# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_georg7
_database_code_depnum_ccdc_archive 'CCDC 2011482'
loop_
_audit_author_name
_audit_author_address
'Khalil Abboud'
;University of Florida
United States of America
;

_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H30 O S2'
_chemical_formula_weight         290.51

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.0392(2)
_cell_length_b                   8.4897(3)
_cell_length_c                   38.3953(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1642.60(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.5159
_exptl_transmission_factor_max   0.5648
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.314
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3--8.'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microsource 3.0'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22184
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         2.457
_diffrn_reflns_theta_max         31.154
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4854
_reflns_number_gt                4580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.879
_reflns_Friedel_fraction_full    0.998

_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 APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_refine_special_details          
; 
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and 
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). 
Methyl ones were allowed to rotate around the corresponding C---C. 

The hydroxyl proton is involved in an intramolecular hydrogen bond with S2 and
 an intermolecular hydrogen bond with S1. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1758 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.006(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4854
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.003
_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 0.86879(9) -0.06353(5) 0.74445(2) 0.03066(10) Uani 1 1 d . . . . .
S2 S 0.65034(9) 0.14051(5) 0.75008(2) 0.03188(10) Uani 1 1 d . . . . .
O1 O 0.3489(2) 0.02864(16) 0.68462(3) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.7634(3) -0.09992(18) 0.69971(4) 0.0238(3) Uani 1 1 d . . . . .
H1A H 0.919444 -0.129478 0.685474 0.029 Uiso 1 1 calc R U . . .
H1B H 0.636881 -0.189100 0.699310 0.029 Uiso 1 1 calc R U . . .
C2 C 0.6301(3) 0.04702(18) 0.68379(3) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.7078(3) 0.19228(18) 0.70508(4) 0.0263(3) Uani 1 1 d . . . . .
H3A H 0.597746 0.283972 0.698354 0.032 Uiso 1 1 calc R U . . .
H3B H 0.896825 0.218916 0.701269 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7111(3) 0.06225(19) 0.64562(4) 0.0233(3) Uani 1 1 d . . . . .
H4A H 0.905729 0.077177 0.644541 0.028 Uiso 1 1 calc R U . . .
H4B H 0.669602 -0.038119 0.633670 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5794(3) 0.19583(19) 0.62562(4) 0.0258(3) Uani 1 1 d . . . . .
H5A H 0.605453 0.295748 0.638467 0.031 Uiso 1 1 calc R U . . .
H5B H 0.386208 0.175677 0.624121 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6922(3) 0.2128(2) 0.58897(4) 0.0270(3) Uani 1 1 d . . . . .
H6A H 0.885981 0.230598 0.590625 0.032 Uiso 1 1 calc R U . . .
H6B H 0.664072 0.112901 0.576191 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5689(3) 0.3467(2) 0.56827(4) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.588894 0.445797 0.581590 0.032 Uiso 1 1 calc R U . . .
H7B H 0.376619 0.326099 0.565535 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6917(3) 0.3683(2) 0.53241(4) 0.0273(3) Uani 1 1 d . . . . .
H8A H 0.884248 0.387920 0.535140 0.033 Uiso 1 1 calc R U . . .
H8B H 0.670354 0.269434 0.519025 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5703(3) 0.5029(2) 0.51177(4) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.588296 0.601411 0.525368 0.032 Uiso 1 1 calc R U . . .
H9B H 0.378526 0.482174 0.508596 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6974(3) 0.52649(19) 0.47620(4) 0.0281(3) Uani 1 1 d . . . . .
H10A H 0.888794 0.548366 0.479425 0.034 Uiso 1 1 calc R U . . .
H10B H 0.681419 0.427471 0.462746 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5748(3) 0.6598(2) 0.45522(4) 0.0272(3) Uani 1 1 d . . . . .
H11A H 0.585506 0.758299 0.468955 0.033 Uiso 1 1 calc R U . . .
H11B H 0.384679 0.636317 0.451279 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7089(3) 0.6859(2) 0.42016(4) 0.0276(3) Uani 1 1 d . . . . .
H12A H 0.700744 0.586883 0.406592 0.033 Uiso 1 1 calc R U . . .
H12B H 0.898309 0.711085 0.424133 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5838(3) 0.8176(2) 0.39883(4) 0.0278(3) Uani 1 1 d . . . . .
H13A H 0.397267 0.789405 0.393669 0.033 Uiso 1 1 calc R U . . .
H13B H 0.582043 0.915160 0.412971 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7269(3) 0.8504(2) 0.36480(4) 0.0303(3) Uani 1 1 d . . . . .
H14A H 0.734289 0.752059 0.350980 0.036 Uiso 1 1 calc R U . . .
H14B H 0.911536 0.882649 0.369965 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5944(4) 0.9781(2) 0.34317(5) 0.0401(4) Uani 1 1 d . . . . .
H15A H 0.699568 0.997593 0.322141 0.060 Uiso 1 1 calc R U . . .
H15B H 0.582502 1.075186 0.356881 0.060 Uiso 1 1 calc R U . . .
H15C H 0.415709 0.943747 0.336548 0.060 Uiso 1 1 calc R U . . .
H1 H 0.311(6) 0.029(3) 0.7036(7) 0.061(8) Uiso 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
S1 C1 1.8240(16) . ?
S1 S2 2.0638(6) . ?
S2 C3 1.8063(15) . ?
O1 C2 1.4263(18) . ?
O1 H1 0.75(3) . ?
C1 C2 1.543(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.5266(19) . ?
C2 C3 1.530(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.525(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1 S1 S2 94.91(5) . . ?
C3 S2 S1 91.05(5) . . ?
C2 O1 H1 106(2) . . ?
C2 C1 S1 111.28(10) . . ?
C2 C1 H1A 109.4 . . ?
S1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
S1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C4 107.24(11) . . ?
O1 C2 C3 109.28(13) . . ?
C4 C2 C3 112.10(13) . . ?
O1 C2 C1 109.58(12) . . ?
C4 C2 C1 109.43(12) . . ?
C3 C2 C1 109.18(12) . . ?
C2 C3 S2 105.90(10) . . ?
C2 C3 H3A 110.6 . . ?
S2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
S2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C2 115.53(12) . . ?
C5 C4 H4A 108.4 . . ?
C2 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C2 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 C6 111.93(13) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 113.63(13) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 113.41(13) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 113.52(14) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 113.43(13) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 113.74(13) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.35(13) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.48(14) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.62(14) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.10(15) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 S1 0.75(3) 2.84(3) 3.4264(13) 137(3) 1_455 yes
O1 H1 S2 0.75(3) 2.65(3) 3.0866(13) 119(3) . yes

