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

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

data_dsrs-62_r
_database_code_depnum_ccdc_archive 'CCDC 1039757'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H14 B F2 N3 S'
_chemical_formula_sum            'C19 H14 B F2 N3 S'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         365.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   13.4997(9)
_cell_length_b                   13.9995(7)
_cell_length_c                   10.1052(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.458(8)
_cell_angle_gamma                90.00
_cell_volume                     1777.40(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    1.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_process_details   
;
SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction  
;

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4211
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         66.38
_reflns_number_total             3125
_reflns_number_gt                2327
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0927P)²+0.3134P] 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         3125
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
S1 S 0.55398(5) 0.41660(5) 0.12845(6) 0.0560(2) Uani 1 1 d . . .
F1 F 0.88433(16) 0.57325(10) 0.00221(16) 0.0701(5) Uani 1 1 d . . .
F2 F 1.01855(12) 0.56916(12) 0.2139(2) 0.0760(5) Uani 1 1 d . . .
N1 N 0.88357(15) 0.44937(13) 0.16579(19) 0.0430(4) Uani 1 1 d . . .
C17 C 0.68555(19) 0.42462(15) 0.6070(2) 0.0435(5) Uani 1 1 d . . .
C6 C 0.78727(18) 0.58475(15) 0.2861(2) 0.0413(5) Uani 1 1 d . . .
C15 C 0.6589(2) 0.38808(19) 0.8240(3) 0.0579(7) Uani 1 1 d . . .
H15 H 0.6837 0.3867 0.9228 0.070 Uiso 1 1 calc R . .
C4 C 0.82187(18) 0.42042(15) 0.2435(2) 0.0435(5) Uani 1 1 d . . .
C14 C 0.5572(2) 0.35486(19) 0.7463(3) 0.0600(7) Uani 1 1 d . . .
H14 H 0.5148 0.3313 0.7936 0.072 Uiso 1 1 calc R . .
C16 C 0.7227(2) 0.42272(18) 0.7574(3) 0.0538(6) Uani 1 1 d . . .
H16 H 0.7905 0.4451 0.8105 0.065 Uiso 1 1 calc R . .
N2 N 0.84641(15) 0.61683(12) 0.20788(19) 0.0427(4) Uani 1 1 d . . .
N3 N 0.54301(16) 0.38786(14) 0.38264(19) 0.0458(5) Uani 1 1 d . . .
C2 C 0.8813(2) 0.28889(18) 0.1687(3) 0.0654(7) Uani 1 1 d . . .
H2 H 0.8944 0.2258 0.1514 0.078 Uiso 1 1 calc R . .
C11 C 0.60382(19) 0.41760(15) 0.3158(2) 0.0416(5) Uani 1 1 d . . .
C10 C 0.70895(18) 0.45396(15) 0.3855(2) 0.0413(5) Uani 1 1 d . . .
C13 C 0.5189(2) 0.35641(19) 0.6009(3) 0.0560(6) Uani 1 1 d . . .
H13 H 0.4503 0.3351 0.5498 0.067 Uiso 1 1 calc R . .
C8 C 0.7782(2) 0.74490(18) 0.2783(3) 0.0678(8) Uani 1 1 d . . .
H8 H 0.7622 0.8081 0.2908 0.081 Uiso 1 1 calc R . .
C9 C 0.8400(2) 0.71307(17) 0.2037(3) 0.0565(6) Uani 1 1 d . . .
H9 H 0.8724 0.7525 0.1574 0.068 Uiso 1 1 calc R . .
C7 C 0.7451(2) 0.66510(17) 0.3302(3) 0.0567(6) Uani 1 1 d . . .
H7 H 0.7026 0.6645 0.3847 0.068 Uiso 1 1 calc R . .
C18 C 0.74815(19) 0.45799(17) 0.5300(2) 0.0466(5) Uani 1 1 d . . .
H18 H 0.8158 0.4826 0.5784 0.056 Uiso 1 1 calc R . .
C12 C 0.58330(19) 0.39023(15) 0.5285(2) 0.0429(5) Uani 1 1 d . . .
C5 C 0.77437(16) 0.48676(15) 0.3031(2) 0.0398(5) Uani 1 1 d . . .
B1 B 0.9111(2) 0.55390(18) 0.1440(3) 0.0430(6) Uani 1 1 d . . .
C1 C 0.9189(2) 0.37044(17) 0.1224(3) 0.0550(6) Uani 1 1 d . . .
H1 H 0.9624 0.3700 0.0690 0.066 Uiso 1 1 calc R . .
C19 C 0.4188(2) 0.38245(19) 0.0880(3) 0.0562(6) Uani 1 1 d . . .
H19A H 0.3827 0.3794 -0.0133 0.084 Uiso 1 1 calc R . .
H19B H 0.3844 0.4287 0.1268 0.084 Uiso 1 1 calc R . .
H19C H 0.4165 0.3209 0.1286 0.084 Uiso 1 1 calc R . .
C3 C 0.8213(2) 0.31959(17) 0.2445(3) 0.0561(6) Uani 1 1 d . . .
H3 H 0.7865 0.2809 0.2886 0.067 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
S1 C11 1.762(2) . ?
S1 C19 1.784(3) . ?
F1 B1 1.371(3) . ?
F2 B1 1.378(3) . ?
N1 C1 1.340(3) . ?
N1 C4 1.397(3) . ?
N1 B1 1.545(3) . ?
