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

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

data_i
_database_code_depnum_ccdc_archive 'CCDC 1402916'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 B F3 N2'
_chemical_formula_sum            'C5 H8 B F3 N2'
_chemical_formula_weight         163.94

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/m

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

_cell_length_a                   7.169(2)
_cell_length_b                   6.8769(19)
_cell_length_c                   7.474(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.675(3)
_cell_angle_gamma                90.00
_cell_volume                     354.77(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       single
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             168
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Histar
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4193
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         28.16
_reflns_number_total             927
_reflns_number_gt                765
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0456P)²+0.1140P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         927
_refine_ls_number_parameters     78
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
F1 F 0.12852(17) 0.2500 0.53019(15) 0.0337(3) Uani 1 2 d S . .
C1 C 0.3123(3) 0.2500 1.1517(3) 0.0230(4) Uani 1 2 d S . .
B1 B 0.2232(3) 0.2500 0.7186(3) 0.0193(4) Uani 1 2 d S . .
F2 F 0.34039(11) 0.08510(12) 0.76220(12) 0.0291(3) Uani 1 1 d . . .
C2 C 0.0661(2) 0.2500 0.8427(2) 0.0155(4) Uani 1 2 d S . .
C3 C -0.2508(3) 0.2500 0.5947(3) 0.0248(4) Uani 1 2 d S . .
C4 C -0.2017(3) 0.2500 0.9400(3) 0.0195(4) Uani 1 2 d S . .
H18A H -0.3348 0.2500 0.9380 0.023 Uiso 1 2 calc SR . .
C5 C -0.0502(3) 0.2500 1.0918(3) 0.0190(4) Uani 1 2 d S . .
H11A H -0.0553 0.2500 1.2175 0.023 Uiso 1 2 calc SR . .
N6 N 0.1143(2) 0.2500 1.02964(19) 0.0159(3) Uani 1 2 d S . .
N7 N -0.1284(2) 0.2500 0.7874(2) 0.0169(3) Uani 1 2 d S . .
H11 H 0.306(4) 0.2500 1.273(5) 0.057(9) Uiso 1 2 d S . .
H12 H 0.380(3) 0.139(3) 1.131(2) 0.037(5) Uiso 1 1 d . . .
H31 H -0.382(4) 0.2500 0.603(4) 0.039(7) Uiso 1 2 d S . .
H32 H -0.227(2) 0.140(3) 0.527(3) 0.039(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0231(6) 0.0632(9) 0.0155(6) 0.000 0.0066(5) 0.000
C1 0.0180(9) 0.0304(11) 0.0183(9) 0.000 0.0010(7) 0.000
B1 0.0158(9) 0.0263(10) 0.0168(10) 0.000 0.0063(7) 0.000
F2 0.0254(5) 0.0316(5) 0.0340(5) 0.0006(4) 0.0143(4) 0.0079(3)
C2 0.0144(8) 0.0151(8) 0.0165(8) 0.000 0.0030(6) 0.000
C3 0.0176(10) 0.0384(12) 0.0163(9) 0.000 0.0010(7) 0.000
C4 0.0178(9) 0.0231(9) 0.0201(9) 0.000 0.0093(7) 0.000
C5 0.0202(9) 0.0214(9) 0.0178(9) 0.000 0.0089(7) 0.000
N6 0.0149(7) 0.0177(7) 0.0148(7) 0.000 0.0033(6) 0.000
N7 0.0154(7) 0.0192(7) 0.0156(7) 0.000 0.0035(6) 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.388(2) . ?
C1 N6 1.465(2) . ?
C1 H11 0.92(3) . ?
C1 H12 0.941(19) . ?
B1 F2 1.3966(14) 4_565 ?
B1 F2 1.3966(14) . ?
B1 C2 1.641(3) . ?
C2 N6 1.345(2) . ?
C2 N7 1.343(2) . ?
C3 N7 1.470(2) . ?
