# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1651

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 B2 I2 N4'
_chemical_formula_sum            'C12 H10 B2 I2 N4'
_chemical_formula_weight         485.66

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'
I I -0.4742 1.8119 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   18.7020(7)
_cell_length_b                   18.7020(7)
_cell_length_c                   23.5495(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7133.3(6)
_cell_formula_units_Z            18
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    57050
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      26.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_F_000             4068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.961
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.693
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35425
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.389
_diffrn_reflns_theta_max         25.828
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3057
_reflns_number_gt                3038
_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. These statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0235P)²+27.8811P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3057
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0533
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_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
I1 I 0.66106(2) 0.16766(2) 0.62151(2) 0.03575(8) Uani 1 1 d . . . . .
I2 I 1.26173(2) 0.51757(2) 0.60483(2) 0.04293(9) Uani 1 1 d . . . . .
B1 B 0.9704(2) 0.2218(2) 0.53213(15) 0.0199(7) Uani 1 1 d . . . . .
H1 H 0.982(3) 0.179(2) 0.5574(17) 0.027(10) Uiso 1 1 d . . . . .
B2 B 0.9531(2) 0.3445(2) 0.48528(15) 0.0198(7) Uani 1 1 d . . . . .
H2 H 0.949(2) 0.395(3) 0.4701(16) 0.027(10) Uiso 1 1 d . . . . .
N1 N 0.88971(17) 0.22280(16) 0.54995(11) 0.0186(5) Uani 1 1 d . . . . .
N2 N 0.88156(16) 0.28529(16) 0.52651(11) 0.0186(5) Uani 1 1 d . . . . .
C3 C 0.81067(19) 0.2780(2) 0.54514(14) 0.0221(6) Uani 1 1 d . . . . .
H3 H 0.7900 0.3137 0.5358 0.027 Uiso 1 1 calc R U . . .
C4 C 0.77268(19) 0.2099(2) 0.58019(13) 0.0233(6) Uani 1 1 d . . . . .
C5 C 0.8243(2) 0.1767(2) 0.58251(12) 0.0195(6) Uani 1 1 d . . . . .
H5 H 0.8148 0.1294 0.6036 0.023 Uiso 1 1 calc R U . . .
N11 N 1.04002(16) 0.31274(16) 0.54860(11) 0.0184(5) Uani 1 1 d . . . . .
N12 N 1.03078(16) 0.37401(16) 0.52517(11) 0.0193(5) Uani 1 1 d . . . . .
C13 C 1.0963(2) 0.4465(2) 0.53917(14) 0.0233(6) Uani 1 1 d . . . . .
H13 H 1.1055 0.4993 0.5283 0.028 Uiso 1 1 calc R U . . .
C14 C 1.14843(19) 0.4313(2) 0.57213(14) 0.0240(7) Uani 1 1 d . . . . .
C15 C 1.1110(2) 0.3465(2) 0.57746(13) 0.0217(6) Uani 1 1 d . . . . .
H15 H 1.1320 0.3173 0.5980 0.026 Uiso 1 1 calc R U . . .
C21 C 0.97082(18) 0.22199(19) 0.46370(13) 0.0201(6) Uani 1 1 d . . . . .
C22 C 0.96171(19) 0.2856(2) 0.43954(14) 0.0220(6) Uani 1 1 d . . . . .
C23 C 0.9616(2) 0.2925(2) 0.38071(15) 0.0299(7) Uani 1 1 d . . . . .
H23 H 0.9544 0.3346 0.3639 0.036 Uiso 1 1 calc R U . . .
C24 C 0.9720(2) 0.2376(3) 0.34622(15) 0.0389(10) Uani 1 1 d . . . . .
H24 H 0.9724 0.2429 0.3061 0.047 Uiso 1 1 calc R U . . .
C25 C 0.9816(2) 0.1760(3) 0.37030(16) 0.0367(9) Uani 1 1 d . . . . .
H25 H 0.9887 0.1388 0.3467 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9811(2) 0.1678(2) 0.42904(16) 0.0277(7) Uani 1 1 d . . . . .
H26 H 0.9878 0.1250 0.4454 0.033 Uiso 1 1 calc R U . . .


_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 C4 2.069(3) . ?
I2 C14 2.066(3) . ?
B1 N1 1.575(4) . ?
B1 N11 1.588(4) . ?
B1 C21 1.611(5) . ?
B1 H1 1.10(4) . ?
B2 N2 1.574(4) . ?
B2 N12 1.579(4) . ?
B2 C22 1.604(5) . ?
B2 H2 1.05(4) . ?
N1 C5 1.331(4) . ?
N1 N2 1.368(4) . ?
N2 C3 1.337(4) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C5 H5 0.9500 . ?
N11 C15 1.336(4) . ?
N11 N12 1.358(4) . ?
N12 C13 1.336(4) . ?
C13 C14 1.382(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(5) . ?
C15 H15 0.9500 . ?
C21 C26 1.388(5) . ?
C21 C22 1.404(5) . ?
C22 C23 1.391(5) . ?
C23 C24 1.396(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(6) . ?
C25 H25 0.9500 . ?
C26 H26 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
N1 B1 N11 101.5(2) . . ?
N1 B1 C21 105.7(3) . . ?
N11 B1 C21 104.0(2) . . ?
N1 B1 H1 114(2) . . ?
N11 B1 H1 107(2) . . ?
C21 B1 H1 123(2) . . ?
N2 B2 N12 100.9(2) . . ?
N2 B2 C22 105.8(3) . . ?
N12 B2 C22 104.4(3) . . ?
N2 B2 H2 115(2) . . ?
N12 B2 H2 111(2) . . ?
C22 B2 H2 118(2) . . ?
C5 N1 N2 109.1(2) . . ?
C5 N1 B1 136.1(3) . . ?
N2 N1 B1 114.8(2) . . ?
C3 N2 N1 108.0(3) . . ?
C3 N2 B2 136.5(3) . . ?
N1 N2 B2 115.5(2) . . ?
N2 C3 C4 108.5(3) . . ?
N2 C3 H3 125.7 . . ?
C4 C3 H3 125.7 . . ?
C3 C4 C5 106.5(3) . . ?
C3 C4 I1 126.2(2) . . ?
C5 C4 I1 127.3(2) . . ?
N1 C5 C4 107.8(3) . . ?
N1 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
C15 N11 N12 108.9(3) . . ?
C15 N11 B1 136.0(3) . . ?
N12 N11 B1 115.0(2) . . ?
C13 N12 N11 108.4(3) . . ?
C13 N12 B2 135.9(3) . . ?
N11 N12 B2 115.4(2) . . ?
N12 C13 C14 108.3(3) . . ?
N12 C13 H13 125.8 . . ?
C14 C13 H13 125.8 . . ?
C13 C14 C15 106.3(3) . . ?
C13 C14 I2 127.1(3) . . ?
C15 C14 I2 126.6(2) . . ?
N11 C15 C14 108.0(3) . . ?
N11 C15 H15 126.0 . . ?
C14 C15 H15 126.0 . . ?
C26 C21 C22 120.0(3) . . ?
C26 C21 B1 126.1(3) . . ?
C22 C21 B1 113.9(3) . . ?
C23 C22 C21 119.2(3) . . ?
C23 C22 B2 126.9(3) . . ?
C21 C22 B2 113.9(3) . . ?
C22 C23 C24 120.3(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.0(4) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?

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
N11 B1 N1 C5 -126.6(4) . . . . ?
C21 B1 N1 C5 125.2(4) . . . . ?
N11 B1 N1 N2 54.4(3) . . . . ?
C21 B1 N1 N2 -53.8(3) . . . . ?
C5 N1 N2 C3 0.4(3) . . . . ?
B1 N1 N2 C3 179.7(3) . . . . ?
C5 N1 N2 B2 -178.5(3) . . . . ?
B1 N1 N2 B2 0.8(4) . . . . ?
N12 B2 N2 C3 125.8(4) . . . . ?
C22 B2 N2 C3 -125.7(4) . . . . ?
N12 B2 N2 N1 -55.8(3) . . . . ?
C22 B2 N2 N1 52.8(3) . . . . ?
N1 N2 C3 C4 -0.7(3) . . . . ?
B2 N2 C3 C4 177.9(3) . . . . ?
N2 C3 C4 C5 0.7(4) . . . . ?
N2 C3 C4 I1 -180.0(2) . . . . ?
N2 N1 C5 C4 0.0(3) . . . . ?
B1 N1 C5 C4 -179.1(3) . . . . ?
C3 C4 C5 N1 -0.4(4) . . . . ?
I1 C4 C5 N1 -179.7(2) . . . . ?
N1 B1 N11 C15 131.0(3) . . . . ?
C21 B1 N11 C15 -119.5(4) . . . . ?
N1 B1 N11 N12 -54.8(3) . . . . ?
C21 B1 N11 N12 54.8(3) . . . . ?
C15 N11 N12 C13 0.2(3) . . . . ?
B1 N11 N12 C13 -175.5(3) . . . . ?
C15 N11 N12 B2 175.3(3) . . . . ?
B1 N11 N12 B2 -0.5(4) . . . . ?
N2 B2 N12 C13 -131.3(4) . . . . ?
C22 B2 N12 C13 119.0(4) . . . . ?
N2 B2 N12 N11 55.5(3) . . . . ?
C22 B2 N12 N11 -54.2(3) . . . . ?
N11 N12 C13 C14 0.0(4) . . . . ?
B2 N12 C13 C14 -173.5(3) . . . . ?
N12 C13 C14 C15 -0.3(4) . . . . ?
N12 C13 C14 I2 177.8(2) . . . . ?
N12 N11 C15 C14 -0.4(3) . . . . ?
B1 N11 C15 C14 174.1(3) . . . . ?
C13 C14 C15 N11 0.4(4) . . . . ?
I2 C14 C15 N11 -177.7(2) . . . . ?
N1 B1 C21 C26 -129.0(3) . . . . ?
N11 B1 C21 C26 124.5(3) . . . . ?
N1 B1 C21 C22 52.7(3) . . . . ?
N11 B1 C21 C22 -53.8(3) . . . . ?
C26 C21 C22 C23 1.2(5) . . . . ?
B1 C21 C22 C23 179.7(3) . . . . ?
C26 C21 C22 B2 -178.3(3) . . . . ?
B1 C21 C22 B2 0.2(4) . . . . ?
N2 B2 C22 C23 128.1(3) . . . . ?
N12 B2 C22 C23 -125.9(3) . . . . ?
N2 B2 C22 C21 -52.5(3) . . . . ?
N12 B2 C22 C21 53.6(3) . . . . ?
C21 C22 C23 C24 -1.2(5) . . . . ?
B2 C22 C23 C24 178.2(3) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C26 0.0(5) . . . . ?
C22 C21 C26 C25 -0.6(5) . . . . ?
B1 C21 C26 C25 -178.8(3) . . . . ?
C24 C25 C26 C21 0.0(5) . . . . ?

_refine_diff_density_max         1.246
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.077

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 985503'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1681

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 B2 N4'
_chemical_formula_sum            'C16 H20 B2 N4'
_chemical_formula_weight         289.98

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9633(10)
_cell_length_b                   8.5150(11)
_cell_length_c                   12.6954(17)
_cell_angle_alpha                71.470(10)
_cell_angle_beta                 81.729(11)
_cell_angle_gamma                77.430(10)
_cell_volume                     794.05(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10227
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      26.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8359
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.473
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2787
_reflns_number_gt                2175
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0440P)²+0.7048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2787
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_restrained_S_all      1.239
_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
B1 B 0.5514(4) 0.6111(4) 0.7129(3) 0.0276(7) Uani 1 1 d . . . . .
H1 H 0.582(4) 0.495(4) 0.680(2) 0.024(7) Uiso 1 1 d . . . . .
B2 B 0.5218(4) 0.8801(4) 0.7861(3) 0.0273(7) Uani 1 1 d . . . . .
H2 H 0.534(4) 0.988(4) 0.814(3) 0.027(8) Uiso 1 1 d . . . . .
N1 N 0.6404(3) 0.5740(3) 0.8237(2) 0.0255(5) Uani 1 1 d . . . . .
N2 N 0.6243(3) 0.7100(3) 0.86158(19) 0.0251(5) Uani 1 1 d . . . . .
C3 C 0.7019(4) 0.6602(4) 0.9573(2) 0.0293(7) Uani 1 1 d . . . . .
C4 C 0.7684(4) 0.4887(4) 0.9800(3) 0.0308(7) Uani 1 1 d . . . . .
H4 H 0.8297 0.4191 1.0423 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7284(4) 0.4392(4) 0.8948(2) 0.0283(6) Uani 1 1 d . . . . .
C6 C 0.7082(4) 0.7764(4) 1.0221(3) 0.0379(8) Uani 1 1 d . . . . .
H6A H 0.8245 0.8024 1.0118 0.057 Uiso 1 1 calc R U . . .
H6B H 0.6794 0.7227 1.1013 0.057 Uiso 1 1 calc R U . . .
H6C H 0.6248 0.8808 0.9958 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7725(4) 0.2698(4) 0.8762(3) 0.0403(8) Uani 1 1 d . . . . .
H7A H 0.6670 0.2363 0.8663 0.060 Uiso 1 1 calc R U . . .
H7B H 0.8272 0.1871 0.9408 0.060 Uiso 1 1 calc R U . . .
H7C H 0.8524 0.2747 0.8093 0.060 Uiso 1 1 calc R U . . .
N11 N 0.6396(3) 0.7577(3) 0.6313(2) 0.0252(5) Uani 1 1 d . . . . .
N12 N 0.6237(3) 0.8953(3) 0.66796(19) 0.0251(5) Uani 1 1 d . . . . .
C13 C 0.7001(4) 1.0120(4) 0.5893(2) 0.0294(7) Uani 1 1 d . . . . .
C14 C 0.7652(4) 0.9484(4) 0.5016(3) 0.0313(7) Uani 1 1 d . . . . .
H14 H 0.8260 1.0032 0.4346 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7248(4) 0.7891(4) 0.5299(2) 0.0278(6) Uani 1 1 d . . . . .
C16 C 0.7076(4) 1.1788(4) 0.6011(3) 0.0378(8) Uani 1 1 d . . . . .
H16A H 0.6288 1.1979 0.6645 0.057 Uiso 1 1 calc R U . . .
H16B H 0.6732 1.2678 0.5328 0.057 Uiso 1 1 calc R U . . .
H16C H 0.8256 1.1806 0.6138 0.057 Uiso 1 1 calc R U . . .
C17 C 0.7646(4) 0.6632(4) 0.4668(3) 0.0394(8) Uani 1 1 d . . . . .
H17A H 0.8442 0.5640 0.5068 0.059 Uiso 1 1 calc R U . . .
H17B H 0.8183 0.7131 0.3926 0.059 Uiso 1 1 calc R U . . .
H17C H 0.6577 0.6298 0.4595 0.059 Uiso 1 1 calc R U . . .
C21 C 0.3541(4) 0.6967(3) 0.7364(2) 0.0262(6) Uani 1 1 d . . . . .
C22 C 0.3388(4) 0.8379(3) 0.7755(2) 0.0263(6) Uani 1 1 d . . . . .
C23 C 0.1752(4) 0.9229(4) 0.7992(2) 0.0297(7) Uani 1 1 d . . . . .
H23 H 0.1633 1.0171 0.8262 0.036 Uiso 1 1 calc R U . . .
C24 C 0.0276(4) 0.8715(4) 0.7838(2) 0.0328(7) Uani 1 1 d . . . . .
H24 H -0.0835 0.9310 0.8002 0.039 Uiso 1 1 calc R U . . .
C25 C 0.0427(4) 0.7352(4) 0.7450(3) 0.0339(7) Uani 1 1 d . . . . .
H25 H -0.0578 0.7007 0.7345 0.041 Uiso 1 1 calc R U . . .
C26 C 0.2062(4) 0.6475(4) 0.7212(2) 0.0296(7) Uani 1 1 d . . . . .
H26 H 0.2163 0.5534 0.6943 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N11 1.573(4) . ?
B1 N1 1.577(4) . ?
B1 C21 1.611(4) . ?
B1 H1 1.15(3) . ?
B2 N12 1.580(4) . ?
B2 N2 1.585(4) . ?
B2 C22 1.607(4) . ?
B2 H2 1.11(3) . ?
N1 C5 1.340(4) . ?
N1 N2 1.364(3) . ?
N2 C3 1.346(4) . ?
C3 C4 1.391(4) . ?
C3 C6 1.487(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 C7 1.494(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N11 C15 1.341(4) . ?
N11 N12 1.368(3) . ?
N12 C13 1.346(4) . ?
C13 C14 1.378(4) . ?
C13 C16 1.489(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C17 1.488(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C26 1.390(4) . ?
C21 C22 1.416(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.398(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.397(4) . ?
C25 H25 0.9500 . ?
C26 H26 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
N11 B1 N1 101.9(2) . . ?
N11 B1 C21 105.4(2) . . ?
N1 B1 C21 105.8(2) . . ?
N11 B1 H1 110.3(15) . . ?
N1 B1 H1 111.5(14) . . ?
C21 B1 H1 120.2(14) . . ?
N12 B2 N2 102.2(2) . . ?
N12 B2 C22 105.3(2) . . ?
N2 B2 C22 105.2(2) . . ?
N12 B2 H2 108.9(16) . . ?
N2 B2 H2 110.4(15) . . ?
C22 B2 H2 122.9(15) . . ?
C5 N1 N2 108.8(2) . . ?
C5 N1 B1 136.5(2) . . ?
N2 N1 B1 114.7(2) . . ?
C3 N2 N1 108.6(2) . . ?
C3 N2 B2 136.7(2) . . ?
N1 N2 B2 114.7(2) . . ?
N2 C3 C4 107.6(3) . . ?
N2 C3 C6 123.1(3) . . ?
C4 C3 C6 129.3(3) . . ?
C5 C4 C3 106.8(3) . . ?
C5 C4 H4 126.6 . . ?
C3 C4 H4 126.6 . . ?
N1 C5 C4 108.2(3) . . ?
N1 C5 C7 122.5(3) . . ?
C4 C5 C7 129.3(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 N11 N12 108.3(2) . . ?
C15 N11 B1 136.8(2) . . ?
N12 N11 B1 114.8(2) . . ?
C13 N12 N11 108.5(2) . . ?
C13 N12 B2 136.8(2) . . ?
N11 N12 B2 114.7(2) . . ?
N12 C13 C14 108.1(3) . . ?
N12 C13 C16 123.3(3) . . ?
C14 C13 C16 128.6(3) . . ?
C13 C14 C15 106.7(3) . . ?
C13 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
N11 C15 C14 108.3(3) . . ?
N11 C15 C17 121.9(3) . . ?
C14 C15 C17 129.8(3) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C21 C22 119.7(3) . . ?
C26 C21 B1 127.1(3) . . ?
C22 C21 B1 113.2(2) . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 B2 127.8(3) . . ?
C21 C22 B2 113.3(2) . . ?
C22 C23 C24 120.8(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.6(3) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 B1 N1 C5 -125.4(3) . . . . ?
C21 B1 N1 C5 124.5(3) . . . . ?
N11 B1 N1 N2 56.2(3) . . . . ?
C21 B1 N1 N2 -53.9(3) . . . . ?
C5 N1 N2 C3 -0.3(3) . . . . ?
B1 N1 N2 C3 178.6(2) . . . . ?
C5 N1 N2 B2 -179.8(2) . . . . ?
B1 N1 N2 B2 -0.9(3) . . . . ?
N12 B2 N2 C3 126.3(3) . . . . ?
C22 B2 N2 C3 -123.9(3) . . . . ?
N12 B2 N2 N1 -54.4(3) . . . . ?
C22 B2 N2 N1 55.4(3) . . . . ?
N1 N2 C3 C4 0.0(3) . . . . ?
B2 N2 C3 C4 179.3(3) . . . . ?
N1 N2 C3 C6 -179.7(3) . . . . ?
B2 N2 C3 C6 -0.3(5) . . . . ?
N2 C3 C4 C5 0.2(3) . . . . ?
C6 C3 C4 C5 179.9(3) . . . . ?
N2 N1 C5 C4 0.4(3) . . . . ?
B1 N1 C5 C4 -178.0(3) . . . . ?
N2 N1 C5 C7 -178.4(3) . . . . ?
B1 N1 C5 C7 3.1(5) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C4 C5 C7 178.4(3) . . . . ?
N1 B1 N11 C15 126.8(3) . . . . ?
C21 B1 N11 C15 -122.9(3) . . . . ?
N1 B1 N11 N12 -56.1(3) . . . . ?
C21 B1 N11 N12 54.2(3) . . . . ?
C15 N11 N12 C13 -0.4(3) . . . . ?
B1 N11 N12 C13 -178.3(2) . . . . ?
C15 N11 N12 B2 178.7(2) . . . . ?
B1 N11 N12 B2 0.8(3) . . . . ?
N2 B2 N12 C13 -126.8(3) . . . . ?
C22 B2 N12 C13 123.5(3) . . . . ?
N2 B2 N12 N11 54.5(3) . . . . ?
C22 B2 N12 N11 -55.2(3) . . . . ?
N11 N12 C13 C14 0.1(3) . . . . ?
B2 N12 C13 C14 -178.6(3) . . . . ?
N11 N12 C13 C16 180.0(2) . . . . ?
B2 N12 C13 C16 1.3(5) . . . . ?
N12 C13 C14 C15 0.2(3) . . . . ?
C16 C13 C14 C15 -179.7(3) . . . . ?
N12 N11 C15 C14 0.5(3) . . . . ?
B1 N11 C15 C14 177.7(3) . . . . ?
N12 N11 C15 C17 179.6(3) . . . . ?
B1 N11 C15 C17 -3.2(5) . . . . ?
C13 C14 C15 N11 -0.4(3) . . . . ?
C13 C14 C15 C17 -179.4(3) . . . . ?
N11 B1 C21 C26 125.1(3) . . . . ?
N1 B1 C21 C26 -127.5(3) . . . . ?
N11 B1 C21 C22 -54.2(3) . . . . ?
N1 B1 C21 C22 53.3(3) . . . . ?
C26 C21 C22 C23 0.8(4) . . . . ?
B1 C21 C22 C23 -179.9(2) . . . . ?
C26 C21 C22 B2 -178.8(2) . . . . ?
B1 C21 C22 B2 0.5(3) . . . . ?
N12 B2 C22 C23 -126.1(3) . . . . ?
N2 B2 C22 C23 126.3(3) . . . . ?
N12 B2 C22 C21 53.5(3) . . . . ?
N2 B2 C22 C21 -54.1(3) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
B2 C22 C23 C24 178.9(3) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C22 C21 C26 C25 -0.6(4) . . . . ?
B1 C21 C26 C25 -179.8(3) . . . . ?
C24 C25 C26 C21 0.1(4) . . . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 985504'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1689

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H44 B2 N4'
_chemical_formula_sum            'C28 H44 B2 N4'
_chemical_formula_weight         458.29

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'

_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                   10.6013(7)
_cell_length_b                   9.5489(6)
_cell_length_c                   28.2614(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.567(5)
_cell_angle_gamma                90
_cell_volume                     2821.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11232
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      25.9

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20700
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.964
_diffrn_reflns_theta_max         25.478
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5184
_reflns_number_gt                3166
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0515P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5184
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
B1 B 0.8940(2) 0.7058(3) 0.60793(9) 0.0333(5) Uani 1 1 d . . . . .
H1 H 0.9944(18) 0.664(2) 0.6102(7) 0.040 Uiso 1 1 d . U . . .
B2 B 0.6555(2) 0.7836(3) 0.61165(9) 0.0346(5) Uani 1 1 d . . . . .
H2 H 0.5543(18) 0.814(2) 0.6164(7) 0.041 Uiso 1 1 d . U . . .
N1 N 0.79692(14) 0.57842(18) 0.60962(6) 0.0315(4) Uani 1 1 d . . . . .
N2 N 0.67124(14) 0.61977(18) 0.60857(6) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.59497(18) 0.5066(2) 0.59734(7) 0.0358(5) Uani 1 1 d . . . . .
C4 C 0.67357(19) 0.3929(2) 0.59259(8) 0.0389(5) Uani 1 1 d . . . . .
H4 H 0.6463 0.2994 0.5856 0.047 Uiso 1 1 calc R U . . .
C5 C 0.79859(19) 0.4400(2) 0.59988(7) 0.0346(5) Uani 1 1 d . . . . .
C6 C 0.44986(19) 0.5086(3) 0.59057(8) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.91817(19) 0.3565(2) 0.59631(8) 0.0383(5) Uani 1 1 d . . . . .
N11 N 0.88027(13) 0.79691(17) 0.65357(6) 0.0281(4) Uani 1 1 d . . . . .
N12 N 0.75560(13) 0.82902(17) 0.65756(6) 0.0288(4) Uani 1 1 d . . . . .
C13 C 0.75734(17) 0.9182(2) 0.69468(7) 0.0310(5) Uani 1 1 d . . . . .
C14 C 0.88334(18) 0.9445(2) 0.71353(8) 0.0369(5) Uani 1 1 d . . . . .
H14 H 0.9134 1.0035 0.7401 0.044 Uiso 1 1 calc R U . . .
C15 C 0.95873(17) 0.8693(2) 0.68666(7) 0.0318(5) Uani 1 1 d . . . . .
C16 C 0.63944(18) 0.9771(2) 0.71187(8) 0.0370(5) Uani 1 1 d . . . . .
C17 C 1.10407(17) 0.8687(2) 0.69224(8) 0.0375(5) Uani 1 1 d . . . . .
C21 C 0.83543(18) 0.8001(2) 0.56348(7) 0.0343(5) Uani 1 1 d . . . . .
C22 C 0.70930(18) 0.8454(2) 0.56599(8) 0.0353(5) Uani 1 1 d . . . . .
C23 C 0.6469(2) 0.9323(3) 0.53057(8) 0.0434(5) Uani 1 1 d . . . . .
H23 H 0.5631 0.9647 0.5324 0.052 Uiso 1 1 calc R U . . .
C24 C 0.7058(2) 0.9729(3) 0.49202(9) 0.0485(6) Uani 1 1 d . . . . .
H24 H 0.6616 1.0313 0.4675 0.058 Uiso 1 1 calc R U . . .
C25 C 0.8282(2) 0.9282(3) 0.48956(8) 0.0449(6) Uani 1 1 d . . . . .
H25 H 0.8683 0.9560 0.4634 0.054 Uiso 1 1 calc R U . . .
C26 C 0.89235(19) 0.8429(2) 0.52506(8) 0.0385(5) Uani 1 1 d . . . . .
H26 H 0.9769 0.8131 0.5232 0.046 Uiso 1 1 calc R U . . .
C61 C 0.4057(2) 0.5465(4) 0.63742(10) 0.0720(9) Uani 1 1 d . . . . .
H61A H 0.3120 0.5477 0.6326 0.108 Uiso 1 1 calc R U . . .
H61B H 0.4387 0.6392 0.6479 0.108 Uiso 1 1 calc R U . . .
H61C H 0.4380 0.4769 0.6619 0.108 Uiso 1 1 calc R U . . .
C62 C 0.3957(2) 0.6102(3) 0.55091(11) 0.0634(8) Uani 1 1 d . . . . .
H62A H 0.3021 0.6102 0.5470 0.095 Uiso 1 1 calc R U . . .
H62B H 0.4221 0.5812 0.5208 0.095 Uiso 1 1 calc R U . . .
H62C H 0.4280 0.7046 0.5594 0.095 Uiso 1 1 calc R U . . .
C63 C 0.4004(2) 0.3617(3) 0.57558(11) 0.0642(8) Uani 1 1 d . . . . .
H63A H 0.3067 0.3612 0.5710 0.096 Uiso 1 1 calc R U . . .
H63B H 0.4341 0.2944 0.6007 0.096 Uiso 1 1 calc R U . . .
H63C H 0.4287 0.3355 0.5455 0.096 Uiso 1 1 calc R U . . .
C71 C 1.0144(2) 0.3646(3) 0.64279(9) 0.0512(6) Uani 1 1 d . . . . .
H71A H 1.0906 0.3099 0.6394 0.077 Uiso 1 1 calc R U . . .
H71B H 0.9757 0.3266 0.6692 0.077 Uiso 1 1 calc R U . . .
H71C H 1.0386 0.4625 0.6496 0.077 Uiso 1 1 calc R U . . .
C72 C 0.9779(2) 0.4089(3) 0.55392(9) 0.0503(6) Uani 1 1 d . . . . .
H72A H 1.0552 0.3546 0.5518 0.076 Uiso 1 1 calc R U . . .
H72B H 1.0003 0.5081 0.5586 0.076 Uiso 1 1 calc R U . . .
H72C H 0.9165 0.3976 0.5242 0.076 Uiso 1 1 calc R U . . .
C73 C 0.8809(2) 0.2025(3) 0.58716(11) 0.0598(7) Uani 1 1 d . . . . .
H73A H 0.9576 0.1473 0.5848 0.090 Uiso 1 1 calc R U . . .
H73B H 0.8200 0.1946 0.5571 0.090 Uiso 1 1 calc R U . . .
H73C H 0.8413 0.1670 0.6137 0.090 Uiso 1 1 calc R U . . .
C161 C 0.5733(2) 1.0832(3) 0.67516(10) 0.0617(8) Uani 1 1 d . . . . .
H16A H 0.4974 1.1210 0.6863 0.092 Uiso 1 1 calc R U . . .
H16B H 0.5476 1.0366 0.6442 0.092 Uiso 1 1 calc R U . . .
H16C H 0.6326 1.1597 0.6716 0.092 Uiso 1 1 calc R U . . .
C162 C 0.54722(19) 0.8603(3) 0.71996(9) 0.0482(6) Uani 1 1 d . . . . .
H16D H 0.4723 0.9007 0.7311 0.072 Uiso 1 1 calc R U . . .
H16E H 0.5902 0.7952 0.7442 0.072 Uiso 1 1 calc R U . . .
H16F H 0.5198 0.8099 0.6898 0.072 Uiso 1 1 calc R U . . .
C163 C 0.6813(2) 1.0501(3) 0.75994(9) 0.0536(7) Uani 1 1 d . . . . .
H16G H 0.6061 1.0884 0.7714 0.080 Uiso 1 1 calc R U . . .
H16H H 0.7405 1.1264 0.7559 0.080 Uiso 1 1 calc R U . . .
H16I H 0.7242 0.9825 0.7833 0.080 Uiso 1 1 calc R U . . .
C171 C 1.1561(2) 0.9724(4) 0.73140(12) 0.0745(10) Uani 1 1 d . . . . .
H17A H 1.2498 0.9735 0.7356 0.112 Uiso 1 1 calc R U . . .
H17B H 1.1292 0.9444 0.7616 0.112 Uiso 1 1 calc R U . . .
H17C H 1.1230 1.0661 0.7223 0.112 Uiso 1 1 calc R U . . .
C172 C 1.15684(19) 0.7244(3) 0.70672(10) 0.0513(6) Uani 1 1 d . . . . .
H17D H 1.2503 0.7260 0.7100 0.077 Uiso 1 1 calc R U . . .
H17E H 1.1221 0.6562 0.6821 0.077 Uiso 1 1 calc R U . . .
H17F H 1.1322 0.6979 0.7374 0.077 Uiso 1 1 calc R U . . .
C173 C 1.1475(2) 0.9161(3) 0.64580(9) 0.0523(7) Uani 1 1 d . . . . .
H17G H 1.2412 0.9146 0.6501 0.078 Uiso 1 1 calc R U . . .
H17H H 1.1168 1.0114 0.6379 0.078 Uiso 1 1 calc R U . . .
H17I H 1.1125 0.8526 0.6197 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N11 1.583(3) . ?
B1 C21 1.586(3) . ?
B1 N1 1.599(3) . ?
B1 H1 1.129(19) . ?
B2 N2 1.578(3) . ?
B2 N12 1.594(3) . ?
B2 C22 1.607(3) . ?
B2 H2 1.139(19) . ?
N1 C5 1.350(3) . ?
N1 N2 1.385(2) . ?
N2 C3 1.356(3) . ?
C3 C4 1.388(3) . ?
C3 C6 1.518(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.515(3) . ?
C6 C61 1.519(3) . ?
C6 C62 1.521(4) . ?
C6 C63 1.533(3) . ?
C7 C71 1.525(3) . ?
C7 C72 1.529(3) . ?
C7 C73 1.534(3) . ?
N11 C15 1.337(3) . ?
N11 N12 1.3795(19) . ?
N12 C13 1.349(3) . ?
C13 C14 1.377(3) . ?
C13 C16 1.522(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.523(3) . ?
C16 C162 1.526(3) . ?
C16 C163 1.526(3) . ?
C16 C161 1.533(3) . ?
C17 C172 1.517(3) . ?
C17 C171 1.519(3) . ?
C17 C173 1.530(3) . ?
C21 C26 1.389(3) . ?
C21 C22 1.418(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.398(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
C162 H16D 0.9800 . ?
C162 H16E 0.9800 . ?
C162 H16F 0.9800 . ?
C163 H16G 0.9800 . ?
C163 H16H 0.9800 . ?
C163 H16I 0.9800 . ?
C171 H17A 0.9800 . ?
C171 H17B 0.9800 . ?
C171 H17C 0.9800 . ?
C172 H17D 0.9800 . ?
C172 H17E 0.9800 . ?
C172 H17F 0.9800 . ?
C173 H17G 0.9800 . ?
C173 H17H 0.9800 . ?
C173 H17I 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 B1 C21 104.84(17) . . ?
N11 B1 N1 104.29(15) . . ?
C21 B1 N1 106.61(16) . . ?
N11 B1 H1 111.2(11) . . ?
C21 B1 H1 119.2(11) . . ?
N1 B1 H1 109.5(11) . . ?
N2 B2 N12 104.60(17) . . ?
N2 B2 C22 105.34(17) . . ?
N12 B2 C22 106.04(16) . . ?
N2 B2 H2 111.5(11) . . ?
N12 B2 H2 110.4(11) . . ?
C22 B2 H2 118.0(11) . . ?
C5 N1 N2 108.64(16) . . ?
C5 N1 B1 135.05(15) . . ?
N2 N1 B1 113.85(15) . . ?
C3 N2 N1 108.17(16) . . ?
C3 N2 B2 137.66(16) . . ?
N1 N2 B2 113.08(15) . . ?
N2 C3 C4 107.55(17) . . ?
N2 C3 C6 124.84(19) . . ?
C4 C3 C6 127.6(2) . . ?
C5 C4 C3 107.91(19) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
N1 C5 C4 107.70(18) . . ?
N1 C5 C7 124.62(18) . . ?
C4 C5 C7 127.7(2) . . ?
C3 C6 C61 110.23(19) . . ?
C3 C6 C62 110.59(18) . . ?
C61 C6 C62 110.9(2) . . ?
C3 C6 C63 108.41(19) . . ?
C61 C6 C63 108.5(2) . . ?
C62 C6 C63 108.1(2) . . ?
C5 C7 C71 111.28(17) . . ?
C5 C7 C72 109.86(18) . . ?
C71 C7 C72 110.70(19) . . ?
C5 C7 C73 108.73(18) . . ?
C71 C7 C73 108.1(2) . . ?
C72 C7 C73 108.09(19) . . ?
C15 N11 N12 108.72(15) . . ?
C15 N11 B1 136.37(14) . . ?
N12 N11 B1 114.10(14) . . ?
C13 N12 N11 108.33(15) . . ?
C13 N12 B2 136.54(15) . . ?
N11 N12 B2 112.99(14) . . ?
N12 C13 C14 107.66(16) . . ?
N12 C13 C16 125.16(17) . . ?
C14 C13 C16 127.18(18) . . ?
C13 C14 C15 107.64(18) . . ?
C13 C14 H14 126.2 . . ?
C15 C14 H14 126.2 . . ?
N11 C15 C14 107.59(15) . . ?
N11 C15 C17 124.86(17) . . ?
C14 C15 C17 127.55(19) . . ?
C13 C16 C162 110.98(17) . . ?
C13 C16 C163 108.69(17) . . ?
C162 C16 C163 107.43(18) . . ?
C13 C16 C161 109.61(17) . . ?
C162 C16 C161 110.61(19) . . ?
C163 C16 C161 109.5(2) . . ?
C172 C17 C171 108.8(2) . . ?
C172 C17 C15 110.69(18) . . ?
C171 C17 C15 108.15(17) . . ?
C172 C17 C173 110.49(18) . . ?
C171 C17 C173 107.9(2) . . ?
C15 C17 C173 110.71(18) . . ?
C26 C21 C22 119.0(2) . . ?
C26 C21 B1 128.51(18) . . ?
C22 C21 B1 112.46(16) . . ?
C23 C22 C21 119.28(18) . . ?
C23 C22 B2 127.66(18) . . ?
C21 C22 B2 113.06(18) . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 121.09(19) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C6 C61 H61A 109.5 . . ?
C6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C6 C62 H62A 109.5 . . ?
C6 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C6 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C6 C63 H63A 109.5 . . ?
C6 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C6 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C7 C72 H72A 109.5 . . ?
C7 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C7 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C7 C73 H73A 109.5 . . ?
C7 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C7 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C16 C161 H16A 109.5 . . ?
C16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
C16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
C16 C162 H16D 109.5 . . ?
C16 C162 H16E 109.5 . . ?
H16D C162 H16E 109.5 . . ?
C16 C162 H16F 109.5 . . ?
H16D C162 H16F 109.5 . . ?
H16E C162 H16F 109.5 . . ?
C16 C163 H16G 109.5 . . ?
C16 C163 H16H 109.5 . . ?
H16G C163 H16H 109.5 . . ?
C16 C163 H16I 109.5 . . ?
H16G C163 H16I 109.5 . . ?
H16H C163 H16I 109.5 . . ?
C17 C171 H17A 109.5 . . ?
C17 C171 H17B 109.5 . . ?
H17A C171 H17B 109.5 . . ?
C17 C171 H17C 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?
C17 C172 H17D 109.5 . . ?
C17 C172 H17E 109.5 . . ?
H17D C172 H17E 109.5 . . ?
C17 C172 H17F 109.5 . . ?
H17D C172 H17F 109.5 . . ?
H17E C172 H17F 109.5 . . ?
C17 C173 H17G 109.5 . . ?
C17 C173 H17H 109.5 . . ?
H17G C173 H17H 109.5 . . ?
C17 C173 H17I 109.5 . . ?
H17G C173 H17I 109.5 . . ?
H17H C173 H17I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 B1 N1 C5 -141.5(2) . . . . ?
C21 B1 N1 C5 107.9(2) . . . . ?
N11 B1 N1 N2 58.9(2) . . . . ?
C21 B1 N1 N2 -51.7(2) . . . . ?
C5 N1 N2 C3 -1.0(2) . . . . ?
B1 N1 N2 C3 163.96(16) . . . . ?
C5 N1 N2 B2 -171.24(17) . . . . ?
B1 N1 N2 B2 -6.3(2) . . . . ?
N12 B2 N2 C3 141.7(2) . . . . ?
C22 B2 N2 C3 -106.7(2) . . . . ?
N12 B2 N2 N1 -52.10(19) . . . . ?
C22 B2 N2 N1 59.5(2) . . . . ?
N1 N2 C3 C4 1.6(2) . . . . ?
B2 N2 C3 C4 168.2(2) . . . . ?
N1 N2 C3 C6 -177.40(19) . . . . ?
B2 N2 C3 C6 -10.8(4) . . . . ?
N2 C3 C4 C5 -1.6(2) . . . . ?
C6 C3 C4 C5 177.4(2) . . . . ?
N2 N1 C5 C4 0.0(2) . . . . ?
B1 N1 C5 C4 -160.4(2) . . . . ?
N2 N1 C5 C7 178.18(18) . . . . ?
B1 N1 C5 C7 17.8(3) . . . . ?
C3 C4 C5 N1 1.0(2) . . . . ?
C3 C4 C5 C7 -177.1(2) . . . . ?
N2 C3 C6 C61 -64.4(3) . . . . ?
C4 C3 C6 C61 116.9(3) . . . . ?
N2 C3 C6 C62 58.7(3) . . . . ?
C4 C3 C6 C62 -120.1(3) . . . . ?
N2 C3 C6 C63 177.0(2) . . . . ?
C4 C3 C6 C63 -1.8(3) . . . . ?
N1 C5 C7 C71 58.4(3) . . . . ?
C4 C5 C7 C71 -123.8(2) . . . . ?
N1 C5 C7 C72 -64.6(3) . . . . ?
C4 C5 C7 C72 113.3(2) . . . . ?
N1 C5 C7 C73 177.3(2) . . . . ?
C4 C5 C7 C73 -4.9(3) . . . . ?
C21 B1 N11 C15 -106.7(3) . . . . ?
N1 B1 N11 C15 141.5(2) . . . . ?
C21 B1 N11 N12 61.54(19) . . . . ?
N1 B1 N11 N12 -50.3(2) . . . . ?
C15 N11 N12 C13 -2.3(2) . . . . ?
B1 N11 N12 C13 -173.73(17) . . . . ?
C15 N11 N12 B2 163.93(17) . . . . ?
B1 N11 N12 B2 -7.5(2) . . . . ?
N2 B2 N12 C13 -138.4(2) . . . . ?
C22 B2 N12 C13 110.5(2) . . . . ?
N2 B2 N12 N11 60.75(19) . . . . ?
C22 B2 N12 N11 -50.3(2) . . . . ?
N11 N12 C13 C14 1.2(2) . . . . ?
B2 N12 C13 C14 -160.2(2) . . . . ?
N11 N12 C13 C16 -178.72(18) . . . . ?
B2 N12 C13 C16 19.9(3) . . . . ?
N12 C13 C14 C15 0.3(2) . . . . ?
C16 C13 C14 C15 -179.8(2) . . . . ?
N12 N11 C15 C14 2.4(2) . . . . ?
B1 N11 C15 C14 171.1(2) . . . . ?
N12 N11 C15 C17 -176.67(19) . . . . ?
B1 N11 C15 C17 -8.0(4) . . . . ?
C13 C14 C15 N11 -1.7(2) . . . . ?
C13 C14 C15 C17 177.4(2) . . . . ?
N12 C13 C16 C162 51.3(3) . . . . ?
C14 C13 C16 C162 -128.6(2) . . . . ?
N12 C13 C16 C163 169.2(2) . . . . ?
C14 C13 C16 C163 -10.7(3) . . . . ?
N12 C13 C16 C161 -71.2(3) . . . . ?
C14 C13 C16 C161 108.9(3) . . . . ?
N11 C15 C17 C172 -65.0(3) . . . . ?
C14 C15 C17 C172 116.1(3) . . . . ?
N11 C15 C17 C171 175.9(2) . . . . ?
C14 C15 C17 C171 -3.0(3) . . . . ?
N11 C15 C17 C173 57.9(3) . . . . ?
C14 C15 C17 C173 -121.1(2) . . . . ?
N11 B1 C21 C26 124.3(2) . . . . ?
N1 B1 C21 C26 -125.5(2) . . . . ?
N11 B1 C21 C22 -54.2(2) . . . . ?
N1 B1 C21 C22 56.0(2) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
B1 C21 C22 C23 177.9(2) . . . . ?
C26 C21 C22 B2 178.4(2) . . . . ?
B1 C21 C22 B2 -2.9(3) . . . . ?
N2 B2 C22 C23 124.9(2) . . . . ?
N12 B2 C22 C23 -124.6(2) . . . . ?
N2 B2 C22 C21 -54.2(2) . . . . ?
N12 B2 C22 C21 56.3(2) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
B2 C22 C23 C24 -177.6(2) . . . . ?
C22 C23 C24 C25 -1.1(4) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C24 C25 C26 C21 0.4(4) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
B1 C21 C26 C25 -178.6(2) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 985505'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1665

