . . . ?
C9 C10 C11 C12 7.5(4) . . . . ?
N2 C10 C11 C12 -176.5(2) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
C10 C11 C12 C13 176.2(2) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C14 C15 C16 C17 -175.0(2) . . . . ?
C12 C11 C16 C15 1.4(3) . . . . ?
C10 C11 C16 C15 -176.65(17) . . . . ?
C12 C11 C16 C17 177.03(17) . . . . ?
C10 C11 C16 C17 -1.1(2) . . . . ?
C10 N2 C17 C16 0.2(2) . . . . ?
B1 N2 C17 C16 -170.90(18) . . . . ?
C10 N2 C17 C31 -178.24(18) . . . . ?
B1 N2 C17 C31 10.7(3) . . . . ?
C15 C16 C17 N2 175.5(2) . . . . ?
C11 C16 C17 N2 0.6(2) . . . . ?
C15 C16 C17 C31 -6.0(3) . . . . ?
C11 C16 C17 C31 179.02(18) . . . . ?
N1 C1 C18 C23 49.7(3) . . . . ?
C2 C1 C18 C23 -131.7(2) . . . . ?
N1 C1 C18 C19 -132.4(2) . . . . ?
C2 C1 C18 C19 46.3(3) . . . . ?
C23 C18 C19 C20 -0.6(3) . . . . ?
C1 C18 C19 C20 -178.63(17) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C19 C20 C21 C24 179.57(17) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C24 C21 C22 C23 179.99(17) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C19 C18 C23 C22 0.2(3) . . . . ?
C1 C18 C23 C22 178.11(17) . . . . ?
C10 C9 C25 C30 -97.2(2) . . . . ?
C8 C9 C25 C30 83.0(2) . . . . ?
C10 C9 C25 C26 85.6(2) . . . . ?
C8 C9 C25 C26 -94.2(2) . . . . ?
C30 C25 C26 C27 -2.4(3) . . . . ?
C9 C25 C26 C27 174.76(18) . . . . ?
C25 C26 C27 C28 0.3(3) . . . . ?
C26 C27 C28 C29 2.1(3) . . . . ?
C27 C28 C29 C30 -2.4(3) . . . . ?
C26 C25 C30 C29 2.1(3) . . . . ?
C9 C25 C30 C29 -175.14(18) . . . . ?
C28 C29 C30 C25 0.3(3) . . . . ?
N2 C17 C31 C32 136.4(2) . . . . ?
C16 C17 C31 C32 -41.8(3) . . . . ?
N2 C17 C31 C36 -45.3(3) . . . . ?
C16 C17 C31 C36 136.5(2) . . . . ?
C36 C31 C32 C33 1.3(3) . . . . ?
C17 C31 C32 C33 179.62(17) . . . . ?
C31 C32 C33 C34 1.2(3) . . . . ?
C32 C33 C34 C35 -3.0(3) . . . . ?
C32 C33 C34 C37 176.11(18) . . . . ?
C33 C34 C35 C36 2.3(3) . . . . ?
C37 C34 C35 C36 -176.80(18) . . . . ?
C34 C35 C36 C31 0.2(3) . . . . ?
C32 C31 C36 C35 -2.0(3) . . . . ?
C17 C31 C36 C35 179.76(17) . . . . ?
C1 N1 B1 F1 46.9(3) . . . . ?
C8 N1 B1 F1 -139.88(16) . . . . ?
C1 N1 B1 F2 -75.7(2) . . . . ?
C8 N1 B1 F2 97.52(19) . . . . ?
C1 N1 B1 N2 168.12(17) . . . . ?
C8 N1 B1 N2 -18.7(2) . . . . ?
C17 N2 B1 F1 -48.3(3) . . . . ?
C10 N2 B1 F1 141.60(16) . . . . ?
C17 N2 B1 F2 74.2(2) . . . . ?
C10 N2 B1 F2 -95.89(19) . . . . ?
C17 N2 B1 N1 -169.45(17) . . . . ?
C10 N2 B1 N1 20.5(2) . . . . ?
C45 N5 C38 C39 0.7(2) . . . . ?
B2 N5 C38 C39 -175.04(18) . . . . ?
C45 N5 C38 C55 -177.47(18) . . . . ?
B2 N5 C38 C55 6.8(3) . . . . ?
N5 C38 C39 C40 175.1(2) . . . . ?
C55 C38 C39 C40 -6.8(3) . . . . ?
N5 C38 C39 C44 -0.4(2) . . . . ?
C55 C38 C39 C44 177.76(18) . . . . ?
C44 C39 C40 C41 -0.5(3) . . . . ?
C38 C39 C40 C41 -175.4(2) . . . . ?
C39 C40 C41 C42 -1.6(3) . . . . ?
C39 C40 C41 Cl2 177.5(5) . . . . ?
C40 C41 C42 C43 1.5(3) . . . . ?
Cl2 C41 C42 C43 -177.7(5) . . . . ?
C41 C42 C43 C44 0.9(3) . . . . ?
C42 C43 C44 C39 -3.0(3) . . . . ?
C42 C43 C44 C45 175.5(2) . . . . ?
C40 C39 C44 C43 2.9(3) . . . . ?
C38 C39 C44 C43 178.88(18) . . . . ?
C40 C39 C44 C45 -176.03(18) . . . . ?
C38 C39 C44 C45 0.0(2) . . . . ?
C38 N5 C45 C46 176.04(18) . . . . ?
B2 N5 C45 C46 -8.1(3) . . . . ?
C38 N5 C45 C44 -0.7(2) . . . . ?
B2 N5 C45 C44 175.18(18) . . . . ?
C43 C44 C45 N5 -178.3(2) . . . . ?
