# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1542452'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
# original saved as ccpe417a_2015_0m_a


# SUBMISSION DETAILS

_audit_creation_method           'manual editing of SHELXL-2013 template'


_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          476-479
_chemical_formula_moiety         'C28 H30 B N3'
_chemical_formula_sum            'C28 H30 B N3'
_chemical_formula_weight         419.36

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1379(4)
_cell_length_b                   9.8806(4)
_cell_length_c                   18.5754(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.151(2)
_cell_angle_gamma                90
_cell_volume                     2227.74(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5383
_cell_measurement_theta_min      2.658
_cell_measurement_theta_max      27.23

_exptl_crystal_description       plate-like
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   0.7060
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.129
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16691
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.002
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4218
_reflns_number_gt                3299
_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 software package v2013.10-0 (Bruker AXS)
;
_computing_cell_refinement       
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)
;
_computing_data_reduction        
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)
;
_computing_structure_solution    
; SHELXT-2014 (Sheldrick, 2014)
;
_computing_structure_refinement  
; SHELXL-2014 (Sheldrick, 2014),
  OLEX2 v1.2.3 (Dolomanov, Bourhis, Gildea, Howard, 
                Puschmann, 2009)
;
_computing_molecular_graphics    
; XP (SHELXTL-NT v6.14, Bruker AXS)
;

