# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_F2PmBTA
_database_code_depnum_ccdc_archive 'CCDC 1560721'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_audit_creation_date             2017-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2,2-difluoro-4,6-bis(2-pyrimidyl)-1,3-dihydro-1,3,5,2-triazaborinine
_chemical_formula_moiety         'C H2 Cl2, C10 H8 B F2 N7'
_chemical_formula_sum            'C11 H10 B Cl2 F2 N7'
_chemical_formula_weight         359.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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                   9.7915(7)
_cell_length_b                   10.7841(8)
_cell_length_c                   28.665(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3026.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      23.87
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0980 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.7537. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13127
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.519
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1709
_reflns_number_total             2913
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0831P)²+3.4864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1955
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All N(H) groups
2. Restrained distances
 Cl1A-C11 \\sim Cl2-C11 \\sim Cl2A-C11 \\sim Cl1-C11
 with sigma of 0.02
 N5-H5 \\sim N3-H3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(Cl2A) = Uanis(Cl1A) = Uanis(Cl1)
4. Others
 Sof(H11C)=Sof(H11D)=Sof(Cl2A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H11A)=Sof(H11B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C2(H2), C8(H8), C3(H3A), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.8961(4) 0.5709(4) 0.42130(15) 0.0563(6) Uani 0.713(8) 1 d D . P A 1
Cl2 Cl 0.6988(4) 0.4052(4) 0.46507(9) 0.0563(6) Uani 0.713(8) 1 d D . P A 1
F1 F 0.8579(3) 0.5527(3) 0.73894(9) 0.0475(7) Uani 1 1 d . . . . .
F2 F 0.9063(2) 0.6802(3) 0.67918(9) 0.0498(8) Uani 1 1 d . . . . .
N7 N 0.4559(4) 0.8047(4) 0.70202(13) 0.0414(10) Uani 1 1 d . . . . .
N3 N 0.7935(4) 0.4889(4) 0.66206(12) 0.0393(10) Uani 1 1 d D . . . .
H3 H 0.857(5) 0.440(5) 0.6532(17) 0.059 Uiso 1 1 d DR . . . .
C4 C 0.6824(4) 0.3582(4) 0.60505(14) 0.0365(11) Uani 1 1 d . . . . .
N5 N 0.6716(3) 0.6534(4) 0.69942(12) 0.0347(9) Uani 1 1 d D . . . .
H5 H 0.658(5) 0.721(4) 0.7149(15) 0.052 Uiso 1 1 d DR . . . .
N1 N 0.8054(4) 0.3087(4) 0.59819(13) 0.0431(10) Uani 1 1 d . . . . .
N4 N 0.5619(3) 0.5262(3) 0.64467(11) 0.0323(9) Uani 1 1 d . . . . .
N2 N 0.5664(4) 0.3250(4) 0.58534(13) 0.0435(10) Uani 1 1 d . . . . .
N6 N 0.3254(3) 0.6564(4) 0.65961(12) 0.0371(9) Uani 1 1 d . . . . .
C11 C 0.7211(5) 0.5317(5) 0.42547(17) 0.0538(14) Uani 1 1 d D . . . .
H11A H 0.686055 0.508309 0.394303 0.065 Uiso 0.713(8) 1 calc R . P A 1
H11B H 0.668584 0.604364 0.436578 0.065 Uiso 0.713(8) 1 calc R . P A 1
H11C H 0.681571 0.502767 0.395616 0.065 Uiso 0.287(8) 1 calc R . P A 2
H11D H 0.686585 0.616820 0.430780 0.065 Uiso 0.287(8) 1 calc R . P A 2
C6 C 0.5647(4) 0.6204(4) 0.67408(14) 0.0312(10) Uani 1 1 d . . . . .
C10 C 0.3438(5) 0.8740(5) 0.70752(17) 0.0465(12) Uani 1 1 d . . . . .
H10 H 0.350537 0.950379 0.723899 0.056 Uiso 1 1 calc R . . . .
C5 C 0.6800(4) 0.4634(4) 0.63947(14) 0.0311(10) Uani 1 1 d . . . . .
