# 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 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_fc082

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3,3'-(ethane-1,2-diyl)bis(2,2-difluoro-2H-benzo[e][1,3,2]oxazaborinin-3-ium-2-uide)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 B2 F4 N2 O2'
_chemical_formula_sum            'C16 H14 B2 F4 N2 O2'
_chemical_formula_weight         363.91

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'
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'
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   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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                   16.417(3)
_cell_length_b                   5.4987(9)
_cell_length_c                   9.0065(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.664(7)
_cell_angle_gamma                90.00
_cell_volume                     782.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9134
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(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
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6664
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.85
_reflns_number_total             1492
_reflns_number_gt                1202
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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 > 2σ(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)+(0.0448P)²+0.4240P] 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         1492
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
F01 F 0.09616(7) 0.5917(2) 0.41699(13) 0.0290(3) Uani 1 1 d . . .
F02 F 0.14327(7) 0.8659(2) 0.27367(13) 0.0334(4) Uani 1 1 d . . .
O01 O 0.23389(8) 0.7298(3) 0.50535(17) 0.0324(4) Uani 1 1 d . . .
N01 N 0.11471(9) 1.0076(3) 0.50385(17) 0.0201(4) Uani 1 1 d . . .
C01 C 0.28441(12) 0.8735(4) 0.6113(2) 0.0261(5) Uani 1 1 d . . .
C06 C 0.25280(11) 1.0821(4) 0.6657(2) 0.0233(4) Uani 1 1 d . . .
C07 C 0.16499(12) 1.1385(4) 0.6089(2) 0.0221(4) Uani 1 1 d . . .
H07 H 0.1429 1.2755 0.6494 0.026 Uiso 1 1 calc R . .
C08 C 0.02433(11) 1.0695(4) 0.4522(2) 0.0235(4) Uani 1 1 d . . .
H08A H 0.0017 1.0271 0.3419 0.028 Uiso 1 1 calc R . .
H08B H 0.0169 1.2466 0.4635 0.028 Uiso 1 1 calc R . .
C02 C 0.36924(12) 0.8135(4) 0.6690(3) 0.0353(5) Uani 1 1 d . . .
H02 H 0.3912 0.6725 0.6325 0.042 Uiso 1 1 calc R . .
C05 C 0.30731(12) 1.2283(4) 0.7773(2) 0.0309(5) Uani 1 1 d . . .
H05 H 0.2861 1.3702 0.8141 0.037 Uiso 1 1 calc R . .
C03 C 0.42154(13) 0.9586(5) 0.7791(3) 0.0399(6) Uani 1 1 d . . .
H03 H 0.4794 0.9158 0.8187 0.048 Uiso 1 1 calc R . .
C04 C 0.39090(13) 1.1673(5) 0.8334(3) 0.0380(6) Uani 1 1 d . . .
H04 H 0.4277 1.2665 0.9089 0.046 Uiso 1 1 calc R . .
B01 B 0.14849(13) 0.7915(4) 0.4238(3) 0.0232(5) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
F01 B01 1.386(2) . ?
F02 B01 1.393(2) . ?
O01 C01 1.340(2) . ?
O01 B01 1.437(3) . ?
N01 C07 1.294(2) . ?
N01 C08 1.470(2) . ?
N01 B01 1.567(3) . ?
C01 C02 1.388(3) . ?
C01 C06 1.401(3) . ?
C06 C05 1.404(3) . ?
C06 C07 1.427(3) . ?
C07 H07 0.9500 . ?
C08 C08 1.528(4) 3_576 ?
C08 H08A 0.9900 . ?
C08 H08B 0.9900 . ?
C02 C03 1.378(3) . ?
C02 H02 0.9500 . ?
C05 C04 1.370(3) . ?
C05 H05 0.9500 . ?
C03 C04 1.393(4) . ?
C03 H03 0.9500 . ?
C04 H04 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
C01 O01 B01 123.77(17) . . ?
C07 N01 C08 119.53(17) . . ?
C07 N01 B01 121.56(16) . . ?
C08 N01 B01 118.84(15) . . ?
O01 C01 C02 119.5(2) . . ?
O01 C01 C06 121.02(17) . . ?
C02 C01 C06 119.53(19) . . ?
C01 C06 C05 119.63(18) . . ?
C01 C06 C07 119.11(17) . . ?
C05 C06 C07 121.24(19) . . ?
N01 C07 C06 121.62(18) . . ?
N01 C07 H07 119.2 . . ?
C06 C07 H07 119.2 . . ?
N01 C08 C08 110.02(19) . 3_576 ?
N01 C08 H08A 109.7 . . ?
C08 C08 H08A 109.7 3_576 . ?
N01 C08 H08B 109.7 . . ?
C08 C08 H08B 109.7 3_576 . ?
H08A C08 H08B 108.2 . . ?
C03 C02 C01 119.9(2) . . ?
C03 C02 H02 120.0 . . ?
C01 C02 H02 120.0 . . ?
C04 C05 C06 120.4(2) . . ?
C04 C05 H05 119.8 . . ?
C06 C05 H05 119.8 . . ?
C02 C03 C04 121.1(2) . . ?
C02 C03 H03 119.5 . . ?
C04 C03 H03 119.5 . . ?
C05 C04 C03 119.5(2) . . ?
C05 C04 H04 120.2 . . ?
C03 C04 H04 120.2 . . ?
F01 B01 F02 108.35(16) . . ?
F01 B01 O01 110.08(17) . . ?
F02 B01 O01 111.18(17) . . ?
F01 B01 N01 109.23(16) . . ?
F02 B01 N01 106.68(16) . . ?
O01 B01 N01 111.20(16) . . ?

