# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_d2
_database_code_depnum_ccdc_archive 'CCDC 1041760'
_audit_update_record             
;
2015-01-01 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 B F2 N2 O2'
_chemical_formula_weight         302.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   18.456(2)
_cell_length_b                   7.9351(7)
_cell_length_c                   19.4327(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2846.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5006
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      21.0

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34754
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         24.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.907
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             2330
_reflns_number_gt                1492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0454P)²+1.1048P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2330
_refine_ls_number_parameters     208
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.71992(17) 0.0911(3) 1.12938(14) 0.0632(8) Uani 1 1 d . . . . .
H1 H 0.6971 0.0611 1.1703 0.076 Uiso 1 1 calc R U . . .
C2 C 0.79303(17) 0.0734(3) 1.11683(14) 0.0648(8) Uani 1 1 d . . . . .
H2 H 0.8277 0.0318 1.1471 0.078 Uiso 1 1 calc R U . . .
C3 C 0.80460(14) 0.1291(3) 1.05112(13) 0.0528(7) Uani 1 1 d . . . . .
H3 H 0.8488 0.1307 1.0281 0.063 Uiso 1 1 calc R U . . .
C4 C 0.73810(13) 0.1833(3) 1.02486(12) 0.0435(6) Uani 1 1 d . . . . .
C5 C 0.71881(12) 0.2512(3) 0.96122(12) 0.0410(6) Uani 1 1 d . . . . .
C6 C 0.64666(13) 0.2909(3) 0.94782(12) 0.0449(6) Uani 1 1 d . . . . .
C7 C 0.61330(14) 0.3726(3) 0.89256(14) 0.0565(7) Uani 1 1 d . . . . .
H7 H 0.6364 0.4126 0.8533 0.068 Uiso 1 1 calc R U . . .
C8 C 0.54090(16) 0.3834(4) 0.90628(16) 0.0714(8) Uani 1 1 d . . . . .
H8 H 0.5056 0.4313 0.8783 0.086 Uiso 1 1 calc R U . . .
C9 C 0.53032(15) 0.3097(4) 0.96964(16) 0.0692(8) Uani 1 1 d . . . . .
H9 H 0.4857 0.2994 0.9914 0.083 Uiso 1 1 calc R U . . .
C10 C 0.77350(12) 0.2796(3) 0.90823(12) 0.0412(6) Uani 1 1 d . . . . .
C11 C 0.83857(13) 0.3585(3) 0.92381(12) 0.0456(6) Uani 1 1 d . . . . .
H11 H 0.8478 0.3908 0.9690 0.055 Uiso 1 1 calc R U . . .
C12 C 0.88950(13) 0.3897(3) 0.87416(12) 0.0484(6) Uani 1 1 d . . . . .
H12 H 0.9324 0.4444 0.8855 0.058 Uiso 1 1 calc R U . . .
C13 C 0.87698(14) 0.3399(3) 0.80746(12) 0.0503(6) Uani 1 1 d . . . . .
C14 C 0.81342(13) 0.2578(3) 0.79117(13) 0.0522(7) Uani 1 1 d . . . . .
H14 H 0.8053 0.2218 0.7463 0.063 Uiso 1 1 calc R U . . .
C15 C 0.76223(13) 0.2292(3) 0.84074(12) 0.0472(6) Uani 1 1 d . . . . .
H15 H 0.7193 0.1752 0.8290 0.057 Uiso 1 1 calc R U . . .
N1 N 0.68640(11) 0.1566(2) 1.07510(10) 0.0497(5) Uani 1 1 d . . . . .
N2 N 0.59314(10) 0.2550(3) 0.99554(11) 0.0520(5) Uani 1 1 d . . . . .
O1 O 0.92534(10) 0.3656(2) 0.75592(9) 0.0704(6) Uani 1 1 d . . . . .
H1A H 0.9613 0.4132 0.7713 0.106 Uiso 1 1 calc R U . . .
O2 O 0.54012(13) 0.5424(3) 0.70965(14) 0.0958(8) Uani 1 1 d D . . . .
B1 B 0.60491(17) 0.1764(4) 1.06583(16) 0.0547(8) Uani 1 1 d . . . . .
F1 F 0.57523(8) 0.2738(2) 1.11708(8) 0.0778(5) Uani 1 1 d . . . . .
F2 F 0.57230(8) 0.01747(19) 1.06896(8) 0.0721(5) Uani 1 1 d . . . . .
H2A H 0.547(2) 0.650(3) 0.7260(19) 0.162(18) Uiso 1 1 d D . . . .
H2B H 0.556(2) 0.546(6) 0.6642(12) 0.19(2) Uiso 1 1 d 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
C1 N1 1.329(3) . ?
C1 C2 1.378(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.381(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.459(3) . ?
C6 N2 1.384(3) . ?
C6 C7 1.397(3) . ?
C7 C8 1.365(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.337(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.387(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 O1 1.357(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 B1 1.523(4) . ?
N2 B1 1.517(4) . ?
O1 H1A 0.8200 . ?
O2 H2A 0.922(19) . ?
O2 H2B 0.928(19) . ?
B1 F1 1.375(3) . ?
B1 F2 1.398(3) . ?

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 C1 C2 110.8(2) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C3 C2 C1 106.6(3) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.6(2) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C5 120.6(2) . . ?
N1 C4 C3 107.6(2) . . ?
C5 C4 C3 131.8(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 C10 119.6(2) . . ?
C4 C5 C10 120.6(2) . . ?
N2 C6 C5 120.7(2) . . ?
N2 C6 C7 107.2(2) . . ?
C5 C6 C7 132.0(2) . . ?
C8 C7 C6 108.1(2) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
C7 C8 C9 106.7(3) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 110.6(3) . . ?
N2 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C15 C10 C11 117.8(2) . . ?
C15 C10 C5 121.3(2) . . ?
C11 C10 C5 121.0(2) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O1 C13 C12 122.8(2) . . ?
O1 C13 C14 117.5(2) . . ?
C12 C13 C14 119.7(2) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C1 N1 C4 107.4(2) . . ?
C1 N1 B1 126.4(2) . . ?
C4 N1 B1 125.7(2) . . ?
C9 N2 C6 107.4(2) . . ?
C9 N2 B1 126.6(2) . . ?
C6 N2 B1 125.8(2) . . ?
C13 O1 H1A 109.5 . . ?
H2A O2 H2B 105(3) . . ?
F1 B1 F2 107.7(2) . . ?
F1 B1 N2 111.3(2) . . ?
F2 B1 N2 110.4(2) . . ?
F1 B1 N1 111.4(2) . . ?
F2 B1 N1 109.1(2) . . ?
N2 B1 N1 106.9(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
N1 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 N1 -1.0(3) . . . . ?
C2 C3 C4 C5 179.9(2) . . . . ?
N1 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C6 178.3(2) . . . . ?
N1 C4 C5 C10 179.86(19) . . . . ?
C3 C4 C5 C10 -1.2(4) . . . . ?
C4 C5 C6 N2 -3.6(3) . . . . ?
C10 C5 C6 N2 175.80(19) . . . . ?
C4 C5 C6 C7 173.3(2) . . . . ?
C10 C5 C6 C7 -7.3(4) . . . . ?
N2 C6 C7 C8 -0.9(3) . . . . ?
C5 C6 C7 C8 -178.1(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 N2 0.4(3) . . . . ?
C6 C5 C10 C15 -46.5(3) . . . . ?
C4 C5 C10 C15 132.9(2) . . . . ?
C6 C5 C10 C11 133.4(2) . . . . ?
C4 C5 C10 C11 -47.2(3) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
C5 C10 C11 C12 -178.3(2) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C11 C12 C13 O1 -179.4(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
O1 C13 C14 C15 -179.5(2) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C13 C14 C15 C10 -0.9(4) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?
C5 C10 C15 C14 179.3(2) . . . . ?
C2 C1 N1 C4 0.2(3) . . . . ?
C2 C1 N1 B1 172.4(2) . . . . ?
C5 C4 N1 C1 179.7(2) . . . . ?
C3 C4 N1 C1 0.5(3) . . . . ?
C5 C4 N1 B1 7.4(3) . . . . ?
C3 C4 N1 B1 -171.8(2) . . . . ?
C8 C9 N2 C6 -0.9(3) . . . . ?
C8 C9 N2 B1 176.1(2) . . . . ?
C5 C6 N2 C9 178.7(2) . . . . ?
C7 C6 N2 C9 1.1(3) . . . . ?
C5 C6 N2 B1 1.7(3) . . . . ?
C7 C6 N2 B1 -175.9(2) . . . . ?
C9 N2 B1 F1 -50.8(3) . . . . ?
C6 N2 B1 F1 125.7(2) . . . . ?
C9 N2 B1 F2 68.8(3) . . . . ?
C6 N2 B1 F2 -114.7(3) . . . . ?
C9 N2 B1 N1 -172.7(2) . . . . ?
C6 N2 B1 N1 3.8(3) . . . . ?
C1 N1 B1 F1 58.9(3) . . . . ?
C4 N1 B1 F1 -130.2(2) . . . . ?
C1 N1 B1 F2 -59.9(3) . . . . ?
C4 N1 B1 F2 111.0(3) . . . . ?
C1 N1 B1 N2 -179.2(2) . . . . ?
C4 N1 B1 N2 -8.3(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
O1 H1A O2 0.82 1.82 2.628(3) 169.1 8_657
O2 H2A O1 0.922(19) 1.88(2) 2.791(3) 171(4) 6_765
O2 H2B F2 0.928(19) 1.94(2) 2.838(3) 162(4) 7_565

