# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1525019'
#Added by publCIF



_audit_update_record             
;
2016-12-30 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  graphite
# publcif _publ_body_element loop end

_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            'C25 H23 N O5 S'
_chemical_formula_weight         449.50

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'
N N 0.0061 0.0033 '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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   11.6942(4)
_cell_length_b                   7.0690(2)
_cell_length_c                   13.1573(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.2100(10)
_cell_angle_gamma                90
_cell_volume                     1066.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(1)
_cell_measurement_reflns_used    9319
_cell_measurement_theta_min      3.155
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Darkyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min  0.8711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku R-axis Rapid S'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10104
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.157
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4786
_reflns_number_gt                4332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.981

_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)+(0.0620P)²] 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_abs_structure_details 
;
 Flack x determined using 1932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4786
_refine_ls_number_parameters     292
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.95089(5) 0.96085(8) 0.68597(5) 0.04362(16) Uani 1 1 d . . . . .
N1 N 0.82409(16) 0.7382(3) 1.16685(14) 0.0348(4) Uani 1 1 d . . . . .
O1 O 0.24190(19) 0.7681(4) 0.61850(17) 0.0660(6) Uani 1 1 d . . . . .
H1 H 0.1875 0.7992 0.6459 0.099 Uiso 1 1 calc R U . . .
O2 O 1.06136(19) 0.8605(5) 0.7013(2) 0.0898(8) Uani 1 1 d . . . . .
O3 O 0.9064(2) 0.9668(4) 0.78020(16) 0.0744(7) Uani 1 1 d . . . . .
O4 O 0.95307(19) 1.1425(3) 0.63694(17) 0.0668(6) Uani 1 1 d . . . . .
O5 O 0.6072(2) 0.4743(3) 0.41690(18) 0.0718(7) Uani 1 1 d . . . . .
C1 C 0.9347(2) 0.7392(3) 1.23122(19) 0.0366(5) Uani 1 1 d . . . . .
C2 C 0.9493(2) 0.7127(4) 1.3390(2) 0.0470(6) Uani 1 1 d . . . . .
H2 H 0.8851 0.6937 1.3699 0.056 Uiso 1 1 calc R U . . .
C3 C 1.0600(3) 0.7154(4) 1.3976(2) 0.0535(7) Uani 1 1 d . . . . .
H3 H 1.0698 0.6971 1.4688 0.064 Uiso 1 1 calc R U . . .
C4 C 1.1571(3) 0.7442(4) 1.3550(2) 0.0558(7) Uani 1 1 d . . . . .
H4 H 1.2307 0.7466 1.3973 0.067 Uiso 1 1 calc R U . . .
C5 C 1.1455(2) 0.7694(4) 1.2503(2) 0.0529(7) Uani 1 1 d . . . . .
H5 H 1.2111 0.7872 1.2213 0.063 Uiso 1 1 calc R U . . .
C6 C 1.0329(2) 0.7683(3) 1.18620(19) 0.0398(5) Uani 1 1 d . . . . .
C7 C 1.0153(2) 0.8003(4) 1.0783(2) 0.0484(6) Uani 1 1 d . . . . .
H7 H 1.0794 0.8159 1.0469 0.058 Uiso 1 1 calc R U . . .
C8 C 0.9061(2) 0.8085(4) 1.01946(19) 0.0452(5) Uani 1 1 d . . . . .
H8 H 0.8962 0.8364 0.9492 0.054 Uiso 1 1 calc R U . . .
C9 C 0.80771(19) 0.7752(3) 1.06429(17) 0.0351(5) Uani 1 1 d . . . . .
C10 C 0.7227(2) 0.6902(4) 1.2148(2) 0.0497(6) Uani 1 1 d . . . . .
H10A H 0.6939 0.8030 1.2418 0.074 Uiso 1 1 calc R U . . .
H10B H 0.7465 0.6015 1.2701 0.074 Uiso 1 1 calc R U . . .
H10C H 0.6622 0.6351 1.1635 0.074 Uiso 1 1 calc R U . . .
C11 C 0.6903(2) 0.7819(3) 1.00206(19) 0.0401(5) Uani 1 1 d . . . . .
H11 H 0.6279 0.8008 1.0352 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6689(2) 0.7620(3) 0.89926(18) 0.0392(5) Uani 1 1 d . . . . .
H12 H 0.7332 0.7441 0.8685 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5546(2) 0.7653(3) 0.82987(17) 0.0370(5) Uani 1 1 d . . . . .
