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

#edited by ppcif program, please check edits
data_m-10
_audit_creation_method                  SHELXL-2014/6
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_melting_point                 ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C32 H24 B2 F4 N8'
_chemical_formula_weight                618.21
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'
 
_space_group_crystal_system             monoclinic
_space_group_IT_number                  15
_space_group_name_H-M_alt               'C 2/c'
_space_group_name_Hall                  '-C 2yc'
_shelx_space_group_comment 
 
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
  _space_group_symop_operation_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                          18.424(7)
_cell_length_b                          17.935(7)
_cell_length_c                          18.574(6)
_cell_angle_alpha                       90
_cell_angle_beta                        110.646(10)
_cell_angle_gamma                       90
_cell_volume                            5743(4)
_cell_formula_units_Z                   8
_cell_measurement_temperature           110
_cell_measurement_reflns_used           7296
_cell_measurement_theta_min             2.24
_cell_measurement_theta_max             26.59
_exptl_crystal_description              Plate
_exptl_crystal_colour                   red
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           ?
_exptl_crystal_density_diffrn           1.430
_exptl_crystal_F_000                    2544
_exptl_transmission_factor_min          ?
_exptl_transmission_factor_max          ?
_exptl_crystal_size_max                 0.528
_exptl_crystal_size_mid                 0.120
_exptl_crystal_size_min                 0.080
_exptl_absorpt_coefficient_mu           0.106
_shelx_estimated_absorpt_T_min          0.946
_shelx_estimated_absorpt_T_max          0.992
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_correction_T_min         0.6765
_exptl_absorpt_correction_T_max         0.7457
_exptl_absorpt_process_details          SADABS
_exptl_absorpt_special_details          ?
_diffrn_ambient_temperature             110
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_source                          'sealed tube'
_diffrn_measurement_device_type         'Bruker Kappa Axis Apex2'
_diffrn_measurement_method              'phi and omega scans'
_diffrn_detector_area_resol_mean        ?
_diffrn_reflns_number                   52269
_diffrn_reflns_av_unetI/netI            0.0608
_diffrn_reflns_av_R_equivalents         0.0708
_diffrn_reflns_limit_h_min              -24
_diffrn_reflns_limit_h_max              24
_diffrn_reflns_limit_k_min              -23
_diffrn_reflns_limit_k_max              23
_diffrn_reflns_limit_l_min              -24
_diffrn_reflns_limit_l_max              24
_diffrn_reflns_theta_min                2.344
_diffrn_reflns_theta_max                28.473
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full    0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total                    7169
_reflns_number_gt                       4497
_reflns_threshold_expression            'I > 2σ(I)'
_reflns_Friedel_coverage                0.000
_reflns_Friedel_fraction_max            .
_reflns_Friedel_fraction_full           .
_reflns_special_details 
 
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection              Apex2
_computing_cell_refinement              SAINT
_computing_data_reduction               SAINT
_computing_structure_solution           SHELXT
_computing_structure_refinement         SHELXL-2014
_computing_molecular_graphics           NRCVAX
_computing_publication_material         cif2tables.py
_refine_special_details                 ?
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
 'w=1/[σ²(Fo²)+(0.0446P)²+1.6682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            dual
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          difmap
_refine_ls_hydrogen_treatment           refall
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              .
_refine_ls_number_reflns                7169
_refine_ls_number_parameters            511
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0932
_refine_ls_R_factor_gt                  0.0460
_refine_ls_wR_factor_ref                0.1079
_refine_ls_wR_factor_gt                 0.0912
_refine_ls_goodness_of_fit_ref          1.018
_refine_ls_restrained_S_all             1.018
_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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
   N1  N  0.40050(8)  0.70780(8)  0.41386(8)  0.0193(3)  Uani  1  1  d  .  .  .
   .
   .
   N2  N  0.38064(8)  0.71188(8)  0.47447(8)  0.0207(3)  Uani  1  1  d  .  .  .
   .
   .
   N3  N  0.39525(8)  0.57066(8)  0.41997(8)  0.0202(3)  Uani  1  1  d  .  .  .
   .
   .
   N4  N  0.37298(8)  0.57890(8)  0.47901(8)  0.0210(3)  Uani  1  1  d  .  .  .
