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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_platon_sq[50a]
_database_code_depnum_ccdc_archive 'CCDC 2108576'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   18.407(3)
_cell_length_b                   6.1109(8)
_cell_length_c                   18.265(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.358(4)
_cell_angle_gamma                90
_cell_volume                     1808.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    138(2)
_cell_measurement_reflns_used    1344
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.67
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      138(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9459
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             3160
_reflns_number_gt                2877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.858
_reflns_Friedel_fraction_full    0.865

_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 1.000 0.125 0.500 22 3 ' '
2 0.500 0.625 0.500 22 3 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.3452P] 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 1086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3160
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73201(15) 0.5322(5) 0.82478(16) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.74808(14) 0.2909(5) 0.81151(14) 0.0245(5) Uani 1 1 d . . . . .
H2A H 0.802402 0.266623 0.814032 0.029 Uiso 1 1 calc R U . . .
H2B H 0.739470 0.187165 0.848300 0.029 Uiso 1 1 calc R U . . .
C3 C 0.67579(14) 0.2982(5) 0.72233(14) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.67114(17) 0.5490(5) 0.73000(16) 0.0257(6) Uani 1 1 d . . . . .
H4A H 0.615590 0.602541 0.717188 0.031 Uiso 1 1 calc R U . . .
H4B H 0.693357 0.632359 0.698552 0.031 Uiso 1 1 calc R U . . .
C5 C 0.59591(17) 0.1685(5) 0.69539(16) 0.0314(7) Uani 1 1 d . . . . .
H5A H 0.549943 0.256824 0.693453 0.038 Uiso 1 1 calc R U . . .
H5B H 0.603414 0.031868 0.727347 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5907(2) 0.1324(6) 0.60961(18) 0.0417(8) Uani 1 1 d . . . . .
H6A H 0.579739 -0.021240 0.590190 0.050 Uiso 1 1 calc R U . . .
H6B H 0.552417 0.233700 0.566086 0.050 Uiso 1 1 calc R U . . .
C7 C 0.68156(18) 0.1984(5) 0.64678(16) 0.0300(7) Uani 1 1 d . . . . .
H7 H 0.717970 0.066206 0.664024 0.036 Uiso 1 1 calc R U . . .
C8 C 0.70539(18) 0.3528(5) 0.59824(17) 0.0307(7) Uani 1 1 d . . . . .
C9 C 0.81856(19) 0.5145(5) 0.58822(18) 0.0350(7) Uani 1 1 d . . . . .
H9 H 0.776450 0.539452 0.528905 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8937(2) 0.4150(6) 0.5912(2) 0.0500(9) Uani 1 1 d . . . . .
H10A H 0.917298 0.516001 0.566467 0.075 Uiso 1 1 calc R U . . .
H10B H 0.934403 0.386116 0.649207 0.075 Uiso 1 1 calc R U . . .
H10C H 0.878915 0.277309 0.559958 0.075 Uiso 1 1 calc R U . . .
C11 C 0.8353(3) 0.7252(6) 0.6349(2) 0.0634(12) Uani 1 1 d . . . . .
H11A H 0.856928 0.832381 0.610256 0.095 Uiso 1 1 calc R U . . .
H11B H 0.783917 0.780605 0.631736 0.095 Uiso 1 1 calc R U . . .
H11C H 0.875936 0.700753 0.693199 0.095 Uiso 1 1 calc R U . . .
C12 C 0.80455(18) 0.6753(5) 0.85080(17) 0.0283(7) Uani 1 1 d . . . . .
C13 C 0.56236(16) 0.6816(5) 0.89220(16) 0.0270(6) Uani 1 1 d . . . . .
C14 C 0.5185(2) 0.8859(6) 0.8983(2) 0.0464(9) Uani 1 1 d . . . . .
H14A H 0.555822 0.970070 0.947624 0.070 Uiso 1 1 calc R U . . .
H14B H 0.501864 0.975650 0.848426 0.070 Uiso 1 1 calc R U . . .
H14C H 0.469393 0.843610 0.902853 0.070 Uiso 1 1 calc R U . . .
C15 C 0.50657(18) 0.5464(6) 0.81657(18) 0.0427(8) Uani 1 1 d . . . . .
H15A H 0.536329 0.415951 0.814134 0.064 Uiso 1 1 calc R U . . .
H15B H 0.457419 0.501847 0.820562 0.064 Uiso 1 1 calc R U . . .
H15C H 0.489890 0.633887 0.766135 0.064 Uiso 1 1 calc R U . . .
C16 C 0.59574(18) 0.5445(6) 0.97067(18) 0.0394(8) Uani 1 1 d . . . . .
H16A H 0.631578 0.634829 1.018717 0.059 Uiso 1 1 calc R U . . .
H16B H 0.549695 0.488368 0.977946 0.059 Uiso 1 1 calc R U . . .
H16C H 0.627523 0.421504 0.966083 0.059 Uiso 1 1 calc R U . . .
N1 N 0.69152(14) 0.5466(4) 0.87627(15) 0.0230(5) Uani 1 1 d . . . . .
N2 N 0.86024(16) 0.7835(5) 0.86546(16) 0.0464(7) Uani 1 1 d . . . . .
O1 O 0.65678(14) 0.4620(4) 0.54170(14) 0.0553(7) Uani 1 1 d . . . . .
O2 O 0.78626(12) 0.3566(3) 0.62593(11) 0.0344(5) Uani 1 1 d . . . . .
O3 O 0.70048(11) 0.9199(3) 0.94898(11) 0.0321(5) Uani 1 1 d . . . . .
S1 S 0.64681(4) 0.78513(11) 0.87535(4) 0.02245(17) Uani 1 1 d . . . . .
H1N H 0.7216(16) 0.495(4) 0.9230(17) 0.018(8) 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
C1 N1 1.454(3) . ?
C1 C12 1.473(4) . ?
C1 C2 1.545(4) . ?
C1 C4 1.556(4) . ?
C2 C3 1.538(3) . ?
C3 C5 1.531(4) . ?
C3 C4 1.545(4) . ?
C3 C7 1.558(3) . ?
C5 C6 1.540(4) . ?
C6 C7 1.530(4) . ?
C7 C8 1.496(4) . ?
C8 O1 1.198(3) . ?
C8 O2 1.325(3) . ?
C9 O2 1.466(3) . ?
C9 C10 1.488(4) . ?
C9 C11 1.493(4) . ?
C12 N2 1.140(4) . ?
C13 C15 1.516(4) . ?
C13 C14 1.520(4) . ?
C13 C16 1.516(4) . ?
C13 S1 1.835(3) . ?
N1 S1 1.670(3) . ?
O3 S1 1.4834(19) . ?

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
N1 C1 C12 114.8(2) . . ?
N1 C1 C2 110.8(2) . . ?
C12 C1 C2 113.9(2) . . ?
N1 C1 C4 113.3(2) . . ?
C12 C1 C4 112.5(2) . . ?
C2 C1 C4 88.78(19) . . ?
C3 C2 C1 90.3(2) . . ?
C5 C3 C2 122.8(2) . . ?
C5 C3 C4 117.2(2) . . ?
C2 C3 C4 89.4(2) . . ?
C5 C3 C7 88.4(2) . . ?
C2 C3 C7 122.5(2) . . ?
C4 C3 C7 119.9(2) . . ?
C3 C4 C1 89.7(2) . . ?
C3 C5 C6 89.2(2) . . ?
C7 C6 C5 89.1(2) . . ?
C8 C7 C6 118.0(2) . . ?
C8 C7 C3 116.1(2) . . ?
C6 C7 C3 88.7(2) . . ?
O1 C8 O2 124.2(3) . . ?
O1 C8 C7 123.6(3) . . ?
O2 C8 C7 112.2(2) . . ?
O2 C9 C10 106.9(3) . . ?
O2 C9 C11 108.6(2) . . ?
C10 C9 C11 113.3(3) . . ?
N2 C12 C1 175.1(3) . . ?
C15 C13 C14 111.2(3) . . ?
C15 C13 C16 110.8(3) . . ?
C14 C13 C16 112.1(2) . . ?
C15 C13 S1 107.24(18) . . ?
C14 C13 S1 104.6(2) . . ?
C16 C13 S1 110.74(18) . . ?
C1 N1 S1 116.62(19) . . ?
C8 O2 C9 117.7(2) . . ?
O3 S1 N1 111.25(12) . . ?
O3 S1 C13 106.97(11) . . ?
N1 S1 C13 98.63(12) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_b2m[50b]
_database_code_depnum_ccdc_archive 'CCDC 2108577'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.091(3)
_cell_length_b                   6.9401(17)
_cell_length_c                   13.251(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.847(10)
_cell_angle_gamma                90
_cell_volume                     925.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    515
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      19.78
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.99
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14193
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.540
_diffrn_reflns_theta_max         26.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3777
_reflns_number_gt                3118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.975

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0422P)²+0.2214P] 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 1182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3777
_refine_ls_number_parameters     197
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0413(3) 0.1258(5) 0.7991(2) 0.0286(8) Uani 1 1 d . . . . .
C2 C -0.0029(4) 0.1449(5) 0.6849(2) 0.0295(8) Uani 1 1 d . . . . .
H2A H -0.084921 0.221516 0.671466 0.035 Uiso 1 1 calc R U . . .
H2B H 0.068398 0.190459 0.642910 0.035 Uiso 1 1 calc R U . . .
C3 C -0.0255(3) -0.0731(5) 0.6798(2) 0.0269(8) Uani 1 1 d . . . . .
C4 C 0.0541(3) -0.0948(6) 0.7829(2) 0.0303(7) Uani 1 1 d . . . . .
H4A H 0.146662 -0.139060 0.777540 0.036 Uiso 1 1 calc R U . . .
H4B H 0.008599 -0.173227 0.832498 0.036 Uiso 1 1 calc R U . . .
C5 C -0.1651(4) -0.1607(5) 0.6700(3) 0.0373(9) Uani 1 1 d . . . . .
H5A H -0.231359 -0.079306 0.631533 0.045 Uiso 1 1 calc R U . . .
H5B H -0.198253 -0.201516 0.735349 0.045 Uiso 1 1 calc R U . . .
C6 C -0.1117(4) -0.3279(6) 0.6079(3) 0.0386(9) Uani 1 1 d . . . . .
H6A H -0.167958 -0.359520 0.546012 0.046 Uiso 1 1 calc R U . . .
H6B H -0.088844 -0.444938 0.648031 0.046 Uiso 1 1 calc R U . . .
C7 C 0.0084(3) -0.1979(5) 0.5891(2) 0.0269(8) Uani 1 1 d . . . . .
H7 H -0.010062 -0.123605 0.525037 0.032 Uiso 1 1 calc R U . . .
C8 C 0.1431(3) -0.2849(6) 0.5900(3) 0.0331(8) Uani 1 1 d . . . . .
C9 C 0.3728(4) -0.2079(7) 0.5976(3) 0.0604(13) Uani 1 1 d D . . . .
H9 H 0.380598 -0.326106 0.555261 0.073 Uiso 1 1 calc R U . . .
C10 C 0.4461(5) -0.0457(9) 0.5526(5) 0.0998(17) Uani 1 1 d D . . . .
H10A H 0.540554 -0.078652 0.552437 0.150 Uiso 1 1 calc R U . . .
H10B H 0.410185 -0.023192 0.483090 0.150 Uiso 1 1 calc R U . . .
H10C H 0.435812 0.071159 0.592861 0.150 Uiso 1 1 calc R U . . .
C11 C 0.4224(5) -0.2497(11) 0.7037(4) 0.0998(17) Uani 1 1 d D . . . .
H11A H 0.515452 -0.290517 0.704921 0.150 Uiso 1 1 calc R U . . .
H11B H 0.415383 -0.133391 0.744888 0.150 Uiso 1 1 calc R U . . .
H11C H 0.368938 -0.352824 0.731017 0.150 Uiso 1 1 calc R U . . .
C12 C 0.1675(4) 0.2254(6) 0.8284(3) 0.0374(9) Uani 1 1 d . . . . .
C13 C -0.2897(4) 0.3403(6) 0.9003(3) 0.0413(10) Uani 1 1 d . . . . .
C14 C -0.3587(4) 0.2364(8) 0.8111(4) 0.0703(17) Uani 1 1 d . . . . .
H14A H -0.356706 0.317209 0.750553 0.105 Uiso 1 1 calc R U . . .
H14B H -0.312894 0.114552 0.799819 0.105 Uiso 1 1 calc R U . . .
H14C H -0.451081 0.210261 0.825141 0.105 Uiso 1 1 calc R U . . .
C15 C -0.3510(5) 0.5378(8) 0.9143(4) 0.0633(14) Uani 1 1 d . . . . .
H15A H -0.350519 0.610406 0.850915 0.095 Uiso 1 1 calc R U . . .
H15B H -0.442714 0.522632 0.933180 0.095 Uiso 1 1 calc R U . . .
H15C H -0.299430 0.607671 0.967876 0.095 Uiso 1 1 calc R U . . .
C16 C -0.2888(5) 0.2244(9) 0.9965(4) 0.0691(16) Uani 1 1 d . . . . .
H16A H -0.243279 0.297333 1.051890 0.104 Uiso 1 1 calc R U . . .
H16B H -0.380387 0.198085 1.012777 0.104 Uiso 1 1 calc R U . . .
H16C H -0.242200 0.102376 0.987455 0.104 Uiso 1 1 calc R U . . .
N1 N -0.0643(3) 0.1650(4) 0.8647(2) 0.0283(7) Uani 1 1 d . . . . .
N2 N 0.2668(4) 0.2997(6) 0.8482(3) 0.0585(11) Uani 1 1 d . . . . .
O1 O 0.2349(2) -0.1472(4) 0.5949(2) 0.0413(7) Uani 1 1 d . . . . .
O2 O 0.1678(3) -0.4539(4) 0.5869(2) 0.0583(9) Uani 1 1 d . . . . .
O3 O -0.0556(3) 0.4978(4) 0.9536(2) 0.0471(8) Uani 1 1 d . . . . .
S1 S -0.11973(8) 0.39107(14) 0.86705(6) 0.0319(2) Uani 1 1 d . . . . .
H1N H -0.042(5) 0.105(7) 0.925(3) 0.074(16) 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
C1 N1 1.445(4) . ?
C1 C12 1.478(5) . ?
C1 C4 1.552(5) . ?
C1 C2 1.555(4) . ?
C2 C3 1.531(5) . ?
C3 C5 1.532(5) . ?
C3 C7 1.538(5) . ?
C3 C4 1.545(4) . ?
C5 C6 1.541(5) . ?
C6 C7 1.545(5) . ?
C7 C8 1.487(5) . ?
C8 O2 1.200(5) . ?
C8 O1 1.329(4) . ?
C9 O1 1.452(5) . ?
C9 C11 1.489(5) . ?
C9 C10 1.493(5) . ?
C12 N2 1.141(5) . ?
C13 C16 1.507(6) . ?
C13 C14 1.514(6) . ?
C13 C15 1.520(6) . ?
C13 S1 1.833(4) . ?
N1 S1 1.667(3) . ?
O3 S1 1.477(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C12 114.3(3) . . ?
N1 C1 C4 109.9(3) . . ?
C12 C1 C4 114.8(3) . . ?
N1 C1 C2 113.2(3) . . ?
C12 C1 C2 113.7(3) . . ?
C4 C1 C2 88.3(2) . . ?
C3 C2 C1 89.5(3) . . ?
C2 C3 C5 121.9(3) . . ?
C2 C3 C7 123.4(3) . . ?
C5 C3 C7 87.9(2) . . ?
C2 C3 C4 89.4(3) . . ?
C5 C3 C4 117.2(3) . . ?
C7 C3 C4 120.4(3) . . ?
C3 C4 C1 89.1(3) . . ?
C3 C5 C6 89.5(3) . . ?
C5 C6 C7 87.3(3) . . ?
C8 C7 C3 118.3(3) . . ?
C8 C7 C6 119.3(3) . . ?
C3 C7 C6 89.1(3) . . ?
O2 C8 O1 124.0(3) . . ?
O2 C8 C7 126.0(3) . . ?
O1 C8 C7 110.0(3) . . ?
O1 C9 C11 109.9(4) . . ?
O1 C9 C10 105.8(4) . . ?
C11 C9 C10 112.3(5) . . ?
N2 C12 C1 177.7(4) . . ?
C16 C13 C14 112.5(4) . . ?
C16 C13 C15 111.0(4) . . ?
C14 C13 C15 110.8(4) . . ?
C16 C13 S1 110.7(3) . . ?
C14 C13 S1 107.0(3) . . ?
C15 C13 S1 104.6(3) . . ?
C1 N1 S1 116.8(2) . . ?
C8 O1 C9 117.2(3) . . ?
O3 S1 N1 110.90(16) . . ?
O3 S1 C13 106.13(17) . . ?
N1 S1 C13 98.29(17) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_xray44[51a]
_database_code_depnum_ccdc_archive 'CCDC 2108578'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.675(2)
_cell_length_b                   8.970(2)
_cell_length_c                   11.079(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.311(9)
_cell_angle_gamma                90
_cell_volume                     889.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    775
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      26.47
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.93
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8575
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_full        25.045
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3026
_reflns_number_gt                2903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.931

