# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_150527i
_database_code_depnum_ccdc_archive 'CCDC 1554082'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 B F2 N4 O'
_chemical_formula_weight         274.04

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   7.2996(6)
_cell_length_b                   9.5435(7)
_cell_length_c                   17.2754(15)
_cell_angle_alpha                84.089(2)
_cell_angle_beta                 80.1410(10)
_cell_angle_gamma                84.539(2)
_cell_volume                     1175.70(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1371
_cell_measurement_theta_min      2.4025
_cell_measurement_theta_max      24.9115

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_T_max  0.9780
_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            5959
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4063
_reflns_number_gt                2128
_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)+(0.0605P)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         4063
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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
N7 N 0.6393(3) 0.3941(2) 0.08942(11) 0.0336(5) Uani 1 1 d . . .
N6 N 0.7450(3) 0.1976(2) -0.00065(12) 0.0356(5) Uani 1 1 d . . .
C20 C 0.7162(3) 0.4895(3) 0.02997(14) 0.0319(6) Uani 1 1 d . . .
O2 O 0.6032(3) 0.80442(18) 0.13143(11) 0.0509(5) Uani 1 1 d . . .
N2 N 0.2518(3) 0.7696(2) 0.52868(12) 0.0433(6) Uani 1 1 d . . .
N3 N 0.2854(3) 0.5780(2) 0.43418(12) 0.0407(6) Uani 1 1 d . . .
F4 F 0.4679(2) 0.19023(15) 0.09647(9) 0.0579(5) Uani 1 1 d . . .
N8 N 0.5406(3) 0.5742(2) 0.17609(12) 0.0427(6) Uani 1 1 d . . .
C23 C 0.6152(4) 0.6676(3) 0.11786(15) 0.0372(7) Uani 1 1 d . . .
C5 C 0.2154(4) 0.6684(3) 0.58976(15) 0.0390(7) Uani 1 1 d . . .
C18 C 0.8029(3) 0.4388(3) -0.04186(14) 0.0349(6) Uani 1 1 d . . .
F3 F 0.7440(2) 0.16143(15) 0.13873(9) 0.0599(5) Uani 1 1 d . . .
C17 C 0.8195(3) 0.2948(3) -0.05741(15) 0.0350(6) Uani 1 1 d . . .
C22 C 0.7019(4) 0.6307(3) 0.04582(15) 0.0377(7) Uani 1 1 d . . .
H22 H 0.7511 0.6990 0.0076 0.045 Uiso 1 1 calc R . .
O1 O 0.2615(3) 0.1739(2) 0.39073(11) 0.0586(6) Uani 1 1 d . . .
C10 C 0.2373(4) 0.3409(3) 0.48142(16) 0.0450(7) Uani 1 1 d . . .
H10 H 0.2090 0.2709 0.5222 0.054 Uiso 1 1 calc R . .
N4 N 0.3209(3) 0.4032(2) 0.34335(13) 0.0495(6) Uani 1 1 d . . .
C8 C 0.2431(3) 0.4797(3) 0.49757(15) 0.0364(7) Uani 1 1 d . . .
C21 C 0.5574(4) 0.4439(3) 0.15827(15) 0.0420(7) Uani 1 1 d . . .
H21 H 0.5071 0.3776 0.1975 0.050 Uiso 1 1 calc R . .
B2 B 0.6475(5) 0.2329(3) 0.08311(18) 0.0381(8) Uani 1 1 d . . .
F1 F 0.1467(3) 0.81024(16) 0.40421(9) 0.0641(5) Uani 1 1 d . . .
F2 F 0.4555(2) 0.78420(17) 0.40458(10) 0.0676(6) Uani 1 1 d . . .
C13 C 0.9102(4) 0.2484(3) -0.12983(15) 0.0437(7) Uani 1 1 d . . .
H13 H 0.9614 0.3137 -0.1694 0.052 Uiso 1 1 calc R . .
C6 C 0.2095(4) 0.5266(3) 0.57385(15) 0.0408(7) Uani 1 1 d . . .
C11 C 0.2735(4) 0.3088(3) 0.40509(17) 0.0433(7) Uani 1 1 d . . .
C19 C 0.8809(4) 0.5388(3) -0.10248(16) 0.0420(7) Uani 1 1 d . . .
