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

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

data_20140423
_database_code_depnum_ccdc_archive 'CCDC 1006185'
_audit_update_record             
;
2014-06-02 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 B2 F4 N4'
_chemical_formula_sum            'C24 H16 B2 F4 N4'
_chemical_formula_weight         458.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   6.06279(19)
_cell_length_b                   11.7071(4)
_cell_length_c                   14.5542(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.260(7)
_cell_angle_gamma                90
_cell_volume                     1026.86(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8890
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.20

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.961
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_T_max  0.771

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            11689
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.859
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1882
_reflns_number_gt                1719
_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

_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)+(0.0680P)²+0.2281P]
 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         1882
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
F1 F 1.07503(15) 0.19630(7) 0.40276(6) 0.0304(3) Uani 1 1 d . . . . .
F2 F 0.87664(15) 0.34948(8) 0.44056(6) 0.0322(3) Uani 1 1 d . . . . .
N1 N 0.8132(2) 0.27732(11) 0.28378(8) 0.0234(3) Uani 1 1 d . . . . .
N2 N 1.1621(2) 0.37869(10) 0.33899(8) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.6337(3) 0.20920(13) 0.27748(11) 0.0283(4) Uani 1 1 d . . . . .
H1 H 0.5797 0.1710 0.3281 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5375(3) 0.20245(13) 0.18552(11) 0.0282(4) Uani 1 1 d . . . . .
H2 H 0.4104 0.1592 0.1630 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6629(2) 0.27071(12) 0.13397(10) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.6389 0.2829 0.0691 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8333(2) 0.31907(12) 0.19551(10) 0.0207(3) Uani 1 1 d . . . . .
C5 C 1.0022(2) 0.39547(12) 0.17959(10) 0.0204(3) Uani 1 1 d . . . . .
C6 C 1.1660(2) 0.42472(12) 0.25093(9) 0.0212(3) Uani 1 1 d . . . . .
C7 C 1.3529(2) 0.49731(13) 0.25269(10) 0.0241(3) Uani 1 1 d . . . . .
H7 H 1.3957 0.5409 0.2025 0.029 Uiso 1 1 calc R U . . .
C8 C 1.4615(3) 0.49297(14) 0.34096(11) 0.0288(4) Uani 1 1 d . . . . .
H8 H 1.5940 0.5323 0.3629 0.035 Uiso 1 1 calc R U . . .
C9 C 1.3393(3) 0.41961(14) 0.39205(11) 0.0294(4) Uani 1 1 d . . . . .
H9 H 1.3767 0.4013 0.4554 0.035 Uiso 1 1 calc R U . . .
C10 C 1.1888(2) 0.44277(12) 0.03864(9) 0.0205(3) Uani 1 1 d . . . . .
H10 H 1.3178 0.4035 0.0648 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0017(2) 0.44768(12) 0.08668(9) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.8127(2) 0.50521(12) 0.04685(9) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.6842 0.5086 0.0788 0.025 Uiso 1 1 calc R U . . .
B1 B 0.9795(3) 0.29933(15) 0.37083(11) 0.0246(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3956(19) . ?
F2 B1 1.3789(19) . ?
N1 C1 1.3442(19) . ?
N1 C4 1.3922(18) . ?
N1 B1 1.552(2) . ?