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0467P)²+0.2200P] 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 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3026
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.40402(7) 0.64439(7) 0.57613(6) 0.02454(17) Uani 1 1 d . . . . .
O1 O 0.8375(3) 0.9234(3) 1.1682(3) 0.0551(7) Uani 1 1 d . . . . .
O2 O 0.6678(3) 0.7450(3) 1.0838(2) 0.0493(6) Uani 1 1 d . . . . .
O3 O 0.4197(2) 0.5913(2) 0.4546(2) 0.0347(5) Uani 1 1 d . . . . .
N1 N 0.5090(3) 0.7956(3) 0.6378(2) 0.0256(5) Uani 1 1 d . . . . .
N2 N 0.8103(3) 0.7579(3) 0.5466(3) 0.0406(6) Uani 1 1 d . . . . .
C1 C 0.6684(3) 0.7693(3) 0.7063(3) 0.0238(6) Uani 1 1 d . . . . .
C2 C 0.7161(3) 0.6361(3) 0.8020(2) 0.0268(6) Uani 1 1 d . . . . .
H2A H 0.638412 0.603478 0.834185 0.032 Uiso 1 1 calc R U . . .
H2B H 0.756300 0.550407 0.769336 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8368(3) 0.7359(3) 0.8980(3) 0.0269(6) Uani 1 1 d . . . . .
C4 C 0.7483(3) 0.8734(3) 0.8246(3) 0.0273(6) Uani 1 1 d . . . . .
H4A H 0.810993 0.951245 0.807403 0.033 Uiso 1 1 calc R U . . .
H4B H 0.680979 0.916632 0.863921 0.033 Uiso 1 1 calc R U . . .
C5 C 1.0032(3) 0.7328(3) 0.9155(3) 0.0337(7) Uani 1 1 d . . . . .
H5A H 1.039843 0.632832 0.903886 0.040 Uiso 1 1 calc R U . . .
H5B H 1.030189 0.808761 0.863360 0.040 Uiso 1 1 calc R U . . .
C6 C 1.0430(3) 0.7772(4) 1.0593(3) 0.0366(7) Uani 1 1 d . . . . .
H6A H 1.126795 0.719299 1.121781 0.044 Uiso 1 1 calc R U . . .
H6B H 1.058837 0.885612 1.075665 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8884(3) 0.7231(3) 1.0485(3) 0.0312(7) Uani 1 1 d . . . . .
H7 H 0.893498 0.615878 1.074609 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8000(3) 0.8101(3) 1.1100(3) 0.0318(7) Uani 1 1 d . . . . .
C9 C 0.5579(4) 0.8178(4) 1.1268(4) 0.0480(9) Uani 1 1 d . . . . .
H9 H 0.591838 0.920920 1.158791 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5480(6) 0.7254(8) 1.2344(4) 0.0920(18) Uani 1 1 d . . . . .
H10A H 0.475691 0.769934 1.266175 0.138 Uiso 1 1 calc R U . . .
H10B H 0.515517 0.624469 1.202179 0.138 Uiso 1 1 calc R U . . .
H10C H 0.646271 0.720760 1.305761 0.138 Uiso 1 1 calc R U . . .
C11 C 0.4151(5) 0.8239(7) 1.0123(4) 0.0774(15) Uani 1 1 d . . . . .
H11A H 0.338752 0.871844 1.037127 0.116 Uiso 1 1 calc R U . . .
H11B H 0.428862 0.881343 0.942482 0.116 Uiso 1 1 calc R U . . .
H11C H 0.383080 0.722403 0.981510 0.116 Uiso 1 1 calc R U . . .
C12 C 0.7480(3) 0.7647(3) 0.6162(3) 0.0289(6) Uani 1 1 d . . . . .
C13 C 0.2212(3) 0.7390(3) 0.5267(3) 0.0266(6) Uani 1 1 d . . . . .
C14 C 0.2133(4) 0.8654(4) 0.4329(3) 0.0401(8) Uani 1 1 d . . . . .
H14A H 0.286982 0.941945 0.478331 0.060 Uiso 1 1 calc R U . . .
H14B H 0.234877 0.826634 0.359191 0.060 Uiso 1 1 calc R U . . .
H14C H 0.112986 0.909149 0.400661 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1080(3) 0.6187(4) 0.4587(3) 0.0391(8) Uani 1 1 d . . . . .
H15A H 0.114689 0.538204 0.520491 0.059 Uiso 1 1 calc R U . . .
H15B H 0.007259 0.661312 0.426587 0.059 Uiso 1 1 calc R U . . .
H15C H 0.129150 0.578797 0.385117 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2023(4) 0.7923(4) 0.6499(3) 0.0414(8) Uani 1 1 d . . . . .
H16A H 0.208266 0.706843 0.706740 0.062 Uiso 1 1 calc R U . . .
H16B H 0.281677 0.863569 0.695764 0.062 Uiso 1 1 calc R U . . .
H16C H 0.104838 0.840823 0.626447 0.062 Uiso 1 1 calc R U . . .
H1N H 0.496(3) 0.862(4) 0.581(3) 0.024(8) 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 O3 1.489(2) . ?
S1 N1 1.677(2) . ?
S1 C13 1.847(3) . ?
O1 C8 1.184(4) . ?
O2 C8 1.334(4) . ?
O2 C9 1.473(4) . ?
N1 C1 1.456(3) . ?
N2 C12 1.147(4) . ?
C1 C12 1.475(4) . ?
C1 C2 1.547(4) . ?
C1 C4 1.555(4) . ?
C2 C3 1.534(4) . ?
C3 C4 1.545(4) . ?
C3 C5 1.548(4) . ?
C3 C7 1.552(4) . ?
C5 C6 1.543(4) . ?
C6 C7 1.534(4) . ?
C7 C8 1.500(4) . ?
C9 C11 1.480(6) . ?
C9 C10 1.485(6) . ?
C13 C14 1.520(4) . ?
C13 C15 1.518(4) . ?
C13 C16 1.521(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 111.89(12) . . ?
O3 S1 C13 107.06(12) . . ?
N1 S1 C13 96.50(12) . . ?
C8 O2 C9 119.1(2) . . ?
C1 N1 S1 116.05(18) . . ?
N1 C1 C12 111.9(2) . . ?
N1 C1 C2 117.6(2) . . ?
C12 C1 C2 110.2(2) . . ?
N1 C1 C4 115.6(2) . . ?
C12 C1 C4 111.5(2) . . ?
C2 C1 C4 87.86(19) . . ?
C3 C2 C1 88.6(2) . . ?
C2 C3 C4 88.7(2) . . ?
C2 C3 C5 123.9(2) . . ?
C4 C3 C5 115.0(2) . . ?
C2 C3 C7 123.4(2) . . ?
C4 C3 C7 120.8(2) . . ?
C5 C3 C7 88.2(2) . . ?
C3 C4 C1 87.9(2) . . ?
C6 C5 C3 88.0(2) . . ?
C7 C6 C5 89.1(2) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 C3 116.3(2) . . ?
C6 C7 C3 88.1(2) . . ?
O1 C8 O2 124.4(3) . . ?
O1 C8 C7 125.8(3) . . ?
O2 C8 C7 109.8(3) . . ?
O2 C9 C11 107.0(3) . . ?
O2 C9 C10 106.6(4) . . ?
C11 C9 C10 112.6(4) . . ?
N2 C12 C1 178.5(3) . . ?
C14 C13 C15 110.6(2) . . ?
C14 C13 C16 112.8(3) . . ?
C15 C13 C16 111.0(2) . . ?
C14 C13 S1 109.8(2) . . ?
C15 C13 S1 104.45(19) . . ?
C16 C13 S1 107.80(18) . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_xray43[51b]
_database_code_depnum_ccdc_archive 'CCDC 2108579'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.705(3)
_cell_length_b                   8.9445(19)
_cell_length_c                   11.226(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.390(4)
_cell_angle_gamma                90
_cell_volume                     913.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    404
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      20.52
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.97
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14266
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.935
_diffrn_reflns_theta_max         27.260
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4062
_reflns_number_gt                3359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.999

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0450P)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_abs_structure_details 
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4062
_refine_ls_number_parameters     203
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.013
_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 0.40606(8) 0.27239(8) 0.58140(7) 0.02708(19) Uani 1 1 d . . . . .
N1 N 0.5065(3) 0.4267(3) 0.6280(2) 0.0259(6) Uani 1 1 d D . . . .
N2 N 0.8023(4) 0.3585(3) 0.5339(3) 0.0464(8) Uani 1 1 d . . . . .
O1 O 0.4257(2) 0.2045(2) 0.4670(2) 0.0373(6) Uani 1 1 d . . . . .
O2 O 0.8098(4) 0.1991(4) 1.1250(4) 0.0834(12) Uani 1 1 d . . . . .
O3 O 0.6600(3) 0.3938(3) 1.0717(2) 0.0472(6) Uani 1 1 d . . . . .
C1 C 0.6630(3) 0.4051(3) 0.6920(3) 0.0252(6) Uani 1 1 d . . . . .
C2 C 0.7411(3) 0.5262(3) 0.7901(3) 0.0294(7) Uani 1 1 d . . . . .
H2A H 0.802728 0.595057 0.760975 0.035 Uiso 1 1 calc R U . . .
H2B H 0.674500 0.582348 0.823533 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8287(3) 0.4026(4) 0.8796(3) 0.0302(7) Uani 1 1 d . . . . .
C4 C 0.7112(3) 0.2902(4) 0.8024(3) 0.0288(7) Uani 1 1 d . . . . .
H4A H 0.634751 0.268875 0.839759 0.035 Uiso 1 1 calc R U . . .
H4B H 0.752259 0.196621 0.781489 0.035 Uiso 1 1 calc R U . . .
C5 C 0.9903(4) 0.3715(4) 0.8945(3) 0.0389(8) Uani 1 1 d . . . . .
H5A H 1.003348 0.282436 0.847127 0.047 Uiso 1 1 calc R U . . .
H5B H 1.041835 0.459242 0.876149 0.047 Uiso 1 1 calc R U . . .
C6 C 1.0251(4) 0.3434(5) 1.0357(4) 0.0578(12) Uani 1 1 d . . . . .
H6A H 1.110231 0.401370 1.091038 0.069 Uiso 1 1 calc R U . . .
H6B H 1.035486 0.236124 1.059011 0.069 Uiso 1 1 calc R U . . .
C7 C 0.8762(4) 0.4097(4) 1.0267(3) 0.0389(8) Uani 1 1 d . . . . .
H7 H 0.887113 0.515616 1.057174 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7824(4) 0.3223(4) 1.0823(3) 0.0425(9) Uani 1 1 d . . . . .
C9 C 0.5485(4) 0.3179(4) 1.1110(3) 0.0455(9) Uani 1 1 d . . . . .
H9 H 0.577947 0.211484 1.133214 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5409(7) 0.3976(8) 1.2243(5) 0.106(2) Uani 1 1 d . . . . .
H10A H 0.467222 0.349639 1.253127 0.158 Uiso 1 1 calc R U . . .
H10B H 0.637109 0.393650 1.292383 0.158 Uiso 1 1 calc R U . . .
H10C H 0.513229 0.502057 1.202300 0.158 Uiso 1 1 calc R U . . .
C11 C 0.4074(5) 0.3233(7) 1.0016(4) 0.0860(18) Uani 1 1 d . . . . .
H11A H 0.330473 0.273424 1.024848 0.129 Uiso 1 1 calc R U . . .
H11B H 0.379617 0.427774 0.979551 0.129 Uiso 1 1 calc R U . . .
H11C H 0.419241 0.272400 0.928512 0.129 Uiso 1 1 calc R U . . .
C12 C 0.7410(3) 0.3781(3) 0.6028(3) 0.0310(7) Uani 1 1 d . . . . .
C13 C 0.2244(4) 0.3631(4) 0.5256(3) 0.0326(8) Uani 1 1 d . . . . .
C14 C 0.1167(4) 0.2327(4) 0.4829(4) 0.0481(10) Uani 1 1 d . . . . .
H14A H 0.126745 0.167648 0.555671 0.072 Uiso 1 1 calc R U . . .
H14B H 0.016057 0.271299 0.448464 0.072 Uiso 1 1 calc R U . . .
H14C H 0.138366 0.175359 0.417064 0.072 Uiso 1 1 calc R U . . .
C15 C 0.2109(4) 0.4646(4) 0.4150(4) 0.0484(10) Uani 1 1 d . . . . .
H15A H 0.225105 0.406402 0.346208 0.073 Uiso 1 1 calc R U . . .
H15B H 0.112955 0.510285 0.384628 0.073 Uiso 1 1 calc R U . . .
H15C H 0.285758 0.543142 0.442168 0.073 Uiso 1 1 calc R U . . .
C16 C 0.2037(4) 0.4449(5) 0.6362(4) 0.0525(11) Uani 1 1 d . . . . .
H16A H 0.213477 0.374110 0.705327 0.079 Uiso 1 1 calc R U . . .
H16B H 0.278469 0.523175 0.666231 0.079 Uiso 1 1 calc R U . . .
H16C H 0.105667 0.490318 0.608691 0.079 Uiso 1 1 calc R U . . .
H1N H 0.493(4) 0.499(3) 0.569(2) 0.034(9) 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 O1 1.492(2) . ?
S1 N1 1.666(3) . ?
S1 C13 1.841(3) . ?
N1 C1 1.449(4) . ?
N2 C12 1.142(4) . ?
O2 C8 1.194(5) . ?
O3 C8 1.317(4) . ?
O3 C9 1.470(4) . ?
C1 C12 1.470(4) . ?
C1 C2 1.543(4) . ?
C1 C4 1.551(4) . ?
C2 C3 1.535(4) . ?
C3 C4 1.541(4) . ?
C3 C5 1.543(5) . ?
C3 C7 1.554(4) . ?
C5 C6 1.523(5) . ?
C6 C7 1.532(5) . ?
C7 C8 1.493(5) . ?
C9 C10 1.483(6) . ?
C9 C11 1.487(6) . ?
C13 C15 1.506(5) . ?
C13 C16 1.514(4) . ?
C13 C14 1.527(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 111.81(13) . . ?
O1 S1 C13 106.31(14) . . ?
N1 S1 C13 97.36(13) . . ?
C1 N1 S1 116.26(19) . . ?
C8 O3 C9 118.9(3) . . ?
N1 C1 C12 112.6(3) . . ?
N1 C1 C2 115.4(2) . . ?
C12 C1 C2 111.1(3) . . ?
N1 C1 C4 117.2(2) . . ?
C12 C1 C4 110.6(3) . . ?
C2 C1 C4 87.6(2) . . ?
C3 C2 C1 89.1(2) . . ?
C2 C3 C4 88.2(2) . . ?
C2 C3 C5 120.7(3) . . ?
C4 C3 C5 117.9(3) . . ?
C2 C3 C7 123.9(3) . . ?
C4 C3 C7 120.8(3) . . ?
C5 C3 C7 88.7(2) . . ?
C3 C4 C1 88.6(2) . . ?
C6 C5 C3 89.5(3) . . ?
C5 C6 C7 90.3(3) . . ?
C8 C7 C6 117.9(3) . . ?
C8 C7 C3 115.2(3) . . ?
C6 C7 C3 88.8(2) . . ?
O2 C8 O3 123.6(4) . . ?
O2 C8 C7 124.6(4) . . ?
O3 C8 C7 111.7(3) . . ?
O3 C9 C10 107.3(3) . . ?
O3 C9 C11 107.4(3) . . ?
C10 C9 C11 112.7(4) . . ?
N2 C12 C1 179.3(3) . . ?
C15 C13 C16 112.7(3) . . ?
C15 C13 C14 110.4(3) . . ?
C16 C13 C14 110.8(3) . . ?
C15 C13 S1 110.1(2) . . ?
C16 C13 S1 108.6(2) . . ?
C14 C13 S1 103.9(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1_$1 0.901(13) 2.10(2) 2.869(3) 143(3) 2_656

