# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

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

data_141126c
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv1t
_database_code_depnum_ccdc_archive 'CCDC 1470176'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H6 B Cl F2 N4 O0 S'
_chemical_formula_weight         334.54

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'
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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   7.645(3)
_cell_length_b                   8.842(3)
_cell_length_c                   10.324(2)
_cell_angle_alpha                104.02(2)
_cell_angle_beta                 94.76(2)
_cell_angle_gamma                100.91(3)
_cell_volume                     658.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    361
_cell_measurement_theta_min      7.8000
_cell_measurement_theta_max      68.9590

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    4.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6991
_exptl_absorpt_correction_T_max  0.7536
_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            3480
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.1576
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         66.14
_reflns_number_total             2294
_reflns_number_gt                935
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0881P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2294
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1778
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.1943
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_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 0.5437(2) 0.5963(2) 0.17946(14) 0.0709(5) Uani 1 1 d . . .
S1 S 0.6295(2) 0.8672(2) 0.87724(14) 0.0673(5) Uani 1 1 d . . .
N2 N 0.4748(6) 0.7341(5) 0.4207(4) 0.0453(13) Uani 1 1 d . . .
F1 F 0.6494(5) 0.5333(4) 0.4331(3) 0.0599(10) Uani 1 1 d . . .
F2 F 0.7988(5) 0.7811(4) 0.4371(3) 0.0626(10) Uani 1 1 d . . .
N1 N 0.6746(6) 0.7428(5) 0.6339(4) 0.0488(13) Uani 1 1 d . . .
C8 C 0.4220(7) 0.8647(6) 0.6472(5) 0.0468(16) Uani 1 1 d . . .
C12 C 0.2150(8) 0.8479(7) 0.4453(6) 0.0563(18) Uani 1 1 d . . .
H12 H 0.1417 0.9006 0.4991 0.068 Uiso 1 1 calc R . .
C7 C 0.5704(8) 0.8217(6) 0.7056(5) 0.0454(15) Uani 1 1 d . . .
N3 N 0.2315(8) 1.0229(6) 0.7969(5) 0.0750(18) Uani 1 1 d . . .
C9 C 0.3118(9) 0.9490(6) 0.7293(6) 0.0530(18) Uani 1 1 d . . .
C2 C 1.0670(8) 0.6048(7) 0.7673(5) 0.0681(19) Uani 1 1 d D . .
H2 H 1.1543 0.5481 0.7403 0.082 Uiso 1 1 calc R . .
N5 N 0.2775(7) 0.7277(6) 0.2280(5) 0.0666(17) Uani 1 1 d . . .
B1 B 0.6546(9) 0.6911(8) 0.4760(6) 0.0440(18) Uani 1 1 d . . .
C4 C 0.9305(7) 0.7491(7) 0.9461(5) 0.077(2) Uani 1 1 d D . .
H4 H 0.9277 0.7904 1.0375 0.092 Uiso 1 1 calc R . .
C10 C 0.3700(8) 0.8148(7) 0.5041(5) 0.0478(16) Uani 1 1 d . . .
C3 C 1.0595(8) 0.6660(7) 0.9036(5) 0.068(2) Uani 1 1 d D . .
H3 H 1.1432 0.6506 0.9672 0.081 Uiso 1 1 calc R . .
C11 C 0.1725(9) 0.8027(8) 0.3095(6) 0.068(2) Uani 1 1 d . . .
H11 H 0.0683 0.8236 0.2712 0.082 Uiso 1 1 calc R . .
C6 C 0.8137(7) 0.7090(6) 0.7146(5) 0.0516(17) Uani 1 1 d D . .
C1 C 0.9441(7) 0.6283(7) 0.6714(5) 0.0616(19) Uani 1 1 d D . .
H1 H 0.9497 0.5902 0.5800 0.074 Uiso 1 1 calc R . .
C13 C 0.4202(9) 0.6988(7) 0.2840(6) 0.0580(19) Uani 1 1 d . . .
C5 C 0.8040(8) 0.7706(7) 0.8508(5) 0.0592(19) Uani 1 1 d 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 C13 1.702(6) . ?
S1 C7 1.720(5) . ?
S1 C5 1.722(6) . ?
N2 C13 1.379(7) . ?
N2 C10 1.387(7) . ?
N2 B1 1.592(8) . ?
F1 B1 1.350(7) . ?
F2 B1 1.381(7) . ?
N1 C7 1.315(7) . ?
N1 C6 1.417(7) . ?
N1 B1 1.569(7) . ?
C8 C7 1.399(8) . ?
C8 C9 1.425(8) . ?
C8 C10 1.434(7) . ?
C12 C11 1.355(8) . ?
C12 C10 1.398(8) . ?
C12 H12 0.9300 . ?
N3 C9 1.137(8) . ?
C2 C1 1.387(6) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9300 . ?
N5 C13 1.289(8) . ?
N5 C11 1.355(8) . ?
C4 C3 1.377(6) . ?
C4 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C6 C1 1.375(6) . ?
C6 C5 1.393(6) . ?
C1 H1 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 C5 89.1(3) . . ?
C13 N2 C10 116.3(5) . . ?
C13 N2 B1 120.5(5) . . ?
C10 N2 B1 123.1(4) . . ?
C7 N1 C6 112.8(4) . . ?
C7 N1 B1 125.3(5) . . ?
C6 N1 B1 121.8(4) . . ?
C7 C8 C9 120.7(5) . . ?
C7 C8 C10 120.5(5) . . ?
C9 C8 C10 118.6(5) . . ?
C11 C12 C10 119.5(6) . . ?
C11 C12 H12 120.2 . . ?
C10 C12 H12 120.2 . . ?
N1 C7 C8 122.8(5) . . ?
N1 C7 S1 114.9(4) . . ?
C8 C7 S1 122.4(4) . . ?
N3 C9 C8 176.4(7) . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C13 N5 C11 117.7(5) . . ?
F1 B1 F2 111.8(5) . . ?
F1 B1 N1 109.6(5) . . ?
F2 B1 N1 107.6(5) . . ?
F1 B1 N2 111.5(5) . . ?
F2 B1 N2 108.6(5) . . ?
N1 B1 N2 107.6(4) . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C10 C12 118.6(5) . . ?
N2 C10 C8 120.3(5) . . ?
C12 C10 C8 121.1(5) . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C12 C11 N5 121.8(6) . . ?
C12 C11 H11 119.1 . . ?
N5 C11 H11 119.1 . . ?
C1 C6 C5 122.1(5) . . ?
C1 C6 N1 127.4(4) . . ?
C5 C6 N1 110.4(5) . . ?
C6 C1 C2 118.5(5) . . ?
C6 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
N5 C13 N2 125.9(6) . . ?
N5 C13 Cl1 116.6(5) . . ?
N2 C13 Cl1 117.4(5) . . ?
C6 C5 C4 118.7(5) . . ?
C6 C5 S1 112.8(4) . . ?
C4 C5 S1 128.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        66.14
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_6221
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv2v
_database_code_depnum_ccdc_archive 'CCDC 1470177'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 B F2 N4 O S'
_chemical_formula_weight         330.12

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'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   4.7639(7)
_cell_length_b                   11.7169(19)
_cell_length_c                   12.608(2)
_cell_angle_alpha                83.834(14)
_cell_angle_beta                 86.891(13)
_cell_angle_gamma                87.700(13)
_cell_volume                     698.21(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    595
_cell_measurement_theta_min      4.8930
_cell_measurement_theta_max      70.3220

