# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ga_200108d_a
_database_code_depnum_ccdc_archive 'CCDC 2033465'
loop_
_audit_author_name
_audit_author_address
'Shengqing Ye'
;Taizhou University
China
;
_audit_update_record             
;
2020-09-23 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N O5 S'
_chemical_formula_weight         339.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.9401(7)
_cell_length_b                   5.3894(2)
_cell_length_c                   32.9348(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.506(2)
_cell_angle_gamma                90
_cell_volume                     3468.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1431
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      30.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.222
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.583
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24549
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         4.768
_diffrn_reflns_theta_max         58.491
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3702
_reflns_number_gt                3489
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1524P)²+1.5374P] 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         3702
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.2091
_refine_ls_wR_factor_gt          0.2052
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.30753(2) 0.30887(8) 0.57729(2) 0.0430(2) Uani 1 1 d . . . . .
O1 O 0.35561(8) 0.7727(3) 0.47418(5) 0.0539(4) Uani 1 1 d . . . . .
O2 O 0.26385(9) 0.1101(3) 0.55928(5) 0.0638(5) Uani 1 1 d . . . . .
O3 O 0.37305(8) 0.2384(4) 0.60186(6) 0.0678(5) Uani 1 1 d . . . . .
N1 N 0.24893(11) 0.7009(4) 0.68894(6) 0.0595(5) Uani 1 1 d . . . . .
C1 C 0.42251(9) 0.4687(3) 0.44884(6) 0.0421(4) Uani 1 1 d . . . . .
C2 C 0.42573(11) 0.6060(4) 0.41341(7) 0.0537(5) Uani 1 1 d . . . . .
H2 H 0.400010 0.750392 0.407765 0.064 Uiso 1 1 calc R U . . .
C3 C 0.46668(13) 0.5297(5) 0.38670(7) 0.0658(6) Uani 1 1 d . . . . .
H3 H 0.468460 0.622654 0.363145 0.079 Uiso 1 1 calc R U . . .
C4 C 0.50536(12) 0.3143(5) 0.39483(8) 0.0610(6) Uani 1 1 d . . . . .
H4 H 0.533160 0.263473 0.376822 0.073 Uiso 1 1 calc R U . . .
C5 C 0.50240(13) 0.1767(4) 0.42950(9) 0.0619(6) Uani 1 1 d . . . . .
H5 H 0.528357 0.032781 0.434997 0.074 Uiso 1 1 calc R U . . .
C6 C 0.46086(11) 0.2513(4) 0.45639(7) 0.0542(5) Uani 1 1 d . . . . .
H6 H 0.458597 0.155784 0.479587 0.065 Uiso 1 1 calc R U . . .
C7 C 0.37994(9) 0.5647(3) 0.47795(6) 0.0417(4) Uani 1 1 d . . . . .
C8 C 0.36901(10) 0.3966(3) 0.51284(6) 0.0445(4) Uani 1 1 d . . . . .
H8A H 0.350143 0.239687 0.501441 0.053 Uiso 1 1 calc R U . . .
H8B H 0.412690 0.363281 0.531011 0.053 Uiso 1 1 calc R U . . .
C9 C 0.32095(10) 0.5129(4) 0.53760(6) 0.0472(4) Uani 1 1 d . . . . .
H9A H 0.277532 0.549800 0.519418 0.057 Uiso 1 1 calc R U . . .
H9B H 0.340302 0.667458 0.549743 0.057 Uiso 1 1 calc R U . . .
C10 C 0.26357(13) 0.4950(4) 0.60770(7) 0.0540(5) Uani 1 1 d . . . . .
H10A H 0.291620 0.636971 0.618199 0.065 Uiso 1 1 calc R U . . .
H10B H 0.221454 0.555949 0.590641 0.065 Uiso 1 1 calc R U . . .
C11 C 0.24710(15) 0.3470(4) 0.64386(8) 0.0617(6) Uani 1 1 d . . . . .
H11A H 0.216953 0.210388 0.633293 0.074 Uiso 1 1 calc R U . . .
H11B H 0.288988 0.277907 0.659959 0.074 Uiso 1 1 calc R U . . .
