# 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_bb
_database_code_depnum_ccdc_archive 'CCDC 1446478'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        BB
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 B F2 N O2'
_chemical_formula_weight         285.05

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   P2(1)/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                   7.1854(14)
_cell_length_b                   12.877(3)
_cell_length_c                   13.705(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.63(3)
_cell_angle_gamma                90.00
_cell_volume                     1265.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9173
_cell_measurement_theta_min      6.25
_cell_measurement_theta_max      55.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11969
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2871
_reflns_number_gt                2044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0711P)²+0.0000P] 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         2871
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
O1 O 0.18271(12) -0.05244(7) 0.16366(7) 0.0435(2) Uani 1 1 d . . .
C7 C 0.27832(16) 0.03663(10) -0.07864(9) 0.0376(3) Uani 1 1 d . . .
O2 O 0.28798(14) 0.13717(7) -0.06130(7) 0.0511(3) Uani 1 1 d . . .
N1 N 0.22330(14) 0.10615(8) 0.10837(8) 0.0374(3) Uani 1 1 d . . .
F1 F 0.39821(16) 0.25244(7) 0.05782(7) 0.0781(4) Uani 1 1 d . . .
C15 C 0.16706(17) 0.01623(10) 0.24168(9) 0.0387(3) Uani 1 1 d . . .
C10 C 0.19196(16) 0.11518(10) 0.20789(9) 0.0381(3) Uani 1 1 d . . .
C6 C 0.31250(16) 0.00773(11) -0.18043(9) 0.0393(3) Uani 1 1 d . . .
F2 F 0.08970(16) 0.24721(8) 0.01675(7) 0.0825(4) Uani 1 1 d . . .
C9 C 0.21669(15) 0.00691(10) 0.08635(9) 0.0364(3) Uani 1 1 d . . .
C11 C 0.18399(19) 0.20001(12) 0.26901(10) 0.0479(3) Uani 1 1 d . . .
H11 H 0.2010 0.2674 0.2469 0.057 Uiso 1 1 calc R . .
C13 C 0.1246(2) 0.07848(13) 0.39788(11) 0.0528(4) Uani 1 1 d . . .
H13 H 0.1019 0.0678 0.4632 0.063 Uiso 1 1 calc R . .
C8 C 0.24162(17) -0.03259(10) -0.00751(10) 0.0412(3) Uani 1 1 d . . .
H8 H 0.2333 -0.1034 -0.0205 0.049 Uiso 1 1 calc R . .
C1 C 0.3427(2) 0.08500(12) -0.24826(11) 0.0489(3) Uani 1 1 d . . .
H1 H 0.3419 0.1543 -0.2292 0.059 Uiso 1 1 calc R . .
C14 C 0.13275(18) -0.00649(12) 0.33682(10) 0.0487(4) Uani 1 1 d . . .
H14 H 0.1162 -0.0741 0.3585 0.058 Uiso 1 1 calc R . .
C4 C 0.3465(2) -0.11879(13) -0.30669(11) 0.0549(4) Uani 1 1 d . . .
H4 H 0.3481 -0.1879 -0.3264 0.066 Uiso 1 1 calc R . .
C5 C 0.31534(19) -0.09495(12) -0.21094(10) 0.0474(3) Uani 1 1 d . . .
H5 H 0.2961 -0.1480 -0.1666 0.057 Uiso 1 1 calc R . .
C3 C 0.3752(2) -0.04195(14) -0.37295(11) 0.0548(4) Uani 1 1 d . . .
H3 H 0.3955 -0.0588 -0.4374 0.066 Uiso 1 1 calc R . .
C12 C 0.1492(2) 0.17897(13) 0.36513(10) 0.0532(4) Uani 1 1 d . . .
H12 H 0.1421 0.2338 0.4089 0.064 Uiso 1 1 calc R . .
B1 B 0.2506(2) 0.19050(12) 0.02953(11) 0.0463(4) Uani 1 1 d . . .
C2 C 0.3739(2) 0.05986(14) -0.34412(11) 0.0566(4) Uani 1 1 d . . .
H2 H 0.3941 0.1122 -0.3890 0.068 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3413(15) . ?
O1 C15 1.3975(16) . ?
C7 O2 1.3173(16) . ?
C7 C8 1.3590(18) . ?
C7 C6 1.4793(18) . ?
O2 B1 1.4614(18) . ?
N1 C9 1.3131(16) . ?
N1 C10 1.4012(17) . ?
N1 B1 1.5533(19) . ?
F1 B1 1.3633(19) . ?
C15 C10 1.3714(18) . ?
C15 C14 1.3738(19) . ?
C10 C11 1.3799(19) . ?
C6 C5 1.3872(19) . ?
C6 C1 1.388(2) . ?
F2 B1 1.370(2) . ?
C9 C8 1.4054(19) . ?
C11 C12 1.383(2) . ?
C13 C14 1.381(2) . ?
C13 C12 1.385(2) . ?
C1 C2 1.385(2) . ?
C4 C3 1.367(2) . ?
C4 C5 1.380(2) . ?
C3 C2 1.369(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
C9 O1 C15 105.74(10) . . ?
O2 C7 C8 121.70(12) . . ?
O2 C7 C6 114.04(12) . . ?
C8 C7 C6 124.25(12) . . ?
C7 O2 B1 127.24(11) . . ?
C9 N1 C10 107.39(11) . . ?
C9 N1 B1 121.66(11) . . ?
C10 N1 B1 130.86(11) . . ?
C10 C15 C14 123.60(13) . . ?
C10 C15 O1 108.12(11) . . ?
C14 C15 O1 128.28(12) . . ?
C15 C10 C11 121.28(13) . . ?
C15 C10 N1 106.50(11) . . ?