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_1b21[52a]
_database_code_depnum_ccdc_archive 'CCDC 2108580'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.5944(16)
_cell_length_b                   12.7794(19)
_cell_length_c                   14.847(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1820.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1142
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      21.30
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.97
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17158
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3577
_reflns_number_gt                2998
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0351P)²+0.1768P] 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 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.76772(8) 0.20955(5) 0.17671(5) 0.0301(2) Uani 1 1 d . . . . .
O1 O 0.4546(2) -0.19859(15) 0.04968(13) 0.0359(5) Uani 1 1 d . . . . .
O2 O 0.5995(2) -0.06115(15) 0.05138(13) 0.0389(6) Uani 1 1 d . . . . .
O3 O 0.6478(2) 0.27195(15) 0.14443(15) 0.0444(6) Uani 1 1 d . . . . .
N1 N 0.7381(3) 0.08271(16) 0.16657(16) 0.0285(6) Uani 1 1 d . . . . .
H1N H 0.717(3) 0.0661(19) 0.1137(19) 0.025(8) Uiso 1 1 d . . . . .
N2 N 0.7757(3) -0.1577(2) 0.25627(17) 0.0485(7) Uani 1 1 d . . . . .
C1 C 0.6606(3) 0.02577(19) 0.23431(17) 0.0248(6) Uani 1 1 d . . . . .
C2 C 0.6295(3) 0.0745(2) 0.3277(2) 0.0329(7) Uani 1 1 d . . . . .
H2A H 0.617534 0.151453 0.326652 0.039 Uiso 1 1 calc R U . . .
H2B H 0.695369 0.052946 0.375557 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4904(3) 0.0126(2) 0.32771(18) 0.0315(7) Uani 1 1 d . . . . .
H3A H 0.496016 -0.056343 0.357983 0.038 Uiso 1 1 calc R U . . .
H3B H 0.409392 0.053276 0.349609 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5015(3) 0.0068(2) 0.22420(17) 0.0255(6) Uani 1 1 d . . . . .
C5 C 0.4086(3) 0.0846(2) 0.1735(2) 0.0350(7) Uani 1 1 d . . . . .
H5A H 0.453748 0.116773 0.120361 0.042 Uiso 1 1 calc R U . . .
H5B H 0.365381 0.138352 0.212538 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3111(3) -0.0075(3) 0.1505(2) 0.0433(8) Uani 1 1 d . . . . .
H6A H 0.280560 -0.008878 0.086790 0.052 Uiso 1 1 calc R U . . .
H6B H 0.230755 -0.014653 0.191834 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4341(3) -0.0839(2) 0.1717(2) 0.0286(6) Uani 1 1 d . . . . .
H7 H 0.407575 -0.145279 0.209772 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5074(3) -0.1118(2) 0.08640(19) 0.0292(7) Uani 1 1 d . . . . .
C9 C 0.5009(4) -0.2243(2) -0.04174(19) 0.0439(8) Uani 1 1 d . . . . .
H9 H 0.602598 -0.208669 -0.047881 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4769(4) -0.3401(2) -0.0530(2) 0.0474(9) Uani 1 1 d . . . . .
H10A H 0.506274 -0.361683 -0.113407 0.071 Uiso 1 1 calc R U . . .
H10B H 0.531077 -0.378424 -0.007797 0.071 Uiso 1 1 calc R U . . .
H10C H 0.377554 -0.355562 -0.045061 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4202(6) -0.1597(3) -0.1074(2) 0.0882(17) Uani 1 1 d . . . . .
H11A H 0.450488 -0.176312 -0.168826 0.132 Uiso 1 1 calc R U . . .
H11B H 0.320589 -0.174989 -0.101221 0.132 Uiso 1 1 calc R U . . .
H11C H 0.436619 -0.085284 -0.095350 0.132 Uiso 1 1 calc R U . . .
C12 C 0.7287(3) -0.0768(2) 0.24700(18) 0.0294(6) Uani 1 1 d . . . . .
C13 C 0.9003(3) 0.2195(2) 0.08738(18) 0.0262(6) Uani 1 1 d . . . . .
C14 C 0.8419(3) 0.1837(2) -0.00209(19) 0.0374(8) Uani 1 1 d . . . . .
H14A H 0.754529 0.220793 -0.014328 0.056 Uiso 1 1 calc R U . . .
H14B H 0.824244 0.108261 0.000052 0.056 Uiso 1 1 calc R U . . .
H14C H 0.909237 0.198989 -0.049979 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9347(4) 0.3364(2) 0.0849(2) 0.0380(8) Uani 1 1 d . . . . .
H15A H 0.964815 0.359230 0.144860 0.057 Uiso 1 1 calc R U . . .
H15B H 0.851684 0.375838 0.066956 0.057 Uiso 1 1 calc R U . . .
H15C H 1.009703 0.348851 0.041436 0.057 Uiso 1 1 calc R U . . .
C16 C 1.0270(3) 0.1551(2) 0.1142(2) 0.0426(8) Uani 1 1 d . . . . .
H16A H 1.063009 0.180301 0.172051 0.064 Uiso 1 1 calc R U . . .
H16B H 1.099347 0.162092 0.068028 0.064 Uiso 1 1 calc R U . . .
H16C H 1.000217 0.081381 0.119877 0.064 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 O3 1.479(2) . ?
S1 N1 1.652(2) . ?
S1 C13 1.842(3) . ?
O1 C8 1.335(3) . ?
O1 C9 1.466(4) . ?
O2 C8 1.213(3) . ?
N1 C1 1.447(3) . ?
N2 C12 1.135(3) . ?
C1 C12 1.477(4) . ?
C1 C2 1.549(4) . ?
C1 C4 1.552(4) . ?
C2 C3 1.552(4) . ?
C3 C4 1.542(4) . ?
C4 C5 1.532(4) . ?
C4 C7 1.540(4) . ?
C5 C6 1.541(4) . ?
C6 C7 1.563(4) . ?
C7 C8 1.492(4) . ?
C9 C11 1.494(5) . ?
C9 C10 1.507(4) . ?
C13 C14 1.512(4) . ?
C13 C16 1.522(4) . ?
C13 C15 1.529(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 111.46(13) . . ?
O3 S1 C13 105.43(12) . . ?
N1 S1 C13 96.95(12) . . ?
C8 O1 C9 116.7(2) . . ?
C1 N1 S1 121.21(18) . . ?
N1 C1 C12 107.9(2) . . ?
N1 C1 C2 121.3(2) . . ?
C12 C1 C2 109.1(2) . . ?
N1 C1 C4 121.1(2) . . ?
C12 C1 C4 108.0(2) . . ?
C2 C1 C4 87.7(2) . . ?
C1 C2 C3 87.7(2) . . ?
C4 C3 C2 88.0(2) . . ?
C5 C4 C7 89.7(2) . . ?
C5 C4 C3 114.7(2) . . ?
C7 C4 C3 120.7(2) . . ?
C5 C4 C1 121.2(2) . . ?
C7 C4 C1 125.4(2) . . ?
C3 C4 C1 88.0(2) . . ?
C4 C5 C6 88.1(2) . . ?
C5 C6 C7 88.5(2) . . ?
C8 C7 C4 114.3(2) . . ?
C8 C7 C6 109.5(2) . . ?
C4 C7 C6 87.1(2) . . ?
O2 C8 O1 123.0(3) . . ?
O2 C8 C7 125.4(2) . . ?
O1 C8 C7 111.5(2) . . ?
O1 C9 C11 108.9(3) . . ?
O1 C9 C10 106.0(2) . . ?
C11 C9 C10 113.0(3) . . ?
N2 C12 C1 177.1(3) . . ?
C14 C13 C16 111.2(2) . . ?
C14 C13 C15 110.8(2) . . ?
C16 C13 C15 111.2(2) . . ?
C14 C13 S1 110.9(2) . . ?
C16 C13 S1 109.0(2) . . ?
C15 C13 S1 103.5(2) . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1b11[52b]
_database_code_depnum_ccdc_archive 'CCDC 2108581'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   11.311(3)
_cell_length_b                   11.311(3)
_cell_length_c                   25.025(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2773(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    362
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      16.94
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.97
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30833
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3791
_reflns_number_gt                2854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0201P)²+0.7755P] 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 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.002
_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 0.24407(9) 0.68741(10) 0.05749(4) 0.0365(2) Uani 1 1 d . . . . .
O1 O 0.6274(2) 0.9747(3) -0.03077(10) 0.0373(6) Uani 1 1 d . . . . .
O2 O 0.8481(2) 1.1391(3) -0.02938(10) 0.0385(7) Uani 1 1 d . . . . .
O3 O 0.2641(3) 0.5718(3) 0.04450(12) 0.0528(8) Uani 1 1 d . . . . .
N1 N 0.3777(3) 0.8364(3) 0.03829(13) 0.0334(8) Uani 1 1 d . . . . .
N2 N 0.6518(4) 0.7997(4) 0.07810(16) 0.0559(10) Uani 1 1 d . . . . .
C1 C 0.4889(4) 0.9014(4) 0.07633(14) 0.0322(8) Uani 1 1 d . . . . .
C2 C 0.4516(4) 0.9224(4) 0.13336(16) 0.0511(11) Uani 1 1 d . . . . .
H2A H 0.451787 0.857674 0.159928 0.061 Uiso 1 1 calc R U . . .
H2B H 0.366235 0.926413 0.135494 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5825(4) 1.0637(4) 0.13376(16) 0.0508(12) Uani 1 1 d . . . . .
H3A H 0.662483 1.063613 0.149832 0.061 Uiso 1 1 calc R U . . .
H3B H 0.569870 1.137374 0.149004 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5803(4) 1.0592(4) 0.07204(14) 0.0332(9) Uani 1 1 d . . . . .
C5 C 0.5257(4) 1.1428(4) 0.04409(18) 0.0452(11) Uani 1 1 d . . . . .
H5A H 0.482233 1.178648 0.068534 0.054 Uiso 1 1 calc R U . . .
H5B H 0.466544 1.096374 0.012928 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6749(4) 1.2482(4) 0.02921(17) 0.0418(10) Uani 1 1 d . . . . .
H6A H 0.717974 1.327913 0.053493 0.050 Uiso 1 1 calc R U . . .
H6B H 0.687194 1.277516 -0.008631 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7153(3) 1.1379(3) 0.04117(14) 0.0313(8) Uani 1 1 d . . . . .
H7 H 0.798454 1.171271 0.064051 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7214(4) 1.0716(4) -0.00961(14) 0.0300(8) Uani 1 1 d . . . . .
C9 C 0.8732(4) 1.0963(4) -0.08142(16) 0.0399(9) Uani 1 1 d . . . . .
H9 H 0.786886 1.051773 -0.102735 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9216(4) 0.9960(5) -0.07162(18) 0.0526(12) Uani 1 1 d . . . . .
H10A H 1.009633 1.041981 -0.053020 0.079 Uiso 1 1 calc R U . . .
H10B H 0.932155 0.960282 -0.105867 0.079 Uiso 1 1 calc R U . . .
H10C H 0.854563 0.920551 -0.049591 0.079 Uiso 1 1 calc R U . . .
C11 C 0.9771(5) 1.2252(4) -0.1087(2) 0.0660(14) Uani 1 1 d . . . . .
H11A H 0.940698 1.287258 -0.112452 0.099 Uiso 1 1 calc R U . . .
H11B H 0.997408 1.203025 -0.144190 0.099 Uiso 1 1 calc R U . . .
H11C H 1.060899 1.269243 -0.087365 0.099 Uiso 1 1 calc R U . . .
C12 C 0.5776(4) 0.8403(4) 0.07741(15) 0.0374(9) Uani 1 1 d . . . . .
C13 C 0.1183(4) 0.6825(4) 0.00977(15) 0.0363(9) Uani 1 1 d . . . . .
C14 C 0.0915(5) 0.7971(5) 0.0237(2) 0.0616(13) Uani 1 1 d . . . . .
H14A H 0.175146 0.885037 0.018566 0.092 Uiso 1 1 calc R U . . .
H14B H 0.062530 0.788291 0.061138 0.092 Uiso 1 1 calc R U . . .
H14C H 0.019324 0.792246 0.000557 0.092 Uiso 1 1 calc R U . . .
C15 C -0.0077(4) 0.5436(4) 0.01937(19) 0.0532(12) Uani 1 1 d . . . . .
H15A H -0.085396 0.538127 -0.000164 0.080 Uiso 1 1 calc R U . . .
H15B H -0.028549 0.531572 0.057668 0.080 Uiso 1 1 calc R U . . .
H15C H 0.009671 0.471623 0.006786 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1679(4) 0.6911(5) -0.04728(16) 0.0540(12) Uani 1 1 d . . . . .
H16A H 0.094133 0.674162 -0.072158 0.081 Uiso 1 1 calc R U . . .
H16B H 0.195309 0.622314 -0.052724 0.081 Uiso 1 1 calc R U . . .
H16C H 0.246190 0.782188 -0.053773 0.081 Uiso 1 1 calc R U . . .
H1N H 0.401(3) 0.832(3) 0.0079(14) 0.019(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 O3 1.471(3) . ?
S1 N1 1.676(3) . ?
S1 C13 1.837(4) . ?
O1 C8 1.202(4) . ?
O2 C8 1.337(4) . ?
O2 C9 1.466(4) . ?
N1 C1 1.450(4) . ?
N2 C12 1.142(5) . ?
C1 C12 1.475(6) . ?
C1 C2 1.540(5) . ?
C1 C4 1.556(5) . ?
C2 C3 1.543(5) . ?
C3 C4 1.545(5) . ?
C4 C5 1.532(5) . ?
C4 C7 1.537(5) . ?
C5 C6 1.548(5) . ?
C6 C7 1.557(5) . ?
C7 C8 1.495(5) . ?
C9 C11 1.503(5) . ?
C9 C10 1.506(5) . ?
C13 C14 1.512(5) . ?
C13 C16 1.519(5) . ?
C13 C15 1.523(5) . ?

