# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_yuk25
_database_code_depnum_ccdc_archive 'CCDC 1921472'
loop_
_audit_author_name
_audit_author_address
'Alexander Volodin'
;INEOS
Russia
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H6 B F7 O2'
_chemical_formula_sum            'C15 H6 B F7 O2'
_chemical_formula_weight         362.01
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.084(4)
_cell_length_b                   13.499(6)
_cell_length_c                   10.890(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.210(10)
_cell_angle_gamma                90
_cell_volume                     1391.1(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1373
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.680
_cell_measurement_theta_min      2.498
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0495 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8752. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8329
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.644
_diffrn_reflns_theta_min         2.375
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2730
_reflns_number_total             4170
_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         0.304
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.036
_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)+(0.0440P)²+0.2183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H8(0.024) H11(0.026) H12(0.028) H13(0.03) H14(0.032) H15(0.029)
 Fixed X: H8(0.7511) H11(0.9563) H12(1.1856) H13(1.3787) H14(1.3426) H15(1.1134)
 Fixed Y: H8(0.6621) H11(0.5958) H12(0.5332) H13(0.6414) H14(0.8122) H15(0.8759)
 Fixed Z: H8(0.2911) H11(0.3999) H12(0.4821) H13(0.5458) H14(0.5239) H15(0.4464)
;
_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 0.35407(11) 0.85541(8) 0.13701(11) 0.0265(3) Uani 1 1 d . . . . .
F2 F 0.10810(11) 0.76040(10) 0.07389(12) 0.0335(3) Uani 1 1 d . . . . .
F3 F 0.09788(12) 0.56958(10) 0.14919(12) 0.0373(3) Uani 1 1 d . . . . .
F4 F 0.34097(13) 0.47483(9) 0.29295(13) 0.0373(3) Uani 1 1 d . . . . .
F5 F 0.58603(11) 0.56998(8) 0.36857(12) 0.0280(3) Uani 1 1 d . . . . .
F6 F 0.71848(12) 0.98893(9) 0.24970(11) 0.0313(3) Uani 1 1 d . . . . .
F7 F 0.72357(12) 0.99340(9) 0.45899(11) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.60405(13) 0.86530(9) 0.32562(13) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.86149(13) 0.87786(9) 0.40132(14) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.48147(18) 0.71677(13) 0.25525(17) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.35515(19) 0.76259(14) 0.18086(17) 0.0200(4) Uani 1 1 d . . . . .
C3 C 0.22737(18) 0.71354(15) 0.14558(18) 0.0238(4) Uani 1 1 d . . . . .
C4 C 0.22164(19) 0.61667(16) 0.18264(19) 0.0258(4) Uani 1 1 d . . . . .
C5 C 0.3444(2) 0.56862(14) 0.25490(19) 0.0245(4) Uani 1 1 d . . . . .
C6 C 0.47161(19) 0.61904(14) 0.29099(18) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.61715(18) 0.77212(13) 0.29986(17) 0.0187(4) Uani 1 1 d . . . . .
C8 C 0.74573(18) 0.72864(14) 0.31758(18) 0.0199(4) Uani 1 1 d . . . . .
H8 H 0.7511 0.6621 0.2911 0.024 Uiso 1 1 calc R . . . .
C9 C 0.86870(18) 0.78460(13) 0.37551(17) 0.0188(4) Uani 1 1 d . . . . .
C10 C 1.01204(18) 0.74213(13) 0.41768(17) 0.0193(4) Uani 1 1 d . . . . .
C11 C 1.03454(19) 0.63982(14) 0.42674(18) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.9563 0.5958 0.3999 0.026 Uiso 1 1 calc R . . . .
C12 C 1.17050(19) 0.60276(15) 0.47468(18) 0.0237(4) Uani 1 1 d . . . . .
H12 H 1.1856 0.5332 0.4821 0.028 Uiso 1 1 calc R . . . .
C13 C 1.28532(19) 0.66707(15) 0.51203(19) 0.0250(4) Uani 1 1 d . . . . .
H13 H 1.3787 0.6414 0.5458 0.030 Uiso 1 1 calc R . . . .
C14 C 1.2639(2) 0.76857(15) 0.5002(2) 0.0267(4) Uani 1 1 d . . . . .
H14 H 1.3426 0.8122 0.5239 0.032 Uiso 1 1 calc R . . . .
C15 C 1.12796(19) 0.80632(15) 0.45374(19) 0.0244(4) Uani 1 1 d . . . . .
H15 H 1.1134 0.8759 0.4464 0.029 Uiso 1 1 calc R . . . .
B1 B 0.7258(2) 0.93483(15) 0.3578(2) 0.0213(4) 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 C2 1.340(2) . ?
F2 C3 1.344(2) . ?
F3 C4 1.334(2) . ?
F4 C5 1.336(2) . ?
F5 C6 1.345(2) . ?
F6 B1 1.365(2) . ?
F7 B1 1.363(2) . ?
O1 C7 1.305(2) . ?
O1 B1 1.488(2) . ?
O2 C9 1.297(2) . ?
O2 B1 1.496(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.389(3) . ?
C1 C7 1.486(2) . ?
C2 C3 1.380(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.384(3) . ?
C7 C8 1.375(2) . ?
C8 C9 1.402(2) . ?
C9 C10 1.473(2) . ?
C10 C11 1.397(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.384(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
C7 O1 B1 121.45(14) . . ?
C9 O2 B1 122.92(14) . . ?
C2 C1 C7 121.31(16) . . ?
C6 C1 C2 116.37(16) . . ?
C6 C1 C7 122.22(16) . . ?
F1 C2 C1 120.98(16) . . ?
F1 C2 C3 117.24(16) . . ?
C3 C2 C1 121.74(18) . . ?
F2 C3 C2 119.86(18) . . ?
F2 C3 C4 119.85(16) . . ?
C4 C3 C2 120.28(17) . . ?
F3 C4 C3 120.19(18) . . ?
F3 C4 C5 120.18(19) . . ?
C3 C4 C5 119.63(17) . . ?
F4 C5 C4 120.57(16) . . ?
F4 C5 C6 119.91(17) . . ?
C4 C5 C6 119.50(18) . . ?
F5 C6 C1 120.98(16) . . ?
F5 C6 C5 116.48(17) . . ?
C5 C6 C1 122.46(17) . . ?
O1 C7 C1 113.88(15) . . ?
O1 C7 C8 122.80(16) . . ?
C8 C7 C1 123.27(17) . . ?
C7 C8 C9 118.54(17) . . ?
O2 C9 C8 120.88(16) . . ?
O2 C9 C10 115.62(15) . . ?
C8 C9 C10 123.41(16) . . ?
C11 C10 C9 121.63(16) . . ?
C11 C10 C15 119.55(17) . . ?
C15 C10 C9 118.78(17) . . ?
C12 C11 C10 120.02(17) . . ?
C11 C12 C13 120.12(19) . . ?
C14 C13 C12 120.18(18) . . ?
C15 C14 C13 120.04(18) . . ?
C14 C15 C10 120.06(18) . . ?
F6 B1 O1 109.88(16) . . ?
F6 B1 O2 108.65(16) . . ?
F7 B1 F6 112.07(17) . . ?
F7 B1 O1 108.23(16) . . ?
F7 B1 O2 108.09(16) . . ?
O1 B1 O2 109.89(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