C11 C10 N1 132.23(12) . . ?
C5 C6 C1 118.39(13) . . ?
C5 C6 C7 122.04(13) . . ?
C1 C6 C7 119.58(12) . . ?
N1 C9 O1 112.25(11) . . ?
N1 C9 C8 123.90(11) . . ?
O1 C9 C8 123.84(12) . . ?
C10 C11 C12 116.11(13) . . ?
C14 C13 C12 122.19(14) . . ?
C7 C8 C9 117.45(12) . . ?
C2 C1 C6 120.62(14) . . ?
C15 C14 C13 115.06(14) . . ?
C3 C4 C5 120.73(15) . . ?
C4 C5 C6 120.34(15) . . ?
C4 C3 C2 119.81(15) . . ?
C11 C12 C13 121.76(15) . . ?
F1 B1 F2 111.08(13) . . ?
F1 B1 O2 109.62(13) . . ?
F2 B1 O2 109.92(12) . . ?
F1 B1 N1 109.98(12) . . ?
F2 B1 N1 108.59(12) . . ?
O2 B1 N1 107.58(11) . . ?
C3 C2 C1 120.12(16) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_b2b
_database_code_depnum_ccdc_archive 'CCDC 1446479'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        B2B
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B F2 N O3'
_chemical_formula_weight         315.08

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'
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   P2(1)/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                   7.7022(15)
_cell_length_b                   8.6623(17)
_cell_length_c                   21.644(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.29(3)
_cell_angle_gamma                90.00
_cell_volume                     1425.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9176
_cell_measurement_theta_min      6.01
_cell_measurement_theta_max      56.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13486
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_sigmaI/netI    0.1274
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.81
_reflns_number_total             3282
_reflns_number_gt                1334
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0345P)²+0.0000P] 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         3282
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.4415(3) 0.2797(2) 0.18788(11) 0.0590(6) Uani 1 1 d . . .
F1 F 0.1606(3) 0.27172(18) 0.12839(10) 0.0750(7) Uani 1 1 d . . .
F2 F 0.3938(3) 0.24395(18) 0.07968(9) 0.0722(6) Uani 1 1 d . . .
O3 O 0.3660(3) -0.1765(2) 0.20142(10) 0.0532(6) Uani 1 1 d . . .
N1 N 0.3239(3) 0.0358(2) 0.14421(12) 0.0446(7) Uani 1 1 d . . .
C11 C 0.2848(4) -0.2167(3) 0.14119(15) 0.0454(8) Uani 1 1 d . . .
O1 O 0.7153(3) 0.1171(3) 0.35803(12) 0.0769(8) Uani 1 1 d . . .
C7 C 0.5914(4) 0.3183(3) 0.29070(16) 0.0507(9) Uani 1 1 d . . .
C10 C 0.3868(4) -0.0223(3) 0.19962(16) 0.0466(8) Uani 1 1 d . . .
C9 C 0.4702(4) 0.0603(3) 0.25125(16) 0.0535(9) Uani 1 1 d . . .
H9 H 0.5045 0.0128 0.2898 0.064 Uiso 1 1 calc R . .
C6 C 0.5730(4) 0.4754(3) 0.27974(18) 0.0597(10) Uani 1 1 d . . .
H6 H 0.5073 0.5100 0.2425 0.072 Uiso 1 1 calc R . .
C12 C 0.2582(4) -0.0862(3) 0.10497(15) 0.0439(8) Uani 1 1 d . . .
C8 C 0.4994(4) 0.2128(3) 0.24296(16) 0.0493(8) Uani 1 1 d . . .
C16 C 0.2381(4) -0.3606(3) 0.11920(16) 0.0558(9) Uani 1 1 d . . .
H16 H 0.2564 -0.4478 0.1445 0.067 Uiso 1 1 calc R . .
C13 C 0.1841(4) -0.0946(3) 0.04260(16) 0.0573(9) Uani 1 1 d . . .
H13 H 0.1685 -0.0071 0.0175 0.069 Uiso 1 1 calc R . .
C5 C 0.6503(5) 0.5812(4) 0.3230(2) 0.0717(11) Uani 1 1 d . . .
H5 H 0.6370 0.6863 0.3148 0.086 Uiso 1 1 calc R . .
C15 C 0.1616(5) -0.3690(4) 0.05695(17) 0.0606(10) Uani 1 1 d . . .
H15 H 0.1274 -0.4648 0.0398 0.073 Uiso 1 1 calc R . .
C2 C 0.6933(5) 0.2706(4) 0.34764(17) 0.0578(9) Uani 1 1 d . . .
B1 B 0.3286(5) 0.2128(4) 0.1338(2) 0.0522(10) Uani 1 1 d . . .
C3 C 0.7703(5) 0.3767(5) 0.39093(17) 0.0690(10) Uani 1 1 d . . .
H3 H 0.8373 0.3439 0.4283 0.083 Uiso 1 1 calc R . .
C4 C 0.7474(5) 0.5313(5) 0.3785(2) 0.0767(13) Uani 1 1 d . . .
H4 H 0.7980 0.6033 0.4079 0.092 Uiso 1 1 calc R . .
C14 C 0.1344(5) -0.2389(4) 0.01930(17) 0.0651(10) Uani 1 1 d . . .
H14 H 0.0818 -0.2492 -0.0223 0.078 Uiso 1 1 calc R . .
C1 C 0.8118(5) 0.0626(5) 0.41572(19) 0.0921(14) Uani 1 1 d . . .
H1A H 0.9319 0.0961 0.4195 0.138 Uiso 1 1 calc R . .
H1B H 0.8079 -0.0482 0.4165 0.138 Uiso 1 1 calc R . .
H1C H 0.7607 0.1031 0.4499 0.138 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.336(4) . ?
