# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_PB-1
_database_code_depnum_ccdc_archive 'CCDC 1447814'
_audit_update_record             
;
2016-01-17 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 B Cl F2 N2 O'
_chemical_formula_weight         356.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   9.7560(8)
_cell_length_b                   17.9551(13)
_cell_length_c                   11.6909(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.720(3)
_cell_angle_gamma                90.00
_cell_volume                     1662.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      2.417
_cell_measurement_theta_max      23.93

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9454
_exptl_absorpt_correction_T_max  0.9550
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8194
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2929
_reflns_number_gt                1832
_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)+(0.0561P)²+0.2127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2929
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Cl1 Cl 0.28687(10) 0.01118(4) 0.68844(9) 0.0656(3) Uani 1 1 d . . .
C6 C 0.8885(3) 0.19164(13) 0.5437(3) 0.0365(6) Uani 1 1 d . . .
O1 O 0.9356(2) 0.07760(9) 0.6566(2) 0.0494(5) Uani 1 1 d . . .
C16 C 0.4966(3) 0.07776(13) 0.6429(3) 0.0416(6) Uani 1 1 d . . .
H16 H 0.4171 0.1157 0.5989 0.050 Uiso 1 1 calc R . .
C8 C 0.6886(3) 0.14012(13) 0.5965(2) 0.0342(6) Uani 1 1 d . . .
C18 C 0.4688(4) 0.01852(15) 0.6987(3) 0.0452(7) Uani 1 1 d . . .
C15 C 0.6457(3) 0.08114(12) 0.6522(3) 0.0354(6) Uani 1 1 d . . .
N2 N 0.5773(3) -0.03806(13) 0.7638(3) 0.0610(7) Uani 1 1 d . . .
C4 C 0.9340(4) 0.31755(15) 0.5051(3) 0.0505(7) Uani 1 1 d . . .
H4 H 0.9239 0.3684 0.5135 0.061 Uiso 1 1 calc R . .
N1 N 0.7554(3) 0.02255(11) 0.7183(2) 0.0414(6) Uani 1 1 d . . .
F1 F 1.0557(2) 0.02486(11) 0.87535(19) 0.0766(6) Uani 1 1 d . . .
C1 C 0.9658(3) 0.16752(15) 0.4814(3) 0.0427(7) Uani 1 1 d . . .
H1 H 0.9778 0.1167 0.4738 0.051 Uiso 1 1 calc R . .
F2 F 0.9354(3) -0.04892(8) 0.6856(2) 0.0812(6) Uani 1 1 d . . .
C2 C 1.0249(4) 0.21757(17) 0.4311(3) 0.0507(7) Uani 1 1 d . . .
H2 H 1.0757 0.2006 0.3890 0.061 Uiso 1 1 calc R . .
B1 B 0.9286(4) 0.01839(16) 0.7344(4) 0.0434(8) Uani 1 1 d . . .
C14 C 0.4702(3) 0.21398(15) 0.3856(3) 0.0446(7) Uani 1 1 d . . .
H14 H 0.4748 0.1793 0.3288 0.054 Uiso 1 1 calc R . .
C3 C 1.0090(4) 0.29278(17) 0.4427(3) 0.0551(8) Uani 1 1 d . . .
H3 H 1.0489 0.3267 0.4085 0.066 Uiso 1 1 calc R . .
C12 C 0.3547(4) 0.32559(17) 0.4061(4) 0.0616(9) Uani 1 1 d . . .
H12 H 0.2826 0.3662 0.3644 0.074 Uiso 1 1 calc R . .
C5 C 0.8736(3) 0.26762(14) 0.5552(3) 0.0450(7) Uani 1 1 d . . .
H5 H 0.8227 0.2849 0.5969 0.054 Uiso 1 1 calc R . .
C7 C 0.8316(3) 0.13573(13) 0.6008(3) 0.0381(6) Uani 1 1 d . . .
C9 C 0.5695(3) 0.20429(13) 0.5304(3) 0.0353(6) Uani 1 1 d . . .
C17 C 0.7146(4) -0.03248(16) 0.7696(3) 0.0575(8) Uani 1 1 d . . .
H17 H 0.7923 -0.0711 0.8143 0.069 Uiso 1 1 calc R . .
C10 C 0.5574(4) 0.25575(13) 0.6113(3) 0.0447(7) Uani 1 1 d . . .
H10 H 0.6211 0.2495 0.7085 0.054 Uiso 1 1 calc R . .
C13 C 0.3649(4) 0.27460(17) 0.3254(3) 0.0591(8) Uani 1 1 d . . .
