# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1_a
_audit_block_doi                 10.5517/ccdc.csd.cc224csd
_database_code_depnum_ccdc_archive 'CCDC 1910833'
loop_
_audit_author_name
_audit_author_address
photoacid
;jlu
China
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O4 S'
_chemical_formula_weight         385.46

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 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.282(6)
_cell_length_b                   15.881(7)
_cell_length_c                   11.591(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.756(12)
_cell_angle_gamma                90
_cell_volume                     1928.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    664
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      20.05

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11443
_diffrn_reflns_av_unetI/netI     0.1474
_diffrn_reflns_av_R_equivalents  0.1443
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         25.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3544
_reflns_number_gt                1769
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0821P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3544
_refine_ls_number_parameters     249
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_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
C1 C 0.4671(4) 0.3238(3) 0.2296(5) 0.0388(11) Uani 1 1 d . . . . .
C2 C 0.4195(5) 0.3165(3) 0.0995(5) 0.0482(13) Uani 1 1 d . . . . .
H2 H 0.3528 0.2796 0.0602 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4702(5) 0.3630(3) 0.0309(5) 0.0568(14) Uani 1 1 d . . . . .
H3 H 0.4373 0.3579 -0.0551 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5699(5) 0.4177(3) 0.0870(5) 0.0620(15) Uani 1 1 d . . . . .
H4 H 0.6049 0.4485 0.0392 0.074 Uiso 1 1 calc R U . . .
C5 C 0.6172(5) 0.4264(3) 0.2139(5) 0.0530(14) Uani 1 1 d . . . . .
H5 H 0.6836 0.4640 0.2513 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5674(4) 0.3797(3) 0.2881(5) 0.0437(12) Uani 1 1 d . . . . .
C7 C 0.6108(5) 0.3895(3) 0.4224(5) 0.0472(13) Uani 1 1 d . . . . .
H7 H 0.5856 0.3490 0.4666 0.057 Uiso 1 1 calc R U . . .
C8 C 0.6849(4) 0.4529(3) 0.4873(5) 0.0476(13) Uani 1 1 d . . . . .
H8 H 0.7135 0.4918 0.4435 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7227(4) 0.4651(3) 0.6171(5) 0.0420(12) Uani 1 1 d . . . . .
C10 C 0.7127(4) 0.4039(3) 0.7148(5) 0.0407(12) Uani 1 1 d . . . . .
C11 C 0.7758(4) 0.4538(3) 0.8325(5) 0.0417(12) Uani 1 1 d . . . . .
C12 C 0.8095(4) 0.5325(3) 0.8046(4) 0.0387(11) Uani 1 1 d . . . . .
C13 C 0.8621(4) 0.5945(3) 0.8911(5) 0.0450(12) Uani 1 1 d . . . . .
H13 H 0.8836 0.6470 0.8691 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8814(4) 0.5744(3) 1.0126(5) 0.0510(13) Uani 1 1 d . . . . .
H14 H 0.9163 0.6147 1.0741 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8505(4) 0.4964(3) 1.0453(5) 0.0535(13) Uani 1 1 d . . . . .
H15 H 0.8646 0.4849 1.1281 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7978(5) 0.4341(3) 0.9548(5) 0.0519(14) Uani 1 1 d . . . . .
H16 H 0.7783 0.3810 0.9765 0.062 Uiso 1 1 calc R U . . .
C17 C 0.7795(5) 0.3195(3) 0.7148(5) 0.0564(15) Uani 1 1 d . . . . .
H17A H 0.8657 0.3298 0.7215 0.085 Uiso 1 1 calc R U . . .
H17B H 0.7345 0.2900 0.6388 0.085 Uiso 1 1 calc R U . . .
H17C H 0.7800 0.2861 0.7839 0.085 Uiso 1 1 calc R U . . .
C18 C 0.5708(4) 0.3900(3) 0.6974(6) 0.0563(14) Uani 1 1 d . . . . .
H18A H 0.5664 0.3549 0.7631 0.085 Uiso 1 1 calc R U . . .
H18B H 0.5266 0.3633 0.6189 0.085 Uiso 1 1 calc R U . . .
H18C H 0.5316 0.4434 0.6996 0.085 Uiso 1 1 calc R U . . .
C19 C 0.8014(4) 0.6112(3) 0.6092(4) 0.0400(11) Uani 1 1 d . . . . .
H19A H 0.7969 0.6616 0.6548 0.048 Uiso 1 1 calc R U . . .
H19B H 0.7360 0.6153 0.5266 0.048 Uiso 1 1 calc R U . . .
C20 C 0.9309(5) 0.6063(3) 0.5994(5) 0.0487(13) Uani 1 1 d . . . . .
H20A H 0.9416 0.5506 0.5703 0.058 Uiso 1 1 calc R U . . .
H20B H 0.9961 0.6136 0.6815 0.058 Uiso 1 1 calc R U . . .
C21 C 0.9510(4) 0.6714(3) 0.5126(5) 0.0451(12) Uani 1 1 d . . . . .
H21A H 1.0417 0.6755 0.5296 0.054 Uiso 1 1 calc R U . . .
H21B H 0.9230 0.7257 0.5313 0.054 Uiso 1 1 calc R U . . .
N1 N 0.7769(3) 0.5365(2) 0.6730(4) 0.0380(9) Uani 1 1 d . . . . .
O1 O 0.4178(3) 0.2799(2) 0.3007(3) 0.0543(10) Uani 1 1 d D . . . .
H1O H 0.361(4) 0.247(3) 0.256(4) 0.065 Uiso 1 1 d D U . . .
O2 O 0.7335(3) 0.6567(2) 0.3282(3) 0.0588(10) Uani 1 1 d . . . . .
O3 O 0.9046(4) 0.5659(2) 0.3311(4) 0.0790(13) Uani 1 1 d . . . . .
O4 O 0.9092(3) 0.7144(2) 0.2837(4) 0.0643(11) Uani 1 1 d . . . . .
S1 S 0.86959(12) 0.65035(7) 0.35059(12) 0.0447(4) 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
C1 O1 1.348(5) . ?
C1 C6 1.399(6) . ?
C1 C2 1.405(7) . ?
C2 C3 1.357(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(7) . ?
C7 C8 1.347(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.416(7) . ?
C8 H8 0.9300 . ?
C9 N1 1.337(5) . ?
C9 C10 1.527(7) . ?
C10 C11 1.509(7) . ?
C10 C17 1.538(6) . ?
C10 C18 1.554(6) . ?
C11 C12 1.379(6) . ?
C11 C16 1.381(7) . ?
C12 C13 1.373(6) . ?
C12 N1 1.432(6) . ?
C13 C14 1.380(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.404(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.477(5) . ?
