# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_201219xl1
_database_code_depnum_ccdc_archive 'CCDC 2152042'
loop_
_audit_author_name
_audit_author_address
'Lei Xie'
;Liaocheng University
China
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2022-02-14
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H18 N2 O4 S'
_chemical_formula_sum            'C17 H18 N2 O4 S'
_chemical_formula_weight         346.39
_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'

_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'

_cell_length_a                   8.3747(10)
_cell_length_b                   10.8310(12)
_cell_length_c                   18.463(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.213(2)
_cell_angle_gamma                90.00
_cell_volume                     1672.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5071
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.527
_cell_measurement_theta_min      2.181
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flack
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9808
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.44
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3143
_reflns_number_total             3790
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.6263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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. Uiso/Uaniso restraints and constraints
N2 \\sim O3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
O3 \\sim C17: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C11(H11), C5(H5), C9(H9), C14(H14), C8(H8), C6(H6), C7(H7)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.01634(4) 0.37298(4) 0.63960(2) 0.03436(12) Uani 1 1 d . . .
O4 O 1.09426(14) 0.27944(11) 0.68361(7) 0.0456(3) Uani 1 1 d . . .
O3 O 0.52072(14) 0.57829(14) 0.73430(7) 0.0514(3) Uani 1 1 d U . .
O2 O 1.09402(15) 0.42574(13) 0.57991(7) 0.0511(3) Uani 1 1 d . . .
N1 N 0.98363(14) 0.49019(11) 0.69486(7) 0.0302(3) Uani 1 1 d . . .
N2 N 0.67933(15) 0.54950(13) 0.71916(7) 0.0360(3) Uani 1 1 d U . .
O1 O 0.66975(17) 0.70217(14) 0.63437(8) 0.0635(4) Uani 1 1 d . . .
C1 C 0.93785(17) 0.47003(13) 0.76726(8) 0.0296(3) Uani 1 1 d . . .
C2 C 0.76703(17) 0.49991(14) 0.78334(8) 0.0317(3) Uani 1 1 d . . .
H2 H 0.7672 0.5613 0.8223 0.038 Uiso 1 1 calc R . .
C4 C 0.92147(19) 0.60613(14) 0.66261(9) 0.0350(3) Uani 1 1 d . . .
H4A H 0.9412 0.6063 0.6113 0.042 Uiso 1 1 calc R . .
H4B H 0.9804 0.6746 0.6849 0.042 Uiso 1 1 calc R . .
C10 C 0.82872(19) 0.31700(14) 0.60693(8) 0.0325(3) Uani 1 1 d . . .
C12 C 0.5963(2) 0.32974(17) 0.52607(9) 0.0416(4) Uani 1 1 d . . .
H12 H 0.5386 0.3698 0.4885 0.050 Uiso 1 1 calc R . .
C3 C 0.74493(19) 0.62680(15) 0.67098(9) 0.0369(3) Uani 1 1 d . . .
C15 C 0.7646(2) 0.21438(16) 0.64003(9) 0.0440(4) Uani 1 1 d . . .
H15 H 0.8198 0.1767 0.6792 0.053 Uiso 1 1 calc R . .
C11 C 0.7448(2) 0.37508(15) 0.54954(8) 0.0379(4) Uani 1 1 d . . .
H11 H 0.7878 0.4435 0.5272 0.046 Uiso 1 1 calc R . .
C13 C 0.5314(2) 0.22557(18) 0.55736(9) 0.0433(4) Uani 1 1 d . . .
C5 C 1.0443(2) 0.43660(14) 0.82094(9) 0.0389(4) Uani 1 1 d . . .
H5 H 1.1501 0.4261 0.8094 0.047 Uiso 1 1 calc R . .
C9 C 0.6899(2) 0.38344(16) 0.80840(10) 0.0439(4) Uani 1 1 d . . .
H9 H 0.6113 0.3453 0.7787 0.053 Uiso 1 1 calc R . .
C14 C 0.6182(2) 0.16903(18) 0.61421(10) 0.0498(5) Uani 1 1 d . . .
