# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_lay39_a
_database_code_depnum_ccdc_archive 'CCDC 2252701'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H25 N3 O4 S'
_chemical_formula_sum            'C17 H25 N3 O4 S'
_chemical_formula_weight         367.46

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/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                   9.8266(17)
_cell_length_b                   19.746(4)
_cell_length_c                   10.400(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.979(13)
_cell_angle_gamma                90
_cell_volume                     1857.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    556
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      17.93
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5489
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12981
_diffrn_reflns_av_unetI/netI     0.1765
_diffrn_reflns_av_R_equivalents  0.1480
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.364
_diffrn_reflns_theta_max         25.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3412
_reflns_number_gt                1671
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0168P)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         3412
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1406
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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
S1 S 0.45084(11) 0.09880(6) 0.27031(13) 0.0302(3) Uani 1 1 d . . . . .
O1 O 0.3996(3) 0.07872(14) 0.1261(3) 0.0393(9) Uani 1 1 d . . . . .
O2 O 0.5633(3) 0.05908(14) 0.3718(3) 0.0383(9) Uani 1 1 d . . . . .
O3 O 0.0706(3) 0.28720(13) 0.0644(3) 0.0318(8) Uani 1 1 d . . . . .
O4 O 0.6051(3) 0.49177(14) 0.2049(3) 0.0380(8) Uani 1 1 d . . . . .
N1 N 0.3090(3) 0.10300(16) 0.3198(4) 0.0312(10) Uani 1 1 d . . . . .
N2 N 0.5052(3) 0.17659(18) 0.2832(4) 0.0257(9) Uani 1 1 d . . . . .
H2N H 0.541(4) 0.1868(19) 0.374(4) 0.035(14) Uiso 1 1 d . . . . .
N3 N 0.1507(3) 0.32296(17) 0.2876(4) 0.0271(9) Uani 1 1 d . . . . .
C1 C 0.2176(4) 0.1617(2) 0.2813(4) 0.0260(11) Uani 1 1 d . . . . .
C2 C 0.2533(4) 0.2185(2) 0.2323(4) 0.0239(10) Uani 1 1 d . . . . .
C3 C 0.3883(4) 0.22395(19) 0.1940(4) 0.0234(10) Uani 1 1 d . . . . .
H3 H 0.357339 0.208563 0.094993 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2528(5) 0.0368(2) 0.3421(6) 0.0511(15) Uani 1 1 d . . . . .
H4A H 0.201144 0.042233 0.405229 0.077 Uiso 1 1 calc R U . . .
H4B H 0.335654 0.005383 0.383484 0.077 Uiso 1 1 calc R U . . .
H4C H 0.184164 0.018846 0.252371 0.077 Uiso 1 1 calc R U . . .
C5 C 0.0784(4) 0.1562(2) 0.3112(5) 0.0383(13) Uani 1 1 d . . . . .
H5A H 0.021899 0.198385 0.283847 0.057 Uiso 1 1 calc R U . . .
H5B H 0.105624 0.148194 0.411134 0.057 Uiso 1 1 calc R U . . .
H5C H 0.017924 0.118408 0.257701 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1508(4) 0.2785(2) 0.1902(5) 0.0237(10) Uani 1 1 d . . . . .
C7 C 0.2474(4) 0.3184(2) 0.4369(5) 0.0344(12) Uani 1 1 d . . . . .
H7A H 0.309510 0.359616 0.464435 0.041 Uiso 1 1 calc R U . . .
H7B H 0.314073 0.278994 0.451528 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1609(5) 0.3110(2) 0.5315(5) 0.0470(14) Uani 1 1 d . . . . .
H8A H 0.230377 0.308235 0.629199 0.070 Uiso 1 1 calc R U . . .
H8B H 0.096301 0.350402 0.519191 0.070 Uiso 1 1 calc R U . . .
H8C H 0.100866 0.269747 0.506278 0.070 Uiso 1 1 calc R U . . .
C9 C 0.0567(4) 0.3832(2) 0.2409(5) 0.0356(12) Uani 1 1 d . . . . .
H9A H 0.066557 0.401666 0.156516 0.043 Uiso 1 1 calc R U . . .
H9B H 0.091728 0.418160 0.314801 0.043 Uiso 1 1 calc R U . . .
C10 C -0.1055(4) 0.3685(2) 0.2077(6) 0.0557(16) Uani 1 1 d . . . . .
H10A H -0.162988 0.410245 0.177163 0.084 Uiso 1 1 calc R U . . .
H10B H -0.141613 0.334591 0.133075 0.084 Uiso 1 1 calc R U . . .
H10C H -0.116432 0.351092 0.291422 0.084 Uiso 1 1 calc R U . . .
C11 C 0.4485(4) 0.29530(19) 0.2031(4) 0.0200(10) Uani 1 1 d . . . . .
C12 C 0.4029(4) 0.3356(2) 0.0833(5) 0.0303(11) Uani 1 1 d . . . . .
H12 H 0.335336 0.317709 -0.002739 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4544(4) 0.4014(2) 0.0874(4) 0.0255(10) Uani 1 1 d . . . . .
H13 H 0.420963 0.428412 0.005289 0.031 Uiso 1 1 calc R U . . .
C14 C 0.5548(4) 0.4272(2) 0.2119(5) 0.0272(11) Uani 1 1 d . . . . .
C15 C 0.5989(4) 0.3889(2) 0.3332(5) 0.0305(12) Uani 1 1 d . . . . .
H15 H 0.665311 0.407052 0.419464 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5443(4) 0.3236(2) 0.3261(5) 0.0311(12) Uani 1 1 d . . . . .
H16 H 0.574148 0.297487 0.409288 0.037 Uiso 1 1 calc R U . . .
C17 C 0.7201(4) 0.5177(2) 0.3270(5) 0.0423(14) Uani 1 1 d . . . . .
H17A H 0.682571 0.524127 0.400662 0.063 Uiso 1 1 calc R U . . .
H17B H 0.754215 0.561204 0.305272 0.063 Uiso 1 1 calc R U . . .
H17C H 0.802675 0.485569 0.358920 0.063 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 1.428(3) . ?
S1 O1 1.439(3) . ?
S1 N2 1.615(4) . ?
S1 N1 1.666(3) . ?
O3 C6 1.248(5) . ?
O4 C14 1.379(4) . ?
O4 C17 1.425(4) . ?
N1 C1 1.424(5) . ?
N1 C4 1.471(5) . ?
N2 C3 1.491(5) . ?
N2 H2N 0.89(4) . ?
N3 C6 1.341(5) . ?
N3 C9 1.467(5) . ?
N3 C7 1.473(5) . ?
C1 C2 1.336(5) . ?
C1 C5 1.520(5) . ?
C2 C6 1.505(5) . ?
C2 C3 1.530(5) . ?
C3 C11 1.517(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 C8 1.537(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.521(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.377(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(6) . ?
C15 C16 1.387(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O1 118.27(18) . . ?
O2 S1 N2 109.00(17) . . ?
O1 S1 N2 108.6(2) . . ?
O2 S1 N1 107.35(19) . . ?
O1 S1 N1 109.96(17) . . ?
N2 S1 N1 102.51(18) . . ?
C14 O4 C17 117.4(3) . . ?
C1 N1 C4 122.1(3) . . ?
C1 N1 S1 117.7(3) . . ?
C4 N1 S1 114.5(3) . . ?
C3 N2 S1 113.3(3) . . ?
C3 N2 H2N 114(2) . . ?
S1 N2 H2N 107(3) . . ?
C6 N3 C9 117.8(4) . . ?
C6 N3 C7 124.4(3) . . ?
C9 N3 C7 117.5(3) . . ?
C2 C1 N1 124.0(4) . . ?
C2 C1 C5 122.0(4) . . ?
N1 C1 C5 113.8(4) . . ?
C1 C2 C6 121.8(4) . . ?
C1 C2 C3 122.8(4) . . ?
C6 C2 C3 114.8(3) . . ?
N2 C3 C11 110.9(3) . . ?
N2 C3 C2 109.2(3) . . ?
C11 C3 C2 113.9(3) . . ?
N2 C3 H3 107.5 . . ?
C11 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 N3 121.0(4) . . ?
O3 C6 C2 119.4(4) . . ?
N3 C6 C2 119.6(4) . . ?
N3 C7 C8 112.9(3) . . ?
N3 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N3 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 112.9(3) . . ?
N3 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N3 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 117.5(4) . . ?
C16 C11 C3 123.0(4) . . ?
C12 C11 C3 119.5(4) . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O4 C14 C13 115.5(4) . . ?
O4 C14 C15 124.1(4) . . ?
C13 C14 C15 120.4(4) . . ?
C14 C15 C16 118.8(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 122.4(4) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_lay20b_sq
_database_code_depnum_ccdc_archive 'CCDC 2252705'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H27 N3 O6 S, C2 H3 N'
_chemical_formula_sum            'C19 H30 N4 O6 S'
_chemical_formula_weight         442.53

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.632(2)
_cell_length_b                   11.210(2)
_cell_length_c                   11.3270(18)
_cell_angle_alpha                95.416(13)
_cell_angle_beta                 109.438(11)
_cell_angle_gamma                117.015(12)
_cell_volume                     1084.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    948
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      18.73
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6008
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11289
_diffrn_reflns_av_unetI/netI     0.1291
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3838
_reflns_number_gt                2165
_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.
 