C19 C20 1.509(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.517(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 S1 1.790(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
O1 H1O 0.846(19) . ?
O2 S1 1.463(3) . ?
O3 S1 1.439(3) . ?
O4 S1 1.446(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
O1 C1 C6 118.3(4) . . ?
O1 C1 C2 122.2(4) . . ?
C6 C1 C2 119.5(4) . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.3(5) . . ?
C1 C6 C7 118.5(4) . . ?
C5 C6 C7 123.1(4) . . ?
C8 C7 C6 124.8(5) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C7 C8 C9 125.1(5) . . ?
C7 C8 H8 117.4 . . ?
C9 C8 H8 117.4 . . ?
N1 C9 C8 122.3(4) . . ?
N1 C9 C10 109.0(4) . . ?
C8 C9 C10 128.7(4) . . ?
C11 C10 C9 101.3(4) . . ?
C11 C10 C17 113.0(4) . . ?
C9 C10 C17 112.5(4) . . ?
C11 C10 C18 108.0(4) . . ?
C9 C10 C18 110.5(4) . . ?
C17 C10 C18 111.0(4) . . ?
C12 C11 C16 119.1(5) . . ?
C12 C11 C10 110.0(4) . . ?
C16 C11 C10 130.8(4) . . ?
C13 C12 C11 124.1(5) . . ?
C13 C12 N1 128.1(4) . . ?
C11 C12 N1 107.8(4) . . ?
C12 C13 C14 116.2(5) . . ?
C12 C13 H13 121.9 . . ?
C14 C13 H13 121.9 . . ?
C15 C14 C13 121.9(5) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 118.2(5) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 111.2(3) . . ?
N1 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
N1 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 113.6(4) . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 S1 115.1(3) . . ?
C20 C21 H21A 108.5 . . ?
S1 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
S1 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C9 N1 C12 111.7(4) . . ?
C9 N1 C19 125.2(4) . . ?
C12 N1 C19 123.2(4) . . ?
C1 O1 H1O 110(4) . . ?
O3 S1 O4 114.4(2) . . ?
O3 S1 O2 111.5(2) . . ?
O4 S1 O2 111.7(2) . . ?
O3 S1 C21 106.0(2) . . ?
O4 S1 C21 106.9(2) . . ?
O2 S1 C21 105.7(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
O1 C1 C2 C3 178.8(4) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 C6 1.0(8) . . . . ?
O1 C1 C6 C5 -179.0(4) . . . . ?
C2 C1 C6 C5 -0.2(7) . . . . ?
O1 C1 C6 C7 -1.9(7) . . . . ?
C2 C1 C6 C7 176.9(4) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C4 C5 C6 C7 -177.2(5) . . . . ?
C1 C6 C7 C8 -164.5(5) . . . . ?
C5 C6 C7 C8 12.4(8) . . . . ?
C6 C7 C8 C9 176.9(5) . . . . ?
C7 C8 C9 N1 -167.9(5) . . . . ?
C7 C8 C9 C10 13.0(8) . . . . ?
N1 C9 C10 C11 -2.2(5) . . . . ?
C8 C9 C10 C11 177.0(5) . . . . ?
N1 C9 C10 C17 -123.2(4) . . . . ?
C8 C9 C10 C17 56.0(6) . . . . ?
N1 C9 C10 C18 112.1(4) . . . . ?
C8 C9 C10 C18 -68.7(6) . . . . ?
C9 C10 C11 C12 2.9(5) . . . . ?
C17 C10 C11 C12 123.6(4) . . . . ?
C18 C10 C11 C12 -113.3(4) . . . . ?
C9 C10 C11 C16 -180.0(5) . . . . ?
C17 C10 C11 C16 -59.3(7) . . . . ?
C18 C10 C11 C16 63.8(6) . . . . ?
C16 C11 C12 C13 -1.4(7) . . . . ?
C10 C11 C12 C13 176.1(4) . . . . ?
C16 C11 C12 N1 179.9(4) . . . . ?
C10 C11 C12 N1 -2.6(5) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
N1 C12 C13 C14 178.6(4) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C12 C11 C16 C15 1.9(7) . . . . ?
C10 C11 C16 C15 -175.0(5) . . . . ?
C14 C15 C16 C11 -1.3(7) . . . . ?
N1 C19 C20 C21 168.2(4) . . . . ?
C19 C20 C21 S1 -75.0(5) . . . . ?
C8 C9 N1 C12 -178.4(4) . . . . ?
C10 C9 N1 C12 0.8(5) . . . . ?
C8 C9 N1 C19 1.6(7) . . . . ?
C10 C9 N1 C19 -179.2(4) . . . . ?
C13 C12 N1 C9 -177.5(4) . . . . ?
C11 C12 N1 C9 1.1(5) . . . . ?
C13 C12 N1 C19 2.4(7) . . . . ?
C11 C12 N1 C19 -178.9(4) . . . . ?
C20 C19 N1 C9 -89.5(5) . . . . ?
C20 C19 N1 C12 90.5(5) . . . . ?
C20 C21 S1 O3 -52.5(4) . . . . ?
C20 C21 S1 O4 -174.9(3) . . . . ?