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 B2 F12 N4'
_chemical_formula_sum            'C16 H8 B2 F12 N4'
_chemical_formula_weight         505.88

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           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                   9.6394(8)
_cell_length_b                   15.7965(13)
_cell_length_c                   12.9452(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.491(7)
_cell_angle_gamma                90
_cell_volume                     1931.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18131
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      26.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29995
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.205
_diffrn_reflns_theta_max         26.197
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3832
_reflns_number_gt                2974
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0430P)²+1.4545P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
B1 B 0.6911(3) 0.2649(2) 0.3103(3) 0.0242(7) Uani 1 1 d . . . . .
H1 H 0.621(3) 0.2687(19) 0.367(2) 0.022(8) Uiso 1 1 d . . . . .
B2 B 0.8938(4) 0.2465(2) 0.1943(3) 0.0246(7) Uani 1 1 d . . . . .
H2 H 0.982(3) 0.2342(18) 0.157(2) 0.021(8) Uiso 1 1 d . . . . .
N1 N 0.7352(2) 0.16946(15) 0.2929(2) 0.0233(5) Uani 1 1 d . . . . .
N2 N 0.8364(2) 0.16017(15) 0.23499(19) 0.0234(5) Uani 1 1 d . . . . .
C3 C 0.8604(3) 0.07768(18) 0.2257(2) 0.0247(6) Uani 1 1 d . . . . .
C4 C 0.7731(3) 0.03208(19) 0.2773(3) 0.0289(7) Uani 1 1 d . . . . .
H4 H 0.7675 -0.0277 0.2836 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6959(3) 0.09226(18) 0.3178(2) 0.0257(6) Uani 1 1 d . . . . .
C6 C 0.9702(3) 0.0471(2) 0.1677(3) 0.0313(7) Uani 1 1 d . . . . .
F61 F 0.9470(2) 0.07528(12) 0.06928(15) 0.0394(5) Uani 1 1 d . . . . .
F62 F 0.9696(2) -0.03677(12) 0.16432(18) 0.0483(6) Uani 1 1 d . . . . .
F63 F 1.0996(2) 0.07204(15) 0.21450(17) 0.0483(6) Uani 1 1 d . . . . .
C7 C 0.5869(3) 0.0786(2) 0.3842(3) 0.0332(7) Uani 1 1 d . . . . .
F71 F 0.5581(3) -0.00239(14) 0.3885(3) 0.0719(9) Uani 1 1 d . . . . .
F72 F 0.4672(2) 0.11862(14) 0.34656(17) 0.0468(5) Uani 1 1 d . . . . .
F73 F 0.6304(2) 0.10678(19) 0.48146(17) 0.0622(7) Uani 1 1 d . . . . .
N11 N 0.8439(3) 0.30282(15) 0.36263(19) 0.0222(5) Uani 1 1 d . . . . .
N12 N 0.9443(2) 0.29353(15) 0.30354(19) 0.0234(5) Uani 1 1 d . . . . .
C13 C 1.0646(3) 0.3281(2) 0.3565(2) 0.0274(6) Uani 1 1 d . . . . .
C14 C 1.0444(3) 0.3602(2) 0.4508(3) 0.0313(7) Uani 1 1 d . . . . .
H14 H 1.1115 0.3883 0.5033 0.038 Uiso 1 1 calc R U . . .
C15 C 0.9047(3) 0.34261(19) 0.4521(2) 0.0278(6) Uani 1 1 d . . . . .
C16 C 1.1964(3) 0.3284(2) 0.3120(3) 0.0372(8) Uani 1 1 d . . . . .
F161 F 1.3006(2) 0.36350(19) 0.3800(2) 0.0697(8) Uani 1 1 d . . . . .
F162 F 1.1785(2) 0.37060(16) 0.22155(19) 0.0568(6) Uani 1 1 d . . . . .
F163 F 1.2377(2) 0.25077(14) 0.29240(18) 0.0482(5) Uani 1 1 d . . . . .
C17 C 0.8276(4) 0.3642(2) 0.5377(3) 0.0354(8) Uani 1 1 d . . . . .
F171 F 0.7564(3) 0.30048(17) 0.5654(2) 0.0674(7) Uani 1 1 d . . . . .
F172 F 0.9186(3) 0.3880(2) 0.62269(19) 0.0780(9) Uani 1 1 d . . . . .
F173 F 0.7385(3) 0.42670(18) 0.5104(2) 0.0736(9) Uani 1 1 d . . . . .
C21 C 0.6513(3) 0.30437(17) 0.1942(2) 0.0226(6) Uani 1 1 d . . . . .
C22 C 0.7579(3) 0.29647(17) 0.1356(2) 0.0236(6) Uani 1 1 d . . . . .
C23 C 0.7392(3) 0.33133(19) 0.0347(2) 0.0299(7) Uani 1 1 d . . . . .
H23 H 0.8121 0.3267 -0.0047 0.036 Uiso 1 1 calc R U . . .
C24 C 0.6134(4) 0.3730(2) -0.0081(3) 0.0368(8) Uani 1 1 d . . . . .
H24 H 0.6014 0.3978 -0.0761 0.044 Uiso 1 1 calc R U . . .
C25 C 0.5068(4) 0.3781(2) 0.0479(3) 0.0373(8) Uani 1 1 d . . . . .
H25 H 0.4204 0.4053 0.0175 0.045 Uiso 1 1 calc R U . . .
C26 C 0.5239(3) 0.34376(19) 0.1488(3) 0.0297(7) Uani 1 1 d . . . . .
H26 H 0.4492 0.3472 0.1867 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.594(4) . ?
B1 C21 1.603(4) . ?
B1 N11 1.609(4) . ?
B1 H1 1.10(3) . ?
B2 N12 1.586(4) . ?
B2 C22 1.587(5) . ?
B2 N2 1.599(4) . ?
B2 H2 1.08(3) . ?
N1 C5 1.335(4) . ?
N1 N2 1.352(3) . ?
N2 C3 1.333(4) . ?
C3 C4 1.378(4) . ?
C3 C6 1.494(4) . ?
C4 C5 1.373(4) . ?
C4 H4 0.9500 . ?
C5 C7 1.501(4) . ?
C6 F62 1.326(4) . ?
C6 F61 1.326(4) . ?
C6 F63 1.333(4) . ?
C7 F71 1.312(4) . ?
C7 F72 1.321(4) . ?
C7 F73 1.322(4) . ?
N11 C15 1.345(4) . ?
N11 N12 1.356(3) . ?
N12 C13 1.340(4) . ?
C13 C14 1.371(4) . ?
C13 C16 1.496(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C17 1.492(4) . ?
C16 F161 1.319(4) . ?
C16 F162 1.328(4) . ?
C16 F163 1.328(4) . ?
C17 F171 1.308(4) . ?
C17 F173 1.310(4) . ?
C17 F172 1.317(4) . ?
C21 C26 1.397(4) . ?
C21 C22 1.399(4) . ?
C22 C23 1.395(4) . ?
C23 C24 1.394(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.372(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(5) . ?
C25 H25 0.9500 . ?
C26 H26 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
N1 B1 C21 104.8(2) . . ?
N1 B1 N11 99.5(2) . . ?
C21 B1 N11 106.1(2) . . ?
N1 B1 H1 111.4(16) . . ?
C21 B1 H1 122.9(16) . . ?
N11 B1 H1 109.6(16) . . ?
N12 B2 C22 105.8(2) . . ?
N12 B2 N2 99.8(2) . . ?
C22 B2 N2 106.0(2) . . ?
N12 B2 H2 110.8(16) . . ?
C22 B2 H2 121.7(16) . . ?
N2 B2 H2 110.5(16) . . ?
C5 N1 N2 107.8(2) . . ?
C5 N1 B1 137.2(2) . . ?
N2 N1 B1 115.0(2) . . ?
C3 N2 N1 108.3(2) . . ?
C3 N2 B2 136.5(2) . . ?
N1 N2 B2 115.2(2) . . ?
N2 C3 C4 109.5(3) . . ?
N2 C3 C6 121.0(3) . . ?
C4 C3 C6 129.6(3) . . ?
C5 C4 C3 104.6(3) . . ?
C5 C4 H4 127.7 . . ?
C3 C4 H4 127.7 . . ?
N1 C5 C4 109.8(3) . . ?
N1 C5 C7 122.3(3) . . ?
C4 C5 C7 127.8(3) . . ?
F62 C6 F61 107.7(3) . . ?
F62 C6 F63 107.9(3) . . ?
F61 C6 F63 107.5(3) . . ?
F62 C6 C3 110.0(3) . . ?
F61 C6 C3 111.9(2) . . ?
F63 C6 C3 111.6(3) . . ?
F71 C7 F72 107.8(3) . . ?
F71 C7 F73 108.6(3) . . ?
F72 C7 F73 106.1(3) . . ?
F71 C7 C5 110.1(3) . . ?
F72 C7 C5 112.3(3) . . ?
F73 C7 C5 111.8(3) . . ?
C15 N11 N12 107.3(2) . . ?
C15 N11 B1 137.9(2) . . ?
N12 N11 B1 114.8(2) . . ?
C13 N12 N11 108.0(2) . . ?
C13 N12 B2 136.7(2) . . ?
N11 N12 B2 115.3(2) . . ?
N12 C13 C14 110.1(3) . . ?
N12 C13 C16 121.2(3) . . ?
C14 C13 C16 128.6(3) . . ?
C13 C14 C15 104.4(3) . . ?
C13 C14 H14 127.8 . . ?
C15 C14 H14 127.8 . . ?
N11 C15 C14 110.1(3) . . ?
N11 C15 C17 123.4(3) . . ?
C14 C15 C17 126.6(3) . . ?
F161 C16 F162 108.9(3) . . ?
F161 C16 F163 107.4(3) . . ?
F162 C16 F163 106.7(3) . . ?
F161 C16 C13 109.6(3) . . ?
F162 C16 C13 111.7(3) . . ?
F163 C16 C13 112.4(3) . . ?
F171 C17 F173 107.6(3) . . ?
F171 C17 F172 106.8(3) . . ?
F173 C17 F172 107.6(3) . . ?
F171 C17 C15 113.2(3) . . ?
F173 C17 C15 111.6(3) . . ?
F172 C17 C15 109.8(3) . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 B1 126.4(3) . . ?
C22 C21 B1 114.2(2) . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 B2 125.8(3) . . ?
C21 C22 B2 114.2(3) . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.7(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?

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
C21 B1 N1 C5 -124.0(4) . . . . ?
N11 B1 N1 C5 126.4(3) . . . . ?
C21 B1 N1 N2 53.4(3) . . . . ?
N11 B1 N1 N2 -56.2(3) . . . . ?
C5 N1 N2 C3 -0.8(3) . . . . ?
B1 N1 N2 C3 -179.0(2) . . . . ?
C5 N1 N2 B2 178.1(2) . . . . ?
B1 N1 N2 B2 0.0(3) . . . . ?
N12 B2 N2 C3 -124.8(3) . . . . ?
C22 B2 N2 C3 125.5(3) . . . . ?
N12 B2 N2 N1 56.6(3) . . . . ?
C22 B2 N2 N1 -53.0(3) . . . . ?
N1 N2 C3 C4 0.5(3) . . . . ?
B2 N2 C3 C4 -178.1(3) . . . . ?
N1 N2 C3 C6 -178.5(3) . . . . ?
B2 N2 C3 C6 2.9(5) . . . . ?
N2 C3 C4 C5 0.0(3) . . . . ?
C6 C3 C4 C5 178.9(3) . . . . ?
N2 N1 C5 C4 0.9(3) . . . . ?
B1 N1 C5 C4 178.4(3) . . . . ?
N2 N1 C5 C7 178.6(3) . . . . ?
B1 N1 C5 C7 -3.9(5) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C3 C4 C5 C7 -178.1(3) . . . . ?
N2 C3 C6 F62 -176.8(3) . . . . ?
C4 C3 C6 F62 4.5(5) . . . . ?
N2 C3 C6 F61 -57.1(4) . . . . ?
C4 C3 C6 F61 124.2(3) . . . . ?
N2 C3 C6 F63 63.5(4) . . . . ?
C4 C3 C6 F63 -115.3(4) . . . . ?
N1 C5 C7 F71 174.0(3) . . . . ?
C4 C5 C7 F71 -8.7(5) . . . . ?
N1 C5 C7 F72 53.9(4) . . . . ?
C4 C5 C7 F72 -128.8(3) . . . . ?
N1 C5 C7 F73 -65.2(4) . . . . ?
C4 C5 C7 F73 112.0(4) . . . . ?
N1 B1 N11 C15 -122.8(3) . . . . ?
C21 B1 N11 C15 128.6(3) . . . . ?
N1 B1 N11 N12 56.7(3) . . . . ?
C21 B1 N11 N12 -51.8(3) . . . . ?
C15 N11 N12 C13 -0.5(3) . . . . ?
B1 N11 N12 C13 179.8(2) . . . . ?
C15 N11 N12 B2 179.3(2) . . . . ?
B1 N11 N12 B2 -0.5(3) . . . . ?
C22 B2 N12 C13 -126.4(3) . . . . ?
N2 B2 N12 C13 123.7(3) . . . . ?
C22 B2 N12 N11 53.9(3) . . . . ?
N2 B2 N12 N11 -56.0(3) . . . . ?
N11 N12 C13 C14 0.1(3) . . . . ?
B2 N12 C13 C14 -179.6(3) . . . . ?
N11 N12 C13 C16 -179.8(3) . . . . ?
B2 N12 C13 C16 0.4(5) . . . . ?
N12 C13 C14 C15 0.3(4) . . . . ?
C16 C13 C14 C15 -179.7(3) . . . . ?
N12 N11 C15 C14 0.8(3) . . . . ?
B1 N11 C15 C14 -179.6(3) . . . . ?
N12 N11 C15 C17 -179.9(3) . . . . ?
B1 N11 C15 C17 -0.3(5) . . . . ?
C13 C14 C15 N11 -0.7(4) . . . . ?
C13 C14 C15 C17 -180.0(3) . . . . ?
N12 C13 C16 F161 -178.1(3) . . . . ?
C14 C13 C16 F161 1.9(5) . . . . ?
N12 C13 C16 F162 61.0(4) . . . . ?
C14 C13 C16 F162 -118.9(4) . . . . ?
N12 C13 C16 F163 -58.8(4) . . . . ?
C14 C13 C16 F163 121.2(4) . . . . ?
N11 C15 C17 F171 49.1(4) . . . . ?
C14 C15 C17 F171 -131.7(4) . . . . ?
N11 C15 C17 F173 -72.5(4) . . . . ?
C14 C15 C17 F173 106.7(4) . . . . ?
N11 C15 C17 F172 168.3(3) . . . . ?
C14 C15 C17 F172 -12.5(5) . . . . ?
N1 B1 C21 C26 125.0(3) . . . . ?
N11 B1 C21 C26 -130.3(3) . . . . ?
N1 B1 C21 C22 -54.6(3) . . . . ?
N11 B1 C21 C22 50.1(3) . . . . ?
C26 C21 C22 C23 3.0(4) . . . . ?
B1 C21 C22 C23 -177.3(3) . . . . ?
C26 C21 C22 B2 -177.1(3) . . . . ?
B1 C21 C22 B2 2.5(3) . . . . ?
N12 B2 C22 C23 125.2(3) . . . . ?
N2 B2 C22 C23 -129.4(3) . . . . ?
N12 B2 C22 C21 -54.6(3) . . . . ?
N2 B2 C22 C21 50.7(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
B2 C22 C23 C24 179.2(3) . . . . ?
C22 C23 C24 C25 -1.4(5) . . . . ?
C23 C24 C25 C26 1.6(5) . . . . ?
C24 C25 C26 C21 0.6(5) . . . . ?
C22 C21 C26 C25 -2.9(4) . . . . ?
B1 C21 C26 C25 177.5(3) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.056

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 985506'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1614

# start Validation Reply Form
_vrf_RINTA01_wa1614              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystal was rather small and weakly diffracting.
;
_vrf_PLAT020_wa1614              
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.276       
RESPONSE:  The crystal was rather small and weakly diffracting.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 B2 Fe I2 N4, C4 H10 O'
_chemical_formula_sum            'C20 H24 B2 Fe I2 N4 O'
_chemical_formula_weight         667.70

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'
Fe Fe 0.3463 0.8444 '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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   11.061(3)
_cell_length_b                   7.8312(14)
_cell_length_c                   27.648(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.73(2)
_cell_angle_gamma                90.00
_cell_volume                     2367.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5393
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.5

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    3.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6402
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18238
_diffrn_reflns_av_R_equivalents  0.2756
_diffrn_reflns_av_sigmaI/netI    0.2649
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.88
_reflns_number_total             4568
_reflns_number_gt                1849
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0534P)²] 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         4568
_refine_ls_number_parameters     271
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.2363
_refine_ls_R_factor_gt           0.1148
_refine_ls_wR_factor_ref         0.2362
_refine_ls_wR_factor_gt          0.1924
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.986
_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
Fe1 Fe 0.7425(2) 0.6375(4) 0.04937(11) 0.0253(7) Uani 1 1 d . . .
I1 I 0.12201(10) 0.7025(2) 0.07665(6) 0.0415(4) Uani 1 1 d . . .
I2 I 0.89152(15) 1.1982(3) 0.26341(7) 0.0616(6) Uani 1 1 d . . .
B1 B 0.6335(15) 0.657(2) 0.1529(7) 0.016(4) Uani 1 1 d U . .
H1 H 0.6231 0.5864 0.1820 0.019 Uiso 1 1 calc R . .
B2 B 0.6082(17) 0.959(3) 0.0854(8) 0.022(5) Uani 1 1 d U . .
H2 H 0.5798 1.0763 0.0749 0.027 Uiso 1 1 calc R . .
N1 N 0.5031(11) 0.721(2) 0.1251(6) 0.022(3) Uani 1 1 d U . .
N2 N 0.4948(13) 0.853(2) 0.0964(6) 0.028(4) Uani 1 1 d U . .
C3 C 0.3734(15) 0.866(3) 0.0762(7) 0.025(4) Uani 1 1 d U . .
H3 H 0.3399 0.9499 0.0532 0.030 Uiso 1 1 calc R . .
C4 C 0.3095(15) 0.740(2) 0.0940(7) 0.026(5) Uani 1 1 d U . .
C5 C 0.3934(16) 0.646(3) 0.1271(8) 0.033(5) Uani 1 1 d U . .
H5 H 0.3768 0.5513 0.1465 0.039 Uiso 1 1 calc R . .
N11 N 0.7021(13) 0.831(2) 0.1693(6) 0.031(4) Uani 1 1 d U . .
N12 N 0.6901(12) 0.972(2) 0.1380(6) 0.024(4) Uani 1 1 d U . .
C13 C 0.7491(15) 1.103(3) 0.1605(7) 0.026(4) Uani 1 1 d U . .
H13 H 0.7587 1.2124 0.1468 0.031 Uiso 1 1 calc R . .
C14 C 0.7950(17) 1.051(3) 0.2087(7) 0.032(5) Uani 1 1 d U . .
C15 C 0.7667(16) 0.880(3) 0.2129(8) 0.028(5) Uani 1 1 d U . .
H15 H 0.7883 0.8103 0.2410 0.033 Uiso 1 1 calc R . .
C21 C 0.7006(15) 0.553(2) 0.1160(7) 0.023(4) Uani 1 1 d U . .
C22 C 0.8314(16) 0.537(3) 0.1144(7) 0.024(4) Uani 1 1 d U . .
H22 H 0.8943 0.5899 0.1366 0.028 Uiso 1 1 calc R . .
C23 C 0.8506(17) 0.430(3) 0.0746(8) 0.032(5) Uani 1 1 d U . .
H23 H 0.9280 0.3996 0.0661 0.039 Uiso 1 1 calc R . .
C24 C 0.7374(14) 0.376(3) 0.0498(8) 0.028(4) Uani 1 1 d U . .
H24 H 0.7238 0.3062 0.0215 0.034 Uiso 1 1 calc R . .
C25 C 0.6450(16) 0.447(3) 0.0755(8) 0.036(5) Uani 1 1 d U . .
H25 H 0.5597 0.4278 0.0670 0.043 Uiso 1 1 calc R . .
C31 C 0.6696(15) 0.880(3) 0.0452(7) 0.026(4) Uani 1 1 d U . .
C32 C 0.7929(17) 0.885(3) 0.0426(8) 0.035(5) Uani 1 1 d U . .
H32 H 0.8517 0.9451 0.0648 0.043 Uiso 1 1 calc R . .
C33 C 0.8212(19) 0.785(3) 0.0014(8) 0.042(5) Uani 1 1 d U . .
H33 H 0.8996 0.7670 -0.0078 0.051 Uiso 1 1 calc R . .
C34 C 0.7023(16) 0.716(3) -0.0232(7) 0.033(5) Uani 1 1 d U . .
H34 H 0.6880 0.6481 -0.0520 0.039 Uiso 1 1 calc R . .
C35 C 0.6155(16) 0.773(3) 0.0055(7) 0.035(5) Uani 1 1 d U . .
H35 H 0.5311 0.7448 -0.0006 0.042 Uiso 1 1 calc R . .
O41 O 0.3042(16) 0.246(3) 0.1805(7) 0.068(6) Uani 1 1 d U . .
C41 C 0.216(4) 0.146(6) 0.1520(16) 0.115(14) Uani 1 1 d U . .
H41A H 0.2294 0.1527 0.1175 0.138 Uiso 1 1 calc R . .
H41B H 0.2269 0.0258 0.1626 0.138 Uiso 1 1 calc R . .
C42 C 0.097(3) 0.194(5) 0.1545(14) 0.091(9) Uani 1 1 d U . .
H42A H 0.0411 0.1172 0.1341 0.136 Uiso 1 1 calc R . .
H42B H 0.0842 0.3113 0.1427 0.136 Uiso 1 1 calc R . .
H42C H 0.0826 0.1870 0.1885 0.136 Uiso 1 1 calc R . .
C43 C 0.418(3) 0.168(5) 0.1892(14) 0.099(12) Uani 1 1 d U . .
H43A H 0.4528 0.1620 0.1584 0.119 Uiso 1 1 calc R . .
H43B H 0.4084 0.0495 0.2008 0.119 Uiso 1 1 calc R . .
C44 C 0.498(3) 0.260(4) 0.2249(12) 0.079(9) Uani 1 1 d U . .
H44A H 0.5779 0.2029 0.2305 0.118 Uiso 1 1 calc R . .
H44B H 0.4638 0.2637 0.2556 0.118 Uiso 1 1 calc R . .
H44C H 0.5080 0.3763 0.2132 0.118 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
Fe1 C35 2.014(19) . ?
Fe1 C32 2.03(2) . ?
Fe1 C25 2.03(2) . ?
Fe1 C24 2.05(2) . ?
Fe1 C33 2.05(2) . ?
Fe1 C31 2.06(2) . ?
Fe1 C22 2.071(18) . ?
Fe1 C23 2.08(2) . ?
Fe1 C21 2.077(19) . ?
Fe1 C34 2.08(2) . ?
I1 C4 2.078(17) . ?
I2 C14 2.064(19) . ?
B1 C21 1.58(3) . ?
B1 N11 1.59(2) . ?
B1 N1 1.61(2) . ?
B1 H1 1.0000 . ?
B2 C31 1.52(3) . ?
B2 N2 1.57(2) . ?
B2 N12 1.60(2) . ?
B2 H2 1.0000 . ?
N1 N2 1.30(2) . ?
N1 C5 1.36(2) . ?
N2 C3 1.38(2) . ?
C3 C4 1.35(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.41(3) . ?
C5 H5 0.9500 . ?
N11 C15 1.36(3) . ?
N11 N12 1.39(2) . ?
N12 C13 1.32(2) . ?
C13 C14 1.41(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.39(3) . ?
C15 H15 0.9500 . ?
C21 C25 1.45(3) . ?
C21 C22 1.46(2) . ?
C22 C23 1.43(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.40(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.44(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C31 C32 1.38(2) . ?
C31 C35 1.43(3) . ?
C32 C33 1.45(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.49(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.41(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
O41 C43 1.38(4) . ?
O41 C41 1.40(4) . ?
C41 C42 1.37(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.42(4) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

