# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1936361'
loop_
_audit_author_name
_audit_author_address
'Yuejuan Wan'
;South China University of Technology
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0199 Ang.
RESPONSE: The typical thickness of \b-DBPA single crystals was less than 500 nm. Though we have taken a very long time (more than 1 month for each batch of crystal) to get thicker crystals, the thicknesses are only about 1 \mm. In the meanwhile, the crystals were highly flexible. Obvious vibration occurred in the protect gas during the collection of diffraction data. As the result of that, the calculated atom positions were not perfect as traditional bulk crystals.
;
# Added during the CSD deposition process: Tuesday 06 October 2020 11:19 AM
# end Validation Reply Form


_audit_creation_date             2020-10-06T12:07:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C28 H16 N2 S2'
_chemical_formula_weight         444.55
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9035(4)
_cell_length_b                   44.025(6)
_cell_length_c                   6.0394(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.692(8)
_cell_angle_gamma                90
_cell_volume                     1032.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    794
_cell_measurement_theta_min      4.05
_cell_measurement_theta_max      70.72
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.087422
_diffrn_orient_matrix_ub_12      0.019424
_diffrn_orient_matrix_ub_13      0.210162
_diffrn_orient_matrix_ub_21      0.015359
_diffrn_orient_matrix_ub_22      0.028563
_diffrn_orient_matrix_ub_23      -0.14611
_diffrn_orient_matrix_ub_31      -0.386373
_diffrn_orient_matrix_ub_32      0.005604
_diffrn_orient_matrix_ub_33      0.015725
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.076
_diffrn_reflns_av_unetI/netI     0.126
_diffrn_reflns_number            2056
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.017
_diffrn_reflns_theta_max         74.099
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.504
_diffrn_reflns_point_group_measured_fraction_max 0.489
_reflns_Friedel_fraction_full    0
_reflns_Friedel_fraction_max     0
_reflns_Friedel_coverage         0
_reflns_number_total             2056
_reflns_number_gt                1201
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1128P)²+1.7639P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2056
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.256
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.51
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.4194(8) 0.20279(9) 0.9915(5) 0.0538(9) Uani 1 1 d . . . . .
S2 S 0.8223(9) 0.08336(9) 0.8738(5) 0.0547(9) Uani 1 1 d . . . . .
C1 C 1.137(3) 0.0146(3) 0.976(2) 0.054(3) Uani 1 1 d . . . . .
C2 C 0.309(3) 0.2717(3) 1.209(2) 0.054(4) Uani 1 1 d . . . . .
C3 C 0.541(3) 0.2185(3) 1.259(2) 0.051(3) Uani 1 1 d . . . . .
N2 N 0.790(4) 0.0235(3) 0.588(2) 0.080(4) Uani 1 1 d . . . . .
C4 C 0.753(3) 0.1686(3) 1.287(2) 0.053(3) Uani 1 1 d . . . . .
C5 C 0.778(4) 0.1181(3) 1.0223(18) 0.054(3) Uani 1 1 d . . . . .
C6 C 1.163(4) 0.0374(3) 1.120(2) 0.058(4) Uani 1 1 d . . . . .
H6 H 1.280399 0.032182 1.25645 0.069 Uiso 1 1 calc R U . . .
C7 C 1.361(5) -0.0675(4) 0.860(3) 0.077(5) Uani 1 1 d . . . . .
H7 H 1.329974 -0.081432 0.744529 0.092 Uiso 1 1 calc R U . . .
