# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_l
#TrackingRef 'lx-8.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 B F2 N O3'
_chemical_formula_sum            'C18 H16 B F2 N O3'
_chemical_formula_weight         343.13

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   26.916(3)
_cell_length_b                   8.0515(9)
_cell_length_c                   17.954(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.571(2)
_cell_angle_gamma                90.00
_cell_volume                     3241.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1512
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10835
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.01
_reflns_number_total             3188
_reflns_number_gt                1875
_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)+(0.0594P)²+0.9031P] 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         3188
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.098
_refine_ls_shift/su_mean         0.002

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
O1 O 0.07033(8) 0.0428(2) 1.04076(12) 0.0491(5) Uani 1 1 d . . .
F1 F 0.11724(8) -0.1382(2) 1.15978(12) 0.0726(6) Uani 1 1 d . . .
O2 O 0.16437(8) 0.1121(2) 1.17726(12) 0.0514(5) Uani 1 1 d . . .
C1 C 0.06801(12) 0.1936(3) 1.01231(17) 0.0411(6) Uani 1 1 d . . .
F2 F 0.15812(7) -0.0921(2) 1.08060(12) 0.0692(5) Uani 1 1 d . . .
C2 C 0.11526(11) 0.3080(3) 1.06133(16) 0.0364(6) Uani 1 1 d . . .
O3 O -0.02744(9) 0.8850(2) 0.81263(14) 0.0663(6) Uani 1 1 d . . .
N1 N 0.01852(11) 0.2353(3) 0.93642(16) 0.0504(7) Uani 1 1 d . . .
C3 C 0.05065(11) 0.5195(3) 0.94358(16) 0.0396(6) Uani 1 1 d . . .
C4 C 0.03689(12) 0.6806(3) 0.91151(17) 0.0458(7) Uani 1 1 d . . .
H4 H 0.0657 0.7630 0.9397 0.055 Uiso 1 1 calc R . .
C5 C 0.00611(12) 0.3999(3) 0.90229(18) 0.0435(7) Uani 1 1 d . . .
C6 C 0.11364(11) 0.4721(3) 1.01757(16) 0.0395(6) Uani 1 1 d . . .
H6 H 0.1296 0.5592 1.0633 0.047 Uiso 1 1 calc R . .
C7 C 0.16058(12) 0.2635(3) 1.14512(17) 0.0435(7) Uani 1 1 d . . .
C8 C 0.15389(11) 0.4585(3) 0.98209(18) 0.0435(7) Uani 1 1 d . . .
C9 C -0.04931(13) 0.4397(4) 0.8285(2) 0.0571(8) Uani 1 1 d . . .
H9 H -0.0785 0.3579 0.8007 0.069 Uiso 1 1 calc R . .
C10 C -0.01925(13) 0.7212(4) 0.83798(19) 0.0488(7) Uani 1 1 d . . .
C11 C -0.06203(13) 0.5998(4) 0.7953(2) 0.0577(8) Uani 1 1 d . . .
H11 H -0.0992 0.6253 0.7445 0.069 Uiso 1 1 calc R . .
C12 C 0.14185(13) 0.3460(4) 0.91643(19) 0.0584(8) Uani 1 1 d . . .
H12 H 0.1077 0.2809 0.8915 0.070 Uiso 1 1 calc R . .
B1 B 0.12871(14) -0.0221(4) 1.1153(2) 0.0467(8) Uani 1 1 d . . .
C18 C -0.07917(16) 0.9257(4) 0.7268(2) 0.0775(11) Uani 1 1 d . . .
H18A H -0.0808 0.8560 0.6821 0.116 Uiso 1 1 calc R . .
H18B H -0.0772 1.0400 0.7134 0.116 Uiso 1 1 calc R . .
H18C H -0.1143 0.9084 0.7273 0.116 Uiso 1 1 calc R . .
C13 C 0.20948(14) 0.3755(4) 1.20937(19) 0.0663(9) Uani 1 1 d . . .
H13A H 0.2224 0.3453 1.2692 0.099 Uiso 1 1 calc R . .
H13B H 0.1954 0.4881 1.1980 0.099 Uiso 1 1 calc R . .
H13C H 0.2423 0.3656 1.2025 0.099 Uiso 1 1 calc R . .