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
C35 Fe1 C32 67.5(8) . . ?
C35 Fe1 C25 104.0(8) . . ?
C32 Fe1 C25 153.9(9) . . ?
C35 Fe1 C24 120.9(8) . . ?
C32 Fe1 C24 164.1(7) . . ?
C25 Fe1 C24 41.3(8) . . ?
C35 Fe1 C33 68.9(8) . . ?
C32 Fe1 C33 41.8(9) . . ?
C25 Fe1 C33 160.4(9) . . ?
C24 Fe1 C33 125.6(9) . . ?
C35 Fe1 C31 41.2(8) . . ?
C32 Fe1 C31 39.3(7) . . ?
C25 Fe1 C31 118.1(8) . . ?
C24 Fe1 C31 155.6(7) . . ?
C33 Fe1 C31 69.3(9) . . ?
C35 Fe1 C22 156.9(8) . . ?
C32 Fe1 C22 110.0(8) . . ?
C25 Fe1 C22 67.7(8) . . ?
C24 Fe1 C22 67.9(8) . . ?
C33 Fe1 C22 125.7(8) . . ?
C31 Fe1 C22 122.0(8) . . ?
C35 Fe1 C23 158.3(9) . . ?
C32 Fe1 C23 128.7(8) . . ?
C25 Fe1 C23 67.4(8) . . ?
C24 Fe1 C23 39.6(7) . . ?
C33 Fe1 C23 112.2(9) . . ?
C31 Fe1 C23 160.4(8) . . ?
C22 Fe1 C23 40.3(8) . . ?
C35 Fe1 C21 118.3(7) . . ?
C32 Fe1 C21 119.2(9) . . ?
C25 Fe1 C21 41.3(8) . . ?
C24 Fe1 C21 70.4(8) . . ?
C33 Fe1 C21 158.2(8) . . ?
C31 Fe1 C21 101.9(7) . . ?
C22 Fe1 C21 41.2(6) . . ?
C23 Fe1 C21 69.3(7) . . ?
C35 Fe1 C34 40.2(8) . . ?
C32 Fe1 C34 69.6(9) . . ?
C25 Fe1 C34 120.7(8) . . ?
C24 Fe1 C34 107.4(9) . . ?
C33 Fe1 C34 42.2(8) . . ?
C31 Fe1 C34 69.5(8) . . ?
C22 Fe1 C34 162.5(7) . . ?
C23 Fe1 C34 125.6(9) . . ?
C21 Fe1 C34 155.0(7) . . ?
C21 B1 N11 112.3(14) . . ?
C21 B1 N1 109.1(14) . . ?
N11 B1 N1 103.1(13) . . ?
C21 B1 H1 110.7 . . ?
N11 B1 H1 110.7 . . ?
N1 B1 H1 110.7 . . ?
C31 B2 N2 112.6(17) . . ?
C31 B2 N12 115.9(15) . . ?
N2 B2 N12 102.5(14) . . ?
C31 B2 H2 108.5 . . ?
N2 B2 H2 108.5 . . ?
N12 B2 H2 108.5 . . ?
N2 N1 C5 112.9(15) . . ?
N2 N1 B1 121.0(13) . . ?
C5 N1 B1 126.1(16) . . ?
N1 N2 C3 106.3(14) . . ?
N1 N2 B2 123.7(14) . . ?
C3 N2 B2 129.8(17) . . ?
C4 C3 N2 109.2(17) . . ?
C4 C3 H3 125.4 . . ?
N2 C3 H3 125.4 . . ?
C3 C4 C5 106.9(16) . . ?
C3 C4 I1 125.3(13) . . ?
C5 C4 I1 127.8(14) . . ?
N1 C5 C4 104.6(18) . . ?
N1 C5 H5 127.7 . . ?
C4 C5 H5 127.7 . . ?
C15 N11 N12 108.3(16) . . ?
C15 N11 B1 131.3(17) . . ?
N12 N11 B1 120.1(15) . . ?
C13 N12 N11 109.2(16) . . ?
C13 N12 B2 130.5(17) . . ?
N11 N12 B2 120.3(15) . . ?
N12 C13 C14 107.6(18) . . ?
N12 C13 H13 126.2 . . ?
C14 C13 H13 126.2 . . ?
C15 C14 C13 107.6(17) . . ?
C15 C14 I2 125.1(16) . . ?
C13 C14 I2 127.2(16) . . ?
N11 C15 C14 107.1(18) . . ?
N11 C15 H15 126.4 . . ?
C14 C15 H15 126.4 . . ?
C25 C21 C22 103.5(16) . . ?
C25 C21 B1 127.5(15) . . ?
C22 C21 B1 129.0(16) . . ?
C25 C21 Fe1 67.8(11) . . ?
C22 C21 Fe1 69.2(10) . . ?
B1 C21 Fe1 126.6(13) . . ?
C23 C22 C21 109.7(16) . . ?
C23 C22 Fe1 70.1(11) . . ?
C21 C22 Fe1 69.6(10) . . ?
C23 C22 H22 125.1 . . ?
C21 C22 H22 125.1 . . ?
Fe1 C22 H22 126.8 . . ?
C24 C23 C22 109.0(17) . . ?
C24 C23 Fe1 69.1(12) . . ?
C22 C23 Fe1 69.7(11) . . ?
C24 C23 H23 125.5 . . ?
C22 C23 H23 125.5 . . ?
Fe1 C23 H23 127.4 . . ?
C23 C24 C25 107.1(18) . . ?
C23 C24 Fe1 71.3(12) . . ?
C25 C24 Fe1 68.9(12) . . ?
C23 C24 H24 126.5 . . ?
C25 C24 H24 126.5 . . ?
Fe1 C24 H24 124.9 . . ?
C24 C25 C21 110.5(15) . . ?
C24 C25 Fe1 69.8(11) . . ?
C21 C25 Fe1 70.9(11) . . ?
C24 C25 H25 124.7 . . ?
C21 C25 H25 124.7 . . ?
Fe1 C25 H25 126.2 . . ?
C32 C31 C35 106.1(18) . . ?
C32 C31 B2 125.6(19) . . ?
C35 C31 B2 128.0(16) . . ?
C32 C31 Fe1 69.2(13) . . ?
C35 C31 Fe1 67.7(12) . . ?
B2 C31 Fe1 123.3(14) . . ?
C31 C32 C33 111.0(19) . . ?
C31 C32 Fe1 71.4(13) . . ?
C33 C32 Fe1 69.8(14) . . ?
C31 C32 H32 124.5 . . ?
C33 C32 H32 124.5 . . ?
Fe1 C32 H32 125.9 . . ?
C32 C33 C34 105.8(17) . . ?
C32 C33 Fe1 68.5(12) . . ?
C34 C33 Fe1 70.1(12) . . ?
C32 C33 H33 127.1 . . ?
C34 C33 H33 127.1 . . ?
Fe1 C33 H33 126.0 . . ?
C35 C34 C33 104.9(18) . . ?
C35 C34 Fe1 67.3(11) . . ?
C33 C34 Fe1 67.7(11) . . ?
C35 C34 H34 127.6 . . ?
C33 C34 H34 127.6 . . ?
Fe1 C34 H34 128.9 . . ?
C34 C35 C31 112.1(16) . . ?
C34 C35 Fe1 72.4(12) . . ?
C31 C35 Fe1 71.1(11) . . ?
C34 C35 H35 124.0 . . ?
C31 C35 H35 124.0 . . ?
Fe1 C35 H35 124.1 . . ?
C43 O41 C41 113(3) . . ?
C42 C41 O41 114(4) . . ?
C42 C41 H41A 108.7 . . ?
O41 C41 H41A 108.7 . . ?
C42 C41 H41B 108.7 . . ?
O41 C41 H41B 108.7 . . ?
H41A C41 H41B 107.6 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O41 C43 C44 111(3) . . ?
O41 C43 H43A 109.5 . . ?
C44 C43 H43A 109.5 . . ?
O41 C43 H43B 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 108.1 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

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
C21 B1 N1 N2 -79(2) . . . . ?
N11 B1 N1 N2 40(2) . . . . ?
C21 B1 N1 C5 99(2) . . . . ?
N11 B1 N1 C5 -141.5(18) . . . . ?
C5 N1 N2 C3 -2(2) . . . . ?
B1 N1 N2 C3 176.1(15) . . . . ?
C5 N1 N2 B2 -177.2(17) . . . . ?
B1 N1 N2 B2 1(3) . . . . ?
C31 B2 N2 N1 83(2) . . . . ?
N12 B2 N2 N1 -42(2) . . . . ?
C31 B2 N2 C3 -90(2) . . . . ?
N12 B2 N2 C3 144.5(18) . . . . ?
N1 N2 C3 C4 1(2) . . . . ?
B2 N2 C3 C4 175.4(19) . . . . ?
N2 C3 C4 C5 1(2) . . . . ?
N2 C3 C4 I1 178.8(13) . . . . ?
N2 N1 C5 C4 3(2) . . . . ?
B1 N1 C5 C4 -175.5(17) . . . . ?
C3 C4 C5 N1 -2(2) . . . . ?
I1 C4 C5 N1 180.0(14) . . . . ?
C21 B1 N11 C15 -110(2) . . . . ?
N1 B1 N11 C15 133.0(18) . . . . ?
C21 B1 N11 N12 77.7(19) . . . . ?
N1 B1 N11 N12 -40(2) . . . . ?
C15 N11 N12 C13 2.2(19) . . . . ?
B1 N11 N12 C13 176.4(14) . . . . ?
C15 N11 N12 B2 -174.5(15) . . . . ?
B1 N11 N12 B2 0(2) . . . . ?
C31 B2 N12 C13 101(2) . . . . ?
N2 B2 N12 C13 -135.6(19) . . . . ?
C31 B2 N12 N11 -83(2) . . . . ?
N2 B2 N12 N11 40(2) . . . . ?
N11 N12 C13 C14 -3(2) . . . . ?
B2 N12 C13 C14 172.9(17) . . . . ?
N12 C13 C14 C15 3(2) . . . . ?
N12 C13 C14 I2 -178.2(14) . . . . ?
N12 N11 C15 C14 -0.1(19) . . . . ?
B1 N11 C15 C14 -173.4(16) . . . . ?
C13 C14 C15 N11 -2(2) . . . . ?
I2 C14 C15 N11 179.5(13) . . . . ?
N11 B1 C21 C25 -145.4(19) . . . . ?
N1 B1 C21 C25 -32(3) . . . . ?
N11 B1 C21 C22 35(3) . . . . ?
N1 B1 C21 C22 148.6(18) . . . . ?
N11 B1 C21 Fe1 -56.8(19) . . . . ?
N1 B1 C21 Fe1 56.9(19) . . . . ?
C35 Fe1 C21 C25 78.7(13) . . . . ?
C32 Fe1 C21 C25 157.3(11) . . . . ?
C24 Fe1 C21 C25 -36.7(11) . . . . ?
C33 Fe1 C21 C25 -177(2) . . . . ?
C31 Fe1 C21 C25 119.3(12) . . . . ?
C22 Fe1 C21 C25 -115.2(16) . . . . ?
C23 Fe1 C21 C25 -79.0(12) . . . . ?
C34 Fe1 C21 C25 53(2) . . . . ?
C35 Fe1 C21 C22 -166.1(12) . . . . ?
C32 Fe1 C21 C22 -87.5(12) . . . . ?
C25 Fe1 C21 C22 115.2(16) . . . . ?
C24 Fe1 C21 C22 78.5(11) . . . . ?
C33 Fe1 C21 C22 -62(3) . . . . ?
C31 Fe1 C21 C22 -125.5(11) . . . . ?
C23 Fe1 C21 C22 36.2(11) . . . . ?
C34 Fe1 C21 C22 167.7(19) . . . . ?
C35 Fe1 C21 B1 -42.4(18) . . . . ?
C32 Fe1 C21 B1 36.3(17) . . . . ?
C25 Fe1 C21 B1 -121.0(18) . . . . ?
C24 Fe1 C21 B1 -157.7(16) . . . . ?
C33 Fe1 C21 B1 62(3) . . . . ?
C31 Fe1 C21 B1 -1.8(16) . . . . ?
C22 Fe1 C21 B1 124(2) . . . . ?
C23 Fe1 C21 B1 160.0(17) . . . . ?
C34 Fe1 C21 B1 -69(3) . . . . ?
C25 C21 C22 C23 1(2) . . . . ?
B1 C21 C22 C23 -179.5(19) . . . . ?
Fe1 C21 C22 C23 -58.7(14) . . . . ?
C25 C21 C22 Fe1 59.5(13) . . . . ?
B1 C21 C22 Fe1 -121(2) . . . . ?
C35 Fe1 C22 C23 154(2) . . . . ?
C32 Fe1 C22 C23 -126.9(12) . . . . ?
C25 Fe1 C22 C23 81.0(13) . . . . ?
C24 Fe1 C22 C23 36.2(11) . . . . ?
C33 Fe1 C22 C23 -82.6(14) . . . . ?
C31 Fe1 C22 C23 -168.9(10) . . . . ?
C21 Fe1 C22 C23 121.2(16) . . . . ?
C34 Fe1 C22 C23 -41(3) . . . . ?
C35 Fe1 C22 C21 33(3) . . . . ?
C32 Fe1 C22 C21 111.9(12) . . . . ?
C25 Fe1 C22 C21 -40.2(12) . . . . ?
C24 Fe1 C22 C21 -85.0(12) . . . . ?
C33 Fe1 C22 C21 156.2(13) . . . . ?
C31 Fe1 C22 C21 69.9(13) . . . . ?
C23 Fe1 C22 C21 -121.2(16) . . . . ?
C34 Fe1 C22 C21 -163(3) . . . . ?
C21 C22 C23 C24 1(2) . . . . ?
Fe1 C22 C23 C24 -57.9(15) . . . . ?
C21 C22 C23 Fe1 58.4(13) . . . . ?
C35 Fe1 C23 C24 -31(3) . . . . ?
C32 Fe1 C23 C24 -164.7(13) . . . . ?
C25 Fe1 C23 C24 39.3(13) . . . . ?
C33 Fe1 C23 C24 -119.5(13) . . . . ?
C31 Fe1 C23 C24 150(2) . . . . ?
C22 Fe1 C23 C24 121.0(17) . . . . ?
C21 Fe1 C23 C24 83.9(13) . . . . ?
C34 Fe1 C23 C24 -73.2(15) . . . . ?
C35 Fe1 C23 C22 -152(2) . . . . ?
C32 Fe1 C23 C22 74.4(14) . . . . ?
C25 Fe1 C23 C22 -81.6(12) . . . . ?
C24 Fe1 C23 C22 -121.0(17) . . . . ?
C33 Fe1 C23 C22 119.6(12) . . . . ?
C31 Fe1 C23 C22 29(3) . . . . ?
C21 Fe1 C23 C22 -37.0(11) . . . . ?
C34 Fe1 C23 C22 165.9(11) . . . . ?
C22 C23 C24 C25 -2(2) . . . . ?
Fe1 C23 C24 C25 -59.9(15) . . . . ?
C22 C23 C24 Fe1 58.3(15) . . . . ?
C35 Fe1 C24 C23 167.2(12) . . . . ?
C32 Fe1 C24 C23 49(4) . . . . ?
C25 Fe1 C24 C23 -117.6(18) . . . . ?
C33 Fe1 C24 C23 82.3(15) . . . . ?
C31 Fe1 C24 C23 -156.1(17) . . . . ?
C22 Fe1 C24 C23 -36.7(12) . . . . ?
C21 Fe1 C24 C23 -80.9(13) . . . . ?
C34 Fe1 C24 C23 125.4(13) . . . . ?
C35 Fe1 C24 C25 -75.2(14) . . . . ?
C32 Fe1 C24 C25 166(3) . . . . ?
C33 Fe1 C24 C25 -160.1(11) . . . . ?
C31 Fe1 C24 C25 -39(2) . . . . ?
C22 Fe1 C24 C25 80.9(12) . . . . ?
C23 Fe1 C24 C25 117.6(18) . . . . ?
C21 Fe1 C24 C25 36.7(11) . . . . ?
C34 Fe1 C24 C25 -117.0(12) . . . . ?
C23 C24 C25 C21 2(2) . . . . ?
Fe1 C24 C25 C21 -59.3(15) . . . . ?
C23 C24 C25 Fe1 61.4(15) . . . . ?
C22 C21 C25 C24 -2(2) . . . . ?
B1 C21 C25 C24 178.5(18) . . . . ?
Fe1 C21 C25 C24 58.7(15) . . . . ?
C22 C21 C25 Fe1 -60.4(13) . . . . ?
B1 C21 C25 Fe1 119.9(19) . . . . ?
C35 Fe1 C25 C24 121.3(12) . . . . ?
C32 Fe1 C25 C24 -171.6(16) . . . . ?
C33 Fe1 C25 C24 55(3) . . . . ?
C31 Fe1 C25 C24 163.1(11) . . . . ?
C22 Fe1 C25 C24 -81.4(12) . . . . ?
C23 Fe1 C25 C24 -37.7(11) . . . . ?
C21 Fe1 C25 C24 -121.5(15) . . . . ?
C34 Fe1 C25 C24 81.4(13) . . . . ?
C35 Fe1 C25 C21 -117.2(11) . . . . ?
C32 Fe1 C25 C21 -50(2) . . . . ?
C24 Fe1 C25 C21 121.5(15) . . . . ?
C33 Fe1 C25 C21 177(2) . . . . ?
C31 Fe1 C25 C21 -75.4(12) . . . . ?
C22 Fe1 C25 C21 40.1(10) . . . . ?
C23 Fe1 C25 C21 83.8(11) . . . . ?
C34 Fe1 C25 C21 -157.0(10) . . . . ?
N2 B2 C31 C32 -147(2) . . . . ?
N12 B2 C31 C32 -29(3) . . . . ?
N2 B2 C31 C35 27(3) . . . . ?
N12 B2 C31 C35 145(2) . . . . ?
N2 B2 C31 Fe1 -59(2) . . . . ?
N12 B2 C31 Fe1 58(2) . . . . ?
C35 Fe1 C31 C32 -118.5(17) . . . . ?
C25 Fe1 C31 C32 162.7(13) . . . . ?
C24 Fe1 C31 C32 -169.5(19) . . . . ?
C33 Fe1 C31 C32 -37.3(12) . . . . ?
C22 Fe1 C31 C32 82.7(14) . . . . ?
C23 Fe1 C31 C32 61(3) . . . . ?
C21 Fe1 C31 C32 121.9(13) . . . . ?
C34 Fe1 C31 C32 -82.5(13) . . . . ?
C32 Fe1 C31 C35 118.5(17) . . . . ?
C25 Fe1 C31 C35 -78.8(13) . . . . ?
C24 Fe1 C31 C35 -51(2) . . . . ?
C33 Fe1 C31 C35 81.2(12) . . . . ?
C22 Fe1 C31 C35 -158.8(11) . . . . ?
C23 Fe1 C31 C35 179(2) . . . . ?
C21 Fe1 C31 C35 -119.6(11) . . . . ?
C34 Fe1 C31 C35 35.9(11) . . . . ?
C35 Fe1 C31 B2 121.8(19) . . . . ?
C32 Fe1 C31 B2 -120(2) . . . . ?
C25 Fe1 C31 B2 43.0(18) . . . . ?
C24 Fe1 C31 B2 71(3) . . . . ?
C33 Fe1 C31 B2 -157.0(17) . . . . ?
C22 Fe1 C31 B2 -37.0(17) . . . . ?
C23 Fe1 C31 B2 -59(3) . . . . ?
C21 Fe1 C31 B2 2.2(16) . . . . ?
C34 Fe1 C31 B2 157.7(17) . . . . ?
C35 C31 C32 C33 1(3) . . . . ?
B2 C31 C32 C33 175(2) . . . . ?
Fe1 C31 C32 C33 58.7(17) . . . . ?
C35 C31 C32 Fe1 -57.9(14) . . . . ?
B2 C31 C32 Fe1 117(2) . . . . ?
C35 Fe1 C32 C31 38.8(12) . . . . ?
C25 Fe1 C32 C31 -37(2) . . . . ?
C24 Fe1 C32 C31 164(3) . . . . ?
C33 Fe1 C32 C31 121.8(17) . . . . ?
C22 Fe1 C32 C31 -116.5(12) . . . . ?
C23 Fe1 C32 C31 -158.0(12) . . . . ?
C21 Fe1 C32 C31 -72.0(13) . . . . ?
C34 Fe1 C32 C31 82.1(12) . . . . ?
C35 Fe1 C32 C33 -83.0(13) . . . . ?
C25 Fe1 C32 C33 -158.4(17) . . . . ?
C24 Fe1 C32 C33 42(4) . . . . ?
C31 Fe1 C32 C33 -121.8(17) . . . . ?
C22 Fe1 C32 C33 121.7(12) . . . . ?
C23 Fe1 C32 C33 80.2(14) . . . . ?
C21 Fe1 C32 C33 166.2(11) . . . . ?
C34 Fe1 C32 C33 -39.7(11) . . . . ?
C31 C32 C33 C34 1(3) . . . . ?
Fe1 C32 C33 C34 60.5(15) . . . . ?
C31 C32 C33 Fe1 -59.7(16) . . . . ?
C35 Fe1 C33 C32 79.4(13) . . . . ?
C25 Fe1 C33 C32 151(2) . . . . ?
C24 Fe1 C33 C32 -166.9(10) . . . . ?
C31 Fe1 C33 C32 35.2(11) . . . . ?
C22 Fe1 C33 C32 -80.0(14) . . . . ?
C23 Fe1 C33 C32 -123.8(12) . . . . ?
C21 Fe1 C33 C32 -34(3) . . . . ?
C34 Fe1 C33 C32 117.1(17) . . . . ?
C35 Fe1 C33 C34 -37.6(13) . . . . ?
C32 Fe1 C33 C34 -117.1(17) . . . . ?
C25 Fe1 C33 C34 34(3) . . . . ?
C24 Fe1 C33 C34 76.0(15) . . . . ?
C31 Fe1 C33 C34 -81.9(13) . . . . ?
C22 Fe1 C33 C34 162.9(12) . . . . ?
C23 Fe1 C33 C34 119.1(13) . . . . ?
C21 Fe1 C33 C34 -151.3(19) . . . . ?
C32 C33 C34 C35 -2(2) . . . . ?
Fe1 C33 C34 C35 57.3(16) . . . . ?
C32 C33 C34 Fe1 -59.4(15) . . . . ?
C32 Fe1 C34 C35 -78.9(14) . . . . ?
C25 Fe1 C34 C35 74.5(16) . . . . ?
C24 Fe1 C34 C35 117.7(13) . . . . ?
C33 Fe1 C34 C35 -118(2) . . . . ?
C31 Fe1 C34 C35 -36.8(12) . . . . ?
C22 Fe1 C34 C35 -171(3) . . . . ?
C23 Fe1 C34 C35 157.4(12) . . . . ?
C21 Fe1 C34 C35 37(3) . . . . ?
C35 Fe1 C34 C33 118(2) . . . . ?
C32 Fe1 C34 C33 39.3(13) . . . . ?
C25 Fe1 C34 C33 -167.4(13) . . . . ?
C24 Fe1 C34 C33 -124.2(13) . . . . ?
C31 Fe1 C34 C33 81.4(14) . . . . ?
C22 Fe1 C34 C33 -53(3) . . . . ?
C23 Fe1 C34 C33 -84.4(16) . . . . ?
C21 Fe1 C34 C33 155.1(19) . . . . ?
C33 C34 C35 C31 3(3) . . . . ?
Fe1 C34 C35 C31 60.3(15) . . . . ?
C33 C34 C35 Fe1 -57.6(15) . . . . ?
C32 C31 C35 C34 -2(3) . . . . ?
B2 C31 C35 C34 -177(2) . . . . ?
Fe1 C31 C35 C34 -61.1(16) . . . . ?
C32 C31 C35 Fe1 58.8(15) . . . . ?
B2 C31 C35 Fe1 -116(2) . . . . ?
C32 Fe1 C35 C34 84.6(14) . . . . ?
C25 Fe1 C35 C34 -121.4(14) . . . . ?
C24 Fe1 C35 C34 -80.3(15) . . . . ?
C33 Fe1 C35 C34 39.4(13) . . . . ?
C31 Fe1 C35 C34 121.7(17) . . . . ?
C22 Fe1 C35 C34 173.0(19) . . . . ?
C23 Fe1 C35 C34 -58(3) . . . . ?
C21 Fe1 C35 C34 -163.3(13) . . . . ?
C32 Fe1 C35 C31 -37.1(11) . . . . ?
C25 Fe1 C35 C31 116.9(12) . . . . ?
C24 Fe1 C35 C31 158.0(10) . . . . ?
C33 Fe1 C35 C31 -82.3(12) . . . . ?
C22 Fe1 C35 C31 51(2) . . . . ?
C23 Fe1 C35 C31 -179.5(19) . . . . ?
C21 Fe1 C35 C31 75.1(12) . . . . ?
C34 Fe1 C35 C31 -121.7(17) . . . . ?
C43 O41 C41 C42 162(4) . . . . ?
C41 O41 C43 C44 -170(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.165
_refine_diff_density_min         -1.555
_refine_diff_density_rms         0.212
_database_code_depnum_ccdc_archive 'CCDC 985507'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1666

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H31 B4 Fe2 I5 N10, 3(C6 H6)'
_chemical_formula_sum            'C53 H49 B4 Fe2 I5 N10'
_chemical_formula_weight         1615.46

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'
Fe Fe 0.3463 0.8444 '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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   21.7729(16)
_cell_length_b                   11.9678(12)
_cell_length_c                   24.4436(18)
_cell_angle_alpha                90
_cell_angle_beta                 115.688(5)
_cell_angle_gamma                90
_cell_volume                     5739.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15740
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      26.49

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_F_000             3096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.240
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_T_max  0.738
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41538
_diffrn_reflns_av_unetI/netI     0.1706
_diffrn_reflns_av_R_equivalents  0.1528
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.255
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_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             10130
_reflns_number_gt                5495
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0176P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10130
_refine_ls_number_parameters     667
_refine_ls_number_restraints     390
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.902
_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_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
Fe1 Fe 0.39287(8) 0.15571(14) 0.45864(7) 0.0230(4) Uani 1 1 d . . . . .
Fe2 Fe 0.22328(9) 0.82873(14) 0.24387(8) 0.0279(4) Uani 1 1 d . . . . .
I1 I 0.00732(4) 0.00743(7) 0.32379(5) 0.0411(2) Uani 1 1 d . . . . .
I2 I 0.24025(5) 0.20699(8) 0.14728(4) 0.0386(2) Uani 1 1 d . . . . .
I3 I 0.59773(4) 0.59514(8) 0.36682(4) 0.0401(2) Uani 1 1 d . . . . .
I4 I 0.35393(5) 0.74016(7) 0.55398(3) 0.0366(2) Uani 1 1 d . . . . .
I5 I -0.05025(5) 0.70705(8) 0.36853(4) 0.0412(2) Uani 1 1 d . . . . .
B1 B 0.2435(6) 0.2707(10) 0.3784(6) 0.022(3) Uani 1 1 d . . . . .
H1 H 0.2497 0.3423 0.4014 0.026 Uiso 1 1 calc R U . . .
B2 B 0.3748(6) 0.3908(10) 0.3884(5) 0.016(3) Uani 1 1 d . U . . .
H2 H 0.3519 0.4305 0.4104 0.020 Uiso 1 1 calc R U . . .
B3 B 0.3168(7) 0.6190(11) 0.3150(7) 0.026(3) Uani 1 1 d . . . . .
H3 H 0.2852 0.5595 0.2893 0.031 Uiso 1 1 calc R U . . .
B4 B 0.1716(6) 0.6354(10) 0.3081(6) 0.019(3) Uani 1 1 d . U . . .
H4 H 0.1739 0.5707 0.2832 0.023 Uiso 1 1 calc R U . . .
N1 N 0.1674(4) 0.2312(7) 0.3521(4) 0.020(2) Uani 1 1 d . . . . .
N2 N 0.1148(5) 0.3039(8) 0.3238(4) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.0588(6) 0.2463(10) 0.3107(5) 0.025(3) Uani 1 1 d . . . . .
H3A H 0.0142 0.2766 0.2908 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0724(6) 0.1367(9) 0.3294(5) 0.019(3) Uani 1 1 d . . . . .
C5 C 0.1434(7) 0.1326(10) 0.3548(6) 0.031(3) Uani 1 1 d . . . . .
H5 H 0.1702 0.0678 0.3715 0.037 Uiso 1 1 calc R U . . .
N11 N 0.2611(5) 0.2874(8) 0.3227(4) 0.023(2) Uani 1 1 d . . . . .
N12 N 0.3194(5) 0.3335(7) 0.3270(4) 0.020(2) Uani 1 1 d . . . . .
C13 C 0.3220(7) 0.3195(10) 0.2737(5) 0.030(3) Uani 1 1 d . . . . .
H13 H 0.3572 0.3458 0.2639 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2653(6) 0.2607(10) 0.2355(5) 0.026(3) Uani 1 1 d . . . . .
C15 C 0.2277(6) 0.2430(9) 0.2679(5) 0.020(3) Uani 1 1 d . . . . .
H15 H 0.1852 0.2054 0.2535 0.024 Uiso 1 1 calc R U . . .
N21 N 0.4163(5) 0.4747(7) 0.3681(4) 0.018(2) Uani 1 1 d . . . . .
N22 N 0.3938(5) 0.5779(8) 0.3416(4) 0.023(2) Uani 1 1 d . . . . .
C23 C 0.4449(6) 0.6276(10) 0.3384(5) 0.023(3) Uani 1 1 d . . . . .
H23 H 0.4429 0.7008 0.3226 0.027 Uiso 1 1 calc R U . . .
C24 C 0.5036(6) 0.5608(9) 0.3610(5) 0.021(3) Uani 1 1 d . . . . .
C25 C 0.4822(6) 0.4657(10) 0.3807(5) 0.030(3) Uani 1 1 d . . . . .
H25 H 0.5104 0.4036 0.4002 0.036 Uiso 1 1 calc R U . . .
N31 N 0.3031(5) 0.6447(7) 0.3725(4) 0.021(2) Uani 1 1 d . . . . .
N32 N 0.2406(5) 0.6470(8) 0.3701(4) 0.023(2) Uani 1 1 d . . . . .
C33 C 0.2461(6) 0.6766(9) 0.4251(5) 0.025(3) Uani 1 1 d . . . . .
H33 H 0.2094 0.6875 0.4357 0.030 Uiso 1 1 calc R U . . .
C34 C 0.3144(6) 0.6885(10) 0.4632(5) 0.026(3) Uani 1 1 d . . . . .
C35 C 0.3484(6) 0.6704(9) 0.4295(5) 0.023(3) Uani 1 1 d . . . . .
H35 H 0.3964 0.6749 0.4435 0.028 Uiso 1 1 calc R U . . .
N41 N 0.1147(5) 0.6192(7) 0.3291(4) 0.022(2) Uani 1 1 d . . . . .
N42 N 0.0964(5) 0.5181(8) 0.3428(4) 0.031(3) Uani 1 1 d . . . . .
H42 H 0.1168 0.4543 0.3433 0.037 Uiso 1 1 calc R U . . .
C43 C 0.0447(7) 0.5296(10) 0.3552(5) 0.029(3) Uani 1 1 d . . . . .
H43 H 0.0221 0.4705 0.3650 0.035 Uiso 1 1 calc R U . . .
C44 C 0.0275(6) 0.6420(10) 0.3518(5) 0.026(3) Uani 1 1 d . . . . .
C45 C 0.0719(5) 0.6927(10) 0.3361(5) 0.022(3) Uani 1 1 d . . . . .
H45 H 0.0732 0.7711 0.3306 0.027 Uiso 1 1 calc R U . . .
C51 C 0.2899(6) 0.1728(10) 0.4227(5) 0.028(3) Uani 1 1 d . . . . .
C52 C 0.3083(6) 0.0705(9) 0.4020(5) 0.025(3) Uani 1 1 d . . . . .
H52 H 0.2962 0.0507 0.3610 0.031 Uiso 1 1 calc R U . . .
C53 C 0.3469(6) 0.0064(11) 0.4529(5) 0.032(3) Uani 1 1 d . . . . .
H53 H 0.3657 -0.0648 0.4521 0.038 Uiso 1 1 calc R U . . .
C54 C 0.3537(6) 0.0616(12) 0.5050(6) 0.035(3) Uani 1 1 d . . . . .
H54 H 0.3776 0.0353 0.5455 0.042 Uiso 1 1 calc R U . . .
C55 C 0.3184(6) 0.1647(10) 0.4868(5) 0.024(3) Uani 1 1 d . . . . .
H55 H 0.3145 0.2194 0.5134 0.029 Uiso 1 1 calc R U . . .
C56 C 0.4244(5) 0.2938(9) 0.4300(5) 0.022(3) Uani 1 1 d . . . . .
C57 C 0.4453(6) 0.1956(10) 0.4106(5) 0.026(3) Uani 1 1 d . . . . .
H57 H 0.4334 0.1757 0.3696 0.031 Uiso 1 1 calc R U . . .
C58 C 0.4865(6) 0.1327(10) 0.4617(7) 0.037(4) Uani 1 1 d . . . . .
H58 H 0.5072 0.0630 0.4615 0.044 Uiso 1 1 calc R U . . .
C59 C 0.4916(6) 0.1903(12) 0.5125(6) 0.041(4) Uani 1 1 d . . . . .
H59 H 0.5166 0.1664 0.5533 0.050 Uiso 1 1 calc R U . . .
C60 C 0.4539(6) 0.2903(10) 0.4940(5) 0.032(3) Uani 1 1 d . . . . .
H60 H 0.4492 0.3453 0.5199 0.038 Uiso 1 1 calc R U . . .
C61 C 0.3082(6) 0.7308(10) 0.2766(5) 0.027(3) Uani 1 1 d . . . . .
C62 C 0.2795(6) 0.7410(12) 0.2127(5) 0.034(3) Uani 1 1 d . . . . .
H62 H 0.2625 0.6812 0.1845 0.040 Uiso 1 1 calc R U . . .
C63 C 0.2801(8) 0.8552(13) 0.1978(7) 0.048(4) Uani 1 1 d . . . . .
H63 H 0.2658 0.8843 0.1580 0.058 Uiso 1 1 calc R U . . .
C64 C 0.3047(6) 0.9167(11) 0.2500(6) 0.034(3) Uani 1 1 d . . . . .
H64 H 0.3081 0.9959 0.2523 0.041 Uiso 1 1 calc R U . . .
C65 C 0.3240(6) 0.8443(11) 0.2993(6) 0.037(3) Uani 1 1 d . . . . .
H65 H 0.3441 0.8657 0.3409 0.044 Uiso 1 1 calc R U . . .
C66 C 0.1570(5) 0.7499(10) 0.2708(5) 0.026(3) Uani 1 1 d . . . . .
C67 C 0.1296(6) 0.7609(12) 0.2064(6) 0.039(4) Uani 1 1 d . . . . .
H67 H 0.1160 0.7011 0.1780 0.047 Uiso 1 1 calc R U . . .
C68 C 0.1261(7) 0.8750(11) 0.1919(6) 0.039(4) Uani 1 1 d . . . . .
H68 H 0.1087 0.9056 0.1521 0.047 Uiso 1 1 calc R U . . .
C69 C 0.1526(7) 0.9358(11) 0.2459(7) 0.042(4) Uani 1 1 d . . . . .
H69 H 0.1572 1.0147 0.2499 0.050 Uiso 1 1 calc R U . . .
C70 C 0.1713(6) 0.8581(10) 0.2932(6) 0.029(3) Uani 1 1 d . . . . .
H70 H 0.1911 0.8769 0.3351 0.035 Uiso 1 1 calc R U . . .
C71 C 0.4735(10) 0.4268(13) 0.1847(10) 0.086(7) Uani 1 1 d D U . . .
H71 H 0.4942 0.3574 0.1839 0.104 Uiso 1 1 calc R U . . .
C72 C 0.4085(9) 0.4285(13) 0.1771(8) 0.069(5) Uani 1 1 d D U . . .
H72 H 0.3827 0.3614 0.1685 0.083 Uiso 1 1 calc R U . . .
C73 C 0.3804(8) 0.5259(14) 0.1818(7) 0.074(6) Uani 1 1 d D U . . .
H73 H 0.3350 0.5271 0.1779 0.089 Uiso 1 1 calc R U . . .
C74 C 0.4161(8) 0.6218(12) 0.1919(6) 0.050(4) Uani 1 1 d D U . . .
H74 H 0.3965 0.6900 0.1963 0.060 Uiso 1 1 calc R U . . .
C75 C 0.4798(8) 0.6210(13) 0.1957(7) 0.064(5) Uani 1 1 d D U . . .
H75 H 0.5038 0.6892 0.1999 0.076 Uiso 1 1 calc R U . . .
C76 C 0.5096(8) 0.5218(14) 0.1934(8) 0.083(7) Uani 1 1 d D U . . .
H76 H 0.5552 0.5199 0.1979 0.100 Uiso 1 1 calc R U . . .
C81 C 0.1756(10) -0.0144(17) 0.0189(8) 0.091(7) Uani 1 1 d D . . . .
H81 H 0.2015 -0.0813 0.0315 0.109 Uiso 1 1 calc R U . . .
C82 C 0.1126(11) -0.0100(19) 0.0174(9) 0.093(8) Uani 1 1 d D . . . .
H82 H 0.0945 -0.0733 0.0289 0.111 Uiso 1 1 calc R U . . .
C83 C 0.0761(9) 0.084(2) -0.0005(9) 0.094(9) Uani 1 1 d D . . . .
H83 H 0.0322 0.0879 -0.0011 0.113 Uiso 1 1 calc R U . . .
C84 C 0.1012(10) 0.1742(17) -0.0177(7) 0.082(7) Uani 1 1 d D . . . .
H84 H 0.0750 0.2407 -0.0309 0.099 Uiso 1 1 calc R U . . .
C85 C 0.1637(10) 0.1677(17) -0.0158(7) 0.075(6) Uani 1 1 d D . . . .
H85 H 0.1813 0.2307 -0.0280 0.091 Uiso 1 1 calc R U . . .
C86 C 0.2022(8) 0.0750(19) 0.0027(7) 0.074(6) Uani 1 1 d D . . . .
H86 H 0.2466 0.0724 0.0044 0.089 Uiso 1 1 calc R U . . .
C91 C 0.155(2) 0.494(4) 0.0794(17) 0.27(2) Uani 1 1 d D U . . .
H91 H 0.1706 0.4520 0.1160 0.320 Uiso 1 1 calc R U . . .
C92 C 0.0957(14) 0.551(2) 0.0599(12) 0.136(10) Uani 1 1 d D U . . .
H92 H 0.0607 0.5317 0.0715 0.163 Uiso 1 1 calc R U . . .
C93 C 0.0897(14) 0.639(2) 0.0227(12) 0.140(11) Uani 1 1 d D U . . .
H93 H 0.0554 0.6934 0.0160 0.168 Uiso 1 1 calc R U . . .
C94 C 0.1310(18) 0.651(3) -0.0051(16) 0.209(17) Uani 1 1 d D U . . .
H94 H 0.1262 0.7136 -0.0304 0.251 Uiso 1 1 calc R U . . .
C95 C 0.1793(14) 0.573(3) 0.0030(12) 0.136(10) Uani 1 1 d D U . . .
H95 H 0.2037 0.5728 -0.0211 0.163 Uiso 1 1 calc R U . . .
C96 C 0.1912(15) 0.496(3) 0.0461(15) 0.183(14) Uani 1 1 d D U . . .
H96 H 0.2259 0.4422 0.0538 0.220 Uiso 1 1 calc R U . . .


