# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_200204_BPT-helicene_toluene-hexatetragonal
_database_code_depnum_ccdc_archive 'CCDC 2103647'
loop_
_audit_author_name
_audit_author_address
'Daisuke Sakamaki'
;Osaka Prefecture University
Japan
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C32 H18 N2 S2'
_chemical_formula_moiety         'C32 H18 N2 S2'
_chemical_formula_weight         494.63
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
_space_group_IT_number           88
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'
#------------------------------------------------------------------------------
_cell_length_a                   20.735(3)
_cell_length_b                   20.735(3)
_cell_length_c                   10.5694(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4544.1(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16267
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      27.41
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048.00
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.974

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            20753
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_theta_max         27.413
_diffrn_reflns_theta_min         3.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2580
_reflns_number_gt                2162
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0786
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0390P)²+4.3925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.25
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.39314(2) 0.59444(2) 0.31255(4) 0.02071(11) Uani 1 1 d . . . . .
N1 N 0.56349(6) 0.77254(6) 0.33477(11) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.60372(7) 0.79037(7) 0.43856(14) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.61975(7) 0.74821(7) 0.53639(14) 0.0193(3) Uani 1 1 d . . . . .
H2 H 0.604366 0.705055 0.535639 0.023 Uiso 1 1 calc R U . . .
C3 C 0.65849(7) 0.76991(8) 0.63522(14) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.670533 0.740917 0.700688 0.027 Uiso 1 1 calc R U . . .
C4 C 0.67977(7) 0.83342(8) 0.63931(15) 0.0242(3) Uani 1 1 d . . . . .
H4 H 0.705560 0.847875 0.707972 0.029 Uiso 1 1 calc R U . . .
C5 C 0.66319(7) 0.87581(8) 0.54249(15) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.677250 0.919393 0.545373 0.027 Uiso 1 1 calc R U . . .
C6 C 0.62586(7) 0.85413(7) 0.44121(14) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.55123(7) 0.70625(7) 0.30889(13) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.48863(7) 0.68434(7) 0.31092(13) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.47495(7) 0.61792(7) 0.29518(13) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.52397(7) 0.57458(7) 0.27619(13) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.514618 0.529869 0.269239 0.023 Uiso 1 1 calc R U . . .
C11 C 0.58867(7) 0.59647(7) 0.26692(13) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.64086(8) 0.55259(7) 0.24850(14) 0.0220(3) Uani 1 1 d . . . . .
H12 H 0.632439 0.507616 0.243778 0.026 Uiso 1 1 calc R U . . .
C13 C 0.70274(8) 0.57439(8) 0.23757(14) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.736986 0.544531 0.226029 0.029 Uiso 1 1 calc R U . . .
C14 C 0.71612(7) 0.64117(8) 0.24334(14) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.759083 0.656030 0.232158 0.028 Uiso 1 1 calc R U . . .
C15 C 0.66755(7) 0.68466(7) 0.26494(13) 0.0194(3) Uani 1 1 d . . . . .
H15 H 0.677278 0.729351 0.270315 0.023 Uiso 1 1 calc R U . . .
C16 C 0.60283(7) 0.66350(7) 0.27936(13) 0.0174(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C6 1.7723(15) 2_665 ?
S1 C9 1.7743(15) . ?
N1 C8 1.4250(18) 2_665 ?
N1 C7 1.4244(18) . ?
N1 C1 1.4268(18) . ?
C1 C2 1.394(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.375(2) . ?
C7 C16 1.4239(19) . ?
C8 C9 1.416(2) . ?
C9 C10 1.372(2) . ?
C10 C11 1.420(2) . ?
C10 H10 0.9500 . ?
C11 C16 1.427(2) . ?
C11 C12 1.427(2) . ?
C12 C13 1.365(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.413(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.420(2) . ?
C15 H15 0.9500 . ?