# REFINEMENT DATA

_refine_special_details          
;The non-hydrogen atoms were refined anisotropically. Hydrogen
 atoms of the phenyl, CH(ipso), and CH₂- groups were included 
 at geometrically idealized positions (C-H bond distances 
 0.95/1.00/0.99 Aå) and were not refined. The isotropic thermal 
 parameters of these hydrogen atoms were fixed at 1.2 (phenyl,
 CH and CH₂-groups) that of the preceding carbon or nitrogen
 atom, respectively.
 The hydrogen atom attached to the carbon atom labelled as
 C(6) was located in the Fourier electron difference map.
 Its coordinates and its isotropic parameter were allowed to
 refine. 
 One of the carbon atoms of the cyclic octane [labelled as 
 C(9A) and C(9B)] was disordered over two sites. The site
 occupancy factors were refined to 0.800(4) and 0.200(4),
 respectively. The hydrogen atoms of the adjacent 
 non-disordered carbon atoms [labelled as C(8)] and C10)]
 were split using the above refined site occupancy factors
 to give the correct orientation for each disordered 
 component (OLEX2). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0458P)²+1.1662P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4218
_refine_ls_number_parameters     297
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.23086(11) 0.45028(15) 0.22740(7) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.32184(10) 0.44826(14) 0.18301(7) 0.0241(3) Uani 1 1 d . . . . .
N4 N 0.44296(10) 0.51243(14) 0.27908(7) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.41788(12) 0.47813(16) 0.20672(9) 0.0223(4) Uani 1 1 d . . . . .
C6 C 0.23522(13) 0.49798(18) 0.30229(8) 0.0237(4) Uani 1 1 d . . . . .
H6 H 0.1994(14) 0.5910(19) 0.3050(9) 0.030(5) Uiso 1 1 d . . . . .
C7 C 0.17142(13) 0.39842(17) 0.35142(9) 0.0261(4) Uani 1 1 d . . . . .
H7 H 0.1073 0.3664 0.3221 0.031 Uiso 1 1 calc R U . . .
C8 C 0.12127(15) 0.4713(2) 0.41707(10) 0.0364(5) Uani 1 1 d D . . . .
H8AA H 0.1118 0.4044 0.4562 0.044 Uiso 0.800(4) 1 calc R U P A 1
H8AB H 0.0471 0.5046 0.4036 0.044 Uiso 0.800(4) 1 calc R U P A 1
H8BC H 0.0828 0.5518 0.3977 0.044 Uiso 0.200(4) 1 calc R U P A 2
H8BD H 0.0632 0.4104 0.4357 0.044 Uiso 0.200(4) 1 calc R U P A 2
C9A C 0.19118(19) 0.5958(3) 0.44759(13) 0.0334(6) Uani 0.800(4) 1 d D . P A 1
H9AA H 0.1905 0.6676 0.4104 0.040 Uiso 0.800(4) 1 calc R U P A 1
H9AB H 0.1514 0.6320 0.4899 0.040 Uiso 0.800(4) 1 calc R U P A 1
C9B C 0.1782(7) 0.5152(11) 0.4759(5) 0.0334(6) Uani 0.200(4) 1 d D . P A 2
H9BA H 0.1809 0.4388 0.5103 0.040 Uiso 0.200(4) 1 calc R U P A 2
H9BB H 0.1334 0.5871 0.4986 0.040 Uiso 0.200(4) 1 calc R U P A 2
C10 C 0.30502(17) 0.5745(2) 0.46898(11) 0.0459(5) Uani 1 1 d D . . . .
H10A H 0.3050 0.5136 0.5113 0.055 Uiso 0.800(4) 1 calc R U P A 1
H10B H 0.3349 0.6626 0.4852 0.055 Uiso 0.800(4) 1 calc R U P A 1
H10D H 0.2990 0.6727 0.4592 0.055 Uiso 0.200(4) 1 calc R U P A 2
H10C H 0.3400 0.5650 0.5169 0.055 Uiso 0.200(4) 1 calc R U P A 2
