# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2ND_a
_database_code_depnum_ccdc_archive 'CCDC 1477173'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 O3 S'
_chemical_formula_sum            'C6 H8 O3 S'
_chemical_formula_weight         160.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1126(2)
_cell_length_b                   8.1510(2)
_cell_length_c                   25.8070(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1496.16(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      68.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    3.436
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.712
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_absorpt_special_details   
'crystal mounted on a Cryoloop using Paratone-N'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13849
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.425
_diffrn_reflns_theta_max         68.728
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2623
_reflns_number_gt                2565
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.989

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.5718P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2623
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S1 S 0.50310(11) -0.02821(7) 0.40246(2) 0.02714(17) Uani 1 1 d . . . . .
S2 S 0.00236(10) 1.23968(7) 0.37112(2) 0.02497(17) Uani 1 1 d . . . . .
O1 O 0.4900(3) 0.19188(19) 0.33135(6) 0.0191(4) Uani 1 1 d . . . . .
O2 O 0.3920(3) 0.4421(2) 0.39654(7) 0.0231(4) Uani 1 1 d . . . . .
O3 O 0.3070(3) 0.5867(2) 0.32818(8) 0.0274(4) Uani 1 1 d . . . . .
O4 O -0.0800(3) 0.8022(2) 0.32230(7) 0.0201(4) Uani 1 1 d . . . . .
O5 O 0.0015(3) 0.9539(2) 0.41364(6) 0.0203(4) Uani 1 1 d . . . . .
O6 O -0.1948(3) 0.5962(2) 0.36793(8) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.5008(4) 0.1607(3) 0.38206(9) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.5138(4) 0.3119(3) 0.41621(9) 0.0228(5) Uani 1 1 d . . . . .
H2 H 0.6466 0.3522 0.4158 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3972(4) 0.4753(3) 0.34550(9) 0.0196(5) Uani 1 1 d . . . . .
C4 C 0.5204(4) 0.3612(3) 0.31414(9) 0.0179(5) Uani 1 1 d . . . . .
H4 H 0.6551 0.3911 0.3200 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4557(4) 0.2841(4) 0.47169(10) 0.0350(7) Uani 1 1 d . . . . .
H5A H 0.4659 0.3873 0.4910 0.052 Uiso 1 1 calc R U . . .
H5B H 0.5382 0.2017 0.4874 0.052 Uiso 1 1 calc R U . . .
H5C H 0.3254 0.2453 0.4727 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4803(4) 0.3658(3) 0.25694(9) 0.0235(6) Uani 1 1 d . . . . .
H6A H 0.5598 0.2853 0.2392 0.035 Uiso 1 1 calc R U . . .
H6B H 0.5074 0.4758 0.2435 0.035 Uiso 1 1 calc R U . . .
H6C H 0.3477 0.3394 0.2509 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0188(4) 1.0411(3) 0.36983(9) 0.0176(5) Uani 1 1 d . . . . .
C8 C 0.0552(3) 0.9362(3) 0.32236(9) 0.0184(5) Uani 1 1 d . . . . .
H8 H 0.1850 0.8895 0.3247 0.022 Uiso 1 1 calc R U . . .
C9 C 0.0341(4) 1.0234(4) 0.27125(10) 0.0269(6) Uani 1 1 d . . . . .
H9A H 0.0523 0.9450 0.2429 0.040 Uiso 1 1 calc R U . . .
H9B H 0.1283 1.1108 0.2687 0.040 Uiso 1 1 calc R U . . .
H9C H -0.0921 1.0711 0.2689 0.040 Uiso 1 1 calc R U . . .
C10 C -0.0938(4) 0.7131(3) 0.36575(10) 0.0201(5) Uani 1 1 d . . . . .
C11 C 0.0256(4) 0.7757(3) 0.41025(9) 0.0209(5) Uani 1 1 d . . . . .
H11 H 0.1607 0.7495 0.4035 0.025 Uiso 1 1 calc R U . . .
C12 C -0.0322(5) 0.7042(4) 0.46164(11) 0.0354(7) Uani 1 1 d . . . . .