H14 H 0.5769 0.0990 0.6355 0.060 Uiso 1 1 calc R . .
C8 C 0.7328(3) 0.33390(19) 0.87273(10) 0.0549(5) Uani 1 1 d . . .
H8 H 0.6701 0.2699 0.8891 0.066 Uiso 1 1 calc R . .
C6 C 1.0060(3) 0.41577(17) 0.89537(10) 0.0502(5) Uani 1 1 d . . .
H6 H 1.0852 0.4349 0.9309 0.060 Uiso 1 1 calc R . .
C7 C 0.8676(3) 0.37152(18) 0.91856(10) 0.0561(5) Uani 1 1 d . . .
H7 H 0.8588 0.3648 0.9684 0.067 Uiso 1 1 calc R . .
C17 C 0.4116(2) 0.5126(3) 0.68548(13) 0.0681(6) Uani 1 1 d U . .
H17A H 0.4363 0.5300 0.6364 0.102 Uiso 1 1 calc R . .
H17B H 0.3042 0.5385 0.6930 0.102 Uiso 1 1 calc R . .
H17C H 0.4214 0.4256 0.6944 0.102 Uiso 1 1 calc R . .
C16 C 0.3717(3) 0.1746(3) 0.52959(12) 0.0664(6) Uani 1 1 d . . .
H16A H 0.2876 0.2265 0.5456 0.100 Uiso 1 1 calc R . .
H16B H 0.3587 0.0926 0.5480 0.100 Uiso 1 1 calc R . .
H16C H 0.3672 0.1724 0.4775 0.100 Uiso 1 1 calc R . .


_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 O4 1.4328(12) . ?
S1 O2 1.4299(13) . ?
S1 N1 1.6610(13) . ?
S1 C10 1.7590(16) . ?
O3 N2 1.4076(17) . ?
O3 C17 1.435(2) . ?
N1 C1 1.4279(19) . ?
N1 C4 1.4723(19) . ?
N2 C2 1.461(2) . ?
N2 C3 1.360(2) . ?
O1 C3 1.2132(19) . ?
C1 C2 1.512(2) . ?
C1 C5 1.345(2) . ?
C2 H2 0.9800 . ?
C2 C9 1.502(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.512(2) . ?
C10 C15 1.391(2) . ?
C10 C11 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(2) . ?
C12 C13 1.392(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.385(3) . ?
C13 C16 1.510(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.446(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.334(3) . ?
C14 H14 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.432(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.346(3) . ?
C7 H7 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O4 S1 N1 106.11(7) . . ?
O4 S1 C10 108.69(8) . . ?
O2 S1 O4 120.48(8) . . ?
O2 S1 N1 105.41(7) . . ?
O2 S1 C10 108.04(8) . . ?
N1 S1 C10 107.41(7) . . ?
N2 O3 C17 109.89(14) . . ?
C1 N1 S1 121.36(10) . . ?
C1 N1 C4 113.68(12) . . ?
C4 N1 S1 118.05(10) . . ?
O3 N2 C2 110.95(12) . . ?
C3 N2 O3 114.45(13) . . ?
C3 N2 C2 123.63(12) . . ?
N1 C1 C2 117.23(12) . . ?
C5 C1 N1 121.96(14) . . ?
C5 C1 C2 120.55(14) . . ?
N2 C2 C1 110.95(12) . . ?
N2 C2 H2 109.1 . . ?
N2 C2 C9 110.69(13) . . ?
C1 C2 H2 109.1 . . ?
C9 C2 C1 107.97(13) . . ?
C9 C2 H2 109.1 . . ?
N1 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
N1 C4 C3 114.24(12) . . ?
H4A C4 H4B 107.6 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C15 C10 S1 118.96(12) . . ?
C11 C10 S1 120.64(12) . . ?
C11 C10 C15 120.40(15) . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.51(15) . . ?
C13 C12 H12 119.2 . . ?
N2 C3 C4 114.14(13) . . ?
O1 C3 N2 124.24(15) . . ?
