# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_DPCP-3
_audit_block_doi                 10.5517/cc149rjq
_database_code_depnum_ccdc_archive 'CCDC 1052063'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.dyepig.2015.09.018 2015
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H24 S'
_chemical_formula_weight         476.60

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   13.805(3)
_cell_length_b                   23.501(6)
_cell_length_c                   7.6773(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2490.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5683
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 'Bruker SMART CCD area'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none'
_diffrn_reflns_number            15774
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5683
_reflns_number_gt                3954
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0496P)²+0.2406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_number_reflns         5683
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3922(2) 0.16543(10) 0.2700(4) 0.0370(6) Uani 1 1 d . . .
C2 C 0.3293(2) 0.12241(10) 0.2278(3) 0.0372(7) Uani 1 1 d . . .
C3 C 0.2294(2) 0.14385(11) 0.2391(4) 0.0428(7) Uani 1 1 d . . .
H3 H 0.1736 0.1234 0.2126 0.051 Uiso 1 1 calc R . .
C4 C 0.2327(2) 0.20062(10) 0.2968(3) 0.0368(7) Uani 1 1 d . . .
C5 C 0.3333(2) 0.21610(10) 0.3171(4) 0.0407(7) Uani 1 1 d . . .
H5A H 0.3462 0.2272 0.4365 0.049 Uiso 1 1 calc R . .
H5B H 0.3492 0.2478 0.2414 0.049 Uiso 1 1 calc R . .
C6 C 0.4980(2) 0.16672(11) 0.2701(4) 0.0404(7) Uani 1 1 d . . .
C7 C 0.5484(2) 0.20282(11) 0.3823(4) 0.0473(7) Uani 1 1 d . . .
H7A H 0.5140 0.2262 0.4579 0.057 Uiso 1 1 calc R . .
C8 C 0.6483(2) 0.20453(13) 0.3832(5) 0.0610(9) Uani 1 1 d . . .
H8A H 0.6801 0.2290 0.4594 0.073 Uiso 1 1 calc R . .
C9 C 0.7009(3) 0.17114(15) 0.2748(6) 0.0644(10) Uani 1 1 d . . .
H9A H 0.7682 0.1715 0.2793 0.077 Uiso 1 1 calc R . .
C10 C 0.6533(3) 0.13666(14) 0.1581(5) 0.0624(10) Uani 1 1 d . . .
H10A H 0.6889 0.1147 0.0802 0.075 Uiso 1 1 calc R . .
C11 C 0.5532(3) 0.13413(12) 0.1550(4) 0.0491(8) Uani 1 1 d . . .
H11A H 0.5223 0.1105 0.0754 0.059 Uiso 1 1 calc R . .
C12 C 0.3516(2) 0.06191(10) 0.1853(4) 0.0377(7) Uani 1 1 d . . .
C13 C 0.3000(2) 0.03393(12) 0.0549(4) 0.0508(8) Uani 1 1 d . . .
H13A H 0.2514 0.0532 -0.0049 0.061 Uiso 1 1 calc R . .
C14 C 0.3197(3) -0.02145(14) 0.0135(5) 0.0614(10) Uani 1 1 d . . .
H14A H 0.2860 -0.0389 -0.0768 0.074 Uiso 1 1 calc R . .
C15 C 0.3886(3) -0.05164(13) 0.1036(5) 0.0634(11) Uani 1 1 d . . .
H15A H 0.4012 -0.0894 0.0755 0.076 Uiso 1 1 calc R . .
C16 C 0.4385(3) -0.02540(12) 0.2355(5) 0.0568(9) Uani 1 1 d . . .
H16A H 0.4848 -0.0456 0.2980 0.068 Uiso 1 1 calc R . .
C17 C 0.4204(2) 0.03109(11) 0.2765(4) 0.0440(7) Uani 1 1 d . . .
H17A H 0.4548 0.0484 0.3660 0.053 Uiso 1 1 calc R . .
C18 C 0.1510(2) 0.23815(10) 0.3395(3) 0.0362(7) Uani 1 1 d . . .
C19 C 0.0540(2) 0.22221(11) 0.3174(4) 0.0449(7) Uani 1 1 d . . .