_exptl_crystal_description       block
_exptl_crystal_colour            Kelly
_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    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8331
_exptl_absorpt_correction_T_max  0.8517
_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            3742
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_sigmaI/netI    0.1401
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         67.22
_reflns_number_total             2482
_reflns_number_gt                1340
_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)+(0.0370P)²+0.5157P] 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         2482
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2286
_refine_ls_wR_factor_gt          0.1955
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_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 0.7905(4) 0.94746(16) 0.88881(16) 0.0606(6) Uani 1 1 d . . .
B1 B 0.6878(16) 0.7091(6) 0.6815(7) 0.0461(19) Uani 1 1 d . . .
F1 F 0.8252(8) 0.7404(3) 0.5855(3) 0.0564(11) Uani 1 1 d . . .
F2 F 0.4196(7) 0.6775(3) 0.6700(3) 0.0555(11) Uani 1 1 d . . .
N1 N 0.6739(10) 0.8123(4) 0.7505(4) 0.0440(13) Uani 1 1 d . . .
N2 N 0.8634(11) 0.6067(4) 0.7458(4) 0.0429(13) Uani 1 1 d . . .
N3 N 1.0434(13) 0.4140(5) 0.7410(5) 0.0614(17) Uani 1 1 d . . .
N4 N 1.2981(15) 0.7508(6) 1.0355(6) 0.084(2) Uani 1 1 d . . .
O1 O 0.7382(10) 0.4986(4) 0.6192(4) 0.0590(14) Uani 1 1 d . . .
C1 C 0.5577(14) 0.9982(6) 0.7898(6) 0.0494(17) Uani 1 1 d . . .
C2 C 0.4292(16) 1.1065(6) 0.7761(7) 0.067(2) Uani 1 1 d . . .
H2 H 0.4564 1.1618 0.8219 0.080 Uiso 1 1 calc R . .
C3 C 0.2568(18) 1.1279(7) 0.6899(7) 0.073(2) Uani 1 1 d . . .
H3 H 0.1688 1.2000 0.6768 0.087 Uiso 1 1 calc R . .
C4 C 0.2137(17) 1.0452(6) 0.6237(7) 0.071(2) Uani 1 1 d . . .
H4 H 0.0932 1.0621 0.5681 0.085 Uiso 1 1 calc R . .
C5 C 0.3429(15) 0.9383(6) 0.6371(6) 0.0574(19) Uani 1 1 d . . .
H5 H 0.3159 0.8833 0.5909 0.069 Uiso 1 1 calc R . .
C6 C 0.5177(14) 0.9153(6) 0.7235(6) 0.0493(17) Uani 1 1 d . . .
C7 C 0.8260(14) 0.8182(6) 0.8355(5) 0.0487(16) Uani 1 1 d . . .
C8 C 0.9943(14) 0.7247(6) 0.8770(5) 0.0510(18) Uani 1 1 d . . .
C9 C 1.1607(16) 0.7373(6) 0.9661(6) 0.0566(19) Uani 1 1 d . . .
C10 C 1.0114(14) 0.6199(6) 0.8335(5) 0.0481(16) Uani 1 1 d . . .
C11 C 1.1793(15) 0.5245(7) 0.8750(6) 0.060(2) Uani 1 1 d . . .
H11 H 1.2831 0.5293 0.9347 0.072 Uiso 1 1 calc R . .
C12 C 1.1869(17) 0.4272(7) 0.8274(7) 0.068(2) Uani 1 1 d . . .
H12 H 1.2977 0.3655 0.8559 0.082 Uiso 1 1 calc R . .
C13 C 0.8890(14) 0.5029(6) 0.7037(6) 0.0501(17) Uani 1 1 d . . .
C14 C 0.7395(18) 0.3904(6) 0.5738(7) 0.074(3) Uani 1 1 d . . .
H14A H 0.9266 0.3715 0.5474 0.112 Uiso 1 1 calc R . .
H14B H 0.6145 0.3967 0.5161 0.112 Uiso 1 1 calc R . .
H14C H 0.6784 0.3312 0.6277 0.112 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 1.720(7) . ?
S1 C1 1.755(7) . ?
B1 F2 1.364(8) . ?
B1 F1 1.366(9) . ?
B1 N1 1.561(9) . ?
B1 N2 1.607(8) . ?
N1 C7 1.335(8) . ?
N1 C6 1.412(7) . ?
N2 C10 1.368(8) . ?
N2 C13 1.377(8) . ?
N3 C13 1.310(8) . ?
N3 C12 1.343(9) . ?
N4 C9 1.149(9) . ?
O1 C13 1.323(8) . ?
O1 C14 1.446(8) . ?
C1 C6 1.372(9) . ?
C1 C2 1.385(9) . ?
C2 C3 1.394(10) . ?
C3 C4 1.374(10) . ?
C4 C5 1.371(9) . ?
C5 C6 1.403(9) . ?
C7 C8 1.403(9) . ?
C8 C10 1.396(9) . ?
C8 C9 1.432(9) . ?
C10 C11 1.418(9) . ?
C11 C12 1.343(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 C1 89.7(3) . . ?
F2 B1 F1 112.2(6) . . ?
F2 B1 N1 108.1(6) . . ?
F1 B1 N1 109.4(6) . . ?
F2 B1 N2 110.6(6) . . ?
F1 B1 N2 109.5(6) . . ?
N1 B1 N2 106.8(5) . . ?
C7 N1 C6 112.0(6) . . ?
C7 N1 B1 124.5(5) . . ?
C6 N1 B1 123.2(5) . . ?
C10 N2 C13 118.1(5) . . ?
C10 N2 B1 123.9(5) . . ?
C13 N2 B1 117.7(5) . . ?
C13 N3 C12 116.1(7) . . ?
C13 O1 C14 117.2(5) . . ?
C6 C1 C2 122.6(7) . . ?
C6 C1 S1 110.8(5) . . ?
C2 C1 S1 126.5(6) . . ?
C1 C2 C3 116.2(7) . . ?
C4 C3 C2 121.6(7) . . ?
C5 C4 C3 122.0(7) . . ?
C4 C5 C6 117.1(7) . . ?
C1 C6 C5 120.5(6) . . ?
C1 C6 N1 113.1(6) . . ?
C5 C6 N1 126.4(6) . . ?
N1 C7 C8 121.6(6) . . ?
N1 C7 S1 114.3(5) . . ?
C8 C7 S1 124.1(5) . . ?
C10 C8 C7 122.5(6) . . ?
C10 C8 C9 118.2(6) . . ?
C7 C8 C9 119.2(6) . . ?
N4 C9 C8 177.6(9) . . ?
N2 C10 C8 119.6(6) . . ?
N2 C10 C11 117.2(6) . . ?
C8 C10 C11 123.2(6) . . ?
C12 C11 C10 119.4(7) . . ?
C11 C12 N3 123.7(7) . . ?
N3 C13 O1 121.0(6) . . ?
N3 C13 N2 125.4(6) . . ?
O1 C13 N2 113.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        67.22
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_150402d
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv5y
_database_code_depnum_ccdc_archive 'CCDC 1470180'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H6 B Cl F2 N4 O0 S'
_chemical_formula_weight         334.54

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   9.628(9)
_cell_length_b                   11.936(12)
_cell_length_c                   12.293(12)
_cell_angle_alpha                100.080(12)
_cell_angle_beta                 93.490(12)
_cell_angle_gamma                103.522(13)
_cell_volume                     1345(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2451
_cell_measurement_theta_min      2.692
_cell_measurement_theta_max      27.2255