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
B01 O01 C01 C02 -171.50(19) . . . . ?
B01 O01 C01 C06 9.0(3) . . . . ?
O01 C01 C06 C05 179.68(19) . . . . ?
C02 C01 C06 C05 0.2(3) . . . . ?
O01 C01 C06 C07 1.3(3) . . . . ?
C02 C01 C06 C07 -178.22(19) . . . . ?
C08 N01 C07 C06 178.41(17) . . . . ?
B01 N01 C07 C06 -4.7(3) . . . . ?
C01 C06 C07 N01 -3.0(3) . . . . ?
C05 C06 C07 N01 178.59(18) . . . . ?
C07 N01 C08 C08 -91.7(3) . . . 3_576 ?
B01 N01 C08 C08 91.3(2) . . . 3_576 ?
O01 C01 C02 C03 -179.3(2) . . . . ?
C06 C01 C02 C03 0.2(3) . . . . ?
C01 C06 C05 C04 -0.2(3) . . . . ?
C07 C06 C05 C04 178.2(2) . . . . ?
C01 C02 C03 C04 -0.5(4) . . . . ?
C06 C05 C04 C03 -0.1(3) . . . . ?
C02 C03 C04 C05 0.5(4) . . . . ?
C01 O01 B01 F01 -136.39(19) . . . . ?
C01 O01 B01 F02 103.5(2) . . . . ?
C01 O01 B01 N01 -15.2(3) . . . . ?
C07 N01 B01 F01 134.78(18) . . . . ?
C08 N01 B01 F01 -48.3(2) . . . . ?
C07 N01 B01 F02 -108.31(19) . . . . ?
C08 N01 B01 F02 68.6(2) . . . . ?
C07 N01 B01 O01 13.1(3) . . . . ?
C08 N01 B01 O01 -170.01(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.85
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1006070'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sg629

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 2,2'-((1E,1'E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(4-benzhydrylphenol)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H36 N2 O2'
_chemical_formula_sum            'C42 H36 N2 O2'
_chemical_formula_weight         600.73