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.036

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_D2
_database_code_depnum_ccdc_archive 'CCDC 1434317'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 B Br2 F2 N2 O'
_chemical_formula_weight         441.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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                   11.5754(8)
_cell_length_b                   15.3509(11)
_cell_length_c                   9.3750(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.989(2)
_cell_angle_gamma                90
_cell_volume                     1533.57(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.310
_shelx_estimated_absorpt_T_min   0.416
_shelx_estimated_absorpt_T_max   0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.351
_exptl_absorpt_correction_T_max  0.578
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30194
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             2693
_reflns_number_gt                2220
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0375P)²+4.6416P] 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         2693
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
C1 C 0.6125(5) 0.8938(4) 0.3098(6) 0.0469(13) Uani 1 1 d . . . . .
H1 H 0.6989 0.8863 0.3451 0.056 Uiso 1 1 calc R U . . .
C2 C 0.5361(5) 0.9205(4) 0.1608(6) 0.0511(14) Uani 1 1 d . . . . .
H2 H 0.5616 0.9341 0.0809 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4161(5) 0.9229(3) 0.1549(5) 0.0422(12) Uani 1 1 d . . . . .
H3 H 0.3447 0.9390 0.0699 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4202(4) 0.8967(3) 0.3009(5) 0.0328(10) Uani 1 1 d . . . . .
C5 C 0.3272(4) 0.8871(3) 0.3591(5) 0.0316(10) Uani 1 1 d . . . . .
C6 C 0.3588(4) 0.8665(3) 0.5146(5) 0.0342(10) Uani 1 1 d . . . . .
C7 C 0.2856(5) 0.8517(3) 0.6011(6) 0.0394(11) Uani 1 1 d . . . . .
H7 H 0.1985 0.8540 0.5640 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3654(5) 0.8330(3) 0.7502(6) 0.0472(13) Uani 1 1 d . . . . .
H8 H 0.3426 0.8215 0.8331 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4852(5) 0.8346(3) 0.7542(6) 0.0463(13) Uani 1 1 d . . . . .
H9 H 0.5575 0.8235 0.8416 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1931(4) 0.8962(3) 0.2538(5) 0.0322(10) Uani 1 1 d . . . . .
C11 C 0.1470(4) 0.8504(3) 0.1156(5) 0.0371(11) Uani 1 1 d . . . . .
H11 H 0.2013 0.8174 0.0860 0.044 Uiso 1 1 calc R U . . .
C12 C 0.0215(4) 0.8534(3) 0.0220(5) 0.0419(12) Uani 1 1 d . . . . .
C13 C -0.0633(4) 0.9035(3) 0.0585(5) 0.0387(11) Uani 1 1 d . . . . .
C14 C -0.0146(4) 0.9484(3) 0.1976(5) 0.0361(11) Uani 1 1 d . . . . .
C15 C 0.1102(4) 0.9456(3) 0.2942(5) 0.0332(10) Uani 1 1 d . . . . .
H15 H 0.1390 0.9768 0.3865 0.040 Uiso 1 1 calc R U . . .
N1 N 0.5455(3) 0.8804(2) 0.3947(4) 0.0352(9) Uani 1 1 d . . . . .
N2 N 0.4831(3) 0.8545(2) 0.6139(4) 0.0359(9) Uani 1 1 d . . . . .
O1 O -0.1865(3) 0.9103(3) -0.0297(4) 0.0540(10) Uani 1 1 d . . . . .
H1A H -0.1982 0.9026 -0.1208 0.081 Uiso 1 1 calc R U . . .
B1 B 0.5945(5) 0.8508(3) 0.5637(6) 0.0367(12) Uani 1 1 d . . . . .
F1 F 0.6900(2) 0.90613(19) 0.6556(3) 0.0490(7) Uani 1 1 d . . . . .
F2 F 0.6423(3) 0.76728(19) 0.5795(3) 0.0518(8) Uani 1 1 d . . . . .
Br1 Br -0.04086(6) 0.78431(5) -0.15967(7) 0.0747(3) Uani 1 1 d . . . . .
Br2 Br -0.12643(5) 1.01535(4) 0.25563(6) 0.0573(2) 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
C1 N1 1.326(6) . ?
C1 C2 1.392(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(6) . ?
C4 N1 1.394(6) . ?
C5 C6 1.394(6) . ?
C5 C10 1.486(6) . ?
C6 N2 1.387(6) . ?
C6 C7 1.401(7) . ?
C7 C8 1.372(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(7) . ?
C8 H8 0.9300 . ?
C9 N2 1.341(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(6) . ?
C10 C15 1.387(6) . ?
C11 C12 1.374(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(7) . ?
C12 Br1 1.894(5) . ?
C13 O1 1.344(5) . ?
C13 C14 1.385(7) . ?
C14 C15 1.374(6) . ?
C14 Br2 1.891(5) . ?
C15 H15 0.9300 . ?
N1 B1 1.529(6) . ?
N2 B1 1.537(7) . ?
O1 H1A 0.8200 . ?
B1 F2 1.382(6) . ?
B1 F1 1.393(6) . ?

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 C1 C2 110.9(4) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C3 C2 C1 106.6(5) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.7(4) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 N1 120.5(4) . . ?
C5 C4 C3 132.3(4) . . ?
N1 C4 C3 107.2(4) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 C10 119.8(4) . . ?
C6 C5 C10 119.7(4) . . ?
N2 C6 C5 120.8(4) . . ?
N2 C6 C7 107.0(4) . . ?
C5 C6 C7 132.2(4) . . ?
C8 C7 C6 107.8(5) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C7 C8 C9 107.1(5) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 110.2(4) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
C11 C10 C15 118.6(4) . . ?
C11 C10 C5 119.6(4) . . ?
C15 C10 C5 121.6(4) . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 122.2(4) . . ?
C11 C12 Br1 119.5(4) . . ?
C13 C12 Br1 118.2(3) . . ?
O1 C13 C14 118.9(4) . . ?
O1 C13 C12 124.9(4) . . ?
C14 C13 C12 116.1(4) . . ?
C15 C14 C13 122.8(4) . . ?
C15 C14 Br2 119.3(4) . . ?
C13 C14 Br2 117.9(3) . . ?
C14 C15 C10 119.9(4) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C1 N1 C4 107.6(4) . . ?
C1 N1 B1 126.9(4) . . ?
C4 N1 B1 125.5(4) . . ?
C9 N2 C6 107.8(4) . . ?
C9 N2 B1 126.5(4) . . ?
C6 N2 B1 125.0(4) . . ?
C13 O1 H1A 109.5 . . ?
F2 B1 F1 108.2(4) . . ?
F2 B1 N1 110.9(4) . . ?
F1 B1 N1 110.1(4) . . ?
F2 B1 N2 110.5(4) . . ?
F1 B1 N2 110.3(4) . . ?
N1 B1 N2 106.9(4) . . ?

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
N1 C1 C2 C3 -0.4(7) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 -179.9(5) . . . . ?
C2 C3 C4 N1 1.2(6) . . . . ?
N1 C4 C5 C6 4.1(7) . . . . ?
C3 C4 C5 C6 -174.7(5) . . . . ?
N1 C4 C5 C10 -173.9(4) . . . . ?
C3 C4 C5 C10 7.3(8) . . . . ?
C4 C5 C6 N2 -0.4(7) . . . . ?
C10 C5 C6 N2 177.6(4) . . . . ?
C4 C5 C6 C7 -178.5(5) . . . . ?
C10 C5 C6 C7 -0.5(8) . . . . ?
N2 C6 C7 C8 1.3(5) . . . . ?
C5 C6 C7 C8 179.6(5) . . . . ?
C6 C7 C8 C9 -1.2(6) . . . . ?
C7 C8 C9 N2 0.7(6) . . . . ?
C4 C5 C10 C11 49.9(6) . . . . ?
C6 C5 C10 C11 -128.1(5) . . . . ?
C4 C5 C10 C15 -133.9(5) . . . . ?
C6 C5 C10 C15 48.1(6) . . . . ?
C15 C10 C11 C12 -0.8(7) . . . . ?
C5 C10 C11 C12 175.6(4) . . . . ?
C10 C11 C12 C13 1.8(8) . . . . ?
C10 C11 C12 Br1 -176.0(4) . . . . ?
C11 C12 C13 O1 178.7(5) . . . . ?
Br1 C12 C13 O1 -3.5(7) . . . . ?
C11 C12 C13 C14 -1.9(7) . . . . ?
Br1 C12 C13 C14 175.9(4) . . . . ?
O1 C13 C14 C15 -179.5(4) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
O1 C13 C14 Br2 1.0(6) . . . . ?
C12 C13 C14 Br2 -178.5(4) . . . . ?
C13 C14 C15 C10 -0.1(7) . . . . ?
Br2 C14 C15 C10 179.4(3) . . . . ?
C11 C10 C15 C14 -0.1(7) . . . . ?
C5 C10 C15 C14 -176.3(4) . . . . ?
C2 C1 N1 C4 1.1(6) . . . . ?
C2 C1 N1 B1 -179.9(5) . . . . ?
C5 C4 N1 C1 179.5(4) . . . . ?
C3 C4 N1 C1 -1.4(5) . . . . ?
C5 C4 N1 B1 0.5(7) . . . . ?
C3 C4 N1 B1 179.6(4) . . . . ?
C8 C9 N2 C6 0.1(6) . . . . ?
C8 C9 N2 B1 -171.1(4) . . . . ?
C5 C6 N2 C9 -179.4(4) . . . . ?
C7 C6 N2 C9 -0.8(5) . . . . ?
C5 C6 N2 B1 -8.0(7) . . . . ?
C7 C6 N2 B1 170.5(4) . . . . ?
C1 N1 B1 F2 -65.4(6) . . . . ?
C4 N1 B1 F2 113.4(5) . . . . ?
C1 N1 B1 F1 54.2(6) . . . . ?
C4 N1 B1 F1 -127.0(5) . . . . ?
C1 N1 B1 N2 174.0(4) . . . . ?
C4 N1 B1 N2 -7.2(6) . . . . ?
C9 N2 B1 F2 59.8(6) . . . . ?
C6 N2 B1 F2 -109.9(5) . . . . ?
C9 N2 B1 F1 -59.7(6) . . . . ?
C6 N2 B1 F1 130.6(4) . . . . ?
C9 N2 B1 N1 -179.3(4) . . . . ?
C6 N2 B1 N1 10.9(6) . . . . ?

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
C9 H9 F2 0.93 2.48 3.274(6) 142.9 4_576
O1 H1A F1 0.82 1.99 2.731(4) 150.4 1_454
O1 H1A Br1 0.82 2.70 3.111(4) 113.1 .