H13 H 0.2999 0.2808 0.2282 0.071 Uiso 1 1 calc R . .
C11 C 0.4517(4) 0.31658(15) 0.5499(4) 0.0575(8) Uani 1 1 d . . .
H11 H 0.4462 0.3515 0.6059 0.069 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
Cl1 C18 1.713(3) . ?
C6 C5 1.387(3) . ?
C6 C1 1.388(3) . ?
C6 C7 1.482(3) . ?
O1 C7 1.331(3) . ?
O1 B1 1.427(3) . ?
C16 C18 1.355(3) . ?
C16 C15 1.396(4) . ?
C16 H16 0.9300 . ?
C8 C7 1.368(3) . ?
C8 C15 1.428(3) . ?
C8 C9 1.492(3) . ?
C18 N2 1.338(4) . ?
C15 N1 1.372(3) . ?
N2 C17 1.305(4) . ?
C4 C3 1.375(4) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
N1 C17 1.331(3) . ?
N1 B1 1.589(4) . ?
F1 B1 1.371(4) . ?
C1 C2 1.372(4) . ?
C1 H1 0.9300 . ?
F2 B1 1.354(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C14 C13 1.375(4) . ?
C14 C9 1.385(3) . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C12 C13 1.360(4) . ?
C12 C11 1.375(4) . ?
C12 H12 0.9300 . ?
C5 H5 0.9300 . ?
C9 C10 1.376(3) . ?
C17 H17 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?

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
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 122.3(2) . . ?
C1 C6 C7 119.1(2) . . ?
C7 O1 B1 126.1(2) . . ?
C18 C16 C15 119.3(2) . . ?
C18 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C7 C8 C15 120.3(2) . . ?
C7 C8 C9 122.1(2) . . ?
C15 C8 C9 117.5(2) . . ?
N2 C18 C16 123.8(3) . . ?
N2 C18 Cl1 115.1(2) . . ?
C16 C18 Cl1 121.1(2) . . ?
N1 C15 C16 116.5(2) . . ?
N1 C15 C8 119.0(2) . . ?
C16 C15 C8 124.5(2) . . ?
C17 N2 C18 114.7(2) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C17 N1 C15 118.8(2) . . ?
C17 N1 B1 119.3(2) . . ?
C15 N1 B1 121.9(2) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
F2 B1 F1 110.4(2) . . ?
F2 B1 O1 111.4(2) . . ?
F1 B1 O1 110.9(3) . . ?
F2 B1 N1 107.6(2) . . ?
F1 B1 N1 106.9(2) . . ?
O1 B1 N1 109.5(2) . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O1 C7 C8 122.2(2) . . ?
O1 C7 C6 111.9(2) . . ?
C8 C7 C6 125.9(2) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C8 121.0(2) . . ?
C14 C9 C8 120.5(2) . . ?
N2 C17 N1 127.0(3) . . ?
N2 C17 H17 116.5 . . ?
N1 C17 H17 116.5 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_PB-2
_database_code_depnum_ccdc_archive 'CCDC 1447815'
_audit_update_record             
;
2016-01-17 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 B F2 N2 O2'
_chemical_formula_weight         352.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.9518(8)
_cell_length_b                   17.5792(15)
_cell_length_c                   10.0373(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.906(2)
_cell_angle_gamma                90.00
_cell_volume                     1670.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2029
_cell_measurement_theta_min      2.419
_cell_measurement_theta_max      25.767

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8281
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2931
_reflns_number_gt                1783
_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)+(0.0444P)²+0.2410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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 0.25719(17) 0.02874(9) 0.26621(18) 0.0390(4) Uani 1 1 d . . .
O4 O -0.12507(15) 0.02615(8) 0.31995(18) 0.0574(5) Uani 1 1 d . . .
F1 F 0.45633(13) -0.05191(6) 0.29780(16) 0.0643(4) Uani 1 1 d . . .
O3 O 0.50165(14) 0.07576(8) 0.33274(16) 0.0510(4) Uani 1 1 d . . .
C9 C 0.2862(2) 0.20843(10) 0.4756(2) 0.0333(5) Uani 1 1 d . . .
N2 N 0.03030(18) -0.02684(10) 0.2180(2) 0.0541(5) Uani 1 1 d . . .
C15 C 0.2236(2) 0.08727(10) 0.3407(2) 0.0354(5) Uani 1 1 d . . .
C7 C 0.4627(2) 0.13542(11) 0.3942(2) 0.0370(5) Uani 1 1 d . . .