O2 B1 1.461(5) . ?
F1 B1 1.378(4) . ?
F2 B1 1.374(4) . ?
O3 C10 1.346(3) . ?
O3 C11 1.396(4) . ?
N1 C10 1.319(4) . ?
N1 C12 1.398(4) . ?
N1 B1 1.551(4) . ?
C11 C16 1.362(4) . ?
C11 C12 1.372(4) . ?
O1 C2 1.355(4) . ?
O1 C1 1.427(4) . ?
C7 C6 1.385(4) . ?
C7 C2 1.412(4) . ?
C7 C8 1.472(4) . ?
C10 C9 1.394(4) . ?
C9 C8 1.357(4) . ?
C6 C5 1.375(4) . ?
C12 C13 1.380(4) . ?
C16 C15 1.382(4) . ?
C13 C14 1.379(4) . ?
C5 C4 1.378(5) . ?
C15 C14 1.386(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.371(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
C8 O2 B1 127.8(3) . . ?
C10 O3 C11 105.0(2) . . ?
C10 N1 C12 107.9(2) . . ?
C10 N1 B1 119.7(3) . . ?
C12 N1 B1 132.3(3) . . ?
C16 C11 C12 123.2(3) . . ?
C16 C11 O3 127.5(3) . . ?
C12 C11 O3 109.3(3) . . ?
C2 O1 C1 120.2(3) . . ?
C6 C7 C2 117.6(3) . . ?
C6 C7 C8 117.8(3) . . ?
C2 C7 C8 124.6(3) . . ?
N1 C10 O3 112.1(3) . . ?
N1 C10 C9 126.0(3) . . ?
O3 C10 C9 121.9(3) . . ?
C8 C9 C10 117.3(3) . . ?
C5 C6 C7 121.2(4) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 N1 105.6(3) . . ?
C13 C12 N1 133.3(3) . . ?
O2 C8 C9 120.1(3) . . ?
O2 C8 C7 114.3(3) . . ?
C9 C8 C7 125.7(3) . . ?
C11 C16 C15 115.8(3) . . ?
C14 C13 C12 116.9(3) . . ?
C6 C5 C4 119.9(4) . . ?
C16 C15 C14 122.0(3) . . ?
O1 C2 C3 120.9(4) . . ?
O1 C2 C7 118.0(3) . . ?
C3 C2 C7 121.1(3) . . ?
F2 B1 F1 108.8(3) . . ?
F2 B1 O2 110.7(3) . . ?
F1 B1 O2 110.5(3) . . ?
F2 B1 N1 109.8(3) . . ?
F1 B1 N1 109.5(3) . . ?
O2 B1 N1 107.5(3) . . ?
C4 C3 C2 119.4(4) . . ?
C3 C4 C5 120.8(4) . . ?
C13 C14 C15 121.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.81
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_b3b
_database_code_depnum_ccdc_archive 'CCDC 1446480'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        B3B
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B F2 N O3'
_chemical_formula_weight         315.08

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'
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   P2(1)/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                   7.1557(14)
_cell_length_b                   8.6916(17)
_cell_length_c                   22.455(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.46(3)
_cell_angle_gamma                90.00
_cell_volume                     1395.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9445
_cell_measurement_theta_min      6.06
_cell_measurement_theta_max      55.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13138
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3194
_reflns_number_gt                2105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0692P)²+0.0550P] 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         3194
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O3 O 0.68457(17) 0.23165(15) 0.02858(5) 0.0442(3) Uani 1 1 d . . .
O2 O 0.79218(19) 0.68871(15) 0.03957(5) 0.0491(3) Uani 1 1 d . . .
N1 N 0.73401(19) 0.43847(17) 0.08468(6) 0.0372(3) Uani 1 1 d . . .
C6 C 0.8069(2) 0.7354(2) -0.06333(7) 0.0371(4) Uani 1 1 d . . .
F1 F 0.6092(2) 0.67144(14) 0.12199(6) 0.0737(4) Uani 1 1 d . . .
F2 F 0.92106(19) 0.63454(16) 0.13330(5) 0.0722(4) Uani 1 1 d . . .
C10 C 0.7218(2) 0.3831(2) 0.02969(7) 0.0374(4) Uani 1 1 d . . .
C8 C 0.7785(2) 0.6252(2) -0.01414(7) 0.0370(4) Uani 1 1 d . . .
C9 C 0.7428(2) 0.4725(2) -0.02146(7) 0.0411(4) Uani 1 1 d . . .
H9 H 0.7328 0.4288 -0.0593 0.049 Uiso 1 1 calc R . .
O1 O 0.8097(2) 0.73003(18) -0.22439(6) 0.0592(4) Uani 1 1 d . . .
C11 C 0.6722(2) 0.1880(2) 0.08805(8) 0.0393(4) Uani 1 1 d . . .
C5 C 0.8437(3) 0.8897(2) -0.05061(8) 0.0456(4) Uani 1 1 d . . .
H5 H 0.8490 0.9239 -0.0113 0.055 Uiso 1 1 calc R . .
C16 C 0.7030(2) 0.3163(2) 0.12350(7) 0.0371(4) Uani 1 1 d . . .
C2 C 0.8245(2) 0.7907(2) -0.16821(8) 0.0430(4) Uani 1 1 d . . .
C7 C 0.7975(2) 0.6871(2) -0.12235(8) 0.0424(4) Uani 1 1 d . . .
H7 H 0.7729 0.5844 -0.1312 0.051 Uiso 1 1 calc R . .
C4 C 0.8724(3) 0.9914(2) -0.09643(9) 0.0519(5) Uani 1 1 d . . .
H4 H 0.8981 1.0941 -0.0878 0.062 Uiso 1 1 calc R . .
