# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1957640'
loop_
_audit_author_name
_audit_author_address
'Satoru Saotome'
;Kyoto University
Japan
;
_audit_update_record             
;
2019-10-05 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 B F2 N O S'
_chemical_formula_weight         327.15

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'
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'
S S 0.1246 0.1234 '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'
B B 0.0013 0.0007 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.3895(5)
_cell_length_b                   10.0595(8)
_cell_length_c                   17.3911(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.872(7)
_cell_angle_gamma                90
_cell_volume                     1441.36(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    11216
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3573
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID F'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13833
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3307
_reflns_number_gt                2718
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+3.2714P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3307
_refine_ls_number_parameters     255
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.2127
_refine_ls_wR_factor_gt          0.2019
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
B1 B 0.8150(5) 0.6454(4) 0.4812(2) 0.0304(8) Uani 1 1 d . . . . .
F1 F 0.9777(2) 0.6783(2) 0.49892(12) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.7732(4) 0.6057(3) 0.39971(14) 0.0392(6) Uani 1 1 d . . . . .
N1 N 0.7828(3) 0.5277(3) 0.53651(16) 0.0287(6) Uani 1 1 d . . . . .
C1 C 0.6236(4) 0.4993(3) 0.2880(2) 0.0318(7) Uani 1 1 d . . . . .
C2 C 0.6922(5) 0.5866(4) 0.2400(2) 0.0393(9) Uani 1 1 d . . . . .
H2 H 0.773197 0.645414 0.262614 0.047 Uiso 1 1 calc R U . . .
F2 F 0.7218(2) 0.7523(2) 0.49702(11) 0.0327(5) Uani 1 1 d . . . . .
C3 C 0.6415(5) 0.5861(4) 0.1604(2) 0.0447(10) Uani 1 1 d . . . . .
H3 H 0.688205 0.644368 0.129521 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5203(5) 0.4990(4) 0.1254(2) 0.0416(9) Uani 1 1 d . . . . .
H4 H 0.484684 0.499230 0.071456 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4534(5) 0.4117(4) 0.1724(2) 0.0377(8) Uani 1 1 d . . . . .
H5 H 0.373545 0.352228 0.149578 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5037(5) 0.4122(4) 0.2523(2) 0.0363(8) Uani 1 1 d . . . . .
H6 H 0.456911 0.353477 0.282902 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6766(4) 0.5046(3) 0.3745(2) 0.0292(7) Uani 1 1 d . . . . .
C8 C 0.6341(4) 0.4129(4) 0.4246(2) 0.0312(7) Uani 1 1 d . . . . .
H8 H 0.565642 0.343330 0.404613 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6923(4) 0.4211(3) 0.50703(19) 0.0273(7) Uani 1 1 d . . . . .
C10 C 0.6617(4) 0.3227(4) 0.5599(2) 0.0337(8) Uani 1 1 d . . . . .
H10 H 0.600522 0.248424 0.541094 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7206(5) 0.3345(4) 0.6384(2) 0.0342(8) Uani 1 1 d . . . . .
H11 H 0.698281 0.268817 0.672534 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8152(4) 0.4457(3) 0.6682(2) 0.0322(7) Uani 1 1 d . U . . .
C13 C 0.8428(4) 0.5386(4) 0.6141(2) 0.0322(7) Uani 1 1 d . . . . .
H13 H 0.905783 0.612464 0.631795 0.039 Uiso 1 1 calc R U . . .
C14A C 0.875(3) 0.467(2) 0.7558(8) 0.034(4) Uani 0.582(6) 1 d . U P A 1
C15A C 0.952(3) 0.590(3) 0.7881(14) 0.081(9) Uani 0.582(6) 1 d . U P A 1
H15A H 0.972761 0.666099 0.761292 0.097 Uiso 0.582(6) 1 calc R U P A 1
C16A C 0.988(3) 0.5666(19) 0.8705(11) 0.044(4) Uani 0.582(6) 1 d . U P A 1
H16A H 1.034408 0.631830 0.905668 0.053 Uiso 0.582(6) 1 calc R U P A 1
C17A C 0.951(5) 0.442(3) 0.8953(12) 0.043(4) Uani 0.582(6) 1 d . U P A 1
H17A H 0.972773 0.413943 0.947173 0.051 Uiso 0.582(6) 1 calc R U P A 1
S1A S 0.8634(6) 0.3476(3) 0.82032(17) 0.0356(7) Uani 0.582(6) 1 d . . P A 1
C14B C 0.876(3) 0.463(3) 0.7443(14) 0.033(4) Uani 0.418(6) 1 d . U P A 2
S1B S 0.9592(7) 0.5983(6) 0.7897(3) 0.0382(11) Uani 0.418(6) 1 d . U P A 2
C15B C 0.864(4) 0.374(3) 0.8070(16) 0.070(8) Uani 0.418(6) 1 d . U P A 2
H15B H 0.818230 0.289995 0.798325 0.084 Uiso 0.418(6) 1 calc R U P A 2
C16B C 0.927(7) 0.425(4) 0.886(2) 0.066(7) Uani 0.418(6) 1 d . U P A 2
H16B H 0.926106 0.379362 0.932790 0.079 Uiso 0.418(6) 1 calc R U P A 2
C17B C 0.988(5) 0.548(4) 0.8817(16) 0.058(6) Uani 0.418(6) 1 d . U P A 2
H17B H 1.038470 0.598245 0.924347 0.070 Uiso 0.418(6) 1 calc R U P A 2