C9 C 0.3223(4) 0.5322(3) 0.36136(16) 0.0488(8) Uani 1 1 d . . .
H9 H 0.3518 0.6001 0.3195 0.059 Uiso 1 1 calc R . .
C7 C 0.1650(4) 0.4241(3) 0.63860(17) 0.0476(8) Uani 1 1 d . . .
C1 C 0.1850(4) 0.7112(3) 0.66742(16) 0.0489(8) Uani 1 1 d . . .
H1 H 0.1610 0.6443 0.7102 0.059 Uiso 1 1 calc R . .
C16 C 0.7572(4) 0.0591(3) -0.01513(17) 0.0471(8) Uani 1 1 d . . .
H16 H 0.7035 -0.0058 0.0241 0.057 Uiso 1 1 calc R . .
B1 B 0.2864(5) 0.7390(3) 0.44058(18) 0.0425(8) Uani 1 1 d . . .
C15 C 0.8447(4) 0.0123(3) -0.08442(18) 0.0542(8) Uani 1 1 d . . .
H15 H 0.8516 -0.0828 -0.0928 0.065 Uiso 1 1 calc R . .
C4 C 0.2569(4) 0.9062(3) 0.54297(18) 0.0593(9) Uani 1 1 d . . .
H4 H 0.2810 0.9732 0.5002 0.071 Uiso 1 1 calc R . .
N5 N 0.9429(4) 0.6202(3) -0.15101(15) 0.0615(8) Uani 1 1 d . . .
C14 C 0.9239(4) 0.1106(3) -0.14267(17) 0.0529(8) Uani 1 1 d . . .
H14 H 0.9863 0.0811 -0.1905 0.063 Uiso 1 1 calc R . .
N1 N 0.1281(4) 0.3409(3) 0.69032(15) 0.0696(8) Uani 1 1 d . . .
C3 C 0.2285(5) 0.9493(4) 0.61648(19) 0.0672(10) Uani 1 1 d . . .
H3 H 0.2341 1.0436 0.6244 0.081 Uiso 1 1 calc R . .
C24 C 0.5299(5) 0.8447(3) 0.20788(16) 0.0600(9) Uani 1 1 d . . .
H24A H 0.4025 0.8218 0.2217 0.090 Uiso 1 1 calc R . .
H24B H 0.5358 0.9446 0.2086 0.090 Uiso 1 1 calc R . .
H24C H 0.6018 0.7950 0.2452 0.090 Uiso 1 1 calc R . .
C2 C 0.1905(4) 0.8482(3) 0.67989(18) 0.0602(9) Uani 1 1 d . . .
H2 H 0.1689 0.8750 0.7311 0.072 Uiso 1 1 calc R . .
C12 C 0.3009(5) 0.1387(3) 0.31109(17) 0.0661(10) Uani 1 1 d . . .
H12A H 0.2273 0.2022 0.2796 0.099 Uiso 1 1 calc R . .
H12B H 0.2710 0.0435 0.3089 0.099 Uiso 1 1 calc R . .
H12C H 0.4309 0.1466 0.2911 0.099 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
N7 C21 1.348(3) . ?
N7 C20 1.380(3) . ?
N7 B2 1.549(3) . ?
N6 C17 1.358(3) . ?
N6 C16 1.362(3) . ?
N6 B2 1.554(3) . ?
C20 C22 1.393(3) . ?
C20 C18 1.404(3) . ?
O2 C23 1.343(3) . ?
O2 C24 1.415(3) . ?
N2 C4 1.357(3) . ?
N2 C5 1.364(3) . ?
N2 B1 1.553(4) . ?
N3 C9 1.350(3) . ?
N3 C8 1.379(3) . ?
N3 B1 1.552(4) . ?
F4 B2 1.384(3) . ?
N8 C21 1.301(3) . ?
N8 C23 1.350(3) . ?
C23 C22 1.361(3) . ?
C5 C6 1.415(4) . ?
C5 C1 1.418(4) . ?
C18 C17 1.417(3) . ?
C18 C19 1.423(4) . ?
F3 B2 1.375(3) . ?
C17 C13 1.405(3) . ?
O1 C11 1.349(3) . ?
O1 C12 1.425(3) . ?
C10 C11 1.361(4) . ?
