# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1453168'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 B Br6.13 Cl0.87 F2 N2'
_chemical_formula_sum            'C9 B Br6.13 Cl0.87 F2 N2'
_chemical_formula_weight         705.37

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn '
_symmetry_space_group_name_H-M   'P 21/n  '

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

_cell_length_a                   8.4388(3)
_cell_length_b                   8.4196(2)
_cell_length_c                   21.5892(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.574(2)
_cell_angle_gamma                90
_cell_volume                     1512.58(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9283
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      36.07

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1281.1
_exptl_absorpt_coefficient_mu    16.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1476
_exptl_absorpt_correction_T_max  0.2433
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29024
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         36.36
_reflns_number_total             7099
_reflns_number_gt                5672
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0238P)²+1.0190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7099
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0533
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.90020(3) 0.37773(3) 0.692913(9) 0.01415(4) Uani 1 1 d . . .
Br2 Br 0.60302(3) 0.37178(3) 0.791660(9) 0.01394(4) Uani 1 1 d . . .
Br3 Br 0.28226(3) 0.61545(3) 0.723599(10) 0.01731(5) Uani 1 1 d . . .
Br4 Br 0.22693(3) 0.93700(3) 0.445803(9) 0.01364(4) Uani 1 1 d . . .
Br5 Br 0.51882(3) 0.90317(3) 0.348985(9) 0.01521(5) Uani 1 1 d . . .
Br6 Br 0.85099(3) 0.68085(3) 0.433700(9) 0.01565(5) Uani 1 1 d . . .
Br7 Br 0.21901(5) 0.76807(6) 0.58231(2) 0.01579(13) Uani 0.1257(19) 1 d P . .
Cl1 Cl 0.21901(5) 0.76807(6) 0.58231(2) 0.01579(13) Uani 0.8743(19) 1 d P . .
F1 F 0.87572(15) 0.69611(15) 0.59175(5) 0.0125(2) Uani 1 1 d . . .
F2 F 0.80116(16) 0.45696(15) 0.54742(6) 0.0132(2) Uani 1 1 d . . .
N1 N 0.6510(2) 0.5611(2) 0.62363(7) 0.0096(3) Uani 1 1 d . . .
N2 N 0.6289(2) 0.6821(2) 0.51743(7) 0.0096(3) Uani 1 1 d . . .
C1 C 0.7024(2) 0.4771(2) 0.67614(9) 0.0105(3) Uani 1 1 d . . .
C2 C 0.5870(2) 0.4778(2) 0.71559(8) 0.0109(3) Uani 1 1 d . . .
C3 C 0.4603(2) 0.5694(2) 0.68640(9) 0.0113(3) Uani 1 1 d . . .
C4 C 0.4983(2) 0.6207(2) 0.62811(9) 0.0104(3) Uani 1 1 d . . .
C5 C 0.4137(2) 0.7082(2) 0.57793(9) 0.0104(3) Uani 1 1 d . . .
C6 C 0.4781(2) 0.7417(2) 0.52364(9) 0.0098(3) Uani 1 1 d . . .
C7 C 0.4170(3) 0.8258(2) 0.46742(9) 0.0111(3) Uani 1 1 d . . .
C8 C 0.5318(3) 0.8151(2) 0.42867(9) 0.0116(3) Uani 1 1 d . . .
C9 C 0.6606(2) 0.7270(2) 0.46095(9) 0.0113(3) Uani 1 1 d . . .
B1 B 0.7489(3) 0.5965(3) 0.56987(10) 0.0109(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.848(2) . ?
Br2 C2 1.8543(19) . ?
Br3 C3 1.858(2) . ?
Br4 C7 1.849(2) . ?
Br5 C8 1.8597(19) . ?
Br6 C9 1.842(2) . ?
Br7 C5 1.736(2) . ?
F1 B1 1.380(3) . ?
F2 B1 1.371(3) . ?
N1 C1 1.345(2) . ?
N1 C4 1.401(3) . ?
N1 B1 1.561(3) . ?
N2 C9 1.345(2) . ?
N2 C6 1.395(3) . ?
N2 B1 1.564(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.417(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.400(3) . ?
C6 C7 1.426(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.402(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
C1 N1 C4 107.54(16) . . ?
C1 N1 B1 126.19(18) . . ?
C4 N1 B1 126.12(16) . . ?
C9 N2 C6 107.93(17) . . ?
C9 N2 B1 125.69(17) . . ?
C6 N2 B1 125.99(16) . . ?
N1 C1 C2 110.60(18) . . ?
N1 C1 Br1 123.86(15) . . ?
C2 C1 Br1 125.54(15) . . ?
C3 C2 C1 106.83(17) . . ?
C3 C2 Br2 127.53(16) . . ?
C1 C2 Br2 125.63(16) . . ?
C2 C3 C4 107.59(18) . . ?
C2 C3 Br3 122.62(15) . . ?
C4 C3 Br3 129.74(16) . . ?
N1 C4 C5 119.36(17) . . ?
N1 C4 C3 107.41(17) . . ?
C5 C4 C3 133.18(19) . . ?
C6 C5 C4 122.28(19) . . ?
C6 C5 Br7 119.30(15) . . ?
C4 C5 Br7 118.35(15) . . ?
N2 C6 C5 119.66(17) . . ?
N2 C6 C7 107.65(17) . . ?
C5 C6 C7 132.65(19) . . ?
C8 C7 C6 106.99(18) . . ?
C8 C7 Br4 123.04(15) . . ?
C6 C7 Br4 129.94(16) . . ?
C7 C8 C9 107.25(17) . . ?
C7 C8 Br5 126.44(16) . . ?
C9 C8 Br5 126.31(16) . . ?
N2 C9 C8 110.17(18) . . ?
N2 C9 Br6 123.06(15) . . ?
C8 C9 Br6 126.74(15) . . ?
F2 B1 F1 111.42(18) . . ?
F2 B1 N1 109.89(17) . . ?
F1 B1 N1 109.74(16) . . ?
F2 B1 N2 110.27(16) . . ?
F1 B1 N2 109.86(17) . . ?
N1 B1 N2 105.49(16) . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.158
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1453169'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 B Br4 Cl3 F2 N2'
_chemical_formula_sum            'C9 B Br4 Cl3 F2 N2'
_chemical_formula_weight         610.91

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn '
_symmetry_space_group_name_H-M   'P 21/n  '

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

_cell_length_a                   8.3531(5)
_cell_length_b                   8.5259(5)
_cell_length_c                   20.7030(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.009(5)
_cell_angle_gamma                90
_cell_volume                     1456.23(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      39.59

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.786
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    11.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1884
_exptl_absorpt_correction_T_max  0.3362
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_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            39613
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         40.03
_reflns_number_total             9029
_reflns_number_gt                7111
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0172P)²+1.3007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9029
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0548
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.167176(19) 0.68167(2) 0.576305(8) 0.01513(3) Uani 1 1 d . . .
Br2 Br 0.786294(18) 0.943377(18) 0.549595(8) 0.01363(3) Uani 1 1 d . . .
Br3 Br 0.716071(18) 0.60296(2) 0.263455(8) 0.01480(3) Uani 1 1 d . . .
Br4 Br 0.100706(18) 0.36957(2) 0.307303(8) 0.01422(3) Uani 1 1 d . . .
Cl1 Cl 0.50171(5) 0.90151(5) 0.649795(19) 0.01556(7) Uani 1 1 d . . .
Cl2 Cl 0.77511(4) 0.77920(5) 0.40592(2) 0.01584(7) Uani 1 1 d . . .
Cl3 Cl 0.39536(5) 0.36457(5) 0.207931(18) 0.01445(6) Uani 1 1 d . . .
F1 F 0.12558(11) 0.69055(11) 0.41037(5) 0.01188(16) Uani 1 1 d . . .
F2 F 0.20942(11) 0.45813(11) 0.45761(5) 0.01250(17) Uani 1 1 d . . .
N1 N 0.38008(14) 0.68502(15) 0.48362(6) 0.0093(2) Uani 1 1 d . . .
N2 N 0.35135(14) 0.55978(15) 0.37409(6) 0.0094(2) Uani 1 1 d . . .
C1 C 0.35387(17) 0.72955(18) 0.54318(7) 0.0107(2) Uani 1 1 d . . .
C2 C 0.48390(18) 0.82049(18) 0.57380(7) 0.0113(2) Uani 1 1 d . . .
C3 C 0.59426(17) 0.83245(18) 0.53051(7) 0.0107(2) Uani 1 1 d . . .
C4 C 0.52925(17) 0.74709(17) 0.47344(7) 0.0096(2) Uani 1 1 d . . .
C5 C 0.58887(16) 0.71278(17) 0.41567(7) 0.0098(2) Uani 1 1 d . . .
C6 C 0.50325(17) 0.61998(17) 0.36617(7) 0.0093(2) Uani 1 1 d . . .
C7 C 0.54004(17) 0.56298(18) 0.30572(7) 0.0102(2) Uani 1 1 d . . .
C8 C 0.41272(18) 0.46765(18) 0.27874(7) 0.0107(2) Uani 1 1 d . . .
C9 C 0.29878(17) 0.47049(18) 0.32150(7) 0.0101(2) Uani 1 1 d . . .
B1 B 0.25675(19) 0.5957(2) 0.43183(8) 0.0094(3) 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
Br1 C1 1.8450(15) . ?
Br2 C3 1.8507(15) . ?
Br3 C7 1.8566(14) . ?
Br4 C9 1.8471(14) . ?
Cl1 C2 1.7033(15) . ?
Cl2 C5 1.6970(14) . ?
Cl3 C8 1.6959(15) . ?
F1 B1 1.3781(18) . ?
F2 B1 1.3723(19) . ?
N1 C1 1.3404(19) . ?
N1 C4 1.3997(18) . ?
N1 B1 1.563(2) . ?
N2 C9 1.3448(19) . ?
N2 C6 1.4019(18) . ?
N2 B1 1.563(2) . ?
C1 C2 1.403(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.421(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.420(2) . ?
C7 C8 1.385(2) . ?
C8 C9 1.398(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
C1 N1 C4 107.99(12) . . ?
C1 N1 B1 125.71(12) . . ?
C4 N1 B1 125.97(12) . . ?
C9 N2 C6 107.41(12) . . ?
C9 N2 B1 126.17(12) . . ?
C6 N2 B1 126.36(12) . . ?
N1 C1 C2 110.24(13) . . ?
N1 C1 Br1 123.27(11) . . ?
C2 C1 Br1 126.45(12) . . ?
C3 C2 C1 107.13(13) . . ?
C3 C2 Cl1 126.63(12) . . ?
C1 C2 Cl1 126.24(12) . . ?
C2 C3 C4 107.07(13) . . ?
C2 C3 Br2 122.77(12) . . ?
C4 C3 Br2 130.16(11) . . ?
C5 C4 N1 119.67(13) . . ?
C5 C4 C3 132.70(13) . . ?
N1 C4 C3 107.56(12) . . ?
C4 C5 C6 122.39(13) . . ?
C4 C5 Cl2 119.24(11) . . ?
C6 C5 Cl2 118.33(11) . . ?
C5 C6 N2 119.30(13) . . ?
C5 C6 C7 133.04(13) . . ?
N2 C6 C7 107.61(12) . . ?
C8 C7 C6 107.32(13) . . ?
C8 C7 Br3 122.18(11) . . ?
C6 C7 Br3 130.47(11) . . ?
C7 C8 C9 106.89(13) . . ?
C7 C8 Cl3 127.52(12) . . ?
C9 C8 Cl3 125.58(12) . . ?
N2 C9 C8 110.74(13) . . ?
N2 C9 Br4 124.28(11) . . ?
C8 C9 Br4 124.96(12) . . ?
F2 B1 F1 111.35(12) . . ?
F2 B1 N2 109.92(13) . . ?
F1 B1 N2 109.88(12) . . ?
F2 B1 N1 110.40(12) . . ?
F1 B1 N1 109.92(13) . . ?
N2 B1 N1 105.20(11) . . ?

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
C4 N1 C1 C2 -0.33(17) . . . . ?
B1 N1 C1 C2 -174.03(13) . . . . ?
C4 N1 C1 Br1 177.33(11) . . . . ?
B1 N1 C1 Br1 3.6(2) . . . . ?
N1 C1 C2 C3 0.32(17) . . . . ?
Br1 C1 C2 C3 -177.24(11) . . . . ?
N1 C1 C2 Cl1 -179.97(11) . . . . ?
Br1 C1 C2 Cl1 2.5(2) . . . . ?
C1 C2 C3 C4 -0.18(17) . . . . ?
Cl1 C2 C3 C4 -179.89(12) . . . . ?
C1 C2 C3 Br2 179.68(11) . . . . ?
Cl1 C2 C3 Br2 0.0(2) . . . . ?
C1 N1 C4 C5 177.48(14) . . . . ?
B1 N1 C4 C5 -8.8(2) . . . . ?
C1 N1 C4 C3 0.21(16) . . . . ?
B1 N1 C4 C3 173.90(13) . . . . ?
C2 C3 C4 C5 -176.79(16) . . . . ?
Br2 C3 C4 C5 3.4(3) . . . . ?
C2 C3 C4 N1 -0.01(17) . . . . ?
Br2 C3 C4 N1 -179.86(11) . . . . ?
N1 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C6 177.71(16) . . . . ?
N1 C4 C5 Cl2 -176.19(11) . . . . ?
C3 C4 C5 Cl2 0.3(2) . . . . ?
C4 C5 C6 N2 0.6(2) . . . . ?
Cl2 C5 C6 N2 178.03(11) . . . . ?
C4 C5 C6 C7 -176.45(16) . . . . ?
Cl2 C5 C6 C7 1.0(2) . . . . ?
C9 N2 C6 C5 -177.48(13) . . . . ?
B1 N2 C6 C5 5.0(2) . . . . ?
C9 N2 C6 C7 0.24(16) . . . . ?
B1 N2 C6 C7 -177.25(13) . . . . ?
C5 C6 C7 C8 176.16(16) . . . . ?
N2 C6 C7 C8 -1.12(17) . . . . ?
C5 C6 C7 Br3 -5.7(3) . . . . ?
N2 C6 C7 Br3 177.05(11) . . . . ?
C6 C7 C8 C9 1.53(17) . . . . ?
Br3 C7 C8 C9 -176.82(11) . . . . ?
C6 C7 C8 Cl3 -178.01(12) . . . . ?
Br3 C7 C8 Cl3 3.6(2) . . . . ?
C6 N2 C9 C8 0.73(17) . . . . ?
B1 N2 C9 C8 178.23(13) . . . . ?
C6 N2 C9 Br4 -177.98(11) . . . . ?
B1 N2 C9 Br4 -0.5(2) . . . . ?
C7 C8 C9 N2 -1.44(18) . . . . ?
Cl3 C8 C9 N2 178.11(11) . . . . ?
C7 C8 C9 Br4 177.26(11) . . . . ?
Cl3 C8 C9 Br4 -3.2(2) . . . . ?
C9 N2 B1 F2 53.86(19) . . . . ?
C6 N2 B1 F2 -129.11(15) . . . . ?
C9 N2 B1 F1 -69.00(19) . . . . ?
C6 N2 B1 F1 108.03(16) . . . . ?
C9 N2 B1 N1 172.73(13) . . . . ?
C6 N2 B1 N1 -10.25(19) . . . . ?
C1 N1 B1 F2 -56.73(19) . . . . ?
C4 N1 B1 F2 130.67(14) . . . . ?
C1 N1 B1 F1 66.49(18) . . . . ?
C4 N1 B1 F1 -106.11(16) . . . . ?
C1 N1 B1 N2 -175.26(13) . . . . ?
C4 N1 B1 N2 12.14(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.036
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.153
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1453170'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 B Br2 Cl5 F2 N2'
_chemical_formula_sum            'C9 B Br2 Cl5 F2 N2'
_chemical_formula_weight         521.99

