# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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/. 
# 
# Audit and citation data items have may 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_pfl01
_database_code_depnum_ccdc_archive 'CCDC 1026287'
_audit_update_record             
;
2014-09-25 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_date             2014-09-23T12:04:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C24 H34 O4 S4'
_chemical_formula_sum            'C24 H34 O4 S4'
_chemical_formula_weight         514.75

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

_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                   4.919(2)
_cell_length_b                   7.285(1)
_cell_length_c                   18.574(2)
_cell_angle_alpha                84.19(1)
_cell_angle_beta                 86.42(1)
_cell_angle_gamma                84.08(2)
_cell_volume                     657.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

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

_exptl_crystal_description       colorless
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.3
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             274
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.959

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4216
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_reflns_number_total             3803
_reflns_number_gt                2847
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_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)+(0.0998P)²+0.3053P] 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_number_reflns         3803
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1763
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.58

#------------------ 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'
O O 0.0106 0.006 '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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.5403(4) 0.5264(3) 0.03395(12) 0.0372(4) Uani 1 d . . .
C2 C 0.4455(4) 0.6815(3) 0.06790(12) 0.0372(4) Uani 1 d . . .
C3 C 0.5695(4) 0.6955(3) 0.13345(12) 0.0396(4) Uani 1 d . . .
C4 C 0.7595(5) 0.5488(3) 0.15056(13) 0.0433(5) Uani 1 d . . .
C5 C 0.2235(10) 0.9734(5) 0.0782(2) 0.0939(14) Uani 1 d . . .
H5A H 0.3389 1.0612 0.0523 0.113 Uiso 1 calc R . .
H5B H 0.0359 1.0278 0.0744 0.113 Uiso 1 calc R . .
C6 C 0.2804(11) 0.9608(5) 0.1489(2) 0.1069(18) Uani 1 d . . .
H6A H 0.1188 0.9242 0.1771 0.128 Uiso 1 calc R . .
H6B H 0.307 1.0845 0.1604 0.128 Uiso 1 calc R . .
C7 C 0.7273(6) 0.4257(4) 0.29609(14) 0.0553(6) Uani 1 d . . .
H7A H 0.8032 0.4343 0.3425 0.066 Uiso 1 calc R . .
H7B H 0.5579 0.5065 0.2941 0.066 Uiso 1 calc R . .
C8 C 0.6623(6) 0.2287(4) 0.29262(15) 0.0582(6) Uani 1 d . . .
H8A H 0.8315 0.1475 0.2919 0.07 Uiso 1 calc R . .
H8B H 0.5738 0.2207 0.248 0.07 Uiso 1 calc R . .
C9 C 0.4778(7) 0.1633(5) 0.35618(17) 0.0639(7) Uani 1 d . . .
H9A H 0.3046 0.24 0.3545 0.077 Uiso 1 calc R . .
H9B H 0.5606 0.1822 0.4006 0.077 Uiso 1 calc R . .
C10 C 0.4213(7) -0.0390(5) 0.35922(18) 0.0684(8) Uani 1 d . . .
H10A H 0.3342 -0.0579 0.3155 0.082 Uiso 1 calc R . .
H10B H 0.5941 -0.1163 0.3602 0.082 Uiso 1 calc R . .
C11 C 0.2420(9) -0.0997(6) 0.4239(2) 0.0863(11) Uani 1 d . . .
H11A H 0.3256 -0.0739 0.4673 0.104 Uiso 1 calc R . .
H11B H 0.0673 -0.025 0.4215 0.104 Uiso 1 calc R . .
C12 C 0.1901(13) -0.2992(7) 0.4315(3) 0.1201(19) Uani 1 d . . .
H12A H 0.1426 -0.3335 0.3857 0.18 Uiso 1 calc R . .
H12B H 0.0423 -0.3182 0.4669 0.18 Uiso 1 calc R . .
H12C H 0.3522 -0.3741 0.4469 0.18 Uiso 1 calc R . .
O1 O 0.2520(3) 0.8125(2) 0.03999(10) 0.0475(4) Uani 1 d . . .
O2 O 0.5074(4) 0.8400(2) 0.17418(10) 0.0510(4) Uani 1 d . . .
S1 S 0.78492(12) 0.39539(8) 0.08513(3) 0.04444(18) Uani 1 d . . .
S2 S 0.96545(13) 0.51026(10) 0.22447(4) 0.0546(2) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0355(9) 0.0340(9) 0.0399(10) 0.0004(8) -0.0042(8) 0.0044(7)
C2 0.0349(9) 0.0326(9) 0.0419(10) 0.0010(8) -0.0042(8) 0.0037(7)
C3 0.0400(10) 0.0371(10) 0.0412(10) -0.0018(8) -0.0046(8) -0.0016(8)
C4 0.0418(11) 0.0437(11) 0.0437(11) 0.0012(9) -0.0099(9) -0.0007(9)
C5 0.126(3) 0.068(2) 0.086(2) -0.0382(18) -0.051(2) 0.058(2)
C6 0.144(4) 0.074(2) 0.105(3) -0.049(2) -0.071(3) 0.060(2)
C7 0.0590(15) 0.0629(16) 0.0439(12) -0.0003(11) -0.0126(11) -0.0047(12)
C8 0.0600(16) 0.0652(16) 0.0496(14) 0.0005(12) -0.0057(12) -0.0121(13)
C9 0.0655(17) 0.0710(19) 0.0536(15) 0.0018(13) -0.0046(13) -0.0047(14)
C10 0.0700(19) 0.076(2) 0.0599(17) -0.0024(15) 0.0011(15) -0.0180(16)
C11 0.100(3) 0.094(3) 0.067(2) -0.0009(19) 0.004(2) -0.035(2)
C12 0.134(4) 0.095(3) 0.130(4) 0.007(3) 0.023(4) -0.043(3)
O1 0.0500(9) 0.0397(8) 0.0513(9) -0.0076(7) -0.0162(7) 0.0141(7)
O2 0.0555(10) 0.0461(9) 0.0521(10) -0.0115(7) -0.0128(8) 0.0040(7)
S1 0.0429(3) 0.0404(3) 0.0471(3) -0.0005(2) -0.0091(2) 0.0107(2)
S2 0.0460(3) 0.0631(4) 0.0551(4) 0.0069(3) -0.0204(3) -0.0084(3)