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6760
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4632
_reflns_number_gt                3291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4632
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.1018
_refine_ls_wR_factor_ref         0.3009
_refine_ls_wR_factor_gt          0.2816
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
Cl1 Cl 0.59475(17) 0.58484(14) 0.23984(13) 0.0481(5) Uani 1 1 d . . .
S1 S 0.48619(17) -0.08521(14) 0.27893(14) 0.0442(5) Uani 1 1 d . . .
N2 N 0.3918(5) 0.2730(4) 0.3701(4) 0.0336(11) Uani 1 1 d . . .
N1 N 0.3540(5) 0.0576(4) 0.3832(4) 0.0334(11) Uani 1 1 d . . .
F2 F 0.3186(4) 0.2022(3) 0.5353(3) 0.0505(10) Uani 1 1 d . . .
F1 F 0.1584(3) 0.1523(3) 0.3833(3) 0.0533(10) Uani 1 1 d . . .
N3 N 0.4265(5) 0.4763(4) 0.3659(4) 0.0422(12) Uani 1 1 d . . .
C8 C 0.5124(6) 0.1474(5) 0.2597(5) 0.0375(13) Uani 1 1 d . . .
C10 C 0.4864(5) 0.2575(5) 0.2915(4) 0.0335(13) Uani 1 1 d . . .
C11 C 0.5513(6) 0.3575(5) 0.2495(5) 0.0356(13) Uani 1 1 d . . .
H11 H 0.6146 0.3530 0.1957 0.043 Uiso 1 1 calc R . .
C13 C 0.3685(6) 0.3804(5) 0.4019(5) 0.0374(13) Uani 1 1 d . . .
H13 H 0.3046 0.3874 0.4549 0.045 Uiso 1 1 calc R . .
C7 C 0.4487(6) 0.0497(5) 0.3075(5) 0.0354(13) Uani 1 1 d . . .
C6 C 0.3061(6) -0.0473(5) 0.4203(4) 0.0337(12) Uani 1 1 d . . .
C3 C 0.2402(7) -0.2660(6) 0.4783(6) 0.0488(16) Uani 1 1 d . . .
H3 H 0.2187 -0.3384 0.5001 0.059 Uiso 1 1 calc R . .
C12 C 0.5189(6) 0.4606(5) 0.2899(4) 0.0327(12) Uani 1 1 d . . .
C1 C 0.3693(6) -0.1358(5) 0.3734(5) 0.0373(13) Uani 1 1 d . . .
B1 B 0.3003(7) 0.1699(6) 0.4222(5) 0.0344(14) Uani 1 1 d . . .
C2 C 0.3383(7) -0.2457(6) 0.4022(5) 0.0447(15) Uani 1 1 d . . .
H2 H 0.3822 -0.3037 0.3713 0.054 Uiso 1 1 calc R . .
C4 C 0.1731(7) -0.1798(6) 0.5228(5) 0.0504(16) Uani 1 1 d . . .
H4 H 0.1051 -0.1963 0.5721 0.060 Uiso 1 1 calc R . .
C9 C 0.6063(8) 0.1304(6) 0.1767(6) 0.0486(16) Uani 1 1 d . . .
C5 C 0.2057(7) -0.0696(6) 0.4950(5) 0.0442(15) Uani 1 1 d . . .
H5 H 0.1613 -0.0119 0.5258 0.053 Uiso 1 1 calc R . .
N4 N 0.6817(8) 0.1197(6) 0.1093(6) 0.079(2) Uani 1 1 d . . .
S2 S 0.96793(17) 0.66615(14) 0.75489(13) 0.0430(5) Uani 1 1 d . . .
Cl2 Cl 1.11445(18) 0.04124(15) 0.75630(15) 0.0531(5) Uani 1 1 d . . .
N6 N 0.8866(5) 0.3142(4) 0.8629(4) 0.0342(11) Uani 1 1 d . . .
N5 N 0.8414(5) 0.5154(4) 0.8666(4) 0.0333(11) Uani 1 1 d . . .
F4 F 0.8321(4) 0.4274(4) 1.0281(3) 0.0536(10) Uani 1 1 d . . .
F3 F 0.6554(3) 0.3489(3) 0.8884(3) 0.0541(10) Uani 1 1 d . . .
C19 C 0.7963(6) 0.6176(5) 0.9034(5) 0.0357(13) Uani 1 1 d . . .
C20 C 0.9313(6) 0.5276(5) 0.7868(4) 0.0342(13) Uani 1 1 d . . .
C23 C 0.9749(5) 0.3301(5) 0.7790(4) 0.0314(12) Uani 1 1 d . . .
C24 C 1.0456(6) 0.2433(5) 0.7424(5) 0.0385(14) Uani 1 1 d . . .
H24 H 1.1058 0.2505 0.6864 0.046 Uiso 1 1 calc R . .
C14 C 0.8580(6) 0.7105(6) 0.8531(5) 0.0395(14) Uani 1 1 d . . .
N7 N 0.9329(6) 0.1289(5) 0.8697(4) 0.0465(13) Uani 1 1 d . . .
C21 C 0.9922(6) 0.4362(5) 0.7401(4) 0.0352(13) Uani 1 1 d . . .
C15 C 0.8298(7) 0.8204(6) 0.8800(5) 0.0478(16) Uani 1 1 d . . .
H15 H 0.8727 0.8821 0.8467 0.057 Uiso 1 1 calc R . .
C22 C 1.0786(6) 0.4553(5) 0.6510(5) 0.0389(14) Uani 1 1 d . . .
N8 N 1.1453(6) 0.4675(5) 0.5788(5) 0.0547(15) Uani 1 1 d . . .
C18 C 0.6994(7) 0.6330(6) 0.9813(5) 0.0439(15) Uani 1 1 d . . .
H18 H 0.6558 0.5715 1.0146 0.053 Uiso 1 1 calc R . .
B2 B 0.7990(7) 0.4023(6) 0.9156(5) 0.0360(15) Uani 1 1 d . . .
C26 C 0.8702(6) 0.2137(6) 0.9012(5) 0.0423(14) Uani 1 1 d . . .