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P -1          '
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_cell_setting           Triclinic

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.775(2)
_cell_length_b                   9.170(3)
_cell_length_c                   9.710(3)
_cell_angle_alpha                98.378(17)
_cell_angle_beta                 106.86(2)
_cell_angle_gamma                105.71(2)
_cell_volume                     698.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    3381
_cell_measurement_theta_min      2.546
_cell_measurement_theta_max      28.283

_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    6.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4608
_exptl_absorpt_correction_T_max  0.6133
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius KappaCCD '
_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            6598
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3450
_reflns_number_gt                2962
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0419P)²+1.1747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3450
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Br1 Br 0.12421(4) 0.05895(4) 0.38817(4) 0.02618(12) Uani 1 1 d . . .
Br2 Br 0.31077(4) 0.65651(4) 0.94117(4) 0.02395(11) Uani 1 1 d . . .
Cl1 Cl 0.80329(10) 0.26770(10) 0.43788(9) 0.02174(18) Uani 1 1 d . . .
Cl2 Cl 0.42079(11) -0.00991(10) 0.25100(10) 0.02606(19) Uani 1 1 d . . .
Cl3 Cl 0.19435(10) 0.34744(10) 0.67236(9) 0.02257(18) Uani 1 1 d . . .
Cl4 Cl 0.71425(11) 0.91446(10) 1.11105(10) 0.02516(19) Uani 1 1 d . . .
Cl5 Cl 0.98338(10) 0.79285(10) 0.97293(10) 0.02275(18) Uani 1 1 d . . .
F1 F 0.8582(3) 0.5840(2) 0.6464(2) 0.0265(5) Uani 1 1 d . . .
F2 F 0.8652(3) 0.4173(2) 0.7982(2) 0.0253(4) Uani 1 1 d . . .
N1 N 0.6125(4) 0.3549(3) 0.5849(3) 0.0207(6) Uani 1 1 d . . .
N2 N 0.6862(4) 0.5764(3) 0.8012(3) 0.0207(6) Uani 1 1 d . . .
C1 C 0.6221(4) 0.2540(4) 0.4748(4) 0.0214(7) Uani 1 1 d . . .
C2 C 0.4626(5) 0.1421(4) 0.3968(4) 0.0218(7) Uani 1 1 d . . .
C3 C 0.3521(4) 0.1767(4) 0.4604(4) 0.0217(7) Uani 1 1 d . . .
C4 C 0.4442(4) 0.3107(4) 0.5797(4) 0.0214(7) Uani 1 1 d . . .
C5 C 0.4000(4) 0.4009(4) 0.6805(4) 0.0196(7) Uani 1 1 d . . .
C6 C 0.5163(4) 0.5341(4) 0.7876(4) 0.0209(7) Uani 1 1 d . . .
C7 C 0.5012(4) 0.6455(4) 0.8978(4) 0.0211(7) Uani 1 1 d . . .
C8 C 0.6595(4) 0.7524(4) 0.9735(4) 0.0215(7) Uani 1 1 d . . .
C9 C 0.7713(4) 0.7053(4) 0.9127(4) 0.0217(7) Uani 1 1 d . . .
B1 B 0.7674(5) 0.4850(5) 0.7099(5) 0.0217(8) 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
Br1 C3 1.858(4) . ?
Br2 C7 1.862(3) . ?
Cl1 C1 1.705(4) . ?
Cl2 C2 1.712(4) . ?
Cl3 C5 1.712(3) . ?
Cl4 C8 1.699(4) . ?
Cl5 C9 1.695(4) . ?
F1 B1 1.377(5) . ?
F2 B1 1.369(5) . ?
N1 C1 1.346(4) . ?
N1 C4 1.405(4) . ?
N1 B1 1.577(5) . ?
N2 C9 1.345(5) . ?
N2 C6 1.397(4) . ?
N2 B1 1.570(5) . ?
C1 C2 1.402(5) . ?
C2 C3 1.371(5) . ?
C3 C4 1.417(5) . ?
C4 C5 1.397(5) . ?
C5 C6 1.398(5) . ?
C6 C7 1.429(5) . ?
C7 C8 1.375(5) . ?
C8 C9 1.410(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
C1 N1 C4 107.9(3) . . ?
C1 N1 B1 125.5(3) . . ?
C4 N1 B1 126.1(3) . . ?
C9 N2 C6 107.9(3) . . ?
C9 N2 B1 125.5(3) . . ?
C6 N2 B1 126.6(3) . . ?
N1 C1 C2 109.7(3) . . ?
N1 C1 Cl1 123.6(3) . . ?
C2 C1 Cl1 126.7(3) . . ?
C3 C2 C1 107.6(3) . . ?
C3 C2 Cl2 127.7(3) . . ?
C1 C2 Cl2 124.7(3) . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 Br1 121.8(3) . . ?
C4 C3 Br1 130.5(3) . . ?
C5 C4 N1 119.1(3) . . ?
C5 C4 C3 133.9(3) . . ?
N1 C4 C3 107.1(3) . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 Cl3 118.8(3) . . ?
C6 C5 Cl3 118.3(3) . . ?
N2 C6 C5 119.5(3) . . ?
N2 C6 C7 107.4(3) . . ?
C5 C6 C7 133.1(3) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 Br2 122.9(3) . . ?
C6 C7 Br2 129.6(3) . . ?
C7 C8 C9 107.0(3) . . ?
C7 C8 Cl4 127.7(3) . . ?
C9 C8 Cl4 125.3(3) . . ?
N2 C9 C8 110.2(3) . . ?
N2 C9 Cl5 124.0(3) . . ?
C8 C9 Cl5 125.7(3) . . ?
F2 B1 F1 111.7(3) . . ?
F2 B1 N2 110.5(3) . . ?
F1 B1 N2 109.8(3) . . ?
F2 B1 N1 110.0(3) . . ?
F1 B1 N1 109.8(3) . . ?
N2 B1 N1 104.7(3) . . ?

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
C4 N1 C1 C2 -0.5(4) . . . . ?
B1 N1 C1 C2 172.0(3) . . . . ?
C4 N1 C1 Cl1 178.3(3) . . . . ?
B1 N1 C1 Cl1 -9.2(5) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
Cl1 C1 C2 C3 -178.1(3) . . . . ?
N1 C1 C2 Cl2 -178.5(3) . . . . ?
Cl1 C1 C2 Cl2 2.8(5) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
Cl2 C2 C3 C4 178.6(3) . . . . ?
C1 C2 C3 Br1 178.8(2) . . . . ?
Cl2 C2 C3 Br1 -2.2(5) . . . . ?
C1 N1 C4 C5 -177.9(3) . . . . ?
B1 N1 C4 C5 9.6(5) . . . . ?
C1 N1 C4 C3 0.2(4) . . . . ?
B1 N1 C4 C3 -172.3(3) . . . . ?
C2 C3 C4 C5 177.9(4) . . . . ?
Br1 C3 C4 C5 -1.3(6) . . . . ?
C2 C3 C4 N1 0.2(4) . . . . ?
Br1 C3 C4 N1 -179.0(3) . . . . ?
N1 C4 C5 C6 -0.2(5) . . . . ?
C3 C4 C5 C6 -177.7(4) . . . . ?
N1 C4 C5 Cl3 179.4(2) . . . . ?
C3 C4 C5 Cl3 1.9(6) . . . . ?
C9 N2 C6 C5 -178.9(3) . . . . ?
B1 N2 C6 C5 -2.3(5) . . . . ?
C9 N2 C6 C7 0.1(4) . . . . ?
B1 N2 C6 C7 176.7(3) . . . . ?
C4 C5 C6 N2 -3.3(5) . . . . ?
Cl3 C5 C6 N2 177.1(3) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
Cl3 C5 C6 C7 -1.6(6) . . . . ?
N2 C6 C7 C8 0.7(4) . . . . ?
C5 C6 C7 C8 179.5(4) . . . . ?
N2 C6 C7 Br2 -179.4(3) . . . . ?
C5 C6 C7 Br2 -0.6(6) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
Br2 C7 C8 C9 178.9(3) . . . . ?
C6 C7 C8 Cl4 177.1(3) . . . . ?
Br2 C7 C8 Cl4 -2.8(5) . . . . ?
C6 N2 C9 C8 -0.9(4) . . . . ?
B1 N2 C9 C8 -177.5(3) . . . . ?
C6 N2 C9 Cl5 177.2(3) . . . . ?
B1 N2 C9 Cl5 0.6(5) . . . . ?
C7 C8 C9 N2 1.3(4) . . . . ?
Cl4 C8 C9 N2 -177.0(3) . . . . ?
C7 C8 C9 Cl5 -176.7(3) . . . . ?
Cl4 C8 C9 Cl5 4.9(5) . . . . ?
C9 N2 B1 F2 66.7(4) . . . . ?
C6 N2 B1 F2 -109.2(4) . . . . ?
C9 N2 B1 F1 -57.0(5) . . . . ?
C6 N2 B1 F1 127.0(3) . . . . ?
C9 N2 B1 N1 -174.8(3) . . . . ?
C6 N2 B1 N1 9.2(5) . . . . ?
C1 N1 B1 F2 -65.3(4) . . . . ?
C4 N1 B1 F2 105.9(4) . . . . ?
C1 N1 B1 F1 58.1(4) . . . . ?
C4 N1 B1 F1 -130.7(3) . . . . ?
C1 N1 B1 N2 175.9(3) . . . . ?
C4 N1 B1 N2 -12.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.126
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1453171'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H15 B Cl4 F2 N2'
_chemical_formula_sum            'C27 H15 B Cl4 F2 N2'
_chemical_formula_weight         558.02

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn '
_symmetry_space_group_name_H-M   'P 21/n  '

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

_cell_length_a                   12.0397(3)
_cell_length_b                   9.5581(2)
_cell_length_c                   21.4720(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.7660(10)
_cell_angle_gamma                90
_cell_volume                     2377.97(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    5058
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.38

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8689
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22356
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         28.70
_reflns_number_total             6116
_reflns_number_gt                4471
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+1.3273P] 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         6116
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.12573(4) 0.08054(6) 0.43197(2) 0.02447(12) Uani 1 1 d . . .
Cl2 Cl 0.07927(4) 0.18522(6) 0.57315(2) 0.02517(12) Uani 1 1 d . . .
Cl3 Cl 0.82222(4) 0.24767(6) 0.43832(2) 0.02600(13) Uani 1 1 d . . .
Cl4 Cl 0.56254(4) 0.13264(6) 0.34943(2) 0.02223(12) Uani 1 1 d . . .
F1 F 0.32451(9) 0.22448(12) 0.38298(5) 0.0199(3) Uani 1 1 d . . .
F2 F 0.38663(10) 0.01088(11) 0.42347(5) 0.0202(2) Uani 1 1 d . . .
N1 N 0.33403(13) 0.17923(16) 0.49409(7) 0.0142(3) Uani 1 1 d . . .
N2 N 0.51252(13) 0.20795(16) 0.45887(7) 0.0126(3) Uani 1 1 d . . .
C1 C 0.22586(16) 0.1531(2) 0.49518(9) 0.0168(4) Uani 1 1 d . . .
C2 C 0.20793(16) 0.1953(2) 0.55402(9) 0.0169(4) Uani 1 1 d . . .
C3 C 0.31044(15) 0.25249(19) 0.59150(9) 0.0140(4) Uani 1 1 d . . .
C4 C 0.39088(15) 0.24083(19) 0.55356(8) 0.0121(4) Uani 1 1 d . . .
C5 C 0.50690(15) 0.28012(18) 0.56642(8) 0.0115(4) Uani 1 1 d . . .
C6 C 0.56798(15) 0.26464(19) 0.51969(8) 0.0122(4) Uani 1 1 d . . .
C7 C 0.68553(16) 0.29027(19) 0.52216(8) 0.0128(4) Uani 1 1 d . . .
C8 C 0.69814(16) 0.2483(2) 0.46245(8) 0.0165(4) Uani 1 1 d . . .
C9 C 0.59163(17) 0.1984(2) 0.42579(8) 0.0159(4) Uani 1 1 d . . .
C10 C 0.32579(15) 0.3096(2) 0.65741(8) 0.0144(4) Uani 1 1 d . . .
C11 C 0.35049(16) 0.4501(2) 0.67148(9) 0.0180(4) Uani 1 1 d . . .
H11 H 0.3559 0.5130 0.6382 0.022 Uiso 1 1 calc R . .
C12 C 0.36719(17) 0.4986(2) 0.73455(10) 0.0217(4) Uani 1 1 d . . .
H12 H 0.3852 0.5943 0.7442 0.026 Uiso 1 1 calc R . .
C13 C 0.35768(17) 0.4082(2) 0.78311(10) 0.0236(5) Uani 1 1 d . . .
H13 H 0.3702 0.4415 0.8262 0.028 Uiso 1 1 calc R . .
C14 C 0.32988(17) 0.2691(2) 0.76891(9) 0.0218(4) Uani 1 1 d . . .
H14 H 0.3216 0.2074 0.8020 0.026 Uiso 1 1 calc R . .
C15 C 0.31415(16) 0.2198(2) 0.70638(9) 0.0177(4) Uani 1 1 d . . .
H15 H 0.2953 0.1243 0.6969 0.021 Uiso 1 1 calc R . .
C16 C 0.56625(15) 0.33432(19) 0.63188(8) 0.0117(4) Uani 1 1 d . . .
C17 C 0.60396(15) 0.47220(19) 0.64016(8) 0.0137(4) Uani 1 1 d . . .
H17 H 0.5943 0.5319 0.6037 0.016 Uiso 1 1 calc R . .
C18 C 0.65590(16) 0.5225(2) 0.70209(9) 0.0156(4) Uani 1 1 d . . .
H18 H 0.6813 0.6169 0.7080 0.019 Uiso 1 1 calc R . .
C19 C 0.67057(16) 0.4351(2) 0.75501(8) 0.0163(4) Uani 1 1 d . . .
H19 H 0.7066 0.4696 0.7971 0.020 Uiso 1 1 calc R . .
C20 C 0.63309(16) 0.2975(2) 0.74710(8) 0.0149(4) Uani 1 1 d . . .
H20 H 0.6433 0.2383 0.7838 0.018 Uiso 1 1 calc R . .
C21 C 0.58048(15) 0.24593(19) 0.68544(8) 0.0126(4) Uani 1 1 d . . .
H21 H 0.5545 0.1517 0.6798 0.015 Uiso 1 1 calc R . .
C22 C 0.78226(15) 0.34473(19) 0.57540(8) 0.0135(4) Uani 1 1 d . . .
C23 C 0.83524(17) 0.4704(2) 0.56793(9) 0.0209(4) Uani 1 1 d . . .
H23 H 0.8086 0.5228 0.5291 0.025 Uiso 1 1 calc R . .
C24 C 0.92742(18) 0.5193(2) 0.61733(10) 0.0260(5) Uani 1 1 d . . .
H24 H 0.9630 0.6057 0.6124 0.031 Uiso 1 1 calc R . .
C25 C 0.96743(17) 0.4427(2) 0.67363(10) 0.0254(5) Uani 1 1 d . . .
H25 H 1.0301 0.4767 0.7073 0.030 Uiso 1 1 calc R . .
C26 C 0.91566(17) 0.3160(2) 0.68075(9) 0.0206(4) Uani 1 1 d . . .
H26 H 0.9435 0.2630 0.7193 0.025 Uiso 1 1 calc R . .
C27 C 0.82367(16) 0.2668(2) 0.63192(8) 0.0147(4) Uani 1 1 d . . .
H27 H 0.7887 0.1799 0.6369 0.018 Uiso 1 1 calc R . .
B1 B 0.38648(18) 0.1518(2) 0.43636(9) 0.0144(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.6992(19) . ?
Cl2 C2 1.7097(19) . ?
Cl3 C8 1.7090(19) . ?
Cl4 C9 1.7013(18) . ?
F1 B1 1.374(2) . ?
F2 B1 1.375(2) . ?
N1 C1 1.333(2) . ?
N1 C4 1.404(2) . ?
N1 B1 1.559(3) . ?
N2 C9 1.337(2) . ?
N2 C6 1.404(2) . ?
N2 B1 1.558(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.429(2) . ?
C3 C10 1.481(2) . ?
C4 C5 1.400(2) . ?
C5 C6 1.404(2) . ?
C5 C16 1.486(2) . ?
C6 C7 1.423(2) . ?
C7 C8 1.391(2) . ?
C7 C22 1.487(2) . ?
C8 C9 1.394(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 C21 1.399(2) . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 C27 1.396(2) . ?
C23 C24 1.391(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.45(15) . . ?
C1 N1 B1 126.26(15) . . ?
C4 N1 B1 126.25(15) . . ?
C9 N2 C6 107.04(15) . . ?
C9 N2 B1 125.89(15) . . ?
C6 N2 B1 126.78(15) . . ?
N1 C1 C2 110.70(16) . . ?
N1 C1 Cl1 123.17(14) . . ?
C2 C1 Cl1 126.12(15) . . ?
C3 C2 C1 107.82(16) . . ?
C3 C2 Cl2 127.11(15) . . ?
C1 C2 Cl2 124.98(15) . . ?
C2 C3 C4 105.79(16) . . ?
C2 C3 C10 124.00(16) . . ?
C4 C3 C10 130.20(16) . . ?
C5 C4 N1 120.38(15) . . ?
C5 C4 C3 131.39(16) . . ?
N1 C4 C3 108.23(15) . . ?
C4 C5 C6 121.29(16) . . ?
C4 C5 C16 118.53(15) . . ?
C6 C5 C16 120.14(16) . . ?
C5 C6 N2 119.76(16) . . ?
C5 C6 C7 131.62(16) . . ?
N2 C6 C7 108.54(15) . . ?
C8 C7 C6 105.82(15) . . ?
C8 C7 C22 123.44(16) . . ?
C6 C7 C22 130.71(16) . . ?
C7 C8 C9 107.77(16) . . ?
C7 C8 Cl3 127.16(15) . . ?
C9 C8 Cl3 124.99(14) . . ?
N2 C9 C8 110.83(16) . . ?
N2 C9 Cl4 123.18(14) . . ?
C8 C9 Cl4 125.98(15) . . ?
C11 C10 C15 119.33(17) . . ?
C11 C10 C3 121.83(17) . . ?
C15 C10 C3 118.84(17) . . ?
C10 C11 C12 119.86(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.40(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.89(18) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.06(19) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.42(19) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C17 C16 C21 120.31(16) . . ?
C17 C16 C5 120.53(16) . . ?
C21 C16 C5 119.13(16) . . ?
C16 C17 C18 119.74(17) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.02(18) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.53(17) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 120.08(17) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 119.32(17) . . ?
C20 C21 H21 120.3 . . ?
C16 C21 H21 120.3 . . ?
C23 C22 C27 119.68(17) . . ?
C23 C22 C7 120.14(16) . . ?
C27 C22 C7 120.12(16) . . ?
C22 C23 C24 119.90(18) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.82(19) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.24(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 120.01(18) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
F1 B1 F2 110.95(15) . . ?
F1 B1 N2 110.30(15) . . ?
F2 B1 N2 110.22(16) . . ?
F1 B1 N1 109.43(16) . . ?
F2 B1 N1 110.37(15) . . ?
N2 B1 N1 105.43(14) . . ?

