# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_EW-KK-21-010
_audit_block_doi                 10.5517/ccdc.csd.cc2c6fbc
_database_code_depnum_ccdc_archive 'CCDC 2180922'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N O4 S'
_chemical_formula_sum            'C15 H19 N O4 S'
_chemical_formula_weight         309.37

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                   10.3124(4)
_cell_length_b                   6.3748(3)
_cell_length_c                   12.1798(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.745(5)
_cell_angle_gamma                90
_cell_volume                     786.66(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3851
_cell_measurement_theta_min      3.7790
_cell_measurement_theta_max      28.8270

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.697
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.159
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.941
_oxdiff_exptl_absorpt_empirical_full_max 1.046
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            11226
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.866
_diffrn_reflns_theta_max         27.874
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3558
_reflns_number_gt                3116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.0651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          <0.001
_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 0.97773(6) 0.48771(11) 0.07675(5) 0.04521(18) Uani 1 1 d . . . . .
O1 O 0.7738(2) 0.1854(3) 0.22895(14) 0.0491(4) Uani 1 1 d . . . . .
H1A H 0.763(3) 0.056(6) 0.2487(11) 0.074 Uiso 1 1 calc R U . . .
O2 O 0.6701(3) 0.0700(3) 0.06488(17) 0.0794(7) Uani 1 1 d . . . . .
O3 O 0.58776(15) 0.5620(3) 0.22572(14) 0.0411(4) Uani 1 1 d . . . . .
O4 O 0.73566(16) 0.8092(2) 0.30123(13) 0.0364(4) Uani 1 1 d . . . . .
N1 N 0.77683(16) 0.5852(3) 0.16702(15) 0.0309(4) Uani 1 1 d . . . . .
C1 C 0.9090(2) 0.6729(4) 0.16430(18) 0.0338(5) Uani 1 1 d . . . . .
H1 H 0.898804 0.809932 0.127192 0.041 Uiso 1 1 calc R U . . .
C2 C 0.7255(2) 0.4325(4) 0.08058(18) 0.0350(5) Uani 1 1 d . . . . .
H2 H 0.636247 0.475109 0.044843 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8159(2) 0.4469(4) -0.00565(18) 0.0438(6) Uani 1 1 d . . . . .
H3A H 0.790578 0.563316 -0.056410 0.053 Uiso 1 1 calc R U . . .
H3B H 0.812869 0.318348 -0.048646 0.053 Uiso 1 1 calc R U . . .
C4 C 0.9996(2) 0.6951(4) 0.27570(19) 0.0361(5) Uani 1 1 d . . . . .
C5 C 1.0656(2) 0.8829(5) 0.3016(2) 0.0473(6) Uani 1 1 d . . . . .
H5 H 1.052302 0.994017 0.251203 0.057 Uiso 1 1 calc R U . . .
C6 C 1.1517(3) 0.9046(6) 0.4031(3) 0.0598(8) Uani 1 1 d . . . . .
H6 H 1.195903 1.030829 0.420630 0.072 Uiso 1 1 calc R U . . .
C7 C 1.1721(3) 0.7421(6) 0.4773(2) 0.0629(9) Uani 1 1 d . . . . .
H7 H 1.230013 0.758151 0.545088 0.076 Uiso 1 1 calc R U . . .
C8 C 1.1070(2) 0.5543(6) 0.4521(2) 0.0574(8) Uani 1 1 d . . . . .
H8 H 1.120894 0.443868 0.502899 0.069 Uiso 1 1 calc R U . . .
C9 C 1.0210(2) 0.5304(4) 0.3510(2) 0.0458(6) Uani 1 1 d . . . . .
H9 H 0.977451 0.403451 0.333749 0.055 Uiso 1 1 calc R U . . .
C10 C 0.7199(2) 0.2102(4) 0.12367(19) 0.0413(6) Uani 1 1 d . . . . .
C11 C 0.7017(2) 0.6643(3) 0.23636(18) 0.0306(4) Uani 1 1 d . . . . .
C12 C 0.4815(2) 0.6334(4) 0.2835(2) 0.0392(6) Uani 1 1 d . . . . .
C13 C 0.3695(2) 0.4869(6) 0.2354(3) 0.0634(8) Uani 1 1 d . . . . .
H13A H 0.350771 0.499862 0.155494 0.095 Uiso 1 1 calc R U . . .
H13B H 0.292295 0.522998 0.264811 0.095 Uiso 1 1 calc R U . . .
H13C H 0.394536 0.344937 0.255494 0.095 Uiso 1 1 calc R U . . .
C14 C 0.4458(3) 0.8586(5) 0.2533(3) 0.0619(8) Uani 1 1 d . . . . .
H14A H 0.437439 0.877111 0.174072 0.093 Uiso 1 1 calc R U . . .
H14B H 0.513848 0.949508 0.291446 0.093 Uiso 1 1 calc R U . . .
H14C H 0.363607 0.892478 0.275243 0.093 Uiso 1 1 calc R U . . .
C15 C 0.5248(3) 0.6033(6) 0.4079(2) 0.0614(8) Uani 1 1 d . . . . .
H15A H 0.554628 0.461686 0.422746 0.092 Uiso 1 1 calc R U . . .
H15B H 0.451788 0.630431 0.444566 0.092 Uiso 1 1 calc R U . . .
H15C H 0.595446 0.698596 0.435409 0.092 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 C3 1.799(2) . ?
S1 C1 1.821(2) . ?
O1 C10 1.309(3) . ?
O1 H1A 0.87(4) . ?
O2 C10 1.199(3) . ?
O3 C11 1.329(3) . ?
O3 C12 1.480(3) . ?
O4 C11 1.224(3) . ?
N1 C11 1.346(3) . ?
N1 C2 1.459(3) . ?
N1 C1 1.479(3) . ?
C1 C4 1.504(3) . ?
C1 H1 0.9800 . ?
C2 C10 1.516(3) . ?
C2 C3 1.532(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.385(4) . ?
C4 C9 1.385(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C12 C15 1.510(3) . ?
C12 C14 1.510(4) . ?
C12 C13 1.515(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 89.91(11) . . ?
C10 O1 H1A 109.5 . . ?
C11 O3 C12 121.47(18) . . ?
C11 N1 C2 121.92(17) . . ?
C11 N1 C1 120.85(18) . . ?
C2 N1 C1 116.63(17) . . ?
N1 C1 C4 115.82(17) . . ?
N1 C1 S1 103.23(15) . . ?
C4 C1 S1 110.17(15) . . ?
N1 C1 H1 109.1 . . ?
C4 C1 H1 109.1 . . ?
S1 C1 H1 109.1 . . ?
N1 C2 C10 113.96(18) . . ?
N1 C2 C3 105.60(18) . . ?
C10 C2 C3 111.1(2) . . ?
N1 C2 H2 108.7 . . ?
C10 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C2 C3 S1 104.26(15) . . ?
C2 C3 H3A 110.9 . . ?
S1 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
S1 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C9 119.6(2) . . ?
C5 C4 C1 118.9(2) . . ?
C9 C4 C1 121.5(2) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 120.1(3) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
O2 C10 O1 123.5(2) . . ?
O2 C10 C2 122.0(2) . . ?
O1 C10 C2 114.57(19) . . ?
O4 C11 O3 125.1(2) . . ?
O4 C11 N1 124.0(2) . . ?
O3 C11 N1 110.89(18) . . ?
O3 C12 C15 109.33(19) . . ?
O3 C12 C14 110.2(2) . . ?
C15 C12 C14 112.2(3) . . ?
O3 C12 C13 101.8(2) . . ?
C15 C12 C13 111.8(2) . . ?
C14 C12 C13 111.0(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C4 50.6(3) . . . . ?
C2 N1 C1 C4 -138.1(2) . . . . ?
C11 N1 C1 S1 171.04(16) . . . . ?
C2 N1 C1 S1 -17.7(2) . . . . ?
C3 S1 C1 N1 34.25(15) . . . . ?
C3 S1 C1 C4 158.51(17) . . . . ?
C11 N1 C2 C10 -79.2(3) . . . . ?
C1 N1 C2 C10 109.6(2) . . . . ?
C11 N1 C2 C3 158.5(2) . . . . ?
C1 N1 C2 C3 -12.7(3) . . . . ?
N1 C2 C3 S1 37.6(2) . . . . ?
C10 C2 C3 S1 -86.5(2) . . . . ?
C1 S1 C3 C2 -42.42(17) . . . . ?
N1 C1 C4 C5 -132.0(2) . . . . ?
S1 C1 C4 C5 111.3(2) . . . . ?
N1 C1 C4 C9 49.8(3) . . . . ?
S1 C1 C4 C9 -66.8(2) . . . . ?
C9 C4 C5 C6 -0.5(4) . . . . ?
C1 C4 C5 C6 -178.7(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C5 C4 C9 C8 0.6(4) . . . . ?
C1 C4 C9 C8 178.7(2) . . . . ?
C7 C8 C9 C4 -0.4(4) . . . . ?
N1 C2 C10 O2 173.7(2) . . . . ?
C3 C2 C10 O2 -67.1(3) . . . . ?
N1 C2 C10 O1 -6.5(3) . . . . ?
C3 C2 C10 O1 112.7(2) . . . . ?
C12 O3 C11 O4 7.9(3) . . . . ?
C12 O3 C11 N1 -173.11(19) . . . . ?
C2 N1 C11 O4 -171.4(2) . . . . ?
C1 N1 C11 O4 -0.6(3) . . . . ?
C2 N1 C11 O3 9.6(3) . . . . ?
C1 N1 C11 O3 -179.61(18) . . . . ?
C11 O3 C12 C15 -68.2(3) . . . . ?
C11 O3 C12 C14 55.6(3) . . . . ?
C11 O3 C12 C13 173.4(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
_geom_hbond_publ_flag
O1 H1A O4 0.87 1.74 2.609(2) 173.5 1_545 yes
C14 H14B O4 0.96 2.44 2.953(3) 113.4 . yes
C15 H15C O4 0.96 2.48 3.032(3) 116.6 . yes

_refine_diff_density_max         0.129
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_EWKK21046kr1abs
_audit_block_doi                 10.5517/ccdc.csd.cc2f3rs3
_database_code_depnum_ccdc_archive 'CCDC 2237945'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H19 N O2 S'
_chemical_formula_sum            'C9 H19 N O2 S'
_chemical_formula_weight         205.31

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                   6.2757(4)
_cell_length_b                   10.0567(8)
_cell_length_c                   18.9671(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1197.06(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2344
_cell_measurement_theta_min      3.3870
_cell_measurement_theta_max      23.5890

