# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1509687'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2018-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            TPECNThi
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C36 H24 N2 S'
_chemical_formula_sum            'C36 H24 N2 S'
_chemical_formula_weight         516.63

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3022(6)
_cell_length_b                   10.3149(7)
_cell_length_c                   13.7990(8)
_cell_angle_alpha                110.494(6)
_cell_angle_beta                 96.161(5)
_cell_angle_gamma                98.769(5)
_cell_volume                     1336.89(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      4.3860
_cell_measurement_theta_max      64.6840

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    1.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6525
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7270
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.4094
_diffrn_reflns_theta_max         64.8204
_reflns_number_total             4349
_reflns_number_gt                3743
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0414P)²+0.3232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4349
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.010

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.22655(4) 0.04320(4) 0.46061(3) 0.02835(12) Uani 1 1 d . . .
N1 N -0.26739(12) -0.08338(13) 0.59077(10) 0.0262(3) Uani 1 1 d . . .
C12 C 0.33189(15) 0.25263(16) 0.87905(12) 0.0261(3) Uani 1 1 d . . .
H12 H 0.4039 0.3160 0.8753 0.031 Uiso 1 1 calc R . .
C30 C 0.32734(14) 0.33329(16) 1.18711(11) 0.0247(3) Uani 1 1 d . . .
C9 C -0.01104(14) 0.05218(16) 0.72596(11) 0.0245(3) Uani 1 1 d . . .
H9 H -0.0681 -0.0214 0.7335 0.029 Uiso 1 1 calc R . .
C6 C -0.37260(15) -0.08054(16) 0.43151(12) 0.0259(3) Uani 1 1 d . . .
C5 C -0.47661(16) -0.12269(18) 0.34653(12) 0.0306(4) Uani 1 1 d . . .
H5 H -0.4734 -0.0834 0.2954 0.037 Uiso 1 1 calc R . .
C2 C -0.48723(15) -0.23910(17) 0.50346(12) 0.0286(3) Uani 1 1 d . . .
H2 H -0.4921 -0.2775 0.5550 0.034 Uiso 1 1 calc R . .
C10 C 0.11051(14) 0.10914(16) 0.80391(11) 0.0240(3) Uani 1 1 d . . .
C13 C 0.34006(14) 0.20479(15) 0.96215(11) 0.0245(3) Uani 1 1 d . . .
C15 C 0.12088(15) 0.05783(16) 0.88548(12) 0.0266(3) Uani 1 1 d . . .
H15 H 0.0511 -0.0096 0.8873 0.032 Uiso 1 1 calc R . .
C11 C 0.21951(15) 0.20807(16) 0.80240(12) 0.0259(3) Uani 1 1 d . . .
H11 H 0.2159 0.2439 0.7492 0.031 Uiso 1 1 calc R . .
C31 C 0.27711(15) 0.28294(16) 1.25987(12) 0.0281(3) Uani 1 1 d . . .
H31 H 0.3201 0.2234 1.2829 0.034 Uiso 1 1 calc R . .
C1 C -0.37673(14) -0.13730(16) 0.51016(11) 0.0247(3) Uani 1 1 d . . .
C14 C 0.23232(15) 0.10527(16) 0.96311(12) 0.0274(3) Uani 1 1 d . . .
H14 H 0.2358 0.0705 1.0169 0.033 Uiso 1 1 calc R . .
C22 C 0.69496(15) 0.37321(17) 1.05238(12) 0.0291(3) Uani 1 1 d . . .
H22 H 0.6831 0.4511 1.1078 0.035 Uiso 1 1 calc R . .
C25 C 0.65129(15) 0.22491(17) 1.22193(12) 0.0279(3) Uani 1 1 d . . .
H25 H 0.6354 0.1436 1.1615 0.033 Uiso 1 1 calc R . .
C8 C -0.05588(14) 0.08705(16) 0.64456(12) 0.0252(3) Uani 1 1 d . . .
C35 C 0.26175(15) 0.42441(17) 1.15559(12) 0.0278(3) Uani 1 1 d . . .
H35 H 0.2942 0.4601 1.1077 0.033 Uiso 1 1 calc R . .
C4 C -0.58316(16) -0.22310(17) 0.34054(12) 0.0320(4) Uani 1 1 d . . .