C17 C12 1.402(3) . ?
C17 C16 1.416(3) . ?
C17 C18 1.420(3) . ?
C6 N2 1.388(3) . ?
C6 C5 1.401(3) . ?
C6 C7 1.405(3) . ?
C15 C16 1.362(4) . ?
C15 C14 1.388(4) . ?
C4 C5 1.385(3) . ?
C4 C3 1.412(3) . ?
C14 C13 1.368(3) . ?
N2 C9 1.350(3) . ?
N2 B1 1.539(3) . ?
N3 C11 1.307(3) . ?
N3 C12 1.372(3) . ?
C2 C3 1.371(4) . ?
C2 C1 1.398(4) . ?
C11 C10 1.428(3) . ?
C10 C18 1.360(3) . ?
C10 C5 1.491(3) . ?
C13 C12 1.407(3) . ?
C8 C7 1.376(4) . ?
C8 C9 1.386(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
C11 S1 C19 101.83(11) . . ?
C1 N1 C4 107.58(19) . . ?
C1 N1 B1 126.95(19) . . ?
C4 N1 B1 125.35(18) . . ?
C12 C17 C16 119.3(2) . . ?
C12 C17 C18 117.6(2) . . ?
C16 C17 C18 123.1(2) . . ?
N2 C6 C5 120.65(19) . . ?
N2 C6 C7 107.79(19) . . ?
C5 C6 C7 131.5(2) . . ?
C16 C15 C14 120.8(2) . . ?
C5 C4 N1 121.05(19) . . ?
C5 C4 C3 131.5(2) . . ?
N1 C4 C3 107.4(2) . . ?
C13 C14 C15 120.6(2) . . ?
C15 C16 C17 119.9(2) . . ?
C9 N2 C6 107.27(19) . . ?
C9 N2 B1 126.75(19) . . ?
C6 N2 B1 125.92(17) . . ?
C11 N3 C12 118.05(19) . . ?
C3 C2 C1 107.0(2) . . ?
N3 C11 C10 123.9(2) . . ?
N3 C11 S1 119.17(18) . . ?
C10 C11 S1 116.95(16) . . ?
C18 C10 C11 118.10(19) . . ?
C18 C10 C5 120.64(19) . . ?
C11 C10 C5 121.26(18) . . ?
C14 C13 C12 120.1(2) . . ?
C7 C8 C9 106.8(2) . . ?
N2 C9 C8 110.4(2) . . ?
C8 C7 C6 107.7(2) . . ?
C10 C18 C17 119.9(2) . . ?
N3 C12 C17 122.49(19) . . ?
N3 C12 C13 118.2(2) . . ?
C17 C12 C13 119.3(2) . . ?
C4 C5 C6 120.33(19) . . ?
C4 C5 C10 119.97(19) . . ?
C6 C5 C10 119.71(19) . . ?
F1 B1 F2 109.3(2) . . ?
F1 B1 N2 110.61(19) . . ?
F2 B1 N2 110.4(2) . . ?
F1 B1 N1 110.54(19) . . ?
F2 B1 N1 109.7(2) . . ?
N2 B1 N1 106.22(17) . . ?
N1 C1 C2 110.3(2) . . ?
C2 C3 C4 107.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.38
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.075

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1039758'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 B F2 N3 S, 0.5(C6 H14)'
_chemical_formula_sum            'C23 H23 B F2 N3 S'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         422.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2yn'

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                   16.3271(10)
_cell_length_b                   8.3270(4)
_cell_length_c                   16.9926(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.759(3)
_cell_angle_gamma                90.00
_cell_volume                     2174.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5023
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.87
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             884
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17292
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         26.78
_reflns_number_total             4650
_reflns_number_gt                3421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0801P)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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.004
_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 0.83590(14) 0.9667(2) 0.81309(11) 0.0523(5) Uani 1 1 d . . .
H1 H 0.8594 0.9205 0.7757 0.063 Uiso 1 1 calc R . .
C2 C 0.75314(15) 0.9376(3) 0.81389(12) 0.0632(6) Uani 1 1 d . . .
H2 H 0.7118 0.8704 0.7778 0.076 Uiso 1 1 calc R . .
C3 C 0.74304(13) 1.0269(3) 0.87825(11) 0.0567(5) Uani 1 1 d . . .
H3 H 0.6937 1.0308 0.8939 0.068 Uiso 1 1 calc R . .
C4 C 0.82108(11) 1.1108(2) 0.91592(10) 0.0421(4) Uani 1 1 d . . .
C5 C 0.84793(11) 1.2129(2) 0.98515(9) 0.0379(4) Uani 1 1 d . . .
C6 C 0.93244(11) 1.27044(19) 1.01501(9) 0.0362(4) Uani 1 1 d . . .
C7 C 0.97796(11) 1.3612(2) 1.08708(10) 0.0418(4) Uani 1 1 d . . .
H7 H 0.9545 1.4044 1.1253 0.050 Uiso 1 1 calc R . .
C8 C 1.06195(12) 1.3738(2) 1.09025(11) 0.0484(5) Uani 1 1 d . . .
H8 H 1.1068 1.4260 1.1312 0.058 Uiso 1 1 calc R . .
C9 C 1.06821(11) 1.2934(2) 1.02035(10) 0.0446(4) Uani 1 1 d . . .
H9 H 1.1189 1.2847 1.0072 0.054 Uiso 1 1 calc R . .