 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.
# SQUEEZE RESULTS (Version =  21116)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.500  0.500  0.500       127        21 ' '
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details                           ?
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1707P)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         3838
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0958
_refine_ls_wR_factor_ref         0.2859
_refine_ls_wR_factor_gt          0.2556
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 1.06931(16) 0.28854(15) 1.25717(13) 0.0315(5) Uani 1 1 d . . . . .
O1 O 1.0868(5) 0.3983(4) 1.3488(4) 0.0411(11) Uani 1 1 d . . . . .
O2 O 1.2017(4) 0.2798(4) 1.2677(4) 0.0349(10) Uani 1 1 d . . . . .
O3 O 1.1723(5) 0.5315(4) 0.9494(4) 0.0406(10) Uani 1 1 d . . . . .
O4 O 1.0369(5) 0.1086(4) 0.8167(4) 0.0381(10) Uani 1 1 d . . . . .
O5 O 0.3890(4) 0.0440(4) 0.8230(4) 0.0403(10) Uani 1 1 d . . . . .
O6 O 0.3108(4) -0.2123(4) 0.7426(4) 0.0425(11) Uani 1 1 d . . . . .
N1 N 0.9474(6) 0.1407(5) 1.2629(5) 0.0338(12) Uani 1 1 d D . . . .
N2 N 1.0013(6) 0.3130(5) 1.1145(4) 0.0328(11) Uani 1 1 d . . . . .
N3 N 0.9201(6) 0.1854(5) 0.6633(5) 0.0393(12) Uani 1 1 d . . . . .
C1 C 0.9541(6) 0.2087(5) 0.9963(5) 0.0283(12) Uani 1 1 d . . . . .
H1 H 1.017143 0.163067 1.019672 0.034 Uiso 1 1 calc R U . . .
C2 C 0.9951(6) 0.2868(5) 0.8959(5) 0.0275(12) Uani 1 1 d . . . . .
H2A H 0.916413 0.314007 0.856921 0.033 Uiso 1 1 calc R U . . .
C3 C 1.1571(6) 0.4191(6) 0.9583(5) 0.0298(13) Uani 1 1 d . . . . .
C4 C 1.2946(7) 0.4045(6) 1.0289(6) 0.0427(15) Uani 1 1 d . . . . .
H4A H 1.258302 0.306184 1.025255 0.064 Uiso 1 1 calc R U . . .
H4B H 1.366227 0.436103 0.986833 0.064 Uiso 1 1 calc R U . . .
H4C H 1.348720 0.461803 1.120417 0.064 Uiso 1 1 calc R U . . .
C5 C 0.9842(6) 0.1857(6) 0.7859(5) 0.0299(13) Uani 1 1 d . . . . .
C6 C 0.8650(7) 0.2820(7) 0.6207(6) 0.0461(16) Uani 1 1 d . . . . .
H6A H 0.886912 0.304855 0.544795 0.055 Uiso 1 1 calc R U . . .
H6B H 0.924986 0.370314 0.692724 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6948(8) 0.2224(8) 0.5836(7) 0.062(2) Uani 1 1 d . . . . .
H7A H 0.666249 0.290543 0.556829 0.094 Uiso 1 1 calc R U . . .
H7B H 0.634339 0.136133 0.510862 0.094 Uiso 1 1 calc R U . . .
H7C H 0.672447 0.201651 0.658923 0.094 Uiso 1 1 calc R U . . .
C8 C 0.9019(8) 0.0821(8) 0.5566(6) 0.0558(19) Uani 1 1 d . . . . .
H8A H 0.995041 0.072965 0.585818 0.067 Uiso 1 1 calc R U . . .
H8B H 0.895734 0.117217 0.479118 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7573(9) -0.0612(8) 0.5177(7) 0.071(2) Uani 1 1 d . . . . .
H9A H 0.750165 -0.125503 0.447485 0.107 Uiso 1 1 calc R U . . .
H9B H 0.763824 -0.097369 0.593641 0.107 Uiso 1 1 calc R U . . .
H9C H 0.664520 -0.053120 0.486945 0.107 Uiso 1 1 calc R U . . .
C10 C 0.7820(6) 0.0940(5) 0.9318(5) 0.0261(12) Uani 1 1 d . . . . .
C11 C 0.6650(6) 0.1247(6) 0.9118(5) 0.0315(13) Uani 1 1 d . . . . .
H11 H 0.693020 0.218901 0.942874 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5106(6) 0.0229(6) 0.8485(5) 0.0309(13) Uani 1 1 d . . . . .
C13 C 0.4684(6) -0.1179(6) 0.8034(6) 0.0344(14) Uani 1 1 d . . . . .
C14 C 0.5832(7) -0.1494(6) 0.8221(6) 0.0371(14) Uani 1 1 d . . . . .
H14 H 0.555509 -0.243200 0.789526 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7394(7) -0.0447(6) 0.8884(5) 0.0337(13) Uani 1 1 d . . . . .
H15 H 0.817617 -0.068171 0.904063 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4248(7) 0.1853(6) 0.8576(7) 0.0432(15) Uani 1 1 d . . . . .
H16A H 0.486751 0.227656 0.952326 0.065 Uiso 1 1 calc R U . . .
H16B H 0.327852 0.186397 0.832194 0.065 Uiso 1 1 calc R U . . .
H16C H 0.484410 0.238804 0.811878 0.065 Uiso 1 1 calc R U . . .
C17 C 0.2632(8) -0.3549(6) 0.6990(7) 0.0488(17) Uani 1 1 d . . . . .
H17A H 0.303877 -0.366417 0.635538 0.073 Uiso 1 1 calc R U . . .
H17B H 0.149101 -0.412025 0.657366 0.073 Uiso 1 1 calc R U . . .
H17C H 0.303630 -0.384966 0.773841 0.073 Uiso 1 1 calc R U . . .
H2 H 0.946(7) 0.354(7) 1.111(6) 0.05(2) Uiso 1 1 d . . . . .
H1A H 0.859(5) 0.131(5) 1.248(5) 0.014(13) Uiso 1 1 d D . . . .
H1B H 0.967(7) 0.079(6) 1.243(6) 0.05(2) Uiso 1 1 d 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 1.422(4) . ?
S1 O1 1.432(4) . ?
S1 N1 1.599(5) . ?
S1 N2 1.642(5) . ?
O3 C3 1.214(6) . ?
O4 C5 1.244(6) . ?
O5 C12 1.361(6) . ?
O5 C16 1.429(7) . ?
O6 C13 1.373(7) . ?
O6 C17 1.417(7) . ?
N1 H1A 0.85(4) . ?
N1 H1B 0.83(4) . ?
N2 C1 1.461(7) . ?
N2 H2 0.89(7) . ?
N3 C5 1.328(7) . ?
N3 C8 1.488(7) . ?
N3 C6 1.495(7) . ?
C1 C10 1.527(7) . ?
C1 C2 1.555(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.528(7) . ?
C2 C5 1.539(7) . ?
C2 H2A 1.0000 . ?
C3 C4 1.505(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.497(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.520(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.390(7) . ?
C10 C11 1.391(7) . ?
C11 C12 1.368(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(7) . ?
C13 C14 1.375(8) . ?
C14 C15 1.390(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O1 119.8(2) . . ?
O2 S1 N1 105.6(3) . . ?
O1 S1 N1 109.1(3) . . ?
O2 S1 N2 106.9(2) . . ?
O1 S1 N2 104.4(2) . . ?
N1 S1 N2 111.0(3) . . ?
C12 O5 C16 117.5(4) . . ?
C13 O6 C17 116.7(5) . . ?
S1 N1 H1A 114(3) . . ?
S1 N1 H1B 111(5) . . ?
H1A N1 H1B 128(6) . . ?
C1 N2 S1 118.6(4) . . ?
C1 N2 H2 118(4) . . ?
S1 N2 H2 114(4) . . ?
C5 N3 C8 118.4(5) . . ?
C5 N3 C6 125.8(5) . . ?
C8 N3 C6 115.8(5) . . ?
N2 C1 C10 115.3(4) . . ?
N2 C1 C2 107.9(4) . . ?
C10 C1 C2 109.1(4) . . ?
N2 C1 H1 108.1 . . ?
C10 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C3 C2 C5 110.0(4) . . ?
C3 C2 C1 112.7(4) . . ?
C5 C2 C1 108.6(4) . . ?
C3 C2 H2A 108.5 . . ?
C5 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
O3 C3 C4 121.9(5) . . ?
O3 C3 C2 120.1(5) . . ?
C4 C3 C2 118.0(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 N3 123.2(5) . . ?
O4 C5 C2 118.2(5) . . ?
N3 C5 C2 118.6(5) . . ?
N3 C6 C7 113.5(5) . . ?
N3 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N3 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 112.4(5) . . ?
N3 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.5(5) . . ?
C15 C10 C1 119.8(5) . . ?
C11 C10 C1 121.7(5) . . ?
C12 C11 C10 121.8(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
O5 C12 C11 125.6(5) . . ?
O5 C12 C13 115.1(5) . . ?
C11 C12 C13 119.2(5) . . ?
O6 C13 C14 125.8(5) . . ?
O6 C13 C12 114.8(5) . . ?
C14 C13 C12 119.4(5) . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 S1 N2 C1 58.6(4) . . . . ?
O1 S1 N2 C1 -173.6(4) . . . . ?
N1 S1 N2 C1 -56.2(5) . . . . ?
S1 N2 C1 C10 93.1(5) . . . . ?
S1 N2 C1 C2 -144.7(4) . . . . ?
N2 C1 C2 C3 44.2(6) . . . . ?
C10 C1 C2 C3 170.2(4) . . . . ?
N2 C1 C2 C5 166.3(4) . . . . ?
C10 C1 C2 C5 -67.7(5) . . . . ?
C5 C2 C3 O3 115.3(5) . . . . ?
C1 C2 C3 O3 -123.4(5) . . . . ?
C5 C2 C3 C4 -64.1(6) . . . . ?
C1 C2 C3 C4 57.2(6) . . . . ?
C8 N3 C5 O4 3.7(8) . . . . ?
C6 N3 C5 O4 -175.4(5) . . . . ?
C8 N3 C5 C2 -176.7(5) . . . . ?
C6 N3 C5 C2 4.1(8) . . . . ?
C3 C2 C5 O4 82.2(6) . . . . ?
C1 C2 C5 O4 -41.5(6) . . . . ?
C3 C2 C5 N3 -97.4(6) . . . . ?
C1 C2 C5 N3 138.9(5) . . . . ?
C5 N3 C6 C7 -94.9(7) . . . . ?
C8 N3 C6 C7 86.0(7) . . . . ?
C5 N3 C8 C9 82.2(7) . . . . ?
C6 N3 C8 C9 -98.5(7) . . . . ?
N2 C1 C10 C15 -135.8(5) . . . . ?
C2 C1 C10 C15 102.6(6) . . . . ?
N2 C1 C10 C11 46.0(7) . . . . ?
C2 C1 C10 C11 -75.6(6) . . . . ?
C15 C10 C11 C12 -1.4(8) . . . . ?
C1 C10 C11 C12 176.8(5) . . . . ?
C16 O5 C12 C11 4.3(8) . . . . ?
C16 O5 C12 C13 -175.5(5) . . . . ?
C10 C11 C12 O5 -178.9(5) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
C17 O6 C13 C14 2.0(8) . . . . ?
C17 O6 C13 C12 -178.4(5) . . . . ?
O5 C12 C13 O6 -1.0(7) . . . . ?
C11 C12 C13 O6 179.3(5) . . . . ?
O5 C12 C13 C14 178.6(5) . . . . ?
C11 C12 C13 C14 -1.1(8) . . . . ?
O6 C13 C14 C15 -178.3(5) . . . . ?
C12 C13 C14 C15 2.1(8) . . . . ?
C13 C14 C15 C10 -2.7(8) . . . . ?
C11 C10 C15 C14 2.3(8) . . . . ?
C1 C10 C15 C14 -175.9(5) . . . . ?

