# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_o-tol
_database_code_depnum_ccdc_archive 'CCDC 1524227'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            o-tol
_chemical_melting_point          124-126
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 B F2 O2'
_chemical_formula_weight         286.07

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'
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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_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                   8.2331(6)
_cell_length_b                   13.1144(10)
_cell_length_c                   25.5836(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2762.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9014
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.35

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0833
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24716
_diffrn_reflns_av_R_equivalents  0.1021
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.36
_reflns_number_total             3121
_reflns_number_gt                1798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.1231P)²+0.7127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3121
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2586
_refine_ls_wR_factor_gt          0.2059
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
O2 O 0.6723(3) 0.12906(15) 0.93933(8) 0.0716(7) Uani 1 1 d . . .
O3 O 0.5379(3) 0.11609(16) 0.85409(8) 0.0722(7) Uani 1 1 d . . .
C1 C 0.5380(3) 0.0169(2) 0.85866(10) 0.0564(7) Uani 1 1 d . . .
C2 C 0.6725(3) 0.0291(2) 0.94225(10) 0.0543(7) Uani 1 1 d . . .
C3 C 0.6136(4) -0.0291(2) 0.90117(11) 0.0586(8) Uani 1 1 d . . .
H1 H 0.6247 -0.0996 0.9020 0.070 Uiso 1 1 calc R . .
F1 F 0.7850(3) 0.2007(2) 0.86471(9) 0.1140(9) Uani 1 1 d . . .
C5 C 0.7368(3) -0.0135(2) 0.99117(10) 0.0521(7) Uani 1 1 d . . .
C6 C 0.8202(4) 0.0483(2) 1.02611(11) 0.0598(8) Uani 1 1 d . . .
H2 H 0.8326 0.1173 1.0187 0.072 Uiso 1 1 calc R . .
C7 C 0.4513(4) -0.0439(2) 0.81839(11) 0.0616(8) Uani 1 1 d . . .
F2 F 0.5558(4) 0.26917(16) 0.89900(10) 0.1147(10) Uani 1 1 d . . .
C8 C 0.8850(4) 0.0094(3) 1.07175(11) 0.0702(9) Uani 1 1 d . . .
H3 H 0.9411 0.0517 1.0947 0.084 Uiso 1 1 calc R . .
C9 C 0.4479(4) -0.0172(3) 0.76551(12) 0.0704(9) Uani 1 1 d . . .
C10 C 0.2879(5) -0.1951(3) 0.80049(15) 0.0869(11) Uani 1 1 d . . .
H4 H 0.2330 -0.2529 0.8120 0.104 Uiso 1 1 calc R . .
C11 C 0.8660(5) -0.0925(3) 1.08301(13) 0.0810(11) Uani 1 1 d . . .
H5 H 0.9096 -0.1193 1.1136 0.097 Uiso 1 1 calc R . .
C12 C 0.7171(5) -0.1162(3) 1.00320(13) 0.0793(11) Uani 1 1 d . . .
H6 H 0.6603 -0.1588 0.9806 0.095 Uiso 1 1 calc R . .
C13 C 0.3680(4) -0.0848(3) 0.73067(14) 0.0773(10) Uani 1 1 d . . .
H7 H 0.3695 -0.0713 0.6950 0.093 Uiso 1 1 calc R . .
C14 C 0.7831(6) -0.1547(3) 1.04932(15) 0.0972(13) Uani 1 1 d . . .
H8 H 0.7707 -0.2235 1.0573 0.117 Uiso 1 1 calc R . .
C15 C 0.3709(4) -0.1332(2) 0.83539(13) 0.0700(9) Uani 1 1 d . . .
H9 H 0.3737 -0.1507 0.8706 0.084 Uiso 1 1 calc R . .
C16 C 0.2887(5) -0.1694(3) 0.74869(16) 0.0862(11) Uani 1 1 d . . .
H10 H 0.2337 -0.2106 0.7250 0.103 Uiso 1 1 calc R . .
B1 B 0.6383(6) 0.1816(3) 0.88875(16) 0.0784(12) Uani 1 1 d . . .
C17 C 0.5285(5) 0.0732(3) 0.74401(16) 0.0925(12) Uani 1 1 d . . .
H11 H 0.4725 0.1334 0.7554 0.139 Uiso 1 1 calc R . .
H12 H 0.5270 0.0700 0.7065 0.139 Uiso 1 1 calc R . .
H13 H 0.6390 0.0754 0.7560 0.139 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.314(3) . ?
O2 B1 1.493(4) . ?
O3 C1 1.306(3) . ?
O3 B1 1.486(5) . ?
C1 C3 1.390(4) . ?
C1 C7 1.485(4) . ?
C2 C3 1.386(4) . ?
C2 C5 1.469(4) . ?
F1 B1 1.379(5) . ?
C5 C6 1.388(4) . ?
C5 C12 1.391(4) . ?
C6 C8 1.382(4) . ?
C7 C9 1.398(4) . ?
C7 C15 1.414(4) . ?
F2 B1 1.360(5) . ?
