# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_200715
_database_code_depnum_ccdc_archive 'CCDC 2080664'
loop_
_audit_author_name
_audit_author_address
'Fumitoshi Maruyama'
;Gifu University
Japan
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 B F2 N4 S'
_chemical_formula_sum            'C20 H15 B F2 N4 S'
_chemical_formula_weight         392.23

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.9896(2)
_cell_length_b                   9.2646(3)
_cell_length_c                   13.4601(4)
_cell_angle_alpha                105.166(3)
_cell_angle_beta                 96.037(2)
_cell_angle_gamma                108.811(3)
_cell_volume                     890.46(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2266
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       'profile data from φ-scans'
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            8310
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4063
_reflns_number_gt                2984
_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       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0537P)²+0.1258P] 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         4063
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 0.96006(6) 0.71408(5) 0.45412(3) 0.05012(16) Uani 1 1 d . . . . .
F1 F 1.35970(15) 0.78966(14) 0.23464(10) 0.0707(4) Uani 1 1 d . . . . .
F2 F 1.19605(16) 0.89511(15) 0.14794(8) 0.0695(4) Uani 1 1 d . . . . .
N1 N 1.22514(18) 0.97442(17) 0.56698(11) 0.0450(3) Uani 1 1 d . . . . .
N2 N 1.07943(19) 0.79487(17) 0.28426(11) 0.0470(4) Uani 1 1 d . . . . .
N3 N 0.8999(2) 0.6959(2) 0.65808(13) 0.0608(4) Uani 1 1 d . . . . .
N4 N 1.35773(19) 1.04810(17) 0.32691(11) 0.0462(4) Uani 1 1 d . . . . .
C1 C 1.0931(2) 0.8545(2) 0.57422(13) 0.0444(4) Uani 1 1 d . . . . .
C2 C 1.0950(2) 0.82918(19) 0.38980(13) 0.0428(4) Uani 1 1 d . . . . .
C3 C 1.2298(2) 0.9622(2) 0.46302(13) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.9237(2) 0.6661(2) 0.21538(13) 0.0478(4) Uani 1 1 d . . . . .
C5 C 0.7508(2) 0.6570(2) 0.22743(14) 0.0518(5) Uani 1 1 d . . . . .
H5 H 0.7344 0.7370 0.2793 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6024(3) 0.5284(2) 0.16209(15) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.4869 0.5230 0.1710 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6223(3) 0.4072(2) 0.08364(15) 0.0603(5) Uani 1 1 d . . . . .
C8 C 0.7947(3) 0.4222(2) 0.07037(16) 0.0678(6) Uani 1 1 d . . . . .
H8 H 0.8109 0.3450 0.0163 0.081 Uiso 1 1 calc R U . . .
C9 C 0.9451(3) 0.5494(2) 0.13540(16) 0.0621(5) Uani 1 1 d . . . . .
H9 H 1.0603 0.5560 0.1251 0.075 Uiso 1 1 calc R U . . .
C10 C 0.4614(3) 0.2627(3) 0.01472(18) 0.0833(8) Uani 1 1 d . . . . .
H10 H 0.4942 0.2142 -0.0487 0.125 Uiso 1 1 calc R U . . .
H10A H 0.3633 0.2961 -0.0027 0.125 Uiso 1 1 calc R U . . .
H10B H 0.4247 0.1861 0.0519 0.125 Uiso 1 1 calc R U . . .
C11 C 1.0451(2) 0.8278(2) 0.67106(14) 0.0475(4) Uani 1 1 d . . . . .
C12 C 1.1428(3) 0.9313(2) 0.76985(15) 0.0579(5) Uani 1 1 d . . . . .
H12 H 1.2443 1.0207 0.7765 0.069 Uiso 1 1 calc R U . . .
C13 C 1.0872(3) 0.8995(3) 0.85734(17) 0.0698(6) Uani 1 1 d . . . . .
H13 H 1.1495 0.9681 0.9243 0.084 Uiso 1 1 calc R U . . .
