# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1033433'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 B F6 N3'
_chemical_formula_weight         383.11
_chemical_absolute_configuration unk


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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C2221

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

_cell_length_a                   6.8499(4)
_cell_length_b                   25.8041(17)
_cell_length_c                   9.4897(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1677.36(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4135
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      29.8

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.989
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9742
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1485
_reflns_number_gt                1177
_reflns_threshold_expression     >2sigma(I)

_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          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0853P)²+0.6766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(16)
_refine_ls_number_reflns         1485
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2971(7) 0.18406(14) 0.4041(5) 0.0983(13) Uani 1 1 d . . .
H1 H 1.3322 0.2182 0.4228 0.118 Uiso 1 1 calc R . .
C2 C 1.3909(8) 0.14133(15) 0.4583(6) 0.1218(19) Uani 1 1 d . . .
H2 H 1.4989 0.1416 0.5177 0.146 Uiso 1 1 calc R . .
C3 C 1.2968(6) 0.09898(13) 0.4093(5) 0.0875(11) Uani 1 1 d . . .
H3 H 1.3277 0.0646 0.4292 0.105 Uiso 1 1 calc R . .
C4 C 1.1440(5) 0.11634(10) 0.3230(3) 0.0600(8) Uani 1 1 d . . .
C5 C 1.0000 0.08969(13) 0.2500 0.0518(10) Uani 1 2 d S . .
C6 C 1.0000 0.03233(13) 0.2500 0.0553(10) Uani 1 2 d S . .
C7 C 0.8451(4) 0.00345(11) 0.3016(3) 0.0637(9) Uani 1 1 d . . .
C9 C 0.8447(5) -0.04960(11) 0.2992(3) 0.0648(9) Uani 1 1 d . . .
C10 C 1.0000 -0.07901(14) 0.2500 0.0612(11) Uani 1 2 d S . .
C11 C 1.1119(9) -0.16240(14) 0.1535(6) 0.1193(17) Uani 1 1 d . . .
H11A H 1.1527 -0.1412 0.0758 0.179 Uiso 1 1 calc R . .
H11B H 1.0334 -0.1905 0.1191 0.179 Uiso 1 1 calc R . .
H11C H 1.2247 -0.1760 0.2008 0.179 Uiso 1 1 calc R . .
N1 N 1.1504(4) 0.17014(8) 0.3218(3) 0.0679(8) Uani 1 1 d . . .
N2 N 1.0000 -0.13188(12) 0.2500 0.0770(13) Uani 1 2 d S . .
B1 B 1.0000 0.20533(17) 0.2500 0.0787(18) Uani 1 2 d S . .
F1 F 0.9118(5) 0.23607(9) 0.3465(3) 0.1420(14) Uani 1 1 d . . .
F2 F 0.6889(3) 0.02743(7) 0.3523(3) 0.1005(8) Uani 1 1 d . . .
F3 F 0.6816(3) -0.07317(8) 0.3443(3) 0.1071(10) 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 1.322(5) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.351(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 N1 1.389(3) . ?
C5 C4 1.388(3) 3_755 ?
C5 C6 1.480(5) . ?
C6 C7 1.386(3) . ?
C6 C7 1.386(3) 3_755 ?
C7 F2 1.326(3) . ?
C7 C9 1.369(4) . ?
C9 F3 1.342(4) . ?
C9 C10 1.388(4) . ?
C10 N2 1.364(5) . ?
C10 C9 1.388(4) 3_755 ?
C11 N2 1.430(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 B1 1.533(4) . ?
N2 C11 1.430(4) 3_755 ?
B1 F1 1.354(3) 3_755 ?
B1 F1 1.354(3) . ?
B1 N1 1.533(4) 3_755 ?

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 111.0(3) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C3 C2 C1 107.3(4) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.4(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C5 C4 N1 120.9(2) . . ?
C5 C4 C3 131.6(3) . . ?
N1 C4 C3 107.5(3) . . ?
C4 C5 C4 120.6(3) . 3_755 ?
C4 C5 C6 119.71(15) . . ?
C4 C5 C6 119.71(15) 3_755 . ?
C7 C6 C7 115.0(3) . 3_755 ?
C7 C6 C5 122.52(16) . . ?
C7 C6 C5 122.52(16) 3_755 . ?
F2 C7 C9 118.1(3) . . ?
F2 C7 C6 119.7(2) . . ?
C9 C7 C6 122.2(3) . . ?
F3 C9 C7 116.7(3) . . ?
F3 C9 C10 119.8(2) . . ?
C7 C9 C10 123.4(3) . . ?
N2 C10 C9 123.15(16) . 3_755 ?
N2 C10 C9 123.15(16) . . ?
C9 C10 C9 113.7(3) 3_755 . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C4 106.9(3) . . ?
C1 N1 B1 127.8(3) . . ?
C4 N1 B1 125.0(3) . . ?
C10 N2 C11 123.4(2) . . ?
C10 N2 C11 123.4(2) . 3_755 ?
C11 N2 C11 113.2(4) . 3_755 ?
F1 B1 F1 108.3(4) 3_755 . ?
F1 B1 N1 110.36(19) 3_755 . ?
F1 B1 N1 110.25(15) . . ?
F1 B1 N1 110.25(15) 3_755 3_755 ?
F1 B1 N1 110.36(19) . 3_755 ?
N1 B1 N1 107.4(3) . 3_755 ?