C8 C11 1.376(5) . ?
C9 C13 1.418(5) . ?
C9 C17 1.466(5) . ?
C10 C16 1.368(5) . ?
C10 C15 1.387(5) . ?
C11 C14 1.369(5) . ?
C12 C14 1.394(5) . ?
C13 C16 1.367(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 O2 B1 120.7(2) . . ?
C1 O3 B1 121.5(2) . . ?
O3 C1 C3 120.1(3) . . ?
O3 C1 C7 118.2(2) . . ?
C3 C1 C7 121.6(3) . . ?
O2 C2 C3 120.4(2) . . ?
O2 C2 C5 115.4(2) . . ?
C3 C2 C5 124.3(3) . . ?
C2 C3 C1 120.8(3) . . ?
C6 C5 C12 118.7(3) . . ?
C6 C5 C2 120.3(3) . . ?
C12 C5 C2 121.0(3) . . ?
C8 C6 C5 121.3(3) . . ?
C9 C7 C15 119.7(3) . . ?
C9 C7 C1 123.1(3) . . ?
C15 C7 C1 117.2(3) . . ?
C11 C8 C6 119.5(3) . . ?
C7 C9 C13 117.4(3) . . ?
C7 C9 C17 123.8(3) . . ?
C13 C9 C17 118.7(3) . . ?
C16 C10 C15 118.5(4) . . ?
C14 C11 C8 120.2(3) . . ?
C5 C12 C14 119.5(3) . . ?
C16 C13 C9 121.1(3) . . ?
C11 C14 C12 120.8(3) . . ?
C10 C15 C7 121.2(3) . . ?
C13 C16 C10 122.0(4) . . ?
F2 B1 F1 111.7(3) . . ?
F2 B1 O3 109.0(3) . . ?
F1 B1 O3 109.0(3) . . ?
F2 B1 O2 108.5(3) . . ?
F1 B1 O2 107.8(3) . . ?
O3 B1 O2 110.8(3) . . ?

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
B1 O3 C1 C3 9.6(4) . . . . ?
B1 O3 C1 C7 -172.3(3) . . . . ?
B1 O2 C2 C3 -11.4(5) . . . . ?
B1 O2 C2 C5 169.1(3) . . . . ?
O2 C2 C3 C1 -6.7(4) . . . . ?
C5 C2 C3 C1 172.7(3) . . . . ?
O3 C1 C3 C2 7.8(4) . . . . ?
C7 C1 C3 C2 -170.3(3) . . . . ?
O2 C2 C5 C6 -12.4(4) . . . . ?
C3 C2 C5 C6 168.2(3) . . . . ?
O2 C2 C5 C12 168.3(3) . . . . ?
C3 C2 C5 C12 -11.2(5) . . . . ?
C12 C5 C6 C8 0.9(5) . . . . ?
C2 C5 C6 C8 -178.4(3) . . . . ?
O3 C1 C7 C9 36.4(4) . . . . ?
C3 C1 C7 C9 -145.6(3) . . . . ?
O3 C1 C7 C15 -144.3(3) . . . . ?
C3 C1 C7 C15 33.8(4) . . . . ?
C5 C6 C8 C11 -0.4(5) . . . . ?
C15 C7 C9 C13 -2.6(4) . . . . ?
C1 C7 C9 C13 176.7(3) . . . . ?
C15 C7 C9 C17 -179.4(3) . . . . ?
C1 C7 C9 C17 -0.1(5) . . . . ?
C6 C8 C11 C14 -0.2(6) . . . . ?
C6 C5 C12 C14 -1.0(6) . . . . ?
C2 C5 C12 C14 178.4(4) . . . . ?
C7 C9 C13 C16 4.0(5) . . . . ?
C17 C9 C13 C16 -179.0(3) . . . . ?
C8 C11 C14 C12 0.1(7) . . . . ?
C5 C12 C14 C11 0.5(7) . . . . ?
C16 C10 C15 C7 1.6(5) . . . . ?
C9 C7 C15 C10 -0.1(5) . . . . ?
C1 C7 C15 C10 -179.5(3) . . . . ?
C9 C13 C16 C10 -2.6(6) . . . . ?
C15 C10 C16 C13 -0.2(6) . . . . ?
C1 O3 B1 F2 -144.2(3) . . . . ?
C1 O3 B1 F1 93.6(3) . . . . ?
C1 O3 B1 O2 -24.9(5) . . . . ?
C2 O2 B1 F2 145.4(3) . . . . ?
C2 O2 B1 F1 -93.5(4) . . . . ?
C2 O2 B1 O3 25.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.36
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1524228'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            p-xyBF2
_chemical_melting_point          126-127
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H30 B2 F4 O4'
_chemical_formula_weight         600.20

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'
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   'P 21/a'

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

_cell_length_a                   14.2946(13)
_cell_length_b                   14.0130(10)
_cell_length_c                   15.2327(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.760(3)
_cell_angle_gamma                90.00
_cell_volume                     2950.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    12341
_cell_measurement_theta_min      3.125
_cell_measurement_theta_max      27.365

_exptl_crystal_description       yellow
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3266
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27624
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0870
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.43
_reflns_number_total             6671
_reflns_number_gt                2816
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0985P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0038(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6671
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_refine_ls_shift/su_max          0.006
_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
C27 C 1.14201(15) -0.29749(14) 0.27455(12) 0.0543(5) Uani 1 1 d . . .
