# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_sv546_cf3
_database_code_depnum_ccdc_archive 'CCDC 1816153'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2017-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H7 B F5 N O3'
_chemical_formula_sum            'C8 H7 B F5 N O3'
_chemical_formula_weight         270.96
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1877(5)
_cell_length_b                   8.3211(6)
_cell_length_c                   11.0677(8)
_cell_angle_alpha                92.0770(10)
_cell_angle_beta                 102.3770(10)
_cell_angle_gamma                104.5810(10)
_cell_volume                     536.23(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5447
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1100 before and 0.0350 after correction. The Ratio of minimum to maximum transmission is 0.9105. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10478
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.731
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2889
_reflns_number_total             3302
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72978(10) 0.13741(8) 0.54456(6) 0.02113(14) Uani 1 1 d . . . . .
F2 F 0.51884(11) 0.14164(8) 0.68993(6) 0.02404(14) Uani 1 1 d . . . . .
F3 F 1.00774(14) 0.29052(9) 0.79653(8) 0.0401(2) Uani 1 1 d . . . . .
F4 F 1.03115(13) 0.45428(10) 0.65018(7) 0.03769(19) Uani 1 1 d . . . . .
F5 F 0.83345(12) 0.48419(8) 0.78350(6) 0.02826(16) Uani 1 1 d . . . . .
O1 O 0.53920(12) 0.35149(8) 0.54905(6) 0.01702(14) Uani 1 1 d . . . . .
O2 O 0.27373(17) 0.10932(14) 0.01572(8) 0.0426(3) Uani 1 1 d . . . . .
O3 O 0.59861(15) 0.29069(13) 0.12039(7) 0.0357(2) Uani 1 1 d . . . . .
N1 N 0.38691(13) 0.27110(10) 0.44208(7) 0.01487(15) Uani 1 1 d . . . . .
C1 C 0.46428(16) 0.27167(12) 0.33758(8) 0.01632(17) Uani 1 1 d . . . . .
H1 H 0.618(2) 0.3250(17) 0.3468(13) 0.020(3) Uiso 1 1 d . . . . .
C2 C 0.31367(16) 0.19069(12) 0.22893(9) 0.01737(18) Uani 1 1 d . . . . .
C3 C 0.08644(17) 0.11212(12) 0.22953(9) 0.01874(18) Uani 1 1 d . . . . .
H3 H -0.012(3) 0.0569(19) 0.1558(14) 0.027(4) Uiso 1 1 d . . . . .
C4 C 0.01330(17) 0.12018(12) 0.33938(10) 0.01999(19) Uani 1 1 d . . . . .
H4 H -0.138(3) 0.0695(18) 0.3424(13) 0.025(3) Uiso 1 1 d . . . . .
C5 C 0.16781(16) 0.20143(12) 0.44644(9) 0.01836(18) Uani 1 1 d . . . . .
H5 H 0.133(3) 0.2116(19) 0.5258(15) 0.032(4) Uiso 1 1 d . . . . .
C6 C 0.88313(17) 0.36686(12) 0.71400(9) 0.01912(18) Uani 1 1 d . . . . .
C7 C 0.38991(18) 0.19050(14) 0.10950(9) 0.0236(2) Uani 1 1 d . . . . .
C8 C 0.6788(3) 0.3062(2) 0.00580(12) 0.0455(4) Uani 1 1 d . . . . .
H8A H 0.690(4) 0.201(3) -0.025(2) 0.070(7) Uiso 1 1 d . . . . .
H8B H 0.568(4) 0.331(2) -0.0572(19) 0.053(5) Uiso 1 1 d . . . . .
H8C H 0.817(4) 0.393(3) 0.027(2) 0.071(7) Uiso 1 1 d . . . . .
B1 B 0.65951(17) 0.23797(13) 0.62318(9) 0.01481(18) 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
F1 B1 1.3924(11) . ?
F2 B1 1.3832(11) . ?
F3 C6 1.3487(11) . ?
F4 C6 1.3587(12) . ?
F5 C6 1.3555(11) . ?
O1 N1 1.3726(10) . ?
O1 B1 1.5060(12) . ?
O2 C7 1.1980(13) . ?
O3 C7 1.3271(13) . ?
O3 C8 1.4564(14) . ?
N1 C1 1.3429(12) . ?
N1 C5 1.3457(12) . ?