C20 C21 S1 O2 66.0(4) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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 2005264'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2019-10-08
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.10.03 svn.r3662 for OlexSys, GUI svn.r5953)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O4 S'
_chemical_formula_sum            'C20 H21 N O4 S'
_chemical_formula_weight         371.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 N1 O4 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.33916(6)
_cell_length_b                   19.51555(15)
_cell_length_c                   11.56961(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.2199(8)
_cell_angle_gamma                90
_cell_volume                     1840.21(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13067
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.8260
_cell_measurement_theta_min      4.4980
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.414
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -8 6 0.0389
0 8 -6 0.0703
0 -9 -5 0.0342
0 9 5 0.0884
0 0 -1 0.0406
0 0 1 0.0572
0 1 0 0.0940
1 -2 0 0.1420
2 1 -1 0.1744
1 0 2 0.1143
-2 -1 1 0.3836

_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.098
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0400 -8.1812 5.5922 -0.9704 0.0251 -0.2404
-0.0464 8.1819 -5.5899 0.9706 -0.0251 0.2392
-0.2493 -8.6848 -5.2585 0.0790 -0.9959 0.0435
0.2043 8.6689 5.2839 -0.0790 0.9955 -0.0521
0.0000 0.0000 -1.0000 0.0971 -0.0903 0.0311
-0.0000 -0.0000 1.0000 -0.0971 0.0903 -0.0311
-0.0000 1.0000 0.0000 0.0518 0.0589 0.0090
1.0000 -2.0000 -0.0000 -0.1776 -0.0784 0.1516
2.0000 1.0000 -1.0000 0.0012 0.0473 0.3790
1.0000 -0.0000 2.0000 -0.2682 0.2200 0.1073
-2.0000 -1.0000 1.0000 -0.0012 -0.0473 -0.3790

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17018
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.101
_diffrn_reflns_theta_min         4.519
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -72.00   1.00    2.00    --  -40.91-153.00  28.00   43
  2  ω   -115.00 -32.00   1.00    2.00    --  -40.91 -38.00 -60.00   83
  3  ω    -73.00  33.00   1.00    2.00    --  -40.91  19.00 120.00  106
  4  ω     70.00  97.00   1.00    2.00    --   40.91-125.00 -90.00   27
  5  ω    -19.00  71.00   1.00    2.00    --   40.91 -77.00-150.00   90
  6  ω     44.00  83.00   1.00    2.00    --   40.91-125.00  90.00   39
  7  ω     62.00  87.00   1.00    8.00    --  112.00 178.00  90.00   25
  8  ω     55.00 109.00   1.00    8.00    --  112.00-111.00 120.00   54
  9  ω     45.00  74.00   1.00    8.00    --  112.00 -45.00  90.00   29
 10  ω     86.00 174.00   1.00    8.00    --  112.00  30.00 -30.00   88
 11  ω     36.00  69.00   1.00    8.00    --  112.00-111.00  30.00   33
 12  ω     95.00 127.00   1.00    8.00    --  112.00  45.00  30.00   32
 13  ω    131.00 177.00   1.00    8.00    --  112.00  45.00  30.00   46
 14  ω     30.00 107.00   1.00    8.00    --  112.00 -94.00-120.00   77
 15  ω     84.00 111.00   1.00    8.00    --  112.00  30.00 120.00   27
 16  ω     69.00  95.00   1.00    8.00    --  112.00 -94.00 150.00   26
 17  ω     74.00 109.00   1.00    8.00    --  112.00-111.00 -30.00   35
 18  ω     37.00 109.00   1.00    8.00    --  112.00-111.00-150.00   72
 19  ω     55.00 104.00   1.00    8.00    --  112.00 -94.00  30.00   49
 20  ω    112.00 139.00   1.00    8.00    --  112.00 178.00  90.00   27
 21  ω    129.00 155.00   1.00    8.00    --  112.00  30.00 120.00   26
 22  ω    113.00 164.00   1.00    8.00    --  112.00 111.00 -30.00   51
 23  ω    119.00 178.00   1.00    8.00    --  112.00  77.00-120.00   59
 24  ω     84.00 109.00   1.00    8.00    --  112.00-111.00  30.00   25
 25  ω     88.00 140.00   1.00    8.00    --  112.00  45.00  60.00   52
 26  ω    146.00 175.00   1.00    8.00    --  112.00  45.00  60.00   29
 27  ω     60.00 112.00   1.00    8.00    --  112.00 -61.00-120.00   52
 28  ω     63.00 108.00   1.00    8.00    --  112.00-111.00 150.00   45
 29  ω     77.00 108.00   1.00    8.00    --  112.00-111.00-120.00   31
 30  ω     35.00  68.00   1.00    8.00    --  112.00 -94.00-180.00   33
 31  ω     42.00 132.00   1.00    8.00    --  112.00 -45.00-150.00   90
 32  ω    108.00 173.00   1.00    8.00    --  112.00 111.00-180.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0738869000
_diffrn_orient_matrix_UB_12      0.0518416000
_diffrn_orient_matrix_UB_13      -0.0971480000
_diffrn_orient_matrix_UB_21      0.0393556000
_diffrn_orient_matrix_UB_22      0.0588598000
_diffrn_orient_matrix_UB_23      0.0903161000
_diffrn_orient_matrix_UB_31      0.1694824000
_diffrn_orient_matrix_UB_32      0.0089550000
_diffrn_orient_matrix_UB_33      -0.0310974000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3742
_reflns_number_total             3828
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_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  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00161(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.8482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0769
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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_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 0.52188(3) 0.57121(2) 0.72099(2) 0.01733(10) Uani 1 1 d . . . . .
O1 O 0.19187(11) 0.23837(5) 0.73467(8) 0.0271(2) Uani 1 1 d . . . . .
H1 H 0.122(2) 0.2067(10) 0.7397(16) 0.044(5) Uiso 1 1 d . . . . .
O2 O 0.50188(11) 0.52804(5) 0.81824(8) 0.0257(2) Uani 1 1 d . . . . .
O3 O 0.52061(11) 0.64437(4) 0.74870(9) 0.0281(2) Uani 1 1 d . . . . .
O4 O 0.41497(11) 0.55352(5) 0.60890(8) 0.0304(2) Uani 1 1 d . . . . .
N1 N 0.77877(11) 0.43473(5) 0.74534(8) 0.01474(19) Uani 1 1 d . . . . .
C1 C 0.66738(13) 0.39049(5) 0.76485(10) 0.0156(2) Uani 1 1 d . . . . .
C2 C 0.93127(13) 0.42588(6) 0.82670(10) 0.0161(2) Uani 1 1 d . . . . .
C3 C 1.07651(14) 0.46158(6) 0.83212(10) 0.0197(2) Uani 1 1 d . . . . .
H3 H 1.0874(18) 0.4986(8) 0.7794(14) 0.023(4) Uiso 1 1 d . . . . .
C4 C 1.21080(14) 0.44007(6) 0.91757(11) 0.0227(2) Uani 1 1 d . . . . .
H4 H 1.314(2) 0.4652(8) 0.9238(14) 0.028(4) Uiso 1 1 d . . . . .
C5 C 1.19713(15) 0.38578(7) 0.99273(11) 0.0238(3) Uani 1 1 d . . . . .
H5 H 1.292(2) 0.3717(8) 1.0502(14) 0.027(4) Uiso 1 1 d . . . . .
C6 C 1.04880(15) 0.35156(6) 0.98647(11) 0.0229(2) Uani 1 1 d . . . . .
H6 H 1.0392(19) 0.3132(8) 1.0388(14) 0.027(4) Uiso 1 1 d . . . . .
C7 C 0.91429(14) 0.37255(6) 0.90181(10) 0.0176(2) Uani 1 1 d . . . . .
C8 C 0.73897(13) 0.34706(6) 0.87340(10) 0.0171(2) Uani 1 1 d . . . . .
C9 C 0.50568(14) 0.38852(6) 0.69312(10) 0.0182(2) Uani 1 1 d . . . . .
H9 H 0.4829(18) 0.4202(8) 0.6305(14) 0.022(4) Uiso 1 1 d . . . . .
C10 C 0.38692(14) 0.34625(6) 0.71346(10) 0.0183(2) Uani 1 1 d . . . . .