O1 O 0.79687(13) 0.02533(9) 0.09655(8) 0.0788(5) Uani 1 1 d . . .
O3 O 0.78961(13) 0.19913(9) 0.09810(8) 0.0807(6) Uani 1 1 d . . .
C28 C 0.86283(14) -0.06659(13) 0.22595(12) 0.0508(5) Uani 1 1 d . . .
O2 O 1.19158(13) -0.20261(10) 0.40416(9) 0.0816(5) Uani 1 1 d . . .
C1 C 0.85340(14) 0.29190(12) 0.22914(11) 0.0480(5) Uani 1 1 d . . .
C2 C 1.16079(15) -0.20301(14) 0.31641(12) 0.0561(5) Uani 1 1 d . . .
O4 O 1.18335(15) -0.02917(10) 0.40011(9) 0.0904(6) Uani 1 1 d . . .
F1 F 0.79582(13) 0.11529(9) -0.03065(8) 0.0981(6) Uani 1 1 d . . .
C5 C 0.83030(14) 0.19873(13) 0.18390(12) 0.0498(5) Uani 1 1 d . . .
C6 C 0.83645(15) 0.02729(13) 0.18315(11) 0.0503(5) Uani 1 1 d . . .
C7 C 1.12630(15) 0.06075(14) 0.26634(12) 0.0543(5) Uani 1 1 d . . .
F3 F 1.16705(15) -0.11498(10) 0.52398(9) 0.1145(7) Uani 1 1 d . . .
C9 C 1.15309(16) -0.03155(14) 0.31290(12) 0.0562(5) Uani 1 1 d . . .
F2 F 0.66061(13) 0.10911(9) 0.01963(10) 0.0994(6) Uani 1 1 d . . .
C11 C 0.87392(15) 0.29449(13) 0.32370(12) 0.0541(5) Uani 1 1 d . . .
H1 H 0.8703 0.2380 0.3547 0.065 Uiso 1 1 calc R . .
C12 C 0.85207(16) 0.11252(13) 0.22865(12) 0.0593(6) Uani 1 1 d . . .
H2 H 0.8780 0.1124 0.2912 0.071 Uiso 1 1 calc R . .
C13 C 0.91132(16) -0.07492(15) 0.31741(13) 0.0625(6) Uani 1 1 d . . .
H3 H 0.9289 -0.0204 0.3525 0.075 Uiso 1 1 calc R . .
C14 C 1.09389(17) -0.30851(16) 0.18350(14) 0.0720(7) Uani 1 1 d . . .
H4 H 1.0745 -0.2549 0.1475 0.086 Uiso 1 1 calc R . .
C15 C 0.89942(16) 0.37750(13) 0.37336(13) 0.0565(6) Uani 1 1 d . . .
F4 F 1.31192(14) -0.10864(10) 0.49233(12) 0.1210(7) Uani 1 1 d . . .
C17 C 1.14485(18) -0.11845(14) 0.26934(13) 0.0672(7) Uani 1 1 d . . .
H5 H 1.1280 -0.1199 0.2062 0.081 Uiso 1 1 calc R . .
C18 C 1.10605(16) 0.06186(15) 0.17195(13) 0.0630(6) Uani 1 1 d . . .
H6 H 1.1104 0.0049 0.1419 0.076 Uiso 1 1 calc R . .
C29 C 0.93346(17) -0.16422(15) 0.35609(14) 0.0709(7) Uani 1 1 d . . .
H7 H 0.9654 -0.1695 0.4172 0.085 Uiso 1 1 calc R . .
C19 C 0.85670(16) 0.37682(13) 0.18027(13) 0.0557(5) Uani 1 1 d . . .
C20 C 1.17020(17) -0.37879(14) 0.32679(14) 0.0621(6) Uani 1 1 d . . .
H8 H 1.2025 -0.3729 0.3878 0.075 Uiso 1 1 calc R . .
C21 C 0.88075(17) 0.46002(14) 0.23181(14) 0.0671(6) Uani 1 1 d . . .
H9 H 0.8828 0.5174 0.2017 0.081 Uiso 1 1 calc R . .
C22 C 0.90141(17) 0.46059(14) 0.32470(14) 0.0668(6) Uani 1 1 d . . .
H10 H 0.9171 0.5179 0.3557 0.080 Uiso 1 1 calc R . .
C23 C 1.12057(16) 0.14639(15) 0.31332(13) 0.0611(6) Uani 1 1 d . . .
C24 C 1.07965(17) 0.14394(15) 0.12052(13) 0.0634(6) Uani 1 1 d . . .
C25 C 0.90822(17) -0.24526(16) 0.30423(15) 0.0721(7) Uani 1 1 d . . .
