# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_d8v21153
_database_code_depnum_ccdc_archive 'CCDC 2092212'
loop_
_audit_author_name
_audit_author_address
'junbo li'
;SIOC
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 B F2 O2'
_chemical_formula_weight         209.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.5443(6)
_cell_length_b                   7.1138(4)
_cell_length_c                   10.9392(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     976.19(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3565
_cell_measurement_theta_min      6.496
_cell_measurement_theta_max      54.502

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8339
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.248
_diffrn_reflns_theta_max         25.980
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1030
_reflns_number_gt                843
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0657P)²+0.1362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.078(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1030
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
F1 F 0.15894(7) 0.59278(14) 0.40273(9) 0.0744(4) Uani 1 1 d . . . . .
O1 O 0.26234(11) 0.7500 0.26163(12) 0.0638(5) Uani 1 2 d S T P . .
O2 O 0.30556(10) 0.7500 0.47936(13) 0.0601(5) Uani 1 2 d S T P . .
C1 C 0.3922(2) 0.7500 0.1077(2) 0.0659(7) Uani 1 2 d S T P . .
C2 C 0.36304(15) 0.7500 0.23907(17) 0.0463(5) Uani 1 2 d S T P . .
C3 C 0.43737(14) 0.7500 0.33151(16) 0.0456(5) Uani 1 2 d S T P . .
H3 H 0.5096 0.7500 0.3124 0.055 Uiso 1 2 calc R U P . .
C4 C 0.40589(13) 0.7500 0.45142(16) 0.0390(5) Uani 1 2 d S T P . .
C5 C 0.47948(14) 0.7500 0.55620(15) 0.0403(5) Uani 1 2 d S T P . .
C6 C 0.43906(16) 0.7500 0.67389(18) 0.0633(7) Uani 1 2 d S T P . .
H6 H 0.3657 0.7500 0.6861 0.076 Uiso 1 2 calc R U P . .
C7 C 0.50714(19) 0.7500 0.7735(2) 0.0715(7) Uani 1 2 d S T P . .
H7 H 0.4794 0.7500 0.8524 0.086 Uiso 1 2 calc R U P . .
C8 C 0.61491(18) 0.7500 0.75638(19) 0.0571(6) Uani 1 2 d S T P . .
H8 H 0.6604 0.7500 0.8235 0.068 Uiso 1 2 calc R U P . .
C9 C 0.65630(15) 0.7500 0.64017(19) 0.0515(5) Uani 1 2 d S T P . .
H9 H 0.7298 0.7500 0.6288 0.062 Uiso 1 2 calc R U P . .
C10 C 0.58953(14) 0.7500 0.54056(17) 0.0461(5) Uani 1 2 d S T P . .
H10 H 0.6181 0.7500 0.4621 0.055 Uiso 1 2 calc R U P . .
B1 B 0.21903(17) 0.7500 0.3870(2) 0.0511(6) Uani 1 2 d S T P . .
H1A H 0.3585(17) 0.852(3) 0.0711(18) 0.109(8) Uiso 1 1 d . . . . .
H1B H 0.469(3) 0.7500 0.093(3) 0.118(11) Uiso 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3597(15) . ?
O1 C2 1.287(2) . ?
O1 B1 1.475(3) . ?
O2 C4 1.295(2) . ?
O2 B1 1.483(3) . ?
C1 C2 1.483(3) . ?
C1 H1A 0.93(2) . ?
C1 H1B 0.97(4) . ?
C2 C3 1.376(3) . ?
C3 C4 1.370(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.472(2) . ?
C5 C6 1.384(3) . ?
C5 C10 1.391(2) . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
B1 F1 1.3596(15) 7_575 ?