C11 C 0.38545(15) 0.51584(19) 0.41373(9) 0.0326(4) Uani 1 1 d . . . . .
H11 H 0.4559 0.5674 0.4193 0.039 Uiso 1 1 calc R U . . .
C12 C 0.41217(15) 0.3662(2) 0.43232(10) 0.0392(5) Uani 1 1 d . . . . .
H12A H 0.4644 0.3312 0.3960 0.047 Uiso 1 1 calc R U . . .
H12B H 0.4500 0.3640 0.4796 0.047 Uiso 1 1 calc R U . . .
C13 C 0.31480(15) 0.27219(19) 0.43542(10) 0.0343(4) Uani 1 1 d . . . . .
H13A H 0.2703 0.2965 0.4781 0.041 Uiso 1 1 calc R U . . .
H13B H 0.3427 0.1791 0.4431 0.041 Uiso 1 1 calc R U . . .
C14 C 0.23844(15) 0.27036(18) 0.36982(10) 0.0321(4) Uani 1 1 d . . . . .
H14A H 0.1856 0.1951 0.3764 0.038 Uiso 1 1 calc R U . . .
H14B H 0.2838 0.2478 0.3273 0.038 Uiso 1 1 calc R U . . .
C15 C 0.13159(13) 0.45480(17) 0.18780(9) 0.0251(4) Uani 1 1 d . . . . .
C16 C 0.12729(13) 0.40013(18) 0.11847(9) 0.0278(4) Uani 1 1 d . . . . .
H16 H 0.1908 0.3577 0.0989 0.033 Uiso 1 1 calc R U . . .
C17 C 0.03196(14) 0.40712(19) 0.07805(10) 0.0317(4) Uani 1 1 d . . . . .
H17 H 0.0307 0.3697 0.0310 0.038 Uiso 1 1 calc R U . . .
C18 C -0.06194(14) 0.46793(19) 0.10511(10) 0.0347(4) Uani 1 1 d . . . . .
H18 H -0.1271 0.4735 0.0768 0.042 Uiso 1 1 calc R U . . .
C19 C -0.05901(14) 0.52022(19) 0.17380(10) 0.0341(4) Uani 1 1 d . . . . .
H19 H -0.1232 0.5614 0.1931 0.041 Uiso 1 1 calc R U . . .
C20 C 0.03627(13) 0.51392(18) 0.21553(10) 0.0302(4) Uani 1 1 d . . . . .
H20 H 0.0364 0.5499 0.2630 0.036 Uiso 1 1 calc R U . . .
C21 C 0.50473(12) 0.48259(17) 0.15036(9) 0.0240(4) Uani 1 1 d . . . . .
C22 C 0.56897(13) 0.59761(19) 0.13966(9) 0.0299(4) Uani 1 1 d . . . . .
H22 H 0.5627 0.6722 0.1716 0.036 Uiso 1 1 calc R U . . .
C23 C 0.64204(14) 0.6035(2) 0.08245(10) 0.0371(5) Uani 1 1 d . . . . .
H23 H 0.6860 0.6820 0.0757 0.045 Uiso 1 1 calc R U . . .
C24 C 0.65123(14) 0.4963(2) 0.03537(10) 0.0402(5) Uani 1 1 d . . . . .
H24 H 0.7007 0.5013 -0.0041 0.048 Uiso 1 1 calc R U . . .
C25 C 0.58838(14) 0.3822(2) 0.04577(10) 0.0394(5) Uani 1 1 d . . . . .
H25 H 0.5947 0.3080 0.0135 0.047 Uiso 1 1 calc R U . . .
C26 C 0.51596(14) 0.3748(2) 0.10301(9) 0.0319(4) Uani 1 1 d . . . . .
H26 H 0.4735 0.2952 0.1100 0.038 Uiso 1 1 calc R U . . .
C27 C 0.55821(13) 0.52083(17) 0.29873(9) 0.0247(4) Uani 1 1 d . . . . .
C28 C 0.62508(15) 0.4081(2) 0.29445(10) 0.0360(4) Uani 1 1 d . . . . .
H28 H 0.5959 0.3240 0.2786 0.043 Uiso 1 1 calc R U . . .
C29 C 0.73562(16) 0.4189(3) 0.31350(11) 0.0490(6) Uani 1 1 d . . . . .
H29 H 0.7824 0.3421 0.3100 0.059 Uiso 1 1 calc R U . . .
C30 C 0.77756(16) 0.5406(3) 0.33752(11) 0.0508(6) Uani 1 1 d . . . . .
H30 H 0.8529 0.5471 0.3512 0.061 Uiso 1 1 calc R U . . .
C31 C 0.71059(15) 0.6526(2) 0.34174(10) 0.0447(5) Uani 1 1 d . . . . .
H31 H 0.7396 0.7364 0.3582 0.054 Uiso 1 1 calc R U . . .
C32 C 0.60072(14) 0.6431(2) 0.32198(9) 0.0315(4) Uani 1 1 d . . . . .
H32 H 0.5546 0.7206 0.3244 0.038 Uiso 1 1 calc R U . . .
B5 B 0.35730(15) 0.51601(18) 0.33098(10) 0.0237(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.
;

