# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_mj19431
_database_code_depnum_ccdc_archive 'CCDC 1938505'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2020-05-05 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O6 S'
_chemical_formula_sum            'C15 H19 N O6 S'
_chemical_formula_weight         341.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   13.3705(2)
_cell_length_b                   7.27390(10)
_cell_length_c                   31.8622(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3098.78(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.93
_cell_measurement_theta_min      5.63
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.851
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0941 before and 0.0493 after correction. The Ratio of minimum to maximum transmission is 0.7898. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30140
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.938
_diffrn_reflns_theta_min         5.625
_diffrn_ambient_temperature      170.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2733
_reflns_number_total             2913
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+1.7663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0877
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.44585(3) 0.75375(5) 0.35894(2) 0.02503(13) Uani 1 1 d . . . . .
O1 O 0.58175(8) 0.61046(15) 0.45050(3) 0.0299(3) Uani 1 1 d . . . . .
O2 O 0.66294(7) 0.41910(14) 0.40684(3) 0.0265(2) Uani 1 1 d . . . . .
O3 O 0.54841(7) 0.17068(16) 0.46863(3) 0.0303(3) Uani 1 1 d . . . . .
O4 O 0.39026(8) 0.07225(15) 0.47407(3) 0.0306(3) Uani 1 1 d . . . . .
H4 H 0.415381 0.000434 0.491821 0.046 Uiso 1 1 calc GR . . . .
O5 O 0.55220(8) 0.76168(16) 0.35354(4) 0.0339(3) Uani 1 1 d . . . . .
O6 O 0.39161(9) 0.91489(15) 0.37143(4) 0.0366(3) Uani 1 1 d . . . . .
N1 N 0.42135(9) 0.59762(17) 0.39328(4) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.48528(10) 0.43323(19) 0.40057(4) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.41556(10) 0.3242(2) 0.43057(4) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.365531 0.259292 0.412552 0.026 Uiso 1 1 calc R . . . .
C3 C 0.35832(11) 0.4714(2) 0.45515(5) 0.0272(3) Uani 1 1 d . . . . .
H3A H 0.296688 0.420468 0.467855 0.033 Uiso 1 1 calc R . . . .
H3B H 0.400401 0.525896 0.477486 0.033 Uiso 1 1 calc R . . . .
C4 C 0.33419(11) 0.6107(2) 0.42141(5) 0.0305(4) Uani 1 1 d . . . . .
H4A H 0.271600 0.578485 0.406535 0.037 Uiso 1 1 calc R . . . .
H4B H 0.327734 0.735849 0.433338 0.037 Uiso 1 1 calc R . . . .
C5 C 0.46027(10) 0.1819(2) 0.45928(4) 0.0225(3) Uani 1 1 d . . . . .
C6 C 0.58156(10) 0.4987(2) 0.42272(4) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.75698(11) 0.4677(2) 0.42653(6) 0.0376(4) Uani 1 1 d . . . . .
H7A H 0.811686 0.401622 0.412700 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.754913 0.434032 0.456293 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.767941 0.600450 0.423898 0.056 Uiso 1 1 calc GR . . . .
C8 C 0.50581(11) 0.3237(2) 0.36076(5) 0.0257(3) Uani 1 1 d . . . . .
H8A H 0.442435 0.296107 0.346650 0.039 Uiso 1 1 calc GR . . . .
H8B H 0.539669 0.208501 0.368048 0.039 Uiso 1 1 calc GR . . . .
H8C H 0.548539 0.395845 0.341978 0.039 Uiso 1 1 calc GR . . . .
C9 C 0.39396(11) 0.6812(2) 0.31072(4) 0.0258(3) Uani 1 1 d . . . . .
C10 C 0.45406(12) 0.6606(2) 0.27576(5) 0.0334(4) Uani 1 1 d . . . . .
H10 H 0.524036 0.681582 0.277704 0.040 Uiso 1 1 calc R . . . .