H11 H 0.9237 -0.3051 0.3304 0.087 Uiso 1 1 calc R . .
C26 C 0.83772(16) -0.14917(14) 0.17518(13) 0.0592(6) Uani 1 1 d . . .
H12 H 0.8052 -0.1447 0.1141 0.071 Uiso 1 1 calc R . .
C30 C 1.10284(19) -0.47819(18) 0.19863(16) 0.0803(7) Uani 1 1 d . . .
H13 H 1.0897 -0.5386 0.1733 0.096 Uiso 1 1 calc R . .
B3 B 0.7595(3) 0.11178(18) 0.04336(16) 0.0720(9) Uani 1 1 d . . .
C31 C 1.15045(19) -0.46857(16) 0.28839(16) 0.0751(7) Uani 1 1 d . . .
H14 H 1.1696 -0.5226 0.3238 0.090 Uiso 1 1 calc R . .
C32 C 1.07642(16) 0.22759(16) 0.16800(15) 0.0689(6) Uani 1 1 d . . .
H15 H 1.0605 0.2844 0.1361 0.083 Uiso 1 1 calc R . .
C33 C 1.0545(2) 0.14253(17) 0.01845(14) 0.0914(8) Uani 1 1 d . . .
H16 H 1.0798 0.0855 -0.0018 0.137 Uiso 1 1 calc R . .
H17 H 1.0823 0.1973 -0.0032 0.137 Uiso 1 1 calc R . .
H18 H 0.9855 0.1439 -0.0048 0.137 Uiso 1 1 calc R . .
C34 C 1.09599(17) 0.22871(15) 0.26038(15) 0.0697(6) Uani 1 1 d . . .
H19 H 1.0929 0.2866 0.2894 0.084 Uiso 1 1 calc R . .
B8 B 1.2148(3) -0.11417(19) 0.45761(17) 0.0795(10) Uani 1 1 d . . .
C35 C 1.07460(19) -0.39836(17) 0.14614(16) 0.0792(7) Uani 1 1 d . . .
H20 H 1.0424 -0.4049 0.0852 0.095 Uiso 1 1 calc R . .
C36 C 0.8416(2) 0.38411(15) 0.07940(13) 0.0840(8) Uani 1 1 d . . .
H21 H 0.7739 0.3790 0.0503 0.126 Uiso 1 1 calc R . .
H22 H 0.8760 0.3335 0.0588 0.126 Uiso 1 1 calc R . .
H23 H 0.8654 0.4445 0.0646 0.126 Uiso 1 1 calc R . .
C37 C 0.9266(2) 0.37680(15) 0.47557(13) 0.0814(8) Uani 1 1 d . . .
H24 H 0.9006 0.3206 0.4968 0.122 Uiso 1 1 calc R . .
H25 H 0.9006 0.4325 0.4975 0.122 Uiso 1 1 calc R . .
H26 H 0.9957 0.3768 0.4976 0.122 Uiso 1 1 calc R . .
C38 C 0.86047(17) -0.23812(14) 0.21434(15) 0.0699(7) Uani 1 1 d . . .
H27 H 0.8433 -0.2930 0.1796 0.084 Uiso 1 1 calc R . .
C39 C 1.1356(2) 0.15584(17) 0.41445(14) 0.0977(10) Uani 1 1 d . . .
H28 H 1.0968 0.1094 0.4352 0.147 Uiso 1 1 calc R . .
H29 H 1.1170 0.2187 0.4285 0.147 Uiso 1 1 calc R . .
H30 H 1.2026 0.1455 0.4441 0.147 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C27 C20 1.389(3) . ?
C27 C14 1.391(3) . ?
C27 C2 1.464(3) . ?
O1 C6 1.2965(19) . ?
O1 B3 1.479(3) . ?
O3 C5 1.2881(19) . ?
O3 B3 1.482(3) . ?
C28 C26 1.387(3) . ?
C28 C13 1.394(2) . ?
C28 C6 1.474(2) . ?
O2 C2 1.296(2) . ?
O2 B8 1.473(3) . ?
C1 C11 1.395(2) . ?
C1 C19 1.411(2) . ?
C1 C5 1.474(2) . ?
C2 C17 1.374(2) . ?
O4 C9 1.288(2) . ?
O4 B8 1.479(3) . ?
F1 B3 1.357(3) . ?
C5 C12 1.383(2) . ?
C6 C12 1.370(2) . ?
C7 C18 1.393(2) . ?
C7 C23 1.410(3) . ?
C7 C9 1.478(2) . ?
F3 B8 1.356(4) . ?
C9 C17 1.377(3) . ?
F2 B3 1.367(4) . ?
C11 C15 1.385(2) . ?
C13 C29 1.385(3) . ?
C14 C35 1.380(3) . ?
C15 C22 1.384(3) . ?
C15 C37 1.506(3) . ?
F4 B8 1.356(4) . ?
C18 C24 1.389(3) . ?
C29 C25 1.378(3) . ?