C6 C 0.5823(2) 0.18751(11) 0.4552(2) 0.0383(5) Uani 1 1 d . . .
F2 F 0.39854(14) 0.02607(8) 0.11294(14) 0.0676(4) Uani 1 1 d . . .
C18 C -0.0005(2) 0.02778(12) 0.2970(2) 0.0437(5) Uani 1 1 d . . .
C8 C 0.32877(19) 0.14411(10) 0.4001(2) 0.0331(5) Uani 1 1 d . . .
C16 C 0.0902(2) 0.08612(11) 0.3559(2) 0.0421(5) Uani 1 1 d . . .
H16 H 0.0621 0.1244 0.4055 0.051 Uiso 1 1 calc R . .
C5 C 0.7166(2) 0.15734(12) 0.5143(2) 0.0455(6) Uani 1 1 d . . .
H5 H 0.7293 0.1049 0.5162 0.055 Uiso 1 1 calc R . .
C10 C 0.3358(2) 0.21325(11) 0.6196(2) 0.0431(5) Uani 1 1 d . . .
H10 H 0.3984 0.1767 0.6704 0.052 Uiso 1 1 calc R . .
C14 C 0.1931(2) 0.26392(11) 0.4023(2) 0.0440(5) Uani 1 1 d . . .
H14 H 0.1588 0.2617 0.3051 0.053 Uiso 1 1 calc R . .
C17 C 0.1584(2) -0.02350(12) 0.2082(3) 0.0519(6) Uani 1 1 d . . .
H17 H 0.1834 -0.0613 0.1554 0.062 Uiso 1 1 calc R . .
C1 C 0.5672(2) 0.26641(11) 0.4505(2) 0.0457(6) Uani 1 1 d . . .
H1 H 0.4785 0.2879 0.4107 0.055 Uiso 1 1 calc R . .
B1 B 0.4088(3) 0.01946(13) 0.2513(3) 0.0403(6) Uani 1 1 d . . .
C4 C 0.8313(2) 0.20420(14) 0.5700(2) 0.0533(6) Uani 1 1 d . . .
H4 H 0.9203 0.1833 0.6113 0.064 Uiso 1 1 calc R . .
C12 C 0.2012(3) 0.32578(13) 0.6158(3) 0.0562(7) Uani 1 1 d . . .
H12 H 0.1725 0.3649 0.6633 0.067 Uiso 1 1 calc R . .
C3 C 0.8138(3) 0.28171(14) 0.5644(3) 0.0568(7) Uani 1 1 d . . .
H3 H 0.8911 0.3134 0.6016 0.068 Uiso 1 1 calc R . .
C2 C 0.6825(3) 0.31268(13) 0.5040(2) 0.0531(6) Uani 1 1 d . . .
H2 H 0.6715 0.3652 0.4994 0.064 Uiso 1 1 calc R . .
C13 C 0.1509(2) 0.32244(11) 0.4727(3) 0.0517(6) Uani 1 1 d . . .
H13 H 0.0887 0.3594 0.4229 0.062 Uiso 1 1 calc R . .
C11 C 0.2935(3) 0.27171(13) 0.6892(3) 0.0544(6) Uani 1 1 d . . .
H11 H 0.3278 0.2744 0.7864 0.065 Uiso 1 1 calc R . .
C19 C -0.2230(2) -0.03333(14) 0.2563(3) 0.0707(8) Uani 1 1 d . . .
H19A H -0.2541 -0.0268 0.1565 0.106 Uiso 1 1 calc R . .
H19B H -0.3029 -0.0311 0.2907 0.106 Uiso 1 1 calc R . .
H19C H -0.1774 -0.0818 0.2792 0.106 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
N1 C17 1.341(2) . ?
N1 C15 1.372(2) . ?
N1 B1 1.570(3) . ?
O4 C18 1.329(2) . ?
O4 C19 1.438(3) . ?
F1 B1 1.371(2) . ?
O3 C7 1.333(2) . ?
O3 B1 1.427(3) . ?
C9 C10 1.379(3) . ?
C9 C14 1.390(3) . ?
C9 C8 1.493(2) . ?
N2 C17 1.309(3) . ?
N2 C18 1.340(3) . ?
C15 C16 1.383(3) . ?
C15 C8 1.437(3) . ?
C7 C8 1.361(2) . ?
C7 C6 1.477(3) . ?
C6 C5 1.390(3) . ?
C6 C1 1.394(3) . ?
F2 B1 1.366(3) . ?
C18 C16 1.374(3) . ?
