# Electronic Supplementary Material (ESI) for ChemComm.
# 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_XA-561
_database_code_depnum_ccdc_archive 'CCDC 2056092'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 N2 O5 S'
_chemical_formula_sum            'C28 H28 N2 O5 S'
_chemical_formula_weight         504.58

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                   9.4255(5)
_cell_length_b                   34.4504(18)
_cell_length_c                   8.2876(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.801(6)
_cell_angle_gamma                90
_cell_volume                     2624.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6107
_cell_measurement_theta_min      3.4760
_cell_measurement_theta_max      23.9120

_exptl_crystal_description       'small bit'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            17083
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4793
_reflns_number_gt                3334
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0556P)²+0.8396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4775
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.57021(7) 0.69752(2) 0.03104(8) 0.0507(2) Uani 1 1 d . . . . .
C1 C 0.5858(3) 0.62981(6) 0.1926(3) 0.0436(6) Uani 1 1 d . . . . .
H1A H 0.594397 0.620293 0.084989 0.052 Uiso 1 1 calc R U . . .
H1AB H 0.491975 0.622005 0.211462 0.052 Uiso 1 1 calc R U . . .
N1 N 0.6002(2) 0.67196(5) 0.1998(2) 0.0470(5) Uani 1 1 d . . . . .
O1 O 0.78662(18) 0.53818(5) 0.6472(2) 0.0540(5) Uani 1 1 d . . . . .
O3 O 0.6128(2) 0.67411(6) -0.0929(2) 0.0693(6) Uani 1 1 d . . . . .
C3 C 0.7019(3) 0.63242(7) 0.4927(3) 0.0427(6) Uani 1 1 d . . . . .
O2 O 0.6363(2) 0.73442(5) 0.0739(2) 0.0700(6) Uani 1 1 d . . . . .
C2 C 0.7084(2) 0.61359(6) 0.3280(3) 0.0402(5) Uani 1 1 d . . . . .
N2 N 0.8077(2) 0.55247(5) 0.2654(2) 0.0440(5) Uani 1 1 d . . . . .
O4 O 0.8942(2) 0.50024(5) 0.1495(2) 0.0654(5) Uani 1 1 d . . . . .
C4 C 0.6424(3) 0.66681(7) 0.5008(3) 0.0544(7) Uani 1 1 d . . . . .
H4 H 0.641015 0.676878 0.604579 0.065 Uiso 1 1 calc R U . . .
O5 O 0.71963(19) 0.49457(5) 0.2984(2) 0.0583(5) Uani 1 1 d . . . . .
C5 C 0.5769(3) 0.69044(7) 0.3512(3) 0.0595(7) Uani 1 1 d . . . . .
H5A H 0.473337 0.693392 0.344045 0.071 Uiso 1 1 calc R U . . .
H5AB H 0.620382 0.716093 0.361750 0.071 Uiso 1 1 calc R U . . .
C9 C 0.8149(3) 0.51401(7) 0.2305(3) 0.0467(6) Uani 1 1 d . . . . .
C8 C 0.8559(2) 0.61755(7) 0.2816(3) 0.0436(6) Uani 1 1 d . . . . .
C7 C 0.9054(3) 0.58174(7) 0.2408(3) 0.0436(6) Uani 1 1 d . . . . .
C6 C 0.7035(2) 0.56875(6) 0.3564(3) 0.0413(5) Uani 1 1 d . . . . .
H6 H 0.605427 0.558119 0.317625 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7514(2) 0.60249(7) 0.6163(3) 0.0448(6) Uani 1 1 d . . . . .
C11 C 0.7506(3) 0.56825(7) 0.5402(3) 0.0438(6) Uani 1 1 d . . . . .
C12 C 0.8134(3) 0.55583(8) 0.8016(3) 0.0597(7) Uani 1 1 d . . . . .
H12 H 0.842787 0.542502 0.900950 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7919(3) 0.59425(8) 0.7908(3) 0.0552(7) Uani 1 1 d . . . . .
H13 H 0.801208 0.611856 0.877608 0.066 Uiso 1 1 calc R U . . .
C14 C 0.3811(3) 0.70513(7) -0.0303(3) 0.0464(6) Uani 1 1 d . . . . .
C15 C 0.3179(3) 0.73694(8) 0.0273(3) 0.0616(7) Uani 1 1 d . . . . .
H15 H 0.375037 0.754730 0.097456 0.074 Uiso 1 1 calc R U . . .
C16 C 0.1695(4) 0.74206(10) -0.0201(4) 0.0744(9) Uani 1 1 d . . . . .
