# Electronic Supplementary Material (ESI) for ChemComm.
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 2266968'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_audit_creation_date             2023-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H14 N2 O3 S'
_chemical_formula_sum            'C7 H14 N2 O3 S'
_chemical_formula_weight         206.26
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4126(2)
_cell_length_b                   9.9316(3)
_cell_length_c                   10.3407(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.903(2)
_cell_angle_gamma                90
_cell_volume                     938.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6889
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9961
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1507
_reflns_number_total             1647
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.7852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.66715(5) 0.70585(5) 0.35265(4) 0.02045(19) Uani 1 1 d . . . . .
O1 O 0.97264(14) 0.30544(14) 0.35037(13) 0.0283(3) Uani 1 1 d . . . . .
O2 O 0.51985(14) 0.67160(16) 0.35551(14) 0.0335(4) Uani 1 1 d . . . . .
O3 O 0.71177(18) 0.84428(14) 0.37116(14) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.77763(16) 0.61401(15) 0.46048(14) 0.0198(4) Uani 1 1 d . . . . .
H1 H 0.872323 0.621804 0.467586 0.024 Uiso 1 1 calc R U . . .
N2 N 0.81210(16) 0.43388(15) 0.20753(15) 0.0204(4) Uani 1 1 d . . . . .
C1 C 0.7262(2) 0.51736(19) 0.54777(18) 0.0240(4) Uani 1 1 d . . . . .
H1A H 0.617905 0.515915 0.523805 0.029 Uiso 1 1 calc R U . . .
H1B H 0.758575 0.548386 0.641222 0.029 Uiso 1 1 calc R U . . .
C2 C 0.7825(2) 0.37594(19) 0.53771(18) 0.0241(4) Uani 1 1 d . . . . .
H2A H 0.744019 0.316366 0.598137 0.029 Uiso 1 1 calc R U . . .
H2B H 0.890535 0.376285 0.568148 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7387(2) 0.31824(19) 0.39607(19) 0.0255(4) Uani 1 1 d . . . . .
H3A H 0.731356 0.219015 0.400937 0.031 Uiso 1 1 calc R U . . .
H3B H 0.641175 0.353442 0.350355 0.031 Uiso 1 1 calc R U . . .
C4 C 0.84825(19) 0.35446(18) 0.31566(17) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.67555(19) 0.50840(19) 0.16190(18) 0.0226(4) Uani 1 1 d . . . . .
H5A H 0.600845 0.470025 0.204302 0.027 Uiso 1 1 calc R U . . .
H5B H 0.640121 0.496870 0.064358 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6920(2) 0.65879(18) 0.19398(17) 0.0214(4) Uani 1 1 d . . . . .
H6A H 0.620230 0.708672 0.124927 0.026 Uiso 1 1 calc R U . . .
H6B H 0.790970 0.687551 0.188062 0.026 Uiso 1 1 calc R U . . .
C8 C 0.9245(2) 0.4618(2) 0.1344(2) 0.0275(4) Uani 1 1 d . . . . .
H8A H 0.991878 0.530621 0.181946 0.041 Uiso 1 1 calc R U . . .
H8B H 0.877759 0.494368 0.044866 0.041 Uiso 1 1 calc R U . . .
H8C H 0.979095 0.379110 0.127691 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4348(14) . ?
S1 O3 1.4369(15) . ?
S1 N1 1.6122(15) . ?
S1 C6 1.7749(18) . ?
O1 C4 1.239(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.476(2) . ?
N2 C4 1.344(2) . ?
N2 C5 1.460(2) . ?
N2 C8 1.467(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.513(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.515(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 118.49(9) . . ?
O2 S1 N1 108.52(8) . . ?
O2 S1 C6 107.42(9) . . ?
O3 S1 N1 109.26(9) . . ?
O3 S1 C6 106.01(9) . . ?
N1 S1 C6 106.50(8) . . ?
S1 N1 H1 118.7 . . ?
C1 N1 S1 122.62(12) . . ?
C1 N1 H1 118.7 . . ?
C4 N2 C5 126.44(15) . . ?
C4 N2 C8 118.03(15) . . ?
C5 N2 C8 115.19(15) . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
N1 C1 C2 112.96(15) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 C3 113.22(15) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.92(15) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
O1 C4 N2 120.30(17) . . ?
O1 C4 C3 117.91(17) . . ?