C5 C4 1.379(3) . ?
C10 C11 1.379(3) . ?
C14 C13 1.384(3) . ?
C1 C2 1.374(3) . ?
C4 C3 1.373(3) . ?
C12 C11 1.369(3) . ?
C12 C13 1.370(3) . ?
C3 C2 1.373(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
C17 N1 C15 118.78(17) . . ?
C17 N1 B1 119.04(16) . . ?
C15 N1 B1 122.15(16) . . ?
C18 O4 C19 118.67(17) . . ?
C7 O3 B1 125.54(16) . . ?
C10 C9 C14 118.51(18) . . ?
C10 C9 C8 120.84(18) . . ?
C14 C9 C8 120.64(18) . . ?
C17 N2 C18 114.67(18) . . ?
N1 C15 C16 116.88(18) . . ?
N1 C15 C8 118.64(16) . . ?
C16 C15 C8 124.46(17) . . ?
O3 C7 C8 122.47(17) . . ?
O3 C7 C6 111.55(16) . . ?
C8 C7 C6 125.97(17) . . ?
C5 C6 C1 118.26(19) . . ?
C5 C6 C7 119.15(18) . . ?
C1 C6 C7 122.53(19) . . ?
O4 C18 N2 118.83(18) . . ?
O4 C18 C16 117.77(18) . . ?
N2 C18 C16 123.40(18) . . ?
C7 C8 C15 120.10(17) . . ?
C7 C8 C9 122.81(17) . . ?
C15 C8 C9 116.95(16) . . ?
C18 C16 C15 119.30(18) . . ?
C4 C5 C6 120.8(2) . . ?
C9 C10 C11 120.7(2) . . ?
C13 C14 C9 120.6(2) . . ?
N2 C17 N1 126.79(19) . . ?
C2 C1 C6 120.5(2) . . ?
F2 B1 F1 109.53(18) . . ?
F2 B1 O3 110.87(18) . . ?
F1 B1 O3 110.2(2) . . ?
F2 B1 N1 108.33(19) . . ?
F1 B1 N1 107.68(16) . . ?
O3 B1 N1 110.19(16) . . ?
C3 C4 C5 119.8(2) . . ?
C11 C12 C13 120.2(2) . . ?
C2 C3 C4 120.2(2) . . ?
C3 C2 C1 120.3(2) . . ?
C12 C13 C14 119.8(2) . . ?
C12 C11 C10 120.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_150602c
_database_code_depnum_ccdc_archive 'CCDC 1447816'
_audit_update_record             
;
2016-01-17 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 B F2 N3 O'
_chemical_formula_weight         365.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.2016(7)
_cell_length_b                   17.9362(15)
_cell_length_c                   10.3169(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.317(2)
_cell_angle_gamma                90.00
_cell_volume                     1781.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1507
_cell_measurement_theta_min      2.253
_cell_measurement_theta_max      22.8215

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9785
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8882
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3149
_reflns_number_gt                1609
_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)+(0.0416P)²+0.3171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3149
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
N1 N -0.0079(2) 0.02201(11) 0.7403(2) 0.0428(6) Uani 1 1 d . . .
O1 O -0.23648(18) 0.08142(11) 0.6562(2) 0.0654(6) Uani 1 1 d . . .
C15 C 0.0409(3) 0.07174(14) 0.6651(3) 0.0385(7) Uani 1 1 d . . .
C7 C -0.1821(3) 0.13399(15) 0.5960(3) 0.0452(7) Uani 1 1 d . . .
C8 C -0.0510(3) 0.13112(14) 0.5939(3) 0.0389(7) Uani 1 1 d . . .
F2 F -0.17043(17) 0.02002(11) 0.86134(18) 0.0805(6) Uani 1 1 d . . .
F1 F -0.22128(17) -0.04599(9) 0.6689(2) 0.0844(6) Uani 1 1 d . . .
C18 C 0.2607(3) 0.00762(14) 0.7473(3) 0.0428(7) Uani 1 1 d . . .
C6 C -0.2862(3) 0.19373(15) 0.5363(3) 0.0427(7) Uani 1 1 d . . .
C16 C 0.1751(3) 0.06323(14) 0.6663(3) 0.0439(7) Uani 1 1 d . . .
H16 H 0.2095 0.0945 0.6131 0.053 Uiso 1 1 calc R . .
N2 N 0.2112(2) -0.03780(13) 0.8266(2) 0.0533(7) Uani 1 1 d . . .