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc


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

_cell_length_a                   11.8811(13)
_cell_length_b                   8.5426(8)
_cell_length_c                   16.4812(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.687(4)
_cell_angle_gamma                90.00
_cell_volume                     1602.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(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
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7080
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2917
_reflns_number_gt                1743
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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 > 2σ(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)+(0.0729P)²+0.3686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
H1 H 0.638(3) 0.832(4) 0.084(2) 0.075(11) Uiso 1 1 d . . .
O1 O 0.66333(17) 0.9187(2) 0.11835(13) 0.0463(5) Uani 1 1 d . . .
C6 C 0.4546(2) 0.9220(3) 0.09693(15) 0.0333(6) Uani 1 1 d . . .
C7 C 0.4364(3) 0.7862(3) 0.04233(16) 0.0384(7) Uani 1 1 d . . .
H7 H 0.3583 0.7518 0.0165 0.046 Uiso 1 1 calc R . .
N1 N 0.5204(2) 0.7109(2) 0.02750(14) 0.0400(6) Uani 1 1 d . . .
C2 C 0.5795(3) 1.1168(3) 0.18356(17) 0.0435(7) Uani 1 1 d . . .
H2 H 0.6551 1.1612 0.2074 0.052 Uiso 1 1 calc R . .
C9 C 0.2632(2) 1.2069(3) 0.17886(17) 0.0407(7) Uani 1 1 d . . .
H9 H 0.2910 1.2581 0.2357 0.049 Uiso 1 1 calc R . .
C5 C 0.3586(2) 0.9936(3) 0.11406(16) 0.0372(7) Uani 1 1 d . . .
H5 H 0.2825 0.9510 0.0898 0.045 Uiso 1 1 calc R . .
C1 C 0.5670(2) 0.9844(3) 0.13255(15) 0.0336(6) Uani 1 1 d . . .
C4 C 0.3699(2) 1.1239(3) 0.16484(16) 0.0365(7) Uani 1 1 d . . .
C3 C 0.4827(2) 1.1836(3) 0.19956(16) 0.0396(7) Uani 1 1 d . . .
H3 H 0.4930 1.2729 0.2353 0.048 Uiso 1 1 calc R . .
C8 C 0.4896(3) 0.5717(3) -0.02743(17) 0.0432(7) Uani 1 1 d . . .
H8A H 0.5386 0.5677 -0.0669 0.052 Uiso 1 1 calc R . .
H8B H 0.4061 0.5769 -0.0613 0.052 Uiso 1 1 calc R . .
C16 C 0.1667(3) 1.0911(3) 0.18402(18) 0.0425(7) Uani 1 1 d . . .
C10 C 0.2202(2) 1.3382(3) 0.11508(17) 0.0398(7) Uani 1 1 d . . .
C15 C 0.1831(3) 1.4780(3) 0.1406(2) 0.0491(8) Uani 1 1 d . . .
H15 H 0.1839 1.4910 0.1980 0.059 Uiso 1 1 calc R . .
C11 C 0.2144(2) 1.3207(3) 0.02988(18) 0.0466(8) Uani 1 1 d . . .
H11 H 0.2386 1.2247 0.0110 0.056 Uiso 1 1 calc R . .
C17 C 0.0571(3) 1.0864(4) 0.1248(2) 0.0562(9) Uani 1 1 d . . .
H17 H 0.0406 1.1557 0.0778 0.067 Uiso 1 1 calc R . .
C12 C 0.1749(3) 1.4378(4) -0.0267(2) 0.0516(8) Uani 1 1 d . . .
H12 H 0.1710 1.4231 -0.0845 0.062 Uiso 1 1 calc R . .
C14 C 0.1442(3) 1.6011(4) 0.0832(3) 0.0615(9) Uani 1 1 d . . .
H14 H 0.1210 1.6981 0.1016 0.074 Uiso 1 1 calc R . .
C20 C 0.1038(4) 0.8796(4) 0.2572(2) 0.0778(12) Uani 1 1 d . . .
H20 H 0.1220 0.8058 0.3022 0.093 Uiso 1 1 calc R . .
C21 C 0.1889(3) 0.9870(4) 0.24933(19) 0.0595(9) Uani 1 1 d . . .
H21 H 0.2636 0.9874 0.2904 0.071 Uiso 1 1 calc R . .
C13 C 0.1403(3) 1.5790(4) 0.0000(3) 0.0627(10) Uani 1 1 d . . .
H13 H 0.1136 1.6611 -0.0397 0.075 Uiso 1 1 calc R . .
C18 C -0.0285(3) 0.9839(4) 0.1326(3) 0.0659(10) Uani 1 1 d . . .
H18 H -0.1034 0.9839 0.0916 0.079 Uiso 1 1 calc R . .
C19 C -0.0056(4) 0.8808(4) 0.2000(3) 0.0762(12) Uani 1 1 d . . .
H19 H -0.0650 0.8117 0.2065 0.091 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C1 1.354(3) . ?
O1 H1 0.93(3) . ?
C6 C5 1.392(4) . ?
C6 C1 1.400(4) . ?
C6 C7 1.447(4) . ?
C7 N1 1.268(3) . ?
C7 H7 0.9500 . ?
N1 C8 1.476(3) . ?
C2 C3 1.375(4) . ?
C2 C1 1.392(4) . ?
C2 H2 0.9500 . ?
C9 C10 1.521(4) . ?
C9 C4 1.527(4) . ?
C9 C16 1.535(4) . ?
C9 H9 1.0000 . ?
C5 C4 1.375(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.394(4) . ?
C3 H3 0.9500 . ?
C8 C8 1.500(5) 3_665 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C16 C21 1.362(4) . ?
C16 C17 1.386(4) . ?
C10 C15 1.381(4) . ?
C10 C11 1.394(4) . ?
C15 C14 1.400(4) . ?
C15 H15 0.9500 . ?
C11 C12 1.356(4) . ?
C11 H11 0.9500 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C14 C13 1.372(5) . ?
C14 H14 0.9500 . ?
C20 C19 1.370(5) . ?
C20 C21 1.398(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C13 H13 0.9500 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9500 . ?
C19 H19 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
C1 O1 H1 107(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 119.6(2) . . ?
C1 C6 C7 121.3(2) . . ?
N1 C7 C6 122.8(3) . . ?
N1 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 N1 C8 117.2(2) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C10 C9 C4 111.5(2) . . ?
C10 C9 C16 113.9(2) . . ?
C4 C9 C16 112.0(2) . . ?
C10 C9 H9 106.3 . . ?
C4 C9 H9 106.3 . . ?
C16 C9 H9 106.3 . . ?
C4 C5 C6 122.4(3) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
O1 C1 C2 119.5(2) . . ?
O1 C1 C6 121.4(2) . . ?
C2 C1 C6 119.1(2) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C9 121.8(2) . . ?
C3 C4 C9 120.7(2) . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C8 C8 108.6(3) . 3_665 ?
N1 C8 H8A 110.0 . . ?
C8 C8 H8A 110.0 3_665 . ?
N1 C8 H8B 110.0 . . ?
C8 C8 H8B 110.0 3_665 . ?
H8A C8 H8B 108.3 . . ?
C21 C16 C17 117.8(3) . . ?
C21 C16 C9 119.1(3) . . ?
C17 C16 C9 123.1(3) . . ?
C15 C10 C11 118.2(3) . . ?
C15 C10 C9 120.0(3) . . ?
C11 C10 C9 121.8(2) . . ?
C10 C15 C14 121.1(3) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 121.4(3) . . ?
C16 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 119.2(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?