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
O3 S1 N1 111.59(17) . . ?
O3 S1 C13 106.92(18) . . ?
N1 S1 C13 98.03(16) . . ?
C8 O2 C9 118.0(3) . . ?
C1 N1 S1 116.1(3) . . ?
N1 C1 C12 113.2(3) . . ?
N1 C1 C2 116.8(3) . . ?
C12 C1 C2 111.0(3) . . ?
N1 C1 C4 116.5(3) . . ?
C12 C1 C4 108.7(3) . . ?
C2 C1 C4 87.9(3) . . ?
C1 C2 C3 88.3(3) . . ?
C2 C3 C4 88.2(3) . . ?
C5 C4 C7 90.2(3) . . ?
C5 C4 C3 116.2(3) . . ?
C7 C4 C3 119.2(3) . . ?
C5 C4 C1 119.8(3) . . ?
C7 C4 C1 126.7(3) . . ?
C3 C4 C1 87.7(3) . . ?
C4 C5 C6 88.0(3) . . ?
C5 C6 C7 88.9(3) . . ?
C8 C7 C4 114.8(3) . . ?
C8 C7 C6 110.2(3) . . ?
C4 C7 C6 87.5(3) . . ?
O1 C8 O2 124.4(3) . . ?
O1 C8 C7 126.1(3) . . ?
O2 C8 C7 109.5(3) . . ?
O2 C9 C11 105.7(3) . . ?
O2 C9 C10 107.9(3) . . ?
C11 C9 C10 113.7(4) . . ?
N2 C12 C1 176.5(4) . . ?
C14 C13 C16 112.9(4) . . ?
C14 C13 C15 111.3(3) . . ?
C16 C13 C15 109.8(4) . . ?
C14 C13 S1 108.0(3) . . ?
C16 C13 S1 110.7(3) . . ?
C15 C13 S1 103.9(3) . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_xray37[54b]
_database_code_depnum_ccdc_archive 'CCDC 2108583'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   9.7014(14)
_cell_length_b                   9.7014(14)
_cell_length_c                   16.297(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1328.3(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1181
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      20.90
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.98
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8230
_diffrn_reflns_av_unetI/netI     0.1105
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.424
_diffrn_reflns_theta_max         25.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.903
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.878
_reflns_number_total             2879
_reflns_number_gt                2074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_max     0.848
_reflns_Friedel_fraction_full    0.853

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)] 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 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   0.728
_refine_ls_restrained_S_all      0.728
_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 0.08124(13) 0.06365(12) 0.23063(6) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.2088(4) 0.2603(4) 0.2250(2) 0.0285(8) Uani 1 1 d . . . . .
N2 N 0.4784(5) 0.1440(5) 0.1699(3) 0.0558(12) Uani 1 1 d . . . . .
O1 O 0.0726(3) 0.0019(4) 0.3144(2) 0.0479(9) Uani 1 1 d . . . . .
O2 O 0.4085(4) 0.6005(3) 0.46957(18) 0.0401(8) Uani 1 1 d . . . . .
O3 O 0.2391(3) 0.5207(3) 0.36288(17) 0.0326(7) Uani 1 1 d . . . . .
C1 C 0.3763(5) 0.3164(5) 0.2409(3) 0.0267(10) Uani 1 1 d . . . . .
C2 C 0.4868(5) 0.4950(5) 0.2215(2) 0.0289(10) Uani 1 1 d . . . . .
H2A H 0.551359 0.514808 0.171252 0.035 Uiso 1 1 calc R U . . .
H2B H 0.431672 0.557547 0.221162 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5788(5) 0.5116(5) 0.3016(3) 0.0343(11) Uani 1 1 d . . . . .
H3A H 0.595652 0.602740 0.336038 0.041 Uiso 1 1 calc R U . . .
H3B H 0.679997 0.511895 0.292963 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4409(4) 0.3498(5) 0.3313(2) 0.0259(9) Uani 1 1 d . . . . .
C5 C 0.4754(6) 0.2405(6) 0.3849(3) 0.0392(12) Uani 1 1 d . . . . .
H5A H 0.588234 0.267505 0.384350 0.047 Uiso 1 1 calc R U . . .
H5B H 0.403300 0.125631 0.374700 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4296(6) 0.3050(5) 0.4600(3) 0.0366(12) Uani 1 1 d . . . . .
H6A H 0.521165 0.395925 0.487143 0.044 Uiso 1 1 calc R U . . .
H6B H 0.362367 0.222070 0.500324 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3356(5) 0.3538(5) 0.4023(2) 0.0264(9) Uani 1 1 d . . . . .
H7 H 0.224189 0.263328 0.396096 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3337(5) 0.5046(5) 0.4172(2) 0.0285(10) Uani 1 1 d . . . . .
C9 C 0.2289(6) 0.6656(5) 0.3677(3) 0.0413(12) Uani 1 1 d . . . . .
H9 H 0.232408 0.696417 0.426604 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3649(7) 0.7974(5) 0.3229(3) 0.0581(15) Uani 1 1 d . . . . .
H10A H 0.357201 0.894169 0.326429 0.087 Uiso 1 1 calc R U . . .
H10B H 0.465301 0.817113 0.347548 0.087 Uiso 1 1 calc R U . . .
H10C H 0.361669 0.767542 0.265165 0.087 Uiso 1 1 calc R U . . .
C11 C 0.0676(6) 0.6216(6) 0.3318(3) 0.0481(13) Uani 1 1 d . . . . .
H11A H 0.053137 0.714550 0.333281 0.072 Uiso 1 1 calc R U . . .
H11B H 0.062057 0.586603 0.274892 0.072 Uiso 1 1 calc R U . . .
H11C H -0.016410 0.535182 0.364077 0.072 Uiso 1 1 calc R U . . .
C12 C 0.4286(5) 0.2161(5) 0.1989(3) 0.0337(10) Uani 1 1 d . . . . .
C13 C -0.1023(5) 0.0760(5) 0.2163(3) 0.0333(10) Uani 1 1 d . . . . .
C14 C -0.1321(6) 0.1493(6) 0.2923(3) 0.0514(14) Uani 1 1 d . . . . .
H14A H -0.140405 0.085539 0.340668 0.077 Uiso 1 1 calc R U . . .
H14B H -0.043633 0.258191 0.299658 0.077 Uiso 1 1 calc R U . . .
H14C H -0.231496 0.151232 0.285416 0.077 Uiso 1 1 calc R U . . .
C15 C -0.0879(6) 0.1667(5) 0.1386(3) 0.0410(12) Uani 1 1 d . . . . .
H15A H -0.068862 0.114336 0.092103 0.062 Uiso 1 1 calc R U . . .
H15B H -0.186588 0.168894 0.129527 0.062 Uiso 1 1 calc R U . . .
H15C H 0.001275 0.275854 0.143769 0.062 Uiso 1 1 calc R U . . .
C16 C -0.2319(6) -0.0982(6) 0.2072(3) 0.0531(14) Uani 1 1 d . . . . .
H16A H -0.239831 -0.155565 0.258057 0.080 Uiso 1 1 calc R U . . .
H16B H -0.334060 -0.104357 0.195949 0.080 Uiso 1 1 calc R U . . .
H16C H -0.204931 -0.146498 0.161649 0.080 Uiso 1 1 calc R U . . .
H1 H 0.184(5) 0.329(5) 0.258(3) 0.041(13) 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 1.477(3) . ?
S1 N1 1.679(4) . ?
S1 C13 1.858(4) . ?
N1 C1 1.455(5) . ?
N2 C12 1.133(5) . ?
O2 C8 1.202(4) . ?
O3 C8 1.339(5) . ?
O3 C9 1.460(5) . ?
C1 C12 1.472(6) . ?
C1 C2 1.547(6) . ?
C1 C4 1.571(5) . ?
C2 C3 1.542(6) . ?
C3 C4 1.546(6) . ?
C4 C5 1.534(5) . ?
C4 C7 1.556(5) . ?
C5 C6 1.537(6) . ?
C6 C7 1.539(6) . ?
C7 C8 1.493(6) . ?
C9 C10 1.491(7) . ?
C9 C11 1.518(6) . ?
C13 C15 1.507(6) . ?
C13 C14 1.527(6) . ?
C13 C16 1.528(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 N1 111.82(18) . . ?
O1 S1 C13 106.3(2) . . ?
N1 S1 C13 96.06(18) . . ?
C1 N1 S1 117.8(3) . . ?
C8 O3 C9 117.2(3) . . ?
N1 C1 C12 111.1(4) . . ?
N1 C1 C2 113.7(3) . . ?
C12 C1 C2 111.8(4) . . ?
N1 C1 C4 120.0(3) . . ?
C12 C1 C4 109.8(3) . . ?
C2 C1 C4 88.8(3) . . ?
C3 C2 C1 89.2(3) . . ?
C2 C3 C4 89.8(3) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 C7 88.1(3) . . ?
C3 C4 C7 117.0(3) . . ?
C5 C4 C1 126.4(3) . . ?
C3 C4 C1 88.2(3) . . ?
C7 C4 C1 120.2(3) . . ?
C4 C5 C6 88.0(3) . . ?
C5 C6 C7 88.6(3) . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 C4 118.4(3) . . ?
C6 C7 C4 87.1(3) . . ?
O2 C8 O3 124.3(4) . . ?
O2 C8 C7 125.1(4) . . ?
O3 C8 C7 110.6(3) . . ?
O3 C9 C10 110.0(4) . . ?
O3 C9 C11 105.3(4) . . ?
C10 C9 C11 113.5(4) . . ?
N2 C12 C1 175.1(5) . . ?
C15 C13 C14 113.1(4) . . ?
C15 C13 C16 110.4(4) . . ?
C14 C13 C16 110.6(4) . . ?
C15 C13 S1 109.3(3) . . ?
C14 C13 S1 109.8(3) . . ?
C16 C13 S1 103.1(3) . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_xray39[59]
_database_code_depnum_ccdc_archive 'CCDC 2108585'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   9.6924(9)
_cell_length_b                   9.6924(9)
_cell_length_c                   16.293(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1325.5(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    848
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.45
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.99
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7786
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         25.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.887
_reflns_number_total             2911
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.835
_reflns_Friedel_fraction_full    0.838

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.1787P)²+3.8763P] 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 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2911
_refine_ls_number_parameters     206
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2967
_refine_ls_wR_factor_gt          0.2876
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.004

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 -0.0175(4) 0.0635(3) 0.28499(16) 0.0321(7) Uani 1 1 d . . . . .
O1 O -0.0689(13) 0.0035(12) 0.3690(6) 0.049(3) Uani 1 1 d . . . . .
O2 O 0.1938(11) 0.6025(12) 0.5237(5) 0.041(2) Uani 1 1 d . . . . .
O3 O 0.2818(10) 0.5207(11) 0.4170(4) 0.0333(19) Uani 1 1 d . . . . .
N1 N 0.0526(12) 0.2606(12) 0.2800(6) 0.029(2) Uani 1 1 d . . . . .
N2 N -0.3324(15) 0.1452(17) 0.2240(7) 0.054(3) Uani 1 1 d . . . . .
C1 C -0.0570(14) 0.3160(14) 0.2952(6) 0.027(2) Uani 1 1 d . . . . .
C2 C 0.0092(14) 0.4967(14) 0.2765(6) 0.029(2) Uani 1 1 d . . . . .
H2A H 0.126972 0.560707 0.276277 0.035 Uiso 1 1 calc R U . . .
H2B H -0.035766 0.516125 0.226183 0.035 Uiso 1 1 calc R U . . .
C3 C -0.0669(16) 0.5129(15) 0.3562(7) 0.032(2) Uani 1 1 d . . . . .
H3A H 0.007062 0.604115 0.390855 0.038 Uiso 1 1 calc R U . . .
H3B H -0.167946 0.512935 0.347395 0.038 Uiso 1 1 calc R U . . .
C4 C -0.0903(15) 0.3524(15) 0.3857(6) 0.031(3) Uani 1 1 d . . . . .
C5 C -0.2324(15) 0.2434(18) 0.4389(7) 0.039(3) Uani 1 1 d . . . . .
H5A H -0.274165 0.128603 0.428578 0.047 Uiso 1 1 calc R U . . .
H5B H -0.319199 0.269124 0.437822 0.047 Uiso 1 1 calc R U . . .
C6 C -0.1256(16) 0.3068(17) 0.5150(7) 0.041(3) Uani 1 1 d . . . . .
H6A H -0.143530 0.223804 0.555868 0.049 Uiso 1 1 calc R U . . .
H6B H -0.124901 0.399219 0.541241 0.049 Uiso 1 1 calc R U . . .
C7 C 0.0172(15) 0.3517(14) 0.4568(6) 0.030(2) Uani 1 1 d . . . . .
H7 H 0.038137 0.261054 0.450621 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1700(14) 0.5062(14) 0.4717(6) 0.027(2) Uani 1 1 d . . . . .
C9 C 0.4397(16) 0.6673(17) 0.4220(7) 0.040(3) Uani 1 1 d . . . . .
H9 H 0.467564 0.697699 0.480889 0.048 Uiso 1 1 calc R U . . .
C10 C 0.431(2) 0.7982(19) 0.3778(10) 0.056(4) Uani 1 1 d . . . . .
H10A H 0.535342 0.896066 0.380654 0.084 Uiso 1 1 calc R U . . .
H10B H 0.403118 0.768005 0.320245 0.084 Uiso 1 1 calc R U . . .
H10C H 0.350524 0.816357 0.403561 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5538(17) 0.625(2) 0.3861(8) 0.049(4) Uani 1 1 d . . . . .
H11A H 0.661394 0.717834 0.387654 0.074 Uiso 1 1 calc R U . . .
H11B H 0.551600 0.537784 0.417739 0.074 Uiso 1 1 calc R U . . .
H11C H 0.524014 0.590812 0.329051 0.074 Uiso 1 1 calc R U . . .
C12 C -0.2156(14) 0.2141(15) 0.2537(7) 0.031(3) Uani 1 1 d . . . . .
C13 C 0.1750(16) 0.0749(15) 0.2706(7) 0.032(2) Uani 1 1 d . . . . .
C14 C 0.137(2) -0.0986(19) 0.2609(10) 0.057(4) Uani 1 1 d . . . . .
H14A H 0.056696 -0.150879 0.217821 0.086 Uiso 1 1 calc R U . . .
H14B H 0.095523 -0.155466 0.312919 0.086 Uiso 1 1 calc R U . . .
H14C H 0.234075 -0.099992 0.245948 0.086 Uiso 1 1 calc R U . . .
C15 C 0.2557(18) 0.1674(17) 0.1923(8) 0.043(3) Uani 1 1 d . . . . .
H15A H 0.352704 0.162281 0.182198 0.065 Uiso 1 1 calc R U . . .
H15B H 0.283445 0.278904 0.198887 0.065 Uiso 1 1 calc R U . . .
H15C H 0.182743 0.120395 0.145818 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2804(19) 0.150(2) 0.3461(10) 0.050(4) Uani 1 1 d . . . . .
H16A H 0.220126 0.097400 0.395823 0.075 Uiso 1 1 calc R U . . .
H16B H 0.314275 0.263800 0.348324 0.075 Uiso 1 1 calc R U . . .
H16C H 0.374443 0.137514 0.342517 0.075 Uiso 1 1 calc R U . . .
H1N H 0.149(14) 0.344(14) 0.296(6) 0.01(2) 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 1.474(9) . ?
S1 N1 1.679(10) . ?
S1 C13 1.828(13) . ?
O2 C8 1.194(14) . ?
O3 C8 1.356(14) . ?
O3 C9 1.481(15) . ?
N1 C1 1.431(16) . ?
N2 C12 1.098(17) . ?
C1 C12 1.509(16) . ?
C1 C2 1.565(16) . ?
C1 C4 1.586(14) . ?
C2 C3 1.540(16) . ?
C3 C4 1.532(17) . ?
C4 C5 1.521(16) . ?
C4 C7 1.561(16) . ?
C5 C6 1.532(16) . ?
C6 C7 1.550(17) . ?
C7 C8 1.509(17) . ?
C9 C11 1.48(2) . ?
C9 C10 1.50(2) . ?
C13 C15 1.530(18) . ?
C13 C16 1.531(18) . ?
C13 C14 1.539(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 111.0(5) . . ?
O1 S1 C13 106.0(6) . . ?
N1 S1 C13 96.0(5) . . ?
C8 O3 C9 116.9(9) . . ?
C1 N1 S1 117.7(8) . . ?
N1 C1 C12 112.4(10) . . ?
N1 C1 C2 114.9(9) . . ?
C12 C1 C2 111.0(9) . . ?
N1 C1 C4 121.1(9) . . ?
C12 C1 C4 107.9(9) . . ?
C2 C1 C4 86.9(8) . . ?
C3 C2 C1 90.1(8) . . ?
C4 C3 C2 89.8(9) . . ?
C5 C4 C3 120.5(11) . . ?
C5 C4 C7 87.0(9) . . ?
C3 C4 C7 118.5(10) . . ?
C5 C4 C1 126.2(11) . . ?
C3 C4 C1 89.5(9) . . ?
C7 C4 C1 118.5(10) . . ?
C4 C5 C6 89.3(9) . . ?
C5 C6 C7 87.0(9) . . ?
C8 C7 C6 118.3(10) . . ?
C8 C7 C4 116.2(9) . . ?
C6 C7 C4 87.2(9) . . ?
O2 C8 O3 123.6(11) . . ?
O2 C8 C7 126.9(11) . . ?
O3 C8 C7 109.5(9) . . ?
O3 C9 C11 105.6(12) . . ?
O3 C9 C10 108.6(11) . . ?
C11 C9 C10 114.2(12) . . ?
N2 C12 C1 176.8(15) . . ?
C15 C13 C16 111.5(12) . . ?
C15 C13 C14 109.2(11) . . ?
C16 C13 C14 109.9(12) . . ?
C15 C13 S1 110.5(9) . . ?
C16 C13 S1 110.1(9) . . ?
C14 C13 S1 105.5(10) . . ?