C14 C 0.17893(14) 0.3272(4) 0.8866(2) 0.0649(9) Uani 1 1 d . . .
H14 H 0.1699 0.2492 0.8427 0.078 Uiso 1 1 calc R . .
C15 C 0.20507(15) 0.5532(4) 1.0181(2) 0.0730(10) Uani 1 1 d . . .
H15 H 0.2146 0.6300 1.0628 0.088 Uiso 1 1 calc R . .
C16 C 0.24231(16) 0.5338(4) 0.9875(3) 0.0866(12) Uani 1 1 d . . .
H16 H 0.2768 0.5973 1.0123 0.104 Uiso 1 1 calc R . .
C17 C 0.22859(17) 0.4221(4) 0.9213(3) 0.0721(10) Uani 1 1 d . . .
H17 H 0.2532 0.4114 0.9002 0.087 Uiso 1 1 calc R . .
H1 H -0.0078(12) 0.161(3) 0.9139(17) 0.045(8) Uiso 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
O1 C1 1.305(3) . ?
O1 B1 1.486(4) . ?
F1 B1 1.371(4) . ?
O2 C7 1.328(3) . ?
O2 B1 1.464(4) . ?
C1 N1 1.318(3) . ?
C1 C2 1.415(3) . ?
F2 B1 1.371(4) . ?
C2 C7 1.360(3) . ?
C2 C6 1.525(3) . ?
O3 C10 1.373(3) . ?
O3 C18 1.431(4) . ?
N1 C5 1.420(3) . ?
C3 C4 1.384(4) . ?
C3 C5 1.389(3) . ?
C3 C6 1.515(3) . ?
C4 C10 1.388(4) . ?
C5 C9 1.378(4) . ?
C6 C8 1.535(4) . ?
C7 C13 1.482(4) . ?
C8 C12 1.375(4) . ?
C8 C15 1.383(4) . ?
C9 C11 1.382(4) . ?
C10 C11 1.376(4) . ?
C12 C14 1.377(4) . ?
C14 C17 1.356(4) . ?
C15 C16 1.393(5) . ?
C16 C17 1.368(5) . ?

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 B1 118.5(2) . . ?
C7 O2 B1 119.1(2) . . ?
O1 C1 N1 116.4(2) . . ?
O1 C1 C2 122.0(2) . . ?
N1 C1 C2 121.6(2) . . ?
C7 C2 C1 117.7(2) . . ?
C7 C2 C6 123.4(2) . . ?
C1 C2 C6 118.9(2) . . ?
C10 O3 C18 117.3(3) . . ?
C1 N1 C5 123.1(2) . . ?
C4 C3 C5 118.3(2) . . ?
C4 C3 C6 120.9(2) . . ?
C5 C3 C6 120.7(2) . . ?
C3 C4 C10 121.1(3) . . ?
C9 C5 C3 120.5(3) . . ?
C9 C5 N1 120.2(3) . . ?
C3 C5 N1 119.3(2) . . ?
C3 C6 C2 111.7(2) . . ?
C3 C6 C8 111.0(2) . . ?
C2 C6 C8 109.0(2) . . ?
O2 C7 C2 121.9(2) . . ?
O2 C7 C13 113.5(2) . . ?
C2 C7 C13 124.6(3) . . ?
C12 C8 C15 117.7(3) . . ?
C12 C8 C6 121.1(2) . . ?
C15 C8 C6 121.1(3) . . ?
C5 C9 C11 120.7(3) . . ?
O3 C10 C11 124.5(3) . . ?
O3 C10 C4 115.6(3) . . ?
C11 C10 C4 119.9(3) . . ?
C10 C11 C9 119.4(3) . . ?
C8 C12 C14 121.8(3) . . ?
F1 B1 F2 110.9(3) . . ?
F1 B1 O2 109.0(2) . . ?
F2 B1 O2 110.4(2) . . ?
F1 B1 O1 107.3(2) . . ?
F2 B1 O1 108.9(2) . . ?
O2 B1 O1 110.3(2) . . ?
C17 C14 C12 120.1(3) . . ?
C8 C15 C16 120.1(3) . . ?
C17 C16 C15 120.6(3) . . ?