C3 C 0.8633(3) 0.9426(2) -0.15527(9) 0.0483(5) Uani 1 1 d . . .
H3 H 0.8832 1.0121 -0.1859 0.058 Uiso 1 1 calc R . .
C13 C 0.6285(3) 0.0357(3) 0.17144(9) 0.0522(5) Uani 1 1 d . . .
H13 H 0.6044 -0.0589 0.1889 0.063 Uiso 1 1 calc R . .
C15 C 0.6965(3) 0.3065(2) 0.18486(8) 0.0458(4) Uani 1 1 d . . .
H15 H 0.7169 0.3918 0.2092 0.055 Uiso 1 1 calc R . .
C12 C 0.6337(3) 0.0446(2) 0.11013(9) 0.0494(5) Uani 1 1 d . . .
H12 H 0.6126 -0.0403 0.0856 0.059 Uiso 1 1 calc R . .
C14 C 0.6582(3) 0.1632(2) 0.20800(9) 0.0509(5) Uani 1 1 d . . .
H14 H 0.6520 0.1518 0.2490 0.061 Uiso 1 1 calc R . .
B1 B 0.7659(3) 0.6131(3) 0.09675(8) 0.0428(5) Uani 1 1 d . . .
C1 C 0.8200(3) 0.8336(3) -0.27337(9) 0.0635(6) Uani 1 1 d . . .
H1A H 0.7243 0.9104 -0.2708 0.095 Uiso 1 1 calc R . .
H1B H 0.8021 0.7777 -0.3101 0.095 Uiso 1 1 calc R . .
H1C H 0.9405 0.8823 -0.2722 0.095 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C10 1.343(2) . ?
O3 C11 1.395(2) . ?
O2 C8 1.326(2) . ?
O2 B1 1.462(2) . ?
N1 C10 1.325(2) . ?
N1 C16 1.398(2) . ?
N1 B1 1.557(3) . ?
C6 C7 1.389(2) . ?
C6 C5 1.394(3) . ?
C6 C8 1.482(2) . ?
F1 B1 1.375(2) . ?
F2 B1 1.365(2) . ?
C10 C9 1.400(2) . ?
C8 C9 1.361(3) . ?
O1 C2 1.367(2) . ?
O1 C1 1.425(2) . ?
C11 C12 1.374(3) . ?
C11 C16 1.382(2) . ?
C5 C4 1.379(3) . ?
C16 C15 1.383(2) . ?
C2 C3 1.377(3) . ?
C2 C7 1.387(2) . ?
C4 C3 1.387(3) . ?
C13 C12 1.381(3) . ?
C13 C14 1.390(3) . ?
C15 C14 1.381(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
C10 O3 C11 105.62(13) . . ?
C8 O2 B1 127.20(15) . . ?
C10 N1 C16 107.42(15) . . ?
C10 N1 B1 121.30(14) . . ?
C16 N1 B1 131.18(14) . . ?
C7 C6 C5 119.13(16) . . ?
C7 C6 C8 120.91(17) . . ?
C5 C6 C8 119.96(15) . . ?
N1 C10 O3 112.24(15) . . ?
N1 C10 C9 123.94(17) . . ?
O3 C10 C9 123.82(15) . . ?
O2 C8 C9 121.48(16) . . ?
O2 C8 C6 113.70(16) . . ?
C9 C8 C6 124.82(15) . . ?
C8 C9 C10 117.92(16) . . ?
C2 O1 C1 117.65(17) . . ?
C12 C11 C16 123.61(17) . . ?
C12 C11 O3 127.89(17) . . ?
C16 C11 O3 108.49(15) . . ?
C4 C5 C6 119.79(17) . . ?
C11 C16 C15 120.86(17) . . ?
C11 C16 N1 106.23(15) . . ?
C15 C16 N1 132.91(17) . . ?
O1 C2 C3 124.82(17) . . ?
O1 C2 C7 115.28(17) . . ?
C3 C2 C7 119.90(17) . . ?
C2 C7 C6 120.66(18) . . ?
C5 C4 C3 120.84(19) . . ?
C2 C3 C4 119.67(17) . . ?
C12 C13 C14 122.26(19) . . ?
C14 C15 C16 116.47(18) . . ?
C11 C12 C13 115.16(19) . . ?
C15 C14 C13 121.63(18) . . ?
F2 B1 F1 111.02(16) . . ?
F2 B1 O2 109.55(16) . . ?
F1 B1 O2 109.54(17) . . ?
F2 B1 N1 110.30(17) . . ?
F1 B1 N1 108.38(15) . . ?
O2 B1 N1 107.99(14) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_b4b
_database_code_depnum_ccdc_archive 'CCDC 1446481'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        B4B
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B F2 N O3'
_chemical_formula_weight         315.08

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'
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   P2(1)/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                   7.1368(14)
_cell_length_b                   15.475(3)
_cell_length_c                   13.122(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.10(3)
_cell_angle_gamma                90.00
_cell_volume                     1411.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7424
_cell_measurement_theta_min      6
_cell_measurement_theta_max      55.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13143
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3217
_reflns_number_gt                1652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0685P)²+0.0000P] 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         3217
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_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
O3 O 0.1566(2) 1.16441(9) -0.08350(11) 0.0526(4) Uani 1 1 d . . .
N1 N 0.2540(2) 1.12179(10) 0.08112(12) 0.0433(4) Uani 1 1 d . . .
O2 O 0.3159(2) 0.97013(9) 0.12467(11) 0.0559(4) Uani 1 1 d . . .
C5 C 0.2908(3) 0.85747(13) 0.00257(16) 0.0442(5) Uani 1 1 d . . .
O1 O 0.3462(2) 0.59398(10) -0.04095(14) 0.0707(5) Uani 1 1 d . . .