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_oa1[62A]
_database_code_depnum_ccdc_archive 'CCDC 2108587'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.1605(12)
_cell_length_b                   9.3672(16)
_cell_length_c                   32.178(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.850(8)
_cell_angle_gamma                90
_cell_volume                     1850.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    557
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      19.88
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.99
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17702
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         0.635
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             6575
_reflns_number_gt                5257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.898
_reflns_Friedel_fraction_full    0.902

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0246P)²+1.0217P] 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 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6575
_refine_ls_number_parameters     479
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.021
_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
S1A S 0.74530(18) 0.54513(15) 0.57739(4) 0.0329(3) Uani 1 1 d . . . . .
N1A N 0.8071(6) 0.6611(5) 0.54019(12) 0.0314(10) Uani 1 1 d . . . . .
H1A H 0.948(7) 0.656(5) 0.5344(13) 0.028(12) Uiso 1 1 d . . . . .
N2A N 0.2676(7) 0.6410(6) 0.50986(13) 0.0442(12) Uani 1 1 d . . . . .
O3A O 0.8420(6) 0.4039(4) 0.57063(11) 0.0481(10) Uani 1 1 d . . . . .
C1A C 0.6835(7) 0.6422(5) 0.50021(14) 0.0278(10) Uani 1 1 d . . . . .
C2A C 0.7350(7) 0.7481(5) 0.46573(14) 0.0298(11) Uani 1 1 d . . . . .
H2A1 H 0.885327 0.786219 0.469035 0.036 Uiso 1 1 calc R U . . .
H2A2 H 0.627349 0.826324 0.461386 0.036 Uiso 1 1 calc R U . . .
C3A C 0.7030(7) 0.6271(5) 0.43321(14) 0.0303(11) Uani 1 1 d . . . . .
C4A C 0.7390(8) 0.5209(5) 0.46959(14) 0.0341(12) Uani 1 1 d . . . . .
H4A1 H 0.890518 0.485481 0.474181 0.041 Uiso 1 1 calc R U . . .
H4A2 H 0.633729 0.440783 0.468169 0.041 Uiso 1 1 calc R U . . .
C5A C 0.4856(7) 0.6291(6) 0.40621(14) 0.0348(11) Uani 1 1 d . . . . .
H5A1 H 0.378267 0.698081 0.415654 0.042 Uiso 1 1 calc R U . . .
H5A2 H 0.419437 0.533680 0.401245 0.042 Uiso 1 1 calc R U . . .
C6A C 0.6129(8) 0.6842(6) 0.37005(15) 0.0375(13) Uani 1 1 d . . . . .
H6A H 0.612358 0.790905 0.369083 0.045 Uiso 1 1 calc R U . . .
C7A C 0.8229(8) 0.6282(6) 0.39396(15) 0.0367(12) Uani 1 1 d . . . . .
H7A1 H 0.867642 0.532311 0.384942 0.044 Uiso 1 1 calc R U . . .
H7A2 H 0.946181 0.696198 0.394886 0.044 Uiso 1 1 calc R U . . .
C8A C 0.5442(9) 0.6229(6) 0.32814(16) 0.0453(14) Uani 1 1 d D . . . .
O1A O 0.378(2) 0.6935(15) 0.3084(4) 0.058(4) Uani 0.67(3) 1 d D . P A 1
O2A O 0.628(3) 0.5198(13) 0.3133(7) 0.061(4) Uani 0.67(3) 1 d D . P A 1
C9A C 0.282(2) 0.6382(18) 0.2684(3) 0.049(4) Uani 0.67(3) 1 d D . P A 1
H9A H 0.304136 0.532648 0.266692 0.059 Uiso 0.67(3) 1 calc R U P A 1
C10A C 0.042(2) 0.673(3) 0.2677(6) 0.097(7) Uani 0.67(3) 1 d D . P A 1
H10A H -0.033393 0.639295 0.241565 0.146 Uiso 0.67(3) 1 calc R U P A 1
H10B H -0.019318 0.626755 0.291319 0.146 Uiso 0.67(3) 1 calc R U P A 1
H10C H 0.023768 0.777018 0.269825 0.146 Uiso 0.67(3) 1 calc R U P A 1
C11A C 0.399(3) 0.714(3) 0.2351(4) 0.091(6) Uani 0.67(3) 1 d D . P A 1
H11A H 0.340444 0.680514 0.207470 0.137 Uiso 0.67(3) 1 calc R U P A 1
H11B H 0.376063 0.816993 0.237181 0.137 Uiso 0.67(3) 1 calc R U P A 1
H11C H 0.554910 0.692744 0.238994 0.137 Uiso 0.67(3) 1 calc R U P A 1
O2C O 0.559(6) 0.4980(14) 0.3186(13) 0.045(7) Uani 0.33(3) 1 d D . P A 2
O1C O 0.433(5) 0.722(2) 0.3057(10) 0.058(4) Uani 0.33(3) 1 d D . P A 2
C9C C 0.345(6) 0.675(3) 0.2641(10) 0.056(10) Uani 0.33(3) 1 d D . P A 2
H9C H 0.445673 0.605307 0.252249 0.067 Uiso 0.33(3) 1 calc R U P A 2
C10C C 0.129(7) 0.604(5) 0.2708(11) 0.105(16) Uani 0.33(3) 1 d D . P A 2
H10D H 0.060676 0.570061 0.244010 0.157 Uiso 0.33(3) 1 calc R U P A 2
H10E H 0.153538 0.523529 0.289966 0.157 Uiso 0.33(3) 1 calc R U P A 2
H10F H 0.032309 0.673686 0.282719 0.157 Uiso 0.33(3) 1 calc R U P A 2
C11C C 0.319(5) 0.807(3) 0.2370(7) 0.074(8) Uani 0.33(3) 1 d D . P A 2
H11D H 0.260171 0.780313 0.208845 0.111 Uiso 0.33(3) 1 calc R U P A 2
H11E H 0.218813 0.874107 0.248988 0.111 Uiso 0.33(3) 1 calc R U P A 2
H11F H 0.461171 0.853145 0.235629 0.111 Uiso 0.33(3) 1 calc R U P A 2
C12A C 0.4498(7) 0.6410(5) 0.50615(14) 0.0283(10) Uani 1 1 d . . . . .
C13A C 0.9115(8) 0.6254(6) 0.62171(14) 0.0375(12) Uani 1 1 d . . . . .
C14A C 1.1475(8) 0.6335(8) 0.61275(16) 0.0571(16) Uani 1 1 d . . . . .
H14A H 1.201461 0.537275 0.607541 0.086 Uiso 1 1 calc R U . . .
H14B H 1.161095 0.693251 0.588113 0.086 Uiso 1 1 calc R U . . .
H14C H 1.233195 0.675173 0.636783 0.086 Uiso 1 1 calc R U . . .
C15A C 0.8791(10) 0.5221(7) 0.65717(15) 0.0562(16) Uani 1 1 d . . . . .
H15A H 0.724476 0.519205 0.662237 0.084 Uiso 1 1 calc R U . . .
H15B H 0.926996 0.426524 0.649611 0.084 Uiso 1 1 calc R U . . .
H15C H 0.964822 0.554129 0.682495 0.084 Uiso 1 1 calc R U . . .
C16A C 0.8167(10) 0.7700(7) 0.63007(18) 0.0571(16) Uani 1 1 d . . . . .
H16A H 0.663696 0.759286 0.635699 0.086 Uiso 1 1 calc R U . . .
H16B H 0.898493 0.813370 0.654309 0.086 Uiso 1 1 calc R U . . .
H16C H 0.826392 0.831448 0.605639 0.086 Uiso 1 1 calc R U . . .
S1B S 0.13136(19) 0.37993(16) -0.07777(4) 0.0339(3) Uani 1 1 d . . . . .
O3B O 0.2417(6) 0.5167(4) -0.07087(11) 0.0477(10) Uani 1 1 d . . . . .
N1B N 0.2214(6) 0.2612(4) -0.04165(12) 0.0300(9) Uani 1 1 d . . . . .
H1B H 0.366(7) 0.262(5) -0.0399(13) 0.022(12) Uiso 1 1 d . . . . .
N2B N -0.2876(6) 0.2768(5) -0.00910(14) 0.0430(11) Uani 1 1 d . . . . .
C1B C 0.1368(7) 0.2802(5) -0.00069(14) 0.0282(11) Uani 1 1 d . . . . .
C2B C 0.2199(8) 0.4046(6) 0.02828(15) 0.0370(13) Uani 1 1 d . . . . .
H2B1 H 0.351407 0.452359 0.019309 0.044 Uiso 1 1 calc R U . . .
H2B2 H 0.105787 0.475297 0.033441 0.044 Uiso 1 1 calc R U . . .
C3B C 0.2677(7) 0.2999(5) 0.06393(15) 0.0307(11) Uani 1 1 d . . . . .
C4B C 0.2333(7) 0.1752(5) 0.03327(14) 0.0287(11) Uani 1 1 d . . . . .
H4B1 H 0.127670 0.103285 0.041651 0.034 Uiso 1 1 calc R U . . .
H4B2 H 0.370440 0.129186 0.026390 0.034 Uiso 1 1 calc R U . . .
C5B C 0.1358(7) 0.2964(6) 0.10284(15) 0.0366(12) Uani 1 1 d . . . . .
H5B1 H 0.084797 0.391299 0.111420 0.044 Uiso 1 1 calc R U . . .
H5B2 H 0.015396 0.226019 0.100974 0.044 Uiso 1 1 calc R U . . .
C6B C 0.3422(8) 0.2446(6) 0.12802(16) 0.0407(13) Uani 1 1 d . . . . .
H6B H 0.347593 0.137929 0.128688 0.049 Uiso 1 1 calc R U . . .
C7B C 0.4763(7) 0.3029(6) 0.09385(16) 0.0391(13) Uani 1 1 d . . . . .
H7B1 H 0.591505 0.237123 0.085901 0.047 Uiso 1 1 calc R U . . .
H7B2 H 0.535033 0.399982 0.099553 0.047 Uiso 1 1 calc R U . . .
C8B C 0.3940(10) 0.3048(7) 0.17072(18) 0.0518(16) Uani 1 1 d D . . . .
O1B O 0.501(11) 0.203(6) 0.1933(15) 0.059(4) Uani 0.27(4) 1 d D . P B 3
O2B O 0.393(11) 0.4336(11) 0.1757(11) 0.080(14) Uani 0.27(4) 1 d D . P B 3
C9B C 0.578(9) 0.251(5) 0.2355(14) 0.063(4) Uani 0.27(4) 1 d D . P B 3
H9B H 0.482157 0.329871 0.243892 0.075 Uiso 0.27(4) 1 calc R U P B 3
C10B C 0.811(9) 0.304(7) 0.2374(18) 0.077(16) Uani 0.27(4) 1 d D . P B 3
H10G H 0.857363 0.335170 0.265928 0.115 Uiso 0.27(4) 1 calc R U P B 3
H10H H 0.906911 0.227502 0.229290 0.115 Uiso 0.27(4) 1 calc R U P B 3
H10I H 0.820091 0.385197 0.218306 0.115 Uiso 0.27(4) 1 calc R U P B 3
C11B C 0.555(10) 0.125(7) 0.2647(13) 0.104(17) Uani 0.27(4) 1 d D . P B 3
H11G H 0.605538 0.152982 0.293268 0.156 Uiso 0.27(4) 1 calc R U P B 3
H11H H 0.402241 0.095775 0.263669 0.156 Uiso 0.27(4) 1 calc R U P B 3
H11I H 0.643708 0.044999 0.256040 0.156 Uiso 0.27(4) 1 calc R U P B 3
O1D O 0.550(4) 0.234(2) 0.1925(5) 0.059(4) Uani 0.73(4) 1 d D . P B 4
O2D O 0.307(3) 0.4065(15) 0.1857(5) 0.081(4) Uani 0.73(4) 1 d D . P B 4
C9D C 0.637(3) 0.286(2) 0.2337(4) 0.063(4) Uani 0.73(4) 1 d D . P B 4
H9D H 0.613931 0.391583 0.236144 0.075 Uiso 0.73(4) 1 calc R U P B 4
C10D C 0.877(3) 0.251(3) 0.2355(7) 0.095(7) Uani 0.73(4) 1 d D . P B 4
H10J H 0.949019 0.282483 0.262290 0.143 Uiso 0.73(4) 1 calc R U P B 4
H10K H 0.895516 0.147178 0.232826 0.143 Uiso 0.73(4) 1 calc R U P B 4
H10L H 0.943160 0.299047 0.212709 0.143 Uiso 0.73(4) 1 calc R U P B 4
C11D C 0.518(3) 0.205(2) 0.2658(5) 0.079(5) Uani 0.73(4) 1 d D . P B 4
H11J H 0.571227 0.237354 0.293877 0.118 Uiso 0.73(4) 1 calc R U P B 4
H11K H 0.361490 0.223989 0.261200 0.118 Uiso 0.73(4) 1 calc R U P B 4
H11L H 0.545423 0.102964 0.263149 0.118 Uiso 0.73(4) 1 calc R U P B 4
C12B C -0.1029(8) 0.2771(5) -0.00579(14) 0.0291(10) Uani 1 1 d . . . . .
C13B C 0.2499(7) 0.2967(6) -0.12279(15) 0.0357(12) Uani 1 1 d . . . . .
C14B C 0.1877(9) 0.4024(7) -0.15800(17) 0.0549(16) Uani 1 1 d . . . . .
H14D H 0.028704 0.408101 -0.162671 0.082 Uiso 1 1 calc R U . . .
H14E H 0.246578 0.496874 -0.150303 0.082 Uiso 1 1 calc R U . . .
H14F H 0.248096 0.370031 -0.183594 0.082 Uiso 1 1 calc R U . . .
C15B C 0.1399(9) 0.1534(6) -0.13079(17) 0.0512(15) Uani 1 1 d . . . . .
H15D H -0.017815 0.167211 -0.135746 0.077 Uiso 1 1 calc R U . . .
H15E H 0.195336 0.108805 -0.155338 0.077 Uiso 1 1 calc R U . . .
H15F H 0.171220 0.091522 -0.106465 0.077 Uiso 1 1 calc R U . . .
C16B C 0.4940(7) 0.2855(7) -0.11482(16) 0.0505(14) Uani 1 1 d . . . . .
H16D H 0.555993 0.381007 -0.109879 0.076 Uiso 1 1 calc R U . . .
H16E H 0.530340 0.225529 -0.090270 0.076 Uiso 1 1 calc R U . . .
H16F H 0.554457 0.242812 -0.139144 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
S1A O3A 1.475(4) . ?
S1A N1A 1.684(4) . ?
S1A C13A 1.844(5) . ?
N1A C1A 1.449(6) . ?
N2A C12A 1.139(5) . ?
C1A C12A 1.469(6) . ?
C1A C2A 1.541(6) . ?
C1A C4A 1.560(7) . ?
C2A C3A 1.544(6) . ?
C3A C7A 1.516(6) . ?
C3A C5A 1.534(6) . ?
C3A C4A 1.538(7) . ?
C5A C6A 1.546(7) . ?
C6A C8A 1.494(6) . ?
C6A C7A 1.540(7) . ?
C8A O2A 1.212(6) . ?
C8A O2C 1.215(7) . ?
C8A O1C 1.332(7) . ?
C8A O1A 1.333(6) . ?
O1A C9A 1.467(6) . ?
C9A C10A 1.514(7) . ?
C9A C11A 1.514(7) . ?
O1C C9C 1.469(7) . ?
C9C C10C 1.517(7) . ?
C9C C11C 1.517(7) . ?
C13A C14A 1.508(7) . ?
C13A C16A 1.508(8) . ?
C13A C15A 1.522(7) . ?
S1B O3B 1.458(4) . ?
S1B N1B 1.669(4) . ?
S1B C13B 1.849(5) . ?
N1B C1B 1.468(6) . ?
N2B C12B 1.134(5) . ?
C1B C12B 1.472(6) . ?
C1B C4B 1.551(6) . ?
C1B C2B 1.551(6) . ?
C2B C3B 1.519(6) . ?
C3B C4B 1.532(6) . ?
C3B C7B 1.539(6) . ?
C3B C5B 1.550(7) . ?
C5B C6B 1.528(6) . ?
C6B C8B 1.494(7) . ?
C6B C7B 1.531(7) . ?
C8B O2D 1.211(6) . ?
C8B O2B 1.217(7) . ?
C8B O1D 1.32(2) . ?
C8B O1B 1.34(6) . ?
O1B C9B 1.471(7) . ?
C9B C10B 1.519(7) . ?
C9B C11B 1.520(7) . ?
O1D C9D 1.471(6) . ?
C9D C10D 1.515(7) . ?
C9D C11D 1.518(7) . ?
C13B C16B 1.508(6) . ?
C13B C15B 1.516(7) . ?
C13B C14B 1.529(7) . ?

