# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_141025g
_audit_block_doi                 10.5517/ccdc.csd.cc1lbvb3
_database_code_depnum_ccdc_archive 'CCDC 1470185'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H22 B4 Cl2 F8 N8 O2 S2'
_chemical_formula_weight         868.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   9.0994(6)
_cell_length_b                   17.1180(10)
_cell_length_c                   11.3594(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.095(2)
_cell_angle_gamma                90.00
_cell_volume                     1751.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1755
_cell_measurement_theta_min      4.694
_cell_measurement_theta_max      70.835

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    3.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_T_max  0.6732
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6076
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.70
_diffrn_reflns_theta_max         67.23
_reflns_number_total             3135
_reflns_number_gt                2354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1471P)²+3.4294P] 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         3135
_refine_ls_number_parameters     268
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0831
_refine_ls_wR_factor_ref         0.2575
_refine_ls_wR_factor_gt          0.2370
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.103
_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
Cl2 Cl 0.2139(15) 0.4498(6) 0.5291(8) 0.196(5) Uani 0.50 1 d PDU . .
S1 S 0.13757(14) 0.82750(7) 1.06346(11) 0.0250(4) Uani 1 1 d . . .
F1 F 0.0970(4) 0.58568(18) 1.2796(3) 0.0423(9) Uani 1 1 d . . .
F2 F -0.0851(4) 0.58093(18) 1.1219(3) 0.0384(8) Uani 1 1 d . . .
F3 F 0.3391(4) 0.55362(18) 0.7467(3) 0.0348(8) Uani 1 1 d . . .
F4 F 0.5457(3) 0.56864(17) 0.8820(3) 0.0306(7) Uani 1 1 d . . .
N1 N 0.0681(4) 0.6954(2) 1.1463(4) 0.0201(9) Uani 1 1 d . . .
N2 N 0.3104(5) 0.5565(2) 0.9501(4) 0.0316(11) Uani 1 1 d . . .
H18 H 0.3153 0.5072 0.9646 0.038 Uiso 1 1 calc R . .
N3 N 0.3759(4) 0.6783(2) 0.8504(4) 0.0213(9) Uani 1 1 d . . .
N4 N 0.2959(4) 0.7174(2) 0.9163(3) 0.0195(9) Uani 1 1 d . . .
O1 O 0.1602(4) 0.56518(19) 1.0920(4) 0.0349(10) Uani 1 1 d . . .
B1 B 0.0563(7) 0.6040(3) 1.1623(6) 0.0267(13) Uani 1 1 d . . .
B2 B 0.3965(7) 0.5865(3) 0.8538(5) 0.0263(12) Uani 1 1 d . . .
C1 C -0.0868(5) 0.7358(3) 1.3006(4) 0.0264(11) Uani 1 1 d . . .
H1 H -0.1059 0.6850 1.3231 0.032 Uiso 1 1 calc R . .
C2 C -0.1431(6) 0.7992(3) 1.3549(5) 0.0303(12) Uani 1 1 d . . .
H2 H -0.2013 0.7909 1.4148 0.036 Uiso 1 1 calc R . .
C3 C -0.1139(6) 0.8758(3) 1.3214(5) 0.0347(13) Uani 1 1 d . . .
H3 H -0.1526 0.9175 1.3597 0.042 Uiso 1 1 calc R . .
C4 C -0.0293(6) 0.8904(3) 1.2329(5) 0.0304(12) Uani 1 1 d . . .
H4 H -0.0103 0.9413 1.2109 0.036 Uiso 1 1 calc R . .
C5 C 0.0274(5) 0.8271(3) 1.1771(4) 0.0236(10) Uani 1 1 d . . .
C6 C -0.0001(5) 0.7504(3) 1.2106(4) 0.0217(10) Uani 1 1 d . . .
C7 C 0.1439(5) 0.7279(3) 1.0670(4) 0.0204(10) Uani 1 1 d . . .
C8 C 0.2243(5) 0.6808(3) 0.9941(4) 0.0185(9) Uani 1 1 d . . .
C9 C 0.2302(5) 0.5981(3) 1.0126(5) 0.0237(10) Uani 1 1 d . . .
C10 C 0.4515(5) 0.7263(3) 0.7732(4) 0.0222(10) Uani 1 1 d . . .
C11 C 0.5174(5) 0.6910(3) 0.6833(4) 0.0272(11) Uani 1 1 d . . .
H11 H 0.5122 0.6372 0.6723 0.033 Uiso 1 1 calc R . .
C12 C 0.5905(6) 0.7373(4) 0.6106(5) 0.0325(12) Uani 1 1 d . . .
H12 H 0.6345 0.7141 0.5502 0.039 Uiso 1 1 calc R . .
C13 C 0.5995(6) 0.8165(3) 0.6255(5) 0.0309(12) Uani 1 1 d . . .
H13 H 0.6489 0.8467 0.5754 0.037 Uiso 1 1 calc R . .
C14 C 0.5344(6) 0.8518(3) 0.7159(5) 0.0326(12) Uani 1 1 d . . .
H14 H 0.5403 0.9056 0.7264 0.039 Uiso 1 1 calc R . .
C15 C 0.4603(6) 0.8060(3) 0.7908(5) 0.0283(11) Uani 1 1 d . . .
H15 H 0.4173 0.8290 0.8518 0.034 Uiso 1 1 calc R . .
Cl1 Cl 0.5000 0.5000 0.5000 0.231(4) Uani 1 2 d SDU . .
C16 C 0.3200(15) 0.489(2) 0.4303(17) 0.222(7) Uani 0.50 1 d PDU . .
H16A H 0.2801 0.5394 0.4028 0.266 Uiso 0.50 1 calc PR . .
H16B H 0.3182 0.4550 0.3619 0.266 Uiso 0.50 1 calc PR . .


_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
Cl2 C16 1.718(10) . ?
S1 C7 1.707(5) . ?
S1 C5 1.743(5) . ?
F1 B1 1.369(7) . ?
F2 B1 1.362(7) . ?
F3 B2 1.375(7) . ?
F4 B2 1.384(7) . ?
N1 C7 1.331(6) . ?
N1 C6 1.391(6) . ?
N1 B1 1.580(6) . ?
N2 C9 1.300(6) . ?
N2 B2 1.521(7) . ?
N3 N4 1.300(6) . ?
N3 C10 1.444(6) . ?
N3 B2 1.583(7) . ?
N4 C8 1.326(6) . ?
O1 C9 1.303(6) . ?
O1 B1 1.478(6) . ?
C1 C2 1.382(7) . ?
C1 C6 1.398(7) . ?
C2 C3 1.402(8) . ?
C3 C4 1.372(8) . ?
C4 C5 1.390(7) . ?
C5 C6 1.400(7) . ?
C7 C8 1.429(7) . ?
C8 C9 1.431(6) . ?
C10 C15 1.380(7) . ?
C10 C11 1.393(7) . ?
C11 C12 1.381(8) . ?
C12 C13 1.367(9) . ?
C13 C14 1.394(8) . ?
C14 C15 1.398(7) . ?
Cl1 C16 1.726(10) 3_666 ?
Cl1 C16 1.726(10) . ?

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
C7 S1 C5 90.0(2) . . ?
C7 N1 C6 112.6(4) . . ?
C7 N1 B1 122.8(4) . . ?