C10 C 0.2087(3) 1.09715(13) -0.01772(15) 0.0442(5) Uani 1 1 d . . .
F2 F 0.1824(2) 1.05723(9) 0.23338(11) 0.0761(5) Uani 1 1 d . . .
F1 F 0.4940(2) 1.07545(9) 0.22892(10) 0.0747(5) Uani 1 1 d . . .
C11 C 0.2339(3) 1.21221(13) 0.08296(16) 0.0433(5) Uani 1 1 d . . .
C8 C 0.2733(3) 0.95001(13) 0.02382(15) 0.0431(5) Uani 1 1 d . . .
C6 C 0.2389(3) 0.82314(14) -0.09747(17) 0.0540(6) Uani 1 1 d . . .
H6 H 0.1916 0.8597 -0.1537 0.065 Uiso 1 1 calc R . .
C16 C 0.1715(3) 1.23779(14) -0.01937(17) 0.0485(5) Uani 1 1 d . . .
C4 C 0.3616(3) 0.80107(14) 0.08537(17) 0.0519(5) Uani 1 1 d . . .
H4 H 0.3991 0.8226 0.1531 0.062 Uiso 1 1 calc R . .
C2 C 0.3251(3) 0.68123(14) -0.03267(19) 0.0528(6) Uani 1 1 d . . .
C9 C 0.2161(3) 1.01194(14) -0.05103(16) 0.0479(5) Uani 1 1 d . . .
H9 H 0.1832 0.9977 -0.1217 0.057 Uiso 1 1 calc R . .
C14 C 0.1665(3) 1.38120(16) 0.0320(2) 0.0664(7) Uani 1 1 d . . .
H14 H 0.1445 1.4395 0.0164 0.080 Uiso 1 1 calc R . .
C3 C 0.3766(3) 0.71392(15) 0.06790(19) 0.0579(6) Uani 1 1 d . . .
H3 H 0.4215 0.6769 0.1239 0.069 Uiso 1 1 calc R . .
C7 C 0.2561(3) 0.73558(15) -0.11561(19) 0.0569(6) Uani 1 1 d . . .
H7 H 0.2213 0.7138 -0.1833 0.068 Uiso 1 1 calc R . .
C15 C 0.1353(3) 1.32209(15) -0.0492(2) 0.0615(6) Uani 1 1 d . . .
H15 H 0.0930 1.3384 -0.1189 0.074 Uiso 1 1 calc R . .
C13 C 0.2293(3) 1.35672(15) 0.1356(2) 0.0616(6) Uani 1 1 d . . .
H13 H 0.2481 1.3988 0.1875 0.074 Uiso 1 1 calc R . .
B1 B 0.3139(4) 1.05593(16) 0.17090(19) 0.0492(6) Uani 1 1 d . . .
C12 C 0.2647(3) 1.27102(14) 0.16336(18) 0.0538(6) Uani 1 1 d . . .
H12 H 0.3072 1.2541 0.2328 0.065 Uiso 1 1 calc R . .
C1 C 0.3020(4) 0.55585(16) -0.1420(2) 0.0811(8) Uani 1 1 d . . .
H1A H 0.1665 0.5607 -0.1715 0.122 Uiso 1 1 calc R . .
H1B H 0.3379 0.4960 -0.1367 0.122 Uiso 1 1 calc R . .
H1C H 0.3719 0.5851 -0.1863 0.122 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C10 1.349(2) . ?
O3 C16 1.403(3) . ?
N1 C10 1.320(3) . ?
N1 C11 1.407(3) . ?
N1 B1 1.543(3) . ?
O2 C8 1.326(2) . ?
O2 B1 1.461(3) . ?
C5 C6 1.386(3) . ?
C5 C4 1.396(3) . ?
C5 C8 1.470(3) . ?
O1 C2 1.366(3) . ?
O1 C1 1.420(3) . ?
C10 C9 1.394(3) . ?
F2 B1 1.379(3) . ?
F1 B1 1.371(3) . ?
C11 C12 1.373(3) . ?
C11 C16 1.374(3) . ?
C8 C9 1.367(3) . ?
C6 C7 1.386(3) . ?
C16 C15 1.370(3) . ?
C4 C3 1.376(3) . ?
C2 C7 1.375(3) . ?
C2 C3 1.383(3) . ?
C14 C15 1.384(3) . ?
C14 C13 1.384(4) . ?
C13 C12 1.384(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
C10 O3 C16 105.55(15) . . ?
C10 N1 C11 107.52(16) . . ?
C10 N1 B1 121.54(17) . . ?
C11 N1 B1 130.94(17) . . ?
C8 O2 B1 127.31(16) . . ?
C6 C5 C4 118.0(2) . . ?
C6 C5 C8 122.5(2) . . ?
C4 C5 C8 119.53(18) . . ?
C2 O1 C1 118.7(2) . . ?
N1 C10 O3 112.11(17) . . ?
N1 C10 C9 124.28(18) . . ?
O3 C10 C9 123.61(18) . . ?
C12 C11 C16 121.4(2) . . ?
C12 C11 N1 132.30(19) . . ?
C16 C11 N1 106.35(18) . . ?
O2 C8 C9 121.07(18) . . ?
O2 C8 C5 114.09(17) . . ?
C9 C8 C5 124.83(18) . . ?
C5 C6 C7 121.5(2) . . ?
C15 C16 C11 123.5(2) . . ?
C15 C16 O3 128.0(2) . . ?
C11 C16 O3 108.47(17) . . ?
C3 C4 C5 120.7(2) . . ?
O1 C2 C7 124.6(2) . . ?
O1 C2 C3 115.3(2) . . ?
C7 C2 C3 120.1(2) . . ?
