# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_g15-2
_database_code_depnum_ccdc_archive 'CCDC 1407672'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 N2 S'
_chemical_formula_weight         402.49

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.303(2)
_cell_length_b                   7.5885(15)
_cell_length_c                   26.330(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.75(3)
_cell_angle_gamma                90.00
_cell_volume                     2039.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      6.21
_cell_measurement_theta_max      55.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19196
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4665
_reflns_number_gt                2009
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1072P)²+1.5932P] 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         4665
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2044
_refine_ls_R_factor_gt           0.0985
_refine_ls_wR_factor_ref         0.2844
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.8776(3) -0.1775(4) 1.00894(8) 0.1292(14) Uani 0.671(8) 1 d P . .
N2' N 0.8776(3) -0.1775(4) 1.00894(8) 0.1292(14) Uani 0.329(8) 1 d P . .
N2 N 0.6547(3) -0.0370(3) 1.04865(11) 0.0998(16) Uani 0.671(8) 1 d P . .
S1' S 0.6547(3) -0.0370(3) 1.04865(11) 0.0998(16) Uani 0.329(8) 1 d P . .
C16 C 0.5843(5) 0.9523(5) 0.82116(15) 0.0580(11) Uani 1 1 d . . .
C13 C 0.6907(4) 0.7132(5) 0.87820(15) 0.0554(11) Uani 1 1 d . . .
N1 N 0.6925(3) 0.8697(4) 0.84875(13) 0.0573(9) Uani 1 1 d . . .
C22 C 0.7696(5) 1.0959(5) 0.80533(15) 0.0588(11) Uani 1 1 d . . .
C21 C 0.6291(5) 1.0940(5) 0.79402(15) 0.0604(11) Uani 1 1 d . . .
C10 C 0.6980(5) 0.4103(6) 0.93803(16) 0.0646(12) Uani 1 1 d . . .
C27 C 0.8051(4) 0.9577(5) 0.83952(14) 0.0560(11) Uani 1 1 d . . .
C14 C 0.7683(5) 0.5722(6) 0.86845(17) 0.0664(12) Uani 1 1 d . . .
H14 H 0.8180 0.5781 0.8415 0.080 Uiso 1 1 calc R . .
C8 C 0.7729(6) 0.1261(8) 0.9735(2) 0.0915(17) Uani 1 1 d . . .
H8 H 0.8356 0.1230 0.9512 0.110 Uiso 1 1 calc R . .
C15 C 0.7724(5) 0.4231(6) 0.89835(17) 0.0715(13) Uani 1 1 d . . .
H15 H 0.8260 0.3296 0.8917 0.086 Uiso 1 1 calc R . .
C1 C 0.7084(6) -0.2175(6) 1.0703(2) 0.0764(15) Uani 1 1 d . . .
C26 C 0.9327(5) 0.9296(6) 0.86032(17) 0.0662(12) Uani 1 1 d . . .
H26 H 0.9546 0.8404 0.8842 0.079 Uiso 1 1 calc R . .
C9 C 0.6969(6) 0.2557(7) 0.9723(2) 0.0855(16) Uani 1 1 d . . .
H9 H 0.6346 0.2545 0.9948 0.103 Uiso 1 1 calc R . .
C17 C 0.4522(5) 0.9109(7) 0.81702(19) 0.0727(13) Uani 1 1 d . . .
H17 H 0.4225 0.8172 0.8351 0.087 Uiso 1 1 calc R . .
C23 C 0.8676(7) 1.2029(7) 0.79055(19) 0.0809(16) Uani 1 1 d . . .
H23 H 0.8465 1.2948 0.7675 0.097 Uiso 1 1 calc R . .
C6 C 0.8143(6) -0.2910(7) 1.0517(2) 0.0813(15) Uani 1 1 d . . .
C24 C 0.9943(7) 1.1721(8) 0.8101(2) 0.0904(18) Uani 1 1 d . . .
H24 H 1.0602 1.2425 0.8000 0.108 Uiso 1 1 calc R . .
C20 C 0.5394(7) 1.1963(7) 0.76287(19) 0.0831(16) Uani 1 1 d . . .
H20 H 0.5673 1.2915 0.7449 0.100 Uiso 1 1 calc R . .
C12 C 0.6152(5) 0.7021(6) 0.91739(16) 0.0656(12) Uani 1 1 d . . .
H12 H 0.5619 0.7958 0.9242 0.079 Uiso 1 1 calc R . .
C7 C 0.7651(7) -0.0249(7) 1.0104(2) 0.0936(19) Uani 1 1 d . . .
C19 C 0.4095(7) 1.1549(8) 0.7591(2) 0.0944(18) Uani 1 1 d . . .
H19 H 0.3488 1.2235 0.7385 0.113 Uiso 1 1 calc R . .
C11 C 0.6194(5) 0.5516(7) 0.94626(18) 0.0738(13) Uani 1 1 d . . .
H11 H 0.5673 0.5445 0.9724 0.089 Uiso 1 1 calc R . .
C4 C 0.7976(11) -0.5289(9) 1.1093(4) 0.131(3) Uani 1 1 d . . .
H4 H 0.8253 -0.6378 1.1230 0.157 Uiso 1 1 calc R . .
C18 C 0.3666(6) 1.0146(8) 0.7849(2) 0.0884(17) Uani 1 1 d . . .
H18 H 0.2776 0.9884 0.7808 0.106 Uiso 1 1 calc R . .
C25 C 1.0267(6) 1.0363(8) 0.8450(2) 0.0835(16) Uani 1 1 d . . .
H25 H 1.1140 1.0180 0.8582 0.100 Uiso 1 1 calc R . .
C3 C 0.6974(12) -0.4498(13) 1.1267(3) 0.134(3) Uani 1 1 d . . .
H3 H 0.6592 -0.5032 1.1528 0.160 Uiso 1 1 calc R . .
C5 C 0.8625(7) -0.4559(10) 1.0717(3) 0.112(2) Uani 1 1 d . . .
H5 H 0.9335 -0.5114 1.0602 0.135 Uiso 1 1 calc R . .
C2 C 0.6502(7) -0.2970(11) 1.1080(3) 0.105(2) Uani 1 1 d . . .
H2 H 0.5789 -0.2449 1.1203 0.126 Uiso 1 1 calc R . .