H19A H 0.0399 0.1869 0.2689 0.054 Uiso 1 1 calc R . .
C20 C -0.0206(2) 0.25726(11) 0.3653(4) 0.0458(8) Uani 1 1 d . . .
H20A H -0.0840 0.2454 0.3468 0.055 Uiso 1 1 calc R . .
C21 C -0.0042(2) 0.31026(11) 0.4410(3) 0.0389(7) Uani 1 1 d . . .
C22 C 0.0921(2) 0.32616(11) 0.4610(4) 0.0465(8) Uani 1 1 d . . .
H22A H 0.1063 0.3615 0.5091 0.056 Uiso 1 1 calc R . .
C23 C 0.1672(2) 0.29107(10) 0.4117(4) 0.0477(7) Uani 1 1 d . . .
H23A H 0.2306 0.3034 0.4275 0.057 Uiso 1 1 calc R . .
C24 C -0.0852(2) 0.34649(12) 0.5033(4) 0.0397(7) Uani 1 1 d . . .
C25 C -0.1656(3) 0.32043(14) 0.5784(4) 0.0563(9) Uani 1 1 d . . .
H25A H -0.1666 0.2810 0.5890 0.068 Uiso 1 1 calc R . .
C26 C -0.2442(3) 0.35168(15) 0.6381(5) 0.0695(10) Uani 1 1 d . . .
H26A H -0.2975 0.3329 0.6849 0.083 Uiso 1 1 calc R . .
C27 C -0.2444(3) 0.40966(15) 0.6288(4) 0.0573(8) Uani 1 1 d . . .
H27A H -0.2971 0.4303 0.6696 0.069 Uiso 1 1 calc R . .
C28 C -0.1651(2) 0.43748(13) 0.5581(4) 0.0449(8) Uani 1 1 d . . .
C29 C -0.0859(2) 0.40597(11) 0.4933(3) 0.0366(6) Uani 1 1 d . . .
C30 C -0.1502(2) 0.49809(13) 0.5358(3) 0.0443(8) Uani 1 1 d . . .
C31 C -0.2078(3) 0.54328(15) 0.5957(4) 0.0589(10) Uani 1 1 d . . .
H31A H -0.2655 0.5360 0.6541 0.071 Uiso 1 1 calc R . .
C32 C -0.1785(3) 0.59764(17) 0.5677(5) 0.0683(11) Uani 1 1 d . . .
H32A H -0.2168 0.6274 0.6080 0.082 Uiso 1 1 calc R . .
C33 C -0.0932(3) 0.60995(13) 0.4807(5) 0.0660(11) Uani 1 1 d . . .
H33A H -0.0751 0.6476 0.4633 0.079 Uiso 1 1 calc R . .
C34 C -0.0339(3) 0.56589(12) 0.4186(4) 0.0609(9) Uani 1 1 d . . .
H34A H 0.0230 0.5735 0.3583 0.073 Uiso 1 1 calc R . .
C35 C -0.0634(2) 0.51098(12) 0.4505(4) 0.0443(8) Uani 1 1 d . . .
S1 S 0.00245(6) 0.44919(3) 0.39835(11) 0.04196(17) 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
C1 C2 1.372(4) . ?
C1 C6 1.461(4) . ?
C1 C5 1.486(4) . ?
C2 C3 1.470(4) . ?
C2 C12 1.491(3) . ?
C3 C4 1.407(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.445(4) . ?
C4 C18 1.469(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.395(4) . ?
C6 C11 1.396(4) . ?
C7 C8 1.380(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.354(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.375(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C17 1.384(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.367(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.372(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.387(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.380(4) . ?
C18 C19 1.401(4) . ?
C19 C20 1.370(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.393(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.389(4) . ?
C21 C24 1.485(4) . ?
C22 C23 1.378(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 C25 1.392(4) . ?
C24 C29 1.400(4) . ?
C25 C26 1.389(5) . ?
C25 H25A 0.9300 . ?
C26 C27 1.365(4) . ?
C26 H26A 0.9300 . ?
C27 C28 1.386(5) . ?