C6 N1 B1 124.6(4) . . ?
C9 N2 B2 126.4(4) . . ?
N4 N3 C10 114.3(4) . . ?
N4 N3 B2 124.7(4) . . ?
C10 N3 B2 121.0(4) . . ?
N3 N4 C8 120.6(4) . . ?
C9 O1 B1 126.3(4) . . ?
F2 B1 F1 112.0(5) . . ?
F2 B1 O1 109.5(4) . . ?
F1 B1 O1 108.5(4) . . ?
F2 B1 N1 108.9(4) . . ?
F1 B1 N1 109.0(4) . . ?
O1 B1 N1 108.9(4) . . ?
F3 B2 F4 110.6(4) . . ?
F3 B2 N2 109.2(4) . . ?
F4 B2 N2 110.3(5) . . ?
F3 B2 N3 110.8(4) . . ?
F4 B2 N3 109.5(4) . . ?
N2 B2 N3 106.4(4) . . ?
C2 C1 C6 117.9(5) . . ?
C1 C2 C3 121.2(5) . . ?
C4 C3 C2 121.1(5) . . ?
C3 C4 C5 118.4(5) . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 S1 128.6(4) . . ?
C6 C5 S1 110.4(4) . . ?
N1 C6 C1 127.0(5) . . ?
N1 C6 C5 112.5(4) . . ?
C1 C6 C5 120.5(5) . . ?
N1 C7 C8 120.9(4) . . ?
N1 C7 S1 114.5(4) . . ?
C8 C7 S1 124.6(4) . . ?
N4 C8 C7 117.4(4) . . ?
N4 C8 C9 123.6(4) . . ?
C7 C8 C9 119.0(4) . . ?
N2 C9 O1 120.5(4) . . ?
N2 C9 C8 118.3(4) . . ?
O1 C9 C8 121.2(4) . . ?
C15 C10 C11 120.9(5) . . ?
C15 C10 N3 119.8(4) . . ?
C11 C10 N3 119.3(4) . . ?
C12 C11 C10 118.9(5) . . ?
C13 C12 C11 121.4(5) . . ?
C12 C13 C14 119.8(5) . . ?
C13 C14 C15 119.8(5) . . ?
C10 C15 C14 119.3(5) . . ?
C16 Cl1 C16 180.000(1) 3_666 . ?
Cl2 C16 Cl1 109.1(10) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.563
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.138

####################################################################### 
# 
# 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_exp_3964
_audit_block_doi                 10.5517/ccdc.csd.cc1lbvg7
_database_code_depnum_ccdc_archive 'CCDC 1470189'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H26 B4 Cl2 F8 N8 O2 S2'
_chemical_formula_weight         968.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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

_cell_length_a                   10.6491(7)
_cell_length_b                   22.7467(13)
_cell_length_c                   17.0946(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.248(7)
_cell_angle_gamma                90.00
_cell_volume                     4013.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4236
_cell_measurement_theta_min      3.0380
_cell_measurement_theta_max      25.8570

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1960
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30469
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.02
_reflns_number_total             7079
_reflns_number_gt                4409
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0975P)²+3.5309P] 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         7079
_refine_ls_number_parameters     586
_refine_ls_number_restraints     2196
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.2083
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29127(11) 0.44951(5) 0.77839(6) 0.0457(3) Uani 1 1 d U . .
S2 S 0.16566(10) 0.45097(5) 0.95271(6) 0.0464(3) Uani 1 1 d U . .
Cl1 Cl 0.89626(15) 0.56166(7) 0.61162(11) 0.0911(5) Uani 1 1 d U . .
Cl2 Cl 0.64235(15) 0.55267(8) 0.63951(9) 0.0902(5) Uani 1 1 d U . .
F1 F 0.5912(3) 0.39369(12) 0.62178(18) 0.0708(8) Uani 1 1 d U . .
F2 F 0.4060(3) 0.34653(11) 0.56291(14) 0.0654(7) Uani 1 1 d U . .
F3 F 0.6344(3) 0.23983(17) 0.93578(17) 0.0975(11) Uani 1 1 d U . .
F4 F 0.4638(3) 0.18643(12) 0.8741(2) 0.0913(10) Uani 1 1 d U . .
F5 F 0.0867(3) 0.35068(11) 1.18640(14) 0.0630(7) Uani 1 1 d U . .
F6 F -0.0966(3) 0.40033(12) 1.13238(16) 0.0689(8) Uani 1 1 d U . .
F7 F 0.0123(4) 0.18070(12) 0.8889(2) 0.0989(11) Uani 1 1 d U . .
F8 F -0.1584(3) 0.23199(17) 0.82311(17) 0.0953(11) Uani 1 1 d U . .
N1 N 0.4068(3) 0.40888(13) 0.67534(17) 0.0358(7) Uani 1 1 d U . .
N2 N 0.5441(4) 0.25767(16) 0.7966(2) 0.0561(10) Uani 1 1 d U . .
H40 H 0.5887 0.2337 0.7754 0.067 Uiso 1 1 calc R . .
N3 N 0.4315(3) 0.28923(14) 0.90015(18) 0.0376(7) Uani 1 1 d U . .
N4 N 0.3922(3) 0.33642(13) 0.85785(17) 0.0335(7) Uani 1 1 d U . .
N5 N 0.0794(3) 0.41080(14) 1.06990(18) 0.0384(7) Uani 1 1 d U . .
N6 N -0.0653(4) 0.25624(16) 0.9607(2) 0.0566(10) Uani 1 1 d U . .
H41 H -0.1079 0.2334 0.9849 0.068 Uiso 1 1 calc R . .
N7 N 0.0437(3) 0.28194(14) 0.85298(18) 0.0382(7) Uani 1 1 d U . .
N8 N 0.0799(3) 0.33161(14) 0.88951(17) 0.0357(7) Uani 1 1 d U . .
O1 O 0.5273(3) 0.31442(13) 0.68651(17) 0.0567(8) Uani 1 1 d U . .
O2 O -0.0462(3) 0.31802(13) 1.06619(16) 0.0581(8) Uani 1 1 d U . .
B1 B 0.4856(5) 0.3659(2) 0.6338(3) 0.0429(11) Uani 1 1 d U . .
B2 B 0.5228(5) 0.2410(2) 0.8787(3) 0.0550(13) Uani 1 1 d U . .
B3 B 0.0034(5) 0.3698(2) 1.1171(3) 0.0445(11) Uani 1 1 d U . .
B4 B -0.0473(5) 0.2350(3) 0.8795(3) 0.0554(12) Uani 1 1 d U . .
C1 C 0.2875(4) 0.49095(17) 0.6926(2) 0.0429(9) Uani 1 1 d U . .
C2 C 0.2284(4) 0.54504(19) 0.6708(3) 0.0558(11) Uani 1 1 d U . .
H2 H 0.1852 0.5644 0.7043 0.067 Uiso 1 1 calc R . .
C3 C 0.2357(5) 0.5686(2) 0.5994(3) 0.0656(13) Uani 1 1 d U . .
H3 H 0.1964 0.6046 0.5836 0.079 Uiso 1 1 calc R . .
C4 C 0.3000(5) 0.5404(2) 0.5497(3) 0.0611(12) Uani 1 1 d U . .