N2 C9 1.3417(19) . ?
N2 C6 1.3929(18) . ?
N2 B1 1.554(2) . ?
C1 C2 1.403(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C5 C6 1.399(2) . ?
C5 C11 1.4837(19) . ?
C6 C7 1.414(2) . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C12 1.3845(19) 3_765 ?
C10 C11 1.398(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3991(19) . ?
C12 C10 1.3845(19) 3_765 ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.28(12) . . ?
C1 N1 B1 127.09(13) . . ?
C4 N1 B1 125.49(12) . . ?
C9 N2 C6 107.36(12) . . ?
C9 N2 B1 126.42(13) . . ?
C6 N2 B1 126.16(12) . . ?
N1 C1 C2 110.35(14) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 106.84(14) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.23(13) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C5 121.13(13) . . ?
N1 C4 C3 108.26(12) . . ?
C5 C4 C3 130.61(13) . . ?
C4 C5 C6 120.48(13) . . ?
C4 C5 C11 119.06(13) . . ?
C6 C5 C11 120.43(13) . . ?
N2 C6 C5 120.41(13) . . ?
N2 C6 C7 108.05(12) . . ?
C5 C6 C7 131.54(14) . . ?
C8 C7 C6 107.15(13) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 106.92(14) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.51(13) . . ?
N2 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C12 C10 C11 120.35(13) 3_765 . ?
C12 C10 H10 119.8 3_765 . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.05(13) . . ?
C10 C11 C5 121.18(12) . . ?
C12 C11 C5 119.76(12) . . ?
C10 C12 C11 120.60(13) 3_765 . ?
C10 C12 H12 119.7 3_765 . ?
C11 C12 H12 119.7 . . ?
F2 B1 F1 109.11(12) . . ?
F2 B1 N1 111.46(13) . . ?
F1 B1 N1 109.72(13) . . ?
F2 B1 N2 111.03(13) . . ?
F1 B1 N2 109.44(13) . . ?
N1 B1 N2 106.03(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 1.69(18) . . . . ?
B1 N1 C1 C2 -174.09(14) . . . . ?
N1 C1 C2 C3 -0.76(19) . . . . ?
C1 C2 C3 C4 -0.48(17) . . . . ?
C1 N1 C4 C5 178.28(13) . . . . ?
B1 N1 C4 C5 -5.9(2) . . . . ?
C1 N1 C4 C3 -1.96(16) . . . . ?
B1 N1 C4 C3 173.90(13) . . . . ?
C2 C3 C4 N1 1.50(16) . . . . ?
C2 C3 C4 C5 -178.77(15) . . . . ?
N1 C4 C5 C6 5.1(2) . . . . ?
C3 C4 C5 C6 -174.56(14) . . . . ?
N1 C4 C5 C11 -173.11(12) . . . . ?
C3 C4 C5 C11 7.2(2) . . . . ?
C9 N2 C6 C5 178.82(13) . . . . ?
B1 N2 C6 C5 -3.9(2) . . . . ?
C9 N2 C6 C7 -0.80(16) . . . . ?
B1 N2 C6 C7 176.50(13) . . . . ?
C4 C5 C6 N2 -0.4(2) . . . . ?
C11 C5 C6 N2 177.77(12) . . . . ?
C4 C5 C6 C7 179.06(14) . . . . ?
C11 C5 C6 C7 -2.7(2) . . . . ?
N2 C6 C7 C8 0.96(17) . . . . ?
C5 C6 C7 C8 -178.60(15) . . . . ?
C6 C7 C8 C9 -0.74(18) . . . . ?
C6 N2 C9 C8 0.34(18) . . . . ?
B1 N2 C9 C8 -176.95(14) . . . . ?
C7 C8 C9 N2 0.26(19) . . . . ?
C12 C10 C11 C12 0.4(2) 3_765 . . . ?
C12 C10 C11 C5 -178.16(12) 3_765 . . . ?
C4 C5 C11 C10 -127.45(14) . . . . ?
C6 C5 C11 C10 54.31(19) . . . . ?
C4 C5 C11 C12 54.00(19) . . . . ?
C6 C5 C11 C12 -124.25(15) . . . . ?
C10 C11 C12 C10 -0.4(2) . . . 3_765 ?
C5 C11 C12 C10 178.18(12) . . . 3_765 ?
C1 N1 B1 F2 -62.3(2) . . . . ?
C4 N1 B1 F2 122.69(15) . . . . ?
C1 N1 B1 F1 58.7(2) . . . . ?
C4 N1 B1 F1 -116.33(15) . . . . ?
C1 N1 B1 N2 176.80(14) . . . . ?
C4 N1 B1 N2 1.75(19) . . . . ?
C9 N2 B1 F2 58.67(19) . . . . ?
C6 N2 B1 F2 -118.13(15) . . . . ?
C9 N2 B1 F1 -61.8(2) . . . . ?
C6 N2 B1 F1 121.37(14) . . . . ?
C9 N2 B1 N1 179.89(13) . . . . ?
C6 N2 B1 N1 3.10(19) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-2