#------------------ 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
C1 C2 1.374(3) . ?
C1 C1 1.445(4) 2_665 ?
C1 S1 1.728(2) . ?
C2 O1 1.364(2) . ?
C2 C3 1.413(3) . ?
C3 O2 1.356(3) . ?
C3 C4 1.371(3) . ?
C4 S1 1.723(2) . ?
C4 S2 1.740(2) . ?
C5 C6 1.353(5) . ?
C5 O1 1.420(3) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 O2 1.421(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.511(4) . ?
C7 S2 1.819(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.512(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.523(5) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.502(5) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.492(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?

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 C1 127.9(2) . 2_665 ?
C2 C1 S1 109.33(16) . . ?
C1 C1 S1 122.7(2) 2_665 . ?
O1 C2 C1 122.9(2) . . ?
O1 C2 C3 122.81(19) . . ?
C1 C2 C3 114.32(18) . . ?
O2 C3 C4 124.2(2) . . ?
O2 C3 C2 123.19(19) . . ?
C4 C3 C2 112.6(2) . . ?
C3 C4 S1 110.59(18) . . ?
C3 C4 S2 128.6(2) . . ?
S1 C4 S2 120.79(13) . . ?
C6 C5 O1 120.3(3) . . ?
C6 C5 H5A 107.2 . . ?
O1 C5 H5A 107.2 . . ?
C6 C5 H5B 107.2 . . ?
O1 C5 H5B 107.2 . . ?
H5A C5 H5B 106.9 . . ?
C5 C6 O2 119.7(3) . . ?
C5 C6 H6A 107.4 . . ?
O2 C6 H6A 107.4 . . ?
C5 C6 H6B 107.4 . . ?
O2 C6 H6B 107.4 . . ?
H6A C6 H6B 106.9 . . ?
C8 C7 S2 114.9(2) . . ?
C8 C7 H7A 108.6 . . ?
S2 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
S2 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 112.1(3) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 114.9(3) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 113.3(3) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 115.7(4) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 O1 C5 112.0(2) . . ?
C3 O2 C6 112.5(2) . . ?
C4 S1 C1 93.13(10) . . ?
C4 S2 C7 101.71(12) . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