H26 H 0.8081 0.2032 0.9557 0.051 Uiso 1 1 calc R . .
C25 C 1.0236(6) 0.1481(5) 0.7913(5) 0.0388(13) Uani 1 1 d . . .
C16 C 0.7342(7) 0.8340(6) 0.9594(5) 0.0499(16) Uani 1 1 d . . .
H16 H 0.7133 0.9065 0.9803 0.060 Uiso 1 1 calc R . .
C17 C 0.6698(7) 0.7405(6) 1.0076(5) 0.0496(16) Uani 1 1 d . . .
H17 H 0.6050 0.7514 1.0590 0.060 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.727(6) . ?
S1 C7 1.713(6) . ?
S1 C1 1.751(6) . ?
N2 C13 1.348(7) . ?
N2 C10 1.386(7) . ?
N2 B1 1.593(8) . ?
N1 C7 1.349(7) . ?
N1 C6 1.395(7) . ?
N1 B1 1.556(8) . ?
F2 B1 1.365(7) . ?
F1 B1 1.374(7) . ?
N3 C13 1.314(7) . ?
N3 C12 1.348(8) . ?
C8 C10 1.389(9) . ?
C8 C9 1.423(8) . ?
C8 C7 1.424(8) . ?
C10 C11 1.410(8) . ?
C11 C12 1.357(8) . ?
C6 C1 1.395(8) . ?
C6 C5 1.387(8) . ?
C3 C4 1.391(10) . ?
C3 C2 1.380(9) . ?
C1 C2 1.389(8) . ?
C4 C5 1.386(9) . ?
C9 N4 1.144(9) . ?
S2 C20 1.728(6) . ?
S2 C14 1.747(6) . ?
Cl2 C25 1.718(6) . ?
N6 C26 1.343(7) . ?
N6 C23 1.387(7) . ?
N6 B2 1.574(8) . ?
N5 C20 1.352(7) . ?
N5 C19 1.400(8) . ?
N5 B2 1.552(8) . ?
F4 B2 1.364(7) . ?
F3 B2 1.374(8) . ?
C19 C14 1.395(8) . ?
C19 C18 1.396(8) . ?
C20 C21 1.408(8) . ?
C23 C21 1.409(8) . ?
C23 C24 1.393(8) . ?
C24 C25 1.357(8) . ?
C14 C15 1.388(9) . ?
N7 C26 1.310(8) . ?
N7 C25 1.353(8) . ?
C21 C22 1.433(8) . ?
C15 C16 1.397(9) . ?
C22 N8 1.138(8) . ?
C18 C17 1.366(9) . ?
C16 C17 1.390(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 C1 90.5(3) . . ?
C13 N2 C10 119.0(5) . . ?
C13 N2 B1 116.6(5) . . ?
C10 N2 B1 124.4(5) . . ?
C7 N1 C6 112.4(5) . . ?
C7 N1 B1 123.9(5) . . ?
C6 N1 B1 123.7(4) . . ?
C13 N3 C12 113.6(5) . . ?
C10 C8 C9 119.4(5) . . ?
C10 C8 C7 122.5(5) . . ?
C9 C8 C7 118.2(6) . . ?
C8 C10 N2 119.2(5) . . ?
C8 C10 C11 124.3(5) . . ?
N2 C10 C11 116.5(5) . . ?
C12 C11 C10 118.2(5) . . ?
N3 C13 N2 126.9(5) . . ?
N1 C7 C8 121.6(5) . . ?
N1 C7 S1 113.8(4) . . ?
C8 C7 S1 124.6(4) . . ?
N1 C6 C1 113.3(5) . . ?
N1 C6 C5 126.9(5) . . ?
C1 C6 C5 119.9(5) . . ?
C4 C3 C2 120.9(6) . . ?
N3 C12 C11 125.8(5) . . ?
N3 C12 Cl1 114.5(4) . . ?
C11 C12 Cl1 119.6(4) . . ?
C2 C1 C6 121.9(6) . . ?
C2 C1 S1 128.1(5) . . ?
C6 C1 S1 110.1(4) . . ?
F2 B1 F1 110.3(5) . . ?
F2 B1 N1 111.0(5) . . ?
F1 B1 N1 110.6(5) . . ?
F2 B1 N2 109.2(5) . . ?
F1 B1 N2 107.8(5) . . ?
N1 B1 N2 107.8(4) . . ?
C1 C2 C3 117.7(6) . . ?
C5 C4 C3 121.2(6) . . ?
N4 C9 C8 178.1(7) . . ?
C4 C5 C6 118.4(6) . . ?
C20 S2 C14 90.6(3) . . ?
C26 N6 C23 117.8(5) . . ?
C26 N6 B2 116.5(5) . . ?
C23 N6 B2 125.7(5) . . ?
C20 N5 C19 112.6(5) . . ?
C20 N5 B2 123.4(5) . . ?
C19 N5 B2 123.9(4) . . ?
C14 C19 N5 113.2(5) . . ?
C14 C19 C18 119.6(6) . . ?
N5 C19 C18 127.2(5) . . ?
N5 C20 C21 121.9(5) . . ?
N5 C20 S2 113.2(4) . . ?
C21 C20 S2 124.9(4) . . ?
N6 C23 C21 117.3(5) . . ?
N6 C23 C24 118.3(5) . . ?
C21 C23 C24 124.3(5) . . ?
C25 C24 C23 117.8(5) . . ?
C19 C14 C15 122.2(6) . . ?
C19 C14 S2 110.4(5) . . ?
C15 C14 S2 127.4(5) . . ?
C26 N7 C25 114.8(5) . . ?
C23 C21 C20 123.1(5) . . ?
C23 C21 C22 119.5(5) . . ?
C20 C21 C22 117.4(5) . . ?
C14 C15 C16 117.0(6) . . ?
N8 C22 C21 178.1(7) . . ?
C17 C18 C19 118.6(6) . . ?
F3 B2 F4 110.4(5) . . ?
F3 B2 N5 110.8(5) . . ?
F4 B2 N5 110.6(5) . . ?
F3 B2 N6 107.9(5) . . ?
F4 B2 N6 108.8(5) . . ?
N5 B2 N6 108.2(4) . . ?
N7 C26 N6 126.6(5) . . ?
N7 C25 C24 124.6(6) . . ?
N7 C25 Cl2 114.8(5) . . ?
C24 C25 Cl2 120.6(5) . . ?
C17 C16 C15 120.8(6) . . ?
C18 C17 C16 121.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.219
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.174