C14 C 0.5494(2) 0.7356(4) 0.7241(2) 0.0444(5) Uani 1 1 d . . . . .
H14 H 0.6180 0.7153 0.6999 0.053 Uiso 1 1 calc R U . . .
C15 C 0.4451(2) 0.7357(4) 0.65532(19) 0.0482(6) Uani 1 1 d . . . . .
H15 H 0.4433 0.7144 0.5853 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3419(2) 0.7677(4) 0.69015(19) 0.0436(5) Uani 1 1 d . . . . .
C17 C 0.3447(2) 0.7973(4) 0.79533(19) 0.0445(5) Uani 1 1 d . . . . .
H17 H 0.2759 0.8175 0.8191 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4502(2) 0.7964(4) 0.86403(17) 0.0414(5) Uani 1 1 d . . . . .
H18 H 0.4519 0.8168 0.9341 0.050 Uiso 1 1 calc R U . . .
C19 C 0.8517(2) 0.8177(3) 0.59876(18) 0.0387(5) Uani 1 1 d . . . . .
C20 C 0.8628(2) 0.6230(4) 0.5984(2) 0.0497(6) Uani 1 1 d . . . . .
H20 H 0.9269 0.5654 0.6398 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7795(3) 0.5144(4) 0.5369(2) 0.0585(7) Uani 1 1 d . . . . .
H21 H 0.7874 0.3835 0.5374 0.070 Uiso 1 1 calc R U . . .
C22 C 0.6838(2) 0.5975(4) 0.47413(18) 0.0486(6) Uani 1 1 d . . . . .
C23 C 0.6727(2) 0.7928(4) 0.47143(19) 0.0442(5) Uani 1 1 d . . . . .
H23 H 0.6093 0.8502 0.4290 0.053 Uiso 1 1 calc R U . . .
C24 C 0.7582(2) 0.9011(3) 0.53349(19) 0.0405(5) Uani 1 1 d . . . . .
H24 H 0.7524 1.0323 0.5311 0.049 Uiso 1 1 calc R U . . .
C25 C 0.4991(3) 0.5491(6) 0.3610(2) 0.0760(10) Uani 1 1 d . . . . .
H25A H 0.4568 0.6058 0.4088 0.114 Uiso 1 1 calc R U . . .
H25B H 0.4536 0.4487 0.3242 0.114 Uiso 1 1 calc R U . . .
H25C H 0.5146 0.6429 0.3127 0.114 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 O3 1.435(2) . ?
S1 O4 1.439(2) . ?
S1 O2 1.453(2) . ?
S1 C19 1.780(3) . ?
N1 C9 1.351(3) . ?
N1 C1 1.402(3) . ?
N1 C10 1.487(3) . ?
O1 C16 1.352(3) . ?
O1 H1 0.8200 . ?
O5 C22 1.366(3) . ?
O5 C25 1.435(5) . ?
C1 C6 1.406(3) . ?
C1 C2 1.408(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(4) . ?
C7 C8 1.359(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.456(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.334(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.465(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(4) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.383(4) . ?
C19 C24 1.384(3) . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(4) . ?
C23 C24 1.391(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
O3 S1 O4 113.70(16) . . ?
O3 S1 O2 110.87(17) . . ?
O4 S1 O2 113.89(18) . . ?
O3 S1 C19 105.87(12) . . ?
O4 S1 C19 106.51(11) . . ?
O2 S1 C19 105.19(14) . . ?
C9 N1 C1 122.50(19) . . ?
C9 N1 C10 119.89(18) . . ?
C1 N1 C10 117.60(18) . . ?
C16 O1 H1 109.5 . . ?
C22 O5 C25 117.7(3) . . ?
N1 C1 C6 118.7(2) . . ?
N1 C1 C2 121.6(2) . . ?
C6 C1 C2 119.7(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 118.3(2) . . ?
C1 C6 C5 119.3(2) . . ?
C7 C6 C5 122.3(2) . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N1 C9 C8 118.8(2) . . ?
N1 C9 C11 120.19(19) . . ?
C8 C9 C11 121.1(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 122.5(2) . . ?
C12 C11 H11 118.8 . . ?
C9 C11 H11 118.8 . . ?
C11 C12 C13 126.8(2) . . ?
C11 C12 H12 116.6 . . ?
C13 C12 H12 116.6 . . ?
C14 C13 C18 118.2(2) . . ?
C14 C13 C12 118.5(2) . . ?
C18 C13 C12 123.4(2) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
O1 C16 C15 117.3(2) . . ?
O1 C16 C17 122.9(2) . . ?
C15 C16 C17 119.8(2) . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 C24 119.0(2) . . ?
C20 C19 S1 121.22(18) . . ?
C24 C19 S1 119.68(18) . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
O5 C22 C21 115.1(3) . . ?
O5 C22 C23 124.9(3) . . ?
C21 C22 C23 119.9(2) . . ?
C22 C23 C24 118.7(2) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C19 C24 C23 121.4(2) . . ?
C19 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.040


