# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_i:\docume~1\struct~1\qwe72b2\qweb2y
_database_code_depnum_ccdc_archive 'CCDC 1052024'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(ethylenedithio)(2-hydroxypropylene-1,3-dithio)Tetrathiafulvalene 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 O S8, C10.58 H9.16 O S8'
_chemical_formula_sum            'C11 H10 O S8'
_chemical_formula_weight         414.67

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.5765(10)
_cell_length_b                   15.314(2)
_cell_length_c                   16.664(2)
_cell_angle_alpha                89.607(7)
_cell_angle_beta                 89.350(8)
_cell_angle_gamma                88.861(7)
_cell_volume                     1677.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6826
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.52

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    1.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      150(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       '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            45625
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         30.68
_reflns_number_total             10176
_reflns_number_gt                8407
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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. 
The cell contains some disordered solvent, most probably hexane from the 
crystallisation (from THF/hexane). No good model could be found, and the
model was subjected to SQUEEZE which found one void containing 40 electrons 
;

_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)+(0.0583P)²+0.3203P] 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         10176
_refine_ls_number_parameters     386
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
S1 S 1.35288(10) 0.62385(5) 0.31826(4) 0.03604(16) Uani 1 1 d A . .
S2 S 0.86288(9) 0.71976(4) 0.30900(4) 0.03031(14) Uani 1 1 d A . .
S3 S 1.23928(7) 0.53806(3) 0.16954(3) 0.01736(11) Uani 1 1 d . . .
S4 S 0.82365(7) 0.61231(3) 0.16142(3) 0.01743(11) Uani 1 1 d . . .
S5 S 1.12200(7) 0.37315(3) 0.06917(3) 0.01947(11) Uani 1 1 d . A .
S6 S 0.70508(7) 0.44108(3) 0.04493(3) 0.01556(10) Uani 1 1 d . A .
S7 S 1.02271(8) 0.18868(3) 0.03300(4) 0.02428(12) Uani 1 1 d . A .
S8 S 0.54508(8) 0.26927(3) -0.00669(3) 0.02033(11) Uani 1 1 d . A .
S21 S 0.99224(9) 0.27976(4) 0.32233(4) 0.03224(15) Uani 1 1 d D . .
S22 S 0.49312(9) 0.36749(4) 0.33700(5) 0.04033(18) Uani 1 1 d D . .
S23 S 0.83689(7) 0.13968(3) 0.42546(3) 0.01825(11) Uani 1 1 d . . .
S24 S 0.41957(7) 0.21255(3) 0.44001(3) 0.01786(11) Uani 1 1 d . . .
S25 S 0.75879(7) 0.01653(3) 0.58281(3) 0.01423(10) Uani 1 1 d . B .
S26 S 0.34348(7) 0.08945(3) 0.59776(3) 0.01483(10) Uani 1 1 d . B .
S27 S 0.78354(7) -0.04277(3) 0.75337(3) 0.01828(11) Uani 1 1 d . B .
S28 S 0.30365(8) 0.04807(3) 0.77314(3) 0.01857(11) Uani 1 1 d . B .
O1 O 0.6925(3) 0.07720(10) -0.05016(11) 0.0323(4) Uani 1 1 d D . .
H1 H 0.642(4) 0.0346(12) -0.0737(16) 0.039 Uiso 1 1 d D . .
O2 O 0.5175(2) -0.07167(10) 0.90825(9) 0.0221(3) Uani 1 1 d . . .
H2 H 0.4181 -0.0611 0.9390 0.027 Uiso 1 1 calc R . .
C1 C 1.2419(6) 0.7074(3) 0.3824(3) 0.0474(14) Uani 0.789(8) 1 d PD A 3
H1A H 1.1685 0.6787 0.4273 0.057 Uiso 0.789(8) 1 calc PR A 3
H1B H 1.3527 0.7416 0.4057 0.057 Uiso 0.789(8) 1 calc PR A 3
C2 C 1.0960(5) 0.7695(2) 0.3398(3) 0.0389(11) Uani 0.789(8) 1 d PD A 3
H2A H 1.1653 0.7936 0.2917 0.047 Uiso 0.789(8) 1 calc PR A 3
H2B H 1.0619 0.8188 0.3759 0.047 Uiso 0.789(8) 1 calc PR A 3
C3 C 1.1599(3) 0.60526(13) 0.24981(12) 0.0190(4) Uani 1 1 d . A .
C4 C 0.9706(3) 0.63973(13) 0.24603(13) 0.0191(4) Uani 1 1 d . A .
C5 C 0.9912(3) 0.52641(12) 0.13353(12) 0.0152(4) Uani 1 1 d . A .
C6 C 0.9418(3) 0.45635(12) 0.09019(12) 0.0143(3) Uani 1 1 d . . .
C7 C 0.9400(3) 0.29775(12) 0.03873(13) 0.0174(4) Uani 1 1 d . . .
C8 C 0.7513(3) 0.32938(12) 0.02610(12) 0.0157(4) Uani 1 1 d . A .
C9 C 0.9903(4) 0.16236(15) -0.07220(16) 0.0321(6) Uani 1 1 d . . .
H9B H 1.0431 0.2113 -0.1049 0.039 Uiso 1 1 calc R A .
H9A H 1.0759 0.1101 -0.0845 0.039 Uiso 1 1 calc R . .
C10 C 0.7741(4) 0.14474(14) -0.09891(14) 0.0288(5) Uani 1 1 d . A .
H10 H 0.7846 0.1214 -0.1547 0.035 Uiso 1 1 calc R . .
C11 C 0.6332(4) 0.22474(15) -0.10224(14) 0.0295(5) Uani 1 1 d . . .
H11A H 0.5124 0.2096 -0.1338 0.035 Uiso 1 1 calc R A .
H11B H 0.7045 0.2714 -0.1320 0.035 Uiso 1 1 calc R . .
C21 C 0.9023(4) 0.38752(18) 0.2963(2) 0.0320(9) Uani 0.845(7) 1 d PD B 1
H21A H 0.9070 0.4248 0.3445 0.038 Uiso 0.845(7) 1 calc PR B 1
H21B H 0.9955 0.4124 0.2555 0.038 Uiso 0.845(7) 1 calc PR B 1
C22 C 0.6881(4) 0.3907(3) 0.2638(2) 0.0381(9) Uani 0.845(7) 1 d PD B 1
H22B H 0.6794 0.3480 0.2196 0.046 Uiso 0.845(7) 1 calc PR B 1
H22A H 0.6610 0.4495 0.2408 0.046 Uiso 0.845(7) 1 calc PR B 1
C21A C 0.855(2) 0.3529(9) 0.2571(7) 0.031(3) Uiso 0.155(7) 1 d PD B 2
H21C H 0.9543 0.3849 0.2236 0.038 Uiso 0.155(7) 1 calc PR B 2