C1 C2 1.3832(13) . ?
C2 C3 1.3950(13) . ?
C2 C7 1.4958(14) . ?
C3 C4 1.3902(14) . ?
C4 C5 1.3806(14) . ?
C6 B1 1.6290(14) . ?

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
N1 O1 B1 112.94(7) . . ?
C7 O3 C8 115.29(9) . . ?
C1 N1 O1 117.70(8) . . ?
C1 N1 C5 123.66(8) . . ?
C5 N1 O1 118.60(8) . . ?
N1 C1 C2 118.56(9) . . ?
C1 C2 C3 119.89(9) . . ?
C1 C2 C7 120.68(9) . . ?
C3 C2 C7 119.40(9) . . ?
C4 C3 C2 119.19(9) . . ?
C5 C4 C3 119.57(9) . . ?
N1 C5 C4 119.06(9) . . ?
F3 C6 F4 105.79(9) . . ?
F3 C6 F5 105.05(8) . . ?
F3 C6 B1 113.26(8) . . ?
F4 C6 B1 112.58(8) . . ?
F5 C6 F4 104.99(8) . . ?
F5 C6 B1 114.35(8) . . ?
O2 C7 O3 124.73(10) . . ?
O2 C7 C2 123.26(10) . . ?
O3 C7 C2 112.01(9) . . ?
F1 B1 O1 110.02(7) . . ?
F1 B1 C6 109.78(8) . . ?
F2 B1 F1 110.68(8) . . ?
F2 B1 O1 110.89(8) . . ?
F2 B1 C6 111.84(8) . . ?
O1 B1 C6 103.40(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_vs2
_database_code_depnum_ccdc_archive 'CCDC 1816154'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-02-05 downloaded from the CCDC.
;
_audit_creation_date             2017-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 B F9 N O3'
_chemical_formula_sum            'C10 H7 B F9 N O3'
_chemical_formula_weight         370.98
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3594(7)
_cell_length_b                   8.1912(4)
_cell_length_c                   12.4704(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.6960(10)
_cell_angle_gamma                90
_cell_volume                     1352.34(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8514
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.518
_cell_measurement_theta_min      2.925
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0746 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.9217. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19148
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.534
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3788
_reflns_number_total             4480
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.3502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.10258(4) 0.64462(8) 0.49487(5) 0.02961(14) Uani 1 1 d . . . . .
F2 F 0.23919(5) 0.70434(8) 0.41183(5) 0.02753(14) Uani 1 1 d . . . . .
F3 F 0.23576(5) 0.47165(8) 0.66484(5) 0.02665(13) Uani 1 1 d . . . . .
F4 F 0.25224(5) 0.73788(8) 0.65698(5) 0.02997(14) Uani 1 1 d . . . . .
F5 F 0.40298(5) 0.45090(8) 0.54445(5) 0.02877(14) Uani 1 1 d . . . . .
F6 F 0.42099(5) 0.71439(8) 0.56903(5) 0.03026(15) Uani 1 1 d . . . . .
F7 F 0.42248(6) 0.40036(10) 0.75868(6) 0.04168(19) Uani 1 1 d . . . . .
F8 F 0.54309(5) 0.54644(11) 0.71068(7) 0.04199(19) Uani 1 1 d . . . . .
F9 F 0.42725(6) 0.65902(10) 0.79089(6) 0.04019(18) Uani 1 1 d . . . . .
O1 O 0.20165(5) 0.42687(8) 0.44197(5) 0.02181(14) Uani 1 1 d . . . . .
O2 O 0.14497(6) 0.42142(9) -0.03634(6) 0.02639(15) Uani 1 1 d . . . . .
O3 O 0.29159(5) 0.40779(9) 0.07653(6) 0.02406(15) Uani 1 1 d . . . . .
N1 N 0.14643(6) 0.41150(10) 0.34150(6) 0.01945(15) Uani 1 1 d . . . . .
C1 C 0.19590(7) 0.41999(11) 0.25508(7) 0.01917(16) Uani 1 1 d . . . . .
H1 H 0.2668 0.4374 0.2635 0.023 Uiso 1 1 calc R . . . .
C2 C 0.14123(7) 0.40274(11) 0.15305(7) 0.01906(16) Uani 1 1 d . . . . .
C3 C 0.03730(7) 0.37849(12) 0.14296(8) 0.02221(18) Uani 1 1 d . . . . .