H16 H 0.127483 0.763596 0.018387 0.089 Uiso 1 1 calc R U . . .
C17 C 0.0818(3) 0.71617(11) -0.1227(4) 0.0766(9) Uani 1 1 d . . . . .
C18 C 0.1467(4) 0.68460(10) -0.1791(4) 0.0805(9) Uani 1 1 d . . . . .
H18 H 0.089366 0.666716 -0.248550 0.097 Uiso 1 1 calc R U . . .
C19 C 0.2957(3) 0.67908(8) -0.1342(4) 0.0650(8) Uani 1 1 d . . . . .
H19 H 0.337917 0.657784 -0.174179 0.078 Uiso 1 1 calc R U . . .
C20 C -0.0798(4) 0.72214(14) -0.1726(6) 0.1279(16) Uani 1 1 d . . . . .
H20A H -0.128145 0.697533 -0.176163 0.192 Uiso 1 1 calc R U . . .
H20B H -0.104129 0.734011 -0.280013 0.192 Uiso 1 1 calc R U . . .
H20C H -0.110368 0.738704 -0.093562 0.192 Uiso 1 1 calc R U . . .
C21 C 1.0343(3) 0.57807(9) 0.1883(3) 0.0579(7) Uani 1 1 d . . . . .
H21 H 1.066429 0.554033 0.159802 0.070 Uiso 1 1 calc R U . . .
C22 C 1.1126(3) 0.61115(10) 0.1801(4) 0.0746(9) Uani 1 1 d . . . . .
H22 H 1.199138 0.609455 0.144187 0.089 Uiso 1 1 calc R U . . .
C23 C 1.0674(3) 0.64673(10) 0.2231(4) 0.0752(9) Uani 1 1 d . . . . .
H23 H 1.124322 0.668546 0.218018 0.090 Uiso 1 1 calc R U . . .
C24 C 0.9372(3) 0.65055(8) 0.2743(3) 0.0586(7) Uani 1 1 d . . . . .
H24 H 0.905848 0.674665 0.302898 0.070 Uiso 1 1 calc R U . . .
C25 C 0.7008(3) 0.45240(7) 0.2819(4) 0.0636(8) Uani 1 1 d . . . . .
C26 C 0.5986(4) 0.44405(10) 0.3944(6) 0.1143(15) Uani 1 1 d . . . . .
H26A H 0.583207 0.416563 0.398759 0.171 Uiso 1 1 calc R U . . .
H26B H 0.507246 0.456780 0.352489 0.171 Uiso 1 1 calc R U . . .
H26C H 0.640295 0.453513 0.503591 0.171 Uiso 1 1 calc R U . . .
C27 C 0.8432(4) 0.43154(10) 0.3429(5) 0.0939(11) Uani 1 1 d . . . . .
H27A H 0.824608 0.404923 0.365589 0.141 Uiso 1 1 calc R U . . .
H27B H 0.896149 0.443753 0.442196 0.141 Uiso 1 1 calc R U . . .
H27C H 0.899580 0.432652 0.259657 0.141 Uiso 1 1 calc R U . . .
C28 C 0.6340(5) 0.44337(11) 0.1042(5) 0.1271(16) Uani 1 1 d . . . . .
H28A H 0.621029 0.415821 0.090791 0.191 Uiso 1 1 calc R U . . .
H28B H 0.696874 0.452450 0.035589 0.191 Uiso 1 1 calc R U . . .
H28C H 0.541279 0.456043 0.072413 0.191 Uiso 1 1 calc R U . . .


_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 1.4257(19) . ?
S1 O3 1.4311(19) . ?
S1 N1 1.6239(19) . ?
S1 C14 1.761(3) . ?
C1 N1 1.458(3) . ?
C1 C2 1.527(3) . ?
C1 H1A 0.9700 . ?
C1 H1AB 0.9700 . ?
N1 C5 1.466(3) . ?
O1 C11 1.357(3) . ?
O1 C12 1.388(3) . ?
C3 C4 1.319(3) . ?
C3 C10 1.456(3) . ?
C3 C2 1.524(3) . ?
C2 C8 1.528(3) . ?
C2 C6 1.565(3) . ?
N2 C9 1.361(3) . ?
N2 C7 1.411(3) . ?
N2 C6 1.475(3) . ?
O4 C9 1.208(3) . ?
C4 C5 1.497(3) . ?
C4 H4 0.9300 . ?
O5 C9 1.340(3) . ?
O5 C25 1.466(3) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C8 C24 1.380(3) . ?