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_oxdiff_exptl_absorpt_empirical_full_max 1.304
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            8475
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.952
_diffrn_reflns_theta_max         26.713
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2504
_reflns_number_gt                1382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.989
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.0547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2504
_refine_ls_number_parameters     152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          <0.001
_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
O1 O 0.0036(3) 0.1009(3) 0.04272(13) 0.0721(7) Uani 1 1 d . . . . .
H1O H -0.126022 0.096285 0.047472 0.108 Uiso 1 1 calc R U . . .
O2 O 0.5769(3) 0.1092(3) 0.05237(16) 0.0846(8) Uani 1 1 d . . . . .
H2O H 0.510588 0.174252 0.066392 0.127 Uiso 1 1 calc R U . . .
C2 C 0.1683(6) 0.1763(5) 0.1483(2) 0.0818(12) Uani 1 1 d . . . . .
H2 H 0.264464 0.147084 0.185959 0.098 Uiso 1 1 calc R U . A 1
N1 N 0.2798(5) 0.2762(4) 0.1049(2) 0.0915(11) Uani 1 1 d D . . . .
H1 H 0.175700 0.281500 0.053500 0.137 Uiso 1 1 d D U . . .
S1A S 0.0763(11) 0.3948(8) 0.2125(5) 0.113(2) Uani 0.605(17) 1 d . . P B 1
C1A C 0.3295(15) 0.3746(9) 0.1649(6) 0.081(4) Uani 0.605(17) 1 d . . P B 1
H1A H 0.440130 0.339034 0.196067 0.097 Uiso 0.605(17) 1 calc R U P B 1
C3A C -0.0243(8) 0.2462(5) 0.1820(3) 0.1151(18) Uani 0.605(17) 1 d . . P B 1
H3A1 H -0.081911 0.193641 0.220395 0.138 Uiso 0.605(17) 1 calc R U P B 1
H3A2 H -0.135563 0.261176 0.147395 0.138 Uiso 0.605(17) 1 calc R U P B 1
C4A C 0.400(3) 0.4969(13) 0.1318(8) 0.105(4) Uani 0.605(17) 1 d . . P B 1
H4A1 H 0.529514 0.480710 0.106229 0.158 Uiso 0.605(17) 1 calc R U P B 1
H4A2 H 0.424904 0.563009 0.167297 0.158 Uiso 0.605(17) 1 calc R U P B 1
H4A3 H 0.292175 0.527803 0.099812 0.158 Uiso 0.605(17) 1 calc R U P B 1
S1B S 0.0417(13) 0.4439(12) 0.1807(7) 0.114(2) Uani 0.395(17) 1 d . . P B 2
C1B C 0.267(2) 0.4246(15) 0.1193(8) 0.069(5) Uani 0.395(17) 1 d . . P B 2
H1B H 0.250139 0.477490 0.076248 0.083 Uiso 0.395(17) 1 calc R U P B 2
C3B C -0.0243(8) 0.2462(5) 0.1820(3) 0.1151(18) Uani 0.395(17) 1 d . . P B 2
H3B1 H -0.044821 0.215522 0.229990 0.138 Uiso 0.395(17) 1 calc R U P B 2
H3B2 H -0.152720 0.227824 0.155252 0.138 Uiso 0.395(17) 1 calc R U P B 2
C4B C 0.485(3) 0.451(2) 0.1579(11) 0.095(6) Uani 0.395(17) 1 d . . P B 2
H4BA H 0.597538 0.456376 0.123553 0.142 Uiso 0.395(17) 1 calc R U P B 2
H4BB H 0.514652 0.378583 0.189719 0.142 Uiso 0.395(17) 1 calc R U P B 2
H4BC H 0.477463 0.532327 0.183813 0.142 Uiso 0.395(17) 1 calc R U P B 2
C5 C 0.1044(5) 0.0563(4) 0.10516(18) 0.0616(9) Uani 1 1 d . . . . .
H5 H -0.002471 0.007347 0.132479 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2791(6) -0.0431(4) 0.0846(2) 0.0721(11) Uani 1 1 d . . . . .
C7 C 0.4329(6) 0.0109(4) 0.0298(2) 0.0763(11) Uani 1 1 d . . . . .
H7A H 0.514564 -0.063152 0.011211 0.092 Uiso 1 1 calc R U . . .
H7B H 0.349982 0.047115 -0.008841 0.092 Uiso 1 1 calc R U . . .
C8 C 0.1672(7) -0.1648(5) 0.0506(3) 0.1138(17) Uani 1 1 d . . . . .
H8A H 0.095450 -0.137453 0.008325 0.171 Uiso 1 1 calc R U . . .
H8B H 0.065321 -0.201007 0.083135 0.171 Uiso 1 1 calc R U . . .
H8C H 0.271524 -0.231298 0.039334 0.171 Uiso 1 1 calc R U . . .
C9 C 0.4050(9) -0.0880(6) 0.1501(3) 0.125(2) Uani 1 1 d . . . . .
H9A H 0.501880 -0.157750 0.137179 0.187 Uiso 1 1 calc R U . . .
H9B H 0.307793 -0.120242 0.185262 0.187 Uiso 1 1 calc R U . . .
H9C H 0.483749 -0.014093 0.168701 0.187 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
O1 C5 1.415(4) . ?
O1 H1O 0.8200 . ?
O2 C7 1.407(4) . ?
O2 H2O 0.8200 . ?
C2 N1 1.475(6) . ?
C2 C5 1.512(5) . ?
C2 C3A 1.537(6) . ?
C2 C3B 1.537(6) . ?
C2 H2 0.9800 . ?
N1 C1B 1.519(15) . ?
N1 C1A 1.539(9) . ?
N1 H1 1.1753 . ?
S1A C3A 1.723(7) . ?
S1A C1A 1.840(9) . ?
C1A C4A 1.450(19) . ?
C1A H1A 0.9800 . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A H4A1 0.9600 . ?
C4A H4A2 0.9600 . ?
C4A H4A3 0.9600 . ?
S1B C1B 1.841(14) . ?
S1B C3B 2.031(13) . ?
C1B C4B 1.58(3) . ?
C1B H1B 0.9800 . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4B H4BA 0.9600 . ?
C4B H4BB 0.9600 . ?
C4B H4BC 0.9600 . ?
C5 C6 1.534(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.519(5) . ?
C6 C9 1.540(6) . ?
C6 C8 1.552(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 H1O 109.5 . . ?
C7 O2 H2O 109.5 . . ?
N1 C2 C5 111.6(3) . . ?
N1 C2 C3A 107.0(4) . . ?
C5 C2 C3A 112.4(3) . . ?
N1 C2 C3B 107.0(4) . . ?
C5 C2 C3B 112.4(3) . . ?
N1 C2 H2 108.6 . . ?
C5 C2 H2 108.6 . . ?
C3A C2 H2 108.6 . . ?
C2 N1 C1B 122.9(6) . . ?
C2 N1 C1A 97.0(5) . . ?
C2 N1 H1 103.3 . . ?
C1B N1 H1 94.3 . . ?
C1A N1 H1 134.2 . . ?
C3A S1A C1A 93.2(3) . . ?
C4A C1A N1 106.7(11) . . ?
C4A C1A S1A 112.5(8) . . ?
N1 C1A S1A 105.0(6) . . ?
C4A C1A H1A 110.8 . . ?
N1 C1A H1A 110.8 . . ?
S1A C1A H1A 110.8 . . ?
C2 C3A S1A 104.4(4) . . ?
C2 C3A H3A1 110.9 . . ?
S1A C3A H3A1 110.9 . . ?
C2 C3A H3A2 110.9 . . ?
S1A C3A H3A2 110.9 . . ?
H3A1 C3A H3A2 108.9 . . ?
C1A C4A H4A1 109.5 . . ?
C1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C1B S1B C3B 93.5(6) . . ?
N1 C1B C4B 101.4(13) . . ?
N1 C1B S1B 105.0(9) . . ?
C4B C1B S1B 110.9(10) . . ?
N1 C1B H1B 112.9 . . ?
C4B C1B H1B 112.9 . . ?
S1B C1B H1B 112.9 . . ?
C2 C3B S1B 106.4(4) . . ?
C2 C3B H3B1 110.4 . . ?
S1B C3B H3B1 110.4 . . ?
C2 C3B H3B2 110.4 . . ?
S1B C3B H3B2 110.4 . . ?
H3B1 C3B H3B2 108.6 . . ?
C1B C4B H4BA 109.5 . . ?
C1B C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
C1B C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
O1 C5 C2 108.6(3) . . ?
O1 C5 C6 108.3(3) . . ?
C2 C5 C6 117.9(3) . . ?
O1 C5 H5 107.2 . . ?
C2 C5 H5 107.2 . . ?
C6 C5 H5 107.2 . . ?
C7 C6 C5 113.3(3) . . ?
C7 C6 C9 109.3(3) . . ?
C5 C6 C9 110.7(3) . . ?
C7 C6 C8 106.6(3) . . ?
C5 C6 C8 107.2(3) . . ?
C9 C6 C8 109.6(4) . . ?
O2 C7 C6 116.8(3) . . ?
O2 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
O2 C7 H7B 108.1 . . ?
C6 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C2 N1 C1B 148.7(8) . . . . ?
C3B C2 N1 C1B 25.3(9) . . . . ?
C5 C2 N1 C1A -176.8(5) . . . . ?
C3A C2 N1 C1A 59.8(6) . . . . ?
C2 N1 C1A C4A -167.7(10) . . . . ?
C2 N1 C1A S1A -48.1(5) . . . . ?
C3A S1A C1A C4A 137.6(13) . . . . ?
C3A S1A C1A N1 21.9(6) . . . . ?
N1 C2 C3A S1A -45.4(6) . . . . ?
C5 C2 C3A S1A -168.3(5) . . . . ?
C1A S1A C3A C2 11.5(6) . . . . ?
C2 N1 C1B C4B 101.1(11) . . . . ?
C2 N1 C1B S1B -14.4(10) . . . . ?
C3B S1B C1B N1 -0.8(7) . . . . ?
C3B S1B C1B C4B -109.5(15) . . . . ?
N1 C2 C3B S1B -21.6(6) . . . . ?
C5 C2 C3B S1B -144.4(5) . . . . ?
N1 C2 C5 O1 -48.2(4) . . . . ?
C3A C2 C5 O1 72.1(4) . . . . ?
C3B C2 C5 O1 72.1(4) . . . . ?
N1 C2 C5 C6 75.3(4) . . . . ?
C3A C2 C5 C6 -164.5(4) . . . . ?
C3B C2 C5 C6 -164.5(4) . . . . ?
O1 C5 C6 C7 52.9(4) . . . . ?
C2 C5 C6 C7 -70.7(4) . . . . ?
O1 C5 C6 C9 176.1(3) . . . . ?
C2 C5 C6 C9 52.5(5) . . . . ?
O1 C5 C6 C8 -64.4(4) . . . . ?
C2 C5 C6 C8 172.0(4) . . . . ?
C5 C6 C7 O2 71.9(4) . . . . ?
C9 C6 C7 O2 -52.0(5) . . . . ?
C8 C6 C7 O2 -170.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O2 0.82 1.87 2.685(3) 172.0 1_455 yes
O2 H2O N1 0.82 1.92 2.701(4) 158.9 . yes
N1 H1 O2 1.18 2.37 3.442(5) 150.3 4_455 yes
C4B^b H4BA^b S1B^b 0.96 2.99 3.52(2) 115.7 1_655 yes

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_EWKK21-015
_audit_block_doi                 10.5517/ccdc.csd.cc2c6fdf
_database_code_depnum_ccdc_archive 'CCDC 2180924'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H13 N O2 S'
_chemical_formula_sum            'C8 H13 N O2 S'
_chemical_formula_weight         187.25

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                   10.0224(6)
_cell_length_b                   6.6552(3)
_cell_length_c                   14.9401(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.562(6)
_cell_angle_gamma                90
_cell_volume                     950.07(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3409
_cell_measurement_theta_min      3.6950
_cell_measurement_theta_max      27.3650

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    0.302
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.901
_oxdiff_exptl_absorpt_empirical_full_max 1.130
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            6887
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0238
_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       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2137
_reflns_number_gt                1788
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_max     0.960
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.2378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 693 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 syn
_refine_ls_number_reflns         2137
_refine_ls_number_parameters     113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          <0.001
_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 0.66385(15) 0.4853(3) 0.45106(9) 0.1304(6) Uani 1 1 d . . . . .
O1 O 0.3253(3) 0.8425(3) 0.2313(2) 0.0861(8) Uani 1 1 d . . . . .
C1 C 0.5668(4) 0.6893(5) 0.3812(2) 0.0797(10) Uani 1 1 d . . . . .
H1A H 0.508094 0.755177 0.413343 0.096 Uiso 1 1 calc R U . . .
H1AB H 0.629822 0.787782 0.368108 0.096 Uiso 1 1 calc R U . . .
N1 N 0.4831(3) 0.5961(3) 0.29591(17) 0.0562(6) Uani 1 1 d . . . . .
C2 C 0.5126(3) 0.3862(4) 0.2800(2) 0.0630(8) Uani 1 1 d . . . . .
H2 H 0.588583 0.378112 0.251473 0.076 Uiso 1 1 calc R U . . .
O2 O 0.2796(3) 0.2410(3) 0.2544(2) 0.0768(7) Uani 1 1 d . . . . .
H2O H 0.296(4) 0.134(8) 0.267(3) 0.115 Uiso 1 1 calc R U . . .
C4 C 0.3718(3) 0.6705(4) 0.2318(2) 0.0538(6) Uani 1 1 d . . . . .
C3 C 0.5578(6) 0.2927(6) 0.3767(3) 0.1083(16) Uani 1 1 d . . . . .
H3A H 0.612065 0.171692 0.377343 0.130 Uiso 1 1 calc R U . . .
H3AB H 0.477341 0.259444 0.397129 0.130 Uiso 1 1 calc R U . . .
C5 C 0.3148(3) 0.5118(4) 0.15654(19) 0.0547(6) Uani 1 1 d . . . . .
C7 C 0.3812(4) 0.5497(6) 0.0780(3) 0.0853(11) Uani 1 1 d . . . . .
H7A H 0.356933 0.682154 0.052852 0.128 Uiso 1 1 calc R U . . .
H7B H 0.347045 0.452151 0.029103 0.128 Uiso 1 1 calc R U . . .
H7C H 0.481078 0.538662 0.102890 0.128 Uiso 1 1 calc R U . . .
C8 C 0.1558(3) 0.5181(6) 0.1186(3) 0.0814(10) Uani 1 1 d . . . . .
H8A H 0.116616 0.492659 0.168708 0.122 Uiso 1 1 calc R U . . .
H8B H 0.124022 0.417297 0.070905 0.122 Uiso 1 1 calc R U . . .
H8C H 0.126587 0.648171 0.092172 0.122 Uiso 1 1 calc R U . . .
C6 C 0.3742(3) 0.3163(4) 0.2095(2) 0.0548(7) Uani 1 1 d . . . . .
H6 H 0.391717 0.216257 0.166278 0.066 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 C1 1.807(4) . ?
S1 C3 1.816(5) . ?
O1 C4 1.235(3) . ?
C1 N1 1.438(4) . ?
C1 H1A 0.9700 . ?
C1 H1AB 0.9700 . ?
N1 C4 1.327(4) . ?
N1 C2 1.462(3) . ?
C2 C3 1.511(5) . ?
C2 C6 1.538(4) . ?
C2 H2 0.9800 . ?
O2 C6 1.408(3) . ?
O2 H2O 0.74(5) . ?
C4 C5 1.523(4) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C5 C8 1.522(4) . ?
C5 C7 1.535(4) . ?
C5 C6 1.546(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6 H6 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C3 93.62(15) . . ?
N1 C1 S1 104.9(2) . . ?
N1 C1 H1A 110.8 . . ?
S1 C1 H1A 110.8 . . ?
N1 C1 H1AB 110.8 . . ?
S1 C1 H1AB 110.8 . . ?
H1A C1 H1AB 108.8 . . ?
C4 N1 C1 128.1(3) . . ?
C4 N1 C2 114.0(2) . . ?
C1 N1 C2 117.6(3) . . ?
N1 C2 C3 104.8(3) . . ?
N1 C2 C6 102.4(2) . . ?
C3 C2 C6 118.6(3) . . ?
N1 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
C6 C2 H2 110.2 . . ?
C6 O2 H2O 109.5 . . ?
O1 C4 N1 125.7(3) . . ?
O1 C4 C5 125.5(3) . . ?
N1 C4 C5 108.7(2) . . ?
C2 C3 S1 104.2(3) . . ?
C2 C3 H3A 110.9 . . ?
S1 C3 H3A 110.9 . . ?
C2 C3 H3AB 110.9 . . ?
S1 C3 H3AB 110.9 . . ?
H3A C3 H3AB 108.9 . . ?
C8 C5 C4 112.0(3) . . ?
C8 C5 C7 110.9(3) . . ?
C4 C5 C7 107.3(2) . . ?
C8 C5 C6 114.3(3) . . ?
C4 C5 C6 101.8(2) . . ?
C7 C5 C6 109.9(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C6 C2 112.3(3) . . ?
O2 C6 C5 109.4(2) . . ?
C2 C6 C5 103.0(2) . . ?
O2 C6 H6 110.6 . . ?
C2 C6 H6 110.6 . . ?
C5 C6 H6 110.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C1 N1 -12.8(3) . . . . ?
S1 C1 N1 C4 163.0(2) . . . . ?
S1 C1 N1 C2 -10.3(3) . . . . ?
C4 N1 C2 C3 -140.7(3) . . . . ?
C1 N1 C2 C3 33.6(4) . . . . ?
C4 N1 C2 C6 -16.4(3) . . . . ?
C1 N1 C2 C6 157.9(3) . . . . ?
C1 N1 C4 O1 5.2(5) . . . . ?
C2 N1 C4 O1 178.8(3) . . . . ?
C1 N1 C4 C5 -177.3(3) . . . . ?
C2 N1 C4 C5 -3.8(3) . . . . ?
N1 C2 C3 S1 -39.1(4) . . . . ?
C6 C2 C3 S1 -152.5(3) . . . . ?
C1 S1 C3 C2 30.8(3) . . . . ?
O1 C4 C5 C8 -37.9(4) . . . . ?
N1 C4 C5 C8 144.6(3) . . . . ?
O1 C4 C5 C7 84.0(4) . . . . ?
N1 C4 C5 C7 -93.4(3) . . . . ?
O1 C4 C5 C6 -160.5(3) . . . . ?
N1 C4 C5 C6 22.1(3) . . . . ?
N1 C2 C6 O2 -88.9(3) . . . . ?
C3 C2 C6 O2 25.7(4) . . . . ?
N1 C2 C6 C5 28.7(3) . . . . ?
C3 C2 C6 C5 143.3(3) . . . . ?
C8 C5 C6 O2 -31.9(3) . . . . ?
C4 C5 C6 O2 89.0(3) . . . . ?
C7 C5 C6 O2 -157.5(3) . . . . ?
C8 C5 C6 C2 -151.5(3) . . . . ?
C4 C5 C6 C2 -30.6(3) . . . . ?
C7 C5 C6 C2 82.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1AB O2 0.97 2.60 3.269(4) 126.1 3 yes
C2 H2 O1 0.98 2.49 3.437(4) 162.0 3_545 yes
O2 H2O O1 0.74 2.06 2.731(3) 150.9 1_545 yes