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 -0.9(6) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 -178.0(4) . . . . ?
C2 C3 C4 N1 0.2(5) . . . . ?
N1 C4 C5 C4 -1.7(2) . . . 3_755 ?
C3 C4 C5 C4 176.3(4) . . . 3_755 ?
N1 C4 C5 C6 178.3(2) . . . . ?
C3 C4 C5 C6 -3.7(4) . . . . ?
C4 C5 C6 C7 120.1(2) . . . . ?
C4 C5 C6 C7 -59.9(2) 3_755 . . . ?
C4 C5 C6 C7 -59.9(2) . . . 3_755 ?
C4 C5 C6 C7 120.1(2) 3_755 . . 3_755 ?
C7 C6 C7 F2 -179.4(4) 3_755 . . . ?
C5 C6 C7 F2 0.6(4) . . . . ?
C7 C6 C7 C9 -1.1(2) 3_755 . . . ?
C5 C6 C7 C9 178.9(2) . . . . ?
F2 C7 C9 F3 2.3(5) . . . . ?
C6 C7 C9 F3 -176.0(3) . . . . ?
F2 C7 C9 C10 -179.4(3) . . . . ?
C6 C7 C9 C10 2.2(5) . . . . ?
F3 C9 C10 N2 -2.9(4) . . . . ?
C7 C9 C10 N2 178.9(2) . . . . ?
F3 C9 C10 C9 177.1(4) . . . 3_755 ?
C7 C9 C10 C9 -1.1(2) . . . 3_755 ?
C2 C1 N1 C4 1.0(5) . . . . ?
C2 C1 N1 B1 175.0(4) . . . . ?
C5 C4 N1 C1 177.7(3) . . . . ?
C3 C4 N1 C1 -0.7(4) . . . . ?
C5 C4 N1 B1 3.4(4) . . . . ?
C3 C4 N1 B1 -174.9(3) . . . . ?
C9 C10 N2 C11 -26.4(3) 3_755 . . . ?
C9 C10 N2 C11 153.6(3) . . . . ?
C9 C10 N2 C11 153.6(3) 3_755 . . 3_755 ?
C9 C10 N2 C11 -26.4(3) . . . 3_755 ?
C1 N1 B1 F1 65.1(4) . . . 3_755 ?
C4 N1 B1 F1 -121.9(3) . . . 3_755 ?
C1 N1 B1 F1 -54.4(4) . . . . ?
C4 N1 B1 F1 118.6(3) . . . . ?
C1 N1 B1 N1 -174.7(4) . . . 3_755 ?
C4 N1 B1 N1 -1.7(2) . . . 3_755 ?

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 2.55 3.236(4) 131.2 8_556
C2 H2 F3 0.93 2.53 3.251(5) 134.7 4_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 982039'
_audit_update_record             
;
2014-01-17 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 B F2 N3'
_chemical_formula_weight         311.14

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.2654(11)
_cell_length_b                   10.5756(10)
_cell_length_c                   13.3074(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.339(2)
_cell_angle_gamma                90.00
_cell_volume                     1547.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3205
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      23.8

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14496
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         24.80
_reflns_number_total             2655
_reflns_number_gt                1786
_reflns_threshold_expression     >2sigma(I)