C8 C9 C10 117.66(18) . . ?
C15 C14 C13 122.4(2) . . ?
C4 C3 C2 120.2(2) . . ?
C2 C7 C6 119.5(2) . . ?
C16 C15 C14 115.0(2) . . ?
C12 C13 C14 121.4(2) . . ?
F1 B1 F2 110.20(19) . . ?
F1 B1 O2 109.54(19) . . ?
F2 B1 O2 109.40(19) . . ?
F1 B1 N1 109.94(19) . . ?
F2 B1 N1 109.64(18) . . ?
O2 B1 N1 108.08(17) . . ?
C11 C12 C13 116.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_b24b
_database_code_depnum_ccdc_archive 'CCDC 1446482'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        B24B
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 B F2 N O4'
_chemical_formula_weight         345.10

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   P2(1)/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                   8.6901(17)
_cell_length_b                   8.0756(16)
_cell_length_c                   22.705(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.06(3)
_cell_angle_gamma                90.00
_cell_volume                     1568.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9364
_cell_measurement_theta_min      6.22
_cell_measurement_theta_max      55.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.573
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.115
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14835
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3592
_reflns_number_gt                2233
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0652P)²+0.0000P] 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         3592
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 -0.4595(3) 0.4504(3) -0.17246(11) 0.0699(7) Uani 1 1 d . . .
H1A H -0.4258 0.5328 -0.1979 0.105 Uiso 1 1 calc R . .
H1B H -0.5608 0.4100 -0.1904 0.105 Uiso 1 1 calc R . .
H1C H -0.3863 0.3603 -0.1673 0.105 Uiso 1 1 calc R . .
C15 C 0.5975(3) 1.1391(3) 0.22843(9) 0.0498(5) Uani 1 1 d . . .
H15 H 0.6250 1.1894 0.2656 0.060 Uiso 1 1 calc R . .
C14 C 0.7116(3) 1.1147(3) 0.19355(9) 0.0505(5) Uani 1 1 d . . .
H14 H 0.8137 1.1468 0.2085 0.061 Uiso 1 1 calc R . .
C13 C 0.6778(2) 1.0439(3) 0.13699(9) 0.0481(5) Uani 1 1 d . . .
H13 H 0.7531 1.0294 0.1129 0.058 Uiso 1 1 calc R . .
C12 C 0.5254(2) 0.9973(2) 0.11940(8) 0.0393(4) Uani 1 1 d . . .
C7 C -0.3568(3) 0.6673(3) -0.03046(9) 0.0502(5) Uani 1 1 d . . .
H7 H -0.4553 0.6733 -0.0198 0.060 Uiso 1 1 calc R . .
C2 C -0.3367(3) 0.5883(3) -0.08292(9) 0.0471(5) Uani 1 1 d . . .
B1 B 0.1094(3) 0.9229(3) 0.13660(9) 0.0365(5) Uani 1 1 d . . .
C16 C 0.4443(3) 1.0908(3) 0.20960(8) 0.0447(5) Uani 1 1 d . . .
H16 H 0.3681 1.1062 0.2332 0.054 Uiso 1 1 calc R . .
C6 C -0.2300(2) 0.7362(3) 0.00537(9) 0.0446(5) Uani 1 1 d . . .
H6 H -0.2444 0.7885 0.0405 0.053 Uiso 1 1 calc R . .
C8 C 0.1067(3) 0.5518(3) -0.12742(9) 0.0547(6) Uani 1 1 d . . .
H8A H 0.0751 0.4386 -0.1245 0.082 Uiso 1 1 calc R . .
H8B H 0.2153 0.5556 -0.1307 0.082 Uiso 1 1 calc R . .
H8C H 0.0456 0.6018 -0.1622 0.082 Uiso 1 1 calc R . .
C3 C -0.1905(2) 0.5794(2) -0.09848(8) 0.0429(5) Uani 1 1 d . . .
H3 H -0.1776 0.5263 -0.1336 0.051 Uiso 1 1 calc R . .
C10 C 0.2006(2) 0.8217(2) 0.02464(8) 0.0405(5) Uani 1 1 d . . .
H10 H 0.2319 0.7813 -0.0098 0.049 Uiso 1 1 calc R . .
C11 C 0.3066(2) 0.8984(2) 0.06935(8) 0.0368(4) Uani 1 1 d . . .
O1 O -0.46802(19) 0.5216(2) -0.11576(7) 0.0672(5) Uani 1 1 d . . .
C5 C -0.0792(2) 0.7312(2) -0.00864(8) 0.0359(4) Uani 1 1 d . . .
C17 C 0.4107(2) 1.0181(2) 0.15371(8) 0.0352(4) Uani 1 1 d . . .
C4 C -0.0625(2) 0.6494(2) -0.06181(8) 0.0371(4) Uani 1 1 d . . .
C9 C 0.0495(2) 0.8076(2) 0.03275(7) 0.0351(4) Uani 1 1 d . . .
N1 N 0.27292(18) 0.95392(18) 0.12040(6) 0.0343(4) Uani 1 1 d . . .
O2 O 0.08320(17) 0.63996(17) -0.07530(6) 0.0469(4) Uani 1 1 d . . .
O4 O 0.45848(16) 0.92110(17) 0.06578(5) 0.0451(4) Uani 1 1 d . . .
O3 O 0.00635(15) 0.86771(18) 0.08240(5) 0.0430(3) Uani 1 1 d . . .
F2 F 0.05259(14) 1.06408(14) 0.15822(5) 0.0547(3) Uani 1 1 d . . .
F1 F 0.12255(15) 0.79917(16) 0.17934(5) 0.0566(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 O1 1.424(3) . ?
C15 C16 1.381(3) . ?
C15 C14 1.386(3) . ?