   .
   .
   C1  C  0.36200(9)  0.64780(9)  0.50107(9)  0.0201(4)  Uani  1  1  d  .  .  .
   .
   .
   B1  B  0.39533(12)  0.63594(11)  0.36510(11)  0.0223(4)  Uani  1  1  d  .  .
   .
   .
   .
   F1  F  0.45880(6)  0.63250(6)  0.34286(6)  0.0321(3)  Uani  1  1  d  .  .  .
   .
   .
   F2  F  0.32676(6)  0.63480(6)  0.30280(5)  0.0317(3)  Uani  1  1  d  .  .  .
   .
   .
   C2  C  0.42644(9)  0.77711(9)  0.39282(9)  0.0190(4)  Uani  1  1  d  .  .  .
   .
   .
   C3  C  0.41053(10)  0.79190(10)  0.31496(10)  0.0219(4)  Uani  1  1  d  .  .
   .
   .
   .
   H3  H  0.3839(10)  0.7560(10)  0.2769(10)  0.022(5)  Uiso  1  1  d  .  .  .
   .
   .
   C4  C  0.43281(10)  0.85971(10)  0.29427(10)  0.0233(4)  Uani  1  1  d  .  .
   .
   .
   .
   H4  H  0.4215(10)  0.8711(10)  0.2416(11)  0.032(5)  Uiso  1  1  d  .  .  .
   .
   .
   C5  C  0.47083(10)  0.91166(10)  0.34919(10)  0.0250(4)  Uani  1  1  d  .  .
   .
   .
   .
   H5  H  0.4856(10)  0.9589(10)  0.3326(10)  0.025(5)  Uiso  1  1  d  .  .  .
   .
   .
   C6  C  0.48732(11)  0.89623(10)  0.42656(11)  0.0250(4)  Uani  1  1  d  .  .
   .
   .
   .
   H6  H  0.5147(10)  0.9308(10)  0.4650(10)  0.021(5)  Uiso  1  1  d  .  .  .
   .
   .
   C7  C  0.46526(10)  0.82866(10)  0.44875(10)  0.0221(4)  Uani  1  1  d  .  .
   .
   .
   .
   H7  H  0.4742(9)  0.8153(9)  0.4987(10)  0.018(4)  Uiso  1  1  d  .  .  .  .
   .
   C8  C  0.41268(9)  0.49503(9)  0.40659(10)  0.0212(4)  Uani  1  1  d  .  .
   .
   .
   .
   C9  C  0.41898(10)  0.47603(11)  0.33620(10)  0.0257(4)  Uani  1  1  d  .  .
   .
   .
   .
   H9  H  0.4103(10)  0.5146(10)  0.2966(10)  0.024(5)  Uiso  1  1  d  .  .  .
   .
   .
   C10  C  0.43445(11)  0.40272(11)  0.32289(11)  0.0301(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H10  H  0.4381(10)  0.3892(10)  0.2742(11)  0.029(5)  Uiso  1  1  d  .  .  .
   .
   .
   C11  C  0.44310(11)  0.34869(11)  0.37821(11)  0.0295(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H11  H  0.4549(11)  0.2983(12)  0.3690(12)  0.042(6)  Uiso  1  1  d  .  .  .
   .
   .
   C12  C  0.43618(10)  0.36762(11)  0.44756(11)  0.0270(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H12  H  0.4418(11)  0.3296(11)  0.4875(11)  0.039(6)  Uiso  1  1  d  .  .  .
   .
   .
   C13  C  0.42121(10)  0.44047(10)  0.46240(10)  0.0239(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H13  H  0.4163(9)  0.4520(9)  0.5115(10)  0.021(4)  Uiso  1  1  d  .  .  .
   .
   .
   C14  C  0.33056(10)  0.65304(9)  0.56396(9)  0.0207(4)  Uani  1  1  d  .  .
   .
   .
   .
   C15  C  0.30669(10)  0.58788(10)  0.58954(10)  0.0213(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H15  H  0.3112(10)  0.5399(10)  0.5669(10)  0.025(5)  Uiso  1  1  d  .  .  .
   .
   .