C10 C8 1.388(3) . ?
N4 C9 1.302(3) . ?
N4 C11 1.343(3) . ?
C8 C6 1.409(3) . ?
F1 B1 1.377(4) . ?
F2 B1 1.371(4) . ?
C13 C14 1.348(3) . ?
C6 C7 1.423(4) . ?
C19 N5 1.146(3) . ?
C7 N1 1.146(3) . ?
C1 C2 1.352(4) . ?
C16 C15 1.354(4) . ?
C15 C14 1.391(4) . ?
C4 C3 1.351(4) . ?
C3 C2 1.392(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
C21 N7 C20 117.9(2) . . ?
C21 N7 B2 117.9(2) . . ?
C20 N7 B2 124.2(2) . . ?
C17 N6 C16 119.9(2) . . ?
C17 N6 B2 124.0(2) . . ?
C16 N6 B2 116.1(2) . . ?
N7 C20 C22 117.1(2) . . ?
N7 C20 C18 118.4(2) . . ?
C22 C20 C18 124.4(2) . . ?
C23 O2 C24 119.5(2) . . ?
C4 N2 C5 120.3(2) . . ?
C4 N2 B1 116.1(2) . . ?
C5 N2 B1 123.6(2) . . ?
C9 N3 C8 118.0(2) . . ?
C9 N3 B1 117.6(2) . . ?
C8 N3 B1 124.4(2) . . ?
C21 N8 C23 114.7(2) . . ?
O2 C23 N8 118.4(2) . . ?
O2 C23 C22 118.0(2) . . ?
N8 C23 C22 123.6(2) . . ?
N2 C5 C6 119.6(2) . . ?
N2 C5 C1 117.7(3) . . ?
C6 C5 C1 122.7(2) . . ?
C20 C18 C17 124.3(2) . . ?
C20 C18 C19 117.6(2) . . ?
C17 C18 C19 118.1(2) . . ?
N6 C17 C13 118.5(2) . . ?
N6 C17 C18 119.2(2) . . ?
C13 C17 C18 122.4(2) . . ?
C23 C22 C20 119.3(2) . . ?
C11 O1 C12 118.5(2) . . ?
C11 C10 C8 119.1(3) . . ?
C9 N4 C11 114.8(2) . . ?
N3 C8 C10 117.3(2) . . ?
N3 C8 C6 118.1(2) . . ?
C10 C8 C6 124.6(2) . . ?
N8 C21 N7 127.4(2) . . ?
F3 B2 F4 108.7(2) . . ?
F3 B2 N7 110.1(2) . . ?
F4 B2 N7 109.3(2) . . ?
F3 B2 N6 109.6(2) . . ?
F4 B2 N6 109.3(2) . . ?
N7 B2 N6 109.9(2) . . ?
C14 C13 C17 120.9(3) . . ?
C8 C6 C5 124.2(2) . . ?
C8 C6 C7 117.5(3) . . ?
C5 C6 C7 118.3(2) . . ?
N4 C11 O1 118.2(3) . . ?
N4 C11 C10 123.9(3) . . ?
O1 C11 C10 118.0(2) . . ?
N5 C19 C18 179.4(3) . . ?
N4 C9 N3 127.0(2) . . ?
N1 C7 C6 179.3(4) . . ?
C2 C1 C5 120.7(3) . . ?
C15 C16 N6 122.5(3) . . ?
F2 B1 F1 109.5(2) . . ?
F2 B1 N3 109.6(2) . . ?
F1 B1 N3 109.3(2) . . ?
F2 B1 N2 109.5(3) . . ?
F1 B1 N2 109.0(2) . . ?
N3 B1 N2 109.9(2) . . ?
C16 C15 C14 118.2(3) . . ?
C3 C4 N2 123.0(3) . . ?
C13 C14 C15 120.1(3) . . ?
C4 C3 C2 117.9(3) . . ?
C1 C2 C3 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_150527g
_database_code_depnum_ccdc_archive 'CCDC 1554081'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.