C19 C21 1.399(3) . ?
C19 C36 1.500(3) . ?
C20 C31 1.386(3) . ?
C21 C22 1.370(3) . ?
C23 C34 1.400(3) . ?
C23 C39 1.506(3) . ?
C24 C32 1.384(3) . ?
C24 C33 1.504(3) . ?
C25 C38 1.369(3) . ?
C26 C38 1.384(3) . ?
C30 C31 1.370(3) . ?
C30 C35 1.374(3) . ?
C32 C34 1.363(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 C27 C14 118.54(19) . . ?
C20 C27 C2 119.85(17) . . ?
C14 C27 C2 121.59(18) . . ?
C6 O1 B3 122.89(15) . . ?
C5 O3 B3 123.97(15) . . ?
C26 C28 C13 118.65(17) . . ?
C26 C28 C6 119.82(16) . . ?
C13 C28 C6 121.52(17) . . ?
C2 O2 B8 122.88(16) . . ?
C11 C1 C19 119.75(16) . . ?
C11 C1 C5 117.96(16) . . ?
C19 C1 C5 122.28(16) . . ?
O2 C2 C17 120.13(17) . . ?
O2 C2 C27 115.43(16) . . ?
C17 C2 C27 124.41(17) . . ?
C9 O4 B8 124.14(17) . . ?
O3 C5 C12 119.38(16) . . ?
O3 C5 C1 117.39(15) . . ?
C12 C5 C1 123.22(16) . . ?
O1 C6 C12 120.38(16) . . ?
O1 C6 C28 115.29(15) . . ?
C12 C6 C28 124.32(16) . . ?
C18 C7 C23 119.39(17) . . ?
C18 C7 C9 117.74(17) . . ?
C23 C7 C9 122.87(17) . . ?
O4 C9 C17 119.00(17) . . ?
O4 C9 C7 116.74(16) . . ?
C17 C9 C7 124.24(17) . . ?
C15 C11 C1 122.87(17) . . ?
C6 C12 C5 121.65(16) . . ?
C29 C13 C28 120.16(19) . . ?
C35 C14 C27 120.6(2) . . ?
C22 C15 C11 116.90(17) . . ?
C22 C15 C37 121.61(17) . . ?
C11 C15 C37 121.48(17) . . ?
C2 C17 C9 121.92(18) . . ?
C24 C18 C7 123.15(19) . . ?
C25 C29 C13 120.18(19) . . ?
C21 C19 C1 116.32(17) . . ?
C21 C19 C36 117.97(17) . . ?
C1 C19 C36 125.64(17) . . ?
C31 C20 C27 120.29(19) . . ?
C22 C21 C19 122.83(18) . . ?
C21 C22 C15 121.31(18) . . ?
C34 C23 C7 116.58(18) . . ?
C34 C23 C39 117.78(19) . . ?
C7 C23 C39 125.61(18) . . ?
C32 C24 C18 116.55(18) . . ?
C32 C24 C33 121.35(19) . . ?
C18 C24 C33 122.1(2) . . ?
C38 C25 C29 120.28(19) . . ?
C38 C26 C28 120.78(18) . . ?
C31 C30 C35 119.9(2) . . ?
F1 B3 F2 111.7(2) . . ?
F1 B3 O1 108.9(2) . . ?
F2 B3 O1 109.1(2) . . ?
F1 B3 O3 108.7(2) . . ?
F2 B3 O3 107.7(2) . . ?
O1 B3 O3 110.83(17) . . ?
C30 C31 C20 120.4(2) . . ?
C34 C32 C24 121.58(19) . . ?
C32 C34 C23 122.7(2) . . ?
F3 B8 F4 111.7(2) . . ?
F3 B8 O2 108.7(2) . . ?
F4 B8 O2 109.1(3) . . ?
F3 B8 O4 108.3(3) . . ?
F4 B8 O4 108.1(2) . . ?
O2 B8 O4 111.01(17) . . ?
C30 C35 C14 120.3(2) . . ?
C25 C38 C26 120.0(2) . . ?

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
B8 O2 C2 C17 -2.5(4) . . . . ?
B8 O2 C2 C27 179.6(2) . . . . ?
C20 C27 C2 O2 -9.1(3) . . . . ?
C14 C27 C2 O2 169.11(19) . . . . ?
C20 C27 C2 C17 173.1(2) . . . . ?
C14 C27 C2 C17 -8.6(4) . . . . ?
B3 O3 C5 C12 3.1(4) . . . . ?
B3 O3 C5 C1 -178.3(2) . . . . ?
C11 C1 C5 O3 163.90(18) . . . . ?
C19 C1 C5 O3 -17.1(3) . . . . ?
C11 C1 C5 C12 -17.5(3) . . . . ?
C19 C1 C5 C12 161.5(2) . . . . ?
B3 O1 C6 C12 -5.0(4) . . . . ?
B3 O1 C6 C28 175.6(2) . . . . ?
C26 C28 C6 O1 -5.2(3) . . . . ?
C13 C28 C6 O1 175.97(19) . . . . ?