   C16  C  0.27326(9)  0.58952(9)  0.64610(9)  0.0195(4)  Uani  1  1  d  .  .
   .
   .
   .
   C17  C  0.26590(10)  0.65771(10)  0.67887(10)  0.0227(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H17  H  0.2451(10)  0.6608(9)  0.7206(10)  0.027(5)  Uiso  1  1  d  .  .  .
   .
   .
   C18  C  0.29041(10)  0.72241(11)  0.65404(10)  0.0251(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H18  H  0.2848(11)  0.7685(11)  0.6751(11)  0.031(5)  Uiso  1  1  d  .  .  .
   .
   .
   C19  C  0.32158(10)  0.72097(10)  0.59617(10)  0.0239(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H19  H  0.3362(10)  0.7647(10)  0.5772(10)  0.027(5)  Uiso  1  1  d  .  .  .
   .
   .
   N5  N  0.22861(8)  0.39434(8)  0.64384(7)  0.0190(3)  Uani  1  1  d  .  .  .
   .
   .
   N6  N  0.26220(8)  0.45659(8)  0.63633(7)  0.0200(3)  Uani  1  1  d  .  .  .
   .
   .
   N7  N  0.17824(8)  0.45862(8)  0.73098(7)  0.0191(3)  Uani  1  1  d  .  .  .
   .
   .
   N8  N  0.21309(8)  0.51975(8)  0.72157(8)  0.0204(3)  Uani  1  1  d  .  .  .
   .
   .
   C20  C  0.24451(9)  0.51884(9)  0.66665(9)  0.0191(4)  Uani  1  1  d  .  .
   .
   .
   .
   B2  B  0.15538(11)  0.39781(11)  0.66709(11)  0.0218(4)  Uani  1  1  d  .  .
   .
   .
   .
   F3  F  0.13987(6)  0.33072(6)  0.69285(6)  0.0321(3)  Uani  1  1  d  .  .  .
   .
   .
   F4  F  0.09362(6)  0.42329(6)  0.60476(6)  0.0312(3)  Uani  1  1  d  .  .  .
   .
   .
   C21  C  0.26471(10)  0.32846(9)  0.62847(9)  0.0193(4)  Uani  1  1  d  .  .
   .
   .
   .
   C22  C  0.22132(11)  0.26425(10)  0.60361(10)  0.0233(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H22  H  0.1684(11)  0.2644(9)  0.5975(10)  0.023(5)  Uiso  1  1  d  .  .  .
   .
   .
   C23  C  0.25618(11)  0.20170(11)  0.58670(11)  0.0268(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H23  H  0.2267(11)  0.1583(11)  0.5697(11)  0.033(5)  Uiso  1  1  d  .  .  .
   .
   .
   C24  C  0.33334(11)  0.20308(10)  0.59383(10)  0.0260(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H24  H  0.3580(10)  0.1590(10)  0.5812(10)  0.029(5)  Uiso  1  1  d  .  .  .
   .
   .
   C25  C  0.37648(11)  0.26736(10)  0.61899(10)  0.0259(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H25  H  0.4295(12)  0.2682(11)  0.6253(11)  0.037(6)  Uiso  1  1  d  .  .  .
   .
   .
   C26  C  0.34281(10)  0.33034(10)  0.63653(10)  0.0223(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H26  H  0.3729(10)  0.3756(10)  0.6551(10)  0.029(5)  Uiso  1  1  d  .  .  .
   .
   .
   C27  C  0.16245(10)  0.45678(9)  0.80114(9)  0.0200(4)  Uani  1  1  d  .  .
   .
   .
   .
   C28  C  0.10375(10)  0.41139(10)  0.80713(11)  0.0247(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H28  H  0.0749(10)  0.3830(10)  0.7651(10)  0.028(5)  Uiso  1  1  d  .  .  .
   .
   .
   C29  C  0.08820(11)  0.41124(11)  0.87499(11)  0.0283(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H29  H  0.0461(12)  0.3797(12)  0.8774(12)  0.046(6)  Uiso  1  1  d  .  .  .
   .
   .
   C30  C  0.13067(11)  0.45550(11)  0.93625(11)  0.0287(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H30  H  0.1213(10)  0.4557(10)  0.9847(11)  0.030(5)  Uiso  1  1  d  .  .  .