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_EWKK21013diolkr1absref
_audit_block_doi                 10.5517/ccdc.csd.cc2f3rt4
_database_code_depnum_ccdc_archive 'CCDC 2237946'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N O2 S'
_chemical_formula_sum            'C14 H21 N O2 S'
_chemical_formula_weight         267.38

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                   9.9519(5)
_cell_length_b                   5.9259(3)
_cell_length_c                   12.0663(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.859(4)
_cell_angle_gamma                90
_cell_volume                     711.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3590
_cell_measurement_theta_min      3.8920
_cell_measurement_theta_max      27.7970

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.846
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            6822
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.634
_diffrn_reflns_theta_max         26.727
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3003
_reflns_number_gt                2732
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.985
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.0046P] 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 1108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3003
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          <0.001
_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 0.53924(6) 0.50466(11) 0.10563(5) 0.0470(2) Uani 1 1 d . . . . .
O1 O 0.71525(16) 0.3054(3) 0.24687(13) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.9769(2) -0.0045(4) 0.12895(16) 0.0600(5) Uani 1 1 d . . . . .
H2O H 0.936264 0.080849 0.086756 0.090 Uiso 1 1 calc R U . . .
N1 N 0.8158(3) 0.2906(4) 0.0206(2) 0.0481(6) Uani 1 1 d . . . . .
H1A H 0.838(4) 0.328(7) -0.044(3) 0.072 Uiso 1 1 d . U . . .
H2B H 0.737(4) 0.229(7) 0.013(3) 0.072 Uiso 1 1 d . U . . .
C1 C 0.5921(2) 0.4262(4) 0.2459(2) 0.0396(5) Uani 1 1 d . . . . .
H1 H 0.601858 0.562575 0.291199 0.048 Uiso 1 1 calc R U . . .
C2 C 0.8286(2) 0.4392(4) 0.21271(19) 0.0343(5) Uani 1 1 d . . . . .
H2 H 0.822082 0.583508 0.251936 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8164(2) 0.4931(4) 0.08938(19) 0.0382(5) Uani 1 1 d . . . . .
H3 H 0.896413 0.580053 0.069830 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6946(3) 0.6461(5) 0.0683(2) 0.0454(6) Uani 1 1 d . . . . .
H4A H 0.690495 0.687651 -0.009438 0.054 Uiso 1 1 calc R U . . .
H4B H 0.704516 0.783235 0.111515 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4877(3) 0.2746(5) 0.2957(2) 0.0435(6) Uani 1 1 d . . . . .
C6 C 0.4254(3) 0.3361(6) 0.3939(2) 0.0541(7) Uani 1 1 d . . . . .
H6 H 0.445107 0.473439 0.427648 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3326(3) 0.1876(8) 0.4410(3) 0.0699(10) Uani 1 1 d . . . . .
H7 H 0.291293 0.226234 0.506983 0.084 Uiso 1 1 calc R U . . .
C8 C 0.3020(3) -0.0141(8) 0.3907(3) 0.0689(9) Uani 1 1 d . . . . .
H8 H 0.240379 -0.111183 0.422909 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3617(3) -0.0729(6) 0.2935(3) 0.0639(9) Uani 1 1 d . . . . .
H9 H 0.340182 -0.209125 0.259325 0.077 Uiso 1 1 calc R U . . .
C10 C 0.4542(3) 0.0705(5) 0.2462(3) 0.0533(7) Uani 1 1 d . . . . .
H10 H 0.494708 0.029491 0.180242 0.064 Uiso 1 1 calc R U . . .
C11 C 0.9565(2) 0.3210(4) 0.2582(2) 0.0371(5) Uani 1 1 d . . . . .
C12 C 1.0821(3) 0.4270(5) 0.2089(3) 0.0503(7) Uani 1 1 d . . . . .
H12A H 1.084916 0.394119 0.131056 0.075 Uiso 1 1 calc R U . . .
H12B H 1.160629 0.366099 0.245093 0.075 Uiso 1 1 calc R U . . .
H12C H 1.079723 0.587520 0.219535 0.075 Uiso 1 1 calc R U . . .
C13 C 0.9582(3) 0.3539(6) 0.3843(2) 0.0596(8) Uani 1 1 d . . . . .
H13A H 0.955178 0.512207 0.401057 0.089 Uiso 1 1 calc R U . . .
H13B H 1.038988 0.289826 0.415326 0.089 Uiso 1 1 calc R U . . .
H13C H 0.881564 0.280401 0.415451 0.089 Uiso 1 1 calc R U . . .
C14 C 0.9576(3) 0.0649(4) 0.2391(2) 0.0461(6) Uani 1 1 d . . . . .
H14A H 1.028330 -0.000408 0.285090 0.055 Uiso 1 1 calc R U . . .
H14B H 0.872887 0.003563 0.264089 0.055 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 C4 1.821(3) . ?
S1 C1 1.825(3) . ?
O1 C1 1.420(3) . ?
O1 C2 1.444(3) . ?
O2 C14 1.408(3) . ?
O2 H2O 0.8200 . ?
N1 C3 1.459(4) . ?
N1 H1A 0.84(4) . ?
N1 H2B 0.87(4) . ?
C1 C5 1.505(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.525(3) . ?
C2 C11 1.546(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.532(4) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.387(4) . ?
C5 C6 1.394(4) . ?
C6 C7 1.402(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.528(3) . ?
C11 C13 1.534(4) . ?
C11 C14 1.535(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C4 S1 C1 96.48(12) . . ?
C1 O1 C2 113.50(17) . . ?
C14 O2 H2O 109.5 . . ?
C3 N1 H1A 108(3) . . ?
C3 N1 H2B 114(3) . . ?
H1A N1 H2B 105(4) . . ?
O1 C1 C5 107.26(19) . . ?
O1 C1 S1 111.92(15) . . ?
C5 C1 S1 109.35(18) . . ?
O1 C1 H1 109.4 . . ?
C5 C1 H1 109.4 . . ?
S1 C1 H1 109.4 . . ?
O1 C2 C3 110.05(19) . . ?
O1 C2 C11 106.98(18) . . ?
C3 C2 C11 119.60(18) . . ?
O1 C2 H2 106.5 . . ?
C3 C2 H2 106.5 . . ?
C11 C2 H2 106.5 . . ?
N1 C3 C2 112.5(2) . . ?
N1 C3 C4 113.3(2) . . ?
C2 C3 C4 109.68(19) . . ?
N1 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
C3 C4 S1 111.06(18) . . ?
C3 C4 H4A 109.4 . . ?
S1 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
S1 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C10 C5 C6 119.1(3) . . ?
C10 C5 C1 120.7(2) . . ?
C6 C5 C1 120.1(3) . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C13 109.7(2) . . ?
C12 C11 C14 109.9(2) . . ?
C13 C11 C14 105.9(2) . . ?
C12 C11 C2 110.5(2) . . ?
C13 C11 C2 106.9(2) . . ?
C14 C11 C2 113.7(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C11 115.6(2) . . ?
O2 C14 H14A 108.4 . . ?
C11 C14 H14A 108.4 . . ?
O2 C14 H14B 108.4 . . ?
C11 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 C1 C5 -173.48(19) . . . . ?
C2 O1 C1 S1 66.6(2) . . . . ?
C4 S1 C1 O1 -53.8(2) . . . . ?
C4 S1 C1 C5 -172.53(18) . . . . ?
C1 O1 C2 C3 -69.2(2) . . . . ?
C1 O1 C2 C11 159.44(18) . . . . ?
O1 C2 C3 N1 -61.3(2) . . . . ?
C11 C2 C3 N1 63.1(3) . . . . ?
O1 C2 C3 C4 65.8(2) . . . . ?
C11 C2 C3 C4 -169.8(2) . . . . ?
N1 C3 C4 S1 64.0(2) . . . . ?
C2 C3 C4 S1 -62.7(2) . . . . ?
C1 S1 C4 C3 52.7(2) . . . . ?
O1 C1 C5 C10 -61.9(3) . . . . ?
S1 C1 C5 C10 59.6(3) . . . . ?
O1 C1 C5 C6 116.6(3) . . . . ?
S1 C1 C5 C6 -121.8(2) . . . . ?
C10 C5 C6 C7 1.2(4) . . . . ?
C1 C5 C6 C7 -177.4(3) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C8 C9 C10 C5 -0.1(5) . . . . ?
C6 C5 C10 C9 -0.8(4) . . . . ?
C1 C5 C10 C9 177.8(3) . . . . ?
O1 C2 C11 C12 169.92(19) . . . . ?
C3 C2 C11 C12 44.1(3) . . . . ?
O1 C2 C11 C13 -70.8(2) . . . . ?
C3 C2 C11 C13 163.4(2) . . . . ?
O1 C2 C11 C14 45.8(2) . . . . ?
C3 C2 C11 C14 -80.1(3) . . . . ?
C12 C11 C14 O2 -52.3(3) . . . . ?
C13 C11 C14 O2 -170.7(2) . . . . ?
C2 C11 C14 O2 72.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O N1 0.82 1.90 2.698(3) 165.7 . yes
N1 H1A O2 0.84(4) 2.34(4) 3.016(3) 138(4) 2_755 yes

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.277
_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_EWKK21-016kr1
_audit_block_doi                 10.5517/ccdc.csd.cc2c6ffg
_database_code_depnum_ccdc_archive 'CCDC 2180925'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 N O2 S'
_chemical_formula_sum            'C9 H15 N O2 S'
_chemical_formula_weight         201.28

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                   19.872(3)
_cell_length_b                   6.6196(7)
_cell_length_c                   16.260(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.918(16)
_cell_angle_gamma                90
_cell_volume                     2023.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1176
_cell_measurement_theta_min      3.6620
_cell_measurement_theta_max      20.7960

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.475
_oxdiff_exptl_absorpt_empirical_full_max 16.455
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            5194
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_point_group_measured_fraction_full 0.780
_reflns_number_total             3217
_reflns_number_gt                1916
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.382
_reflns_Friedel_fraction_max     0.454
_reflns_Friedel_fraction_full    0.515