2017-07-11 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 H12 B F2 N5'
_chemical_formula_weight         287.09

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

_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                   7.2050(6)
_cell_length_b                   18.0229(15)
_cell_length_c                   11.3751(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.152(3)
_cell_angle_gamma                90.00
_cell_volume                     1302.37(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1727
_cell_measurement_theta_min      2.3165
_cell_measurement_theta_max      26.528

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_T_max  0.9801
_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            6441
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2290
_reflns_number_gt                1418
_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)+(0.1486P)²+3.0739P] 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       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2290
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.2508(4) 0.99277(13) 1.0014(2) 0.0337(6) Uani 1 1 d . . .
C5 C 0.4271(4) 1.05715(14) 1.2217(2) 0.0351(6) Uani 1 1 d . . .
C11 C 0.0844(4) 0.93483(16) 0.7861(3) 0.0425(7) Uani 1 1 d . . .
B1 B 0.2645(5) 1.13660(17) 1.0086(3) 0.0433(8) Uani 1 1 d . . .
F2 F 0.0828(3) 1.17521(9) 0.97958(16) 0.0578(5) Uani 1 1 d . . .
C2 C 0.6021(5) 1.11767(17) 1.4351(3) 0.0527(8) Uani 1 1 d . . .
H2 H 0.6726 1.1151 1.5277 0.063 Uiso 1 1 calc R . .
F1 F 0.3841(3) 1.17751(9) 0.96653(17) 0.0639(6) Uani 1 1 d . . .
C13 C -0.0921(5) 0.8817(2) 0.5612(3) 0.0646(9) Uani 1 1 d . . .
H13A H -0.2406 0.8760 0.5296 0.097 Uiso 1 1 calc R . .
H13B H -0.0439 0.8440 0.5224 0.097 Uiso 1 1 calc R . .
H13C H -0.0648 0.9297 0.5361 0.097 Uiso 1 1 calc R . .
N3 N 0.2103(3) 1.06055(12) 0.93799(19) 0.0404(6) Uani 1 1 d . . .
N5 N 0.0186(4) 0.87472(14) 0.7058(2) 0.0537(7) Uani 1 1 d . . .
C9 C 0.1101(5) 1.06017(17) 0.8026(3) 0.0514(8) Uani 1 1 d . . .
H9 H 0.0854 1.1062 0.7609 0.062 Uiso 1 1 calc R . .
C10 C 0.1875(4) 0.92914(15) 0.9241(2) 0.0398(7) Uani 1 1 d . . .
H10 H 0.2139 0.8827 0.9645 0.048 Uiso 1 1 calc R . .
C4 C 0.4607(5) 1.18776(15) 1.2363(3) 0.0495(8) Uani 1 1 d . . .
H4 H 0.4360 1.2332 1.1929 0.059 Uiso 1 1 calc R . .
N2 N 0.3911(3) 1.12495(11) 1.1621(2) 0.0385(6) Uani 1 1 d . . .
C1 C 0.5364(4) 1.05488(16) 1.3627(2) 0.0445(7) Uani 1 1 d . . .
H1 H 0.5632 1.0093 1.4060 0.053 Uiso 1 1 calc R . .
C12 C 0.0474(5) 0.80106(17) 0.7614(3) 0.0626(9) Uani 1 1 d . . .
H12A H 0.1927 0.7939 0.8250 0.094 Uiso 1 1 calc R . .
H12B H 0.0066 0.7651 0.6913 0.094 Uiso 1 1 calc R . .
H12C H -0.0380 0.7951 0.8048 0.094 Uiso 1 1 calc R . .
C3 C 0.5649(5) 1.18645(17) 1.3717(3) 0.0567(9) Uani 1 1 d . . .
H3 H 0.6102 1.2301 1.4207 0.068 Uiso 1 1 calc R . .
C7 C 0.3957(5) 0.92296(15) 1.2087(2) 0.0437(7) Uani 1 1 d . . .
C6 C 0.3561(4) 0.99235(13) 1.1425(2) 0.0363(6) Uani 1 1 d . . .
N4 N 0.0451(4) 1.00270(14) 0.7249(2) 0.0545(7) Uani 1 1 d . . .
N1 N 0.4265(5) 0.86753(14) 1.2638(2) 0.0668(9) 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
C8 N3 1.378(3) . ?
C8 C10 1.385(3) . ?
C8 C6 1.415(3) . ?
C5 N2 1.362(3) . ?
C5 C1 1.415(3) . ?
C5 C6 1.415(3) . ?