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

data_20140423_2
_database_code_depnum_ccdc_archive 'CCDC 1006186'
_audit_update_record             
;
2014-06-02 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 B2 F4 N4'
_chemical_formula_sum            'C24 H16 B2 F4 N4'
_chemical_formula_weight         458.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   13.0203(3)
_cell_length_b                   10.3330(2)
_cell_length_c                   15.098(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.005(9)
_cell_angle_gamma                90
_cell_volume                     2031.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9342
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      68.17

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.972
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.925

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            11638
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.187
_diffrn_reflns_theta_max         68.167
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1865
_reflns_number_gt                1691
_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

_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)+(0.0621P)²+1.3552P]
 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         1865
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
F1 F 0.08786(7) 0.33760(8) 0.34160(5) 0.0282(2) Uani 1 1 d . . . . .
F2 F -0.02604(6) 0.17275(8) 0.33346(6) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.04807(9) 0.25069(11) 0.19729(8) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.15188(9) 0.12507(12) 0.30364(7) 0.0224(3) Uani 1 1 d . . . . .
C1 C -0.01397(12) 0.33918(15) 0.16110(10) 0.0282(4) Uani 1 1 d . . . . .
H1 H -0.0509 0.4030 0.1933 0.034 Uiso 1 1 calc R U . . .
C2 C -0.01667(12) 0.32420(15) 0.06882(10) 0.0294(4) Uani 1 1 d . . . . .
H2 H -0.0545 0.3756 0.0281 0.035 Uiso 1 1 calc R U . . .
C3 C 0.04555(11) 0.22135(14) 0.04847(10) 0.0257(3) Uani 1 1 d . . . . .
H3 H 0.0576 0.1870 -0.0090 0.031 Uiso 1 1 calc R U . . .
C4 C 0.08853(11) 0.17581(13) 0.12881(9) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.16126(10) 0.07984(13) 0.14578(9) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.19384(10) 0.05630(13) 0.23292(9) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.27209(11) -0.02372(14) 0.26680(10) 0.0251(3) Uani 1 1 d . . . . .
H7 H 0.3144 -0.0808 0.2336 0.030 Uiso 1 1 calc R U . . .
C8 C 0.27600(11) -0.00394(15) 0.35749(10) 0.0273(4) Uani 1 1 d . . . . .
H8 H 0.3212 -0.0450 0.3981 0.033 Uiso 1 1 calc R U . . .
C9 C 0.20150(11) 0.08711(14) 0.37771(9) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.1873 0.1184 0.4356 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2500 0.07247(19) 0.0000 0.0217(4) Uani 1 2 d S T P . .
H10 H 0.2500 0.1644 0.0000 0.026 Uiso 1 2 calc R U P . .
C11 C 0.20687(10) 0.00613(14) 0.07128(9) 0.0221(3) Uani 1 1 d . . . . .
C12 C 0.20774(11) -0.12895(14) 0.07112(10) 0.0260(3) Uani 1 1 d . . . . .
H12 H 0.1795 -0.1755 0.1196 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2500 -0.1947(2) 0.0000 0.0284(5) Uani 1 2 d S T P . .
H13 H 0.2500 -0.2867 0.0000 0.034 Uiso 1 2 calc R U P . .
B1 B 0.06303(12) 0.22489(15) 0.29736(11) 0.0224(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3809(18) . ?
F2 B1 1.3901(18) . ?
N1 C1 1.3368(19) . ?
N1 C4 1.3948(18) . ?
N1 B1 1.5466(19) . ?
N2 C9 1.3498(18) . ?
N2 C6 1.3941(18) . ?
N2 B1 1.553(2) . ?
C1 C2 1.402(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C5 C6 1.404(2) . ?
C5 C11 1.4826(19) . ?
C6 C7 1.408(2) . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3941(17) 2 ?
C10 C11 1.3941(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C12 C13 1.3849(18) . ?
C12 H12 0.9500 . ?
C13 C12 1.3849(18) 2 ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.74(12) . . ?
C1 N1 B1 126.39(12) . . ?
C4 N1 B1 125.52(12) . . ?
C9 N2 C6 107.39(12) . . ?
C9 N2 B1 126.88(12) . . ?
C6 N2 B1 125.72(11) . . ?
N1 C1 C2 110.23(13) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C3 C2 C1 107.06(13) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 107.40(13) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C5 120.97(13) . . ?
N1 C4 C3 107.54(12) . . ?
C5 C4 C3 131.43(13) . . ?
C4 C5 C6 120.04(13) . . ?
C4 C5 C11 119.85(12) . . ?
C6 C5 C11 120.07(12) . . ?
N2 C6 C5 120.74(12) . . ?
N2 C6 C7 107.74(12) . . ?
C5 C6 C7 131.36(13) . . ?
C8 C7 C6 107.39(13) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.00(13) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.48(13) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C11 C10 C11 121.10(18) 2 . ?
C11 C10 H10 119.4 2 . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 119.14(13) . . ?
C10 C11 C5 119.64(13) . . ?
C12 C11 C5 121.22(12) . . ?
C13 C12 C11 119.70(14) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C12 121.21(19) . 2 ?
C12 C13 H13 119.4 . . ?
C12 C13 H13 119.4 2 . ?
F1 B1 F2 109.43(12) . . ?
F1 B1 N1 110.89(12) . . ?
F2 B1 N1 110.17(12) . . ?
F1 B1 N2 110.87(12) . . ?
F2 B1 N2 109.89(12) . . ?
N1 B1 N2 105.54(11) . . ?

