# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2090931'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2021-06-17 deposited with the CCDC.	2021-08-08 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.06.11 svn.re2ff6fc5 for OlexSys, GUI svn.r6348)
;
_chemical_formula_moiety         'C16 H22 N2 O6 S'
_chemical_formula_sum            'C16 H22 N2 O6 S'
_chemical_formula_weight         370.429
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.0035(10)
_cell_length_b                   12.9016(10)
_cell_length_c                   12.5654(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.836(8)
_cell_angle_gamma                90
_cell_volume                     1745.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    162(17)
_cell_measurement_theta_max      28.6870
_cell_measurement_theta_min      3.7940
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             784.935
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.9975
_diffrn_reflns_Laue_measured_fraction_max 0.9977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11808
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9977
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      162(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5148
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  99.00   1.00    5.50    --   10.21 178.00   0.00   64
  2  ω    -31.00  90.00   1.00    5.50    --   10.21  19.00 150.00  121
  3  ω    -20.00  29.00   1.00    5.50    --  -11.93 -99.00-180.00   49
  4  ω     35.00  60.00   1.00    5.50    --   10.21 178.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0304212000
_diffrn_orient_matrix_UB_12      -0.0312943000
_diffrn_orient_matrix_UB_13      0.0328797000
_diffrn_orient_matrix_UB_21      -0.0347643000
_diffrn_orient_matrix_UB_22      0.0435721000
_diffrn_orient_matrix_UB_23      0.0110526000
_diffrn_orient_matrix_UB_31      -0.0470177000
_diffrn_orient_matrix_UB_32      -0.0118916000
_diffrn_orient_matrix_UB_33      -0.0460666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2610
_reflns_number_total             3436
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.5115
_refine_diff_density_min         -0.3741
_refine_diff_density_rms         0.0853
_refine_ls_d_res_high            0.8101
_refine_ls_d_res_low             5.7126
_refine_ls_goodness_of_fit_ref   1.0432
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.0432
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.4711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1028
_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:
 C4(H4a,H4b), C6(H6a,H6b), C12(H12a,H12b), C9(H9a,H9b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C5(H5a,H5b,H5c), C16(H16a,H16b,H16c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S1 S 0.86635(5) 0.10786(4) 0.96563(4) 0.02259(16) Uani 1.000000 .
O6 O 1.00197(14) -0.17271(11) 0.78528(11) 0.0270(4) Uani 1.000000 .
O5 O 0.81940(13) -0.23841(11) 0.91231(11) 0.0266(4) Uani 1.000000 .
N1 N 0.90784(15) -0.01466(13) 0.79596(12) 0.0187(4) Uani 1.000000 .
N2 N 0.76648(15) -0.06627(12) 0.89436(12) 0.0180(4) Uani 1.000000 .
C1 C 0.80692(18) 0.02730(15) 0.84502(14) 0.0183(4) Uani 1.000000 .
C2 C 0.92396(19) -0.11777(16) 0.81247(14) 0.0191(4) Uani 1.000000 .
C4 C 0.67604(19) -0.07409(16) 0.96612(14) 0.0222(5) Uani 1.000000 .
H4a H 0.71357(19) -0.11137(16) 1.03167(14) 0.0266(6) Uiso 1.000000 R
H4b H 0.65524(19) -0.00501(16) 0.98712(14) 0.0266(6) Uiso 1.000000 R
C3 C 0.83063(19) -0.15157(16) 0.87770(15) 0.0203(4) Uani 1.000000 .
C7 C 1.0077(2) 0.03756(19) 0.64267(16) 0.0317(5) Uani 1.000000 .
H7a H 0.9291(5) 0.0604(11) 0.60119(16) 0.0476(8) Uiso 1.000000 GR
H7b H 1.0727(9) 0.0804(9) 0.6261(3) 0.0476(8) Uiso 1.000000 GR
H7c H 1.0216(14) -0.0331(3) 0.6246(3) 0.0476(8) Uiso 1.000000 GR
C5 C 0.5583(2) -0.12938(17) 0.91103(16) 0.0262(5) Uani 1.000000 .
H5a H 0.5193(7) -0.0913(6) 0.8475(6) 0.0393(7) Uiso 1.000000 GR
H5b H 0.5785(2) -0.1978(4) 0.8902(10) 0.0393(7) Uiso 1.000000 GR
H5c H 0.5026(5) -0.1340(9) 0.9605(4) 0.0393(7) Uiso 1.000000 GR
C6 C 1.0071(2) 0.04540(17) 0.76272(16) 0.0258(5) Uani 1.000000 .
H6a H 0.9982(2) 0.11765(17) 0.78105(16) 0.0309(6) Uiso 1.000000 R
H6b H 1.0865(2) 0.02145(17) 0.80384(16) 0.0309(6) Uiso 1.000000 R
C8 C 0.70303(18) 0.07519(15) 0.75053(14) 0.0176(4) Uani 1.000000 .
C12 C 0.8920(2) 0.24066(16) 0.92667(16) 0.0269(5) Uani 1.000000 .
H12a H 0.9353(2) 0.27798(16) 0.99026(16) 0.0323(6) Uiso 1.000000 R
H12b H 0.9453(2) 0.23989(16) 0.87400(16) 0.0323(6) Uiso 1.000000 R
C9 C 0.7370(2) 0.18574(15) 0.71388(15) 0.0220(5) Uani 1.000000 .