   .
   .
   C31  C  0.18858(11)  0.50121(11)  0.92965(10)  0.0267(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H31  H  0.2196(11)  0.5305(11)  0.9721(11)  0.035(5)  Uiso  1  1  d  .  .  .
   .
   .
   C32  C  0.20502(10)  0.50183(10)  0.86252(10)  0.0227(4)  Uani  1  1  d  .
   .
   .
   .
   .
   H32  H  0.2469(10)  0.5323(10)  0.8585(10)  0.025(5)  Uiso  1  1  d  .  .  .
   .
   .
 
 
_geom_special_details 
 
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
   N1  N2  1.3026(18)  .  ?
   N1  C2  1.435(2)  .  ?
   N1  B1  1.559(2)  .  ?
   N2  C1  1.343(2)  .  ?
   N3  N4  1.3077(18)  .  ?
   N3  C8  1.436(2)  .  ?
   N3  B1  1.553(2)  .  ?
   N4  C1  1.340(2)  .  ?
   C1  C14  1.478(2)  .  ?
   B1  F1  1.372(2)  .  ?
   B1  F2  1.380(2)  .  ?
   C2  C7  1.386(2)  .  ?
   C2  C3  1.396(2)  .  ?
   C3  C4  1.381(2)  .  ?
   C3  H3  0.954(18)  .  ?
   C4  C5  1.377(3)  .  ?
   C4  H4  0.949(19)  .  ?
   C5  C6  1.388(3)  .  ?
   C5  H5  0.974(18)  .  ?
   C6  C7  1.386(2)  .  ?
   C6  H6  0.945(18)  .  ?
   C7  H7  0.915(17)  .  ?
   C8  C13  1.394(2)  .  ?
   C8  C9  1.395(2)  .  ?
   C9  C10  1.386(3)  .  ?
   C9  H9  0.981(18)  .  ?
   C10  C11  1.380(3)  .  ?
   C10  H10  0.962(18)  .  ?
   C11  C12  1.381(3)  .  ?
   C11  H11  0.96(2)  .  ?
   C12  C13  1.383(3)  .  ?
   C12  H12  0.99(2)  .  ?
   C13  H13  0.969(17)  .  ?
   C14  C15  1.390(2)  .  ?
   C14  C19  1.393(2)  .  ?
   C15  C16  1.393(2)  .  ?
   C15  H15  0.975(18)  .  ?
   C16  C17  1.394(2)  .  ?
   C16  C20  1.475(2)  .  ?
   C17  C18  1.382(2)  .  ?
   C17  H17  0.979(17)  .  ?
   C18  C19  1.386(2)  .  ?
   C18  H18  0.936(19)  .  ?
   C19  H19  0.938(18)  .  ?
   N5  N6  1.3078(19)  .  ?
   N5  C21  1.433(2)  .  ?
   N5  B2  1.556(2)  .  ?
   N6  C20  1.341(2)  .  ?
   N7  N8  1.3130(19)  .  ?
   N7  C27  1.432(2)  .  ?
   N7  B2  1.556(2)  .  ?
   N8  C20  1.339(2)  .  ?
   B2  F3  1.362(2)  .  ?
   B2  F4  1.384(2)  .  ?
   C21  C22  1.385(2)  .  ?
   C21  C26  1.394(2)  .  ?
   C22  C23  1.383(3)  .  ?
   C22  H22  0.940(18)  .  ?
   C23  C24  1.381(3)  .  ?
   C23  H23  0.938(19)  .  ?
   C24  C25  1.385(3)  .  ?
   C24  H24  0.981(18)  .  ?
   C25  C26  1.382(3)  .  ?
   C25  H25  0.94(2)  .  ?
   C26  H26  0.975(19)  .  ?
   C27  C28  1.389(2)  .  ?
   C27  C32  1.392(2)  .  ?
   C28  C29  1.388(2)  .  ?
   C28  H28  0.927(19)  .  ?
   C29  C30  1.382(3)  .  ?
   C29  H29  0.97(2)  .  ?
   C30  C31  1.385(3)  .  ?
   C30  H30  0.974(18)  .  ?
   C31  C32  1.383(2)  .  ?