C3 H31 0.96(3) . ?
C3 H32 0.954(19) . ?
C4 C5 1.342(3) . ?
C4 N7 1.378(2) . ?
C4 H18A 0.9500 . ?
C5 N6 1.380(2) . ?
C5 H11A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 C1 H11 108.6(19) . . ?
N6 C1 H12 110.7(11) . . ?
H11 C1 H12 108.9(14) . . ?
F1 B1 F2 109.58(11) . 4_565 ?
F1 B1 F2 109.58(11) . . ?
F2 B1 F2 108.58(15) 4_565 . ?
F1 B1 C2 110.58(15) . . ?
F2 B1 C2 109.25(10) 4_565 . ?
F2 B1 C2 109.25(10) . . ?
N6 C2 N7 105.90(15) . . ?
N6 C2 B1 124.32(15) . . ?
N7 C2 B1 129.78(16) . . ?
N7 C3 H31 105.8(16) . . ?
N7 C3 H32 112.0(11) . . ?
H31 C3 H32 110.8(14) . . ?
C5 C4 N7 107.29(16) . . ?
C5 C4 H18A 126.4 . . ?
N7 C4 H18A 126.4 . . ?
C4 C5 N6 106.58(16) . . ?
C4 C5 H11A 126.7 . . ?
N6 C5 H11A 126.7 . . ?
C2 N6 C5 110.26(15) . . ?
C2 N6 C1 125.48(15) . . ?
C5 N6 C1 124.25(15) . . ?
C2 N7 C4 109.97(15) . . ?
C2 N7 C3 126.64(15) . . ?
C4 N7 C3 123.39(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 B1 C2 N6 180.0 . . . . ?
F2 B1 C2 N6 -59.32(11) 4_565 . . . ?
F2 B1 C2 N6 59.32(11) . . . . ?
F1 B1 C2 N7 0.0 . . . . ?
F2 B1 C2 N7 120.68(11) 4_565 . . . ?
F2 B1 C2 N7 -120.68(11) . . . . ?
N7 C4 C5 N6 0.0 . . . . ?
N7 C2 N6 C5 0.0 . . . . ?
B1 C2 N6 C5 180.0 . . . . ?
N7 C2 N6 C1 180.0 . . . . ?
B1 C2 N6 C1 0.0 . . . . ?
C4 C5 N6 C2 0.0 . . . . ?
C4 C5 N6 C1 180.0 . . . . ?
N6 C2 N7 C4 0.0 . . . . ?
B1 C2 N7 C4 180.0 . . . . ?
N6 C2 N7 C3 180.0 . . . . ?
B1 C2 N7 C3 0.0 . . . . ?
C5 C4 N7 C2 0.0 . . . . ?
C5 C4 N7 C3 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.16
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_i
_database_code_depnum_ccdc_archive 'CCDC 1402917'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H7 B F3 N3 O2'
_chemical_formula_weight         208.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/c

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

_cell_length_a                   7.4533(5)
_cell_length_b                   9.5695(6)
_cell_length_c                   11.8645(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0490(10)
_cell_angle_gamma                90.00
_cell_volume                     817.21(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       single
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9885
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0282
_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       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         28.32
_reflns_number_total             2039
_reflns_number_gt                1868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0579P)²+0.3922P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2039
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
F1 F 0.50235(11) -0.11523(8) 0.70893(7) 0.0249(2) Uani 1 1 d . . .
O1 O 0.81512(14) 0.46021(11) 0.52755(9) 0.0245(2) Uani 1 1 d . . .
N1 N 0.37963(14) 0.20118(11) 0.52065(9) 0.0146(2) Uani 1 1 d . . .
C1 C 0.18569(17) 0.19109(15) 0.45065(12) 0.0221(3) Uani 1 1 d . . .
H1A H 0.1257 0.1146 0.4784 0.033 Uiso 1 1 calc R . .
H1B H 0.1832 0.1757 0.3703 0.033 Uiso 1 1 calc R . .