H10 H 0.4111(18) 0.3131(8) 0.7781(13) 0.022(4) Uiso 1 1 d . . . . .
C11 C 0.22007(13) 0.34440(6) 0.64498(10) 0.0167(2) Uani 1 1 d . . . . .
C12 C 0.12195(14) 0.28754(6) 0.65913(10) 0.0183(2) Uani 1 1 d . . . . .
C13 C -0.03949(14) 0.28341(6) 0.59361(11) 0.0211(2) Uani 1 1 d . . . . .
H13 H -0.1040(19) 0.2449(8) 0.6042(14) 0.027(4) Uiso 1 1 d . . . . .
C14 C -0.10314(14) 0.33521(7) 0.51602(11) 0.0221(2) Uani 1 1 d . . . . .
H14 H -0.211(2) 0.3322(9) 0.4711(15) 0.032(4) Uiso 1 1 d . . . . .
C15 C -0.00805(15) 0.39242(6) 0.50262(11) 0.0214(2) Uani 1 1 d . . . . .
H15 H -0.0559(19) 0.4276(8) 0.4475(14) 0.026(4) Uiso 1 1 d . . . . .
C16 C 0.15132(14) 0.39691(6) 0.56694(10) 0.0192(2) Uani 1 1 d . . . . .
H16 H 0.2135(19) 0.4386(8) 0.5620(13) 0.023(4) Uiso 1 1 d . . . . .
C17 C 0.75848(13) 0.48831(5) 0.65426(10) 0.0156(2) Uani 1 1 d . . . . .
H17A H 0.6719(18) 0.4759(7) 0.5893(13) 0.018(3) Uiso 1 1 d . . . . .
H17B H 0.8623(17) 0.4897(7) 0.6266(12) 0.016(3) Uiso 1 1 d . . . . .
C18 C 0.72711(14) 0.55865(6) 0.70195(10) 0.0175(2) Uani 1 1 d . . . . .
H18A H 0.7997(19) 0.5678(8) 0.7789(14) 0.025(4) Uiso 1 1 d . . . . .
H18B H 0.7443(19) 0.5939(8) 0.6476(14) 0.025(4) Uiso 1 1 d . . . . .
C19 C 0.65412(15) 0.36710(7) 0.97525(11) 0.0233(2) Uani 1 1 d . . . . .
H19A H 0.541(2) 0.3509(8) 0.9580(14) 0.026(4) Uiso 1 1 d . . . . .
H19B H 0.715(2) 0.3481(9) 1.0503(16) 0.036(4) Uiso 1 1 d . . . . .
H19C H 0.652(2) 0.4165(9) 0.9843(15) 0.035(4) Uiso 1 1 d . . . . .
C20 C 0.73164(16) 0.26930(6) 0.85129(12) 0.0240(3) Uani 1 1 d . . . . .
H20A H 0.620(2) 0.2519(9) 0.8377(15) 0.034(4) Uiso 1 1 d . . . . .
H20B H 0.797(2) 0.2458(9) 0.9227(15) 0.035(4) Uiso 1 1 d . . . . .
H20C H 0.780(2) 0.2573(9) 0.7839(16) 0.038(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 1.4431(9) . ?
S1 O3 1.4640(9) . ?
S1 O4 1.4513(9) . ?
S1 C18 1.7880(12) . ?
O1 H1 0.86(2) . ?
O1 C12 1.3450(14) . ?
N1 C1 1.3220(14) . ?
N1 C2 1.4235(14) . ?
N1 C17 1.4687(13) . ?
C1 C8 1.5280(15) . ?
C1 C9 1.4265(15) . ?
C2 C3 1.3871(16) . ?
C2 C7 1.3823(16) . ?
C3 H3 0.962(16) . ?
C3 C4 1.3924(17) . ?
C4 H4 0.978(16) . ?
C4 C5 1.3906(19) . ?
C5 H5 0.957(16) . ?
C5 C6 1.3941(18) . ?
C6 H6 0.977(16) . ?
C6 C7 1.3857(16) . ?
C7 C8 1.5131(15) . ?
C8 C19 1.5476(16) . ?
C8 C20 1.5379(15) . ?
C9 H9 0.940(15) . ?
C9 C10 1.3474(16) . ?
C10 H10 0.978(15) . ?
C10 C11 1.4486(15) . ?
C11 C12 1.4086(15) . ?
C11 C16 1.4054(16) . ?
C12 C13 1.4005(16) . ?
C13 H13 0.947(16) . ?
C13 C14 1.3812(17) . ?
C14 H14 0.943(17) . ?
C14 C15 1.3970(17) . ?
C15 H15 0.964(16) . ?
C15 C16 1.3817(17) . ?
C16 H16 0.973(16) . ?
C17 H17A 0.957(15) . ?
C17 H17B 0.985(14) . ?
C17 C18 1.5226(15) . ?
C18 H18A 0.981(16) . ?
C18 H18B 0.962(16) . ?
C19 H19A 0.972(16) . ?
C19 H19B 0.980(18) . ?
C19 H19C 0.970(18) . ?
C20 H20A 0.974(18) . ?
C20 H20B 1.000(17) . ?
C20 H20C 0.981(18) . ?

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 113.03(6) . . ?
O2 S1 O4 114.03(6) . . ?
O2 S1 C18 106.72(5) . . ?
O3 S1 C18 102.25(5) . . ?
O4 S1 O3 113.33(6) . . ?
O4 S1 C18 106.28(6) . . ?
C12 O1 H1 110.5(13) . . ?
C1 N1 C2 111.69(9) . . ?
C1 N1 C17 127.52(9) . . ?
C2 N1 C17 120.79(9) . . ?
N1 C1 C8 109.64(9) . . ?
N1 C1 C9 122.02(10) . . ?
C9 C1 C8 128.31(10) . . ?
C3 C2 N1 128.19(10) . . ?
C7 C2 N1 108.12(10) . . ?
C7 C2 C3 123.67(11) . . ?
C2 C3 H3 123.2(9) . . ?
C2 C3 C4 116.36(11) . . ?
C4 C3 H3 120.4(9) . . ?
C3 C4 H4 117.6(9) . . ?
C5 C4 C3 120.90(11) . . ?
C5 C4 H4 121.5(9) . . ?
C4 C5 H5 119.3(10) . . ?
C4 C5 C6 121.45(11) . . ?
C6 C5 H5 119.2(10) . . ?
C5 C6 H6 121.6(9) . . ?
C7 C6 C5 118.15(11) . . ?
C7 C6 H6 120.3(9) . . ?
C2 C7 C6 119.45(11) . . ?
C2 C7 C8 109.50(10) . . ?
C6 C7 C8 131.05(11) . . ?
C1 C8 C19 108.87(9) . . ?
C1 C8 C20 114.57(10) . . ?