C8 C 0.279(3) 0.3035(3) 1.287(2) 0.052(3) Uani 1 1 d . . . . .
C9 C 0.489(3) 0.2494(3) 1.318(2) 0.056(4) Uani 1 1 d . . . . .
H9 H 0.597378 0.255062 1.456224 0.067 Uiso 1 1 calc R U . . .
C10 C 0.146(3) 0.2661(3) 0.989(2) 0.054(3) Uani 1 1 d . . . . .
C11 C 0.935(3) 0.1167(3) 1.239(2) 0.051(3) Uani 1 1 d . . . . .
C12 C 0.943(4) 0.0200(3) 0.758(3) 0.060(4) Uani 1 1 d . . . . .
C13 C 1.052(4) 0.0676(3) 1.113(2) 0.050(3) Uani 1 1 d . . . . .
C14 C 1.242(5) -0.0377(4) 0.829(2) 0.070(4) Uani 1 1 d . . . . .
H14 H 1.152061 -0.031385 0.687978 0.083 Uiso 1 1 calc R U . . .
C15 C 0.720(3) 0.1974(3) 1.389(2) 0.054(4) Uani 1 1 d . . . . .
H15 H 0.814387 0.201507 1.533061 0.065 Uiso 1 1 calc R U . . .
C16 C 1.524(4) -0.0761(4) 1.065(3) 0.070(4) Uani 1 1 d . . . . .
H16 H 1.625144 -0.09516 1.082833 0.084 Uiso 1 1 calc R U . . .
N1 N 0.014(3) 0.2621(3) 0.812(2) 0.076(4) Uani 1 1 d . . . . .
C17 C 1.258(3) -0.0170(3) 1.010(2) 0.049(3) Uani 1 1 d . . . . .
C18 C 1.080(3) 0.0876(3) 1.2853(18) 0.052(3) Uani 1 1 d . . . . .
H18 H 1.188327 0.08252 1.424607 0.062 Uiso 1 1 calc R U . . .
C19 C 0.106(4) 0.3248(4) 1.151(3) 0.062(4) Uani 1 1 d . . . . .
H19 H 0.008785 0.319283 1.0098 0.075 Uiso 1 1 calc R U . . .
C20 C 0.607(4) 0.1689(3) 1.065(2) 0.057(4) Uani 1 1 d . . . . .
C21 C 0.075(4) 0.3546(4) 1.224(3) 0.076(5) Uani 1 1 d . . . . .
H21 H -0.0418 0.368814 1.130721 0.092 Uiso 1 1 calc R U . . .
C22 C 0.418(4) 0.3120(4) 1.501(3) 0.064(4) Uani 1 1 d . . . . .
H22 H 0.528597 0.297808 1.597414 0.076 Uiso 1 1 calc R U . . .
C23 C 0.603(4) 0.1436(4) 0.925(2) 0.056(3) Uani 1 1 d . . . . .
H23 H 0.49483 0.143603 0.780895 0.067 Uiso 1 1 calc R U . . .
C24 C 0.921(3) 0.1422(3) 1.3754(19) 0.050(3) Uani 1 1 d . . . . .
H24 H 1.020523 0.141904 1.521816 0.06 Uiso 1 1 calc R U . . .
C25 C 1.424(4) -0.0263(3) 1.217(3) 0.064(4) Uani 1 1 d . . . . .
H25 H 1.457177 -0.012594 1.334151 0.077 Uiso 1 1 calc R U . . .
C26 C 1.534(5) -0.0556(4) 1.245(2) 0.077(5) Uani 1 1 d . . . . .
H26 H 1.618205 -0.062263 1.386317 0.093 Uiso 1 1 calc R U . . .
C27 C 0.215(4) 0.3629(4) 1.432(3) 0.077(5) Uani 1 1 d . . . . .
H27 H 0.193036 0.382847 1.479863 0.093 Uiso 1 1 calc R U . . .
C28 C 0.387(4) 0.3422(4) 1.567(3) 0.072(4) Uani 1 1 d . . . . .
H28 H 0.485344 0.348204 1.706821 0.087 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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 C20 1.702(16) . ?
S1 C3 1.777(14) . ?
S2 C13 1.764(14) . ?
S2 C5 1.791(14) . ?
C1 C6 1.329(18) . ?
C1 C12 1.472(19) . ?
C1 C17 1.47(2) . ?
C2 C9 1.341(18) . ?
C2 C10 1.436(19) . ?
C2 C8 1.48(2) . ?
C3 C15 1.363(18) . ?
C3 C9 1.43(2) . ?
N2 C12 1.148(18) . ?
C4 C20 1.404(18) . ?
C4 C24 1.412(19) . ?
C4 C15 1.420(19) . ?
C5 C11 1.391(15) . ?
C5 C23 1.41(2) . ?
C6 C13 1.397(19) . ?
C6 H6 0.93 . ?
C7 C16 1.38(2) . ?
C7 C14 1.40(2) . ?
C7 H7 0.93 . ?
C8 C19 1.384(19) . ?
C8 C22 1.401(18) . ?
C9 H9 0.93 . ?
C10 N1 1.156(17) . ?
C11 C24 1.399(19) . ?
C11 C18 1.42(2) . ?
C13 C18 1.359(18) . ?
C14 C17 1.421(19) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 C26 1.41(2) . ?
C16 H16 0.93 . ?
C17 C25 1.413(19) . ?
C18 H18 0.93 . ?
C19 C21 1.39(2) . ?
C19 H19 0.93 . ?
C20 C23 1.39(2) . ?
C21 C27 1.37(2) . ?
C21 H21 0.93 . ?
C22 C28 1.40(2) . ?
C22 H22 0.93 . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C26 1.37(2) . ?
C25 H25 0.93 . ?
C26 H26 0.93 . ?
C27 C28 1.36(2) . ?
C27 H27 0.93 . ?
C28 H28 0.93 . ?