H21D H 0.7719 0.3178 0.2207 0.038 Uiso 0.155(7) 1 calc PR B 2
C22A C 0.7166(17) 0.4187(8) 0.2990(11) 0.031(3) Uiso 0.155(7) 1 d PD B 2
H22C H 0.6775 0.4657 0.2608 0.038 Uiso 0.155(7) 1 calc PR B 2
H22D H 0.7902 0.4455 0.3438 0.038 Uiso 0.155(7) 1 calc PR B 2
C23 C 0.7852(3) 0.23988(12) 0.37651(13) 0.0187(4) Uani 1 1 d . B .
C24 C 0.5947(3) 0.27332(13) 0.38292(13) 0.0198(4) Uani 1 1 d . B .
C25 C 0.6066(3) 0.14075(12) 0.47893(12) 0.0137(3) Uani 1 1 d . B .
C26 C 0.5747(3) 0.09035(11) 0.54422(11) 0.0127(3) Uani 1 1 d . . .
C27 C 0.6417(3) 0.00908(12) 0.67802(11) 0.0148(4) Uani 1 1 d . . .
C28 C 0.4519(3) 0.04367(12) 0.68530(11) 0.0146(4) Uani 1 1 d . B .
C29 C 0.6278(3) -0.13415(13) 0.78278(12) 0.0189(4) Uani 1 1 d . . .
H29B H 0.5745 -0.1607 0.7335 0.023 Uiso 1 1 calc R B .
H29A H 0.7166 -0.1786 0.8090 0.023 Uiso 1 1 calc R . .
C30 C 0.4493(3) -0.11438(12) 0.83879(12) 0.0167(4) Uani 1 1 d . B .
H30 H 0.3970 -0.1721 0.8572 0.020 Uiso 1 1 calc R . .
C31 C 0.2707(3) -0.06599(14) 0.79994(13) 0.0197(4) Uani 1 1 d . . .
H31A H 0.1525 -0.0695 0.8371 0.024 Uiso 1 1 calc R B .
H31B H 0.2353 -0.0977 0.7506 0.024 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 C3 1.745(2) . ?
S1 C1 1.809(3) . ?
S2 C4 1.752(2) . ?
S2 C2 1.806(3) . ?
S3 C5 1.758(2) . ?
S3 C3 1.761(2) . ?
S4 C5 1.7607(19) . ?
S4 C4 1.776(2) . ?
S5 C6 1.7571(19) . ?
S5 C7 1.7609(19) . ?
S6 C6 1.7578(19) . ?
S6 C8 1.7611(19) . ?
S7 C7 1.7492(19) . ?
S7 C9 1.817(3) . ?
S8 C8 1.7489(19) . ?
S8 C11 1.821(2) . ?
S21 C23 1.744(2) . ?
S21 C21A 1.793(6) . ?
S21 C21 1.794(3) . ?
S22 C24 1.752(2) . ?
S22 C22A 1.787(6) . ?
S22 C22 1.798(3) . ?
S23 C25 1.7483(19) . ?
S23 C23 1.762(2) . ?
S24 C25 1.7599(19) . ?
S24 C24 1.762(2) . ?
S25 C27 1.760(2) . ?
S25 C26 1.7638(18) . ?
S26 C26 1.7543(19) . ?
S26 C28 1.7657(19) . ?
S27 C27 1.7496(19) . ?
S27 C29 1.812(2) . ?
S28 C28 1.751(2) . ?
S28 C31 1.816(2) . ?
O1 C10 1.421(3) . ?
O2 C30 1.415(2) . ?
C1 C2 1.517(5) . ?
C3 C4 1.345(3) . ?
C5 C6 1.345(3) . ?
C7 C8 1.341(3) . ?
C9 C10 1.524(4) . ?
C10 C11 1.522(3) . ?
C21 C22 1.514(4) . ?
C21A C22A 1.513(7) . ?
C23 C24 1.347(3) . ?
C25 C26 1.347(3) . ?
C27 C28 1.350(3) . ?
C29 C30 1.519(3) . ?
C30 C31 1.525(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
C3 S1 C1 102.87(13) . . ?
C3 S1 C1A 96.9(5) . . ?
C1 S1 C1A 29.2(4) . . ?
C4 S2 C2 97.91(13) . . ?
C4 S2 C2A 102.6(4) . . ?
C2 S2 C2A 21.7(4) . . ?
C5 S3 C3 93.59(9) . . ?
C5 S4 C4 92.95(9) . . ?
C6 S5 C7 94.42(9) . . ?
C6 S6 C8 94.21(9) . . ?
C7 S7 C9 103.41(11) . . ?
C8 S8 C11 103.68(11) . . ?
C23 S21 C21A 98.0(6) . . ?
C23 S21 C21 101.41(11) . . ?
C21A S21 C21 29.2(5) . . ?
C24 S22 C22A 101.9(6) . . ?
C24 S22 C22 101.07(12) . . ?
C22A S22 C22 24.4(5) . . ?
C25 S23 C23 93.97(9) . . ?
C25 S24 C24 94.05(9) . . ?
C27 S25 C26 94.33(9) . . ?
C26 S26 C28 94.17(9) . . ?
C27 S27 C29 103.44(9) . . ?
C28 S28 C31 103.74(9) . . ?
C2 C1 S1 114.0(3) . . ?
C1 C2 S2 114.0(3) . . ?
C4 C3 S1 130.01(16) . . ?
C4 C3 S3 116.69(15) . . ?
S1 C3 S3 113.04(12) . . ?
C3 C4 S2 126.87(16) . . ?
C3 C4 S4 117.06(15) . . ?
S2 C4 S4 115.56(12) . . ?
C6 C5 S3 120.86(15) . . ?
C6 C5 S4 125.55(15) . . ?
S3 C5 S4 113.58(10) . . ?
C5 C6 S5 121.03(15) . . ?
C5 C6 S6 125.08(15) . . ?
S5 C6 S6 113.79(10) . . ?
C8 C7 S7 127.11(15) . . ?
C8 C7 S5 116.66(14) . . ?
S7 C7 S5 116.15(11) . . ?
C7 C8 S8 125.79(15) . . ?
C7 C8 S6 117.47(14) . . ?
S8 C8 S6 116.74(11) . . ?
C10 C9 S7 116.54(16) . . ?
O1 C10 C11 112.0(2) . . ?
O1 C10 C9 109.0(2) . . ?
C11 C10 C9 115.09(18) . . ?
C10 C11 S8 116.91(17) . . ?
C22 C21 S21 114.0(2) . . ?
C21 C22 S22 114.5(2) . . ?
C22A C21A S21 115.2(10) . . ?
C21A C22A S22 110.7(9) . . ?
C24 C23 S21 129.02(15) . . ?
C24 C23 S23 117.41(15) . . ?
S21 C23 S23 113.52(11) . . ?
C23 C24 S22 128.20(16) . . ?
C23 C24 S24 116.72(15) . . ?
S22 C24 S24 114.98(11) . . ?
C26 C25 S23 122.73(15) . . ?
C26 C25 S24 122.79(15) . . ?
S23 C25 S24 114.47(11) . . ?
C25 C26 S26 123.34(14) . . ?
C25 C26 S25 123.34(15) . . ?
S26 C26 S25 113.30(10) . . ?
C28 C27 S27 126.82(15) . . ?
C28 C27 S25 116.76(15) . . ?
S27 C27 S25 116.42(11) . . ?
C27 C28 S28 126.35(15) . . ?
C27 C28 S26 116.78(15) . . ?
S28 C28 S26 116.87(11) . . ?
C30 C29 S27 116.72(14) . . ?
O2 C30 C29 110.00(16) . . ?
O2 C30 C31 112.22(16) . . ?
C29 C30 C31 114.90(17) . . ?
C30 C31 S28 117.66(14) . . ?
C2A C1A S1 110.6(8) . . ?
C1A C2A S2 117.6(8) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        30.68
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.115
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.016 0.500 0.500 106 40 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_i:\docume~1\struct~1\qwe88b~1\reproc1
_database_code_depnum_ccdc_archive 'CCDC 1052025'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(4,4-(Bishydroxymethyl)cyclopentan-1,2-dithio)(ethylenedithio)-tetrathiafulvalene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 O2 S8'
_chemical_formula_sum            'C15 H16 O2 S8'
_chemical_formula_weight         484.76