_refine_diff_density_max         1.210
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.146




####################################################################### 
# 
# 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_lay20_a
_database_code_depnum_ccdc_archive 'CCDC 2252704'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT410_lay20_a             
;
PROBLEM:  Short Intra H...H Contact  H2..H8B 1.84 Ang. 
RESPONSE: The alarm is related to the short intramolecular H..H 
contact in the crystal for hydrogen atoms due to sterical 
reasons. There is no doubt that the structure model is correct 
and the number of hydrogen atoms for the C2(sp3)H and C8(sp3)H2 
is determined correctly since the normal range for bonds/angles 
in the molecule and ADP for non-H atoms is also not bad. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H25 N3 O5 S'
_chemical_formula_sum            'C17 H25 N3 O5 S'
_chemical_formula_weight         383.46

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                   7.7579(18)
_cell_length_b                   23.890(5)
_cell_length_c                   10.813(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.028(11)
_cell_angle_gamma                90
_cell_volume                     1926.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    725
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      18.44
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17341
_diffrn_reflns_av_unetI/netI     0.1610
_diffrn_reflns_av_R_equivalents  0.1214
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         25.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3508
_reflns_number_gt                1864
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0485P)²+0.4029P] 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         3508
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
S1 S 0.93268(13) 0.18575(4) 0.31966(9) 0.0251(3) Uani 1 1 d . . . . .
O1 O 1.0588(3) 0.18919(11) 0.4437(2) 0.0340(8) Uani 1 1 d . . . . .
O2 O 0.9755(3) 0.15277(10) 0.2215(2) 0.0320(7) Uani 1 1 d . . . . .
O3 O 0.5860(3) 0.27290(10) 0.5331(2) 0.0264(7) Uani 1 1 d . . . . .
O4 O 0.7795(4) 0.48307(10) 0.4447(3) 0.0364(8) Uani 1 1 d . . . . .
O5 O 0.7543(4) 0.51289(11) 0.2107(3) 0.0390(8) Uani 1 1 d . . . . .
N1 N 0.7455(4) 0.15950(13) 0.3430(3) 0.0246(8) Uani 1 1 d . . . . .
N2 N 0.8877(4) 0.24853(12) 0.2630(3) 0.0202(8) Uani 1 1 d D . . . .
H2N H 0.828(5) 0.2441(16) 0.1804(14) 0.043(13) Uiso 1 1 d D . . . .
N3 N 0.3642(4) 0.31104(12) 0.3749(3) 0.0222(8) Uani 1 1 d . . . . .
C1 C 0.6118(5) 0.19133(16) 0.3416(3) 0.0232(10) Uani 1 1 d . . . . .
C2 C 0.6047(5) 0.25499(15) 0.3225(4) 0.0210(10) Uani 1 1 d . . . . .
H2 H 0.535(5) 0.2632(13) 0.235(3) 0.025 Uiso 1 1 d . U . . .
C3 C 0.7904(5) 0.28175(14) 0.3380(3) 0.0212(10) Uani 1 1 d . . . . .
H3 H 0.859070 0.279243 0.430856 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4450(5) 0.16438(16) 0.3567(4) 0.0320(11) Uani 1 1 d . . . . .
H4A H 0.341263 0.178127 0.289554 0.048 Uiso 1 1 calc R U . . .
H4B H 0.430249 0.173667 0.441502 0.048 Uiso 1 1 calc R U . . .
H4C H 0.454113 0.123685 0.349073 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5140(5) 0.28113(15) 0.4159(4) 0.0199(9) Uani 1 1 d . . . . .
C6 C 0.2814(5) 0.33415(16) 0.4719(4) 0.0307(11) Uani 1 1 d . . . . .
H6A H 0.281092 0.304877 0.536620 0.037 Uiso 1 1 calc R U . . .
H6B H 0.155131 0.344024 0.428941 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3768(6) 0.38534(17) 0.5400(4) 0.0413(12) Uani 1 1 d . . . . .
H7A H 0.308983 0.400821 0.596252 0.062 Uiso 1 1 calc R U . . .
H7B H 0.385896 0.413506 0.476190 0.062 Uiso 1 1 calc R U . . .
H7C H 0.497324 0.374895 0.591660 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2687(5) 0.32376(17) 0.2388(4) 0.0277(11) Uani 1 1 d D . . . .
H8A H 0.150(4) 0.3071(14) 0.222(3) 0.033 Uiso 1 1 d D U . . .
H8B H 0.321(5) 0.3013(14) 0.181(3) 0.033 Uiso 1 1 d D U . . .
C9 C 0.2737(6) 0.38479(17) 0.2058(4) 0.0452(13) Uani 1 1 d . . . . .
H9A H 0.211978 0.390378 0.114515 0.068 Uiso 1 1 calc R U . . .
H9B H 0.398626 0.397042 0.223057 0.068 Uiso 1 1 calc R U . . .
H9C H 0.213655 0.406722 0.258371 0.068 Uiso 1 1 calc R U . . .
C10 C 0.7801(5) 0.34273(15) 0.2996(3) 0.0191(9) Uani 1 1 d . . . . .
C11 C 0.7867(5) 0.38400(15) 0.3930(4) 0.0245(10) Uani 1 1 d . . . . .
H11 H 0.798882 0.373301 0.479620 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7757(5) 0.44034(16) 0.3602(4) 0.0276(10) Uani 1 1 d . . . . .
C13 C 0.7598(5) 0.45620(16) 0.2333(4) 0.0278(10) Uani 1 1 d . . . . .
C14 C 0.7558(5) 0.41550(16) 0.1417(4) 0.0271(10) Uani 1 1 d . . . . .
H14 H 0.747854 0.426026 0.055546 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7634(5) 0.35950(16) 0.1751(4) 0.0278(10) Uani 1 1 d . . . . .
H15 H 0.757023 0.331967 0.110593 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8247(6) 0.46952(17) 0.5788(4) 0.0404(12) Uani 1 1 d . . . . .
H16A H 0.729740 0.446290 0.595932 0.061 Uiso 1 1 calc R U . . .
H16B H 0.836871 0.504075 0.629293 0.061 Uiso 1 1 calc R U . . .
H16C H 0.938309 0.448931 0.602823 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7834(7) 0.53067(17) 0.0932(4) 0.0504(14) Uani 1 1 d . . . . .
H17A H 0.889576 0.511814 0.080739 0.076 Uiso 1 1 calc R U . . .
H17B H 0.802294 0.571266 0.095523 0.076 Uiso 1 1 calc R U . . .
H17C H 0.678529 0.521252 0.021905 0.076 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 O1 1.428(3) . ?
S1 O2 1.432(3) . ?
S1 N2 1.621(3) . ?
S1 N1 1.664(3) . ?
O3 C5 1.250(4) . ?
O4 C12 1.365(4) . ?
O4 C16 1.431(4) . ?
O5 C13 1.375(4) . ?
O5 C17 1.416(5) . ?
N1 C1 1.283(5) . ?
N2 C3 1.482(5) . ?
N2 H2N 0.892(10) . ?
N3 C5 1.331(4) . ?
N3 C6 1.479(5) . ?
N3 C8 1.486(5) . ?
C1 C4 1.494(5) . ?
C1 C2 1.534(5) . ?
C2 C5 1.516(5) . ?
C2 C3 1.543(5) . ?
C2 H2 0.97(3) . ?
C3 C10 1.511(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.511(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.504(6) . ?
C8 H8A 0.97(3) . ?
C8 H8B 1.00(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.376(5) . ?
C10 C11 1.402(5) . ?
C11 C12 1.388(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(5) . ?
C13 C14 1.382(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O2 119.25(16) . . ?
O1 S1 N2 108.78(16) . . ?
O2 S1 N2 107.39(16) . . ?
O1 S1 N1 106.22(17) . . ?
O2 S1 N1 107.19(16) . . ?
N2 S1 N1 107.48(16) . . ?
C12 O4 C16 117.6(3) . . ?
C13 O5 C17 116.8(3) . . ?
C1 N1 S1 120.8(3) . . ?
C3 N2 S1 112.2(2) . . ?
C3 N2 H2N 114(3) . . ?
S1 N2 H2N 106(3) . . ?
C5 N3 C6 118.3(3) . . ?
C5 N3 C8 126.2(3) . . ?
C6 N3 C8 115.5(3) . . ?
N1 C1 C4 117.7(3) . . ?
N1 C1 C2 126.0(4) . . ?
C4 C1 C2 116.2(3) . . ?
C5 C2 C1 109.0(3) . . ?
C5 C2 C3 110.4(3) . . ?
C1 C2 C3 113.5(3) . . ?
C5 C2 H2 110(2) . . ?
C1 C2 H2 108.6(19) . . ?
C3 C2 H2 106(2) . . ?
N2 C3 C10 111.2(3) . . ?
N2 C3 C2 108.7(3) . . ?
C10 C3 C2 113.1(3) . . ?
N2 C3 H3 107.9 . . ?
C10 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 N3 121.7(3) . . ?
O3 C5 C2 116.8(3) . . ?
N3 C5 C2 121.5(3) . . ?
N3 C6 C7 113.4(3) . . ?
N3 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N3 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 113.2(3) . . ?
N3 C8 H8A 107(2) . . ?
C9 C8 H8A 116(2) . . ?
N3 C8 H8B 110(2) . . ?
C9 C8 H8B 109(2) . . ?
H8A C8 H8B 101(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C3 122.2(3) . . ?
C11 C10 C3 119.4(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
O4 C12 C11 124.4(3) . . ?
O4 C12 C13 115.8(3) . . ?
C11 C12 C13 119.8(4) . . ?
O5 C13 C14 124.9(4) . . ?
O5 C13 C12 115.6(4) . . ?
C14 C13 C12 119.5(4) . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 121.6(4) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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_lay06
_database_code_depnum_ccdc_archive 'CCDC 2252702'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br N3 O3 S, C3 H7 N O'
_chemical_formula_sum            'C21 H25 Br N4 O4 S'
_chemical_formula_weight         509.42