O1 C3 C4 121.51(15) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.32(16) . . ?
C14 C15 H15 120.3 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.05(15) . . ?
C12 C11 H11 120.5 . . ?
C12 C13 C16 120.96(17) . . ?
C14 C13 C12 118.19(16) . . ?
C14 C13 C16 120.85(17) . . ?
C1 C5 H5 117.7 . . ?
C1 C5 C6 124.68(17) . . ?
C6 C5 H5 117.7 . . ?
C2 C9 H9 119.6 . . ?
C8 C9 C2 120.88(17) . . ?
C8 C9 H9 119.6 . . ?
C15 C14 C13 121.49(16) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C9 C8 H8 117.4 . . ?
C9 C8 C7 125.14(18) . . ?
C7 C8 H8 117.4 . . ?
C5 C6 H6 116.6 . . ?
C7 C6 C5 126.76(17) . . ?
C7 C6 H6 116.6 . . ?
C8 C7 H7 117.3 . . ?
C6 C7 C8 125.30(17) . . ?
C6 C7 H7 117.3 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
S1 N1 C1 C2 -108.15(13) . . . . ?
S1 N1 C1 C5 77.74(17) . . . . ?
S1 N1 C4 C3 102.84(14) . . . . ?
S1 C10 C15 C14 -179.30(15) . . . . ?
S1 C10 C11 C12 -178.91(12) . . . . ?
O4 S1 N1 C1 -38.07(13) . . . . ?
O4 S1 N1 C4 172.89(11) . . . . ?
O4 S1 C10 C15 16.48(16) . . . . ?
O4 S1 C10 C11 -164.28(13) . . . . ?
O3 N2 C2 C1 -179.51(12) . . . . ?
O3 N2 C2 C9 60.65(17) . . . . ?
O3 N2 C3 O1 -11.5(2) . . . . ?
O3 N2 C3 C4 172.18(13) . . . . ?
O2 S1 N1 C1 -166.93(11) . . . . ?
O2 S1 N1 C4 44.03(12) . . . . ?
O2 S1 C10 C15 148.81(14) . . . . ?
O2 S1 C10 C11 -31.95(15) . . . . ?
N1 S1 C10 C15 -97.92(14) . . . . ?
N1 S1 C10 C11 81.32(14) . . . . ?
N1 C1 C2 N2 -1.82(18) . . . . ?
N1 C1 C2 C9 119.64(14) . . . . ?
N1 C1 C5 C6 179.47(15) . . . . ?
N1 C4 C3 N2 12.9(2) . . . . ?
N1 C4 C3 O1 -163.48(16) . . . . ?
N2 C2 C9 C8 -168.42(17) . . . . ?
C1 N1 C4 C3 -48.49(18) . . . . ?
C1 C2 C9 C8 70.0(2) . . . . ?
C1 C5 C6 C7 32.2(3) . . . . ?
C2 N2 C3 O1 -152.25(17) . . . . ?
C2 N2 C3 C4 31.5(2) . . . . ?
C2 C1 C5 C6 5.6(2) . . . . ?
C2 C9 C8 C7 -10.1(3) . . . . ?
C4 N1 C1 C2 42.13(17) . . . . ?
C4 N1 C1 C5 -131.98(15) . . . . ?
C10 S1 N1 C1 78.04(12) . . . . ?
C10 S1 N1 C4 -71.00(12) . . . . ?
C10 C15 C14 C13 -1.9(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C3 N2 C2 C1 -37.6(2) . . . . ?
C3 N2 C2 C9 -157.46(15) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C11 C10 C15 C14 1.5(3) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C11 C12 C13 C16 -177.98(18) . . . . ?
C13 C12 C11 C10 -1.8(3) . . . . ?
C5 C1 C2 N2 172.38(14) . . . . ?
C5 C1 C2 C9 -66.16(18) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C9 C8 C7 C6 -32.1(4) . . . . ?
C17 O3 N2 C2 -123.05(17) . . . . ?
C17 O3 N2 C3 91.32(19) . . . . ?
C16 C13 C14 C15 179.82(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