_refine_diff_density_max         0.989
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_D3
_database_code_depnum_ccdc_archive 'CCDC 1434318'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B Br F2 N2'
_chemical_formula_weight         361.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   20.8544(14)
_cell_length_b                   7.3456(5)
_cell_length_c                   22.1366(17)
_cell_angle_alpha                90
_cell_angle_beta                 117.420(2)
_cell_angle_gamma                90
_cell_volume                     3010.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8191
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      24.2

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.748
_shelx_estimated_absorpt_T_min   0.493
_shelx_estimated_absorpt_T_max   0.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.66
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24867
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.200
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2950
_reflns_number_gt                2160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0612P)²+7.8880P] 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         2950
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.6416(2) 0.3320(6) 0.3992(2) 0.0453(10) Uani 1 1 d . . . . .
H1 H 0.6901 0.3650 0.4194 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5857(2) 0.4325(5) 0.35011(19) 0.0428(9) Uani 1 1 d . . . . .
C3 C 0.52215(19) 0.3426(5) 0.33381(18) 0.0370(8) Uani 1 1 d . . . . .
H3 H 0.4760 0.3802 0.3029 0.044 Uiso 1 1 calc R U . . .
C4 C 0.54040(17) 0.1829(5) 0.37286(17) 0.0348(8) Uani 1 1 d . . . . .
C5 C 0.49833(17) 0.0384(5) 0.37710(17) 0.0328(8) Uani 1 1 d . . . . .
C6 C 0.53085(18) -0.1051(5) 0.42223(18) 0.0373(8) Uani 1 1 d . . . . .
C7 C 0.5037(2) -0.2723(6) 0.4313(2) 0.0482(10) Uani 1 1 d . . . . .
H7 H 0.4556 -0.3088 0.4096 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5609(2) -0.3728(6) 0.4781(2) 0.0578(12) Uani 1 1 d . . . . .
H8 H 0.5588 -0.4884 0.4942 0.069 Uiso 1 1 calc R U . . .
C9 C 0.6222(2) -0.2678(6) 0.4963(2) 0.0538(11) Uani 1 1 d . . . . .
H9 H 0.6687 -0.3037 0.5269 0.065 Uiso 1 1 calc R U . . .
C10 C 0.41961(17) 0.0352(5) 0.33090(17) 0.0307(7) Uani 1 1 d . . . . .
C11 C 0.39313(18) 0.0559(5) 0.26092(18) 0.0369(8) Uani 1 1 d . . . . .
H11 H 0.4250 0.0757 0.2430 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3199(2) 0.0472(5) 0.21805(19) 0.0415(9) Uani 1 1 d . . . . .
H12 H 0.3032 0.0605 0.1714 0.050 Uiso 1 1 calc R U . . .
C13 C 0.27088(18) 0.0193(5) 0.2430(2) 0.0406(9) Uani 1 1 d . . . . .
C14 C 0.29726(19) 0.0009(5) 0.3122(2) 0.0427(9) Uani 1 1 d . . . . .
H14 H 0.2651 -0.0159 0.3301 0.051 Uiso 1 1 calc R U . . .
C15 C 0.37038(18) 0.0070(5) 0.35565(19) 0.0385(8) Uani 1 1 d . . . . .
H15 H 0.3868 -0.0081 0.4022 0.046 Uiso 1 1 calc R U . . .
C16 C 0.1907(2) 0.0101(6) 0.1951(2) 0.0602(12) Uani 1 1 d . . . . .
H16A H 0.1742 -0.1131 0.1925 0.090 Uiso 1 1 calc R U . . .
H16B H 0.1819 0.0500 0.1506 0.090 Uiso 1 1 calc R U . . .
H16C H 0.1652 0.0874 0.2117 0.090 Uiso 1 1 calc R U . . .
N1 N 0.61546(15) 0.1810(5) 0.41314(15) 0.0411(8) Uani 1 1 d . . . . .
N2 N 0.60545(16) -0.1080(5) 0.46415(16) 0.0425(8) Uani 1 1 d . . . . .
B1 B 0.6586(2) 0.0453(8) 0.4704(2) 0.0497(12) Uani 1 1 d . . . . .
F1 F 0.68276(14) 0.1328(4) 0.53294(12) 0.0710(8) Uani 1 1 d . . . . .
F2 F 0.71642(12) -0.0213(4) 0.46358(14) 0.0710(8) Uani 1 1 d . . . . .
Br1 Br 0.60021(3) 0.65320(6) 0.31612(2) 0.0602(2) 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
C1 N1 1.333(5) . ?
C1 C2 1.385(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(5) . ?
C2 Br1 1.870(4) . ?
C3 C4 1.402(5) . ?
C3 H3 0.9300 . ?
C4 N1 1.400(4) . ?
C4 C5 1.408(5) . ?
C5 C6 1.395(5) . ?
C5 C10 1.482(5) . ?
C6 N2 1.397(4) . ?
C6 C7 1.405(6) . ?
C7 C8 1.380(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 N2 1.333(5) . ?
C9 H9 0.9300 . ?
C10 C15 1.384(5) . ?
C10 C11 1.393(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(6) . ?
C13 C16 1.514(5) . ?
C14 C15 1.379(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 B1 1.536(6) . ?
N2 B1 1.541(6) . ?
B1 F2 1.372(6) . ?
B1 F1 1.394(6) . ?

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 C1 C2 109.8(3) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C3 C2 C1 108.2(3) . . ?
C3 C2 Br1 128.9(3) . . ?
C1 C2 Br1 123.0(3) . . ?
C2 C3 C4 106.6(3) . . ?
C2 C3 H3 126.7 . . ?
C4 C3 H3 126.7 . . ?
N1 C4 C3 107.9(3) . . ?
N1 C4 C5 119.9(3) . . ?
C3 C4 C5 132.2(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 C10 120.1(3) . . ?
C4 C5 C10 119.5(3) . . ?
C5 C6 N2 120.8(3) . . ?
C5 C6 C7 131.9(3) . . ?
N2 C6 C7 106.9(3) . . ?
C8 C7 C6 107.9(4) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
C7 C8 C9 106.5(4) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 110.8(4) . . ?
N2 C9 H9 124.6 . . ?
C8 C9 H9 124.6 . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C5 121.1(3) . . ?
C11 C10 C5 120.8(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 C16 121.5(4) . . ?
C12 C13 C16 120.5(4) . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
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 . . ?
C1 N1 C4 107.5(3) . . ?
C1 N1 B1 125.8(3) . . ?
C4 N1 B1 126.2(3) . . ?
C9 N2 C6 107.8(3) . . ?
C9 N2 B1 126.5(3) . . ?
C6 N2 B1 125.7(3) . . ?
F2 B1 F1 109.9(3) . . ?
F2 B1 N1 110.6(3) . . ?
F1 B1 N1 109.1(4) . . ?
F2 B1 N2 111.2(4) . . ?
F1 B1 N2 110.0(3) . . ?
N1 B1 N2 106.0(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
N1 C1 C2 C3 1.2(5) . . . . ?
N1 C1 C2 Br1 -179.5(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
Br1 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 N1 0.8(4) . . . . ?
C2 C3 C4 C5 -179.3(4) . . . . ?
N1 C4 C5 C6 1.3(5) . . . . ?
C3 C4 C5 C6 -178.7(4) . . . . ?
N1 C4 C5 C10 -175.8(3) . . . . ?
C3 C4 C5 C10 4.3(6) . . . . ?
C4 C5 C6 N2 0.3(5) . . . . ?
C10 C5 C6 N2 177.3(3) . . . . ?
C4 C5 C6 C7 -171.9(4) . . . . ?
C10 C5 C6 C7 5.1(6) . . . . ?
C5 C6 C7 C8 173.4(4) . . . . ?
N2 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
C7 C8 C9 N2 0.9(6) . . . . ?
C6 C5 C10 C15 52.5(5) . . . . ?
C4 C5 C10 C15 -130.5(4) . . . . ?
C6 C5 C10 C11 -125.9(4) . . . . ?
C4 C5 C10 C11 51.2(5) . . . . ?
C15 C10 C11 C12 -0.4(5) . . . . ?
C5 C10 C11 C12 178.0(3) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C11 C12 C13 C16 -180.0(4) . . . . ?
C12 C13 C14 C15 -1.1(6) . . . . ?
C16 C13 C14 C15 179.1(4) . . . . ?
C13 C14 C15 C10 1.2(6) . . . . ?
C11 C10 C15 C14 -0.5(5) . . . . ?
C5 C10 C15 C14 -178.9(3) . . . . ?
C2 C1 N1 C4 -0.7(4) . . . . ?
C2 C1 N1 B1 -172.5(4) . . . . ?
C3 C4 N1 C1 -0.1(4) . . . . ?
C5 C4 N1 C1 180.0(3) . . . . ?
C3 C4 N1 B1 171.7(4) . . . . ?
C5 C4 N1 B1 -8.3(6) . . . . ?
C8 C9 N2 C6 -0.7(5) . . . . ?
C8 C9 N2 B1 -179.4(4) . . . . ?
C5 C6 N2 C9 -173.8(4) . . . . ?
C7 C6 N2 C9 0.2(4) . . . . ?
C5 C6 N2 B1 5.0(6) . . . . ?
C7 C6 N2 B1 178.9(4) . . . . ?
C1 N1 B1 F2 -57.6(6) . . . . ?
C4 N1 B1 F2 132.2(4) . . . . ?
C1 N1 B1 F1 63.4(5) . . . . ?
C4 N1 B1 F1 -106.9(4) . . . . ?
C1 N1 B1 N2 -178.2(4) . . . . ?
C4 N1 B1 N2 11.5(6) . . . . ?
C9 N2 B1 F2 48.4(6) . . . . ?
C6 N2 B1 F2 -130.0(4) . . . . ?
C9 N2 B1 F1 -73.5(6) . . . . ?
C6 N2 B1 F1 108.0(4) . . . . ?
C9 N2 B1 N1 168.7(4) . . . . ?
C6 N2 B1 N1 -9.8(6) . . . . ?