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   19.6398(7)
_cell_length_b                   11.7177(4)
_cell_length_c                   10.0007(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2301.49(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5507
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.24
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.911
_shelx_estimated_absorpt_T_min   0.436
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18097
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.929
_reflns_number_total             3915
_reflns_number_gt                3321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.844
_reflns_Friedel_fraction_full    0.848

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0272P)²+0.0723P] 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_abs_structure_details 
;
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3915
_refine_ls_number_parameters     286
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_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
BR1 Br 1.04052(2) 0.53438(4) 0.86925(6) 0.04469(17) Uani 1 1 d . . . . .
S2 S 0.70892(6) 0.16017(9) 1.19786(12) 0.0269(3) Uani 1 1 d . . . . .
O1 O 0.64148(15) 0.2024(3) 1.1856(4) 0.0371(8) Uani 1 1 d . . . . .
O2 O 0.73463(16) 0.1370(3) 1.3285(3) 0.0363(9) Uani 1 1 d . . . . .
O3 O 0.90497(18) -0.0108(3) 1.1048(4) 0.0340(8) Uani 1 1 d . . . . .
O4 O 0.70222(16) 0.2833(3) 0.8678(4) 0.0448(8) Uani 1 1 d . . . . .
N1 N 0.7121(2) 0.0382(3) 1.1146(4) 0.0293(9) Uani 1 1 d . . . . .
N2 N 0.75880(19) 0.2499(3) 1.1218(4) 0.0244(9) Uani 1 1 d D . . . .
H2N H 0.737(2) 0.277(4) 1.050(3) 0.028(13) Uiso 1 1 d D . . . .
N3 N 0.91942(17) 0.0134(3) 0.8818(5) 0.0286(9) Uani 1 1 d . . . . .
N4 N 0.64317(18) 0.2059(3) 0.6945(4) 0.0297(9) Uani 1 1 d . . . . .
C1 C 0.7602(2) 0.0178(4) 1.0312(5) 0.0267(11) Uani 1 1 d . . . . .
C2 C 0.8193(2) 0.0971(3) 0.9972(4) 0.0221(10) Uani 1 1 d . . . . .
H2 H 0.812206 0.127866 0.904926 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8264(2) 0.1987(4) 1.0950(5) 0.0232(10) Uani 1 1 d . . . . .
H3 H 0.844280 0.168069 1.181532 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7586(3) -0.0942(4) 0.9595(5) 0.0405(13) Uani 1 1 d . . . . .
H4A H 0.797729 -0.099407 0.899089 0.061 Uiso 1 1 calc R U . . .
H4B H 0.760503 -0.156508 1.024732 0.061 Uiso 1 1 calc R U . . .
H4C H 0.716362 -0.100031 0.907627 0.061 Uiso 1 1 calc R U . . .
C5 C 0.8852(2) 0.0289(4) 0.9991(5) 0.0233(11) Uani 1 1 d . . . . .
C6 C 0.9000(2) 0.0616(4) 0.7560(5) 0.0240(11) Uani 1 1 d . . . . .
C7 C 0.8700(2) -0.0051(4) 0.6582(5) 0.0308(12) Uani 1 1 d . . . . .
H7 H 0.861236 -0.083650 0.674463 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8528(2) 0.0430(4) 0.5375(5) 0.0363(13) Uani 1 1 d . . . . .
H8 H 0.832025 -0.002905 0.470683 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8653(2) 0.1572(5) 0.5115(5) 0.0358(12) Uani 1 1 d . . . . .
H9 H 0.852599 0.190093 0.428292 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8968(2) 0.2226(4) 0.6091(5) 0.0325(11) Uani 1 1 d . . . . .
H10 H 0.906075 0.300822 0.592078 0.039 Uiso 1 1 calc R U . . .
C11 C 0.9146(2) 0.1759(4) 0.7299(5) 0.0284(11) Uani 1 1 d . . . . .
H11 H 0.936782 0.221273 0.795519 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9822(3) -0.0550(4) 0.8807(8) 0.0498(14) Uani 1 1 d . . . . .
H12A H 1.000507 -0.058026 0.789636 0.075 Uiso 1 1 calc R U . . .
H12B H 1.015886 -0.020046 0.940350 0.075 Uiso 1 1 calc R U . . .
H12C H 0.972122 -0.132599 0.911558 0.075 Uiso 1 1 calc R U . . .
C13 C 0.8772(2) 0.2861(3) 1.0440(4) 0.0230(10) Uani 1 1 d . . . . .
C14 C 0.9450(2) 0.2761(4) 1.0804(5) 0.0276(11) Uani 1 1 d . . . . .
H14 H 0.958201 0.218015 1.141452 0.033 Uiso 1 1 calc R U . . .
C15 C 0.9941(2) 0.3493(4) 1.0294(5) 0.0328(11) Uani 1 1 d . . . . .
H15 H 1.040448 0.342088 1.054893 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9738(2) 0.4328(4) 0.9408(5) 0.0277(11) Uani 1 1 d . . . . .
C17 C 0.9072(2) 0.4454(4) 0.9025(5) 0.0298(12) Uani 1 1 d . . . . .
H17 H 0.894579 0.504176 0.841985 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8582(2) 0.3713(4) 0.9532(5) 0.0304(11) Uani 1 1 d . . . . .
H18 H 0.811973 0.378490 0.926259 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6525(3) 0.2798(4) 0.7933(5) 0.0357(12) Uani 1 1 d . . . . .
H19 H 0.617693 0.334765 0.807753 0.043 Uiso 1 1 calc R U . . .
C20 C 0.5829(3) 0.2063(4) 0.6115(6) 0.0425(14) Uani 1 1 d . . . . .
H20A H 0.555699 0.274391 0.631216 0.064 Uiso 1 1 calc R U . . .
H20B H 0.555836 0.137821 0.630013 0.064 Uiso 1 1 calc R U . . .
H20C H 0.596270 0.206947 0.517135 0.064 Uiso 1 1 calc R U . . .
C21 C 0.6932(3) 0.1181(5) 0.6668(5) 0.0476(15) Uani 1 1 d . . . . .
H21A H 0.736932 0.139643 0.706792 0.071 Uiso 1 1 calc R U . . .
H21B H 0.698695 0.109913 0.569843 0.071 Uiso 1 1 calc R U . . .
H21C H 0.677898 0.045518 0.704921 0.071 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
BR1 C16 1.909(5) . ?
S2 O1 1.419(3) . ?
S2 O2 1.426(3) . ?
S2 N2 1.626(4) . ?
S2 N1 1.656(4) . ?
O3 C5 1.219(6) . ?
O4 C19 1.229(5) . ?
N1 C1 1.282(6) . ?
N2 C3 1.482(5) . ?
N3 C5 1.364(7) . ?
N3 C6 1.431(7) . ?
N3 C12 1.471(5) . ?
N4 C19 1.326(6) . ?
N4 C20 1.446(6) . ?
N4 C21 1.450(6) . ?
C1 C4 1.495(7) . ?
C1 C2 1.526(6) . ?
C2 C5 1.521(6) . ?
C2 C3 1.547(6) . ?
C3 C13 1.517(6) . ?
C6 C7 1.384(7) . ?
C6 C11 1.395(6) . ?
C7 C8 1.374(7) . ?
C8 C9 1.385(7) . ?
C9 C10 1.386(7) . ?
C10 C11 1.372(7) . ?
C13 C14 1.386(6) . ?
C13 C18 1.401(6) . ?
C14 C15 1.387(6) . ?
C15 C16 1.378(7) . ?
C16 C17 1.372(6) . ?
C17 C18 1.392(6) . ?