H12A H 0.0417 0.7551 0.4894 0.053 Uiso 1 1 calc R U . . .
H12B H -0.0097 0.5856 0.4615 0.053 Uiso 1 1 calc R U . . .
H12C H -0.1661 0.7254 0.4675 0.053 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 1.628(2) . ?
S2 C7 1.623(2) . ?
O1 C1 1.335(3) . ?
O1 C4 1.466(3) . ?
O2 C3 1.345(3) . ?
O2 C2 1.461(3) . ?
O3 C3 1.198(3) . ?
O4 C10 1.339(3) . ?
O4 C8 1.456(3) . ?
O5 C7 1.341(3) . ?
O5 C11 1.466(3) . ?
O6 C10 1.195(3) . ?
C1 C2 1.518(3) . ?
C2 C5 1.507(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(3) . ?
C4 C6 1.504(3) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.516(3) . ?
C8 C9 1.506(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.516(3) . ?
C11 C12 1.506(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 O1 C4 117.87(18) . . ?
C3 O2 C2 118.03(19) . . ?
C10 O4 C8 117.01(18) . . ?
C7 O5 C11 117.66(18) . . ?
O1 C1 C2 114.7(2) . . ?
O1 C1 S1 119.84(17) . . ?
C2 C1 S1 125.43(18) . . ?
O2 C2 C5 106.1(2) . . ?
O2 C2 C1 110.6(2) . . ?
C5 C2 C1 114.4(2) . . ?
O2 C2 H2 108.5 . . ?
C5 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
O3 C3 O2 120.2(2) . . ?
O3 C3 C4 125.2(2) . . ?
O2 C3 C4 114.6(2) . . ?
O1 C4 C6 107.02(18) . . ?
O1 C4 C3 109.34(19) . . ?
C6 C4 C3 113.6(2) . . ?
O1 C4 H4 108.9 . . ?
C6 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 C8 113.4(2) . . ?
O5 C7 S2 120.30(17) . . ?
C8 C7 S2 126.25(18) . . ?
O4 C8 C9 106.70(19) . . ?
O4 C8 C7 108.13(19) . . ?
C9 C8 C7 115.1(2) . . ?
O4 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C10 O4 121.0(2) . . ?
O6 C10 C11 124.7(2) . . ?
O4 C10 C11 114.3(2) . . ?
O5 C11 C12 107.4(2) . . ?
O5 C11 C10 108.3(2) . . ?
C12 C11 C10 112.6(2) . . ?
O5 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_151117RAL_AM_DA_L_LA_100K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1477174'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 O3 S'
_chemical_formula_sum            'C11 H14 O3 S'
_chemical_formula_weight         226.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7606(5)
_cell_length_b                   10.8844(8)
_cell_length_c                   12.686(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1071.60(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4038
_cell_measurement_theta_min      6.69
_cell_measurement_theta_max      68.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    2.568
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_T_max  0.696
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_absorpt_special_details   
'crystal mounted on a Cryoloop using Paratone-N'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10091
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.355
_diffrn_reflns_theta_max         68.390
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1918
_reflns_number_gt                1729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0485P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1918
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
S1 S 0.68484(9) 0.14697(6) 0.85075(6) 0.0218(2) Uani 1 1 d . . . . .
O1 O 0.9904(3) 0.25064(19) 0.71613(15) 0.0220(5) Uani 1 1 d . . . . .
O2 O 0.6471(2) 0.22649(16) 0.64786(16) 0.0204(4) Uani 1 1 d . . . . .
O3 O 1.0694(3) 0.09441(19) 0.61730(16) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.6831(4) 0.2720(3) 0.7503(2) 0.0189(6) Uani 1 1 d . . . . .
C2 C 0.5303(4) 0.3552(3) 0.7830(2) 0.0217(6) Uani 1 1 d . . . . .
H2 H 0.4925 0.4142 0.7272 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5707(3) 0.4145(3) 0.8879(2) 0.0227(7) Uani 1 1 d . . . . .
H3 H 0.6075 0.4969 0.8982 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5461(4) 0.3321(3) 0.9625(2) 0.0251(7) Uani 1 1 d . . . . .