C39 C44 C45 N5 0.4(2) . . . . ?
C43 C44 C45 C46 5.5(4) . . . . ?
C39 C44 C45 C46 -175.8(2) . . . . ?
N5 C45 C46 C47 -0.7(3) . . . . ?
C44 C45 C46 C47 175.1(2) . . . . ?
N5 C45 C46 C62 -179.37(18) . . . . ?
C44 C45 C46 C62 -3.5(3) . . . . ?
C45 C46 C47 N6 -1.1(3) . . . . ?
C62 C46 C47 N6 177.53(17) . . . . ?
C45 C46 C47 C48 -178.1(2) . . . . ?
C62 C46 C47 C48 0.5(3) . . . . ?
C54 N6 C47 C46 -175.76(18) . . . . ?
B2 N6 C47 C46 11.6(3) . . . . ?
C54 N6 C47 C48 1.9(2) . . . . ?
B2 N6 C47 C48 -170.75(17) . . . . ?
C46 C47 C48 C49 -5.4(4) . . . . ?
N6 C47 C48 C49 177.3(2) . . . . ?
C46 C47 C48 C53 175.9(2) . . . . ?
N6 C47 C48 C53 -1.4(2) . . . . ?
C53 C48 C49 C50 1.1(3) . . . . ?
C47 C48 C49 C50 -177.5(2) . . . . ?
C48 C49 C50 C51 1.0(3) . . . . ?
C49 C50 C51 C52 -2.1(3) . . . . ?
C50 C51 C52 C53 0.8(3) . . . . ?
C51 C52 C53 C48 1.3(3) . . . . ?
C51 C52 C53 C54 176.4(2) . . . . ?
C49 C48 C53 C52 -2.3(3) . . . . ?
C47 C48 C53 C52 176.63(18) . . . . ?
C49 C48 C53 C54 -178.48(17) . . . . ?
C47 C48 C53 C54 0.5(2) . . . . ?
C47 N6 C54 C53 -1.6(2) . . . . ?
B2 N6 C54 C53 170.64(18) . . . . ?
C47 N6 C54 C68 176.28(18) . . . . ?
B2 N6 C54 C68 -11.5(3) . . . . ?
C52 C53 C54 N6 -174.9(2) . . . . ?
C48 C53 C54 N6 0.7(2) . . . . ?
C52 C53 C54 C68 7.1(3) . . . . ?
C48 C53 C54 C68 -177.23(18) . . . . ?
N5 C38 C55 C56 132.5(2) . . . . ?
C39 C38 C55 C56 -45.3(3) . . . . ?
N5 C38 C55 C60 -49.6(3) . . . . ?
C39 C38 C55 C60 132.6(2) . . . . ?
C60 C55 C56 C57 2.0(3) . . . . ?
C38 C55 C56 C57 179.93(17) . . . . ?
C55 C56 C57 C58 -0.7(3) . . . . ?
C56 C57 C58 C59 -0.8(3) . . . . ?
C56 C57 C58 C61 179.36(17) . . . . ?
C57 C58 C59 C60 1.0(3) . . . . ?
C61 C58 C59 C60 -179.18(18) . . . . ?
C58 C59 C60 C55 0.3(3) . . . . ?
C56 C55 C60 C59 -1.8(3) . . . . ?
C38 C55 C60 C59 -179.63(18) . . . . ?
C47 C46 C62 C63 99.6(2) . . . . ?
C45 C46 C62 C63 -81.7(2) . . . . ?
C47 C46 C62 C67 -80.9(2) . . . . ?
C45 C46 C62 C67 97.8(2) . . . . ?
C67 C62 C63 C64 -2.2(3) . . . . ?
C46 C62 C63 C64 177.33(18) . . . . ?
C62 C63 C64 C65 0.9(3) . . . . ?
C63 C64 C65 C66 1.5(3) . . . . ?
C64 C65 C66 C67 -2.5(3) . . . . ?
C65 C66 C67 C62 1.2(3) . . . . ?
C63 C62 C67 C66 1.1(3) . . . . ?
C46 C62 C67 C66 -178.37(17) . . . . ?
N6 C54 C68 C73 -132.4(2) . . . . ?
C53 C54 C68 C73 45.2(3) . . . . ?
N6 C54 C68 C69 49.1(3) . . . . ?
C53 C54 C68 C69 -133.4(2) . . . . ?
C73 C68 C69 C70 1.6(3) . . . . ?
C54 C68 C69 C70 -179.81(17) . . . . ?
C68 C69 C70 C71 0.3(3) . . . . ?
C69 C70 C71 C72 -1.8(3) . . . . ?
C69 C70 C71 C74 176.66(18) . . . . ?
C70 C71 C72 C73 1.2(3) . . . . ?
C74 C71 C72 C73 -177.24(18) . . . . ?
C71 C72 C73 C68 0.8(3) . . . . ?
C69 C68 C73 C72 -2.2(3) . . . . ?
C54 C68 C73 C72 179.15(18) . . . . ?
C38 N5 B2 F4 -48.3(3) . . . . ?
C45 N5 B2 F4 136.54(18) . . . . ?
C38 N5 B2 F3 74.0(2) . . . . ?
C45 N5 B2 F3 -101.13(19) . . . . ?
C38 N5 B2 N6 -168.98(18) . . . . ?
C45 N5 B2 N6 15.9(2) . . . . ?
C54 N6 B2 F4 50.2(3) . . . . ?
C47 N6 B2 F4 -138.47(17) . . . . ?
C54 N6 B2 F3 -72.0(2) . . . . ?
C47 N6 B2 F3 99.32(19) . . . . ?
C54 N6 B2 N5 171.15(17) . . . . ?
C47 N6 B2 N5 -17.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
# END OF CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
