# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1
_database_code_depnum_ccdc_archive 'CCDC 1534913'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.	2021-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N2 O6 S'
_chemical_formula_weight         424.50

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.617(5)
_cell_length_b                   13.441(5)
_cell_length_c                   8.825(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.752(4)
_cell_angle_gamma                90.00
_cell_volume                     2053.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4320
_cell_measurement_theta_min      2.3535
_cell_measurement_theta_max      24.9265

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14908
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3809
_reflns_number_gt                2981
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0711P)²+1.6210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3809
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.002

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
C1 C 0.38131(18) 0.5303(2) -0.0240(4) 0.0506(8) Uani 1 1 d . . .
H1A H 0.4345 0.5529 -0.0076 0.061 Uiso 1 1 calc R . .
H1B H 0.3787 0.4671 -0.0779 0.061 Uiso 1 1 calc R . .
C2 C 0.35851(16) 0.5143(2) 0.1303(3) 0.0434(7) Uani 1 1 d . . .
H2A H 0.3042 0.4969 0.1137 0.052 Uiso 1 1 calc R . .
H2B H 0.3875 0.4583 0.1808 0.052 Uiso 1 1 calc R . .
C3 C 0.27302(16) 0.6459(2) 0.3907(4) 0.0463(7) Uani 1 1 d . . .
H3A H 0.3147 0.6506 0.4792 0.056 Uiso 1 1 calc R . .
H3B H 0.2360 0.6979 0.4000 0.056 Uiso 1 1 calc R . .
C4 C 0.30496(15) 0.6631(2) 0.2466(3) 0.0455(7) Uani 1 1 d . . .
H4A H 0.2643 0.6515 0.1579 0.055 Uiso 1 1 calc R . .
H4B H 0.3205 0.7322 0.2438 0.055 Uiso 1 1 calc R . .
C5 C 0.44315(15) 0.6193(2) 0.3188(3) 0.0390(6) Uani 1 1 d . . .
C6 C 0.45687(17) 0.7044(2) 0.4128(4) 0.0479(7) Uani 1 1 d . . .
H6 H 0.4171 0.7500 0.4127 0.057 Uiso 1 1 calc R . .
C7 C 0.52734(16) 0.7216(2) 0.5043(4) 0.0461(7) Uani 1 1 d . . .
H7 H 0.5343 0.7785 0.5651 0.055 Uiso 1 1 calc R . .
C8 C 0.58944(14) 0.6555(2) 0.5086(3) 0.0371(6) Uani 1 1 d . . .
C9 C 0.57647(15) 0.5726(2) 0.4125(3) 0.0378(6) Uani 1 1 d . . .
H9 H 0.6166 0.5278 0.4117 0.045 Uiso 1 1 calc R . .
C10 C 0.50626(16) 0.5548(2) 0.3190(3) 0.0398(6) Uani 1 1 d . . .
H10 H 0.5003 0.4994 0.2548 0.048 Uiso 1 1 calc R . .
C11 C 0.66379(15) 0.6691(2) 0.6104(3) 0.0381(6) Uani 1 1 d . . .
H11 H 0.6982 0.6162 0.6162 0.046 Uiso 1 1 calc R . .
C12 C 0.68843(15) 0.7483(2) 0.6961(3) 0.0392(6) Uani 1 1 d . . .
H12 H 0.6560 0.8034 0.6871 0.047 Uiso 1 1 calc R . .
C13 C 0.76143(15) 0.7558(2) 0.8021(3) 0.0351(6) Uani 1 1 d . . .
C14 C 0.81076(15) 0.6747(2) 0.8459(3) 0.0393(6) Uani 1 1 d . . .
H14 H 0.7976 0.6124 0.8031 0.047 Uiso 1 1 calc R . .
C15 C 0.87810(16) 0.6860(2) 0.9510(3) 0.0400(6) Uani 1 1 d . . .
H15 H 0.9098 0.6312 0.9793 0.048 Uiso 1 1 calc R . .
C16 C 0.85283(16) 0.8552(2) 0.9733(3) 0.0409(6) Uani 1 1 d . . .
H16 H 0.8675 0.9168 1.0173 0.049 Uiso 1 1 calc R . .
C17 C 0.78582(16) 0.8471(2) 0.8702(3) 0.0415(7) Uani 1 1 d . . .
H17 H 0.7554 0.9033 0.8441 0.050 Uiso 1 1 calc R . .
C18 C 0.97223(16) 0.7880(2) 1.1269(3) 0.0437(7) Uani 1 1 d . . .
H18A H 0.9903 0.7236 1.1682 0.052 Uiso 1 1 calc R . .
H18B H 0.9629 0.8292 1.2118 0.052 Uiso 1 1 calc R . .
C19 C 1.03381(15) 0.8360(2) 1.0520(3) 0.0401(6) Uani 1 1 d . . .
H19A H 1.0150 0.8998 1.0094 0.048 Uiso 1 1 calc R . .
H19B H 1.0428 0.7944 0.9673 0.048 Uiso 1 1 calc R . .
C20 C 1.10996(16) 0.8516(2) 1.1630(3) 0.0447(7) Uani 1 1 d . . .
H20A H 1.1481 0.8750 1.1050 0.054 Uiso 1 1 calc R . .
H20B H 1.1276 0.7880 1.2083 0.054 Uiso 1 1 calc R . .
N1 N 0.37135(13) 0.59965(19) 0.2330(3) 0.0464(6) Uani 1 1 d . . .
N2 N 0.89878(12) 0.77540(17) 1.0135(2) 0.0369(5) Uani 1 1 d . . .
O3 O 1.06460(14) 0.88776(18) 1.4208(2) 0.0624(7) Uani 1 1 d . . .
O4 O 1.06186(12) 1.02234(15) 1.2422(2) 0.0502(5) Uani 1 1 d . . .
O5 O 1.18395(13) 0.96282(19) 1.3819(3) 0.0670(7) Uani 1 1 d . . .
O6 O 0.09138(13) 0.5520(2) 0.2267(3) 0.0675(7) Uani 1 1 d . . .
H6A H 0.0571 0.5817 0.2659 0.101 Uiso 1 1 d R . .
H6B H 0.0866 0.5679 0.1321 0.101 Uiso 1 1 d R . .
S1 S 1.10505(4) 0.93749(5) 1.31373(8) 0.0388(2) Uani 1 1 d . . .
O2 O 0.23640(13) 0.55200(16) 0.3929(3) 0.0553(6) Uani 1 1 d . . .
H2D H 0.2336 0.5375 0.4820 0.083 Uiso 1 1 calc R . .
O1 O 0.33462(14) 0.5997(2) -0.1180(3) 0.0685(7) Uani 1 1 d . . .
H1C H 0.2906 0.5776 -0.1421 0.103 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
C1 O1 1.407(4) . ?
C1 C2 1.506(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.453(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.419(4) . ?
C3 C4 1.501(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.470(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.373(3) . ?
C5 C6 1.407(4) . ?
C5 C10 1.409(4) . ?
C6 C7 1.368(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(4) . ?
C8 C11 1.455(4) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.331(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.446(4) . ?
C12 H12 0.9300 . ?
C13 C17 1.398(4) . ?
C13 C14 1.403(4) . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 N2 1.344(4) . ?
C15 H15 0.9300 . ?
C16 N2 1.350(4) . ?
C16 C17 1.354(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N2 1.491(3) . ?
C18 C19 1.516(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.521(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 S1 1.776(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
O3 S1 1.449(2) . ?
O4 S1 1.449(2) . ?
O5 S1 1.448(2) . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?
O2 H2D 0.8200 . ?
O1 H1C 0.8200 . ?

