# 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_150402_gsf_20
_audit_block_doi                 10.5517/cc1k2j7d
_database_code_depnum_ccdc_archive 'CCDC 1432393'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;
_audit_creation_date             2015-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        DBTO-PTZ
_chemical_formula_moiety         'C36 H22 N2 O2 S3'
_chemical_formula_sum            'C36 H22 N2 O2 S3'
_chemical_formula_weight         610.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.891(3)
_cell_length_b                   7.4319(4)
_cell_length_c                   18.017(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.410(17)
_cell_angle_gamma                90.00
_cell_volume                     2934.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2099
_cell_measurement_temperature    170.
_cell_measurement_theta_max      29.4573
_cell_measurement_theta_min      2.8883
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6001
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      170.
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0043335000
_diffrn_orient_matrix_UB_12      -0.0008611000
_diffrn_orient_matrix_UB_13      -0.0427534000
_diffrn_orient_matrix_UB_21      0.0253273000
_diffrn_orient_matrix_UB_22      -0.0586091000
_diffrn_orient_matrix_UB_23      0.0179573000
_diffrn_orient_matrix_UB_31      -0.0196572000
_diffrn_orient_matrix_UB_32      -0.0753718000
_diffrn_orient_matrix_UB_33      -0.0134781000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2209
_reflns_number_total             2682
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0569P)²+3.6622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1274
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.0000 0.40828(11) 0.2500 0.0235(2) Uani 1 d . . 2 S T P
S2 S 0.22560(3) 1.31354(9) 0.25492(5) 0.0303(2) Uani 1 d . . 1 . . .
O1 O 0.03215(8) 0.3070(2) 0.33299(13) 0.0374(5) Uani 1 d . . 1 . . .
N1 N 0.14461(9) 1.0132(3) 0.25268(13) 0.0210(5) Uani 1 d . . 1 . . .
C1 C 0.13029(11) 0.6874(3) 0.25161(17) 0.0245(5) Uani 1 d . . 1 . . .
H1 H 0.1655 0.6702 0.2521 0.029 Uiso 1 calc . . 1 R . .
C2 C 0.09863(10) 0.5399(3) 0.25069(16) 0.0236(5) Uani 1 d . . 1 . . .
H2 H 0.1113 0.4207 0.2504 0.028 Uiso 1 calc . . 1 R . .
C3 C 0.04772(10) 0.5723(3) 0.25024(16) 0.0206(5) Uani 1 d . . 1 . . .
C4 C 0.02756(10) 0.7449(3) 0.25008(15) 0.0183(5) Uani 1 d . . 1 . . .
C5 C 0.05938(10) 0.8915(3) 0.25067(15) 0.0181(5) Uani 1 d . . 1 . . .
H5 H 0.0463 1.0105 0.2503 0.022 Uiso 1 calc . . 1 R . .
C6 C 0.11088(10) 0.8615(3) 0.25187(15) 0.0195(5) Uani 1 d . . 1 . . .
C7 C 0.20050(10) 1.0502(3) 0.33794(16) 0.0205(5) Uani 1 d . . 1 . . .
C8 C 0.21445(11) 0.9662(3) 0.41697(17) 0.0255(6) Uani 1 d . . 1 . . .
H8 H 0.1866 0.8819 0.4134 0.031 Uiso 1 calc . . 1 R . .
C9 C 0.26862(12) 1.0039(3) 0.50110(18) 0.0308(6) Uani 1 d . . 1 . . .
H9 H 0.2768 0.9477 0.5545 0.037 Uiso 1 calc . . 1 R . .
C10 C 0.31018(11) 1.1215(4) 0.50748(18) 0.0336(7) Uani 1 d . . 1 . . .
H10 H 0.3478 1.1438 0.5646 0.040 Uiso 1 calc . . 1 R . .
C11 C 0.29673(11) 1.2073(4) 0.42979(19) 0.0316(6) Uani 1 d . . 1 . . .
H11 H 0.3254 1.2888 0.4338 0.038 Uiso 1 calc . . 1 R . .
C12 C 0.24204(11) 1.1762(3) 0.34605(17) 0.0237(5) Uani 1 d . . 1 . . .
C13 C 0.16904(11) 1.1859(3) 0.16116(17) 0.0257(6) Uani 1 d . . 1 . . .
C14 C 0.15789(13) 1.2254(4) 0.0782(2) 0.0361(7) Uani 1 d . . 1 . . .
H14 H 0.1826 1.3116 0.0748 0.043 Uiso 1 calc . . 1 R . .
C15 C 0.11080(13) 1.1407(5) -0.0010(2) 0.0429(8) Uani 1 d . . 1 . . .
H15 H 0.1031 1.1694 -0.0581 0.051 Uiso 1 calc . . 1 R . .
C16 C 0.07590(12) 1.0163(4) 0.00450(19) 0.0369(7) Uani 1 d . . 1 . . .
H16 H 0.0435 0.9587 -0.0492 0.044 Uiso 1 calc . . 1 R . .
C17 C 0.08739(11) 0.9726(4) 0.08834(17) 0.0277(6) Uani 1 d . . 1 . . .
H17 H 0.0628 0.8848 0.0910 0.033 Uiso 1 calc . . 1 R . .
C18 C 0.13409(10) 1.0551(3) 0.16803(16) 0.0216(5) Uani 1 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4324(19) . ?
S1 O1 1.4324(19) 2 ?
S1 C3 1.768(2) 2 ?
S1 C3 1.768(2) . ?
S2 C12 1.758(3) . ?
S2 C13 1.758(3) . ?
N1 C6 1.442(3) . ?
N1 C7 1.421(3) . ?
N1 C18 1.415(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 C4 1.392(3) . ?
C4 C4 1.481(4) 2 ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.399(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.370(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C13 C14 1.376(4) . ?
C13 C18 1.407(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?