H1C H 0.1217 0.2764 0.4575 0.033 Uiso 1 1 calc R . .
B1 B 0.3703(2) -0.01165(14) 0.66770(12) 0.0165(3) Uani 1 1 d . . .
F2 F 0.30370(13) 0.03983(9) 0.75911(7) 0.0263(2) Uani 1 1 d . . .
O2 O 0.97051(13) 0.31931(12) 0.66152(9) 0.0270(2) Uani 1 1 d . . .
N2 N 0.64077(13) 0.16712(11) 0.64989(8) 0.0137(2) Uani 1 1 d . . .
C2 C 0.46557(16) 0.11903(12) 0.61203(9) 0.0135(2) Uani 1 1 d . . .
F3 F 0.22507(11) -0.06858(9) 0.58143(7) 0.0254(2) Uani 1 1 d . . .
N3 N 0.82716(14) 0.35793(12) 0.59167(9) 0.0176(2) Uani 1 1 d . . .
C3 C 0.77818(18) 0.11727(14) 0.75538(11) 0.0215(3) Uani 1 1 d . . .
H3A H 0.7295 0.0371 0.7862 0.032 Uiso 1 1 calc R . .
H3B H 0.8034 0.1902 0.8129 0.032 Uiso 1 1 calc R . .
H3C H 0.8910 0.0921 0.7357 0.032 Uiso 1 1 calc R . .
C4 C 0.66054(16) 0.27990(12) 0.58168(10) 0.0140(2) Uani 1 1 d . . .
C5 C 0.49791(17) 0.30107(12) 0.50031(10) 0.0153(2) Uani 1 1 d . . .
H5A H 0.4723 0.3694 0.4426 0.018 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0266(4) 0.0173(4) 0.0303(4) 0.0060(3) 0.0066(3) 0.0010(3)
O1 0.0267(5) 0.0254(5) 0.0241(5) 0.0024(4) 0.0113(4) -0.0071(4)
N1 0.0129(5) 0.0168(5) 0.0123(5) -0.0002(4) 0.0002(4) -0.0013(4)
C1 0.0131(6) 0.0257(6) 0.0227(6) 0.0015(5) -0.0037(5) -0.0019(5)
B1 0.0198(6) 0.0153(6) 0.0148(6) -0.0008(5) 0.0051(5) -0.0034(5)
F2 0.0385(5) 0.0235(4) 0.0224(4) -0.0014(3) 0.0179(4) -0.0035(3)
O2 0.0148(4) 0.0327(6) 0.0300(5) -0.0012(4) -0.0004(4) -0.0036(4)
N2 0.0136(5) 0.0150(5) 0.0114(4) -0.0008(3) 0.0012(3) -0.0003(3)
C2 0.0142(5) 0.0148(5) 0.0108(5) -0.0024(4) 0.0019(4) -0.0003(4)
F3 0.0263(4) 0.0230(4) 0.0236(4) -0.0017(3) 0.0007(3) -0.0112(3)
N3 0.0157(5) 0.0208(5) 0.0172(5) -0.0038(4) 0.0063(4) -0.0033(4)
C3 0.0201(6) 0.0211(6) 0.0176(6) 0.0031(5) -0.0051(4) 0.0005(5)
C4 0.0143(5) 0.0149(5) 0.0133(5) -0.0020(4) 0.0046(4) -0.0017(4)
C5 0.0170(5) 0.0163(5) 0.0125(5) 0.0005(4) 0.0037(4) -0.0010(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3928(16) . ?
O1 N3 1.2285(15) . ?
N1 C2 1.3576(15) . ?
N1 C5 1.3637(15) . ?
N1 C1 1.4715(15) . ?
B1 F3 1.3933(15) . ?
B1 F2 1.3948(16) . ?
B1 C2 1.6575(18) . ?
O2 N3 1.2269(15) . ?
N2 C2 1.3468(15) . ?
N2 C4 1.3796(15) . ?