# MOLECULAR GEOMETRY

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 1.3801(18) . ?
N1 C15 1.411(2) . ?
N1 C6 1.470(2) . ?
N2 C3 1.280(2) . ?
N4 C3 1.419(2) . ?
N4 B5 1.420(2) . ?
N4 C27 1.447(2) . ?
C3 C21 1.488(2) . ?
C6 C7 1.550(2) . ?
C6 B5 1.583(2) . ?
C6 H6 1.018(19) . ?
C7 C14 1.542(2) . ?
C7 C8 1.543(2) . ?
C7 H7 1.0000 . ?
C8 C9B 1.362(8) . ?
C8 C9A 1.597(3) . ?
C8 H8AA 0.9900 . ?
C8 H8AB 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C9A C10 1.452(3) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9B C10 1.652(8) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10 C11 1.532(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10D 0.9900 . ?
C10 H10C 0.9900 . ?
C11 C12 1.552(3) . ?
C11 B5 1.574(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.396(2) . ?
C15 C16 1.397(2) . ?
C16 C17 1.379(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.388(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.381(2) . ?
C27 C32 1.383(2) . ?
C28 C29 1.391(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(2) . ?
C31 H31 0.9500 . ?
C32 H32 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
N2 N1 C15 111.87(13) . . ?
N2 N1 C6 122.91(12) . . ?
C15 N1 C6 120.80(13) . . ?
C3 N2 N1 121.39(13) . . ?
C3 N4 B5 119.58(13) . . ?
C3 N4 C27 117.23(13) . . ?
B5 N4 C27 122.43(14) . . ?
N2 C3 N4 125.04(14) . . ?
N2 C3 C21 114.28(14) . . ?
N4 C3 C21 120.59(13) . . ?
N1 C6 C7 109.69(13) . . ?
N1 C6 B5 112.71(13) . . ?
C7 C6 B5 109.98(13) . . ?
N1 C6 H6 108.8(10) . . ?
C7 C6 H6 109.3(10) . . ?
B5 C6 H6 106.3(10) . . ?
C14 C7 C8 114.63(14) . . ?
C14 C7 C6 112.77(13) . . ?
C8 C7 C6 111.58(14) . . ?
C14 C7 H7 105.7 . . ?
C8 C7 H7 105.7 . . ?
C6 C7 H7 105.7 . . ?
C9B C8 C7 125.6(4) . . ?
C7 C8 C9A 115.44(15) . . ?
C7 C8 H8AA 108.4 . . ?
C9A C8 H8AA 108.4 . . ?
C7 C8 H8AB 108.4 . . ?
C9A C8 H8AB 108.4 . . ?
H8AA C8 H8AB 107.5 . . ?
C9B C8 H8BC 105.9 . . ?
C7 C8 H8BC 105.9 . . ?
C9B C8 H8BD 105.9 . . ?
C7 C8 H8BD 105.9 . . ?
H8BC C8 H8BD 106.2 . . ?
C10 C9A C8 119.32(19) . . ?
C10 C9A H9AA 107.5 . . ?
C8 C9A H9AA 107.5 . . ?
C10 C9A H9AB 107.5 . . ?
C8 C9A H9AB 107.5 . . ?
H9AA C9A H9AB 107.0 . . ?
C8 C9B C10 121.5(7) . . ?
C8 C9B H9BA 107.0 . . ?
C10 C9B H9BA 107.0 . . ?
C8 C9B H9BB 107.0 . . ?
C10 C9B H9BB 107.0 . . ?
H9BA C9B H9BB 106.7 . . ?
C9A C10 C11 118.63(18) . . ?
C11 C10 C9B 120.9(3) . . ?
C9A C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C9A C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
C11 C10 H10D 107.1 . . ?
C9B C10 H10D 107.1 . . ?
C11 C10 H10C 107.1 . . ?
C9B C10 H10C 107.1 . . ?
H10D C10 H10C 106.8 . . ?
C10 C11 C12 110.14(15) . . ?
C10 C11 B5 121.11(16) . . ?
C12 C11 B5 105.25(14) . . ?
C10 C11 H11 106.5 . . ?
C12 C11 H11 106.5 . . ?
B5 C11 H11 106.5 . . ?
C13 C12 C11 115.66(15) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 C14 116.83(15) . . ?
C12 C13 H13A 108.1 . . ?
C14 C13 H13A 108.1 . . ?
C12 C13 H13B 108.1 . . ?
C14 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 C7 119.03(15) . . ?
C13 C14 H14A 107.6 . . ?
C7 C14 H14A 107.6 . . ?
C13 C14 H14B 107.6 . . ?
C7 C14 H14B 107.6 . . ?
H14A C14 H14B 107.0 . . ?
C20 C15 C16 118.23(15) . . ?
C20 C15 N1 121.90(15) . . ?
C16 C15 N1 119.87(15) . . ?
C17 C16 C15 120.76(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.97(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 118.69(16) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 121.24(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 120.10(17) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C26 C21 C22 118.66(16) . . ?
C26 C21 C3 119.60(15) . . ?
C22 C21 C3 121.49(15) . . ?