   C31  H31  0.95(2)  .  ?
   C32  H32  0.971(18)  .  ?
 
loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
   N2  N1  C2  114.13(13)  .  .  ?
   N2  N1  B1  124.77(13)  .  .  ?
   C2  N1  B1  121.08(13)  .  .  ?
   N1  N2  C1  117.15(14)  .  .  ?
   N4  N3  C8  114.04(13)  .  .  ?
   N4  N3  B1  122.58(14)  .  .  ?
   C8  N3  B1  123.15(13)  .  .  ?
   N3  N4  C1  119.12(14)  .  .  ?
   N4  C1  N2  126.24(15)  .  .  ?
   N4  C1  C14  116.35(14)  .  .  ?
   N2  C1  C14  117.30(15)  .  .  ?
   F1  B1  F2  111.86(15)  .  .  ?
   F1  B1  N3  111.21(15)  .  .  ?
   F2  B1  N3  109.07(14)  .  .  ?
   F1  B1  N1  109.16(14)  .  .  ?
   F2  B1  N1  110.47(15)  .  .  ?
   N3  B1  N1  104.84(13)  .  .  ?
   C7  C2  C3  120.92(16)  .  .  ?
   C7  C2  N1  120.48(15)  .  .  ?
   C3  C2  N1  118.58(15)  .  .  ?
   C4  C3  C2  118.77(17)  .  .  ?
   C4  C3  H3  120.9(10)  .  .  ?
   C2  C3  H3  120.3(10)  .  .  ?
   C5  C4  C3  120.89(17)  .  .  ?
   C5  C4  H4  119.2(11)  .  .  ?
   C3  C4  H4  119.9(11)  .  .  ?
   C4  C5  C6  120.05(17)  .  .  ?
   C4  C5  H5  118.7(10)  .  .  ?
   C6  C5  H5  121.2(10)  .  .  ?
   C7  C6  C5  120.13(17)  .  .  ?
   C7  C6  H6  118.8(10)  .  .  ?
   C5  C6  H6  121.0(10)  .  .  ?
   C2  C7  C6  119.23(16)  .  .  ?
   C2  C7  H7  116.4(11)  .  .  ?
   C6  C7  H7  124.3(11)  .  .  ?
   C13  C8  C9  120.05(17)  .  .  ?
   C13  C8  N3  120.55(15)  .  .  ?
   C9  C8  N3  119.38(15)  .  .  ?
   C10  C9  C8  119.29(18)  .  .  ?
   C10  C9  H9  121.6(10)  .  .  ?
   C8  C9  H9  119.0(10)  .  .  ?
   C11  C10  C9  120.69(18)  .  .  ?
   C11  C10  H10  119.7(11)  .  .  ?
   C9  C10  H10  119.6(11)  .  .  ?
   C10  C11  C12  119.84(18)  .  .  ?
   C10  C11  H11  120.2(12)  .  .  ?
   C12  C11  H11  120.0(12)  .  .  ?
   C11  C12  C13  120.58(18)  .  .  ?
   C11  C12  H12  120.7(11)  .  .  ?
   C13  C12  H12  118.7(11)  .  .  ?
   C12  C13  C8  119.56(17)  .  .  ?
   C12  C13  H13  118.7(10)  .  .  ?
   C8  C13  H13  121.7(10)  .  .  ?
   C15  C14  C19  119.26(15)  .  .  ?
   C15  C14  C1  118.41(15)  .  .  ?
   C19  C14  C1  122.28(15)  .  .  ?
   C14  C15  C16  121.15(16)  .  .  ?
   C14  C15  H15  120.6(10)  .  .  ?
   C16  C15  H15  118.2(10)  .  .  ?
   C15  C16  C17  119.01(15)  .  .  ?
   C15  C16  C20  118.14(15)  .  .  ?
   C17  C16  C20  122.82(14)  .  .  ?
   C18  C17  C16  119.82(16)  .  .  ?
   C18  C17  H17  118.8(10)  .  .  ?
   C16  C17  H17  121.3(10)  .  .  ?
   C17  C18  C19  121.11(17)  .  .  ?
   C17  C18  H18  120.3(11)  .  .  ?
   C19  C18  H18  118.6(11)  .  .  ?