N2 C3 1.4756(15) . ?
N3 C4 1.4274(15) . ?
C4 C5 1.3545(16) . ?

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
C2 N1 C5 110.77(10) . . ?
C2 N1 C1 127.12(11) . . ?
C5 N1 C1 122.11(10) . . ?
F1 B1 F3 108.85(10) . . ?
F1 B1 F2 109.87(10) . . ?
F3 B1 F2 110.10(11) . . ?
F1 B1 C2 109.90(10) . . ?
F3 B1 C2 109.50(10) . . ?
F2 B1 C2 108.61(10) . . ?
C2 N2 C4 108.28(10) . . ?
C2 N2 C3 124.87(10) . . ?
C4 N2 C3 126.45(10) . . ?
N2 C2 N1 106.50(10) . . ?
N2 C2 B1 127.11(10) . . ?
N1 C2 B1 126.37(10) . . ?
O2 N3 O1 124.69(11) . . ?
O2 N3 C4 119.00(11) . . ?
O1 N3 C4 116.31(10) . . ?
C5 C4 N2 108.85(10) . . ?
C5 C4 N3 125.40(11) . . ?
N2 C4 N3 125.71(10) . . ?
C4 C5 N1 105.60(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 1402918'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 B F3 N3 O2'
_chemical_formula_weight         259.00

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.5804(12)
_cell_length_b                   7.9279(13)
_cell_length_c                   18.431(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1107.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       single
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4976
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         27.44
_reflns_number_total             2523
_reflns_number_gt                2421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+7.4553P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2523
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.1079
_refine_ls_wR_factor_ref         0.2763
_refine_ls_wR_factor_gt          0.2751
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.012

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
F1 F 0.6181(7) 0.5752(9) 0.3421(5) 0.109(3) Uani 1 1 d . . .
F2 F 0.5834(5) 0.7614(6) 0.4338(2) 0.0341(9) Uani 1 1 d . . .
F3 F 0.5132(7) 0.8353(8) 0.3212(3) 0.0636(18) Uani 1 1 d . . .
O1 O -0.0893(7) 0.2770(6) 0.4913(2) 0.0343(12) Uani 1 1 d . . .
O2 O -0.0811(7) 0.3585(8) 0.2468(2) 0.0407(13) Uani 1 1 d . . .
N1 N 0.2369(6) 0.4870(6) 0.3659(3) 0.0182(10) Uani 1 1 d . . .
N2 N 0.1795(6) 0.7358(6) 0.4050(2) 0.0177(9) Uani 1 1 d . . .
N3 N -0.0524(6) 0.3541(6) 0.3720(3) 0.0209(10) Uani 1 1 d . . .
C1 C 0.3089(7) 0.6371(7) 0.3805(3) 0.0186(10) Uani 1 1 d . . .
C2 C 0.0582(7) 0.4932(7) 0.3810(3) 0.0191(11) Uani 1 1 d . . .
C3 C 0.0212(8) 0.6507(7) 0.4043(3) 0.0209(11) Uani 1 1 d . . .
H3A H -0.0911 0.6940 0.4176 0.025 Uiso 1 1 calc R . .
C4 C 0.3282(8) 0.3354(7) 0.3386(3) 0.0235(12) Uani 1 1 d . . .
H4A H 0.4540 0.3601 0.3324 0.035 Uiso 1 1 calc R . .
H4B H 0.2774 0.3025 0.2918 0.035 Uiso 1 1 calc R . .
H4C H 0.3139 0.2430 0.3734 0.035 Uiso 1 1 calc R . .
C5 C 0.1965(9) 0.9162(7) 0.4223(4) 0.0252(13) Uani 1 1 d . . .
H5A H 0.3210 0.9492 0.4198 0.038 Uiso 1 1 calc R . .
H5B H 0.1516 0.9371 0.4714 0.038 Uiso 1 1 calc R . .