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.2374(17)
_cell_length_b                   6.1992(6)
_cell_length_c                   34.267(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.472(4)
_cell_angle_gamma                90.00
_cell_volume                     3767.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9308
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.29

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      150(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       '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            37900
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3326
_reflns_number_gt                3152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0000P)²+131.7439P] 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         3326
_refine_ls_number_parameters     232
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1811
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_restrained_S_all      1.334
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

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 0.85619(11) 0.3079(4) 0.18809(7) 0.0236(5) Uani 1 1 d . . .
S2 S 0.79851(11) -0.1916(3) 0.21941(6) 0.0175(4) Uani 1 1 d . . .
S3 S 0.69399(10) 0.4126(3) 0.16968(6) 0.0155(4) Uani 1 1 d . . .
S4 S 0.64491(10) -0.0126(3) 0.19248(6) 0.0155(4) Uani 1 1 d . . .
S5 S 0.52061(10) 0.5308(3) 0.12624(6) 0.0148(4) Uani 1 1 d . . .
S6 S 0.47342(10) 0.0937(3) 0.14486(6) 0.0167(4) Uani 1 1 d . . .
S7 S 0.37547(10) 0.6167(3) 0.06576(6) 0.0162(4) Uani 1 1 d . . .
S8 S 0.32052(10) 0.1416(3) 0.08648(6) 0.0149(4) Uani 1 1 d . . .
O1 O 0.0844(3) 0.8285(9) 0.03422(16) 0.0177(12) Uani 1 1 d D . .
O2 O 0.0387(3) 0.2539(9) 0.02501(17) 0.0173(12) Uani 1 1 d D . .
C1 C 0.9112(4) 0.0701(14) 0.2045(3) 0.0210(18) Uani 1 1 d . . .
H1A H 0.9079 -0.0271 0.1812 0.025 Uiso 1 1 calc R . .
H1B H 0.9647 0.1125 0.2142 0.025 Uiso 1 1 calc R . .
C2 C 0.8866(4) -0.0526(15) 0.2375(3) 0.0241(19) Uani 1 1 d . . .
H2A H 0.8814 0.0495 0.2589 0.029 Uiso 1 1 calc R . .
H2B H 0.9261 -0.1589 0.2494 0.029 Uiso 1 1 calc R . .
C3 C 0.7648(4) 0.2191(13) 0.1870(2) 0.0145(16) Uani 1 1 d . . .
C4 C 0.7426(4) 0.0241(12) 0.1978(2) 0.0128(15) Uani 1 1 d . . .
C5 C 0.6189(4) 0.2300(13) 0.1665(2) 0.0138(16) Uani 1 1 d . . .
C6 C 0.5478(4) 0.2773(12) 0.1478(2) 0.0124(15) Uani 1 1 d . . .
C7 C 0.4322(4) 0.4385(12) 0.0994(2) 0.0120(15) Uani 1 1 d . . .
C8 C 0.4105(4) 0.2400(13) 0.1070(2) 0.0162(17) Uani 1 1 d . . .
C9 C 0.2806(4) 0.5801(12) 0.0757(2) 0.0125(15) Uani 1 1 d . . .
H9 H 0.2696 0.7073 0.0914 0.015 Uiso 1 1 calc R . .
C10 C 0.2690(4) 0.3742(11) 0.0984(2) 0.0087(14) Uani 1 1 d . . .
H10 H 0.2827 0.4014 0.1280 0.010 Uiso 1 1 calc R . .
C11 C 0.2211(4) 0.5707(13) 0.0362(2) 0.0141(16) Uani 1 1 d . . .
H11A H 0.2373 0.4747 0.0167 0.017 Uiso 1 1 calc R . .
H11B H 0.2109 0.7162 0.0243 0.017 Uiso 1 1 calc R . .
C12 C 0.1836(4) 0.3272(13) 0.0844(2) 0.0140(16) Uani 1 1 d . . .
H12A H 0.1584 0.3538 0.1066 0.017 Uiso 1 1 calc R . .
H12B H 0.1755 0.1745 0.0760 0.017 Uiso 1 1 calc R . .
C13 C 0.1503(4) 0.4787(12) 0.0484(2) 0.0111(15) Uani 1 1 d . . .
C14 C 0.1070(4) 0.6604(13) 0.0628(2) 0.0153(16) Uani 1 1 d . . .
H14A H 0.0615 0.5992 0.0697 0.018 Uiso 1 1 calc R . .
H14B H 0.1389 0.7228 0.0875 0.018 Uiso 1 1 calc R . .
C15 C 0.1009(4) 0.3585(13) 0.0132(2) 0.0150(16) Uani 1 1 d . . .
H15A H 0.0812 0.4611 -0.0089 0.018 Uiso 1 1 calc R . .
H15B H 0.1316 0.2490 0.0032 0.018 Uiso 1 1 calc R . .
H2 H 0.051(5) 0.124(7) 0.037(3) 0.025 Uiso 1 1 d D . .
H1 H 0.053(4) 0.803(16) 0.0103(13) 0.025 Uiso 1 1 d 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 C3 1.747(7) . ?
S1 C1 1.798(8) . ?
S2 C4 1.738(8) . ?
S2 C2 1.801(9) . ?
S3 C3 1.761(8) . ?
S3 C5 1.761(8) . ?
S4 C5 1.757(8) . ?
S4 C4 1.764(8) . ?
S5 C6 1.757(8) . ?
S5 C7 1.755(7) . ?
S6 C6 1.756(8) . ?
S6 C8 1.770(8) . ?
S7 C7 1.750(8) . ?
S7 C9 1.853(7) . ?
S8 C8 1.738(8) . ?
S8 C10 1.819(7) . ?
O1 C14 1.423(9) . ?
O2 C15 1.443(9) . ?
C1 C2 1.514(12) . ?
C3 C4 1.354(11) . ?
C5 C6 1.338(11) . ?
C7 C8 1.337(11) . ?
C9 C11 1.527(10) . ?
C9 C10 1.536(10) . ?
C10 C12 1.547(10) . ?
C11 C13 1.555(10) . ?
C12 C13 1.557(10) . ?
C13 C15 1.520(10) . ?
C13 C14 1.522(10) . ?

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
C3 S1 C1 102.0(4) . . ?
C4 S2 C2 99.6(4) . . ?
C3 S3 C5 94.7(4) . . ?
C5 S4 C4 95.1(4) . . ?
C6 S5 C7 93.6(4) . . ?
C6 S6 C8 94.0(4) . . ?
C7 S7 C9 103.6(3) . . ?
C8 S8 C10 96.9(3) . . ?
C2 C1 S1 113.9(6) . . ?
C1 C2 S2 112.3(6) . . ?
C4 C3 S1 128.3(6) . . ?
C4 C3 S3 117.2(6) . . ?
S1 C3 S3 114.4(4) . . ?
C3 C4 S2 128.4(6) . . ?
C3 C4 S4 116.5(6) . . ?
S2 C4 S4 115.0(4) . . ?
C6 C5 S4 123.2(6) . . ?
C6 C5 S3 122.8(6) . . ?
S4 C5 S3 113.8(4) . . ?
C5 C6 S5 123.0(6) . . ?
C5 C6 S6 122.3(6) . . ?
S5 C6 S6 114.7(4) . . ?
C8 C7 S5 118.4(6) . . ?
C8 C7 S7 123.5(6) . . ?
S5 C7 S7 118.0(4) . . ?
C7 C8 S8 122.7(6) . . ?
C7 C8 S6 116.3(6) . . ?
S8 C8 S6 120.4(5) . . ?
C11 C9 C10 105.3(6) . . ?
C11 C9 S7 110.1(5) . . ?
C10 C9 S7 116.1(5) . . ?
C9 C10 C12 104.3(6) . . ?
C9 C10 S8 113.9(5) . . ?
C12 C10 S8 108.4(5) . . ?
C9 C11 C13 103.9(6) . . ?
C10 C12 C13 108.2(6) . . ?
C15 C13 C14 111.3(6) . . ?
C15 C13 C12 112.4(6) . . ?
C14 C13 C12 109.0(6) . . ?
C15 C13 C11 110.0(6) . . ?
C14 C13 C11 110.0(6) . . ?
C12 C13 C11 103.8(6) . . ?
O1 C14 C13 114.1(6) . . ?
O2 C15 C13 110.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.156
####################################################################### 
# 
# 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_QWE87
_database_code_depnum_ccdc_archive 'CCDC 1052026'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
cis-4",4"-bis(acetoxymethyl)cyclopenta-1,2-dithio)(ethylenedithio)tetrathiafulvalene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 O4 S8'
_chemical_formula_weight         568.83

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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5807(3)
_cell_length_b                   12.1870(7)
_cell_length_c                   15.5413(9)
_cell_angle_alpha                111.004(3)
_cell_angle_beta                 100.434(3)
_cell_angle_gamma                91.420(3)
_cell_volume                     1138.86(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7396
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.46