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 S2 O2 118.4(2) . . ?
O1 S2 N2 107.2(2) . . ?
O2 S2 N2 109.8(2) . . ?
O1 S2 N1 107.1(2) . . ?
O2 S2 N1 106.4(2) . . ?
N2 S2 N1 107.45(19) . . ?
C1 N1 S2 121.1(3) . . ?
C3 N2 S2 111.3(3) . . ?
C5 N3 C6 124.9(3) . . ?
C5 N3 C12 119.5(5) . . ?
C6 N3 C12 115.6(5) . . ?
C19 N4 C20 122.6(4) . . ?
C19 N4 C21 120.8(4) . . ?
C20 N4 C21 116.6(4) . . ?
N1 C1 C4 117.4(4) . . ?
N1 C1 C2 126.3(4) . . ?
C4 C1 C2 116.4(4) . . ?
C5 C2 C1 108.9(3) . . ?
C5 C2 C3 108.6(4) . . ?
C1 C2 C3 113.4(4) . . ?
N2 C3 C13 112.1(3) . . ?
N2 C3 C2 110.1(3) . . ?
C13 C3 C2 111.5(4) . . ?
O3 C5 N3 122.6(4) . . ?
O3 C5 C2 118.8(4) . . ?
N3 C5 C2 118.6(4) . . ?
C7 C6 C11 119.9(5) . . ?
C7 C6 N3 120.8(4) . . ?
C11 C6 N3 119.3(4) . . ?
C8 C7 C6 119.6(4) . . ?
C7 C8 C9 121.2(5) . . ?
C8 C9 C10 118.7(5) . . ?
C11 C10 C9 120.9(4) . . ?
C10 C11 C6 119.7(4) . . ?
C14 C13 C18 119.2(4) . . ?
C14 C13 C3 119.1(4) . . ?
C18 C13 C3 121.6(4) . . ?
C15 C14 C13 121.2(4) . . ?
C16 C15 C14 118.4(4) . . ?
C17 C16 C15 122.1(4) . . ?
C17 C16 BR1 118.9(4) . . ?
C15 C16 BR1 119.1(4) . . ?
C16 C17 C18 119.4(4) . . ?
C17 C18 C13 119.7(4) . . ?
O4 C19 N4 125.6(5) . . ?

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_lay40
_database_code_depnum_ccdc_archive 'CCDC 2252703'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N3 O4 S'
_chemical_formula_sum            'C22 H27 N3 O4 S'
_chemical_formula_weight         429.52