C10 C 0.78577(11) 1.2571(2) 1.02872(10) 0.0378(4) Uani 1 1 d . . .
C11 C 0.71745(10) 1.3696(2) 0.99177(9) 0.0378(4) Uani 1 1 d . . .
C12 C 0.66350(10) 1.3436(2) 1.09983(10) 0.0378(4) Uani 1 1 d . . .
C13 C 0.60068(11) 1.3869(2) 1.13547(11) 0.0461(4) Uani 1 1 d . . .
H13 H 0.5544 1.4525 1.1060 0.055 Uiso 1 1 calc R . .
C14 C 0.60743(12) 1.3327(2) 1.21338(11) 0.0486(5) Uani 1 1 d . . .
H14 H 0.5653 1.3624 1.2362 0.058 Uiso 1 1 calc R . .
C15 C 0.67628(13) 1.2336(2) 1.25972(11) 0.0506(5) Uani 1 1 d . . .
C16 C 0.73602(13) 1.1856(2) 1.22450(11) 0.0524(5) Uani 1 1 d . . .
H16 H 0.7807 1.1167 1.2540 0.063 Uiso 1 1 calc R . .
C17 C 0.73123(11) 1.2390(2) 1.14367(10) 0.0407(4) Uani 1 1 d . . .
C18 C 0.79217(11) 1.1948(2) 1.10473(10) 0.0434(4) Uani 1 1 d . . .
H18 H 0.8367 1.1232 1.1311 0.052 Uiso 1 1 calc R . .
C19 C 0.63283(16) 1.6093(3) 0.88473(15) 0.0806(8) Uani 1 1 d . . .
H19A H 0.6264 1.6714 0.8354 0.121 Uiso 1 1 calc R . .
H19B H 0.6471 1.6792 0.9324 0.121 Uiso 1 1 calc R . .
H19C H 0.5793 1.5545 0.8785 0.121 Uiso 1 1 calc R . .
C20 C 0.68326(17) 1.1827(3) 1.34745(13) 0.0787(8) Uani 1 1 d . . .
H20A H 0.6309 1.1283 1.3458 0.118 Uiso 1 1 calc R . .
H20B H 0.6913 1.2759 1.3825 0.118 Uiso 1 1 calc R . .
H20C H 0.7320 1.1117 1.3695 0.118 Uiso 1 1 calc R . .
C21 C 0.5136(2) 0.0172(4) 0.96201(17) 0.0949(9) Uani 1 1 d . . .
H21A H 0.5723 0.0602 0.9815 0.114 Uiso 1 1 calc R . .
H21B H 0.5151 -0.0835 0.9339 0.114 Uiso 1 1 calc R . .
C22 C 0.4567(2) 0.1308(5) 0.9003(2) 0.1201(12) Uani 1 1 d . . .
H22A H 0.4547 0.2316 0.9281 0.144 Uiso 1 1 calc R . .
H22B H 0.3981 0.0875 0.8797 0.144 Uiso 1 1 calc R . .
C23 C 0.4869(3) 0.1633(5) 0.8258(2) 0.1261(12) Uani 1 1 d . . .
H23A H 0.4469 0.2353 0.7876 0.189 Uiso 1 1 calc R . .
H23B H 0.4891 0.0641 0.7978 0.189 Uiso 1 1 calc R . .
H23C H 0.5438 0.2110 0.8453 0.189 Uiso 1 1 calc R . .
N1 N 0.87795(10) 1.07052(18) 0.87360(8) 0.0427(4) Uani 1 1 d . . .
N2 N 0.99180(9) 1.23117(16) 0.97511(8) 0.0371(3) Uani 1 1 d . . .
N3 N 0.65784(8) 1.40853(18) 1.02391(8) 0.0418(3) Uani 1 1 d . . .
B1 B 0.96639(13) 1.1525(2) 0.88764(11) 0.0398(4) Uani 1 1 d . . .
F1 F 0.95626(8) 1.26965(12) 0.82669(6) 0.0545(3) Uani 1 1 d . . .
F2 F 1.02823(7) 1.04393(13) 0.88344(7) 0.0573(3) Uani 1 1 d . . .
S1 S 0.71723(3) 1.46668(7) 0.89929(3) 0.05680(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.341(2) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.394(2) . ?
C4 C5 1.396(2) . ?
C5 C6 1.385(2) . ?
C5 C10 1.491(2) . ?
C6 N2 1.396(2) . ?
C6 C7 1.417(2) . ?
C7 C8 1.358(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9300 . ?
C9 N2 1.330(2) . ?
C9 H9 0.9300 . ?
C10 C18 1.363(2) . ?
C10 C11 1.429(2) . ?
C11 N3 1.308(2) . ?
C11 S1 1.7662(16) . ?
C12 N3 1.373(2) . ?
C12 C13 1.403(2) . ?
C12 C17 1.407(2) . ?
C13 C14 1.367(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(3) . ?
C15 C20 1.517(3) . ?
C16 C17 1.420(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.417(2) . ?
C18 H18 0.9300 . ?
C19 S1 1.772(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.483(4) . ?
C21 C21 1.528(6) 3_657 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.530(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 B1 1.541(2) . ?
N2 B1 1.547(2) . ?
B1 F2 1.375(2) . ?
B1 F1 1.391(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.81(18) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C1 C2 C3 107.12(18) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C2 C3 C4 107.26(18) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C5 120.46(15) . . ?
N1 C4 C3 107.77(15) . . ?