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
C4 N1 C1 C2 0.54(17) . . . . ?
B1 N1 C1 C2 -172.98(13) . . . . ?
N1 C1 C2 C3 0.66(18) . . . . ?
C1 C2 C3 C4 -1.57(17) . . . . ?
C1 N1 C4 C5 176.08(13) . . . . ?
B1 N1 C4 C5 -10.3(2) . . . . ?
C1 N1 C4 C3 -1.51(15) . . . . ?
B1 N1 C4 C3 172.09(13) . . . . ?
C2 C3 C4 N1 1.91(16) . . . . ?
C2 C3 C4 C5 -175.33(15) . . . . ?
N1 C4 C5 C6 0.8(2) . . . . ?
C3 C4 C5 C6 177.74(14) . . . . ?
N1 C4 C5 C11 -176.93(12) . . . . ?
C3 C4 C5 C11 0.0(2) . . . . ?
C9 N2 C6 C5 -176.73(12) . . . . ?
B1 N2 C6 C5 4.3(2) . . . . ?
C9 N2 C6 C7 -0.85(15) . . . . ?
B1 N2 C6 C7 -179.86(12) . . . . ?
C4 C5 C6 N2 2.1(2) . . . . ?
C11 C5 C6 N2 179.82(12) . . . . ?
C4 C5 C6 C7 -172.68(14) . . . . ?
C11 C5 C6 C7 5.1(2) . . . . ?
N2 C6 C7 C8 0.70(16) . . . . ?
C5 C6 C7 C8 175.98(14) . . . . ?
C6 C7 C8 C9 -0.28(16) . . . . ?
C6 N2 C9 C8 0.69(16) . . . . ?
B1 N2 C9 C8 179.69(13) . . . . ?
C7 C8 C9 N2 -0.25(17) . . . . ?
C11 C10 C11 C12 0.42(10) 2 . . . ?
C11 C10 C11 C5 -179.72(14) 2 . . . ?
C4 C5 C11 C10 52.00(17) . . . . ?
C6 C5 C11 C10 -125.74(13) . . . . ?
C4 C5 C11 C12 -128.14(15) . . . . ?
C6 C5 C11 C12 54.12(19) . . . . ?
C10 C11 C12 C13 -0.83(19) . . . . ?
C5 C11 C12 C13 179.31(11) . . . . ?
C11 C12 C13 C12 0.42(10) . . . 2 ?
C1 N1 B1 F1 -53.32(18) . . . . ?
C4 N1 B1 F1 134.27(13) . . . . ?
C1 N1 B1 F2 67.98(18) . . . . ?
C4 N1 B1 F2 -104.44(14) . . . . ?
C1 N1 B1 N2 -173.45(13) . . . . ?
C4 N1 B1 N2 14.14(18) . . . . ?
C9 N2 B1 F1 49.89(19) . . . . ?
C6 N2 B1 F1 -131.28(13) . . . . ?
C9 N2 B1 F2 -71.20(17) . . . . ?
C6 N2 B1 F2 107.62(15) . . . . ?
C9 N2 B1 N1 170.04(12) . . . . ?
C6 N2 B1 N1 -11.14(18) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-2

