# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1529635'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;

_audit_creation_date             2017-01-24T17:18:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
"'1,1-difluoro-3-(p-tolyl)-1H-pyrido[1,2-C][1,3,5,2]        oxadiazaborinin-9-ium-1-uide'"
_chemical_name_common            Oxadiazaborinium
_chemical_formula_moiety         'C13 H11 B F2 N2 O'
_chemical_formula_sum            'C13 H11 B F2 N2 O'
_chemical_formula_weight         260.05
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   10.662(5)
_cell_length_b                   9.759(5)
_cell_length_c                   12.764(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.318(16)
_cell_angle_gamma                90
_cell_volume                     1219.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9293
_cell_measurement_theta_min      2.946
_cell_measurement_theta_max      28.505
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.256
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.7317
_exptl_absorpt_correction_T_max  0.7458
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.972

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_number            40632
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         28.793
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             3132
_reflns_number_gt                2610
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.0636P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.152
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.27796(15) 0.38481(19) 0.74292(14) 0.1029(6) Uani 1 1 d . . . . .
F2 F 0.41160(16) 0.56801(15) 0.77614(12) 0.0974(6) Uani 1 1 d . . . . .
N9 N 0.24101(12) 0.53782(12) 0.58910(11) 0.0398(3) Uani 1 1 d . . . . .
N4 N 0.33111(13) 0.41201(14) 0.47544(11) 0.0434(3) Uani 1 1 d . . . . .
O2 O 0.44361(14) 0.39245(16) 0.67096(10) 0.0678(4) Uani 1 1 d . . . . .
C7 C 0.05658(18) 0.69148(18) 0.50457(18) 0.0573(5) Uani 1 1 d . . . . .
H7 H -0.0048 0.7545 0.5121 0.069 Uiso 1 1 calc R U . . .
C8 C 0.15063(18) 0.62946(17) 0.59812(16) 0.0512(4) Uani 1 1 d . . . . .
H8 H 0.1529 0.6505 0.6699 0.061 Uiso 1 1 calc R U . . .
C4A C 0.24022(15) 0.50522(14) 0.48630(13) 0.0385(3) Uani 1 1 d . . . . .
C3 C 0.42500(15) 0.36193(15) 0.56590(13) 0.0403(3) Uani 1 1 d . . . . .
C31 C 0.52280(15) 0.26138(15) 0.55562(13) 0.0401(3) Uani 1 1 d . . . . .
C32 C 0.51665(17) 0.22358(18) 0.44899(14) 0.0482(4) Uani 1 1 d . . . . .
H32 H 0.4527 0.2641 0.3837 0.058 Uiso 1 1 calc R U . . .
C33 C 0.60534(18) 0.12589(19) 0.43952(15) 0.0505(4) Uani 1 1 d . . . . .
H33 H 0.6004 0.1016 0.3675 0.061 Uiso 1 1 calc R U . . .
C34 C 0.70163(15) 0.06332(16) 0.53506(14) 0.0435(4) Uani 1 1 d . . . . .
C341 C 0.79569(18) -0.04427(19) 0.52263(18) 0.0565(4) Uani 1 1 d . . . . .
H341 H 0.8815 -0.0031 0.5327 0.085 Uiso 1 1 calc R U . . .
H342 H 0.7553 -0.0844 0.448 0.085 Uiso 1 1 calc R U . . .
H343 H 0.8104 -0.1141 0.5793 0.085 Uiso 1 1 calc R U . . .
C6 C 0.05353(18) 0.65973(19) 0.39875(17) 0.0563(4) Uani 1 1 d . . . . .
H6 H -0.0103 0.7011 0.3339 0.068 Uiso 1 1 calc R U . . .
C5 C 0.14460(18) 0.56716(18) 0.38887(15) 0.0507(4) Uani 1 1 d . . . . .
H5 H 0.1428 0.5455 0.3173 0.061 Uiso 1 1 calc R U . . .
C35 C 0.70888(16) 0.10333(17) 0.64138(14) 0.0472(4) Uani 1 1 d . . . . .
H35 H 0.7742 0.0641 0.7066 0.057 Uiso 1 1 calc R U . . .
C36 C 0.62044(16) 0.20072(17) 0.65211(14) 0.0463(4) Uani 1 1 d . . . . .
H36 H 0.6263 0.2258 0.7242 0.056 Uiso 1 1 calc R U . . .
B1 B 0.3464(2) 0.4690(2) 0.69990(16) 0.0472(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.351(2) . ?
F2 B1 1.352(2) . ?
N9 C4A 1.347(2) . ?
N9 C8 1.353(2) . ?
N9 B1 1.567(2) . ?
N4 C3 1.288(2) . ?
N4 C4A 1.3755(19) . ?
O2 C3 1.310(2) . ?
O2 B1 1.440(2) . ?
C7 C8 1.360(3) . ?
C7 C6 1.374(3) . ?
C7 H7 0.93 . ?
C8 H8 0.93 . ?
C4A C5 1.396(2) . ?
C3 C31 1.475(2) . ?
C31 C32 1.386(2) . ?
C31 C36 1.391(2) . ?
C32 C33 1.381(2) . ?
C32 H32 0.93 . ?
C33 C34 1.387(2) . ?
C33 H33 0.93 . ?
C34 C35 1.385(2) . ?
C34 C341 1.503(2) . ?
C341 H341 0.96 . ?
C341 H342 0.96 . ?
C341 H343 0.96 . ?
C6 C5 1.368(2) . ?
C6 H6 0.93 . ?
C5 H5 0.93 . ?
C35 C36 1.383(2) . ?
C35 H35 0.93 . ?
C36 H36 0.93 . ?