C8 C7 1.387(3) . ?
C7 C21 1.384(3) . ?
C6 C11 1.490(3) . ?
C6 H6 0.9800 . ?
C10 C11 1.337(3) . ?
C10 C13 1.440(3) . ?
C12 C13 1.339(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.374(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.378(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(5) . ?
C17 C20 1.502(5) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.368(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C28 1.501(5) . ?
C25 C27 1.508(4) . ?
C25 C26 1.510(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
O2 S1 O3 120.33(13) . . ?
O2 S1 N1 106.61(11) . . ?
O3 S1 N1 106.84(11) . . ?
O2 S1 C14 107.30(12) . . ?
O3 S1 C14 107.65(12) . . ?
N1 S1 C14 107.53(11) . . ?
N1 C1 C2 106.61(17) . . ?
N1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
N1 C1 H1AB 110.4 . . ?
C2 C1 H1AB 110.4 . . ?
H1A C1 H1AB 108.6 . . ?
C1 N1 C5 115.96(19) . . ?
C1 N1 S1 120.50(14) . . ?
C5 N1 S1 118.12(16) . . ?
C11 O1 C12 103.64(19) . . ?
C4 C3 C10 132.4(2) . . ?
C4 C3 C2 122.0(2) . . ?
C10 C3 C2 104.97(19) . . ?
C3 C2 C1 109.15(18) . . ?
C3 C2 C8 113.99(19) . . ?
C1 C2 C8 111.37(18) . . ?
C3 C2 C6 106.10(17) . . ?
C1 C2 C6 115.39(18) . . ?
C8 C2 C6 100.66(17) . . ?
C9 N2 C7 126.87(19) . . ?
C9 N2 C6 123.29(19) . . ?
C7 N2 C6 109.41(18) . . ?
C3 C4 C5 123.2(2) . . ?
C3 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C9 O5 C25 122.33(19) . . ?
N1 C5 C4 111.1(2) . . ?
N1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N1 C5 H5AB 109.4 . . ?
C4 C5 H5AB 109.4 . . ?
H5A C5 H5AB 108.0 . . ?
O4 C9 O5 126.3(2) . . ?
O4 C9 N2 124.5(2) . . ?
O5 C9 N2 109.1(2) . . ?
C24 C8 C7 120.1(2) . . ?
C24 C8 C2 129.0(2) . . ?
C7 C8 C2 110.8(2) . . ?
C21 C7 C8 121.6(2) . . ?
C21 C7 N2 128.8(2) . . ?
C8 C7 N2 109.54(19) . . ?
N2 C6 C11 115.95(19) . . ?
N2 C6 C2 104.66(17) . . ?
C11 C6 C2 98.79(17) . . ?
N2 C6 H6 112.1 . . ?
C11 C6 H6 112.1 . . ?
C2 C6 H6 112.1 . . ?
C11 C10 C13 105.8(2) . . ?
C11 C10 C3 109.0(2) . . ?
C13 C10 C3 145.0(2) . . ?
C10 C11 O1 113.0(2) . . ?
C10 C11 C6 116.2(2) . . ?
O1 C11 C6 130.7(2) . . ?
C13 C12 O1 112.2(2) . . ?
C13 C12 H12 123.9 . . ?
O1 C12 H12 123.9 . . ?
C12 C13 C10 105.3(2) . . ?
C12 C13 H13 127.3 . . ?
C10 C13 H13 127.3 . . ?
C19 C14 C15 119.8(3) . . ?
C19 C14 S1 119.9(2) . . ?
C15 C14 S1 120.3(2) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 C20 121.0(4) . . ?
C18 C17 C20 120.9(4) . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 119.9(3) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C7 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C7 C21 H21 121.3 . . ?
C21 C22 C23 122.0(3) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C8 C24 C23 118.1(3) . . ?
C8 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
O5 C25 C28 108.2(3) . . ?
O5 C25 C27 111.2(2) . . ?
C28 C25 C27 112.3(3) . . ?
O5 C25 C26 102.2(2) . . ?
C28 C25 C26 112.3(3) . . ?
C27 C25 C26 110.2(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C2 C1 N1 C5 -65.1(3) . . . . ?
C2 C1 N1 S1 141.39(16) . . . . ?
O2 S1 N1 C1 -161.82(18) . . . . ?
O3 S1 N1 C1 -32.0(2) . . . . ?
C14 S1 N1 C1 83.4(2) . . . . ?
O2 S1 N1 C5 45.2(2) . . . . ?
O3 S1 N1 C5 175.06(19) . . . . ?