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

data_ProfFuruta
_audit_block_doi                 10.5517/cc13hysb
_database_code_depnum_ccdc_archive 'CCDC 1028232'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s11243-015-9912-7 2015
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H25 B2 F4 N5'
_chemical_formula_sum            'C36 H25 B2 F4 N5'
_chemical_formula_weight         625.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   25.107(13)
_cell_length_b                   9.399(4)
_cell_length_c                   13.496(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.599(6)
_cell_angle_gamma                90
_cell_volume                     2981(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4521
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      31.06

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.998

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            24454
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3597
_reflns_number_gt                3004
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'

_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)+(0.0570P)²+2.4655P] 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         3597
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_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
F1 F 0.23547(5) 0.21933(15) 0.15294(10) 0.0343(4) Uani 1 1 d . . . . .
F2 F 0.30932(6) 0.16084(14) 0.10124(10) 0.0345(4) Uani 1 1 d . . . . .
N1 N 0.31114(7) 0.38969(18) 0.18514(13) 0.0201(4) Uani 1 1 d . . . . .
N2 N 0.32542(7) 0.16590(18) 0.28786(13) 0.0214(4) Uani 1 1 d . . . . .
N3 N 0.5000 0.6782(2) 0.7500 0.0200(5) Uani 1 2 d S T P . .
C1 C 0.29573(9) 0.4838(2) 0.10527(16) 0.0247(5) Uani 1 1 d . . . . .
H1 H 0.2713 0.4634 0.0350 0.030 Uiso 1 1 calc R U . . .
C2 C 0.32073(9) 0.6165(2) 0.14007(17) 0.0252(5) Uani 1 1 d . . . . .
H2 H 0.3162 0.7005 0.0988 0.030 Uiso 1 1 calc R U . . .
C3 C 0.35321(8) 0.6018(2) 0.24573(16) 0.0215(4) Uani 1 1 d . . . . .
H3 H 0.3756 0.6738 0.2906 0.026 Uiso 1 1 calc R U . . .
C4 C 0.34708(8) 0.4593(2) 0.27529(15) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.36978(8) 0.3870(2) 0.37234(15) 0.0173(4) Uani 1 1 d . . . . .
C6 C 0.35815(8) 0.2409(2) 0.37826(15) 0.0189(4) Uani 1 1 d . . . . .
C7 C 0.37269(9) 0.1446(2) 0.46438(17) 0.0230(5) Uani 1 1 d . . . . .
H7 H 0.3945 0.1657 0.5361 0.028 Uiso 1 1 calc R U . . .
C8 C 0.34937(9) 0.0141(2) 0.42504(17) 0.0273(5) Uani 1 1 d . . . . .
H8 H 0.3526 -0.0713 0.4643 0.033 Uiso 1 1 calc R U . . .
C9 C 0.32034(9) 0.0315(2) 0.31706(18) 0.0271(5) Uani 1 1 d . . . . .
H9 H 0.2998 -0.0415 0.2705 0.033 Uiso 1 1 calc R U . . .
C10 C 0.40464(8) 0.4632(2) 0.46885(15) 0.0172(4) Uani 1 1 d . . . . .
C11 C 0.38775(8) 0.5968(2) 0.49367(15) 0.0198(4) Uani 1 1 d . . . . .
H11 H 0.3543 0.6400 0.4461 0.024 Uiso 1 1 calc R U . . .
C12 C 0.41881(8) 0.6668(2) 0.58609(15) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.4062 0.7564 0.6020 0.024 Uiso 1 1 calc R U . . .
C13 C 0.46858(8) 0.6063(2) 0.65609(15) 0.0175(4) Uani 1 1 d . . . . .