C11 C 0.41173(13) 0.6094(2) 0.23793(5) 0.0357(4) Uani 1 1 d . . . . .
H11 H 0.453407 0.595359 0.213997 0.043 Uiso 1 1 calc R . . . .
C12 C 0.30965(13) 0.5781(2) 0.23413(5) 0.0321(4) Uani 1 1 d . . . . .
C13 C 0.25106(14) 0.5954(3) 0.26987(5) 0.0403(4) Uani 1 1 d . . . . .
H13 H 0.181400 0.570803 0.268163 0.048 Uiso 1 1 calc R . . . .
C14 C 0.29199(12) 0.6478(3) 0.30796(5) 0.0379(4) Uani 1 1 d . . . . .
H14 H 0.250581 0.660773 0.332008 0.045 Uiso 1 1 calc R . . . .
C15 C 0.26429(15) 0.5256(3) 0.19262(5) 0.0430(4) Uani 1 1 d . . . . .
H15A H 0.247476 0.636986 0.176834 0.064 Uiso 1 1 calc GR . . . .
H15B H 0.203492 0.453309 0.197420 0.064 Uiso 1 1 calc GR . . . .
H15C H 0.312363 0.452115 0.176553 0.064 Uiso 1 1 calc GR . . . .


_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 O5 1.4334(12) . ?
S1 O6 1.4347(12) . ?
S1 N1 1.6106(12) . ?
S1 C9 1.7665(15) . ?
O1 C6 1.2016(18) . ?
O2 C6 1.3324(17) . ?
O2 C7 1.4489(18) . ?
O3 C5 1.2183(18) . ?
O4 H4 0.8400 . ?
O4 C5 1.3170(17) . ?
N1 C1 1.4881(17) . ?
N1 C4 1.4734(18) . ?
C1 C2 1.5527(19) . ?
C1 C6 1.5434(19) . ?
C1 C8 1.5230(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.531(2) . ?
C2 C5 1.505(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.512(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.382(2) . ?
C9 C14 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 C13 1.388(2) . ?
C12 C15 1.504(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9500 . ?
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
O5 S1 O6 120.13(7) . . ?
O5 S1 N1 108.16(7) . . ?
O5 S1 C9 107.29(7) . . ?
O6 S1 N1 106.55(7) . . ?
O6 S1 C9 106.67(7) . . ?
N1 S1 C9 107.47(7) . . ?
C6 O2 C7 115.99(12) . . ?
C5 O4 H4 109.5 . . ?
C1 N1 S1 123.77(9) . . ?
C4 N1 S1 121.90(10) . . ?
C4 N1 C1 114.29(11) . . ?
N1 C1 C2 99.29(11) . . ?
N1 C1 C6 107.60(11) . . ?
N1 C1 C8 113.20(11) . . ?
C6 C1 C2 112.15(11) . . ?
C8 C1 C2 110.71(12) . . ?
C8 C1 C6 113.08(11) . . ?
C1 C2 H2 106.8 . . ?
C3 C2 C1 104.95(12) . . ?
C3 C2 H2 106.8 . . ?
C5 C2 C1 119.13(11) . . ?
C5 C2 H2 106.8 . . ?
C5 C2 C3 111.60(12) . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 C2 102.21(12) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
N1 C4 C3 102.73(11) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O3 C5 O4 124.02(13) . . ?
O3 C5 C2 125.37(13) . . ?
O4 C5 C2 110.59(12) . . ?
O1 C6 O2 124.89(13) . . ?
O1 C6 C1 123.18(13) . . ?
O2 C6 C1 111.92(12) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S1 120.34(12) . . ?
C10 C9 C14 120.09(15) . . ?
C14 C9 S1 119.56(12) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.60(15) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.49(15) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C15 120.96(16) . . ?
C13 C12 C11 117.92(15) . . ?
C13 C12 C15 121.12(16) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.40(16) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.47(16) . . ?
C13 C14 H14 120.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