C9 C 0.0061(2) 0.18737(14) 0.5200(3) 0.0362(6) Uani 1 1 d . . .
C14 C 0.1128(3) 0.23472(14) 0.5920(3) 0.0458(7) Uani 1 1 d . . .
H14 H 0.1489 0.2316 0.6872 0.055 Uiso 1 1 calc R . .
N3 N 0.3923(2) -0.00276(12) 0.7536(2) 0.0501(6) Uani 1 1 d . . .
C17 C 0.0810(3) -0.02898(15) 0.8165(3) 0.0536(8) Uani 1 1 d . . .
H17 H 0.0463 -0.0614 0.8675 0.064 Uiso 1 1 calc R . .
C20 C 0.4810(3) -0.05841(17) 0.8431(3) 0.0675(9) Uani 1 1 d . . .
H20A H 0.4452 -0.0705 0.9157 0.101 Uiso 1 1 calc R . .
H20B H 0.5734 -0.0389 0.8817 0.101 Uiso 1 1 calc R . .
H20C H 0.4828 -0.1025 0.7910 0.101 Uiso 1 1 calc R . .
C10 C -0.0445(3) 0.19318(16) 0.3792(3) 0.0521(8) Uani 1 1 d . . .
H10 H -0.1161 0.1619 0.3290 0.062 Uiso 1 1 calc R . .
C1 C -0.4243(3) 0.17400(16) 0.4737(3) 0.0488(7) Uani 1 1 d . . .
H1 H -0.4492 0.1239 0.4653 0.059 Uiso 1 1 calc R . .
C13 C 0.1658(3) 0.28633(15) 0.5239(3) 0.0531(8) Uani 1 1 d . . .
H13 H 0.2365 0.3182 0.5735 0.064 Uiso 1 1 calc R . .
C2 C -0.5247(3) 0.22764(19) 0.4240(3) 0.0591(9) Uani 1 1 d . . .
H2 H -0.6167 0.2138 0.3811 0.071 Uiso 1 1 calc R . .
C5 C -0.2516(3) 0.26868(16) 0.5481(3) 0.0537(8) Uani 1 1 d . . .
H5 H -0.1594 0.2828 0.5890 0.064 Uiso 1 1 calc R . .
C4 C -0.3520(3) 0.32251(17) 0.5002(3) 0.0611(9) Uani 1 1 d . . .
H4 H -0.3277 0.3727 0.5098 0.073 Uiso 1 1 calc R . .
B1 B -0.1626(3) 0.01899(19) 0.7315(4) 0.0475(9) Uani 1 1 d . . .
C19 C 0.4510(3) 0.04129(17) 0.6683(3) 0.0649(9) Uani 1 1 d . . .
H19A H 0.3919 0.0380 0.5742 0.097 Uiso 1 1 calc R . .
H19B H 0.5416 0.0226 0.6767 0.097 Uiso 1 1 calc R . .
H19C H 0.4582 0.0924 0.6975 0.097 Uiso 1 1 calc R . .
C12 C 0.1151(3) 0.29093(17) 0.3838(3) 0.0611(9) Uani 1 1 d . . .
H12 H 0.1523 0.3253 0.3381 0.073 Uiso 1 1 calc R . .
C3 C -0.4886(3) 0.3020(2) 0.4380(3) 0.0661(10) Uani 1 1 d . . .
H3 H -0.5565 0.3384 0.4053 0.079 Uiso 1 1 calc R . .
C11 C 0.0098(3) 0.24491(17) 0.3111(3) 0.0648(9) Uani 1 1 d . . .
H11 H -0.0255 0.2483 0.2159 0.078 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
N1 C17 1.344(3) . ?
N1 C15 1.379(3) . ?
N1 B1 1.551(4) . ?
O1 C7 1.345(3) . ?
O1 B1 1.427(4) . ?
C15 C16 1.373(3) . ?
C15 C8 1.448(3) . ?
C7 C8 1.346(3) . ?
C7 C6 1.490(3) . ?
C8 C9 1.494(3) . ?
F2 B1 1.368(4) . ?
F1 B1 1.370(4) . ?
C18 N3 1.335(3) . ?
C18 N2 1.364(3) . ?
C18 C16 1.405(3) . ?
C6 C5 1.385(4) . ?
C6 C1 1.388(3) . ?
N2 C17 1.307(3) . ?
C9 C10 1.376(3) . ?
C9 C14 1.386(3) . ?
C14 C13 1.376(4) . ?
N3 C19 1.452(3) . ?
N3 C20 1.454(3) . ?
C10 C11 1.385(4) . ?
