# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1887226'
loop_
_audit_author_name
_audit_author_address
'Guoqiang Li'
;South China University of Technology
China
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;
_audit_creation_date             2016-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.17(C19 H23 N O5 S)'
_chemical_formula_sum            'C3.17 H3.83 N0.17 O0.83 S0.17'
_chemical_formula_weight         62.91
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.417(3)
_cell_length_b                   6.0979(12)
_cell_length_c                   25.184(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.93(3)
_cell_angle_gamma                90
_cell_volume                     1865.8(7)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    3292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.026
_cell_measurement_theta_min      2.586
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6139
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3083
_reflns_number_total             3292
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.7115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0895
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C13(H13a,H13b), C1aa(H1aa,H1ab)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C21(H21), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C2(H2a,H2b,H2c), C0aa(H0aa,H0ab,H0ac), C2aa(H2aa,H2ab,H2ac)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.19604(3) 0.39609(5) 0.25910(2) 0.01298(12) Uani 1 1 d . . . . .
O2 O 0.20690(8) 0.63041(16) 0.25988(4) 0.0183(2) Uani 1 1 d . . . . .
O3 O 0.14955(8) 0.28315(16) 0.20975(4) 0.0181(2) Uani 1 1 d . . . . .
O5 O 0.24464(9) 0.5379(2) 0.57069(4) 0.0271(3) Uani 1 1 d . . . . .
N6 N 0.11833(9) 0.33705(19) 0.30202(4) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.08780(11) 0.1043(2) 0.30761(6) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.1524 0.0109 0.3151 0.020 Uiso 1 1 calc R U . . .
H9B H 0.0381 0.0524 0.2751 0.020 Uiso 1 1 calc R U . . .
C10 C 0.45588(12) -0.0126(2) 0.29123(6) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.4735 -0.1521 0.2807 0.023 Uiso 1 1 calc R U . . .
C11 C 0.09422(11) 0.3134(2) 0.44663(6) 0.0159(3) Uani 1 1 d . . . . .
H11 H 0.0589 0.2030 0.4620 0.019 Uiso 1 1 calc R U . . .
C12 C 0.40398(12) 0.4051(2) 0.32196(6) 0.0188(3) Uani 1 1 d . . . . .
H12 H 0.3866 0.5452 0.3321 0.023 Uiso 1 1 calc R U . . .
C13 C 0.14339(12) 0.4431(2) 0.35603(6) 0.0165(3) Uani 1 1 d . . . . .
H13A H 0.1256 0.5981 0.3534 0.020 Uiso 1 1 calc R U . . .
H13B H 0.2204 0.4257 0.3731 0.020 Uiso 1 1 calc R U . . .
C14 C 0.03171(11) 0.1123(2) 0.35519(6) 0.0165(3) Uani 1 1 d . . . . .
C15 C 0.07003(11) 0.3215(2) 0.38721(6) 0.0155(3) Uani 1 1 d . . . . .
C16 C 0.35299(12) 0.0746(2) 0.26941(6) 0.0175(3) Uani 1 1 d . . . . .
H16 H 0.3019 -0.0058 0.2448 0.021 Uiso 1 1 calc R U . . .
C17 C 0.32745(11) 0.2844(2) 0.28500(6) 0.0157(3) Uani 1 1 d . . . . .
C19 C 0.16056(11) 0.4440(2) 0.48180(6) 0.0157(3) Uani 1 1 d . . . . .
C20 C 0.53325(12) 0.1043(2) 0.32849(6) 0.0194(3) Uani 1 1 d . . . . .
C21 C 0.50592(12) 0.3149(3) 0.34335(6) 0.0207(3) Uani 1 1 d . . . . .
H21 H 0.5570 0.3953 0.3680 0.025 Uiso 1 1 calc R U . . .
C25 C 0.21293(12) 0.6476(2) 0.46500(6) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.64549(12) 0.0107(3) 0.35158(7) 0.0257(3) Uani 1 1 d . . . . .
H2A H 0.6432 -0.1460 0.3479 0.039 Uiso 1 1 calc R U . . .
H2B H 0.6668 0.0489 0.3893 0.039 Uiso 1 1 calc R U . . .
H2C H 0.6980 0.0696 0.3323 0.039 Uiso 1 1 calc R U . . .
C4 C 0.18188(11) 0.4120(2) 0.54168(6) 0.0189(3) Uani 1 1 d . . . . .
C0AA C 0.12526(12) 0.2285(3) 0.56472(6) 0.0221(3) Uani 1 1 d . . . . .
H0AA H 0.1468 0.0908 0.5516 0.033 Uiso 1 1 calc R U . . .
H0AB H 0.0470 0.2457 0.5536 0.033 Uiso 1 1 calc R U . . .
H0AC H 0.1458 0.2316 0.6036 0.033 Uiso 1 1 calc R U . . .