_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
Fe1 C57 2.019(12) . ?
Fe1 C59 2.019(12) . ?
Fe1 C55 2.022(13) . ?
Fe1 C53 2.024(13) . ?
Fe1 C56 2.026(12) . ?
Fe1 C58 2.026(14) . ?
Fe1 C60 2.027(12) . ?
Fe1 C54 2.029(12) . ?
Fe1 C51 2.034(12) . ?
Fe1 C52 2.034(11) . ?
Fe2 C62 1.997(13) . ?
Fe2 C67 2.010(13) . ?
Fe2 C70 2.010(13) . ?
Fe2 C64 2.011(13) . ?
Fe2 C68 2.017(13) . ?
Fe2 C69 2.019(14) . ?
Fe2 C63 2.026(15) . ?
Fe2 C65 2.026(13) . ?
Fe2 C61 2.037(12) . ?
Fe2 C66 2.055(12) . ?
I1 C4 2.061(11) . ?
I2 C14 2.084(11) . ?
I3 C24 2.034(12) . ?
I4 C34 2.095(11) . ?
I5 C44 2.059(13) . ?
B1 N1 1.568(15) . ?
B1 N11 1.580(16) . ?
B1 C51 1.618(17) . ?
B1 H1 1.0000 . ?
B2 N21 1.568(15) . ?
B2 C56 1.611(16) . ?
B2 N12 1.614(14) . ?
B2 H2 1.0000 . ?
B3 N31 1.587(18) . ?
B3 N22 1.591(17) . ?
B3 C61 1.599(18) . ?
B3 H3 1.0000 . ?
B4 N41 1.542(17) . ?
B4 C66 1.600(16) . ?
B4 N32 1.611(14) . ?
B4 H4 1.0000 . ?
N1 C5 1.303(14) . ?
N1 N2 1.364(12) . ?
N2 C3 1.315(15) . ?
C3 C4 1.378(15) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(17) . ?
C5 H5 0.9500 . ?
N11 C15 1.326(13) . ?
N11 N12 1.345(13) . ?
N12 C13 1.341(15) . ?
C13 C14 1.375(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(16) . ?
C15 H15 0.9500 . ?
N21 C25 1.336(15) . ?
N21 N22 1.381(12) . ?
N22 C23 1.293(15) . ?
C23 C24 1.402(16) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(17) . ?
C25 H25 0.9500 . ?
N31 N32 1.338(13) . ?
N31 C35 1.349(14) . ?
N32 C33 1.345(15) . ?
C33 C34 1.378(16) . ?
C33 H33 0.9500 . ?
C34 C35 1.342(17) . ?
C35 H35 0.9500 . ?
N41 C45 1.347(15) . ?
N41 N42 1.361(13) . ?
N42 C43 1.293(16) . ?
N42 H42 0.8800 . ?
C43 C44 1.390(16) . ?
C43 H43 0.9500 . ?
C44 C45 1.330(17) . ?
C45 H45 0.9500 . ?
C51 C55 1.417(16) . ?
C51 C52 1.447(17) . ?
C52 C53 1.392(15) . ?
C52 H52 0.9500 . ?
C53 C54 1.384(18) . ?
C53 H53 0.9500 . ?
C54 C55 1.419(17) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C60 1.410(16) . ?
C56 C57 1.415(16) . ?
C57 C58 1.400(16) . ?
C57 H57 0.9500 . ?
C58 C59 1.38(2) . ?
C58 H58 0.9500 . ?
C59 C60 1.411(18) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
C61 C62 1.413(16) . ?
C61 C65 1.452(18) . ?
C62 C63 1.416(19) . ?
C62 H62 0.9500 . ?
C63 C64 1.36(2) . ?
C63 H63 0.9500 . ?
C64 C65 1.393(17) . ?
C64 H64 0.9500 . ?
C65 H65 0.9500 . ?
C66 C70 1.388(16) . ?
C66 C67 1.427(17) . ?
C67 C68 1.405(19) . ?
C67 H67 0.9500 . ?
C68 C69 1.395(19) . ?
C68 H68 0.9500 . ?
C69 C70 1.398(18) . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
C71 C72 1.345(13) . ?
C71 C76 1.346(13) . ?
C71 H71 0.9500 . ?
C72 C73 1.344(12) . ?
C72 H72 0.9500 . ?
C73 C74 1.348(12) . ?
C73 H73 0.9500 . ?
C74 C75 1.348(12) . ?
C74 H74 0.9500 . ?
C75 C76 1.366(13) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
C81 C86 1.356(13) . ?
C81 C82 1.358(13) . ?
C81 H81 0.9500 . ?
C82 C83 1.339(13) . ?
C82 H82 0.9500 . ?
C83 C84 1.355(13) . ?
C83 H83 0.9500 . ?
C84 C85 1.344(13) . ?
C84 H84 0.9500 . ?
C85 C86 1.345(13) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C91 C92 1.349(14) . ?
C91 C96 1.361(14) . ?
C91 H91 0.9500 . ?
C92 C93 1.357(14) . ?
C92 H92 0.9500 . ?
C93 C94 1.351(14) . ?
C93 H93 0.9500 . ?
C94 C95 1.352(14) . ?
C94 H94 0.9500 . ?
C95 C96 1.336(14) . ?
C95 H95 0.9500 . ?
C96 H96 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
C57 Fe1 C59 67.7(5) . . ?
C57 Fe1 C55 157.8(5) . . ?
C59 Fe1 C55 123.5(6) . . ?
C57 Fe1 C53 123.8(5) . . ?
C59 Fe1 C53 125.6(5) . . ?
C55 Fe1 C53 67.9(5) . . ?
C57 Fe1 C56 41.0(5) . . ?
C59 Fe1 C56 68.5(5) . . ?
C55 Fe1 C56 121.0(5) . . ?
C53 Fe1 C56 158.1(5) . . ?
C57 Fe1 C58 40.5(5) . . ?
C59 Fe1 C58 40.0(6) . . ?
C55 Fe1 C58 159.7(5) . . ?
C53 Fe1 C58 110.0(5) . . ?
C56 Fe1 C58 68.8(5) . . ?
C57 Fe1 C60 68.2(5) . . ?
C59 Fe1 C60 40.8(5) . . ?
C55 Fe1 C60 106.7(5) . . ?
C53 Fe1 C60 160.8(5) . . ?
C56 Fe1 C60 40.7(5) . . ?
C58 Fe1 C60 68.2(5) . . ?
C57 Fe1 C54 159.6(6) . . ?
C59 Fe1 C54 109.7(5) . . ?
C55 Fe1 C54 41.0(5) . . ?
C53 Fe1 C54 39.9(5) . . ?
C56 Fe1 C54 158.8(5) . . ?
C58 Fe1 C54 124.3(5) . . ?
C60 Fe1 C54 124.0(5) . . ?
C57 Fe1 C51 121.4(5) . . ?
C59 Fe1 C51 157.6(6) . . ?
C55 Fe1 C51 40.9(5) . . ?
C53 Fe1 C51 68.8(5) . . ?
C56 Fe1 C51 104.1(4) . . ?
C58 Fe1 C51 159.0(6) . . ?
C60 Fe1 C51 120.0(5) . . ?
C54 Fe1 C51 69.2(5) . . ?
C57 Fe1 C52 107.2(5) . . ?
C59 Fe1 C52 160.2(6) . . ?
C55 Fe1 C52 68.6(5) . . ?
C53 Fe1 C52 40.1(4) . . ?
C56 Fe1 C52 121.1(4) . . ?
C58 Fe1 C52 123.8(6) . . ?
C60 Fe1 C52 157.1(5) . . ?
C54 Fe1 C52 68.0(5) . . ?
C51 Fe1 C52 41.7(5) . . ?
C62 Fe2 C67 106.4(6) . . ?
C62 Fe2 C70 156.7(5) . . ?
C67 Fe2 C70 67.7(5) . . ?
C62 Fe2 C64 68.8(6) . . ?
C67 Fe2 C64 159.0(5) . . ?
C70 Fe2 C64 124.8(6) . . ?
C62 Fe2 C68 123.6(6) . . ?
C67 Fe2 C68 40.8(5) . . ?
C70 Fe2 C68 67.7(6) . . ?
C64 Fe2 C68 123.6(5) . . ?
C62 Fe2 C69 160.5(6) . . ?
C67 Fe2 C69 68.5(6) . . ?
C70 Fe2 C69 40.6(5) . . ?
C64 Fe2 C69 108.8(6) . . ?
C68 Fe2 C69 40.5(6) . . ?
C62 Fe2 C63 41.2(5) . . ?
C67 Fe2 C63 123.6(6) . . ?
C70 Fe2 C63 160.7(6) . . ?
C64 Fe2 C63 39.5(6) . . ?
C68 Fe2 C63 109.5(6) . . ?
C69 Fe2 C63 124.7(6) . . ?
C62 Fe2 C65 68.9(6) . . ?
C67 Fe2 C65 158.9(5) . . ?
C70 Fe2 C65 108.1(6) . . ?
C64 Fe2 C65 40.4(5) . . ?
C68 Fe2 C65 158.7(6) . . ?
C69 Fe2 C65 122.7(6) . . ?
C63 Fe2 C65 67.2(6) . . ?
C62 Fe2 C61 41.0(5) . . ?
C67 Fe2 C61 121.1(5) . . ?
C70 Fe2 C61 121.1(5) . . ?
C64 Fe2 C61 69.6(5) . . ?
C68 Fe2 C61 158.6(6) . . ?
C69 Fe2 C61 158.0(5) . . ?
C63 Fe2 C61 68.8(5) . . ?
C65 Fe2 C61 41.9(5) . . ?
C62 Fe2 C66 120.8(5) . . ?
C67 Fe2 C66 41.1(5) . . ?
C70 Fe2 C66 39.9(5) . . ?
C64 Fe2 C66 159.2(5) . . ?
C68 Fe2 C66 68.8(5) . . ?
C69 Fe2 C66 68.6(5) . . ?
C63 Fe2 C66 158.7(6) . . ?
C65 Fe2 C66 122.3(5) . . ?
C61 Fe2 C66 104.7(5) . . ?
N1 B1 N11 107.0(8) . . ?
N1 B1 C51 107.3(9) . . ?
N11 B1 C51 110.8(10) . . ?
N1 B1 H1 110.5 . . ?
N11 B1 H1 110.5 . . ?
C51 B1 H1 110.5 . . ?
N21 B2 C56 110.0(9) . . ?
N21 B2 N12 106.2(8) . . ?
C56 B2 N12 107.9(9) . . ?
N21 B2 H2 110.9 . . ?
C56 B2 H2 110.9 . . ?
N12 B2 H2 110.9 . . ?
N31 B3 N22 105.5(10) . . ?
N31 B3 C61 109.8(10) . . ?
N22 B3 C61 109.5(10) . . ?
N31 B3 H3 110.6 . . ?
N22 B3 H3 110.6 . . ?
C61 B3 H3 110.6 . . ?
N41 B4 C66 108.0(10) . . ?
N41 B4 N32 104.8(9) . . ?
C66 B4 N32 109.6(8) . . ?
N41 B4 H4 111.4 . . ?
C66 B4 H4 111.4 . . ?
N32 B4 H4 111.4 . . ?
C5 N1 N2 109.7(10) . . ?
C5 N1 B1 128.9(10) . . ?
N2 N1 B1 121.4(9) . . ?
C3 N2 N1 105.9(9) . . ?
N2 C3 C4 112.1(10) . . ?
N2 C3 H3A 124.0 . . ?
C4 C3 H3A 124.0 . . ?
C3 C4 C5 102.6(10) . . ?
C3 C4 I1 130.5(9) . . ?
C5 C4 I1 126.9(8) . . ?
N1 C5 C4 109.7(10) . . ?
N1 C5 H5 125.1 . . ?
C4 C5 H5 125.1 . . ?
C15 N11 N12 109.2(9) . . ?
C15 N11 B1 126.0(10) . . ?
N12 N11 B1 123.9(8) . . ?
C13 N12 N11 108.0(9) . . ?
C13 N12 B2 128.8(10) . . ?
N11 N12 B2 123.2(9) . . ?
N12 C13 C14 108.6(12) . . ?
N12 C13 H13 125.7 . . ?
C14 C13 H13 125.7 . . ?
C13 C14 C15 105.7(10) . . ?
C13 C14 I2 128.0(10) . . ?
C15 C14 I2 126.3(8) . . ?
N11 C15 C14 108.4(10) . . ?
N11 C15 H15 125.8 . . ?
C14 C15 H15 125.8 . . ?
C25 N21 N22 107.8(9) . . ?
C25 N21 B2 125.7(9) . . ?
N22 N21 B2 125.9(9) . . ?
C23 N22 N21 107.5(9) . . ?
C23 N22 B3 127.9(10) . . ?
N21 N22 B3 124.3(9) . . ?
N22 C23 C24 112.0(10) . . ?
N22 C23 H23 124.0 . . ?
C24 C23 H23 124.0 . . ?
C25 C24 C23 102.6(10) . . ?
C25 C24 I3 128.2(9) . . ?
C23 C24 I3 129.2(8) . . ?
N21 C25 C24 110.0(10) . . ?
N21 C25 H25 125.0 . . ?
C24 C25 H25 125.0 . . ?
N32 N31 C35 108.3(10) . . ?
N32 N31 B3 122.9(9) . . ?
C35 N31 B3 128.8(10) . . ?
N31 N32 C33 108.2(9) . . ?
N31 N32 B4 123.8(10) . . ?
C33 N32 B4 127.2(10) . . ?
N32 C33 C34 107.9(11) . . ?
N32 C33 H33 126.1 . . ?
C34 C33 H33 126.1 . . ?
C35 C34 C33 106.7(10) . . ?
C35 C34 I4 127.9(9) . . ?
C33 C34 I4 125.1(9) . . ?
C34 C35 N31 108.8(11) . . ?
C34 C35 H35 125.6 . . ?
N31 C35 H35 125.6 . . ?
C45 N41 N42 104.8(10) . . ?
C45 N41 B4 131.3(10) . . ?
N42 N41 B4 123.8(9) . . ?
C43 N42 N41 109.9(10) . . ?
C43 N42 H42 125.1 . . ?
N41 N42 H42 125.1 . . ?
N42 C43 C44 109.2(11) . . ?
N42 C43 H43 125.4 . . ?
C44 C43 H43 125.4 . . ?
C45 C44 C43 104.3(12) . . ?
C45 C44 I5 130.3(9) . . ?
C43 C44 I5 125.3(10) . . ?
C44 C45 N41 111.7(11) . . ?
C44 C45 H45 124.2 . . ?
N41 C45 H45 124.2 . . ?
C55 C51 C52 105.9(10) . . ?
C55 C51 B1 129.6(11) . . ?
C52 C51 B1 124.4(11) . . ?
C55 C51 Fe1 69.1(7) . . ?
C52 C51 Fe1 69.2(7) . . ?
B1 C51 Fe1 127.8(8) . . ?
C53 C52 C51 107.8(11) . . ?
C53 C52 Fe1 69.5(7) . . ?
C51 C52 Fe1 69.2(7) . . ?
C53 C52 H52 126.1 . . ?
C51 C52 H52 126.1 . . ?
Fe1 C52 H52 126.8 . . ?
C54 C53 C52 109.9(12) . . ?
C54 C53 Fe1 70.3(8) . . ?
C52 C53 Fe1 70.3(7) . . ?
C54 C53 H53 125.0 . . ?
C52 C53 H53 125.0 . . ?
Fe1 C53 H53 126.0 . . ?
C53 C54 C55 107.5(10) . . ?
C53 C54 Fe1 69.8(8) . . ?
C55 C54 Fe1 69.2(7) . . ?
C53 C54 H54 126.2 . . ?
C55 C54 H54 126.2 . . ?
Fe1 C54 H54 126.3 . . ?
C51 C55 C54 108.9(11) . . ?
C51 C55 Fe1 70.0(7) . . ?
C54 C55 Fe1 69.8(7) . . ?
C51 C55 H55 125.6 . . ?
C54 C55 H55 125.6 . . ?
Fe1 C55 H55 126.2 . . ?
C60 C56 C57 106.8(10) . . ?
C60 C56 B2 125.5(10) . . ?
C57 C56 B2 127.7(10) . . ?
C60 C56 Fe1 69.7(7) . . ?
C57 C56 Fe1 69.2(7) . . ?
B2 C56 Fe1 124.9(7) . . ?
C58 C57 C56 108.8(11) . . ?
C58 C57 Fe1 70.0(8) . . ?
C56 C57 Fe1 69.8(7) . . ?
C58 C57 H57 125.6 . . ?
C56 C57 H57 125.6 . . ?
Fe1 C57 H57 126.1 . . ?
C59 C58 C57 107.8(11) . . ?
C59 C58 Fe1 69.7(8) . . ?
C57 C58 Fe1 69.5(7) . . ?
C59 C58 H58 126.1 . . ?
C57 C58 H58 126.1 . . ?
Fe1 C58 H58 126.3 . . ?
C58 C59 C60 109.0(10) . . ?
C58 C59 Fe1 70.3(7) . . ?
C60 C59 Fe1 69.9(7) . . ?
C58 C59 H59 125.5 . . ?
C60 C59 H59 125.5 . . ?
Fe1 C59 H59 125.8 . . ?
C56 C60 C59 107.7(11) . . ?
C56 C60 Fe1 69.6(7) . . ?
C59 C60 Fe1 69.3(7) . . ?
C56 C60 H60 126.2 . . ?
C59 C60 H60 126.2 . . ?
Fe1 C60 H60 126.5 . . ?
C62 C61 C65 105.1(11) . . ?
C62 C61 B3 127.2(11) . . ?
C65 C61 B3 127.6(11) . . ?
C62 C61 Fe2 68.0(7) . . ?
C65 C61 Fe2 68.7(7) . . ?
B3 C61 Fe2 124.6(8) . . ?
C61 C62 C63 108.5(12) . . ?
C61 C62 Fe2 71.0(7) . . ?
C63 C62 Fe2 70.5(8) . . ?
C61 C62 H62 125.8 . . ?
C63 C62 H62 125.8 . . ?
Fe2 C62 H62 124.3 . . ?
C64 C63 C62 108.9(12) . . ?
C64 C63 Fe2 69.6(8) . . ?
C62 C63 Fe2 68.3(8) . . ?
C64 C63 H63 125.5 . . ?
C62 C63 H63 125.5 . . ?
Fe2 C63 H63 128.1 . . ?
C63 C64 C65 108.8(13) . . ?
C63 C64 Fe2 70.8(8) . . ?
C65 C64 Fe2 70.4(8) . . ?
C63 C64 H64 125.6 . . ?
C65 C64 H64 125.6 . . ?
Fe2 C64 H64 124.7 . . ?
C64 C65 C61 108.5(12) . . ?
C64 C65 Fe2 69.2(7) . . ?
C61 C65 Fe2 69.5(7) . . ?
C64 C65 H65 125.7 . . ?
C61 C65 H65 125.7 . . ?
Fe2 C65 H65 127.2 . . ?
C70 C66 C67 105.3(11) . . ?
C70 C66 B4 128.2(10) . . ?
C67 C66 B4 126.4(11) . . ?
C70 C66 Fe2 68.3(7) . . ?
C67 C66 Fe2 67.7(7) . . ?
B4 C66 Fe2 125.7(8) . . ?
C68 C67 C66 108.6(12) . . ?
C68 C67 Fe2 69.9(8) . . ?
C66 C67 Fe2 71.2(7) . . ?
C68 C67 H67 125.7 . . ?
C66 C67 H67 125.7 . . ?
Fe2 C67 H67 124.9 . . ?
C69 C68 C67 108.2(11) . . ?
C69 C68 Fe2 69.9(8) . . ?
C67 C68 Fe2 69.3(7) . . ?
C69 C68 H68 125.9 . . ?
C67 C68 H68 125.9 . . ?
Fe2 C68 H68 126.5 . . ?
C68 C69 C70 106.8(12) . . ?
C68 C69 Fe2 69.7(8) . . ?
C70 C69 Fe2 69.3(7) . . ?
C68 C69 H69 126.6 . . ?
C70 C69 H69 126.6 . . ?
Fe2 C69 H69 125.9 . . ?
C66 C70 C69 111.1(11) . . ?
C66 C70 Fe2 71.8(8) . . ?
C69 C70 Fe2 70.1(8) . . ?
C66 C70 H70 124.5 . . ?
C69 C70 H70 124.5 . . ?
Fe2 C70 H70 125.2 . . ?
C72 C71 C76 121.1(13) . . ?
C72 C71 H71 119.4 . . ?
C76 C71 H71 119.4 . . ?
C73 C72 C71 119.5(13) . . ?
C73 C72 H72 120.2 . . ?
C71 C72 H72 120.2 . . ?
C72 C73 C74 120.3(13) . . ?
C72 C73 H73 119.8 . . ?
C74 C73 H73 119.8 . . ?
C73 C74 C75 120.1(12) . . ?
C73 C74 H74 119.9 . . ?
C75 C74 H74 119.9 . . ?
C74 C75 C76 119.7(13) . . ?
C74 C75 H75 120.1 . . ?
C76 C75 H75 120.1 . . ?
C71 C76 C75 119.0(13) . . ?
C71 C76 H76 120.5 . . ?
C75 C76 H76 120.5 . . ?
C86 C81 C82 121.1(14) . . ?
C86 C81 H81 119.5 . . ?
C82 C81 H81 119.5 . . ?
C83 C82 C81 119.4(14) . . ?
C83 C82 H82 120.3 . . ?
C81 C82 H82 120.3 . . ?
C82 C83 C84 120.6(14) . . ?
C82 C83 H83 119.7 . . ?
C84 C83 H83 119.7 . . ?
C85 C84 C83 118.8(14) . . ?
C85 C84 H84 120.6 . . ?
C83 C84 H84 120.6 . . ?
C84 C85 C86 122.2(14) . . ?
C84 C85 H85 118.9 . . ?
C86 C85 H85 118.9 . . ?
C85 C86 C81 117.8(14) . . ?
C85 C86 H86 121.1 . . ?
C81 C86 H86 121.1 . . ?
C92 C91 C96 119.5(19) . . ?
C92 C91 H91 120.3 . . ?
C96 C91 H91 120.3 . . ?
C91 C92 C93 115.5(17) . . ?
C91 C92 H92 122.2 . . ?
C93 C92 H92 122.2 . . ?
C94 C93 C92 121.8(17) . . ?
C94 C93 H93 119.1 . . ?
C92 C93 H93 119.1 . . ?
C93 C94 C95 120.0(17) . . ?
C93 C94 H94 120.0 . . ?
C95 C94 H94 120.0 . . ?
C96 C95 C94 117.5(17) . . ?
C96 C95 H95 121.3 . . ?
C94 C95 H95 121.3 . . ?
C95 C96 C91 121.5(18) . . ?
C95 C96 H96 119.3 . . ?
C91 C96 H96 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 B1 N1 C5 107.8(13) . . . . ?
C51 B1 N1 C5 -11.2(16) . . . . ?
N11 B1 N1 N2 -75.4(12) . . . . ?
C51 B1 N1 N2 165.7(9) . . . . ?
C5 N1 N2 C3 1.2(13) . . . . ?
B1 N1 N2 C3 -176.2(10) . . . . ?
N1 N2 C3 C4 -0.2(13) . . . . ?
N2 C3 C4 C5 -0.8(14) . . . . ?
N2 C3 C4 I1 178.5(9) . . . . ?
N2 N1 C5 C4 -1.8(14) . . . . ?
B1 N1 C5 C4 175.4(11) . . . . ?
C3 C4 C5 N1 1.6(14) . . . . ?
I1 C4 C5 N1 -177.8(8) . . . . ?
N1 B1 N11 C15 -20.1(14) . . . . ?
C51 B1 N11 C15 96.6(12) . . . . ?
N1 B1 N11 N12 171.9(9) . . . . ?
C51 B1 N11 N12 -71.4(13) . . . . ?
C15 N11 N12 C13 1.2(12) . . . . ?
B1 N11 N12 C13 170.9(10) . . . . ?
C15 N11 N12 B2 -177.2(9) . . . . ?
B1 N11 N12 B2 -7.5(15) . . . . ?
N21 B2 N12 C13 25.4(14) . . . . ?
C56 B2 N12 C13 -92.6(12) . . . . ?
N21 B2 N12 N11 -156.6(9) . . . . ?
C56 B2 N12 N11 85.5(12) . . . . ?
N11 N12 C13 C14 -1.8(12) . . . . ?
B2 N12 C13 C14 176.5(10) . . . . ?
N12 C13 C14 C15 1.7(13) . . . . ?
N12 C13 C14 I2 -177.8(8) . . . . ?
N12 N11 C15 C14 -0.1(12) . . . . ?
B1 N11 C15 C14 -169.5(10) . . . . ?
C13 C14 C15 N11 -1.0(13) . . . . ?
I2 C14 C15 N11 178.5(8) . . . . ?
C56 B2 N21 C25 2.9(15) . . . . ?
N12 B2 N21 C25 -113.6(11) . . . . ?
C56 B2 N21 N22 -167.6(9) . . . . ?
N12 B2 N21 N22 75.9(12) . . . . ?
C25 N21 N22 C23 0.4(12) . . . . ?
B2 N21 N22 C23 172.2(10) . . . . ?
C25 N21 N22 B3 175.2(11) . . . . ?
B2 N21 N22 B3 -12.9(16) . . . . ?
N31 B3 N22 C23 -112.9(13) . . . . ?
C61 B3 N22 C23 5.2(17) . . . . ?
N31 B3 N22 N21 73.3(12) . . . . ?
C61 B3 N22 N21 -168.6(9) . . . . ?
N21 N22 C23 C24 1.3(13) . . . . ?
B3 N22 C23 C24 -173.3(11) . . . . ?
N22 C23 C24 C25 -2.4(13) . . . . ?
N22 C23 C24 I3 179.6(8) . . . . ?
N22 N21 C25 C24 -1.9(12) . . . . ?
B2 N21 C25 C24 -173.8(10) . . . . ?
C23 C24 C25 N21 2.5(12) . . . . ?
I3 C24 C25 N21 -179.4(8) . . . . ?
N22 B3 N31 N32 -158.2(9) . . . . ?
C61 B3 N31 N32 83.9(12) . . . . ?
N22 B3 N31 C35 23.8(15) . . . . ?
C61 B3 N31 C35 -94.1(13) . . . . ?
C35 N31 N32 C33 1.5(11) . . . . ?
B3 N31 N32 C33 -176.9(10) . . . . ?
C35 N31 N32 B4 172.4(9) . . . . ?
B3 N31 N32 B4 -5.9(14) . . . . ?
N41 B4 N32 N31 169.1(9) . . . . ?
C66 B4 N32 N31 -75.2(13) . . . . ?
N41 B4 N32 C33 -21.7(14) . . . . ?
C66 B4 N32 C33 93.9(13) . . . . ?
N31 N32 C33 C34 -2.6(12) . . . . ?
B4 N32 C33 C34 -173.1(10) . . . . ?
N32 C33 C34 C35 2.7(13) . . . . ?
N32 C33 C34 I4 177.4(8) . . . . ?
C33 C34 C35 N31 -1.8(13) . . . . ?
I4 C34 C35 N31 -176.2(8) . . . . ?
N32 N31 C35 C34 0.2(12) . . . . ?
B3 N31 C35 C34 178.4(10) . . . . ?
C66 B4 N41 C45 -21.1(15) . . . . ?
N32 B4 N41 C45 95.7(12) . . . . ?
C66 B4 N41 N42 156.4(9) . . . . ?
N32 B4 N41 N42 -86.9(11) . . . . ?
C45 N41 N42 C43 2.1(12) . . . . ?
B4 N41 N42 C43 -175.9(10) . . . . ?
N41 N42 C43 C44 -1.8(13) . . . . ?
N42 C43 C44 C45 0.8(13) . . . . ?
N42 C43 C44 I5 -179.0(8) . . . . ?
C43 C44 C45 N41 0.6(13) . . . . ?
I5 C44 C45 N41 -179.6(8) . . . . ?
N42 N41 C45 C44 -1.6(12) . . . . ?
B4 N41 C45 C44 176.2(10) . . . . ?
N1 B1 C51 C55 -99.5(14) . . . . ?
N11 B1 C51 C55 144.0(12) . . . . ?
N1 B1 C51 C52 78.0(14) . . . . ?
N11 B1 C51 C52 -38.5(15) . . . . ?
N1 B1 C51 Fe1 167.2(8) . . . . ?
N11 B1 C51 Fe1 50.7(13) . . . . ?
C55 C51 C52 C53 -0.6(13) . . . . ?
B1 C51 C52 C53 -178.6(11) . . . . ?
Fe1 C51 C52 C53 59.0(8) . . . . ?
C55 C51 C52 Fe1 -59.6(8) . . . . ?
B1 C51 C52 Fe1 122.4(11) . . . . ?
C51 C52 C53 C54 0.5(14) . . . . ?
Fe1 C52 C53 C54 59.2(9) . . . . ?
C51 C52 C53 Fe1 -58.8(8) . . . . ?
C52 C53 C54 C55 -0.1(15) . . . . ?
Fe1 C53 C54 C55 59.2(8) . . . . ?
C52 C53 C54 Fe1 -59.3(9) . . . . ?
C52 C51 C55 C54 0.6(13) . . . . ?
B1 C51 C55 C54 178.4(11) . . . . ?
Fe1 C51 C55 C54 -59.1(9) . . . . ?
C52 C51 C55 Fe1 59.7(8) . . . . ?
B1 C51 C55 Fe1 -122.4(12) . . . . ?
C53 C54 C55 C51 -0.3(14) . . . . ?
Fe1 C54 C55 C51 59.3(9) . . . . ?
C53 C54 C55 Fe1 -59.6(9) . . . . ?
N21 B2 C56 C60 99.3(13) . . . . ?
N12 B2 C56 C60 -145.3(11) . . . . ?
N21 B2 C56 C57 -82.5(14) . . . . ?
N12 B2 C56 C57 32.9(15) . . . . ?
N21 B2 C56 Fe1 -172.1(7) . . . . ?
N12 B2 C56 Fe1 -56.6(12) . . . . ?
C60 C56 C57 C58 0.4(13) . . . . ?
B2 C56 C57 C58 -178.1(11) . . . . ?
Fe1 C56 C57 C58 -59.4(8) . . . . ?
C60 C56 C57 Fe1 59.8(8) . . . . ?
B2 C56 C57 Fe1 -118.6(11) . . . . ?
C56 C57 C58 C59 -0.2(14) . . . . ?
Fe1 C57 C58 C59 -59.4(10) . . . . ?
C56 C57 C58 Fe1 59.3(8) . . . . ?
C57 C58 C59 C60 -0.2(15) . . . . ?
Fe1 C58 C59 C60 -59.4(9) . . . . ?
C57 C58 C59 Fe1 59.3(9) . . . . ?
C57 C56 C60 C59 -0.5(14) . . . . ?
B2 C56 C60 C59 178.0(11) . . . . ?
Fe1 C56 C60 C59 59.0(9) . . . . ?
C57 C56 C60 Fe1 -59.5(8) . . . . ?
B2 C56 C60 Fe1 119.0(11) . . . . ?
C58 C59 C60 C56 0.4(15) . . . . ?
Fe1 C59 C60 C56 -59.2(9) . . . . ?
C58 C59 C60 Fe1 59.7(10) . . . . ?
N31 B3 C61 C62 -142.3(12) . . . . ?
N22 B3 C61 C62 102.3(14) . . . . ?
N31 B3 C61 C65 33.3(16) . . . . ?
N22 B3 C61 C65 -82.1(15) . . . . ?
N31 B3 C61 Fe2 -55.1(13) . . . . ?
N22 B3 C61 Fe2 -170.5(8) . . . . ?
C65 C61 C62 C63 1.9(14) . . . . ?
B3 C61 C62 C63 178.3(12) . . . . ?
Fe2 C61 C62 C63 60.8(9) . . . . ?
C65 C61 C62 Fe2 -58.9(9) . . . . ?
B3 C61 C62 Fe2 117.5(12) . . . . ?
C61 C62 C63 C64 -3.3(16) . . . . ?
Fe2 C62 C63 C64 57.8(10) . . . . ?
C61 C62 C63 Fe2 -61.2(9) . . . . ?
C62 C63 C64 C65 3.4(16) . . . . ?
Fe2 C63 C64 C65 60.4(10) . . . . ?
C62 C63 C64 Fe2 -57.0(10) . . . . ?
C63 C64 C65 C61 -2.2(16) . . . . ?
Fe2 C64 C65 C61 58.5(9) . . . . ?
C63 C64 C65 Fe2 -60.7(10) . . . . ?
C62 C61 C65 C64 0.2(14) . . . . ?
B3 C61 C65 C64 -176.2(12) . . . . ?
Fe2 C61 C65 C64 -58.3(9) . . . . ?
C62 C61 C65 Fe2 58.5(8) . . . . ?
B3 C61 C65 Fe2 -117.9(12) . . . . ?
N41 B4 C66 C70 80.0(14) . . . . ?
N32 B4 C66 C70 -33.6(17) . . . . ?
N41 B4 C66 C67 -103.7(13) . . . . ?
N32 B4 C66 C67 142.7(12) . . . . ?
N41 B4 C66 Fe2 169.1(7) . . . . ?
N32 B4 C66 Fe2 55.5(13) . . . . ?
C70 C66 C67 C68 -1.9(15) . . . . ?
B4 C66 C67 C68 -178.8(12) . . . . ?
Fe2 C66 C67 C68 -60.1(10) . . . . ?
C70 C66 C67 Fe2 58.2(8) . . . . ?
B4 C66 C67 Fe2 -118.8(12) . . . . ?
C66 C67 C68 C69 1.7(16) . . . . ?
Fe2 C67 C68 C69 -59.2(10) . . . . ?
C66 C67 C68 Fe2 60.9(9) . . . . ?
C67 C68 C69 C70 -0.8(16) . . . . ?
Fe2 C68 C69 C70 -59.7(9) . . . . ?
C67 C68 C69 Fe2 58.9(10) . . . . ?
C67 C66 C70 C69 1.4(15) . . . . ?
B4 C66 C70 C69 178.3(12) . . . . ?
Fe2 C66 C70 C69 59.3(10) . . . . ?
C67 C66 C70 Fe2 -57.9(9) . . . . ?
B4 C66 C70 Fe2 119.0(12) . . . . ?
C68 C69 C70 C66 -0.4(16) . . . . ?
Fe2 C69 C70 C66 -60.3(10) . . . . ?
C68 C69 C70 Fe2 59.9(10) . . . . ?
C76 C71 C72 C73 -4(3) . . . . ?
C71 C72 C73 C74 2(3) . . . . ?
C72 C73 C74 C75 2(3) . . . . ?
C73 C74 C75 C76 -4(2) . . . . ?
C72 C71 C76 C75 1(3) . . . . ?
C74 C75 C76 C71 3(3) . . . . ?
C86 C81 C82 C83 0(3) . . . . ?
C81 C82 C83 C84 1(3) . . . . ?
C82 C83 C84 C85 -1(3) . . . . ?
C83 C84 C85 C86 0(3) . . . . ?
C84 C85 C86 C81 1(3) . . . . ?
C82 C81 C86 C85 -1(3) . . . . ?
C96 C91 C92 C93 -24(6) . . . . ?
C91 C92 C93 C94 16(5) . . . . ?
C92 C93 C94 C95 1(6) . . . . ?
C93 C94 C95 C96 -10(6) . . . . ?
C94 C95 C96 C91 2(6) . . . . ?
C92 C91 C96 C95 16(7) . . . . ?