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
C6 S1 C9 97.28(7) 2_665 . ?
C8 N1 C7 115.86(12) 2_665 . ?
C8 N1 C1 114.63(11) 2_665 . ?
C7 N1 C1 120.13(12) . . ?
C2 C1 C6 119.95(14) . . ?
C2 C1 N1 123.17(13) . . ?
C6 C1 N1 116.86(13) . . ?
C3 C2 C1 119.43(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.84(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.81(14) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.84(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 120.10(14) . . ?
C5 C6 S1 121.21(11) . 2_665 ?
C1 C6 S1 118.68(11) . 2_665 ?
C8 C7 C16 120.46(13) . . ?
C8 C7 N1 118.96(13) . . ?
C16 C7 N1 120.58(13) . . ?
C7 C8 C9 120.56(13) . . ?
C7 C8 N1 120.75(13) . 2_665 ?
C9 C8 N1 118.62(13) . 2_665 ?
C10 C9 C8 120.40(13) . . ?
C10 C9 S1 122.94(11) . . ?
C8 C9 S1 116.51(11) . . ?
C9 C10 C11 120.06(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C16 119.98(13) . . ?
C10 C11 C12 121.47(13) . . ?
C16 C11 C12 118.53(13) . . ?
C13 C12 C11 120.86(14) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.35(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.49(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.59(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C7 122.77(13) . . ?
C15 C16 C11 119.05(13) . . ?
C7 C16 C11 118.16(13) . . ?

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
C8 N1 C1 C2 128.84(14) 2_665 . . . ?
C7 N1 C1 C2 -16.3(2) . . . . ?
C8 N1 C1 C6 -49.32(17) 2_665 . . . ?
C7 N1 C1 C6 165.51(13) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
N1 C1 C2 C3 -178.97(13) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 1.7(2) . . . . ?
C4 C5 C6 S1 -177.05(11) . . . 2_665 ?
C2 C1 C6 C5 -0.9(2) . . . . ?
N1 C1 C6 C5 177.33(13) . . . . ?
C2 C1 C6 S1 177.85(11) . . . 2_665 ?
N1 C1 C6 S1 -3.93(17) . . . 2_665 ?
C8 N1 C7 C8 -24.42(16) 2_665 . . . ?
C1 N1 C7 C8 120.34(15) . . . . ?
C8 N1 C7 C16 154.57(13) 2_665 . . . ?
C1 N1 C7 C16 -60.67(18) . . . . ?
C16 C7 C8 C9 5.8(2) . . . . ?
N1 C7 C8 C9 -175.19(12) . . . . ?
C16 C7 C8 N1 -177.14(12) . . . 2_665 ?
N1 C7 C8 N1 1.85(19) . . . 2_665 ?
C7 C8 C9 C10 -0.8(2) . . . . ?
N1 C8 C9 C10 -177.87(13) 2_665 . . . ?
C7 C8 C9 S1 174.95(11) . . . . ?
N1 C8 C9 S1 -2.16(17) 2_665 . . . ?
C6 S1 C9 C10 136.34(13) 2_665 . . . ?
C6 S1 C9 C8 -39.26(12) 2_665 . . . ?
C8 C9 C10 C11 -2.6(2) . . . . ?
S1 C9 C10 C11 -178.07(11) . . . . ?
C9 C10 C11 C16 1.0(2) . . . . ?
C9 C10 C11 C12 179.34(14) . . . . ?
C10 C11 C12 C13 178.87(14) . . . . ?
C16 C11 C12 C13 -2.8(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C12 C13 C14 C15 2.6(2) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C15 C16 C7 176.40(13) . . . . ?
C14 C15 C16 C11 -2.0(2) . . . . ?
C8 C7 C16 C15 174.27(13) . . . . ?
N1 C7 C16 C15 -4.7(2) . . . . ?
C8 C7 C16 C11 -7.3(2) . . . . ?
N1 C7 C16 C11 173.75(12) . . . . ?
C10 C11 C16 C15 -177.61(13) . . . . ?
C12 C11 C16 C15 4.0(2) . . . . ?
C10 C11 C16 C7 3.9(2) . . . . ?
C12 C11 C16 C7 -174.52(13) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