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
O3A S1A N1A 110.8(2) . . ?
O3A S1A C13A 106.0(2) . . ?
N1A S1A C13A 98.2(2) . . ?
C1A N1A S1A 114.7(3) . . ?
N1A C1A C12A 109.4(4) . . ?
N1A C1A C2A 115.8(4) . . ?
C12A C1A C2A 111.2(4) . . ?
N1A C1A C4A 121.5(4) . . ?
C12A C1A C4A 110.3(4) . . ?
C2A C1A C4A 86.9(3) . . ?
C1A C2A C3A 89.6(3) . . ?
C7A C3A C5A 89.5(4) . . ?
C7A C3A C4A 126.1(4) . . ?
C5A C3A C4A 120.1(4) . . ?
C7A C3A C2A 121.1(4) . . ?
C5A C3A C2A 115.5(4) . . ?
C4A C3A C2A 87.6(3) . . ?
C3A C4A C1A 89.1(4) . . ?
C3A C5A C6A 87.5(3) . . ?
C8A C6A C7A 118.8(4) . . ?
C8A C6A C5A 115.4(4) . . ?
C7A C6A C5A 88.2(4) . . ?
C3A C7A C6A 88.3(3) . . ?
O2C C8A O1C 126(2) . . ?
O2A C8A O1A 122.9(14) . . ?
O2A C8A C6A 124.4(12) . . ?
O2C C8A C6A 125(2) . . ?
O1C C8A C6A 108.3(14) . . ?
O1A C8A C6A 112.7(8) . . ?
C8A O1A C9A 118.6(11) . . ?
O1A C9A C10A 104.8(11) . . ?
O1A C9A C11A 106.1(12) . . ?
C10A C9A C11A 114.1(14) . . ?
C8A O1C C9C 115(2) . . ?
O1C C9C C10C 105(3) . . ?
O1C C9C C11C 106.9(18) . . ?
C10C C9C C11C 113(3) . . ?
N2A C12A C1A 178.5(5) . . ?
C14A C13A C16A 112.5(5) . . ?
C14A C13A C15A 111.4(5) . . ?
C16A C13A C15A 111.1(5) . . ?
C14A C13A S1A 110.7(3) . . ?
C16A C13A S1A 107.8(4) . . ?
C15A C13A S1A 102.8(4) . . ?
O3B S1B N1B 110.9(2) . . ?
O3B S1B C13B 106.2(2) . . ?
N1B S1B C13B 97.7(2) . . ?
C1B N1B S1B 114.9(3) . . ?
N1B C1B C12B 109.0(3) . . ?
N1B C1B C4B 114.3(4) . . ?
C12B C1B C4B 112.8(4) . . ?
N1B C1B C2B 120.5(4) . . ?
C12B C1B C2B 111.0(4) . . ?
C4B C1B C2B 88.0(3) . . ?
C3B C2B C1B 90.1(4) . . ?
C2B C3B C4B 89.9(4) . . ?
C2B C3B C7B 124.0(4) . . ?
C4B C3B C7B 118.7(4) . . ?
C2B C3B C5B 122.8(4) . . ?
C4B C3B C5B 116.8(4) . . ?
C7B C3B C5B 87.8(4) . . ?
C3B C4B C1B 89.7(3) . . ?
C6B C5B C3B 88.0(3) . . ?
C8B C6B C5B 118.1(4) . . ?
C8B C6B C7B 116.1(5) . . ?
C5B C6B C7B 88.9(4) . . ?
C6B C7B C3B 88.3(3) . . ?
O2D C8B O1D 120.7(13) . . ?
O2B C8B O1B 130(3) . . ?
O2D C8B C6B 126.5(9) . . ?
O2B C8B C6B 119.5(18) . . ?
O1D C8B C6B 112.8(9) . . ?
O1B C8B C6B 106.7(19) . . ?
C8B O1B C9B 113(4) . . ?
O1B C9B C10B 112(4) . . ?
O1B C9B C11B 107(4) . . ?
C10B C9B C11B 112(5) . . ?
C8B O1D C9D 120.1(17) . . ?
O1D C9D C10D 104.0(16) . . ?
O1D C9D C11D 106.6(12) . . ?
C10D C9D C11D 112.9(17) . . ?
N2B C12B C1B 178.6(5) . . ?
C16B C13B C15B 113.1(5) . . ?
C16B C13B C14B 110.8(4) . . ?
C15B C13B C14B 111.6(4) . . ?
C16B C13B S1B 110.5(3) . . ?
C15B C13B S1B 107.8(3) . . ?
C14B C13B S1B 102.5(4) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_xray38[55b]
_database_code_depnum_ccdc_archive 'CCDC 2108584'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   10.673(3)
_cell_length_b                   10.673(3)
_cell_length_c                   13.675(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1349.0(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    450
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      19.43
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.34
_exptl_absorpt_correction_T_max  0.98
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4749
_diffrn_reflns_av_unetI/netI     0.1517
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.203
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.920
_reflns_number_total             3326
_reflns_number_gt                1947
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_max     0.806
_reflns_Friedel_fraction_full    0.840

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0413P)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_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3326
_refine_ls_number_parameters     206
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_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 0.5634(2) 0.3891(2) 0.22239(13) 0.0300(5) Uani 1 1 d . . . . .
O1 O 0.1812(6) -0.1509(6) -0.1271(5) 0.0530(18) Uani 1 1 d . . . . .
O2 O 0.4204(5) -0.0564(5) -0.1268(4) 0.0323(13) Uani 1 1 d . . . . .
O3 O 0.6543(5) 0.3332(6) 0.2662(4) 0.0348(13) Uani 1 1 d . . . . .
N1 N 0.5174(7) 0.3320(6) 0.1066(4) 0.0284(15) Uani 1 1 d . . . . .
N2 N 0.5311(7) 0.0159(7) 0.1047(5) 0.0405(17) Uani 1 1 d . . . . .
C1 C 0.4137(8) 0.1796(8) 0.0977(5) 0.0276(18) Uani 1 1 d . . . . .
C2 C 0.2773(8) 0.1104(8) 0.1644(6) 0.037(2) Uani 1 1 d . . . . .
H2A H 0.282461 0.051953 0.218803 0.045 Uiso 1 1 calc R U . . .
H2B H 0.248244 0.179769 0.188161 0.045 Uiso 1 1 calc R U . . .
C3 C 0.1892(8) 0.0198(8) 0.0753(5) 0.0347(19) Uani 1 1 d . . . . .
H3A H 0.093789 0.013148 0.067982 0.042 Uiso 1 1 calc R U . . .
H3B H 0.180397 -0.076898 0.071280 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3088(7) 0.1351(7) 0.0086(5) 0.0264(17) Uani 1 1 d . . . . .
C5 C 0.3358(8) 0.1018(8) -0.0973(5) 0.0260(18) Uani 1 1 d . . . . .
H5 H 0.436667 0.172284 -0.118634 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2293(8) 0.1538(9) -0.1291(6) 0.035(2) Uani 1 1 d . . . . .
H6A H 0.259103 0.213568 -0.189209 0.042 Uiso 1 1 calc R U . . .
H6B H 0.127187 0.075288 -0.133296 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2667(9) 0.2423(8) -0.0339(5) 0.0333(19) Uani 1 1 d . . . . .
H7A H 0.348468 0.342576 -0.039979 0.040 Uiso 1 1 calc R U . . .
H7B H 0.182598 0.239830 -0.001403 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2999(9) -0.0477(9) -0.1197(6) 0.0342(19) Uani 1 1 d . . . . .
C9 C 0.4051(9) -0.1985(9) -0.1414(5) 0.037(2) Uani 1 1 d . . . . .
H9 H 0.314720 -0.273566 -0.108640 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3964(11) -0.2298(9) -0.2502(6) 0.050(2) Uani 1 1 d . . . . .
H10A H 0.386101 -0.325344 -0.260546 0.076 Uiso 1 1 calc R U . . .
H10B H 0.312666 -0.228143 -0.278098 0.076 Uiso 1 1 calc R U . . .
H10C H 0.484948 -0.155988 -0.282237 0.076 Uiso 1 1 calc R U . . .
C11 C 0.5348(10) -0.1934(9) -0.0935(6) 0.046(2) Uani 1 1 d . . . . .
H11A H 0.529561 -0.287130 -0.101378 0.069 Uiso 1 1 calc R U . . .
H11B H 0.623380 -0.117677 -0.124342 0.069 Uiso 1 1 calc R U . . .
H11C H 0.535710 -0.171966 -0.023759 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4824(8) 0.0890(8) 0.1010(5) 0.0278(18) Uani 1 1 d . . . . .
C13 C 0.6865(8) 0.5806(8) 0.1950(6) 0.0321(18) Uani 1 1 d . . . . .
C14 C 0.5963(9) 0.6438(9) 0.1538(7) 0.045(2) Uani 1 1 d . . . . .
H14A H 0.517421 0.624003 0.199089 0.068 Uiso 1 1 calc R U . . .
H14B H 0.555927 0.599283 0.090280 0.068 Uiso 1 1 calc R U . . .
H14C H 0.658001 0.748609 0.145516 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7494(9) 0.6461(9) 0.2951(6) 0.046(2) Uani 1 1 d . . . . .
H15A H 0.670427 0.624615 0.340776 0.070 Uiso 1 1 calc R U . . .
H15B H 0.811362 0.751127 0.288737 0.070 Uiso 1 1 calc R U . . .
H15C H 0.806814 0.604382 0.319923 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8052(9) 0.6012(8) 0.1262(6) 0.044(2) Uani 1 1 d . . . . .
H16A H 0.765367 0.570641 0.060265 0.066 Uiso 1 1 calc R U . . .
H16B H 0.847242 0.542834 0.148321 0.066 Uiso 1 1 calc R U . . .
H16C H 0.880395 0.703519 0.125002 0.066 Uiso 1 1 calc R U . . .
H1N H 0.604(8) 0.370(8) 0.067(5) 0.05(2) 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 O3 1.495(5) . ?
S1 N1 1.680(6) . ?
S1 C13 1.833(8) . ?
O1 C8 1.197(9) . ?
O2 C8 1.338(8) . ?
O2 C9 1.455(9) . ?
N1 C1 1.444(9) . ?
N2 C12 1.135(9) . ?
C1 C12 1.477(10) . ?
C1 C2 1.556(10) . ?
C1 C4 1.560(10) . ?
C2 C3 1.547(10) . ?
C3 C4 1.550(10) . ?
C4 C7 1.536(10) . ?
C4 C5 1.553(10) . ?
C5 C8 1.475(10) . ?
C5 C6 1.556(9) . ?
C6 C7 1.540(10) . ?
C9 C11 1.507(11) . ?
C9 C10 1.518(10) . ?
C13 C16 1.504(10) . ?
C13 C15 1.531(11) . ?
C13 C14 1.533(10) . ?