C12 C 0.21332(11) 0.5073(4) 0.67130(6) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.14894(13) 0.4527(6) 0.67798(8) 0.0679(6) Uani 1 1 d . . . . .
H13 H 0.124847 0.316150 0.665390 0.081 Uiso 1 1 calc R U . . .
C14 C 0.12052(15) 0.6091(8) 0.70437(10) 0.0849(9) Uani 1 1 d . . . . .
H14 H 0.077511 0.575626 0.709954 0.102 Uiso 1 1 calc R U . . .
C15 C 0.1563(2) 0.8072(6) 0.72135(10) 0.0832(9) Uani 1 1 d . . . . .
H15 H 0.137998 0.915323 0.738281 0.100 Uiso 1 1 calc R U . . .
C16 C 0.22016(18) 0.8470(5) 0.71332(8) 0.0741(7) Uani 1 1 d . . . . .
H16 H 0.244831 0.983412 0.725530 0.089 Uiso 1 1 calc R U . . .
O4 O 0.44123(16) 0.2074(8) 0.68656(12) 0.1363(12) Uani 1 1 d . . . . .
O5 O 0.39650(18) 0.7357(9) 0.70172(16) 0.1614(16) 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 O2 1.4322(16) . ?
S1 O3 1.4437(16) . ?
S1 C10 1.769(2) . ?
S1 C9 1.7688(19) . ?
O1 C7 1.218(2) . ?
N1 C12 1.329(3) . ?
N1 C16 1.334(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.494(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.513(2) . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.377(3) . ?
C13 C14 1.408(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.342(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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 O3 116.29(12) . . ?
O2 S1 C10 109.24(11) . . ?
O3 S1 C10 109.08(11) . . ?
O2 S1 C9 109.16(10) . . ?
O3 S1 C9 108.92(10) . . ?
C10 S1 C9 103.36(9) . . ?
C12 N1 C16 118.1(2) . . ?
C6 C1 C2 118.69(18) . . ?
C6 C1 C7 122.59(17) . . ?
C2 C1 C7 118.69(17) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 C1 121.27(17) . . ?
O1 C7 C8 120.93(17) . . ?
C1 C7 C8 117.79(15) . . ?
C9 C8 C7 111.33(15) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 S1 110.25(13) . . ?
C8 C9 H9A 109.6 . . ?
S1 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
S1 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 S1 110.77(15) . . ?
C11 C10 H10A 109.5 . . ?
S1 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 111.20(18) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C13 122.1(2) . . ?
N1 C12 C11 116.7(2) . . ?
C13 C12 C11 121.1(2) . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N1 C16 C15 123.5(3) . . ?
N1 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?

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
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C1 C2 C3 177.2(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C7 C1 C6 C5 -176.6(2) . . . . ?
C6 C1 C7 O1 168.34(19) . . . . ?
C2 C1 C7 O1 -9.5(3) . . . . ?
C6 C1 C7 C8 -10.6(3) . . . . ?
C2 C1 C7 C8 171.52(17) . . . . ?
O1 C7 C8 C9 5.1(3) . . . . ?
C1 C7 C8 C9 -175.96(15) . . . . ?
C7 C8 C9 S1 178.53(13) . . . . ?
O2 S1 C9 C8 -73.71(17) . . . . ?
O3 S1 C9 C8 54.22(18) . . . . ?
C10 S1 C9 C8 170.12(15) . . . . ?
O2 S1 C10 C11 63.6(2) . . . . ?
O3 S1 C10 C11 -64.5(2) . . . . ?
C9 S1 C10 C11 179.68(17) . . . . ?
S1 C10 C11 C12 176.74(18) . . . . ?
C16 N1 C12 C13 -1.0(3) . . . . ?
C16 N1 C12 C11 179.7(2) . . . . ?
C10 C11 C12 N1 -60.4(3) . . . . ?
C10 C11 C12 C13 120.4(2) . . . . ?
N1 C12 C13 C14 0.1(4) . . . . ?
C11 C12 C13 C14 179.4(2) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C13 C14 C15 C16 -1.7(5) . . . . ?
C12 N1 C16 C15 0.5(4) . . . . ?
C14 C15 C16 N1 0.9(5) . . . . ?

_refine_diff_density_max         0.977
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.076