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.3766(9)
_cell_length_b                   11.5993(10)
_cell_length_c                   18.4820(17)
_cell_angle_alpha                75.938(6)
_cell_angle_beta                 78.395(6)
_cell_angle_gamma                88.468(5)
_cell_volume                     2113.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2189
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      22.41
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30122
_diffrn_reflns_av_unetI/netI     0.1214
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         25.891
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8102
_reflns_number_gt                4693
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0594P)²+0.2790P] 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         8102
_refine_ls_number_parameters     553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
S1 S 0.82664(9) 0.93262(7) 0.18173(5) 0.0241(2) Uani 1 1 d . . . . .
S2 S 0.52269(9) 0.44784(7) 0.17014(5) 0.0233(2) Uani 1 1 d . . . . .
O1 O 0.8566(2) 0.80896(19) 0.20043(13) 0.0310(6) Uani 1 1 d . . . . .
O2 O 0.9304(2) 1.01976(19) 0.15129(13) 0.0300(6) Uani 1 1 d . . . . .
O3 O 0.4327(2) 0.68869(19) 0.29240(13) 0.0291(6) Uani 1 1 d . . . . .
O4 O 0.2588(3) 1.1315(2) 0.47491(14) 0.0377(7) Uani 1 1 d . . . . .
O5 O 0.4805(2) 0.32673(18) 0.18442(13) 0.0291(6) Uani 1 1 d . . . . .
O6 O 0.4512(2) 0.54061(19) 0.13094(13) 0.0285(6) Uani 1 1 d . . . . .
O7 O 0.7836(2) 0.17333(19) 0.31064(14) 0.0315(6) Uani 1 1 d . . . . .
O8 O 0.7739(3) 0.6126(2) 0.50736(14) 0.0389(7) Uani 1 1 d . . . . .
N1 N 0.7287(3) 0.9478(2) 0.11881(15) 0.0224(7) Uani 1 1 d . . . . .
N2 N 0.7365(3) 0.9613(3) 0.25638(17) 0.0269(8) Uani 1 1 d . . . . .
N3 N 0.3053(3) 0.8402(2) 0.24762(16) 0.0242(7) Uani 1 1 d . . . . .
N4 N 0.6766(3) 0.4564(2) 0.12099(15) 0.0236(7) Uani 1 1 d . . . . .
N5 N 0.5333(3) 0.4724(3) 0.25094(16) 0.0255(7) Uani 1 1 d . . . . .
N6 N 0.9423(3) 0.3114(2) 0.29722(15) 0.0241(7) Uani 1 1 d . . . . .
C1 C 0.5998(3) 0.8926(3) 0.15007(19) 0.0210(8) Uani 1 1 d . . . . .
C2 C 0.5471(3) 0.8690(3) 0.22500(19) 0.0198(8) Uani 1 1 d . . . . .
C3 C 0.6113(3) 0.8922(3) 0.28743(19) 0.0244(8) Uani 1 1 d . . . . .
H3 H 0.631723 0.813425 0.318985 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7346(3) 1.0594(3) 0.06193(19) 0.0225(8) Uani 1 1 d . . . . .
C5 C 0.8282(3) 1.0756(3) -0.00461(19) 0.0266(9) Uani 1 1 d . . . . .
H5 H 0.889150 1.015021 -0.012201 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8327(3) 1.1815(3) -0.0606(2) 0.0286(9) Uani 1 1 d . . . . .
H6 H 0.898062 1.193863 -0.106051 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7422(4) 1.2679(3) -0.0500(2) 0.0304(9) Uani 1 1 d . . . . .
H7 H 0.744820 1.339822 -0.088183 0.036 Uiso 1 1 calc R U . . .
C8 C 0.6479(4) 1.2502(3) 0.0161(2) 0.0293(9) Uani 1 1 d . . . . .
H8 H 0.585525 1.310001 0.022884 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6428(3) 1.1468(3) 0.0727(2) 0.0261(8) Uani 1 1 d . . . . .
H9 H 0.577782 1.135358 0.118200 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5339(3) 0.8626(3) 0.09129(19) 0.0267(8) Uani 1 1 d . . . . .
H10A H 0.462038 0.804622 0.116604 0.040 Uiso 1 1 calc R U . . .
H10B H 0.598252 0.828617 0.056049 0.040 Uiso 1 1 calc R U . . .
H10C H 0.498529 0.934873 0.062936 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4229(3) 0.7933(3) 0.25644(19) 0.0236(8) Uani 1 1 d . . . . .
C12 C 0.2856(3) 0.9626(3) 0.2061(2) 0.0299(9) Uani 1 1 d . . . . .
H12A H 0.256264 0.960066 0.158688 0.036 Uiso 1 1 calc R U . . .
H12B H 0.370942 1.006677 0.191356 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1863(4) 1.0295(3) 0.2509(2) 0.0379(10) Uani 1 1 d . . . . .
H13A H 0.178175 1.109855 0.219891 0.057 Uiso 1 1 calc R U . . .
H13B H 0.100760 0.987682 0.264598 0.057 Uiso 1 1 calc R U . . .
H13C H 0.215575 1.034349 0.297305 0.057 Uiso 1 1 calc R U . . .
C14 C 0.1881(3) 0.7620(3) 0.2786(2) 0.0337(9) Uani 1 1 d . . . . .
H14A H 0.210536 0.681481 0.271426 0.040 Uiso 1 1 calc R U . . .
H14B H 0.118786 0.792192 0.249430 0.040 Uiso 1 1 calc R U . . .
C15 C 0.1339(4) 0.7531(3) 0.3623(2) 0.0445(11) Uani 1 1 d . . . . .
H15A H 0.056142 0.699978 0.379524 0.067 Uiso 1 1 calc R U . . .
H15B H 0.201165 0.721452 0.391713 0.067 Uiso 1 1 calc R U . . .
H15C H 0.109349 0.832241 0.369702 0.067 Uiso 1 1 calc R U . . .
C16 C 0.5180(3) 0.9544(3) 0.33931(19) 0.0215(8) Uani 1 1 d . . . . .
C17 C 0.4834(3) 1.0722(3) 0.31360(19) 0.0252(8) Uani 1 1 d . . . . .
H17 H 0.520532 1.114678 0.263168 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3973(3) 1.1272(3) 0.3596(2) 0.0266(9) Uani 1 1 d . . . . .
H18 H 0.374155 1.207099 0.340727 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3430(3) 1.0674(3) 0.4339(2) 0.0261(8) Uani 1 1 d . . . . .
C20 C 0.3758(3) 0.9503(3) 0.4608(2) 0.0294(9) Uani 1 1 d . . . . .
H20 H 0.338889 0.907883 0.511232 0.035 Uiso 1 1 calc R U . . .
C21 C 0.4637(3) 0.8961(3) 0.4126(2) 0.0282(9) Uani 1 1 d . . . . .
H21 H 0.486718 0.816040 0.431114 0.034 Uiso 1 1 calc R U . . .
C22 C 0.1998(4) 1.0750(3) 0.5515(2) 0.0386(10) Uani 1 1 d . . . . .
H22A H 0.145524 1.006749 0.552126 0.058 Uiso 1 1 calc R U . . .
H22B H 0.144458 1.131656 0.574584 0.058 Uiso 1 1 calc R U . . .
H22C H 0.268695 1.047681 0.580621 0.058 Uiso 1 1 calc R U . . .
C23 C 0.7697(3) 0.3921(3) 0.16370(19) 0.0209(8) Uani 1 1 d . . . . .
C24 C 0.7452(3) 0.3643(3) 0.23924(19) 0.0190(8) Uani 1 1 d . . . . .
C25 C 0.6235(3) 0.3947(3) 0.29230(18) 0.0225(8) Uani 1 1 d . . . . .
H25 H 0.574685 0.318578 0.320150 0.027 Uiso 1 1 calc R U . . .
C26 C 0.7227(3) 0.5646(3) 0.06413(18) 0.0208(8) Uani 1 1 d . . . . .
C27 C 0.6799(3) 0.5903(3) -0.00426(19) 0.0253(8) Uani 1 1 d . . . . .
H27 H 0.620075 0.537537 -0.013495 0.030 Uiso 1 1 calc R U . . .
C28 C 0.7247(3) 0.6928(3) -0.0590(2) 0.0285(9) Uani 1 1 d . . . . .
H28 H 0.693644 0.711664 -0.105401 0.034 Uiso 1 1 calc R U . . .
C29 C 0.8147(3) 0.7684(3) -0.0465(2) 0.0281(9) Uani 1 1 d . . . . .
H29 H 0.846274 0.838232 -0.084543 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8585(3) 0.7415(3) 0.0217(2) 0.0293(9) Uani 1 1 d . . . . .
H30 H 0.921038 0.792452 0.030280 0.035 Uiso 1 1 calc R U . . .
C31 C 0.8111(3) 0.6407(3) 0.07689(19) 0.0249(8) Uani 1 1 d . . . . .
H31 H 0.839501 0.623451 0.124080 0.030 Uiso 1 1 calc R U . . .
C32 C 0.8886(3) 0.3541(3) 0.11429(19) 0.0292(9) Uani 1 1 d . . . . .
H32A H 0.945400 0.423657 0.087111 0.044 Uiso 1 1 calc R U . . .
H32B H 0.860463 0.317278 0.077397 0.044 Uiso 1 1 calc R U . . .
H32C H 0.937436 0.296520 0.146171 0.044 Uiso 1 1 calc R U . . .
C33 C 0.8283(3) 0.2763(3) 0.28400(19) 0.0233(8) Uani 1 1 d . . . . .
C34 C 0.9983(3) 0.4330(3) 0.2701(2) 0.0315(9) Uani 1 1 d . . . . .
H34A H 1.003871 0.464452 0.314611 0.038 Uiso 1 1 calc R U . . .
H34B H 0.938123 0.484064 0.241493 0.038 Uiso 1 1 calc R U . . .
C35 C 1.1335(4) 0.4410(3) 0.2195(2) 0.0439(11) Uani 1 1 d . . . . .
H35A H 1.165162 0.523893 0.203362 0.066 Uiso 1 1 calc R U . . .
H35B H 1.194297 0.392265 0.247704 0.066 Uiso 1 1 calc R U . . .
H35C H 1.128492 0.411894 0.174523 0.066 Uiso 1 1 calc R U . . .
C36 C 1.0059(4) 0.2293(3) 0.35217(19) 0.0318(9) Uani 1 1 d . . . . .
H36A H 1.102181 0.244656 0.338064 0.038 Uiso 1 1 calc R U . . .
H36B H 0.989055 0.146680 0.350053 0.038 Uiso 1 1 calc R U . . .
C37 C 0.9559(4) 0.2421(3) 0.4332(2) 0.0425(11) Uani 1 1 d . . . . .
H37A H 1.000808 0.185819 0.468114 0.064 Uiso 1 1 calc R U . . .
H37B H 0.974000 0.323388 0.435724 0.064 Uiso 1 1 calc R U . . .
H37C H 0.860914 0.225447 0.447708 0.064 Uiso 1 1 calc R U . . .
C38 C 0.6590(3) 0.4530(3) 0.35158(19) 0.0208(8) Uani 1 1 d . . . . .
C39 C 0.7237(3) 0.5626(3) 0.3304(2) 0.0258(8) Uani 1 1 d . . . . .
H39 H 0.743164 0.603525 0.278118 0.031 Uiso 1 1 calc R U . . .
C40 C 0.7603(3) 0.6132(3) 0.3830(2) 0.0267(9) Uani 1 1 d . . . . .
H40 H 0.805742 0.687938 0.366962 0.032 Uiso 1 1 calc R U . . .
C41 C 0.7308(3) 0.5553(3) 0.4602(2) 0.0259(8) Uani 1 1 d . . . . .
C42 C 0.6637(4) 0.4470(3) 0.4835(2) 0.0288(9) Uani 1 1 d . . . . .
H42 H 0.641942 0.407347 0.535957 0.035 Uiso 1 1 calc R U . . .
C43 C 0.6285(3) 0.3970(3) 0.42810(19) 0.0252(8) Uani 1 1 d . . . . .
H43 H 0.582410 0.322566 0.443666 0.030 Uiso 1 1 calc R U . . .
C44 C 0.7342(4) 0.5652(3) 0.5880(2) 0.0406(10) Uani 1 1 d . . . . .
H44A H 0.638292 0.554137 0.601478 0.061 Uiso 1 1 calc R U . . .
H44B H 0.761479 0.620541 0.614870 0.061 Uiso 1 1 calc R U . . .
H44C H 0.775730 0.488472 0.602704 0.061 Uiso 1 1 calc R U . . .
H2N H 0.741(4) 1.027(3) 0.261(2) 0.045(14) Uiso 1 1 d . . . . .
H5N H 0.523(4) 0.544(3) 0.253(2) 0.036(11) 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 1.426(2) . ?
S1 O1 1.432(2) . ?
S1 N2 1.605(3) . ?
S1 N1 1.668(3) . ?
S2 O6 1.424(2) . ?
S2 O5 1.429(2) . ?
S2 N5 1.612(3) . ?
S2 N4 1.663(3) . ?
O3 C11 1.247(4) . ?
O4 C19 1.365(4) . ?
O4 C22 1.426(4) . ?
O7 C33 1.239(4) . ?
O8 C41 1.362(4) . ?
O8 C44 1.435(4) . ?
N1 C1 1.444(4) . ?
N1 C4 1.450(4) . ?
N2 C3 1.480(4) . ?
N2 H2N 0.79(4) . ?
N3 C11 1.346(4) . ?
N3 C14 1.469(4) . ?
N3 C12 1.471(4) . ?
N4 C23 1.447(4) . ?
N4 C26 1.448(4) . ?
N5 C25 1.477(4) . ?
N5 H5N 0.84(3) . ?
N6 C33 1.347(4) . ?
N6 C36 1.463(4) . ?
N6 C34 1.471(4) . ?
C1 C2 1.346(4) . ?
C1 C10 1.505(4) . ?
C2 C11 1.510(5) . ?
C2 C3 1.523(5) . ?
C3 C16 1.518(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.381(5) . ?
C4 C9 1.394(5) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.508(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.515(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.371(4) . ?
C16 C17 1.395(4) . ?
C17 C18 1.363(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(4) . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.327(4) . ?
C23 C32 1.505(4) . ?
C24 C33 1.517(4) . ?
C24 C25 1.525(4) . ?
C25 C38 1.526(5) . ?
C25 H25 1.0000 . ?
C26 C31 1.382(5) . ?
C26 C27 1.385(4) . ?
C27 C28 1.383(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C34 C35 1.513(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.524(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C43 1.381(4) . ?
C38 C39 1.385(4) . ?
C39 C40 1.368(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.397(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.382(5) . ?
C42 C43 1.404(5) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