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0103(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3217
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.2078
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          <0.001
_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 0.39840(13) 0.4922(4) 0.41311(16) 0.0647(7) Uani 1 1 d . . . . .
O1 O 0.2817(3) 0.0030(9) 0.5137(4) 0.0561(15) Uani 1 1 d . . . . .
O2 O 0.3277(3) 0.5437(10) 0.6442(4) 0.0639(17) Uani 1 1 d . . . . .
H2O2 H 0.296679 0.537851 0.596530 0.096 Uiso 1 1 calc R U . . .
N1 N 0.3642(3) 0.2437(10) 0.5150(4) 0.0521(17) Uani 1 1 d . . . . .
C1 C 0.3552(4) 0.2570(14) 0.4218(5) 0.053(2) Uani 1 1 d . . . . .
H1 H 0.304464 0.266083 0.388426 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4082(5) 0.3945(12) 0.5724(6) 0.053(2) Uani 1 1 d . . . . .
H2 H 0.458005 0.351069 0.591810 0.064 Uiso 1 1 calc R U . . .
C3 C 0.3996(5) 0.5848(14) 0.5177(6) 0.060(2) Uani 1 1 d . . . . .
H3A H 0.439184 0.676564 0.541930 0.072 Uiso 1 1 calc R U . . .
H3B H 0.355631 0.653991 0.513491 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3267(4) 0.1272(12) 0.5511(5) 0.0474(19) Uani 1 1 d . . . . .
C5 C 0.3513(4) 0.1760(13) 0.6492(5) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.3789(4) 0.3925(14) 0.6498(5) 0.054(2) Uani 1 1 d . . . . .
H6 H 0.418724 0.412703 0.703644 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3868(6) 0.0831(16) 0.3906(6) 0.076(3) Uani 1 1 d . . . . .
H7A H 0.359955 -0.036654 0.392120 0.114 Uiso 1 1 calc R U . . .
H7B H 0.435115 0.065047 0.427440 0.114 Uiso 1 1 calc R U . . .
H7C H 0.385855 0.107814 0.332101 0.114 Uiso 1 1 calc R U . . .
C8 C 0.4130(5) 0.0327(15) 0.6913(6) 0.064(2) Uani 1 1 d . . . . .
H8A H 0.433680 0.065570 0.751823 0.095 Uiso 1 1 calc R U . . .
H8B H 0.448385 0.046373 0.663072 0.095 Uiso 1 1 calc R U . . .
H8C H 0.395915 -0.103875 0.685571 0.095 Uiso 1 1 calc R U . . .
C9 C 0.2927(5) 0.1511(15) 0.6873(6) 0.065(3) Uani 1 1 d . . . . .
H9A H 0.309471 0.189366 0.747479 0.098 Uiso 1 1 calc R U . . .
H9B H 0.277665 0.012511 0.682348 0.098 Uiso 1 1 calc R U . . .
H9C H 0.253249 0.235449 0.656511 0.098 Uiso 1 1 calc R U . . .
S2 S 0.42122(14) 0.3438(4) 0.18797(16) 0.0714(8) Uani 1 1 d . . . . .
O3 O 0.2796(3) 0.8141(9) 0.0034(4) 0.0607(16) Uani 1 1 d . . . . .
O4 O 0.3160(4) 0.2704(10) -0.0935(4) 0.0716(18) Uani 1 1 d . . . . .
H4O4 H 0.285462 0.292991 -0.070724 0.107 Uiso 1 1 calc DR U . . .
N2 N 0.3675(4) 0.5819(10) 0.0572(4) 0.0521(18) Uani 1 1 d . . . . .
C10 C 0.3713(5) 0.5751(13) 0.1481(5) 0.056(2) Uani 1 1 d . . . . .
H10 H 0.323394 0.564564 0.152433 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4082(5) 0.4353(13) 0.0263(5) 0.054(2) Uani 1 1 d . . . . .
H11 H 0.456672 0.484733 0.036125 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4095(5) 0.2480(14) 0.0804(6) 0.065(2) Uani 1 1 d . . . . .
H12A H 0.448507 0.159802 0.080648 0.079 Uiso 1 1 calc R U . . .
H12B H 0.365179 0.173628 0.058229 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3215(4) 0.6929(14) -0.0065(5) 0.051(2) Uani 1 1 d . . . . .
C14 C 0.3362(5) 0.6413(13) -0.0897(5) 0.052(2) Uani 1 1 d . . . . .
C15 C 0.3675(5) 0.4243(13) -0.0710(6) 0.057(2) Uani 1 1 d . . . . .
H15 H 0.401359 0.403330 -0.102579 0.069 Uiso 1 1 calc R U . . .
C16 C 0.4095(7) 0.7543(18) 0.1993(6) 0.093(4) Uani 1 1 d . . . . .
H16A H 0.383004 0.875027 0.177482 0.139 Uiso 1 1 calc R U . . .
H16B H 0.456011 0.764921 0.193690 0.139 Uiso 1 1 calc R U . . .
H16C H 0.413919 0.737050 0.259464 0.139 Uiso 1 1 calc R U . . .
C17 C 0.3914(5) 0.7872(18) -0.1019(6) 0.074(3) Uani 1 1 d . . . . .
H17A H 0.400875 0.755057 -0.154665 0.111 Uiso 1 1 calc R U . . .
H17B H 0.434578 0.775669 -0.053524 0.111 Uiso 1 1 calc R U . . .
H17C H 0.373718 0.922879 -0.105079 0.111 Uiso 1 1 calc R U . . .
C18 C 0.2680(5) 0.6529(18) -0.1680(6) 0.078(3) Uani 1 1 d . . . . .
H18A H 0.277867 0.610126 -0.219374 0.118 Uiso 1 1 calc R U . . .
H18B H 0.250909 0.789554 -0.175392 0.118 Uiso 1 1 calc R U . . .
H18C H 0.232535 0.566379 -0.158397 0.118 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 C3 1.800(9) . ?
S1 C1 1.806(9) . ?
O1 C4 1.221(9) . ?
O2 C6 1.410(10) . ?
O2 H2O2 0.8200 . ?
N1 C4 1.333(10) . ?
N1 C2 1.450(11) . ?
N1 C1 1.470(10) . ?
C1 C7 1.477(13) . ?
C1 H1 0.9800 . ?
C2 C3 1.520(12) . ?
C2 C6 1.549(11) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.543(11) . ?
C5 C9 1.495(11) . ?
C5 C8 1.527(12) . ?
C5 C6 1.533(11) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
S2 C12 1.803(9) . ?
S2 C10 1.825(9) . ?
O3 C13 1.205(10) . ?
O4 C15 1.406(11) . ?
O4 H4O4 0.8200 . ?
N2 C13 1.354(10) . ?
N2 C11 1.454(10) . ?
N2 C10 1.456(9) . ?
C10 C16 1.506(13) . ?
C10 H10 0.9800 . ?
C11 C12 1.516(12) . ?
C11 C15 1.526(11) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(11) . ?
C14 C17 1.522(13) . ?
C14 C18 1.531(12) . ?
C14 C15 1.556(12) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 94.7(4) . . ?
C6 O2 H2O2 109.5 . . ?
C4 N1 C2 114.9(7) . . ?
C4 N1 C1 126.2(7) . . ?
C2 N1 C1 117.9(6) . . ?
N1 C1 C7 112.6(8) . . ?
N1 C1 S1 103.3(5) . . ?
C7 C1 S1 112.3(6) . . ?
N1 C1 H1 109.5 . . ?
C7 C1 H1 109.5 . . ?
S1 C1 H1 109.5 . . ?
N1 C2 C3 105.4(7) . . ?
N1 C2 C6 102.1(6) . . ?
C3 C2 C6 118.9(7) . . ?
N1 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C6 C2 H2 110.0 . . ?
C2 C3 S1 103.6(6) . . ?
C2 C3 H3A 111.0 . . ?
S1 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
S1 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O1 C4 N1 126.4(8) . . ?
O1 C4 C5 126.2(7) . . ?
N1 C4 C5 107.4(7) . . ?
C9 C5 C8 111.5(7) . . ?
C9 C5 C6 115.2(7) . . ?
C8 C5 C6 110.1(7) . . ?
C9 C5 C4 112.2(7) . . ?
C8 C5 C4 105.8(7) . . ?
C6 C5 C4 101.3(6) . . ?
O2 C6 C5 114.4(6) . . ?
O2 C6 C2 113.2(7) . . ?
C5 C6 C2 103.3(7) . . ?
O2 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C2 C6 H6 108.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 S2 C10 93.8(4) . . ?
C15 O4 H4O4 109.5 . . ?
C13 N2 C11 114.3(6) . . ?
C13 N2 C10 126.4(7) . . ?
C11 N2 C10 118.6(6) . . ?
N2 C10 C16 112.9(7) . . ?
N2 C10 S2 103.3(6) . . ?
C16 C10 S2 110.2(6) . . ?
N2 C10 H10 110.1 . . ?
C16 C10 H10 110.1 . . ?
S2 C10 H10 110.1 . . ?
N2 C11 C12 104.6(7) . . ?
N2 C11 C15 102.8(6) . . ?
C12 C11 C15 117.8(8) . . ?
N2 C11 H11 110.4 . . ?
C12 C11 H11 110.4 . . ?
C15 C11 H11 110.4 . . ?
C11 C12 S2 104.4(6) . . ?
C11 C12 H12A 110.9 . . ?
S2 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
S2 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O3 C13 N2 125.6(8) . . ?
O3 C13 C14 127.8(8) . . ?
N2 C13 C14 106.5(7) . . ?
C13 C14 C17 109.2(8) . . ?
C13 C14 C18 110.9(7) . . ?
C17 C14 C18 110.0(8) . . ?
C13 C14 C15 102.3(7) . . ?
C17 C14 C15 110.6(7) . . ?
C18 C14 C15 113.5(8) . . ?
O4 C15 C11 113.6(7) . . ?
O4 C15 C14 114.0(7) . . ?
C11 C15 C14 101.7(7) . . ?
O4 C15 H15 109.1 . . ?
C11 C15 H15 109.1 . . ?
C14 C15 H15 109.1 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C7 -77.1(10) . . . . ?
C2 N1 C1 C7 114.8(9) . . . . ?
C4 N1 C1 S1 161.5(7) . . . . ?
C2 N1 C1 S1 -6.6(8) . . . . ?
C3 S1 C1 N1 -16.0(6) . . . . ?
C3 S1 C1 C7 -137.6(7) . . . . ?
C4 N1 C2 C3 -138.4(7) . . . . ?
C1 N1 C2 C3 31.0(10) . . . . ?
C4 N1 C2 C6 -13.5(9) . . . . ?
C1 N1 C2 C6 155.9(7) . . . . ?
N1 C2 C3 S1 -39.3(8) . . . . ?
C6 C2 C3 S1 -152.9(6) . . . . ?
C1 S1 C3 C2 32.8(7) . . . . ?
C2 N1 C4 O1 173.2(8) . . . . ?
C1 N1 C4 O1 4.9(13) . . . . ?
C2 N1 C4 C5 -7.5(9) . . . . ?
C1 N1 C4 C5 -175.9(7) . . . . ?
O1 C4 C5 C9 -32.1(11) . . . . ?
N1 C4 C5 C9 148.7(7) . . . . ?
O1 C4 C5 C8 89.7(9) . . . . ?
N1 C4 C5 C8 -89.5(8) . . . . ?
O1 C4 C5 C6 -155.4(8) . . . . ?
N1 C4 C5 C6 25.3(8) . . . . ?
C9 C5 C6 O2 -29.9(10) . . . . ?
C8 C5 C6 O2 -157.0(7) . . . . ?
C4 C5 C6 O2 91.3(8) . . . . ?
C9 C5 C6 C2 -153.5(7) . . . . ?
C8 C5 C6 C2 79.4(8) . . . . ?
C4 C5 C6 C2 -32.2(8) . . . . ?
N1 C2 C6 O2 -95.9(8) . . . . ?
C3 C2 C6 O2 19.5(11) . . . . ?
N1 C2 C6 C5 28.5(8) . . . . ?
C3 C2 C6 C5 143.8(8) . . . . ?
C13 N2 C10 C16 -79.1(11) . . . . ?
C11 N2 C10 C16 111.3(9) . . . . ?
C13 N2 C10 S2 161.9(7) . . . . ?
C11 N2 C10 S2 -7.7(8) . . . . ?
C12 S2 C10 N2 -15.3(6) . . . . ?
C12 S2 C10 C16 -136.1(7) . . . . ?
C13 N2 C11 C12 -138.9(7) . . . . ?
C10 N2 C11 C12 32.0(10) . . . . ?
C13 N2 C11 C15 -15.3(9) . . . . ?
C10 N2 C11 C15 155.6(7) . . . . ?
N2 C11 C12 S2 -39.7(8) . . . . ?
C15 C11 C12 S2 -153.1(7) . . . . ?
C10 S2 C12 C11 32.7(7) . . . . ?
C11 N2 C13 O3 175.3(8) . . . . ?
C10 N2 C13 O3 5.3(14) . . . . ?
C11 N2 C13 C14 -7.4(9) . . . . ?
C10 N2 C13 C14 -177.4(7) . . . . ?
O3 C13 C14 C17 86.3(10) . . . . ?
N2 C13 C14 C17 -90.9(8) . . . . ?
O3 C13 C14 C18 -35.0(12) . . . . ?
N2 C13 C14 C18 147.8(8) . . . . ?
O3 C13 C14 C15 -156.4(9) . . . . ?
N2 C13 C14 C15 26.4(8) . . . . ?
N2 C11 C15 O4 -92.9(8) . . . . ?
C12 C11 C15 O4 21.4(11) . . . . ?
N2 C11 C15 C14 30.1(8) . . . . ?
C12 C11 C15 C14 144.4(8) . . . . ?
C13 C14 C15 O4 88.3(8) . . . . ?
C17 C14 C15 O4 -155.4(7) . . . . ?
C18 C14 C15 O4 -31.3(10) . . . . ?
C13 C14 C15 C11 -34.4(8) . . . . ?
C17 C14 C15 C11 81.9(9) . . . . ?
C18 C14 C15 C11 -154.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O2 O1 0.82 1.97 2.788(8) 174.7 4_556 yes
O4 H4O4 O3 0.82 1.95 2.764(8) 171.0 4_545 yes
C2 H2 S1 0.98 3.03 3.829(9) 139.8 2_656 yes

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_EWKK21-004
_audit_block_doi                 10.5517/ccdc.csd.cc2f3rr2
_database_code_depnum_ccdc_archive 'CCDC 2237944'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 N O5 S'
_chemical_formula_sum            'C14 H23 N O5 S'
_chemical_formula_weight         317.39

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                   10.0040(3)
_cell_length_b                   6.04477(15)
_cell_length_c                   14.4466(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.076(3)
_cell_angle_gamma                90
_cell_volume                     843.54(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11288
_cell_measurement_theta_min      3.6370
_cell_measurement_theta_max      27.9440