C14 C 0.9380(3) 0.7651(3) 0.84490(18) 0.0726(6) Uani 1 1 d . . . . .
H14 H 0.8977 0.7405 0.9029 0.087 Uiso 1 1 calc R U . . .
C15 C 0.8504(3) 0.6681(3) 0.74441(18) 0.0738(6) Uani 1 1 d . . . . .
H15 H 0.7498 0.5771 0.7364 0.089 Uiso 1 1 calc R U . . .
C16 C 1.3576(2) 1.0810(2) 0.43157(13) 0.0429(4) Uani 1 1 d . . . . .
C17 C 1.4776(2) 1.2282(2) 0.50242(15) 0.0495(4) Uani 1 1 d . . . . .
H17 H 1.4795 1.2507 0.5741 0.059 Uiso 1 1 calc R U . . .
C18 C 1.5916(2) 1.3384(2) 0.46586(16) 0.0550(5) Uani 1 1 d . . . . .
H18 H 1.6717 1.4358 0.5126 0.066 Uiso 1 1 calc R U . . .
C19 C 1.5870(3) 1.3039(2) 0.35849(16) 0.0585(5) Uani 1 1 d . . . . .
H19 H 1.6621 1.3785 0.3324 0.070 Uiso 1 1 calc R U . . .
C20 C 1.4706(2) 1.1590(2) 0.29190(16) 0.0549(5) Uani 1 1 d . . . . .
H20 H 1.4687 1.1355 0.2202 0.066 Uiso 1 1 calc R U . . .
B1 B 1.2449(3) 0.8746(3) 0.24291(16) 0.0511(5) 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
S1 C2 1.7283(18) . ?
S1 C1 1.7557(17) . ?
F1 B1 1.384(3) . ?
F2 B1 1.375(2) . ?
N1 C1 1.296(2) . ?
N1 C3 1.379(2) . ?
N2 C2 1.355(2) . ?
N2 C4 1.433(2) . ?
N2 B1 1.531(3) . ?
N3 C15 1.327(3) . ?
N3 C11 1.342(2) . ?
N4 C20 1.355(2) . ?
N4 C16 1.361(2) . ?
C1 C11 1.456(3) . ?
C2 C3 1.391(2) . ?
C3 C16 1.430(2) . ?
C4 C9 1.381(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.386(2) . ?
C6 C7 1.389(3) . ?
C7 C8 1.374(3) . ?
C7 C10 1.515(3) . ?
C8 C9 1.387(3) . ?
C11 C12 1.389(2) . ?
C12 C13 1.370(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.373(3) . ?
C16 C17 1.404(2) . ?
C17 C18 1.368(3) . ?
C18 C19 1.390(3) . ?
C19 C20 1.364(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
C2 S1 C1 88.61(8) . . ?
C1 N1 C3 110.78(14) . . ?
C2 N2 C4 119.55(15) . . ?
C2 N2 B1 118.04(14) . . ?
C4 N2 B1 121.44(14) . . ?
C15 N3 C11 117.15(17) . . ?
C20 N4 C16 119.73(15) . . ?
N1 C1 C11 126.37(15) . . ?
N1 C1 S1 115.54(14) . . ?
C11 C1 S1 118.09(12) . . ?
N2 C2 C3 123.95(16) . . ?
N2 C2 S1 126.24(12) . . ?
C3 C2 S1 109.77(13) . . ?
N1 C3 C2 115.28(15) . . ?
N1 C3 C16 122.92(14) . . ?
C2 C3 C16 121.72(16) . . ?
C9 C4 C5 119.22(16) . . ?
C9 C4 N2 119.85(17) . . ?
C5 C4 N2 120.93(16) . . ?
C4 C5 C6 119.88(19) . . ?
C5 C6 C7 121.5(2) . . ?
C8 C7 C6 117.62(17) . . ?
C8 C7 C10 120.5(2) . . ?
C6 C7 C10 121.9(2) . . ?
C7 C8 C9 121.8(2) . . ?
C4 C9 C8 120.0(2) . . ?