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      150(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50303
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.683
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5642
_reflns_number_gt                4940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.8775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5642
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29234(6) 0.23040(3) 0.20185(3) 0.01924(9) Uani 1 1 d . . . . .
S2 S 0.83585(6) 0.28973(4) 0.27061(3) 0.02232(10) Uani 1 1 d . . . . .
S3 S 0.28966(6) 0.46523(3) 0.34916(3) 0.01620(9) Uani 1 1 d . . . . .
S4 S 0.74751(6) 0.51421(3) 0.40609(3) 0.01620(9) Uani 1 1 d . . . . .
S5 S 0.23970(6) 0.72729(3) 0.49369(3) 0.01553(9) Uani 1 1 d . . . . .
S6 S 0.70043(6) 0.77610(3) 0.54649(3) 0.01510(9) Uani 1 1 d . . . . .
S7 S 0.18297(6) 0.96024(3) 0.64196(3) 0.01520(10) Uani 0.9389(7) 1 d . . P A 1
S8 S 0.67228(6) 1.01731(3) 0.69209(3) 0.01503(10) Uani 0.9389(7) 1 d . . P A 1
O1 O 0.16986(18) 1.20486(11) 0.87506(9) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.2829(2) 1.08078(12) 0.94605(9) 0.0287(3) Uani 1 1 d . . . . .
O3 O 0.13447(18) 1.41709(10) 0.83321(9) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.2538(2) 1.59637(11) 0.94165(9) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.4909(2) 0.13511(13) 0.16397(11) 0.0161(3) Uani 1 1 d . . . . .
H1A H 0.5318 0.0954 0.2091 0.019 Uiso 1 1 calc R U . . .
H1B H 0.4319 0.0732 0.1018 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6834(3) 0.19952(14) 0.15636(11) 0.0190(3) Uani 1 1 d . . . . .
H2A H 0.6411 0.2502 0.1200 0.023 Uiso 1 1 calc R U . . .
H2B H 0.7698 0.1410 0.1216 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4388(2) 0.35510(13) 0.29003(10) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.6464(2) 0.37818(13) 0.31617(11) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.5043(2) 0.56462(13) 0.42103(10) 0.0134(3) Uani 1 1 d . . . . .
C6 C 0.4833(2) 0.67344(13) 0.48111(10) 0.0132(3) Uani 1 1 d . . . . .
C7 C 0.3456(3) 0.86030(14) 0.58563(13) 0.0139(3) Uani 0.9389(7) 1 d . . P A 1
C8 C 0.5535(3) 0.88356(14) 0.60764(12) 0.0129(3) Uani 0.9389(7) 1 d . . P A 1
C9 C 0.2820(3) 1.09253(14) 0.62553(11) 0.0148(3) Uani 0.9389(7) 1 d . . P A 1
H9 H 0.2352 1.0828 0.5581 0.018 Uiso 0.9389(7) 1 calc R U P A 1
C10 C 0.5207(3) 1.12235(14) 0.65371(11) 0.0153(3) Uani 0.9389(7) 1 d . . P A 1
H10 H 0.5717 1.1310 0.5994 0.018 Uiso 0.9389(7) 1 calc R U P A 1
C11 C 0.1906(3) 1.20154(14) 0.68794(12) 0.0192(3) Uani 0.9389(7) 1 d . . P A 1
H11A H 0.1518 1.2549 0.6536 0.023 Uiso 0.9389(7) 1 calc R U P A 1
H11B H 0.0652 1.1766 0.7057 0.023 Uiso 0.9389(7) 1 calc R U P A 1
C12 C 0.3600(2) 1.26497(13) 0.77628(11) 0.0172(3) Uani 1 1 d . . . . .
C13 C 0.5615(3) 1.24366(15) 0.73692(13) 0.0200(3) Uani 0.9389(7) 1 d . . P A 1
H13A H 0.6789 1.2426 0.7864 0.024 Uiso 0.9389(7) 1 calc R U P A 1
H13B H 0.5961 1.3072 0.7148 0.024 Uiso 0.9389(7) 1 calc R U P A 1
C14 C 0.3716(3) 1.20773(15) 0.84921(12) 0.0208(3) Uani 1 1 d . . . . .
H14A H 0.4115 1.1264 0.8230 0.025 Uiso 1 1 calc R U . . .
H14B H 0.4783 1.2533 0.9057 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1468(3) 1.13532(14) 0.92374(11) 0.0190(3) Uani 1 1 d . . . . .
C16 C -0.0657(3) 1.13355(16) 0.94504(12) 0.0256(4) Uani 1 1 d . . . . .
H16A H -0.1674 1.0929 0.8865 0.038 Uiso 1 1 calc R U . . .
H16B H -0.0994 1.2148 0.9743 0.038 Uiso 1 1 calc R U . . .
H16C H -0.0696 1.0918 0.9882 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3432(3) 1.39739(14) 0.81781(12) 0.0213(3) Uani 1 1 d . . . . .
H17A H 0.4443 1.4335 0.8782 0.026 Uiso 1 1 calc R U . . .
H17B H 0.3751 1.4346 0.7741 0.026 Uiso 1 1 calc R U . . .
C18 C 0.1115(3) 1.52245(14) 0.89650(11) 0.0180(3) Uani 1 1 d . . . . .
C19 C -0.1119(3) 1.53303(16) 0.90280(13) 0.0261(4) Uani 1 1 d . . . . .
H19A H -0.1220 1.5988 0.9605 0.039 Uiso 1 1 calc R U . . .
H19B H -0.1730 1.4596 0.9040 0.039 Uiso 1 1 calc R U . . .
H19C H -0.1869 1.5476 0.8480 0.039 Uiso 1 1 calc R U . . .
S7A S 0.1628(10) 0.9822(5) 0.5658(4) 0.016 Uiso 0.0611(7) 1 d . U P A 2
S8A S 0.6525(10) 1.0410(5) 0.6262(4) 0.016 Uiso 0.0611(7) 1 d . U P A 2
C7A C 0.335(5) 0.868(3) 0.552(2) 0.016 Uiso 0.0611(7) 1 d . U P A 2
C8A C 0.540(5) 0.895(3) 0.576(2) 0.016 Uiso 0.0611(7) 1 d . U P A 2
C9A C 0.266(4) 1.070(2) 0.6874(18) 0.016 Uiso 0.0611(7) 1 d . U P A 2
H9A H 0.2075 1.0418 0.7318 0.019 Uiso 0.0611(7) 1 calc R U P A 2
C10A C 0.514(4) 1.100(2) 0.7165(18) 0.016 Uiso 0.0611(7) 1 d . U P A 2
H10A H 0.5734 1.0810 0.7731 0.019 Uiso 0.0611(7) 1 calc R U P A 2
C11A C 0.1906 1.2015 0.6879 0.016 Uiso 0.0611(7) 1 d . U P A 2
H11C H 0.2108 1.2183 0.6321 0.019 Uiso 0.0611(7) 1 calc R U P A 2
H11D H 0.0477 1.2139 0.6985 0.019 Uiso 0.0611(7) 1 calc R U P A 2
C13A C 0.5615 1.2436 0.7369 0.016 Uiso 0.0611(7) 1 d . U P A 2
H13C H 0.6895 1.2823 0.7843 0.019 Uiso 0.0611(7) 1 calc R U P A 2
H13D H 0.5569 1.2612 0.6792 0.019 Uiso 0.0611(7) 1 calc R U P A 2