C14 C17 C16 119.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.040


_database_code_depnum_ccdc_archive 'CCDC 922666'
#######################################################################
#
#                 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_p

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            
8-(2-Chlorophenyl)-2,2-difluoro-7-(4-methoxyphenyl)-4-methyl-7,8-dihydro-2H-[1,3,2]dioxaborinino[4,5-b]pyridin-1-ium-2-uide
_chemical_melting_point          151-155
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H38 B2 Cl2 F4 N2 O6'
_chemical_formula_weight         871.29

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   7.643(5)
_cell_length_b                   12.269(5)
_cell_length_c                   12.840(5)
_cell_angle_alpha                101.954(5)
_cell_angle_beta                 104.028(5)
_cell_angle_gamma                98.284(5)
_cell_volume                     1118.6(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6123
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.07
_reflns_number_total             4318
_reflns_number_gt                3256
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.1848P)²+0.6504P] 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         4318
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2992
_refine_ls_wR_factor_gt          0.2757
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.2789(7) -0.0017(5) 0.1248(4) 0.0864(14) Uani 1 1 d . . .
H1A H 0.2709 -0.0781 0.1329 0.130 Uiso 1 1 calc R . .
H1B H 0.1866 0.0310 0.1519 0.130 Uiso 1 1 calc R . .
H1C H 0.3987 0.0429 0.1666 0.130 Uiso 1 1 calc R . .
C2 C 0.2483(5) -0.0028(4) 0.0045(3) 0.0656(10) Uani 1 1 d . . .
C3 C 0.2502(5) 0.0922(3) -0.0350(3) 0.0549(8) Uani 1 1 d . . .
C4 C 0.2274(5) 0.0776(3) -0.1516(3) 0.0525(8) Uani 1 1 d . . .
C5 C 0.2719(6) 0.2069(4) 0.0299(3) 0.0648(10) Uani 1 1 d . . .
H5 H 0.2745 0.2191 0.1043 0.078 Uiso 1 1 calc R . .
C6 C 0.2882(6) 0.2949(3) -0.0138(3) 0.0672(10) Uani 1 1 d . . .
H6 H 0.2967 0.3665 0.0311 0.081 Uiso 1 1 calc R . .
C7 C 0.2936(5) 0.2873(3) -0.1299(3) 0.0563(8) Uani 1 1 d . . .
C8 C 0.2177(5) 0.1459(3) -0.3154(3) 0.0582(9) Uani 1 1 d . . .
C9 C 0.0564(5) 0.1566(3) -0.3853(3) 0.0618(9) Uani 1 1 d . . .
C10 C 0.0404(7) 0.1443(3) -0.4973(3) 0.0728(11) Uani 1 1 d . . .
H10 H -0.0679 0.1526 -0.5440 0.087 Uiso 1 1 calc R . .
C11 C 0.1812(7) 0.1201(4) -0.5394(4) 0.0768(12) Uani 1 1 d . . .
H11 H 0.1685 0.1103 -0.6148 0.092 Uiso 1 1 calc R . .
C12 C 0.3447(7) 0.1102(4) -0.4685(4) 0.0772(12) Uani 1 1 d . . .
H12 H 0.4412 0.0971 -0.4985 0.093 Uiso 1 1 calc R . .
C13 C 0.3722(5) 0.1186(3) -0.3577(3) 0.0617(9) Uani 1 1 d . . .
H13 H 0.4803 0.1079 -0.3127 0.074 Uiso 1 1 calc R . .
C14 C 0.4810(5) 0.3382(3) -0.1375(3) 0.0501(8) Uani 1 1 d . . .
C15 C 0.4984(6) 0.4058(3) -0.2096(3) 0.0612(9) Uani 1 1 d . . .
H15 H 0.3929 0.4222 -0.2519 0.073 Uiso 1 1 calc R . .
C16 C 0.6674(6) 0.4496(3) -0.2207(3) 0.0651(10) Uani 1 1 d . . .
H16 H 0.6757 0.4943 -0.2703 0.078 Uiso 1 1 calc R . .
C17 C 0.6409(5) 0.3153(3) -0.0746(3) 0.0573(9) Uani 1 1 d . . .