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
C4 N1 C1 C2 -0.1(2) . . . . ?
B1 N1 C1 C2 -177.93(17) . . . . ?
C4 N1 C1 Cl1 179.02(14) . . . . ?
B1 N1 C1 Cl1 1.2(3) . . . . ?
N1 C1 C2 C3 0.7(2) . . . . ?
Cl1 C1 C2 C3 -178.37(15) . . . . ?
N1 C1 C2 Cl2 177.57(14) . . . . ?
Cl1 C1 C2 Cl2 -1.5(3) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
Cl2 C2 C3 C4 -177.78(15) . . . . ?
C1 C2 C3 C10 179.83(18) . . . . ?
Cl2 C2 C3 C10 3.1(3) . . . . ?
C1 N1 C4 C5 -179.96(17) . . . . ?
B1 N1 C4 C5 -2.1(3) . . . . ?
C1 N1 C4 C3 -0.5(2) . . . . ?
B1 N1 C4 C3 177.30(16) . . . . ?
C2 C3 C4 C5 -179.71(19) . . . . ?
C10 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 N1 1.0(2) . . . . ?
C10 C3 C4 N1 -179.94(18) . . . . ?
N1 C4 C5 C6 2.7(3) . . . . ?
C3 C4 C5 C6 -176.60(18) . . . . ?
N1 C4 C5 C16 -175.14(16) . . . . ?
C3 C4 C5 C16 5.6(3) . . . . ?
C4 C5 C6 N2 -0.4(3) . . . . ?
C16 C5 C6 N2 177.37(16) . . . . ?
C4 C5 C6 C7 -176.66(18) . . . . ?
C16 C5 C6 C7 1.1(3) . . . . ?
C9 N2 C6 C5 -176.74(16) . . . . ?
B1 N2 C6 C5 -2.7(3) . . . . ?
C9 N2 C6 C7 0.3(2) . . . . ?
B1 N2 C6 C7 174.40(16) . . . . ?
C5 C6 C7 C8 176.64(19) . . . . ?
N2 C6 C7 C8 0.1(2) . . . . ?
C5 C6 C7 C22 -1.2(3) . . . . ?
N2 C6 C7 C22 -177.80(18) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C22 C7 C8 C9 177.66(17) . . . . ?
C6 C7 C8 Cl3 -177.12(15) . . . . ?
C22 C7 C8 Cl3 0.9(3) . . . . ?
C6 N2 C9 C8 -0.6(2) . . . . ?
B1 N2 C9 C8 -174.72(17) . . . . ?
C6 N2 C9 Cl4 179.12(14) . . . . ?
B1 N2 C9 Cl4 5.0(3) . . . . ?
C7 C8 C9 N2 0.6(2) . . . . ?
Cl3 C8 C9 N2 177.43(14) . . . . ?
C7 C8 C9 Cl4 -179.06(14) . . . . ?
Cl3 C8 C9 Cl4 -2.2(3) . . . . ?
C2 C3 C10 C11 -116.5(2) . . . . ?
C4 C3 C10 C11 64.5(3) . . . . ?
C2 C3 C10 C15 62.9(3) . . . . ?
C4 C3 C10 C15 -116.0(2) . . . . ?
C15 C10 C11 C12 2.2(3) . . . . ?
C3 C10 C11 C12 -178.34(17) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 -1.6(3) . . . . ?
C3 C10 C15 C14 178.89(17) . . . . ?
C4 C5 C16 C17 -114.27(19) . . . . ?
C6 C5 C16 C17 67.9(2) . . . . ?
C4 C5 C16 C21 63.7(2) . . . . ?
C6 C5 C16 C21 -114.09(19) . . . . ?
C21 C16 C17 C18 -0.1(3) . . . . ?
C5 C16 C17 C18 177.83(16) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C5 C16 C21 C20 -178.16(16) . . . . ?
C8 C7 C22 C23 65.2(3) . . . . ?
C6 C7 C22 C23 -117.2(2) . . . . ?
C8 C7 C22 C27 -111.8(2) . . . . ?
C6 C7 C22 C27 65.7(3) . . . . ?
C27 C22 C23 C24 -1.5(3) . . . . ?
C7 C22 C23 C24 -178.55(18) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C26 C27 C22 -0.3(3) . . . . ?
C23 C22 C27 C26 1.3(3) . . . . ?
C7 C22 C27 C26 178.36(17) . . . . ?
C9 N2 B1 F1 -66.1(2) . . . . ?
C6 N2 B1 F1 120.93(18) . . . . ?
C9 N2 B1 F2 56.8(2) . . . . ?
C6 N2 B1 F2 -116.22(19) . . . . ?
C9 N2 B1 N1 175.90(16) . . . . ?
C6 N2 B1 N1 2.9(2) . . . . ?
C1 N1 B1 F1 58.3(2) . . . . ?
C4 N1 B1 F1 -119.10(19) . . . . ?
C1 N1 B1 F2 -64.0(2) . . . . ?
C4 N1 B1 F2 118.53(19) . . . . ?
C1 N1 B1 N2 176.96(16) . . . . ?
C4 N1 B1 N2 -0.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.066
# END OF CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1453172'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H9 B Cl4 F2 N2 S3'
_chemical_formula_sum            'C21 H9 B Cl4 F2 N2 S3'
_chemical_formula_weight         576.09

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1 '
_symmetry_space_group_name_H-M   'P -1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0519(9)
_cell_length_b                   10.7177(9)
_cell_length_c                   11.8528(10)
_cell_angle_alpha                102.040(4)
_cell_angle_beta                 91.199(4)
_cell_angle_gamma                114.330(4)
_cell_volume                     1129.73(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9850
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      33.18