_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 C3 1.7528(15) . ?
S1 C1 1.8072(16) . ?
S2 C4 1.7483(15) . ?
S2 C2 1.8080(17) . ?
S3 C5 1.7559(15) . ?
S3 C3 1.7654(15) . ?
S4 C5 1.7535(15) . ?
S4 C4 1.7584(15) . ?
S5 C7A 1.67(3) . ?
S5 C7 1.7544(17) . ?
S5 C6 1.7639(15) . ?
S6 C8 1.7484(16) . ?
S6 C6 1.7647(15) . ?
S6 C8A 1.79(3) . ?
S7 C7 1.7420(17) . ?
S7 C9 1.8419(17) . ?
S8 C8 1.7386(17) . ?
S8 C10 1.8396(17) . ?
O1 C15 1.3448(19) . ?
O1 C14 1.458(2) . ?
O2 C15 1.203(2) . ?
O3 C18 1.3405(19) . ?
O3 C17 1.4477(19) . ?
O4 C18 1.203(2) . ?
C1 C2 1.519(2) . ?
C3 C4 1.345(2) . ?
C5 C6 1.348(2) . ?
C7 C8 1.345(2) . ?
C9 C11 1.547(2) . ?
C9 C10 1.549(2) . ?
C10 C13 1.554(2) . ?
C11 C12 1.539(2) . ?
C12 C14 1.522(2) . ?
C12 C17 1.524(2) . ?
C12 C11A 1.5388(16) . ?
C12 C13 1.548(2) . ?
C12 C13A 1.5480(16) . ?
C15 C16 1.496(2) . ?
C18 C19 1.497(2) . ?
S7A C7A 1.79(3) . ?
S7A C9A 1.80(3) . ?
S8A C8A 1.75(3) . ?
S8A C10A 1.76(3) . ?
C7A C8A 1.34(5) . ?
C9A C10A 1.61(4) . ?
C9A C11A 1.69(3) . ?
C10A C13A 1.68(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
C3 S1 C1 102.11(7) . . ?
C4 S2 C2 99.20(7) . . ?
C5 S3 C3 95.11(7) . . ?
C5 S4 C4 94.93(7) . . ?
C7A S5 C6 95.2(11) . . ?
C7 S5 C6 94.07(7) . . ?
C8 S6 C6 94.36(7) . . ?
C6 S6 C8A 91.8(11) . . ?
C7 S7 C9 99.30(8) . . ?
C8 S8 C10 100.95(8) . . ?
C15 O1 C14 115.09(13) . . ?
C18 O3 C17 116.04(13) . . ?
C2 C1 S1 113.71(11) . . ?
C1 C2 S2 112.06(11) . . ?
C4 C3 S1 128.67(12) . . ?
C4 C3 S3 116.84(11) . . ?
S1 C3 S3 114.47(8) . . ?
C3 C4 S2 128.14(12) . . ?
C3 C4 S4 117.86(11) . . ?
S2 C4 S4 114.00(9) . . ?
C6 C5 S4 122.43(12) . . ?
C6 C5 S3 122.29(12) . . ?
S4 C5 S3 115.24(8) . . ?
C5 C6 S5 122.92(12) . . ?
C5 C6 S6 121.69(12) . . ?
S5 C6 S6 115.23(8) . . ?
C8 C7 S7 122.00(13) . . ?
C8 C7 S5 117.79(13) . . ?
S7 C7 S5 120.16(10) . . ?
C7 C8 S8 121.23(13) . . ?
C7 C8 S6 117.80(13) . . ?
S8 C8 S6 120.95(10) . . ?
C11 C9 C10 105.65(13) . . ?
C11 C9 S7 108.91(11) . . ?
C10 C9 S7 115.54(11) . . ?
C9 C10 C13 106.30(13) . . ?
C9 C10 S8 116.64(11) . . ?
C13 C10 S8 107.65(12) . . ?
C12 C11 C9 106.95(13) . . ?
C14 C12 C17 112.52(14) . . ?
C14 C12 C11 112.63(14) . . ?
C17 C12 C11 112.36(14) . . ?
C14 C12 C11A 112.63(12) . . ?
C17 C12 C11A 112.36(12) . . ?
C14 C12 C13 107.26(13) . . ?
C17 C12 C13 109.01(13) . . ?
C11 C12 C13 102.38(13) . . ?
C14 C12 C13A 107.27(11) . . ?
C17 C12 C13A 109.01(11) . . ?
C11A C12 C13A 102.37(9) . . ?
C12 C13 C10 106.98(13) . . ?
O1 C14 C12 109.41(13) . . ?
O2 C15 O1 122.89(16) . . ?
O2 C15 C16 124.95(16) . . ?
O1 C15 C16 112.16(14) . . ?
O3 C17 C12 109.09(13) . . ?
O4 C18 O3 123.54(15) . . ?
O4 C18 C19 125.88(15) . . ?
O3 C18 C19 110.57(14) . . ?
C7A S7A C9A 98.1(13) . . ?
C8A S8A C10A 100.6(14) . . ?
C8A C7A S5 119(3) . . ?
C8A C7A S7A 121(2) . . ?
S5 C7A S7A 119.6(19) . . ?
C7A C8A S8A 122(3) . . ?
C7A C8A S6 118(2) . . ?
S8A C8A S6 120.2(18) . . ?
C10A C9A C11A 100.7(16) . . ?
C10A C9A S7A 116.2(17) . . ?
C11A C9A S7A 98.6(13) . . ?
C9A C10A C13A 106.6(17) . . ?
C9A C10A S8A 116.2(17) . . ?
C13A C10A S8A 98.9(13) . . ?
C12 C11A C9A 89.8(9) . . ?
C12 C13A C10A 88.2(9) . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.068


_vrf_PLAT410_QWE87               
; 
PROBLEM: short H--H contacts from H14A  and H9A to H10A       

RESPONSE: The apparent contacts are between the major
conformation and the minor conformation in the disordered model.
H9A and H10A belong to a minor (6%) conformation of the
molecule, which is clear to locate for cyclopentane ring and fused
dithiolodithiin ring in the difference map, but is too diffuse to
be modelled in the CH2OAc side chains. 
;

_vrf_PLAT163_QWE87               
; 
PROBLEM: zero esd for x, y and z for C11A and C13A

RESPONSE: These atoms belong to the minor conformation (6%) of the molecule, 
and were fixed to be in the same position and C11 and C13 for the major
conformation.
;
_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_p1J
_database_code_depnum_ccdc_archive 'CCDC 1052027'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT434_p1J                 
;
PROBLEM: Short Inter HL..HL Contact I2 .. I3A .. 3.23 Ang.
RESPONSE: This short intermolecular contact is a halogen bond
;
_vrf_PLAT019_p1J                 
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0 0.973 Report
RESPONSE: The crystals of this compound diffracted weakly
;
_vrf_PLAT420_p1J                 
;
PROBLEM: D-H Without Acceptor O1 - H1 .. Please Check
RESPONSE: OH group has no acceptor
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "'2(C11 H10 O S8), 2(I1.52),I2, 1.556(I)'"
_chemical_formula_sum            'C22 H20 I6.60 O2 S16'
_chemical_formula_weight         1666.37

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'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9246(4)
_cell_length_b                   8.6449(4)
_cell_length_c                   16.2901(8)
_cell_angle_alpha                87.891(2)
_cell_angle_beta                 86.545(2)
_cell_angle_gamma                76.982(2)
_cell_volume                     1085.02(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8829
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.99

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.550
_exptl_crystal_F_000             530
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    5.51
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42831
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3808
_reflns_number_gt                3214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+21.0514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3808
_refine_ls_number_parameters     232
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.1787
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.4459(4) 0.0329(5) 0.16871(19) 0.0591(9) Uani 1 1 d . . . . .
S12 S 0.8068(3) -0.2513(3) 0.21162(15) 0.0303(5) Uani 1 1 d . . . . .
S13 S 0.4681(3) 0.1462(3) 0.33597(16) 0.0335(6) Uani 1 1 d . . . . .
S14 S 0.7773(3) -0.0924(3) 0.37367(14) 0.0258(5) Uani 1 1 d . . . . .
S15 S 0.4649(3) 0.3007(3) 0.51273(15) 0.0276(5) Uani 1 1 d . . . . .
S16 S 0.7763(3) 0.0642(3) 0.55167(16) 0.0290(5) Uani 1 1 d . . . . .
S17 S 0.4298(3) 0.4717(3) 0.66624(16) 0.0305(5) Uani 1 1 d . . . . .
S18 S 0.8133(4) 0.1942(4) 0.71200(19) 0.0481(8) Uani 1 1 d . . . . .
O1 O 0.826(2) -0.0192(19) -0.0067(8) 0.106(5) Uani 1 1 d . . . . .
H1 H 0.7663 0.0626 -0.0256 0.159 Uiso 1 1 calc R U . . .
C11 C 0.8805(14) -0.1368(14) 0.1269(7) 0.041(2) Uani 1 1 d . . . . .
H11A H 0.9226 -0.0511 0.1496 0.049 Uiso 1 1 calc R U . . .
H11B H 0.9781 -0.2048 0.0978 0.049 Uiso 1 1 calc R U . . .
C12 C 0.7454(17) -0.0648(17) 0.0646(7) 0.054(3) Uani 1 1 d . . . . .
H12 H 0.6843 -0.1465 0.0510 0.065 Uiso 1 1 calc R U . . .
C13 C 0.6132(19) 0.0766(18) 0.0970(8) 0.063(4) Uani 1 1 d . . . . .
H13A H 0.5578 0.1364 0.0506 0.076 Uiso 1 1 calc R U . . .
H13B H 0.6740 0.1447 0.1238 0.076 Uiso 1 1 calc R U . . .
C14 C 0.5523(13) 0.0093(12) 0.2607(7) 0.036(2) Uani 1 1 d . . . . .
C15 C 0.6982(12) -0.1017(11) 0.2774(6) 0.0266(19) Uani 1 1 d . . . . .
C16 C 0.6216(11) 0.0685(10) 0.4057(6) 0.0256(19) Uani 1 1 d . . . . .
C17 C 0.6200(11) 0.1360(10) 0.4818(6) 0.027(2) Uani 1 1 d . . . . .
C18 C 0.5507(11) 0.3178(10) 0.6071(6) 0.0246(18) Uani 1 1 d . . . . .
C19 C 0.6968(11) 0.2082(11) 0.6244(6) 0.027(2) Uani 1 1 d . . . . .
C20 C 0.7408(18) 0.4065(18) 0.7436(10) 0.065(4) Uani 1 1 d . . . . .
H20A H 0.7924 0.4195 0.7947 0.077 Uiso 1 1 calc R U . . .
H20B H 0.7820 0.4744 0.7020 0.077 Uiso 1 1 calc R U . . .
C21 C 0.5572(18) 0.4553(15) 0.7545(8) 0.055(4) Uani 1 1 d . . . . .
H21A H 0.5305 0.5579 0.7803 0.066 Uiso 1 1 calc R U . . .
H21B H 0.5183 0.3810 0.7933 0.066 Uiso 1 1 calc R U . . .
I1 I 0.01330(9) 0.58545(8) 0.57116(6) 0.0538(3) Uani 1 1 d . . . . .
I2 I 0.95248(12) 0.24151(10) 0.25610(8) 0.0785(4) Uani 1 1 d . . . . .
I3A I 0.0006(9) 0.4162(4) 0.0806(3) 0.0700(8) Uani 0.324(2) 1 d . . P A 1
I3B I 0.1365(7) 0.3947(5) 0.1037(4) 0.0700(8) Uani 0.252(3) 1 d . . P B 2
I3C I -0.0857(8) 0.4180(6) 0.0818(4) 0.0700(8) Uani 0.268(3) 1 d . . P C 3
I3D I 0.1149(16) 0.4098(9) 0.0698(6) 0.0700(8) Uani 0.155(3) 1 d . . P B 4
I4 I 0.3717(7) 0.5129(4) -0.0059(2) 0.0884(13) Uani 0.2987 1 d . . P . .