####################################################################### 
# 
# 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_6510
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv6z
_database_code_depnum_ccdc_archive 'CCDC 1470181'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 B F2 N4 O S'
_chemical_formula_weight         330.12

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   4.7955(5)
_cell_length_b                   9.1763(13)
_cell_length_c                   16.9010(17)
_cell_angle_alpha                100.887(10)
_cell_angle_beta                 93.936(9)
_cell_angle_gamma                103.046(11)
_cell_volume                     706.67(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    719
_cell_measurement_theta_min      2.6750
_cell_measurement_theta_max      71.0640

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_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    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    2.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8349
_exptl_absorpt_correction_T_max  0.8533
_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            4168
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         71.42
_reflns_number_total             2692
_reflns_number_gt                1683
_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)+(0.1820P)²+1.4155P] 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         2692
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.2270
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   0.687
_refine_ls_restrained_S_all      0.687
_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 0.7331(2) -0.01840(13) 0.58394(6) 0.0520(4) Uani 1 1 d . . .
F1 F 0.8178(6) 0.0772(3) 0.86927(15) 0.0567(7) Uani 1 1 d . . .
F2 F 0.4635(5) 0.1972(3) 0.85009(15) 0.0584(7) Uani 1 1 d . . .
N1 N 0.6467(7) 0.0765(4) 0.7318(2) 0.0439(8) Uani 1 1 d . . .
O1 O 1.5854(8) 0.6990(4) 0.8751(2) 0.0694(10) Uani 1 1 d . . .
N2 N 0.9409(7) 0.3151(4) 0.8256(2) 0.0443(8) Uani 1 1 d . . .
N3 N 1.2053(9) 0.5411(5) 0.9179(2) 0.0580(10) Uani 1 1 d . . .
C7 C 0.8182(9) 0.1113(5) 0.6756(2) 0.0431(9) Uani 1 1 d . . .
C6 C 0.4323(9) -0.0598(5) 0.7032(2) 0.0450(9) Uani 1 1 d . . .
C10 C 1.1058(9) 0.3488(5) 0.7646(2) 0.0450(9) Uani 1 1 d . . .
C12 C 1.3678(11) 0.5738(5) 0.8581(3) 0.0521(11) Uani 1 1 d . . .
C1 C 0.4479(9) -0.1272(5) 0.6232(3) 0.0478(10) Uani 1 1 d . . .
C11 C 1.3229(10) 0.4823(5) 0.7818(3) 0.0524(11) Uani 1 1 d . . .
H11 H 1.4371 0.5097 0.7421 0.063 Uiso 1 1 calc R . .
C13 C 1.0003(10) 0.4151(6) 0.8975(3) 0.0557(12) Uani 1 1 d . . .
H13 H 0.8823 0.3920 0.9371 0.067 Uiso 1 1 calc R . .
N4 N 1.3682(11) 0.2985(6) 0.5782(3) 0.0787(14) Uani 1 1 d . . .
C8 C 1.0440(9) 0.2439(5) 0.6892(2) 0.0432(9) Uani 1 1 d . . .
C5 C 0.2170(9) -0.1263(5) 0.7452(3) 0.0532(11) Uani 1 1 d . . .
H5 H 0.2045 -0.0819 0.7986 0.064 Uiso 1 1 calc R . .
B1 B 0.7087(10) 0.1623(6) 0.8211(3) 0.0444(11) Uani 1 1 d . . .
C4 C 0.0233(10) -0.2584(6) 0.7064(3) 0.0555(11) Uani 1 1 d . . .
H4 H -0.1240 -0.3029 0.7337 0.067 Uiso 1 1 calc R . .
C2 C 0.2554(10) -0.2617(6) 0.5836(3) 0.0583(12) Uani 1 1 d . . .
H2 H 0.2681 -0.3063 0.5302 0.070 Uiso 1 1 calc R . .
C9 C 1.2195(11) 0.2736(5) 0.6265(3) 0.0552(11) Uani 1 1 d . . .
C3 C 0.0422(11) -0.3278(6) 0.6266(3) 0.0630(13) Uani 1 1 d . . .
H3 H -0.0891 -0.4190 0.6021 0.076 Uiso 1 1 calc R . .
C14 C 1.6377(15) 0.7919(7) 0.9556(3) 0.0830(19) Uani 1 1 d . . .
H14A H 1.6634 0.7300 0.9941 0.124 Uiso 1 1 calc R . .
H14B H 1.4763 0.8352 0.9666 0.124 Uiso 1 1 calc R . .
H14C H 1.8084 0.8727 0.9601 0.124 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 1.727(4) . ?
S1 C1 1.751(4) . ?
F1 B1 1.384(6) . ?
F2 B1 1.384(5) . ?
N1 C7 1.335(5) . ?
N1 C6 1.407(5) . ?
N1 B1 1.538(6) . ?
O1 C12 1.336(6) . ?
O1 C14 1.436(6) . ?
N2 C13 1.346(5) . ?
N2 C10 1.381(5) . ?
N2 B1 1.566(6) . ?
N3 C13 1.308(6) . ?
N3 C12 1.354(6) . ?
C7 C8 1.404(6) . ?
C6 C5 1.386(6) . ?
C6 C1 1.391(6) . ?
C10 C11 1.385(6) . ?
C10 C8 1.413(6) . ?
C12 C11 1.373(6) . ?
C1 C2 1.383(6) . ?
N4 C9 1.142(6) . ?
C8 C9 1.425(6) . ?
C5 C4 1.367(7) . ?
C4 C3 1.397(7) . ?
C2 C3 1.389(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 89.8(2) . . ?
C7 N1 C6 112.3(3) . . ?
C7 N1 B1 123.0(4) . . ?
C6 N1 B1 124.0(3) . . ?
C12 O1 C14 118.7(4) . . ?
C13 N2 C10 117.7(4) . . ?
C13 N2 B1 116.7(3) . . ?
C10 N2 B1 125.3(3) . . ?
C13 N3 C12 114.9(4) . . ?
N1 C7 C8 123.0(4) . . ?
N1 C7 S1 114.3(3) . . ?
C8 C7 S1 122.8(3) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 N1 127.1(4) . . ?
C1 C6 N1 112.8(4) . . ?
N2 C10 C11 117.7(4) . . ?
N2 C10 C8 117.8(4) . . ?
C11 C10 C8 124.4(4) . . ?
O1 C12 N3 118.2(4) . . ?
O1 C12 C11 118.8(4) . . ?
N3 C12 C11 123.0(4) . . ?
C2 C1 C6 121.8(4) . . ?
C2 C1 S1 127.4(4) . . ?
C6 C1 S1 110.8(3) . . ?
C12 C11 C10 119.3(4) . . ?
N3 C13 N2 127.3(4) . . ?
C10 C8 C7 121.4(4) . . ?
C10 C8 C9 118.6(4) . . ?
C7 C8 C9 120.0(4) . . ?
C4 C5 C6 118.7(4) . . ?
F2 B1 F1 109.5(3) . . ?
F2 B1 N1 111.4(4) . . ?
F1 B1 N1 110.9(4) . . ?
F2 B1 N2 108.7(4) . . ?
F1 B1 N2 108.5(4) . . ?
N1 B1 N2 107.7(3) . . ?
C5 C4 C3 121.3(4) . . ?
C1 C2 C3 117.5(4) . . ?
N4 C9 C8 177.7(6) . . ?
C2 C3 C4 120.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        71.42
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.061
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6642
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv70
_database_code_depnum_ccdc_archive 'CCDC 1470182'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 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 H12 B F2 N5 O0 S'
_chemical_formula_weight         391.21

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'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   7.1001(6)
_cell_length_b                   41.434(3)
_cell_length_c                   11.4739(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3375.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    843
_cell_measurement_theta_min      4.2640
_cell_measurement_theta_max      69.9740