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.938
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            22584
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         27.872
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3942
_reflns_number_gt                3443
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_max     0.965
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.0784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(16)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3942
_refine_ls_number_parameters     206
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          <0.001
_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
S1A S 0.08445(19) 0.3908(3) 0.4309(2) 0.0951(7) Uani 0.775(7) 1 d . . P A 1
C1A C 0.1049(3) 0.1021(6) 0.40252(17) 0.0775(8) Uani 0.775(7) 1 d . . P A 1
H1AA H 0.168225 0.026707 0.455405 0.093 Uiso 0.775(7) 1 calc R U P A 1
H1AB H 0.016666 0.025480 0.386808 0.093 Uiso 0.775(7) 1 calc R U P A 1
C3A C 0.2429(3) 0.4595(5) 0.4037(2) 0.0717(7) Uani 0.775(7) 1 d . . P A 1
H3AA H 0.239723 0.609998 0.379991 0.086 Uiso 0.775(7) 1 calc R U P A 1
H3AB H 0.319496 0.447041 0.460643 0.086 Uiso 0.775(7) 1 calc R U P A 1
S1B S 0.1534(10) 0.3157(10) 0.4817(6) 0.089(3) Uani 0.225(7) 1 d . . P A 2
C1B C 0.1049(3) 0.1021(6) 0.40252(17) 0.0775(8) Uani 0.225(7) 1 d . . P A 2
H1BA H 0.134725 -0.036042 0.435642 0.093 Uiso 0.225(7) 1 calc R U P A 2
H1BB H 0.004674 0.098982 0.380541 0.093 Uiso 0.225(7) 1 calc R U P A 2
C3B C 0.2429(3) 0.4595(5) 0.4037(2) 0.0717(7) Uani 0.225(7) 1 d . . P A 2
H3BA H 0.189025 0.585987 0.373860 0.086 Uiso 0.225(7) 1 calc R U P A 2
H3BB H 0.332504 0.511746 0.440892 0.086 Uiso 0.225(7) 1 calc R U P A 2
O1 O 0.44025(18) 0.0578(3) 0.41390(12) 0.0676(5) Uani 1 1 d . . . . .
O2 O 0.4531(3) 0.3769(3) 0.13610(13) 0.0899(7) Uani 1 1 d . . . . .
O3 O 0.45843(19) 0.0321(3) 0.18769(10) 0.0607(4) Uani 1 1 d . . . . .
O4 O 0.12982(18) 0.0853(3) 0.16071(11) 0.0671(5) Uani 1 1 d . . . . .
O5 O -0.00666(17) -0.1004(3) 0.23761(10) 0.0640(4) Uani 1 1 d . . . . .
N1 N 0.1610(2) 0.1166(4) 0.32046(12) 0.0586(5) Uani 1 1 d . . . . .
C2 C 0.2615(2) 0.2948(4) 0.32620(14) 0.0481(4) Uani 1 1 d . . . . .
H2 H 0.244498 0.370207 0.264174 0.058 Uiso 1 1 calc R U . A 1
C4 C 0.4087(2) 0.2014(3) 0.35403(13) 0.0448(4) Uani 1 1 d . . . . .
C5 C 0.5141(2) 0.3070(3) 0.30685(14) 0.0476(4) Uani 1 1 d . . . . .
C6 C 0.5132(3) 0.5591(4) 0.31947(19) 0.0655(6) Uani 1 1 d . . . . .
H6A H 0.582552 0.624384 0.292993 0.098 Uiso 1 1 calc R U . . .
H6B H 0.532583 0.594224 0.386462 0.098 Uiso 1 1 calc R U . . .
H6C H 0.423849 0.616378 0.286855 0.098 Uiso 1 1 calc R U . . .
C7 C 0.4706(2) 0.2478(3) 0.19988(14) 0.0481(4) Uani 1 1 d . . . . .
C8 C 0.6591(2) 0.2120(5) 0.35078(19) 0.0664(6) Uani 1 1 d . . . . .
H8A H 0.656295 0.053721 0.344905 0.100 Uiso 1 1 calc R U . . .
H8B H 0.688898 0.251881 0.417301 0.100 Uiso 1 1 calc R U . . .
H8C H 0.722831 0.270825 0.317593 0.100 Uiso 1 1 calc R U . . .
C9 C 0.4139(3) -0.0474(5) 0.09032(17) 0.0710(7) Uani 1 1 d . . . . .
H9A H 0.320886 0.001159 0.061973 0.106 Uiso 1 1 calc R U . . .
H9B H 0.417099 -0.206081 0.090143 0.106 Uiso 1 1 calc R U . . .
H9C H 0.474142 0.009970 0.054066 0.106 Uiso 1 1 calc R U . . .
C10 C 0.0954(2) 0.0379(4) 0.23207(13) 0.0485(4) Uani 1 1 d . . . . .
C11 C -0.0995(2) -0.1952(4) 0.14987(16) 0.0581(5) Uani 1 1 d . . . . .
C12 C -0.0186(3) -0.3353(6) 0.0976(2) 0.0855(9) Uani 1 1 d . . . . .
H12A H -0.080746 -0.400724 0.042316 0.128 Uiso 1 1 calc R U . . .
H12B H 0.028915 -0.449896 0.139370 0.128 Uiso 1 1 calc R U . . .
H12C H 0.047591 -0.244659 0.077581 0.128 Uiso 1 1 calc R U . . .
C13 C -0.1980(4) -0.3309(7) 0.1904(2) 0.0986(12) Uani 1 1 d . . . . .
H13A H -0.267007 -0.396501 0.138808 0.148 Uiso 1 1 calc R U . . .
H13B H -0.241977 -0.237077 0.227254 0.148 Uiso 1 1 calc R U . . .
H13C H -0.147427 -0.445383 0.230802 0.148 Uiso 1 1 calc R U . . .
C14 C -0.1768(3) -0.0112(6) 0.0883(2) 0.0859(9) Uani 1 1 d . . . . .
H14A H -0.112347 0.082593 0.068070 0.129 Uiso 1 1 calc R U . . .
H14B H -0.226406 0.074053 0.124640 0.129 Uiso 1 1 calc R U . . .
H14C H -0.241037 -0.072899 0.033128 0.129 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 C3A 1.779(3) . ?
S1A C1A 1.816(4) . ?
C1A N1 1.440(3) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C3A C2 1.545(3) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
S1B C1B 1.710(5) . ?
S1B C3B 1.831(5) . ?
C1B N1 1.440(3) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C3B C2 1.545(3) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
O1 C4 1.208(2) . ?
O2 C7 1.185(3) . ?
O3 C7 1.317(3) . ?
O3 C9 1.443(3) . ?
O4 C10 1.203(2) . ?
O5 C10 1.338(2) . ?
O5 C11 1.478(3) . ?
N1 C10 1.361(3) . ?
N1 C2 1.461(3) . ?
C2 C4 1.530(3) . ?
C2 H2 0.9800 . ?
C4 C5 1.535(3) . ?
C5 C7 1.535(3) . ?
C5 C6 1.535(3) . ?
C5 C8 1.536(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.503(4) . ?
C11 C14 1.506(4) . ?
C11 C13 1.512(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A S1A C1A 90.87(14) . . ?
N1 C1A S1A 102.6(2) . . ?
N1 C1A H1AA 111.2 . . ?
S1A C1A H1AA 111.2 . . ?
N1 C1A H1AB 111.2 . . ?
S1A C1A H1AB 111.2 . . ?
H1AA C1A H1AB 109.2 . . ?
C2 C3A S1A 106.96(18) . . ?
C2 C3A H3AA 110.3 . . ?
S1A C3A H3AA 110.3 . . ?
C2 C3A H3AB 110.3 . . ?
S1A C3A H3AB 110.3 . . ?
H3AA C3A H3AB 108.6 . . ?
C1B S1B C3B 92.6(2) . . ?
N1 C1B S1B 113.6(2) . . ?
N1 C1B H1BA 108.8 . . ?
S1B C1B H1BA 108.8 . . ?
N1 C1B H1BB 108.8 . . ?
S1B C1B H1BB 108.8 . . ?
H1BA C1B H1BB 107.7 . . ?
C2 C3B S1B 108.1(2) . . ?
C2 C3B H3BA 110.1 . . ?
S1B C3B H3BA 110.1 . . ?
C2 C3B H3BB 110.1 . . ?
S1B C3B H3BB 110.1 . . ?
H3BA C3B H3BB 108.4 . . ?
C7 O3 C9 117.02(18) . . ?
C10 O5 C11 120.66(16) . . ?
C10 N1 C1A 123.70(18) . . ?
C10 N1 C1B 123.70(18) . . ?
C10 N1 C2 117.89(17) . . ?
C1A N1 C2 114.09(19) . . ?
C1B N1 C2 114.09(19) . . ?
N1 C2 C4 110.12(18) . . ?
N1 C2 C3B 107.78(18) . . ?
C4 C2 C3B 109.64(17) . . ?
N1 C2 C3A 107.78(18) . . ?
C4 C2 C3A 109.64(17) . . ?
N1 C2 H2 109.8 . . ?
C4 C2 H2 109.8 . . ?
C3A C2 H2 109.8 . . ?
O1 C4 C2 120.48(19) . . ?
O1 C4 C5 122.4(2) . . ?
C2 C4 C5 117.07(16) . . ?
C7 C5 C6 110.00(18) . . ?
C7 C5 C4 107.59(16) . . ?
C6 C5 C4 109.51(19) . . ?
C7 C5 C8 108.60(19) . . ?
C6 C5 C8 110.9(2) . . ?
C4 C5 C8 110.17(18) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O3 123.9(2) . . ?
O2 C7 C5 125.1(2) . . ?
O3 C7 C5 110.95(16) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O5 126.36(18) . . ?
O4 C10 N1 123.03(18) . . ?
O5 C10 N1 110.58(16) . . ?
O5 C11 C12 110.5(2) . . ?
O5 C11 C14 109.3(2) . . ?
C12 C11 C14 112.4(3) . . ?
O5 C11 C13 101.87(19) . . ?
C12 C11 C13 112.3(3) . . ?
C14 C11 C13 110.0(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A S1A C1A N1 -38.9(2) . . . . ?
C1A S1A C3A C2 29.9(2) . . . . ?
C3B S1B C1B N1 4.9(6) . . . . ?
C1B S1B C3B C2 -14.5(6) . . . . ?
S1A C1A N1 C10 -117.2(2) . . . . ?
S1A C1A N1 C2 38.8(3) . . . . ?
S1B C1B N1 C10 -149.0(5) . . . . ?
S1B C1B N1 C2 7.1(5) . . . . ?
C10 N1 C2 C4 -100.6(2) . . . . ?
C1A N1 C2 C4 101.8(2) . . . . ?
C1B N1 C2 C4 101.8(2) . . . . ?
C10 N1 C2 C3B 139.8(2) . . . . ?
C1B N1 C2 C3B -17.8(3) . . . . ?
C10 N1 C2 C3A 139.8(2) . . . . ?
C1A N1 C2 C3A -17.8(3) . . . . ?
S1B C3B C2 N1 20.2(5) . . . . ?
S1B C3B C2 C4 -99.7(4) . . . . ?
S1A C3A C2 N1 -12.8(3) . . . . ?
S1A C3A C2 C4 -132.6(2) . . . . ?
N1 C2 C4 O1 -40.4(3) . . . . ?
C3B C2 C4 O1 78.0(3) . . . . ?
C3A C2 C4 O1 78.0(3) . . . . ?
N1 C2 C4 C5 142.88(17) . . . . ?
C3B C2 C4 C5 -98.7(2) . . . . ?
C3A C2 C4 C5 -98.7(2) . . . . ?
O1 C4 C5 C7 115.3(2) . . . . ?
C2 C4 C5 C7 -68.0(2) . . . . ?
O1 C4 C5 C6 -125.1(2) . . . . ?
C2 C4 C5 C6 51.5(2) . . . . ?
O1 C4 C5 C8 -2.9(3) . . . . ?
C2 C4 C5 C8 173.76(18) . . . . ?
C9 O3 C7 O2 -3.4(4) . . . . ?
C9 O3 C7 C5 178.21(19) . . . . ?
C6 C5 C7 O2 7.4(3) . . . . ?
C4 C5 C7 O2 126.7(3) . . . . ?
C8 C5 C7 O2 -114.1(3) . . . . ?
C6 C5 C7 O3 -174.2(2) . . . . ?
C4 C5 C7 O3 -55.0(2) . . . . ?
C8 C5 C7 O3 64.2(2) . . . . ?
C11 O5 C10 O4 -6.2(4) . . . . ?
C11 O5 C10 N1 175.7(2) . . . . ?
C1A N1 C10 O4 166.0(3) . . . . ?
C1B N1 C10 O4 166.0(3) . . . . ?
C2 N1 C10 O4 10.8(4) . . . . ?
C1A N1 C10 O5 -15.8(3) . . . . ?
C1B N1 C10 O5 -15.8(3) . . . . ?
C2 N1 C10 O5 -171.0(2) . . . . ?
C10 O5 C11 C12 62.2(3) . . . . ?
C10 O5 C11 C14 -61.9(3) . . . . ?
C10 O5 C11 C13 -178.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9B O2 0.96 2.61 3.545(4) 165.4 1_545 yes
C3A^a H3AB^a O1 0.97 2.69 3.605(3) 157.2 2_656 yes
C3B^b H3BB^b O1 0.97 2.68 3.605(3) 160.3 2_656 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_EW-KK-21-002kr2
_audit_block_doi                 10.5517/ccdc.csd.cc2c6f9b
_database_code_depnum_ccdc_archive 'CCDC 2180921'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 N O4 S'
_chemical_formula_sum            'C10 H17 N O4 S'
_chemical_formula_weight         247.30

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                   6.5356(2)
_cell_length_b                   9.8260(3)
_cell_length_c                   20.5497(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1319.67(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    12334
_cell_measurement_theta_min      3.6240
_cell_measurement_theta_max      26.6050

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.183
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.894
_oxdiff_exptl_absorpt_empirical_full_max 1.086
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            39826
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.868
_diffrn_reflns_theta_max         29.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3480
_reflns_number_gt                2745
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.916
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+0.1929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(17)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          <0.001
_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 0.66679(19) 0.37957(12) 0.47519(5) 0.0867(4) Uani 1 1 d . . . . .
O1 O 0.3283(3) 0.5201(3) 0.61941(10) 0.0630(6) Uani 1 1 d . . . . .
H1A H 0.214(8) 0.523(4) 0.6304(12) 0.095 Uiso 1 1 calc R U . . .
O2 O 0.2037(4) 0.6021(3) 0.52771(14) 0.0915(10) Uani 1 1 d . . . . .
O3 O 0.7390(3) 0.70205(19) 0.64727(10) 0.0574(5) Uani 1 1 d . . . . .
O4 O 0.9457(3) 0.51854(19) 0.66183(9) 0.0475(4) Uani 1 1 d . . . . .
N1 N 0.7168(3) 0.5276(2) 0.57951(10) 0.0417(4) Uani 1 1 d . . . . .
C1 C 0.7779(4) 0.3917(3) 0.55602(14) 0.0518(6) Uani 1 1 d . . . . .
H1 H 0.927383 0.387356 0.552722 0.062 Uiso 1 1 calc R U . . .
C2 C 0.5667(4) 0.6003(3) 0.54119(12) 0.0472(6) Uani 1 1 d . . . . .
H2 H 0.593204 0.698086 0.545425 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6087(6) 0.5586(4) 0.47115(15) 0.0751(10) Uani 1 1 d . . . . .
H3A H 0.723489 0.609152 0.453529 0.090 Uiso 1 1 calc R U . . .
H3B H 0.489603 0.574638 0.444048 0.090 Uiso 1 1 calc R U . . .
C4 C 0.7027(6) 0.2762(3) 0.59762(19) 0.0739(10) Uani 1 1 d . . . . .
H4A H 0.765114 0.281582 0.639832 0.111 Uiso 1 1 calc R U . . .
H4B H 0.738302 0.191203 0.577547 0.111 Uiso 1 1 calc R U . . .
H4C H 0.556770 0.282053 0.602029 0.111 Uiso 1 1 calc R U . . .
C5 C 0.3459(4) 0.5728(3) 0.56162(14) 0.0513(6) Uani 1 1 d . . . . .
C6 C 0.8101(3) 0.5791(2) 0.63205(12) 0.0404(5) Uani 1 1 d . . . . .
C7 C 0.8026(5) 0.7731(3) 0.70775(14) 0.0566(7) Uani 1 1 d . . . . .
C8 C 0.6855(9) 0.9059(4) 0.7013(2) 0.1017(16) Uani 1 1 d . . . . .
H8A H 0.715670 0.963400 0.737815 0.153 Uiso 1 1 calc R U . . .
H8B H 0.541323 0.887386 0.700079 0.153 Uiso 1 1 calc R U . . .
H8C H 0.725489 0.951009 0.661823 0.153 Uiso 1 1 calc R U . . .
C9 C 1.0314(6) 0.7987(4) 0.70673(18) 0.0784(10) Uani 1 1 d . . . . .
H9A H 1.102738 0.713545 0.710045 0.118 Uiso 1 1 calc R U . . .
H9B H 1.068206 0.855818 0.742773 0.118 Uiso 1 1 calc R U . . .
H9C H 1.068131 0.842857 0.666739 0.118 Uiso 1 1 calc R U . . .
C10 C 0.7373(8) 0.6935(4) 0.76620(19) 0.0896(13) Uani 1 1 d . . . . .
H10A H 0.759248 0.746837 0.804698 0.134 Uiso 1 1 calc R U . . .
H10B H 0.815966 0.611152 0.768851 0.134 Uiso 1 1 calc R U . . .
H10C H 0.594667 0.671283 0.762571 0.134 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 C3 1.801(4) . ?
S1 C1 1.817(3) . ?
O1 C5 1.300(3) . ?
O1 H1A 0.78(5) . ?
O2 C5 1.197(3) . ?
O3 C6 1.331(3) . ?
O3 C7 1.485(3) . ?
O4 C6 1.231(3) . ?
N1 C6 1.340(3) . ?
N1 C2 1.447(3) . ?
N1 C1 1.475(3) . ?
C1 C4 1.503(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.522(4) . ?
C2 C5 1.527(4) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C7 C10 1.496(5) . ?
C7 C9 1.517(5) . ?
C7 C8 1.519(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 93.58(14) . . ?
C5 O1 H1A 109.5 . . ?
C6 O3 C7 121.7(2) . . ?
C6 N1 C2 124.1(2) . . ?
C6 N1 C1 118.8(2) . . ?
C2 N1 C1 116.9(2) . . ?
N1 C1 C4 114.1(2) . . ?
N1 C1 S1 104.49(19) . . ?
C4 C1 S1 109.8(2) . . ?
N1 C1 H1 109.4 . . ?
C4 C1 H1 109.4 . . ?
S1 C1 H1 109.4 . . ?
N1 C2 C3 105.0(3) . . ?
N1 C2 C5 113.8(2) . . ?
C3 C2 C5 112.5(3) . . ?
N1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C5 C2 H2 108.4 . . ?
C2 C3 S1 104.9(2) . . ?
C2 C3 H3A 110.8 . . ?
S1 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
S1 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 O1 124.0(3) . . ?
O2 C5 C2 122.1(3) . . ?
O1 C5 C2 113.9(2) . . ?
O4 C6 O3 125.0(2) . . ?
O4 C6 N1 123.1(2) . . ?
O3 C6 N1 111.9(2) . . ?
O3 C7 C10 110.3(3) . . ?
O3 C7 C9 110.0(3) . . ?
C10 C7 C9 112.3(3) . . ?
O3 C7 C8 100.9(3) . . ?
C10 C7 C8 112.1(3) . . ?
C9 C7 C8 110.7(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C4 73.9(3) . . . . ?
C2 N1 C1 C4 -109.8(3) . . . . ?
C6 N1 C1 S1 -166.07(18) . . . . ?
C2 N1 C1 S1 10.2(3) . . . . ?
C3 S1 C1 N1 13.0(2) . . . . ?
C3 S1 C1 C4 135.8(2) . . . . ?
C6 N1 C2 C3 142.8(3) . . . . ?
C1 N1 C2 C3 -33.3(3) . . . . ?
C6 N1 C2 C5 -93.8(3) . . . . ?
C1 N1 C2 C5 90.2(3) . . . . ?
N1 C2 C3 S1 39.8(3) . . . . ?
C5 C2 C3 S1 -84.5(3) . . . . ?
C1 S1 C3 C2 -31.0(3) . . . . ?
N1 C2 C5 O2 -164.8(3) . . . . ?
C3 C2 C5 O2 -45.5(5) . . . . ?
N1 C2 C5 O1 17.7(4) . . . . ?
C3 C2 C5 O1 137.0(3) . . . . ?
C7 O3 C6 O4 -7.2(4) . . . . ?
C7 O3 C6 N1 173.2(2) . . . . ?
C2 N1 C6 O4 -175.7(2) . . . . ?
C1 N1 C6 O4 0.2(4) . . . . ?
C2 N1 C6 O3 3.9(3) . . . . ?
C1 N1 C6 O3 179.9(2) . . . . ?
C6 O3 C7 C10 -62.5(4) . . . . ?
C6 O3 C7 C9 61.9(4) . . . . ?
C6 O3 C7 C8 178.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O4 0.78 1.87 2.648(3) 175.0 1_455 yes
C2 H2 O2 0.98 2.58 3.370(4) 138.1 4_566 yes
C9 H9B O4 0.96 2.53 3.462(4) 163.3 3_756 yes
C10 H10B O4 0.96 2.53 3.068(4) 115.7 . yes