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 O1 B1 122.66(15) . . ?
C4 O2 B1 123.41(15) . . ?
C2 C1 H1A 107.7(13) . . ?
C2 C1 H1B 113.8(19) . . ?
H1A C1 H1B 112.2(16) . . ?
O1 C2 C3 121.62(17) . . ?
O1 C2 C1 115.36(18) . . ?
C3 C2 C1 123.01(18) . . ?
C4 C3 C2 120.56(17) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 C4 C3 120.41(15) . . ?
O2 C4 C5 115.19(15) . . ?
C3 C4 C5 124.40(16) . . ?
C6 C5 C10 118.56(17) . . ?
C6 C5 C4 119.66(16) . . ?
C10 C5 C4 121.78(16) . . ?
C5 C6 C7 120.43(19) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.11(19) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 120.24(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.48(17) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
F1 B1 F1 110.69(17) 7_575 . ?
F1 B1 O1 108.76(12) 7_575 . ?
F1 B1 O1 108.76(12) . . ?
F1 B1 O2 108.66(12) 7_575 . ?
F1 B1 O2 108.66(12) . . ?
O1 B1 O2 111.34(15) . . ?

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 C3 0.000(0) . . . . ?
B1 O1 C2 C1 180.000(0) . . . . ?
O1 C2 C3 C4 0.000(0) . . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
B1 O2 C4 C3 0.000(0) . . . . ?
B1 O2 C4 C5 180.000(0) . . . . ?
C2 C3 C4 O2 0.000(0) . . . . ?
C2 C3 C4 C5 180.000(0) . . . . ?
O2 C4 C5 C6 0.000(0) . . . . ?
C3 C4 C5 C6 180.000(0) . . . . ?
O2 C4 C5 C10 180.000(0) . . . . ?
C3 C4 C5 C10 0.000(0) . . . . ?
C10 C5 C6 C7 0.000(0) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C7 C8 C9 C10 0.000(1) . . . . ?
C8 C9 C10 C5 0.000(0) . . . . ?
C6 C5 C10 C9 0.000(0) . . . . ?
C4 C5 C10 C9 180.000(0) . . . . ?
C2 O1 B1 F1 119.69(11) . . . 7_575 ?
C2 O1 B1 F1 -119.69(11) . . . . ?
C2 O1 B1 O2 0.000(0) . . . . ?
C4 O2 B1 F1 -119.75(12) . . . 7_575 ?
C4 O2 B1 F1 119.75(12) . . . . ?
C4 O2 B1 O1 0.000(0) . . . . ?

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
C1 H1B F1 0.97(4) 2.63(3) 3.529(3) 152.9(10) 4_565
C1 H1B F1 0.97(4) 2.63(3) 3.529(3) 152.9(10) 6_656
C1 H1A F1 0.93(2) 2.52(2) 3.3745(18) 151.9(17) 8_665

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v20839_0m
_database_code_depnum_ccdc_archive 'CCDC 2092213'
loop_
_audit_author_name
_audit_author_address
'junbo li'
;SIOC
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 B F2 I O2'
_chemical_formula_weight         335.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6012(3)
_cell_length_b                   14.2747(5)
_cell_length_c                   10.6115(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.8010(10)
_cell_angle_gamma                90
_cell_volume                     1150.83(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      4.786
_cell_measurement_theta_max      54.959