C1 C2 1.375(4) . ?
C13 C12 1.367(4) . ?
C2 C3 1.379(4) . ?
C5 C4 1.375(4) . ?
C4 C3 1.377(4) . ?
C12 C11 1.366(4) . ?

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
C17 N1 C15 118.0(2) . . ?
C17 N1 B1 119.2(2) . . ?
C15 N1 B1 122.6(2) . . ?
C7 O1 B1 125.2(2) . . ?
C16 C15 N1 117.9(2) . . ?
C16 C15 C8 124.2(2) . . ?
N1 C15 C8 117.8(2) . . ?
C8 C7 O1 123.0(2) . . ?
C8 C7 C6 126.6(3) . . ?
O1 C7 C6 110.4(2) . . ?
C7 C8 C15 120.0(2) . . ?
C7 C8 C9 122.7(2) . . ?
C15 C8 C9 117.3(2) . . ?
N3 C18 N2 116.9(2) . . ?
N3 C18 C16 123.0(3) . . ?
N2 C18 C16 120.0(3) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 122.4(2) . . ?
C1 C6 C7 118.9(2) . . ?
C15 C16 C18 120.4(3) . . ?
C17 N2 C18 116.6(2) . . ?
C10 C9 C14 118.2(2) . . ?
C10 C9 C8 121.1(2) . . ?
C14 C9 C8 120.7(2) . . ?
C13 C14 C9 120.7(3) . . ?
C18 N3 C19 120.3(2) . . ?
C18 N3 C20 122.1(2) . . ?
C19 N3 C20 117.6(2) . . ?
N2 C17 N1 126.9(3) . . ?
C9 C10 C11 120.9(3) . . ?
C2 C1 C6 120.8(3) . . ?
C12 C13 C14 120.3(3) . . ?
C1 C2 C3 119.9(3) . . ?
C4 C5 C6 120.8(3) . . ?
C5 C4 C3 119.9(3) . . ?
F2 B1 F1 108.4(3) . . ?
F2 B1 O1 109.3(3) . . ?
F1 B1 O1 109.9(2) . . ?
F2 B1 N1 109.2(2) . . ?
F1 B1 N1 109.5(3) . . ?
O1 B1 N1 110.4(2) . . ?
C11 C12 C13 119.8(3) . . ?
C4 C3 C2 120.1(3) . . ?
C12 C11 C10 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_PB-4
_database_code_depnum_ccdc_archive 'CCDC 1447817'
_audit_update_record             
;
2016-01-17 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 B F2 N3 O'
_chemical_formula_weight         489.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   5.7410(5)
_cell_length_b                   24.007(2)
_cell_length_c                   21.4981(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.489(2)
_cell_angle_gamma                90.00
_cell_volume                     2855.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5018
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_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            14167
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_av_sigmaI/netI    0.1622
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5018
_reflns_number_gt                1674
_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)+(0.0804P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5018
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2180
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.868
_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
B1 B 0.6111(15) 0.2063(3) 0.3273(3) 0.089(2) Uani 1 1 d . . .
F1 F 0.4843(11) 0.16407(18) 0.3459(3) 0.215(3) Uani 1 1 d . . .
F2 F 0.7976(8) 0.2187(2) 0.37640(15) 0.186(2) Uani 1 1 d . . .
N1 N 0.8997(6) 0.10485(15) 0.12614(16) 0.0581(10) Uani 1 1 d . . .
N2 N 0.9235(7) 0.11336(16) 0.23428(19) 0.0713(12) Uani 1 1 d . . .
N3 N 0.7065(7) 0.18386(17) 0.27108(17) 0.0687(11) Uani 1 1 d . . .
O1 O 0.4600(7) 0.25243(17) 0.30962(17) 0.0981(12) Uani 1 1 d . . .
C1 C 1.2925(9) 0.0636(2) 0.1823(2) 0.0659(13) Uani 1 1 d . . .
H1 H 1.3237 0.0932 0.2113 0.079 Uiso 1 1 calc R . .
C2 C 1.4610(9) 0.0221(2) 0.1859(2) 0.0708(14) Uani 1 1 d . . .
H2 H 1.6060 0.0235 0.2181 0.085 Uiso 1 1 calc R . .
C3 C 1.4192(10) -0.0211(2) 0.1431(3) 0.0733(15) Uani 1 1 d . . .
H3 H 1.5357 -0.0485 0.1454 0.088 Uiso 1 1 calc R . .
C4 C 1.2042(10) -0.0235(2) 0.0968(2) 0.0735(14) Uani 1 1 d . . .