C14 S1 N1 C5 -69.6(2) . . . . ?
C4 C3 C2 C1 -25.0(3) . . . . ?
C10 C3 C2 C1 146.86(19) . . . . ?
C4 C3 C2 C8 100.3(3) . . . . ?
C10 C3 C2 C8 -87.9(2) . . . . ?
C4 C3 C2 C6 -149.9(2) . . . . ?
C10 C3 C2 C6 21.9(2) . . . . ?
N1 C1 C2 C3 53.9(2) . . . . ?
N1 C1 C2 C8 -72.8(2) . . . . ?
N1 C1 C2 C6 173.27(17) . . . . ?
C10 C3 C4 C5 -169.6(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C1 N1 C5 C4 39.5(3) . . . . ?
S1 N1 C5 C4 -166.34(19) . . . . ?
C3 C4 C5 N1 -5.2(4) . . . . ?
C25 O5 C9 O4 0.4(4) . . . . ?
C25 O5 C9 N2 179.7(2) . . . . ?
C7 N2 C9 O4 -12.0(4) . . . . ?
C6 N2 C9 O4 176.3(2) . . . . ?
C7 N2 C9 O5 168.7(2) . . . . ?
C6 N2 C9 O5 -3.0(3) . . . . ?
C3 C2 C8 C24 -52.2(3) . . . . ?
C1 C2 C8 C24 71.8(3) . . . . ?
C6 C2 C8 C24 -165.4(2) . . . . ?
C3 C2 C8 C7 128.8(2) . . . . ?
C1 C2 C8 C7 -107.2(2) . . . . ?
C6 C2 C8 C7 15.7(2) . . . . ?
C24 C8 C7 C21 -1.5(4) . . . . ?
C2 C8 C7 C21 177.5(2) . . . . ?
C24 C8 C7 N2 177.2(2) . . . . ?
C2 C8 C7 N2 -3.7(3) . . . . ?
C9 N2 C7 C21 -5.2(4) . . . . ?
C6 N2 C7 C21 167.5(2) . . . . ?
C9 N2 C7 C8 176.2(2) . . . . ?
C6 N2 C7 C8 -11.1(2) . . . . ?
C9 N2 C6 C11 86.1(3) . . . . ?
C7 N2 C6 C11 -86.9(2) . . . . ?
C9 N2 C6 C2 -166.3(2) . . . . ?
C7 N2 C6 C2 20.7(2) . . . . ?
C3 C2 C6 N2 -140.08(18) . . . . ?
C1 C2 C6 N2 98.9(2) . . . . ?
C8 C2 C6 N2 -21.1(2) . . . . ?
C3 C2 C6 C11 -20.2(2) . . . . ?
C1 C2 C6 C11 -141.20(19) . . . . ?
C8 C2 C6 C11 98.81(18) . . . . ?
C4 C3 C10 C11 156.2(3) . . . . ?
C2 C3 C10 C11 -14.4(3) . . . . ?
C4 C3 C10 C13 -17.2(6) . . . . ?
C2 C3 C10 C13 172.2(3) . . . . ?
C13 C10 C11 O1 0.0(3) . . . . ?
C3 C10 C11 O1 -176.09(19) . . . . ?
C13 C10 C11 C6 176.8(2) . . . . ?
C3 C10 C11 C6 0.7(3) . . . . ?
C12 O1 C11 C10 -0.8(3) . . . . ?
C12 O1 C11 C6 -177.0(2) . . . . ?
N2 C6 C11 C10 123.8(2) . . . . ?
C2 C6 C11 C10 12.7(3) . . . . ?
N2 C6 C11 O1 -60.1(3) . . . . ?
C2 C6 C11 O1 -171.2(2) . . . . ?
C11 O1 C12 C13 1.4(3) . . . . ?
O1 C12 C13 C10 -1.4(3) . . . . ?
C11 C10 C13 C12 0.9(3) . . . . ?
C3 C10 C13 C12 174.4(3) . . . . ?
O2 S1 C14 C19 155.6(2) . . . . ?
O3 S1 C14 C19 24.7(2) . . . . ?
N1 S1 C14 C19 -90.1(2) . . . . ?
O2 S1 C14 C15 -25.3(2) . . . . ?
O3 S1 C14 C15 -156.2(2) . . . . ?
N1 S1 C14 C15 89.0(2) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
S1 C14 C15 C16 -179.0(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C15 C16 C17 C20 179.8(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C20 C17 C18 C19 179.7(3) . . . . ?
C15 C14 C19 C18 -0.7(4) . . . . ?