C11 N5 1.351(3) . ?
C11 N4 1.369(4) . ?
C11 C10 1.387(3) . ?
B1 F2 1.378(4) . ?
B1 F1 1.380(4) . ?
B1 N3 1.543(4) . ?
B1 N2 1.556(4) . ?
C2 C1 1.347(4) . ?
C2 C3 1.395(4) . ?
C2 H2 0.9300 . ?
C13 N5 1.456(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N3 C9 1.358(3) . ?
N5 C12 1.443(4) . ?
C9 N4 1.297(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C4 C3 1.358(4) . ?
C4 N2 1.359(3) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C3 H3 0.9300 . ?
C7 N1 1.144(3) . ?
C7 C6 1.418(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
N3 C8 C10 118.5(2) . . ?
N3 C8 C6 117.8(2) . . ?
C10 C8 C6 123.7(2) . . ?
N2 C5 C1 117.6(2) . . ?
N2 C5 C6 119.8(2) . . ?
C1 C5 C6 122.6(2) . . ?
N5 C11 N4 116.8(2) . . ?
N5 C11 C10 122.4(3) . . ?
N4 C11 C10 120.9(2) . . ?
F2 B1 F1 109.0(2) . . ?
F2 B1 N3 110.2(2) . . ?
F1 B1 N3 109.8(2) . . ?
F2 B1 N2 109.0(2) . . ?
F1 B1 N2 109.3(2) . . ?
N3 B1 N2 109.6(2) . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 N3 C8 117.2(2) . . ?
C9 N3 B1 117.6(2) . . ?
C8 N3 B1 125.2(2) . . ?
C11 N5 C12 120.6(2) . . ?
C11 N5 C13 121.7(3) . . ?
C12 N5 C13 117.6(2) . . ?
N4 C9 N3 127.2(3) . . ?
N4 C9 H9 116.4 . . ?
N3 C9 H9 116.4 . . ?
C8 C10 C11 119.8(2) . . ?
C8 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C3 C4 N2 122.3(3) . . ?
C3 C4 H4 118.8 . . ?
N2 C4 H4 118.8 . . ?
C4 N2 C5 120.7(2) . . ?
C4 N2 B1 115.7(2) . . ?
C5 N2 B1 123.6(2) . . ?
C2 C1 C5 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C5 C1 H1 119.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
N1 C7 C6 178.7(3) . . ?
C8 C6 C7 118.2(2) . . ?
C8 C6 C5 123.9(2) . . ?
C7 C6 C5 117.9(2) . . ?
C9 N4 C11 116.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.173
_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_150527h
_database_code_depnum_ccdc_archive 'CCDC 1554080'
_audit_update_record             
;
2017-06-04 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 B Cl F2 N4'
_chemical_formula_weight         278.46

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   10.4083(9)
_cell_length_b                   5.5521(5)
_cell_length_c                   19.6438(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8410(10)
_cell_angle_gamma                90.00
_cell_volume                     1132.62(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1805
_cell_measurement_theta_min      3.5515
_cell_measurement_theta_max      26.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9266
_exptl_absorpt_correction_T_max  0.9394
_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            5351
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2000
_reflns_number_gt                1430
_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)+(0.0431P)²+0.1181P] 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         2000
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.43255(6) 1.26833(12) 0.04841(3) 0.0564(2) Uani 1 1 d . . .
F2 F 0.07709(12) 0.8210(3) 0.26183(5) 0.0527(4) Uani 1 1 d . . .
F1 F 0.11618(11) 0.4618(2) 0.21230(6) 0.0516(4) Uani 1 1 d . . .
N3 N 0.15452(14) 0.8234(3) 0.15018(8) 0.0317(4) Uani 1 1 d . . .
N2 N -0.07012(15) 0.6889(3) 0.17179(8) 0.0328(4) Uani 1 1 d . . .
C5 C -0.11786(18) 0.8660(4) 0.12925(9) 0.0320(5) Uani 1 1 d . . .
N4 N 0.36644(16) 0.8999(4) 0.11920(9) 0.0418(5) Uani 1 1 d . . .
C8 C 0.10350(19) 1.0056(4) 0.10929(9) 0.0306(5) Uani 1 1 d . . .
C11 C 0.31819(19) 1.0927(4) 0.08443(10) 0.0368(5) Uani 1 1 d . . .