H4 H -0.6531 -0.2535 0.2840 0.038 Uiso 1 1 calc R . .
C29 C 0.59457(15) 0.44228(17) 1.32405(12) 0.0287(3) Uani 1 1 d . . .
H29 H 0.5396 0.5077 1.3328 0.034 Uiso 1 1 calc R . .
C3 C -0.58910(16) -0.28123(17) 0.41818(13) 0.0323(4) Uani 1 1 d . . .
H3 H -0.6630 -0.3495 0.4122 0.039 Uiso 1 1 calc R . .
C17 C 0.59134(14) 0.25543(16) 1.00669(11) 0.0243(3) Uani 1 1 d . . .
C24 C 0.56847(14) 0.32228(16) 1.23209(11) 0.0243(3) Uani 1 1 d . . .
C20 C 0.83428(17) 0.2610(2) 0.93360(14) 0.0374(4) Uani 1 1 d . . .
H20 H 0.9156 0.2624 0.9101 0.045 Uiso 1 1 calc R . .
C23 C 0.45257(14) 0.29860(15) 1.14873(11) 0.0243(3) Uani 1 1 d . . .
C26 C 0.75702(16) 0.24809(18) 1.30108(13) 0.0321(4) Uani 1 1 d . . .
H26 H 0.8115 0.1823 1.2934 0.038 Uiso 1 1 calc R . .
C27 C 0.78211(16) 0.36829(19) 1.39136(13) 0.0338(4) Uani 1 1 d . . .
H27 H 0.8533 0.3835 1.4443 0.041 Uiso 1 1 calc R . .
C36 C 0.01360(16) 0.19907(18) 0.61850(14) 0.0350(4) Uani 1 1 d . . .
C28 C 0.70125(16) 0.46565(18) 1.40271(13) 0.0330(4) Uani 1 1 d . . .
H28 H 0.7182 0.5471 1.4632 0.040 Uiso 1 1 calc R . .
C16 C 0.46121(15) 0.25431(16) 1.04480(12) 0.0248(3) Uani 1 1 d . . .
C18 C 0.61110(16) 0.14170(17) 0.92209(12) 0.0293(3) Uani 1 1 d . . .
H18 H 0.5424 0.0629 0.8892 0.035 Uiso 1 1 calc R . .
C32 C 0.16350(16) 0.32065(17) 1.29842(13) 0.0321(4) Uani 1 1 d . . .
H32 H 0.1304 0.2852 1.3463 0.038 Uiso 1 1 calc R . .
C19 C 0.73226(17) 0.14457(19) 0.88621(13) 0.0350(4) Uani 1 1 d . . .
H19 H 0.7443 0.0677 0.8301 0.042 Uiso 1 1 calc R . .
C7 C -0.18257(15) 0.01047(16) 0.57460(11) 0.0246(3) Uani 1 1 d . . .
C21 C 0.81556(16) 0.37604(19) 1.01648(14) 0.0349(4) Uani 1 1 d . . .
H21 H 0.8840 0.4553 1.0481 0.042 Uiso 1 1 calc R . .
C33 C 0.09949(16) 0.41066(18) 1.26592(14) 0.0357(4) Uani 1 1 d . . .
H33 H 0.0236 0.4361 1.2919 0.043 Uiso 1 1 calc R . .
C34 C 0.14911(16) 0.46263(18) 1.19453(13) 0.0335(4) Uani 1 1 d . . .
H34 H 0.1066 0.5235 1.1726 0.040 Uiso 1 1 calc R . .
N2 N 0.05954(17) 0.28529(19) 0.59101(16) 0.0576(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 C6 1.7263(16) . ?
S1 C7 1.7490(14) . ?
N1 C7 1.2984(19) . ?
N1 C1 1.3866(19) . ?
C12 C11 1.380(2) . ?
C12 C13 1.398(2) . ?
C30 C31 1.393(2) . ?
C30 C35 1.395(2) . ?
C30 C23 1.493(2) . ?
C9 C8 1.351(2) . ?
C9 C10 1.454(2) . ?
C6 C5 1.394(2) . ?
C6 C1 1.403(2) . ?
C5 C4 1.363(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.397(2) . ?
