# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_dDTCB
_database_code_depnum_ccdc_archive 'CCDC 2046285'
loop_
_audit_author_name
_audit_author_address
'Yohei Adachi'
;Hiroshima University
Japan
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
_chemical_name_systematic        dDTCB
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H12 B2 F18 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         936.32

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   27.083(3)
_cell_length_b                   8.0051(10)
_cell_length_c                   15.9067(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3448.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.6532
_cell_measurement_theta_max      27.8957
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'metallic dark brown'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856

_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            36923
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4135
_reflns_number_gt                3644
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0995
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_number_reflns         4135
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+5.4756P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.679
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.60863(8) 0.4631(3) 0.39194(13) 0.0137(4) Uani d . . . 1 . .
C C1 0.52433(7) 0.0580(3) 0.40351(13) 0.0177(4) Uani d . . . 1 . .
H H1 0.510368 -0.046255 0.419207 0.021 Uiso calc U . R 1 . .
C C2 0.50476(7) 0.1596(2) 0.34448(12) 0.0159(4) Uani d . . . 1 . .
H H2 0.474879 0.13606 0.315533 0.019 Uiso calc U . R 1 . .
C C3 0.57471(7) 0.3127(2) 0.38415(12) 0.0141(4) Uani d . . . 1 . .
C C4 0.53382(7) 0.3067(2) 0.33005(12) 0.0132(4) Uani d . . . 1 . .
C C5 0.52110(6) 0.4484(2) 0.27623(11) 0.0125(4) Uani d . . . 1 . .
C C6 0.55330(7) 0.5950(2) 0.27890(12) 0.0133(4) Uani d . . . 1 . .
C C7 0.59350(7) 0.6051(2) 0.33412(12) 0.0139(4) Uani d . . . 1 . .
C C8 0.55357(7) 0.7286(3) 0.21911(13) 0.0173(4) Uani d . . . 1 . .
H H8 0.529727 0.740285 0.175707 0.021 Uiso calc U . R 1 . .
C C9 0.59168(7) 0.8372(3) 0.23106(14) 0.0194(4) Uani d . . . 1 . .
H H9 0.597141 0.933681 0.197534 0.023 Uiso calc U . R 1 . .
C C10 0.65590(7) 0.4743(2) 0.45161(12) 0.0130(4) Uani d . . . 1 . .
C C11 0.70209(7) 0.4100(2) 0.42735(12) 0.0143(4) Uani d . . . 1 . .
C C12 0.74439(7) 0.4303(2) 0.47559(12) 0.0153(4) Uani d . . . 1 . .
H H12 0.775106 0.387139 0.456616 0.018 Uiso calc U . R 1 . .
C C13 0.74144(7) 0.5142(2) 0.55163(12) 0.0158(4) Uani d . . . 1 . .
C C14 0.69643(7) 0.5749(2) 0.57967(12) 0.0157(4) Uani d . . . 1 . .
H H14 0.69417 0.62922 0.632642 0.019 Uiso calc U . R 1 . .
C C15 0.65464(7) 0.5561(2) 0.52988(12) 0.0138(4) Uani d . . . 1 . .
C C16 0.70655(7) 0.3110(3) 0.34696(13) 0.0187(4) Uani d . . . 1 . .
C C17 0.60664(7) 0.6293(3) 0.56163(12) 0.0172(4) Uani d . . . 1 . .
C C18 0.78657(7) 0.5364(3) 0.60601(13) 0.0199(4) Uani d . . . 1 . .
F F1 0.75303(5) 0.2896(2) 0.32292(9) 0.0362(4) Uani d . . . 1 . .
F F2 0.68742(6) 0.15697(18) 0.35542(9) 0.0361(4) Uani d . . . 1 . .
F F3 0.68216(6) 0.3811(2) 0.28364(8) 0.0361(4) Uani d . . . 1 . .
F F4 0.56863(5) 0.52464(18) 0.55176(9) 0.0318(3) Uani d . . . 1 . .
F F5 0.59439(5) 0.76890(18) 0.52041(9) 0.0311(3) Uani d . . . 1 . .
F F6 0.60857(5) 0.66841(19) 0.64296(8) 0.0290(3) Uani d . . . 1 . .
F F7 0.78471(6) 0.4433(2) 0.67512(10) 0.0395(4) Uani d . . . 1 . .
F F8 0.82766(5) 0.4920(3) 0.56658(10) 0.0518(5) Uani d . . . 1 . .
F F9 0.79170(6) 0.69221(18) 0.63234(11) 0.0437(4) Uani d . . . 1 . .
S S1 0.57713(2) 0.13821(6) 0.44694(3) 0.01798(12) Uani d . . . 1 . .