H4 H 1.1732 -0.0530 0.0676 0.088 Uiso 1 1 calc R . .
C5 C 1.0342(9) 0.0172(2) 0.0930(2) 0.0663(13) Uani 1 1 d . . .
H5 H 0.8878 0.0151 0.0614 0.080 Uiso 1 1 calc R . .
C6 C 1.0778(8) 0.06074(19) 0.1352(2) 0.0543(11) Uani 1 1 d . . .
C7 C 0.7829(8) 0.12115(18) 0.0608(2) 0.0529(12) Uani 1 1 d . . .
C8 C 0.9053(9) 0.15307(19) 0.0274(2) 0.0690(13) Uani 1 1 d . . .
H8 H 1.0658 0.1626 0.0461 0.083 Uiso 1 1 calc R . .
C9 C 0.7916(12) 0.1711(2) -0.0337(3) 0.0781(15) Uani 1 1 d . . .
H9 H 0.8748 0.1925 -0.0568 0.094 Uiso 1 1 calc R . .
C10 C 0.5558(13) 0.1572(2) -0.0604(2) 0.0842(17) Uani 1 1 d . . .
H10 H 0.4770 0.1701 -0.1015 0.101 Uiso 1 1 calc R . .
C11 C 0.4349(9) 0.1247(2) -0.0277(3) 0.0809(16) Uani 1 1 d . . .
H11 H 0.2747 0.1150 -0.0466 0.097 Uiso 1 1 calc R . .
C12 C 0.5481(9) 0.10639(19) 0.0328(2) 0.0658(13) Uani 1 1 d . . .
H12 H 0.4659 0.0839 0.0550 0.079 Uiso 1 1 calc R . .
C13 C 0.8416(8) 0.1344(2) 0.1742(2) 0.0566(12) Uani 1 1 d . . .
C14 C 0.8496(10) 0.1390(2) 0.2784(2) 0.0778(15) Uani 1 1 d . . .
H14 H 0.9019 0.1246 0.3200 0.093 Uiso 1 1 calc R . .
C15 C 0.6352(8) 0.2073(2) 0.2109(2) 0.0601(13) Uani 1 1 d . . .
C16 C 0.7039(8) 0.18179(19) 0.1623(2) 0.0591(12) Uani 1 1 d . . .
H16 H 0.6573 0.1965 0.1208 0.071 Uiso 1 1 calc R . .
C17 C 0.4855(8) 0.25719(19) 0.2019(2) 0.0589(12) Uani 1 1 d . . .
C18 C 0.4264(9) 0.2825(2) 0.1368(2) 0.0625(13) Uani 1 1 d . . .
C19 C 0.2022(10) 0.2758(2) 0.0946(3) 0.0788(15) Uani 1 1 d . . .
H19 H 0.0838 0.2565 0.1080 0.095 Uiso 1 1 calc R . .
C20 C 0.1485(13) 0.2966(3) 0.0334(3) 0.106(2) Uani 1 1 d . . .
H20 H -0.0049 0.2914 0.0058 0.128 Uiso 1 1 calc R . .
C21 C 0.3187(18) 0.3248(3) 0.0128(3) 0.127(3) Uani 1 1 d . . .
H21 H 0.2846 0.3383 -0.0292 0.152 Uiso 1 1 calc R . .
C22 C 0.5474(13) 0.3333(2) 0.0560(4) 0.109(2) Uani 1 1 d . . .
H22 H 0.6647 0.3534 0.0430 0.131 Uiso 1 1 calc R . .
C23 C 0.5970(10) 0.3122(2) 0.1168(3) 0.0818(15) Uani 1 1 d . . .
H23 H 0.7486 0.3179 0.1452 0.098 Uiso 1 1 calc R . .
C24 C 0.4041(8) 0.2766(2) 0.2512(2) 0.0689(14) Uani 1 1 d . . .
C25 C 0.2438(9) 0.3253(2) 0.2501(3) 0.0708(14) Uani 1 1 d . . .
C26 C 0.2579(9) 0.3726(3) 0.2151(3) 0.0803(15) Uani 1 1 d . . .
H26 H 0.3668 0.3742 0.1899 0.096 Uiso 1 1 calc R . .
C27 C 0.1081(12) 0.4184(2) 0.2172(3) 0.0962(19) Uani 1 1 d . . .
H27 H 0.1168 0.4506 0.1939 0.115 Uiso 1 1 calc R . .
C28 C -0.0527(11) 0.4146(3) 0.2548(4) 0.102(2) Uani 1 1 d . . .