C5 C4 C3 131.70(16) . . ?
C6 C5 C4 120.64(15) . . ?
C6 C5 C10 119.60(15) . . ?
C4 C5 C10 119.75(15) . . ?
C5 C6 N2 120.67(15) . . ?
C5 C6 C7 131.90(15) . . ?
N2 C6 C7 107.29(14) . . ?
C8 C7 C6 107.64(15) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 107.01(16) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.75(15) . . ?
N2 C9 H9 124.6 . . ?
C8 C9 H9 124.6 . . ?
C18 C10 C11 117.65(15) . . ?
C18 C10 C5 122.01(15) . . ?
C11 C10 C5 120.33(14) . . ?
N3 C11 C10 124.03(14) . . ?
N3 C11 S1 118.68(12) . . ?
C10 C11 S1 117.23(12) . . ?
N3 C12 C13 118.54(15) . . ?
N3 C12 C17 122.17(14) . . ?
C13 C12 C17 119.26(14) . . ?
C14 C13 C12 120.13(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.65(16) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 118.82(16) . . ?
C16 C15 C20 121.44(18) . . ?
C14 C15 C20 119.75(17) . . ?
C15 C16 C17 121.23(17) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C18 117.62(14) . . ?
C12 C17 C16 118.82(15) . . ?
C18 C17 C16 123.55(16) . . ?
C10 C18 C17 120.20(16) . . ?
C10 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C21 115.2(4) . 3_657 ?
C22 C21 H21A 108.5 . . ?
C21 C21 H21A 108.5 3_657 . ?
C22 C21 H21B 108.5 . . ?
C21 C21 H21B 108.5 3_657 . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 113.5(3) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C4 107.04(15) . . ?
C1 N1 B1 127.90(15) . . ?
C4 N1 B1 124.48(14) . . ?
C9 N2 C6 107.31(14) . . ?
C9 N2 B1 127.94(14) . . ?
C6 N2 B1 124.12(14) . . ?
C11 N3 C12 118.14(14) . . ?
F2 B1 F1 109.09(14) . . ?
F2 B1 N1 111.50(15) . . ?
F1 B1 N1 109.03(15) . . ?
F2 B1 N2 111.42(14) . . ?
F1 B1 N2 110.14(15) . . ?
N1 B1 N2 105.61(12) . . ?
C11 S1 C19 101.46(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.3(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 N1 -0.2(2) . . . . ?
C2 C3 C4 C5 -177.15(19) . . . . ?
N1 C4 C5 C6 -2.7(2) . . . . ?
C3 C4 C5 C6 173.99(19) . . . . ?
N1 C4 C5 C10 178.89(15) . . . . ?
C3 C4 C5 C10 -4.4(3) . . . . ?
C4 C5 C6 N2 1.8(2) . . . . ?
C10 C5 C6 N2 -179.78(14) . . . . ?
C4 C5 C6 C7 -173.27(17) . . . . ?
C10 C5 C6 C7 5.2(3) . . . . ?
C5 C6 C7 C8 174.89(18) . . . . ?
N2 C6 C7 C8 -0.64(19) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 N2 -0.6(2) . . . . ?
C6 C5 C10 C18 -72.2(2) . . . . ?
C4 C5 C10 C18 106.2(2) . . . . ?
C6 C5 C10 C11 106.85(19) . . . . ?
C4 C5 C10 C11 -74.7(2) . . . . ?
C18 C10 C11 N3 -4.4(3) . . . . ?
C5 C10 C11 N3 176.48(16) . . . . ?
C18 C10 C11 S1 172.93(13) . . . . ?
C5 C10 C11 S1 -6.2(2) . . . . ?
N3 C12 C13 C14 -175.80(16) . . . . ?
C17 C12 C13 C14 2.6(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 -2.5(3) . . . . ?
C13 C14 C15 C20 177.3(2) . . . . ?
C14 C15 C16 C17 2.3(3) . . . . ?
C20 C15 C16 C17 -177.4(2) . . . . ?
N3 C12 C17 C18 -3.2(3) . . . . ?
C13 C12 C17 C18 178.44(17) . . . . ?
N3 C12 C17 C16 175.65(17) . . . . ?
C13 C12 C17 C16 -2.7(3) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C15 C16 C17 C18 179.03(19) . . . . ?
C11 C10 C18 C17 1.5(3) . . . . ?
C5 C10 C18 C17 -179.44(16) . . . . ?
C12 C17 C18 C10 2.1(3) . . . . ?
C16 C17 C18 C10 -176.77(18) . . . . ?
C21 C21 C22 C23 179.3(3) 3_657 . . . ?
C2 C1 N1 C4 0.2(2) . . . . ?
C2 C1 N1 B1 -171.23(17) . . . . ?
C5 C4 N1 C1 177.34(16) . . . . ?
C3 C4 N1 C1 -0.05(19) . . . . ?
C5 C4 N1 B1 -10.8(2) . . . . ?
C3 C4 N1 B1 171.80(16) . . . . ?
C8 C9 N2 C6 0.16(19) . . . . ?
C8 C9 N2 B1 171.32(16) . . . . ?
C5 C6 N2 C9 -175.85(15) . . . . ?
C7 C6 N2 C9 0.29(18) . . . . ?
C5 C6 N2 B1 12.6(2) . . . . ?
C7 C6 N2 B1 -171.29(14) . . . . ?
C10 C11 N3 C12 3.3(3) . . . . ?