_exptl_crystal_description       fragment
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7965
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_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            36429
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         33.19
_reflns_number_total             8575
_reflns_number_gt                7372
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0675P)²+0.8625P] 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         8575
_refine_ls_number_parameters     331
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.096
_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 0.12019(6) 0.66056(5) 0.21038(4) 0.03350(11) Uani 1 1 d . . .
Cl2 Cl 0.13396(7) 0.37467(6) 0.04135(4) 0.03878(12) Uani 1 1 d . . .
Cl3 Cl 0.26938(6) 0.67851(5) 0.91927(4) 0.03428(11) Uani 1 1 d . . .
Cl4 Cl 0.22137(6) 0.85036(4) 0.72519(4) 0.03255(11) Uani 1 1 d . . .
F1 F 0.06832(11) 0.68273(11) 0.47471(9) 0.02360(19) Uani 1 1 d . . .
F2 F 0.31347(11) 0.79105(10) 0.46301(10) 0.0247(2) Uani 1 1 d . . .
N1 N 0.18377(15) 0.54439(14) 0.37055(12) 0.0196(2) Uani 1 1 d . . .
N2 N 0.23075(14) 0.62513(13) 0.58431(12) 0.0187(2) Uani 1 1 d . . .
C1 C 0.1544(2) 0.53710(18) 0.25807(15) 0.0243(3) Uani 1 1 d . . .
C2 C 0.1606(2) 0.41718(19) 0.18908(14) 0.0258(3) Uani 1 1 d . . .
C3 C 0.20104(18) 0.34887(16) 0.26228(14) 0.0215(3) Uani 1 1 d . A .
C4 C 0.21237(16) 0.42914(15) 0.37807(13) 0.0180(2) Uani 1 1 d . . .
C5 C 0.24149(15) 0.40732(14) 0.48698(13) 0.0161(2) Uani 1 1 d . B .
C6 C 0.24889(15) 0.50430(14) 0.59009(13) 0.0168(2) Uani 1 1 d . . .
C7 C 0.26525(16) 0.50103(15) 0.70932(13) 0.0192(2) Uani 1 1 d . D .
C8 C 0.25761(19) 0.62303(16) 0.77252(14) 0.0224(3) Uani 1 1 d . . .
C9 C 0.23652(19) 0.69525(16) 0.69346(15) 0.0227(3) Uani 1 1 d . . .
C10 C 0.2298(2) 0.22513(18) 0.21995(14) 0.0253(3) Uani 1 1 d D . .
S1 S 0.10020(14) 0.07945(10) 0.12966(10) 0.0365(2) Uani 0.758(3) 1 d PD A 1
C11 C 0.3612(12) 0.2138(12) 0.2409(11) 0.0318(9) Uani 0.758(3) 1 d PD A 1
H11 H 0.4462 0.2849 0.2894 0.038 Uiso 0.758(3) 1 calc PR A 1
C12 C 0.3484(6) 0.0786(4) 0.1780(4) 0.0380(8) Uani 0.758(3) 1 d PD A 1
H12 H 0.4258 0.0497 0.1804 0.046 Uiso 0.758(3) 1 calc PR A 1
C13 C 0.2136(7) -0.0049(8) 0.1142(7) 0.0395(10) Uani 0.758(3) 1 d PD A 1
H13 H 0.1867 -0.0972 0.0676 0.047 Uiso 0.758(3) 1 calc PR A 1
C11A C 0.120(2) 0.0991(16) 0.1422(15) 0.0365(2) Uani 0.242(3) 1 d PD A 2
H11A H 0.0231 0.0846 0.1174 0.044 Uiso 0.242(3) 1 calc PR A 2
C12A C 0.184(3) -0.003(3) 0.108(2) 0.0395(10) Uani 0.242(3) 1 d PD A 2
H12A H 0.1301 -0.0948 0.0599 0.047 Uiso 0.242(3) 1 calc PR A 2
C13A C 0.326(2) 0.0459(14) 0.1517(14) 0.0380(8) Uani 0.242(3) 1 d PD A 2
H13A H 0.3844 -0.0043 0.1351 0.046 Uiso 0.242(3) 1 calc PR A 2
S1A S 0.3844(8) 0.2084(9) 0.2396(8) 0.0318(9) Uani 0.242(3) 1 d PD A 2
C14 C 0.25828(15) 0.27879(14) 0.49146(13) 0.0168(2) Uani 1 1 d D . .
S2 S 0.42033(6) 0.28235(7) 0.54256(7) 0.02005(17) Uani 0.702(3) 1 d PD B 1
C15 C 0.1534(5) 0.1412(5) 0.4497(5) 0.0187(5) Uani 0.702(3) 1 d PD B 1
H15 H 0.0569 0.1166 0.4156 0.022 Uiso 0.702(3) 1 calc PR B 1
S2A S 0.1168(2) 0.1207(3) 0.4403(3) 0.0187(5) Uani 0.298(3) 1 d PD B 2
C15A C 0.3831(8) 0.2668(8) 0.5352(8) 0.02005(17) Uani 0.298(3) 1 d PD B 2
H15A H 0.4727 0.3435 0.5723 0.024 Uiso 0.298(3) 1 calc PR B 2
C16 C 0.20878(19) 0.03898(16) 0.46455(17) 0.0264(3) Uani 1 1 d D . .
H16 H 0.1538 -0.0605 0.4434 0.032 Uiso 1 1 calc R B 1
C17 C 0.35085(19) 0.10767(19) 0.51312(18) 0.0290(3) Uani 1 1 d D B .
H17 H 0.4069 0.0591 0.5292 0.035 Uiso 1 1 calc R C 1
C18 C 0.28975(18) 0.39967(16) 0.76341(14) 0.0220(3) Uani 1 1 d D . .
S3 S 0.17018(17) 0.23158(11) 0.75780(13) 0.0227(3) Uani 0.507(3) 1 d PD D 1
C19 C 0.4232(13) 0.4359(14) 0.8350(10) 0.0312(3) Uani 0.507(3) 1 d PD D 1
H19 H 0.5048 0.5256 0.8502 0.037 Uiso 0.507(3) 1 calc PR D 1
C20 C 0.4194(9) 0.3202(6) 0.8815(8) 0.0319(11) Uani 0.507(3) 1 d PD D 1
H20 H 0.4978 0.3241 0.9304 0.038 Uiso 0.507(3) 1 calc PR D 1
C21 C 0.2888(8) 0.2050(7) 0.8459(5) 0.0317(10) Uani 0.507(3) 1 d PD D 1
H21 H 0.2655 0.1186 0.8677 0.038 Uiso 0.507(3) 1 calc PR D 1
S3A S 0.4435(3) 0.4434(3) 0.8472(2) 0.0312(3) Uani 0.493(3) 1 d PD D 2
C19A C 0.1872(9) 0.2598(6) 0.7520(7) 0.0227(3) Uani 0.493(3) 1 d PD D 2
H19A H 0.0929 0.2166 0.7080 0.027 Uiso 0.493(3) 1 calc PR D 2
C20A C 0.2470(8) 0.1919(8) 0.8171(5) 0.0317(10) Uani 0.493(3) 1 d PD D 2
H20A H 0.1964 0.0964 0.8211 0.038 Uiso 0.493(3) 1 calc PR D 2
C21A C 0.3839(9) 0.2795(6) 0.8723(9) 0.0319(11) Uani 0.493(3) 1 d PD D 2
H21A H 0.4399 0.2523 0.9194 0.038 Uiso 0.493(3) 1 calc PR D 2
B1 B 0.19873(18) 0.66789(17) 0.47282(16) 0.0190(3) 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
Cl1 C1 1.6936(16) . ?
Cl2 C2 1.7008(17) . ?
Cl3 C8 1.7014(17) . ?
Cl4 C9 1.6966(15) . ?
F1 B1 1.3841(18) . ?
F2 B1 1.3788(19) . ?
N1 C1 1.338(2) . ?
N1 C4 1.3977(18) . ?
N1 B1 1.550(2) . ?
N2 C9 1.341(2) . ?
N2 C6 1.3950(18) . ?
N2 B1 1.555(2) . ?
C1 C2 1.398(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.434(2) . ?
C3 C10 1.462(2) . ?
C4 C5 1.405(2) . ?
C5 C6 1.4079(19) . ?
C5 C14 1.4666(19) . ?
C6 C7 1.429(2) . ?
C7 C8 1.398(2) . ?
C7 C18 1.468(2) . ?
C8 C9 1.397(2) . ?
C10 C11 1.396(9) . ?
C10 C11A 1.450(13) . ?
C10 S1A 1.653(7) . ?
C10 S1 1.688(2) . ?
S1 C13 1.714(4) . ?
C11 C12 1.437(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C11A C12A 1.477(15) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.344(14) . ?
C12A H12A 0.9500 . ?
C13A S1A 1.684(12) . ?
C13A H13A 0.9500 . ?
C14 C15 1.387(5) . ?
C14 C15A 1.412(7) . ?
C14 S2A 1.677(3) . ?
C14 S2 1.7087(15) . ?
S2 C17 1.660(2) . ?
C15 C16 1.456(6) . ?
C15 H15 0.9500 . ?
S2A C16 1.570(3) . ?
C15A C17 1.561(8) . ?
C15A H15A 0.9500 . ?
C16 C17 1.355(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19A 1.402(6) . ?
C18 C19 1.434(9) . ?
C18 S3A 1.655(2) . ?
C18 S3 1.6904(19) . ?
S3 C21 1.716(5) . ?
C19 C20 1.445(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.360(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
S3A C21A 1.700(7) . ?
C19A C20A 1.435(9) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.358(8) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 108.11(13) . . ?
C1 N1 B1 125.29(13) . . ?
C4 N1 B1 126.33(13) . . ?
C9 N2 C6 107.61(13) . . ?
C9 N2 B1 125.20(12) . . ?
C6 N2 B1 127.06(12) . . ?
N1 C1 C2 110.13(14) . . ?
N1 C1 Cl1 123.38(13) . . ?
C2 C1 Cl1 126.47(13) . . ?
C3 C2 C1 108.04(14) . . ?
C3 C2 Cl2 128.08(13) . . ?
C1 C2 Cl2 123.76(13) . . ?
C2 C3 C4 105.58(13) . . ?
C2 C3 C10 123.43(15) . . ?
C4 C3 C10 130.94(14) . . ?
N1 C4 C5 120.39(13) . . ?
N1 C4 C3 108.09(13) . . ?
C5 C4 C3 131.50(13) . . ?
C4 C5 C6 120.66(12) . . ?
C4 C5 C14 118.76(12) . . ?
C6 C5 C14 120.54(13) . . ?
N2 C6 C5 119.82(13) . . ?
N2 C6 C7 108.71(12) . . ?
C5 C6 C7 131.38(13) . . ?
C8 C7 C6 105.40(13) . . ?
C8 C7 C18 123.54(14) . . ?
C6 C7 C18 131.03(13) . . ?
C9 C8 C7 107.94(14) . . ?
C9 C8 Cl3 124.17(12) . . ?
C7 C8 Cl3 127.89(13) . . ?
N2 C9 C8 110.33(13) . . ?
N2 C9 Cl4 122.76(13) . . ?
C8 C9 Cl4 126.90(13) . . ?
C11 C10 C11A 112.2(10) . . ?
C11 C10 C3 126.8(5) . . ?
C11A C10 C3 120.9(9) . . ?
C11A C10 S1A 110.5(9) . . ?
C3 C10 S1A 128.4(3) . . ?
C11 C10 S1 113.0(5) . . ?
C3 C10 S1 120.12(14) . . ?
S1A C10 S1 111.3(3) . . ?
C10 S1 C13 92.6(3) . . ?
C10 C11 C12 109.9(8) . . ?
C10 C11 H11 125.1 . . ?
C12 C11 H11 125.1 . . ?
C13 C12 C11 113.5(6) . . ?
C13 C12 H12 123.3 . . ?
C11 C12 H12 123.3 . . ?
C12 C13 S1 111.1(5) . . ?
C12 C13 H13 124.5 . . ?
S1 C13 H13 124.5 . . ?
C10 C11A C12A 108.5(17) . . ?
C10 C11A H11A 125.8 . . ?
C12A C11A H11A 125.8 . . ?
C13A C12A C11A 114(2) . . ?
C13A C12A H12A 123.1 . . ?
C11A C12A H12A 123.1 . . ?
C12A C13A S1A 110.8(17) . . ?
C12A C13A H13A 124.6 . . ?
S1A C13A H13A 124.6 . . ?
C10 S1A C13A 96.3(8) . . ?
C15 C14 C15A 105.2(4) . . ?
C15 C14 C5 126.5(3) . . ?
C15A C14 C5 128.3(3) . . ?
C15A C14 S2A 111.9(3) . . ?
C5 C14 S2A 119.78(14) . . ?
C15 C14 S2 110.9(2) . . ?
C5 C14 S2 122.49(10) . . ?
S2A C14 S2 117.69(13) . . ?
C17 S2 C14 92.16(8) . . ?
C14 C15 C16 111.9(3) . . ?
C14 C15 H15 124.0 . . ?
C16 C15 H15 124.0 . . ?
C16 S2A C14 93.01(13) . . ?
C14 C15A C17 109.3(5) . . ?
C14 C15A H15A 125.3 . . ?
C17 C15A H15A 125.3 . . ?
C17 C16 C15 109.5(2) . . ?
C17 C16 S2A 121.69(15) . . ?
C17 C16 H16 125.3 . . ?
C15 C16 H16 125.3 . . ?
S2A C16 H16 113.0 . . ?
C16 C17 C15A 104.0(3) . . ?
C16 C17 S2 115.44(13) . . ?
C16 C17 H17 122.3 . . ?
C15A C17 H17 133.7 . . ?
S2 C17 H17 122.3 . . ?
C19A C18 C19 113.1(7) . . ?
C19A C18 C7 124.4(4) . . ?
C19 C18 C7 122.5(6) . . ?
C19A C18 S3A 113.5(4) . . ?
C7 C18 S3A 122.05(16) . . ?
C19 C18 S3 110.1(6) . . ?
C7 C18 S3 127.35(13) . . ?
S3A C18 S3 110.53(15) . . ?
C18 S3 C21 93.4(3) . . ?
C18 C19 C20 112.3(10) . . ?
C18 C19 H19 123.8 . . ?
C20 C19 H19 123.8 . . ?
C21 C20 C19 111.0(8) . . ?
C21 C20 H20 124.5 . . ?
C19 C20 H20 124.5 . . ?
C20 C21 S3 113.2(6) . . ?
C20 C21 H21 123.4 . . ?
S3 C21 H21 123.4 . . ?
C18 S3A C21A 92.4(3) . . ?
C18 C19A C20A 109.4(6) . . ?
C18 C19A H19A 125.3 . . ?
C20A C19A H19A 125.3 . . ?
C21A C20A C19A 112.6(7) . . ?
C21A C20A H20A 123.7 . . ?
C19A C20A H20A 123.7 . . ?
C20A C21A S3A 112.1(7) . . ?
C20A C21A H21A 123.9 . . ?
S3A C21A H21A 123.9 . . ?
F2 B1 F1 110.66(12) . . ?
F2 B1 N1 110.21(13) . . ?
F1 B1 N1 109.96(13) . . ?
F2 B1 N2 110.51(13) . . ?
F1 B1 N2 110.10(13) . . ?
N1 B1 N2 105.28(11) . . ?

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
C4 N1 C1 C2 0.86(19) . . . . ?
B1 N1 C1 C2 175.17(15) . . . . ?
C4 N1 C1 Cl1 -177.54(13) . . . . ?
B1 N1 C1 Cl1 -3.2(2) . . . . ?
N1 C1 C2 C3 -2.2(2) . . . . ?
Cl1 C1 C2 C3 176.17(14) . . . . ?
N1 C1 C2 Cl2 -178.31(13) . . . . ?
Cl1 C1 C2 Cl2 0.0(3) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
Cl2 C2 C3 C4 178.43(14) . . . . ?
C1 C2 C3 C10 -175.01(16) . . . . ?
Cl2 C2 C3 C10 0.9(3) . . . . ?
C1 N1 C4 C5 -177.68(14) . . . . ?
B1 N1 C4 C5 8.1(2) . . . . ?
C1 N1 C4 C3 0.74(17) . . . . ?
B1 N1 C4 C3 -173.49(14) . . . . ?
C2 C3 C4 N1 -2.01(18) . . . . ?
C10 C3 C4 N1 175.24(17) . . . . ?
C2 C3 C4 C5 176.16(16) . . . . ?
C10 C3 C4 C5 -6.6(3) . . . . ?
N1 C4 C5 C6 -2.9(2) . . . . ?
C3 C4 C5 C6 179.14(15) . . . . ?
N1 C4 C5 C14 174.75(13) . . . . ?
C3 C4 C5 C14 -3.2(2) . . . . ?
C9 N2 C6 C5 177.43(13) . . . . ?
B1 N2 C6 C5 1.3(2) . . . . ?
C9 N2 C6 C7 0.50(17) . . . . ?
B1 N2 C6 C7 -175.62(13) . . . . ?
C4 C5 C6 N2 -1.6(2) . . . . ?
C14 C5 C6 N2 -179.15(13) . . . . ?
C4 C5 C6 C7 174.54(15) . . . . ?
C14 C5 C6 C7 -3.0(2) . . . . ?
N2 C6 C7 C8 -0.54(16) . . . . ?
C5 C6 C7 C8 -176.99(15) . . . . ?
N2 C6 C7 C18 -178.79(15) . . . . ?
C5 C6 C7 C18 4.8(3) . . . . ?
C6 C7 C8 C9 0.38(18) . . . . ?
C18 C7 C8 C9 178.79(15) . . . . ?
C6 C7 C8 Cl3 179.80(13) . . . . ?
C18 C7 C8 Cl3 -1.8(2) . . . . ?
C6 N2 C9 C8 -0.26(18) . . . . ?
B1 N2 C9 C8 175.95(14) . . . . ?
C6 N2 C9 Cl4 179.15(12) . . . . ?
B1 N2 C9 Cl4 -4.6(2) . . . . ?
C7 C8 C9 N2 -0.1(2) . . . . ?
Cl3 C8 C9 N2 -179.53(12) . . . . ?
C7 C8 C9 Cl4 -179.47(13) . . . . ?
Cl3 C8 C9 Cl4 1.1(2) . . . . ?
C2 C3 C10 C11 119.9(7) . . . . ?
C4 C3 C10 C11 -56.9(7) . . . . ?
C2 C3 C10 S1 -56.2(2) . . . . ?
C4 C3 C10 S1 126.94(18) . . . . ?
C11 C10 S1 C13 -0.2(6) . . . . ?
C3 C10 S1 C13 176.5(3) . . . . ?
C3 C10 C11 C12 -176.2(4) . . . . ?
S1 C10 C11 C12 0.1(9) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C11 C12 C13 S1 -0.1(9) . . . . ?
C10 S1 C13 C12 0.1(5) . . . . ?
C4 C5 C14 C15 -60.4(4) . . . . ?
C6 C5 C14 C15 117.2(4) . . . . ?
C4 C5 C14 S2 115.12(14) . . . . ?
C6 C5 C14 S2 -67.27(17) . . . . ?
C15 C14 S2 C17 -1.4(3) . . . . ?
C5 C14 S2 C17 -177.52(14) . . . . ?
C5 C14 C15 C16 177.8(2) . . . . ?
S2 C14 C15 C16 1.9(5) . . . . ?
C14 C15 C16 C17 -1.5(5) . . . . ?
C15 C16 C17 S2 0.5(3) . . . . ?
C14 S2 C17 C16 0.48(17) . . . . ?
C8 C7 C18 C19 -64.2(7) . . . . ?
C6 C7 C18 C19 113.8(7) . . . . ?
C8 C7 C18 S3 113.03(18) . . . . ?
C6 C7 C18 S3 -69.0(2) . . . . ?
C19 C18 S3 C21 -0.3(6) . . . . ?
C7 C18 S3 C21 -177.8(3) . . . . ?
C7 C18 C19 C20 178.0(6) . . . . ?
S3 C18 C19 C20 0.4(10) . . . . ?
C18 C19 C20 C21 -0.3(12) . . . . ?
C19 C20 C21 S3 0.1(9) . . . . ?
C18 S3 C21 C20 0.1(6) . . . . ?
C1 N1 B1 F2 -61.5(2) . . . . ?
C4 N1 B1 F2 111.76(16) . . . . ?
C1 N1 B1 F1 60.7(2) . . . . ?
C4 N1 B1 F1 -125.99(15) . . . . ?
C1 N1 B1 N2 179.30(14) . . . . ?
C4 N1 B1 N2 -7.4(2) . . . . ?
C9 N2 B1 F2 68.26(19) . . . . ?
C6 N2 B1 F2 -116.27(15) . . . . ?
C9 N2 B1 F1 -54.3(2) . . . . ?
C6 N2 B1 F1 121.19(15) . . . . ?
C9 N2 B1 N1 -172.76(14) . . . . ?
C6 N2 B1 N1 2.71(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.103
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1453173'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H25 B Cl2 F2 N2'
_chemical_formula_sum            'C39 H25 B Cl2 F2 N2'
_chemical_formula_weight         641.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
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_Hall  '-P 2ybc '
_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                   26.1253(10)
_cell_length_b                   12.6428(5)
_cell_length_c                   18.6230(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.840(2)
_cell_angle_gamma                90
_cell_volume                     6147.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      60.12