C14 C13 1.389(3) . ?
C13 C12 1.367(3) . ?
C12 C17 1.378(3) . ?
C12 O4 1.397(2) . ?
C7 C6 1.369(3) . ?
C7 C2 1.389(3) . ?
C2 O1 1.361(2) . ?
C2 C3 1.379(3) . ?
B1 F2 1.367(2) . ?
B1 F1 1.384(2) . ?
B1 O3 1.459(2) . ?
B1 N1 1.549(3) . ?
C16 C17 1.382(3) . ?
C6 C5 1.402(3) . ?
C8 O2 1.426(2) . ?
C3 C4 1.388(3) . ?
C10 C9 1.362(3) . ?
C10 C11 1.392(3) . ?
C11 N1 1.323(2) . ?
C11 O4 1.348(2) . ?
C5 C4 1.406(3) . ?
C5 C9 1.466(3) . ?
C17 N1 1.399(2) . ?
C4 O2 1.356(2) . ?
C9 O3 1.340(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
C16 C15 C14 121.99(19) . . ?
C13 C14 C15 122.0(2) . . ?
C12 C13 C14 114.88(19) . . ?
C13 C12 C17 124.09(18) . . ?
C13 C12 O4 127.62(18) . . ?
C17 C12 O4 108.29(16) . . ?
C6 C7 C2 119.2(2) . . ?
O1 C2 C3 124.2(2) . . ?
O1 C2 C7 115.6(2) . . ?
C3 C2 C7 120.22(19) . . ?
F2 B1 F1 109.96(16) . . ?
F2 B1 O3 110.52(17) . . ?
F1 B1 O3 109.53(16) . . ?
F2 B1 N1 110.73(16) . . ?
F1 B1 N1 108.44(16) . . ?
O3 B1 N1 107.60(15) . . ?
C17 C16 C15 116.21(19) . . ?
C7 C6 C5 122.8(2) . . ?
C2 C3 C4 120.18(19) . . ?
C9 C10 C11 118.02(17) . . ?
N1 C11 O4 112.06(16) . . ?
N1 C11 C10 124.77(18) . . ?
O4 C11 C10 123.16(16) . . ?
C2 O1 C1 118.96(19) . . ?
C4 C5 C6 116.68(18) . . ?
C4 C5 C9 124.54(18) . . ?
C6 C5 C9 118.77(17) . . ?
C12 C17 C16 120.85(18) . . ?
C12 C17 N1 106.53(16) . . ?
C16 C17 N1 132.62(18) . . ?
O2 C4 C3 121.57(17) . . ?
O2 C4 C5 117.44(17) . . ?
C3 C4 C5 120.98(19) . . ?
O3 C9 C10 120.13(17) . . ?
O3 C9 C5 113.43(16) . . ?
C10 C9 C5 126.45(17) . . ?
C11 N1 C17 107.43(16) . . ?
C11 N1 B1 120.40(16) . . ?
C17 N1 B1 131.72(15) . . ?
C4 O2 C8 119.37(16) . . ?
C11 O4 C12 105.69(14) . . ?
C9 O3 B1 126.83(15) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1446483'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        B25B
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 B F2 N O4'
_chemical_formula_weight         345.10

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           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                   7.7008(15)
_cell_length_b                   11.481(2)
_cell_length_c                   18.166(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.52(3)
_cell_angle_gamma                90.00
_cell_volume                     1554.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11344
_cell_measurement_theta_min      6.22
_cell_measurement_theta_max      55.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.474
_exptl_crystal_size_min          0.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14992
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3552
_reflns_number_gt                2602
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0649P)²+0.1199P] 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         3552
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
N1 N 0.06075(16) 0.27345(10) -0.05017(7) 0.0410(3) Uani 1 1 d . . .
F2 F 0.18425(18) 0.13086(9) 0.04365(6) 0.0821(4) Uani 1 1 d . . .
F1 F -0.07776(16) 0.21065(13) 0.04733(6) 0.0886(4) Uani 1 1 d . . .
O1 O 0.3449(2) 0.46574(11) 0.33362(7) 0.0718(4) Uani 1 1 d . . .
O2 O 0.41796(18) 0.63983(10) 0.06100(7) 0.0644(4) Uani 1 1 d . . .
O3 O 0.17926(19) 0.32047(10) 0.08373(6) 0.0630(4) Uani 1 1 d . . .
O4 O 0.10544(14) 0.39457(8) -0.13833(6) 0.0476(3) Uani 1 1 d . . .
B1 B 0.0844(3) 0.23062(14) 0.03310(10) 0.0474(4) Uani 1 1 d . . .
C1 C 0.3723(3) 0.53548(17) 0.39916(10) 0.0698(5) Uani 1 1 d . . .
H1A H 0.4981 0.5512 0.4180 0.105 Uiso 1 1 calc R . .
H1B H 0.3291 0.4953 0.4374 0.105 Uiso 1 1 calc R . .
H1C H 0.3085 0.6076 0.3868 0.105 Uiso 1 1 calc R . .
C2 C 0.4776(3) 0.75509(15) 0.05449(12) 0.0622(5) Uani 1 1 d . . .
H2A H 0.3979 0.8089 0.0699 0.093 Uiso 1 1 calc R . .
H2B H 0.4787 0.7701 0.0026 0.093 Uiso 1 1 calc R . .
H2C H 0.5965 0.7644 0.0866 0.093 Uiso 1 1 calc R . .
C15 C -0.1475(2) 0.09200(15) -0.21808(10) 0.0584(4) Uani 1 1 d . . .
H15 H -0.2064 0.0224 -0.2344 0.070 Uiso 1 1 calc R . .
C14 C -0.1155(2) 0.16890(15) -0.27199(10) 0.0586(4) Uani 1 1 d . . .