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.789
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4111
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15738
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2235
_reflns_number_gt                2104
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0380P)²+1.2206P] 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     SHELXL
_refine_ls_extinction_coef       0.0151(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2235
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_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
I1 I 0.81751(3) 0.34426(2) 0.84771(2) 0.05798(16) Uani 1 1 d . . . . .
F1 F 0.5421(4) 0.80271(18) 0.3294(2) 0.0745(7) Uani 1 1 d . . . . .
F2 F 0.8303(4) 0.83709(15) 0.3103(3) 0.0767(8) Uani 1 1 d . . . . .
O1 O 0.6992(3) 0.73083(17) 0.1715(2) 0.0473(6) Uani 1 1 d . . . . .
O2 O 0.7517(3) 0.69521(15) 0.3954(2) 0.0474(6) Uani 1 1 d . . . . .
C1 C 0.7083(4) 0.4498(2) 0.4701(3) 0.0429(7) Uani 1 1 d . . . . .
H1 H 0.6629 0.4256 0.3945 0.052 Uiso 1 1 calc R U . . .
C2 C 0.7257(5) 0.3924(2) 0.5756(3) 0.0458(7) Uani 1 1 d . . . . .
H2 H 0.6904 0.3300 0.5712 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7956(4) 0.4285(2) 0.6866(3) 0.0393(7) Uani 1 1 d . . . . .
C4 C 0.8489(5) 0.5209(2) 0.6950(3) 0.0446(7) Uani 1 1 d . . . . .
H4 H 0.8971 0.5442 0.7702 0.054 Uiso 1 1 calc R U . . .
C5 C 0.8302(4) 0.5782(2) 0.5907(3) 0.0405(7) Uani 1 1 d . . . . .
H5 H 0.8654 0.6405 0.5960 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7587(4) 0.5434(2) 0.4773(3) 0.0345(6) Uani 1 1 d . . . . .
C7 C 0.7339(4) 0.60633(19) 0.3694(3) 0.0349(6) Uani 1 1 d . . . . .
C8 C 0.6983(4) 0.5769(2) 0.2468(3) 0.0408(7) Uani 1 1 d . . . . .
H8 H 0.6805 0.5137 0.2295 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6893(4) 0.6421(2) 0.1502(3) 0.0398(7) Uani 1 1 d . . . . .
C10 C 0.6753(5) 0.6151(3) 0.0155(3) 0.0544(9) Uani 1 1 d . . . . .
H10A H 0.5669 0.6385 -0.0211 0.082 Uiso 1 1 calc R U . . .
H10B H 0.6775 0.5480 0.0085 0.082 Uiso 1 1 calc R U . . .
H10C H 0.7725 0.6411 -0.0283 0.082 Uiso 1 1 calc R U . . .
B1 B 0.7055(6) 0.7695(3) 0.3024(4) 0.0479(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C3 2.092(3) . ?
F1 B1 1.368(5) . ?
F2 B1 1.353(5) . ?
O1 C9 1.289(4) . ?
O1 B1 1.494(4) . ?
O2 C7 1.304(4) . ?
O2 B1 1.484(4) . ?
C1 C2 1.390(5) . ?
C1 C6 1.391(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.463(4) . ?
C7 C8 1.385(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.482(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C9 O1 B1 121.8(2) . . ?
C7 O2 B1 122.3(2) . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 I1 120.2(2) . . ?
C4 C3 I1 118.7(2) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 121.2(3) . . ?
C5 C6 C7 119.6(3) . . ?
O2 C7 C8 120.6(3) . . ?
O2 C7 C6 114.9(2) . . ?
C8 C7 C6 124.4(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O1 C9 C8 122.0(3) . . ?
O1 C9 C10 115.3(3) . . ?
C8 C9 C10 122.7(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 B1 F1 112.3(3) . . ?
F2 B1 O2 108.5(3) . . ?
F1 B1 O2 107.8(3) . . ?
F2 B1 O1 108.9(3) . . ?
F1 B1 O1 108.6(3) . . ?
O2 B1 O1 110.7(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
C6 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 I1 178.6(2) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
I1 C3 C4 C5 -177.9(2) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
C2 C1 C6 C7 -177.0(3) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
B1 O2 C7 C8 10.7(4) . . . . ?
B1 O2 C7 C6 -170.7(3) . . . . ?
C1 C6 C7 O2 166.3(3) . . . . ?
C5 C6 C7 O2 -12.1(4) . . . . ?
C1 C6 C7 C8 -15.1(5) . . . . ?
C5 C6 C7 C8 166.4(3) . . . . ?
O2 C7 C8 C9 2.9(5) . . . . ?
C6 C7 C8 C9 -175.5(3) . . . . ?
B1 O1 C9 C8 -5.3(5) . . . . ?
B1 O1 C9 C10 177.1(3) . . . . ?
C7 C8 C9 O1 -5.6(5) . . . . ?
C7 C8 C9 C10 171.7(3) . . . . ?
C7 O2 B1 F2 -138.9(3) . . . . ?
C7 O2 B1 F1 99.2(3) . . . . ?
C7 O2 B1 O1 -19.5(5) . . . . ?
C9 O1 B1 F2 135.9(3) . . . . ?
C9 O1 B1 F1 -101.5(3) . . . . ?
C9 O1 B1 O2 16.7(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
C10 H10A F2 0.96 2.52 3.424(4) 156.8 4_575
C8 H8 F2 0.93 2.56 3.483(4) 173.3 2_645
C4 H4 F1 0.93 2.52 3.225(4) 133.0 4_676

_refine_diff_density_max         1.001
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4