S1 C11 N3 C12 -173.96(12) . . . . ?
C13 C12 N3 C11 178.92(16) . . . . ?
C17 C12 N3 C11 0.6(2) . . . . ?
C1 N1 B1 F2 -47.7(2) . . . . ?
C4 N1 B1 F2 142.23(15) . . . . ?
C1 N1 B1 F1 72.8(2) . . . . ?
C4 N1 B1 F1 -97.26(18) . . . . ?
C1 N1 B1 N2 -168.84(16) . . . . ?
C4 N1 B1 N2 21.1(2) . . . . ?
C9 N2 B1 F2 47.1(2) . . . . ?
C6 N2 B1 F2 -143.13(15) . . . . ?
C9 N2 B1 F1 -74.1(2) . . . . ?
C6 N2 B1 F1 95.67(18) . . . . ?
C9 N2 B1 N1 168.29(16) . . . . ?
C6 N2 B1 N1 -21.9(2) . . . . ?
N3 C11 S1 C19 4.80(18) . . . . ?
C10 C11 S1 C19 -172.68(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.78
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.214
_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_dsrs-63
_database_code_depnum_ccdc_archive 'CCDC 1039759'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 B F2 N3 O S'
_chemical_formula_sum            'C20 H16 B F2 N3 O S'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         395.23

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   10.5497(15)
_cell_length_b                   19.995(3)
_cell_length_c                   9.2865(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.898(15)
_cell_angle_gamma                90.00
_cell_volume                     1893.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
;
SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6997
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.24
_reflns_number_total             4679
_reflns_number_gt                2357
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0565P)²+0.6726P] 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         4679
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1799
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.95425(10) 0.20703(5) 0.89993(10) 0.0594(3) Uani 1 1 d . . .
F1 F 0.3815(2) 0.09940(10) 0.5336(2) 0.0761(7) Uani 1 1 d . . .
F2 F 0.4724(2) 0.05368(10) 0.7593(3) 0.0775(7) Uani 1 1 d . . .
O1 O 0.7943(3) 0.56973(12) 0.5158(3) 0.0777(9) Uani 1 1 d . . .
N2 N 0.4718(3) 0.17436(14) 0.7374(3) 0.0494(7) Uani 1 1 d . . .
N3 N 0.9714(3) 0.33178(14) 0.8041(3) 0.0494(7) Uani 1 1 d . . .
N1 N 0.6160(3) 0.10478(14) 0.6259(3) 0.0532(8) Uani 1 1 d . . .
C11 C 0.8946(3) 0.27947(16) 0.7934(3) 0.0445(8) Uani 1 1 d . . .
C10 C 0.7609(3) 0.27856(16) 0.7029(3) 0.0433(8) Uani 1 1 d . . .
C6 C 0.5598(3) 0.22699(16) 0.7470(3) 0.0442(8) Uani 1 1 d . . .
C12 C 0.9223(3) 0.38900(17) 0.7270(4) 0.0478(8) Uani 1 1 d . . .
C5 C 0.6735(3) 0.22001(16) 0.6963(3) 0.0436(8) Uani 1 1 d . . .
C4 C 0.7008(3) 0.15875(17) 0.6371(4) 0.0471(8) Uani 1 1 d . . .
C17 C 0.7929(3) 0.39334(16) 0.6354(4) 0.0450(8) Uani 1 1 d . . .
C18 C 0.7136(3) 0.33589(16) 0.6261(3) 0.0463(8) Uani 1 1 d . . .
H11 H 0.6278 0.3368 0.5671 0.056 Uiso 1 1 calc R . .
C7 C 0.5124(4) 0.28121(18) 0.8144(4) 0.0519(9) Uani 1 1 d . . .
H7 H 0.5516 0.3230 0.8342 0.062 Uiso 1 1 calc R . .
C15 C 0.8275(4) 0.50808(18) 0.5796(4) 0.0591(10) Uani 1 1 d . . .
C3 C 0.8041(4) 0.14021(18) 0.5736(4) 0.0551(9) Uani 1 1 d . . .
H3 H 0.8747 0.1667 0.5663 0.066 Uiso 1 1 calc R . .
C9 C 0.3750(4) 0.1950(2) 0.7969(4) 0.0610(10) Uani 1 1 d . . .
H9 H 0.3037 0.1692 0.8046 0.073 Uiso 1 1 calc R . .
C19 C 1.1039(4) 0.2370(2) 1.0229(4) 0.0689(11) Uani 1 1 d . . .
H19A H 1.1455 0.2013 1.0870 0.103 Uiso 1 1 calc R . .
H19B H 1.0846 0.2731 1.0820 0.103 Uiso 1 1 calc R . .
H19C H 1.1616 0.2526 0.9652 0.103 Uiso 1 1 calc R . .
C16 C 0.7481(4) 0.45376(17) 0.5602(4) 0.0540(9) Uani 1 1 d . . .
H13 H 0.6639 0.4562 0.4973 0.065 Uiso 1 1 calc R . .
C8 C 0.3977(4) 0.2611(2) 0.8455(4) 0.0615(10) Uani 1 1 d . . .
H8 H 0.3451 0.2868 0.8905 0.074 Uiso 1 1 calc R . .
C2 C 0.7797(4) 0.07534(19) 0.5249(4) 0.0620(11) Uani 1 1 d . . .
H2 H 0.8310 0.0498 0.4780 0.074 Uiso 1 1 calc R . .