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_EWKK21045kr1_twin1_hklf5
_audit_block_doi                 10.5517/ccdc.csd.cc2f3rv5
_database_code_depnum_ccdc_archive 'CCDC 2237947'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H21 N O2 S'
_chemical_formula_sum            'C10 H21 N O2 S'
_chemical_formula_weight         219.34

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                   5.9251(4)
_cell_length_b                   11.4025(8)
_cell_length_c                   18.0255(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1217.81(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2271
_cell_measurement_theta_min      3.5760
_cell_measurement_theta_max      23.2630

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.863
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            7693
_diffrn_reflns_av_unetI/netI     0.1716
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.881
_diffrn_reflns_theta_max         26.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.943
_reflns_number_total             7693
_reflns_number_gt                3609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_max     0.802
_reflns_Friedel_fraction_full    0.901

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 3-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.35(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7693
_refine_ls_number_parameters     140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_restrained_S_all      0.832
_refine_ls_shift/su_max          <0.001
_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 0.7278(3) 0.69192(16) 0.74459(12) 0.0568(6) Uani 1 1 d . . . . .
O1 O 0.5014(7) 0.5200(4) 0.6739(3) 0.0375(12) Uani 1 1 d . . . . .
O2 O 0.2086(10) 0.5934(4) 0.5077(3) 0.0658(17) Uani 1 1 d . . . . .
H2A H 0.276352 0.644578 0.530609 0.099 Uiso 1 1 calc R U . . .
N1 N 0.4870(11) 0.7292(5) 0.5877(4) 0.0511(18) Uani 1 1 d D . . . .
H1A H 0.508(14) 0.796(5) 0.564(4) 0.077 Uiso 1 1 d D U . . .
H1B H 0.437(12) 0.736(7) 0.636(3) 0.077 Uiso 1 1 d D U . . .
C1 C 0.6152(11) 0.5411(6) 0.7420(4) 0.0413(18) Uani 1 1 d . . . . .
C2 C 0.6298(11) 0.5281(6) 0.6070(4) 0.0348(18) Uani 1 1 d . . . . .
H2 H 0.772650 0.487804 0.617065 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6912(11) 0.6556(6) 0.5929(4) 0.041(2) Uani 1 1 d . . . . .
H3 H 0.770537 0.659958 0.545259 0.049 Uiso 1 1 calc R U . . .
C4 C 0.8521(12) 0.6974(7) 0.6533(4) 0.055(2) Uani 1 1 d . . . . .
H4A H 0.897618 0.777341 0.642634 0.066 Uiso 1 1 calc R U . . .
H4B H 0.986487 0.648811 0.652629 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4348(13) 0.5359(7) 0.8014(4) 0.060(3) Uani 1 1 d . . . . .
H5A H 0.498192 0.559445 0.848156 0.091 Uiso 1 1 calc R U . . .
H5B H 0.378503 0.457227 0.805320 0.091 Uiso 1 1 calc R U . . .
H5C H 0.313465 0.587827 0.788537 0.091 Uiso 1 1 calc R U . . .
C6 C 0.8011(13) 0.4512(6) 0.7558(4) 0.062(2) Uani 1 1 d . . . . .
H6A H 0.743670 0.373833 0.746549 0.092 Uiso 1 1 calc R U . . .
H6B H 0.850909 0.456592 0.806387 0.092 Uiso 1 1 calc R U . . .
H6C H 0.925743 0.466510 0.723204 0.092 Uiso 1 1 calc R U . . .
C7 C 0.5118(12) 0.4556(6) 0.5472(4) 0.0375(18) Uani 1 1 d . . . . .
C8 C 0.2583(12) 0.4829(6) 0.5388(4) 0.0465(18) Uani 1 1 d . . . . .
H8A H 0.190472 0.422729 0.507981 0.056 Uiso 1 1 calc R U . . .
H8B H 0.188272 0.478281 0.587349 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6283(13) 0.4732(7) 0.4728(4) 0.059(2) Uani 1 1 d . . . . .
H9A H 0.787762 0.461496 0.478554 0.088 Uiso 1 1 calc R U . . .
H9B H 0.600496 0.551462 0.455404 0.088 Uiso 1 1 calc R U . . .
H9C H 0.570049 0.417831 0.437573 0.088 Uiso 1 1 calc R U . . .
C10 C 0.5270(13) 0.3270(6) 0.5703(4) 0.055(2) Uani 1 1 d . . . . .
H10A H 0.441259 0.314987 0.614854 0.082 Uiso 1 1 calc R U . . .
H10B H 0.681888 0.306611 0.579084 0.082 Uiso 1 1 calc R U . . .
H10C H 0.467263 0.278410 0.531456 0.082 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 C4 1.804(7) . ?
S1 C1 1.845(7) . ?
O1 C1 1.423(8) . ?
O1 C2 1.429(8) . ?
O2 C8 1.410(8) . ?
O2 H2A 0.8200 . ?
N1 C3 1.475(9) . ?
N1 H1A 0.88(4) . ?
N1 H1B 0.91(4) . ?
C1 C5 1.514(9) . ?
C1 C6 1.525(9) . ?
C2 C3 1.520(9) . ?
C2 C7 1.527(9) . ?
C2 H2 0.9800 . ?
C3 C4 1.524(9) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C9 1.521(9) . ?
C7 C10 1.527(10) . ?
C7 C8 1.541(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C1 99.0(4) . . ?
C1 O1 C2 117.7(5) . . ?
C8 O2 H2A 109.5 . . ?
C3 N1 H1A 114(6) . . ?
C3 N1 H1B 105(5) . . ?
H1A N1 H1B 115(8) . . ?
O1 C1 C5 105.6(6) . . ?
O1 C1 C6 111.7(6) . . ?
C5 C1 C6 111.6(6) . . ?
O1 C1 S1 110.5(5) . . ?
C5 C1 S1 105.9(5) . . ?
C6 C1 S1 111.2(5) . . ?
O1 C2 C3 109.3(5) . . ?
O1 C2 C7 108.4(5) . . ?
C3 C2 C7 120.6(6) . . ?
O1 C2 H2 105.8 . . ?
C3 C2 H2 105.8 . . ?
C7 C2 H2 105.8 . . ?
N1 C3 C2 111.0(5) . . ?
N1 C3 C4 112.4(6) . . ?
C2 C3 C4 109.2(6) . . ?
N1 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C3 C4 S1 112.7(5) . . ?
C3 C4 H4A 109.1 . . ?
S1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
S1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C7 C10 109.9(6) . . ?
C9 C7 C2 110.0(6) . . ?
C10 C7 C2 107.5(6) . . ?
C9 C7 C8 109.2(6) . . ?
C10 C7 C8 106.2(6) . . ?
C2 C7 C8 114.0(6) . . ?
O2 C8 C7 115.0(6) . . ?
O2 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
O2 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 C1 C5 175.6(5) . . . . ?
C2 O1 C1 C6 -62.8(7) . . . . ?
C2 O1 C1 S1 61.5(6) . . . . ?
C4 S1 C1 O1 -45.9(5) . . . . ?
C4 S1 C1 C5 -159.8(5) . . . . ?
C4 S1 C1 C6 78.7(6) . . . . ?
C1 O1 C2 C3 -70.1(7) . . . . ?
C1 O1 C2 C7 156.7(5) . . . . ?
O1 C2 C3 N1 -58.1(7) . . . . ?
C7 C2 C3 N1 68.5(8) . . . . ?
O1 C2 C3 C4 66.3(7) . . . . ?
C7 C2 C3 C4 -167.1(6) . . . . ?
N1 C3 C4 S1 61.7(7) . . . . ?
C2 C3 C4 S1 -61.9(7) . . . . ?
C1 S1 C4 C3 49.1(6) . . . . ?
O1 C2 C7 C9 173.5(6) . . . . ?
C3 C2 C7 C9 46.5(8) . . . . ?
O1 C2 C7 C10 -66.8(7) . . . . ?
C3 C2 C7 C10 166.2(6) . . . . ?
O1 C2 C7 C8 50.5(8) . . . . ?
C3 C2 C7 C8 -76.5(8) . . . . ?
C9 C7 C8 O2 -53.2(8) . . . . ?
C10 C7 C8 O2 -171.6(6) . . . . ?
C2 C7 C8 O2 70.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A N1 0.82 1.88 2.683(9) 164.6 . yes
N1 H1A O2 0.88(4) 2.16(6) 2.962(8) 150(7) 4_566 yes

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_EWKK21017-2kr1absref
_audit_block_doi                 10.5517/ccdc.csd.cc2c6fgh
_database_code_depnum_ccdc_archive 'CCDC 2180926'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N O2 S'
_chemical_formula_sum            'C14 H17 N O2 S'
_chemical_formula_weight         263.34

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                   5.6555(3)
_cell_length_b                   8.2434(3)
_cell_length_c                   14.8956(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.631(5)
_cell_angle_gamma                90
_cell_volume                     682.52(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3726
_cell_measurement_theta_min      3.6630
_cell_measurement_theta_max      27.5650