C26 C28 C6 C12 175.4(2) . . . . ?
C13 C28 C6 C12 -3.4(3) . . . . ?
B8 O4 C9 C17 3.0(4) . . . . ?
B8 O4 C9 C7 -178.9(2) . . . . ?
C18 C7 C9 O4 171.5(2) . . . . ?
C23 C7 C9 O4 -8.5(3) . . . . ?
C18 C7 C9 C17 -10.6(3) . . . . ?
C23 C7 C9 C17 169.4(2) . . . . ?
C19 C1 C11 C15 -1.1(3) . . . . ?
C5 C1 C11 C15 178.0(2) . . . . ?
O1 C6 C12 C5 -2.8(4) . . . . ?
C28 C6 C12 C5 176.6(2) . . . . ?
O3 C5 C12 C6 3.7(3) . . . . ?
C1 C5 C12 C6 -174.8(2) . . . . ?
C26 C28 C13 C29 -0.1(3) . . . . ?
C6 C28 C13 C29 178.7(2) . . . . ?
C20 C27 C14 C35 0.1(4) . . . . ?
C2 C27 C14 C35 -178.2(2) . . . . ?
C1 C11 C15 C22 1.7(3) . . . . ?
C1 C11 C15 C37 -176.5(2) . . . . ?
O2 C2 C17 C9 -5.3(4) . . . . ?
C27 C2 C17 C9 172.3(2) . . . . ?
O4 C9 C17 C2 5.1(4) . . . . ?
C7 C9 C17 C2 -172.8(2) . . . . ?
C23 C7 C18 C24 -0.3(3) . . . . ?
C9 C7 C18 C24 179.7(2) . . . . ?
C28 C13 C29 C25 0.4(4) . . . . ?
C11 C1 C19 C21 -0.2(3) . . . . ?
C5 C1 C19 C21 -179.21(19) . . . . ?
C11 C1 C19 C36 176.6(2) . . . . ?
C5 C1 C19 C36 -2.5(3) . . . . ?
C14 C27 C20 C31 0.0(3) . . . . ?
C2 C27 C20 C31 178.3(2) . . . . ?
C1 C19 C21 C22 0.8(3) . . . . ?
C36 C19 C21 C22 -176.2(2) . . . . ?
C19 C21 C22 C15 -0.1(4) . . . . ?
C11 C15 C22 C21 -1.1(4) . . . . ?
C37 C15 C22 C21 177.1(2) . . . . ?
C18 C7 C23 C34 -1.1(3) . . . . ?
C9 C7 C23 C34 178.9(2) . . . . ?
C18 C7 C23 C39 176.9(2) . . . . ?
C9 C7 C23 C39 -3.1(4) . . . . ?
C7 C18 C24 C32 1.6(3) . . . . ?
C7 C18 C24 C33 -177.7(2) . . . . ?
C13 C29 C25 C38 -0.5(4) . . . . ?
C13 C28 C26 C38 -0.1(3) . . . . ?
C6 C28 C26 C38 -179.0(2) . . . . ?
C6 O1 B3 F1 129.8(2) . . . . ?
C6 O1 B3 F2 -108.0(2) . . . . ?
C6 O1 B3 O3 10.4(4) . . . . ?
C5 O3 B3 F1 -129.0(2) . . . . ?
C5 O3 B3 F2 109.8(2) . . . . ?
C5 O3 B3 O1 -9.5(4) . . . . ?
C35 C30 C31 C20 0.2(4) . . . . ?
C27 C20 C31 C30 -0.1(4) . . . . ?
C18 C24 C32 C34 -1.5(3) . . . . ?
C33 C24 C32 C34 177.8(2) . . . . ?
C24 C32 C34 C23 0.1(4) . . . . ?
C7 C23 C34 C32 1.3(3) . . . . ?
C39 C23 C34 C32 -176.9(2) . . . . ?
C2 O2 B8 F3 128.2(2) . . . . ?
C2 O2 B8 F4 -109.8(2) . . . . ?
C2 O2 B8 O4 9.2(4) . . . . ?
C9 O4 B8 F3 -128.7(2) . . . . ?
C9 O4 B8 F4 110.1(3) . . . . ?
C9 O4 B8 O2 -9.6(4) . . . . ?
C31 C30 C35 C14 -0.1(4) . . . . ?
C27 C14 C35 C30 0.0(4) . . . . ?
C29 C25 C38 C26 0.3(4) . . . . ?
C28 C26 C38 C25 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.075
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_m-tol
_database_code_depnum_ccdc_archive 'CCDC 1524230'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            m-tolBF2
_chemical_melting_point          179-180
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 B F2 O2'
_chemical_formula_weight         286.07

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'
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   'P 21/c'

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

_cell_length_a                   7.1998(17)
_cell_length_b                   14.199(3)
_cell_length_c                   14.276(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.928(5)
_cell_angle_gamma                90.00
_cell_volume                     1422.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4740
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21581
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3211
_reflns_number_gt                805
_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    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_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)+(0.1243P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0000(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3211
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2200
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2597
_refine_ls_wR_factor_gt          0.2089
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_restrained_S_all      0.801
_refine_ls_shift/su_max          0.423
_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
C1 C 0.0582(5) 0.3009(2) 0.1412(2) 0.0867(9) Uani 1 1 d . . .