_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 1.623(6) . ?
S1 C7 1.643(7) . ?
N2 C1 1.556(5) . ?
N2 C7 1.620(8) . ?
C16 C17 1.386(7) . ?
C16 N1 1.394(5) . ?
C16 C21 1.403(6) . ?
C13 C12 1.376(6) . ?
C13 C14 1.380(6) . ?
C13 N1 1.420(5) . ?
N1 C27 1.388(5) . ?
C22 C23 1.391(7) . ?
C22 C27 1.399(6) . ?
C22 C21 1.438(6) . ?
C21 C20 1.388(7) . ?
C10 C11 1.378(7) . ?
C10 C15 1.380(6) . ?
C10 C9 1.482(7) . ?
C27 C26 1.371(6) . ?
C14 C15 1.376(6) . ?
C8 C9 1.255(7) . ?
C8 C7 1.511(8) . ?
C1 C2 1.368(8) . ?
C1 C6 1.373(8) . ?
C26 C25 1.365(7) . ?
C17 C18 1.383(7) . ?
C23 C24 1.357(8) . ?
C6 C5 1.421(9) . ?
C24 C25 1.392(8) . ?
C20 C19 1.366(8) . ?
C12 C11 1.370(6) . ?
C19 C18 1.368(8) . ?
C4 C3 1.328(12) . ?
C4 C5 1.383(11) . ?
C3 C2 1.326(11) . ?

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 90.4(4) . . ?
C1 N2 C7 91.9(4) . . ?
C17 C16 N1 130.2(4) . . ?
C17 C16 C21 121.4(4) . . ?
N1 C16 C21 108.3(4) . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 N1 120.7(4) . . ?
C14 C13 N1 119.8(4) . . ?
C27 N1 C16 108.7(3) . . ?
C27 N1 C13 124.8(4) . . ?
C16 N1 C13 126.3(4) . . ?
C23 C22 C27 118.8(5) . . ?
C23 C22 C21 134.1(5) . . ?
C27 C22 C21 107.1(4) . . ?
C20 C21 C16 119.4(5) . . ?
C20 C21 C22 133.5(5) . . ?
C16 C21 C22 107.1(4) . . ?
C11 C10 C15 117.5(4) . . ?
C11 C10 C9 117.9(5) . . ?
C15 C10 C9 124.6(5) . . ?
C26 C27 N1 129.4(4) . . ?
C26 C27 C22 121.8(4) . . ?
N1 C27 C22 108.7(4) . . ?
C15 C14 C13 120.3(4) . . ?
C9 C8 C7 121.6(6) . . ?
C14 C15 C10 120.9(5) . . ?
C2 C1 C6 121.8(6) . . ?
C2 C1 N2 119.0(6) . . ?
C6 C1 N2 119.2(5) . . ?
C25 C26 C27 118.0(5) . . ?
C8 C9 C10 125.5(6) . . ?
C18 C17 C16 117.2(5) . . ?
C24 C23 C22 119.4(5) . . ?
C1 C6 C5 118.7(6) . . ?
C1 C6 S1 116.4(5) . . ?
C5 C6 S1 124.9(6) . . ?
C23 C24 C25 120.7(5) . . ?
C19 C20 C21 118.8(5) . . ?
C11 C12 C13 119.2(5) . . ?
C8 C7 N2 123.0(5) . . ?
C8 C7 S1 114.9(5) . . ?
N2 C7 S1 122.1(4) . . ?
C20 C19 C18 121.5(6) . . ?
C12 C11 C10 122.5(4) . . ?
C3 C4 C5 122.6(7) . . ?
C19 C18 C17 121.6(6) . . ?
C26 C25 C24 121.2(6) . . ?
C2 C3 C4 122.0(8) . . ?
C4 C5 C6 116.1(7) . . ?
C3 C2 C1 118.7(8) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.054