_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
S11 C14 1.747(10) . ?
S11 C13 1.809(16) . ?
S12 C15 1.746(10) . ?
S12 C11 1.813(11) . ?
S13 C16 1.721(9) . ?
S13 C14 1.732(11) . ?
S14 C16 1.713(9) . ?
S14 C15 1.735(9) . ?
S15 C17 1.727(9) . ?
S15 C18 1.742(9) . ?
S16 C17 1.728(9) . ?
S16 C19 1.737(9) . ?
S17 C18 1.739(9) . ?
S17 C21 1.790(12) . ?
S18 C19 1.731(10) . ?
S18 C20 1.877(15) . ?
O1 C12 1.380(17) . ?
O1 H1 0.8200 . ?
C11 C12 1.533(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.508(18) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.361(13) . ?
C16 C17 1.387(14) . ?
C18 C19 1.359(13) . ?
C20 C21 1.423(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
I1 I1 2.8377(18) 2_566 ?
I3A I3A 2.951(10) 2_565 ?
I3B I4 2.833(7) . ?
I3C I4 2.587(8) 2_565 ?
I3D I4 2.625(13) . ?
I3D I3D 3.14(2) 2_565 ?
I4 I4 2.016(10) 2_665 ?
I4 I3C 2.587(8) 2_565 ?

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
C14 S11 C13 101.1(6) . . ?
C15 S12 C11 101.7(5) . . ?
C16 S13 C14 95.3(5) . . ?
C16 S14 C15 96.1(5) . . ?
C17 S15 C18 96.1(4) . . ?
C17 S16 C19 95.8(4) . . ?
C18 S17 C21 101.2(5) . . ?
C19 S18 C20 98.0(6) . . ?
C12 O1 H1 109.5 . . ?
C12 C11 S12 116.0(8) . . ?
C12 C11 H11A 108.3 . . ?
S12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
S12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
O1 C12 C13 108.8(12) . . ?
O1 C12 C11 110.1(12) . . ?
C13 C12 C11 112.9(10) . . ?
O1 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C11 C12 H12 108.3 . . ?
C12 C13 S11 116.0(11) . . ?
C12 C13 H13A 108.3 . . ?
S11 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
S11 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C15 C14 S13 117.2(8) . . ?
C15 C14 S11 126.3(8) . . ?
S13 C14 S11 116.4(6) . . ?
C14 C15 S14 115.7(8) . . ?
C14 C15 S12 125.7(8) . . ?
S14 C15 S12 118.6(5) . . ?
C17 C16 S14 122.9(7) . . ?
C17 C16 S13 121.4(7) . . ?
S14 C16 S13 115.7(6) . . ?
C16 C17 S15 122.6(7) . . ?
C16 C17 S16 122.4(7) . . ?
S15 C17 S16 115.0(6) . . ?
C19 C18 S17 129.9(8) . . ?
C19 C18 S15 116.1(7) . . ?
S17 C18 S15 113.9(5) . . ?
C18 C19 S18 127.2(7) . . ?
C18 C19 S16 117.0(7) . . ?
S18 C19 S16 115.8(5) . . ?
C21 C20 S18 112.3(11) . . ?
C21 C20 H20A 109.1 . . ?
S18 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
S18 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 S17 118.8(10) . . ?
C20 C21 H21A 107.6 . . ?
S17 C21 H21A 107.6 . . ?
C20 C21 H21B 107.6 . . ?
S17 C21 H21B 107.6 . . ?
H21A C21 H21B 107.1 . . ?
I4 I3D I3D 86.2(5) . 2_565 ?
I4 I4 I3C 155.8(3) 2_665 2_565 ?
I4 I4 I3D 137.4(4) 2_665 . ?
I4 I4 I3B 126.8(3) 2_665 . ?

_refine_diff_density_max         3.861
_refine_diff_density_min         -2.560
_refine_diff_density_rms         0.230

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_absnew
_database_code_depnum_ccdc_archive 'CCDC 1052028'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT019_absnew              
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.972 Report
RESPONSE: ...
;
_vrf_PLAT201_absnew              
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          6 Report
RESPONSE: Substantial disorder in main residue led to multiple part occupancy
          C and O atoms which were not refined anisotropically.
;
_vrf_PLAT041_absnew              
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Due to substantial disorder not all H atoms were included in the 
          structure. In addition checkcif identifies a close O...O contact
          which leads to an erroneous formula. This contact arises between
          symmetry equivalent part-occupancy disordered CH2OH side chains
          and the reported chemical formula is correct.   
;
_vrf_PLAT043_absnew              
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      11.97 Check 
RESPONSE: See above.
;
_vrf_PLAT068_absnew              
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check
RESPONSE: See above
;
_vrf_PLAT241_absnew              
;
PROBLEM: High      Ueq as Compared to Neighbors for .....        C25 Check 
RESPONSE: This report and related ALERT C reports (below) arise from 
          substantial disorder of the CH2OH group. A discussion of the 
          crystallographic issues arising with disorder of the CH2OH pendant 
          groups is discussed in the cif, as well as disorder in one of the 
          two crystallographially independent I3- anions.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            
;
Hydroxymethyl-(BEDT-TTF) triiodide
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 O S8, I3'
_chemical_formula_sum            'C11 H10 I3 O S8'
_chemical_formula_weight         795.37

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'
I I -0.4742 1.8119 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           ?
_space_group_name_H-M_alt        I2/c
_space_group_name_Hall           ?

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.5595(7)
_cell_length_b                   13.7315(7)
_cell_length_c                   33.707(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.022(6)
_cell_angle_gamma                90
_cell_volume                     6672.9(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4567
_cell_measurement_theta_min      3.2130
_cell_measurement_theta_max      23.9440