H4 H 0.3028 0.5579 0.5010 0.073 Uiso 1 1 calc R . .
C5 C 0.3605(4) 0.48717(19) 0.5699(2) 0.0503(10) Uani 1 1 d U . .
H5 H 0.4041 0.4684 0.5361 0.060 Uiso 1 1 calc R . .
C6 C 0.3535(4) 0.46276(17) 0.6431(2) 0.0397(9) Uani 1 1 d U . .
C7 C 0.3800(3) 0.39696(16) 0.7455(2) 0.0337(8) Uani 1 1 d U . .
C8 C 0.4259(3) 0.34450(16) 0.7883(2) 0.0342(8) Uani 1 1 d U . .
C9 C 0.5013(4) 0.30453(18) 0.7556(2) 0.0405(9) Uani 1 1 d U . .
C10 C 0.3904(3) 0.28568(17) 0.9746(2) 0.0367(8) Uani 1 1 d U . .
C11 C 0.3249(4) 0.23713(18) 0.9878(2) 0.0444(9) Uani 1 1 d U . .
H11 H 0.3082 0.2073 0.9494 0.053 Uiso 1 1 calc R . .
C12 C 0.2821(4) 0.2312(2) 1.0583(3) 0.0503(10) Uani 1 1 d U . .
H12 H 0.2370 0.1977 1.0664 0.060 Uiso 1 1 calc R . .
C13 C 0.3060(4) 0.2741(2) 1.1148(2) 0.0489(10) Uani 1 1 d U . .
H13 H 0.2765 0.2698 1.1614 0.059 Uiso 1 1 calc R . .
C14 C 0.3753(4) 0.32516(19) 1.1040(2) 0.0428(9) Uani 1 1 d U . .
C15 C 0.4186(3) 0.33176(18) 1.0325(2) 0.0393(9) Uani 1 1 d U . .
C16 C 0.4918(4) 0.38262(19) 1.0241(2) 0.0508(10) Uani 1 1 d U . .
H16 H 0.5231 0.3873 0.9783 0.061 Uiso 1 1 calc R . .
C17 C 0.5165(5) 0.4248(2) 1.0828(3) 0.0625(12) Uani 1 1 d U . .
H17 H 0.5647 0.4578 1.0770 0.075 Uiso 1 1 calc R . .
C18 C 0.4691(5) 0.4182(2) 1.1522(3) 0.0640(13) Uani 1 1 d U . .
H18 H 0.4845 0.4476 1.1912 0.077 Uiso 1 1 calc R . .
C19 C 0.4021(4) 0.3701(2) 1.1630(3) 0.0559(11) Uani 1 1 d U . .
H19 H 0.3729 0.3663 1.2097 0.067 Uiso 1 1 calc R . .
C20 C 0.1845(4) 0.49392(19) 1.0390(2) 0.0449(10) Uani 1 1 d U . .
C21 C 0.2418(4) 0.5486(2) 1.0530(3) 0.0571(11) Uani 1 1 d U . .
H21 H 0.2707 0.5684 1.0131 0.069 Uiso 1 1 calc R . .
C22 C 0.2545(4) 0.5728(2) 1.1292(3) 0.0599(12) Uani 1 1 d U . .
H22 H 0.2927 0.6096 1.1408 0.072 Uiso 1 1 calc R . .
C23 C 0.2113(4) 0.5432(2) 1.1880(3) 0.0576(12) Uani 1 1 d U . .
H23 H 0.2251 0.5595 1.2392 0.069 Uiso 1 1 calc R . .
C24 C 0.1485(4) 0.4900(2) 1.1727(2) 0.0523(11) Uani 1 1 d U . .
H24 H 0.1161 0.4713 1.2120 0.063 Uiso 1 1 calc R . .
C25 C 0.1347(4) 0.46510(17) 1.0966(2) 0.0406(9) Uani 1 1 d U . .
C26 C 0.0929(3) 0.39768(17) 0.9963(2) 0.0365(8) Uani 1 1 d U . .
C27 C 0.0478(3) 0.34342(16) 0.9583(2) 0.0352(8) Uani 1 1 d U . .
C28 C -0.0233(4) 0.30507(19) 0.9973(2) 0.0463(10) Uani 1 1 d U . .
C29 C 0.0878(4) 0.27382(18) 0.7802(2) 0.0385(9) Uani 1 1 d U . .
C30 C 0.1533(4) 0.22436(19) 0.7718(2) 0.0480(10) Uani 1 1 d U . .
H30 H 0.1655 0.1955 0.8115 0.058 Uiso 1 1 calc R . .
C31 C 0.2034(4) 0.2159(2) 0.7038(3) 0.0564(11) Uani 1 1 d U . .
H31 H 0.2483 0.1817 0.6987 0.068 Uiso 1 1 calc R . .
C32 C 0.1861(4) 0.2577(2) 0.6456(3) 0.0525(11) Uani 1 1 d U . .
H32 H 0.2219 0.2524 0.6016 0.063 Uiso 1 1 calc R . .
C33 C 0.1145(4) 0.30879(19) 0.6510(2) 0.0423(9) Uani 1 1 d U . .
C34 C 0.0627(4) 0.31748(17) 0.7193(2) 0.0387(9) Uani 1 1 d U . .
C35 C -0.0168(4) 0.36739(19) 0.7200(2) 0.0484(10) Uani 1 1 d U . .
H35 H -0.0545 0.3731 0.7630 0.058 Uiso 1 1 calc R . .
C36 C -0.0385(5) 0.4067(2) 0.6588(3) 0.0598(12) Uani 1 1 d U . .
H36 H -0.0924 0.4388 0.6597 0.072 Uiso 1 1 calc R . .
C37 C 0.0191(5) 0.3999(2) 0.5943(3) 0.0606(12) Uani 1 1 d U . .
H37 H 0.0069 0.4282 0.5540 0.073 Uiso 1 1 calc R . .
C38 C 0.0920(4) 0.3525(2) 0.5903(2) 0.0516(11) Uani 1 1 d U . .
H38 H 0.1287 0.3483 0.5466 0.062 Uiso 1 1 calc R . .
C39 C 0.7617(5) 0.5997(2) 0.6227(3) 0.0733(15) Uani 1 1 d U . .
H39A H 0.7269 0.6226 0.5743 0.088 Uiso 1 1 calc R . .
H39B H 0.7869 0.6267 0.6677 0.088 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.703(4) . ?
S1 C1 1.736(4) . ?
S2 C26 1.705(4) . ?
S2 C20 1.740(4) . ?
Cl1 C39 1.723(5) . ?
Cl2 C39 1.738(5) . ?
F1 B1 1.350(5) . ?
F2 B1 1.369(5) . ?
F3 B2 1.339(6) . ?
F4 B2 1.385(6) . ?
F5 B3 1.365(5) . ?
F6 B3 1.350(5) . ?
F7 B4 1.381(6) . ?
F8 B4 1.332(6) . ?
N1 C7 1.327(4) . ?
N1 C6 1.404(5) . ?
N1 B1 1.568(5) . ?
N2 C9 1.295(5) . ?
N2 B2 1.524(6) . ?
N3 N4 1.304(4) . ?
N3 C10 1.446(4) . ?
N3 B2 1.568(6) . ?
N4 C8 1.336(4) . ?
N5 C26 1.335(4) . ?
N5 C25 1.396(5) . ?