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2640
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_T_max  0.9352
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_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            34476
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         60.95
_reflns_number_total             9079
_reflns_number_gt                7087
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0526P)²+3.2593P] 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         9079
_refine_ls_number_parameters     1025
_refine_ls_number_restraints     721
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      0.977
_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 0.46849(2) 0.85659(5) 0.36685(3) 0.05265(17) Uani 1 1 d U . .
Cl2 Cl 0.39402(3) 0.07070(5) 0.37915(3) 0.05614(18) Uani 1 1 d U . .
F1 F 0.34938(5) 0.48349(11) 0.29238(7) 0.0555(4) Uani 1 1 d U . .
F2 F 0.33243(5) 0.50811(11) 0.41078(8) 0.0568(4) Uani 1 1 d U . .
N1 N 0.41321(7) 0.57124(15) 0.36770(10) 0.0464(5) Uani 1 1 d U . .
N2 N 0.39490(8) 0.37726(15) 0.37768(10) 0.0463(5) Uani 1 1 d U . .
C1 C 0.40727(9) 0.67758(19) 0.36518(12) 0.0475(6) Uani 1 1 d U . .
C2 C 0.45639(10) 0.72288(19) 0.36987(12) 0.0476(6) Uani 1 1 d U . .
C3 C 0.49365(9) 0.64499(19) 0.37440(12) 0.0464(6) Uani 1 1 d U . .
C4 C 0.46543(9) 0.54805(19) 0.37275(12) 0.0459(6) Uani 1 1 d U . .
C5 C 0.48237(9) 0.44227(19) 0.37468(12) 0.0467(6) Uani 1 1 d U . .
C6 C 0.44760(9) 0.35817(19) 0.37686(12) 0.0467(6) Uani 1 1 d U . .
C7 C 0.45590(10) 0.24659(19) 0.37936(12) 0.0470(6) Uani 1 1 d U . .
C8 C 0.40762(10) 0.20382(19) 0.38228(12) 0.0494(6) Uani 1 1 d U . .
C9 C 0.37002(10) 0.28327(19) 0.38160(12) 0.0472(6) Uani 1 1 d U . .
C10 C 0.35827(10) 0.7347(2) 0.35525(14) 0.0515(6) Uani 1 1 d U . .
C11 C 0.34765(11) 0.8197(2) 0.39964(16) 0.0599(7) Uani 1 1 d U . .
H11 H 0.3703 0.8370 0.4388 0.072 Uiso 1 1 calc R . .
C12 C 0.30363(12) 0.8793(2) 0.38640(18) 0.0732(8) Uani 1 1 d U . .
H12 H 0.2962 0.9374 0.4167 0.088 Uiso 1 1 calc R . .
C13 C 0.27059(12) 0.8545(3) 0.32937(19) 0.0786(9) Uani 1 1 d U . .
H13 H 0.2409 0.8963 0.3204 0.094 Uiso 1 1 calc R . .
C14 C 0.28034(11) 0.7701(2) 0.28572(17) 0.0692(8) Uani 1 1 d U . .
H14 H 0.2572 0.7525 0.2471 0.083 Uiso 1 1 calc R . .
C15 C 0.32402(10) 0.7112(2) 0.29840(15) 0.0589(7) Uani 1 1 d U . .
H15 H 0.3310 0.6532 0.2678 0.071 Uiso 1 1 calc R . .
C16 C 0.54929(9) 0.66520(19) 0.37832(12) 0.0474(6) Uani 1 1 d U . .
C17 C 0.57193(10) 0.7243(2) 0.32438(14) 0.0556(7) Uani 1 1 d U . .
H17 H 0.5513 0.7516 0.2858 0.067 Uiso 1 1 calc R . .
C18 C 0.62385(11) 0.7433(2) 0.32670(15) 0.0635(7) Uani 1 1 d U . .
H18 H 0.6387 0.7836 0.2897 0.076 Uiso 1 1 calc R . .
C19 C 0.65451(11) 0.7045(2) 0.38210(15) 0.0617(7) Uani 1 1 d U . .
H19 H 0.6904 0.7165 0.3829 0.074 Uiso 1 1 calc R . .
C20 C 0.63248(10) 0.6477(2) 0.43667(14) 0.0551(6) Uani 1 1 d U . .
H20 H 0.6533 0.6214 0.4754 0.066 Uiso 1 1 calc R . .
C21 C 0.58061(10) 0.6293(2) 0.43508(13) 0.0506(6) Uani 1 1 d U . .
H21 H 0.5659 0.5914 0.4733 0.061 Uiso 1 1 calc R . .
C22 C 0.53800(9) 0.41860(19) 0.37318(12) 0.0469(6) Uani 1 1 d U . .
C23 C 0.56455(10) 0.4408(2) 0.31103(13) 0.0500(6) Uani 1 1 d U . .
H23 H 0.5474 0.4738 0.2713 0.060 Uiso 1 1 calc R . .
C24 C 0.61554(10) 0.4149(2) 0.30723(14) 0.0558(7) Uani 1 1 d U . .
H24 H 0.6333 0.4286 0.2645 0.067 Uiso 1 1 calc R . .
C25 C 0.64105(10) 0.3690(2) 0.36561(15) 0.0588(7) Uani 1 1 d U . .
H25 H 0.6762 0.3508 0.3627 0.071 Uiso 1 1 calc R . .
C26 C 0.61538(10) 0.3494(2) 0.42819(14) 0.0555(6) Uani 1 1 d U . .
H26 H 0.6332 0.3197 0.4687 0.067 Uiso 1 1 calc R . .
C27 C 0.56416(10) 0.3729(2) 0.43157(13) 0.0520(6) Uani 1 1 d U . .
H27 H 0.5465 0.3578 0.4741 0.062 Uiso 1 1 calc R . .
C28 C 0.50267(10) 0.18077(19) 0.38095(13) 0.0496(6) Uani 1 1 d U . .
C29 C 0.53151(10) 0.1640(2) 0.32092(14) 0.0577(7) Uani 1 1 d U . .
H29 H 0.5243 0.2033 0.2783 0.069 Uiso 1 1 calc R . .
C30 C 0.57069(11) 0.0906(2) 0.32240(15) 0.0653(8) Uani 1 1 d U . .
H30 H 0.5898 0.0786 0.2806 0.078 Uiso 1 1 calc R . .
C31 C 0.58208(11) 0.0346(2) 0.38485(16) 0.0653(7) Uani 1 1 d U . .
H31 H 0.6085 -0.0171 0.3857 0.078 Uiso 1 1 calc R . .
C32 C 0.55516(11) 0.0539(2) 0.44526(15) 0.0613(7) Uani 1 1 d U . .
H32 H 0.5641 0.0180 0.4887 0.074 Uiso 1 1 calc R . .
C33 C 0.51527(10) 0.1249(2) 0.44350(14) 0.0553(6) Uani 1 1 d U . .
H33 H 0.4961 0.1359 0.4854 0.066 Uiso 1 1 calc R . .
C34 C 0.31473(10) 0.26495(19) 0.38484(12) 0.0476(6) Uani 1 1 d U . .
C35 C 0.29798(10) 0.19762(19) 0.43982(13) 0.0510(6) Uani 1 1 d U . .
H35 H 0.3221 0.1708 0.4745 0.061 Uiso 1 1 calc R . .
C36 C 0.24738(10) 0.1704(2) 0.44380(14) 0.0585(7) Uani 1 1 d U . .
H36 H 0.2365 0.1265 0.4818 0.070 Uiso 1 1 calc R . .
C37 C 0.21232(11) 0.2068(2) 0.39281(16) 0.0708(8) Uani 1 1 d U . .
H37 H 0.1773 0.1870 0.3949 0.085 Uiso 1 1 calc R . .
C38 C 0.22846(12) 0.2726(2) 0.33820(16) 0.0714(8) Uani 1 1 d U . .
H38 H 0.2043 0.2976 0.3029 0.086 Uiso 1 1 calc R . .
C39 C 0.27911(11) 0.3017(2) 0.33481(14) 0.0578(7) Uani 1 1 d U . .
H39 H 0.2896 0.3475 0.2976 0.069 Uiso 1 1 calc R . .
B1 B 0.36949(11) 0.4865(2) 0.36257(15) 0.0494(7) Uani 1 1 d U . .
Cl3 Cl 0.03253(3) -0.01315(5) 0.09860(4) 0.0650(2) Uani 1 1 d U . .
Cl4 Cl 0.10478(3) 0.77127(6) 0.13612(4) 0.0784(2) Uani 1 1 d U . .
F3 F 0.16304(6) 0.35128(11) 0.06842(8) 0.0633(4) Uani 1 1 d U A .
F4 F 0.15395(6) 0.33378(14) 0.18793(9) 0.0788(5) Uani 1 1 d U A .
N3 N 0.08516(8) 0.27267(16) 0.11140(10) 0.0487(5) Uani 1 1 d U A .
N4 N 0.10363(8) 0.46541(17) 0.12458(11) 0.0544(5) Uani 1 1 d U A .
C40 C 0.09179(9) 0.1674(2) 0.10419(13) 0.0495(6) Uani 1 1 d DU . .
C41 C 0.04302(10) 0.1204(2) 0.10518(13) 0.0511(6) Uani 1 1 d U A .
C42 C 0.00578(9) 0.1964(2) 0.11247(12) 0.0492(6) Uani 1 1 d U . .
C43 C 0.03291(9) 0.2943(2) 0.11673(12) 0.0463(6) Uani 1 1 d U A .
C44 C 0.01623(10) 0.3983(2) 0.12489(12) 0.0511(6) Uani 1 1 d U . .
C45 C 0.05104(10) 0.4833(2) 0.12841(13) 0.0542(6) Uani 1 1 d U A .
C46 C 0.04274(11) 0.5946(2) 0.13218(14) 0.0586(7) Uani 1 1 d U . .
C47 C 0.09081(12) 0.6381(2) 0.12876(16) 0.0669(8) Uani 1 1 d U A .
C48 C 0.12841(11) 0.5593(2) 0.12402(15) 0.0619(7) Uani 1 1 d U . .
C49 C 0.1400(2) 0.1095(6) 0.0909(3) 0.0482(14) Uani 0.675(4) 1 d PDU A 1
C50 C 0.15689(15) 0.0331(3) 0.1399(2) 0.0614(12) Uani 0.675(4) 1 d PDU A 1
H50 H 0.1370 0.0172 0.1803 0.074 Uiso 0.675(4) 1 calc PR A 1
C51 C 0.20240(16) -0.0198(3) 0.1303(3) 0.0725(14) Uani 0.675(4) 1 d PDU A 1
H51 H 0.2133 -0.0726 0.1637 0.087 Uiso 0.675(4) 1 calc PR A 1
C52 C 0.2320(3) 0.0033(6) 0.0727(5) 0.070(2) Uani 0.675(4) 1 d PDU A 1
H52 H 0.2635 -0.0326 0.0667 0.084 Uiso 0.675(4) 1 calc PR A 1
C53 C 0.21569(18) 0.0793(5) 0.0235(3) 0.0604(13) Uani 0.675(4) 1 d PDU A 1
H53 H 0.2358 0.0949 -0.0167 0.072 Uiso 0.675(4) 1 calc PR A 1
C54 C 0.17046(16) 0.1322(4) 0.0327(2) 0.0558(11) Uani 0.675(4) 1 d PDU A 1
H54 H 0.1598 0.1847 -0.0010 0.067 Uiso 0.675(4) 1 calc PR A 1
C49A C 0.1446(5) 0.1242(15) 0.1076(7) 0.0482(14) Uani 0.325(4) 1 d PDU A 2
C50A C 0.1787(3) 0.1327(6) 0.1649(5) 0.057(2) Uani 0.325(4) 1 d PDU A 2
H50A H 0.1693 0.1707 0.2064 0.069 Uiso 0.325(4) 1 calc PR A 2
C51A C 0.2264(3) 0.0867(8) 0.1629(6) 0.079(3) Uani 0.325(4) 1 d PDU A 2
H51A H 0.2497 0.0920 0.2030 0.095 Uiso 0.325(4) 1 calc PR A 2
C52A C 0.2400(6) 0.0325(15) 0.1016(9) 0.096(7) Uani 0.325(4) 1 d PDU A 2
H52A H 0.2732 0.0022 0.0995 0.116 Uiso 0.325(4) 1 calc PR A 2
C53A C 0.2062(5) 0.0220(11) 0.0438(8) 0.077(4) Uani 0.325(4) 1 d PDU A 2
H53A H 0.2163 -0.0144 0.0019 0.093 Uiso 0.325(4) 1 calc PR A 2
C54A C 0.1571(4) 0.0644(8) 0.0464(6) 0.066(3) Uani 0.325(4) 1 d PDU A 2
H54A H 0.1328 0.0535 0.0082 0.079 Uiso 0.325(4) 1 calc PR A 2
C55 C -0.04945(10) 0.1718(2) 0.11506(16) 0.0585(7) Uani 1 1 d DU A .
C56 C -0.0839(3) 0.1864(5) 0.0563(4) 0.069(2) Uani 0.672(5) 1 d PDU A 1
H56 H -0.0719 0.2187 0.0140 0.082 Uiso 0.672(5) 1 calc PR A 1
C57 C -0.1340(4) 0.1558(6) 0.0577(6) 0.097(4) Uani 0.672(5) 1 d PDU A 1
H57 H -0.1562 0.1708 0.0176 0.116 Uiso 0.672(5) 1 calc PR A 1
C58 C -0.1514(4) 0.1082(9) 0.1111(6) 0.085(3) Uani 0.672(5) 1 d PDU A 1
H58 H -0.1867 0.0906 0.1108 0.102 Uiso 0.672(5) 1 calc PR A 1
C59 C -0.11931(18) 0.0792(4) 0.1731(3) 0.0827(17) Uani 0.672(5) 1 d PDU A 1
H59 H -0.1325 0.0429 0.2131 0.099 Uiso 0.672(5) 1 calc PR A 1
C60 C -0.06848(16) 0.1078(3) 0.1703(2) 0.0642(13) Uani 0.672(5) 1 d PDU A 1
H60 H -0.0453 0.0834 0.2070 0.077 Uiso 0.672(5) 1 calc PR A 1
C56A C -0.0759(3) 0.2037(6) 0.1832(4) 0.047(2) Uani 0.328(5) 1 d PDU A 2
H56A H -0.0581 0.2374 0.2222 0.057 Uiso 0.328(5) 1 calc PR A 2
C57A C -0.1272(3) 0.1802(6) 0.1845(4) 0.054(2) Uani 0.328(5) 1 d PDU A 2
H57A H -0.1447 0.2030 0.2257 0.065 Uiso 0.328(5) 1 calc PR A 2
C58A C -0.1547(10) 0.1296(18) 0.1352(8) 0.063(5) Uani 0.328(5) 1 d PDU A 2
H58A H -0.1882 0.1032 0.1424 0.075 Uiso 0.328(5) 1 calc PR A 2
C59A C -0.1258(7) 0.1179(11) 0.0626(8) 0.050(3) Uani 0.328(5) 1 d PDU A 2
H59A H -0.1436 0.0945 0.0202 0.060 Uiso 0.328(5) 1 calc PR A 2
C60A C -0.0738(6) 0.1421(9) 0.0612(7) 0.049(3) Uani 0.328(5) 1 d PDU A 2
H60A H -0.0566 0.1355 0.0172 0.059 Uiso 0.328(5) 1 calc PR A 2
C61 C -0.0408(7) 0.4119(8) 0.1222(7) 0.051(3) Uani 0.666(5) 1 d PDU A 1
C62 C -0.0663(3) 0.4665(5) 0.0635(4) 0.0470(15) Uani 0.666(5) 1 d PDU A 1
H62 H -0.0468 0.4897 0.0243 0.056 Uiso 0.666(5) 1 calc PR A 1
C63 C -0.1170(3) 0.4859(5) 0.0626(4) 0.0626(18) Uani 0.666(5) 1 d PDU A 1
H63 H -0.1328 0.5234 0.0235 0.075 Uiso 0.666(5) 1 calc PR A 1
C64 C -0.1460(3) 0.4514(6) 0.1182(5) 0.089(3) Uani 0.666(5) 1 d PDU A 1
H64 H -0.1819 0.4636 0.1170 0.107 Uiso 0.666(5) 1 calc PR A 1
C65 C -0.12343(19) 0.3993(4) 0.1755(3) 0.0825(18) Uani 0.666(5) 1 d PDU A 1
H65 H -0.1438 0.3757 0.2137 0.099 Uiso 0.666(5) 1 calc PR A 1
C66 C -0.07144(17) 0.3809(3) 0.1780(2) 0.0602(13) Uani 0.666(5) 1 d PDU A 1
H66 H -0.0562 0.3465 0.2186 0.072 Uiso 0.666(5) 1 calc PR A 1
C61A C -0.0367(11) 0.4357(14) 0.1409(13) 0.040(4) Uani 0.334(5) 1 d PDU A 2
C62A C -0.0494(3) 0.4607(6) 0.2096(4) 0.052(2) Uani 0.334(5) 1 d PDU A 2
H62A H -0.0246 0.4594 0.2479 0.062 Uiso 0.334(5) 1 calc PR A 2
C63A C -0.0992(3) 0.4875(6) 0.2211(5) 0.061(2) Uani 0.334(5) 1 d PDU A 2
H63A H -0.1096 0.5043 0.2682 0.073 Uiso 0.334(5) 1 calc PR A 2
C64A C -0.1348(4) 0.4902(8) 0.1631(6) 0.062(3) Uani 0.334(5) 1 d PDU A 2
H64A H -0.1693 0.5099 0.1706 0.075 Uiso 0.334(5) 1 calc PR A 2
C65A C -0.1199(7) 0.4646(12) 0.0964(7) 0.059(4) Uani 0.334(5) 1 d PDU A 2
H65A H -0.1434 0.4671 0.0565 0.070 Uiso 0.334(5) 1 calc PR A 2
C66A C -0.0673(7) 0.4333(11) 0.0871(7) 0.056(4) Uani 0.334(5) 1 d PDU A 2
H66A H -0.0560 0.4115 0.0415 0.067 Uiso 0.334(5) 1 calc PR A 2
C67 C -0.00445(11) 0.6581(2) 0.13702(13) 0.0554(7) Uani 1 1 d DU A .
C68 C -0.0199(2) 0.7342(5) 0.0866(3) 0.0535(13) Uani 0.677(4) 1 d PDU A 1
H68 H -0.0016 0.7407 0.0436 0.064 Uiso 0.677(4) 1 calc PR A 1
C69 C -0.0611(2) 0.8006(5) 0.0971(4) 0.0530(14) Uani 0.677(4) 1 d PDU A 1
H69 H -0.0694 0.8537 0.0626 0.064 Uiso 0.677(4) 1 calc PR A 1
C70 C -0.0903(3) 0.7905(6) 0.1575(4) 0.058(2) Uani 0.677(4) 1 d PDU A 1
H70 H -0.1176 0.8381 0.1656 0.069 Uiso 0.677(4) 1 calc PR A 1
C71 C -0.07914(16) 0.7103(3) 0.2056(2) 0.0570(12) Uani 0.677(4) 1 d PDU A 1
H71 H -0.0999 0.7012 0.2461 0.068 Uiso 0.677(4) 1 calc PR A 1
C72 C -0.03835(16) 0.6428(3) 0.1959(2) 0.0556(11) Uani 0.677(4) 1 d PDU A 1
H72 H -0.0325 0.5857 0.2283 0.067 Uiso 0.677(4) 1 calc PR A 1
C68A C -0.0108(3) 0.7284(6) 0.1969(4) 0.050(2) Uani 0.323(4) 1 d PDU A 2
H68A H 0.0113 0.7255 0.2384 0.060 Uiso 0.323(4) 1 calc PR A 2
C69A C -0.0504(3) 0.8001(6) 0.1911(4) 0.050(2) Uani 0.323(4) 1 d PDU A 2
H69A H -0.0574 0.8449 0.2306 0.060 Uiso 0.323(4) 1 calc PR A 2
C70A C -0.0797(5) 0.8074(11) 0.1295(8) 0.042(3) Uani 0.323(4) 1 d PDU A 2
H70A H -0.1078 0.8549 0.1261 0.051 Uiso 0.323(4) 1 calc PR A 2
C71A C -0.0674(4) 0.7439(9) 0.0717(5) 0.050(2) Uani 0.323(4) 1 d PDU A 2
H71A H -0.0873 0.7477 0.0282 0.060 Uiso 0.323(4) 1 calc PR A 2
C72A C -0.0271(4) 0.6767(9) 0.0772(5) 0.046(2) Uani 0.323(4) 1 d PDU A 2
H72A H -0.0155 0.6427 0.0352 0.055 Uiso 0.323(4) 1 calc PR A 2
C73 C 0.18366(12) 0.5751(2) 0.11673(15) 0.0630(7) Uani 1 1 d U A .
C74 C 0.19921(12) 0.6479(3) 0.06468(16) 0.0724(8) Uani 1 1 d U . .
H74 H 0.1742 0.6834 0.0355 0.087 Uiso 1 1 calc R A .
C75 C 0.25028(14) 0.6683(3) 0.05570(18) 0.0819(10) Uani 1 1 d U A .
H75 H 0.2602 0.7179 0.0205 0.098 Uiso 1 1 calc R . .
C76 C 0.28739(13) 0.6172(3) 0.09748(18) 0.0818(10) Uani 1 1 d U . .
H76 H 0.3226 0.6315 0.0910 0.098 Uiso 1 1 calc R A .
C77 C 0.27273(12) 0.5452(3) 0.14859(17) 0.0745(8) Uani 1 1 d U A .
H77 H 0.2981 0.5093 0.1771 0.089 Uiso 1 1 calc R . .
C78 C 0.22142(12) 0.5250(2) 0.15865(16) 0.0662(8) Uani 1 1 d U . .
H78 H 0.2119 0.4763 0.1947 0.079 Uiso 1 1 calc R A .
B2 B 0.12922(12) 0.3549(2) 0.12254(16) 0.0529(7) Uani 1 1 d U . .