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
C4A N9 C8 120.60(14) . . ?
C4A N9 B1 120.26(13) . . ?
C8 N9 B1 119.13(14) . . ?
C3 N4 C4A 119.28(13) . . ?
C3 O2 B1 123.23(14) . . ?
C8 C7 C6 119.02(16) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N9 C8 C7 121.47(17) . . ?
N9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
N9 C4A N4 121.42(13) . . ?
N9 C4A C5 119.11(14) . . ?
N4 C4A C5 119.47(14) . . ?
N4 C3 O2 125.49(14) . . ?
N4 C3 C31 119.91(14) . . ?
O2 C3 C31 114.60(13) . . ?
C32 C31 C36 118.94(14) . . ?
C32 C31 C3 120.26(14) . . ?
C36 C31 C3 120.79(14) . . ?
C33 C32 C31 120.10(15) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 121.41(15) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C35 C34 C33 118.19(14) . . ?
C35 C34 C341 121.32(15) . . ?
C33 C34 C341 120.49(16) . . ?
C34 C341 H341 109.5 . . ?
C34 C341 H342 109.5 . . ?
H341 C341 H342 109.5 . . ?
C34 C341 H343 109.5 . . ?
H341 C341 H343 109.5 . . ?
H342 C341 H343 109.5 . . ?
C5 C6 C7 119.88(17) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C5 C4A 119.91(17) . . ?
C6 C5 H5 120 . . ?
C4A C5 H5 120 . . ?
C36 C35 C34 121.00(15) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C31 120.34(15) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
F1 B1 F2 110.41(18) . . ?
F1 B1 O2 110.36(17) . . ?
F2 B1 O2 109.75(17) . . ?
F1 B1 N9 108.54(15) . . ?
F2 B1 N9 108.92(15) . . ?
O2 B1 N9 108.82(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A N9 C8 C7 0.0(2) . . . . ?
B1 N9 C8 C7 -179.61(16) . . . . ?
C6 C7 C8 N9 0.2(3) . . . . ?
C8 N9 C4A N4 -179.84(14) . . . . ?
B1 N9 C4A N4 -0.3(2) . . . . ?
C8 N9 C4A C5 -0.1(2) . . . . ?
B1 N9 C4A C5 179.48(15) . . . . ?
C3 N4 C4A N9 -4.9(2) . . . . ?
C3 N4 C4A C5 175.41(15) . . . . ?
C4A N4 C3 O2 -0.3(3) . . . . ?
C4A N4 C3 C31 179.70(13) . . . . ?
B1 O2 C3 N4 11.2(3) . . . . ?
B1 O2 C3 C31 -168.83(16) . . . . ?
N4 C3 C31 C32 1.9(2) . . . . ?
O2 C3 C31 C32 -178.03(15) . . . . ?
N4 C3 C31 C36 -176.62(15) . . . . ?
O2 C3 C31 C36 3.4(2) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C3 C31 C32 C33 -177.76(15) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 -1.3(3) . . . . ?
C32 C33 C34 C341 179.07(16) . . . . ?
C8 C7 C6 C5 -0.2(3) . . . . ?
C7 C6 C5 C4A 0.0(3) . . . . ?
N9 C4A C5 C6 0.1(2) . . . . ?
N4 C4A C5 C6 179.83(15) . . . . ?
C33 C34 C35 C36 1.5(2) . . . . ?
C341 C34 C35 C36 -178.88(15) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C32 C31 C36 C35 -0.6(2) . . . . ?
C3 C31 C36 C35 177.94(15) . . . . ?
C3 O2 B1 F1 104.7(2) . . . . ?
C3 O2 B1 F2 -133.35(19) . . . . ?
C3 O2 B1 N9 -14.3(2) . . . . ?
C4A N9 B1 F1 -111.17(17) . . . . ?
C8 N9 B1 F1 68.4(2) . . . . ?
C4A N9 B1 F2 128.58(16) . . . . ?
C8 N9 B1 F2 -51.8(2) . . . . ?
C4A N9 B1 O2 9.0(2) . . . . ?
C8 N9 B1 O2 -171.44(14) . . . . ?

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
C8 H8 F1 0.93 2.52 3.112(2) 121.6 2_556
C8 H8 F1 0.93 2.52 3.112(2) 121.6 2_556


# END of CIF