N2 C4 C3 121.76(16) . . ?
N2 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
N2 C5 C6 112.92(14) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
S1 C6 H6A 108.4 . . ?
S1 C6 H6B 108.4 . . ?
C5 C6 S1 115.37(13) . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
S1 N1 C1 C2 125.04(15) . . . . ?
O2 S1 N1 C1 -2.40(17) . . . . ?
O2 S1 C6 C5 -62.10(15) . . . . ?
O3 S1 N1 C1 128.14(15) . . . . ?
O3 S1 C6 C5 170.29(13) . . . . ?
N1 S1 C6 C5 54.01(15) . . . . ?
N1 C1 C2 C3 -58.5(2) . . . . ?
N2 C5 C6 S1 -87.88(17) . . . . ?
C1 C2 C3 C4 87.67(19) . . . . ?
C2 C3 C4 O1 66.8(2) . . . . ?
C2 C3 C4 N2 -115.12(18) . . . . ?
C4 N2 C5 C6 103.20(19) . . . . ?
C5 N2 C4 O1 -173.88(16) . . . . ?
C5 N2 C4 C3 8.1(3) . . . . ?
C6 S1 N1 C1 -117.77(15) . . . . ?
C8 N2 C4 O1 -1.0(2) . . . . ?
C8 N2 C4 C3 -179.00(16) . . . . ?
C8 N2 C5 C6 -69.87(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11g
_database_code_depnum_ccdc_archive 'CCDC 2266969'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2023-06-01 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H20 N2 O2 S, H2 O'
_chemical_formula_sum            'C9 H22 N2 O3 S'
_chemical_formula_weight         238.34
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7318(3)
_cell_length_b                   8.4291(3)
_cell_length_c                   13.9477(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.819(2)
_cell_angle_gamma                90
_cell_volume                     1243.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5031
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15580
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1855
_reflns_number_total             2190
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.5581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0972
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C1(H1A,H1B), C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B),
 C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.73192(5) 0.82710(6) 0.38265(3) 0.04311(17) Uani 1 1 d . . . . .
O1 O 0.83576(15) 0.89382(17) 0.34288(11) 0.0598(4) Uani 1 1 d . . . . .
O1W O 0.56021(13) 0.8619(2) 0.59811(14) 0.0642(5) Uani 1 1 d G . . . .
H1WA H 0.510522 0.785883 0.605127 0.096 Uiso 1 1 d G U . . .
H1WB H 0.517084 0.945083 0.603217 0.096 Uiso 1 1 d G U . . .
O2 O 0.60734(15) 0.88941(19) 0.35171(11) 0.0649(5) Uani 1 1 d . . . . .
N2 N 0.76258(15) 0.8405(2) 0.49805(11) 0.0450(4) Uani 1 1 d . . . . .
H2 H 0.701530 0.858386 0.529317 0.054 Uiso 1 1 calc R U . . .
N1 N 0.63554(16) 0.3578(2) 0.38309(14) 0.0489(4) Uani 1 1 d . . . . .
C2 C 0.62103(18) 0.5308(2) 0.38695(15) 0.0457(5) Uani 1 1 d . . . . .
H2A H 0.617381 0.561536 0.453435 0.055 Uiso 1 1 calc R U . . .
H2B H 0.541244 0.560270 0.347136 0.055 Uiso 1 1 calc R U . . .
C7 C 0.83228(19) 0.6044(3) 0.66566(15) 0.0483(5) Uani 1 1 d . . . . .
H7A H 0.824196 0.587761 0.733142 0.058 Uiso 1 1 calc R U . . .
H7B H 0.747850 0.602675 0.627413 0.058 Uiso 1 1 calc R U . . .
C1 C 0.72722(18) 0.6231(2) 0.35218(15) 0.0448(5) Uani 1 1 d . . . . .
H1A H 0.717698 0.613132 0.282026 0.054 Uiso 1 1 calc R U . . .
H1B H 0.807441 0.575300 0.380103 0.054 Uiso 1 1 calc R U . . .
C3 C 0.7453(2) 0.2953(2) 0.45057(15) 0.0498(5) Uani 1 1 d . . . . .
H3A H 0.818452 0.361328 0.446989 0.060 Uiso 1 1 calc R U . . .