H14 H -0.1519 0.1491 -0.3232 0.070 Uiso 1 1 calc R . .
C6 C 0.3735(2) 0.51522(14) 0.26930(9) 0.0496(4) Uani 1 1 d . . .
C16 C -0.0953(2) 0.11466(13) -0.14119(10) 0.0522(4) Uani 1 1 d . . .
H16 H -0.1158 0.0621 -0.1053 0.063 Uiso 1 1 calc R . .
C5 C 0.4594(2) 0.62037(14) 0.26617(10) 0.0544(4) Uani 1 1 d . . .
H5 H 0.5068 0.6623 0.3105 0.065 Uiso 1 1 calc R . .
C13 C -0.0308(2) 0.27430(15) -0.25145(9) 0.0531(4) Uani 1 1 d . . .
H13 H -0.0089 0.3267 -0.2871 0.064 Uiso 1 1 calc R . .
C10 C 0.2148(2) 0.45366(12) -0.00789(8) 0.0455(4) Uani 1 1 d . . .
H10 H 0.2561 0.5249 -0.0209 0.055 Uiso 1 1 calc R . .
C9 C 0.23716(19) 0.42246(12) 0.06579(8) 0.0420(3) Uani 1 1 d . . .
C17 C -0.01064(19) 0.22045(12) -0.12045(8) 0.0427(3) Uani 1 1 d . . .
C4 C 0.4744(2) 0.66262(14) 0.19684(10) 0.0533(4) Uani 1 1 d . . .
H4 H 0.5318 0.7334 0.1949 0.064 Uiso 1 1 calc R . .
C12 C 0.0185(2) 0.29626(12) -0.17494(9) 0.0442(3) Uani 1 1 d . . .
C7 C 0.3078(2) 0.45297(13) 0.20347(8) 0.0461(3) Uani 1 1 d . . .
H7 H 0.2530 0.3815 0.2062 0.055 Uiso 1 1 calc R . .
C11 C 0.12734(19) 0.37494(12) -0.06367(8) 0.0416(3) Uani 1 1 d . . .
C8 C 0.3208(2) 0.49355(12) 0.13307(8) 0.0424(3) Uani 1 1 d . . .
C3 C 0.4057(2) 0.60160(12) 0.13023(9) 0.0464(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
N1 C11 1.3206(18) . ?
N1 C17 1.3967(19) . ?
N1 B1 1.557(2) . ?
F2 B1 1.366(2) . ?
F1 B1 1.357(2) . ?
O1 C6 1.366(2) . ?
O1 C1 1.406(2) . ?
O2 C3 1.3575(19) . ?
O2 C2 1.4153(19) . ?
O3 C9 1.3225(17) . ?
O3 B1 1.451(2) . ?
O4 C11 1.3431(18) . ?
O4 C12 1.3932(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C15 C16 1.378(2) . ?
C15 C14 1.386(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.381(2) . ?
C14 H14 0.9300 . ?
C6 C7 1.376(2) . ?
C6 C5 1.385(2) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C5 C4 1.381(2) . ?
C5 H5 0.9300 . ?
C13 C12 1.369(2) . ?
C13 H13 0.9300 . ?
C10 C9 1.354(2) . ?
C10 C11 1.398(2) . ?
C10 H10 0.9300 . ?
C9 C8 1.476(2) . ?
C17 C12 1.378(2) . ?
C4 C3 1.383(2) . ?
C4 H4 0.9300 . ?
C7 C8 1.388(2) . ?
C7 H7 0.9300 . ?
C8 C3 1.409(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
C11 N1 C17 107.27(12) . . ?
C11 N1 B1 120.18(12) . . ?
C17 N1 B1 132.37(11) . . ?
C6 O1 C1 117.72(14) . . ?
C3 O2 C2 118.63(13) . . ?
C9 O3 B1 128.34(13) . . ?
C11 O4 C12 105.66(11) . . ?
F1 B1 F2 110.13(14) . . ?
F1 B1 O3 109.90(15) . . ?
F2 B1 O3 109.33(14) . . ?
F1 B1 N1 110.45(14) . . ?
F2 B1 N1 109.01(14) . . ?
O3 B1 N1 107.99(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 C15 C14 122.54(16) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C13 C14 C15 121.53(16) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
O1 C6 C7 115.10(14) . . ?
O1 C6 C5 125.38(15) . . ?
C7 C6 C5 119.52(15) . . ?
C15 C16 C17 116.03(16) . . ?
C15 C16 H16 122.0 . . ?
C17 C16 H16 122.0 . . ?
C4 C5 C6 119.58(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C12 C13 C14 115.33(16) . . ?
C12 C13 H13 122.3 . . ?
C14 C13 H13 122.3 . . ?
C9 C10 C11 117.66(13) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
O3 C9 C10 120.69(13) . . ?
O3 C9 C8 112.93(13) . . ?
C10 C9 C8 126.37(13) . . ?
C12 C17 C16 120.59(15) . . ?
C12 C17 N1 106.49(12) . . ?
C16 C17 N1 132.92(14) . . ?
C5 C4 C3 121.23(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C13 C12 C17 123.98(14) . . ?
C13 C12 O4 127.71(14) . . ?
C17 C12 O4 108.30(13) . . ?
C6 C7 C8 122.04(14) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
N1 C11 O4 112.29(12) . . ?
N1 C11 C10 125.07(13) . . ?
O4 C11 C10 122.62(13) . . ?
C7 C8 C3 118.07(13) . . ?
C7 C8 C9 117.38(13) . . ?
C3 C8 C9 124.50(13) . . ?
O2 C3 C4 123.11(14) . . ?
O2 C3 C8 117.34(13) . . ?
C4 C3 C8 119.54(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.089