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
C1 H1 F1 0.93 2.36 3.267(5) 165.1 7_656
C3 H3 Br1 0.93 3.10 3.864(4) 140.2 2_655
C1 H1 F1 0.93 2.36 3.267(5) 165.1 7_656
C3 H3 Br1 0.93 3.10 3.864(4) 140.2 2_655

_refine_diff_density_max         1.331
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_D4
_database_code_depnum_ccdc_archive 'CCDC 1434319'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 B F2 N2'
_chemical_formula_weight         324.17

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.1279(6)
_cell_length_b                   11.6936(9)
_cell_length_c                   15.8335(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1690.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9127
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.1

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26059
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.996
_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             3333
_reflns_number_gt                2442
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0622P)²+0.7112P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3333
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 1.2954(5) 0.6700(4) 0.1311(3) 0.0537(11) Uani 1 1 d . . . . .
H1 H 1.3659 0.6774 0.0891 0.064 Uiso 1 1 calc R U . . .
C2 C 1.1903(5) 0.7517(4) 0.1501(3) 0.0575(12) Uani 1 1 d . . . . .
H2 H 1.1782 0.8224 0.1241 0.069 Uiso 1 1 calc R U . . .
C3 C 1.1072(5) 0.7076(4) 0.2154(3) 0.0518(11) Uani 1 1 d . . . . .
H3 H 1.0286 0.7435 0.2417 0.062 Uiso 1 1 calc R U . . .
C4 C 1.1632(4) 0.5988(3) 0.2348(2) 0.0402(9) Uani 1 1 d . . . . .
C5 C 1.1235(4) 0.5200(3) 0.2978(2) 0.0374(9) Uani 1 1 d . . . . .
C6 C 1.2110(4) 0.4226(3) 0.3110(2) 0.0386(8) Uani 1 1 d . . . . .
C7 C 1.1987(5) 0.3326(4) 0.3685(2) 0.0472(10) Uani 1 1 d . . . . .
H7 H 1.1257 0.3234 0.4089 0.057 Uiso 1 1 calc R U . . .
C8 C 1.3154(5) 0.2596(4) 0.3541(3) 0.0585(12) Uani 1 1 d . . . . .
H8 H 1.3366 0.1928 0.3836 0.070 Uiso 1 1 calc R U . . .
C9 C 1.3939(5) 0.3047(4) 0.2878(3) 0.0535(11) Uani 1 1 d . . . . .
H9 H 1.4772 0.2715 0.2646 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9892(4) 0.5381(3) 0.3469(2) 0.0392(9) Uani 1 1 d . . . . .
C11 C 0.8560(4) 0.5591(3) 0.3072(2) 0.0463(10) Uani 1 1 d . . . . .
H11 H 0.8527 0.5641 0.2486 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7289(4) 0.5726(4) 0.3529(2) 0.0471(10) Uani 1 1 d . . . . .
H12 H 0.6418 0.5860 0.3241 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7266(4) 0.5667(3) 0.4406(2) 0.0412(9) Uani 1 1 d . . . . .
C14 C 0.8607(4) 0.5477(3) 0.4807(2) 0.0448(9) Uani 1 1 d . . . . .
H14 H 0.8639 0.5443 0.5394 0.054 Uiso 1 1 calc R U . . .
C15 C 0.9891(4) 0.5336(3) 0.4352(2) 0.0430(9) Uani 1 1 d . . . . .
H15 H 1.0765 0.5209 0.4638 0.052 Uiso 1 1 calc R U . . .
C16 C 0.5854(4) 0.5762(3) 0.4920(3) 0.0462(9) Uani 1 1 d . . . . .
C17 C 0.4619(6) 0.6291(6) 0.4410(4) 0.092(2) Uani 1 1 d . . . . .
H17A H 0.4445 0.5839 0.3914 0.138 Uiso 1 1 calc R U . . .
H17B H 0.4887 0.7053 0.4247 0.138 Uiso 1 1 calc R U . . .
H17C H 0.3745 0.6315 0.4747 0.138 Uiso 1 1 calc R U . . .
C18 C 0.5387(7) 0.4577(5) 0.5171(5) 0.106(2) Uani 1 1 d . . . . .
H18A H 0.5344 0.4099 0.4679 0.159 Uiso 1 1 calc R U . . .
H18B H 0.4437 0.4610 0.5431 0.159 Uiso 1 1 calc R U . . .
H18C H 0.6082 0.4267 0.5565 0.159 Uiso 1 1 calc R U . . .
C19 C 0.6084(7) 0.6504(7) 0.5697(4) 0.113(3) Uani 1 1 d . . . . .
H19A H 0.5162 0.6626 0.5974 0.169 Uiso 1 1 calc R U . . .
H19B H 0.6489 0.7227 0.5529 0.169 Uiso 1 1 calc R U . . .
H19C H 0.6747 0.6129 0.6077 0.169 Uiso 1 1 calc R U . . .
N1 N 1.2813(3) 0.5785(3) 0.18205(19) 0.0424(8) Uani 1 1 d . . . . .
N2 N 1.3340(3) 0.4028(3) 0.26143(19) 0.0424(8) Uani 1 1 d . . . . .
B1 B 1.3762(5) 0.4706(4) 0.1817(3) 0.0482(11) Uani 1 1 d . . . . .
F1 F 1.5225(3) 0.4985(3) 0.18189(18) 0.0730(8) Uani 1 1 d . . . . .
F2 F 1.3448(3) 0.4053(2) 0.11037(15) 0.0724(8) 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
C1 N1 1.346(5) . ?
C1 C2 1.388(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(6) . ?
C3 H3 0.9300 . ?
C4 N1 1.385(5) . ?
C4 C5 1.405(5) . ?
C5 C6 1.407(5) . ?
C5 C10 1.466(5) . ?
C6 N2 1.390(5) . ?
C6 C7 1.395(5) . ?
C7 C8 1.384(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(6) . ?
C8 H8 0.9300 . ?
C9 N2 1.338(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(5) . ?
C10 C15 1.400(5) . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(5) . ?
C13 C16 1.528(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C18 1.502(7) . ?
C16 C17 1.518(7) . ?
C16 C19 1.520(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 B1 1.530(6) . ?
N2 B1 1.539(6) . ?
B1 F1 1.374(5) . ?
B1 F2 1.393(5) . ?

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 C1 C2 110.6(4) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C3 C2 C1 106.5(4) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.6(4) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C5 121.1(3) . . ?
N1 C4 C3 107.8(3) . . ?
C5 C4 C3 130.9(4) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 C10 119.8(3) . . ?
C6 C5 C10 120.8(3) . . ?
N2 C6 C7 107.9(3) . . ?
N2 C6 C5 120.6(3) . . ?
C7 C6 C5 131.5(3) . . ?
C8 C7 C6 107.2(4) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C9 C8 C7 106.8(4) . . ?
C9 C8 H8 126.6 . . ?
C7 C8 H8 126.6 . . ?
N2 C9 C8 110.7(4) . . ?
N2 C9 H9 124.6 . . ?
C8 C9 H9 124.6 . . ?
C11 C10 C15 117.2(3) . . ?
C11 C10 C5 121.1(3) . . ?
C15 C10 C5 121.6(3) . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 122.2(4) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 116.6(3) . . ?
C12 C13 C16 122.8(3) . . ?
C14 C13 C16 120.6(3) . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C18 C16 C17 107.8(5) . . ?
C18 C16 C19 110.6(5) . . ?
C17 C16 C19 107.5(5) . . ?
C18 C16 C13 108.3(4) . . ?
C17 C16 C13 111.9(3) . . ?
C19 C16 C13 110.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C4 107.5(3) . . ?
C1 N1 B1 126.8(3) . . ?
C4 N1 B1 125.8(3) . . ?
C9 N2 C6 107.2(3) . . ?
C9 N2 B1 126.5(4) . . ?
C6 N2 B1 125.5(3) . . ?
F1 B1 F2 109.4(4) . . ?
F1 B1 N1 110.8(4) . . ?
F2 B1 N1 109.7(3) . . ?
F1 B1 N2 111.4(4) . . ?
F2 B1 N2 109.3(4) . . ?
N1 B1 N2 106.2(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
N1 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 N1 0.9(4) . . . . ?
C2 C3 C4 C5 177.0(4) . . . . ?
N1 C4 C5 C6 4.2(5) . . . . ?
C3 C4 C5 C6 -171.4(4) . . . . ?
N1 C4 C5 C10 -173.7(3) . . . . ?
C3 C4 C5 C10 10.7(6) . . . . ?
C4 C5 C6 N2 -1.3(5) . . . . ?
C10 C5 C6 N2 176.7(3) . . . . ?
C4 C5 C6 C7 179.3(4) . . . . ?
C10 C5 C6 C7 -2.8(6) . . . . ?
N2 C6 C7 C8 0.8(4) . . . . ?
C5 C6 C7 C8 -179.8(4) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 N2 1.2(5) . . . . ?
C4 C5 C10 C11 51.0(5) . . . . ?
C6 C5 C10 C11 -126.9(4) . . . . ?
C4 C5 C10 C15 -129.8(4) . . . . ?
C6 C5 C10 C15 52.2(5) . . . . ?
C15 C10 C11 C12 -1.3(6) . . . . ?
C5 C10 C11 C12 177.9(4) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C11 C12 C13 C16 -177.2(4) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C16 C13 C14 C15 177.0(4) . . . . ?
C13 C14 C15 C10 0.1(6) . . . . ?
C11 C10 C15 C14 1.0(6) . . . . ?
C5 C10 C15 C14 -178.2(4) . . . . ?
C12 C13 C16 C18 100.4(5) . . . . ?
C14 C13 C16 C18 -77.4(5) . . . . ?
C12 C13 C16 C17 -18.3(6) . . . . ?
C14 C13 C16 C17 163.9(4) . . . . ?
C12 C13 C16 C19 -138.2(5) . . . . ?
C14 C13 C16 C19 44.0(6) . . . . ?
C2 C1 N1 C4 1.1(5) . . . . ?
C2 C1 N1 B1 -179.6(4) . . . . ?
C5 C4 N1 C1 -177.7(3) . . . . ?
C3 C4 N1 C1 -1.2(4) . . . . ?
C5 C4 N1 B1 3.0(5) . . . . ?
C3 C4 N1 B1 179.5(4) . . . . ?
C8 C9 N2 C6 -0.8(5) . . . . ?
C8 C9 N2 B1 -171.1(4) . . . . ?
C7 C6 N2 C9 0.0(4) . . . . ?
C5 C6 N2 C9 -179.6(3) . . . . ?
C7 C6 N2 B1 170.4(4) . . . . ?
C5 C6 N2 B1 -9.1(5) . . . . ?
C1 N1 B1 F1 48.8(5) . . . . ?
C4 N1 B1 F1 -132.0(4) . . . . ?
C1 N1 B1 F2 -72.0(5) . . . . ?
C4 N1 B1 F2 107.2(4) . . . . ?
C1 N1 B1 N2 169.9(3) . . . . ?
C4 N1 B1 N2 -10.9(5) . . . . ?
C9 N2 B1 F1 -56.7(5) . . . . ?
C6 N2 B1 F1 134.6(4) . . . . ?
C9 N2 B1 F2 64.3(5) . . . . ?
C6 N2 B1 F2 -104.4(4) . . . . ?
C9 N2 B1 N1 -177.4(3) . . . . ?
C6 N2 B1 N1 14.0(5) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_D5
_database_code_depnum_ccdc_archive 'CCDC 1434320'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 B F2 N2'
_chemical_formula_weight         282.09