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
C5 C6 C7 N1 -176.4(2) . . . . ?
C1 C6 C7 N1 4.1(4) . . . . ?
C6 C7 N1 C8 178.2(2) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C7 C6 C5 C4 -179.4(2) . . . . ?
C3 C2 C1 O1 -179.1(2) . . . . ?
C3 C2 C1 C6 1.0(4) . . . . ?
C5 C6 C1 O1 179.6(2) . . . . ?
C7 C6 C1 O1 -1.0(4) . . . . ?
C5 C6 C1 C2 -0.5(4) . . . . ?
C7 C6 C1 C2 179.0(2) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C6 C5 C4 C9 176.3(2) . . . . ?
C10 C9 C4 C5 -92.0(3) . . . . ?
C16 C9 C4 C5 37.0(3) . . . . ?
C10 C9 C4 C3 84.2(3) . . . . ?
C16 C9 C4 C3 -146.8(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C9 C4 C3 C2 -175.8(2) . . . . ?
C7 N1 C8 C8 -100.5(3) . . . 3_665 ?
C10 C9 C16 C21 -167.6(2) . . . . ?
C4 C9 C16 C21 64.7(3) . . . . ?
C10 C9 C16 C17 12.6(4) . . . . ?
C4 C9 C16 C17 -115.1(3) . . . . ?
C4 C9 C10 C15 -140.0(3) . . . . ?
C16 C9 C10 C15 92.1(3) . . . . ?
C4 C9 C10 C11 41.5(3) . . . . ?
C16 C9 C10 C11 -86.4(3) . . . . ?
C11 C10 C15 C14 -2.1(4) . . . . ?
C9 C10 C15 C14 179.4(3) . . . . ?
C15 C10 C11 C12 0.8(4) . . . . ?
C9 C10 C11 C12 179.4(3) . . . . ?
C21 C16 C17 C18 2.0(4) . . . . ?
C9 C16 C17 C18 -178.3(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C10 C15 C14 C13 1.9(5) . . . . ?
C17 C16 C21 C20 -0.5(5) . . . . ?
C9 C16 C21 C20 179.7(3) . . . . ?
C19 C20 C21 C16 -2.1(5) . . . . ?
C15 C14 C13 C12 -0.5(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C21 C20 C19 C18 3.2(5) . . . . ?
C17 C18 C19 C20 -1.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1006071'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 2,2-difluoro-3-propyl-2H-benzo[e][1,3,2]oxazaborinin-3-ium-2-uide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 B F2 N O'
_chemical_formula_sum            'C10 H12 B F2 N O'
_chemical_formula_weight         211.02