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
O3 S1 N1 111.3(3) . . ?
O3 S1 C13 106.3(3) . . ?
N1 S1 C13 97.4(3) . . ?
C8 O2 C9 118.1(6) . . ?
C1 N1 S1 114.1(5) . . ?
N1 C1 C12 112.5(6) . . ?
N1 C1 C2 119.6(6) . . ?
C12 C1 C2 108.9(6) . . ?
N1 C1 C4 116.0(6) . . ?
C12 C1 C4 109.9(6) . . ?
C2 C1 C4 87.4(5) . . ?
C3 C2 C1 88.1(6) . . ?
C2 C3 C4 88.0(5) . . ?
C7 C4 C3 112.5(6) . . ?
C7 C4 C5 88.6(5) . . ?
C3 C4 C5 122.7(6) . . ?
C7 C4 C1 120.1(6) . . ?
C3 C4 C1 87.9(5) . . ?
C5 C4 C1 127.7(6) . . ?
C8 C5 C4 117.7(6) . . ?
C8 C5 C6 119.1(6) . . ?
C4 C5 C6 85.8(5) . . ?
C7 C6 C5 88.3(5) . . ?
C4 C7 C6 86.9(5) . . ?
O1 C8 O2 122.8(7) . . ?
O1 C8 C5 126.6(7) . . ?
O2 C8 C5 110.6(7) . . ?
O2 C9 C11 106.3(6) . . ?
O2 C9 C10 109.1(6) . . ?
C11 C9 C10 112.8(7) . . ?
N2 C12 C1 177.8(8) . . ?
C16 C13 C15 110.4(6) . . ?
C16 C13 C14 112.0(7) . . ?
C15 C13 C14 110.9(7) . . ?
C16 C13 S1 111.9(5) . . ?
C15 C13 S1 103.4(6) . . ?
C14 C13 S1 107.9(5) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_xray40[60]
_database_code_depnum_ccdc_archive 'CCDC 2108586'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   10.6671(8)
_cell_length_b                   10.6671(8)
_cell_length_c                   13.665(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1346.5(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1353
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.79
_exptl_crystal_description       'trigonal needle'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.97
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10864
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3414
_reflns_number_gt                2876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_max     0.956
_reflns_Friedel_fraction_full    0.957

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0330P)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_abs_structure_details 
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     206
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_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 0.23001(9) 0.50764(8) 0.26950(6) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.1843(3) 0.5186(3) 0.1546(2) 0.0234(6) Uani 1 1 d . . . . .
H1N H 0.258(4) 0.563(4) 0.119(2) 0.027(10) Uiso 1 1 d . . . . .
N2 N 0.1978(3) 0.8488(3) 0.1523(2) 0.0359(7) Uani 1 1 d . . . . .
O1 O -0.1523(3) 0.6658(3) -0.0797(2) 0.0484(8) Uani 1 1 d . . . . .
O2 O 0.0876(2) 0.8106(2) -0.07974(16) 0.0279(6) Uani 1 1 d . . . . .
O3 O 0.3204(2) 0.6535(2) 0.31372(16) 0.0299(6) Uani 1 1 d . . . . .
C1 C 0.0809(3) 0.5678(3) 0.1443(2) 0.0228(8) Uani 1 1 d . . . . .
C2 C -0.0556(4) 0.5000(4) 0.2111(3) 0.0295(8) Uani 1 1 d . . . . .
H2A H -0.084681 0.401332 0.234504 0.035 Uiso 1 1 calc R U . . .
H2B H -0.050452 0.563184 0.265890 0.035 Uiso 1 1 calc R U . . .
C3 C -0.1434(4) 0.5031(4) 0.1229(2) 0.0301(8) Uani 1 1 d . . . . .
H3A H -0.151423 0.591490 0.118986 0.036 Uiso 1 1 calc R U . . .
H3B H -0.239272 0.414728 0.115827 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0258(3) 0.5062(4) 0.0563(2) 0.0235(7) Uani 1 1 d . . . . .
C5 C -0.0659(4) 0.3586(3) 0.0128(3) 0.0281(8) Uani 1 1 d . . . . .
H5A H -0.149844 0.275982 0.044852 0.034 Uiso 1 1 calc R U . . .
H5B H 0.016590 0.341105 0.006878 0.034 Uiso 1 1 calc R U . . .
C6 C -0.1035(4) 0.4089(4) -0.0824(3) 0.0306(9) Uani 1 1 d . . . . .
H6A H -0.205818 0.384597 -0.086915 0.037 Uiso 1 1 calc R U . . .
H6B H -0.072678 0.379708 -0.142469 0.037 Uiso 1 1 calc R U . . .
C7 C 0.0013(4) 0.5658(3) -0.0496(2) 0.0243(8) Uani 1 1 d . . . . .
H7 H 0.102386 0.595902 -0.070333 0.029 Uiso 1 1 calc R U . . .
C8 C -0.0328(4) 0.6823(3) -0.0723(2) 0.0269(8) Uani 1 1 d . . . . .
C9 C 0.0725(4) 0.9378(4) -0.0945(2) 0.0306(8) Uani 1 1 d . . . . .
H9 H -0.017943 0.922328 -0.061657 0.037 Uiso 1 1 calc R U . . .
C10 C 0.0631(5) 0.9596(4) -0.2023(3) 0.0450(11) Uani 1 1 d . . . . .
H10A H 0.052849 1.044920 -0.212716 0.068 Uiso 1 1 calc R U . . .
H10B H 0.151276 0.973922 -0.234667 0.068 Uiso 1 1 calc R U . . .
H10C H -0.021088 0.874061 -0.229831 0.068 Uiso 1 1 calc R U . . .
C11 C 0.2006(4) 1.0608(4) -0.0465(3) 0.0398(10) Uani 1 1 d . . . . .
H11A H 0.195628 1.149537 -0.054342 0.060 Uiso 1 1 calc R U . . .
H11B H 0.200854 1.039960 0.023332 0.060 Uiso 1 1 calc R U . . .
H11C H 0.289497 1.073752 -0.076953 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1492(4) 0.7268(4) 0.1477(2) 0.0242(8) Uani 1 1 d . . . . .
C13 C 0.3532(4) 0.4386(4) 0.2430(3) 0.0273(8) Uani 1 1 d . . . . .
C14 C 0.2624(4) 0.2863(4) 0.2019(3) 0.0420(10) Uani 1 1 d . . . . .
H14A H 0.183596 0.227471 0.247426 0.063 Uiso 1 1 calc R U . . .
H14B H 0.323405 0.242536 0.193115 0.063 Uiso 1 1 calc R U . . .
H14C H 0.221670 0.290988 0.138579 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4162(4) 0.4365(4) 0.3423(3) 0.0421(10) Uani 1 1 d . . . . .
H15A H 0.337385 0.379062 0.388209 0.063 Uiso 1 1 calc R U . . .
H15B H 0.473718 0.535690 0.366944 0.063 Uiso 1 1 calc R U . . .
H15C H 0.478130 0.393310 0.335838 0.063 Uiso 1 1 calc R U . . .
C16 C 0.4725(4) 0.5383(4) 0.1733(3) 0.0386(9) Uani 1 1 d . . . . .
H16A H 0.431859 0.530317 0.107777 0.058 Uiso 1 1 calc R U . . .
H16B H 0.547249 0.510662 0.170900 0.058 Uiso 1 1 calc R U . . .
H16C H 0.515269 0.638469 0.196352 0.058 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 O3 1.489(2) . ?
S1 N1 1.665(3) . ?
S1 C13 1.835(3) . ?
N1 C1 1.447(4) . ?
N2 C12 1.136(4) . ?
O1 C8 1.200(4) . ?
O2 C8 1.333(4) . ?
O2 C9 1.458(4) . ?
C1 C12 1.474(5) . ?
C1 C2 1.557(4) . ?
C1 C4 1.557(4) . ?
C2 C3 1.537(5) . ?
C3 C4 1.537(4) . ?
C4 C5 1.530(5) . ?
C4 C7 1.549(4) . ?
C5 C6 1.535(5) . ?
C6 C7 1.543(4) . ?
C7 C8 1.492(5) . ?
C9 C11 1.492(5) . ?
C9 C10 1.503(5) . ?
C13 C16 1.517(5) . ?
C13 C15 1.519(5) . ?
C13 C14 1.523(5) . ?

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
O3 S1 N1 111.63(14) . . ?
O3 S1 C13 106.28(14) . . ?
N1 S1 C13 97.79(15) . . ?
C1 N1 S1 114.9(2) . . ?
C8 O2 C9 117.9(3) . . ?
N1 C1 C12 112.7(3) . . ?
N1 C1 C2 118.7(3) . . ?
C12 C1 C2 109.0(3) . . ?
N1 C1 C4 116.8(3) . . ?
C12 C1 C4 110.3(3) . . ?
C2 C1 C4 86.6(2) . . ?
C3 C2 C1 88.2(3) . . ?
C2 C3 C4 88.0(2) . . ?
C5 C4 C3 113.7(3) . . ?
C5 C4 C7 87.6(2) . . ?
C3 C4 C7 123.0(3) . . ?
C5 C4 C1 120.3(3) . . ?
C3 C4 C1 88.2(2) . . ?
C7 C4 C1 127.0(3) . . ?
C4 C5 C6 87.5(2) . . ?
C5 C6 C7 87.6(2) . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 C4 117.6(3) . . ?
C6 C7 C4 86.6(2) . . ?
O1 C8 O2 123.5(3) . . ?
O1 C8 C7 125.4(3) . . ?
O2 C8 C7 111.1(3) . . ?
O2 C9 C11 106.2(3) . . ?
O2 C9 C10 109.1(3) . . ?
C11 C9 C10 113.4(3) . . ?
N2 C12 C1 177.6(4) . . ?
C16 C13 C15 110.4(3) . . ?
C16 C13 C14 112.3(3) . . ?
C15 C13 C14 111.3(3) . . ?
C16 C13 S1 111.1(2) . . ?
C15 C13 S1 103.9(3) . . ?
C14 C13 S1 107.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O3_$1 0.84(3) 2.16(3) 2.903(4) 148(3) 2_664

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_xray90[53a]
_database_code_depnum_ccdc_archive 'CCDC 2108582'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S, C9 H10 N2 O'
_chemical_formula_sum            'C25 H36 N4 O4 S'
_chemical_formula_weight         488.64

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.3229(14)
_cell_length_b                   12.9953(15)
_cell_length_c                   17.423(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2563.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    138(2)
_cell_measurement_reflns_used    1286
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      20.86
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      138(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26501
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4768
_reflns_number_gt                3834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0357P)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_abs_structure_details 
;
 Flack x determined using 1404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4768
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.35694(7) 0.44361(6) 0.85597(5) 0.0225(2) Uani 1 1 d . . . . .
O1 O -0.00595(19) 0.35004(17) 0.91404(14) 0.0287(6) Uani 1 1 d . . . . .
O2 O -0.11564(18) 0.29274(16) 0.81621(13) 0.0254(6) Uani 1 1 d . . . . .
O3 O 0.3451(2) 0.53084(16) 0.91003(13) 0.0318(6) Uani 1 1 d . . . . .
O4 O 0.7829(2) 0.36651(18) 0.59428(14) 0.0332(6) Uani 1 1 d . . . . .
N1 N 0.2044(3) 0.3521(2) 1.06053(17) 0.0361(8) Uani 1 1 d . . . . .
N2 N 0.2407(2) 0.3650(2) 0.86337(16) 0.0219(7) Uani 1 1 d . . . . .
H2N H 0.175(3) 0.390(2) 0.8608(19) 0.023(10) Uiso 1 1 d . . . . .
N3 N 0.3673(3) 0.1679(2) 0.60019(19) 0.0424(8) Uani 1 1 d . . . . .
N4 N 0.6499(3) 0.2417(2) 0.56227(17) 0.0280(7) Uani 1 1 d . . . . .
H4N H 0.686(3) 0.193(3) 0.585(2) 0.036(12) Uiso 1 1 d . . . . .
C1 C 0.2441(3) 0.2841(2) 0.92160(19) 0.0203(7) Uani 1 1 d . . . . .
C2 C 0.3530(3) 0.2131(2) 0.9128(2) 0.0255(8) Uani 1 1 d . . . . .
H2A H 0.420871 0.246299 0.886860 0.031 Uiso 1 1 calc R U . . .
H2B H 0.377817 0.179478 0.961118 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2793(3) 0.1438(2) 0.8600(2) 0.0252(8) Uani 1 1 d . . . . .
H3A H 0.288722 0.069368 0.870451 0.030 Uiso 1 1 calc R U . . .
H3B H 0.289203 0.158910 0.804693 0.030 Uiso 1 1 calc R U . . .
C4 C 0.1671(3) 0.1913(2) 0.89564(19) 0.0206(7) Uani 1 1 d . . . . .
C5 C 0.1024(3) 0.1237(3) 0.9549(2) 0.0280(8) Uani 1 1 d . . . . .
H5A H 0.147933 0.062635 0.971612 0.034 Uiso 1 1 calc R U . . .
H5B H 0.071128 0.162305 0.999454 0.034 Uiso 1 1 calc R U . . .
C6 C 0.0105(3) 0.1009(2) 0.8931(2) 0.0267(8) Uani 1 1 d . . . . .
H6A H -0.072050 0.106054 0.911492 0.032 Uiso 1 1 calc R U . . .
H6B H 0.023784 0.035119 0.865801 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0529(3) 0.1974(2) 0.8473(2) 0.0209(7) Uani 1 1 d . . . . .
H7 H 0.065579 0.184038 0.791423 0.025 Uiso 1 1 calc R U . . .
C8 C -0.0233(3) 0.2889(2) 0.8632(2) 0.0219(8) Uani 1 1 d . . . . .
C9 C -0.2013(3) 0.3751(2) 0.8292(2) 0.0261(8) Uani 1 1 d . . . . .
H9 H -0.212174 0.385374 0.885664 0.031 Uiso 1 1 calc R U . . .
C10 C -0.3154(3) 0.3392(3) 0.7945(2) 0.0394(10) Uani 1 1 d . . . . .
H10A H -0.376092 0.392111 0.801815 0.059 Uiso 1 1 calc R U . . .
H10B H -0.304204 0.326770 0.739535 0.059 Uiso 1 1 calc R U . . .
H10C H -0.340531 0.275330 0.819581 0.059 Uiso 1 1 calc R U . . .
C11 C -0.1574(3) 0.4732(2) 0.7937(2) 0.0382(10) Uani 1 1 d . . . . .
H11A H -0.215081 0.528198 0.802578 0.057 Uiso 1 1 calc R U . . .
H11B H -0.081728 0.492293 0.817032 0.057 Uiso 1 1 calc R U . . .
H11C H -0.146743 0.463264 0.738402 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2216(3) 0.3241(2) 0.9996(2) 0.0235(8) Uani 1 1 d . . . . .
C13 C 0.3229(3) 0.4954(3) 0.7603(2) 0.0276(9) Uani 1 1 d . . . . .
C14 C 0.3194(4) 0.4053(3) 0.7045(2) 0.0440(11) Uani 1 1 d . . . . .
H14A H 0.391600 0.364371 0.710039 0.066 Uiso 1 1 calc R U . . .
H14B H 0.313768 0.431360 0.651886 0.066 Uiso 1 1 calc R U . . .
H14C H 0.250564 0.362134 0.715788 0.066 Uiso 1 1 calc R U . . .
C15 C 0.4265(3) 0.5657(3) 0.7430(2) 0.0310(9) Uani 1 1 d . . . . .
H15A H 0.430126 0.620378 0.781657 0.047 Uiso 1 1 calc R U . . .
H15B H 0.416355 0.596244 0.692033 0.047 Uiso 1 1 calc R U . . .
H15C H 0.499927 0.525781 0.744232 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2081(3) 0.5542(3) 0.7616(2) 0.0413(10) Uani 1 1 d . . . . .
H16A H 0.200480 0.594494 0.714322 0.062 Uiso 1 1 calc R U . . .
H16B H 0.207214 0.600672 0.805954 0.062 Uiso 1 1 calc R U . . .
H16C H 0.142000 0.505831 0.765499 0.062 Uiso 1 1 calc R U . . .
C17 C 0.6968(3) 0.3376(3) 0.5584(2) 0.0243(8) Uani 1 1 d . . . . .
C18 C 0.6217(3) 0.3993(2) 0.5043(2) 0.0242(8) Uani 1 1 d . . . . .
H18 H 0.667567 0.440477 0.466066 0.029 Uiso 1 1 calc R U . . .
C19 C 0.5314(3) 0.3253(2) 0.46847(19) 0.0231(8) Uani 1 1 d . . . . .
C20 C 0.5467(3) 0.2237(2) 0.5159(2) 0.0244(8) Uani 1 1 d . . . . .
C21 C 0.5168(3) 0.4580(2) 0.5410(2) 0.0300(9) Uani 1 1 d . . . . .
H21A H 0.504821 0.442234 0.596045 0.036 Uiso 1 1 calc R U . . .
H21B H 0.518958 0.533216 0.532163 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4319(3) 0.4004(2) 0.4874(2) 0.0294(9) Uani 1 1 d . . . . .
H22A H 0.364215 0.368234 0.514206 0.035 Uiso 1 1 calc R U . . .
H22B H 0.405046 0.441652 0.442975 0.035 Uiso 1 1 calc R U . . .
C23 C 0.5503(3) 0.2645(3) 0.3940(2) 0.0354(10) Uani 1 1 d . . . . .
H23A H 0.622738 0.284357 0.365917 0.042 Uiso 1 1 calc R U . . .
H23B H 0.480831 0.265021 0.359497 0.042 Uiso 1 1 calc R U . . .
C24 C 0.5634(3) 0.1637(3) 0.4404(2) 0.0328(9) Uani 1 1 d . . . . .
H24A H 0.499951 0.113099 0.430260 0.039 Uiso 1 1 calc R U . . .
H24B H 0.642170 0.131414 0.435410 0.039 Uiso 1 1 calc R U . . .
C25 C 0.4465(3) 0.1914(3) 0.5633(2) 0.0298(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.480(2) . ?
S1 N2 1.672(3) . ?
S1 C13 1.839(3) . ?
O1 C8 1.206(4) . ?
O2 C8 1.329(4) . ?
O2 C9 1.462(4) . ?
O4 C17 1.217(4) . ?
N1 C12 1.138(4) . ?
N2 C1 1.462(4) . ?
N3 C25 1.144(4) . ?
N4 C17 1.356(4) . ?
N4 C20 1.439(4) . ?
C1 C12 1.478(5) . ?
C1 C2 1.547(4) . ?
C1 C4 1.555(4) . ?
C2 C3 1.534(4) . ?
C3 C4 1.543(4) . ?
C4 C5 1.540(4) . ?
C4 C7 1.545(4) . ?
C5 C6 1.527(5) . ?
C6 C7 1.562(4) . ?
C7 C8 1.495(4) . ?
C9 C10 1.501(5) . ?
C9 C11 1.502(4) . ?
C13 C16 1.509(5) . ?
C13 C15 1.517(4) . ?
C13 C14 1.521(5) . ?
C17 C18 1.501(5) . ?
C18 C19 1.536(4) . ?
C18 C21 1.550(4) . ?
C19 C22 1.526(4) . ?
C19 C23 1.534(5) . ?
C19 C20 1.568(4) . ?
C20 C25 1.465(5) . ?
C20 C24 1.541(5) . ?
C21 C22 1.535(5) . ?
C23 C24 1.546(5) . ?