N5 B3 1.579(6) . ?
N6 C28 1.299(5) . ?
N6 B4 1.525(6) . ?
N7 N8 1.302(4) . ?
N7 C29 1.446(5) . ?
N7 B4 1.581(6) . ?
N8 C27 1.331(4) . ?
O1 C9 1.298(4) . ?
O1 B1 1.477(5) . ?
O2 C28 1.294(5) . ?
O2 B3 1.483(6) . ?
C1 C6 1.383(5) . ?
C1 C2 1.391(6) . ?
C2 C3 1.353(7) . ?
C3 C4 1.373(7) . ?
C4 C5 1.376(6) . ?
C5 C6 1.388(5) . ?
C7 C8 1.422(5) . ?
C8 C9 1.416(5) . ?
C10 C11 1.355(5) . ?
C10 C15 1.422(5) . ?
C11 C12 1.396(5) . ?
C12 C13 1.351(6) . ?
C13 C14 1.413(6) . ?
C14 C19 1.415(6) . ?
C14 C15 1.417(5) . ?
C15 C16 1.421(6) . ?
C16 C17 1.366(6) . ?
C17 C18 1.406(6) . ?
C18 C19 1.343(7) . ?
C20 C21 1.381(6) . ?
C20 C25 1.392(6) . ?
C21 C22 1.390(6) . ?
C22 C23 1.379(7) . ?
C23 C24 1.375(6) . ?
C24 C25 1.392(5) . ?
C26 C27 1.422(5) . ?
C27 C28 1.423(5) . ?
C29 C30 1.350(5) . ?
C29 C34 1.416(5) . ?
C30 C31 1.408(6) . ?
C31 C32 1.354(6) . ?
C32 C33 1.406(6) . ?
C33 C38 1.414(6) . ?
C33 C34 1.423(5) . ?
C34 C35 1.418(6) . ?
C35 C36 1.353(6) . ?
C36 C37 1.395(6) . ?
C37 C38 1.339(6) . ?

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
C7 S1 C1 90.07(18) . . ?
C26 S2 C20 89.93(19) . . ?
C7 N1 C6 112.1(3) . . ?
C7 N1 B1 122.6(3) . . ?
C6 N1 B1 125.2(3) . . ?
C9 N2 B2 126.2(4) . . ?
N4 N3 C10 114.1(3) . . ?
N4 N3 B2 125.4(3) . . ?
C10 N3 B2 120.4(3) . . ?
N3 N4 C8 119.1(3) . . ?
C26 N5 C25 111.8(3) . . ?
C26 N5 B3 122.5(3) . . ?
C25 N5 B3 125.6(3) . . ?
C28 N6 B4 127.1(4) . . ?
N8 N7 C29 113.8(3) . . ?
N8 N7 B4 125.3(3) . . ?
C29 N7 B4 120.8(3) . . ?
N7 N8 C27 119.3(3) . . ?
C9 O1 B1 126.4(3) . . ?
C28 O2 B3 126.5(3) . . ?
F1 B1 F2 111.9(4) . . ?
F1 B1 O1 109.1(4) . . ?
F2 B1 O1 108.3(4) . . ?
F1 B1 N1 109.6(4) . . ?
F2 B1 N1 108.5(3) . . ?
O1 B1 N1 109.4(3) . . ?
F3 B2 F4 109.4(4) . . ?
F3 B2 N2 111.7(4) . . ?
F4 B2 N2 109.8(4) . . ?
F3 B2 N3 109.5(4) . . ?
F4 B2 N3 109.9(4) . . ?
N2 B2 N3 106.4(3) . . ?
F6 B3 F5 111.7(4) . . ?
F6 B3 O2 109.7(4) . . ?
F5 B3 O2 108.5(4) . . ?
F6 B3 N5 108.9(4) . . ?
F5 B3 N5 109.1(3) . . ?
O2 B3 N5 108.9(3) . . ?
F8 B4 F7 109.8(5) . . ?
F8 B4 N6 112.8(4) . . ?
F7 B4 N6 109.6(4) . . ?
F8 B4 N7 109.0(4) . . ?
F7 B4 N7 109.9(4) . . ?
N6 B4 N7 105.7(4) . . ?
C6 C1 C2 120.7(4) . . ?
C6 C1 S1 110.8(3) . . ?
C2 C1 S1 128.5(3) . . ?
C3 C2 C1 118.0(5) . . ?
C2 C3 C4 121.4(5) . . ?
C3 C4 C5 122.0(5) . . ?
C4 C5 C6 116.9(4) . . ?
C1 C6 C5 120.9(4) . . ?
C1 C6 N1 112.4(3) . . ?
C5 C6 N1 126.6(4) . . ?
N1 C7 C8 120.9(3) . . ?
N1 C7 S1 114.5(3) . . ?
C8 C7 S1 124.6(3) . . ?
N4 C8 C9 124.4(3) . . ?
N4 C8 C7 116.1(3) . . ?
C9 C8 C7 119.5(3) . . ?
N2 C9 O1 120.6(4) . . ?
N2 C9 C8 118.3(3) . . ?
O1 C9 C8 121.1(3) . . ?
C11 C10 C15 120.9(4) . . ?
C11 C10 N3 118.2(3) . . ?
C15 C10 N3 120.9(3) . . ?
C10 C11 C12 120.9(4) . . ?
C13 C12 C11 120.3(4) . . ?
C12 C13 C14 120.8(4) . . ?
C13 C14 C19 121.4(4) . . ?
C13 C14 C15 119.4(4) . . ?
C19 C14 C15 119.1(4) . . ?
C14 C15 C16 118.4(4) . . ?
C14 C15 C10 117.7(4) . . ?
C16 C15 C10 123.9(4) . . ?
C17 C16 C15 120.6(4) . . ?
C16 C17 C18 120.1(5) . . ?
C19 C18 C17 121.0(4) . . ?
C18 C19 C14 120.7(4) . . ?
C21 C20 C25 122.1(4) . . ?
C21 C20 S2 127.4(3) . . ?
C25 C20 S2 110.5(3) . . ?
C20 C21 C22 117.1(4) . . ?
C23 C22 C21 121.1(5) . . ?
C24 C23 C22 121.7(4) . . ?
C23 C24 C25 118.0(4) . . ?
C24 C25 C20 119.8(4) . . ?
C24 C25 N5 127.2(4) . . ?
C20 C25 N5 112.9(3) . . ?
N5 C26 C27 121.4(3) . . ?
N5 C26 S2 114.8(3) . . ?
C27 C26 S2 123.8(3) . . ?
N8 C27 C26 116.6(3) . . ?
N8 C27 C28 124.9(4) . . ?
C26 C27 C28 118.5(3) . . ?
O2 C28 N6 120.9(4) . . ?
O2 C28 C27 121.8(4) . . ?
N6 C28 C27 117.3(4) . . ?
C30 C29 C34 121.0(4) . . ?
C30 C29 N7 118.9(4) . . ?
C34 C29 N7 120.0(3) . . ?
C29 C30 C31 120.8(4) . . ?
C32 C31 C30 120.1(4) . . ?
C31 C32 C33 120.6(4) . . ?
C32 C33 C38 122.0(4) . . ?
C32 C33 C34 119.7(4) . . ?
C38 C33 C34 118.3(4) . . ?