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 O1 120.01(15) . . ?
O2 S1 N2 109.51(16) . . ?
O1 S1 N2 107.31(15) . . ?
O2 S1 N1 107.88(13) . . ?
O1 S1 N1 105.84(14) . . ?
N2 S1 N1 105.32(15) . . ?
O6 S2 O5 120.13(14) . . ?
O6 S2 N5 109.27(15) . . ?
O5 S2 N5 107.15(15) . . ?
O6 S2 N4 107.91(13) . . ?
O5 S2 N4 106.09(14) . . ?
N5 S2 N4 105.31(15) . . ?
C19 O4 C22 118.2(3) . . ?
C41 O8 C44 118.1(3) . . ?
C1 N1 C4 116.3(3) . . ?
C1 N1 S1 114.2(2) . . ?
C4 N1 S1 118.2(2) . . ?
C3 N2 S1 116.4(3) . . ?
C3 N2 H2N 120(3) . . ?
S1 N2 H2N 116(3) . . ?
C11 N3 C14 117.7(3) . . ?
C11 N3 C12 125.0(3) . . ?
C14 N3 C12 117.2(3) . . ?
C23 N4 C26 117.8(3) . . ?
C23 N4 S2 114.1(2) . . ?
C26 N4 S2 119.1(2) . . ?
C25 N5 S2 115.3(2) . . ?
C25 N5 H5N 121(3) . . ?
S2 N5 H5N 115(2) . . ?
C33 N6 C36 118.3(3) . . ?
C33 N6 C34 124.9(3) . . ?
C36 N6 C34 116.0(3) . . ?
C2 C1 N1 122.2(3) . . ?
C2 C1 C10 124.3(3) . . ?
N1 C1 C10 113.5(3) . . ?
C1 C2 C11 120.0(3) . . ?
C1 C2 C3 126.6(3) . . ?
C11 C2 C3 112.5(3) . . ?
N2 C3 C16 110.2(3) . . ?
N2 C3 C2 112.3(3) . . ?
C16 C3 C2 111.1(3) . . ?
N2 C3 H3 107.7 . . ?
C16 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C5 C4 C9 120.5(3) . . ?
C5 C4 N1 119.1(3) . . ?
C9 C4 N1 120.3(3) . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C4 C9 H9 120.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N3 121.8(3) . . ?
O3 C11 C2 118.1(3) . . ?
N3 C11 C2 120.2(3) . . ?
N3 C12 C13 113.9(3) . . ?
N3 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N3 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.3(3) . . ?
N3 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 117.9(3) . . ?
C21 C16 C3 121.0(3) . . ?
C17 C16 C3 121.1(3) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
O4 C19 C20 125.0(3) . . ?
O4 C19 C18 115.5(3) . . ?
C20 C19 C18 119.5(3) . . ?
C19 C20 C21 118.9(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 122.1(3) . . ?
C16 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N4 121.7(3) . . ?
C24 C23 C32 124.8(3) . . ?
N4 C23 C32 113.4(3) . . ?
C23 C24 C33 121.6(3) . . ?
C23 C24 C25 127.2(3) . . ?
C33 C24 C25 110.4(3) . . ?
N5 C25 C24 112.7(3) . . ?
N5 C25 C38 108.9(3) . . ?
C24 C25 C38 112.2(3) . . ?
N5 C25 H25 107.6 . . ?
C24 C25 H25 107.6 . . ?
C38 C25 H25 107.6 . . ?
C31 C26 C27 119.9(3) . . ?
C31 C26 N4 120.5(3) . . ?
C27 C26 N4 119.5(3) . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 120.3(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C26 120.5(3) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
C23 C32 H32A 109.5 . . ?
C23 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C23 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O7 C33 N6 122.0(3) . . ?
O7 C33 C24 117.2(3) . . ?
N6 C33 C24 120.7(3) . . ?
N6 C34 C35 113.5(3) . . ?
N6 C34 H34A 108.9 . . ?
C35 C34 H34A 108.9 . . ?
N6 C34 H34B 108.9 . . ?
C35 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N6 C36 C37 112.0(3) . . ?
N6 C36 H36A 109.2 . . ?
C37 C36 H36A 109.2 . . ?
N6 C36 H36B 109.2 . . ?
C37 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C43 C38 C39 118.1(3) . . ?
C43 C38 C25 120.7(3) . . ?
C39 C38 C25 121.2(3) . . ?
C40 C39 C38 121.5(3) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C41 120.1(3) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
O8 C41 C42 124.9(3) . . ?
O8 C41 C40 115.2(3) . . ?
C42 C41 C40 119.9(3) . . ?
C41 C42 C43 118.6(3) . . ?
C41 C42 H42 120.7 . . ?
C43 C42 H42 120.7 . . ?
C38 C43 C42 121.8(3) . . ?
C38 C43 H43 119.1 . . ?
C42 C43 H43 119.1 . . ?
O8 C44 H44A 109.5 . . ?
O8 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O8 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_lay50
_database_code_depnum_ccdc_archive 'CCDC 2309237'
loop_
_audit_author_name
_audit_author_address
'Eduard B. Rusanov'
;Institute of Organic Chemistry, National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-11-20 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N6 O8 S2, C5 H12 N O, C3 H6 O, Cl'
_chemical_formula_sum            'C24 H36 Cl N7 O10 S2'
_chemical_formula_weight         682.17