S1 C14 C19 C18 178.4(2) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
C8 C7 C21 C22 0.8(4) . . . . ?
N2 C7 C21 C22 -177.7(2) . . . . ?
C7 C21 C22 C23 0.6(4) . . . . ?
C21 C22 C23 C24 -1.2(5) . . . . ?
C7 C8 C24 C23 0.9(4) . . . . ?
C2 C8 C24 C23 -178.0(2) . . . . ?
C22 C23 C24 C8 0.5(4) . . . . ?
C9 O5 C25 C28 -68.0(3) . . . . ?
C9 O5 C25 C27 55.8(3) . . . . ?
C9 O5 C25 C26 173.3(3) . . . . ?

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
C4 H4 O3 0.93 2.58 3.449(3) 155.5 1_556 yes
C5 H5AB O2 0.97 2.43 3.156(3) 131.4 4_576 yes
C12 H12 O4 0.93 2.48 3.404(3) 171.9 1_556 yes
C21 H21 O4 0.93 2.45 2.974(3) 115.5 . yes
C28 H28B O4 0.96 2.51 3.097(5) 119.7 . yes

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_XA-849
_database_code_depnum_ccdc_archive 'CCDC 2127769'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-12-10 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O3 S'
_chemical_formula_sum            'C23 H21 N3 O3 S'
_chemical_formula_weight         419.49

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.1095(3)
_cell_length_b                   8.1293(2)
_cell_length_c                   22.4667(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.438(2)
_cell_angle_gamma                90
_cell_volume                     1973.47(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    32743
_cell_measurement_theta_min      2.6620
_cell_measurement_theta_max      29.3270

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.37426
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            41286
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.673
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4183
_reflns_number_gt                3654
_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       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0508P)²+0.6757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4182
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36793(3) 0.02151(4) 0.60942(2) 0.03855(12) Uani 1 1 d . . . . .
C1 C 0.53164(12) 0.17530(17) 0.55775(6) 0.0328(3) Uani 1 1 d . . . . .
H1A H 0.486204 0.214322 0.518075 0.039 Uiso 1 1 calc R U . . .
H1B H 0.558801 0.063499 0.553331 0.039 Uiso 1 1 calc R U . . .
N1 N 0.45332(11) 0.18176(14) 0.60235(6) 0.0348(3) Uani 1 1 d . . . . .
O1 O 0.84027(10) 0.59788(14) 0.53436(5) 0.0492(3) Uani 1 1 d . . . . .
O2 O 0.43817(12) -0.12005(13) 0.60059(6) 0.0546(3) Uani 1 1 d . . . . .
N2 N 0.83766(11) 0.20308(16) 0.56282(6) 0.0400(3) Uani 1 1 d . . . . .
C2 C 0.64244(12) 0.28658(16) 0.58300(6) 0.0292(3) Uani 1 1 d . . . . .
C24 C 0.71866(15) 0.18306(19) 0.69662(7) 0.0411(3) Uani 1 1 d . . . . .
H24 H 0.649090 0.217443 0.709583 0.049 Uiso 1 1 calc R U . . .
C5 C 0.39596(14) 0.34232(17) 0.60782(8) 0.0405(3) Uani 1 1 d . . . . .
H5A H 0.367860 0.345775 0.645573 0.049 Uiso 1 1 calc R U . . .
H5B H 0.324438 0.356540 0.574019 0.049 Uiso 1 1 calc R U . . .
C4 C 0.48547(14) 0.47919(17) 0.60749(7) 0.0378(3) Uani 1 1 d . . . . .
H4 H 0.462650 0.585317 0.615758 0.045 Uiso 1 1 calc R U . . .
O3 O 0.24453(10) 0.03751(16) 0.57274(6) 0.0539(3) Uani 1 1 d . . . . .
N3 N 0.93380(12) 0.08588(18) 0.65886(7) 0.0506(4) Uani 1 1 d . . . . .
C3 C 0.59574(13) 0.45627(16) 0.59599(6) 0.0317(3) Uani 1 1 d . . . . .
C8 C 0.72994(12) 0.21119(16) 0.63819(6) 0.0312(3) Uani 1 1 d . . . . .
C22 C 0.91676(16) 0.0542(2) 0.71543(9) 0.0589(5) Uani 1 1 d . . . . .
H22 H 0.978667 -0.003744 0.742233 0.071 Uiso 1 1 calc R U . . .
C7 C 0.83990(13) 0.16297(17) 0.62231(7) 0.0359(3) Uani 1 1 d . . . . .