O1 O 0.31786(8) 0.61922(17) 0.46169(4) 0.0215(2) Uani 1 1 d . . . . .
O0AA O 0.16448(9) 0.81886(18) 0.45585(5) 0.0298(3) Uani 1 1 d . . . . .
C1AA C 0.37205(14) 0.8130(3) 0.44541(7) 0.0312(4) Uani 1 1 d . . . . .
H1AA H 0.3589 0.9390 0.4667 0.037 Uiso 1 1 calc R U . . .
H1AB H 0.3436 0.8451 0.4074 0.037 Uiso 1 1 calc R U . . .
C2AA C 0.49292(14) 0.7640(3) 0.45495(8) 0.0397(5) Uani 1 1 d . . . . .
H2AA H 0.5047 0.6373 0.4342 0.060 Uiso 1 1 calc R U . . .
H2AB H 0.5204 0.7358 0.4928 0.060 Uiso 1 1 calc R U . . .
H2AC H 0.5310 0.8874 0.4439 0.060 Uiso 1 1 calc R U . . .
C1 C -0.04933(11) 0.2899(3) 0.35688(6) 0.0191(3) Uani 1 1 d . . . . .
H14 H 0.0266(14) -0.020(3) 0.3737(7) 0.026(5) Uiso 1 1 d . . . . .
H1A H -0.0714(14) 0.383(3) 0.3252(7) 0.025(4) Uiso 1 1 d . . . . .
H1B H -0.1026(14) 0.268(3) 0.3800(7) 0.024(4) 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 O2 1.4350(11) . ?
S1 O3 1.4336(11) . ?
S1 N6 1.6311(12) . ?
S1 C17 1.7641(14) . ?
O5 C4 1.2228(18) . ?
N6 C9 1.4830(17) . ?
N6 C13 1.4798(17) . ?
C9 C14 1.506(2) . ?
C10 C16 1.388(2) . ?
C10 C20 1.393(2) . ?
C11 C15 1.4651(19) . ?
C11 C19 1.340(2) . ?
C12 C17 1.395(2) . ?
C12 C21 1.383(2) . ?
C13 C15 1.5136(19) . ?
C14 C15 1.5317(19) . ?
C14 C1 1.485(2) . ?
C15 C1 1.5329(19) . ?
C16 C17 1.394(2) . ?
C19 C25 1.502(2) . ?
C19 C4 1.489(2) . ?
C20 C21 1.399(2) . ?
C20 C2 1.507(2) . ?
C25 O1 1.3341(18) . ?
C25 O0AA 1.2036(19) . ?
C4 C0AA 1.500(2) . ?
O1 C1AA 1.4597(19) . ?
C1AA C2AA 1.500(3) . ?

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
O2 S1 N6 106.10(6) . . ?
O2 S1 C17 107.59(6) . . ?
O3 S1 O2 120.67(6) . . ?
O3 S1 N6 106.33(6) . . ?
O3 S1 C17 108.13(7) . . ?
N6 S1 C17 107.36(6) . . ?
C9 N6 S1 118.15(9) . . ?
C9 N6 C13 109.89(11) . . ?
C13 N6 S1 118.16(9) . . ?
N6 C9 C14 102.35(11) . . ?
C16 C10 C20 121.40(14) . . ?
C19 C11 C15 128.55(13) . . ?
C21 C12 C17 119.50(13) . . ?
N6 C13 C15 103.19(11) . . ?
C9 C14 C15 107.53(11) . . ?
C1 C14 C9 118.28(12) . . ?
C1 C14 C15 61.06(9) . . ?
C11 C15 C13 121.88(12) . . ?
C11 C15 C14 119.03(12) . . ?
C11 C15 C1 118.54(12) . . ?
C13 C15 C14 106.84(11) . . ?
C13 C15 C1 115.26(12) . . ?
C14 C15 C1 57.96(9) . . ?
C10 C16 C17 118.97(13) . . ?
C12 C17 S1 119.58(11) . . ?
C12 C17 C16 120.60(13) . . ?
C16 C17 S1 119.80(11) . . ?
C11 C19 C25 123.21(13) . . ?
C11 C19 C4 123.20(13) . . ?
C4 C19 C25 113.39(12) . . ?
C10 C20 C21 118.60(13) . . ?
C10 C20 C2 121.35(14) . . ?
C21 C20 C2 120.04(13) . . ?
C12 C21 C20 120.93(13) . . ?
O1 C25 C19 113.31(12) . . ?
O0AA C25 C19 122.88(13) . . ?
O0AA C25 O1 123.81(14) . . ?
O5 C4 C19 118.73(14) . . ?
O5 C4 C0AA 121.93(13) . . ?
C19 C4 C0AA 119.35(13) . . ?
C25 O1 C1AA 115.18(12) . . ?
O1 C1AA C2AA 107.32(15) . . ?
C14 C1 C15 60.98(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