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
C20 S1 C3 92.0(7) . . ?
C13 S2 C5 89.5(6) . . ?
C6 C1 C12 117.5(14) . . ?
C6 C1 C17 128.4(13) . . ?
C12 C1 C17 113.9(12) . . ?
C9 C2 C10 119.3(13) . . ?
C9 C2 C8 125.9(13) . . ?
C10 C2 C8 114.6(12) . . ?
C15 C3 C9 125.7(12) . . ?
C15 C3 S1 109.5(11) . . ?
C9 C3 S1 124.5(10) . . ?
C20 C4 C24 119.9(13) . . ?
C20 C4 C15 111.2(12) . . ?
C24 C4 C15 128.8(13) . . ?
C11 C5 C23 125.3(13) . . ?
C11 C5 S2 112.1(11) . . ?
C23 C5 S2 122.6(9) . . ?
C1 C6 C13 134.2(13) . . ?
C1 C6 H6 112.9 . . ?
C13 C6 H6 112.9 . . ?
C16 C7 C14 119.7(16) . . ?
C16 C7 H7 120.1 . . ?
C14 C7 H7 120.1 . . ?
C19 C8 C22 119.2(14) . . ?
C19 C8 C2 120.0(12) . . ?
C22 C8 C2 120.8(13) . . ?
C2 C9 C3 130.9(12) . . ?
C2 C9 H9 114.5 . . ?
C3 C9 H9 114.5 . . ?
N1 C10 C2 178.7(17) . . ?
C5 C11 C24 118.5(13) . . ?
C5 C11 C18 111.0(12) . . ?
C24 C11 C18 130.5(12) . . ?
N2 C12 C1 178.3(17) . . ?
C18 C13 C6 126.1(12) . . ?
C18 C13 S2 111.7(10) . . ?
C6 C13 S2 122.0(10) . . ?
C7 C14 C17 120.6(14) . . ?
C7 C14 H14 119.7 . . ?
C17 C14 H14 119.7 . . ?
C3 C15 C4 114.9(12) . . ?
C3 C15 H15 122.6 . . ?
C4 C15 H15 122.6 . . ?
C7 C16 C26 119.2(16) . . ?
C7 C16 H16 120.4 . . ?
C26 C16 H16 120.4 . . ?
C25 C17 C14 118.4(14) . . ?
C25 C17 C1 120.6(12) . . ?
C14 C17 C1 120.7(12) . . ?
C13 C18 C11 115.7(12) . . ?
C13 C18 H18 122.2 . . ?
C11 C18 H18 122.2 . . ?
C8 C19 C21 120.4(16) . . ?
C8 C19 H19 119.8 . . ?
C21 C19 H19 119.8 . . ?
C23 C20 C4 123.4(14) . . ?
C23 C20 S1 124.4(11) . . ?
C4 C20 S1 112.2(11) . . ?
C27 C21 C19 120.3(17) . . ?
C27 C21 H21 119.9 . . ?
C19 C21 H21 119.9 . . ?
C28 C22 C8 118.8(15) . . ?
C28 C22 H22 120.6 . . ?
C8 C22 H22 120.6 . . ?
C20 C23 C5 114.0(12) . . ?
C20 C23 H23 123 . . ?
C5 C23 H23 123 . . ?
C11 C24 C4 118.8(12) . . ?
C11 C24 H24 120.6 . . ?
C4 C24 H24 120.6 . . ?
C26 C25 C17 119.8(15) . . ?
C26 C25 H25 120.1 . . ?
C17 C25 H25 120.1 . . ?
C25 C26 C16 121.5(15) . . ?
C25 C26 H26 119.2 . . ?
C16 C26 H26 119.2 . . ?
C28 C27 C21 120.0(17) . . ?
C28 C27 H27 120 . . ?
C21 C27 H27 120 . . ?
C27 C28 C22 121.3(15) . . ?
C27 C28 H28 119.3 . . ?
C22 C28 H28 119.3 . . ?