C14 C 0.48687(8) 0.4753(2) 0.63045(14) 0.0172(4) Uani 1 1 d . . . . .
H14 H 0.5214 0.4348 0.6764 0.021 Uiso 1 1 calc R U . . .
C15 C 0.45520(8) 0.4045(2) 0.53903(15) 0.0167(4) Uani 1 1 d . . . . .
H15 H 0.4679 0.3149 0.5235 0.020 Uiso 1 1 calc R U . . .
C16 C 0.5000 0.8307(3) 0.7500 0.0182(6) Uani 1 2 d S T P . .
C17 C 0.47837(9) 0.9049(2) 0.81675(17) 0.0248(5) Uani 1 1 d . . . . .
H17 H 0.4636 0.8545 0.8624 0.030 Uiso 1 1 calc R U . . .
C18 C 0.47837(10) 1.0522(2) 0.81661(18) 0.0319(5) Uani 1 1 d . . . . .
H18 H 0.4636 1.1030 0.8621 0.038 Uiso 1 1 calc R U . . .
C19 C 0.5000 1.1253(3) 0.7500 0.0355(8) Uani 1 2 d S T P . .
H19 H 0.5000 1.2264 0.7500 0.043 Uiso 1 2 calc R U P . .
B1 B 0.29373(10) 0.2313(3) 0.17730(18) 0.0234(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.386(3) . ?
F2 B1 1.389(3) . ?
N1 C1 1.342(3) . ?
N1 C4 1.396(2) . ?
N1 B1 1.545(3) . ?
N2 C9 1.343(3) . ?
N2 C6 1.398(3) . ?
N2 B1 1.550(3) . ?
N3 C13 1.408(2) 2_656 ?
N3 C13 1.408(2) . ?
N3 C16 1.433(4) . ?
C1 C2 1.400(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.421(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(3) . ?
C5 C6 1.412(3) . ?
C5 C10 1.474(3) . ?
C6 C7 1.416(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.402(3) . ?
C10 C11 1.404(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.392(3) 2_656 ?
C16 C17 1.392(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C18 1.385(3) 2_656 ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.84(17) . . ?
C1 N1 B1 125.86(17) . . ?
C4 N1 B1 126.27(17) . . ?
C9 N2 C6 107.78(17) . . ?
C9 N2 B1 125.87(17) . . ?
C6 N2 B1 125.83(18) . . ?
C13 N3 C13 122.6(2) 2_656 . ?
C13 N3 C16 118.70(11) 2_656 . ?
C13 N3 C16 118.70(11) . . ?
N1 C1 C2 110.42(18) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 106.88(19) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.55(18) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C5 120.74(18) . . ?
N1 C4 C3 107.30(17) . . ?
C5 C4 C3 131.96(18) . . ?
C4 C5 C6 119.91(18) . . ?
C4 C5 C10 120.55(18) . . ?
C6 C5 C10 119.53(17) . . ?
N2 C6 C5 120.70(18) . . ?
N2 C6 C7 107.26(18) . . ?
C5 C6 C7 132.02(19) . . ?
C8 C7 C6 107.44(19) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.1(2) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.41(19) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C15 C10 C11 117.91(17) . . ?
C15 C10 C5 121.39(18) . . ?
C11 C10 C5 120.69(17) . . ?
C12 C11 C10 121.28(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.21(19) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.01(17) . . ?
C12 C13 N3 119.88(18) . . ?
C14 C13 N3 121.10(17) . . ?
C15 C14 C13 120.60(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.93(18) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C17 119.9(3) 2_656 . ?
C17 C16 N3 120.07(14) 2_656 . ?
C17 C16 N3 120.07(14) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C18 120.5(3) . 2_656 ?
C18 C19 H19 119.7 . . ?
C18 C19 H19 119.7 2_656 . ?
F1 B1 F2 109.53(17) . . ?
F1 B1 N1 110.12(19) . . ?
F2 B1 N1 111.32(18) . . ?
F1 B1 N2 109.74(17) . . ?
F2 B1 N2 109.87(19) . . ?
N1 B1 N2 106.21(16) . . ?