_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.375
_exptl_crystal_F_000             4452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    4.965
_shelx_estimated_absorpt_T_min   0.291
_shelx_estimated_absorpt_T_max   0.543
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 7.9916
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            19151
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.032
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             5873
_reflns_number_gt                4400
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
_computing_structure_solution     'SHELXS'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
;
_refine_special_details          
;
The structure was initially solved by direct methods to reveal three BEDT cations
and three I3- anions in the asymmetric unit of the C2/c space group.  ADDSYMM 
revealed a missing symmetry element and further refinement was undertaken 
in I2/a with 1.5 BDT cations and 1.5 tri-iodide anions in the asymmetric unit.
One I3- located on a general position refined satisfactorily but the I3- located on a
special position was significantly disordered and refined over multiple 
positions such that the total site occupancy of the I atoms fo this I3- ion summed
to 1.5 with additional sites included until the residual electron density reduced 
below 2e-. The BEDT units appeared well located with one cation on a general position 
and one on a special position. For both cations the CH2OH side chain was poorly defined 
and apparently disordered over multiple sites. One CH2OH group was added 
to each crystallographically independent unsaturated C of the BEDT backbone using a 
FRAG FEND command and refined with a series of 1,2- and 1,3-distance 
constraints (DFIX). These sidechains shared a common U(iso) and their sof's refined
and finally fixed in the latter stages of refinement.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)²+188.7567P] 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       .
_refine_ls_number_reflns         5873
_refine_ls_number_parameters     313
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_ref         0.2140
_refine_ls_wR_factor_gt          0.1987
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.43921(8) 0.75819(8) 0.11648(4) 0.0650(4) Uani 1 1 d . . . . .
I2 I 0.35477(7) 0.78559(6) 0.03402(3) 0.0493(3) Uani 1 1 d . . . . .
I3 I 0.28074(8) 0.80480(7) -0.05066(4) 0.0607(4) Uani 1 1 d . . . . .
I4 I 1.0000 0.4303(5) 0.2500 0.1406(19) Uani 0.681(5) 2 d S TU P . .
I6 I 1.0000 0.693(3) 0.2500 0.1406(19) Uani 0.099(4) 2 d S TU P . .
I7 I 1.0000 0.5070(15) 0.2500 0.1406(19) Uani 0.221(5) 2 d S TU P . .
I5 I 0.8343(4) 0.3121(4) 0.24968(11) 0.229(2) Uani 0.741(3) 1 d . U P . .
I8 I 1.0635(19) 0.8767(19) 0.2513(6) 0.229(2) Uani 0.132(3) 1 d . U P . .
I9 I 0.740(3) 0.340(2) 0.2623(6) 0.229(2) Uani 0.127(3) 1 d . . P . .
S12 S 0.4554(3) 0.7336(3) -0.11930(13) 0.0605(11) Uani 1 1 d D . . . .
S11 S 0.5568(4) 0.5212(3) -0.14466(13) 0.0718(14) Uani 1 1 d D . . . .
C1 C 0.525(2) 0.628(2) -0.1747(8) 0.138(10) Uiso 1 1 d D . . . .
H1 H 0.4603 0.6196 -0.1887 0.166 Uiso 1 1 calc R U . A 1
C2 C 0.5312(15) 0.7229(16) -0.1551(7) 0.093(6) Uiso 1 1 d D . . . .
H2 H 0.5187 0.7758 -0.1755 0.111 Uiso 1 1 calc R U . B 2
C13 C 0.590(5) 0.627(3) -0.2056(13) 0.28(4) Uiso 0.42 1 d D . P C 1
H13A H 0.6470 0.6639 -0.1961 0.342 Uiso 0.42 1 calc R U P C 1
H13B H 0.6069 0.5592 -0.2115 0.342 Uiso 0.42 1 calc R U P C 1
O14 O 0.542(7) 0.670(11) -0.2392(16) 0.55(7) Uiso 0.42 1 d D . P C 1
C14 C 0.6270(13) 0.734(6) -0.1325(16) 0.28(4) Uiso 0.25 1 d D . P D 2
H14A H 0.6698 0.7613 -0.1501 0.342 Uiso 0.25 1 calc R U P D 2
H14B H 0.6264 0.7781 -0.1093 0.342 Uiso 0.25 1 calc R U P D 2
O15 O 0.653(9) 0.641(8) -0.120(8) 0.55(7) Uiso 0.25 1 d D . P D 2
S13 S 0.6027(3) 0.4912(2) -0.05771(11) 0.0422(8) Uani 1 1 d . . . . .
S14 S 0.5138(2) 0.6694(2) -0.03552(11) 0.0389(8) Uani 1 1 d . . . . .
S15 S 0.6867(2) 0.4559(2) 0.03431(12) 0.0439(9) Uani 1 1 d . . . . .
S16 S 0.5965(2) 0.6325(2) 0.05678(11) 0.0404(8) Uani 1 1 d . . . . .
C3 C 0.5486(10) 0.5633(9) -0.0968(4) 0.043(3) Uani 1 1 d . . . . .
C4 C 0.5076(10) 0.6437(9) -0.0866(4) 0.043(3) Uani 1 1 d . . . . .
C5 C 0.5806(9) 0.5682(9) -0.0201(4) 0.040(3) Uani 1 1 d . . . . .
C6 C 0.6170(9) 0.5538(9) 0.0192(4) 0.036(3) Uani 1 1 d . . . . .
C7 C 0.7059(10) 0.4891(11) 0.0850(5) 0.051(4) Uani 1 1 d . . . . .
C8 C 0.6633(10) 0.5701(10) 0.0953(5) 0.049(4) Uani 1 1 d . . . . .
S17 S 0.7808(3) 0.4125(3) 0.11599(15) 0.0694(13) Uani 1 1 d D . . . .
S18 S 0.6681(4) 0.6207(3) 0.14295(14) 0.0697(13) Uani 1 1 d D . . . .
C9 C 0.8215(18) 0.5013(16) 0.1526(7) 0.115(8) Uiso 1 1 d D . . . .
H9 H 0.8696 0.4704 0.1728 0.138 Uiso 1 1 calc R U . E 4
C10 C 0.7542(16) 0.5512(18) 0.1741(7) 0.127(9) Uiso 1 1 d D . . . .
H10 H 0.7238 0.5036 0.1905 0.152 Uiso 1 1 calc R U . F 3
C11 C 0.806(3) 0.627(4) 0.2006(17) 0.28(4) Uiso 0.21 1 d D . P G 3
H11A H 0.8375 0.5970 0.2255 0.342 Uiso 0.21 1 calc R U P G 3
H11B H 0.8524 0.6600 0.1866 0.342 Uiso 0.21 1 calc R U P G 3
O12 O 0.739(5) 0.692(13) 0.209(8) 0.55(7) Uiso 0.21 1 d D . P G 3
C12 C 0.868(6) 0.577(4) 0.1300(18) 0.28(4) Uiso 0.12 1 d D . P H 4
H12A H 0.8593 0.6425 0.1408 0.342 Uiso 0.12 1 calc R U P H 4
H12B H 0.9351 0.5632 0.1317 0.342 Uiso 0.12 1 calc R U P H 4
O13 O 0.82(3) 0.57(3) 0.091(4) 0.55(7) Uiso 0.12 1 d D . P H 4
S21 S 1.1150(3) 0.5844(3) 0.02989(11) 0.0459(9) Uani 1 1 d . . . . .
S22 S 0.9852(3) 0.4523(3) 0.06000(11) 0.0458(9) Uani 1 1 d . . . . .
C21 C 1.0216(9) 0.5077(9) 0.0189(4) 0.041(3) Uani 1 1 d . . . . .
C22 C 1.1278(10) 0.5669(9) 0.0805(5) 0.045(4) Uani 1 1 d . . . . .
C23 C 1.0685(10) 0.5039(10) 0.0950(4) 0.045(3) Uani 1 1 d . . . . .
S24 S 1.0633(3) 0.4749(3) 0.14523(12) 0.0605(11) Uani 1 1 d D . . . .
S23 S 1.2198(3) 0.6326(3) 0.10642(13) 0.0599(11) Uani 1 1 d D . . . .
C25 C 1.1770(15) 0.510(2) 0.1671(10) 0.171(13) Uiso 1 1 d D . . . .
H25 H 1.1822 0.5030 0.1968 0.205 Uiso 1 1 calc R U . I 1
C24 C 1.2103(17) 0.6077(17) 0.1579(5) 0.105(7) Uiso 1 1 d D . . . .
H24 H 1.2717 0.6197 0.1745 0.126 Uiso 1 1 calc R U . J 2
C27 C 1.2392(17) 0.437(3) 0.151(3) 0.28(4) Uiso 0.14 1 d D . P K 1
H27A H 1.3000 0.4664 0.1483 0.342 Uiso 0.14 1 calc R U P K 1
H27B H 1.2493 0.3803 0.1694 0.342 Uiso 0.14 1 calc R U P K 1
O28 O 1.193(16) 0.41(2) 0.114(6) 0.55(7) Uiso 0.14 1 d D . P K 1
C26 C 1.141(5) 0.680(3) 0.1693(15) 0.28(4) Uiso 0.36 1 d D . P L 2
H26A H 1.1717 0.7283 0.1884 0.342 Uiso 0.36 1 calc R U P L 2
H26B H 1.1094 0.7137 0.1454 0.342 Uiso 0.36 1 calc R U P L 2
O27 O 1.079(8) 0.623(6) 0.187(5) 0.55(7) Uiso 0.36 1 d D . P L 2