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

_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                   8.0364(3)
_cell_length_b                   8.0696(4)
_cell_length_c                   11.0822(5)
_cell_angle_alpha                88.549(2)
_cell_angle_beta                 84.664(2)
_cell_angle_gamma                71.997(2)
_cell_volume                     680.53(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9127
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      29.7

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18363
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.997
_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             2671
_reflns_number_gt                2063
_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.
;
_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)+(0.0288P)²+0.3317P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.1390(2) 0.6875(3) 0.5806(2) 0.0595(5) Uani 1 1 d . . . . .
H1 H 0.0576 0.6790 0.5286 0.071 Uiso 1 1 calc R U . . .
C2 C 0.1499(3) 0.8425(3) 0.6248(2) 0.0629(6) Uani 1 1 d . . . . .
H2 H 0.0789 0.9541 0.6080 0.075 Uiso 1 1 calc R U . . .
C3 C 0.2854(2) 0.7998(2) 0.69776(18) 0.0507(5) Uani 1 1 d . . . . .
H3 H 0.3229 0.8776 0.7402 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3574(2) 0.6180(2) 0.69707(15) 0.0409(4) Uani 1 1 d . . . . .
C5 C 0.50804(19) 0.5092(2) 0.74479(14) 0.0364(4) Uani 1 1 d . . . . .
C6 C 0.5642(2) 0.3311(2) 0.71890(14) 0.0377(4) Uani 1 1 d . . . . .
C7 C 0.7057(2) 0.1944(2) 0.75595(16) 0.0469(4) Uani 1 1 d . . . . .
H7 H 0.7912 0.2049 0.8037 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6953(3) 0.0426(2) 0.70908(18) 0.0537(5) Uani 1 1 d . . . . .
H8 H 0.7722 -0.0687 0.7187 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5483(2) 0.0872(2) 0.64482(17) 0.0496(4) Uani 1 1 d . . . . .
H9 H 0.5100 0.0083 0.6041 0.060 Uiso 1 1 calc R U . . .
C10 C 0.6082(2) 0.5835(2) 0.82089(15) 0.0384(4) Uani 1 1 d . . . . .
C11 C 0.7875(2) 0.5520(2) 0.79433(15) 0.0415(4) Uani 1 1 d . . . . .
H11 H 0.8456 0.4813 0.7288 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8803(2) 0.6249(2) 0.86447(16) 0.0468(4) Uani 1 1 d . . . . .
H12 H 1.0004 0.6021 0.8453 0.056 Uiso 1 1 calc R U . . .
C13 C 0.7986(3) 0.7306(2) 0.96241(16) 0.0483(4) Uani 1 1 d . . . . .
C14 C 0.6210(3) 0.7597(2) 0.98971(17) 0.0533(5) Uani 1 1 d . . . . .
H14 H 0.5638 0.8289 1.0562 0.064 Uiso 1 1 calc R U . . .
C15 C 0.5263(2) 0.6882(2) 0.92042(16) 0.0478(4) Uani 1 1 d . . . . .
H15 H 0.4065 0.7103 0.9405 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8990(3) 0.8152(3) 1.0354(2) 0.0736(7) Uani 1 1 d . . . . .
H16A H 0.8599 0.9389 1.0227 0.110 Uiso 1 1 calc R U . . .
H16B H 1.0222 0.7698 1.0102 0.110 Uiso 1 1 calc R U . . .
H16C H 0.8789 0.7911 1.1198 0.110 Uiso 1 1 calc R U . . .
B1 B 0.2939(3) 0.3579(3) 0.59779(18) 0.0455(5) Uani 1 1 d . . . . .
N1 N 0.26228(17) 0.55158(19) 0.62333(13) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.46903(17) 0.25896(18) 0.64929(12) 0.0406(3) Uani 1 1 d . . . . .
F1 F 0.15962(14) 0.30334(16) 0.65578(12) 0.0681(4) Uani 1 1 d . . . . .
F2 F 0.30197(16) 0.32675(17) 0.47573(10) 0.0713(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
C1 N1 1.341(2) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.389(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.396(2) . ?
C5 C10 1.473(2) . ?
C6 N2 1.388(2) . ?
C6 C7 1.402(2) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.335(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(3) . ?
C13 C16 1.503(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 F2 1.374(2) . ?
B1 F1 1.386(2) . ?
B1 N1 1.534(3) . ?
B1 N2 1.541(2) . ?

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 C1 C2 110.50(17) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 106.84(17) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.79(18) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C5 120.95(15) . . ?
N1 C4 C3 107.59(15) . . ?
C5 C4 C3 131.05(16) . . ?
C6 C5 C4 119.91(15) . . ?
C6 C5 C10 120.25(14) . . ?
C4 C5 C10 119.83(14) . . ?
N2 C6 C5 120.78(14) . . ?
N2 C6 C7 107.47(14) . . ?
C5 C6 C7 131.67(15) . . ?
C8 C7 C6 107.66(16) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 106.76(16) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
N2 C9 C8 110.63(16) . . ?
N2 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C11 C10 C15 118.06(15) . . ?
C11 C10 C5 120.72(14) . . ?
C15 C10 C5 121.22(15) . . ?
C12 C11 C10 120.55(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 121.43(17) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 117.92(16) . . ?
C14 C13 C16 120.89(19) . . ?
C12 C13 C16 121.17(19) . . ?
C13 C14 C15 121.35(17) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 120.69(17) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
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 . . ?
F2 B1 F1 108.47(15) . . ?
F2 B1 N1 111.21(16) . . ?
F1 B1 N1 110.37(15) . . ?
F2 B1 N2 110.90(15) . . ?
F1 B1 N2 109.66(15) . . ?
N1 B1 N2 106.23(14) . . ?
C1 N1 C4 107.28(16) . . ?
C1 N1 B1 127.17(16) . . ?
C4 N1 B1 125.55(14) . . ?
C9 N2 C6 107.48(14) . . ?
C9 N2 B1 126.46(15) . . ?
C6 N2 B1 125.80(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 N1 -0.5(2) . . . . ?
C2 C3 C4 C5 172.01(18) . . . . ?
N1 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C6 -171.96(17) . . . . ?
N1 C4 C5 C10 178.89(14) . . . . ?
C3 C4 C5 C10 7.2(3) . . . . ?
C4 C5 C6 N2 -2.1(2) . . . . ?
C10 C5 C6 N2 178.72(14) . . . . ?
C4 C5 C6 C7 -178.56(17) . . . . ?
C10 C5 C6 C7 2.3(3) . . . . ?
N2 C6 C7 C8 0.00(19) . . . . ?
C5 C6 C7 C8 176.81(17) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 N2 0.5(2) . . . . ?
C6 C5 C10 C11 52.0(2) . . . . ?
C4 C5 C10 C11 -127.14(17) . . . . ?
C6 C5 C10 C15 -128.58(17) . . . . ?
C4 C5 C10 C15 52.2(2) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
C5 C10 C11 C12 178.67(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 C16 -177.53(17) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C16 C13 C14 C15 177.40(18) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
C5 C10 C15 C14 -178.80(16) . . . . ?
C2 C1 N1 C4 -0.2(2) . . . . ?
C2 C1 N1 B1 179.28(17) . . . . ?
C5 C4 N1 C1 -172.98(16) . . . . ?
C3 C4 N1 C1 0.44(19) . . . . ?
C5 C4 N1 B1 7.5(2) . . . . ?
C3 C4 N1 B1 -179.07(16) . . . . ?
F2 B1 N1 C1 49.5(2) . . . . ?
F1 B1 N1 C1 -71.0(2) . . . . ?
N2 B1 N1 C1 170.24(17) . . . . ?
F2 B1 N1 C4 -131.11(17) . . . . ?
F1 B1 N1 C4 108.45(18) . . . . ?
N2 B1 N1 C4 -10.3(2) . . . . ?
C8 C9 N2 C6 -0.5(2) . . . . ?
C8 C9 N2 B1 -174.88(16) . . . . ?
C5 C6 N2 C9 -176.94(15) . . . . ?
C7 C6 N2 C9 0.29(18) . . . . ?
C5 C6 N2 B1 -2.5(2) . . . . ?
C7 C6 N2 B1 174.74(15) . . . . ?
F2 B1 N2 C9 -57.8(2) . . . . ?
F1 B1 N2 C9 62.0(2) . . . . ?
N1 B1 N2 C9 -178.71(15) . . . . ?
F2 B1 N2 C6 128.84(17) . . . . ?
F1 B1 N2 C6 -111.39(18) . . . . ?
N1 B1 N2 C6 7.9(2) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_D6
_database_code_depnum_ccdc_archive 'CCDC 1434321'
_audit_update_record             
;
2015-10-30 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15.33 H11.33 B Cl F2 N2'
_chemical_formula_weight         307.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   8.1738(5)
_cell_length_b                   10.1538(6)
_cell_length_c                   27.9370(17)
_cell_angle_alpha                80.058(3)
_cell_angle_beta                 89.870(3)
_cell_angle_gamma                72.418(3)
_cell_volume                     2174.1(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      23.1