C23 C22 C21 120.20(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.44(18) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.68(17) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.31(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.70(18) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C28 C27 C32 120.27(16) . . ?
C28 C27 N4 120.48(16) . . ?
C32 C27 N4 119.25(15) . . ?
C27 C28 C29 119.37(19) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.15(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 119.9(2) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 120.02(18) . . ?
C27 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
N4 B5 C11 120.37(15) . . ?
N4 B5 C6 117.05(15) . . ?
C11 B5 C6 121.95(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 N2 C3 162.18(15) . . . . ?
C6 N1 N2 C3 5.7(2) . . . . ?
N1 N2 C3 N4 1.6(2) . . . . ?
N1 N2 C3 C21 -174.90(14) . . . . ?
B5 N4 C3 N2 -0.4(2) . . . . ?
C27 N4 C3 N2 169.80(15) . . . . ?
B5 N4 C3 C21 175.90(15) . . . . ?
C27 N4 C3 C21 -13.9(2) . . . . ?
N2 N1 C6 C7 -135.23(15) . . . . ?
C15 N1 C6 C7 70.29(19) . . . . ?
N2 N1 C6 B5 -12.3(2) . . . . ?
C15 N1 C6 B5 -166.81(14) . . . . ?
N1 C6 C7 C14 78.98(17) . . . . ?
B5 C6 C7 C14 -45.52(18) . . . . ?
N1 C6 C7 C8 -150.32(14) . . . . ?
B5 C6 C7 C8 85.18(17) . . . . ?
C14 C7 C8 C9B 54.8(6) . . . . ?
C6 C7 C8 C9B -74.9(6) . . . . ?
C14 C7 C8 C9A 96.62(19) . . . . ?
C6 C7 C8 C9A -33.1(2) . . . . ?
C9B C8 C9A C10 59.9(6) . . . . ?
C7 C8 C9A C10 -56.1(3) . . . . ?
C7 C8 C9B C10 34.9(11) . . . . ?
C9A C8 C9B C10 -51.0(6) . . . . ?
C8 C9A C10 C11 56.3(3) . . . . ?
C8 C9A C10 C9B -47.7(5) . . . . ?
C8 C9B C10 C9A 62.4(7) . . . . ?
C8 C9B C10 C11 -34.7(10) . . . . ?
C9A C10 C11 C12 -106.4(2) . . . . ?
C9B C10 C11 C12 -65.2(5) . . . . ?
C9A C10 C11 B5 16.9(3) . . . . ?
C9B C10 C11 B5 58.0(5) . . . . ?
C10 C11 C12 C13 58.4(2) . . . . ?
B5 C11 C12 C13 -73.7(2) . . . . ?
C11 C12 C13 C14 52.7(2) . . . . ?
C12 C13 C14 C7 -65.8(2) . . . . ?
C8 C7 C14 C13 -41.2(2) . . . . ?
C6 C7 C14 C13 87.94(19) . . . . ?
N2 N1 C15 C20 -151.90(16) . . . . ?
C6 N1 C15 C20 5.2(2) . . . . ?
N2 N1 C15 C16 27.5(2) . . . . ?
C6 N1 C15 C16 -175.45(15) . . . . ?
C20 C15 C16 C17 1.4(3) . . . . ?
N1 C15 C16 C17 -178.06(15) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C16 C15 C20 C19 -1.5(3) . . . . ?
N1 C15 C20 C19 177.91(16) . . . . ?
N2 C3 C21 C26 -50.2(2) . . . . ?
N4 C3 C21 C26 133.08(16) . . . . ?
N2 C3 C21 C22 123.96(17) . . . . ?
N4 C3 C21 C22 -52.7(2) . . . . ?
C26 C21 C22 C23 0.3(2) . . . . ?
C3 C21 C22 C23 -173.91(15) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C24 C25 C26 C21 0.6(3) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
C3 C21 C26 C25 173.47(16) . . . . ?
C3 N4 C27 C28 -62.4(2) . . . . ?
B5 N4 C27 C28 107.50(19) . . . . ?
C3 N4 C27 C32 117.66(17) . . . . ?
B5 N4 C27 C32 -72.4(2) . . . . ?
C32 C27 C28 C29 -0.2(3) . . . . ?
N4 C27 C28 C29 179.87(16) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C28 C29 C30 C31 -1.0(3) . . . . ?
C29 C30 C31 C32 0.1(3) . . . . ?
C28 C27 C32 C31 -0.6(3) . . . . ?
N4 C27 C32 C31 179.31(15) . . . . ?
C30 C31 C32 C27 0.6(3) . . . . ?
C3 N4 B5 C11 163.98(15) . . . . ?
C27 N4 B5 C11 -5.7(2) . . . . ?
C3 N4 B5 C6 -7.1(2) . . . . ?
C27 N4 B5 C6 -176.81(15) . . . . ?
C10 C11 B5 N4 155.43(16) . . . . ?
C12 C11 B5 N4 -79.02(19) . . . . ?
C10 C11 B5 C6 -33.9(2) . . . . ?
C12 C11 B5 C6 91.63(19) . . . . ?
N1 C6 B5 N4 12.7(2) . . . . ?
C7 C6 B5 N4 135.41(15) . . . . ?
N1 C6 B5 C11 -158.27(15) . . . . ?
C7 C6 B5 C11 -35.5(2) . . . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.049

_shelxl_version_number           2012-9


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane and hexane'