_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 C2 1.721(2) . ?
Cl2 C8 1.721(2) . ?
F1 B1 1.394(3) . ?
F2 B1 1.369(3) . ?
N1 C1 1.354(3) . ?
N1 C4 1.395(3) . ?
N1 B1 1.567(4) . ?
N2 C9 1.358(3) . ?
N2 C6 1.398(3) . ?
N2 B1 1.554(4) . ?
C1 C2 1.406(3) . ?
C1 C10 1.476(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.430(3) . ?
C3 C16 1.475(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.400(3) . ?
C5 C22 1.485(3) . ?
C6 C7 1.428(3) . ?
C7 C8 1.375(3) . ?
C7 C28 1.478(3) . ?
C8 C9 1.405(3) . ?
C9 C34 1.466(3) . ?
C10 C11 1.389(4) . ?
C10 C15 1.396(4) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.392(3) . ?
C16 C17 1.398(3) . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.391(3) . ?
C22 C23 1.397(3) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.374(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.384(3) . ?
C28 C33 1.393(3) . ?
C29 C30 1.381(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.368(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.375(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C39 1.376(4) . ?
C34 C35 1.412(3) . ?
C35 C36 1.370(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.377(4) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
Cl3 C41 1.714(3) . ?
Cl4 C47 1.728(3) . ?
F3 B2 1.362(3) . ?
F4 B2 1.386(3) . ?
N3 C40 1.350(3) . ?
N3 C43 1.399(3) . ?
N3 B2 1.560(4) . ?
N4 C48 1.352(3) . ?
N4 C45 1.396(3) . ?
N4 B2 1.550(4) . ?
C40 C41 1.406(3) . ?
C40 C49A 1.483(11) . ?
C40 C49 1.485(6) . ?
C41 C42 1.377(4) . ?
C42 C43 1.427(4) . ?
C42 C55 1.478(4) . ?
C43 C44 1.395(4) . ?
C44 C45 1.408(4) . ?
C44 C61A 1.50(3) . ?
C44 C61 1.500(18) . ?
C45 C46 1.426(4) . ?
C46 C47 1.374(4) . ?
C46 C67 1.477(4) . ?
C47 C48 1.404(4) . ?
C48 C73 1.468(4) . ?
C49 C50 1.391(8) . ?
C49 C54 1.395(8) . ?
C50 C51 1.381(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.373(10) . ?
C51 H51 0.9500 . ?
C52 C53 1.386(9) . ?
C52 H52 0.9500 . ?
C53 C54 1.373(6) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C49A C50A 1.373(13) . ?
C49A C54A 1.414(13) . ?
C50A C51A 1.375(11) . ?
C50A H50A 0.9500 . ?
C51A C52A 1.387(14) . ?
C51A H51A 0.9500 . ?
C52A C53A 1.378(14) . ?
C52A H52A 0.9500 . ?
C53A C54A 1.391(12) . ?
C53A H53A 0.9500 . ?
C54A H54A 0.9500 . ?
C55 C60A 1.230(14) . ?
C55 C56 1.407(8) . ?
C55 C60 1.412(5) . ?
C55 C56A 1.518(8) . ?
C56 C57 1.364(13) . ?
C56 H56 0.9500 . ?
C57 C58 1.260(13) . ?
C57 H57 0.9500 . ?
C58 C59 1.451(13) . ?
C58 H58 0.9500 . ?
C59 C60 1.379(6) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
C56A C57A 1.375(11) . ?
C56A H56A 0.9500 . ?
C57A C58A 1.31(2) . ?
C57A H57A 0.9500 . ?
C58A C59A 1.577(19) . ?
C58A H58A 0.9500 . ?
C59A C60A 1.39(2) . ?
C59A H59A 0.9500 . ?
C60A H60A 0.9500 . ?
C61 C66 1.387(15) . ?
C61 C62 1.437(17) . ?
C62 C63 1.348(9) . ?
C62 H62 0.9500 . ?
C63 C64 1.373(9) . ?
C63 H63 0.9500 . ?
C64 C65 1.371(10) . ?
C64 H64 0.9500 . ?
C65 C66 1.377(6) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C61A C66A 1.26(3) . ?
C61A C62A 1.37(2) . ?
C62A C63A 1.368(11) . ?
C62A H62A 0.9500 . ?
C63A C64A 1.404(13) . ?
C63A H63A 0.9500 . ?
C64A C65A 1.354(18) . ?
C64A H64A 0.9500 . ?
C65A C66A 1.44(2) . ?
C65A H65A 0.9500 . ?
C66A H66A 0.9500 . ?
C67 C72A 1.266(10) . ?
C67 C68 1.394(6) . ?
C67 C68A 1.440(8) . ?
C67 C72 1.444(5) . ?
C68 C69 1.383(9) . ?
C68 H68 0.9500 . ?
C69 C70 1.385(8) . ?
C69 H69 0.9500 . ?
C70 C71 1.378(9) . ?
C70 H70 0.9500 . ?
C71 C72 1.381(6) . ?
C71 H71 0.9500 . ?
C72 H72 0.9500 . ?
C68A C69A 1.377(11) . ?
C68A H68A 0.9500 . ?
C69A C70A 1.361(17) . ?
C69A H69A 0.9500 . ?
C70A C71A 1.388(16) . ?
C70A H70A 0.9500 . ?
C71A C72A 1.354(14) . ?
C71A H71A 0.9500 . ?
C72A H72A 0.9500 . ?
C73 C78 1.391(4) . ?
C73 C74 1.407(4) . ?
C74 C75 1.374(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.384(5) . ?
C75 H75 0.9500 . ?
C76 C77 1.380(4) . ?
C76 H76 0.9500 . ?
C77 C78 1.383(4) . ?
C77 H77 0.9500 . ?
C78 H78 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 108.8(2) . . ?
C1 N1 B1 126.5(2) . . ?
C4 N1 B1 124.7(2) . . ?
C9 N2 C6 108.84(19) . . ?
C9 N2 B1 125.8(2) . . ?
C6 N2 B1 124.5(2) . . ?
N1 C1 C2 107.4(2) . . ?
N1 C1 C10 126.0(2) . . ?
C2 C1 C10 126.5(2) . . ?
C3 C2 C1 110.6(2) . . ?
C3 C2 Cl1 124.8(2) . . ?
C1 C2 Cl1 124.50(19) . . ?
C2 C3 C4 104.3(2) . . ?
C2 C3 C16 124.7(2) . . ?
C4 C3 C16 131.0(2) . . ?
N1 C4 C5 120.5(2) . . ?
N1 C4 C3 108.9(2) . . ?
C5 C4 C3 130.7(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 C22 118.9(2) . . ?
C4 C5 C22 119.8(2) . . ?
N2 C6 C5 120.6(2) . . ?
N2 C6 C7 108.6(2) . . ?
C5 C6 C7 130.8(2) . . ?
C8 C7 C6 104.6(2) . . ?
C8 C7 C28 122.5(2) . . ?
C6 C7 C28 133.0(2) . . ?
C7 C8 C9 111.1(2) . . ?
C7 C8 Cl2 124.9(2) . . ?
C9 C8 Cl2 123.7(2) . . ?
N2 C9 C8 106.9(2) . . ?
N2 C9 C34 127.9(2) . . ?
C8 C9 C34 125.2(2) . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C1 119.5(2) . . ?
C15 C10 C1 121.5(2) . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C21 C16 C17 117.9(2) . . ?
C21 C16 C3 122.4(2) . . ?
C17 C16 C3 119.7(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.3(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 121.1(2) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C27 C22 C23 119.1(2) . . ?
C27 C22 C5 121.7(2) . . ?
C23 C22 C5 119.2(2) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.1(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C22 120.6(2) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C29 C28 C33 118.5(2) . . ?
C29 C28 C7 122.8(2) . . ?
C33 C28 C7 118.4(2) . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C32 C31 C30 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C28 120.6(2) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C39 C34 C35 118.4(2) . . ?
C39 C34 C9 124.4(2) . . ?
C35 C34 C9 117.0(2) . . ?
C36 C35 C34 120.8(2) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C35 C36 C37 120.0(2) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C38 119.6(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 120.5(3) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C34 C39 C38 120.6(2) . . ?
C34 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
F2 B1 F1 111.6(2) . . ?
F2 B1 N2 111.4(2) . . ?
F1 B1 N2 107.0(2) . . ?
F2 B1 N1 110.7(2) . . ?
F1 B1 N1 109.1(2) . . ?
N2 B1 N1 106.9(2) . . ?
C40 N3 C43 109.2(2) . . ?
C40 N3 B2 125.0(2) . . ?
C43 N3 B2 125.3(2) . . ?
C48 N4 C45 109.3(2) . . ?
C48 N4 B2 125.7(2) . . ?
C45 N4 B2 125.0(2) . . ?
N3 C40 C41 107.2(2) . . ?
N3 C40 C49A 118.8(8) . . ?
C41 C40 C49A 133.3(8) . . ?
N3 C40 C49 127.9(4) . . ?
C41 C40 C49 124.7(4) . . ?
C42 C41 C40 110.5(2) . . ?
C42 C41 Cl3 125.6(2) . . ?
C40 C41 Cl3 123.9(2) . . ?
C41 C42 C43 105.0(2) . . ?
C41 C42 C55 123.4(2) . . ?
C43 C42 C55 131.6(2) . . ?
C44 C43 N3 120.0(2) . . ?
C44 C43 C42 131.8(2) . . ?
N3 C43 C42 108.1(2) . . ?
C43 C44 C45 121.4(2) . . ?
C43 C44 C61A 127.8(7) . . ?
C45 C44 C61A 110.4(6) . . ?
C43 C44 C61 114.7(4) . . ?
C45 C44 C61 123.6(4) . . ?
N4 C45 C44 120.6(2) . . ?
N4 C45 C46 108.3(2) . . ?
C44 C45 C46 131.0(3) . . ?
C47 C46 C45 104.6(2) . . ?
C47 C46 C67 123.4(3) . . ?
C45 C46 C67 132.0(3) . . ?
C46 C47 C48 111.2(2) . . ?
C46 C47 Cl4 125.3(2) . . ?
C48 C47 Cl4 123.4(2) . . ?
N4 C48 C47 106.6(2) . . ?
N4 C48 C73 126.4(2) . . ?
C47 C48 C73 127.0(3) . . ?
C50 C49 C54 118.4(5) . . ?
C50 C49 C40 119.1(5) . . ?
C54 C49 C40 122.4(5) . . ?
C51 C50 C49 120.4(4) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C52 C51 C50 120.5(5) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
C51 C52 C53 119.6(6) . . ?
C51 C52 H52 120.2 . . ?
C53 C52 H52 120.2 . . ?
C54 C53 C52 120.2(5) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C49 120.7(5) . . ?
C53 C54 H54 119.6 . . ?
C49 C54 H54 119.6 . . ?
C50A C49A C54A 120.4(10) . . ?
C50A C49A C40 125.7(10) . . ?
C54A C49A C40 113.7(10) . . ?
C49A C50A C51A 120.8(9) . . ?
C49A C50A H50A 119.6 . . ?
C51A C50A H50A 119.6 . . ?
C50A C51A C52A 119.2(10) . . ?
C50A C51A H51A 120.4 . . ?
C52A C51A H51A 120.4 . . ?
C53A C52A C51A 121.0(12) . . ?
C53A C52A H52A 119.5 . . ?
C51A C52A H52A 119.5 . . ?
C52A C53A C54A 120.2(11) . . ?
C52A C53A H53A 119.9 . . ?
C54A C53A H53A 119.9 . . ?
C53A C54A C49A 118.2(10) . . ?
C53A C54A H54A 120.9 . . ?
C49A C54A H54A 120.9 . . ?
C60A C55 C60 103.5(7) . . ?
C56 C55 C60 114.2(4) . . ?
C60A C55 C42 121.2(7) . . ?
C56 C55 C42 123.3(4) . . ?
C60 C55 C42 120.7(3) . . ?
C60A C55 C56A 121.8(7) . . ?
C56 C55 C56A 108.6(4) . . ?
C42 C55 C56A 116.2(4) . . ?
C57 C56 C55 122.6(7) . . ?
C57 C56 H56 118.7 . . ?
C55 C56 H56 118.7 . . ?
C58 C57 C56 121.4(9) . . ?
C58 C57 H57 119.3 . . ?
C56 C57 H57 119.3 . . ?
C57 C58 C59 122.3(9) . . ?
C57 C58 H58 118.8 . . ?
C59 C58 H58 118.8 . . ?
C60 C59 C58 115.8(6) . . ?
C60 C59 H59 122.1 . . ?
C58 C59 H59 122.1 . . ?
C59 C60 C55 122.7(4) . . ?
C59 C60 H60 118.7 . . ?
C55 C60 H60 118.7 . . ?
C57A C56A C55 115.3(6) . . ?
C57A C56A H56A 122.4 . . ?
C55 C56A H56A 122.4 . . ?
C58A C57A C56A 127.2(11) . . ?
C58A C57A H57A 116.4 . . ?
C56A C57A H57A 116.4 . . ?
C57A C58A C59A 112.3(18) . . ?
C57A C58A H58A 123.8 . . ?
C59A C58A H58A 123.8 . . ?
C60A C59A C58A 119.3(14) . . ?
C60A C59A H59A 120.4 . . ?
C58A C59A H59A 120.4 . . ?
C55 C60A C59A 122.1(11) . . ?
C55 C60A H60A 119.0 . . ?
C59A C60A H60A 119.0 . . ?
C66 C61 C62 116.1(13) . . ?
C66 C61 C44 122.6(11) . . ?
C62 C61 C44 121.1(10) . . ?
C63 C62 C61 121.9(9) . . ?
C63 C62 H62 119.1 . . ?
C61 C62 H62 119.1 . . ?
C62 C63 C64 119.8(6) . . ?
C62 C63 H63 120.1 . . ?
C64 C63 H63 120.1 . . ?
C65 C64 C63 120.5(6) . . ?
C65 C64 H64 119.8 . . ?
C63 C64 H64 119.8 . . ?
C64 C65 C66 120.3(5) . . ?
C64 C65 H65 119.8 . . ?
C66 C65 H65 119.8 . . ?
C65 C66 C61 121.3(8) . . ?
C65 C66 H66 119.4 . . ?
C61 C66 H66 119.4 . . ?
C66A C61A C62A 125(2) . . ?
C66A C61A C44 113.6(16) . . ?
C62A C61A C44 121(2) . . ?
C63A C62A C61A 117.8(14) . . ?
C63A C62A H62A 121.1 . . ?
C61A C62A H62A 121.1 . . ?
C62A C63A C64A 119.6(8) . . ?
C62A C63A H63A 120.2 . . ?
C64A C63A H63A 120.2 . . ?
C65A C64A C63A 119.8(11) . . ?
C65A C64A H64A 120.1 . . ?
C63A C64A H64A 120.1 . . ?
C64A C65A C66A 118.6(13) . . ?
C64A C65A H65A 120.7 . . ?
C66A C65A H65A 120.7 . . ?
C61A C66A C65A 118.7(17) . . ?
C61A C66A H66A 120.6 . . ?
C65A C66A H66A 120.6 . . ?
C72A C67 C68A 120.3(6) . . ?
C72A C67 C72 114.3(5) . . ?
C68 C67 C72 115.6(3) . . ?
C72A C67 C46 114.5(5) . . ?
C68 C67 C46 124.0(3) . . ?
C68A C67 C46 120.0(4) . . ?
C72 C67 C46 120.4(3) . . ?
C69 C68 C67 122.2(4) . . ?
C69 C68 H68 118.9 . . ?
C67 C68 H68 118.9 . . ?
C68 C69 C70 120.7(7) . . ?
C68 C69 H69 119.7 . . ?
C70 C69 H69 119.7 . . ?
C71 C70 C69 119.0(8) . . ?
C71 C70 H70 120.5 . . ?
C69 C70 H70 120.5 . . ?
C70 C71 C72 121.2(4) . . ?
C70 C71 H71 119.4 . . ?
C72 C71 H71 119.4 . . ?
C71 C72 C67 120.7(3) . . ?
C71 C72 H72 119.6 . . ?
C67 C72 H72 119.6 . . ?
C69A C68A C67 116.7(6) . . ?
C69A C68A H68A 121.6 . . ?
C67 C68A H68A 121.6 . . ?
C70A C69A C68A 120.7(8) . . ?
C70A C69A H69A 119.6 . . ?
C68A C69A H69A 119.6 . . ?
C69A C70A C71A 118.4(11) . . ?
C69A C70A H70A 120.8 . . ?
C71A C70A H70A 120.8 . . ?
C72A C71A C70A 120.2(10) . . ?
C72A C71A H71A 119.9 . . ?
C70A C71A H71A 119.9 . . ?
C67 C72A C71A 121.5(8) . . ?
C67 C72A H72A 119.3 . . ?
C71A C72A H72A 119.3 . . ?
C78 C73 C74 118.0(3) . . ?
C78 C73 C48 124.6(3) . . ?
C74 C73 C48 117.4(3) . . ?
C75 C74 C73 120.6(3) . . ?
C75 C74 H74 119.7 . . ?
C73 C74 H74 119.7 . . ?
C74 C75 C76 120.6(3) . . ?
C74 C75 H75 119.7 . . ?
C76 C75 H75 119.7 . . ?
C77 C76 C75 119.4(3) . . ?
C77 C76 H76 120.3 . . ?
C75 C76 H76 120.3 . . ?
C76 C77 C78 120.5(3) . . ?
C76 C77 H77 119.8 . . ?
C78 C77 H77 119.8 . . ?
C77 C78 C73 120.9(3) . . ?
C77 C78 H78 119.6 . . ?
C73 C78 H78 119.6 . . ?
F3 B2 F4 110.4(2) . . ?
F3 B2 N4 109.8(2) . . ?
F4 B2 N4 110.0(2) . . ?
F3 B2 N3 111.9(2) . . ?
F4 B2 N3 108.0(2) . . ?
N4 B2 N3 106.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        60.95
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1453174'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H15 B Cl2 F2 N2 S5'
_chemical_formula_sum            'C29 H15 B Cl2 F2 N2 S5'
_chemical_formula_weight         671.44