C29 C34 C35 124.1(4) . . ?
C29 C34 C33 117.7(4) . . ?
C35 C34 C33 118.1(4) . . ?
C36 C35 C34 120.8(4) . . ?
C35 C36 C37 120.8(5) . . ?
C38 C37 C36 120.2(4) . . ?
C37 C38 C33 121.6(4) . . ?
Cl1 C39 Cl2 111.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_exp_3965
_audit_block_doi                 10.5517/ccdc.csd.cc1lbvd5
_database_code_depnum_ccdc_archive 'CCDC 1470187'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 B F2 N4 S'
_chemical_formula_weight         376.19

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'
S S 0.1246 0.1234 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   13.7279(18)
_cell_length_b                   8.6809(13)
_cell_length_c                   14.7591(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.207(12)
_cell_angle_gamma                90.00
_cell_volume                     1697.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    980
_cell_measurement_theta_min      2.8490
_cell_measurement_theta_max      23.4570

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6609
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3000
_reflns_number_gt                1821
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0382P)²+0.0311P] 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         3000
_refine_ls_number_parameters     244
_refine_ls_number_restraints     780
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08993(6) 0.63774(10) 0.46504(5) 0.0498(3) Uani 1 1 d U . .
F1 F 0.32036(14) 0.3964(2) 0.31488(11) 0.0683(6) Uani 1 1 d U . .
F2 F 0.40376(12) 0.6090(2) 0.37825(11) 0.0710(6) Uani 1 1 d U . .
N1 N 0.24053(16) 0.5632(3) 0.40290(14) 0.0393(6) Uani 1 1 d U . .
N2 N 0.25878(17) 0.6382(3) 0.24571(15) 0.0453(6) Uani 1 1 d U . .
N3 N 0.17210(18) 0.7104(3) 0.22690(15) 0.0454(6) Uani 1 1 d U . .
N4 N -0.0456(2) 0.8640(4) 0.25158(19) 0.0734(9) Uani 1 1 d U . .
B1 B 0.3110(3) 0.5496(5) 0.3359(2) 0.0466(9) Uani 1 1 d U . .
C1 C 0.1830(2) 0.5231(3) 0.53534(19) 0.0446(7) Uani 1 1 d U . .
C2 C 0.1876(2) 0.4628(4) 0.6234(2) 0.0559(9) Uani 1 1 d U . .
H2 H 0.1368 0.4822 0.6530 0.067 Uiso 1 1 calc R . .
C3 C 0.2689(3) 0.3745(4) 0.6653(2) 0.0632(10) Uani 1 1 d U . .
H3 H 0.2729 0.3314 0.7239 0.076 Uiso 1 1 calc R . .
C4 C 0.3457(3) 0.3476(4) 0.6224(2) 0.0643(9) Uani 1 1 d U . .
H4 H 0.4008 0.2882 0.6535 0.077 Uiso 1 1 calc R . .
C5 C 0.3429(2) 0.4060(4) 0.5355(2) 0.0567(9) Uani 1 1 d U . .
H5 H 0.3947 0.3875 0.5071 0.068 Uiso 1 1 calc R . .
C6 C 0.2592(2) 0.4941(3) 0.49166(19) 0.0437(7) Uani 1 1 d U . .
C7 C 0.1546(2) 0.6402(3) 0.38007(19) 0.0388(7) Uani 1 1 d U . .
C8 C 0.1212(2) 0.7143(3) 0.29194(19) 0.0416(7) Uani 1 1 d U . .
C9 C 0.3085(2) 0.6404(4) 0.1706(2) 0.0470(8) Uani 1 1 d U . .
C10 C 0.3982(2) 0.7166(4) 0.1855(2) 0.0637(9) Uani 1 1 d U . .
H10 H 0.4240 0.7688 0.2418 0.076 Uiso 1 1 calc R . .
C11 C 0.4517(3) 0.7168(5) 0.1167(2) 0.0730(11) Uani 1 1 d U . .
H11 H 0.5133 0.7677 0.1275 0.088 Uiso 1 1 calc R . .
C12 C 0.4136(3) 0.6431(4) 0.0346(2) 0.0656(10) Uani 1 1 d U . .
H12 H 0.4501 0.6430 -0.0103 0.079 Uiso 1 1 calc R . .
C13 C 0.3193(2) 0.5654(4) 0.0151(2) 0.0515(8) Uani 1 1 d U . .
C14 C 0.2658(2) 0.5632(3) 0.08488(19) 0.0432(7) Uani 1 1 d U . .
C15 C 0.1724(2) 0.4818(4) 0.0660(2) 0.0553(8) Uani 1 1 d U . .
H15 H 0.1364 0.4773 0.1113 0.066 Uiso 1 1 calc R . .
C16 C 0.1360(3) 0.4106(4) -0.0186(2) 0.0641(9) Uani 1 1 d U . .
H16 H 0.0748 0.3583 -0.0310 0.077 Uiso 1 1 calc R . .
C17 C 0.1903(3) 0.4155(4) -0.0871(2) 0.0714(10) Uani 1 1 d U . .
H17 H 0.1650 0.3660 -0.1443 0.086 Uiso 1 1 calc R . .
C18 C 0.2788(3) 0.4916(4) -0.0704(2) 0.0695(10) Uani 1 1 d U . .
H18 H 0.3135 0.4950 -0.1168 0.083 Uiso 1 1 calc R . .
C19 C 0.0291(2) 0.7978(4) 0.2679(2) 0.0498(8) 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
S1 C7 1.717(3) . ?
S1 C1 1.733(3) . ?
F1 B1 1.379(4) . ?
F2 B1 1.364(4) . ?
N1 C7 1.320(3) . ?
N1 C6 1.402(3) . ?
N1 B1 1.558(4) . ?
N2 N3 1.309(3) . ?
N2 C9 1.446(3) . ?
N2 B1 1.542(4) . ?
N3 C8 1.327(3) . ?
N4 C19 1.145(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.361(4) . ?
C3 C4 1.386(4) . ?
C4 C5 1.370(4) . ?
C5 C6 1.390(4) . ?
C7 C8 1.415(4) . ?
C8 C19 1.420(4) . ?
C9 C10 1.364(4) . ?
C9 C14 1.416(4) . ?
C10 C11 1.402(4) . ?
C11 C12 1.348(4) . ?
C12 C13 1.421(4) . ?
C13 C18 1.394(4) . ?
C13 C14 1.413(3) . ?
C14 C15 1.426(4) . ?
C15 C16 1.366(4) . ?
C16 C17 1.405(4) . ?
C17 C18 1.348(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C1 90.17(13) . . ?
C7 N1 C6 112.8(2) . . ?
C7 N1 B1 122.5(2) . . ?
C6 N1 B1 124.6(2) . . ?
N3 N2 C9 114.6(2) . . ?
N3 N2 B1 127.8(2) . . ?
C9 N2 B1 117.6(2) . . ?
N2 N3 C8 118.7(2) . . ?
F2 B1 F1 109.7(3) . . ?
F2 B1 N2 112.0(3) . . ?
F1 B1 N2 109.7(2) . . ?
F2 B1 N1 109.9(2) . . ?
F1 B1 N1 109.0(3) . . ?
N2 B1 N1 106.5(2) . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 S1 128.5(2) . . ?
C6 C1 S1 110.7(2) . . ?