C7 C8 C1 100.81(9) . . ?
C7 C8 C19 109.14(9) . . ?
C7 C8 C20 111.29(9) . . ?
C20 C8 C19 111.56(10) . . ?
C1 C9 H9 116.3(9) . . ?
C10 C9 C1 123.65(11) . . ?
C10 C9 H9 120.0(9) . . ?
C9 C10 H10 119.9(9) . . ?
C9 C10 C11 125.18(11) . . ?
C11 C10 H10 114.9(9) . . ?
C12 C11 C10 118.06(10) . . ?
C16 C11 C10 123.17(10) . . ?
C16 C11 C12 118.76(10) . . ?
O1 C12 C11 117.06(10) . . ?
O1 C12 C13 123.06(10) . . ?
C13 C12 C11 119.86(10) . . ?
C12 C13 H13 118.9(10) . . ?
C14 C13 C12 120.19(11) . . ?
C14 C13 H13 120.9(10) . . ?
C13 C14 H14 120.3(10) . . ?
C13 C14 C15 120.53(11) . . ?
C15 C14 H14 119.2(10) . . ?
C14 C15 H15 118.5(9) . . ?
C16 C15 C14 119.66(11) . . ?
C16 C15 H15 121.9(9) . . ?
C11 C16 H16 119.8(9) . . ?
C15 C16 C11 120.98(11) . . ?
C15 C16 H16 119.0(9) . . ?
N1 C17 H17A 109.6(9) . . ?
N1 C17 H17B 106.1(8) . . ?
N1 C17 C18 112.61(9) . . ?
H17A C17 H17B 108.7(11) . . ?
C18 C17 H17A 110.7(8) . . ?
C18 C17 H17B 108.9(8) . . ?
S1 C18 H18A 106.7(9) . . ?
S1 C18 H18B 105.1(9) . . ?
C17 C18 S1 114.24(8) . . ?
C17 C18 H18A 111.8(9) . . ?
C17 C18 H18B 110.3(9) . . ?
H18A C18 H18B 108.3(13) . . ?
C8 C19 H19A 109.9(9) . . ?
C8 C19 H19B 110.2(10) . . ?
C8 C19 H19C 110.9(10) . . ?
H19A C19 H19B 110.7(14) . . ?
H19A C19 H19C 107.8(14) . . ?
H19B C19 H19C 107.4(14) . . ?
C8 C20 H20A 111.9(10) . . ?
C8 C20 H20B 108.6(10) . . ?
C8 C20 H20C 111.1(10) . . ?
H20A C20 H20B 108.1(14) . . ?
H20A C20 H20C 109.4(14) . . ?
H20B C20 H20C 107.6(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.86(2) 1.73(2) 2.5856(12) 179(2) 2_546 yes

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
O1 C12 C13 C14 -178.94(11) . . . . ?
O2 S1 C18 C17 69.57(9) . . . . ?
O3 S1 C18 C17 -171.53(8) . . . . ?
O4 S1 C18 C17 -52.48(10) . . . . ?
N1 C1 C8 C7 -4.55(11) . . . . ?
N1 C1 C8 C19 110.17(10) . . . . ?
N1 C1 C8 C20 -124.14(10) . . . . ?
N1 C1 C9 C10 -176.98(11) . . . . ?
N1 C2 C3 C4 -176.85(11) . . . . ?
N1 C2 C7 C6 177.08(10) . . . . ?
N1 C2 C7 C8 -3.24(12) . . . . ?
N1 C17 C18 S1 -77.60(11) . . . . ?
C1 N1 C2 C3 178.55(11) . . . . ?
C1 N1 C2 C7 0.15(13) . . . . ?
C1 N1 C17 C18 98.78(13) . . . . ?
C1 C9 C10 C11 177.85(11) . . . . ?
C2 N1 C1 C8 2.97(12) . . . . ?
C2 N1 C1 C9 -178.79(10) . . . . ?
C2 N1 C17 C18 -80.62(12) . . . . ?
C2 C3 C4 C5 -0.19(17) . . . . ?
C2 C7 C8 C1 4.62(12) . . . . ?
C2 C7 C8 C19 -109.89(11) . . . . ?
C2 C7 C8 C20 126.55(11) . . . . ?
C3 C2 C7 C6 -1.41(18) . . . . ?
C3 C2 C7 C8 178.27(10) . . . . ?
C3 C4 C5 C6 -0.84(19) . . . . ?
C4 C5 C6 C7 0.77(18) . . . . ?
C5 C6 C7 C2 0.32(17) . . . . ?
C5 C6 C7 C8 -179.29(11) . . . . ?
C6 C7 C8 C1 -175.74(12) . . . . ?
C6 C7 C8 C19 69.75(16) . . . . ?
C6 C7 C8 C20 -53.82(17) . . . . ?
C7 C2 C3 C4 1.33(17) . . . . ?
C8 C1 C9 C10 0.90(19) . . . . ?
C9 C1 C8 C7 177.36(11) . . . . ?
C9 C1 C8 C19 -67.93(14) . . . . ?
C9 C1 C8 C20 57.76(15) . . . . ?
C9 C10 C11 C12 165.43(11) . . . . ?
C9 C10 C11 C16 -15.57(18) . . . . ?
C10 C11 C12 O1 -0.87(16) . . . . ?
C10 C11 C12 C13 -179.31(10) . . . . ?
C10 C11 C16 C15 179.33(11) . . . . ?
C11 C12 C13 C14 -0.59(17) . . . . ?
C12 C11 C16 C15 -1.69(17) . . . . ?
C12 C13 C14 C15 -0.48(18) . . . . ?
C13 C14 C15 C16 0.46(18) . . . . ?
C14 C15 C16 C11 0.64(18) . . . . ?
C16 C11 C12 O1 -179.91(10) . . . . ?
C16 C11 C12 C13 1.65(16) . . . . ?
C17 N1 C1 C8 -176.48(9) . . . . ?
C17 N1 C1 C9 1.76(17) . . . . ?
C17 N1 C2 C3 -1.95(17) . . . . ?
C17 N1 C2 C7 179.64(9) . . . . ?