C7 C 0.4395(4) 0.6993(4) 0.67897(14) 0.0317(10) Uani 1 1 d . . . . .
C9 C 0.2191(5) 0.8379(5) 0.69013(17) 0.0485(13) Uani 1 1 d . . . . .
H9 H 0.139375 0.886356 0.694929 0.058 Uiso 1 1 calc R . . . .
B1 B 0.8138(5) 0.5949(5) 0.69585(18) 0.0372(12) Uani 1 1 d . . . . .
C2 C 0.6945(6) 0.1686(5) 0.54734(16) 0.0510(14) Uani 1 1 d . . . . .
H2 H 0.697347 0.099175 0.526973 0.061 Uiso 1 1 calc R . . . .
C8 C 0.2149(5) 0.7290(5) 0.66560(17) 0.0466(13) Uani 1 1 d . . . . .
H8 H 0.130552 0.703703 0.652260 0.056 Uiso 1 1 calc R . . . .
C3 C 0.5760(5) 0.2278(5) 0.55677(17) 0.0491(13) Uani 1 1 d . . . . .
H3A H 0.494975 0.198441 0.542237 0.059 Uiso 1 1 calc R . . . .
C1 C 0.8109(5) 0.2130(5) 0.56840(16) 0.0482(13) Uani 1 1 d . . . . .
H1 H 0.896386 0.175227 0.561752 0.058 Uiso 1 1 calc R . . . .
Cl2A Cl 0.6565(9) 0.4401(8) 0.4686(2) 0.0563(6) Uani 0.287(8) 1 d D . P A 2
Cl1A Cl 0.8926(11) 0.5417(10) 0.4181(4) 0.0563(6) Uani 0.287(8) 1 d D . P A 2


_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 1.769(6) . ?
Cl2 C11 1.788(6) . ?
F1 B1 1.385(6) . ?
F2 B1 1.376(6) . ?
N7 C10 1.337(6) . ?
N7 C7 1.325(6) . ?
N3 C5 1.315(5) . ?
N3 B1 1.511(7) . ?
C4 N1 1.332(5) . ?
C4 N2 1.318(5) . ?
C4 C5 1.504(6) . ?
N5 C6 1.323(5) . ?
N5 B1 1.532(6) . ?
N1 C1 1.341(6) . ?
N4 C6 1.321(5) . ?
N4 C5 1.348(5) . ?
N2 C3 1.334(6) . ?
N6 C7 1.331(5) . ?
N6 C8 1.347(6) . ?
C11 Cl2A 1.705(7) . ?
C11 Cl1A 1.695(11) . ?
C6 C7 1.499(6) . ?
C10 C9 1.375(7) . ?
C9 C8 1.369(7) . ?
C2 C3 1.352(7) . ?
C2 C1 1.375(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
C7 N7 C10 116.1(4) . . ?
C5 N3 B1 125.8(4) . . ?
N1 C4 C5 114.4(4) . . ?
N2 C4 N1 127.4(4) . . ?
N2 C4 C5 118.2(4) . . ?
C6 N5 B1 124.9(4) . . ?
C4 N1 C1 116.1(4) . . ?
C6 N4 C5 116.0(3) . . ?
C4 N2 C3 114.6(4) . . ?
C7 N6 C8 114.8(4) . . ?
Cl1 C11 Cl2 110.1(3) . . ?
Cl1A C11 Cl2A 119.7(6) . . ?
N5 C6 C7 116.3(4) . . ?
N4 C6 N5 125.0(4) . . ?
N4 C6 C7 118.7(4) . . ?
N7 C10 C9 121.8(5) . . ?
N3 C5 C4 117.9(4) . . ?
N3 C5 N4 124.4(4) . . ?
N4 C5 C4 117.7(4) . . ?
N7 C7 N6 127.5(4) . . ?
N7 C7 C6 115.8(4) . . ?
N6 C7 C6 116.7(4) . . ?
C8 C9 C10 117.2(4) . . ?
F1 B1 N3 111.3(4) . . ?
F1 B1 N5 111.0(4) . . ?
F2 B1 F1 108.9(4) . . ?
F2 B1 N3 111.7(4) . . ?