S S2 0.62851(2) 0.77967(6) 0.31345(3) 0.01810(12) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C7 . 1.518(3) ?
B1 C3 . 1.519(3) ?
B1 C10 . 1.596(3) ?
C1 C2 . 1.350(3) ?
C1 S1 . 1.713(2) ?
C1 H1 . 0.95 ?
C2 C4 . 1.435(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.403(3) ?
C3 S1 . 1.7187(19) ?
C4 C5 . 1.462(3) ?
C5 C5 3_655 1.415(3) ?
C5 C6 . 1.463(3) ?
C6 C7 . 1.401(3) ?
C6 C8 . 1.431(3) ?
C7 S2 . 1.7208(19) ?
C8 C9 . 1.363(3) ?
C8 H8 . 0.95 ?
C9 S2 . 1.710(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.407(3) ?
C10 C15 . 1.407(3) ?
C11 C12 . 1.388(3) ?
C11 C16 . 1.509(3) ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.386(3) ?
C13 C18 . 1.508(3) ?
C14 C15 . 1.390(3) ?
C14 H14 . 0.95 ?
C15 C17 . 1.513(3) ?
C16 F1 . 1.327(2) ?
C16 F3 . 1.329(2) ?
C16 F2 . 1.344(3) ?
C17 F6 . 1.332(2) ?
C17 F4 . 1.336(2) ?
C17 F5 . 1.338(2) ?
C18 F9 . 1.323(3) ?
C18 F8 . 1.326(3) ?
C18 F7 . 1.329(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 B1 C3 . . 112.36(17) ?
C7 B1 C10 . . 122.31(17) ?
C3 B1 C10 . . 125.32(17) ?
C2 C1 S1 . . 112.50(15) ?
C2 C1 H1 . . 123.8 ?
S1 C1 H1 . . 123.8 ?
C1 C2 C4 . . 112.96(17) ?
C1 C2 H2 . . 123.5 ?
C4 C2 H2 . . 123.5 ?
C4 C3 B1 . . 123.67(17) ?
C4 C3 S1 . . 111.02(14) ?
B1 C3 S1 . . 125.00(14) ?
C3 C4 C2 . . 111.27(17) ?
C3 C4 C5 . . 121.23(17) ?
C2 C4 C5 . . 126.95(17) ?
C5 C5 C4 3_655 . 122.39(12) ?
C5 C5 C6 3_655 . 119.91(12) ?
C4 C5 C6 . . 117.70(16) ?
C7 C6 C8 . . 111.69(17) ?
C7 C6 C5 . . 121.84(17) ?
C8 C6 C5 . . 125.68(17) ?
C6 C7 B1 . . 123.12(17) ?
C6 C7 S2 . . 110.80(14) ?
B1 C7 S2 . . 125.10(14) ?
C9 C8 C6 . . 112.83(18) ?
C9 C8 H8 . . 123.6 ?
C6 C8 H8 . . 123.6 ?
C8 C9 S2 . . 112.12(15) ?
C8 C9 H9 . . 123.9 ?
S2 C9 H9 . . 123.9 ?
C11 C10 C15 . . 115.77(17) ?
C11 C10 B1 . . 121.96(17) ?
C15 C10 B1 . . 122.20(16) ?
C12 C11 C10 . . 122.63(18) ?
C12 C11 C16 . . 117.63(17) ?
C10 C11 C16 . . 119.73(17) ?
C13 C12 C11 . . 119.45(18) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.11(17) ?
C12 C13 C18 . . 120.75(18) ?
C14 C13 C18 . . 119.12(18) ?
C13 C14 C15 . . 119.65(18) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C10 . . 122.34(18) ?
C14 C15 C17 . . 117.88(17) ?
C10 C15 C17 . . 119.77(17) ?
F1 C16 F3 . . 107.92(17) ?
F1 C16 F2 . . 106.02(18) ?
F3 C16 F2 . . 105.74(17) ?
F1 C16 C11 . . 112.84(17) ?
F3 C16 C11 . . 112.40(17) ?
F2 C16 C11 . . 111.46(17) ?
F6 C17 F4 . . 106.96(16) ?
F6 C17 F5 . . 106.81(17) ?
F4 C17 F5 . . 105.96(16) ?
F6 C17 C15 . . 112.44(16) ?
F4 C17 C15 . . 112.34(16) ?
F5 C17 C15 . . 111.91(16) ?
F9 C18 F8 . . 108.34(19) ?
F9 C18 F7 . . 105.72(18) ?
F8 C18 F7 . . 105.80(19) ?
F9 C18 C13 . . 112.23(17) ?
F8 C18 C13 . . 112.16(18) ?
F7 C18 C13 . . 112.17(17) ?
C1 S1 C3 . . 92.20(10) ?
C9 S2 C7 . . 92.51(10) ?