H3B H 0.763987 0.189001 0.430475 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8894(2) 0.7675(3) 0.65624(14) 0.0516(5) Uani 1 1 d . . . . .
H8A H 0.842725 0.844117 0.688016 0.062 Uiso 1 1 calc R U . . .
H8B H 0.975758 0.766639 0.691078 0.062 Uiso 1 1 calc R U . . .
C9 C 0.89072(18) 0.8236(3) 0.55295(15) 0.0478(5) Uani 1 1 d . . . . .
H9A H 0.933954 0.924873 0.554783 0.057 Uiso 1 1 calc R U . . .
H9B H 0.937201 0.748004 0.520202 0.057 Uiso 1 1 calc R U . . .
C6 C 0.90745(19) 0.4678(3) 0.63329(15) 0.0508(5) Uani 1 1 d . . . . .
H6A H 0.988128 0.461766 0.676759 0.061 Uiso 1 1 calc R U . . .
H6B H 0.924598 0.491186 0.568692 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7226(2) 0.2905(3) 0.55571(16) 0.0547(5) Uani 1 1 d . . . . .
H4A H 0.681522 0.191203 0.566497 0.066 Uiso 1 1 calc R U . . .
H4B H 0.665502 0.375948 0.565447 0.066 Uiso 1 1 calc R U . . .
C5 C 0.8435(2) 0.3061(3) 0.63088(16) 0.0560(6) Uani 1 1 d . . . . .
H5A H 0.823459 0.284343 0.694816 0.067 Uiso 1 1 calc R U . . .
H5B H 0.903107 0.225923 0.617529 0.067 Uiso 1 1 calc R U . . .
H1 H 0.639(2) 0.332(3) 0.3262(19) 0.062(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4411(15) . ?
S1 O2 1.4327(15) . ?
S1 N2 1.5910(16) . ?
S1 C1 1.770(2) . ?
O1W H1WA 0.8498 . ?
O1W H1WB 0.8499 . ?
N2 H2 0.8600 . ?
N2 C9 1.462(2) . ?
N1 C2 1.468(3) . ?
N1 C3 1.474(3) . ?
N1 H1 0.83(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.520(3) . ?
C7 C6 1.518(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.524(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.529(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 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
O1 S1 N2 108.76(9) . . ?
O1 S1 C1 106.20(9) . . ?
O2 S1 O1 118.96(10) . . ?
O2 S1 N2 107.46(9) . . ?
O2 S1 C1 107.28(10) . . ?
N2 S1 C1 107.73(9) . . ?
H1WA O1W H1WB 104.5 . . ?
S1 N2 H2 118.8 . . ?
C9 N2 S1 122.45(13) . . ?
C9 N2 H2 118.8 . . ?
C2 N1 C3 114.19(16) . . ?
C2 N1 H1 108.6(17) . . ?
C3 N1 H1 110.8(17) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
N1 C2 C1 113.89(16) . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C6 C7 C8 114.66(17) . . ?
S1 C1 H1A 108.7 . . ?
S1 C1 H1B 108.7 . . ?
C2 C1 S1 114.29(14) . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
N1 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
N1 C3 C4 112.41(17) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 C7 115.64(17) . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
N2 C9 C8 111.54(16) . . ?
N2 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
C7 C6 C5 115.15(17) . . ?
H6A C6 H6B 107.5 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 113.60(18) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C6 C5 C4 114.72(17) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?

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
S1 N2 C9 C8 -154.23(16) . . . . ?
O1 S1 N2 C9 -35.22(18) . . . . ?
O1 S1 C1 C2 -179.11(14) . . . . ?
O2 S1 N2 C9 -165.22(16) . . . . ?
O2 S1 C1 C2 -50.92(18) . . . . ?
N2 S1 C1 C2 64.51(17) . . . . ?
N1 C2 C1 S1 -165.85(14) . . . . ?
N1 C3 C4 C5 -151.88(18) . . . . ?
C2 N1 C3 C4 76.2(2) . . . . ?
C7 C8 C9 N2 62.8(2) . . . . ?
C7 C6 C5 C4 65.5(2) . . . . ?
C1 S1 N2 C9 79.48(17) . . . . ?
C3 N1 C2 C1 66.0(2) . . . . ?
C3 C4 C5 C6 67.8(2) . . . . ?
C8 C7 C6 C5 -173.00(17) . . . . ?
C6 C7 C8 C9 67.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