F2 B1 N5 110.3(4) . . ?
N3 B1 N5 103.6(4) . . ?
C3 C2 C1 117.4(5) . . ?
N6 C8 C9 122.7(4) . . ?
N2 C3 C2 123.6(5) . . ?
N1 C1 C2 120.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_PmImBF3
_database_code_depnum_ccdc_archive 'CCDC 1560722'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_audit_creation_date             2017-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H6 B F3 N4'
_chemical_formula_sum            'C5 H6 B F3 N4'
_chemical_formula_weight         189.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1901(2)
_cell_length_b                   6.2150(2)
_cell_length_c                   14.8496(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.216(2)
_cell_angle_gamma                90
_cell_volume                     755.30(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3300
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      32.00
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0605 before and 0.0314 after correction. The Ratio of minimum to maximum transmission is 0.9448. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and chloroform'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.745
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1522
_reflns_number_total             1873
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.1034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups, All N(H,H) groups
2. Restrained distances
 N3-H3 \\sim N4-H4A \\sim N4-H4B
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C3(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.26701(9) -0.45297(13) 0.32553(5) 0.0407(2) Uani 1 1 d . . . . .
F2 F 0.51522(10) -0.49897(14) 0.39565(5) 0.0507(3) Uani 1 1 d . . . . .
F3 F 0.46696(10) -0.21068(14) 0.30363(6) 0.0493(3) Uani 1 1 d . . . . .
N3 N 0.34446(13) -0.21796(18) 0.44823(7) 0.0332(3) Uani 1 1 d D . . . .
H3 H 0.3463(19) -0.276(3) 0.4988(9) 0.050 Uiso 1 1 d D . . . .
N1 N 0.15149(13) 0.26520(19) 0.52197(7) 0.0379(3) Uani 1 1 d . . . . .
N2 N 0.22023(13) -0.05536(19) 0.60255(7) 0.0378(3) Uani 1 1 d . . . . .
N4 N 0.25646(15) 0.0866(2) 0.37195(7) 0.0395(3) Uani 1 1 d D . . . .
H4A H 0.293(2) 0.041(3) 0.3214(10) 0.059 Uiso 1 1 d D . . . .
H4B H 0.222(2) 0.214(2) 0.3780(12) 0.059 Uiso 1 1 d D . . . .
C5 C 0.27721(13) -0.0279(2) 0.44550(7) 0.0298(3) Uani 1 1 d . . . . .
C4 C 0.21274(13) 0.0685(2) 0.52991(7) 0.0293(3) Uani 1 1 d . . . . .
C2 C 0.09073(15) 0.2340(3) 0.67637(9) 0.0416(3) Uani 1 1 d . . . . .
H2 H 0.046356 0.292973 0.729134 0.050 Uiso 1 1 calc R . . . .
C1 C 0.09078(16) 0.3475(2) 0.59699(9) 0.0427(3) Uani 1 1 d . . . . .
H1 H 0.046394 0.488773 0.595272 0.051 Uiso 1 1 calc R . . . .
C3 C 0.15761(16) 0.0315(3) 0.67607(9) 0.0428(3) Uani 1 1 d . . . . .
H3A H 0.159511 -0.050122 0.730181 0.051 Uiso 1 1 calc R . . . .
B1 B 0.40235(16) -0.3494(3) 0.36671(9) 0.0330(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.4017(15) . ?
F2 B1 1.3686(16) . ?
F3 B1 1.3924(16) . ?
N3 C5 1.3032(17) . ?
N3 B1 1.5496(17) . ?
N1 C4 1.3251(17) . ?
N1 C1 1.3390(16) . ?
N2 C4 1.3246(16) . ?
N2 C3 1.3378(16) . ?
N4 C5 1.3091(16) . ?
C5 C4 1.5034(16) . ?
C2 C1 1.374(2) . ?
C2 C3 1.372(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N3 B1 126.52(10) . . ?
C4 N1 C1 115.47(11) . . ?
C4 N2 C3 115.01(12) . . ?
N3 C5 N4 124.03(11) . . ?
N3 C5 C4 119.79(10) . . ?