_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          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.5962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0068(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5199(2) -0.0304(2) 0.8424(2) 0.0605(7) Uani 1 1 d . . .
H1 H 0.4805 -0.0405 0.8876 0.073 Uiso 1 1 calc R . .
C2 C 0.4688(2) -0.0561(2) 0.7291(2) 0.0651(7) Uani 1 1 d . . .
H2 H 0.3907 -0.0866 0.6855 0.078 Uiso 1 1 calc R . .
C3 C 0.5548(2) -0.0281(2) 0.69278(19) 0.0532(6) Uani 1 1 d . . .
H3 H 0.5452 -0.0351 0.6196 0.064 Uiso 1 1 calc R . .
C4 C 0.65968(19) 0.01278(19) 0.78585(17) 0.0429(5) Uani 1 1 d . . .
C5 C 0.77137(19) 0.05892(18) 0.79517(17) 0.0400(5) Uani 1 1 d . . .
C6 C 0.85605(19) 0.1107(2) 0.89664(17) 0.0418(5) Uani 1 1 d . . .
C7 C 0.9727(2) 0.1603(2) 0.92947(19) 0.0512(6) Uani 1 1 d . . .
H7 H 1.0131 0.1668 0.8849 0.061 Uiso 1 1 calc R . .
C8 C 1.0166(2) 0.1978(2) 1.0393(2) 0.0634(7) Uani 1 1 d . . .
H8 H 1.0914 0.2357 1.0825 0.076 Uiso 1 1 calc R . .
C9 C 0.9285(2) 0.1684(2) 1.0733(2) 0.0626(7) Uani 1 1 d . . .
H9 H 0.9358 0.1829 1.1450 0.075 Uiso 1 1 calc R . .
C10 C 0.79575(18) 0.05394(19) 0.69695(16) 0.0403(5) Uani 1 1 d . . .
C11 C 0.7767(2) -0.0556(2) 0.63331(18) 0.0488(6) Uani 1 1 d . . .
H11 H 0.7497 -0.1280 0.6551 0.059 Uiso 1 1 calc R . .
C12 C 0.7964(2) -0.0604(2) 0.53966(18) 0.0515(6) Uani 1 1 d . . .
H12 H 0.7854 -0.1363 0.5011 0.062 Uiso 1 1 calc R . .
C13 C 0.83283(18) 0.0476(2) 0.50125(17) 0.0453(5) Uani 1 1 d . . .
C14 C 0.8516(2) 0.1583(2) 0.56460(18) 0.0490(6) Uani 1 1 d . . .
H14 H 0.8753 0.2319 0.5414 0.059 Uiso 1 1 calc R . .
C15 C 0.83568(19) 0.1601(2) 0.66057(17) 0.0455(5) Uani 1 1 d . . .
H15 H 0.8520 0.2341 0.7024 0.055 Uiso 1 1 calc R . .
C16 C 0.8307(3) -0.0702(3) 0.3418(2) 0.0754(8) Uani 1 1 d . . .
H16A H 0.8800 -0.1364 0.3898 0.113 Uiso 1 1 calc R . .
H16B H 0.8535 -0.0563 0.2823 0.113 Uiso 1 1 calc R . .
H16C H 0.7466 -0.0942 0.3105 0.113 Uiso 1 1 calc R . .
C17 C 0.8749(3) 0.1590(3) 0.3607(2) 0.0845(9) Uani 1 1 d . . .
H17A H 0.8156 0.2225 0.3528 0.127 Uiso 1 1 calc R . .
H17B H 0.8717 0.1412 0.2887 0.127 Uiso 1 1 calc R . .
H17C H 0.9546 0.1891 0.4106 0.127 Uiso 1 1 calc R . .
B1 B 0.7226(3) 0.0528(3) 0.9973(2) 0.0524(7) Uani 1 1 d . . .
N1 N 0.63475(16) 0.01127(17) 0.87834(14) 0.0472(5) Uani 1 1 d . . .
N2 N 0.83111(16) 0.11618(17) 0.98945(14) 0.0474(5) Uani 1 1 d . . .
N3 N 0.84890(18) 0.0449(2) 0.40597(15) 0.0593(6) Uani 1 1 d . . .
F1 F 0.66569(14) 0.13626(15) 1.03931(13) 0.0822(5) Uani 1 1 d . . .
F2 F 0.76179(14) -0.05115(14) 1.06791(11) 0.0763(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.345(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.394(2) . ?
C4 C5 1.407(3) . ?
C5 C6 1.399(3) . ?
C5 C10 1.465(3) . ?
C6 C7 1.399(3) . ?
C6 N2 1.399(2) . ?
C7 C8 1.373(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.340(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.403(3) . ?
C12 H12 0.9300 . ?
C13 N3 1.367(3) . ?
C13 C14 1.401(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N3 1.446(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N3 1.446(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
B1 F2 1.386(3) . ?
B1 F1 1.388(3) . ?
B1 N1 1.532(3) . ?
B1 N2 1.534(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 110.5(2) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 107.1(2) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.6(2) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C3 107.59(18) . . ?
N1 C4 C5 120.84(19) . . ?
C3 C4 C5 131.40(19) . . ?
C6 C5 C4 119.84(18) . . ?
C6 C5 C10 121.13(18) . . ?
C4 C5 C10 119.01(19) . . ?
C7 C6 C5 131.80(19) . . ?
C7 C6 N2 107.60(18) . . ?
C5 C6 N2 120.58(18) . . ?
C8 C7 C6 107.8(2) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C7 C8 C9 106.8(2) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
N2 C9 C8 111.0(2) . . ?
N2 C9 H9 124.5 . . ?
C8 C9 H9 124.5 . . ?
C11 C10 C15 116.67(18) . . ?
C11 C10 C5 121.78(18) . . ?
C15 C10 C5 121.52(18) . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N3 C13 C14 121.5(2) . . ?
N3 C13 C12 121.4(2) . . ?
C14 C13 C12 117.07(18) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F2 B1 F1 108.41(19) . . ?
F2 B1 N1 110.3(2) . . ?
F1 B1 N1 110.5(2) . . ?
F2 B1 N2 110.0(2) . . ?
F1 B1 N2 110.9(2) . . ?
N1 B1 N2 106.80(17) . . ?
C1 N1 C4 107.17(19) . . ?
C1 N1 B1 127.39(18) . . ?
C4 N1 B1 125.43(18) . . ?
C9 N2 C6 106.80(18) . . ?
C9 N2 B1 127.11(19) . . ?
C6 N2 B1 125.29(18) . . ?
C13 N3 C17 121.2(2) . . ?
C13 N3 C16 121.2(2) . . ?
C17 N3 C16 117.43(19) . . ?