H3 H -0.0010 0.3693 0.0733 0.027 Uiso 1 1 calc R . . . .
C4 C -0.01015(7) 0.36780(13) 0.23497(9) 0.02560(19) Uani 1 1 d . . . . .
H4 H -0.0809 0.3495 0.2289 0.031 Uiso 1 1 calc R . . . .
C5 C 0.04617(7) 0.38393(12) 0.33543(8) 0.02379(18) Uani 1 1 d . . . . .
H5 H 0.0150 0.3758 0.3993 0.029 Uiso 1 1 calc R . . . .
C6 C 0.26832(7) 0.59548(11) 0.60300(7) 0.01825(16) Uani 1 1 d . . . . .
C7 C 0.38343(7) 0.57717(11) 0.60806(7) 0.01949(16) Uani 1 1 d . . . . .
C8 C 0.44463(8) 0.54519(15) 0.71973(9) 0.0286(2) Uani 1 1 d . . . . .
C9 C 0.19185(7) 0.41192(11) 0.05313(8) 0.02028(17) Uani 1 1 d . . . . .
C10 C 0.34668(8) 0.41919(13) -0.01573(9) 0.0279(2) Uani 1 1 d . . . . .
H10A H 0.3291 0.3263 -0.0641 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.4194 0.4178 0.0093 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.3288 0.5212 -0.0548 0.042 Uiso 1 1 calc GR . . . .
B1 B 0.20140(8) 0.59970(12) 0.48301(8) 0.01964(18) 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
F1 B1 1.3974(12) . ?
F2 B1 1.3775(12) . ?
F3 C6 1.3793(10) . ?
F4 C6 1.3779(10) . ?
F5 C7 1.3501(11) . ?
F6 C7 1.3481(11) . ?
F7 C8 1.3302(14) . ?
F8 C8 1.3352(13) . ?
F9 C8 1.3289(14) . ?
O1 N1 1.3720(10) . ?
O1 B1 1.5055(12) . ?
O2 C9 1.2067(12) . ?
O3 C9 1.3257(11) . ?
O3 C10 1.4494(12) . ?
N1 C1 1.3393(12) . ?
N1 C5 1.3503(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.3869(12) . ?
C2 C3 1.3915(12) . ?
C2 C9 1.4970(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.3859(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3787(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.5379(13) . ?
C6 B1 1.6373(14) . ?
C7 C8 1.5400(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 B1 111.80(7) . . ?
C9 O3 C10 115.21(8) . . ?
C1 N1 O1 117.85(7) . . ?
C1 N1 C5 123.80(8) . . ?
C5 N1 O1 118.33(8) . . ?
N1 C1 H1 120.8 . . ?
N1 C1 C2 118.49(8) . . ?
C2 C1 H1 120.8 . . ?
C1 C2 C3 119.60(9) . . ?
C1 C2 C9 121.16(8) . . ?
C3 C2 C9 119.24(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.71(8) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.46(9) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 118.91(9) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
F3 C6 C7 107.09(7) . . ?
F3 C6 B1 110.61(7) . . ?
F4 C6 F3 105.54(7) . . ?
F4 C6 C7 106.43(7) . . ?
F4 C6 B1 109.08(7) . . ?
C7 C6 B1 117.40(7) . . ?
F5 C7 C6 108.76(7) . . ?
F5 C7 C8 106.26(8) . . ?
F6 C7 F5 108.42(8) . . ?
F6 C7 C6 108.80(7) . . ?
F6 C7 C8 106.86(8) . . ?
C6 C7 C8 117.42(8) . . ?
F7 C8 F8 107.91(9) . . ?
F7 C8 C7 111.39(9) . . ?
F8 C8 C7 109.39(9) . . ?
F9 C8 F7 108.34(10) . . ?
F9 C8 F8 108.26(9) . . ?
F9 C8 C7 111.43(9) . . ?
O2 C9 O3 125.94(9) . . ?
O2 C9 C2 122.45(9) . . ?
O3 C9 C2 111.61(8) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F1 B1 O1 109.19(8) . . ?
F1 B1 C6 108.47(8) . . ?
F2 B1 F1 109.71(8) . . ?
F2 B1 O1 110.39(8) . . ?
F2 B1 C6 113.56(8) . . ?
O1 B1 C6 105.37(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