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
C20 S1 C3 C15 0.6(11) . . . . ?
C20 S1 C3 C9 174.8(12) . . . . ?
C13 S2 C5 C11 0.3(11) . . . . ?
C13 S2 C5 C23 -179.7(13) . . . . ?
C12 C1 C6 C13 -2(3) . . . . ?
C17 C1 C6 C13 -177.7(16) . . . . ?
C9 C2 C8 C19 175.3(14) . . . . ?
C10 C2 C8 C19 0.1(18) . . . . ?
C9 C2 C8 C22 -7(2) . . . . ?
C10 C2 C8 C22 178.2(12) . . . . ?
C10 C2 C9 C3 -3(2) . . . . ?
C8 C2 C9 C3 -178.5(14) . . . . ?
C15 C3 C9 C2 -177.2(15) . . . . ?
S1 C3 C9 C2 10(2) . . . . ?
C23 C5 C11 C24 0(2) . . . . ?
S2 C5 C11 C24 -180.0(10) . . . . ?
C23 C5 C11 C18 178.6(14) . . . . ?
S2 C5 C11 C18 -1.4(15) . . . . ?
C1 C6 C13 C18 174.8(16) . . . . ?
C1 C6 C13 S2 0(3) . . . . ?
C5 S2 C13 C18 0.9(12) . . . . ?
C5 S2 C13 C6 176.4(13) . . . . ?
C16 C7 C14 C17 -6(3) . . . . ?
C9 C3 C15 C4 -176.6(13) . . . . ?
S1 C3 C15 C4 -2.5(15) . . . . ?
C20 C4 C15 C3 3.7(17) . . . . ?
C24 C4 C15 C3 179.9(13) . . . . ?
C14 C7 C16 C26 7(3) . . . . ?
C7 C14 C17 C25 6(2) . . . . ?
C7 C14 C17 C1 179.2(15) . . . . ?
C6 C1 C17 C25 1(2) . . . . ?
C12 C1 C17 C25 -174.9(13) . . . . ?
C6 C1 C17 C14 -173.0(16) . . . . ?
C12 C1 C17 C14 11.5(19) . . . . ?
C6 C13 C18 C11 -177.3(14) . . . . ?
S2 C13 C18 C11 -2.0(17) . . . . ?
C5 C11 C18 C13 2.2(18) . . . . ?
C24 C11 C18 C13 -179.4(14) . . . . ?
C22 C8 C19 C21 1(2) . . . . ?
C2 C8 C19 C21 179.5(14) . . . . ?
C24 C4 C20 C23 3(2) . . . . ?
C15 C4 C20 C23 179.9(14) . . . . ?
C24 C4 C20 S1 -179.7(10) . . . . ?
C15 C4 C20 S1 -3.1(15) . . . . ?
C3 S1 C20 C23 178.5(14) . . . . ?
C3 S1 C20 C4 1.4(11) . . . . ?
C8 C19 C21 C27 0(2) . . . . ?
C19 C8 C22 C28 -2(2) . . . . ?
C2 C8 C22 C28 179.5(14) . . . . ?
C4 C20 C23 C5 -4(2) . . . . ?
S1 C20 C23 C5 179.5(11) . . . . ?
C11 C5 C23 C20 2(2) . . . . ?
S2 C5 C23 C20 -177.8(11) . . . . ?
C5 C11 C24 C4 -0.8(19) . . . . ?
C18 C11 C24 C4 -179.0(13) . . . . ?
C20 C4 C24 C11 -0.8(19) . . . . ?
C15 C4 C24 C11 -176.7(13) . . . . ?
C14 C17 C25 C26 -6(2) . . . . ?
C1 C17 C25 C26 -180.0(15) . . . . ?
C17 C25 C26 C16 7(3) . . . . ?
C7 C16 C26 C25 -8(3) . . . . ?
C19 C21 C27 C28 0(3) . . . . ?
C21 C27 C28 C22 -1(3) . . . . ?
C8 C22 C28 C27 2(3) . . . . ?