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9051
_exptl_absorpt_correction_T_max  0.9230
_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            6772
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.27
_diffrn_reflns_theta_max         67.24
_reflns_number_total             3026
_reflns_number_gt                1673
_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)+(0.0665P)²+5.0420P] 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         3026
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.2418
_refine_ls_wR_factor_gt          0.2071
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3427(3) 0.53559(4) 0.45699(18) 0.0606(6) Uani 1 1 d . . .
F1 F 0.1545(6) 0.64770(9) 0.4280(4) 0.0714(13) Uani 1 1 d . . .
F2 F 0.4707(7) 0.64870(9) 0.4326(4) 0.0688(13) Uani 1 1 d . . .
N2 N 0.3083(7) 0.63736(11) 0.6110(5) 0.0452(13) Uani 1 1 d . . .
N1 N 0.3173(8) 0.59748(11) 0.4422(4) 0.0447(13) Uani 1 1 d . . .
N5 N 0.2819(8) 0.69308(12) 0.5872(5) 0.0511(15) Uani 1 1 d . . .
H20 H 0.2638 0.6881 0.5153 0.061 Uiso 1 1 calc R . .
N3 N 0.2961(9) 0.67354(12) 0.7748(5) 0.0582(16) Uani 1 1 d . . .
C7 C 0.3317(9) 0.57368(14) 0.5199(6) 0.0479(16) Uani 1 1 d . . .
C6 C 0.3216(10) 0.58629(14) 0.3258(6) 0.0457(16) Uani 1 1 d . . .
C13 C 0.2953(9) 0.66769(15) 0.6598(6) 0.0467(16) Uani 1 1 d . . .
C14 C 0.2929(9) 0.72655(15) 0.6100(6) 0.0451(16) Uani 1 1 d . . .
C9 C 0.3226(9) 0.61121(15) 0.6866(6) 0.0491(17) Uani 1 1 d . . .
C5 C 0.3089(11) 0.60456(16) 0.2270(6) 0.0582(19) Uani 1 1 d . . .
H5 H 0.2957 0.6269 0.2315 0.070 Uiso 1 1 calc R . .
C1 C 0.3368(10) 0.55267(14) 0.3184(6) 0.0460(16) Uani 1 1 d . . .
C11 C 0.3261(11) 0.61681(16) 0.8064(6) 0.0560(18) Uani 1 1 d . . .
H11 H 0.3373 0.5998 0.8590 0.067 Uiso 1 1 calc R . .
C19 C 0.3732(9) 0.74020(16) 0.7094(6) 0.0512(17) Uani 1 1 d . . .
H19 H 0.4181 0.7270 0.7688 0.061 Uiso 1 1 calc R . .
C18 C 0.3859(9) 0.77358(16) 0.7191(6) 0.0531(18) Uani 1 1 d . . .
H18 H 0.4392 0.7826 0.7856 0.064 Uiso 1 1 calc R . .
C8 C 0.3346(10) 0.57960(15) 0.6394(6) 0.0528(18) Uani 1 1 d . . .
C17 C 0.3213(10) 0.79334(17) 0.6324(7) 0.061(2) Uani 1 1 d . . .
H17 H 0.3311 0.8156 0.6395 0.073 Uiso 1 1 calc R . .
C15 C 0.2262(9) 0.74671(15) 0.5230(7) 0.0549(19) Uani 1 1 d . . .
H15 H 0.1710 0.7378 0.4568 0.066 Uiso 1 1 calc R . .
N4 N 0.3660(11) 0.53317(14) 0.7877(6) 0.081(2) Uani 1 1 d . . .
C4 C 0.3162(11) 0.58917(18) 0.1202(7) 0.064(2) Uani 1 1 d . . .
H4 H 0.3073 0.6014 0.0524 0.077 Uiso 1 1 calc R . .
B1 B 0.3122(12) 0.63347(18) 0.4740(7) 0.051(2) Uani 1 1 d . . .
C16 C 0.2405(10) 0.77958(16) 0.5332(7) 0.059(2) Uani 1 1 d . . .
H16 H 0.1962 0.7928 0.4737 0.071 Uiso 1 1 calc R . .
C3 C 0.3366(11) 0.55593(18) 0.1119(7) 0.063(2) Uani 1 1 d . . .
H3 H 0.3432 0.5461 0.0392 0.076 Uiso 1 1 calc R . .
C12 C 0.3128(11) 0.64752(17) 0.8437(7) 0.062(2) Uani 1 1 d . . .
H12 H 0.3155 0.6510 0.9238 0.074 Uiso 1 1 calc R . .
C2A C 0.3471(10) 0.53745(17) 0.2128(7) 0.061(2) Uani 1 1 d . . .
H2A H 0.3609 0.5152 0.2086 0.073 Uiso 1 1 calc R . .
C10B C 0.3519(11) 0.55344(17) 0.7207(7) 0.064(2) 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
S1 C7 1.737(6) . ?
S1 C1 1.741(7) . ?
F1 B1 1.372(9) . ?
F2 B1 1.375(9) . ?
N2 C13 1.379(8) . ?
N2 C9 1.392(8) . ?
N2 B1 1.580(10) . ?
N1 C7 1.333(7) . ?
N1 C6 1.414(8) . ?
N1 B1 1.535(9) . ?
N5 C13 1.345(8) . ?
N5 C14 1.414(8) . ?
N3 C13 1.342(8) . ?
N3 C12 1.342(8) . ?
C7 C8 1.393(9) . ?
C6 C5 1.367(9) . ?
C6 C1 1.400(8) . ?
C14 C15 1.385(9) . ?
C14 C19 1.394(9) . ?
C9 C11 1.394(9) . ?
C9 C8 1.420(9) . ?
C5 C4 1.382(9) . ?
C1 C2A 1.368(9) . ?
C11 C12 1.346(9) . ?
C19 C18 1.390(9) . ?
C18 C17 1.367(9) . ?
C8 C10B 1.435(10) . ?
C17 C16 1.397(10) . ?
C15 C16 1.371(8) . ?
N4 C10B 1.143(9) . ?
C4 C3 1.388(9) . ?
C3 C2A 1.390(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 C1 90.5(3) . . ?
C13 N2 C9 117.4(6) . . ?
C13 N2 B1 119.9(5) . . ?
C9 N2 B1 122.7(5) . . ?
C7 N1 C6 112.8(5) . . ?
C7 N1 B1 124.2(6) . . ?
C6 N1 B1 122.9(5) . . ?
C13 N5 C14 130.5(6) . . ?
C13 N3 C12 115.8(6) . . ?
N1 C7 C8 121.9(6) . . ?
N1 C7 S1 113.4(5) . . ?
C8 C7 S1 124.6(5) . . ?
C5 C6 C1 120.4(6) . . ?
C5 C6 N1 126.9(6) . . ?
C1 C6 N1 112.7(5) . . ?
N3 C13 N5 117.9(6) . . ?
N3 C13 N2 124.3(6) . . ?
N5 C13 N2 117.8(6) . . ?
C15 C14 C19 119.0(6) . . ?
C15 C14 N5 116.1(6) . . ?
C19 C14 N5 124.8(6) . . ?
N2 C9 C11 119.1(6) . . ?
N2 C9 C8 118.9(6) . . ?
C11 C9 C8 122.0(6) . . ?
C6 C5 C4 118.5(6) . . ?
C2A C1 C6 121.1(6) . . ?
C2A C1 S1 128.3(5) . . ?
C6 C1 S1 110.5(5) . . ?
C12 C11 C9 118.0(7) . . ?
C18 C19 C14 119.7(6) . . ?
C17 C18 C19 121.0(7) . . ?
C7 C8 C9 122.5(6) . . ?
C7 C8 C10B 120.5(6) . . ?
C9 C8 C10B 116.9(6) . . ?
C18 C17 C16 119.1(7) . . ?
C16 C15 C14 120.8(7) . . ?
C5 C4 C3 121.5(7) . . ?
F1 B1 F2 109.8(6) . . ?
F1 B1 N1 110.2(6) . . ?
F2 B1 N1 110.2(6) . . ?
F1 B1 N2 109.0(6) . . ?
F2 B1 N2 108.1(6) . . ?
N1 B1 N2 109.6(5) . . ?
C15 C16 C17 120.4(7) . . ?
C4 C3 C2A 119.6(7) . . ?
N3 C12 C11 125.3(7) . . ?
C1 C2A C3 118.8(6) . . ?
N4 C10B C8 178.3(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.337
_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_6378
_audit_block_doi                 10.5517/ccdc.csd.cc1lbv81
_database_code_depnum_ccdc_archive 'CCDC 1470183'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 B F2 N5 O S2'
_chemical_formula_weight         469.33

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'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.9073(10)
_cell_length_b                   11.0350(15)
_cell_length_c                   11.0926(11)
_cell_angle_alpha                103.584(10)
_cell_angle_beta                 95.854(9)
_cell_angle_gamma                113.279(11)
_cell_volume                     1056.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1250
_cell_measurement_theta_min      4.19
_cell_measurement_theta_max      70.096