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57302
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7632
_reflns_number_gt                5222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0404P)²+2.0832P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0058(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7632
_refine_ls_number_parameters     615
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.103
_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
C1 C 0.9987(4) 0.1321(4) 0.45334(12) 0.0601(9) Uani 1 1 d . . . . .
H1 H 1.1130 0.0766 0.4581 0.072 Uiso 1 1 calc R U . . .
C2 C 0.9107(5) 0.2158(4) 0.48505(12) 0.0673(10) Uani 1 1 d . . . . .
H2 H 0.9546 0.2269 0.5143 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7467(4) 0.2793(4) 0.46532(11) 0.0559(8) Uani 1 1 d . . . . .
H3 H 0.6582 0.3408 0.4789 0.067 Uiso 1 1 calc R U . . .
C4 C 0.7362(4) 0.2350(3) 0.42099(10) 0.0430(7) Uani 1 1 d . . . . .
C5 C 0.5996(4) 0.2655(3) 0.38636(10) 0.0415(7) Uani 1 1 d . . . . .
C6 C 0.6226(4) 0.2019(3) 0.34567(10) 0.0462(7) Uani 1 1 d . . . . .
C7 C 0.5125(4) 0.2198(4) 0.30488(12) 0.0644(9) Uani 1 1 d . . . . .
H7 H 0.4002 0.2793 0.2994 0.077 Uiso 1 1 calc R U . . .
C8 C 0.6004(5) 0.1340(5) 0.27482(13) 0.0835(13) Uani 1 1 d . . . . .
H8 H 0.5586 0.1228 0.2453 0.100 Uiso 1 1 calc R U . . .
C9 C 0.7634(5) 0.0665(4) 0.29631(13) 0.0737(11) Uani 1 1 d . . . . .
H9 H 0.8501 0.0030 0.2829 0.088 Uiso 1 1 calc R U . . .
C10 C 0.4319(4) 0.3653(3) 0.39361(10) 0.0457(7) Uani 1 1 d . . . . .
C11 C 0.4222(4) 0.4961(3) 0.40375(11) 0.0545(8) Uani 1 1 d . . . . .
H11 H 0.5221 0.5209 0.4061 0.065 Uiso 1 1 calc R U . . .
C12 C 0.2669(5) 0.5894(4) 0.41036(13) 0.0692(10) Uani 1 1 d . . . . .
H12 H 0.2615 0.6769 0.4174 0.083 Uiso 1 1 calc R U . . .
C13 C 0.1210(5) 0.5537(4) 0.40663(14) 0.0786(12) Uani 1 1 d . . . . .
H13 H 0.0157 0.6175 0.4110 0.094 Uiso 1 1 calc R U . . .
C14 C 0.1261(4) 0.4252(4) 0.39654(14) 0.0729(11) Uani 1 1 d . . . . .
H14 H 0.0250 0.4020 0.3944 0.087 Uiso 1 1 calc R U . . .
C15 C 0.2820(4) 0.3302(3) 0.38960(12) 0.0560(8) Uani 1 1 d . . . . .
H15 H 0.2861 0.2433 0.3823 0.067 Uiso 1 1 calc R U . . .
C16 C 0.8903(6) 0.4023(5) 0.27331(15) 0.0924(14) Uani 1 1 d . . . . .
H16 H 0.9259 0.3137 0.2929 0.111 Uiso 1 1 calc R U . . .
C17 C 0.7743(7) 0.5175(5) 0.28623(15) 0.0946(14) Uani 1 1 d . . . . .
H17 H 0.7176 0.5206 0.3151 0.114 Uiso 1 1 calc R U . . .
C18 C 0.7576(5) 0.6277(4) 0.24847(12) 0.0662(9) Uani 1 1 d . . . . .
H18 H 0.6878 0.7197 0.2470 0.079 Uiso 1 1 calc R U . . .
C19 C 0.8650(4) 0.5756(3) 0.21269(11) 0.0499(8) Uani 1 1 d . . . . .
C20 C 0.8899(4) 0.6384(3) 0.16581(10) 0.0435(7) Uani 1 1 d . . . . .
C21 C 0.9923(4) 0.5586(3) 0.13471(12) 0.0502(8) Uani 1 1 d . . . . .
C22 C 1.0380(5) 0.5938(4) 0.08711(13) 0.0667(10) Uani 1 1 d . . . . .
H22 H 1.0044 0.6829 0.0679 0.080 Uiso 1 1 calc R U . . .
C23 C 1.1412(6) 0.4734(5) 0.07383(17) 0.0852(13) Uani 1 1 d . . . . .
H23 H 1.1906 0.4651 0.0440 0.102 Uiso 1 1 calc R U . . .
C24 C 1.1578(5) 0.3668(5) 0.11322(18) 0.0824(12) Uani 1 1 d . . . . .
H24 H 1.2217 0.2735 0.1139 0.099 Uiso 1 1 calc R U . . .
C25 C 0.8041(4) 0.7902(3) 0.14942(10) 0.0430(7) Uani 1 1 d . . . . .
C26 C 0.8207(4) 0.8879(3) 0.17661(11) 0.0510(8) Uani 1 1 d . . . . .
H26 H 0.8874 0.8584 0.2057 0.061 Uiso 1 1 calc R U . . .
C27 C 0.7382(4) 1.0290(3) 0.16057(13) 0.0610(9) Uani 1 1 d . . . . .
H27 H 0.7517 1.0944 0.1785 0.073 Uiso 1 1 calc R U . . .
C28 C 0.6362(4) 1.0735(4) 0.11818(14) 0.0661(10) Uani 1 1 d . . . . .
H28 H 0.5796 1.1686 0.1078 0.079 Uiso 1 1 calc R U . . .
C29 C 0.6180(4) 0.9778(4) 0.09136(13) 0.0614(9) Uani 1 1 d . . . . .
H29 H 0.5478 1.0080 0.0629 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7027(4) 0.8370(3) 0.10608(11) 0.0514(8) Uani 1 1 d . . . . .
H30 H 0.6923 0.7729 0.0871 0.062 Uiso 1 1 calc R U . . .
C31 C 0.5902(4) 0.5000(3) 0.07695(12) 0.0570(8) Uani 1 1 d . . . . .
H31 H 0.6328 0.4680 0.0488 0.068 Uiso 1 1 calc R U . . .
C32 C 0.6418(4) 0.4276(3) 0.12351(13) 0.0574(8) Uani 1 1 d . . . . .
H32 H 0.7241 0.3402 0.1321 0.069 Uiso 1 1 calc R U . . .
C33 C 0.5493(4) 0.5082(3) 0.15479(11) 0.0487(7) Uani 1 1 d . . . . .
H33 H 0.5566 0.4853 0.1886 0.058 Uiso 1 1 calc R U . . .
C34 C 0.4413(4) 0.6320(3) 0.12634(10) 0.0406(6) Uani 1 1 d . . . . .
C35 C 0.3301(3) 0.7539(3) 0.13887(10) 0.0378(6) Uani 1 1 d . . . . .
C36 C 0.2493(4) 0.8691(3) 0.10268(10) 0.0404(6) Uani 1 1 d . . . . .
C37 C 0.1316(4) 1.0005(3) 0.10495(11) 0.0500(7) Uani 1 1 d . . . . .
H37 H 0.0869 1.0320 0.1330 0.060 Uiso 1 1 calc R U . . .
C38 C 0.0941(4) 1.0744(3) 0.05819(12) 0.0617(9) Uani 1 1 d . . . . .
H38 H 0.0200 1.1651 0.0487 0.074 Uiso 1 1 calc R U . . .
C39 C 0.1873(4) 0.9883(3) 0.02809(12) 0.0578(8) Uani 1 1 d . . . . .
H39 H 0.1854 1.0129 -0.0056 0.069 Uiso 1 1 calc R U . . .
C40 C 0.3014(3) 0.7628(3) 0.19054(10) 0.0420(7) Uani 1 1 d . . . . .
C41 C 0.2615(4) 0.6563(3) 0.22179(10) 0.0497(7) Uani 1 1 d . . . . .
H41 H 0.2572 0.5765 0.2104 0.060 Uiso 1 1 calc R U . . .
C42 C 0.2282(4) 0.6675(4) 0.26954(12) 0.0652(9) Uani 1 1 d . . . . .
H42 H 0.2003 0.5961 0.2902 0.078 Uiso 1 1 calc R U . . .
C43 C 0.2364(5) 0.7856(4) 0.28674(12) 0.0745(11) Uani 1 1 d . . . . .
H43 H 0.2139 0.7933 0.3190 0.089 Uiso 1 1 calc R U . . .
C44 C 0.2774(5) 0.8910(4) 0.25647(12) 0.0687(10) Uani 1 1 d . . . . .
H44 H 0.2827 0.9701 0.2681 0.082 Uiso 1 1 calc R U . . .
C45 C 0.3108(4) 0.8798(3) 0.20852(11) 0.0529(8) Uani 1 1 d . . . . .
H45 H 0.3398 0.9511 0.1882 0.064 Uiso 1 1 calc R U . . .
B1 B 0.9396(4) 0.0583(4) 0.37343(13) 0.0486(8) Uani 1 1 d . . . . .
B2 B 1.0645(6) 0.3305(4) 0.20091(18) 0.0688(12) Uani 1 1 d . . . . .
B3 B 0.3918(5) 0.7378(4) 0.03351(12) 0.0499(9) Uani 1 1 d . . . . .
N1 N 0.8957(3) 0.1424(2) 0.41479(8) 0.0452(6) Uani 1 1 d . . . . .
N2 N 0.7791(3) 0.1050(3) 0.33898(9) 0.0510(6) Uani 1 1 d . . . . .
N3 N 0.9455(4) 0.4330(3) 0.22926(10) 0.0620(7) Uani 1 1 d . . . . .
N4 N 1.0707(3) 0.4149(3) 0.14999(11) 0.0592(7) Uani 1 1 d . . . . .
N5 N 0.4705(3) 0.6226(2) 0.07783(8) 0.0436(6) Uani 1 1 d . . . . .
N6 N 0.2809(3) 0.8647(2) 0.05386(8) 0.0443(6) Uani 1 1 d . . . . .
F1 F 0.9808(3) -0.08390(19) 0.39206(7) 0.0693(6) Uani 1 1 d . . . . .
F2 F 1.0767(2) 0.0847(2) 0.34918(7) 0.0699(6) Uani 1 1 d . . . . .
F3 F 1.2263(3) 0.2790(3) 0.22325(10) 0.1170(10) Uani 1 1 d . . . . .
F4 F 1.0010(3) 0.2210(2) 0.19727(9) 0.0951(8) Uani 1 1 d . . . . .
F5 F 0.5205(3) 0.7710(2) 0.00685(7) 0.0762(6) Uani 1 1 d . . . . .
F6 F 0.2899(3) 0.6949(2) 0.00397(7) 0.0745(6) Uani 1 1 d . . . . .
C46 C 0.3663(11) 0.1677(11) 0.5906(4) 0.085(3) Uani 0.482(3) 1 d D U P A 1
H46 H 0.3026 0.0995 0.5916 0.101 Uiso 0.482(3) 1 calc R U P A 1
Cl1 Cl 0.3191(19) 0.2805(9) 0.5344(5) 0.122(3) Uani 0.482(3) 1 d D U P A 1
Cl2 Cl 0.5839(4) 0.0765(4) 0.59957(19) 0.1130(13) Uani 0.482(3) 1 d D U P A 1
Cl3 Cl 0.3085(3) 0.2560(3) 0.63861(9) 0.1013(10) Uani 0.482(3) 1 d D U P A 1
C46' C 0.3672(16) 0.1523(11) 0.5619(4) 0.107(4) Uani 0.518(3) 1 d D U P A 2
H46' H 0.2619 0.1337 0.5737 0.128 Uiso 0.518(3) 1 calc R U P A 2
Cl1' Cl 0.3092(16) 0.3257(8) 0.5316(5) 0.0910(14) Uani 0.518(3) 1 d D U P A 2
Cl2' Cl 0.4972(9) 0.1346(6) 0.6116(2) 0.197(3) Uani 0.518(3) 1 d D U P A 2
Cl3' Cl 0.4502(5) 0.0397(3) 0.52375(15) 0.1542(15) Uani 0.518(3) 1 d D U P A 2