C23 C 0.81577(18) 0.1006(2) 0.73623(8) 0.0559(5) Uani 1 1 d . . . . .
H23 H 0.811531 0.077608 0.776249 0.067 Uiso 1 1 calc R U . . .
C6 C 0.73408(13) 0.31411(17) 0.53969(6) 0.0346(3) Uani 1 1 d . . . . .
H6 H 0.694507 0.292672 0.496669 0.041 Uiso 1 1 calc R U . . .
C10 C 0.68747(13) 0.57163(17) 0.58368(7) 0.0359(3) Uani 1 1 d . . . . .
C9 C 0.94566(16) 0.2018(2) 0.53750(9) 0.0534(4) Uani 1 1 d . . . . .
H9A H 1.004269 0.123226 0.559156 0.080 Uiso 1 1 calc R U . . .
H9B H 0.982572 0.309227 0.541483 0.080 Uiso 1 1 calc R U . . .
H9C H 0.922010 0.172153 0.495019 0.080 Uiso 1 1 calc R U . . .
C11 C 0.75911(14) 0.49359(18) 0.55203(7) 0.0370(3) Uani 1 1 d . . . . .
C12 C 0.81633(17) 0.7492(2) 0.55808(9) 0.0549(5) Uani 1 1 d . . . . .
H12 H 0.858686 0.845468 0.553753 0.066 Uiso 1 1 calc R U . . .
C13 C 0.72524(15) 0.74018(19) 0.58788(8) 0.0467(4) Uani 1 1 d . . . . .
H13 H 0.693340 0.825385 0.607188 0.056 Uiso 1 1 calc R U . . .
C14 C 0.36094(13) 0.03613(17) 0.68668(7) 0.0376(3) Uani 1 1 d . . . . .
C19 C 0.46305(15) -0.0072(2) 0.73243(8) 0.0462(4) Uani 1 1 d . . . . .
H19 H 0.532359 -0.053670 0.722498 0.055 Uiso 1 1 calc R U . . .
C18 C 0.46066(16) 0.0193(2) 0.79301(9) 0.0528(4) Uani 1 1 d . . . . .
H18 H 0.528961 -0.009729 0.823748 0.063 Uiso 1 1 calc R U . . .
C17 C 0.35766(16) 0.0889(2) 0.80869(8) 0.0500(4) Uani 1 1 d . . . . .
C16 C 0.25592(15) 0.1257(2) 0.76221(8) 0.0505(4) Uani 1 1 d . . . . .
H16 H 0.185541 0.168984 0.772075 0.061 Uiso 1 1 calc R U . . .
C15 C 0.25606(14) 0.0998(2) 0.70141(8) 0.0444(4) Uani 1 1 d . . . . .
H15 H 0.186509 0.124909 0.670785 0.053 Uiso 1 1 calc R U . . .
C20 C 0.3577(2) 0.1279(3) 0.87419(9) 0.0737(6) Uani 1 1 d . . . . .
H20A H 0.274198 0.144389 0.877897 0.111 Uiso 1 1 calc R U . . .
H20B H 0.404929 0.226123 0.886518 0.111 Uiso 1 1 calc R U . . .
H20C H 0.394050 0.038144 0.899935 0.111 Uiso 1 1 calc R U . . .


_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 1.4298(12) . ?
S1 O3 1.4319(12) . ?
S1 N1 1.6408(12) . ?
S1 C14 1.7595(16) . ?
C1 N1 1.4727(18) . ?
C1 C2 1.5267(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 C5 1.4701(17) . ?
O1 C11 1.3622(17) . ?
O1 C12 1.391(2) . ?
N2 C7 1.370(2) . ?
N2 C9 1.442(2) . ?
N2 C6 1.4598(19) . ?
C2 C8 1.5158(18) . ?
C2 C3 1.5257(18) . ?
C2 C6 1.5791(19) . ?
C24 C8 1.367(2) . ?
C24 C23 1.400(2) . ?
C24 H24 0.9300 . ?
C5 C4 1.493(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.323(2) . ?
C4 H4 0.9300 . ?
N3 C7 1.3255(19) . ?
N3 C22 1.352(2) . ?
C3 C10 1.458(2) . ?
C8 C7 1.406(2) . ?
C22 C23 1.365(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C6 C11 1.499(2) . ?
C6 H6 0.9800 . ?
C10 C11 1.343(2) . ?
C10 C13 1.430(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C13 1.339(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 C19 1.388(2) . ?
C19 C18 1.384(3) . ?
C19 H19 0.9300 . ?
C18 C17 1.393(3) . ?