C10 C15 1.403(2) . ?
C10 C11 1.405(2) . ?
C13 C14 1.397(2) . ?
C13 C16 1.487(2) . ?
C15 C14 1.379(2) . ?
C31 C32 1.390(2) . ?
C22 C21 1.386(2) . ?
C22 C17 1.392(2) . ?
C25 C26 1.385(2) . ?
C25 C24 1.395(2) . ?
C8 C36 1.439(2) . ?
C8 C7 1.463(2) . ?
C35 C34 1.384(2) . ?
C4 C3 1.401(2) . ?
C29 C28 1.387(2) . ?
C29 C24 1.393(2) . ?
C17 C18 1.395(2) . ?
C17 C16 1.492(2) . ?
C24 C23 1.493(2) . ?
C20 C19 1.375(3) . ?
C20 C21 1.386(3) . ?
C23 C16 1.362(2) . ?
C26 C27 1.381(3) . ?
C27 C28 1.378(2) . ?
C36 N2 1.142(2) . ?
C18 C19 1.391(2) . ?
C32 C33 1.383(2) . ?
C33 C34 1.383(2) . ?

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 C7 88.91(7) . . ?
C7 N1 C1 110.25(12) . . ?
C11 C12 C13 121.60(14) . . ?
C31 C30 C35 118.10(14) . . ?
C31 C30 C23 121.25(13) . . ?
C35 C30 C23 120.54(13) . . ?
C8 C9 C10 131.53(14) . . ?
C5 C6 C1 121.65(14) . . ?
C5 C6 S1 128.83(12) . . ?
C1 C6 S1 109.51(11) . . ?
C4 C5 C6 118.13(15) . . ?
C3 C2 C1 118.27(14) . . ?
C15 C10 C11 117.54(13) . . ?
C15 C10 C9 117.11(13) . . ?
C11 C10 C9 125.32(13) . . ?
C14 C13 C12 117.75(13) . . ?
C14 C13 C16 121.04(13) . . ?
C12 C13 C16 121.18(13) . . ?
C14 C15 C10 121.43(14) . . ?
C12 C11 C10 120.67(14) . . ?
C32 C31 C30 120.80(15) . . ?
N1 C1 C2 125.25(13) . . ?
N1 C1 C6 115.20(13) . . ?
C2 C1 C6 119.54(13) . . ?
C15 C14 C13 120.95(14) . . ?
C21 C22 C17 120.93(15) . . ?
C26 C25 C24 120.62(15) . . ?
C9 C8 C36 124.41(14) . . ?
C9 C8 C7 121.22(13) . . ?
C36 C8 C7 114.37(13) . . ?
C34 C35 C30 121.05(14) . . ?
C5 C4 C3 121.09(14) . . ?
C28 C29 C24 121.01(15) . . ?
C2 C3 C4 121.30(15) . . ?
C22 C17 C18 118.13(14) . . ?
C22 C17 C16 120.52(14) . . ?
C18 C17 C16 121.30(14) . . ?
C29 C24 C25 118.16(14) . . ?
C29 C24 C23 120.17(13) . . ?
C25 C24 C23 121.66(14) . . ?
C19 C20 C21 119.80(15) . . ?
C16 C23 C30 121.83(13) . . ?
C16 C23 C24 122.61(13) . . ?
C30 C23 C24 115.50(12) . . ?
C27 C26 C25 120.43(15) . . ?
C28 C27 C26 119.72(14) . . ?
N2 C36 C8 174.05(18) . . ?
C27 C28 C29 120.05(15) . . ?
C23 C16 C13 121.49(13) . . ?
C23 C16 C17 122.61(13) . . ?
C13 C16 C17 115.89(12) . . ?
C19 C18 C17 120.87(15) . . ?
C33 C32 C31 120.26(15) . . ?
C20 C19 C18 120.12(16) . . ?
N1 C7 C8 124.18(13) . . ?
N1 C7 S1 116.13(11) . . ?
C8 C7 S1 119.69(11) . . ?
C22 C21 C20 120.12(16) . . ?
C32 C33 C34 119.54(15) . . ?
C33 C34 C35 120.23(15) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        100
_diffrn_measured_fraction_theta_full 0.9932
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.037