_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.396
_oxdiff_exptl_absorpt_empirical_full_min 0.832
####################################################################### 
# 
# 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_cp38
_database_code_depnum_ccdc_archive 'CCDC 2005262'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2020-05-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N O4 S'
_chemical_formula_sum            'C22 H25 N O4 S'
_chemical_formula_weight         399.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H33 N1 O6 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   17.1075(3)
_cell_length_b                   6.98646(10)
_cell_length_c                   19.6635(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2350.19(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12532
_cell_measurement_temperature    139.99(10)
_cell_measurement_theta_max      72.4240
_cell_measurement_theta_min      4.4830
_shelx_estimated_absorpt_T_max   0.803
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 0 0.1087
-2 1 0 0.1032
1 2 1 0.1229
0 2 1 0.1113
0 -2 -1 0.1056
1 0 0 0.1128
1 1 2 0.1103
-2 1 1 0.1194
2 -1 -1 0.1177
1 -2 -2 0.0993
1 1 0 0.1184
0 1 0 0.0936
1 -1 0 0.0993
-2 -2 -1 0.0942
-1 -1 0 0.0585
0 0 -1 0.1105
-2 0 -1 0.1124
2 0 -1 0.1338
2 11 -2 0.1154
-10 3 -2 0.1059
0 -13 0 0.0666
7 -9 1 0.0892
-7 -10 -1 0.0625
2 11 2 0.0991
6 -10 -1 0.0934
-8 -7 -2 0.0745
2 -9 3 0.0655
-7 -9 2 0.0596
-10 -6 1 0.0670
9 -4 2 0.1066
3 12 0 0.0922
-6 6 3 0.1121

_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.161
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0023 -0.9976 -0.0006 0.0942 -0.0045 0.1724
-2.0023 0.9976 0.0006 -0.0942 0.0045 -0.1724
1.0017 2.0015 1.0019 -0.2346 -0.0642 0.1495
0.0009 2.0003 1.0020 -0.2495 -0.0843 0.0630
-0.0009 -2.0003 -1.0020 0.2495 0.0843 -0.0630
1.0007 0.0012 -0.0000 0.0150 0.0201 0.0866
1.0049 1.0021 2.0023 -0.2914 -0.2830 0.2105
-1.9998 0.9981 1.0015 -0.2153 -0.1694 -0.1108
1.9998 -0.9981 -1.0015 0.2153 0.1694 0.1108
0.9974 -1.9997 -2.0029 0.3856 0.2784 -0.0380
1.0000 1.0010 0.0005 -0.0493 0.0650 0.0872
-0.0008 0.9999 0.0005 -0.0642 0.0448 0.0007
1.0015 -0.9987 -0.0005 0.0792 -0.0247 0.0859
-2.0024 -2.0026 -1.0019 0.2196 0.0440 -0.2361
-1.0000 -1.0010 -0.0005 0.0493 -0.0650 -0.0872
-0.0025 -0.0005 -1.0009 0.1211 0.1740 -0.0616
-2.0039 -0.0028 -1.0009 0.0911 0.1337 -0.2347
1.9990 0.0018 -1.0010 0.1510 0.2142 0.1115
1.8578 11.4153 -1.8806 -0.4771 0.8773 0.0534
-9.7967 3.2772 -1.7891 -0.1412 0.2617 -0.9548
-0.2286 -12.7523 0.1755 0.7936 -0.6082 -0.0180
7.1415 -9.3587 0.9985 0.5871 -0.4509 0.6723
-7.0202 -9.7064 -0.6810 0.5996 -0.4587 -0.6558
1.6308 11.4847 1.8662 -0.9382 0.2243 0.2636
6.0969 -10.4237 -0.8057 0.8580 -0.2060 0.4705
-7.6932 -7.3466 -1.9732 0.5944 -0.1414 -0.7916
1.9889 -9.3262 2.9860 0.2671 -0.8984 0.3486
-6.8470 -8.7589 1.7499 0.2474 -0.8353 -0.4910
-9.7387 -5.9255 0.5660 0.1653 -0.5601 -0.8117
9.1680 -3.6923 2.1962 0.1091 -0.3638 0.9251
3.0642 12.2611 0.1697 -0.7612 0.5830 0.2841
-6.0244 6.4362 3.0471 -0.8722 -0.3615 -0.3296

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19755
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.568
_diffrn_reflns_theta_min         5.171
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -22.00   1.00    5.00    --  -40.85 -38.00  60.00   83
  2  ω   -103.00 -73.00   1.00    5.00    --  -40.85 -57.00 150.00   30
  3  ω    -66.00 -20.00   1.00    5.00    --  -40.85 -57.00 -60.00   46
  4  ω   -111.00 -13.00   1.00    5.00    --  -40.85 -57.00   0.00   98
  5  ω    -76.00 -51.00   1.00    5.00    --  -40.85 -57.00  60.00   25
  6  ω    -19.00  69.00   1.00    5.00    --   40.85 -77.00 -60.00   88
  7  ω      7.00  64.00   1.00    5.00    --   40.85 -99.00-150.00   57
  8  ω      7.00  80.00   1.00    5.00    --   40.85 -99.00-180.00   73
  9  ω     22.00  52.00   1.00    5.00    --   40.85  57.00 120.00   30
 10  ω     23.00  95.00   1.00   20.00    --  105.15 -94.00 -30.00   72
 11  ω     80.00 107.00   1.00   20.00    --  105.15  45.00  60.00   27
 12  ω     28.00 100.00   1.00   20.00    --  105.15 -94.00  30.00   72
 13  ω    114.00 177.00   1.00   20.00    --  105.15  61.00 120.00   63
 14  ω     76.00 105.00   1.00   20.00    --  105.15  61.00  90.00   29
 15  ω     78.00 168.00   1.00   20.00    --  105.15  54.00  76.20   90
 16  ω     79.00 120.00   1.00   20.00    --  105.15  49.00 119.85   41
 17  ω    104.00 160.00   1.00   20.00    --  105.15 111.00-150.00   56
 18  ω     76.00 103.00   1.00   20.00    --  105.15  61.00  60.00   27
 19  ω    122.00 158.00   1.00   20.00    --  105.15  45.00 150.00   36
 20  ω     78.00 104.00   1.00   20.00    --  105.15  53.00 125.02   26
 21  ω     79.00 106.00   1.00   20.00    --  105.15  45.00 150.00   27
 22  ω     77.00 136.00   1.00   20.00    --  105.15  61.00   0.00   59
 23  ω    142.00 171.00   1.00   20.00    --  105.15  61.00  30.00   29
 24  ω     79.00 111.00   1.00   20.00    --  105.15  45.00   0.00   32
 25  ω     80.00 106.00   1.00   20.00    --  105.15  45.00 120.00   26
 26  ω     79.00 106.00   1.00   20.00    --  105.15  61.00 120.00   27
 27  ω     24.00  96.00   1.00   20.00    --  105.15 -94.00-150.00   72
 28  ω     76.00 102.00   1.00   20.00    --  105.15  61.00  30.00   26
 29  ω     81.00 108.00   1.00   20.00    --  105.15  30.00  60.00   27
 30  ω     81.00 108.00   1.00   20.00    --  105.15  45.00  30.00   27
 31  ω     76.00 102.00   1.00   20.00    --  105.15  60.00  -5.57   26
 32  ω    125.00 174.00   1.00   20.00    --  105.15  62.00  11.16   49
 33  ω     77.00 102.00   1.00   20.00    --  105.15  62.00  11.16   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0150368000
_diffrn_orient_matrix_UB_12      -0.0641668000
_diffrn_orient_matrix_UB_13      -0.1209715000
_diffrn_orient_matrix_UB_21      0.0200684000
_diffrn_orient_matrix_UB_22      0.0449382000
_diffrn_orient_matrix_UB_23      -0.1738763000
_diffrn_orient_matrix_UB_31      0.0864891000
_diffrn_orient_matrix_UB_32      0.0007047000
_diffrn_orient_matrix_UB_33      0.0613503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                4388
_reflns_number_total             4466
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       0.00076(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.3364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.96(2)
 0.04(2)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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_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 0.38044(3) 0.75779(8) 0.66947(4) 0.03921(15) Uani 1 1 d . . . . .