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
N42 H42 N2 0.88 1.86 2.666(14) 151.8 .

_refine_diff_density_max         1.494
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.158

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 985508'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1655

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 B2 Br N6, Br C H2 Cl2'
_chemical_formula_sum            'C16 H16 B2 Br2 Cl2 N6'
_chemical_formula_weight         544.69

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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   12.0607(5)
_cell_length_b                   9.6544(6)
_cell_length_c                   18.1880(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2117.79(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    40520
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.095
_shelx_estimated_absorpt_T_min   0.495
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37320
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.378
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2170
_reflns_number_gt                2070
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0352P)²+2.0261P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_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_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
Br1 Br 0.99831(3) 0.7500 0.46015(2) 0.02714(13) Uani 1 2 d S T P . .
Br2 Br 1.22518(3) 0.7500 0.35129(2) 0.02520(13) Uani 1 2 d S T P . .
B1 B 0.5731(3) 0.7500 0.6582(2) 0.0195(8) Uani 1 2 d S T P . .
B2 B 0.3964(4) 0.7500 0.7472(3) 0.0244(9) Uani 1 2 d S T P . .
H2 H 0.319(4) 0.7500 0.788(3) 0.029 Uiso 1 2 d S U P . .
N1 N 0.4579(3) 0.7500 0.61923(18) 0.0216(6) Uani 1 2 d S T P . .
N2 N 0.3675(3) 0.7500 0.66461(19) 0.0239(7) Uani 1 2 d S T P . .
C3 C 0.2770(3) 0.7500 0.6227(3) 0.0303(9) Uani 1 2 d S T P . .
H3 H 0.2028 0.7500 0.6402 0.036 Uiso 1 2 calc R U P . .
C4 C 0.3082(4) 0.7500 0.5497(3) 0.0338(10) Uani 1 2 d S T P . .
H4 H 0.2609 0.7500 0.5080 0.041 Uiso 1 2 calc R U P . .
C5 C 0.4229(3) 0.7500 0.5501(2) 0.0272(9) Uani 1 2 d S T P . .
H5 H 0.4690 0.7500 0.5078 0.033 Uiso 1 2 calc R U P . .
N11 N 0.56735(18) 0.6239(2) 0.71297(12) 0.0202(5) Uani 1 1 d . . . . .
N12 N 0.47516(18) 0.6247(2) 0.75736(13) 0.0235(5) Uani 1 1 d . . . . .
C13 C 0.4860(2) 0.5234(3) 0.80701(16) 0.0271(6) Uani 1 1 d . . . . .
H13 H 0.4337 0.5009 0.8442 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5856(3) 0.4570(3) 0.79519(17) 0.0298(6) Uani 1 1 d . . . . .
H14 H 0.6149 0.3811 0.8222 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6343(2) 0.5232(3) 0.73623(16) 0.0249(6) Uani 1 1 d . . . . .
H15 H 0.7043 0.5006 0.7155 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6735(3) 0.7500 0.6022(2) 0.0199(7) Uani 1 2 d S T P . .
C22 C 0.7204(2) 0.6263(3) 0.57684(15) 0.0226(6) Uani 1 1 d . . . . .
H22 H 0.6867 0.5407 0.5898 0.027 Uiso 1 1 calc R U . . .
C23 C 0.8150(2) 0.6253(3) 0.53317(15) 0.0235(6) Uani 1 1 d . . . . .
H23 H 0.8461 0.5403 0.5168 0.028 Uiso 1 1 calc R U . . .
C24 C 0.8629(3) 0.7500 0.5140(2) 0.0217(8) Uani 1 2 d S T P . .
C1L C 0.4390(4) 0.2500 0.6660(3) 0.0343(10) Uani 1 2 d S T P . .
H1L1 H 0.5209 0.2500 0.6696 0.041 Uiso 1 2 calc R U P . .
H1L2 H 0.4082 0.2500 0.7164 0.041 Uiso 1 2 calc R U P . .
Cl1 Cl 0.39452(9) 0.39951(9) 0.61892(6) 0.0550(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
Br1 C24 1.905(4) . ?
B1 N1 1.561(5) . ?
B1 N11 1.574(3) 7_575 ?
B1 N11 1.574(3) . ?
B1 C21 1.582(5) . ?
B2 N2 1.541(6) . ?
B2 N12 1.549(3) 7_575 ?
B2 N12 1.549(3) . ?
B2 H2 1.19(5) . ?
N1 C5 1.325(5) . ?
N1 N2 1.368(5) . ?
N2 C3 1.331(5) . ?
C3 C4 1.379(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N11 C15 1.333(3) . ?
N11 N12 1.374(3) . ?
N12 C13 1.337(4) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C22 1.401(3) 7_575 ?
C21 C22 1.401(3) . ?
C22 C23 1.390(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(3) . ?
C23 H23 0.9500 . ?
C24 C23 1.380(3) 7_575 ?
C1L Cl1 1.761(3) 7_565 ?
C1L Cl1 1.761(3) . ?
C1L H1L1 0.9900 . ?
C1L H1L2 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
N1 B1 N11 104.4(2) . 7_575 ?
N1 B1 N11 104.4(2) . . ?
N11 B1 N11 101.3(3) 7_575 . ?
N1 B1 C21 112.9(3) . . ?
N11 B1 C21 116.2(2) 7_575 . ?
N11 B1 C21 116.2(2) . . ?
N2 B2 N12 104.8(2) . 7_575 ?
N2 B2 N12 104.8(2) . . ?
N12 B2 N12 102.7(3) 7_575 . ?
N2 B2 H2 115(2) . . ?
N12 B2 H2 114.0(12) 7_575 . ?
N12 B2 H2 114.0(12) . . ?
C5 N1 N2 108.6(3) . . ?
C5 N1 B1 135.6(3) . . ?
N2 N1 B1 115.8(3) . . ?
C3 N2 N1 107.9(3) . . ?
C3 N2 B2 138.1(4) . . ?
N1 N2 B2 114.1(3) . . ?
N2 C3 C4 109.2(4) . . ?
N2 C3 H3 125.4 . . ?
C4 C3 H3 125.4 . . ?
C3 C4 C5 105.5(4) . . ?
C3 C4 H4 127.2 . . ?
C5 C4 H4 127.2 . . ?
N1 C5 C4 108.9(4) . . ?
N1 C5 H5 125.6 . . ?
C4 C5 H5 125.6 . . ?
C15 N11 N12 107.9(2) . . ?
C15 N11 B1 137.6(2) . . ?
N12 N11 B1 113.8(2) . . ?
C13 N12 N11 108.3(2) . . ?
C13 N12 B2 135.4(3) . . ?
N11 N12 B2 115.5(2) . . ?
N12 C13 C14 108.6(3) . . ?
N12 C13 H13 125.7 . . ?
C14 C13 H13 125.7 . . ?
C13 C14 C15 106.1(3) . . ?
C13 C14 H14 127.0 . . ?
C15 C14 H14 127.0 . . ?
N11 C15 C14 109.1(2) . . ?
N11 C15 H15 125.5 . . ?
C14 C15 H15 125.5 . . ?
C22 C21 C22 117.1(3) 7_575 . ?
C22 C21 B1 121.45(17) 7_575 . ?
C22 C21 B1 121.45(17) . . ?
C23 C22 C21 121.8(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C24 C23 C22 118.8(3) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C23 121.5(3) . 7_575 ?
C23 C24 Br1 119.25(17) . . ?
C23 C24 Br1 119.25(17) 7_575 . ?
Cl1 C1L Cl1 110.1(2) 7_565 . ?
Cl1 C1L H1L1 109.6 7_565 . ?
Cl1 C1L H1L1 109.6 . . ?
Cl1 C1L H1L2 109.6 7_565 . ?
Cl1 C1L H1L2 109.6 . . ?
H1L1 C1L H1L2 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 B1 N1 C5 127.03(18) 7_575 . . . ?
N11 B1 N1 C5 -127.03(18) . . . . ?
C21 B1 N1 C5 0.000(2) . . . . ?
N11 B1 N1 N2 -52.97(18) 7_575 . . . ?
N11 B1 N1 N2 52.97(18) . . . . ?
C21 B1 N1 N2 180.000(1) . . . . ?
C5 N1 N2 C3 0.000(1) . . . . ?
B1 N1 N2 C3 180.000(1) . . . . ?
C5 N1 N2 B2 180.000(1) . . . . ?
B1 N1 N2 B2 0.000(1) . . . . ?
N12 B2 N2 C3 -126.15(19) 7_575 . . . ?
N12 B2 N2 C3 126.15(19) . . . . ?
N12 B2 N2 N1 53.85(19) 7_575 . . . ?
N12 B2 N2 N1 -53.85(19) . . . . ?
N1 N2 C3 C4 0.000(1) . . . . ?
B2 N2 C3 C4 180.000(1) . . . . ?
N2 C3 C4 C5 0.000(1) . . . . ?
N2 N1 C5 C4 0.000(1) . . . . ?
B1 N1 C5 C4 180.000(1) . . . . ?
C3 C4 C5 N1 0.000(1) . . . . ?
N1 B1 N11 C15 140.0(3) . . . . ?
N11 B1 N11 C15 -111.8(3) 7_575 . . . ?
C21 B1 N11 C15 15.1(5) . . . . ?
N1 B1 N11 N12 -51.4(3) . . . . ?
N11 B1 N11 N12 56.8(3) 7_575 . . . ?
C21 B1 N11 N12 -176.3(2) . . . . ?
C15 N11 N12 C13 -0.6(3) . . . . ?
B1 N11 N12 C13 -172.6(2) . . . . ?
C15 N11 N12 B2 170.3(2) . . . . ?
B1 N11 N12 B2 -1.6(3) . . . . ?
N2 B2 N12 C13 -137.1(3) . . . . ?
N12 B2 N12 C13 113.6(3) 7_575 . . . ?
N2 B2 N12 N11 55.1(3) . . . . ?
N12 B2 N12 N11 -54.2(4) 7_575 . . . ?
N11 N12 C13 C14 0.3(3) . . . . ?
B2 N12 C13 C14 -168.0(3) . . . . ?
N12 C13 C14 C15 0.1(3) . . . . ?
N12 N11 C15 C14 0.7(3) . . . . ?
B1 N11 C15 C14 169.7(3) . . . . ?
C13 C14 C15 N11 -0.5(3) . . . . ?
N1 B1 C21 C22 90.5(3) . . . 7_575 ?
N11 B1 C21 C22 -29.9(5) 7_575 . . 7_575 ?
N11 B1 C21 C22 -149.0(3) . . . 7_575 ?
N1 B1 C21 C22 -90.5(3) . . . . ?
N11 B1 C21 C22 149.0(3) 7_575 . . . ?
N11 B1 C21 C22 29.9(5) . . . . ?
C22 C21 C22 C23 5.1(5) 7_575 . . . ?
B1 C21 C22 C23 -173.8(3) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C23 -4.3(6) . . . 7_575 ?
C22 C23 C24 Br1 175.6(2) . . . . ?

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
C4 H4 Br2 0.95 2.88 3.745(5) 151.7 1_455
C13 H13 Br2 0.95 3.09 3.755(3) 128.3 2_665
C14 H14 Br1 0.95 3.12 3.744(3) 124.4 2_665
C15 H15 Br2 0.95 2.84 3.516(3) 129.2 5_766
C1L H1L1 Br2 0.99 3.09 4.063(5) 169.1 5_766
C1L H1L2 Br2 0.99 2.93 3.909(5) 168.8 2_665

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.083

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 985509'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1474

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 B2 Br2 N6, Br'
_chemical_formula_sum            'C21 H17 B2 Br3 N6'
_chemical_formula_weight         614.76

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'
Br Br -0.2901 2.4595 '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_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.7625(8)
_cell_length_b                   11.1593(8)
_cell_length_c                   11.5455(9)
_cell_angle_alpha                90.305(6)
_cell_angle_beta                 107.707(6)
_cell_angle_gamma                106.691(6)
_cell_volume                     1141.79(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17122
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    5.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4158
_exptl_absorpt_correction_T_max  0.6182
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10831
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.41
_reflns_number_total             4185
_reflns_number_gt                3470
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0543P)²] 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         4185
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
Br1 Br 0.12453(5) -0.41842(4) 0.91414(4) 0.04727(13) Uani 1 1 d . . .
Br2 Br 0.93376(5) 0.74168(4) 0.42146(4) 0.04992(14) Uani 1 1 d . . .
Br3 Br 0.75892(4) -0.23769(4) 0.87793(3) 0.03625(12) Uani 1 1 d . . .
B1 B 0.4589(5) 0.0895(4) 0.7506(3) 0.0299(8) Uani 1 1 d . . .
B2 B 0.5858(5) 0.2915(4) 0.6489(3) 0.0314(8) Uani 1 1 d . . .
N1 N 0.6337(3) 0.1225(3) 0.7839(2) 0.0307(6) Uani 1 1 d . . .
N2 N 0.6953(3) 0.2243(3) 0.7297(2) 0.0305(6) Uani 1 1 d . . .
C3 C 0.8454(4) 0.2569(3) 0.7780(3) 0.0344(8) Uani 1 1 d . . .
H3 H 0.9150 0.3252 0.7575 0.041 Uiso 1 1 calc R . .
C4 C 0.8829(4) 0.1751(4) 0.8626(3) 0.0379(8) Uani 1 1 d . . .
H4 H 0.9814 0.1747 0.9093 0.045 Uiso 1 1 calc R . .
C5 C 0.7481(4) 0.0945(3) 0.8652(3) 0.0345(8) Uani 1 1 d . . .
H5 H 0.7376 0.0287 0.9168 0.041 Uiso 1 1 calc R . .
N11 N 0.4381(3) 0.2154(3) 0.7894(2) 0.0315(6) Uani 1 1 d . . .
N12 N 0.5013(3) 0.3197(3) 0.7374(2) 0.0311(6) Uani 1 1 d . . .
C13 C 0.4797(4) 0.4197(4) 0.7849(3) 0.0353(8) Uani 1 1 d . . .
H13 H 0.5120 0.5034 0.7648 0.042 Uiso 1 1 calc R . .
C14 C 0.4032(4) 0.3821(4) 0.8677(3) 0.0385(8) Uani 1 1 d . . .
H14 H 0.3726 0.4337 0.9143 0.046 Uiso 1 1 calc R . .
C15 C 0.3804(4) 0.2546(4) 0.8690(3) 0.0350(8) Uani 1 1 d . . .
H15 H 0.3314 0.2024 0.9184 0.042 Uiso 1 1 calc R . .
N21 N 0.4021(3) 0.0810(3) 0.6079(2) 0.0310(6) Uani 1 1 d . . .
N22 N 0.4611(3) 0.1844(3) 0.5556(2) 0.0306(6) Uani 1 1 d . . .
C23 C 0.3813(4) 0.1670(4) 0.4361(3) 0.0354(8) Uani 1 1 d . . .
H23 H 0.3976 0.2249 0.3781 0.042 Uiso 1 1 calc R . .
C24 C 0.2719(5) 0.0513(4) 0.4112(3) 0.0404(9) Uani 1 1 d . . .
H24 H 0.2006 0.0143 0.3340 0.048 Uiso 1 1 calc R . .
C25 C 0.2875(4) 0.0006(4) 0.5213(3) 0.0362(8) Uani 1 1 d . . .
H25 H 0.2269 -0.0785 0.5337 0.043 Uiso 1 1 calc R . .
C31 C 0.6741(4) 0.4059(3) 0.5919(3) 0.0326(8) Uani 1 1 d . . .
C32 C 0.7391(4) 0.5267(4) 0.6532(3) 0.0366(8) Uani 1 1 d . . .
H32 H 0.7292 0.5415 0.7309 0.044 Uiso 1 1 calc R . .
C33 C 0.8180(4) 0.6259(4) 0.6037(3) 0.0366(8) Uani 1 1 d . . .
H33 H 0.8595 0.7079 0.6461 0.044 Uiso 1 1 calc R . .
C34 C 0.8349(4) 0.6037(3) 0.4932(3) 0.0364(8) Uani 1 1 d . . .
C35 C 0.7807(4) 0.4844(4) 0.4314(3) 0.0401(9) Uani 1 1 d . . .
H35 H 0.7979 0.4697 0.3566 0.048 Uiso 1 1 calc R . .
C36 C 0.7009(5) 0.3870(4) 0.4816(3) 0.0377(8) Uani 1 1 d . . .
H36 H 0.6632 0.3048 0.4399 0.045 Uiso 1 1 calc R . .
C41 C 0.3735(4) -0.0351(3) 0.7967(3) 0.0309(7) Uani 1 1 d . . .
C42 C 0.2293(4) -0.0569(3) 0.8086(3) 0.0329(8) Uani 1 1 d . . .
H42 H 0.1825 0.0077 0.7934 0.040 Uiso 1 1 calc R . .
C43 C 0.1532(4) -0.1699(4) 0.8417(3) 0.0365(8) Uani 1 1 d . . .
H43 H 0.0564 -0.1824 0.8500 0.044 Uiso 1 1 calc R . .
C44 C 0.2217(4) -0.2638(3) 0.8625(3) 0.0343(8) Uani 1 1 d . . .
C45 C 0.3599(4) -0.2488(3) 0.8482(3) 0.0339(8) Uani 1 1 d . . .
H45 H 0.4040 -0.3152 0.8607 0.041 Uiso 1 1 calc R . .
C46 C 0.4344(4) -0.1349(3) 0.8151(3) 0.0343(8) Uani 1 1 d . . .
H46 H 0.5298 -0.1248 0.8047 0.041 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
Br1 C44 1.910(3) . ?
Br2 C34 1.906(3) . ?
B1 N11 1.558(5) . ?
B1 N1 1.561(5) . ?
B1 N21 1.563(4) . ?
B1 C41 1.589(5) . ?
B2 N22 1.556(5) . ?
B2 N2 1.561(5) . ?
B2 N12 1.575(5) . ?
B2 C31 1.590(5) . ?
N1 C5 1.338(5) . ?
N1 N2 1.373(4) . ?
N2 C3 1.336(5) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N11 C15 1.343(4) . ?
N11 N12 1.385(4) . ?
N12 C13 1.338(5) . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C25 1.337(5) . ?
N21 N22 1.365(4) . ?
N22 C23 1.343(4) . ?
C23 C24 1.381(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C31 C32 1.395(5) . ?
C31 C36 1.404(5) . ?
C32 C33 1.389(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.367(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(5) . ?
C35 C36 1.385(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.395(5) . ?
C41 C42 1.407(5) . ?
C42 C43 1.389(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.381(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.372(5) . ?
C45 C46 1.390(5) . ?
C45 H45 0.9500 . ?
C46 H46 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
N11 B1 N1 102.8(3) . . ?
N11 B1 N21 103.2(3) . . ?
N1 B1 N21 103.9(3) . . ?
N11 B1 C41 117.5(3) . . ?
N1 B1 C41 117.3(3) . . ?
N21 B1 C41 110.4(3) . . ?
N22 B2 N2 104.5(3) . . ?
N22 B2 N12 102.5(3) . . ?
N2 B2 N12 102.6(3) . . ?
N22 B2 C31 116.0(3) . . ?
N2 B2 C31 111.1(3) . . ?
N12 B2 C31 118.5(3) . . ?
C5 N1 N2 107.3(3) . . ?
C5 N1 B1 138.6(3) . . ?
N2 N1 B1 113.0(3) . . ?
C3 N2 N1 108.4(3) . . ?
C3 N2 B2 133.0(3) . . ?
N1 N2 B2 117.4(3) . . ?
N2 C3 C4 109.0(3) . . ?
N2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
C5 C4 C3 105.6(3) . . ?
C5 C4 H4 127.2 . . ?
C3 C4 H4 127.2 . . ?
N1 C5 C4 109.7(3) . . ?
N1 C5 H5 125.2 . . ?
C4 C5 H5 125.2 . . ?
C15 N11 N12 107.5(3) . . ?
C15 N11 B1 136.5(3) . . ?
N12 N11 B1 115.8(3) . . ?
C13 N12 N11 108.0(3) . . ?
C13 N12 B2 138.0(3) . . ?
N11 N12 B2 113.9(3) . . ?
N12 C13 C14 109.2(3) . . ?
N12 C13 H13 125.4 . . ?
C14 C13 H13 125.4 . . ?
C15 C14 C13 105.9(3) . . ?
C15 C14 H14 127.1 . . ?
C13 C14 H14 127.1 . . ?
N11 C15 C14 109.4(3) . . ?
N11 C15 H15 125.3 . . ?
C14 C15 H15 125.3 . . ?
C25 N21 N22 108.7(3) . . ?
C25 N21 B1 133.6(3) . . ?
N22 N21 B1 116.7(3) . . ?
C23 N22 N21 107.7(3) . . ?
C23 N22 B2 138.0(3) . . ?
N21 N22 B2 113.9(2) . . ?
N22 C23 C24 109.0(3) . . ?
N22 C23 H23 125.5 . . ?
C24 C23 H23 125.5 . . ?
C25 C24 C23 105.8(3) . . ?
C25 C24 H24 127.1 . . ?
C23 C24 H24 127.1 . . ?
N21 C25 C24 108.8(3) . . ?
N21 C25 H25 125.6 . . ?
C24 C25 H25 125.6 . . ?
C32 C31 C36 116.8(3) . . ?
C32 C31 B2 122.1(3) . . ?
C36 C31 B2 120.9(3) . . ?
C33 C32 C31 121.8(3) . . ?
C33 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
C34 C33 C32 118.9(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 121.9(3) . . ?
C33 C34 Br2 118.8(3) . . ?
C35 C34 Br2 119.3(3) . . ?
C34 C35 C36 118.2(3) . . ?
C34 C35 H35 120.9 . . ?
C36 C35 H35 120.9 . . ?
C35 C36 C31 122.1(4) . . ?
C35 C36 H36 119.0 . . ?
C31 C36 H36 119.0 . . ?
C46 C41 C42 116.5(3) . . ?
C46 C41 B1 119.7(3) . . ?
C42 C41 B1 123.4(3) . . ?
C43 C42 C41 122.2(3) . . ?
C43 C42 H42 118.9 . . ?
C41 C42 H42 118.9 . . ?
C44 C43 C42 118.5(3) . . ?
C44 C43 H43 120.8 . . ?
C42 C43 H43 120.8 . . ?
C45 C44 C43 121.7(3) . . ?
C45 C44 Br1 118.4(3) . . ?
C43 C44 Br1 119.9(3) . . ?
C44 C45 C46 119.0(4) . . ?
C44 C45 H45 120.5 . . ?
C46 C45 H45 120.5 . . ?
C45 C46 C41 122.1(3) . . ?
C45 C46 H46 119.0 . . ?
C41 C46 H46 119.0 . . ?