C10 C 0.19211(19) 1.1510(4) 0.07626(10) 0.0355(5) Uani 1 1 d . . .
H10 H 0.1644 1.2823 0.0498 0.043 Uiso 1 1 calc R . .
C6 C -0.03027(18) 1.0318(4) 0.10191(10) 0.0319(5) Uani 1 1 d . . .
C4 C -0.1496(2) 0.5182(4) 0.19589(10) 0.0413(5) Uani 1 1 d . . .
H4 H -0.1144 0.3975 0.2242 0.050 Uiso 1 1 calc R . .
N1 N -0.12822(19) 1.3649(4) 0.02373(10) 0.0528(5) Uani 1 1 d . . .
C9 C 0.28223(19) 0.7772(4) 0.15087(10) 0.0380(5) Uani 1 1 d . . .
H9 H 0.3127 0.6454 0.1764 0.046 Uiso 1 1 calc R . .
C7 C -0.0830(2) 1.2192(4) 0.05855(10) 0.0368(5) Uani 1 1 d . . .
C1 C -0.25164(19) 0.8718(4) 0.11337(11) 0.0409(5) Uani 1 1 d . . .
H1 H -0.2870 0.9936 0.0855 0.049 Uiso 1 1 calc R . .
C3 C -0.2780(2) 0.5192(5) 0.17986(12) 0.0497(6) Uani 1 1 d . . .
H3 H -0.3306 0.4003 0.1964 0.060 Uiso 1 1 calc R . .
B1 B 0.0726(2) 0.6921(5) 0.20169(12) 0.0356(6) Uani 1 1 d . . .
C2 C -0.3296(2) 0.7019(5) 0.13814(11) 0.0485(6) Uani 1 1 d . . .
H2 H -0.4179 0.7077 0.1272 0.058 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.727(2) . ?
F2 B1 1.380(3) . ?
F1 B1 1.368(3) . ?
N3 C9 1.353(2) . ?
N3 C8 1.376(2) . ?
N3 B1 1.548(3) . ?
N2 C5 1.363(3) . ?
N2 C4 1.363(3) . ?
N2 B1 1.561(3) . ?
C5 C1 1.407(3) . ?
C5 C6 1.426(3) . ?
N4 C9 1.301(3) . ?
N4 C11 1.348(3) . ?
C8 C6 1.398(3) . ?
C8 C10 1.415(3) . ?
C11 C10 1.351(3) . ?
C6 C7 1.430(3) . ?
C4 C3 1.352(3) . ?
N1 C7 1.140(3) . ?
C1 C2 1.356(3) . ?
C3 C2 1.389(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N3 C8 119.06(17) . . ?
C9 N3 B1 119.19(17) . . ?
C8 N3 B1 121.32(16) . . ?
C5 N2 C4 120.66(17) . . ?
C5 N2 B1 121.44(17) . . ?
C4 N2 B1 117.48(17) . . ?
N2 C5 C1 117.85(19) . . ?
N2 C5 C6 118.74(17) . . ?
C1 C5 C6 123.39(19) . . ?
C9 N4 C11 114.72(18) . . ?
N3 C8 C6 118.68(18) . . ?
N3 C8 C10 116.68(17) . . ?
C6 C8 C10 124.63(18) . . ?
N4 C11 C10 125.2(2) . . ?
N4 C11 Cl1 114.35(15) . . ?
C10 C11 Cl1 120.47(17) . . ?
C11 C10 C8 117.82(19) . . ?
C8 C6 C5 123.46(18) . . ?
C8 C6 C7 118.52(18) . . ?
C5 C6 C7 117.65(17) . . ?
C3 C4 N2 121.9(2) . . ?
N4 C9 N3 126.1(2) . . ?
N1 C7 C6 178.1(2) . . ?
C2 C1 C5 120.8(2) . . ?
C4 C3 C2 118.5(2) . . ?
F1 B1 F2 111.27(18) . . ?
F1 B1 N3 110.38(18) . . ?
F2 B1 N3 109.07(18) . . ?
F1 B1 N2 110.15(18) . . ?
F2 B1 N2 107.75(18) . . ?
N3 B1 N2 108.14(15) . . ?
C1 C2 C3 120.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.050