C18 H18 0.9300 . ?
C17 C16 1.382(2) . ?
C17 C20 1.505(3) . ?
C16 C15 1.382(2) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O2 S1 O3 118.27(8) . . ?
O2 S1 N1 106.21(6) . . ?
O3 S1 N1 111.71(7) . . ?
O2 S1 C14 109.99(7) . . ?
O3 S1 C14 107.80(7) . . ?
N1 S1 C14 101.59(7) . . ?
N1 C1 C2 106.19(10) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C5 N1 C1 115.12(11) . . ?
C5 N1 S1 115.16(9) . . ?
C1 N1 S1 118.93(9) . . ?
C11 O1 C12 103.90(12) . . ?
C7 N2 C9 123.69(13) . . ?
C7 N2 C6 109.17(11) . . ?
C9 N2 C6 121.55(13) . . ?
C8 C2 C3 113.03(11) . . ?
C8 C2 C1 111.88(11) . . ?
C3 C2 C1 109.04(11) . . ?
C8 C2 C6 100.29(10) . . ?
C3 C2 C6 106.63(11) . . ?
C1 C2 C6 115.76(11) . . ?
C8 C24 C23 117.50(15) . . ?
C8 C24 H24 121.3 . . ?
C23 C24 H24 121.3 . . ?
N1 C5 C4 111.04(12) . . ?
N1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C3 C4 C5 122.95(13) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C7 N3 C22 114.23(15) . . ?
C4 C3 C10 131.80(13) . . ?
C4 C3 C2 122.43(12) . . ?
C10 C3 C2 105.16(11) . . ?
C24 C8 C7 118.43(13) . . ?
C24 C8 C2 131.98(13) . . ?
C7 C8 C2 109.58(12) . . ?
N3 C22 C23 125.09(16) . . ?
N3 C22 H22 117.5 . . ?
C23 C22 H22 117.5 . . ?
N3 C7 N2 123.37(14) . . ?
N3 C7 C8 125.44(14) . . ?
N2 C7 C8 111.18(12) . . ?
C22 C23 C24 119.21(16) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
N2 C6 C11 116.04(12) . . ?
N2 C6 C2 105.12(11) . . ?
C11 C6 C2 98.19(11) . . ?
N2 C6 H6 112.1 . . ?
C11 C6 H6 112.1 . . ?
C2 C6 H6 112.1 . . ?
C11 C10 C13 106.66(14) . . ?
C11 C10 C3 108.84(13) . . ?
C13 C10 C3 144.23(15) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C11 O1 111.96(13) . . ?
C10 C11 C6 116.76(13) . . ?
O1 C11 C6 131.21(14) . . ?
C13 C12 O1 112.18(14) . . ?
C13 C12 H12 123.9 . . ?
O1 C12 H12 123.9 . . ?
C12 C13 C10 105.29(15) . . ?
C12 C13 H13 127.4 . . ?
C10 C13 H13 127.4 . . ?
C15 C14 C19 120.45(15) . . ?
C15 C14 S1 119.60(12) . . ?
C19 C14 S1 119.84(12) . . ?
C18 C19 C14 119.30(15) . . ?
C18 C19 H19 120.4 . . ?
C14 C19 H19 120.4 . . ?
C19 C18 C17 121.10(15) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C16 C17 C18 118.19(16) . . ?
C16 C17 C20 120.51(17) . . ?
C18 C17 C20 121.27(17) . . ?
C17 C16 C15 121.70(16) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C15 C14 119.18(15) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C2 C1 N1 C5 66.42(15) . . . . ?
C2 C1 N1 S1 -150.84(9) . . . . ?
O2 S1 N1 C5 178.03(11) . . . . ?
O3 S1 N1 C5 47.73(13) . . . . ?
C14 S1 N1 C5 -66.95(12) . . . . ?
O2 S1 N1 C1 35.31(13) . . . . ?
O3 S1 N1 C1 -94.99(11) . . . . ?
C14 S1 N1 C1 150.33(11) . . . . ?
N1 C1 C2 C8 71.82(13) . . . . ?
N1 C1 C2 C3 -53.95(14) . . . . ?
N1 C1 C2 C6 -174.13(11) . . . . ?
C1 N1 C5 C4 -41.95(17) . . . . ?
S1 N1 C5 C4 173.89(11) . . . . ?
N1 C5 C4 C3 7.8(2) . . . . ?
C5 C4 C3 C10 168.59(15) . . . . ?
C5 C4 C3 C2 -1.1(2) . . . . ?
C8 C2 C3 C4 -99.96(16) . . . . ?