   C18  C19  C14  119.60(17)  .  .  ?
   C18  C19  H19  121.8(11)  .  .  ?
   C14  C19  H19  118.6(11)  .  .  ?
   N6  N5  C21  114.35(13)  .  .  ?
   N6  N5  B2  118.99(14)  .  .  ?
   C21  N5  B2  126.66(14)  .  .  ?
   N5  N6  C20  118.14(13)  .  .  ?
   N8  N7  C27  113.96(13)  .  .  ?
   N8  N7  B2  119.82(13)  .  .  ?
   C27  N7  B2  126.18(13)  .  .  ?
   N7  N8  C20  117.02(14)  .  .  ?
   N8  C20  N6  124.37(15)  .  .  ?
   N8  C20  C16  118.54(15)  .  .  ?
   N6  C20  C16  116.36(14)  .  .  ?
   F3  B2  F4  111.91(15)  .  .  ?
   F3  B2  N5  111.84(15)  .  .  ?
   F4  B2  N5  108.59(14)  .  .  ?
   F3  B2  N7  112.65(14)  .  .  ?
   F4  B2  N7  109.15(15)  .  .  ?
   N5  B2  N7  102.22(13)  .  .  ?
   C22  C21  C26  120.57(16)  .  .  ?
   C22  C21  N5  119.87(15)  .  .  ?
   C26  C21  N5  119.53(15)  .  .  ?
   C23  C22  C21  119.38(17)  .  .  ?
   C23  C22  H22  121.3(11)  .  .  ?
   C21  C22  H22  119.3(10)  .  .  ?
   C24  C23  C22  120.57(18)  .  .  ?
   C24  C23  H23  120.1(12)  .  .  ?
   C22  C23  H23  119.3(12)  .  .  ?
   C23  C24  C25  119.77(18)  .  .  ?
   C23  C24  H24  120.8(11)  .  .  ?
   C25  C24  H24  119.5(10)  .  .  ?
   C26  C25  C24  120.54(18)  .  .  ?
   C26  C25  H25  119.3(12)  .  .  ?
   C24  C25  H25  120.2(12)  .  .  ?
   C25  C26  C21  119.16(17)  .  .  ?
   C25  C26  H26  121.2(10)  .  .  ?
   C21  C26  H26  119.6(10)  .  .  ?
   C28  C27  C32  120.29(15)  .  .  ?
   C28  C27  N7  120.00(15)  .  .  ?
   C32  C27  N7  119.69(15)  .  .  ?
   C29  C28  C27  119.33(18)  .  .  ?
   C29  C28  H28  121.5(11)  .  .  ?
   C27  C28  H28  119.1(11)  .  .  ?
   C30  C29  C28  120.57(18)  .  .  ?
   C30  C29  H29  121.6(12)  .  .  ?
   C28  C29  H29  117.8(12)  .  .  ?
   C29  C30  C31  119.82(17)  .  .  ?
   C29  C30  H30  122.0(11)  .  .  ?
   C31  C30  H30  118.2(11)  .  .  ?
   C32  C31  C30  120.33(18)  .  .  ?
   C32  C31  H31  119.0(12)  .  .  ?
   C30  C31  H31  120.6(12)  .  .  ?
   C31  C32  C27  119.64(17)  .  .  ?
   C31  C32  H32  120.4(10)  .  .  ?
   C27  C32  H32  119.9(10)  .  .  ?
 
loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
   C2  N1  N2  C1  -174.58(14)  .  .  .  .  ?
   B1  N1  N2  C1  7.1(2)  .  .  .  .  ?
   C8  N3  N4  C1  174.00(14)  .  .  .  .  ?
   B1  N3  N4  C1  -11.4(2)  .  .  .  .  ?
   N3  N4  C1  N2  -8.8(3)  .  .  .  .  ?
   N3  N4  C1  C14  175.03(14)  .  .  .  .  ?
   N1  N2  C1  N4  10.9(2)  .  .  .  .  ?
   N1  N2  C1  C14  -172.92(14)  .  .  .  .  ?
   N4  N3  B1  F1  141.57(15)  .  .  .  .  ?
   C8  N3  B1  F1  -44.3(2)  .  .  .  .  ?