C3 C2 C1 117.9(3) . . ?
C2 C3 C4 121.3(3) . . ?
C5 C4 C3 121.8(3) . . ?
C4 C5 C6 117.2(3) . . ?
C1 C6 C5 121.0(3) . . ?
C1 C6 N1 112.4(3) . . ?
C5 C6 N1 126.7(3) . . ?
N1 C7 C8 121.2(2) . . ?
N1 C7 S1 113.9(2) . . ?
C8 C7 S1 124.9(2) . . ?
N3 C8 C7 123.2(3) . . ?
N3 C8 C19 115.8(3) . . ?
C7 C8 C19 120.9(2) . . ?
C10 C9 C14 121.2(3) . . ?
C10 C9 N2 118.1(3) . . ?
C14 C9 N2 120.7(3) . . ?
C9 C10 C11 120.4(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 121.7(3) . . ?
C18 C13 C14 119.6(3) . . ?
C18 C13 C12 121.8(3) . . ?
C14 C13 C12 118.6(3) . . ?
C13 C14 C9 118.2(3) . . ?
C13 C14 C15 118.5(3) . . ?
C9 C14 C15 123.3(2) . . ?
C16 C15 C14 119.8(3) . . ?
C15 C16 C17 120.6(3) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C13 121.1(3) . . ?
N4 C19 C8 177.7(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_exp_6214
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv92
_database_code_depnum_ccdc_archive 'CCDC 1470184'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 B F2 N4 O0 S'
_chemical_formula_weight         326.13

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   11.0689(6)
_cell_length_b                   10.5398(5)
_cell_length_c                   25.7733(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.097(5)
_cell_angle_gamma                90.00
_cell_volume                     2841.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1785
_cell_measurement_theta_min      4.2170
_cell_measurement_theta_max      66.5680

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8394
_exptl_absorpt_correction_T_max  0.8574
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9841
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.1158
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         67.25
_reflns_number_total             5092
_reflns_number_gt                2235
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1215P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5092
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.3081
_refine_ls_wR_factor_gt          0.2111
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27914(19) 0.76599(18) 0.90764(9) 0.0748(6) Uani 1 1 d . . .
S2 S 0.59913(18) 1.02924(18) 0.95468(9) 0.0739(6) Uani 1 1 d . . .
B1 B 0.3915(8) 0.4706(8) 0.8326(4) 0.074(2) Uani 1 1 d . . .
B2 B 0.7270(8) 0.7710(8) 0.8677(4) 0.071(2) Uani 1 1 d . . .
F1 F 0.3116(4) 0.3674(3) 0.82815(18) 0.0764(12) Uani 1 1 d . . .
F2 F 0.4165(4) 0.4945(4) 0.78524(18) 0.0835(13) Uani 1 1 d . . .
F3 F 0.6490(4) 0.6684(4) 0.8467(2) 0.0885(14) Uani 1 1 d . . .
F4 F 0.7640(4) 0.8295(4) 0.82767(18) 0.0852(13) Uani 1 1 d . . .
N1 N 0.3282(5) 0.5877(5) 0.8488(2) 0.0612(15) Uani 1 1 d . . .
N2 N 0.5610(5) 0.5095(5) 0.9274(3) 0.0648(15) Uani 1 1 d . . .
N3 N 0.5201(5) 0.4446(5) 0.8807(3) 0.0618(15) Uani 1 1 d . . .
N4 N 0.5828(7) 0.7277(7) 1.0269(3) 0.094(2) Uani 1 1 d . . .
N5 N 0.6507(5) 0.8669(5) 0.8912(2) 0.0622(15) Uani 1 1 d . . .
N6 N 0.8862(6) 0.7852(6) 0.9649(3) 0.0741(17) Uani 1 1 d . . .
N7 N 0.8455(5) 0.7285(5) 0.9161(3) 0.0691(16) Uani 1 1 d . . .
N8 N 0.9011(8) 0.9786(9) 1.0728(4) 0.123(3) Uani 1 1 d . . .
C1 C 0.1728(7) 0.7415(6) 0.8413(3) 0.0644(18) Uani 1 1 d . . .
C2 C 0.0594(7) 0.8075(7) 0.8151(4) 0.077(2) Uani 1 1 d . . .
H2 H 0.0310 0.8730 0.8324 0.093 Uiso 1 1 calc R . .
C3 C -0.0072(7) 0.7701(8) 0.7628(4) 0.084(2) Uani 1 1 d . . .
H3 H -0.0841 0.8103 0.7443 0.100 Uiso 1 1 calc R . .
C4 C 0.0354(7) 0.6749(7) 0.7364(4) 0.075(2) Uani 1 1 d . . .
H4 H -0.0118 0.6553 0.7002 0.090 Uiso 1 1 calc R . .
C5 C 0.1461(6) 0.6079(7) 0.7620(3) 0.0653(18) Uani 1 1 d . . .
H5 H 0.1740 0.5427 0.7444 0.078 Uiso 1 1 calc R . .
C6 C 0.2137(6) 0.6437(6) 0.8158(3) 0.0602(17) Uani 1 1 d . . .
C7 C 0.3727(7) 0.6455(6) 0.8980(3) 0.0638(18) Uani 1 1 d . . .
C8 C 0.4892(7) 0.6019(6) 0.9352(3) 0.0605(17) Uani 1 1 d . . .
C9 C 0.5411(7) 0.6700(7) 0.9858(4) 0.072(2) Uani 1 1 d . . .
C10 C 0.6092(7) 0.3507(6) 0.8766(3) 0.0629(18) Uani 1 1 d . . .
C11 C 0.7287(8) 0.3385(8) 0.9151(3) 0.083(2) Uani 1 1 d . . .
H11 H 0.7531 0.3934 0.9450 0.099 Uiso 1 1 calc R . .
C12 C 0.8124(8) 0.2474(8) 0.9103(4) 0.101(3) Uani 1 1 d . . .
H12 H 0.8929 0.2412 0.9367 0.122 Uiso 1 1 calc R . .
C13 C 0.7783(7) 0.1648(7) 0.8666(4) 0.081(2) Uani 1 1 d . . .
H13 H 0.8341 0.1011 0.8639 0.097 Uiso 1 1 calc R . .
C14 C 0.6618(8) 0.1776(7) 0.8271(3) 0.074(2) Uani 1 1 d . . .
H14 H 0.6401 0.1248 0.7966 0.088 Uiso 1 1 calc R . .
C15 C 0.5752(7) 0.2679(7) 0.8319(3) 0.0688(19) Uani 1 1 d . . .
H15 H 0.4947 0.2733 0.8055 0.083 Uiso 1 1 calc R . .
C16 C 0.4891(7) 1.0077(6) 0.8894(3) 0.0648(18) Uani 1 1 d . . .
C17 C 0.3730(7) 1.0702(7) 0.8655(4) 0.078(2) Uani 1 1 d . . .
H17 H 0.3441 1.1317 0.8845 0.093 Uiso 1 1 calc R . .
C18 C 0.3029(8) 1.0369(8) 0.8125(4) 0.089(3) Uani 1 1 d . . .
H18 H 0.2254 1.0777 0.7956 0.107 Uiso 1 1 calc R . .
C19 C 0.3438(8) 0.9442(8) 0.7833(4) 0.091(3) Uani 1 1 d . . .