C27 H27A 0.9300 . ?
C28 C29 1.411(4) . ?
C28 C30 1.449(4) . ?
C29 S1 1.747(3) . ?
C30 C35 1.398(4) . ?
C30 C31 1.404(4) . ?
C31 C32 1.357(5) . ?
C31 H31A 0.9300 . ?
C32 C33 1.384(5) . ?
C32 H32A 0.9300 . ?
C33 C34 1.403(5) . ?
C33 H33A 0.9300 . ?
C34 C35 1.375(4) . ?
C34 H34A 0.9300 . ?
C35 S1 1.760(3) . ?

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
C2 C1 C6 130.4(3) . . ?
C2 C1 C5 107.6(3) . . ?
C6 C1 C5 122.0(2) . . ?
C1 C2 C3 109.1(2) . . ?
C1 C2 C12 128.6(3) . . ?
C3 C2 C12 122.3(2) . . ?
C4 C3 C2 108.3(3) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
C3 C4 C5 107.7(3) . . ?
C3 C4 C18 128.0(3) . . ?
C5 C4 C18 124.3(2) . . ?
C4 C5 C1 107.3(2) . . ?
C4 C5 H5A 110.3 . . ?
C1 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
C1 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C7 C6 C11 116.9(3) . . ?
C7 C6 C1 120.8(3) . . ?
C11 C6 C1 122.3(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C10 C11 C6 120.7(3) . . ?
C10 C11 H11A 119.6 . . ?
C6 C11 H11A 119.6 . . ?
C17 C12 C13 117.8(3) . . ?
C17 C12 C2 122.0(3) . . ?
C13 C12 C2 120.1(3) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C12 C17 C16 120.7(3) . . ?
C12 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C23 C18 C19 116.4(3) . . ?
C23 C18 C4 120.4(3) . . ?
C19 C18 C4 123.1(2) . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
C19 C20 C21 121.8(3) . . ?
C19 C20 H20A 119.1 . . ?
C21 C20 H20A 119.1 . . ?
C22 C21 C20 116.2(3) . . ?
C22 C21 C24 122.1(2) . . ?
C20 C21 C24 121.6(3) . . ?
C23 C22 C21 121.9(3) . . ?
C23 C22 H22A 119.0 . . ?
C21 C22 H22A 119.0 . . ?
C22 C23 C18 121.8(3) . . ?
C22 C23 H23A 119.1 . . ?
C18 C23 H23A 119.1 . . ?
C25 C24 C29 117.2(3) . . ?
C25 C24 C21 118.8(3) . . ?
C29 C24 C21 124.1(3) . . ?
C26 C25 C24 121.8(3) . . ?
C26 C25 H25A 119.1 . . ?
C24 C25 H25A 119.1 . . ?
C27 C26 C25 120.8(4) . . ?
C27 C26 H26A 119.6 . . ?
C25 C26 H26A 119.6 . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27A 120.3 . . ?
C28 C27 H27A 120.3 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 C30 128.5(3) . . ?
C29 C28 C30 111.4(3) . . ?
C24 C29 C28 120.7(3) . . ?
C24 C29 S1 126.8(2) . . ?
C28 C29 S1 112.5(2) . . ?
C35 C30 C31 118.3(3) . . ?
C35 C30 C28 112.9(3) . . ?
C31 C30 C28 128.6(3) . . ?
C32 C31 C30 119.4(4) . . ?
C32 C31 H31A 120.3 . . ?
C30 C31 H31A 120.3 . . ?
C31 C32 C33 121.8(3) . . ?
C31 C32 H32A 119.1 . . ?
C33 C32 H32A 119.1 . . ?
C32 C33 C34 120.4(3) . . ?
C32 C33 H33A 119.8 . . ?
C34 C33 H33A 119.8 . . ?
C35 C34 C33 117.3(4) . . ?
C35 C34 H34A 121.3 . . ?
C33 C34 H34A 121.3 . . ?
C34 C35 C30 122.7(3) . . ?
C34 C35 S1 125.5(3) . . ?
C30 C35 S1 111.7(2) . . ?
C29 S1 C35 91.37(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