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
O3 S1 N2 110.35(14) . . ?
O3 S1 C13 106.14(15) . . ?
N2 S1 C13 97.37(14) . . ?
C8 O2 C9 117.0(2) . . ?
C1 N2 S1 118.2(2) . . ?
C17 N4 C20 116.1(3) . . ?
N2 C1 C12 112.4(3) . . ?
N2 C1 C2 112.4(3) . . ?
C12 C1 C2 116.0(3) . . ?
N2 C1 C4 109.9(3) . . ?
C12 C1 C4 116.4(3) . . ?
C2 C1 C4 87.5(2) . . ?
C3 C2 C1 88.6(2) . . ?
C2 C3 C4 88.4(2) . . ?
C5 C4 C3 115.7(3) . . ?
C5 C4 C7 89.8(2) . . ?
C3 C4 C7 119.4(3) . . ?
C5 C4 C1 120.9(3) . . ?
C3 C4 C1 88.0(2) . . ?
C7 C4 C1 126.0(3) . . ?
C6 C5 C4 87.8(3) . . ?
C5 C6 C7 89.7(2) . . ?
C8 C7 C4 115.1(3) . . ?
C8 C7 C6 111.5(3) . . ?
C4 C7 C6 86.5(2) . . ?
O1 C8 O2 123.8(3) . . ?
O1 C8 C7 124.5(3) . . ?
O2 C8 C7 111.7(3) . . ?
O2 C9 C10 106.4(3) . . ?
O2 C9 C11 109.7(3) . . ?
C10 C9 C11 112.5(3) . . ?
N1 C12 C1 178.0(4) . . ?
C16 C13 C15 111.3(3) . . ?
C16 C13 C14 112.2(3) . . ?
C15 C13 C14 110.9(3) . . ?
C16 C13 S1 110.6(2) . . ?
C15 C13 S1 103.8(2) . . ?
C14 C13 S1 107.6(2) . . ?
O4 C17 N4 124.8(3) . . ?
O4 C17 C18 127.7(3) . . ?
N4 C17 C18 107.5(3) . . ?
C17 C18 C19 107.3(3) . . ?
C17 C18 C21 116.0(3) . . ?
C19 C18 C21 88.0(2) . . ?
C22 C19 C23 128.0(3) . . ?
C22 C19 C18 90.2(2) . . ?
C23 C19 C18 125.0(3) . . ?
C22 C19 C20 120.4(3) . . ?
C23 C19 C20 89.8(2) . . ?
C18 C19 C20 103.8(3) . . ?
N4 C20 C25 111.1(3) . . ?
N4 C20 C24 117.5(3) . . ?
C25 C20 C24 115.5(3) . . ?
N4 C20 C19 104.4(3) . . ?
C25 C20 C19 116.9(3) . . ?
C24 C20 C19 89.4(3) . . ?
C22 C21 C18 89.4(3) . . ?
C19 C22 C21 88.9(2) . . ?
C19 C23 C24 90.5(3) . . ?
C20 C24 C23 90.4(2) . . ?
N3 C25 C20 178.7(4) . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_xray74[62B]
_database_code_depnum_ccdc_archive 'CCDC 2108588'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;Institute of Organic Chemistry NAS Ukraine
Ukraine
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-03-03 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 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.0729(19)
_cell_length_b                   9.1807(18)
_cell_length_c                   28.272(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1835.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    826
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      19.84
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.99
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19832
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3753
_reflns_number_gt                2940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0339P)²+0.6714P] 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 969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3753
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.34700(13) 0.20576(10) 0.92947(3) 0.0366(2) Uani 1 1 d . . . . .
O1 O -0.4404(4) 0.2609(3) 0.97270(9) 0.0551(8) Uani 1 1 d . . . . .
O2 O 0.6012(4) -0.1214(4) 0.80132(9) 0.0584(9) Uani 1 1 d . . . . .
O3 O 0.3179(5) -0.0943(5) 0.77000(11) 0.0966(15) Uani 1 1 d . . . . .
N1 N -0.1247(4) 0.1567(3) 0.94118(9) 0.0304(7) Uani 1 1 d . . . . .
H1N H -0.073(5) 0.212(4) 0.9656(13) 0.042(10) Uiso 1 1 d . . . . .
N2 N -0.2897(8) -0.1028(5) 1.01964(16) 0.0955(18) Uani 1 1 d . . . . .
C1 C -0.0932(6) 0.0016(4) 0.94930(12) 0.0409(9) Uani 1 1 d . . . . .
C2 C 0.1211(6) -0.0312(5) 0.94980(12) 0.0505(11) Uani 1 1 d . . . . .
H2A H 0.201132 0.055465 0.955597 0.061 Uiso 1 1 calc R U . . .
H2B H 0.157242 -0.112824 0.970803 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1045(6) -0.0737(4) 0.89712(13) 0.0413(10) Uani 1 1 d . . . . .
C4 C -0.1091(6) -0.0867(4) 0.90303(14) 0.0464(10) Uani 1 1 d . . . . .
H4A H -0.153880 -0.187832 0.907640 0.056 Uiso 1 1 calc R U . . .
H4B H -0.182365 -0.036967 0.877924 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2309(6) -0.1927(5) 0.87616(14) 0.0568(12) Uani 1 1 d . . . . .
H5A H 0.166129 -0.255443 0.852755 0.068 Uiso 1 1 calc R U . . .
H5B H 0.297423 -0.251938 0.900215 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3551(6) -0.0729(5) 0.85373(13) 0.0524(11) Uani 1 1 d . . . . .
H6 H 0.463727 -0.047157 0.874764 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1880(5) 0.0329(4) 0.86094(13) 0.0428(10) Uani 1 1 d . . . . .
H7A H 0.225076 0.127995 0.874629 0.051 Uiso 1 1 calc R U . . .
H7B H 0.108743 0.046282 0.832412 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4192(6) -0.0966(5) 0.80395(14) 0.0516(11) Uani 1 1 d . . . . .
C9 C 0.6833(6) -0.1485(6) 0.75460(14) 0.0587(13) Uani 1 1 d . . . . .
H9 H 0.587770 -0.196490 0.733688 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7396(11) -0.0056(7) 0.73418(19) 0.095(2) Uani 1 1 d . . . . .
H10A H 0.795151 -0.020704 0.702809 0.143 Uiso 1 1 calc R U . . .
H10B H 0.627962 0.057067 0.731391 0.143 Uiso 1 1 calc R U . . .
H10C H 0.832737 0.041059 0.754900 0.143 Uiso 1 1 calc R U . . .
C11 C 0.8462(8) -0.2486(7) 0.76254(18) 0.092(2) Uani 1 1 d . . . . .
H11A H 0.906845 -0.270562 0.732205 0.138 Uiso 1 1 calc R U . . .
H11B H 0.937807 -0.201934 0.783659 0.138 Uiso 1 1 calc R U . . .
H11C H 0.800882 -0.339175 0.776982 0.138 Uiso 1 1 calc R U . . .
C12 C -0.2037(7) -0.0547(5) 0.98946(16) 0.0602(13) Uani 1 1 d . . . . .
C13 C -0.2985(6) 0.3649(4) 0.89286(13) 0.0479(11) Uani 1 1 d . . . . .
C14 C -0.4909(8) 0.4320(7) 0.88308(19) 0.090(2) Uani 1 1 d . . . . .
H14A H -0.551952 0.457407 0.913093 0.136 Uiso 1 1 calc R U . . .
H14B H -0.569814 0.361900 0.865952 0.136 Uiso 1 1 calc R U . . .
H14C H -0.475150 0.520099 0.863895 0.136 Uiso 1 1 calc R U . . .
C15 C -0.2109(7) 0.3105(6) 0.84759(14) 0.0709(15) Uani 1 1 d . . . . .
H15A H -0.082512 0.275586 0.853951 0.106 Uiso 1 1 calc R U . . .
H15B H -0.206048 0.390069 0.824507 0.106 Uiso 1 1 calc R U . . .
H15C H -0.287352 0.230556 0.834867 0.106 Uiso 1 1 calc R U . . .
C16 C -0.1676(10) 0.4687(5) 0.91872(18) 0.0877(19) Uani 1 1 d . . . . .
H16A H -0.222315 0.493421 0.949544 0.132 Uiso 1 1 calc R U . . .
H16B H -0.151677 0.557656 0.899978 0.132 Uiso 1 1 calc R U . . .
H16C H -0.044334 0.422143 0.923356 0.132 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 1.478(3) . ?
S1 N1 1.669(3) . ?
S1 C13 1.823(4) . ?
O2 C8 1.309(5) . ?
O2 C9 1.464(5) . ?
O3 C8 1.198(5) . ?
N1 C1 1.459(5) . ?
N2 C12 1.137(5) . ?
C1 C12 1.473(6) . ?
C1 C4 1.543(5) . ?
C1 C2 1.545(6) . ?
C2 C3 1.544(5) . ?
C3 C4 1.525(5) . ?
C3 C5 1.531(5) . ?
C3 C7 1.534(6) . ?
C5 C6 1.543(6) . ?
C6 C8 1.495(5) . ?
C6 C7 1.543(5) . ?
C9 C10 1.488(7) . ?
C9 C11 1.490(7) . ?
C13 C15 1.507(5) . ?
C13 C16 1.516(7) . ?
C13 C14 1.520(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 N1 110.44(16) . . ?
O1 S1 C13 106.20(18) . . ?
N1 S1 C13 98.73(17) . . ?
C8 O2 C9 118.1(3) . . ?
C1 N1 S1 116.0(2) . . ?
N1 C1 C12 112.5(3) . . ?
N1 C1 C4 111.6(3) . . ?
C12 C1 C4 115.5(3) . . ?
N1 C1 C2 110.0(3) . . ?
C12 C1 C2 116.5(4) . . ?
C4 C1 C2 88.7(3) . . ?
C3 C2 C1 88.0(3) . . ?
C4 C3 C5 124.5(4) . . ?
C4 C3 C7 120.3(3) . . ?
C5 C3 C7 88.4(3) . . ?
C4 C3 C2 89.4(3) . . ?
C5 C3 C2 120.6(3) . . ?
C7 C3 C2 116.9(3) . . ?
C3 C4 C1 88.8(3) . . ?
C3 C5 C6 89.0(3) . . ?
C8 C6 C7 116.7(4) . . ?
C8 C6 C5 117.1(4) . . ?
C7 C6 C5 87.6(3) . . ?
C3 C7 C6 88.9(3) . . ?
O3 C8 O2 123.1(4) . . ?
O3 C8 C6 124.8(4) . . ?
O2 C8 C6 112.2(3) . . ?
O2 C9 C10 107.8(4) . . ?
O2 C9 C11 106.0(4) . . ?
C10 C9 C11 113.3(5) . . ?
N2 C12 C1 177.6(5) . . ?
C15 C13 C16 111.5(4) . . ?
C15 C13 C14 110.4(4) . . ?
C16 C13 C14 112.3(4) . . ?
C15 C13 S1 107.1(3) . . ?
C16 C13 S1 110.2(3) . . ?
C14 C13 S1 105.1(3) . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041