N4 C5 C4 116.14(11) . . ?
N1 C4 C5 115.94(10) . . ?
N2 C4 N1 127.88(11) . . ?
N2 C4 C5 116.15(11) . . ?
C3 C2 C1 117.05(12) . . ?
N1 C1 C2 121.99(13) . . ?
N2 C3 C2 122.58(12) . . ?
F1 B1 N3 108.80(10) . . ?
F2 B1 F1 109.76(12) . . ?
F2 B1 F3 111.23(10) . . ?
F2 B1 N3 109.64(10) . . ?
F3 B1 F1 107.79(10) . . ?
F3 B1 N3 109.57(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A F3 0.867(13) 2.138(16) 2.7477(15) 127.0(15) .

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_F2PyBTA
_database_code_depnum_ccdc_archive 'CCDC 1560720'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_audit_creation_date             2017-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        
2,2-difluoro-4,6-bis(2-pyridyl)-1,3-dihydro-1,3,5,2-triazaborinine
_chemical_formula_moiety         'C12 H10 B F2 N5'
_chemical_formula_sum            'C12 H10 B F2 N5'
_chemical_formula_weight         273.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7785(3)
_cell_length_b                   8.8782(3)
_cell_length_c                   9.6210(4)
_cell_angle_alpha                91.401(2)
_cell_angle_beta                 102.708(2)
_cell_angle_gamma                109.795(2)
_cell_volume                     606.29(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5286
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1216 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.7863. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_recrystallization_method 'Recrystallization from chloroform'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10741
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.183
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2499
_reflns_number_total             3153
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
%$getVar(solution_reference_short)%
;
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1176P)²+0.0029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N4-H4 \\sim N2-H2
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4A), C12(H12), C11(H11), C3(H3), C1(H1), C2(H2A), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.65951(12) 0.83732(9) 0.75000(8) 0.0496(3) Uani 1 1 d . . . . .
F2 F 0.93355(11) 0.82454(10) 0.87875(8) 0.0509(3) Uani 1 1 d . . . . .
N3 N 0.69380(14) 0.45567(12) 0.57203(10) 0.0333(3) Uani 1 1 d . . . . .
N4 N 0.84173(14) 0.73620(12) 0.62554(10) 0.0352(3) Uani 1 1 d D . . . .
H4 H 0.907(2) 0.8245(16) 0.5882(15) 0.042 Uiso 1 1 d DR . . . .
N2 N 0.67732(14) 0.57550(12) 0.78757(10) 0.0354(3) Uani 1 1 d D . . . .
H2 H 0.631(2) 0.5471(17) 0.8678(14) 0.042 Uiso 1 1 d DR . . . .
N5 N 0.96619(15) 0.75579(12) 0.38525(10) 0.0371(3) Uani 1 1 d . . . . .
N1 N 0.49575(15) 0.28562(12) 0.86171(11) 0.0392(3) Uani 1 1 d . . . . .
C7 C 0.79461(16) 0.60115(14) 0.54321(11) 0.0313(3) Uani 1 1 d . . . . .
C6 C 0.64008(15) 0.44982(14) 0.69573(12) 0.0310(3) Uani 1 1 d . . . . .
C5 C 0.52926(16) 0.28843(14) 0.73037(12) 0.0319(3) Uani 1 1 d . . . . .
C8 C 0.85567(16) 0.60925(13) 0.40628(11) 0.0309(3) Uani 1 1 d . . . . .
C9 C 0.79647(18) 0.47382(15) 0.30894(13) 0.0363(3) Uani 1 1 d . . . . .
H9 H 0.718611 0.372369 0.328515 0.044 Uiso 1 1 calc R . . . .
C4 C 0.46378(17) 0.15438(15) 0.63098(13) 0.0376(3) Uani 1 1 d . . . . .
H4A H 0.490680 0.162050 0.539212 0.045 Uiso 1 1 calc R . . . .
C12 C 1.02041(19) 0.76875(16) 0.26202(13) 0.0417(3) Uani 1 1 d . . . . .
H12 H 1.098752 0.871279 0.244957 0.050 Uiso 1 1 calc R . . . .