H9a H 0.8251(2) 0.18744(15) 0.71379(15) 0.0263(6) Uiso 1.000000 R
H9b H 0.6926(2) 0.19738(15) 0.63980(15) 0.0263(6) Uiso 1.000000 R
C10 C 0.7075(2) 0.27276(16) 0.78382(16) 0.0263(5) Uani 1.000000 .
H10 H 0.6366(2) 0.31182(16) 0.75791(16) 0.0316(6) Uiso 1.000000 R
C11 C 0.7753(2) 0.29740(16) 0.87914(16) 0.0267(5) Uani 1.000000 .
H11 H 0.7498(2) 0.35169(16) 0.91809(16) 0.0321(6) Uiso 1.000000 R
O3 O 0.65305(13) -0.09253(10) 0.67546(9) 0.0214(3) Uani 1.000000 .
O4 O 0.69983(14) 0.02763(11) 0.56230(10) 0.0261(4) Uani 1.000000 .
C13 C 0.57563(19) 0.08734(15) 0.77904(15) 0.0193(4) Uani 1.000000 .
C15 C 0.68717(18) 0.00226(16) 0.65083(14) 0.0184(4) Uani 1.000000 .
O1 O 0.55451(14) 0.11451(11) 0.86474(10) 0.0263(4) Uani 1.000000 .
O2 O 0.48677(13) 0.07081(12) 0.69032(10) 0.0255(3) Uani 1.000000 .
C16 C 0.6220(2) -0.16302(17) 0.58378(16) 0.0321(6) Uani 1.000000 .
H16a H 0.5593(10) -0.1323(5) 0.5284(5) 0.0482(8) Uiso 1.000000 GR
H16b H 0.6949(4) -0.1765(9) 0.5550(8) 0.0482(8) Uiso 1.000000 GR
H16c H 0.5915(13) -0.2269(5) 0.6073(3) 0.0482(8) Uiso 1.000000 GR
C14 C 0.3596(2) 0.08003(19) 0.70315(17) 0.0305(5) Uani 1.000000 .
H14a H 0.3045(2) 0.0632(11) 0.6357(4) 0.0458(8) Uiso 1.000000 GR
H14b H 0.3456(4) 0.0332(8) 0.7587(8) 0.0458(8) Uiso 1.000000 GR
H14c H 0.3443(4) 0.1498(3) 0.7235(11) 0.0458(8) Uiso 1.000000 GR


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 C1 1.8434(18) . ?
S1 C12 1.820(2) . ?
O6 C2 1.215(2) . ?
O5 C3 1.217(2) . ?
N1 C1 1.479(2) . ?
N1 C2 1.352(2) . ?
N1 C6 1.468(3) . ?
N2 C1 1.467(2) . ?
N2 C4 1.477(2) . ?
N2 C3 1.347(3) . ?
C1 C8 1.594(3) . ?
C2 C3 1.504(3) . ?
C4 C5 1.516(3) . ?
C7 C6 1.513(3) . ?
C8 C9 1.567(3) . ?
C8 C13 1.525(3) . ?
C8 C15 1.548(3) . ?
C12 C11 1.493(3) . ?
C9 C10 1.501(3) . ?
C10 C11 1.313(3) . ?
O3 C15 1.334(2) . ?
O3 C16 1.452(2) . ?
O4 C15 1.195(2) . ?
C13 O1 1.200(2) . ?
C13 O2 1.341(2) . ?
O2 C14 1.446(2) . ?

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
C12 S1 C1 110.99(9) . . ?
C2 N1 C1 112.47(16) . . ?
C6 N1 C1 126.27(16) . . ?
C6 N1 C2 118.75(17) . . ?
C4 N2 C1 127.94(16) . . ?
C3 N2 C1 113.11(16) . . ?
C3 N2 C4 118.64(16) . . ?
N1 C1 S1 112.27(13) . . ?
N2 C1 S1 101.75(11) . . ?
N2 C1 N1 101.17(15) . . ?
C8 C1 S1 118.23(13) . . ?
C8 C1 N1 108.45(14) . . ?
C8 C1 N2 113.60(15) . . ?
N1 C2 O6 127.49(19) . . ?
C3 C2 O6 125.79(18) . . ?
C3 C2 N1 106.63(17) . . ?
C5 C4 N2 111.90(15) . . ?
N2 C3 O5 126.99(19) . . ?
C2 C3 O5 126.32(19) . . ?
C2 C3 N2 106.62(17) . . ?
C7 C6 N1 113.81(17) . . ?
C9 C8 C1 113.19(16) . . ?
C13 C8 C1 114.72(14) . . ?
C13 C8 C9 105.16(16) . . ?
C15 C8 C1 108.17(15) . . ?
C15 C8 C9 108.03(14) . . ?
C15 C8 C13 107.23(15) . . ?
C11 C12 S1 113.65(16) . . ?
C10 C9 C8 114.55(16) . . ?
C11 C10 C9 124.4(2) . . ?
C10 C11 C12 121.81(19) . . ?
C16 O3 C15 114.93(14) . . ?
O1 C13 C8 126.71(18) . . ?
O2 C13 C8 109.70(15) . . ?
O2 C13 O1 123.40(19) . . ?
O3 C15 C8 111.09(14) . . ?
O4 C15 C8 124.87(18) . . ?
O4 C15 O3 124.00(17) . . ?
C14 O2 C13 116.85(15) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.444
_oxdiff_exptl_absorpt_empirical_full_min 0.287