O1 O 0.3351(3) 0.20887(16) 0.18377(18) 0.1207(9) Uani 1 1 d . . .
O2 O 0.3345(4) 0.03701(16) 0.17845(18) 0.1244(10) Uani 1 1 d . . .
C21 C 0.0586(5) -0.0534(2) 0.1325(2) 0.0930(10) Uani 1 1 d . . .
C2 C 0.1494(5) 0.2080(2) 0.1596(2) 0.0880(9) Uani 1 1 d . . .
C3 C 0.1679(6) 0.3815(3) 0.1569(2) 0.1161(12) Uani 1 1 d . . .
H4 H 0.2992 0.3774 0.1797 0.139 Uiso 1 1 calc R . .
C4 C -0.1362(6) 0.3088(2) 0.1088(2) 0.1090(11) Uani 1 1 d . C .
H5 H -0.2121 0.2551 0.0991 0.131 Uiso 1 1 calc R . .
C5 C 0.1491(5) 0.0379(2) 0.1549(2) 0.0899(10) Uani 1 1 d . . .
F1 F 0.6012(3) 0.12363(15) 0.1769(2) 0.1840(12) Uani 1 1 d . . .
C7 C 0.0548(4) 0.1232(2) 0.1490(2) 0.0886(9) Uani 1 1 d . . .
H15 H -0.0776 0.1232 0.1374 0.106 Uiso 1 1 calc R . .
C22 C -0.1374(6) -0.0607(3) 0.1001(2) 0.1093(11) Uani 1 1 d . D .
H6 H -0.2113 -0.0063 0.0918 0.131 Uiso 1 1 calc R . .
F2 F 0.4906(3) 0.11926(15) 0.3126(2) 0.1655(11) Uani 1 1 d . . .
C9 C 0.0800(10) 0.4693(3) 0.1383(3) 0.150(2) Uani 1 1 d . . .
H7 H 0.1531 0.5239 0.1485 0.180 Uiso 1 1 calc R . .
C10 C -0.2178(8) 0.3967(4) 0.0909(3) 0.1307(14) Uani 1 1 d . . .
H16 H -0.3489 0.4017 0.0682 0.157 Uiso 0.50 1 calc PR A 1
C11 C -0.2256(8) -0.1484(4) 0.0798(3) 0.1305(14) Uani 1 1 d . . .
H17 H -0.3571 -0.1528 0.0582 0.157 Uiso 0.50 1 calc PR B 2
C12 C -0.1111(11) 0.4752(4) 0.1057(3) 0.152(2) Uani 1 1 d . C .
H8 H -0.1689 0.5339 0.0934 0.182 Uiso 1 1 calc R . .
C13 C 0.1642(7) -0.1351(3) 0.1457(3) 0.1309(14) Uani 1 1 d . D .
H9 H 0.2955 -0.1321 0.1687 0.157 Uiso 1 1 calc R . .
C14 C -0.1145(12) -0.2277(4) 0.0922(4) 0.169(3) Uani 1 1 d . D .
H10 H -0.1714 -0.2864 0.0779 0.203 Uiso 1 1 calc R . .
B1 B 0.4456(6) 0.1223(4) 0.2123(4) 0.1243(15) Uani 1 1 d . . .
C16 C 0.0752(11) -0.2223(4) 0.1248(4) 0.169(2) Uani 1 1 d . . .
H11 H 0.1479 -0.2771 0.1334 0.203 Uiso 1 1 calc R D .
C23 C -0.4051(14) 0.4106(5) 0.0585(7) 0.169(4) Uani 0.50 1 d P C 2
H18 H -0.4423 0.4672 0.0863 0.253 Uiso 0.50 1 calc PR C 2
H19 H -0.4739 0.3581 0.0761 0.253 Uiso 0.50 1 calc PR C 2
H20 H -0.4333 0.4166 -0.0102 0.253 Uiso 0.50 1 calc PR C 2
C24 C -0.4141(12) -0.1638(5) 0.0560(6) 0.145(3) Uani 0.50 1 d P D 1
H21 H -0.4527 -0.1761 -0.0117 0.217 Uiso 0.50 1 calc PR D 1
H22 H -0.4799 -0.1092 0.0715 0.217 Uiso 0.50 1 calc PR D 1
H23 H -0.4446 -0.2171 0.0911 0.217 Uiso 0.50 1 calc PR D 1


_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
C1 C4 1.377(4) . ?
C1 C3 1.380(4) . ?
C1 C2 1.471(4) . ?
O1 C2 1.304(3) . ?
O1 B1 1.471(5) . ?
O2 C5 1.302(3) . ?
O2 B1 1.472(5) . ?
C21 C13 1.376(4) . ?
C21 C22 1.387(4) . ?