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
O1 C1 C2 113.7(3) . . ?
O1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
O1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 C1 114.5(3) . . ?
N1 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
N1 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
O2 C3 C4 113.1(3) . . ?
O2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
O2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 114.1(2) . . ?
N1 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 C6 121.4(3) . . ?
N1 C5 C10 121.9(3) . . ?
C6 C5 C10 116.8(2) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 116.8(2) . . ?
C9 C8 C11 120.2(2) . . ?
C7 C8 C11 123.0(3) . . ?
C10 C9 C8 122.1(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C8 127.7(3) . . ?
C12 C11 H11 116.1 . . ?
C8 C11 H11 116.1 . . ?
C11 C12 C13 125.5(3) . . ?
C11 C12 H12 117.3 . . ?
C13 C12 H12 117.3 . . ?
C17 C13 C14 116.0(2) . . ?
C17 C13 C12 120.3(2) . . ?
C14 C13 C12 123.7(2) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N2 C15 C14 120.7(3) . . ?
N2 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N2 C16 C17 121.1(3) . . ?
N2 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C13 121.3(3) . . ?
C16 C17 H17 119.4 . . ?
C13 C17 H17 119.4 . . ?
N2 C18 C19 111.0(2) . . ?
N2 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N2 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 113.3(2) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 S1 114.3(2) . . ?
C19 C20 H20A 108.7 . . ?
S1 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
S1 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C5 N1 C2 121.1(2) . . ?
C5 N1 C4 120.6(2) . . ?
C2 N1 C4 118.4(2) . . ?
C15 N2 C16 119.9(2) . . ?
C15 N2 C18 120.8(2) . . ?
C16 N2 C18 119.2(2) . . ?
H6A O6 H6B 109.5 . . ?
O5 S1 O4 112.42(14) . . ?
O5 S1 O3 112.84(15) . . ?
O4 S1 O3 111.41(14) . . ?
O5 S1 C20 106.68(14) . . ?
O4 S1 C20 106.27(14) . . ?
O3 S1 C20 106.70(15) . . ?
C3 O2 H2D 109.5 . . ?
C1 O1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.064