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc '
_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                   9.9110(2)
_cell_length_b                   24.3651(5)
_cell_length_c                   12.2192(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.9070(10)
_cell_angle_gamma                90
_cell_volume                     2756.45(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.12

_exptl_crystal_description       lath
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8889
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41084
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         28.39
_reflns_number_total             6904
_reflns_number_gt                5832
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1274P)²+26.3943P] 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         6904
_refine_ls_number_parameters     383
_refine_ls_number_restraints     362
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.1135
_refine_ls_wR_factor_ref         0.2958
_refine_ls_wR_factor_gt          0.2844
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.074
_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 0.34670(14) 0.52204(5) 0.03591(11) 0.0232(3) Uani 1 1 d U . .
Cl2 Cl 1.06973(16) 0.62017(5) 0.83660(11) 0.0269(3) Uani 1 1 d U . .
F1 F 0.6165(4) 0.67449(13) 0.4039(3) 0.0322(8) Uani 1 1 d U . .
F2 F 0.7973(4) 0.65319(14) 0.3356(3) 0.0303(8) Uani 1 1 d U . .
N1 N 0.6186(5) 0.58531(16) 0.3206(4) 0.0166(8) Uani 1 1 d U . .
N2 N 0.8003(5) 0.61113(16) 0.5147(4) 0.0178(8) Uani 1 1 d U . .
C1 C 0.5206(5) 0.5897(2) 0.2105(4) 0.0189(9) Uani 1 1 d U A .
C2 C 0.4703(5) 0.5361(2) 0.1713(4) 0.0174(9) Uani 1 1 d U . .
C3 C 0.5380(5) 0.49836(19) 0.2589(4) 0.0156(9) Uani 1 1 d U B .
C4 C 0.6330(5) 0.53051(18) 0.3546(4) 0.0152(9) Uani 1 1 d U . .
C5 C 0.7275(5) 0.51565(18) 0.4658(4) 0.0139(8) Uani 1 1 d U C .
C6 C 0.8088(5) 0.55572(19) 0.5453(4) 0.0165(9) Uani 1 1 d U . .
C7 C 0.9058(5) 0.55073(19) 0.6637(4) 0.0153(9) Uani 1 1 d U D .
C8 C 0.9499(6) 0.6034(2) 0.7005(4) 0.0188(9) Uani 1 1 d U . .
C9 C 0.8864(6) 0.6409(2) 0.6075(4) 0.0198(10) Uani 1 1 d U . .
C10 C 0.4742(6) 0.6408(2) 0.1472(5) 0.0249(11) Uani 1 1 d DU . .
S1 S 0.5759(8) 0.6912(2) 0.1232(6) 0.0421(14) Uani 0.426(9) 1 d PDU A 1
C11 C 0.3097(19) 0.6524(10) 0.093(2) 0.0492(11) Uani 0.426(9) 1 d PDU A 1
H11 H 0.2327 0.6300 0.0962 0.059 Uiso 0.426(9) 1 calc PR A 1
C12 C 0.300(2) 0.7062(9) 0.0359(19) 0.050(3) Uiso 0.426(9) 1 d PD A 1
H12 H 0.2113 0.7238 -0.0057 0.060 Uiso 0.426(9) 1 calc PR A 1
C13 C 0.4265(19) 0.7277(8) 0.0474(16) 0.044(2) Uiso 0.426(9) 1 d PD A 1
H13 H 0.4334 0.7624 0.0145 0.052 Uiso 0.426(9) 1 calc PR A 1
S1A S 0.3070(5) 0.66183(17) 0.1046(4) 0.0492(11) Uani 0.574(9) 1 d PDU A 2
C11A C 0.575(2) 0.6800(7) 0.1106(17) 0.0421(14) Uani 0.574(9) 1 d PDU A 2
H11A H 0.6752 0.6762 0.1264 0.050 Uiso 0.574(9) 1 calc PR A 2
C12A C 0.4776(16) 0.7248(6) 0.0453(12) 0.044(2) Uiso 0.574(9) 1 d PD A 2
H12A H 0.5070 0.7534 0.0060 0.052 Uiso 0.574(9) 1 calc PR A 2
C13A C 0.3447(19) 0.7205(6) 0.0478(14) 0.050(3) Uiso 0.574(9) 1 d PD A 2
H13A H 0.2751 0.7488 0.0192 0.060 Uiso 0.574(9) 1 calc PR A 2
C14 C 0.5112(6) 0.4396(2) 0.2502(5) 0.0323(14) Uani 1 1 d DU . .
S2 S 0.3649(3) 0.40608(11) 0.2163(3) 0.0333(6) Uani 0.55 1 d PDU B 1
C15 C 0.6357(11) 0.4017(4) 0.2512(10) 0.033(2) Uani 0.55 1 d PDU B 1
H15 H 0.7319 0.4128 0.2632 0.040 Uiso 0.55 1 d PR B 1
C16 C 0.5805(16) 0.3467(5) 0.2308(15) 0.065(5) Uani 0.55 1 d PDU B 1
H16 H 0.6373 0.3156 0.2288 0.078 Uiso 0.55 1 d PR B 1
C17 C 0.439(3) 0.3444(6) 0.215(3) 0.043(4) Uani 0.55 1 d PDU B 1
H17 H 0.3869 0.3110 0.2043 0.052 Uiso 0.55 1 d PR B 1
S2A S 0.5078(5) 0.39740(14) 0.1482(3) 0.0298(12) Uani 0.359(8) 1 d PDU B 2
C15A C 0.4317(7) 0.4104(3) 0.3316(7) 0.025(2) Uani 0.359(8) 1 d PDU B 2
H15A H 0.4101 0.4264 0.3944 0.030 Uiso 0.359(8) 1 d PR B 2
C16A C 0.4029(13) 0.3550(5) 0.2863(13) 0.034(3) Uani 0.45 1 d PDU B 2
H16A H 0.3569 0.3290 0.3193 0.041 Uiso 0.45 1 d PR B 2
C17A C 0.443(4) 0.3423(9) 0.195(4) 0.043(4) Uani 0.45 1 d PDU B 2
H17A H 0.4353 0.3067 0.1614 0.052 Uiso 0.45 1 d PR B 2
C15B C 0.5078(5) 0.39740(14) 0.1482(3) 0.0298(12) Uani 0.091(8) 1 d PU B 3
H15B H 0.5446 0.4029 0.0865 0.036 Uiso 0.091(8) 1 d PR B 3
S2B S 0.4317(7) 0.4104(3) 0.3316(7) 0.025(2) Uani 0.091(8) 1 d PU B 3
C18 C 0.7423(5) 0.45770(18) 0.5027(4) 0.0144(8) Uani 1 1 d DU . .
S3 S 0.6102(3) 0.42455(11) 0.5293(2) 0.0291(3) Uiso 0.57 1 d PD C 1
C19 C 0.8804(10) 0.4236(4) 0.5216(8) 0.0291(3) Uiso 0.57 1 d PD C 1
H19 H 0.9679 0.4337 0.5117 0.035 Uiso 0.57 1 calc PR C 1
C20 C 0.8371(12) 0.3703(4) 0.5596(9) 0.0291(3) Uiso 0.57 1 d PD C 1
H20 H 0.9015 0.3400 0.5800 0.035 Uiso 0.57 1 calc PR C 1
C21 C 0.7101(13) 0.3670(4) 0.5639(9) 0.0291(3) Uiso 0.57 1 d PD C 1
H21 H 0.6746 0.3341 0.5853 0.035 Uiso 0.57 1 calc PR C 1
S3A S 0.6847(6) 0.4314(2) 0.6054(4) 0.0291(3) Uiso 0.239(4) 1 d PD C 2
C19B C 0.6847(6) 0.4314(2) 0.6054(4) 0.0291(3) Uiso 0.196(4) 1 d P C 2
C19A C 0.8078(6) 0.4115(2) 0.4440(5) 0.0291(3) Uiso 0.239(4) 1 d PD C 2
S3B S 0.8078(6) 0.4115(2) 0.4440(5) 0.0291(3) Uiso 0.196(4) 1 d P C 2
H19A H 0.8489 0.4147 0.3849 0.035 Uiso 0.43 1 d PR C 2
C20A C 0.7861(14) 0.3621(5) 0.5092(11) 0.0291(3) Uiso 0.43 1 d PD C 2
H20A H 0.8130 0.3270 0.4901 0.035 Uiso 0.43 1 d PR C 2
C21A C 0.7272(17) 0.3680(5) 0.5965(12) 0.0291(3) Uiso 0.43 1 d PD C 2
H21A H 0.7135 0.3386 0.6426 0.035 Uiso 0.43 1 d PR C 2
C22 C 0.9576(5) 0.50300(19) 0.7403(4) 0.0166(9) Uani 1 1 d DU . .
S4 S 1.1248(3) 0.47831(11) 0.7804(2) 0.0291(3) Uiso 0.545(3) 1 d PD D 1
C23 C 0.8652(11) 0.4756(4) 0.8010(9) 0.0291(3) Uiso 0.545(3) 1 d PD D 1
H23 H 0.7674 0.4825 0.7918 0.035 Uiso 0.545(3) 1 calc PR D 1
C24 C 0.9665(12) 0.4360(4) 0.8773(9) 0.0291(3) Uiso 0.545(3) 1 d PD D 1
H24 H 0.9375 0.4123 0.9267 0.035 Uiso 0.545(3) 1 calc PR D 1
C25 C 1.0956(13) 0.4339(5) 0.8762(10) 0.0291(3) Uiso 0.545(3) 1 d PD D 1
H25 H 1.1677 0.4098 0.9244 0.035 Uiso 0.545(3) 1 calc PR D 1
S4A S 1.0723(4) 0.45718(14) 0.7159(3) 0.0291(3) Uiso 0.455(3) 1 d PD D 2
C23A C 0.9440(13) 0.4939(5) 0.8590(9) 0.0291(3) Uiso 0.455(3) 1 d PD D 2
H23A H 0.8864 0.5143 0.8922 0.035 Uiso 0.455(3) 1 calc PR D 2
C24A C 1.0372(14) 0.4475(5) 0.9115(12) 0.0291(3) Uiso 0.455(3) 1 d PD D 2
H24A H 1.0445 0.4326 0.9853 0.035 Uiso 0.455(3) 1 calc PR D 2
C25A C 1.1120(15) 0.4274(6) 0.8480(10) 0.0291(3) Uiso 0.455(3) 1 d PD D 2
H25A H 1.1813 0.3989 0.8752 0.035 Uiso 0.455(3) 1 calc PR D 2
S5 S 0.9677(3) 0.73598(7) 0.73841(16) 0.0652(8) Uani 1 1 d U . .
C26 C 0.9113(6) 0.7001(2) 0.6087(4) 0.0238(11) Uani 1 1 d U . .
C27 C 0.9009(8) 0.7354(2) 0.5183(6) 0.0360(15) Uani 1 1 d U . .
H27 H 0.8744 0.7240 0.4391 0.043 Uiso 1 1 calc R . .
C28 C 0.9339(8) 0.7905(2) 0.5556(6) 0.0353(14) Uani 1 1 d U . .
H28 H 0.9299 0.8200 0.5038 0.042 Uiso 1 1 calc R . .
C29 C 0.9704(9) 0.7963(2) 0.6692(6) 0.0424(17) Uani 1 1 d U . .
H29 H 0.9956 0.8305 0.7086 0.051 Uiso 1 1 calc R . .
B1 B 0.7065(7) 0.6341(2) 0.3925(5) 0.0190(11) Uani 1 1 d U . .