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'
Cl Cl 0.1484 0.1585 '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                   12.0653(10)
_cell_length_b                   25.2004(18)
_cell_length_c                   11.6530(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.003(5)
_cell_angle_gamma                90
_cell_volume                     3236.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2930
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      22.06
_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.309
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5913
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31683
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6649
_reflns_number_gt                4181
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0709P)²+1.2749P] 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         6649
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1442
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
S1 S 0.21713(8) 0.03061(4) 0.30531(8) 0.0268(2) Uani 1 1 d . . . . .
S2 S 0.36910(8) 0.03326(3) 0.67400(8) 0.0251(2) Uani 1 1 d . . . . .
CL1 Cl 0.89036(8) 0.07375(4) 0.32274(8) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.1797(3) 0.07579(11) 0.3815(3) 0.0266(7) Uani 1 1 d . . . . .
N2 N 0.2279(3) -0.02831(11) 0.3712(3) 0.0272(7) Uani 1 1 d . . . . .
N3 N 0.2751(3) 0.08273(11) 0.6106(3) 0.0250(7) Uani 1 1 d . . . . .
N4 N 0.3168(3) -0.02177(11) 0.6010(3) 0.0261(7) Uani 1 1 d . . . . .
N5 N 0.4908(3) -0.25573(13) 0.5159(3) 0.0390(8) Uani 1 1 d . . . . .
N6 N 0.1819(4) 0.32887(14) 0.4584(4) 0.0535(10) Uani 1 1 d . . . . .
N7 N 0.7774(3) 0.03904(12) 0.0431(3) 0.0316(8) Uani 1 1 d . . . . .
O1 O 0.3349(2) 0.04330(9) 0.3136(2) 0.0327(6) Uani 1 1 d . . . . .
O2 O 0.1150(2) 0.02603(10) 0.1872(2) 0.0349(6) Uani 1 1 d . . . . .
O3 O 0.3711(2) 0.02661(10) 0.7968(2) 0.0325(6) Uani 1 1 d . . . . .
O4 O 0.4774(2) 0.04533(10) 0.6574(2) 0.0307(6) Uani 1 1 d . . . . .
O5 O 0.5455(3) -0.27572(11) 0.6187(3) 0.0571(9) Uani 1 1 d . . . . .
O6 O 0.4680(3) -0.27917(11) 0.4162(3) 0.0509(8) Uani 1 1 d . . . . .
O7 O 0.1208(4) 0.34773(12) 0.3553(3) 0.0772(12) Uani 1 1 d . . . . .
O8 O 0.2226(4) 0.35406(13) 0.5554(4) 0.0829(13) Uani 1 1 d . . . . .
O9 O 0.7007(3) 0.13983(12) -0.0754(3) 0.0596(9) Uani 1 1 d . . . . .
O10 O 0.9917(3) 0.26897(13) 0.5327(4) 0.0661(10) Uani 1 1 d . . . . .
C1 C 0.2681(3) 0.10340(14) 0.4893(3) 0.0248(8) Uani 1 1 d . . . . .
H1 H 0.349521 0.098337 0.487338 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3330(3) -0.03857(14) 0.4891(3) 0.0261(8) Uani 1 1 d . . . . .
H2 H 0.402252 -0.017558 0.486437 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1126(3) -0.05118(15) 0.3618(4) 0.0348(9) Uani 1 1 d . . . . .
H3A H 0.128743 -0.083364 0.413274 0.052 Uiso 1 1 calc R U . . .
H3B H 0.062341 -0.060106 0.274016 0.052 Uiso 1 1 calc R U . . .
H3C H 0.069868 -0.025336 0.391884 0.052 Uiso 1 1 calc R U . . .
C4 C 0.1594(3) 0.08042(15) 0.6247(3) 0.0315(9) Uani 1 1 d . . . . .
H4A H 0.110749 0.111860 0.585957 0.047 Uiso 1 1 calc R U . . .
H4B H 0.175443 0.079444 0.714207 0.047 Uiso 1 1 calc R U . . .
H4C H 0.114820 0.048410 0.583468 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3693(3) -0.09702(13) 0.4979(3) 0.0241(8) Uani 1 1 d . . . . .
C6 C 0.4212(3) -0.12293(15) 0.6123(3) 0.0331(9) Uani 1 1 d . . . . .
H6 H 0.429986 -0.104813 0.687060 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4606(4) -0.17524(15) 0.6192(4) 0.0368(9) Uani 1 1 d . . . . .
H7 H 0.494753 -0.193238 0.697470 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4488(3) -0.20038(14) 0.5094(3) 0.0298(8) Uani 1 1 d . . . . .
C9 C 0.3995(3) -0.17540(14) 0.3949(3) 0.0298(9) Uani 1 1 d . . . . .
H9 H 0.392843 -0.193432 0.320772 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3594(3) -0.12338(14) 0.3889(3) 0.0298(8) Uani 1 1 d . . . . .
H10 H 0.325033 -0.105690 0.310200 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2420(3) 0.16268(14) 0.4806(3) 0.0268(8) Uani 1 1 d . . . . .
C12 C 0.1848(4) 0.18750(15) 0.3640(4) 0.0349(9) Uani 1 1 d . . . . .
H12 H 0.158585 0.166846 0.289469 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1659(4) 0.24173(15) 0.3557(4) 0.0386(10) Uani 1 1 d . . . . .
H13 H 0.126108 0.258493 0.276409 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2062(4) 0.27091(15) 0.4652(4) 0.0374(10) Uani 1 1 d . . . . .
C15 C 0.2648(4) 0.24824(15) 0.5818(4) 0.0372(10) Uani 1 1 d . . . . .
H15 H 0.292159 0.269386 0.655630 0.045 Uiso 1 1 calc R U . . .
C16 C 0.2830(3) 0.19412(15) 0.5890(3) 0.0327(9) Uani 1 1 d . . . . .
H16 H 0.323978 0.177897 0.668822 0.039 Uiso 1 1 calc R U . . .
C17 C 0.8253(5) 0.12810(17) -0.0076(4) 0.0584(13) Uani 1 1 d . . . . .
H17A H 0.850688 0.139338 0.080862 0.070 Uiso 1 1 calc R U . . .
H17B H 0.873640 0.148461 -0.043711 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8509(4) 0.06970(16) -0.0115(4) 0.0410(10) Uani 1 1 d . . . . .
H18A H 0.829380 0.058446 -0.099360 0.049 Uiso 1 1 calc R U . . .
H18B H 0.938324 0.062697 0.037422 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6474(4) 0.05291(17) -0.0224(4) 0.0445(11) Uani 1 1 d . . . . .
H19A H 0.600476 0.035078 0.019183 0.053 Uiso 1 1 calc R U . . .
H19B H 0.616087 0.040525 -0.110572 0.053 Uiso 1 1 calc R U . . .
C20 C 0.6318(5) 0.1122(2) -0.0195(5) 0.0649(14) Uani 1 1 d . . . . .
H20A H 0.544844 0.121159 -0.065060 0.078 Uiso 1 1 calc R U . . .
H20B H 0.657805 0.123907 0.068701 0.078 Uiso 1 1 calc R U . . .
C21 C 0.7975(4) -0.01902(15) 0.0408(4) 0.0423(11) Uani 1 1 d . . . . .
H21A H 0.884315 -0.026709 0.084887 0.063 Uiso 1 1 calc R U . . .
H21B H 0.752717 -0.037549 0.082540 0.063 Uiso 1 1 calc R U . . .
H21C H 0.768830 -0.031109 -0.046445 0.063 Uiso 1 1 calc R U . . .
C22 C 0.8543(5) 0.2383(2) 0.3334(5) 0.0826(18) Uani 1 1 d . . . . .
H22A H 0.799491 0.207900 0.302415 0.124 Uiso 1 1 calc R U . . .
H22B H 0.807440 0.271280 0.309883 0.124 Uiso 1 1 calc R U . . .
H22C H 0.914036 0.237723 0.296227 0.124 Uiso 1 1 calc R U . . .
C23 C 0.9176(4) 0.23523(18) 0.4712(5) 0.0496(12) Uani 1 1 d . . . . .
C24 C 0.8902(5) 0.18876(19) 0.5325(5) 0.0627(14) Uani 1 1 d . . . . .
H24A H 0.829429 0.166494 0.468764 0.094 Uiso 1 1 calc R U . . .
H24B H 0.964442 0.168151 0.576024 0.094 Uiso 1 1 calc R U . . .
H24C H 0.858472 0.200816 0.593230 0.094 Uiso 1 1 calc R U . . .
H1N H 0.107(3) 0.0728(14) 0.372(3) 0.029(11) Uiso 1 1 d . . . . .
H4N H 0.260(4) -0.0368(15) 0.624(4) 0.041(11) Uiso 1 1 d . . . . .
H7N H 0.797(3) 0.0459(14) 0.121(3) 0.029(10) 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 O1 1.421(3) . ?
S1 O2 1.430(3) . ?
S1 N1 1.617(3) . ?
S1 N2 1.652(3) . ?
S2 O4 1.429(2) . ?
S2 O3 1.432(2) . ?
S2 N4 1.615(3) . ?
S2 N3 1.645(3) . ?
N1 C1 1.452(4) . ?
N2 C2 1.465(4) . ?
N2 C3 1.468(4) . ?
N3 C4 1.472(4) . ?
N3 C1 1.477(4) . ?
N4 C2 1.458(4) . ?
N5 O5 1.217(4) . ?
N5 O6 1.231(4) . ?
N5 C8 1.475(5) . ?
N6 O8 1.213(5) . ?
N6 O7 1.221(5) . ?
N6 C14 1.485(5) . ?
N7 C19 1.480(5) . ?
N7 C21 1.485(5) . ?
N7 C18 1.499(5) . ?
O9 C17 1.416(6) . ?
O9 C20 1.429(6) . ?
O10 C23 1.231(5) . ?
C1 C11 1.522(5) . ?
C2 C5 1.528(5) . ?
C5 C6 1.385(5) . ?
C5 C10 1.394(5) . ?
C6 C7 1.393(5) . ?
C7 C8 1.382(5) . ?
C8 C9 1.373(5) . ?
C9 C10 1.389(5) . ?
C11 C12 1.396(5) . ?
C11 C16 1.400(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.379(5) . ?
C14 C15 1.375(5) . ?
C15 C16 1.379(5) . ?
C17 C18 1.508(6) . ?
C19 C20 1.507(6) . ?
C22 C23 1.473(7) . ?
C23 C24 1.477(6) . ?

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 O2 121.97(15) . . ?
O1 S1 N1 107.42(16) . . ?
O2 S1 N1 105.16(16) . . ?
O1 S1 N2 106.45(15) . . ?
O2 S1 N2 104.41(15) . . ?
N1 S1 N2 111.37(15) . . ?
O4 S2 O3 121.04(15) . . ?
O4 S2 N4 107.13(15) . . ?
O3 S2 N4 105.67(15) . . ?
O4 S2 N3 106.21(15) . . ?
O3 S2 N3 105.41(15) . . ?
N4 S2 N3 111.35(16) . . ?
C1 N1 S1 122.7(3) . . ?
C2 N2 C3 115.6(3) . . ?
C2 N2 S1 118.0(2) . . ?
C3 N2 S1 115.1(2) . . ?
C4 N3 C1 115.7(3) . . ?
C4 N3 S2 115.6(2) . . ?
C1 N3 S2 117.2(2) . . ?
C2 N4 S2 123.7(2) . . ?
O5 N5 O6 123.6(4) . . ?
O5 N5 C8 118.6(3) . . ?
O6 N5 C8 117.7(3) . . ?
O8 N6 O7 124.5(4) . . ?
O8 N6 C14 117.9(4) . . ?
O7 N6 C14 117.6(4) . . ?
C19 N7 C21 111.7(3) . . ?
C19 N7 C18 110.2(3) . . ?
C21 N7 C18 111.8(3) . . ?
C17 O9 C20 109.0(3) . . ?
N1 C1 N3 113.2(3) . . ?
N1 C1 C11 110.7(3) . . ?
N3 C1 C11 109.8(3) . . ?
N4 C2 N2 114.1(3) . . ?
N4 C2 C5 111.1(3) . . ?
N2 C2 C5 110.4(3) . . ?
C6 C5 C10 119.4(3) . . ?
C6 C5 C2 121.6(3) . . ?
C10 C5 C2 118.9(3) . . ?
C5 C6 C7 120.7(4) . . ?
C8 C7 C6 118.5(4) . . ?
C9 C8 C7 122.0(3) . . ?
C9 C8 N5 119.2(3) . . ?
C7 C8 N5 118.8(3) . . ?
C8 C9 C10 119.1(3) . . ?
C9 C10 C5 120.3(3) . . ?
C12 C11 C16 118.5(3) . . ?
C12 C11 C1 120.7(3) . . ?
C16 C11 C1 120.5(3) . . ?
C13 C12 C11 120.9(4) . . ?
C14 C13 C12 118.5(4) . . ?
C15 C14 C13 122.6(4) . . ?
C15 C14 N6 118.2(4) . . ?
C13 C14 N6 119.2(4) . . ?
C14 C15 C16 118.5(4) . . ?
C15 C16 C11 121.0(4) . . ?
O9 C17 C18 111.8(4) . . ?
N7 C18 C17 109.1(3) . . ?
N7 C19 C20 109.8(4) . . ?
O9 C20 C19 111.8(4) . . ?
O10 C23 C22 122.0(5) . . ?
O10 C23 C24 121.3(5) . . ?
C22 C23 C24 116.7(4) . . ?

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.076