O1 O 0.38729(12) 0.7859(3) 0.59655(9) 0.0505(5) Uani 1 1 d . . . . .
O2 O 0.30293(13) 0.7996(3) 0.69490(11) 0.0632(6) Uani 1 1 d . . . . .
O3 O 0.44013(15) 0.8590(3) 0.70718(11) 0.0635(6) Uani 1 1 d . . . . .
O4 O 0.55392(13) 0.8615(3) 0.29951(10) 0.0560(5) Uani 1 1 d . . . . .
H4 H 0.563(3) 0.954(8) 0.278(3) 0.102(16) Uiso 1 1 d . . . . .
N1 N 0.36920(11) 0.2673(3) 0.47344(10) 0.0361(4) Uani 1 1 d . . . . .
C1 C 0.39346(14) 0.3929(3) 0.42826(11) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.35892(13) 0.3445(3) 0.35851(11) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.30871(13) 0.1747(3) 0.37562(11) 0.0371(5) Uani 1 1 d . . . . .
C4 C 0.25834(15) 0.0683(3) 0.33570(12) 0.0442(5) Uani 1 1 d . . . . .
H4A H 0.251895 0.096274 0.288755 0.053 Uiso 1 1 calc R U . . .
C5 C 0.21770(16) -0.0796(3) 0.36582(14) 0.0499(6) Uani 1 1 d . . . . .
H5 H 0.182377 -0.153575 0.339369 0.060 Uiso 1 1 calc R U . . .
C6 C 0.22768(16) -0.1221(3) 0.43432(14) 0.0471(6) Uani 1 1 d . . . . .
H6 H 0.199067 -0.225215 0.453616 0.057 Uiso 1 1 calc R U . . .
C7 C 0.27838(15) -0.0179(3) 0.47547(12) 0.0410(5) Uani 1 1 d . . . . .
H7 H 0.285594 -0.047299 0.522217 0.049 Uiso 1 1 calc R U . . .
C8 C 0.31777(13) 0.1317(3) 0.44401(11) 0.0349(4) Uani 1 1 d . . . . .
C9 C 0.30761(15) 0.5091(3) 0.33261(13) 0.0446(5) Uani 1 1 d . . . . .
H9A H 0.267058 0.537680 0.366314 0.067 Uiso 1 1 calc R U . . .
H9B H 0.282980 0.471823 0.289605 0.067 Uiso 1 1 calc R U . . .
H9C H 0.340002 0.622982 0.325355 0.067 Uiso 1 1 calc R U . . .
C10 C 0.42111(16) 0.2924(4) 0.30507(13) 0.0505(6) Uani 1 1 d . . . . .
H10A H 0.452354 0.406010 0.294279 0.076 Uiso 1 1 calc R U . . .
H10B H 0.395322 0.246104 0.263721 0.076 Uiso 1 1 calc R U . . .
H10C H 0.455256 0.191993 0.323179 0.076 Uiso 1 1 calc R U . . .
C11 C 0.38441(14) 0.2692(3) 0.54774(12) 0.0385(5) Uani 1 1 d . . . . .
H11A H 0.433882 0.337967 0.557008 0.046 Uiso 1 1 calc R U . . .
H11B H 0.389983 0.136315 0.564492 0.046 Uiso 1 1 calc R U . . .
C12 C 0.31766(14) 0.3673(3) 0.58483(12) 0.0426(5) Uani 1 1 d . . . . .
H12A H 0.268538 0.296706 0.575896 0.051 Uiso 1 1 calc R U . . .
H12B H 0.311405 0.498768 0.566869 0.051 Uiso 1 1 calc R U . . .
C13 C 0.33158(16) 0.3768(4) 0.66189(12) 0.0472(5) Uani 1 1 d . . . . .
H13A H 0.282253 0.417239 0.683956 0.057 Uiso 1 1 calc R U . . .
H13B H 0.343646 0.246111 0.678239 0.057 Uiso 1 1 calc R U . . .
C14 C 0.39685(16) 0.5109(4) 0.68578(11) 0.0443(5) Uani 1 1 d . . . . .
H14A H 0.446143 0.472426 0.663221 0.053 Uiso 1 1 calc R U . . .
H14B H 0.404087 0.493396 0.735341 0.053 Uiso 1 1 calc R U . . .
C15 C 0.44145(14) 0.5516(4) 0.44663(12) 0.0411(5) Uani 1 1 d . . . . .
H15 H 0.451171 0.573710 0.493546 0.049 Uiso 1 1 calc R U . . .
C16 C 0.47396(14) 0.6728(3) 0.40071(12) 0.0418(5) Uani 1 1 d . . . . .
H16 H 0.465394 0.644751 0.354029 0.050 Uiso 1 1 calc R U . . .
C17 C 0.52028(14) 0.8400(3) 0.41589(12) 0.0416(5) Uani 1 1 d . . . . .
C18 C 0.52645(16) 0.9160(4) 0.48201(13) 0.0472(5) Uani 1 1 d . . . . .
H18 H 0.500392 0.854687 0.518690 0.057 Uiso 1 1 calc R U . . .
C19 C 0.56979(18) 1.0779(4) 0.49392(16) 0.0560(6) Uani 1 1 d . . . . .
H19 H 0.573721 1.127767 0.538743 0.067 Uiso 1 1 calc R U . . .
C20 C 0.60789(17) 1.1690(4) 0.44066(17) 0.0567(7) Uani 1 1 d . . . . .
H20 H 0.637576 1.281318 0.449306 0.068 Uiso 1 1 calc R U . . .
C21 C 0.60312(15) 1.0982(4) 0.37530(16) 0.0520(6) Uani 1 1 d . . . . .
H21 H 0.629398 1.161485 0.339162 0.062 Uiso 1 1 calc R U . . .
C22 C 0.55957(14) 0.9333(4) 0.36246(13) 0.0440(5) 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 O1 1.4521(19) . ?