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.842
_oxdiff_exptl_absorpt_empirical_full_max 1.083
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            8211
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.783
_diffrn_reflns_theta_max         29.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3249
_reflns_number_gt                2608
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.815
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.0247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          <0.001
_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 0.29196(16) 0.65912(7) 0.27704(5) 0.0593(3) Uani 1 1 d . . . . .
O1 O 0.3055(3) 0.33784(19) 0.27696(10) 0.0360(4) Uani 1 1 d . . . . .
O2 O -0.0665(3) 0.2577(2) 0.01620(13) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.2018(4) 0.4528(3) 0.07888(14) 0.0432(5) Uani 1 1 d . . . . .
H1 H 0.130056 0.534301 0.049725 0.052 Uiso 1 1 calc R U . . .
C1 C 0.3927(5) 0.4702(3) 0.33432(16) 0.0396(6) Uani 1 1 d . . . . .
H1A H 0.568974 0.467728 0.346252 0.048 Uiso 1 1 calc R U . . .
C2 C 0.4267(5) 0.3147(3) 0.20195(17) 0.0356(6) Uani 1 1 d . . . . .
H2 H 0.590483 0.274417 0.223298 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4296(5) 0.4663(3) 0.14178(17) 0.0430(6) Uani 1 1 d . . . . .
H3 H 0.557672 0.451219 0.106329 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4692(6) 0.6304(3) 0.1886(2) 0.0591(9) Uani 1 1 d . . . . .
H4A H 0.428980 0.715039 0.143088 0.071 Uiso 1 1 calc R U . . .
H4B H 0.638238 0.641624 0.215341 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2783(4) 0.1914(3) 0.13717(16) 0.0340(6) Uani 1 1 d . . . . .
C6 C 0.1135(5) 0.3018(3) 0.07042(16) 0.0362(6) Uani 1 1 d . . . . .
C7 C 0.4403(5) 0.0988(4) 0.0826(2) 0.0544(8) Uani 1 1 d . . . . .
H7A H 0.342459 0.034391 0.036391 0.082 Uiso 1 1 calc R U . . .
H7B H 0.547395 0.029430 0.122999 0.082 Uiso 1 1 calc R U . . .
H7C H 0.532345 0.174758 0.054296 0.082 Uiso 1 1 calc R U . . .
C8 C 0.1342(5) 0.0715(3) 0.18296(17) 0.0414(6) Uani 1 1 d . . . . .
H8A H 0.048255 -0.000726 0.137855 0.062 Uiso 1 1 calc R U . . .
H8B H 0.021977 0.129438 0.212115 0.062 Uiso 1 1 calc R U . . .
H8C H 0.241468 0.010015 0.227827 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3067(5) 0.4573(3) 0.42348(16) 0.0391(6) Uani 1 1 d . . . . .
C10 C 0.4361(6) 0.5361(3) 0.49948(19) 0.0520(8) Uani 1 1 d . . . . .
H10 H 0.572596 0.595737 0.494355 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3618(7) 0.5257(4) 0.58266(19) 0.0643(10) Uani 1 1 d . . . . .
H11 H 0.448126 0.579287 0.633209 0.077 Uiso 1 1 calc R U . . .
C12 C 0.1631(7) 0.4375(4) 0.5913(2) 0.0665(9) Uani 1 1 d . . . . .
H12 H 0.115329 0.430310 0.647699 0.080 Uiso 1 1 calc R U . . .
C13 C 0.0340(7) 0.3596(4) 0.5169(2) 0.0637(9) Uani 1 1 d . . . . .
H13 H -0.102194 0.300365 0.522792 0.076 Uiso 1 1 calc R U . . .
C14 C 0.1052(5) 0.3687(4) 0.43316(19) 0.0493(7) Uani 1 1 d . . . . .
H14 H 0.017188 0.314943 0.383022 0.059 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 C4 1.812(3) . ?
S1 C1 1.816(2) . ?
O1 C1 1.417(3) . ?
O1 C2 1.427(3) . ?
O2 C6 1.232(3) . ?
N1 C6 1.338(3) . ?
N1 C3 1.451(3) . ?
N1 H1 0.8600 . ?
C1 C9 1.500(3) . ?
C1 H1A 0.9800 . ?
C2 C5 1.539(3) . ?
C2 C3 1.540(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.519(4) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.520(3) . ?
C5 C6 1.531(3) . ?
C5 C7 1.535(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.383(4) . ?
C9 C10 1.391(4) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C4 S1 C1 93.55(13) . . ?
C1 O1 C2 114.25(19) . . ?
C6 N1 C3 113.8(2) . . ?
C6 N1 H1 123.1 . . ?
C3 N1 H1 123.1 . . ?
O1 C1 C9 110.2(2) . . ?
O1 C1 S1 109.44(15) . . ?
C9 C1 S1 110.59(18) . . ?
O1 C1 H1A 108.9 . . ?
C9 C1 H1A 108.9 . . ?
S1 C1 H1A 108.9 . . ?
O1 C2 C5 107.1(2) . . ?
O1 C2 C3 113.9(2) . . ?
C5 C2 C3 103.54(19) . . ?
O1 C2 H2 110.7 . . ?
C5 C2 H2 110.7 . . ?
C3 C2 H2 110.7 . . ?
N1 C3 C4 113.8(2) . . ?
N1 C3 C2 102.1(2) . . ?
C4 C3 C2 118.2(2) . . ?
N1 C3 H3 107.4 . . ?
C4 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C3 C4 S1 113.3(2) . . ?
C3 C4 H4A 108.9 . . ?
S1 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
S1 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C8 C5 C6 111.4(2) . . ?
C8 C5 C7 109.6(2) . . ?
C6 C5 C7 107.6(2) . . ?
C8 C5 C2 115.05(19) . . ?
C6 C5 C2 102.17(19) . . ?
C7 C5 C2 110.5(2) . . ?
O2 C6 N1 125.8(2) . . ?
O2 C6 C5 125.5(2) . . ?
N1 C6 C5 108.7(2) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.8(2) . . ?
C14 C9 C1 122.5(2) . . ?
C10 C9 C1 118.7(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 C1 C9 -164.0(2) . . . . ?
C2 O1 C1 S1 74.1(2) . . . . ?
C4 S1 C1 O1 -66.07(19) . . . . ?
C4 S1 C1 C9 172.32(19) . . . . ?
C1 O1 C2 C5 -168.67(18) . . . . ?
C1 O1 C2 C3 -54.8(3) . . . . ?
C6 N1 C3 C4 -150.6(2) . . . . ?
C6 N1 C3 C2 -22.1(3) . . . . ?
O1 C2 C3 N1 -85.7(2) . . . . ?
C5 C2 C3 N1 30.2(2) . . . . ?
O1 C2 C3 C4 39.9(3) . . . . ?
C5 C2 C3 C4 155.9(3) . . . . ?
N1 C3 C4 S1 74.5(3) . . . . ?
C2 C3 C4 S1 -45.2(3) . . . . ?
C1 S1 C4 C3 51.9(2) . . . . ?
O1 C2 C5 C8 -28.2(3) . . . . ?
C3 C2 C5 C8 -148.8(2) . . . . ?
O1 C2 C5 C6 92.7(2) . . . . ?
C3 C2 C5 C6 -28.0(2) . . . . ?
O1 C2 C5 C7 -153.0(2) . . . . ?
C3 C2 C5 C7 86.3(3) . . . . ?
C3 N1 C6 O2 -174.0(2) . . . . ?
C3 N1 C6 C5 4.1(3) . . . . ?
C8 C5 C6 O2 -42.7(3) . . . . ?
C7 C5 C6 O2 77.5(3) . . . . ?
C2 C5 C6 O2 -166.1(2) . . . . ?
C8 C5 C6 N1 139.1(2) . . . . ?
C7 C5 C6 N1 -100.6(2) . . . . ?
C2 C5 C6 N1 15.8(3) . . . . ?
O1 C1 C9 C14 -22.4(3) . . . . ?
S1 C1 C9 C14 98.7(3) . . . . ?
O1 C1 C9 C10 156.9(2) . . . . ?
S1 C1 C9 C10 -82.0(3) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C1 C9 C10 C11 -179.7(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C1 C9 C14 C13 179.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.86 2.09 2.917(3) 162.1 2 yes
C8 H8C S1 0.96 2.98 3.722(3) 134.6 1_545 yes
C7 H7C O2 0.96 2.53 3.390(4) 148.8 1_655 yes

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.209
_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_KKYM2NHKWAS
_audit_block_doi                 10.5517/ccdc.csd.cc2c6fcd
_database_code_depnum_ccdc_archive 'CCDC 2180923'
loop_
_audit_author_name
_audit_author_address
'Marek Daszkiewicz'
;Institute of Low Temperature and Structure Research Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 N O2 S'
_chemical_formula_sum            'C10 H17 N O2 S'
_chemical_formula_weight         215.30

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                   14.7795(2)
_cell_length_b                   8.01466(11)
_cell_length_c                   15.0100(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.4776(18)
_cell_angle_gamma                90
_cell_volume                     1695.89(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    24200
_cell_measurement_theta_min      3.4110
_cell_measurement_theta_max      32.2200