H5C H 0.1283 0.9827 0.3873 0.038 Uiso 1 1 calc R . .
C6 C -0.1233(8) 0.2594(7) 0.4284(3) 0.0226(12) Uani 1 1 d . . .
C7 C -0.2430(8) 0.1338(8) 0.3943(4) 0.0273(13) Uani 1 1 d . . .
H7A H -0.3099 0.0508 0.4193 0.033 Uiso 1 1 calc R . .
C8 C -0.2406(10) 0.1571(9) 0.3224(4) 0.0353(16) Uani 1 1 d . . .
H8A H -0.3061 0.0932 0.2881 0.042 Uiso 1 1 calc R . .
C9 C -0.1203(8) 0.2978(8) 0.3048(3) 0.0252(13) Uani 1 1 d . . .
B1 B 0.5155(10) 0.6993(10) 0.3687(4) 0.0294(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.021(2) 0.083(4) 0.223(9) -0.101(5) 0.026(4) -0.011(3)
F2 0.0178(16) 0.045(2) 0.039(2) 0.0023(19) -0.0066(16) -0.0131(17)
F3 0.054(3) 0.094(4) 0.043(3) 0.025(3) 0.000(2) -0.047(3)
O1 0.049(3) 0.030(3) 0.024(2) 0.0009(19) 0.000(2) -0.010(2)
O2 0.042(3) 0.059(3) 0.021(2) -0.002(2) 0.003(2) -0.022(3)
N1 0.012(2) 0.020(2) 0.022(2) -0.0033(19) -0.0029(18) -0.0019(18)
N2 0.023(2) 0.0106(19) 0.020(2) -0.0022(17) -0.0012(18) -0.0014(19)
N3 0.020(2) 0.022(2) 0.021(2) -0.005(2) -0.0005(19) -0.008(2)
C1 0.021(3) 0.016(2) 0.019(2) -0.001(2) 0.001(2) -0.008(2)
C2 0.018(3) 0.019(3) 0.020(2) 0.002(2) 0.001(2) -0.004(2)
C3 0.027(3) 0.015(2) 0.021(3) -0.001(2) -0.001(2) -0.002(2)
C4 0.021(3) 0.017(3) 0.033(3) -0.002(2) 0.002(2) 0.002(2)
C5 0.033(3) 0.008(2) 0.035(3) 0.001(2) -0.005(3) -0.002(2)
C6 0.021(3) 0.018(3) 0.029(3) 0.001(2) 0.006(2) 0.009(2)
C7 0.020(3) 0.021(3) 0.041(4) -0.001(3) 0.002(2) -0.001(2)
C8 0.036(4) 0.028(3) 0.042(4) -0.016(3) -0.001(3) -0.010(3)
C9 0.017(3) 0.034(3) 0.025(3) -0.005(3) -0.001(2) -0.009(2)
B1 0.021(3) 0.032(4) 0.035(4) -0.007(3) 0.003(3) -0.006(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.347(9) . ?
F2 B1 1.395(9) . ?
F3 B1 1.390(10) . ?
O1 C6 1.195(8) . ?
O2 C9 1.209(8) . ?
N1 C1 1.337(7) . ?
N1 C2 1.383(7) . ?
N1 C4 1.476(7) . ?
N2 C1 1.334(7) . ?
N2 C3 1.376(7) . ?
N2 C5 1.471(7) . ?
N3 C6 1.392(8) . ?
N3 C2 1.395(7) . ?
N3 C9 1.413(7) . ?
C1 B1 1.656(9) . ?
C2 C3 1.351(8) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.487(9) . ?
C7 C8 1.337(10) . ?
C7 H7A 0.9500 . ?
C8 C9 1.477(9) . ?
C8 H8A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.2(5) . . ?
C1 N1 C4 127.0(5) . . ?
C2 N1 C4 123.8(5) . . ?
C1 N2 C3 110.6(4) . . ?
C1 N2 C5 125.4(5) . . ?
C3 N2 C5 123.7(5) . . ?