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_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    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8155
_exptl_absorpt_correction_T_max  0.8358
_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            6345
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.20
_diffrn_reflns_theta_max         67.23
_reflns_number_total             3782
_reflns_number_gt                2325
_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)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3782
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.8836(5) 0.2795(5) 0.3293(5) 0.0452(11) Uani 1 1 d . . .
F1 F 0.8416(3) 0.1520(2) 0.2420(2) 0.0590(7) Uani 1 1 d . . .
F2 F 0.7653(2) 0.2766(3) 0.3867(2) 0.0605(7) Uani 1 1 d . . .
N1 N 1.0255(3) 0.3177(3) 0.4277(3) 0.0420(8) Uani 1 1 d . . .
N2 N 0.9191(3) 0.3931(3) 0.2594(3) 0.0426(8) Uani 1 1 d . . .
N3 N 0.8059(4) 0.4703(3) 0.1140(3) 0.0503(9) Uani 1 1 d . . .
N4 N 1.4469(4) 0.6976(4) 0.3857(4) 0.0652(11) Uani 1 1 d . . .
N5 N 0.9559(3) 0.6665(3) 0.0589(3) 0.0437(8) Uani 1 1 d . . .
H27 H 1.0466 0.7271 0.0678 0.052 Uiso 1 1 calc R . .
O1 O 0.7396(4) 0.1322(4) 0.8982(3) 0.0860(12) Uani 1 1 d . . .
S1 S 1.30578(11) 0.42561(11) 0.53997(11) 0.0524(3) Uani 1 1 d . . .
S2 S 0.57627(13) 0.03859(12) 0.84918(12) 0.0610(4) Uani 1 1 d . . .
C1 C 1.1772(4) 0.2906(4) 0.5846(4) 0.0454(10) Uani 1 1 d . . .
C2 C 1.2072(5) 0.2319(4) 0.6763(4) 0.0531(11) Uani 1 1 d . . .
H2 H 1.3045 0.2626 0.7223 0.064 Uiso 1 1 calc R . .
C3 C 1.0866(5) 0.1265(4) 0.6962(4) 0.0549(11) Uani 1 1 d . . .
H3 H 1.1030 0.0856 0.7570 0.066 Uiso 1 1 calc R . .
C5 C 0.9126(5) 0.1392(4) 0.5366(4) 0.0494(10) Uani 1 1 d . . .
H5 H 0.8150 0.1082 0.4911 0.059 Uiso 1 1 calc R . .
C6 C 1.0325(4) 0.2454(4) 0.5155(4) 0.0430(9) Uani 1 1 d . . .
C7 C 1.1612(4) 0.4180(4) 0.4319(4) 0.0423(9) Uani 1 1 d . . .
C8 C 1.1828(4) 0.5056(4) 0.3563(4) 0.0403(9) Uani 1 1 d . . .
C9 C 1.3292(4) 0.6120(4) 0.3714(4) 0.0453(10) Uani 1 1 d . . .
C10 C 1.0597(4) 0.4979(4) 0.2716(3) 0.0394(9) Uani 1 1 d . . .
C11 C 1.0715(4) 0.5888(4) 0.2029(3) 0.0396(9) Uani 1 1 d . . .
H11 H 1.1650 0.6595 0.2084 0.048 Uiso 1 1 calc R . .
C12 C 0.9436(4) 0.5755(4) 0.1248(4) 0.0421(9) Uani 1 1 d . . .
C13 C 0.8026(5) 0.3874(4) 0.1804(4) 0.0514(11) Uani 1 1 d . . .
H13 H 0.7091 0.3157 0.1726 0.062 Uiso 1 1 calc R . .
C14 C 0.8467(4) 0.6798(4) -0.0218(4) 0.0440(10) Uani 1 1 d . . .
C15 C 0.6942(5) 0.5903(4) -0.0564(4) 0.0524(11) Uani 1 1 d . . .
H15 H 0.6564 0.5155 -0.0246 0.063 Uiso 1 1 calc R . .
C18 C 0.8029(6) 0.8132(5) -0.1506(5) 0.0697(14) Uani 1 1 d . . .
H18 H 0.8399 0.8888 -0.1815 0.084 Uiso 1 1 calc R . .
C4A C 0.9424(5) 0.0806(5) 0.6277(4) 0.0565(12) Uani 1 1 d . . .
H4A H 0.8635 0.0089 0.6429 0.068 Uiso 1 1 calc R . .
C19B C 0.8996(5) 0.7918(4) -0.0681(4) 0.0550(11) Uani 1 1 d . . .
H19B H 1.0012 0.8534 -0.0437 0.066 Uiso 1 1 calc R . .
C1C C 0.5448(6) -0.0014(5) 0.6811(5) 0.0811(17) Uani 1 1 d . . .
H1C1 H 0.5884 0.0825 0.6584 0.122 Uiso 1 1 calc R . .
H1C2 H 0.4385 -0.0475 0.6454 0.122 Uiso 1 1 calc R . .
H1C3 H 0.5905 -0.0608 0.6486 0.122 Uiso 1 1 calc R . .
C16D C 0.5993(5) 0.6137(5) -0.1389(4) 0.0605(12) Uani 1 1 d . . .
H16D H 0.4972 0.5538 -0.1620 0.073 Uiso 1 1 calc R . .
C17E C 0.6520(5) 0.7232(5) -0.1874(4) 0.0618(12) Uani 1 1 d . . .
H17E H 0.5870 0.7363 -0.2441 0.074 Uiso 1 1 calc R . .
C1F C 0.4790(5) 0.1440(5) 0.8774(5) 0.0796(16) Uani 1 1 d . . .
H1F1 H 0.4912 0.1814 0.9673 0.119 Uiso 1 1 calc R . .
H1F2 H 0.3739 0.0893 0.8390 0.119 Uiso 1 1 calc R . .
H1F3 H 0.5192 0.2182 0.8411 0.119 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.381(5) . ?
B1 F2 1.383(5) . ?
B1 N1 1.533(5) . ?
B1 N2 1.568(5) . ?
N1 C7 1.350(4) . ?
N1 C6 1.409(5) . ?
N2 C13 1.347(5) . ?
N2 C10 1.382(4) . ?
N3 C13 1.295(5) . ?
N3 C12 1.369(5) . ?
N4 C9 1.140(5) . ?
N5 C12 1.351(5) . ?
N5 C14 1.408(5) . ?
O1 S2 1.489(3) . ?
S1 C7 1.733(4) . ?
S1 C1 1.750(4) . ?
S2 C1C 1.776(5) . ?
S2 C1F 1.777(5) . ?
C1 C6 1.387(5) . ?
C1 C2 1.393(5) . ?
C2 C3 1.380(5) . ?
C3 C4A 1.379(6) . ?
C5 C4A 1.386(5) . ?
C5 C6 1.388(5) . ?
C7 C8 1.392(5) . ?
C8 C9 1.422(5) . ?
C8 C10 1.423(5) . ?
C10 C11 1.373(5) . ?
C11 C12 1.395(5) . ?
C14 C19B 1.382(5) . ?
C14 C15 1.389(5) . ?
C15 C16D 1.384(5) . ?
C18 C17E 1.378(6) . ?
C18 C19B 1.383(6) . ?
C16D C17E 1.373(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
F1 B1 F2 109.2(3) . . ?
F1 B1 N1 110.5(4) . . ?
F2 B1 N1 111.3(4) . . ?
F1 B1 N2 109.6(4) . . ?
F2 B1 N2 108.0(3) . . ?
N1 B1 N2 108.2(3) . . ?
C7 N1 C6 112.6(3) . . ?
C7 N1 B1 122.9(3) . . ?
C6 N1 B1 124.3(3) . . ?
C13 N2 C10 117.4(3) . . ?
C13 N2 B1 117.1(3) . . ?
C10 N2 B1 125.6(3) . . ?
C13 N3 C12 116.4(3) . . ?
C12 N5 C14 131.4(3) . . ?
C7 S1 C1 90.45(19) . . ?
O1 S2 C1C 106.0(2) . . ?
O1 S2 C1F 106.7(2) . . ?
C1C S2 C1F 98.2(3) . . ?
C6 C1 C2 121.7(4) . . ?
C6 C1 S1 110.7(3) . . ?
C2 C1 S1 127.6(3) . . ?
C3 C2 C1 117.3(4) . . ?
C4A C3 C2 121.4(4) . . ?
C4A C5 C6 118.1(4) . . ?
C1 C6 C5 120.2(4) . . ?
C1 C6 N1 113.1(3) . . ?
C5 C6 N1 126.7(4) . . ?
N1 C7 C8 123.3(3) . . ?
N1 C7 S1 113.1(3) . . ?
C8 C7 S1 123.5(3) . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 C10 121.4(3) . . ?
C9 C8 C10 119.3(3) . . ?
N4 C9 C8 178.8(4) . . ?
C11 C10 N2 118.2(3) . . ?
C11 C10 C8 124.2(3) . . ?
N2 C10 C8 117.6(3) . . ?
C10 C11 C12 120.2(3) . . ?
N5 C12 N3 119.8(3) . . ?
N5 C12 C11 119.8(3) . . ?
N3 C12 C11 120.4(4) . . ?
N3 C13 N2 127.5(4) . . ?
C19B C14 C15 119.3(4) . . ?
C19B C14 N5 115.6(4) . . ?
C15 C14 N5 125.1(4) . . ?
C16D C15 C14 119.2(4) . . ?
C17E C18 C19B 120.4(4) . . ?
C3 C4A C5 121.3(4) . . ?
C14 C19B C18 120.6(4) . . ?
C17E C16D C15 121.7(4) . . ?
C16D C17E C18 118.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_150313a
_database_code_depnum_ccdc_archive 'CCDC 1470214'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-09-23 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 H12 B F2 N5 O0 S'
_chemical_formula_weight         343.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   9.1073(8)
_cell_length_b                   22.539(2)
_cell_length_c                   7.3835(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.260(2)
_cell_angle_gamma                90.00
_cell_volume                     1503.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1358
_cell_measurement_theta_min      2.430
_cell_measurement_theta_max      25.959