N3 C11 C12 122.36(18) . . ?
N3 C11 C1 115.24(16) . . ?
C12 C11 C1 122.40(17) . . ?
C13 C12 C11 118.96(19) . . ?
C12 C13 C14 119.1(2) . . ?
C15 C14 C13 118.2(2) . . ?
N3 C15 C14 124.2(2) . . ?
N4 C16 C17 119.59(16) . . ?
N4 C16 C3 117.05(14) . . ?
C17 C16 C3 123.35(17) . . ?
C18 C17 C16 119.95(18) . . ?
C17 C18 C19 119.57(17) . . ?
C20 C19 C18 119.04(18) . . ?
N4 C20 C19 122.11(19) . . ?
F2 B1 F1 110.26(17) . . ?
F2 B1 N2 111.68(16) . . ?
F1 B1 N2 111.77(17) . . ?

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
C3 N1 C1 C11 -179.31(17) . . . . ?
C3 N1 C1 S1 -0.2(2) . . . . ?
C2 S1 C1 N1 -0.32(15) . . . . ?
C2 S1 C1 C11 178.91(15) . . . . ?
C4 N2 C2 C3 -172.50(17) . . . . ?
B1 N2 C2 C3 18.6(3) . . . . ?
C4 N2 C2 S1 10.2(2) . . . . ?
B1 N2 C2 S1 -158.69(14) . . . . ?
C1 S1 C2 N2 178.31(16) . . . . ?
C1 S1 C2 C3 0.69(14) . . . . ?
C1 N1 C3 C2 0.7(2) . . . . ?
C1 N1 C3 C16 177.69(16) . . . . ?
N2 C2 C3 N1 -178.65(16) . . . . ?
S1 C2 C3 N1 -1.0(2) . . . . ?
N2 C2 C3 C16 4.4(3) . . . . ?
S1 C2 C3 C16 -177.96(14) . . . . ?
C2 N2 C4 C9 -128.9(2) . . . . ?
B1 N2 C4 C9 39.6(3) . . . . ?
C2 N2 C4 C5 51.4(2) . . . . ?
B1 N2 C4 C5 -140.14(19) . . . . ?
C9 C4 C5 C6 2.4(3) . . . . ?
N2 C4 C5 C6 -177.83(17) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -2.3(3) . . . . ?
C5 C6 C7 C10 177.44(18) . . . . ?
C6 C7 C8 C9 2.8(3) . . . . ?
C10 C7 C8 C9 -177.0(2) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
N2 C4 C9 C8 178.27(18) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C15 N3 C11 C12 0.9(3) . . . . ?
C15 N3 C11 C1 -179.25(18) . . . . ?
N1 C1 C11 N3 178.75(18) . . . . ?
S1 C1 C11 N3 -0.4(2) . . . . ?
N1 C1 C11 C12 -1.4(3) . . . . ?
S1 C1 C11 C12 179.47(15) . . . . ?
N3 C11 C12 C13 -1.3(3) . . . . ?
C1 C11 C12 C13 178.84(19) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C11 N3 C15 C14 -0.1(4) . . . . ?
C13 C14 C15 N3 -0.2(4) . . . . ?
C20 N4 C16 C17 -1.5(3) . . . . ?
C20 N4 C16 C3 177.24(16) . . . . ?
N1 C3 C16 N4 174.60(15) . . . . ?
C2 C3 C16 N4 -8.6(3) . . . . ?
N1 C3 C16 C17 -6.7(3) . . . . ?
C2 C3 C16 C17 170.02(17) . . . . ?
N4 C16 C17 C18 1.0(3) . . . . ?
C3 C16 C17 C18 -177.62(17) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C16 N4 C20 C19 0.6(3) . . . . ?
C18 C19 C20 N4 0.7(3) . . . . ?
C2 N2 B1 F2 -151.04(16) . . . . ?
C4 N2 B1 F2 40.3(2) . . . . ?
C2 N2 B1 F1 84.90(19) . . . . ?
C4 N2 B1 F1 -83.8(2) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039