C1 C 0.6654(4) 0.05506(19) 0.5583(4) 0.0644(11) Uani 1 1 d . . .
H1 H 0.6277 0.0130 0.5371 0.077 Uiso 1 1 calc R . .
C13 C 1.0038(4) 0.44596(19) 0.7433(4) 0.0620(10) Uani 1 1 d . . .
H16 H 1.0893 0.4439 0.8030 0.074 Uiso 1 1 calc R . .
C14 C 0.9572(4) 0.50406(19) 0.6717(4) 0.0663(11) Uani 1 1 d . . .
H15 H 1.0113 0.5415 0.6834 0.080 Uiso 1 1 calc R . .
B1 B 0.4820(5) 0.1056(2) 0.6636(5) 0.0562(11) Uani 1 1 d . . .
C20 C 0.6697(5) 0.5747(2) 0.4100(5) 0.0917(16) Uani 1 1 d . . .
H20A H 0.6568 0.6197 0.3729 0.138 Uiso 1 1 calc R . .
H20B H 0.6016 0.5633 0.4573 0.138 Uiso 1 1 calc R . .
H20C H 0.6669 0.5446 0.3289 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
S1 C11 1.776(3) . ?
S1 C19 1.796(4) . ?
F1 B1 1.393(4) . ?
F2 B1 1.387(5) . ?
O1 C15 1.373(4) . ?
O1 C20 1.428(5) . ?
N2 C9 1.345(5) . ?
N2 C6 1.391(4) . ?
N2 B1 1.552(5) . ?
N3 C11 1.311(4) . ?
N3 C12 1.378(4) . ?
N1 C1 1.350(5) . ?
N1 C4 1.389(4) . ?
N1 B1 1.541(6) . ?
C11 C10 1.444(4) . ?
C10 C18 1.374(4) . ?
C10 C5 1.482(4) . ?
C6 C5 1.404(5) . ?
C6 C7 1.406(5) . ?
C12 C13 1.411(5) . ?
C12 C17 1.414(5) . ?
C5 C4 1.403(4) . ?
C4 C3 1.415(5) . ?
C17 C18 1.411(4) . ?
C17 C16 1.415(5) . ?
C7 C8 1.375(5) . ?
C15 C16 1.355(5) . ?
C15 C14 1.418(5) . ?
C3 C2 1.376(5) . ?
C9 C8 1.398(5) . ?
C2 C1 1.381(6) . ?
C13 C14 1.366(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
C11 S1 C19 102.12(18) . . ?
C15 O1 C20 116.5(3) . . ?
C9 N2 C6 107.8(3) . . ?
C9 N2 B1 126.8(3) . . ?
C6 N2 B1 125.3(3) . . ?
C11 N3 C12 118.7(3) . . ?
C1 N1 C4 106.7(3) . . ?
C1 N1 B1 126.9(3) . . ?
C4 N1 B1 125.9(3) . . ?
N3 C11 C10 123.1(3) . . ?
N3 C11 S1 119.0(2) . . ?
C10 C11 S1 117.8(3) . . ?
C18 C10 C11 117.5(3) . . ?
C18 C10 C5 119.9(3) . . ?
C11 C10 C5 122.6(3) . . ?
N2 C6 C5 121.1(3) . . ?
N2 C6 C7 107.7(3) . . ?
C5 C6 C7 131.1(3) . . ?
N3 C12 C13 118.5(3) . . ?
N3 C12 C17 122.7(3) . . ?
C13 C12 C17 118.8(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 C10 121.2(3) . . ?
C6 C5 C10 119.0(3) . . ?
N1 C4 C5 120.9(3) . . ?
N1 C4 C3 108.4(3) . . ?
C5 C4 C3 130.5(3) . . ?
C18 C17 C12 116.9(3) . . ?
C18 C17 C16 123.2(3) . . ?
C12 C17 C16 119.9(3) . . ?
C10 C18 C17 121.1(3) . . ?
C8 C7 C6 107.5(3) . . ?
C16 C15 O1 125.6(4) . . ?
C16 C15 C14 120.2(3) . . ?
O1 C15 C14 114.2(3) . . ?
C2 C3 C4 106.6(4) . . ?
N2 C9 C8 109.7(3) . . ?
C15 C16 C17 120.1(3) . . ?
C7 C8 C9 107.2(4) . . ?
C3 C2 C1 107.7(4) . . ?
N1 C1 C2 110.6(3) . . ?
C14 C13 C12 120.1(4) . . ?
C13 C14 C15 120.8(3) . . ?
F2 B1 F1 108.9(3) . . ?
F2 B1 N1 111.1(3) . . ?
F1 B1 N1 109.9(3) . . ?
F2 B1 N2 110.8(3) . . ?
F1 B1 N2 109.8(3) . . ?
N1 B1 N2 106.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_bhu051
_database_code_depnum_ccdc_archive 'CCDC 1039760'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-04-09 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 H11 B Cl F2 N3'
_chemical_formula_weight         353.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   9.7361(2)
_cell_length_b                   14.5464(2)
_cell_length_c                   12.2140(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.146(2)
_cell_angle_gamma                90.00
_cell_volume                     1613.33(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7513
_cell_measurement_theta_min      4.8830
_cell_measurement_theta_max      70.8140

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_T_max  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10167
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.87
_diffrn_reflns_theta_max         71.33
_reflns_number_total             3131
_reflns_number_gt                3038
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0733P)²+1.1421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.61194(5) 0.00163(3) 0.23104(4) 0.02573(16) Uani 1 1 d . . .