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
O1 S1 O1 116.59(17) . 2 ?
O1 S1 C3 111.20(10) . . ?
O1 S1 C3 111.30(11) 2 . ?
O1 S1 C3 111.20(10) 2 2 ?
O1 S1 C3 111.30(11) . 2 ?
C3 S1 C3 92.82(15) . 2 ?
C13 S2 C12 101.16(12) . . ?
C7 N1 C6 115.30(18) . . ?
C18 N1 C6 115.42(18) . . ?
C18 N1 C7 123.25(19) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(2) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.5(2) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 S1 126.38(18) . . ?
C2 C3 C4 122.9(2) . . ?
C4 C3 S1 110.75(17) . . ?
C3 C4 C4 112.85(13) . 2 ?
C5 C4 C3 119.2(2) . . ?
C5 C4 C4 127.95(13) . 2 ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 N1 119.4(2) . . ?
C5 C6 N1 119.3(2) . . ?
C5 C6 C1 121.3(2) . . ?
C8 C7 N1 120.6(2) . . ?
C8 C7 C12 117.9(2) . . ?
C12 C7 N1 121.5(2) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 S2 122.52(19) . . ?
C11 C12 S2 116.99(19) . . ?
C11 C12 C7 120.3(2) . . ?
C14 C13 S2 116.9(2) . . ?
C14 C13 C18 120.5(2) . . ?
C18 C13 S2 122.59(19) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 N1 121.3(2) . . ?
C17 C18 N1 120.9(2) . . ?
C17 C18 C13 117.7(2) . . ?

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
S1 C3 C4 C4 0.1(3) . . . 2 ?
S1 C3 C4 C5 179.69(17) . . . . ?
S2 C13 C14 C15 -175.1(2) . . . . ?
S2 C13 C18 N1 -2.9(3) . . . . ?
S2 C13 C18 C17 174.91(18) . . . . ?
O1 S1 C3 C2 65.7(2) . . . . ?
O1 S1 C3 C2 -66.1(2) 2 . . . ?
O1 S1 C3 C4 -114.19(18) . . . . ?
O1 S1 C3 C4 114.02(18) 2 . . . ?
N1 C7 C8 C9 -178.9(2) . . . . ?
N1 C7 C12 S2 6.3(3) . . . . ?
N1 C7 C12 C11 -178.8(2) . . . . ?
C1 C2 C3 S1 -179.45(18) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C1 C6 N1 -179.9(2) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C3 C4 C4 -179.8(2) . . . 2 ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 S1 C3 C2 179.9(3) 2 . . . ?
C3 S1 C3 C4 -0.04(12) 2 . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C4 C5 C6 179.2(3) 2 . . . ?
C4 C5 C6 N1 -179.88(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 N1 C7 C8 -11.7(3) . . . . ?
C6 N1 C7 C12 170.8(2) . . . . ?
C6 N1 C18 C13 -172.5(2) . . . . ?
C6 N1 C18 C17 9.8(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 N1 C6 C1 -76.0(3) . . . . ?
C7 N1 C6 C5 104.4(2) . . . . ?
C7 N1 C18 C13 -21.2(3) . . . . ?
C7 N1 C18 C17 161.1(2) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C8 C7 C12 S2 -171.27(18) . . . . ?
C8 C7 C12 C11 3.6(3) . . . . ?
C8 C9 C10 C11 2.3(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 S2 172.1(2) . . . . ?
C10 C11 C12 C7 -3.1(4) . . . . ?
C12 S2 C13 C14 -161.5(2) . . . . ?
C12 S2 C13 C18 21.6(2) . . . . ?
C12 C7 C8 C9 -1.3(3) . . . . ?
C13 S2 C12 C7 -23.3(2) . . . . ?
C13 S2 C12 C11 161.64(19) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C13 C18 N1 -179.6(2) . . . . ?
C14 C13 C18 C17 -1.8(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 N1 178.5(2) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C18 N1 C6 C1 77.6(3) . . . . ?
C18 N1 C6 C5 -101.9(2) . . . . ?
C18 N1 C7 C8 -163.1(2) . . . . ?
C18 N1 C7 C12 19.4(3) . . . . ?
C18 C13 C14 C15 1.8(4) . . . . ?

_platon_squeeze_details          
;
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 77 13 ' '
2 0.500 0.000 1.000 77 13 ' '
3 0.000 0.500 0.000 77 13 ' '
4 1.000 0.500 0.500 77 13 ' '

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/MeOH'
_exptl_crystal_preparation       Luminescent