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 -0.6(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 N1 -1.1(3) . . . . ?
C2 C3 C4 C5 -176.2(2) . . . . ?
N1 C4 C5 C6 -3.7(3) . . . . ?
C3 C4 C5 C6 170.9(2) . . . . ?
N1 C4 C5 C10 177.51(18) . . . . ?
C3 C4 C5 C10 -7.9(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C10 C5 C6 C7 -2.6(4) . . . . ?
C4 C5 C6 N2 0.5(3) . . . . ?
C10 C5 C6 N2 179.28(18) . . . . ?
C5 C6 C7 C8 -179.6(2) . . . . ?
N2 C6 C7 C8 -1.3(3) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C7 C8 C9 N2 -0.9(3) . . . . ?
C6 C5 C10 C11 132.6(2) . . . . ?
C4 C5 C10 C11 -48.6(3) . . . . ?
C6 C5 C10 C15 -49.4(3) . . . . ?
C4 C5 C10 C15 129.4(2) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C5 C10 C11 C12 178.4(2) . . . . ?
C10 C11 C12 C13 -2.3(3) . . . . ?
C11 C12 C13 N3 -177.9(2) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
N3 C13 C14 C15 -179.8(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 -2.5(3) . . . . ?
C11 C10 C15 C14 2.1(3) . . . . ?
C5 C10 C15 C14 -175.9(2) . . . . ?
C2 C1 N1 C4 -0.1(3) . . . . ?
C2 C1 N1 B1 178.6(2) . . . . ?
C3 C4 N1 C1 0.7(2) . . . . ?
C5 C4 N1 C1 176.4(2) . . . . ?
C3 C4 N1 B1 -178.0(2) . . . . ?
C5 C4 N1 B1 -2.3(3) . . . . ?
F2 B1 N1 C1 71.5(3) . . . . ?
F1 B1 N1 C1 -48.3(3) . . . . ?
N2 B1 N1 C1 -168.9(2) . . . . ?
F2 B1 N1 C4 -110.0(2) . . . . ?
F1 B1 N1 C4 130.2(2) . . . . ?
N2 B1 N1 C4 9.5(3) . . . . ?
C8 C9 N2 C6 0.1(3) . . . . ?
C8 C9 N2 B1 170.2(2) . . . . ?
C7 C6 N2 C9 0.7(2) . . . . ?
C5 C6 N2 C9 179.2(2) . . . . ?
C7 C6 N2 B1 -169.6(2) . . . . ?
C5 C6 N2 B1 8.9(3) . . . . ?
F2 B1 N2 C9 -61.5(3) . . . . ?
F1 B1 N2 C9 58.4(3) . . . . ?
N1 B1 N2 C9 178.8(2) . . . . ?
F2 B1 N2 C6 106.8(2) . . . . ?
F1 B1 N2 C6 -133.3(2) . . . . ?
N1 B1 N2 C6 -12.9(3) . . . . ?
C14 C13 N3 C17 -5.9(3) . . . . ?
C12 C13 N3 C17 173.9(2) . . . . ?
C14 C13 N3 C16 179.3(2) . . . . ?
C12 C13 N3 C16 -1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 F1 0.93 2.60 3.477(3) 158.6 3_657
C2 H2 N3 0.93 2.67 3.495(3) 147.8 3_656
C12 H12 F1 0.93 2.59 3.471(3) 157.7 2_646
C16 H16B F2 0.96 2.56 3.362(3) 140.9 1_554

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.80
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