B1 B 0.9054(3) 0.31712(16) 0.2394(2) 0.0315(5) Uani 1 1 d . . .
F1 F 0.8406(2) 0.37919(10) 0.28945(13) 0.0595(5) Uani 1 1 d . . .
F2 F 1.03683(16) 0.35319(10) 0.23750(12) 0.0482(4) Uani 1 1 d . . .
N1 N 0.93620(18) 0.22470(11) 0.30842(14) 0.0245(3) Uani 1 1 d . . .
N2 N 0.80152(17) 0.29417(11) 0.11366(14) 0.0241(3) Uani 1 1 d . . .
N3 N 0.63305(16) -0.10663(10) 0.07137(13) 0.0216(3) Uani 1 1 d . . .
C1 C 1.0217(2) 0.21253(14) 0.42158(17) 0.0287(4) Uani 1 1 d . . .
H1 H 1.0619 0.2607 0.4764 0.034 Uiso 1 1 calc R . .
C2 C 1.0430(2) 0.11879(14) 0.44687(16) 0.0284(4) Uani 1 1 d . . .
H2 H 1.0998 0.0924 0.5205 0.034 Uiso 1 1 calc R . .
C3 C 0.9661(2) 0.07160(13) 0.34506(16) 0.0241(4) Uani 1 1 d . . .
H3 H 0.9601 0.0068 0.3352 0.029 Uiso 1 1 calc R . .
C4 C 0.89840(19) 0.13815(12) 0.25859(15) 0.0204(4) Uani 1 1 d . . .
C5 C 0.80844(19) 0.12886(12) 0.14032(15) 0.0196(4) Uani 1 1 d . . .
C6 C 0.76128(19) 0.20617(12) 0.06884(15) 0.0209(4) Uani 1 1 d . . .
C7 C 0.6687(2) 0.21476(14) -0.05032(16) 0.0252(4) Uani 1 1 d . . .
H7 H 0.6242 0.1659 -0.1027 0.030 Uiso 1 1 calc R . .
C8 C 0.6551(2) 0.30705(15) -0.07601(19) 0.0336(5) Uani 1 1 d . . .
H8 H 0.5999 0.3340 -0.1496 0.040 Uiso 1 1 calc R . .
C9 C 0.7377(2) 0.35371(14) 0.02652(18) 0.0311(4) Uani 1 1 d . . .
H9 H 0.7472 0.4187 0.0335 0.037 Uiso 1 1 calc R . .
C10 C 0.76542(18) 0.03700(12) 0.08613(14) 0.0189(4) Uani 1 1 d . . .
C11 C 0.67694(19) -0.02762(12) 0.11948(15) 0.0195(4) Uani 1 1 d . . .
C12 C 0.67326(19) -0.13213(13) -0.02103(15) 0.0222(4) Uani 1 1 d . . .
C13 C 0.6238(2) -0.21751(14) -0.07636(18) 0.0286(4) Uani 1 1 d . . .
H13 H 0.5659 -0.2569 -0.0483 0.034 Uiso 1 1 calc R . .
C14 C 0.6597(2) -0.24320(15) -0.17066(18) 0.0323(5) Uani 1 1 d . . .
H14 H 0.6263 -0.3006 -0.2078 0.039 Uiso 1 1 calc R . .
C15 C 0.7456(2) -0.18548(16) -0.21324(17) 0.0336(5) Uani 1 1 d . . .
H15 H 0.7693 -0.2043 -0.2788 0.040 Uiso 1 1 calc R . .
C16 C 0.7949(2) -0.10287(15) -0.16102(16) 0.0293(4) Uani 1 1 d . . .
H16 H 0.8525 -0.0644 -0.1905 0.035 Uiso 1 1 calc R . .
C17 C 0.76045(19) -0.07419(13) -0.06268(15) 0.0221(4) Uani 1 1 d . . .
C18 C 0.8051(2) 0.01088(13) -0.00630(16) 0.0217(4) Uani 1 1 d . . .
H18 H 0.8637 0.0510 -0.0327 0.026 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 C11 1.7493(17) . ?
B1 F1 1.366(3) . ?
B1 F2 1.390(3) . ?
B1 N2 1.540(3) . ?
B1 N1 1.558(3) . ?
N1 C1 1.343(3) . ?
N1 C4 1.389(2) . ?
N2 C9 1.339(2) . ?
N2 C6 1.392(2) . ?
N3 C11 1.291(2) . ?
N3 C12 1.372(2) . ?
C1 C2 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(2) . ?
C5 C6 1.396(2) . ?
C5 C10 1.483(2) . ?
C6 C7 1.414(3) . ?
C7 C8 1.374(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C18 1.372(2) . ?
C10 C11 1.430(2) . ?
C12 C13 1.413(3) . ?
C12 C17 1.415(3) . ?
C13 C14 1.371(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.410(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.421(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.407(3) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 109.54(19) . . ?
F1 B1 N2 110.2(2) . . ?
F2 B1 N2 110.06(17) . . ?
F1 B1 N1 110.94(17) . . ?
F2 B1 N1 109.65(19) . . ?
N2 B1 N1 106.36(16) . . ?
C1 N1 C4 107.42(16) . . ?
C1 N1 B1 126.70(16) . . ?
C4 N1 B1 125.18(15) . . ?
C9 N2 C6 107.36(16) . . ?