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
N11 B1 N1 C5 110.4(4) . . . . ?
N21 B1 N1 C5 -142.3(4) . . . . ?
C41 B1 N1 C5 -20.2(6) . . . . ?
N11 B1 N1 N2 -55.7(3) . . . . ?
N21 B1 N1 N2 51.6(3) . . . . ?
C41 B1 N1 N2 173.7(3) . . . . ?
C5 N1 N2 C3 0.1(4) . . . . ?
B1 N1 N2 C3 170.5(3) . . . . ?
C5 N1 N2 B2 -168.9(3) . . . . ?
B1 N1 N2 B2 1.6(4) . . . . ?
N22 B2 N2 C3 140.8(3) . . . . ?
N12 B2 N2 C3 -112.6(4) . . . . ?
C31 B2 N2 C3 15.0(5) . . . . ?
N22 B2 N2 N1 -53.6(4) . . . . ?
N12 B2 N2 N1 53.1(4) . . . . ?
C31 B2 N2 N1 -179.4(3) . . . . ?
N1 N2 C3 C4 1.0(4) . . . . ?
B2 N2 C3 C4 167.6(3) . . . . ?
N2 C3 C4 C5 -1.7(4) . . . . ?
N2 N1 C5 C4 -1.2(4) . . . . ?
B1 N1 C5 C4 -167.8(4) . . . . ?
C3 C4 C5 N1 1.8(4) . . . . ?
N1 B1 N11 C15 -119.0(4) . . . . ?
N21 B1 N11 C15 133.2(4) . . . . ?
C41 B1 N11 C15 11.5(6) . . . . ?
N1 B1 N11 N12 56.0(3) . . . . ?
N21 B1 N11 N12 -51.8(4) . . . . ?
C41 B1 N11 N12 -173.6(3) . . . . ?
C15 N11 N12 C13 -0.6(4) . . . . ?
B1 N11 N12 C13 -177.0(3) . . . . ?
C15 N11 N12 B2 175.4(3) . . . . ?
B1 N11 N12 B2 -1.0(4) . . . . ?
N22 B2 N12 C13 -129.9(4) . . . . ?
N2 B2 N12 C13 121.9(4) . . . . ?
C31 B2 N12 C13 -0.8(6) . . . . ?
N22 B2 N12 N11 55.8(3) . . . . ?
N2 B2 N12 N11 -52.4(4) . . . . ?
C31 B2 N12 N11 -175.2(3) . . . . ?
N11 N12 C13 C14 0.1(4) . . . . ?
B2 N12 C13 C14 -174.5(4) . . . . ?
N12 C13 C14 C15 0.5(4) . . . . ?
N12 N11 C15 C14 0.9(4) . . . . ?
B1 N11 C15 C14 176.2(4) . . . . ?
C13 C14 C15 N11 -0.9(4) . . . . ?
N11 B1 N21 C25 -116.5(4) . . . . ?
N1 B1 N21 C25 136.6(4) . . . . ?
C41 B1 N21 C25 10.0(6) . . . . ?
N11 B1 N21 N22 50.6(4) . . . . ?
N1 B1 N21 N22 -56.3(4) . . . . ?
C41 B1 N21 N22 177.1(3) . . . . ?
C25 N21 N22 C23 0.2(4) . . . . ?
B1 N21 N22 C23 -170.0(3) . . . . ?
C25 N21 N22 B2 174.4(3) . . . . ?
B1 N21 N22 B2 4.3(4) . . . . ?
N2 B2 N22 C23 -139.1(4) . . . . ?
N12 B2 N22 C23 114.2(4) . . . . ?
C31 B2 N22 C23 -16.4(6) . . . . ?
N2 B2 N22 N21 49.1(4) . . . . ?
N12 B2 N22 N21 -57.6(4) . . . . ?
C31 B2 N22 N21 171.9(3) . . . . ?
N21 N22 C23 C24 -0.7(4) . . . . ?
B2 N22 C23 C24 -172.8(4) . . . . ?
N22 C23 C24 C25 1.0(5) . . . . ?
N22 N21 C25 C24 0.4(4) . . . . ?
B1 N21 C25 C24 168.2(4) . . . . ?
C23 C24 C25 N21 -0.8(4) . . . . ?
N22 B2 C31 C32 152.7(4) . . . . ?
N2 B2 C31 C32 -88.2(4) . . . . ?
N12 B2 C31 C32 30.2(5) . . . . ?
N22 B2 C31 C36 -32.8(5) . . . . ?
N2 B2 C31 C36 86.3(4) . . . . ?
N12 B2 C31 C36 -155.3(4) . . . . ?
C36 C31 C32 C33 4.3(6) . . . . ?
B2 C31 C32 C33 179.1(4) . . . . ?
C31 C32 C33 C34 -1.4(6) . . . . ?
C32 C33 C34 C35 -2.5(6) . . . . ?
C32 C33 C34 Br2 176.7(3) . . . . ?
C33 C34 C35 C36 3.2(6) . . . . ?
Br2 C34 C35 C36 -176.0(3) . . . . ?
C34 C35 C36 C31 0.0(6) . . . . ?
C32 C31 C36 C35 -3.6(6) . . . . ?
B2 C31 C36 C35 -178.4(4) . . . . ?
N11 B1 C41 C46 -151.0(3) . . . . ?
N1 B1 C41 C46 -27.6(4) . . . . ?
N21 B1 C41 C46 91.1(4) . . . . ?
N11 B1 C41 C42 35.9(5) . . . . ?
N1 B1 C41 C42 159.2(3) . . . . ?
N21 B1 C41 C42 -82.1(4) . . . . ?
C46 C41 C42 C43 2.5(5) . . . . ?
B1 C41 C42 C43 175.9(3) . . . . ?
C41 C42 C43 C44 -0.6(5) . . . . ?
C42 C43 C44 C45 -1.6(5) . . . . ?
C42 C43 C44 Br1 177.7(3) . . . . ?
C43 C44 C45 C46 1.7(5) . . . . ?
Br1 C44 C45 C46 -177.6(3) . . . . ?
C44 C45 C46 C41 0.4(5) . . . . ?
C42 C41 C46 C45 -2.5(5) . . . . ?
B1 C41 C46 C45 -176.0(3) . . . . ?

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
C46 H46 Br3 0.95 2.79 3.547(4) 137.2 .
C4 H4 Br3 0.95 2.85 3.727(4) 153.9 2_757
C15 H15 Br3 0.95 2.81 3.564(3) 136.6 2_657
C23 H23 Br3 0.95 2.91 3.643(3) 134.8 2_656
C32 H32 Br3 0.95 2.88 3.607(4) 134.5 1_565
C43 H43 Br3 0.95 2.91 3.857(4) 176.2 1_455
C25 H25 Br2 0.95 2.88 3.663(4) 140.1 1_445

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 985510'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1089

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 B2 Br2 N4 O2'
_chemical_formula_sum            'C20 H20 B2 Br2 N4 O2'
_chemical_formula_weight         529.84

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   15.7852(7)
_cell_length_b                   22.9613(10)
_cell_length_c                   12.9046(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.391(3)
_cell_angle_gamma                90.00
_cell_volume                     4292.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    39094
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2112
_exptl_absorpt_coefficient_mu    3.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3759
_exptl_absorpt_correction_T_max  0.3853
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            92971
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         26.99
_reflns_number_total             9294
_reflns_number_gt                5805
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0675P)²] 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         9294
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Br1 Br 1.09173(4) 0.90294(2) 0.76202(5) 0.04748(15) Uani 1 1 d . . .
Br2 Br 0.78166(4) 0.89943(2) 0.59059(5) 0.04775(16) Uani 1 1 d . . .
B1 B 1.0455(4) 0.6293(2) 0.7285(5) 0.0343(11) Uani 1 1 d . . .
O1 O 1.1314(2) 0.59996(14) 0.7695(3) 0.0375(8) Uani 1 1 d . . .
C1 C 1.1328(3) 0.5381(2) 0.7655(5) 0.0457(12) Uani 1 1 d . . .
H1A H 1.1968 0.5244 0.7964 0.069 Uiso 1 1 calc R . .
H1B H 1.1018 0.5251 0.6870 0.069 Uiso 1 1 calc R . .
H1C H 1.1006 0.5221 0.8103 0.069 Uiso 1 1 calc R . .
B2 B 0.8305(3) 0.6271(2) 0.6291(4) 0.0315(11) Uani 1 1 d . . .
O2 O 0.7448(2) 0.59518(14) 0.5875(3) 0.0367(8) Uani 1 1 d . . .
C2 C 0.7476(3) 0.53352(19) 0.5903(4) 0.0432(12) Uani 1 1 d . . .
H2A H 0.6845 0.5182 0.5592 0.065 Uiso 1 1 calc R . .
H2B H 0.7795 0.5203 0.6684 0.065 Uiso 1 1 calc R . .
H2C H 0.7806 0.5194 0.5450 0.065 Uiso 1 1 calc R . .
N11 N 0.9850(2) 0.60916(16) 0.6041(3) 0.0326(8) Uani 1 1 d . . .
N12 N 0.8908(3) 0.60883(17) 0.5598(3) 0.0327(9) Uani 1 1 d . . .
C13 C 0.8605(3) 0.5980(2) 0.4494(4) 0.0372(11) Uani 1 1 d . . .
H13 H 0.7976 0.5957 0.3985 0.045 Uiso 1 1 calc R . .
C14 C 0.9359(4) 0.5907(2) 0.4212(4) 0.0393(11) Uani 1 1 d . . .
H14 H 0.9349 0.5820 0.3488 0.047 Uiso 1 1 calc R . .
C15 C 1.0122(3) 0.5986(2) 0.5197(4) 0.0387(11) Uani 1 1 d . . .
H15 H 1.0744 0.5969 0.5269 0.046 Uiso 1 1 calc R . .
N21 N 0.9873(3) 0.60891(16) 0.7980(3) 0.0318(8) Uani 1 1 d . . .
N22 N 0.8926(2) 0.60738(16) 0.7534(3) 0.0312(8) Uani 1 1 d . . .
C23 C 0.8656(3) 0.59339(19) 0.8365(4) 0.0356(10) Uani 1 1 d . . .
H23 H 0.8034 0.5898 0.8286 0.043 Uiso 1 1 calc R . .
C24 C 0.9432(3) 0.5850(2) 0.9361(4) 0.0366(10) Uani 1 1 d . . .
H24 H 0.9448 0.5744 1.0081 0.044 Uiso 1 1 calc R . .
C25 C 1.0170(4) 0.5954(2) 0.9072(4) 0.0393(11) Uani 1 1 d . . .
H25 H 1.0800 0.5932 0.9578 0.047 Uiso 1 1 calc R . .
C31 C 1.0567(3) 0.69866(19) 0.7354(4) 0.0307(9) Uani 1 1 d . . .
C32 C 1.0300(3) 0.7345(2) 0.6398(4) 0.0353(10) Uani 1 1 d . . .
H32 H 1.0040 0.7168 0.5674 0.042 Uiso 1 1 calc R . .
C33 C 1.0395(3) 0.7946(2) 0.6458(4) 0.0393(11) Uani 1 1 d . . .
H33 H 1.0210 0.8175 0.5792 0.047 Uiso 1 1 calc R . .
C34 C 1.0766(3) 0.8201(2) 0.7513(4) 0.0375(11) Uani 1 1 d . . .
C35 C 1.1046(3) 0.7874(2) 0.8489(4) 0.0421(11) Uani 1 1 d . . .
H35 H 1.1301 0.8056 0.9209 0.051 Uiso 1 1 calc R . .
C36 C 1.0945(3) 0.7276(2) 0.8395(4) 0.0412(11) Uani 1 1 d . . .
H36 H 1.1141 0.7050 0.9066 0.049 Uiso 1 1 calc R . .
C41 C 0.8153(3) 0.69564(19) 0.6222(4) 0.0329(10) Uani 1 1 d . . .
C42 C 0.8409(3) 0.7319(2) 0.7166(4) 0.0354(10) Uani 1 1 d . . .
H42 H 0.8656 0.7145 0.7894 0.043 Uiso 1 1 calc R . .
C43 C 0.8321(3) 0.7916(2) 0.7093(4) 0.0381(10) Uani 1 1 d . . .
H43 H 0.8512 0.8150 0.7754 0.046 Uiso 1 1 calc R . .
C44 C 0.7945(3) 0.81667(19) 0.6026(4) 0.0363(11) Uani 1 1 d . . .
C45 C 0.7665(3) 0.78360(19) 0.5065(4) 0.0392(11) Uani 1 1 d . . .
H45 H 0.7410 0.8014 0.4342 0.047 Uiso 1 1 calc R . .
C46 C 0.7761(3) 0.7235(2) 0.5170(4) 0.0392(11) Uani 1 1 d . . .
H46 H 0.7554 0.7004 0.4504 0.047 Uiso 1 1 calc R . .
Br1A Br 0.58818(4) 0.59296(2) 0.74937(5) 0.04495(15) Uani 1 1 d . . .
Br2A Br 0.28490(4) 0.59604(2) 0.60686(5) 0.04380(15) Uani 1 1 d . . .
B1A B 0.5454(4) 0.8670(2) 0.7277(4) 0.0337(11) Uani 1 1 d . . .
O1A O 0.6329(2) 0.89667(14) 0.7653(3) 0.0353(8) Uani 1 1 d . . .
C1A C 0.6325(4) 0.9580(2) 0.7607(4) 0.0450(12) Uani 1 1 d . . .
H1A1 H 0.6961 0.9724 0.7888 0.068 Uiso 1 1 calc R . .
H1A2 H 0.6019 0.9735 0.8077 0.068 Uiso 1 1 calc R . .
H1A3 H 0.5991 0.9708 0.6825 0.068 Uiso 1 1 calc R . .
B2A B 0.3311(3) 0.8696(2) 0.6303(4) 0.0316(11) Uani 1 1 d . . .
O2A O 0.2463(2) 0.90048(14) 0.5929(3) 0.0367(8) Uani 1 1 d . . .
C2A C 0.2470(3) 0.9621(2) 0.5972(4) 0.0428(12) Uani 1 1 d . . .
H2A1 H 0.1834 0.9766 0.5688 0.064 Uiso 1 1 calc R . .
H2A2 H 0.2779 0.9775 0.5503 0.064 Uiso 1 1 calc R . .
H2A3 H 0.2803 0.9750 0.6754 0.064 Uiso 1 1 calc R . .
N11A N 0.4882(2) 0.88779(16) 0.7975(3) 0.0318(8) Uani 1 1 d . . .
N12A N 0.3944(2) 0.88812(16) 0.7549(3) 0.0309(8) Uani 1 1 d . . .
C13A C 0.3686(3) 0.90252(19) 0.8393(4) 0.0370(10) Uani 1 1 d . . .
H13A H 0.3067 0.9058 0.8327 0.044 Uiso 1 1 calc R . .
C14A C 0.4463(3) 0.9117(2) 0.9370(4) 0.0393(11) Uani 1 1 d . . .
H14A H 0.4484 0.9230 1.0088 0.047 Uiso 1 1 calc R . .
C15A C 0.5208(3) 0.9010(2) 0.9075(4) 0.0349(10) Uani 1 1 d . . .
H15A H 0.5841 0.9027 0.9572 0.042 Uiso 1 1 calc R . .
N21A N 0.4827(2) 0.88723(16) 0.6029(3) 0.0321(8) Uani 1 1 d . . .
N22A N 0.3880(3) 0.88871(16) 0.5594(3) 0.0313(8) Uani 1 1 d . . .
C23A C 0.3577(4) 0.90141(19) 0.4499(4) 0.0369(11) Uani 1 1 d . . .
H23A H 0.2946 0.9045 0.3999 0.044 Uiso 1 1 calc R . .
C24A C 0.4323(4) 0.9094(2) 0.4198(4) 0.0389(11) Uani 1 1 d . . .
H24A H 0.4307 0.9192 0.3475 0.047 Uiso 1 1 calc R . .
C25A C 0.5088(3) 0.90009(19) 0.5178(4) 0.0378(10) Uani 1 1 d . . .
H25A H 0.5709 0.9024 0.5246 0.045 Uiso 1 1 calc R . .
C31A C 0.5575(3) 0.7975(2) 0.7342(4) 0.0333(10) Uani 1 1 d . . .
C32A C 0.5300(3) 0.7632(2) 0.8053(4) 0.0346(10) Uani 1 1 d . . .
H32A H 0.5050 0.7819 0.8526 0.042 Uiso 1 1 calc R . .
C33A C 0.5380(3) 0.7028(2) 0.8091(4) 0.0370(11) Uani 1 1 d . . .
H33A H 0.5185 0.6807 0.8579 0.044 Uiso 1 1 calc R . .
C34A C 0.5746(3) 0.6756(2) 0.7414(4) 0.0352(10) Uani 1 1 d . . .
C35A C 0.6032(3) 0.7071(2) 0.6695(4) 0.0379(10) Uani 1 1 d . . .
H35A H 0.6285 0.6880 0.6229 0.045 Uiso 1 1 calc R . .
C36A C 0.5940(3) 0.7674(2) 0.6675(4) 0.0372(10) Uani 1 1 d . . .
H36A H 0.6136 0.7891 0.6183 0.045 Uiso 1 1 calc R . .
C41A C 0.3160(3) 0.80000(19) 0.6206(4) 0.0319(10) Uani 1 1 d . . .
C42A C 0.3431(3) 0.7658(2) 0.5500(4) 0.0355(10) Uani 1 1 d . . .
H42A H 0.3684 0.7843 0.5029 0.043 Uiso 1 1 calc R . .
C43A C 0.3346(3) 0.7059(2) 0.5463(4) 0.0383(11) Uani 1 1 d . . .
H43A H 0.3540 0.6837 0.4976 0.046 Uiso 1 1 calc R . .
C44A C 0.2977(3) 0.67882(19) 0.6138(4) 0.0349(10) Uani 1 1 d . . .
C45A C 0.2689(3) 0.7105(2) 0.6850(4) 0.0387(10) Uani 1 1 d . . .
H45A H 0.2432 0.6914 0.7312 0.046 Uiso 1 1 calc R . .
C46A C 0.2784(3) 0.7707(2) 0.6877(4) 0.0379(10) Uani 1 1 d . . .
H46A H 0.2588 0.7927 0.7366 0.045 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
Br1 C34 1.914(5) . ?
Br2 C44 1.911(5) . ?
B1 O1 1.415(6) . ?
B1 N11 1.577(6) . ?
B1 N21 1.587(6) . ?
B1 C31 1.602(7) . ?
O1 C1 1.422(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
B2 O2 1.442(6) . ?
B2 N22 1.578(6) . ?
B2 C41 1.589(7) . ?
B2 N12 1.600(6) . ?
O2 C2 1.417(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N11 C15 1.343(6) . ?
N11 N12 1.364(5) . ?
N12 C13 1.333(6) . ?
C13 C14 1.386(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C25 1.333(6) . ?
N21 N22 1.373(5) . ?
N22 C23 1.340(6) . ?
C23 C24 1.393(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C31 C36 1.401(6) . ?
C31 C32 1.402(6) . ?
C32 C33 1.386(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(7) . ?
C35 C36 1.383(7) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.396(6) . ?
C41 C46 1.403(6) . ?
C42 C43 1.378(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.389(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.369(7) . ?
C45 C46 1.389(6) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
Br1A C34A 1.908(5) . ?
Br2A C44A 1.910(4) . ?
B1A O1A 1.441(6) . ?
B1A N11A 1.581(6) . ?
B1A N21A 1.588(6) . ?
B1A C31A 1.605(7) . ?
O1A C1A 1.410(5) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
B2A O2A 1.420(6) . ?
B2A N22A 1.576(6) . ?
B2A N12A 1.578(6) . ?
B2A C41A 1.614(7) . ?
O2A C2A 1.416(5) . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 0.9800 . ?
N11A C15A 1.338(6) . ?
N11A N12A 1.359(5) . ?
N12A C13A 1.347(6) . ?
C13A C14A 1.381(6) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.394(7) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
N21A C25A 1.350(6) . ?
N21A N22A 1.374(5) . ?
N22A C23A 1.332(6) . ?
C23A C24A 1.391(7) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.376(7) . ?
C24A H24A 0.9500 . ?
C25A H25A 0.9500 . ?
C31A C36A 1.395(6) . ?
C31A C32A 1.402(6) . ?
C32A C33A 1.393(6) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.374(7) . ?
C33A H33A 0.9500 . ?
C34A C35A 1.386(6) . ?
C35A C36A 1.392(6) . ?
C35A H35A 0.9500 . ?
C36A H36A 0.9500 . ?
C41A C42A 1.392(6) . ?
C41A C46A 1.401(6) . ?
C42A C43A 1.380(6) . ?
C42A H42A 0.9500 . ?
C43A C44A 1.375(7) . ?
C43A H43A 0.9500 . ?
C44A C45A 1.381(6) . ?
C45A C46A 1.390(6) . ?
C45A H45A 0.9500 . ?
C46A H46A 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
O1 B1 N11 110.2(4) . . ?
O1 B1 N21 109.4(4) . . ?
N11 B1 N21 103.7(4) . . ?
O1 B1 C31 112.6(4) . . ?
N11 B1 C31 110.9(4) . . ?
N21 B1 C31 109.8(4) . . ?
B1 O1 C1 119.2(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 B2 N22 110.2(4) . . ?
O2 B2 C41 112.6(4) . . ?
N22 B2 C41 111.1(4) . . ?
O2 B2 N12 109.7(4) . . ?
N22 B2 N12 103.0(3) . . ?
C41 B2 N12 109.8(4) . . ?
C2 O2 B2 118.9(4) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C15 N11 N12 107.7(4) . . ?
C15 N11 B1 128.3(4) . . ?
N12 N11 B1 123.2(4) . . ?
C13 N12 N11 108.6(4) . . ?
C13 N12 B2 127.3(4) . . ?
N11 N12 B2 123.7(4) . . ?
N12 C13 C14 108.8(4) . . ?
N12 C13 H13 125.6 . . ?
C14 C13 H13 125.6 . . ?
C15 C14 C13 105.6(4) . . ?
C15 C14 H14 127.2 . . ?
C13 C14 H14 127.2 . . ?
N11 C15 C14 109.2(4) . . ?
N11 C15 H15 125.4 . . ?
C14 C15 H15 125.4 . . ?
C25 N21 N22 107.7(4) . . ?
C25 N21 B1 128.8(4) . . ?
N22 N21 B1 123.3(4) . . ?
C23 N22 N21 108.1(4) . . ?
C23 N22 B2 128.0(4) . . ?
N21 N22 B2 123.5(4) . . ?
N22 C23 C24 109.3(4) . . ?
N22 C23 H23 125.4 . . ?
C24 C23 H23 125.4 . . ?
C25 C24 C23 104.7(4) . . ?
C25 C24 H24 127.7 . . ?
C23 C24 H24 127.7 . . ?
N21 C25 C24 110.3(5) . . ?
N21 C25 H25 124.9 . . ?
C24 C25 H25 124.9 . . ?
C36 C31 C32 115.5(4) . . ?
C36 C31 B1 121.4(4) . . ?
C32 C31 B1 123.2(4) . . ?
C33 C32 C31 123.2(4) . . ?
C33 C32 H32 118.4 . . ?
C31 C32 H32 118.4 . . ?
C34 C33 C32 118.2(4) . . ?
C34 C33 H33 120.9 . . ?
C32 C33 H33 120.9 . . ?
C35 C34 C33 121.7(4) . . ?
C35 C34 Br1 119.3(4) . . ?
C33 C34 Br1 119.0(4) . . ?
C34 C35 C36 118.4(5) . . ?
C34 C35 H35 120.8 . . ?
C36 C35 H35 120.8 . . ?
C35 C36 C31 123.1(5) . . ?
C35 C36 H36 118.5 . . ?
C31 C36 H36 118.5 . . ?
C42 C41 C46 115.9(4) . . ?
C42 C41 B2 123.8(4) . . ?
C46 C41 B2 120.3(4) . . ?
C43 C42 C41 123.1(4) . . ?
C43 C42 H42 118.4 . . ?
C41 C42 H42 118.4 . . ?
C42 C43 C44 118.2(4) . . ?
C42 C43 H43 120.9 . . ?
C44 C43 H43 120.9 . . ?
C45 C44 C43 121.7(4) . . ?
C45 C44 Br2 119.5(4) . . ?
C43 C44 Br2 118.8(4) . . ?
C44 C45 C46 118.7(4) . . ?
C44 C45 H45 120.7 . . ?
C46 C45 H45 120.7 . . ?
C45 C46 C41 122.4(4) . . ?
C45 C46 H46 118.8 . . ?
C41 C46 H46 118.8 . . ?
O1A B1A N11A 110.7(4) . . ?
O1A B1A N21A 109.3(4) . . ?
N11A B1A N21A 102.9(3) . . ?
O1A B1A C31A 112.0(4) . . ?
N11A B1A C31A 110.7(4) . . ?
N21A B1A C31A 110.9(4) . . ?
C1A O1A B1A 118.0(4) . . ?
O1A C1A H1A1 109.5 . . ?
O1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O2A B2A N22A 110.0(4) . . ?
O2A B2A N12A 110.0(4) . . ?
N22A B2A N12A 103.9(3) . . ?
O2A B2A C41A 112.2(4) . . ?
N22A B2A C41A 109.4(4) . . ?
N12A B2A C41A 111.1(4) . . ?
C2A O2A B2A 119.6(4) . . ?
O2A C2A H2A1 109.5 . . ?
O2A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
O2A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
C15A N11A N12A 109.0(4) . . ?
C15A N11A B1A 127.4(4) . . ?
N12A N11A B1A 123.2(4) . . ?
C13A N12A N11A 107.7(4) . . ?
C13A N12A B2A 128.2(4) . . ?
N11A N12A B2A 123.9(4) . . ?
N12A C13A C14A 109.4(4) . . ?
N12A C13A H13A 125.3 . . ?
C14A C13A H13A 125.3 . . ?
C13A C14A C15A 105.2(4) . . ?
C13A C14A H14A 127.4 . . ?
C15A C14A H14A 127.4 . . ?
N11A C15A C14A 108.6(4) . . ?
N11A C15A H15A 125.7 . . ?
C14A C15A H15A 125.7 . . ?
C25A N21A N22A 107.3(4) . . ?
C25A N21A B1A 128.3(4) . . ?
N22A N21A B1A 124.1(3) . . ?
C23A N22A N21A 108.2(4) . . ?
C23A N22A B2A 129.0(4) . . ?
N21A N22A B2A 122.3(4) . . ?
N22A C23A C24A 109.8(4) . . ?
N22A C23A H23A 125.1 . . ?
C24A C23A H23A 125.1 . . ?
C25A C24A C23A 104.7(4) . . ?
C25A C24A H24A 127.7 . . ?
C23A C24A H24A 127.7 . . ?
N21A C25A C24A 110.0(4) . . ?
N21A C25A H25A 125.0 . . ?
C24A C25A H25A 125.0 . . ?
C36A C31A C32A 115.9(4) . . ?
C36A C31A B1A 122.0(4) . . ?
C32A C31A B1A 122.0(4) . . ?
C33A C32A C31A 122.4(4) . . ?
C33A C32A H32A 118.8 . . ?
C31A C32A H32A 118.8 . . ?
C34A C33A C32A 119.0(4) . . ?
C34A C33A H33A 120.5 . . ?
C32A C33A H33A 120.5 . . ?
C33A C34A C35A 121.3(4) . . ?
C33A C34A Br1A 119.0(4) . . ?
C35A C34A Br1A 119.7(4) . . ?
C34A C35A C36A 118.2(4) . . ?
C34A C35A H35A 120.9 . . ?
C36A C35A H35A 120.9 . . ?
C35A C36A C31A 123.2(4) . . ?
C35A C36A H36A 118.4 . . ?
C31A C36A H36A 118.4 . . ?
C42A C41A C46A 116.7(4) . . ?
C42A C41A B2A 122.3(4) . . ?
C46A C41A B2A 120.9(4) . . ?
C43A C42A C41A 122.2(4) . . ?
C43A C42A H42A 118.9 . . ?
C41A C42A H42A 118.9 . . ?
C44A C43A C42A 119.2(5) . . ?
C44A C43A H43A 120.4 . . ?
C42A C43A H43A 120.4 . . ?
C43A C44A C45A 121.2(4) . . ?
C43A C44A Br2A 118.9(4) . . ?
C45A C44A Br2A 119.9(4) . . ?
C44A C45A C46A 118.7(4) . . ?
C44A C45A H45A 120.7 . . ?
C46A C45A H45A 120.7 . . ?
C45A C46A C41A 122.0(4) . . ?
C45A C46A H46A 119.0 . . ?
C41A C46A H46A 119.0 . . ?

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
N11 B1 O1 C1 -53.6(6) . . . . ?
N21 B1 O1 C1 59.7(5) . . . . ?
C31 B1 O1 C1 -178.0(4) . . . . ?
N22 B2 O2 C2 -54.3(5) . . . . ?
C41 B2 O2 C2 -178.9(4) . . . . ?
N12 B2 O2 C2 58.5(5) . . . . ?
O1 B1 N11 C15 -40.1(6) . . . . ?
N21 B1 N11 C15 -157.0(4) . . . . ?
C31 B1 N11 C15 85.2(6) . . . . ?
O1 B1 N11 N12 151.2(4) . . . . ?
N21 B1 N11 N12 34.2(5) . . . . ?
C31 B1 N11 N12 -83.5(5) . . . . ?
C15 N11 N12 C13 0.2(5) . . . . ?
B1 N11 N12 C13 171.0(4) . . . . ?
C15 N11 N12 B2 -172.4(4) . . . . ?
B1 N11 N12 B2 -1.7(6) . . . . ?
O2 B2 N12 C13 39.0(6) . . . . ?
N22 B2 N12 C13 156.3(4) . . . . ?
C41 B2 N12 C13 -85.2(6) . . . . ?
O2 B2 N12 N11 -149.8(4) . . . . ?
N22 B2 N12 N11 -32.4(5) . . . . ?
C41 B2 N12 N11 86.0(5) . . . . ?
N11 N12 C13 C14 0.5(5) . . . . ?
B2 N12 C13 C14 172.8(4) . . . . ?
N12 C13 C14 C15 -1.0(6) . . . . ?
N12 N11 C15 C14 -0.8(5) . . . . ?
B1 N11 C15 C14 -171.0(4) . . . . ?
C13 C14 C15 N11 1.1(5) . . . . ?
O1 B1 N21 C25 35.8(7) . . . . ?
N11 B1 N21 C25 153.3(4) . . . . ?
C31 B1 N21 C25 -88.2(6) . . . . ?
O1 B1 N21 N22 -150.3(4) . . . . ?
N11 B1 N21 N22 -32.8(5) . . . . ?
C31 B1 N21 N22 85.8(5) . . . . ?
C25 N21 N22 C23 0.6(5) . . . . ?
B1 N21 N22 C23 -174.5(4) . . . . ?
C25 N21 N22 B2 173.5(4) . . . . ?
B1 N21 N22 B2 -1.6(6) . . . . ?
O2 B2 N22 C23 -37.7(6) . . . . ?
C41 B2 N22 C23 87.8(5) . . . . ?
N12 B2 N22 C23 -154.7(4) . . . . ?
O2 B2 N22 N21 150.8(4) . . . . ?
C41 B2 N22 N21 -83.7(5) . . . . ?
N12 B2 N22 N21 33.9(5) . . . . ?
N21 N22 C23 C24 -0.7(5) . . . . ?
B2 N22 C23 C24 -173.2(4) . . . . ?
N22 C23 C24 C25 0.6(5) . . . . ?
N22 N21 C25 C24 -0.2(5) . . . . ?
B1 N21 C25 C24 174.5(4) . . . . ?
C23 C24 C25 N21 -0.2(6) . . . . ?
O1 B1 C31 C36 -66.7(6) . . . . ?
N11 B1 C31 C36 169.4(4) . . . . ?
N21 B1 C31 C36 55.4(6) . . . . ?
O1 B1 C31 C32 113.5(5) . . . . ?
N11 B1 C31 C32 -10.5(6) . . . . ?
N21 B1 C31 C32 -124.5(4) . . . . ?
C36 C31 C32 C33 -0.1(7) . . . . ?
B1 C31 C32 C33 179.8(4) . . . . ?
C31 C32 C33 C34 -0.5(7) . . . . ?
C32 C33 C34 C35 0.6(7) . . . . ?
C32 C33 C34 Br1 179.4(3) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
Br1 C34 C35 C36 -178.9(4) . . . . ?
C34 C35 C36 C31 -0.4(8) . . . . ?
C32 C31 C36 C35 0.5(7) . . . . ?
B1 C31 C36 C35 -179.4(5) . . . . ?
O2 B2 C41 C42 114.5(5) . . . . ?
N22 B2 C41 C42 -9.7(6) . . . . ?
N12 B2 C41 C42 -123.0(5) . . . . ?
O2 B2 C41 C46 -67.1(6) . . . . ?
N22 B2 C41 C46 168.7(4) . . . . ?
N12 B2 C41 C46 55.4(5) . . . . ?
C46 C41 C42 C43 -2.3(7) . . . . ?
B2 C41 C42 C43 176.2(4) . . . . ?
C41 C42 C43 C44 1.0(7) . . . . ?
C42 C43 C44 C45 0.1(7) . . . . ?
C42 C43 C44 Br2 180.0(3) . . . . ?
C43 C44 C45 C46 0.1(7) . . . . ?
Br2 C44 C45 C46 -179.8(4) . . . . ?
C44 C45 C46 C41 -1.4(7) . . . . ?
C42 C41 C46 C45 2.4(7) . . . . ?
B2 C41 C46 C45 -176.1(4) . . . . ?
N11A B1A O1A C1A -57.8(5) . . . . ?
N21A B1A O1A C1A 54.8(5) . . . . ?
C31A B1A O1A C1A 178.1(4) . . . . ?
N22A B2A O2A C2A -58.9(5) . . . . ?
N12A B2A O2A C2A 54.9(5) . . . . ?
C41A B2A O2A C2A 179.1(4) . . . . ?
O1A B1A N11A C15A -37.4(6) . . . . ?
N21A B1A N11A C15A -154.0(4) . . . . ?
C31A B1A N11A C15A 87.4(6) . . . . ?
O1A B1A N11A N12A 151.0(4) . . . . ?
N21A B1A N11A N12A 34.4(5) . . . . ?
C31A B1A N11A N12A -84.2(5) . . . . ?
C15A N11A N12A C13A 0.9(5) . . . . ?
B1A N11A N12A C13A 173.9(4) . . . . ?
C15A N11A N12A B2A -174.8(4) . . . . ?
B1A N11A N12A B2A -1.8(6) . . . . ?
O2A B2A N12A C13A 34.8(6) . . . . ?
N22A B2A N12A C13A 152.5(4) . . . . ?
C41A B2A N12A C13A -90.0(5) . . . . ?
O2A B2A N12A N11A -150.4(4) . . . . ?
N22A B2A N12A N11A -32.8(5) . . . . ?
C41A B2A N12A N11A 84.7(5) . . . . ?
N11A N12A C13A C14A 0.2(5) . . . . ?
B2A N12A C13A C14A 175.6(4) . . . . ?
N12A C13A C14A C15A -1.1(5) . . . . ?
N12A N11A C15A C14A -1.6(5) . . . . ?
B1A N11A C15A C14A -174.2(4) . . . . ?
C13A C14A C15A N11A 1.7(5) . . . . ?
O1A B1A N21A C25A 36.3(6) . . . . ?
N11A B1A N21A C25A 154.0(4) . . . . ?
C31A B1A N21A C25A -87.6(5) . . . . ?
O1A B1A N21A N22A -151.0(4) . . . . ?
N11A B1A N21A N22A -33.4(5) . . . . ?
C31A B1A N21A N22A 85.1(5) . . . . ?
C25A N21A N22A C23A 0.8(5) . . . . ?
B1A N21A N22A C23A -173.2(4) . . . . ?
C25A N21A N22A B2A 173.5(4) . . . . ?
B1A N21A N22A B2A -0.5(6) . . . . ?
O2A B2A N22A C23A -37.8(6) . . . . ?
N12A B2A N22A C23A -155.5(4) . . . . ?
C41A B2A N22A C23A 85.8(5) . . . . ?
O2A B2A N22A N21A 151.2(4) . . . . ?
N12A B2A N22A N21A 33.5(5) . . . . ?
C41A B2A N22A N21A -85.2(5) . . . . ?
N21A N22A C23A C24A -0.9(5) . . . . ?
B2A N22A C23A C24A -172.9(4) . . . . ?
N22A C23A C24A C25A 0.6(5) . . . . ?
N22A N21A C25A C24A -0.5(5) . . . . ?
B1A N21A C25A C24A 173.2(4) . . . . ?
C23A C24A C25A N21A -0.1(5) . . . . ?
O1A B1A C31A C36A -64.9(6) . . . . ?
N11A B1A C31A C36A 171.0(4) . . . . ?
N21A B1A C31A C36A 57.4(6) . . . . ?
O1A B1A C31A C32A 116.6(5) . . . . ?
N11A B1A C31A C32A -7.5(6) . . . . ?
N21A B1A C31A C32A -121.1(4) . . . . ?
C36A C31A C32A C33A -0.4(7) . . . . ?
B1A C31A C32A C33A 178.2(4) . . . . ?
C31A C32A C33A C34A 0.4(7) . . . . ?
C32A C33A C34A C35A -0.2(7) . . . . ?
C32A C33A C34A Br1A 178.5(3) . . . . ?
C33A C34A C35A C36A 0.0(7) . . . . ?
Br1A C34A C35A C36A -178.7(3) . . . . ?
C34A C35A C36A C31A 0.0(7) . . . . ?
C32A C31A C36A C35A 0.2(7) . . . . ?
B1A C31A C36A C35A -178.4(4) . . . . ?
O2A B2A C41A C42A 116.7(5) . . . . ?
N22A B2A C41A C42A -5.6(6) . . . . ?
N12A B2A C41A C42A -119.7(5) . . . . ?
O2A B2A C41A C46A -66.4(6) . . . . ?
N22A B2A C41A C46A 171.3(4) . . . . ?
N12A B2A C41A C46A 57.2(5) . . . . ?
C46A C41A C42A C43A -0.6(7) . . . . ?
B2A C41A C42A C43A 176.5(4) . . . . ?
C41A C42A C43A C44A 0.3(7) . . . . ?
C42A C43A C44A C45A 0.1(7) . . . . ?
C42A C43A C44A Br2A 179.3(3) . . . . ?
C43A C44A C45A C46A -0.3(7) . . . . ?
Br2A C44A C45A C46A -179.5(3) . . . . ?
C44A C45A C46A C41A 0.0(7) . . . . ?
C42A C41A C46A C45A 0.4(7) . . . . ?
B2A C41A C46A C45A -176.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.553
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.103
_database_code_depnum_ccdc_archive 'CCDC 985511'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1090