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
C4 N1 C1 C2 0.0(2) . . . . ?
B1 N1 C1 C2 -178.12(19) . . . . ?
N1 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 N1 C4 C5 179.49(18) . . . . ?
B1 N1 C4 C5 -2.4(3) . . . . ?
C1 N1 C4 C3 -0.5(2) . . . . ?
B1 N1 C4 C3 177.60(18) . . . . ?
C2 C3 C4 N1 0.8(2) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
N1 C4 C5 C6 2.6(3) . . . . ?
C3 C4 C5 C6 -177.4(2) . . . . ?
N1 C4 C5 C10 -175.98(17) . . . . ?
C3 C4 C5 C10 4.0(3) . . . . ?
C9 N2 C6 C5 -178.72(18) . . . . ?
B1 N2 C6 C5 -6.6(3) . . . . ?
C9 N2 C6 C7 -0.1(2) . . . . ?
B1 N2 C6 C7 172.07(18) . . . . ?
C4 C5 C6 N2 1.7(3) . . . . ?
C10 C5 C6 N2 -179.72(17) . . . . ?
C4 C5 C6 C7 -176.6(2) . . . . ?
C10 C5 C6 C7 2.0(3) . . . . ?
N2 C6 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C8 179.1(2) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C6 N2 C9 C8 -0.5(2) . . . . ?
B1 N2 C9 C8 -172.67(19) . . . . ?
C7 C8 C9 N2 0.9(3) . . . . ?
C4 C5 C10 C15 -135.9(2) . . . . ?
C6 C5 C10 C15 45.5(3) . . . . ?
C4 C5 C10 C11 44.6(3) . . . . ?
C6 C5 C10 C11 -134.0(2) . . . . ?
C15 C10 C11 C12 -2.1(3) . . . . ?
C5 C10 C11 C12 177.32(18) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 N3 179.96(17) . . . . ?
C13 N3 C13 C12 148.3(2) 2_656 . . . ?
C16 N3 C13 C12 -31.7(2) . . . . ?
C13 N3 C13 C14 -32.75(14) 2_656 . . . ?
C16 N3 C13 C14 147.25(14) . . . . ?
C12 C13 C14 C15 -2.2(3) . . . . ?
N3 C13 C14 C15 178.87(16) . . . . ?
C13 C14 C15 C10 1.2(3) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C5 C10 C15 C14 -178.51(17) . . . . ?
C13 N3 C16 C17 118.32(14) 2_656 . . 2_656 ?
C13 N3 C16 C17 -61.68(14) . . . 2_656 ?
C13 N3 C16 C17 -61.68(14) 2_656 . . . ?
C13 N3 C16 C17 118.32(14) . . . . ?
C17 C16 C17 C18 0.03(15) 2_656 . . . ?
N3 C16 C17 C18 -179.97(15) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C18 0.03(15) . . . 2_656 ?
C1 N1 B1 F1 -65.1(3) . . . . ?
C4 N1 B1 F1 117.2(2) . . . . ?
C1 N1 B1 F2 56.6(3) . . . . ?
C4 N1 B1 F2 -121.2(2) . . . . ?
C1 N1 B1 N2 176.16(18) . . . . ?
C4 N1 B1 N2 -1.6(3) . . . . ?
C9 N2 B1 F1 57.9(3) . . . . ?
C6 N2 B1 F1 -112.9(2) . . . . ?
C9 N2 B1 F2 -62.6(3) . . . . ?
C6 N2 B1 F2 126.6(2) . . . . ?
C9 N2 B1 N1 176.85(19) . . . . ?
C6 N2 B1 N1 6.1(3) . . . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