   N4  N3  B1  F2  -94.59(18)  .  .  .  .  ?
   C8  N3  B1  F2  79.57(19)  .  .  .  .  ?
   N4  N3  B1  N1  23.7(2)  .  .  .  .  ?
   C8  N3  B1  N1  -162.12(14)  .  .  .  .  ?
   N2  N1  B1  F1  -141.16(15)  .  .  .  .  ?
   C2  N1  B1  F1  40.7(2)  .  .  .  .  ?
   N2  N1  B1  F2  95.43(18)  .  .  .  .  ?
   C2  N1  B1  F2  -82.72(18)  .  .  .  .  ?
   N2  N1  B1  N3  -21.9(2)  .  .  .  .  ?
   C2  N1  B1  N3  159.91(14)  .  .  .  .  ?
   N2  N1  C2  C7  32.4(2)  .  .  .  .  ?
   B1  N1  C2  C7  -149.31(16)  .  .  .  .  ?
   N2  N1  C2  C3  -146.55(15)  .  .  .  .  ?
   B1  N1  C2  C3  31.8(2)  .  .  .  .  ?
   C7  C2  C3  C4  -1.3(2)  .  .  .  .  ?
   N1  C2  C3  C4  177.58(15)  .  .  .  .  ?
   C2  C3  C4  C5  0.8(3)  .  .  .  .  ?
   C3  C4  C5  C6  0.0(3)  .  .  .  .  ?
   C4  C5  C6  C7  -0.3(3)  .  .  .  .  ?
   C3  C2  C7  C6  1.1(3)  .  .  .  .  ?
   N1  C2  C7  C6  -177.81(15)  .  .  .  .  ?
   C5  C6  C7  C2  -0.3(3)  .  .  .  .  ?
   N4  N3  C8  C13  -13.4(2)  .  .  .  .  ?
   B1  N3  C8  C13  171.96(15)  .  .  .  .  ?
   N4  N3  C8  C9  164.85(15)  .  .  .  .  ?
   B1  N3  C8  C9  -9.8(2)  .  .  .  .  ?
   C13  C8  C9  C10  -0.6(3)  .  .  .  .  ?
   N3  C8  C9  C10  -178.86(16)  .  .  .  .  ?
   C8  C9  C10  C11  0.4(3)  .  .  .  .  ?
   C9  C10  C11  C12  0.1(3)  .  .  .  .  ?
   C10  C11  C12  C13  -0.5(3)  .  .  .  .  ?
   C11  C12  C13  C8  0.3(3)  .  .  .  .  ?
   C9  C8  C13  C12  0.2(3)  .  .  .  .  ?
   N3  C8  C13  C12  178.48(15)  .  .  .  .  ?
   N4  C1  C14  C15  -7.1(2)  .  .  .  .  ?
   N2  C1  C14  C15  176.40(15)  .  .  .  .  ?
   N4  C1  C14  C19  175.29(16)  .  .  .  .  ?
   N2  C1  C14  C19  -1.2(2)  .  .  .  .  ?
   C19  C14  C15  C16  0.7(3)  .  .  .  .  ?
   C1  C14  C15  C16  -177.00(16)  .  .  .  .  ?
   C14  C15  C16  C17  -1.9(3)  .  .  .  .  ?
   C14  C15  C16  C20  175.93(15)  .  .  .  .  ?
   C15  C16  C17  C18  1.1(3)  .  .  .  .  ?
   C20  C16  C17  C18  -176.55(16)  .  .  .  .  ?
   C16  C17  C18  C19  0.8(3)  .  .  .  .  ?
   C17  C18  C19  C14  -1.9(3)  .  .  .  .  ?
   C15  C14  C19  C18  1.2(3)  .  .  .  .  ?
   C1  C14  C19  C18  178.80(16)  .  .  .  .  ?
   C21  N5  N6  C20  -164.44(14)  .  .  .  .  ?
   B2  N5  N6  C20  16.0(2)  .  .  .  .  ?
   C27  N7  N8  C20  165.92(13)  .  .  .  .  ?
   B2  N7  N8  C20  -16.3(2)  .  .  .  .  ?
   N7  N8  C20  N6  -19.6(2)  .  .  .  .  ?