_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
C1 N1 1.338(4) . ?
C1 C2 1.383(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.389(4) . ?
C4 C5 1.403(4) . ?
C5 C6 1.387(4) . ?
C5 C10 1.476(4) . ?
C6 N2 1.393(4) . ?
C6 C7 1.405(4) . ?
C7 C8 1.361(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(5) . ?
C8 H8 0.9300 . ?
C9 N2 1.335(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(4) . ?
C10 C15 1.385(4) . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.357(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N3 1.328(5) . ?
C16 C17 1.369(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(5) . ?
C18 H18 0.9300 . ?
C19 N3 1.392(4) . ?
C19 C20 1.397(4) . ?
C20 C21 1.393(4) . ?
C20 C25 1.477(4) . ?
C21 N4 1.394(4) . ?
C21 C22 1.396(5) . ?
C22 C23 1.370(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(6) . ?
C23 H23 0.9300 . ?
C24 N4 1.327(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(4) . ?
C25 C30 1.395(4) . ?
C26 C27 1.379(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.366(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.376(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 N5 1.335(4) . ?
C31 C32 1.377(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.369(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.407(4) . ?
C33 H33 0.9300 . ?
C34 N5 1.390(3) . ?
C34 C35 1.396(4) . ?
C35 C36 1.398(4) . ?
C35 C40 1.476(4) . ?
C36 N6 1.393(3) . ?
C36 C37 1.402(4) . ?
C37 C38 1.374(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.378(4) . ?
C38 H38 0.9300 . ?
C39 N6 1.338(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.387(4) . ?
C40 C45 1.389(4) . ?
C41 C42 1.378(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.386(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.370(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.384(4) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
B1 F2 1.379(4) . ?
B1 F1 1.385(4) . ?
B1 N2 1.531(4) . ?
B1 N1 1.531(4) . ?
B2 F3 1.373(4) . ?
B2 F4 1.380(5) . ?
B2 N3 1.525(5) . ?
B2 N4 1.538(5) . ?
B3 F5 1.378(4) . ?
B3 F6 1.383(4) . ?
B3 N6 1.532(4) . ?
B3 N5 1.537(4) . ?
C46 Cl3 1.728(9) . ?
C46 Cl2 1.735(8) . ?
C46 Cl1 1.742(11) . ?
C46 H46 0.9800 . ?
C46' Cl3' 1.689(10) . ?
C46' Cl2' 1.702(10) . ?
C46' Cl1' 1.739(9) . ?
C46' H46' 0.9800 . ?
Cl3' Cl3' 1.744(7) 2_656 ?

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 C1 C2 110.3(3) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C3 C2 C1 107.1(3) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C3 107.5(3) . . ?
N1 C4 C5 120.7(2) . . ?
C3 C4 C5 131.8(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 C10 120.4(3) . . ?
C4 C5 C10 119.6(3) . . ?
C5 C6 N2 120.9(3) . . ?
C5 C6 C7 131.4(3) . . ?
N2 C6 C7 107.7(3) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.2(3) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 110.7(3) . . ?
N2 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C11 C10 C15 119.2(3) . . ?
C11 C10 C5 120.4(3) . . ?
C15 C10 C5 120.5(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 119.7(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
N3 C16 C17 111.4(4) . . ?
N3 C16 H16 124.3 . . ?
C17 C16 H16 124.3 . . ?
C16 C17 C18 107.0(4) . . ?
C16 C17 H17 126.5 . . ?
C18 C17 H17 126.5 . . ?
C17 C18 C19 107.1(4) . . ?
C17 C18 H18 126.5 . . ?
C19 C18 H18 126.5 . . ?
N3 C19 C18 108.0(3) . . ?
N3 C19 C20 120.3(3) . . ?
C18 C19 C20 131.6(3) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 C25 120.5(3) . . ?
C19 C20 C25 119.0(3) . . ?
C20 C21 N4 120.3(3) . . ?
C20 C21 C22 132.2(3) . . ?
N4 C21 C22 107.5(3) . . ?
C23 C22 C21 107.6(4) . . ?
C23 C22 H22 126.2 . . ?
C21 C22 H22 126.2 . . ?
C22 C23 C24 106.7(4) . . ?
C22 C23 H23 126.6 . . ?
C24 C23 H23 126.6 . . ?
N4 C24 C23 111.0(4) . . ?
N4 C24 H24 124.5 . . ?
C23 C24 H24 124.5 . . ?
C26 C25 C30 118.9(3) . . ?
C26 C25 C20 121.2(3) . . ?
C30 C25 C20 119.8(3) . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.5(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.2(3) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
N5 C31 C32 110.6(3) . . ?
N5 C31 H31 124.7 . . ?
C32 C31 H31 124.7 . . ?
C33 C32 C31 107.3(3) . . ?
C33 C32 H32 126.4 . . ?
C31 C32 H32 126.4 . . ?
C32 C33 C34 107.3(3) . . ?
C32 C33 H33 126.3 . . ?
C34 C33 H33 126.3 . . ?
N5 C34 C35 120.5(2) . . ?
N5 C34 C33 107.4(2) . . ?
C35 C34 C33 131.9(3) . . ?
C34 C35 C36 120.2(2) . . ?
C34 C35 C40 119.9(2) . . ?
C36 C35 C40 119.8(2) . . ?
N6 C36 C35 120.5(2) . . ?
N6 C36 C37 107.6(2) . . ?
C35 C36 C37 131.9(3) . . ?
C38 C37 C36 107.6(3) . . ?
C38 C37 H37 126.2 . . ?
C36 C37 H37 126.2 . . ?
C37 C38 C39 106.9(3) . . ?
C37 C38 H38 126.6 . . ?
C39 C38 H38 126.6 . . ?
N6 C39 C38 110.9(3) . . ?
N6 C39 H39 124.6 . . ?
C38 C39 H39 124.6 . . ?
C41 C40 C45 118.8(3) . . ?
C41 C40 C35 120.9(3) . . ?
C45 C40 C35 120.3(3) . . ?
C42 C41 C40 120.6(3) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C43 119.8(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 120.3(3) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.0(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C40 120.5(3) . . ?
C44 C45 H45 119.7 . . ?
C40 C45 H45 119.7 . . ?
F2 B1 F1 109.3(3) . . ?
F2 B1 N2 110.4(3) . . ?
F1 B1 N2 110.0(3) . . ?
F2 B1 N1 110.5(3) . . ?
F1 B1 N1 109.8(3) . . ?
N2 B1 N1 106.8(2) . . ?
F3 B2 F4 109.8(3) . . ?
F3 B2 N3 110.3(3) . . ?
F4 B2 N3 110.6(4) . . ?
F3 B2 N4 109.9(4) . . ?
F4 B2 N4 110.0(3) . . ?
N3 B2 N4 106.2(3) . . ?
F5 B3 F6 109.1(3) . . ?
F5 B3 N6 110.9(3) . . ?
F6 B3 N6 109.5(3) . . ?
F5 B3 N5 109.9(3) . . ?
F6 B3 N5 111.2(3) . . ?
N6 B3 N5 106.2(2) . . ?
C1 N1 C4 107.5(2) . . ?
C1 N1 B1 126.6(3) . . ?
C4 N1 B1 125.7(2) . . ?
C9 N2 C6 107.0(3) . . ?
C9 N2 B1 127.3(3) . . ?
C6 N2 B1 125.7(2) . . ?
C16 N3 C19 106.6(3) . . ?
C16 N3 B2 126.8(3) . . ?
C19 N3 B2 126.5(3) . . ?
C24 N4 C21 107.1(3) . . ?
C24 N4 B2 126.7(3) . . ?
C21 N4 B2 126.1(3) . . ?
C31 N5 C34 107.4(2) . . ?
C31 N5 B3 126.1(3) . . ?
C34 N5 B3 126.3(2) . . ?
C39 N6 C36 107.1(2) . . ?
C39 N6 B3 126.6(3) . . ?
C36 N6 B3 126.1(2) . . ?
Cl3 C46 Cl2 107.2(5) . . ?
Cl3 C46 Cl1 112.2(7) . . ?
Cl2 C46 Cl1 111.8(7) . . ?
Cl3 C46 H46 108.5 . . ?
Cl2 C46 H46 108.5 . . ?
Cl1 C46 H46 108.5 . . ?
Cl3' C46' Cl2' 114.7(7) . . ?
Cl3' C46' Cl1' 111.3(7) . . ?
Cl2' C46' Cl1' 108.9(8) . . ?
Cl3' C46' H46' 107.2 . . ?
Cl2' C46' H46' 107.2 . . ?
Cl1' C46' H46' 107.2 . . ?
C46' Cl3' Cl3' 165.3(5) . 2_656 ?