#----------------------------------------------------------------------------#
#                   Validation response form                                       #
#----------------------------------------------------------------------------#

# start Validation Reply Form
_vrf_PLAT340_ALERT_3_B           
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0199 Ang.
RESPONSE: The typical thickness of \b-DBPA single crystals was less than 500 nm. Though we have taken a very long time (more than 1 month for each batch of crystal) to get thicker crystals, the thicknesses are only about 1 \mm. In the meanwhile, the crystals were highly flexible. Obvious vibration occurred in the protect gas during the collection of diffraction data. As the result of that, the calculated atom positions were not perfect as traditional bulk crystals.
;


# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2032334'
loop_
_audit_author_name
_audit_author_address
'Jian Deng'
;South China University of Technology
China
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;

_audit_creation_date             2020-10-06T10:57:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C10 H6 N S'
_chemical_formula_weight         172.22

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.938(4)
_cell_length_b                   5.870(5)
_cell_length_c                   18.06(2)
_cell_angle_alpha                80.84(4)
_cell_angle_beta                 87.25(5)
_cell_angle_gamma                86.08(4)
_cell_volume                     411.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3042
_cell_measurement_theta_min      6.86
_cell_measurement_theta_max      55.11
_cell_measurement_wavelength     0

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             178

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_number            3787
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.923
_reflns_Friedel_coverage         0
_reflns_number_total             1736
_reflns_number_gt                1138
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015), SORTAV (Blessing, 1995)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1736
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0942
_refine_ls_wR_factor_ref         0.3228
_refine_ls_wR_factor_gt          0.2976
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.135

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.1117(4) 0.7111(3) 0.07711(7) 0.0705(7) Uani 1 1 d . U . . .
C1 C 0.2819(11) 0.4408(7) 0.0928(2) 0.0436(9) Uani 1 1 d . U . . .
H1 H 0.314749 0.341078 0.057529 0.052 Uiso 1 1 calc R U . . .
N1 N 0.7904(11) 0.0623(6) 0.3140(2) 0.0523(11) Uani 1 1 d . . . . .
C2 C 0.4867(9) 0.4710(6) 0.4238(2) 0.0302(8) Uani 1 1 d . . . . .
C3 C 0.4773(10) 0.4359(6) 0.34504(19) 0.0305(8) Uani 1 1 d . . . . .
C4 C 0.3704(12) 0.3879(7) 0.1714(2) 0.0444(10) Uani 1 1 d . . . . .
H4 H 0.475937 0.24776 0.192584 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6461(11) 0.3024(6) 0.4771(2) 0.0374(9) Uani 1 1 d . . . . .
H5 H 0.745049 0.168096 0.461886 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3397(11) 0.6706(6) 0.4496(2) 0.0384(10) Uani 1 1 d . . . . .
H6 H 0.231 0.786076 0.416044 0.046 Uiso 1 1 calc R U . . .
C7 C 0.6476(10) 0.2279(6) 0.3269(2) 0.0348(9) Uani 1 1 d . . . . .
C8 C 0.2786(10) 0.5732(6) 0.2125(2) 0.0354(9) Uani 1 1 d . . . . .
C9 C 0.3116(10) 0.5874(6) 0.2904(2) 0.0354(9) Uani 1 1 d . . . . .
H9 H 0.205066 0.718427 0.306328 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1281(13) 0.7590(8) 0.1662(2) 0.0494(11) Uani 1 1 d . . . . .
H10 H 0.045048 0.895472 0.182473 0.059 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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 C1 1.666(5) . ?
S1 C10 1.682(5) . ?
C1 C4 1.458(6) . ?
N1 C7 1.141(5) . ?
C2 C5 1.403(5) . ?
C2 C6 1.407(5) . ?
C2 C3 1.472(5) . ?
C3 C9 1.376(5) . ?
C3 C7 1.429(5) . ?
C4 C8 1.430(6) . ?
C5 C6 1.363(5) 2_666 ?
C8 C10 1.382(5) . ?
C8 C9 1.435(5) . ?

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
C1 S1 C10 95.8(2) . . ?
C4 C1 S1 108.1(3) . . ?
C5 C2 C6 116.9(4) . . ?
C5 C2 C3 120.4(3) . . ?
C6 C2 C3 122.7(3) . . ?
C9 C3 C7 119.9(3) . . ?
C9 C3 C2 123.9(3) . . ?
C7 C3 C2 116.2(3) . . ?
C8 C4 C1 113.3(4) . . ?
C6 C5 C2 122.0(3) 2_666 . ?
C5 C6 C2 121.2(3) 2_666 . ?
N1 C7 C3 178.0(4) . . ?
C10 C8 C4 110.3(4) . . ?
C10 C8 C9 119.3(4) . . ?
C4 C8 C9 130.5(3) . . ?
C3 C9 C8 129.6(4) . . ?
C8 C10 S1 112.6(4) . . ?


# END of CIF
_exptl_crystal_preparation       OFETs