C21 C5 1.454(4) . ?
C2 C7 1.376(3) . ?
C3 C9 1.396(5) . ?
C4 C10 1.378(5) . ?
C5 C7 1.382(3) . ?
F1 B1 1.328(5) . ?
C22 C11 1.398(5) . ?
F2 B1 1.397(6) . ?
C9 C12 1.353(6) . ?
C10 C23 1.339(8) . ?
C10 C12 1.344(5) . ?
C11 C24 1.342(7) . ?
C11 C14 1.370(6) . ?
C13 C16 1.395(5) . ?
C14 C16 1.343(6) . ?

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
C4 C1 C3 119.3(3) . . ?
C4 C1 C2 120.8(3) . . ?
C3 C1 C2 119.9(4) . . ?
C2 O1 B1 121.6(3) . . ?
C5 O2 B1 121.8(3) . . ?
C13 C21 C22 118.2(3) . . ?
C13 C21 C5 120.9(4) . . ?
C22 C21 C5 120.8(3) . . ?
O1 C2 C7 119.4(3) . . ?
O1 C2 C1 115.4(3) . . ?
C7 C2 C1 125.1(3) . . ?
C1 C3 C9 119.4(4) . . ?
C1 C4 C10 119.7(4) . . ?
O2 C5 C7 119.1(3) . . ?
O2 C5 C21 115.6(3) . . ?
C7 C5 C21 125.3(3) . . ?
C2 C7 C5 122.4(3) . . ?
C21 C22 C11 121.1(4) . . ?
C12 C9 C3 120.3(5) . . ?
C23 C10 C12 115.3(6) . . ?
C23 C10 C4 123.6(6) . . ?
C12 C10 C4 121.2(5) . . ?
C24 C11 C14 115.3(6) . . ?
C24 C11 C22 125.8(6) . . ?
C14 C11 C22 118.7(5) . . ?
C10 C12 C9 120.2(5) . . ?
C21 C13 C16 120.3(5) . . ?
C16 C14 C11 121.1(6) . . ?
F1 B1 F2 111.6(4) . . ?
F1 B1 O1 109.4(4) . . ?
F2 B1 O1 107.3(4) . . ?
F1 B1 O2 109.2(4) . . ?
F2 B1 O2 107.2(4) . . ?
O1 B1 O2 112.1(3) . . ?
C14 C16 C13 120.5(6) . . ?

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
B1 O1 C2 C7 -8.1(5) . . . . ?
B1 O1 C2 C1 174.7(3) . . . . ?
C4 C1 C2 O1 175.6(3) . . . . ?
C3 C1 C2 O1 -4.8(4) . . . . ?
C4 C1 C2 C7 -1.4(5) . . . . ?
C3 C1 C2 C7 178.2(3) . . . . ?
C4 C1 C3 C9 -1.0(5) . . . . ?
C2 C1 C3 C9 179.4(3) . . . . ?
C3 C1 C4 C10 1.2(5) . . . . ?
C2 C1 C4 C10 -179.1(3) . . . . ?
B1 O2 C5 C7 9.0(5) . . . . ?
B1 O2 C5 C21 -173.8(3) . . . . ?
C13 C21 C5 O2 6.6(4) . . . . ?
C22 C21 C5 O2 -175.5(3) . . . . ?
C13 C21 C5 C7 -176.4(3) . . . . ?
C22 C21 C5 C7 1.5(5) . . . . ?
O1 C2 C7 C5 -5.7(5) . . . . ?
C1 C2 C7 C5 171.2(3) . . . . ?
O2 C5 C7 C2 5.3(5) . . . . ?
C21 C5 C7 C2 -171.7(3) . . . . ?
C13 C21 C22 C11 -1.1(5) . . . . ?
C5 C21 C22 C11 -179.0(3) . . . . ?
C1 C3 C9 C12 0.3(7) . . . . ?
C1 C4 C10 C23 179.3(6) . . . . ?
C1 C4 C10 C12 -0.9(6) . . . . ?
C21 C22 C11 C24 174.1(6) . . . . ?
C21 C22 C11 C14 -0.1(6) . . . . ?
C23 C10 C12 C9 -180.0(6) . . . . ?
C4 C10 C12 C9 0.2(8) . . . . ?
C3 C9 C12 C10 0.1(8) . . . . ?
C22 C21 C13 C16 1.4(5) . . . . ?
C5 C21 C13 C16 179.3(4) . . . . ?
C24 C11 C14 C16 -173.7(6) . . . . ?
C22 C11 C14 C16 1.1(8) . . . . ?
C2 O1 B1 F1 141.3(4) . . . . ?
C2 O1 B1 F2 -97.4(4) . . . . ?
C2 O1 B1 O2 20.0(6) . . . . ?
C5 O2 B1 F1 -142.0(4) . . . . ?
C5 O2 B1 F2 97.0(4) . . . . ?
C5 O2 B1 O1 -20.5(6) . . . . ?
C11 C14 C16 C13 -0.8(9) . . . . ?
C21 C13 C16 C14 -0.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.052