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   6.9487(12)
_cell_length_b                   12.624(2)
_cell_length_c                   11.3238(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.457(7)
_cell_angle_gamma                90
_cell_volume                     991.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1063
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      26.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.6893
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4103
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         26.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2008
_reflns_number_gt                1485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.6642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2008
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_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_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
F02 F 0.6351(2) 0.80649(13) 0.20698(13) 0.0403(5) Uani 1 1 d . . . . .
F01 F 0.9598(2) 0.81488(12) 0.20625(13) 0.0376(5) Uani 1 1 d . . . . .
O01 O 0.7936(3) 0.96153(14) 0.26891(15) 0.0330(5) Uani 1 1 d . . . . .
N01 N 0.8187(3) 0.79903(16) 0.39383(17) 0.0224(5) Uani 1 1 d . . . . .
C01 C 0.7616(3) 1.0171(2) 0.3664(2) 0.0251(6) Uani 1 1 d . . . . .
C07 C 0.7964(3) 0.8565(2) 0.4860(2) 0.0241(5) Uani 1 1 d . . . . .
H07 H 0.8036 0.8238 0.5617 0.029 Uiso 1 1 calc R U . . .
C06 C 0.7611(3) 0.96822(19) 0.4780(2) 0.0227(5) Uani 1 1 d . . . . .
C05 C 0.7323(4) 1.0290(2) 0.5786(2) 0.0286(6) Uani 1 1 d . . . . .
H05 H 0.7334 0.9958 0.6540 0.034 Uiso 1 1 calc R U . . .
C08 C 0.8591(4) 0.68429(19) 0.4087(2) 0.0266(6) Uani 1 1 d . . . . .
H08A H 0.9212 0.6719 0.4885 0.032 Uiso 1 1 calc R U . . .
H08B H 0.9509 0.6620 0.3500 0.032 Uiso 1 1 calc R U . . .
C02 C 0.7342(4) 1.1262(2) 0.3582(2) 0.0302(6) Uani 1 1 d . . . . .
H02 H 0.7363 1.1605 0.2836 0.036 Uiso 1 1 calc R U . . .
C04 C 0.7024(4) 1.1367(2) 0.5693(2) 0.0323(6) Uani 1 1 d . . . . .
H04 H 0.6811 1.1778 0.6375 0.039 Uiso 1 1 calc R U . . .
C09 C 0.6793(4) 0.6173(2) 0.3937(2) 0.0316(6) Uani 1 1 d . . . . .
H09A H 0.6224 0.6248 0.3118 0.038 Uiso 1 1 calc R U . . .
H09B H 0.5833 0.6426 0.4484 0.038 Uiso 1 1 calc R U . . .
C03 C 0.7039(4) 1.1843(2) 0.4586(3) 0.0334(6) Uani 1 1 d . . . . .
H03 H 0.6836 1.2586 0.4519 0.040 Uiso 1 1 calc R U . . .
B01 B 0.8006(4) 0.8470(2) 0.2651(2) 0.0262(6) Uani 1 1 d . . . . .
C10 C 0.7241(4) 0.5010(2) 0.4188(2) 0.0358(7) Uani 1 1 d . . . . .
H10B H 0.8287 0.4779 0.3705 0.054 Uiso 1 1 calc R U . . .
H10A H 0.6089 0.4582 0.3992 0.054 Uiso 1 1 calc R U . . .
H10C H 0.7637 0.4921 0.5027 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F02 B01 1.388(3) . ?
F01 B01 1.386(3) . ?
O01 C01 1.338(3) . ?
O01 B01 1.447(3) . ?
N01 C07 1.288(3) . ?
N01 C08 1.483(3) . ?
N01 B01 1.577(3) . ?
C01 C02 1.392(4) . ?
C01 C06 1.407(3) . ?
C07 C06 1.434(3) . ?
C07 H07 0.9500 . ?
C06 C05 1.398(3) . ?
C05 C04 1.379(4) . ?
C05 H05 0.9500 . ?
C08 C09 1.510(4) . ?
C08 H08A 0.9900 . ?
C08 H08B 0.9900 . ?
C02 C03 1.380(4) . ?
C02 H02 0.9500 . ?
C04 C03 1.391(4) . ?
C04 H04 0.9500 . ?
C09 C10 1.524(4) . ?
C09 H09A 0.9900 . ?
C09 H09B 0.9900 . ?
C03 H03 0.9500 . ?
C10 H10B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10C 0.9800 . ?