C11 C 0.96801(19) 0.64007(17) 0.15798(13) 0.0425(3) Uani 1 1 d . . . . .
H11 H 1.009652 0.654557 0.071893 0.051 Uiso 1 1 calc R . . . .
C3 C 0.35779(19) 0.00838(16) 0.66871(15) 0.0435(3) Uani 1 1 d . . . . .
H3 H 0.309601 -0.086203 0.602941 0.052 Uiso 1 1 calc R . . . .
C1 C 0.3941(2) 0.14311(16) 0.89589(14) 0.0449(3) Uani 1 1 d . . . . .
H1 H 0.369164 0.138005 0.988321 0.054 Uiso 1 1 calc R . . . .
C2 C 0.32373(19) 0.00315(16) 0.80341(16) 0.0457(3) Uani 1 1 d . . . . .
H2A H 0.252673 -0.095569 0.832325 0.055 Uiso 1 1 calc R . . . .
C10 C 0.85447(19) 0.49080(16) 0.18165(13) 0.0417(3) Uani 1 1 d . . . . .
H10 H 0.816354 0.400760 0.111941 0.050 Uiso 1 1 calc R . . . .
B1 B 0.7800(2) 0.74922(16) 0.76447(14) 0.0368(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3975(16) . ?
F2 B1 1.3887(16) . ?
N3 C7 1.3369(15) . ?
N3 C6 1.3418(15) . ?
N4 H4 0.909(13) . ?
N4 C7 1.3144(15) . ?
N4 B1 1.5309(15) . ?
N2 H2 0.927(13) . ?
N2 C6 1.3153(15) . ?
N2 B1 1.5252(16) . ?
N5 C8 1.3433(15) . ?
N5 C12 1.3381(15) . ?
N1 C5 1.3444(15) . ?
N1 C1 1.3384(15) . ?
C7 C8 1.4910(16) . ?
C6 C5 1.4900(16) . ?
C5 C4 1.3820(17) . ?
C8 C9 1.3838(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3900(17) . ?
C4 H4A 0.9500 . ?
C4 C3 1.3865(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.3779(19) . ?
C3 H3 0.9500 . ?
C3 C2 1.378(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(2) . ?
C2 H2A 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N3 C6 116.38(10) . . ?
C7 N4 H4 113.3(9) . . ?
C7 N4 B1 124.39(10) . . ?
B1 N4 H4 122.1(9) . . ?
C6 N2 H2 112.3(9) . . ?
C6 N2 B1 124.45(9) . . ?
B1 N2 H2 123.2(9) . . ?
C12 N5 C8 116.93(11) . . ?
C1 N1 C5 116.85(11) . . ?
N3 C7 C8 116.91(10) . . ?
N4 C7 N3 124.94(10) . . ?
N4 C7 C8 118.14(10) . . ?
N3 C6 C5 117.13(10) . . ?
N2 C6 N3 124.89(10) . . ?
N2 C6 C5 117.98(10) . . ?
N1 C5 C6 115.14(10) . . ?
N1 C5 C4 123.75(10) . . ?
C4 C5 C6 121.09(10) . . ?
N5 C8 C7 115.13(10) . . ?
N5 C8 C9 123.92(10) . . ?
C9 C8 C7 120.93(11) . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 117.94(12) . . ?
C10 C9 H9 121.0 . . ?
C5 C4 H4A 120.9 . . ?
C5 C4 C3 118.26(11) . . ?
C3 C4 H4A 120.9 . . ?
N5 C12 H12 118.3 . . ?
N5 C12 C11 123.30(12) . . ?
C11 C12 H12 118.3 . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.83(11) . . ?
C10 C11 H11 120.6 . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.71(12) . . ?
C2 C3 H3 120.6 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.22(12) . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 119.20(11) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.07(12) . . ?
C11 C10 H10 120.5 . . ?
F1 B1 N4 110.64(9) . . ?
F1 B1 N2 110.75(10) . . ?
F2 B1 F1 108.30(10) . . ?
F2 B1 N4 111.37(10) . . ?
F2 B1 N2 111.13(10) . . ?
N2 B1 N4 104.65(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       ', Luminescent'