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 B2 Br2 N4 O2'
_chemical_formula_sum            'C20 H20 B2 Br2 N4 O2'
_chemical_formula_weight         529.84

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   7.6702(5)
_cell_length_b                   12.4132(7)
_cell_length_c                   11.2406(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.351(5)
_cell_angle_gamma                90.00
_cell_volume                     1045.47(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12016
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      26.7

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    3.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4544
_exptl_absorpt_correction_T_max  0.6309
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14759
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         26.41
_reflns_number_total             2137
_reflns_number_gt                1756
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0369P)²] 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         2137
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
Br1 Br 0.25481(4) 0.56426(2) -0.08580(2) 0.03336(10) Uani 1 1 d . . .
B1 B 0.1737(3) 0.4594(2) 0.4500(2) 0.0194(5) Uani 1 1 d . . .
C1 C 0.3407(4) 0.3635(2) 0.6296(2) 0.0302(6) Uani 1 1 d . . .
H1A H 0.4476 0.3188 0.6546 0.045 Uiso 1 1 calc R . .
H1B H 0.2354 0.3225 0.6393 0.045 Uiso 1 1 calc R . .
H1C H 0.3519 0.4283 0.6804 0.045 Uiso 1 1 calc R . .
O1 O 0.3220(2) 0.39378(15) 0.50513(14) 0.0217(3) Uani 1 1 d . . .
N11 N 0.1599(2) 0.56297(17) 0.52726(17) 0.0192(4) Uani 1 1 d . . .
N12 N 0.0079(2) 0.60452(17) 0.55308(17) 0.0194(4) Uani 1 1 d . . .
C13 C 0.0465(3) 0.7024(2) 0.6016(2) 0.0249(5) Uani 1 1 d . . .
H13 H -0.0361 0.7490 0.6278 0.030 Uiso 1 1 calc R . .
C14 C 0.2251(3) 0.7254(2) 0.6079(2) 0.0249(5) Uani 1 1 d . . .
H14 H 0.2883 0.7887 0.6390 0.030 Uiso 1 1 calc R . .
C15 C 0.2912(3) 0.6362(2) 0.5590(2) 0.0233(5) Uani 1 1 d . . .
H15 H 0.4104 0.6277 0.5494 0.028 Uiso 1 1 calc R . .
C21 C 0.1913(3) 0.4903(2) 0.31351(19) 0.0195(5) Uani 1 1 d . . .
C22 C 0.1410(3) 0.5893(2) 0.2584(2) 0.0225(5) Uani 1 1 d . . .
H22 H 0.0934 0.6427 0.3031 0.027 Uiso 1 1 calc R . .
C23 C 0.1579(3) 0.6128(2) 0.1398(2) 0.0253(5) Uani 1 1 d . . .
H23 H 0.1225 0.6809 0.1041 0.030 Uiso 1 1 calc R . .
C24 C 0.2277(3) 0.5343(2) 0.0756(2) 0.0246(5) Uani 1 1 d . . .
C25 C 0.2789(3) 0.4348(2) 0.1260(2) 0.0278(5) Uani 1 1 d . . .
H25 H 0.3263 0.3816 0.0809 0.033 Uiso 1 1 calc R . .
C26 C 0.2598(3) 0.4141(2) 0.2433(2) 0.0252(5) Uani 1 1 d . . .
H26 H 0.2945 0.3455 0.2779 0.030 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
Br1 C24 1.906(2) . ?
B1 O1 1.428(3) . ?
B1 N11 1.568(3) . ?
B1 N12 1.597(3) 3_566 ?
B1 C21 1.615(3) . ?
C1 O1 1.426(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N11 C15 1.346(3) . ?
N11 N12 1.362(3) . ?
N12 C13 1.339(3) . ?
N12 B1 1.597(3) 3_566 ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C22 1.392(3) . ?
C21 C26 1.404(3) . ?
C22 C23 1.398(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(4) . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 H26 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
O1 B1 N11 111.65(18) . . ?
O1 B1 N12 109.7(2) . 3_566 ?
N11 B1 N12 104.93(17) . 3_566 ?
O1 B1 C21 109.11(19) . . ?
N11 B1 C21 111.1(2) . . ?
N12 B1 C21 110.32(18) 3_566 . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 O1 B1 118.68(19) . . ?
C15 N11 N12 108.27(19) . . ?
C15 N11 B1 124.44(19) . . ?
N12 N11 B1 126.21(18) . . ?
C13 N12 N11 107.81(19) . . ?
C13 N12 B1 125.1(2) . 3_566 ?
N11 N12 B1 126.2(2) . 3_566 ?
N12 C13 C14 109.7(2) . . ?
N12 C13 H13 125.1 . . ?
C14 C13 H13 125.1 . . ?
C15 C14 C13 104.9(2) . . ?
C15 C14 H14 127.5 . . ?
C13 C14 H14 127.5 . . ?
N11 C15 C14 109.3(2) . . ?
N11 C15 H15 125.4 . . ?
C14 C15 H15 125.4 . . ?
C22 C21 C26 116.5(2) . . ?
C22 C21 B1 124.1(2) . . ?
C26 C21 B1 119.4(2) . . ?
C21 C22 C23 122.3(2) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C24 C23 C22 118.4(2) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C25 C24 C23 121.5(2) . . ?
C25 C24 Br1 119.06(19) . . ?
C23 C24 Br1 119.4(2) . . ?
C24 C25 C26 118.6(2) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C25 C26 C21 122.7(2) . . ?
C25 C26 H26 118.7 . . ?
C21 C26 H26 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 B1 O1 C1 52.2(3) . . . . ?
N12 B1 O1 C1 -63.6(3) 3_566 . . . ?
C21 B1 O1 C1 175.4(2) . . . . ?
O1 B1 N11 C15 56.8(3) . . . . ?
N12 B1 N11 C15 175.5(2) 3_566 . . . ?
C21 B1 N11 C15 -65.3(3) . . . . ?
O1 B1 N11 N12 -136.5(2) . . . . ?
N12 B1 N11 N12 -17.8(3) 3_566 . . . ?
C21 B1 N11 N12 101.4(2) . . . . ?
C15 N11 N12 C13 -0.6(2) . . . . ?
B1 N11 N12 C13 -169.1(2) . . . . ?
C15 N11 N12 B1 -170.1(2) . . . 3_566 ?
B1 N11 N12 B1 21.5(4) . . . 3_566 ?
N11 N12 C13 C14 0.0(3) . . . . ?
B1 N12 C13 C14 169.6(2) 3_566 . . . ?
N12 C13 C14 C15 0.6(3) . . . . ?
N12 N11 C15 C14 1.0(3) . . . . ?
B1 N11 C15 C14 169.7(2) . . . . ?
C13 C14 C15 N11 -1.0(3) . . . . ?
O1 B1 C21 C22 -143.8(2) . . . . ?
N11 B1 C21 C22 -20.3(3) . . . . ?
N12 B1 C21 C22 95.6(3) 3_566 . . . ?
O1 B1 C21 C26 36.7(3) . . . . ?
N11 B1 C21 C26 160.2(2) . . . . ?
N12 B1 C21 C26 -83.9(3) 3_566 . . . ?
C26 C21 C22 C23 -0.3(3) . . . . ?
B1 C21 C22 C23 -179.8(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C22 C23 C24 Br1 -179.39(17) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
Br1 C24 C25 C26 179.58(18) . . . . ?
C24 C25 C26 C21 -0.3(4) . . . . ?
C22 C21 C26 C25 0.5(4) . . . . ?
B1 C21 C26 C25 -179.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 985512'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1304

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H38 B2 N4 O2 Si2'
_chemical_formula_sum            'C26 H38 B2 N4 O2 Si2'
_chemical_formula_weight         516.40

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.4434(10)
_cell_length_b                   20.6663(13)
_cell_length_c                   12.4374(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.677(6)
_cell_angle_gamma                90.00
_cell_volume                     3011.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15750
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9279
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20886
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.98
_reflns_number_total             5851
_reflns_number_gt                4430
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0743P)²+0.9916P] 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         5851
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Si1 Si 0.84764(6) 0.64338(3) 0.94126(7) 0.0372(2) Uani 1 1 d . . .
Si2 Si 0.25828(6) 0.76359(3) 0.34990(7) 0.0364(2) Uani 1 1 d . . .
B1 B 0.4388(2) 0.44411(13) 0.7486(2) 0.0272(5) Uani 1 1 d . . .
O1 O 0.46712(15) 0.38305(8) 0.80557(16) 0.0350(4) Uani 1 1 d . . .
C1 C 0.3878(3) 0.33114(13) 0.7668(3) 0.0478(7) Uani 1 1 d . . .
H1A H 0.4172 0.2926 0.8133 0.072 Uiso 1 1 calc R . .
H1B H 0.3773 0.3217 0.6867 0.072 Uiso 1 1 calc R . .
H1C H 0.3144 0.3435 0.7738 0.072 Uiso 1 1 calc R . .
B2 B 0.2113(2) 0.48225(13) 0.5331(2) 0.0280(5) Uani 1 1 d . . .
O2 O 0.11070(15) 0.44874(8) 0.46665(15) 0.0343(4) Uani 1 1 d . . .
C2 C 0.0946(3) 0.38379(13) 0.4972(3) 0.0473(7) Uani 1 1 d . . .
H2A H 0.0229 0.3669 0.4439 0.071 Uiso 1 1 calc R . .
H2B H 0.0917 0.3830 0.5749 0.071 Uiso 1 1 calc R . .
H2C H 0.1582 0.3569 0.4936 0.071 Uiso 1 1 calc R . .
N11 N 0.41941(17) 0.43563(9) 0.61618(18) 0.0293(4) Uani 1 1 d . . .
N12 N 0.32087(18) 0.44472(10) 0.52786(18) 0.0297(4) Uani 1 1 d . . .
C13 C 0.3370(3) 0.42588(14) 0.4311(2) 0.0408(6) Uani 1 1 d . . .
H13 H 0.2812 0.4276 0.3570 0.049 Uiso 1 1 calc R . .
C14 C 0.4471(3) 0.40371(14) 0.4562(3) 0.0436(7) Uani 1 1 d . . .
H14 H 0.4816 0.3872 0.4044 0.052 Uiso 1 1 calc R . .
C15 C 0.4962(2) 0.41064(14) 0.5726(2) 0.0403(6) Uani 1 1 d . . .
H15 H 0.5727 0.3995 0.6157 0.048 Uiso 1 1 calc R . .
N21 N 0.32047(16) 0.46999(9) 0.75336(17) 0.0268(4) Uani 1 1 d . . .
N22 N 0.22413(16) 0.48267(9) 0.66369(17) 0.0254(4) Uani 1 1 d . . .
C23 C 0.1420(2) 0.50094(11) 0.7048(2) 0.0309(5) Uani 1 1 d . . .
H23 H 0.0664 0.5128 0.6601 0.037 Uiso 1 1 calc R . .
C24 C 0.1852(2) 0.49974(12) 0.8226(2) 0.0351(6) Uani 1 1 d . . .
H24 H 0.1460 0.5101 0.8740 0.042 Uiso 1 1 calc R . .
C25 C 0.2977(2) 0.48019(13) 0.8500(2) 0.0345(5) Uani 1 1 d . . .
H25 H 0.3504 0.4749 0.9251 0.041 Uiso 1 1 calc R . .
C31 C 0.5402(2) 0.49483(11) 0.8050(2) 0.0273(5) Uani 1 1 d . . .
C32 C 0.5240(2) 0.56012(12) 0.8249(2) 0.0332(5) Uani 1 1 d . . .
H32 H 0.4485 0.5757 0.8097 0.040 Uiso 1 1 calc R . .
C33 C 0.6147(2) 0.60297(12) 0.8664(2) 0.0343(6) Uani 1 1 d . . .
H33 H 0.5995 0.6468 0.8793 0.041 Uiso 1 1 calc R . .
C34 C 0.7276(2) 0.58329(11) 0.8896(2) 0.0292(5) Uani 1 1 d . . .
C35 C 0.7445(2) 0.51758(12) 0.8729(2) 0.0315(5) Uani 1 1 d . . .
H35 H 0.8201 0.5019 0.8896 0.038 Uiso 1 1 calc R . .
C36 C 0.6538(2) 0.47470(11) 0.8327(2) 0.0307(5) Uani 1 1 d . . .
H36 H 0.6692 0.4304 0.8238 0.037 Uiso 1 1 calc R . .
C37 C 0.9858(3) 0.59963(18) 0.9926(4) 0.0757(13) Uani 1 1 d . . .
H37A H 0.9952 0.5741 0.9299 0.113 Uiso 1 1 calc R . .
H37B H 0.9869 0.5707 1.0554 0.113 Uiso 1 1 calc R . .
H37C H 1.0483 0.6309 1.0195 0.113 Uiso 1 1 calc R . .
C38 C 0.8305(4) 0.6917(2) 1.0605(4) 0.0854(15) Uani 1 1 d . . .
H38A H 0.7575 0.7147 1.0338 0.128 Uiso 1 1 calc R . .
H38B H 0.8930 0.7230 1.0871 0.128 Uiso 1 1 calc R . .
H38C H 0.8320 0.6627 1.1234 0.128 Uiso 1 1 calc R . .
C39 C 0.8430(4) 0.6990(2) 0.8215(4) 0.0799(13) Uani 1 1 d . . .
H39A H 0.7696 0.7217 0.7954 0.120 Uiso 1 1 calc R . .
H39B H 0.8519 0.6739 0.7582 0.120 Uiso 1 1 calc R . .
H39C H 0.9051 0.7306 0.8479 0.120 Uiso 1 1 calc R . .
C41 C 0.2131(2) 0.55480(11) 0.4864(2) 0.0272(5) Uani 1 1 d . . .
C42 C 0.1662(3) 0.57010(13) 0.3706(2) 0.0392(6) Uani 1 1 d . . .
H42 H 0.1267 0.5376 0.3182 0.047 Uiso 1 1 calc R . .
C43 C 0.1758(3) 0.63160(13) 0.3300(2) 0.0412(6) Uani 1 1 d . . .
H43 H 0.1429 0.6399 0.2505 0.049 Uiso 1 1 calc R . .
C44 C 0.2325(2) 0.68189(12) 0.4026(2) 0.0327(5) Uani 1 1 d . . .
C45 C 0.2781(3) 0.66665(12) 0.5181(2) 0.0391(6) Uani 1 1 d . . .
H45 H 0.3175 0.6991 0.5707 0.047 Uiso 1 1 calc R . .
C46 C 0.2674(2) 0.60503(12) 0.5585(2) 0.0375(6) Uani 1 1 d . . .
H46 H 0.2984 0.5970 0.6383 0.045 Uiso 1 1 calc R . .
C47 C 0.2815(4) 0.82521(15) 0.4659(4) 0.0648(10) Uani 1 1 d . . .
H47A H 0.2124 0.8289 0.4866 0.097 Uiso 1 1 calc R . .
H47B H 0.2987 0.8672 0.4390 0.097 Uiso 1 1 calc R . .
H47C H 0.3456 0.8118 0.5330 0.097 Uiso 1 1 calc R . .
C48 C 0.1346(3) 0.78626(18) 0.2228(3) 0.0622(10) Uani 1 1 d . . .
H48A H 0.0660 0.7896 0.2444 0.093 Uiso 1 1 calc R . .
H48B H 0.1230 0.7531 0.1636 0.093 Uiso 1 1 calc R . .
H48C H 0.1496 0.8280 0.1933 0.093 Uiso 1 1 calc R . .
C49 C 0.3902(2) 0.75795(14) 0.3120(3) 0.0459(7) Uani 1 1 d . . .
H49A H 0.4059 0.8000 0.2841 0.069 Uiso 1 1 calc R . .
H49B H 0.3797 0.7253 0.2522 0.069 Uiso 1 1 calc R . .
H49C H 0.4544 0.7456 0.3796 0.069 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C37 1.855(4) . ?
Si1 C38 1.858(4) . ?
Si1 C39 1.867(4) . ?
Si1 C34 1.881(2) . ?
Si2 C48 1.857(3) . ?
Si2 C49 1.858(3) . ?
Si2 C47 1.873(4) . ?
Si2 C44 1.878(3) . ?
B1 O1 1.432(3) . ?
B1 N21 1.586(3) . ?
B1 N11 1.592(3) . ?
B1 C31 1.609(3) . ?
O1 C1 1.427(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
B2 O2 1.426(3) . ?
B2 N22 1.578(3) . ?
B2 N12 1.588(3) . ?
B2 C41 1.611(3) . ?
O2 C2 1.427(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N11 C15 1.351(3) . ?
N11 N12 1.356(3) . ?
N12 C13 1.343(3) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C25 1.341(3) . ?
N21 N22 1.360(3) . ?
N22 C23 1.342(3) . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C31 C32 1.399(3) . ?
C31 C36 1.400(3) . ?
C32 C33 1.390(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.396(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.400(3) . ?
C35 C36 1.389(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C41 C46 1.389(3) . ?
C41 C42 1.396(4) . ?
C42 C43 1.388(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.401(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.391(4) . ?
C45 C46 1.392(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?

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
C37 Si1 C38 109.2(2) . . ?
C37 Si1 C39 110.5(2) . . ?
C38 Si1 C39 109.0(2) . . ?
C37 Si1 C34 109.46(14) . . ?
C38 Si1 C34 109.62(14) . . ?
C39 Si1 C34 109.04(16) . . ?
C48 Si2 C49 110.44(16) . . ?
C48 Si2 C47 110.68(19) . . ?
C49 Si2 C47 108.55(17) . . ?
C48 Si2 C44 109.51(14) . . ?
C49 Si2 C44 107.56(12) . . ?
C47 Si2 C44 110.03(15) . . ?
O1 B1 N21 110.8(2) . . ?
O1 B1 N11 110.0(2) . . ?
N21 B1 N11 104.87(18) . . ?
O1 B1 C31 109.41(19) . . ?
N21 B1 C31 111.47(19) . . ?
N11 B1 C31 110.23(19) . . ?
C1 O1 B1 117.9(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 B2 N22 111.3(2) . . ?
O2 B2 N12 109.7(2) . . ?
N22 B2 N12 104.73(18) . . ?
O2 B2 C41 111.1(2) . . ?
N22 B2 C41 110.92(19) . . ?
N12 B2 C41 108.90(19) . . ?
B2 O2 C2 118.5(2) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C15 N11 N12 107.3(2) . . ?
C15 N11 B1 125.2(2) . . ?
N12 N11 B1 127.13(19) . . ?
C13 N12 N11 108.6(2) . . ?
C13 N12 B2 124.6(2) . . ?
N11 N12 B2 126.08(19) . . ?
N12 C13 C14 109.3(2) . . ?
N12 C13 H13 125.3 . . ?
C14 C13 H13 125.3 . . ?
C15 C14 C13 105.1(2) . . ?
C15 C14 H14 127.5 . . ?
C13 C14 H14 127.5 . . ?
N11 C15 C14 109.7(2) . . ?
N11 C15 H15 125.1 . . ?
C14 C15 H15 125.1 . . ?
C25 N21 N22 108.12(19) . . ?
C25 N21 B1 124.4(2) . . ?
N22 N21 B1 127.40(19) . . ?
C23 N22 N21 108.4(2) . . ?
C23 N22 B2 124.6(2) . . ?
N21 N22 B2 126.77(18) . . ?
N22 C23 C24 109.0(2) . . ?
N22 C23 H23 125.5 . . ?
C24 C23 H23 125.5 . . ?
C23 C24 C25 105.4(2) . . ?
C23 C24 H24 127.3 . . ?
C25 C24 H24 127.3 . . ?
N21 C25 C24 109.1(2) . . ?
N21 C25 H25 125.5 . . ?
C24 C25 H25 125.5 . . ?
C32 C31 C36 115.9(2) . . ?
C32 C31 B1 124.5(2) . . ?
C36 C31 B1 119.5(2) . . ?
C33 C32 C31 122.2(2) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C32 C33 C34 121.7(2) . . ?
C32 C33 H33 119.1 . . ?
C34 C33 H33 119.1 . . ?
C33 C34 C35 116.3(2) . . ?
C33 C34 Si1 120.41(18) . . ?
C35 C34 Si1 123.32(18) . . ?
C36 C35 C34 121.9(2) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C35 C36 C31 122.0(2) . . ?
C35 C36 H36 119.0 . . ?
C31 C36 H36 119.0 . . ?
Si1 C37 H37A 109.5 . . ?
Si1 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
Si1 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
Si1 C38 H38A 109.5 . . ?
Si1 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
Si1 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
Si1 C39 H39A 109.5 . . ?
Si1 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
Si1 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C46 C41 C42 116.1(2) . . ?
C46 C41 B2 121.7(2) . . ?
C42 C41 B2 122.1(2) . . ?
C43 C42 C41 121.7(2) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C42 C43 C44 122.1(3) . . ?
C42 C43 H43 118.9 . . ?
C44 C43 H43 118.9 . . ?
C45 C44 C43 116.0(2) . . ?
C45 C44 Si2 120.39(19) . . ?
C43 C44 Si2 123.4(2) . . ?
C44 C45 C46 121.7(2) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
C41 C46 C45 122.3(2) . . ?
C41 C46 H46 118.8 . . ?
C45 C46 H46 118.8 . . ?
Si2 C47 H47A 109.5 . . ?
Si2 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
Si2 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
Si2 C48 H48A 109.5 . . ?
Si2 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
Si2 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
Si2 C49 H49A 109.5 . . ?
Si2 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
Si2 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?

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
N21 B1 O1 C1 57.4(3) . . . . ?
N11 B1 O1 C1 -58.1(3) . . . . ?
C31 B1 O1 C1 -179.3(2) . . . . ?
N22 B2 O2 C2 -55.2(3) . . . . ?
N12 B2 O2 C2 60.3(3) . . . . ?
C41 B2 O2 C2 -179.3(2) . . . . ?
O1 B1 N11 C15 -56.4(3) . . . . ?
N21 B1 N11 C15 -175.6(2) . . . . ?
C31 B1 N11 C15 64.3(3) . . . . ?
O1 B1 N11 N12 115.4(2) . . . . ?
N21 B1 N11 N12 -3.8(3) . . . . ?
C31 B1 N11 N12 -123.9(2) . . . . ?
C15 N11 N12 C13 -0.3(3) . . . . ?
B1 N11 N12 C13 -173.3(2) . . . . ?
C15 N11 N12 B2 -170.6(2) . . . . ?
B1 N11 N12 B2 16.4(4) . . . . ?
O2 B2 N12 C13 51.3(3) . . . . ?
N22 B2 N12 C13 170.9(2) . . . . ?
C41 B2 N12 C13 -70.4(3) . . . . ?
O2 B2 N12 N11 -139.9(2) . . . . ?
N22 B2 N12 N11 -20.3(3) . . . . ?
C41 B2 N12 N11 98.4(3) . . . . ?
N11 N12 C13 C14 0.5(3) . . . . ?
B2 N12 C13 C14 170.9(2) . . . . ?
N12 C13 C14 C15 -0.4(3) . . . . ?
N12 N11 C15 C14 0.0(3) . . . . ?
B1 N11 C15 C14 173.2(2) . . . . ?
C13 C14 C15 N11 0.2(3) . . . . ?
O1 B1 N21 C25 57.4(3) . . . . ?
N11 B1 N21 C25 176.1(2) . . . . ?
C31 B1 N21 C25 -64.7(3) . . . . ?
O1 B1 N21 N22 -119.2(2) . . . . ?
N11 B1 N21 N22 -0.5(3) . . . . ?
C31 B1 N21 N22 118.7(2) . . . . ?
C25 N21 N22 C23 0.2(3) . . . . ?
B1 N21 N22 C23 177.3(2) . . . . ?
C25 N21 N22 B2 175.4(2) . . . . ?
B1 N21 N22 B2 -7.6(3) . . . . ?
O2 B2 N22 C23 -51.0(3) . . . . ?
N12 B2 N22 C23 -169.5(2) . . . . ?
C41 B2 N22 C23 73.1(3) . . . . ?
O2 B2 N22 N21 134.6(2) . . . . ?
N12 B2 N22 N21 16.1(3) . . . . ?
C41 B2 N22 N21 -101.2(2) . . . . ?
N21 N22 C23 C24 -0.4(3) . . . . ?
B2 N22 C23 C24 -175.7(2) . . . . ?
N22 C23 C24 C25 0.4(3) . . . . ?
N22 N21 C25 C24 0.0(3) . . . . ?
B1 N21 C25 C24 -177.2(2) . . . . ?
C23 C24 C25 N21 -0.2(3) . . . . ?
O1 B1 C31 C32 -140.5(2) . . . . ?
N21 B1 C31 C32 -17.6(3) . . . . ?
N11 B1 C31 C32 98.4(3) . . . . ?
O1 B1 C31 C36 42.3(3) . . . . ?
N21 B1 C31 C36 165.2(2) . . . . ?
N11 B1 C31 C36 -78.8(3) . . . . ?
C36 C31 C32 C33 2.0(4) . . . . ?
B1 C31 C32 C33 -175.3(2) . . . . ?
C31 C32 C33 C34 0.6(4) . . . . ?
C32 C33 C34 C35 -2.4(4) . . . . ?
C32 C33 C34 Si1 178.1(2) . . . . ?
C37 Si1 C34 C33 168.2(3) . . . . ?
C38 Si1 C34 C33 48.4(3) . . . . ?
C39 Si1 C34 C33 -70.8(3) . . . . ?
C37 Si1 C34 C35 -11.3(3) . . . . ?
C38 Si1 C34 C35 -131.1(3) . . . . ?
C39 Si1 C34 C35 109.6(3) . . . . ?
C33 C34 C35 C36 1.6(4) . . . . ?
Si1 C34 C35 C36 -178.8(2) . . . . ?
C34 C35 C36 C31 0.9(4) . . . . ?
C32 C31 C36 C35 -2.7(4) . . . . ?
B1 C31 C36 C35 174.7(2) . . . . ?
O2 B2 C41 C46 150.2(2) . . . . ?
N22 B2 C41 C46 25.9(3) . . . . ?
N12 B2 C41 C46 -88.8(3) . . . . ?
O2 B2 C41 C42 -33.6(3) . . . . ?
N22 B2 C41 C42 -157.9(2) . . . . ?
N12 B2 C41 C42 87.4(3) . . . . ?
C46 C41 C42 C43 1.4(4) . . . . ?
B2 C41 C42 C43 -174.9(3) . . . . ?
C41 C42 C43 C44 -0.3(5) . . . . ?
C42 C43 C44 C45 -0.4(4) . . . . ?
C42 C43 C44 Si2 174.6(2) . . . . ?
C48 Si2 C44 C45 -149.4(2) . . . . ?
C49 Si2 C44 C45 90.5(2) . . . . ?
C47 Si2 C44 C45 -27.6(3) . . . . ?
C48 Si2 C44 C43 35.8(3) . . . . ?
C49 Si2 C44 C43 -84.2(3) . . . . ?
C47 Si2 C44 C43 157.7(3) . . . . ?
C43 C44 C45 C46 -0.2(4) . . . . ?
Si2 C44 C45 C46 -175.3(2) . . . . ?
C42 C41 C46 C45 -2.0(4) . . . . ?
B2 C41 C46 C45 174.4(2) . . . . ?
C44 C45 C46 C41 1.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 985513'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1646

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H10 B4 F24 N8, 3(C7 H8)'
_chemical_formula_sum            'C47 H34 B4 F24 N8'
_chemical_formula_weight         1210.06

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.8267(8)
_cell_length_b                   11.3525(11)
_cell_length_c                   14.2556(14)
_cell_angle_alpha                99.583(8)
_cell_angle_beta                 106.299(7)
_cell_angle_gamma                106.005(7)
_cell_volume                     1271.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17458
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      26.76