C9 N2 B1 127.01(17) . . ?
C6 N2 B1 125.59(15) . . ?
C11 N3 C12 117.97(16) . . ?
N1 C1 C2 110.09(17) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C3 C2 C1 107.29(17) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 106.78(17) . . ?
C2 C3 H3 126.6 . . ?
C4 C3 H3 126.6 . . ?
N1 C4 C5 120.53(16) . . ?
N1 C4 C3 108.41(15) . . ?
C5 C4 C3 131.05(17) . . ?
C6 C5 C4 120.66(16) . . ?
C6 C5 C10 118.07(15) . . ?
C4 C5 C10 121.23(15) . . ?
N2 C6 C5 120.83(16) . . ?
N2 C6 C7 107.93(15) . . ?
C5 C6 C7 131.20(17) . . ?
C8 C7 C6 107.13(17) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 107.06(18) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.52(18) . . ?
N2 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C18 C10 C11 115.45(16) . . ?
C18 C10 C5 119.92(15) . . ?
C11 C10 C5 124.57(15) . . ?
N3 C11 C10 126.15(16) . . ?
N3 C11 Cl1 114.68(13) . . ?
C10 C11 Cl1 119.10(13) . . ?
N3 C12 C13 118.79(17) . . ?
N3 C12 C17 121.40(16) . . ?
C13 C12 C17 119.80(17) . . ?
C14 C13 C12 119.68(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.83(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.51(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.20(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C12 117.88(16) . . ?
C18 C17 C16 123.12(17) . . ?
C12 C17 C16 118.97(17) . . ?
C10 C18 C17 121.16(17) . . ?
C10 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 B1 N1 C1 -60.2(3) . . . . ?
F2 B1 N1 C1 60.9(3) . . . . ?
N2 B1 N1 C1 179.89(17) . . . . ?
F1 B1 N1 C4 130.6(2) . . . . ?
F2 B1 N1 C4 -108.2(2) . . . . ?
N2 B1 N1 C4 10.7(3) . . . . ?
F1 B1 N2 C9 54.3(3) . . . . ?
F2 B1 N2 C9 -66.6(3) . . . . ?
N1 B1 N2 C9 174.67(17) . . . . ?
F1 B1 N2 C6 -128.25(19) . . . . ?
F2 B1 N2 C6 110.8(2) . . . . ?
N1 B1 N2 C6 -7.9(3) . . . . ?
C4 N1 C1 C2 0.9(2) . . . . ?
B1 N1 C1 C2 -169.80(18) . . . . ?
N1 C1 C2 C3 -0.5(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 N1 C4 C5 179.76(16) . . . . ?
B1 N1 C4 C5 -9.3(3) . . . . ?
C1 N1 C4 C3 -1.0(2) . . . . ?
B1 N1 C4 C3 169.93(18) . . . . ?
C2 C3 C4 N1 0.7(2) . . . . ?
C2 C3 C4 C5 179.80(19) . . . . ?
N1 C4 C5 C6 3.3(3) . . . . ?
C3 C4 C5 C6 -175.76(17) . . . . ?
N1 C4 C5 C10 -179.18(15) . . . . ?
C3 C4 C5 C10 1.8(3) . . . . ?
C9 N2 C6 C5 -178.46(17) . . . . ?
B1 N2 C6 C5 3.7(3) . . . . ?
C9 N2 C6 C7 -0.3(2) . . . . ?
B1 N2 C6 C7 -178.15(18) . . . . ?
C4 C5 C6 N2 -0.5(3) . . . . ?
C10 C5 C6 N2 -178.14(15) . . . . ?
C4 C5 C6 C7 -178.21(18) . . . . ?
C10 C5 C6 C7 4.2(3) . . . . ?
N2 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C8 178.32(19) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C6 N2 C9 C8 0.1(2) . . . . ?
B1 N2 C9 C8 177.88(19) . . . . ?
C7 C8 C9 N2 0.2(2) . . . . ?
C6 C5 C10 C18 58.5(2) . . . . ?
C4 C5 C10 C18 -119.08(19) . . . . ?
C6 C5 C10 C11 -118.32(18) . . . . ?
C4 C5 C10 C11 64.1(2) . . . . ?
C12 N3 C11 C10 -0.4(3) . . . . ?
C12 N3 C11 Cl1 176.63(13) . . . . ?
C18 C10 C11 N3 0.3(3) . . . . ?
C5 C10 C11 N3 177.29(16) . . . . ?
C18 C10 C11 Cl1 -176.53(13) . . . . ?
C5 C10 C11 Cl1 0.4(2) . . . . ?
C11 N3 C12 C13 -178.72(16) . . . . ?
C11 N3 C12 C17 0.2(3) . . . . ?
N3 C12 C13 C14 178.37(17) . . . . ?
C17 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
N3 C12 C17 C18 0.0(3) . . . . ?
C13 C12 C17 C18 178.89(16) . . . . ?
N3 C12 C17 C16 -178.04(16) . . . . ?
C13 C12 C17 C16 0.8(3) . . . . ?
C15 C16 C17 C18 -178.61(18) . . . . ?
C15 C16 C17 C12 -0.7(3) . . . . ?
C11 C10 C18 C17 -0.1(2) . . . . ?
C5 C10 C18 C17 -177.23(16) . . . . ?
C12 C17 C18 C10 0.0(3) . . . . ?
C16 C17 C18 C10 177.94(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        71.33
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.061