_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 C2 1.706(5) . ?
Cl2 C8 1.713(5) . ?
F1 B1 1.368(6) . ?
F2 B1 1.399(7) . ?
N1 C1 1.353(6) . ?
N1 C4 1.390(6) . ?
N1 B1 1.548(7) . ?
N2 C9 1.361(6) . ?
N2 C6 1.395(6) . ?
N2 B1 1.555(7) . ?
C1 C2 1.418(7) . ?
C1 C10 1.452(7) . ?
C2 C3 1.389(7) . ?
C3 C4 1.443(6) . ?
C3 C14 1.452(7) . ?
C4 C5 1.395(6) . ?
C5 C6 1.409(6) . ?
C5 C18 1.473(6) . ?
C6 C7 1.429(6) . ?
C7 C8 1.379(7) . ?
C7 C22 1.466(6) . ?
C8 C9 1.418(7) . ?
C9 C26 1.462(7) . ?
C10 C11 1.551(16) . ?
C10 C11A 1.557(15) . ?
C10 S1A 1.632(7) . ?
C10 S1 1.679(8) . ?
S1 C13 1.691(13) . ?
C11 C12 1.472(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.31(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
S1A C13A 1.688(12) . ?
C11A C12A 1.484(16) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.33(2) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14 C15 1.538(10) . ?
C14 S2 1.585(6) . ?
C14 S2A 1.607(6) . ?
C14 C15A 1.635(9) . ?
S2 C17 1.676(16) . ?
C15 C16 1.435(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.34(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 H17A 1.1204 . ?
S2A C17A 1.673(16) . ?
S2A H15B 0.9573 . ?
C15A C16A 1.448(12) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.35(4) . ?
C16A H16A 0.9500 . ?
C17A H17 0.9761 . ?
C17A H17A 0.9500 . ?
C18 C19 1.546(10) . ?
C18 C19A 1.594(7) . ?
C18 S3 1.666(5) . ?
C18 S3A 1.680(6) . ?
S3 C21 1.681(10) . ?
C19 C20 1.492(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.281(17) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
S3A C21A 1.616(12) . ?
C19A C20A 1.500(11) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.39(2) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
C22 C23A 1.520(11) . ?
C22 C23 1.522(10) . ?
C22 S4 1.664(5) . ?
C22 S4A 1.694(5) . ?
S4 C25 1.692(10) . ?
C23 C24 1.464(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.286(16) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
S4A C25A 1.682(11) . ?
C23A C24A 1.455(13) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.343(18) . ?
C24A H24A 0.9500 . ?
C25A H25A 0.9500 . ?
S5 C29 1.701(7) . ?
S5 C26 1.720(5) . ?
C26 C27 1.373(8) . ?
C27 C28 1.417(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.311(10) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 109.5(4) . . ?
C1 N1 B1 124.2(4) . . ?
C4 N1 B1 126.2(4) . . ?
C9 N2 C6 109.5(4) . . ?
C9 N2 B1 126.2(4) . . ?
C6 N2 B1 124.3(4) . . ?
N1 C1 C2 107.7(4) . . ?
N1 C1 C10 125.2(4) . . ?
C2 C1 C10 127.1(4) . . ?
C3 C2 C1 109.5(4) . . ?
C3 C2 Cl1 126.6(4) . . ?
C1 C2 Cl1 123.9(4) . . ?
C2 C3 C4 105.1(4) . . ?
C2 C3 C14 124.8(4) . . ?
C4 C3 C14 130.0(4) . . ?
N1 C4 C5 120.1(4) . . ?
N1 C4 C3 108.1(4) . . ?
C5 C4 C3 131.7(4) . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 C18 120.4(4) . . ?
C6 C5 C18 118.9(4) . . ?
N2 C6 C5 121.4(4) . . ?
N2 C6 C7 107.9(4) . . ?
C5 C6 C7 130.7(4) . . ?
C8 C7 C6 105.7(4) . . ?
C8 C7 C22 122.2(4) . . ?
C6 C7 C22 132.1(4) . . ?
C7 C8 C9 109.9(4) . . ?
C7 C8 Cl2 124.6(4) . . ?
C9 C8 Cl2 125.5(4) . . ?
N2 C9 C8 106.9(4) . . ?
N2 C9 C26 126.0(4) . . ?
C8 C9 C26 127.1(5) . . ?
C1 C10 C11 117.9(11) . . ?
C1 C10 C11A 124.5(9) . . ?
C11 C10 C11A 116.6(14) . . ?
C1 C10 S1A 122.1(4) . . ?
C11A C10 S1A 113.3(9) . . ?
C1 C10 S1 128.6(5) . . ?
C11 C10 S1 113.4(11) . . ?
S1A C10 S1 108.6(4) . . ?
C10 S1 C13 91.0(9) . . ?
C12 C11 C10 104.0(18) . . ?
C12 C11 H11 128.0 . . ?
C10 C11 H11 128.0 . . ?
C13 C12 C11 114.1(19) . . ?
C13 C12 H12 123.0 . . ?
C11 C12 H12 123.0 . . ?
C12 C13 S1 117.5(16) . . ?
C12 C13 H13 121.2 . . ?
S1 C13 H13 121.2 . . ?
C10 S1A C13A 92.8(7) . . ?
C12A C11A C10 104.3(14) . . ?
C12A C11A H11A 127.8 . . ?
C10 C11A H11A 127.8 . . ?
C13A C12A C11A 112.7(14) . . ?
C13A C12A H12A 123.6 . . ?
C11A C12A H12A 123.6 . . ?
C12A C13A S1A 116.2(12) . . ?
C12A C13A H13A 121.9 . . ?
S1A C13A H13A 121.9 . . ?
C3 C14 C15 117.8(6) . . ?
C3 C14 S2 130.8(5) . . ?
C15 C14 S2 110.4(5) . . ?
C3 C14 S2A 129.8(5) . . ?
C3 C14 C15A 120.0(5) . . ?
C15 C14 C15A 107.1(6) . . ?
S2A C14 C15A 108.1(4) . . ?
C14 S2 C17 95.8(11) . . ?
C16 C15 C14 107.7(9) . . ?
C16 C15 H15 126.2 . . ?
C14 C15 H15 126.1 . . ?
C17 C16 C15 112.1(12) . . ?
C17 C16 H16 124.0 . . ?
C15 C16 H16 123.9 . . ?
C16 C17 S2 113.6(16) . . ?
C16 C17 H17 123.0 . . ?
S2 C17 H17 123.4 . . ?
C14 S2A C17A 98.9(16) . . ?
C14 S2A H15B 127.8 . . ?
C17A S2A H15B 133.0 . . ?
C16A C15A C14 104.2(8) . . ?
C16A C15A H15A 128.2 . . ?
C14 C15A H15A 127.6 . . ?
C17A C16A C15A 117.0(14) . . ?
C17A C16A H16A 121.7 . . ?
C15A C16A H16A 121.3 . . ?
C16A C17A S2A 111(2) . . ?
C16A C17A H17A 124.3 . . ?
S2A C17A H17A 124.6 . . ?
C5 C18 C19 123.1(5) . . ?
C5 C18 C19A 123.5(4) . . ?
C5 C18 S3 121.7(3) . . ?
C19 C18 S3 115.2(5) . . ?
C19A C18 S3 102.7(3) . . ?
C5 C18 S3A 124.8(4) . . ?
C19 C18 S3A 101.7(5) . . ?
C19A C18 S3A 111.6(4) . . ?
C18 S3 C21 91.2(5) . . ?
C20 C19 C18 100.2(7) . . ?
C20 C19 H19 129.9 . . ?
C18 C19 H19 129.9 . . ?
C21 C20 C19 117.6(10) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C20 C21 S3 115.8(9) . . ?
C20 C21 H21 122.1 . . ?
S3 C21 H21 122.1 . . ?
C20 C21 H21A 109.2 . . ?
S3 C21 H21A 122.6 . . ?
C21A S3A C18 98.5(6) . . ?
C20A C19A C18 99.7(7) . . ?
C20A C19A H19A 130.7 . . ?
C18 C19A H19A 129.6 . . ?
C21A C20A C19A 120.2(11) . . ?
C21A C20A H20A 120.7 . . ?
C19A C20A H20A 119.0 . . ?
C20A C21A S3A 109.9(11) . . ?
C20A C21A H21A 124.4 . . ?
S3A C21A H21A 125.7 . . ?
C7 C22 C23A 126.5(6) . . ?
C7 C22 C23 121.6(5) . . ?
C7 C22 S4 124.0(4) . . ?
C23A C22 S4 94.8(5) . . ?
C23 C22 S4 114.0(5) . . ?
C7 C22 S4A 121.0(4) . . ?
C23A C22 S4A 111.4(5) . . ?
C23 C22 S4A 110.8(5) . . ?
C22 S4 C25 92.1(5) . . ?
C24 C23 C22 101.8(8) . . ?
C24 C23 H23 129.1 . . ?
C22 C23 H23 129.1 . . ?
C25 C24 C23 118.5(10) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C24 C25 S4 113.5(9) . . ?
C24 C25 H25 123.2 . . ?
S4 C25 H25 123.2 . . ?
C25A S4A C22 93.3(5) . . ?
C24A C23A C22 106.0(9) . . ?
C24A C23A H23A 127.0 . . ?
C22 C23A H23A 127.0 . . ?
C25A C24A C23A 115.0(11) . . ?
C25A C24A H24A 122.5 . . ?
C23A C24A H24A 122.5 . . ?
C24A C25A S4A 114.1(10) . . ?
C24A C25A H25A 122.9 . . ?
S4A C25A H25A 122.9 . . ?
C29 S5 C26 92.2(3) . . ?
C27 C26 C9 130.2(5) . . ?
C27 C26 S5 109.2(4) . . ?
C9 C26 S5 120.5(4) . . ?
C26 C27 C28 113.0(5) . . ?
C26 C27 H27 123.5 . . ?
C28 C27 H27 123.5 . . ?
C29 C28 C27 112.9(6) . . ?
C29 C28 H28 123.6 . . ?
C27 C28 H28 123.6 . . ?
C28 C29 S5 112.6(5) . . ?
C28 C29 H29 123.7 . . ?
S5 C29 H29 123.7 . . ?
F1 B1 F2 111.7(4) . . ?
F1 B1 N1 110.8(5) . . ?
F2 B1 N1 107.8(4) . . ?
F1 B1 N2 110.4(4) . . ?
F2 B1 N2 109.1(4) . . ?
N1 B1 N2 106.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         3.092
_refine_diff_density_min         -2.202
_refine_diff_density_rms         0.172
# END OF CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