   N7  N8  C20  C16  170.60(14)  .  .  .  .  ?
   N5  N6  C20  N8  19.7(2)  .  .  .  .  ?
   N5  N6  C20  C16  -170.22(14)  .  .  .  .  ?
   C15  C16  C20  N8  179.25(15)  .  .  .  .  ?
   C17  C16  C20  N8  -3.0(2)  .  .  .  .  ?
   C15  C16  C20  N6  8.6(2)  .  .  .  .  ?
   C17  C16  C20  N6  -173.68(15)  .  .  .  .  ?
   N6  N5  B2  F3  -163.23(14)  .  .  .  .  ?
   C21  N5  B2  F3  17.3(2)  .  .  .  .  ?
   N6  N5  B2  F4  72.80(18)  .  .  .  .  ?
   C21  N5  B2  F4  -106.65(18)  .  .  .  .  ?
   N6  N5  B2  N7  -42.47(18)  .  .  .  .  ?
   C21  N5  B2  N7  138.08(15)  .  .  .  .  ?
   N8  N7  B2  F3  163.08(14)  .  .  .  .  ?
   C27  N7  B2  F3  -19.4(2)  .  .  .  .  ?
   N8  N7  B2  F4  -71.97(18)  .  .  .  .  ?
   C27  N7  B2  F4  105.53(17)  .  .  .  .  ?
   N8  N7  B2  N5  42.89(19)  .  .  .  .  ?
   C27  N7  B2  N5  -139.60(15)  .  .  .  .  ?
   N6  N5  C21  C22  -153.70(15)  .  .  .  .  ?
   B2  N5  C21  C22  25.8(2)  .  .  .  .  ?
   N6  N5  C21  C26  24.4(2)  .  .  .  .  ?
   B2  N5  C21  C26  -156.14(16)  .  .  .  .  ?
   C26  C21  C22  C23  0.0(2)  .  .  .  .  ?
   N5  C21  C22  C23  178.04(15)  .  .  .  .  ?
   C21  C22  C23  C24  -0.5(3)  .  .  .  .  ?
   C22  C23  C24  C25  0.8(3)  .  .  .  .  ?
   C23  C24  C25  C26  -0.5(3)  .  .  .  .  ?
   C24  C25  C26  C21  -0.1(3)  .  .  .  .  ?
   C22  C21  C26  C25  0.3(2)  .  .  .  .  ?
   N5  C21  C26  C25  -177.74(15)  .  .  .  .  ?
   N8  N7  C27  C28  156.92(15)  .  .  .  .  ?
   B2  N7  C27  C28  -20.7(2)  .  .  .  .  ?
   N8  N7  C27  C32  -21.7(2)  .  .  .  .  ?
   B2  N7  C27  C32  160.68(16)  .  .  .  .  ?
   C32  C27  C28  C29  -0.2(3)  .  .  .  .  ?
   N7  C27  C28  C29  -178.83(15)  .  .  .  .  ?
   C27  C28  C29  C30  -0.2(3)  .  .  .  .  ?
   C28  C29  C30  C31  0.9(3)  .  .  .  .  ?
   C29  C30  C31  C32  -1.1(3)  .  .  .  .  ?
   C30  C31  C32  C27  0.7(3)  .  .  .  .  ?
   C28  C27  C32  C31  0.0(3)  .  .  .  .  ?
   N7  C27  C32  C31  178.60(15)  .  .  .  .  ?
 
loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
   C3  H3  F2  0.954(18)  2.534(17)  3.182(2)  125.3(13)  .
   C9  H9  F1  0.981(18)  2.338(17)  2.892(2)  114.9(12)  .
   C22  H22  F3  0.940(18)  2.342(17)  2.859(2)  114.2(13)  .
   C28  H28  F3  0.927(19)  2.291(17)  2.835(2)  117.0(13)  .
 
_refine_diff_density_max                0.253
_refine_diff_density_min                -0.326
_refine_diff_density_rms                0.054
_shelxl_version_number                  2014/6


_diffrn_detector                        'CCD plate'
_diffrn_detector_type                   'Bruker Apex2'
_diffrn_measurement_device              'κ-geometry diffractometer'