C1 C2 C3 C4 25.15(18) . . . . ?
C6 C2 C3 C4 150.80(14) . . . . ?
C8 C2 C3 C10 88.02(13) . . . . ?
C1 C2 C3 C10 -146.88(11) . . . . ?
C6 C2 C3 C10 -21.22(14) . . . . ?
C23 C24 C8 C7 -2.9(2) . . . . ?
C23 C24 C8 C2 176.16(15) . . . . ?
C3 C2 C8 C24 53.7(2) . . . . ?
C1 C2 C8 C24 -69.86(19) . . . . ?
C6 C2 C8 C24 166.84(15) . . . . ?
C3 C2 C8 C7 -127.16(12) . . . . ?
C1 C2 C8 C7 109.29(13) . . . . ?
C6 C2 C8 C7 -14.00(14) . . . . ?
C7 N3 C22 C23 -2.6(3) . . . . ?
C22 N3 C7 N2 -178.52(15) . . . . ?
C22 N3 C7 C8 0.1(2) . . . . ?
C9 N2 C7 N3 -15.0(2) . . . . ?
C6 N2 C7 N3 -168.86(14) . . . . ?
C9 N2 C7 C8 166.16(14) . . . . ?
C6 N2 C7 C8 12.33(16) . . . . ?
C24 C8 C7 N3 2.6(2) . . . . ?
C2 C8 C7 N3 -176.67(14) . . . . ?
C24 C8 C7 N2 -178.60(13) . . . . ?
C2 C8 C7 N2 2.12(16) . . . . ?
N3 C22 C23 C24 2.1(3) . . . . ?
C8 C24 C23 C22 0.8(3) . . . . ?
C7 N2 C6 C11 86.38(15) . . . . ?
C9 N2 C6 C11 -68.11(19) . . . . ?
C7 N2 C6 C2 -20.85(15) . . . . ?
C9 N2 C6 C2 -175.34(13) . . . . ?
C8 C2 C6 N2 20.39(13) . . . . ?
C3 C2 C6 N2 138.37(11) . . . . ?
C1 C2 C6 N2 -100.16(13) . . . . ?
C8 C2 C6 C11 -99.50(11) . . . . ?
C3 C2 C6 C11 18.48(13) . . . . ?
C1 C2 C6 C11 139.95(12) . . . . ?
C4 C3 C10 C11 -155.95(16) . . . . ?
C2 C3 C10 C11 15.01(15) . . . . ?
C4 C3 C10 C13 16.6(3) . . . . ?
C2 C3 C10 C13 -172.4(2) . . . . ?
C13 C10 C11 O1 -0.73(17) . . . . ?
C3 C10 C11 O1 174.73(11) . . . . ?
C13 C10 C11 C6 -178.07(13) . . . . ?
C3 C10 C11 C6 -2.61(18) . . . . ?
C12 O1 C11 C10 0.90(17) . . . . ?
C12 O1 C11 C6 177.74(16) . . . . ?
N2 C6 C11 C10 -121.64(15) . . . . ?
C2 C6 C11 C10 -10.32(16) . . . . ?
N2 C6 C11 O1 61.6(2) . . . . ?
C2 C6 C11 O1 172.96(14) . . . . ?
C11 O1 C12 C13 -0.75(19) . . . . ?
O1 C12 C13 C10 0.3(2) . . . . ?
C11 C10 C13 C12 0.23(18) . . . . ?
C3 C10 C13 C12 -172.4(2) . . . . ?
O2 S1 C14 C15 -146.65(13) . . . . ?
O3 S1 C14 C15 -16.39(15) . . . . ?
N1 S1 C14 C15 101.16(13) . . . . ?
O2 S1 C14 C19 37.07(14) . . . . ?
O3 S1 C14 C19 167.32(12) . . . . ?
N1 S1 C14 C19 -75.13(13) . . . . ?
C15 C14 C19 C18 -2.3(2) . . . . ?
S1 C14 C19 C18 173.95(13) . . . . ?
C14 C19 C18 C17 -0.1(3) . . . . ?
C19 C18 C17 C16 2.2(3) . . . . ?
C19 C18 C17 C20 -176.07(18) . . . . ?
C18 C17 C16 C15 -2.0(3) . . . . ?
C20 C17 C16 C15 176.26(19) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C19 C14 C15 C16 2.5(2) . . . . ?
S1 C14 C15 C16 -173.78(13) . . . . ?

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
C4 H4 O2 0.93 2.43 3.2979(18) 156.2 1_565 yes

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.037




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