H17 H 0.6324 0.2705 -0.0251 0.069 Uiso 1 1 calc R . .
C18 C 0.8101(5) 0.3574(3) -0.0844(3) 0.0641(9) Uani 1 1 d . . .
H18 H 0.9152 0.3401 -0.0427 0.077 Uiso 1 1 calc R . .
C19 C 0.8250(5) 0.4262(3) -0.1568(3) 0.0591(9) Uani 1 1 d . . .
C20 C 1.0262(9) 0.5445(5) -0.2230(6) 0.1069(19) Uani 1 1 d . . .
H20A H 1.1546 0.5645 -0.2182 0.160 Uiso 1 1 calc R . .
H20B H 0.9840 0.6116 -0.1950 0.160 Uiso 1 1 calc R . .
H20C H 0.9571 0.5113 -0.2991 0.160 Uiso 1 1 calc R . .
C21 C 0.325(3) 0.5845(17) 0.5696(13) 0.119(5) Uani 0.50 1 d P . .
C22 C 0.450(5) 0.535(3) 0.5224(17) 0.189(13) Uani 0.50 1 d P . .
C23 C 0.615(2) 0.5808(12) 0.5287(12) 0.083(4) Uani 0.50 1 d P . .
C24 C 0.699(4) 0.543(4) 0.494(3) 0.24(2) Uani 0.50 1 d P . .
C25 C 0.496(5) 0.6372(15) 0.5809(16) 0.180(12) Uani 0.50 1 d P . .
B1 B 0.1735(7) -0.1288(4) -0.1792(4) 0.0691(12) Uani 1 1 d . . .
N1 N 0.2381(4) 0.1652(2) -0.1966(2) 0.0530(7) Uani 1 1 d . . .
O1 O 0.1954(4) -0.0222(2) -0.2182(2) 0.0667(7) Uani 1 1 d . . .
O2 O 0.2240(5) -0.1058(3) -0.0601(3) 0.0826(9) Uani 1 1 d . . .
O3 O 1.0009(4) 0.4652(2) -0.1594(3) 0.0767(8) Uani 1 1 d . . .
F1 F 0.2809(5) -0.1941(3) -0.2189(3) 0.1118(11) Uani 1 1 d . . .
F2 F -0.0100(4) -0.1815(2) -0.2210(2) 0.0968(9) Uani 1 1 d . . .
Cl1 Cl -0.12428(15) 0.18465(12) -0.33274(10) 0.0877(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
C1 C2 1.502(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.320(5) . ?
C2 C3 1.365(5) . ?
C3 C4 1.434(5) . ?
C3 C5 1.443(5) . ?
C4 O1 1.293(4) . ?
C4 N1 1.323(4) . ?
C5 C6 1.319(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(6) . ?
C6 H6 0.9300 . ?
C7 N1 1.505(4) . ?
C7 C14 1.512(5) . ?
C8 C9 1.380(5) . ?
C8 N1 1.459(5) . ?
C8 C13 1.467(6) . ?
C9 C10 1.387(6) . ?
C9 Cl1 1.724(4) . ?
C10 C11 1.359(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C14 C17 1.392(5) . ?
C15 C16 1.378(6) . ?
C15 H15 0.9300 . ?
C16 C19 1.388(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(6) . ?
C18 H18 0.9300 . ?
C19 O3 1.372(5) . ?
C20 O3 1.415(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C25 1.33(3) . ?
C21 C22 1.39(2) . ?
C21 C24 1.57(5) 2_666 ?
C22 C25 1.27(3) . ?
C22 C23 1.28(4) . ?
C22 C24 1.32(5) 2_666 ?
C22 C22 1.36(3) 2_666 ?
C22 C23 1.40(4) 2_666 ?
C22 C24 2.01(5) . ?
C23 C24 0.98(5) . ?
C23 C22 1.40(4) 2_666 ?
C23 C25 1.43(4) . ?
C24 C22 1.32(5) 2_666 ?
C24 C21 1.57(5) 2_666 ?
B1 F1 1.341(6) . ?
B1 F2 1.380(6) . ?
B1 O2 1.439(6) . ?
B1 O1 1.496(5) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C3 122.7(3) . . ?
O2 C2 C1 113.0(4) . . ?