H28 H -0.1534 0.4445 0.2566 0.123 Uiso 1 1 calc R . .
C29 C -0.0661(10) 0.3675(4) 0.2894(3) 0.0948(19) Uani 1 1 d . . .
H29 H -0.1759 0.3654 0.3142 0.114 Uiso 1 1 calc R . .
C30 C 0.0809(10) 0.3240(3) 0.2873(2) 0.0847(17) Uani 1 1 d . . .
H30 H 0.0725 0.2924 0.3116 0.102 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
B1 F2 1.322(8) . ?
B1 F1 1.369(8) . ?
B1 O1 1.395(7) . ?
B1 N3 1.550(7) . ?
N1 C13 1.366(5) . ?
N1 C7 1.440(5) . ?
N1 C6 1.448(5) . ?
N2 C14 1.294(5) . ?
N2 C13 1.348(5) . ?
N3 C14 1.338(6) . ?
N3 C15 1.369(5) . ?
O1 C24 1.342(5) . ?
C1 C6 1.372(5) . ?
C1 C2 1.377(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(5) . ?
C5 H5 0.9300 . ?
C7 C12 1.368(6) . ?
C7 C8 1.366(6) . ?
C8 C9 1.371(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C16 1.370(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(5) . ?
C15 C17 1.457(6) . ?
C16 H16 0.9300 . ?
C17 C24 1.351(6) . ?
C17 C18 1.480(6) . ?
C18 C23 1.370(6) . ?
C18 C19 1.372(6) . ?
C19 C20 1.362(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.357(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.406(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.360(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.483(6) . ?
C25 C26 1.375(6) . ?
C25 C30 1.385(7) . ?
C26 C27 1.405(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.366(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.350(7) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
F2 B1 F1 108.3(6) . . ?
F2 B1 O1 110.5(6) . . ?
F1 B1 O1 109.1(6) . . ?
F2 B1 N3 108.8(6) . . ?
F1 B1 N3 107.2(5) . . ?
O1 B1 N3 112.8(5) . . ?
C13 N1 C7 116.9(4) . . ?
C13 N1 C6 125.7(4) . . ?
C7 N1 C6 117.3(3) . . ?
C14 N2 C13 115.2(4) . . ?
C14 N3 C15 117.5(4) . . ?
C14 N3 B1 121.4(5) . . ?
C15 N3 B1 121.0(5) . . ?
C24 O1 B1 125.0(4) . . ?
C6 C1 C2 119.0(4) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 N1 118.3(4) . . ?
C1 C6 N1 121.7(4) . . ?
C12 C7 C8 120.0(4) . . ?
C12 C7 N1 120.4(4) . . ?
C8 C7 N1 119.6(4) . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 119.9(5) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
N2 C13 N1 115.9(4) . . ?
N2 C13 C16 121.8(4) . . ?
N1 C13 C16 122.3(4) . . ?
N2 C14 N3 127.4(5) . . ?
N2 C14 H14 116.3 . . ?
N3 C14 H14 116.3 . . ?
C16 C15 N3 117.9(4) . . ?
C16 C15 C17 123.4(4) . . ?
N3 C15 C17 118.7(4) . . ?
C15 C16 C13 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C13 C16 H16 119.9 . . ?
C24 C17 C15 119.7(4) . . ?
C24 C17 C18 124.1(5) . . ?
C15 C17 C18 116.2(4) . . ?
C23 C18 C19 118.4(5) . . ?
C23 C18 C17 120.5(5) . . ?
C19 C18 C17 121.0(5) . . ?
C20 C19 C18 121.7(6) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C21 C20 C19 120.1(6) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.0(6) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 119.9(6) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C18 120.8(5) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
O1 C24 C17 122.5(5) . . ?
O1 C24 C25 110.4(5) . . ?
C17 C24 C25 127.0(5) . . ?
C26 C25 C30 118.8(5) . . ?
C26 C25 C24 122.2(6) . . ?
C30 C25 C24 119.0(6) . . ?
C25 C26 C27 120.1(6) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 118.5(6) . . ?
C28 C27 H27 120.8 . . ?
C26 C27 H27 120.8 . . ?
C29 C28 C27 121.1(6) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 119.7(6) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C25 121.8(6) . . ?
C29 C30 H30 119.1 . . ?
C25 C30 H30 119.1 . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.051 0.500 0.000 277 28 ' '
2 0.106 0.000 0.500 277 28 ' '
_platon_squeeze_details          
;
;


_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.048