_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
B1 F1 1.382(4) . ?
B1 F2 1.387(4) . ?
B1 O1 1.451(5) . ?
B1 N1 1.581(5) . ?
O1 C7 1.323(4) . ?
N1 C13 1.353(4) . ?
N1 C9 1.357(4) . ?
C1 C6 1.389(5) . ?
C1 C2 1.408(5) . ?
C1 C7 1.487(5) . ?
C2 C3 1.369(6) . ?
C3 C4 1.393(6) . ?
C4 C5 1.388(6) . ?
C5 C6 1.374(5) . ?
C7 C8 1.362(5) . ?
C8 C9 1.427(5) . ?
C9 C10 1.407(5) . ?
C10 C11 1.368(5) . ?
C11 C12 1.412(5) . ?
C12 C14B 1.34(2) . ?
C12 C13 1.375(5) . ?
C12 C14A 1.526(13) . ?
C14A C15A 1.46(3) . ?
C14A S1A 1.659(16) . ?
C15A C16A 1.43(3) . ?
C16A C17A 1.38(2) . ?
C17A S1A 1.667(17) . ?
C14B C15B 1.43(3) . ?
C14B S1B 1.66(3) . ?
S1B C17B 1.65(3) . ?
C15B C16B 1.48(4) . ?
C16B C17B 1.35(4) . ?

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
F1 B1 F2 109.9(3) . . ?
F1 B1 O1 109.3(3) . . ?
F2 B1 O1 111.5(3) . . ?
F1 B1 N1 108.6(3) . . ?
F2 B1 N1 107.0(3) . . ?
O1 B1 N1 110.5(3) . . ?
C7 O1 B1 123.7(3) . . ?
C13 N1 C9 121.1(3) . . ?
C13 N1 B1 118.1(3) . . ?
C9 N1 B1 120.7(3) . . ?
C6 C1 C2 118.1(3) . . ?
C6 C1 C7 121.9(3) . . ?
C2 C1 C7 120.0(3) . . ?
C3 C2 C1 120.9(4) . . ?
C2 C3 C4 120.4(4) . . ?
C5 C4 C3 118.9(3) . . ?
C6 C5 C4 120.8(4) . . ?
C5 C6 C1 120.8(4) . . ?
O1 C7 C8 121.8(3) . . ?
O1 C7 C1 114.2(3) . . ?
C8 C7 C1 123.9(3) . . ?
C7 C8 C9 121.5(3) . . ?
N1 C9 C10 117.8(3) . . ?
N1 C9 C8 119.1(3) . . ?
C10 C9 C8 123.1(3) . . ?
C11 C10 C9 121.0(3) . . ?
C10 C11 C12 120.4(3) . . ?
C14B C12 C13 120.4(11) . . ?
C14B C12 C11 123.2(11) . . ?
C13 C12 C11 116.3(3) . . ?
C13 C12 C14A 121.4(8) . . ?
C11 C12 C14A 122.1(8) . . ?
N1 C13 C12 123.2(3) . . ?
C15A C14A C12 122.8(15) . . ?
C15A C14A S1A 115.5(13) . . ?
C12 C14A S1A 121.7(13) . . ?
C16A C15A C14A 104.0(19) . . ?
C17A C16A C15A 116.4(17) . . ?
C16A C17A S1A 111.4(15) . . ?
C14A S1A C17A 92.5(10) . . ?
C12 C14B C15B 127(2) . . ?
C12 C14B S1B 128.6(18) . . ?
C15B C14B S1B 103.6(18) . . ?
C17B S1B C14B 100.4(15) . . ?
C14B C15B C16B 116(3) . . ?
C17B C16B C15B 110(3) . . ?
C16B C17B S1B 111(2) . . ?

_refine_diff_density_max         0.821
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.184



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