C3 C2 C1 124.2(4) . . ?
C2 C3 C4 117.5(3) . . ?
C2 C3 C5 125.9(3) . . ?
C4 C3 C5 116.6(3) . . ?
O1 C4 N1 116.5(3) . . ?
O1 C4 C3 121.5(3) . . ?
N1 C4 C3 122.0(3) . . ?
C6 C5 C3 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C3 C5 H5 119.2 . . ?
C5 C6 C7 124.5(3) . . ?
C5 C6 H6 117.8 . . ?
C7 C6 H6 117.8 . . ?
C6 C7 N1 110.4(3) . . ?
C6 C7 C14 112.8(3) . . ?
N1 C7 C14 109.1(3) . . ?
C9 C8 N1 119.8(3) . . ?
C9 C8 C13 121.1(3) . . ?
N1 C8 C13 119.1(3) . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 Cl1 119.6(3) . . ?
C10 C9 Cl1 120.5(3) . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 124.1(4) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C12 C13 C8 114.7(4) . . ?
C12 C13 H13 122.7 . . ?
C8 C13 H13 122.7 . . ?
C15 C14 C17 118.0(3) . . ?
C15 C14 C7 121.0(3) . . ?
C17 C14 C7 121.0(3) . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C19 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C19 C16 H16 120.5 . . ?
C18 C17 C14 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C14 C17 H17 119.4 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
O3 C19 C16 124.7(3) . . ?
O3 C19 C18 115.4(3) . . ?
C16 C19 C18 119.8(4) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 C21 C22 56(2) . . ?
C25 C21 C24 107.8(19) . 2_666 ?
C22 C21 C24 53(2) . 2_666 ?
C25 C22 C23 68(3) . . ?
C25 C22 C24 130(3) . 2_666 ?
C23 C22 C24 161(3) . 2_666 ?
C25 C22 C22 132(6) . 2_666 ?
C23 C22 C22 64(3) . 2_666 ?
C24 C22 C22 97(4) 2_666 2_666 ?
C25 C22 C21 59.6(18) . . ?
C23 C22 C21 128(3) . . ?
C24 C22 C21 71(3) 2_666 . ?
C22 C22 C21 167(5) 2_666 . ?
C25 C22 C23 170(3) . 2_666 ?
C23 C22 C23 119.1(15) . 2_666 ?
C24 C22 C23 42(3) 2_666 2_666 ?
C22 C22 C23 55(3) 2_666 2_666 ?
C21 C22 C23 113(3) . 2_666 ?
C25 C22 C24 92(3) . . ?
C23 C22 C24 23.5(17) . . ?
C24 C22 C24 138(2) 2_666 . ?
C22 C22 C24 41(3) 2_666 . ?
C21 C22 C24 151(3) . . ?
C23 C22 C24 95.7(16) 2_666 . ?
C24 C23 C22 125(3) . . ?
C24 C23 C22 65(2) . 2_666 ?
C22 C23 C22 60.9(15) . 2_666 ?
C24 C23 C25 179(3) . . ?
C22 C23 C25 55.7(16) . . ?
C22 C23 C25 116(2) 2_666 . ?
C23 C24 C22 73(2) . 2_666 ?
C23 C24 C21 130(3) . 2_666 ?
C22 C24 C21 56.9(18) 2_666 2_666 ?
C23 C24 C22 31.1(15) . . ?
C22 C24 C22 42(2) 2_666 . ?
C21 C24 C22 98.8(18) 2_666 . ?
C22 C25 C21 64.8(19) . . ?
C22 C25 C23 56(2) . . ?
C21 C25 C23 120.9(17) . . ?
F1 B1 F2 111.2(4) . . ?
F1 B1 O2 109.7(4) . . ?
F2 B1 O2 109.0(4) . . ?
F1 B1 O1 107.9(4) . . ?
F2 B1 O1 107.0(4) . . ?
O2 B1 O1 112.2(3) . . ?
C4 N1 C8 119.8(3) . . ?
C4 N1 C7 123.4(3) . . ?
C8 N1 C7 116.4(3) . . ?
C4 O1 B1 122.1(3) . . ?
C2 O2 B1 122.6(3) . . ?
C19 O3 C20 117.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 938933'