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
C01 O01 B01 123.8(2) . . ?
C07 N01 C08 119.3(2) . . ?
C07 N01 B01 121.7(2) . . ?
C08 N01 B01 119.0(2) . . ?
O01 C01 C02 119.5(2) . . ?
O01 C01 C06 121.4(2) . . ?
C02 C01 C06 119.1(2) . . ?
N01 C07 C06 122.1(2) . . ?
N01 C07 H07 118.9 . . ?
C06 C07 H07 118.9 . . ?
C05 C06 C01 120.0(2) . . ?
C05 C06 C07 121.4(2) . . ?
C01 C06 C07 118.6(2) . . ?
C04 C05 C06 120.5(2) . . ?
C04 C05 H05 119.8 . . ?
C06 C05 H05 119.8 . . ?
N01 C08 C09 112.6(2) . . ?
N01 C08 H08A 109.1 . . ?
C09 C08 H08A 109.1 . . ?
N01 C08 H08B 109.1 . . ?
C09 C08 H08B 109.1 . . ?
H08A C08 H08B 107.8 . . ?
C03 C02 C01 119.9(3) . . ?
C03 C02 H02 120.1 . . ?
C01 C02 H02 120.1 . . ?
C05 C04 C03 119.1(2) . . ?
C05 C04 H04 120.5 . . ?
C03 C04 H04 120.5 . . ?
C08 C09 C10 111.1(2) . . ?
C08 C09 H09A 109.4 . . ?
C10 C09 H09A 109.4 . . ?
C08 C09 H09B 109.4 . . ?
C10 C09 H09B 109.4 . . ?
H09A C09 H09B 108.0 . . ?
C02 C03 C04 121.5(3) . . ?
C02 C03 H03 119.3 . . ?
C04 C03 H03 119.3 . . ?
F01 B01 F02 109.1(2) . . ?
F01 B01 O01 109.6(2) . . ?
F02 B01 O01 110.7(2) . . ?
F01 B01 N01 108.1(2) . . ?
F02 B01 N01 108.3(2) . . ?
O01 B01 N01 110.9(2) . . ?
C09 C10 H10B 109.5 . . ?
C09 C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
C09 C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?

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
C07 H07 F01 0.95 2.59 3.442(3) 149.5 4_576
C08 H08A F01 0.99 2.47 3.399(3) 156.3 4_576
C09 H09A F02 0.99 2.59 3.193(3) 119.5 .

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.070

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       Luminescent
_database_code_depnum_ccdc_archive 'CCDC 1017586'