H4 H 0.5626 0.3451 1.0359 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4876(4) 0.2146(3) 0.9124(2) 0.0254(7) Uani 1 1 d . . . . .
H5 H 0.4207 0.1581 0.9591 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3914(4) 0.2624(3) 0.8162(2) 0.0257(7) Uani 1 1 d . . . . .
H6A H 0.2809 0.3024 0.8348 0.031 Uiso 1 1 calc R U . . .
H6B H 0.3719 0.1979 0.7625 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8556(4) 0.3375(3) 0.7467(2) 0.0206(6) Uani 1 1 d . . . . .
H7 H 0.8823 0.3689 0.8190 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8582(4) 0.4451(3) 0.6708(2) 0.0258(7) Uani 1 1 d . . . . .
H8A H 0.9755 0.4778 0.6659 0.039 Uiso 1 1 calc R U . . .
H8B H 0.7804 0.5095 0.6965 0.039 Uiso 1 1 calc R U . . .
H8C H 0.8201 0.4175 0.6011 0.039 Uiso 1 1 calc R U . . .
C9 C 0.9556(4) 0.1609(2) 0.6467(2) 0.0204(6) Uani 1 1 d . . . . .
C10 C 0.7717(3) 0.1410(3) 0.6093(2) 0.0221(6) Uani 1 1 d . . . . .
H10 H 0.7353 0.0569 0.6319 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7648(4) 0.1456(3) 0.4899(2) 0.0302(7) Uani 1 1 d . . . . .
H11A H 0.6492 0.1225 0.4659 0.045 Uiso 1 1 calc R U . . .
H11B H 0.8495 0.0881 0.4606 0.045 Uiso 1 1 calc R U . . .
H11C H 0.7913 0.2290 0.4659 0.045 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 1.865(3) . ?
S1 C5 1.870(3) . ?
O1 C9 1.343(3) . ?
O1 C7 1.462(3) . ?
O2 C1 1.419(3) . ?
O2 C10 1.428(3) . ?
O3 C9 1.201(3) . ?
C1 C7 1.518(4) . ?
C1 C2 1.548(4) . ?
C2 C3 1.512(4) . ?
C2 C6 1.536(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.317(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.498(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.522(4) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.516(4) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.519(4) . ?
C10 C11 1.517(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 C5 89.56(13) . . ?
C9 O1 C7 120.1(2) . . ?
C1 O2 C10 114.1(2) . . ?
O2 C1 C7 108.1(2) . . ?
O2 C1 C2 107.4(2) . . ?
C7 C1 C2 114.1(2) . . ?
O2 C1 S1 111.87(19) . . ?
C7 C1 S1 110.92(19) . . ?
C2 C1 S1 104.41(18) . . ?
C3 C2 C6 100.7(2) . . ?
C3 C2 C1 109.1(2) . . ?
C6 C2 C1 103.1(2) . . ?
C3 C2 H2 114.2 . . ?
C6 C2 H2 114.2 . . ?
C1 C2 H2 114.2 . . ?
C4 C3 C2 108.1(3) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
C3 C4 C5 108.7(3) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
C4 C5 C6 101.4(3) . . ?
C4 C5 S1 105.4(2) . . ?
C6 C5 S1 101.6(2) . . ?
C4 C5 H5 115.5 . . ?
C6 C5 H5 115.5 . . ?
S1 C5 H5 115.5 . . ?
C5 C6 C2 95.7(2) . . ?
C5 C6 H6A 112.6 . . ?
C2 C6 H6A 112.6 . . ?
C5 C6 H6B 112.6 . . ?
C2 C6 H6B 112.6 . . ?
H6A C6 H6B 110.1 . . ?
O1 C7 C8 108.8(2) . . ?
O1 C7 C1 109.6(2) . . ?
C8 C7 C1 113.2(2) . . ?
O1 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C1 C7 H7 108.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 O1 119.6(3) . . ?
O3 C9 C10 120.5(3) . . ?
O1 C9 C10 119.8(2) . . ?
O2 C10 C11 107.3(2) . . ?
O2 C10 C9 115.9(2) . . ?
C11 C10 C9 109.9(2) . . ?