_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
I1 C12 2.56(2) 8_465 ?
I1 I2 2.9028(17) . ?
I2 I3 2.9187(17) . ?
I4 I7 1.053(18) . ?
I4 I5 2.906(7) . ?
I4 I5 2.906(7) 2_755 ?
I6 I7 2.56(4) . ?
I6 I8 2.68(4) 2_755 ?
I6 I8 2.68(4) . ?
I5 I9 1.54(3) . ?
I5 I9 2.36(3) 7_655 ?
I5 I5 2.993(12) 7_655 ?
I8 I8 1.84(6) 2_755 ?
I9 I5 2.36(3) 7_655 ?
I9 I9 2.63(6) 7_655 ?
S12 C2 1.75(2) . ?
S12 C4 1.757(14) . ?
S11 C3 1.733(15) . ?
S11 C1 1.81(3) . ?
C1 C2 1.46(3) . ?
C1 C13 1.498(10) . ?
C1 H1 1.0000 . ?
C2 C14 1.499(10) . ?
C2 H2 1.0000 . ?
C13 O14 1.381(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O14 O14 1.3(2) 2_654 ?
C14 O15 1.381(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
S13 C5 1.715(14) . ?
S13 C3 1.745(15) . ?
S14 C5 1.733(13) . ?
S14 C4 1.746(15) . ?
S15 C6 1.717(12) . ?
S15 C7 1.751(16) . ?
S16 C6 1.723(13) . ?
S16 C8 1.737(15) . ?
C3 C4 1.324(18) . ?
C5 C6 1.373(19) . ?
C7 C8 1.34(2) . ?
C7 S17 1.753(15) . ?
C8 S18 1.742(16) . ?
S17 C9 1.777(17) . ?
S18 C10 1.793(18) . ?
C9 C10 1.47(3) . ?
C9 C12 1.500(10) . ?
C9 H9 1.0000 . ?
C10 C11 1.501(10) . ?
C10 H10 1.0000 . ?
C11 O12 1.381(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O13 1.381(10) . ?
C12 I1 2.56(2) 8_565 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
S21 C22 1.706(16) . ?
S21 C21 1.719(14) . ?
S22 C23 1.723(15) . ?
S22 C21 1.728(14) . ?
C21 C21 1.36(3) 5_765 ?
C22 C23 1.361(19) . ?
C22 S23 1.745(14) . ?
C23 S24 1.750(15) . ?
S24 C25 1.784(19) . ?
S23 C24 1.792(17) . ?
C25 C24 1.47(3) . ?
C25 C27 1.501(10) . ?
C25 H25 1.0000 . ?
C24 C26 1.497(10) . ?
C24 H24 1.0000 . ?
C27 O28 1.380(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C26 O27 1.382(10) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

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
C12 I1 I2 85.8(16) 8_465 . ?
I1 I2 I3 175.87(4) . . ?
I7 I4 I5 123.96(14) . . ?
I7 I4 I5 123.95(14) . 2_755 ?
I5 I4 I5 112.1(3) . 2_755 ?
I7 I6 I8 159.9(6) . 2_755 ?
I7 I6 I8 159.9(6) . . ?
I8 I6 I8 40.1(12) 2_755 . ?
I4 I7 I6 180.000(11) . . ?
I9 I5 I9 82.0(14) . 7_655 ?
I9 I5 I4 129.2(13) . . ?
I9 I5 I4 148.9(10) 7_655 . ?
I9 I5 I5 51.4(12) . 7_655 ?
I9 I5 I5 30.6(8) 7_655 7_655 ?
I4 I5 I5 179.0(3) . 7_655 ?
I8 I8 I6 69.9(6) 2_755 . ?
I5 I9 I5 98.0(14) . 7_655 ?
I5 I9 I9 62.7(14) . 7_655 ?
I5 I9 I9 35.4(10) 7_655 7_655 ?
C2 S12 C4 96.6(9) . . ?
C3 S11 C1 101.9(10) . . ?
C2 C1 C13 109(2) . . ?
C2 C1 S11 118(2) . . ?
C13 C1 S11 104.1(18) . . ?
C2 C1 H1 108.4 . . ?
C13 C1 H1 108.4 . . ?
S11 C1 H1 108.4 . . ?
C1 C2 C14 109(2) . . ?
C1 C2 S12 112.6(17) . . ?
C14 C2 S12 105.9(17) . . ?
C1 C2 H2 109.9 . . ?
C14 C2 H2 109.9 . . ?
S12 C2 H2 109.9 . . ?
O14 C13 C1 105.5(15) . . ?
O14 C13 H13A 110.6 . . ?
C1 C13 H13A 110.6 . . ?
O14 C13 H13B 110.6 . . ?
C1 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
O14 O14 C13 141(6) 2_654 . ?
O15 C14 C2 104.9(15) . . ?
O15 C14 H14A 110.8 . . ?
C2 C14 H14A 110.8 . . ?
O15 C14 H14B 110.8 . . ?
C2 C14 H14B 110.8 . . ?
H14A C14 H14B 108.8 . . ?
C5 S13 C3 95.5(7) . . ?
C5 S14 C4 94.7(7) . . ?
C6 S15 C7 95.3(7) . . ?
C6 S16 C8 96.0(7) . . ?
C4 C3 S11 127.8(12) . . ?
C4 C3 S13 116.7(11) . . ?
S11 C3 S13 115.6(8) . . ?
C3 C4 S14 117.5(11) . . ?
C3 C4 S12 126.4(12) . . ?
S14 C4 S12 115.8(7) . . ?
C6 C5 S13 122.5(10) . . ?
C6 C5 S14 122.0(10) . . ?
S13 C5 S14 115.4(9) . . ?
C5 C6 S15 122.2(10) . . ?
C5 C6 S16 122.4(10) . . ?
S15 C6 S16 115.4(8) . . ?
C8 C7 S15 116.9(12) . . ?
C8 C7 S17 127.8(13) . . ?
S15 C7 S17 115.3(9) . . ?
C7 C8 S16 116.4(12) . . ?
C7 C8 S18 127.5(12) . . ?
S16 C8 S18 116.0(8) . . ?
C7 S17 C9 97.0(10) . . ?
C8 S18 C10 105.2(10) . . ?
C10 C9 C12 108(2) . . ?
C10 C9 S17 118.9(18) . . ?
C12 C9 S17 104.5(15) . . ?
C10 C9 H9 108.4 . . ?
C12 C9 H9 108.4 . . ?
S17 C9 H9 108.4 . . ?
C9 C10 C11 108(2) . . ?
C9 C10 S18 114.9(18) . . ?
C11 C10 S18 103.3(15) . . ?
C9 C10 H10 110.2 . . ?
C11 C10 H10 110.2 . . ?
S18 C10 H10 110.2 . . ?
O12 C11 C10 105.0(15) . . ?
O12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
O12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
O13 C12 C9 104.9(15) . . ?
O13 C12 I1 92(8) . 8_565 ?
C9 C12 I1 157(2) . 8_565 ?
O13 C12 H12A 110.8 . . ?
C9 C12 H12A 110.8 . . ?
I1 C12 H12A 48.0 8_565 . ?
O13 C12 H12B 110.8 . . ?
C9 C12 H12B 110.8 . . ?
I1 C12 H12B 75.7 8_565 . ?
H12A C12 H12B 108.8 . . ?
C22 S21 C21 95.8(7) . . ?
C23 S22 C21 95.9(7) . . ?
C21 C21 S21 123.2(14) 5_765 . ?
C21 C21 S22 122.0(14) 5_765 . ?
S21 C21 S22 114.8(8) . . ?
C23 C22 S21 117.6(11) . . ?
C23 C22 S23 129.0(12) . . ?
S21 C22 S23 113.4(8) . . ?
C22 C23 S22 115.8(11) . . ?
C22 C23 S24 127.5(12) . . ?
S22 C23 S24 116.6(9) . . ?
C23 S24 C25 100.0(12) . . ?
C22 S23 C24 103.2(10) . . ?
C24 C25 C27 108(2) . . ?
C24 C25 S24 118(2) . . ?
C27 C25 S24 103.9(15) . . ?
C24 C25 H25 108.8 . . ?
C27 C25 H25 108.8 . . ?
S24 C25 H25 108.8 . . ?
C25 C24 C26 106.9(19) . . ?
C25 C24 S23 116.8(19) . . ?
C26 C24 S23 105.6(15) . . ?
C25 C24 H24 109.1 . . ?
C26 C24 H24 109.1 . . ?
S23 C24 H24 109.1 . . ?
O28 C27 C25 105.0(15) . . ?
O28 C27 H27A 110.7 . . ?
C25 C27 H27A 110.7 . . ?
O28 C27 H27B 110.7 . . ?
C25 C27 H27B 110.7 . . ?
H27A C27 H27B 108.8 . . ?
O27 C26 C24 104.2(15) . . ?
O27 C26 H26A 110.9 . . ?
C24 C26 H26A 110.9 . . ?
O27 C26 H26B 110.9 . . ?
C24 C26 H26B 110.9 . . ?
H26A C26 H26B 108.9 . . ?

_refine_diff_density_max         1.294
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.198

_shelxl_version_number           2013-3