C6 N3 C2 124.7(5) . . ?
C6 N3 C9 110.1(5) . . ?
C2 N3 C9 125.0(5) . . ?
N2 C1 N1 106.8(5) . . ?
N2 C1 B1 124.5(5) . . ?
N1 C1 B1 128.7(5) . . ?
C3 C2 N1 107.5(5) . . ?
C3 C2 N3 130.1(5) . . ?
N1 C2 N3 122.4(5) . . ?
C2 C3 N2 105.9(5) . . ?
C2 C3 H3A 127.0 . . ?
N2 C3 H3A 127.0 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N3 125.4(6) . . ?
O1 C6 C7 128.4(6) . . ?
N3 C6 C7 106.3(5) . . ?
C8 C7 C6 108.6(6) . . ?
C8 C7 H7A 125.7 . . ?
C6 C7 H7A 125.7 . . ?
C7 C8 C9 109.3(6) . . ?
C7 C8 H8A 125.4 . . ?
C9 C8 H8A 125.4 . . ?
O2 C9 N3 124.0(6) . . ?
O2 C9 C8 130.3(6) . . ?
N3 C9 C8 105.8(5) . . ?
F1 B1 F3 110.1(7) . . ?
F1 B1 F2 111.0(7) . . ?
F3 B1 F2 105.9(6) . . ?
F1 B1 C1 112.1(6) . . ?
F3 B1 C1 107.6(6) . . ?
F2 B1 C1 110.0(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N1 -1.8(6) . . . . ?
C5 N2 C1 N1 -175.0(5) . . . . ?
C3 N2 C1 B1 176.1(6) . . . . ?
C5 N2 C1 B1 2.9(9) . . . . ?
C2 N1 C1 N2 0.6(6) . . . . ?
C4 N1 C1 N2 -179.0(5) . . . . ?
C2 N1 C1 B1 -177.1(6) . . . . ?
C4 N1 C1 B1 3.2(10) . . . . ?
C1 N1 C2 C3 0.7(6) . . . . ?
C4 N1 C2 C3 -179.6(5) . . . . ?
C1 N1 C2 N3 -179.2(5) . . . . ?
C4 N1 C2 N3 0.5(8) . . . . ?
C6 N3 C2 C3 -72.8(8) . . . . ?
C9 N3 C2 C3 101.6(8) . . . . ?
C6 N3 C2 N1 107.1(6) . . . . ?
C9 N3 C2 N1 -78.5(8) . . . . ?
N1 C2 C3 N2 -1.7(6) . . . . ?
N3 C2 C3 N2 178.1(5) . . . . ?
C1 N2 C3 C2 2.2(6) . . . . ?
C5 N2 C3 C2 175.6(5) . . . . ?
C2 N3 C6 O1 -5.6(9) . . . . ?
C9 N3 C6 O1 179.3(6) . . . . ?
C2 N3 C6 C7 175.6(5) . . . . ?
C9 N3 C6 C7 0.5(6) . . . . ?
O1 C6 C7 C8 -179.1(7) . . . . ?
N3 C6 C7 C8 -0.4(7) . . . . ?
C6 C7 C8 C9 0.1(8) . . . . ?
C6 N3 C9 O2 179.8(7) . . . . ?
C2 N3 C9 O2 4.7(10) . . . . ?
C6 N3 C9 C8 -0.5(7) . . . . ?
C2 N3 C9 C8 -175.6(6) . . . . ?
C7 C8 C9 O2 179.9(8) . . . . ?
C7 C8 C9 N3 0.2(8) . . . . ?
N2 C1 B1 F1 -178.8(7) . . . . ?
N1 C1 B1 F1 -1.4(11) . . . . ?
N2 C1 B1 F3 -57.6(8) . . . . ?
N1 C1 B1 F3 119.8(7) . . . . ?
N2 C1 B1 F2 57.2(8) . . . . ?
N1 C1 B1 F2 -125.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.147