H19 H 0.2940 0.9241 0.7475 0.109 Uiso 1 1 calc R . .
C20 C 0.4581(7) 0.8828(8) 0.8075(4) 0.081(2) Uani 1 1 d . . .
H20 H 0.4860 0.8202 0.7886 0.097 Uiso 1 1 calc R . .
C21 C 0.5306(7) 0.9159(6) 0.8603(3) 0.0666(19) Uani 1 1 d . . .
C22 C 0.6971(7) 0.9189(7) 0.9415(3) 0.0645(18) Uani 1 1 d . . .
C23 C 0.8160(7) 0.8744(7) 0.9752(3) 0.070(2) Uani 1 1 d . . .
C24 C 0.8654(8) 0.9305(9) 1.0294(4) 0.092(3) Uani 1 1 d . . .
C25 C 0.9282(7) 0.6301(6) 0.9099(3) 0.0644(18) Uani 1 1 d . . .
C26 C 1.0317(8) 0.5913(9) 0.9509(4) 0.097(3) Uani 1 1 d . . .
H26 H 1.0511 0.6302 0.9850 0.116 Uiso 1 1 calc R . .
C27 C 1.1104(9) 0.4954(9) 0.9440(5) 0.108(3) Uani 1 1 d . . .
H27 H 1.1818 0.4719 0.9733 0.130 Uiso 1 1 calc R . .
C28 C 1.0847(9) 0.4354(8) 0.8952(4) 0.089(3) Uani 1 1 d . . .
H28 H 1.1360 0.3693 0.8906 0.106 Uiso 1 1 calc R . .
C29 C 0.9811(9) 0.4751(8) 0.8529(4) 0.096(3) Uani 1 1 d . . .
H29 H 0.9636 0.4366 0.8188 0.115 Uiso 1 1 calc R . .
C30 C 0.9022(8) 0.5696(8) 0.8590(4) 0.088(2) Uani 1 1 d . . .
H30 H 0.8316 0.5936 0.8294 0.106 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.708(7) . ?
S1 C1 1.748(8) . ?
S2 C22 1.699(7) . ?
S2 C16 1.739(8) . ?
B1 F2 1.361(10) . ?
B1 F1 1.383(9) . ?
B1 N1 1.542(10) . ?
B1 N3 1.576(11) . ?
B2 F4 1.375(9) . ?
B2 F3 1.379(9) . ?
B2 N7 1.551(11) . ?
B2 N5 1.561(9) . ?
N1 C7 1.347(8) . ?
N1 C6 1.404(8) . ?
N2 C8 1.313(8) . ?
N2 N3 1.329(8) . ?
N3 C10 1.426(8) . ?
N4 C9 1.176(9) . ?
N5 C22 1.344(9) . ?
N5 C21 1.405(8) . ?
N6 C23 1.300(8) . ?
N6 N7 1.330(8) . ?
N7 C25 1.427(8) . ?
N8 C24 1.172(10) . ?
C1 C6 1.377(9) . ?
C1 C2 1.400(10) . ?
C2 C3 1.367(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(9) . ?
C5 H5 0.9300 . ?
C7 C8 1.408(9) . ?
C8 C9 1.435(10) . ?
C10 C11 1.375(10) . ?
C10 C15 1.394(9) . ?
C11 C12 1.368(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.391(9) . ?
C16 C17 1.395(10) . ?
C17 C18 1.377(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(10) . ?
C20 H20 0.9300 . ?
C22 C23 1.401(10) . ?
C23 C24 1.449(11) . ?
C25 C26 1.343(10) . ?
C25 C30 1.403(10) . ?
C26 C27 1.383(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.353(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.363(12) . ?
C28 H28 0.9300 . ?
C29 C30 1.366(10) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C1 89.7(4) . . ?
C22 S2 C16 90.5(4) . . ?
F2 B1 F1 112.5(8) . . ?
F2 B1 N1 109.8(7) . . ?
F1 B1 N1 108.5(6) . . ?
F2 B1 N3 109.9(6) . . ?
F1 B1 N3 108.5(7) . . ?
N1 B1 N3 107.5(7) . . ?
F4 B2 F3 111.0(8) . . ?
F4 B2 N7 110.6(6) . . ?
F3 B2 N7 110.3(6) . . ?
F4 B2 N5 109.4(6) . . ?
F3 B2 N5 108.1(6) . . ?
N7 B2 N5 107.3(7) . . ?
C7 N1 C6 111.1(6) . . ?
C7 N1 B1 123.9(6) . . ?
C6 N1 B1 125.0(6) . . ?
C8 N2 N3 118.5(6) . . ?
N2 N3 C10 112.7(6) . . ?
N2 N3 B1 125.1(6) . . ?
C10 N3 B1 122.1(6) . . ?
C22 N5 C21 112.9(6) . . ?
C22 N5 B2 123.6(6) . . ?
C21 N5 B2 123.4(7) . . ?
C23 N6 N7 118.6(7) . . ?
N6 N7 C25 113.7(6) . . ?
N6 N7 B2 124.5(6) . . ?
C25 N7 B2 121.6(6) . . ?
C6 C1 C2 121.6(7) . . ?
C6 C1 S1 110.9(6) . . ?
C2 C1 S1 127.5(6) . . ?
C3 C2 C1 116.3(7) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 122.4(8) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 121.9(8) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 116.2(7) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C1 C6 C5 121.6(7) . . ?
C1 C6 N1 113.5(7) . . ?
C5 C6 N1 124.9(6) . . ?
N1 C7 C8 117.7(6) . . ?
N1 C7 S1 114.9(5) . . ?
C8 C7 S1 127.4(6) . . ?
N2 C8 C7 127.1(7) . . ?
N2 C8 C9 115.3(7) . . ?
C7 C8 C9 117.5(6) . . ?
N4 C9 C8 178.9(9) . . ?
C11 C10 C15 118.2(7) . . ?
C11 C10 N3 122.5(7) . . ?
C15 C10 N3 119.3(7) . . ?
C12 C11 C10 121.4(8) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.4(8) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.2(7) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.0(8) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 119.7(7) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
C21 C16 C17 120.6(7) . . ?
C21 C16 S2 111.2(6) . . ?
C17 C16 S2 128.2(6) . . ?
C18 C17 C16 117.2(8) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 C19 122.4(8) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C20 C19 C18 119.8(9) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 118.7(8) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C16 121.3(7) . . ?
C20 C21 N5 127.1(7) . . ?
C16 C21 N5 111.6(7) . . ?
N5 C22 C23 116.6(6) . . ?
N5 C22 S2 113.9(6) . . ?
C23 C22 S2 129.5(6) . . ?
N6 C23 C22 128.1(7) . . ?
N6 C23 C24 115.5(7) . . ?
C22 C23 C24 116.3(7) . . ?
N8 C24 C23 177.4(9) . . ?
C26 C25 C30 117.3(7) . . ?
C26 C25 N7 123.2(7) . . ?
C30 C25 N7 119.5(7) . . ?
C25 C26 C27 122.2(9) . . ?
C25 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C28 C27 C26 120.8(9) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 117.7(8) . . ?
C27 C28 H28 121.1 . . ?
C29 C28 H28 121.1 . . ?
C28 C29 C30 122.4(9) . . ?
C28 C29 H29 118.8 . . ?