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.915
_oxdiff_exptl_absorpt_empirical_full_max 1.068
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            57514
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10359
_reflns_number_gt                9890
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+0.1735P] 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 4459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(12)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         10359
_refine_ls_number_parameters     400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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
O1 O 0.64794(8) 0.74129(14) 0.21619(8) 0.0182(2) Uani 1 1 d . . . . .
S1 S 0.28766(2) 0.34548(4) 0.09086(3) 0.01554(8) Uani 1 1 d . . . . .
C1 C 0.56592(10) 0.69509(17) 0.17675(10) 0.0129(3) Uani 1 1 d . . . . .
N1 N 0.54140(9) 0.55818(16) 0.12357(9) 0.0135(2) Uani 1 1 d . . . . .
H1 H 0.5834(14) 0.485(3) 0.1185(13) 0.016 Uiso 1 1 d . U . . .
O4 O 0.38631(7) 0.56488(13) 0.22217(7) 0.01177(19) Uani 1 1 d . . . . .
C4 C 0.43902(10) 0.53377(17) 0.08475(10) 0.0119(2) Uani 1 1 d . . . . .
H4 H 0.417928 0.568045 0.019052 0.014 Uiso 1 1 calc R U . . .
S2 S 0.98459(2) -0.18390(4) 0.19006(3) 0.01545(7) Uani 1 1 d . . . . .
C2 C 0.47561(10) 0.78775(17) 0.17775(10) 0.0126(3) Uani 1 1 d . . . . .
N2 N 0.74240(9) 0.03899(16) 0.19280(9) 0.0147(2) Uani 1 1 d . . . . .
H2 H 0.6987(14) -0.030(3) 0.1952(14) 0.018 Uiso 1 1 d . U . . .
N3 N 0.07971(9) 0.77208(16) 0.46605(9) 0.0146(2) Uani 1 1 d . . . . .
H3 H 0.0378(14) 0.842(3) 0.4650(14) 0.018 Uiso 1 1 d . U . . .
S3 S 0.32316(3) 0.97238(5) 0.45256(3) 0.01822(8) Uani 1 1 d . . . . .
O3 O 0.91656(7) 0.11511(13) 0.11246(7) 0.01256(19) Uani 1 1 d . . . . .
C3 C 0.39839(10) 0.65362(17) 0.14378(10) 0.0112(2) Uani 1 1 d . . . . .
H3A H 0.338451 0.703062 0.106150 0.013 Uiso 1 1 calc R U . . .
O12 O 0.64318(8) 0.25500(14) 0.12721(8) 0.0171(2) Uani 1 1 d . . . . .
C12 C 0.81689(10) 0.28960(17) 0.17726(10) 0.0116(2) Uani 1 1 d . . . . .
C13 C 0.89204(10) 0.14888(17) 0.19579(10) 0.0112(2) Uani 1 1 d . . . . .
H13 H 0.948493 0.180041 0.246753 0.013 Uiso 1 1 calc R U . . .
C14 C 0.84259(10) -0.00495(17) 0.22365(10) 0.0124(2) Uani 1 1 d . . . . .
H14 H 0.864321 -0.020208 0.291552 0.015 Uiso 1 1 calc R U . . .
C17 C 0.83090(11) 0.39236(19) 0.26741(11) 0.0166(3) Uani 1 1 d . . . . .
H17A H 0.890071 0.451367 0.281807 0.025 Uiso 1 1 calc R U . . .
H17B H 0.831491 0.318794 0.318058 0.025 Uiso 1 1 calc R U . . .
H17C H 0.779853 0.470808 0.258427 0.025 Uiso 1 1 calc R U . . .
C16 C 0.99510(10) 0.00558(17) 0.12178(10) 0.0133(3) Uani 1 1 d . . . . .
C15 C 0.85933(10) -0.16337(18) 0.17499(10) 0.0138(2) Uani 1 1 d . . . . .
H15A H 0.824615 -0.157945 0.108999 0.017 Uiso 1 1 calc R U . . .
H15B H 0.836920 -0.259448 0.201547 0.017 Uiso 1 1 calc R U . . .
C18 C 0.81434(11) 0.40335(19) 0.09497(11) 0.0164(3) Uani 1 1 d . . . . .
H18A H 0.803660 0.337519 0.039332 0.025 Uiso 1 1 calc R U . . .
H18B H 0.873771 0.460991 0.107243 0.025 Uiso 1 1 calc R U . . .
H18C H 0.763995 0.483077 0.086592 0.025 Uiso 1 1 calc R U . . .
O2 O 0.02582(8) 0.56658(14) 0.54320(8) 0.0177(2) Uani 1 1 d . . . . .
O5 O 0.29242(7) 0.70286(13) 0.54969(7) 0.01215(19) Uani 1 1 d . . . . .
C5 C 0.41063(10) 0.35239(18) 0.09369(10) 0.0138(3) Uani 1 1 d . . . . .
H5A H 0.450223 0.305549 0.151955 0.017 Uiso 1 1 calc R U . . .
H5AB H 0.419573 0.286801 0.042673 0.017 Uiso 1 1 calc R U . . .
C7 C 0.48501(12) 0.8609(2) 0.27420(11) 0.0200(3) Uani 1 1 d . . . . .
H7A H 0.534064 0.943956 0.289059 0.030 Uiso 1 1 calc R U . . .
H7B H 0.500935 0.773622 0.320103 0.030 Uiso 1 1 calc R U . . .
H7C H 0.425947 0.910939 0.274010 0.030 Uiso 1 1 calc R U . . .
C6 C 0.30382(10) 0.46088(19) 0.20203(10) 0.0128(2) Uani 1 1 d . . . . .
C8 C 0.45750(12) 0.92698(19) 0.10391(12) 0.0188(3) Uani 1 1 d . . . . .
H8A H 0.448955 0.878616 0.043429 0.028 Uiso 1 1 calc R U . . .
H8B H 0.510790 1.001520 0.118538 0.028 Uiso 1 1 calc R U . . .
H8C H 0.401439 0.987700 0.103702 0.028 Uiso 1 1 calc R U . . .
C9 C 0.32378(10) 0.3383(2) 0.28315(10) 0.0168(3) Uani 1 1 d . . . . .
H9A H 0.270044 0.266224 0.275101 0.025 Uiso 1 1 calc R U . . .
H9B H 0.335294 0.398770 0.340698 0.025 Uiso 1 1 calc R U . . .
H9C H 0.378597 0.272681 0.284791 0.025 Uiso 1 1 calc R U . . .
C10 C 0.21472(11) 0.5647(2) 0.19224(11) 0.0168(3) Uani 1 1 d . . . . .
H10A H 0.203606 0.636471 0.138842 0.025 Uiso 1 1 calc R U . . .
H10B H 0.223195 0.630983 0.247402 0.025 Uiso 1 1 calc R U . . .
H10C H 0.161341 0.491749 0.184318 0.025 Uiso 1 1 calc R U . . .
C11 C 0.72326(10) 0.19495(18) 0.16098(10) 0.0124(2) Uani 1 1 d . . . . .
C22 C 0.16058(10) 0.51902(17) 0.48091(10) 0.0116(2) Uani 1 1 d . . . . .
C21 C 0.08114(10) 0.61929(18) 0.50249(10) 0.0124(3) Uani 1 1 d . . . . .
C20 C 0.98901(12) -0.0441(2) 0.02255(11) 0.0189(3) Uani 1 1 d . . . . .
H20A H 0.928872 -0.096238 -0.006468 0.028 Uiso 1 1 calc R U . . .
H20B H 1.039149 -0.121020 0.023667 0.028 Uiso 1 1 calc R U . . .
H20C H 0.995164 0.053411 -0.012295 0.028 Uiso 1 1 calc R U . . .
C19 C 1.08982(11) 0.0886(2) 0.17177(13) 0.0208(3) Uani 1 1 d . . . . .
H19A H 1.140442 0.010544 0.177057 0.031 Uiso 1 1 calc R U . . .
H19B H 1.089851 0.123291 0.232992 0.031 Uiso 1 1 calc R U . . .
H19C H 1.098674 0.184055 0.136673 0.031 Uiso 1 1 calc R U . . .
C25 C 0.20396(10) 0.97382(19) 0.46209(11) 0.0163(3) Uani 1 1 d . . . . .
H25A H 0.205934 0.991058 0.526608 0.020 Uiso 1 1 calc R U . . .
H25B H 0.167708 1.063921 0.424861 0.020 Uiso 1 1 calc R U . . .
C24 C 0.15722(9) 0.80663(18) 0.42729(10) 0.0126(2) Uani 1 1 d . . . . .
H24 H 0.133910 0.805763 0.358885 0.015 Uiso 1 1 calc R U . . .
C23 C 0.22506(10) 0.65806(17) 0.46301(10) 0.0107(2) Uani 1 1 d . . . . .
H23 H 0.256344 0.623612 0.416931 0.013 Uiso 1 1 calc R U . . .
C27 C 0.21032(11) 0.39640(18) 0.55788(11) 0.0154(3) Uani 1 1 d . . . . .
H27A H 0.164953 0.317747 0.567092 0.023 Uiso 1 1 calc R U . . .
H27B H 0.238355 0.456321 0.614889 0.023 Uiso 1 1 calc R U . . .
H27C H 0.258909 0.338015 0.540066 0.023 Uiso 1 1 calc R U . . .
C28 C 0.11358(11) 0.42550(19) 0.38893(10) 0.0161(3) Uani 1 1 d . . . . .
H28A H 0.083010 0.504265 0.341195 0.024 Uiso 1 1 calc R U . . .
H28B H 0.067380 0.348544 0.398047 0.024 Uiso 1 1 calc R U . . .
H28C H 0.161083 0.365423 0.370240 0.024 Uiso 1 1 calc R U . . .
C30 C 0.40516(11) 0.8884(2) 0.63944(11) 0.0217(3) Uani 1 1 d . . . . .
H30A H 0.459365 0.956379 0.642073 0.033 Uiso 1 1 calc R U . . .
H30B H 0.423094 0.802269 0.685904 0.033 Uiso 1 1 calc R U . . .
H30C H 0.356419 0.956251 0.651127 0.033 Uiso 1 1 calc R U . . .
C29 C 0.44443(11) 0.7108(2) 0.51663(12) 0.0192(3) Uani 1 1 d . . . . .
H29A H 0.417383 0.659689 0.456649 0.029 Uiso 1 1 calc R U . . .
H29B H 0.469289 0.625851 0.562581 0.029 Uiso 1 1 calc R U . . .
H29C H 0.494678 0.784640 0.513957 0.029 Uiso 1 1 calc R U . . .
C26 C 0.36807(10) 0.80941(19) 0.54315(10) 0.0144(3) 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
O1 C1 1.2352(18) . ?
S1 C5 1.8060(14) . ?
S1 C6 1.8593(15) . ?
C1 N1 1.3411(19) . ?
C1 C2 1.532(2) . ?
N1 C4 1.4622(18) . ?
N1 H1 0.87(2) . ?
O4 C3 1.4311(17) . ?
O4 C6 1.4322(17) . ?
C4 C5 1.530(2) . ?
C4 C3 1.5453(19) . ?
C4 H4 0.9800 . ?
S2 C15 1.8039(14) . ?
S2 C16 1.8645(15) . ?
C2 C7 1.529(2) . ?
C2 C8 1.538(2) . ?
C2 C3 1.539(2) . ?
N2 C11 1.3376(19) . ?
N2 C14 1.4558(18) . ?
N2 H2 0.86(2) . ?
N3 C21 1.3387(19) . ?
N3 C24 1.4588(18) . ?
N3 H3 0.83(2) . ?
S3 C25 1.8099(15) . ?
S3 C26 1.8583(15) . ?
O3 C16 1.4283(17) . ?
O3 C13 1.4288(17) . ?
C3 H3A 0.9800 . ?
O12 C11 1.2365(18) . ?
C12 C18 1.526(2) . ?
C12 C11 1.5320(19) . ?
C12 C17 1.544(2) . ?
C12 C13 1.5483(19) . ?
C13 C14 1.5532(19) . ?
C13 H13 0.9800 . ?
C14 C15 1.522(2) . ?
C14 H14 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 C20 1.518(2) . ?
C16 C19 1.528(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O2 C21 1.2331(18) . ?
O5 C23 1.4265(16) . ?
O5 C26 1.4335(17) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C9 1.523(2) . ?
C6 C10 1.527(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C22 C27 1.527(2) . ?
C22 C21 1.536(2) . ?
C22 C28 1.541(2) . ?
C22 C23 1.541(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C25 C24 1.526(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C24 C23 1.545(2) . ?
C24 H24 0.9800 . ?
C23 H23 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 C26 1.521(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 C26 1.525(2) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C6 96.12(6) . . ?
O1 C1 N1 125.54(14) . . ?
O1 C1 C2 125.64(13) . . ?
N1 C1 C2 108.79(12) . . ?
C1 N1 C4 114.14(12) . . ?
C1 N1 H1 121.9(13) . . ?
C4 N1 H1 123.6(13) . . ?
C3 O4 C6 115.10(10) . . ?
N1 C4 C5 111.74(11) . . ?
N1 C4 C3 102.83(11) . . ?
C5 C4 C3 112.10(11) . . ?
N1 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
C15 S2 C16 96.23(6) . . ?
C7 C2 C1 111.31(12) . . ?
C7 C2 C8 110.53(12) . . ?
C1 C2 C8 107.95(12) . . ?
C7 C2 C3 115.39(12) . . ?
C1 C2 C3 102.70(11) . . ?
C8 C2 C3 108.47(12) . . ?
C11 N2 C14 115.18(12) . . ?
C11 N2 H2 122.4(14) . . ?
C14 N2 H2 122.5(14) . . ?
C21 N3 C24 114.74(12) . . ?
C21 N3 H3 123.1(15) . . ?
C24 N3 H3 122.2(14) . . ?
C25 S3 C26 95.11(7) . . ?
C16 O3 C13 116.30(11) . . ?
O4 C3 C2 109.76(11) . . ?
O4 C3 C4 109.17(11) . . ?
C2 C3 C4 104.30(11) . . ?
O4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C18 C12 C11 111.41(12) . . ?
C18 C12 C17 110.78(12) . . ?
C11 C12 C17 106.31(11) . . ?
C18 C12 C13 114.99(12) . . ?
C11 C12 C13 103.46(11) . . ?
C17 C12 C13 109.33(12) . . ?
O3 C13 C12 109.73(11) . . ?
O3 C13 C14 110.42(11) . . ?
C12 C13 C14 104.86(11) . . ?
O3 C13 H13 110.6 . . ?
C12 C13 H13 110.6 . . ?
C14 C13 H13 110.6 . . ?
N2 C14 C15 110.22(12) . . ?
N2 C14 C13 103.78(11) . . ?
C15 C14 C13 112.06(11) . . ?
N2 C14 H14 110.2 . . ?
C15 C14 H14 110.2 . . ?
C13 C14 H14 110.2 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C16 C20 104.97(12) . . ?
O3 C16 C19 112.23(12) . . ?
C20 C16 C19 111.83(13) . . ?
O3 C16 S2 110.79(9) . . ?
C20 C16 S2 109.59(10) . . ?
C19 C16 S2 107.45(10) . . ?
C14 C15 S2 108.94(10) . . ?
C14 C15 H15A 109.9 . . ?
S2 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
S2 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 O5 C26 115.63(11) . . ?
C4 C5 S1 109.12(10) . . ?
C4 C5 H5A 109.9 . . ?
S1 C5 H5A 109.9 . . ?
C4 C5 H5AB 109.9 . . ?
S1 C5 H5AB 109.9 . . ?
H5A C5 H5AB 108.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C6 C9 104.98(11) . . ?
O4 C6 C10 110.99(12) . . ?
C9 C6 C10 112.50(12) . . ?
O4 C6 S1 110.53(9) . . ?
C9 C6 S1 109.79(10) . . ?
C10 C6 S1 108.06(10) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 C11 N2 125.72(14) . . ?
O12 C11 C12 125.46(13) . . ?
N2 C11 C12 108.77(12) . . ?
C27 C22 C21 113.71(12) . . ?
C27 C22 C28 110.49(12) . . ?
C21 C22 C28 106.03(11) . . ?
C27 C22 C23 114.52(12) . . ?
C21 C22 C23 102.14(11) . . ?
C28 C22 C23 109.36(12) . . ?
O2 C21 N3 125.76(14) . . ?
O2 C21 C22 126.02(13) . . ?
N3 C21 C22 108.17(12) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 C25 S3 108.58(10) . . ?
C24 C25 H25A 110.0 . . ?
S3 C25 H25A 110.0 . . ?
C24 C25 H25B 110.0 . . ?
S3 C25 H25B 110.0 . . ?
H25A C25 H25B 108.4 . . ?
N3 C24 C25 111.04(12) . . ?
N3 C24 C23 102.75(11) . . ?
C25 C24 C23 112.21(11) . . ?
N3 C24 H24 110.2 . . ?
C25 C24 H24 110.2 . . ?
C23 C24 H24 110.2 . . ?
O5 C23 C22 108.76(11) . . ?
O5 C23 C24 108.96(11) . . ?
C22 C23 C24 104.30(11) . . ?
O5 C23 H23 111.5 . . ?
C22 C23 H23 111.5 . . ?
C24 C23 H23 111.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O5 C26 C30 104.39(12) . . ?
O5 C26 C29 111.25(12) . . ?
C30 C26 C29 112.33(12) . . ?
O5 C26 S3 110.75(9) . . ?
C30 C26 S3 110.51(11) . . ?
C29 C26 S3 107.64(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C4 -179.58(14) . . . . ?
C2 C1 N1 C4 -1.50(16) . . . . ?
C1 N1 C4 C5 -135.62(13) . . . . ?
C1 N1 C4 C3 -15.20(16) . . . . ?
O1 C1 C2 C7 -40.3(2) . . . . ?
N1 C1 C2 C7 141.63(13) . . . . ?
O1 C1 C2 C8 81.19(18) . . . . ?
N1 C1 C2 C8 -96.89(14) . . . . ?
O1 C1 C2 C3 -164.33(14) . . . . ?
N1 C1 C2 C3 17.59(15) . . . . ?
C6 O4 C3 C2 167.67(11) . . . . ?
C6 O4 C3 C4 -78.58(14) . . . . ?
C7 C2 C3 O4 -30.22(16) . . . . ?
C1 C2 C3 O4 91.07(13) . . . . ?
C8 C2 C3 O4 -154.83(11) . . . . ?
C7 C2 C3 C4 -147.08(12) . . . . ?
C1 C2 C3 C4 -25.78(14) . . . . ?
C8 C2 C3 C4 88.32(13) . . . . ?
N1 C4 C3 O4 -92.22(13) . . . . ?
C5 C4 C3 O4 27.95(16) . . . . ?
N1 C4 C3 C2 25.04(14) . . . . ?
C5 C4 C3 C2 145.21(12) . . . . ?
C16 O3 C13 C12 171.11(11) . . . . ?
C16 O3 C13 C14 -73.79(14) . . . . ?
C18 C12 C13 O3 -22.76(16) . . . . ?
C11 C12 C13 O3 98.95(12) . . . . ?
C17 C12 C13 O3 -148.09(11) . . . . ?
C18 C12 C13 C14 -141.36(12) . . . . ?
C11 C12 C13 C14 -19.64(14) . . . . ?
C17 C12 C13 C14 93.31(13) . . . . ?
C11 N2 C14 C15 -126.80(13) . . . . ?
C11 N2 C14 C13 -6.64(17) . . . . ?
O3 C13 C14 N2 -101.76(13) . . . . ?
C12 C13 C14 N2 16.37(14) . . . . ?
O3 C13 C14 C15 17.15(16) . . . . ?
C12 C13 C14 C15 135.29(12) . . . . ?
C13 O3 C16 C20 165.44(12) . . . . ?
C13 O3 C16 C19 -72.89(15) . . . . ?
C13 O3 C16 S2 47.23(13) . . . . ?
C15 S2 C16 O3 18.73(11) . . . . ?
C15 S2 C16 C20 -96.64(11) . . . . ?
C15 S2 C16 C19 141.65(11) . . . . ?
N2 C14 C15 S2 165.00(10) . . . . ?
C13 C14 C15 S2 49.96(13) . . . . ?
C16 S2 C15 C14 -64.91(10) . . . . ?
N1 C4 C5 S1 156.66(10) . . . . ?
C3 C4 C5 S1 41.82(14) . . . . ?
C6 S1 C5 C4 -65.24(11) . . . . ?
C3 O4 C6 C9 160.82(11) . . . . ?
C3 O4 C6 C10 -77.38(14) . . . . ?
C3 O4 C6 S1 42.50(14) . . . . ?
C5 S1 C6 O4 24.55(11) . . . . ?
C5 S1 C6 C9 -90.80(10) . . . . ?
C5 S1 C6 C10 146.17(10) . . . . ?
C14 N2 C11 O12 176.15(14) . . . . ?
C14 N2 C11 C12 -6.36(17) . . . . ?
C18 C12 C11 O12 -42.0(2) . . . . ?
C17 C12 C11 O12 78.83(18) . . . . ?
C13 C12 C11 O12 -166.04(14) . . . . ?
C18 C12 C11 N2 140.55(13) . . . . ?
C17 C12 C11 N2 -98.66(14) . . . . ?
C13 C12 C11 N2 16.47(15) . . . . ?
C24 N3 C21 O2 175.93(14) . . . . ?
C24 N3 C21 C22 -6.58(17) . . . . ?
C27 C22 C21 O2 -36.9(2) . . . . ?
C28 C22 C21 O2 84.64(17) . . . . ?
C23 C22 C21 O2 -160.87(14) . . . . ?
C27 C22 C21 N3 145.57(13) . . . . ?
C28 C22 C21 N3 -92.84(14) . . . . ?
C23 C22 C21 N3 21.65(15) . . . . ?
C26 S3 C25 C24 -66.95(11) . . . . ?
C21 N3 C24 C25 -131.63(13) . . . . ?
C21 N3 C24 C23 -11.47(16) . . . . ?
S3 C25 C24 N3 157.20(10) . . . . ?
S3 C25 C24 C23 42.83(14) . . . . ?
C26 O5 C23 C22 169.44(11) . . . . ?
C26 O5 C23 C24 -77.46(14) . . . . ?
C27 C22 C23 O5 -34.82(16) . . . . ?
C21 C22 C23 O5 88.55(13) . . . . ?
C28 C22 C23 O5 -159.43(11) . . . . ?
C27 C22 C23 C24 -150.97(12) . . . . ?
C21 C22 C23 C24 -27.59(13) . . . . ?
C28 C22 C23 C24 84.42(13) . . . . ?
N3 C24 C23 O5 -91.79(13) . . . . ?
C25 C24 C23 O5 27.56(15) . . . . ?
N3 C24 C23 C22 24.22(14) . . . . ?
C25 C24 C23 C22 143.57(12) . . . . ?
C23 O5 C26 C30 159.39(12) . . . . ?
C23 O5 C26 C29 -79.24(15) . . . . ?
C23 O5 C26 S3 40.44(14) . . . . ?
C25 S3 C26 O5 26.87(11) . . . . ?
C25 S3 C26 C30 -88.32(11) . . . . ?
C25 S3 C26 C29 148.68(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O12 0.87(2) 2.03(2) 2.8497(16) 155.4(19) . yes
C4 H4 O12 0.98 2.59 3.5243(18) 160.2 2_655 yes
N2 H2 O1 0.86(2) 2.04(2) 2.8390(17) 154.2(19) 1_545 yes
N3 H3 O2 0.83(2) 2.02(2) 2.8094(16) 159(2) 2_556 yes
C14 H14 O2 0.98 2.62 3.5029(18) 150.3 2_646 yes
C15 H15A S1 0.97 2.96 3.9294(15) 177.2 2_645 yes
C24 H24 S2 0.98 2.82 3.7065(14) 151.2 1_465 yes

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042