S1 O2 1.447(2) . ?
S1 O3 1.447(2) . ?
S1 C14 1.777(3) . ?
O4 C22 1.339(3) . ?
N1 C1 1.316(3) . ?
N1 C8 1.416(3) . ?
N1 C11 1.484(3) . ?
C1 C2 1.531(3) . ?
C1 C15 1.426(3) . ?
C2 C3 1.503(3) . ?
C2 C9 1.534(3) . ?
C2 C10 1.539(3) . ?
C3 C4 1.383(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.379(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.392(4) . ?
C7 C8 1.389(3) . ?
C11 C12 1.518(3) . ?
C12 C13 1.535(3) . ?
C13 C14 1.531(4) . ?
C15 C16 1.357(3) . ?
C16 C17 1.443(3) . ?
C17 C18 1.408(4) . ?
C17 C22 1.407(3) . ?
C18 C19 1.373(4) . ?
C19 C20 1.388(5) . ?
C20 C21 1.380(4) . ?
C21 C22 1.395(4) . ?

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 S1 C14 107.27(12) . . ?
O2 S1 O1 112.81(13) . . ?
O2 S1 C14 106.18(14) . . ?
O3 S1 O1 112.52(13) . . ?
O3 S1 O2 111.77(15) . . ?
O3 S1 C14 105.71(12) . . ?
C1 N1 C8 111.5(2) . . ?
C1 N1 C11 127.1(2) . . ?
C8 N1 C11 121.16(19) . . ?
N1 C1 C2 109.6(2) . . ?
N1 C1 C15 121.9(2) . . ?
C15 C1 C2 128.4(2) . . ?
C1 C2 C9 110.7(2) . . ?
C1 C2 C10 113.4(2) . . ?
C3 C2 C1 101.20(17) . . ?
C3 C2 C9 109.82(19) . . ?
C3 C2 C10 111.2(2) . . ?
C9 C2 C10 110.3(2) . . ?
C4 C3 C2 130.8(2) . . ?
C4 C3 C8 120.2(2) . . ?
C8 C3 C2 108.94(19) . . ?
C5 C4 C3 118.3(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 C7 121.9(2) . . ?
C8 C7 C6 115.9(2) . . ?
C3 C8 N1 108.7(2) . . ?
C3 C8 C7 122.7(2) . . ?
C7 C8 N1 128.5(2) . . ?
N1 C11 C12 110.20(19) . . ?
C11 C12 C13 112.2(2) . . ?
C14 C13 C12 116.3(2) . . ?
C13 C14 S1 115.04(19) . . ?
C16 C15 C1 123.5(2) . . ?
C15 C16 C17 126.3(2) . . ?
C18 C17 C16 122.5(2) . . ?
C22 C17 C16 118.9(2) . . ?
C22 C17 C18 118.6(2) . . ?
C19 C18 C17 120.6(2) . . ?
C18 C19 C20 120.2(3) . . ?
C21 C20 C19 120.7(3) . . ?
C20 C21 C22 119.8(3) . . ?
O4 C22 C17 118.8(2) . . ?
O4 C22 C21 121.0(2) . . ?
C21 C22 C17 120.2(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O3 0.79(5) 1.90(5) 2.668(3) 162(5) 2_674 yes

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
O1 S1 C14 C13 -70.6(2) . . . . ?
O2 S1 C14 C13 50.2(2) . . . . ?
O3 S1 C14 C13 169.10(18) . . . . ?
N1 C1 C2 C3 2.5(2) . . . . ?
N1 C1 C2 C9 118.9(2) . . . . ?
N1 C1 C2 C10 -116.6(2) . . . . ?
N1 C1 C15 C16 173.1(2) . . . . ?
N1 C11 C12 C13 -178.74(19) . . . . ?
C1 N1 C8 C3 -0.2(3) . . . . ?
C1 N1 C8 C7 -177.7(2) . . . . ?
C1 N1 C11 C12 94.0(3) . . . . ?
C1 C2 C3 C4 176.3(2) . . . . ?
C1 C2 C3 C8 -2.6(2) . . . . ?
C1 C15 C16 C17 177.3(2) . . . . ?
C2 C1 C15 C16 -10.3(4) . . . . ?
C2 C3 C4 C5 -178.4(2) . . . . ?
C2 C3 C8 N1 1.8(2) . . . . ?
C2 C3 C8 C7 179.5(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C3 C8 N1 -177.1(2) . . . . ?
C4 C3 C8 C7 0.6(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C6 C7 C8 N1 176.3(2) . . . . ?
C6 C7 C8 C3 -0.9(3) . . . . ?
C8 N1 C1 C2 -1.6(3) . . . . ?
C8 N1 C1 C15 175.6(2) . . . . ?
C8 N1 C11 C12 -79.4(3) . . . . ?
C8 C3 C4 C5 0.3(3) . . . . ?
C9 C2 C3 C4 59.3(3) . . . . ?
C9 C2 C3 C8 -119.5(2) . . . . ?
C10 C2 C3 C4 -63.0(3) . . . . ?
C10 C2 C3 C8 118.2(2) . . . . ?
C11 N1 C1 C2 -175.5(2) . . . . ?
C11 N1 C1 C15 1.6(4) . . . . ?
C11 N1 C8 C3 174.18(19) . . . . ?
C11 N1 C8 C7 -3.3(4) . . . . ?
C11 C12 C13 C14 69.4(3) . . . . ?
C12 C13 C14 S1 64.7(3) . . . . ?
C15 C1 C2 C3 -174.4(2) . . . . ?
C15 C1 C2 C9 -58.0(3) . . . . ?
C15 C1 C2 C10 66.5(3) . . . . ?
C15 C16 C17 C18 -11.0(4) . . . . ?
C15 C16 C17 C22 170.3(2) . . . . ?
C16 C17 C18 C19 -178.6(3) . . . . ?
C16 C17 C22 O4 -1.3(3) . . . . ?
C16 C17 C22 C21 178.3(2) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C17 C22 O4 180.0(2) . . . . ?
C18 C17 C22 C21 -0.4(4) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C19 C20 C21 C22 0.0(5) . . . . ?
C20 C21 C22 O4 180.0(3) . . . . ?
C20 C21 C22 C17 0.3(4) . . . . ?
C22 C17 C18 C19 0.1(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.117 -0.065 0.140 127.5 32.6 '1.9 MeOH'
2 0.117 -0.980 0.640 127.5 32.7 '1.9 MeOH'
3 0.383 -0.893 0.140 127.5 32.7 '1.9 MeOH'
4 0.617 -0.538 0.640 127.5 32.6 '1.9 MeOH'

_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.494
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.96(2)
2 0.04(2)