C30 C29 H29 118.8 . . ?
C29 C30 C25 119.6(9) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?

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
F2 B1 N1 C7 -125.5(7) . . . . ?
F1 B1 N1 C7 111.2(8) . . . . ?
N3 B1 N1 C7 -5.9(9) . . . . ?
F2 B1 N1 C6 58.3(9) . . . . ?
F1 B1 N1 C6 -65.1(10) . . . . ?
N3 B1 N1 C6 177.8(6) . . . . ?
C8 N2 N3 C10 177.6(6) . . . . ?
C8 N2 N3 B1 1.0(10) . . . . ?
F2 B1 N3 N2 122.4(7) . . . . ?
F1 B1 N3 N2 -114.2(7) . . . . ?
N1 B1 N3 N2 3.0(10) . . . . ?
F2 B1 N3 C10 -53.9(9) . . . . ?
F1 B1 N3 C10 69.5(9) . . . . ?
N1 B1 N3 C10 -173.4(5) . . . . ?
F4 B2 N5 C22 -108.0(8) . . . . ?
F3 B2 N5 C22 131.0(7) . . . . ?
N7 B2 N5 C22 12.0(9) . . . . ?
F4 B2 N5 C21 66.4(9) . . . . ?
F3 B2 N5 C21 -54.6(9) . . . . ?
N7 B2 N5 C21 -173.5(6) . . . . ?
C23 N6 N7 C25 -178.3(6) . . . . ?
C23 N6 N7 B2 7.1(11) . . . . ?
F4 B2 N7 N6 106.4(8) . . . . ?
F3 B2 N7 N6 -130.5(7) . . . . ?
N5 B2 N7 N6 -13.0(9) . . . . ?
F4 B2 N7 C25 -67.8(8) . . . . ?
F3 B2 N7 C25 55.4(9) . . . . ?
N5 B2 N7 C25 172.9(6) . . . . ?
C7 S1 C1 C6 0.2(5) . . . . ?
C7 S1 C1 C2 179.7(7) . . . . ?
C6 C1 C2 C3 -0.7(11) . . . . ?
S1 C1 C2 C3 179.9(6) . . . . ?
C1 C2 C3 C4 -1.5(12) . . . . ?
C2 C3 C4 C5 2.5(12) . . . . ?
C3 C4 C5 C6 -1.2(11) . . . . ?
C2 C1 C6 C5 1.9(11) . . . . ?
S1 C1 C6 C5 -178.6(5) . . . . ?
C2 C1 C6 N1 -179.0(6) . . . . ?
S1 C1 C6 N1 0.5(7) . . . . ?
C4 C5 C6 C1 -0.9(10) . . . . ?
C4 C5 C6 N1 -179.9(6) . . . . ?
C7 N1 C6 C1 -1.1(8) . . . . ?
B1 N1 C6 C1 175.5(6) . . . . ?
C7 N1 C6 C5 177.9(6) . . . . ?
B1 N1 C6 C5 -5.4(10) . . . . ?
C6 N1 C7 C8 -178.3(6) . . . . ?
B1 N1 C7 C8 5.0(10) . . . . ?
C6 N1 C7 S1 1.3(7) . . . . ?
B1 N1 C7 S1 -175.4(5) . . . . ?
C1 S1 C7 N1 -0.9(5) . . . . ?
C1 S1 C7 C8 178.7(7) . . . . ?
N3 N2 C8 C7 -2.9(11) . . . . ?
N3 N2 C8 C9 -178.3(6) . . . . ?
N1 C7 C8 N2 -0.1(11) . . . . ?
S1 C7 C8 N2 -179.7(5) . . . . ?
N1 C7 C8 C9 175.3(6) . . . . ?
S1 C7 C8 C9 -4.3(10) . . . . ?
N2 C8 C9 N4 144(46) . . . . ?
C7 C8 C9 N4 -32(47) . . . . ?
N2 N3 C10 C11 -5.5(10) . . . . ?
B1 N3 C10 C11 171.2(7) . . . . ?
N2 N3 C10 C15 174.7(6) . . . . ?
B1 N3 C10 C15 -8.6(10) . . . . ?
C15 C10 C11 C12 -0.4(13) . . . . ?
N3 C10 C11 C12 179.8(8) . . . . ?
C10 C11 C12 C13 -0.3(15) . . . . ?
C11 C12 C13 C14 2.2(14) . . . . ?
C12 C13 C14 C15 -3.3(12) . . . . ?
C13 C14 C15 C10 2.6(11) . . . . ?
C11 C10 C15 C14 -0.7(11) . . . . ?
N3 C10 C15 C14 179.1(6) . . . . ?
C22 S2 C16 C21 0.8(6) . . . . ?
C22 S2 C16 C17 -178.6(7) . . . . ?
C21 C16 C17 C18 0.0(11) . . . . ?
S2 C16 C17 C18 179.3(6) . . . . ?
C16 C17 C18 C19 0.4(13) . . . . ?
C17 C18 C19 C20 -0.1(14) . . . . ?
C18 C19 C20 C21 -0.8(12) . . . . ?
C19 C20 C21 C16 1.2(12) . . . . ?
C19 C20 C21 N5 -178.2(7) . . . . ?
C17 C16 C21 C20 -0.8(11) . . . . ?
S2 C16 C21 C20 179.8(6) . . . . ?
C17 C16 C21 N5 178.6(6) . . . . ?
S2 C16 C21 N5 -0.8(8) . . . . ?
C22 N5 C21 C20 179.8(7) . . . . ?
B2 N5 C21 C20 4.8(11) . . . . ?
C22 N5 C21 C16 0.4(8) . . . . ?
B2 N5 C21 C16 -174.6(6) . . . . ?
C21 N5 C22 C23 179.4(6) . . . . ?
B2 N5 C22 C23 -5.7(10) . . . . ?
C21 N5 C22 S2 0.2(8) . . . . ?
B2 N5 C22 S2 175.2(5) . . . . ?
C16 S2 C22 N5 -0.6(6) . . . . ?
C16 S2 C22 C23 -179.6(7) . . . . ?
N7 N6 C23 C22 1.9(12) . . . . ?
N7 N6 C23 C24 179.2(7) . . . . ?
N5 C22 C23 N6 -2.6(12) . . . . ?
S2 C22 C23 N6 176.4(6) . . . . ?
N5 C22 C23 C24 -179.9(7) . . . . ?
S2 C22 C23 C24 -0.9(12) . . . . ?
N6 C23 C24 N8 -173(27) . . . . ?
C22 C23 C24 N8 5(27) . . . . ?
N6 N7 C25 C26 5.1(11) . . . . ?
B2 N7 C25 C26 179.8(8) . . . . ?
N6 N7 C25 C30 -174.8(7) . . . . ?
B2 N7 C25 C30 -0.1(10) . . . . ?
C30 C25 C26 C27 -0.2(14) . . . . ?
N7 C25 C26 C27 179.8(8) . . . . ?
C25 C26 C27 C28 -0.8(16) . . . . ?
C26 C27 C28 C29 1.8(15) . . . . ?
C27 C28 C29 C30 -1.9(14) . . . . ?
C28 C29 C30 C25 0.9(14) . . . . ?
C26 C25 C30 C29 0.1(13) . . . . ?
N7 C25 C30 C29 -179.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.088