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_georg8
_database_code_depnum_ccdc_archive 'CCDC 2011483'
loop_
_audit_author_name
_audit_author_address
'Khalil Abboud'
;University of Florida
United States of America
;

_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H9 O S2'
_chemical_formula_weight         149.24

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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   19.7501(18)
_cell_length_b                   19.7501(18)
_cell_length_c                   7.4965(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2924.1(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0


_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   0.4221
_exptl_transmission_factor_max   0.4920
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.635
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3--8.'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19828
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.906
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1815
_reflns_number_gt                1382
_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 APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_refine_special_details          
; 
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and 
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). 
Methyl ones were allowed to rotate around the corresponding C---C. 

The hydroxyl proton was obtained from a Difference Fourier map and refined
 freely.  The hydrogen bonding among hydroxyl group lead to the formation of
 double layered sheet connected by S...S interactions.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+3.0365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1815
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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_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 0.54929(3) 0.57175(3) 0.04351(8) 0.04012(19) Uani 1 1 d . . . . .
S2 S 0.54167(3) 0.53242(3) 0.29789(8) 0.03851(19) Uani 1 1 d . . . . .
O1 O 0.69783(9) 0.54707(9) 0.2630(2) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.7234(18) 0.5491(18) 0.336(5) 0.074(12) Uiso 1 1 d . . . . .
C1 C 0.62929(12) 0.61636(12) 0.0775(3) 0.0389(5) Uani 1 1 d . . . . .
H1A H 0.663192 0.599763 -0.009441 0.047 Uiso 1 1 calc R U . . .
H1B H 0.622568 0.665392 0.056472 0.047 Uiso 1 1 calc R U . . .
C2 C 0.65553(11) 0.60531(11) 0.2661(3) 0.0322(4) Uani 1 1 d . . . . .
H2A H 0.683308 0.645410 0.301872 0.039 Uiso 1 1 calc R U . . .
C3 C 0.59625(11) 0.59765(12) 0.3979(3) 0.0389(5) Uani 1 1 d . . . . .
C4 C 0.55809(15) 0.66514(15) 0.4133(5) 0.0622(8) Uani 1 1 d . . . . .
H4A H 0.543982 0.680113 0.294319 0.093 Uiso 1 1 calc R U . . .
H4B H 0.518053 0.659080 0.488833 0.093 Uiso 1 1 calc R U . . .
H4C H 0.587884 0.699297 0.466482 0.093 Uiso 1 1 calc R U . . .
C5 C 0.61931(16) 0.57213(18) 0.5791(3) 0.0630(9) Uani 1 1 d . . . . .
H5A H 0.643405 0.529109 0.564437 0.095 Uiso 1 1 calc R U . . .
H5B H 0.649610 0.605507 0.633668 0.095 Uiso 1 1 calc R U . . .
H5C H 0.579779 0.565290 0.656020 0.095 Uiso 1 1 calc R U . . .


_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 C1 1.827(2) . ?
S1 S2 2.0646(8) . ?
S2 C3 1.840(2) . ?
O1 C2 1.422(3) . ?
O1 H1 0.75(4) . ?
C1 C2 1.522(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.540(3) . ?
C2 H2A 1.0000 . ?
C3 C5 1.518(4) . ?
C3 C4 1.536(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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
C1 S1 S2 96.65(8) . . ?
C3 S2 S1 94.03(8) . . ?
C2 O1 H1 110(3) . . ?
C2 C1 S1 110.79(15) . . ?
C2 C1 H1A 109.5 . . ?
S1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C1 107.53(18) . . ?
O1 C2 C3 112.18(18) . . ?
C1 C2 C3 110.59(18) . . ?
O1 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C5 C3 C4 111.6(2) . . ?
C5 C3 C2 112.3(2) . . ?
C4 C3 C2 109.6(2) . . ?
C5 C3 S2 107.93(18) . . ?
C4 C3 S2 110.53(17) . . ?
C2 C3 S2 104.64(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 S1 C1 C2 0.98(17) . . . . ?
S1 C1 C2 O1 90.57(19) . . . . ?
S1 C1 C2 C3 -32.2(2) . . . . ?
O1 C2 C3 C5 48.0(3) . . . . ?
C1 C2 C3 C5 168.0(2) . . . . ?
O1 C2 C3 C4 172.7(2) . . . . ?
C1 C2 C3 C4 -67.3(2) . . . . ?
O1 C2 C3 S2 -68.8(2) . . . . ?
C1 C2 C3 S2 51.3(2) . . . . ?
S1 S2 C3 C5 -162.97(18) . . . . ?
S1 S2 C3 C4 74.71(18) . . . . ?
S1 S2 C3 C2 -43.23(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O1 0.75(4) 1.97(4) 2.7137(18) 175(4) 3_565 yes

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.117




_publcif_funding_html            
;
;