O2 C10 H10 107.9 . . ?
C11 C10 H10 107.9 . . ?
C9 C10 H10 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_ROGER_a
_database_code_depnum_ccdc_archive 'CCDC 1477175'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 O2 S2'
_chemical_formula_sum            'C6 H8 O2 S2'
_chemical_formula_weight         176.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   12.8947(2)
_cell_length_b                   8.5141(1)
_cell_length_c                   7.3227(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     803.936(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6838
_cell_measurement_theta_min      5.20
_cell_measurement_theta_max      70.28

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    5.519
_shelx_estimated_absorpt_T_min   0.371
_shelx_estimated_absorpt_T_max   0.628
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.453
_exptl_absorpt_correction_T_max  0.688
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_absorpt_special_details   
'crystal mounted on a Cryoloop using Paratone-N'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7284
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.195
_diffrn_reflns_theta_max         70.270
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1463
_reflns_number_gt                1455
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.997

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.1146P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1463
_refine_ls_number_parameters     94
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0194
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0515
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.152
_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 0.71867(4) 0.10153(6) 0.63307(8) 0.02346(15) Uani 1 1 d . . . . .
S2 S 0.46335(4) 0.64962(6) 0.41771(9) 0.02135(15) Uani 1 1 d . . . . .
O1 O 0.69729(12) 0.38014(17) 0.5027(2) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.49153(11) 0.35193(16) 0.4392(2) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.65798(16) 0.2362(3) 0.5176(3) 0.0183(4) Uani 1 1 d . . . . .
C2 C 0.64940(15) 0.4862(2) 0.3693(3) 0.0193(4) Uani 1 1 d . . . . .
H2 H 0.6598 0.4423 0.2440 0.023 Uiso 1 1 calc R U . . .
C3 C 0.53430(14) 0.4922(2) 0.4098(4) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.55657(15) 0.2119(2) 0.4170(4) 0.0194(4) Uani 1 1 d . . . . .
H4 H 0.5717 0.1972 0.2842 0.023 Uiso 1 1 calc R U . . .
C5 C 0.70571(18) 0.6413(3) 0.3833(4) 0.0278(5) Uani 1 1 d . . . . .
H5A H 0.6906 0.6899 0.5017 0.042 Uiso 1 1 calc R U . . .
H5B H 0.6825 0.7111 0.2850 0.042 Uiso 1 1 calc R U . . .
H5C H 0.7805 0.6236 0.3722 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4910(2) 0.0766(3) 0.4821(4) 0.0261(5) Uani 1 1 d . . . . .
H6A H 0.4731 0.0922 0.6109 0.039 Uiso 1 1 calc R U . . .
H6B H 0.5299 -0.0216 0.4686 0.039 Uiso 1 1 calc R U . . .
H6C H 0.4274 0.0712 0.4091 0.039 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 1.625(2) . ?
S2 C3 1.6241(19) . ?
O1 C1 1.331(3) . ?
O1 C2 1.467(2) . ?
O2 C3 1.333(2) . ?
O2 C4 1.467(2) . ?
C1 C4 1.515(3) . ?
C2 C5 1.510(3) . ?
C2 C3 1.514(3) . ?
C2 H2 1.0000 . ?
C4 C6 1.506(3) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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 O1 C2 117.47(16) . . ?
C3 O2 C4 118.28(15) . . ?
O1 C1 C4 114.49(18) . . ?
O1 C1 S1 120.59(16) . . ?
C4 C1 S1 124.92(16) . . ?
O1 C2 C5 106.90(17) . . ?
O1 C2 C3 107.61(17) . . ?
C5 C2 C3 115.38(18) . . ?
O1 C2 H2 108.9 . . ?
C5 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
O2 C3 C2 114.03(16) . . ?
O2 C3 S2 120.04(14) . . ?
C2 C3 S2 125.92(14) . . ?
O2 C4 C6 105.41(17) . . ?
O2 C4 C1 109.19(17) . . ?
C6 C4 C1 115.77(19) . . ?
O2 C4 H4 108.8 . . ?
C6 C4 H4 108.8 . . ?
C1 C4 H4 108.8 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043