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9193
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7139
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2637
_reflns_number_gt                1485
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.1705P)²+0.7398P] 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       0.030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2637
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.3028
_refine_ls_wR_factor_gt          0.2745
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2915(6) 0.3855(2) 0.7289(8) 0.0417(14) Uani 1 1 d . . .
F1 F 0.3305(3) 0.37972(14) 0.5555(4) 0.0543(8) Uani 1 1 d . . .
F2 F 0.3240(3) 0.44169(12) 0.7919(4) 0.0570(9) Uani 1 1 d . . .
N1 N 0.1252(4) 0.37012(17) 0.7254(5) 0.0397(10) Uani 1 1 d . . .
N2 N 0.3799(4) 0.33487(17) 0.8485(5) 0.0377(10) Uani 1 1 d . . .
N3 N 0.6288(4) 0.30231(18) 0.9311(6) 0.0470(12) Uani 1 1 d . . .
N4 N 0.0915(6) 0.1599(2) 0.6704(8) 0.0702(16) Uani 1 1 d . . .
N5 N 0.5565(4) 0.39123(18) 1.0395(6) 0.0441(11) Uani 1 1 d . . .
S1 S -0.10199(14) 0.30178(6) 0.6605(2) 0.0516(4) Uani 1 1 d . . .
C1 C -0.1304(5) 0.3785(3) 0.6627(7) 0.0475(14) Uani 1 1 d . . .
C2 C -0.2650(6) 0.4086(3) 0.6263(7) 0.0570(16) Uani 1 1 d . . .
H2 H -0.3531 0.3881 0.5952 0.068 Uiso 1 1 calc R . .
C3 C -0.2632(6) 0.4689(3) 0.6376(8) 0.0644(17) Uani 1 1 d . . .
H3 H -0.3513 0.4900 0.6127 0.077 Uiso 1 1 calc R . .
C4 C -0.1315(7) 0.4994(3) 0.6860(9) 0.0678(18) Uani 1 1 d . . .
H4 H -0.1333 0.5406 0.6958 0.081 Uiso 1 1 calc R . .
C5 C 0.0010(6) 0.4702(2) 0.7194(8) 0.0546(15) Uani 1 1 d . . .
H5 H 0.0885 0.4911 0.7521 0.065 Uiso 1 1 calc R . .
C6 C 0.0022(5) 0.4083(2) 0.7034(6) 0.0420(13) Uani 1 1 d . . .
C7 C 0.0849(5) 0.3127(2) 0.7109(6) 0.0394(12) Uani 1 1 d . . .
C8 C 0.1878(5) 0.2662(2) 0.7339(7) 0.0408(12) Uani 1 1 d . . .
C9 C 0.1354(6) 0.2073(2) 0.6981(7) 0.0475(14) Uani 1 1 d . . .
C10 C 0.3386(5) 0.2764(2) 0.8041(6) 0.0390(12) Uani 1 1 d . . .
C11 C 0.4426(5) 0.2313(2) 0.8252(6) 0.0413(13) Uani 1 1 d . . .
H11 H 0.4155 0.1917 0.8099 0.050 Uiso 1 1 calc R . .
C12 C 0.5868(5) 0.2478(2) 0.8692(7) 0.0431(13) Uani 1 1 d . . .
H12 H 0.6601 0.2200 0.8560 0.052 Uiso 1 1 calc R . .
C13 C 0.5233(5) 0.3418(2) 0.9381(6) 0.0374(12) Uani 1 1 d . . .
C14 C 0.4504(7) 0.4227(2) 1.1346(8) 0.0559(15) Uani 1 1 d . . .
H14A H 0.3562 0.4031 1.1134 0.084 Uiso 1 1 calc R . .
H14B H 0.4406 0.4627 1.0903 0.084 Uiso 1 1 calc R . .
H14C H 0.4842 0.4230 1.2632 0.084 Uiso 1 1 calc R . .
C15 C 0.7126(6) 0.4027(3) 1.1063(8) 0.0622(17) Uani 1 1 d . . .
H15A H 0.7443 0.3763 1.2058 0.093 Uiso 1 1 calc R . .
H15B H 0.7239 0.4430 1.1475 0.093 Uiso 1 1 calc R . .
H15C H 0.7718 0.3961 1.0094 0.093 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F2 1.370(6) . ?
B1 F1 1.378(7) . ?
B1 N1 1.550(7) . ?
B1 N2 1.596(7) . ?
N1 C7 1.346(6) . ?
N1 C6 1.406(6) . ?
N2 C13 1.396(6) . ?
N2 C10 1.397(6) . ?
N3 C13 1.315(6) . ?
N3 C12 1.349(6) . ?
N4 C9 1.150(7) . ?
N5 C13 1.356(6) . ?
N5 C14 1.449(7) . ?
N5 C15 1.468(6) . ?
S1 C7 1.714(5) . ?
S1 C1 1.748(6) . ?
C1 C6 1.382(7) . ?
C1 C2 1.397(7) . ?
C2 C3 1.363(9) . ?
C3 C4 1.390(9) . ?
C4 C5 1.369(8) . ?
C5 C6 1.401(7) . ?
C7 C8 1.402(7) . ?
C8 C10 1.424(7) . ?
C8 C9 1.424(7) . ?
C10 C11 1.386(7) . ?
C11 C12 1.363(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 B1 F1 109.4(4) . . ?
F2 B1 N1 112.4(4) . . ?
F1 B1 N1 109.3(4) . . ?
F2 B1 N2 113.6(4) . . ?
F1 B1 N2 106.0(4) . . ?
N1 B1 N2 105.9(4) . . ?
C7 N1 C6 111.9(4) . . ?
C7 N1 B1 118.2(4) . . ?
C6 N1 B1 128.9(4) . . ?
C13 N2 C10 115.1(4) . . ?
C13 N2 B1 124.0(4) . . ?
C10 N2 B1 116.2(4) . . ?
C13 N3 C12 116.9(4) . . ?
C13 N5 C14 123.7(4) . . ?
C13 N5 C15 117.9(4) . . ?
C14 N5 C15 115.3(4) . . ?
C7 S1 C1 90.0(2) . . ?
C6 C1 C2 121.8(5) . . ?
C6 C1 S1 110.9(4) . . ?
C2 C1 S1 127.3(4) . . ?
C3 C2 C1 118.0(5) . . ?
C2 C3 C4 120.8(5) . . ?
C5 C4 C3 121.4(6) . . ?
C4 C5 C6 118.7(5) . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 N1 112.9(5) . . ?
C5 C6 N1 127.9(5) . . ?
N1 C7 C8 122.5(4) . . ?
N1 C7 S1 114.1(4) . . ?
C8 C7 S1 123.3(4) . . ?
C7 C8 C10 121.4(4) . . ?
C7 C8 C9 118.1(4) . . ?
C10 C8 C9 120.3(4) . . ?
N4 C9 C8 179.0(6) . . ?
C11 C10 N2 120.4(4) . . ?
C11 C10 C8 122.4(4) . . ?
N2 C10 C8 117.2(4) . . ?
C12 C11 C10 116.8(5) . . ?
N3 C12 C11 123.5(5) . . ?
N3 C13 N5 117.7(4) . . ?
N3 C13 N2 123.4(4) . . ?
N5 C13 N2 118.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.123
