# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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#######################################################################

data_pbca
_database_code_depnum_ccdc_archive 'CCDC 1518254'
_audit_update_record             
;
2016-11-21 deposited with the CCDC.
2017-01-03 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         ?
_chemical_formula_sum            'C2.38 H1.70 O0.17 S0.17'
_chemical_formula_weight         38.52

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'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.5863(5)
_cell_length_b                   6.0552(4)
_cell_length_c                   46.173(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2121.0(2)
_cell_formula_units_Z            47
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.466
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23574
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         3.829
_diffrn_reflns_theta_max         68.329
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1946
_reflns_number_gt                1662
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0382P)²+4.6206P] 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         1946
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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 0.60240(11) 0.79058(14) 0.48221(2) 0.0346(3) Uani 1 1 d . . . . .
C1 C 0.4186(8) 0.0229(9) 0.72461(9) 0.0821(17) Uani 1 1 d . . . . .
H1A H 0.4352 0.0047 0.7451 0.123 Uiso 1 1 calc R U . . .
H1B H 0.4624 -0.1050 0.7147 0.123 Uiso 1 1 calc R U . . .
H1C H 0.2952 0.0405 0.7206 0.123 Uiso 1 1 calc R U . . .
C3 C 0.5955(5) 0.4508(7) 0.67767(7) 0.0460(9) Uani 1 1 d . . . . .
H3 H 0.6587 0.5317 0.6913 0.055 Uiso 1 1 calc R U . . .
C2 C 0.5009(5) 0.2659(6) 0.68627(7) 0.0413(8) Uani 1 1 d . . . . .
O2 O 0.5115(4) 0.2130(5) 0.71506(5) 0.0611(8) Uani 1 1 d . . . . .
C4 C 0.5961(5) 0.5145(6) 0.64911(7) 0.0412(8) Uani 1 1 d . . . . .
H4 H 0.6632 0.6361 0.6437 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4994(4) 0.4032(5) 0.62800(7) 0.0317(7) Uani 1 1 d . . . . .
C6 C 0.4026(5) 0.2219(6) 0.63749(7) 0.0434(9) Uani 1 1 d . . . . .
H6 H 0.3356 0.1439 0.6241 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4021(5) 0.1525(7) 0.66618(7) 0.0480(10) Uani 1 1 d . . . . .
H7 H 0.3356 0.0307 0.6717 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5032(4) 0.4675(5) 0.59695(6) 0.0296(7) Uani 1 1 d . . . . .
C9 C 0.5718(4) 0.6736(6) 0.58790(7) 0.0344(7) Uani 1 1 d . . . . .
H9 H 0.6096 0.7740 0.6018 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5842(4) 0.7299(5) 0.55917(7) 0.0331(7) Uani 1 1 d . . . . .
H10 H 0.6292 0.8670 0.5539 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5292(4) 0.5812(5) 0.53767(6) 0.0278(7) Uani 1 1 d . . . . .
C12 C 0.4578(4) 0.3783(5) 0.54668(7) 0.0294(7) Uani 1 1 d . . . . .
C13 C 0.4451(4) 0.3227(5) 0.57570(6) 0.0314(7) Uani 1 1 d . . . . .
H13 H 0.3971 0.1872 0.5810 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5320(4) 0.5919(5) 0.50669(6) 0.0291(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C14 1.735(3) . ?
S1 C12 1.742(3) 5_666 ?
C1 O2 1.420(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.374(5) . ?
C3 C2 1.388(5) . ?
C3 H3 0.9300 . ?
C2 O2 1.370(4) . ?
C2 C7 1.376(5) . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(5) . ?
C5 C8 1.486(4) . ?
C6 C7 1.390(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.388(4) . ?
C8 C9 1.415(5) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.404(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.406(4) . ?
C11 C14 1.432(4) . ?
C12 C13 1.385(4) . ?
C12 S1 1.742(3) 5_666 ?
C13 H13 0.9300 . ?
C14 C14 1.362(6) 5_666 ?

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 S1 C12 90.64(15) . 5_666 ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O2 C2 C7 124.7(3) . . ?
O2 C2 C3 115.9(3) . . ?
C7 C2 C3 119.4(3) . . ?
C2 O2 C1 117.5(3) . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 116.1(3) . . ?
C6 C5 C8 121.4(3) . . ?
C4 C5 C8 122.5(3) . . ?
C7 C6 C5 122.7(3) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C2 C7 C6 119.4(4) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C13 C8 C9 117.7(3) . . ?
C13 C8 C5 120.7(3) . . ?
C9 C8 C5 121.6(3) . . ?
C10 C9 C8 121.9(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 117.8(3) . . ?
C10 C11 C14 132.3(3) . . ?
C12 C11 C14 109.9(3) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 S1 125.5(2) . 5_666 ?
C11 C12 S1 112.8(2) . 5_666 ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C14 C14 C11 114.2(4) 5_666 . ?
C14 C14 S1 112.4(3) 5_666 . ?
C11 C14 S1 133.4(2) . . ?

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
C4 C3 C2 O2 178.7(4) . . . . ?
C4 C3 C2 C7 -2.6(6) . . . . ?
C7 C2 O2 C1 2.3(6) . . . . ?
C3 C2 O2 C1 -179.1(4) . . . . ?
C2 C3 C4 C5 2.0(6) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C4 C5 C8 -178.3(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C8 C5 C6 C7 177.4(3) . . . . ?
O2 C2 C7 C6 -179.7(4) . . . . ?
C3 C2 C7 C6 1.7(6) . . . . ?
C5 C6 C7 C2 -0.1(6) . . . . ?
C6 C5 C8 C13 -14.9(5) . . . . ?
C4 C5 C8 C13 162.9(3) . . . . ?
C6 C5 C8 C9 167.5(3) . . . . ?
C4 C5 C8 C9 -14.8(5) . . . . ?
C13 C8 C9 C10 -1.1(5) . . . . ?
C5 C8 C9 C10 176.6(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 1.6(5) . . . . ?
C9 C10 C11 C14 -177.6(3) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C14 C11 C12 C13 178.0(3) . . . . ?
C10 C11 C12 S1 -179.3(2) . . . 5_666 ?
C14 C11 C12 S1 0.0(3) . . . 5_666 ?
C11 C12 C13 C8 -0.1(5) . . . . ?
S1 C12 C13 C8 177.6(2) 5_666 . . . ?
C9 C8 C13 C12 1.3(5) . . . . ?
C5 C8 C13 C12 -176.4(3) . . . . ?
C10 C11 C14 C14 178.9(4) . . . 5_666 ?
C12 C11 C14 C14 -0.4(5) . . . 5_666 ?
C10 C11 C14 S1 -0.4(6) . . . . ?
C12 C11 C14 S1 -179.7(3) . . . . ?
C12 S1 C14 C14 0.4(3) 5_666 . . 5_666 ?
C12 S1 C14 C11 179.8(3) 5_666 . . . ?

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
C1 H1A O2 0.96 2.58 3.400(5) 143.2 3_646

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.061