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15695
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.181
_diffrn_reflns_theta_max         25.914
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4864
_reflns_number_gt                3949
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0608P)²+0.3938P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4864
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
B1 B 0.6835(2) 0.37083(19) 0.39516(14) 0.0217(4) Uani 1 1 d . . . . .
H1 H 0.814(2) 0.3933(18) 0.4194(14) 0.017(4) Uiso 1 1 d . . . . .
B2 B 0.3444(2) 0.28894(18) 0.30928(14) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.207(3) 0.244(2) 0.2653(15) 0.026(5) Uiso 1 1 d . . . . .
N2 N 0.44533(17) 0.34069(14) 0.23869(11) 0.0215(3) Uani 1 1 d . . . . .
N1 N 0.61436(17) 0.38150(14) 0.28154(11) 0.0220(3) Uani 1 1 d . . . . .
C3 C 0.4085(2) 0.36160(17) 0.14645(13) 0.0247(4) Uani 1 1 d . . . . .
C4 C 0.5542(2) 0.41617(18) 0.12858(14) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.5649 0.4409 0.0696 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6811(2) 0.42678(17) 0.21584(13) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.2311(2) 0.3255(2) 0.07672(14) 0.0305(4) Uani 1 1 d . . . . .
F61 F 0.23046(17) 0.36280(18) -0.00682(10) 0.0592(4) Uani 1 1 d . . . . .
F62 F 0.14078(14) 0.37852(13) 0.11770(9) 0.0424(3) Uani 1 1 d . . . . .
F63 F 0.15144(16) 0.20181(13) 0.04987(11) 0.0538(4) Uani 1 1 d . . . . .
C7 C 0.8669(2) 0.4770(2) 0.23900(15) 0.0321(4) Uani 1 1 d . . . . .
F71 F 0.90028(17) 0.52105(17) 0.16402(11) 0.0592(4) Uani 1 1 d . . . . .
F72 F 0.93520(15) 0.38695(13) 0.24958(11) 0.0469(3) Uani 1 1 d . . . . .
F73 F 0.94552(16) 0.56847(14) 0.32349(11) 0.0525(4) Uani 1 1 d . . . . .
N11 N 0.59111(18) 0.22284(14) 0.37810(11) 0.0226(3) Uani 1 1 d . . . . .
N12 N 0.42208(18) 0.18141(14) 0.33493(11) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.3641(2) 0.05652(17) 0.32524(14) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.4967(3) 0.01502(18) 0.36268(15) 0.0316(4) Uani 1 1 d . . . . .
H14 H 0.4920 -0.0689 0.3654 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6372(2) 0.12266(18) 0.39519(14) 0.0278(4) Uani 1 1 d . . . . .
C16 C 0.1811(3) -0.01846(19) 0.27905(16) 0.0334(4) Uani 1 1 d . . . . .
F161 F 0.15506(17) -0.13852(12) 0.28276(13) 0.0537(4) Uani 1 1 d . . . . .
F162 F 0.11879(16) -0.02009(14) 0.18208(10) 0.0500(3) Uani 1 1 d . . . . .
F163 F 0.09139(16) 0.02592(13) 0.32640(12) 0.0496(3) Uani 1 1 d . . . . .
C17 C 0.8170(3) 0.1359(2) 0.44128(16) 0.0377(5) Uani 1 1 d . . . . .
F171 F 0.83029(19) 0.02612(14) 0.45325(14) 0.0670(5) Uani 1 1 d . . . . .
F172 F 0.90692(17) 0.17544(17) 0.38467(13) 0.0611(4) Uani 1 1 d . . . . .
F173 F 0.88867(18) 0.21858(15) 0.53147(11) 0.0585(4) Uani 1 1 d . . . . .
C21 C 0.5942(2) 0.44311(16) 0.45603(12) 0.0202(3) Uani 1 1 d . . . . .
C22 C 0.4177(2) 0.39980(16) 0.41176(12) 0.0203(3) Uani 1 1 d . . . . .
C23 C 0.3245(2) 0.45713(16) 0.45628(12) 0.0202(3) Uani 1 1 d . . . . .
H23 H 0.2056 0.4280 0.4267 0.024 Uiso 1 1 calc R U . . .
C31 C 0.4129(7) -0.0268(5) -0.0413(4) 0.0551(14) Uani 0.5 1 d . . P . .
C32 C 0.4421(5) 0.0373(3) 0.0600(2) 0.0579(8) Uani 1 1 d . . . . .
H32 H 0.3507 0.0440 0.0806 0.070 Uiso 0.5 1 d R U P A 1
H32A H 0.4556 0.0835 0.1256 0.070 Uiso 0.5 1 d R U P A 2
C33 C 0.5970(8) 0.0872(5) 0.1252(4) 0.0545(13) Uani 0.5 1 d . . P . .
H33 H 0.6100 0.1342 0.1904 0.065 Uiso 0.5 1 d R U P . .
C34 C 0.7433(6) 0.0791(4) 0.1099(4) 0.0997(15) Uani 1 1 d . . . . .
H34 H 0.8513 0.1127 0.1611 0.120 Uiso 0.5 1 d R U P B 1
H34A H 0.7374 0.1184 0.1748 0.150 Uiso 0.5 1 d R U P B 2
H34B H 0.7938 0.0130 0.1184 0.150 Uiso 0.5 1 d R U P B 2
H34C H 0.8121 0.1439 0.0871 0.150 Uiso 0.5 1 d R U P B 2
C35 C 0.7118(9) 0.0141(6) 0.0086(6) 0.0703(19) Uani 0.5 1 d . . P . .
H35 H 0.8037 0.0071 -0.0114 0.084 Uiso 0.5 1 d R U P . .
C41 C 0.3798(3) 0.70478(19) 0.16205(16) 0.0339(4) Uani 1 1 d . . . . .
C42 C 0.3761(3) 0.66773(19) 0.24954(17) 0.0369(5) Uani 1 1 d . . . . .
H42 H 0.2710 0.6313 0.2571 0.044 Uiso 1 1 calc R U . . .
C43 C 0.5227(3) 0.6829(2) 0.32601(18) 0.0448(5) Uani 1 1 d . . . . .
H43 H 0.5181 0.6572 0.3855 0.054 Uiso 1 1 calc R U . . .
C44 C 0.6747(3) 0.7352(2) 0.3153(2) 0.0556(7) Uani 1 1 d . . . . .
H44 H 0.7758 0.7459 0.3675 0.067 Uiso 1 1 calc R U . . .
C45 C 0.6805(3) 0.7725(3) 0.2284(3) 0.0603(7) Uani 1 1 d . . . . .
H45 H 0.7859 0.8085 0.2210 0.072 Uiso 1 1 calc R U . . .
C46 C 0.5344(3) 0.7576(2) 0.1524(2) 0.0462(5) Uani 1 1 d . . . . .
H46 H 0.5397 0.7838 0.0931 0.055 Uiso 1 1 calc R U . . .
C47 C 0.2189(3) 0.6880(3) 0.07918(19) 0.0519(6) Uani 1 1 d . . . . .
H47A H 0.2456 0.7221 0.0247 0.078 Uiso 1 1 calc R U . . .
H47B H 0.1550 0.7336 0.1069 0.078 Uiso 1 1 calc R U . . .
H47C H 0.1519 0.5974 0.0522 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N11 1.595(3) . ?
B1 C21 1.597(2) . ?
B1 N1 1.601(2) . ?
B1 H1 1.045(19) . ?
B2 C22 1.595(3) . ?
B2 N2 1.601(2) . ?
B2 N12 1.601(2) . ?
B2 H2 1.12(2) . ?
N2 C3 1.341(2) . ?
N2 N1 1.3517(19) . ?
N1 C5 1.339(2) . ?
C3 C4 1.378(3) . ?
C3 C6 1.498(2) . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.497(3) . ?
C6 F63 1.318(3) . ?
C6 F62 1.322(2) . ?
C6 F61 1.328(2) . ?
C7 F73 1.315(2) . ?
C7 F71 1.324(2) . ?
C7 F72 1.331(2) . ?
N11 C15 1.345(2) . ?
N11 N12 1.352(2) . ?
N12 C13 1.336(2) . ?
C13 C14 1.384(3) . ?
C13 C16 1.491(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.491(3) . ?
C16 F163 1.320(2) . ?
C16 F161 1.331(2) . ?
C16 F162 1.332(3) . ?
C17 F171 1.318(2) . ?
C17 F173 1.322(3) . ?
C17 F172 1.329(3) . ?
C21 C23 1.392(2) 2_666 ?
C21 C22 1.411(2) . ?
C22 C23 1.398(2) . ?
C23 C21 1.392(2) 2_666 ?
C23 H23 0.9500 . ?
C31 C33 1.243(8) 2_655 ?
C31 C35 1.342(9) 2_655 ?
C31 C34 1.345(7) 2_655 ?
C31 C32 1.411(7) 2_655 ?
C31 C32 1.421(6) . ?
C31 C31 1.533(10) 2_655 ?
C32 C33 1.318(7) . ?
C32 C35 1.331(8) 2_655 ?
C32 C31 1.411(7) 2_655 ?
C32 H32 0.9499 . ?
C32 H32A 0.9500 . ?
C33 C31 1.243(8) 2_655 ?
C33 C34 1.393(8) . ?
C33 H32A 1.2387 . ?
C33 H33 0.9500 . ?
C33 H34A 1.1598 . ?
C34 C31 1.345(7) 2_655 ?
C34 C35 1.419(9) . ?
C34 H34 0.9500 . ?
C34 H34A 0.9799 . ?
C34 H34B 0.9801 . ?
C34 H34C 0.9800 . ?
C35 C32 1.331(8) 2_655 ?
C35 C31 1.342(9) 2_655 ?
C35 H35 0.9500 . ?
C41 C46 1.387(3) . ?
C41 C42 1.387(3) . ?
C41 C47 1.511(3) . ?
C42 C43 1.384(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.372(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.384(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.379(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 B1 C21 106.09(14) . . ?
N11 B1 N1 99.65(13) . . ?
C21 B1 N1 105.10(13) . . ?
N11 B1 H1 111.0(10) . . ?
C21 B1 H1 122.2(11) . . ?
N1 B1 H1 110.3(10) . . ?
C22 B2 N2 105.51(14) . . ?
C22 B2 N12 106.04(13) . . ?
N2 B2 N12 99.50(12) . . ?
C22 B2 H2 122.7(11) . . ?
N2 B2 H2 110.7(11) . . ?
N12 B2 H2 109.8(11) . . ?
C3 N2 N1 107.69(14) . . ?
C3 N2 B2 137.12(14) . . ?
N1 N2 B2 115.09(13) . . ?
C5 N1 N2 108.34(14) . . ?
C5 N1 B1 136.39(14) . . ?
N2 N1 B1 115.19(13) . . ?
N2 C3 C4 110.02(15) . . ?
N2 C3 C6 122.03(16) . . ?
C4 C3 C6 127.93(16) . . ?
C3 C4 C5 104.35(16) . . ?
C3 C4 H4 127.8 . . ?
C5 C4 H4 127.8 . . ?
N1 C5 C4 109.58(15) . . ?
N1 C5 C7 122.00(16) . . ?
C4 C5 C7 128.41(17) . . ?
F63 C6 F62 106.51(17) . . ?
F63 C6 F61 108.04(17) . . ?
F62 C6 F61 107.56(16) . . ?
F63 C6 C3 112.27(16) . . ?
F62 C6 C3 112.70(16) . . ?
F61 C6 C3 109.54(16) . . ?
F73 C7 F71 108.41(18) . . ?
F73 C7 F72 106.36(16) . . ?
F71 C7 F72 107.18(17) . . ?
F73 C7 C5 112.70(16) . . ?
F71 C7 C5 110.12(16) . . ?
F72 C7 C5 111.83(17) . . ?
C15 N11 N12 108.01(15) . . ?
C15 N11 B1 136.55(15) . . ?
N12 N11 B1 115.44(13) . . ?
C13 N12 N11 108.19(14) . . ?
C13 N12 B2 136.88(15) . . ?
N11 N12 B2 114.93(13) . . ?
N12 C13 C14 109.68(17) . . ?
N12 C13 C16 121.49(16) . . ?
C14 C13 C16 128.82(18) . . ?
C15 C14 C13 104.57(16) . . ?
C15 C14 H14 127.7 . . ?
C13 C14 H14 127.7 . . ?
N11 C15 C14 109.54(16) . . ?
N11 C15 C17 121.58(17) . . ?
C14 C15 C17 128.87(17) . . ?
F163 C16 F161 107.58(17) . . ?
F163 C16 F162 107.19(17) . . ?
F161 C16 F162 107.19(17) . . ?
F163 C16 C13 112.52(17) . . ?
F161 C16 C13 109.89(16) . . ?
F162 C16 C13 112.21(17) . . ?
F171 C17 F173 107.42(17) . . ?
F171 C17 F172 107.86(18) . . ?
F173 C17 F172 106.88(19) . . ?
F171 C17 C15 110.45(18) . . ?
F173 C17 C15 111.70(17) . . ?
F172 C17 C15 112.30(17) . . ?
C23 C21 C22 120.09(15) 2_666 . ?
C23 C21 B1 125.79(15) 2_666 . ?
C22 C21 B1 114.10(15) . . ?
C23 C22 C21 119.85(16) . . ?
C23 C22 B2 126.11(15) . . ?
C21 C22 B2 114.00(15) . . ?
C21 C23 C22 120.06(15) 2_666 . ?
C21 C23 H23 120.0 2_666 . ?
C22 C23 H23 120.0 . . ?
C33 C31 C35 128.6(6) 2_655 2_655 ?
C34 C31 C32 124.1(5) 2_655 2_655 ?
C34 C31 C32 121.3(6) 2_655 . ?
C32 C31 C32 114.4(4) 2_655 . ?
C33 C31 C31 116.5(8) 2_655 2_655 ?
C35 C31 C31 114.3(7) 2_655 2_655 ?
C35 C32 C31 123.7(4) 2_655 2_655 ?
C33 C32 C31 119.5(4) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.2 . . ?
C35 C32 H32A 118.4 2_655 . ?
C31 C32 H32A 117.9 2_655 . ?
C32 C33 C34 127.8(5) . . ?
C31 C33 H32A 110.3 2_655 . ?
C32 C33 H33 115.9 . . ?
C34 C33 H33 116.3 . . ?
C31 C33 H34A 104.9 2_655 . ?
C33 C34 C35 111.9(4) . . ?
C33 C34 H34 124.2 . . ?
C35 C34 H34 123.9 . . ?
C31 C34 H34A 109.1 2_655 . ?
C31 C34 H34B 109.5 2_655 . ?
C33 C34 H34B 128.8 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.8 2_655 . ?
C33 C34 H34C 121.7 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 C34 122.4(5) 2_655 . ?
C32 C35 H35 118.5 2_655 . ?
C34 C35 H35 119.1 . . ?
C46 C41 C42 118.5(2) . . ?
C46 C41 C47 120.8(2) . . ?
C42 C41 C47 120.7(2) . . ?
C43 C42 C41 121.2(2) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C44 C43 C42 119.6(2) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 119.9(2) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C44 120.4(2) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C45 C46 C41 120.3(2) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C41 C47 H47A 109.5 . . ?
C41 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C41 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?

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
C22 B2 N2 C3 -122.5(2) . . . . ?
N12 B2 N2 C3 127.8(2) . . . . ?
C22 B2 N2 N1 53.40(17) . . . . ?
N12 B2 N2 N1 -56.31(17) . . . . ?
C3 N2 N1 C5 -0.25(19) . . . . ?
B2 N2 N1 C5 -177.31(14) . . . . ?
C3 N2 N1 B1 177.08(14) . . . . ?
B2 N2 N1 B1 0.02(19) . . . . ?
N11 B1 N1 C5 -127.5(2) . . . . ?
C21 B1 N1 C5 122.8(2) . . . . ?
N11 B1 N1 N2 56.15(16) . . . . ?
C21 B1 N1 N2 -53.55(18) . . . . ?
N1 N2 C3 C4 0.1(2) . . . . ?
B2 N2 C3 C4 176.22(18) . . . . ?
N1 N2 C3 C6 178.99(16) . . . . ?
B2 N2 C3 C6 -4.9(3) . . . . ?
N2 C3 C4 C5 0.0(2) . . . . ?
C6 C3 C4 C5 -178.74(18) . . . . ?
N2 N1 C5 C4 0.3(2) . . . . ?
B1 N1 C5 C4 -176.22(18) . . . . ?
N2 N1 C5 C7 -178.54(16) . . . . ?
B1 N1 C5 C7 5.0(3) . . . . ?
C3 C4 C5 N1 -0.2(2) . . . . ?
C3 C4 C5 C7 178.54(19) . . . . ?
N2 C3 C6 F63 -63.3(2) . . . . ?
C4 C3 C6 F63 115.4(2) . . . . ?
N2 C3 C6 F62 57.0(2) . . . . ?
C4 C3 C6 F62 -124.4(2) . . . . ?
N2 C3 C6 F61 176.69(17) . . . . ?
C4 C3 C6 F61 -4.7(3) . . . . ?
N1 C5 C7 F73 -56.0(2) . . . . ?
C4 C5 C7 F73 125.4(2) . . . . ?
N1 C5 C7 F71 -177.19(17) . . . . ?
C4 C5 C7 F71 4.2(3) . . . . ?
N1 C5 C7 F72 63.8(2) . . . . ?
C4 C5 C7 F72 -114.8(2) . . . . ?
C21 B1 N11 C15 -127.4(2) . . . . ?
N1 B1 N11 C15 123.6(2) . . . . ?
C21 B1 N11 N12 52.98(18) . . . . ?
N1 B1 N11 N12 -55.93(17) . . . . ?
C15 N11 N12 C13 -0.10(19) . . . . ?
B1 N11 N12 C13 179.59(14) . . . . ?
C15 N11 N12 B2 179.87(14) . . . . ?
B1 N11 N12 B2 -0.4(2) . . . . ?
C22 B2 N12 C13 127.3(2) . . . . ?
N2 B2 N12 C13 -123.5(2) . . . . ?
C22 B2 N12 N11 -52.69(18) . . . . ?
N2 B2 N12 N11 56.59(17) . . . . ?
N11 N12 C13 C14 0.1(2) . . . . ?
B2 N12 C13 C14 -179.87(18) . . . . ?
N11 N12 C13 C16 -179.47(16) . . . . ?
B2 N12 C13 C16 0.6(3) . . . . ?
N12 C13 C14 C15 0.0(2) . . . . ?
C16 C13 C14 C15 179.47(19) . . . . ?
N12 N11 C15 C14 0.1(2) . . . . ?
B1 N11 C15 C14 -179.52(18) . . . . ?
N12 N11 C15 C17 179.19(17) . . . . ?
B1 N11 C15 C17 -0.4(3) . . . . ?
C13 C14 C15 N11 0.0(2) . . . . ?
C13 C14 C15 C17 -179.05(19) . . . . ?
N12 C13 C16 F163 -57.0(2) . . . . ?
C14 C13 C16 F163 123.5(2) . . . . ?
N12 C13 C16 F161 -176.88(17) . . . . ?
C14 C13 C16 F161 3.7(3) . . . . ?
N12 C13 C16 F162 64.0(2) . . . . ?
C14 C13 C16 F162 -115.5(2) . . . . ?
N11 C15 C17 F171 178.12(19) . . . . ?
C14 C15 C17 F171 -3.0(3) . . . . ?
N11 C15 C17 F173 58.6(3) . . . . ?
C14 C15 C17 F173 -122.4(2) . . . . ?
N11 C15 C17 F172 -61.4(2) . . . . ?
C14 C15 C17 F172 117.5(2) . . . . ?
N11 B1 C21 C23 130.09(17) . . . 2_666 ?
N1 B1 C21 C23 -124.93(17) . . . 2_666 ?
N11 B1 C21 C22 -51.60(18) . . . . ?
N1 B1 C21 C22 53.38(18) . . . . ?
C23 C21 C22 C23 -0.1(3) 2_666 . . . ?
B1 C21 C22 C23 -178.54(15) . . . . ?
C23 C21 C22 B2 177.60(15) 2_666 . . . ?
B1 C21 C22 B2 -0.8(2) . . . . ?
N2 B2 C22 C23 125.33(17) . . . . ?
N12 B2 C22 C23 -129.72(16) . . . . ?
N2 B2 C22 C21 -52.24(17) . . . . ?
N12 B2 C22 C21 52.71(18) . . . . ?
C21 C22 C23 C21 0.1(3) . . . 2_666 ?
B2 C22 C23 C21 -177.31(15) . . . 2_666 ?
C35 C31 C32 C33 -179.7(5) 2_655 . . . ?
C34 C31 C32 C33 179.9(4) 2_655 . . . ?
C32 C31 C32 C33 3.9(5) 2_655 . . . ?
C31 C31 C32 C33 3.9(5) 2_655 . . . ?
C34 C31 C32 C35 -0.4(4) 2_655 . . 2_655 ?
C32 C31 C32 C35 -176.3(5) 2_655 . . 2_655 ?
C31 C31 C32 C35 -176.3(5) 2_655 . . 2_655 ?
C35 C31 C32 C31 176.3(5) 2_655 . . 2_655 ?
C34 C31 C32 C31 175.9(6) 2_655 . . 2_655 ?
C32 C31 C32 C31 0.000(0) 2_655 . . 2_655 ?
C31 C32 C33 C31 -4.4(5) . . . 2_655 ?
C31 C32 C33 C34 -0.1(4) 2_655 . . . ?
C31 C32 C33 C34 -4.5(7) . . . . ?
C32 C33 C34 C31 0.1(5) . . . 2_655 ?
C31 C33 C34 C35 3.8(4) 2_655 . . . ?
C32 C33 C34 C35 3.9(7) . . . . ?
C31 C34 C35 C32 0.4(4) 2_655 . . 2_655 ?
C33 C34 C35 C32 -3.2(7) . . . 2_655 ?
C33 C34 C35 C31 -3.6(4) . . . 2_655 ?
C46 C41 C42 C43 0.1(3) . . . . ?
C47 C41 C42 C43 -179.9(2) . . . . ?
C41 C42 C43 C44 -0.1(3) . . . . ?
C42 C43 C44 C45 0.0(4) . . . . ?
C43 C44 C45 C46 0.2(4) . . . . ?
C44 C45 C46 C41 -0.2(4) . . . . ?
C42 C41 C46 C45 0.1(3) . . . . ?
C47 C41 C46 C45 -179.9(2) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 985514'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wa1778

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H50 B4 N8 Si4, 2(C H2 Cl2)'
_chemical_formula_sum            'C32 H54 B4 Cl4 N8 Si4'
_chemical_formula_weight         848.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.610(2)
_cell_length_b                   11.003(3)
_cell_length_c                   12.115(3)
_cell_angle_alpha                63.855(17)
_cell_angle_beta                 70.231(17)
_cell_angle_gamma                80.803(17)
_cell_volume                     1194.7(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3900
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      24.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             446
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.380
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10352
_diffrn_reflns_av_unetI/netI     0.2173
_diffrn_reflns_av_R_equivalents  0.1236
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.382
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4202
_reflns_number_gt                1714
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0561P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.1809
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_restrained_S_all      0.856
_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
Si1 Si 0.27037(19) -0.17011(18) 0.62434(19) 0.0358(5) Uani 1 1 d . . . . .
Si2 Si 0.6313(2) 0.72572(19) 0.06290(19) 0.0424(5) Uani 1 1 d . . . . .
B1 B 0.1903(7) 0.3793(7) 0.3265(7) 0.0293(16) Uani 1 1 d . . . . .
H1 H 0.169(5) 0.371(5) 0.249(5) 0.028(14) Uiso 1 1 d . . . . .
B2 B 0.2728(7) 0.3807(6) 0.5138(7) 0.0264(15) Uani 1 1 d . . . . .
H2 H 0.320(6) 0.368(6) 0.582(6) 0.040(16) Uiso 1 1 d . . . . .
N1 N 0.2276(5) 0.2358(4) 0.4212(5) 0.0278(11) Uani 1 1 d . . . . .
N2 N 0.2687(5) 0.2358(5) 0.5154(5) 0.0306(12) Uani 1 1 d . . . . .
C3 C 0.2905(6) 0.1069(6) 0.5915(6) 0.0293(14) Uani 1 1 d . . . . .
H3 H 0.3200 0.0793 0.6650 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2639(6) 0.0195(6) 0.5476(6) 0.0293(14) Uani 1 1 d . . . . .
C5 C 0.2250(6) 0.1065(6) 0.4404(6) 0.0335(15) Uani 1 1 d . . . . .
H5 H 0.1998 0.0782 0.3872 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3359(8) -0.2332(7) 0.4963(7) 0.056(2) Uani 1 1 d . . . . .
H6A H 0.4267 -0.1993 0.4444 0.084 Uiso 1 1 calc R U . . .
H6B H 0.2776 -0.2011 0.4408 0.084 Uiso 1 1 calc R U . . .
H6C H 0.3381 -0.3324 0.5359 0.084 Uiso 1 1 calc R U . . .
C7 C 0.3826(8) -0.2219(7) 0.7272(7) 0.056(2) Uani 1 1 d . . . . .
H7A H 0.4727 -0.1873 0.6734 0.084 Uiso 1 1 calc R U . . .
H7B H 0.3863 -0.3209 0.7705 0.084 Uiso 1 1 calc R U . . .
H7C H 0.3478 -0.1846 0.7921 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1002(8) -0.2340(7) 0.7222(9) 0.066(2) Uani 1 1 d . . . . .
H8A H 0.1027 -0.3332 0.7626 0.099 Uiso 1 1 calc R U . . .
H8B H 0.0418 -0.2029 0.6669 0.099 Uiso 1 1 calc R U . . .
H8C H 0.0653 -0.1998 0.7893 0.099 Uiso 1 1 calc R U . . .
N11 N 0.3242(5) 0.4606(5) 0.2760(5) 0.0305(12) Uani 1 1 d . . . . .
N12 N 0.3643(5) 0.4603(5) 0.3716(5) 0.0293(12) Uani 1 1 d . . . . .
C13 C 0.4681(6) 0.5443(5) 0.3152(6) 0.0302(14) Uani 1 1 d . . . . .
H13 H 0.5157 0.5623 0.3602 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4963(6) 0.6010(6) 0.1832(6) 0.0306(14) Uani 1 1 d . . . . .
C15 C 0.4019(6) 0.5436(6) 0.1642(6) 0.0328(14) Uani 1 1 d . . . . .
H15 H 0.3944 0.5616 0.0824 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5955(8) 0.7999(8) -0.0923(7) 0.058(2) Uani 1 1 d . . . . .
H16A H 0.5989 0.7287 -0.1210 0.087 Uiso 1 1 calc R U . . .
H16B H 0.6625 0.8685 -0.1565 0.087 Uiso 1 1 calc R U . . .
H16C H 0.5062 0.8421 -0.0820 0.087 Uiso 1 1 calc R U . . .
C17 C 0.7963(8) 0.6362(9) 0.0499(8) 0.082(3) Uani 1 1 d . . . . .
H17A H 0.7976 0.5672 0.0190 0.123 Uiso 1 1 calc R U . . .
H17B H 0.8108 0.5927 0.1348 0.123 Uiso 1 1 calc R U . . .
H17C H 0.8676 0.7014 -0.0109 0.123 Uiso 1 1 calc R U . . .
C18 C 0.6277(11) 0.8552(8) 0.1212(8) 0.085(3) Uani 1 1 d . . . . .
H18A H 0.6470 0.8126 0.2039 0.127 Uiso 1 1 calc R U . . .
H18B H 0.5388 0.8984 0.1327 0.127 Uiso 1 1 calc R U . . .
H18C H 0.6953 0.9237 0.0581 0.127 Uiso 1 1 calc R U . . .
C21 C 0.0824(6) 0.4435(5) 0.4155(6) 0.0283(14) Uani 1 1 d . . . . .
C22 C 0.1270(6) 0.4452(5) 0.5129(5) 0.0257(13) Uani 1 1 d . . . . .
C23 C 0.0426(6) 0.5018(5) 0.5954(6) 0.0312(15) Uani 1 1 d . . . . .
H23 H 0.0715 0.5029 0.6611 0.037 Uiso 1 1 calc R U . . .
C1L C 0.1492(12) 0.7934(10) 0.2357(10) 0.098(3) Uani 1 1 d . . . . .
H1L1 H 0.0994 0.7151 0.3109 0.118 Uiso 1 1 calc R U . . .
H1L2 H 0.2451 0.7789 0.2310 0.118 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1312(4) 0.7974(3) 0.0946(4) 0.1343(13) Uani 1 1 d . . . . .
Cl2 Cl 0.0952(4) 0.9330(3) 0.2599(4) 0.1234(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
Si1 C8 1.840(7) . ?
Si1 C6 1.854(7) . ?
Si1 C7 1.859(7) . ?
Si1 C4 1.874(6) . ?
Si2 C16 1.837(8) . ?
Si2 C18 1.839(7) . ?
Si2 C17 1.860(9) . ?
Si2 C14 1.874(6) . ?
B1 N1 1.574(9) . ?
B1 N11 1.590(8) . ?
B1 C21 1.597(9) . ?
B1 H1 1.08(5) . ?
B2 N12 1.578(8) . ?
B2 N2 1.593(7) . ?
B2 C22 1.597(9) . ?
B2 H2 1.06(6) . ?
N1 C5 1.340(7) . ?
N1 N2 1.353(6) . ?
N2 C3 1.343(7) . ?
C3 C4 1.387(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(9) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N11 C15 1.320(7) . ?
N11 N12 1.361(6) . ?
N12 C13 1.339(7) . ?
C13 C14 1.376(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(8) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C23 1.390(8) 2_566 ?
C21 C22 1.420(8) . ?
C22 C23 1.398(8) . ?
C23 C21 1.390(8) 2_566 ?
C23 H23 0.9500 . ?
C1L Cl2 1.666(10) . ?
C1L Cl1 1.764(10) . ?
C1L H1L1 0.9900 . ?
C1L H1L2 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
C8 Si1 C6 109.6(4) . . ?
C8 Si1 C7 110.7(4) . . ?
C6 Si1 C7 110.9(3) . . ?
C8 Si1 C4 109.0(3) . . ?
C6 Si1 C4 109.1(3) . . ?
C7 Si1 C4 107.5(3) . . ?
C16 Si2 C18 111.4(4) . . ?
C16 Si2 C17 110.9(4) . . ?
C18 Si2 C17 109.9(5) . . ?
C16 Si2 C14 107.5(3) . . ?
C18 Si2 C14 107.9(3) . . ?
C17 Si2 C14 109.1(3) . . ?
N1 B1 N11 101.7(5) . . ?
N1 B1 C21 105.9(5) . . ?
N11 B1 C21 105.3(4) . . ?
N1 B1 H1 110(3) . . ?
N11 B1 H1 112(3) . . ?
C21 B1 H1 121(3) . . ?
N12 B2 N2 100.9(5) . . ?
N12 B2 C22 104.1(5) . . ?
N2 B2 C22 105.3(4) . . ?
N12 B2 H2 111(3) . . ?
N2 B2 H2 107(3) . . ?
C22 B2 H2 125(3) . . ?
C5 N1 N2 107.3(5) . . ?
C5 N1 B1 137.7(5) . . ?
N2 N1 B1 115.0(4) . . ?
C3 N2 N1 108.1(4) . . ?
C3 N2 B2 136.4(5) . . ?
N1 N2 B2 115.4(5) . . ?
N2 C3 C4 110.4(5) . . ?
N2 C3 H3 124.8 . . ?
C4 C3 H3 124.8 . . ?
C5 C4 C3 103.0(5) . . ?
C5 C4 Si1 129.7(4) . . ?
C3 C4 Si1 127.1(5) . . ?
N1 C5 C4 111.2(5) . . ?
N1 C5 H5 124.4 . . ?
C4 C5 H5 124.4 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 N11 N12 108.2(4) . . ?
C15 N11 B1 137.2(5) . . ?
N12 N11 B1 114.0(5) . . ?
C13 N12 N11 107.4(5) . . ?
C13 N12 B2 136.0(5) . . ?
N11 N12 B2 116.1(4) . . ?
N12 C13 C14 110.6(5) . . ?
N12 C13 H13 124.7 . . ?
C14 C13 H13 124.7 . . ?
C13 C14 C15 103.4(5) . . ?
C13 C14 Si2 126.5(4) . . ?
C15 C14 Si2 130.1(5) . . ?
N11 C15 C14 110.4(5) . . ?
N11 C15 H15 124.8 . . ?
C14 C15 H15 124.8 . . ?
Si2 C16 H16A 109.5 . . ?
Si2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si2 C17 H17A 109.5 . . ?
Si2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si2 C18 H18A 109.5 . . ?
Si2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C21 C22 119.4(5) 2_566 . ?
C23 C21 B1 127.5(5) 2_566 . ?
C22 C21 B1 113.0(5) . . ?
C23 C22 C21 118.5(6) . . ?
C23 C22 B2 127.3(5) . . ?
C21 C22 B2 114.3(5) . . ?
C21 C23 C22 122.1(5) 2_566 . ?
C21 C23 H23 119.0 2_566 . ?
C22 C23 H23 119.0 . . ?
Cl2 C1L Cl1 114.4(6) . . ?
Cl2 C1L H1L1 108.7 . . ?
Cl1 C1L H1L1 108.7 . . ?
Cl2 C1L H1L2 108.7 . . ?
Cl1 C1L H1L2 108.7 . . ?
H1L1 C1L H1L2 107.6 . . ?

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
N11 B1 N1 C5 -128.2(7) . . . . ?
C21 B1 N1 C5 122.0(7) . . . . ?
N11 B1 N1 N2 55.7(6) . . . . ?
C21 B1 N1 N2 -54.1(6) . . . . ?
C5 N1 N2 C3 -0.2(6) . . . . ?
B1 N1 N2 C3 177.1(5) . . . . ?
C5 N1 N2 B2 -177.5(5) . . . . ?
B1 N1 N2 B2 -0.2(7) . . . . ?
N12 B2 N2 C3 129.0(7) . . . . ?
C22 B2 N2 C3 -122.9(7) . . . . ?
N12 B2 N2 N1 -54.7(6) . . . . ?
C22 B2 N2 N1 53.3(6) . . . . ?
N1 N2 C3 C4 0.1(7) . . . . ?
B2 N2 C3 C4 176.6(6) . . . . ?
N2 C3 C4 C5 0.0(7) . . . . ?
N2 C3 C4 Si1 -176.7(4) . . . . ?
C8 Si1 C4 C5 -78.7(7) . . . . ?
C6 Si1 C4 C5 40.9(7) . . . . ?
C7 Si1 C4 C5 161.2(6) . . . . ?
C8 Si1 C4 C3 97.1(6) . . . . ?
C6 Si1 C4 C3 -143.3(5) . . . . ?
C7 Si1 C4 C3 -22.9(6) . . . . ?
N2 N1 C5 C4 0.2(7) . . . . ?
B1 N1 C5 C4 -176.1(6) . . . . ?
C3 C4 C5 N1 -0.2(7) . . . . ?
Si1 C4 C5 N1 176.4(4) . . . . ?
N1 B1 N11 C15 134.5(6) . . . . ?
C21 B1 N11 C15 -115.2(7) . . . . ?
N1 B1 N11 N12 -55.6(6) . . . . ?
C21 B1 N11 N12 54.7(6) . . . . ?
C15 N11 N12 C13 -0.3(6) . . . . ?
B1 N11 N12 C13 -173.1(5) . . . . ?
C15 N11 N12 B2 172.8(5) . . . . ?
B1 N11 N12 B2 0.1(7) . . . . ?
N2 B2 N12 C13 -134.9(6) . . . . ?
C22 B2 N12 C13 116.1(7) . . . . ?
N2 B2 N12 N11 54.6(6) . . . . ?
C22 B2 N12 N11 -54.4(6) . . . . ?
N11 N12 C13 C14 0.5(6) . . . . ?
B2 N12 C13 C14 -170.6(6) . . . . ?
N12 C13 C14 C15 -0.5(6) . . . . ?
N12 C13 C14 Si2 179.5(4) . . . . ?
C16 Si2 C14 C13 -165.3(5) . . . . ?
C18 Si2 C14 C13 -45.0(7) . . . . ?
C17 Si2 C14 C13 74.4(6) . . . . ?
C16 Si2 C14 C15 14.7(7) . . . . ?
C18 Si2 C14 C15 135.0(6) . . . . ?
C17 Si2 C14 C15 -105.7(7) . . . . ?
N12 N11 C15 C14 0.0(6) . . . . ?
B1 N11 C15 C14 170.2(6) . . . . ?
C13 C14 C15 N11 0.3(7) . . . . ?
Si2 C14 C15 N11 -179.6(4) . . . . ?
N1 B1 C21 C23 -127.9(6) . . . 2_566 ?
N11 B1 C21 C23 124.9(6) . . . 2_566 ?
N1 B1 C21 C22 54.0(6) . . . . ?
N11 B1 C21 C22 -53.2(6) . . . . ?
C23 C21 C22 C23 0.3(9) 2_566 . . . ?
B1 C21 C22 C23 178.6(5) . . . . ?
C23 C21 C22 B2 -179.4(5) 2_566 . . . ?
B1 C21 C22 B2 -1.1(7) . . . . ?
N12 B2 C22 C23 -125.5(6) . . . . ?
N2 B2 C22 C23 128.8(6) . . . . ?
N12 B2 C22 C21 54.2(6) . . . . ?
N2 B2 C22 C21 -51.5(6) . . . . ?
C21 C22 C23 C21 -0.3(9) . . . 2_566 ?
B2 C22 C23 C21 179.3(5) . . . 2_566 ?

_refine_diff_density_max         0.681
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 985515'