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
N1 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 N1 0.8(4) . . . . ?
C2 C3 C4 C5 179.1(3) . . . . ?
N1 C4 C5 C6 0.6(4) . . . . ?
C3 C4 C5 C6 -177.4(3) . . . . ?
N1 C4 C5 C10 -179.4(3) . . . . ?
C3 C4 C5 C10 2.5(5) . . . . ?
C4 C5 C6 N2 1.4(4) . . . . ?
C10 C5 C6 N2 -178.5(3) . . . . ?
C4 C5 C6 C7 -175.8(3) . . . . ?
C10 C5 C6 C7 4.3(5) . . . . ?
C5 C6 C7 C8 178.4(4) . . . . ?
N2 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 N2 1.2(5) . . . . ?
C6 C5 C10 C11 -129.3(3) . . . . ?
C4 C5 C10 C11 50.8(4) . . . . ?
C6 C5 C10 C15 49.7(4) . . . . ?
C4 C5 C10 C15 -130.2(3) . . . . ?
C15 C10 C11 C12 0.8(5) . . . . ?
C5 C10 C11 C12 179.8(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 C15 -0.5(6) . . . . ?
C13 C14 C15 C10 0.9(5) . . . . ?
C11 C10 C15 C14 -1.0(5) . . . . ?
C5 C10 C15 C14 180.0(3) . . . . ?
N3 C16 C17 C18 -1.0(6) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 N3 0.3(4) . . . . ?
C17 C18 C19 C20 175.2(4) . . . . ?
N3 C19 C20 C21 1.5(4) . . . . ?
C18 C19 C20 C21 -172.8(3) . . . . ?
N3 C19 C20 C25 -179.4(3) . . . . ?
C18 C19 C20 C25 6.3(5) . . . . ?
C19 C20 C21 N4 0.2(4) . . . . ?
C25 C20 C21 N4 -178.9(3) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?
C25 C20 C21 C22 1.0(5) . . . . ?
C20 C21 C22 C23 -179.6(3) . . . . ?
N4 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 N4 0.0(5) . . . . ?
C21 C20 C25 C26 -128.1(3) . . . . ?
C19 C20 C25 C26 52.8(4) . . . . ?
C21 C20 C25 C30 52.6(4) . . . . ?
C19 C20 C25 C30 -126.5(3) . . . . ?
C30 C25 C26 C27 -0.3(4) . . . . ?
C20 C25 C26 C27 -179.6(3) . . . . ?
C25 C26 C27 C28 1.4(5) . . . . ?
C26 C27 C28 C29 -0.9(5) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C28 C29 C30 C25 1.9(5) . . . . ?
C26 C25 C30 C29 -1.4(4) . . . . ?
C20 C25 C30 C29 177.9(3) . . . . ?
N5 C31 C32 C33 0.4(4) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 N5 0.4(3) . . . . ?
C32 C33 C34 C35 -174.7(3) . . . . ?
N5 C34 C35 C36 -1.2(4) . . . . ?
C33 C34 C35 C36 173.4(3) . . . . ?
N5 C34 C35 C40 -179.5(2) . . . . ?
C33 C34 C35 C40 -4.9(5) . . . . ?
C34 C35 C36 N6 -1.2(4) . . . . ?
C40 C35 C36 N6 177.2(2) . . . . ?
C34 C35 C36 C37 178.5(3) . . . . ?
C40 C35 C36 C37 -3.2(5) . . . . ?
N6 C36 C37 C38 -0.5(3) . . . . ?
C35 C36 C37 C38 179.8(3) . . . . ?
C36 C37 C38 C39 0.3(4) . . . . ?
C37 C38 C39 N6 0.0(4) . . . . ?
C34 C35 C40 C41 -49.3(4) . . . . ?
C36 C35 C40 C41 132.3(3) . . . . ?
C34 C35 C40 C45 131.9(3) . . . . ?
C36 C35 C40 C45 -46.5(4) . . . . ?
C45 C40 C41 C42 1.4(4) . . . . ?
C35 C40 C41 C42 -177.4(3) . . . . ?
C40 C41 C42 C43 -0.7(5) . . . . ?
C41 C42 C43 C44 0.0(6) . . . . ?
C42 C43 C44 C45 0.0(6) . . . . ?
C43 C44 C45 C40 0.7(5) . . . . ?
C41 C40 C45 C44 -1.3(5) . . . . ?
C35 C40 C45 C44 177.5(3) . . . . ?
C2 C1 N1 C4 0.1(4) . . . . ?
C2 C1 N1 B1 -175.1(3) . . . . ?
C3 C4 N1 C1 -0.6(3) . . . . ?
C5 C4 N1 C1 -179.1(3) . . . . ?
C3 C4 N1 B1 174.6(3) . . . . ?
C5 C4 N1 B1 -3.9(4) . . . . ?
F2 B1 N1 C1 -61.3(4) . . . . ?
F1 B1 N1 C1 59.3(4) . . . . ?
N2 B1 N1 C1 178.6(3) . . . . ?
F2 B1 N1 C4 124.4(3) . . . . ?
F1 B1 N1 C4 -115.1(3) . . . . ?
N2 B1 N1 C4 4.2(4) . . . . ?
C8 C9 N2 C6 -0.7(5) . . . . ?
C8 C9 N2 B1 -178.0(3) . . . . ?
C5 C6 N2 C9 -178.0(3) . . . . ?
C7 C6 N2 C9 -0.1(4) . . . . ?
C5 C6 N2 B1 -0.5(5) . . . . ?
C7 C6 N2 B1 177.3(3) . . . . ?
F2 B1 N2 C9 54.7(5) . . . . ?
F1 B1 N2 C9 -66.0(4) . . . . ?
N1 B1 N2 C9 174.9(3) . . . . ?
F2 B1 N2 C6 -122.2(3) . . . . ?
F1 B1 N2 C6 117.1(3) . . . . ?
N1 B1 N2 C6 -2.1(4) . . . . ?
C17 C16 N3 C19 1.2(5) . . . . ?
C17 C16 N3 B2 -175.1(4) . . . . ?
C18 C19 N3 C16 -0.9(4) . . . . ?
C20 C19 N3 C16 -176.4(3) . . . . ?
C18 C19 N3 B2 175.4(3) . . . . ?
C20 C19 N3 B2 -0.1(5) . . . . ?
F3 B2 N3 C16 -67.8(5) . . . . ?
F4 B2 N3 C16 53.9(5) . . . . ?
N4 B2 N3 C16 173.2(4) . . . . ?
F3 B2 N3 C19 116.6(4) . . . . ?
F4 B2 N3 C19 -121.8(3) . . . . ?
N4 B2 N3 C19 -2.4(4) . . . . ?
C23 C24 N4 C21 0.3(4) . . . . ?
C23 C24 N4 B2 -176.7(3) . . . . ?
C20 C21 N4 C24 179.6(3) . . . . ?
C22 C21 N4 C24 -0.4(4) . . . . ?
C20 C21 N4 B2 -3.4(5) . . . . ?
C22 C21 N4 B2 176.6(3) . . . . ?
F3 B2 N4 C24 61.4(5) . . . . ?
F4 B2 N4 C24 -59.7(5) . . . . ?
N3 B2 N4 C24 -179.3(3) . . . . ?
F3 B2 N4 C21 -115.1(4) . . . . ?
F4 B2 N4 C21 123.9(3) . . . . ?
N3 B2 N4 C21 4.2(4) . . . . ?
C32 C31 N5 C34 -0.1(3) . . . . ?
C32 C31 N5 B3 174.8(3) . . . . ?
C35 C34 N5 C31 175.6(3) . . . . ?
C33 C34 N5 C31 -0.2(3) . . . . ?
C35 C34 N5 B3 0.6(4) . . . . ?
C33 C34 N5 B3 -175.1(3) . . . . ?
F5 B3 N5 C31 -52.1(4) . . . . ?
F6 B3 N5 C31 68.8(4) . . . . ?
N6 B3 N5 C31 -172.2(3) . . . . ?
F5 B3 N5 C34 121.9(3) . . . . ?
F6 B3 N5 C34 -117.2(3) . . . . ?
N6 B3 N5 C34 1.8(4) . . . . ?
C38 C39 N6 C36 -0.3(4) . . . . ?
C38 C39 N6 B3 175.6(3) . . . . ?
C35 C36 N6 C39 -179.8(3) . . . . ?
C37 C36 N6 C39 0.5(3) . . . . ?
C35 C36 N6 B3 4.3(4) . . . . ?
C37 C36 N6 B3 -175.4(3) . . . . ?
F5 B3 N6 C39 61.2(4) . . . . ?
F6 B3 N6 C39 -59.3(4) . . . . ?
N5 B3 N6 C39 -179.4(3) . . . . ?
F5 B3 N6 C36 -123.7(3) . . . . ?
F6 B3 N6 C36 115.8(3) . . . . ?
N5 B3 N6 C36 -4.3(4) . . . . ?
Cl2' C46' Cl3' Cl3' -98(2) . . . 2_656 ?
Cl1' C46' Cl3' Cl3' 26(3) . . . 2_656 ?

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
C7 H7 F3 0.93 2.56 3.120(4) 118.9 1_455
C16 H16 F2 0.93 2.53 3.449(5) 168.6 .
C17 H17 Cl3 0.93 2.75 3.298(6) 118.3 2_666
C31 H31 F6 0.93 2.35 3.217(4) 155.5 2_665
C46 H46 F1 0.98 2.41 3.212(11) 139.0 2_656
C46' H46' F1 0.98 2.35 3.331(13) 175.7 2_656
C7 H7 F3 0.93 2.56 3.120(4) 118.9 1_455
C16 H16 F2 0.93 2.53 3.449(5) 168.6 .
C17 H17 Cl3 0.93 2.75 3.298(6) 118.3 2_666
C31 H31 F6 0.93 2.35 3.217(4) 155.5 2_665
C46 H46 F1 0.98 2.41 3.212(11) 139.0 2_656
C46' H46' F1 0.98 2.35 3.331(13) 175.7 2_656

_refine_diff_density_max         0.680
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.041

