# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20kaw05
_database_code_depnum_ccdc_archive 'CCDC 2017257'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 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         "C5 H12 N O2 S, C5 H12 N O2, 2(C2 H O4')"
_chemical_formula_sum            'C14 H26 N2 O12 S'
_chemical_formula_weight         446.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   5.6669(3)
_cell_length_b                   19.0508(9)
_cell_length_c                   9.7996(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.181(1)
_cell_angle_gamma                90
_cell_volume                     1037.87(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      74.55

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.074
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_max          0.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.973
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            17076
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.599
_diffrn_reflns_theta_max         74.698
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4136
_reflns_number_gt                4079
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.972

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.3722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4136
_refine_ls_number_parameters     295
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.94253(16) 0.74214(4) 0.11028(9) 0.0407(2) Uani 1 1 d . . . . .
O1 O 0.9647(4) 0.61486(10) 0.38825(19) 0.0255(4) Uani 1 1 d . . . . .
H1 H 1.055(8) 0.598(2) 0.475(4) 0.038 Uiso 1 1 d . U . . .
O2 O 0.8317(3) 0.50470(9) 0.34771(18) 0.0175(4) Uani 1 1 d . . . . .
O3 O 0.1661(3) 0.38308(10) 0.26402(19) 0.0212(4) Uani 1 1 d . . . . .
H3 H 0.097(7) 0.396(2) 0.179(4) 0.032 Uiso 1 1 d . U . . .
O4 O 0.3128(3) 0.49257(10) 0.29843(18) 0.0187(4) Uani 1 1 d . . . . .
O5 O -0.1440(3) 0.58954(10) -0.29522(18) 0.0190(4) Uani 1 1 d . . . . .
H5 H -0.270(7) 0.5897(19) -0.254(4) 0.028 Uiso 1 1 d . U . . .
O6 O 0.0665(3) 0.57226(11) -0.07834(18) 0.0213(4) Uani 1 1 d . . . . .
O7 O 0.4790(3) 0.58161(10) -0.18010(17) 0.0183(4) Uani 1 1 d . . . . .
O8 O 0.2628(3) 0.57290(9) -0.39503(17) 0.0166(3) Uani 1 1 d . . . . .
O9 O 1.2788(3) 0.41130(10) 0.94330(17) 0.0166(3) Uani 1 1 d . . . . .
H9 H 1.387(7) 0.411(2) 0.911(4) 0.025 Uiso 1 1 d . U . . .
O10 O 1.0644(3) 0.42165(10) 0.72610(18) 0.0201(4) Uani 1 1 d . . . . .
O11 O 0.6554(3) 0.41583(10) 0.82819(17) 0.0181(4) Uani 1 1 d . . . . .
O12 O 0.8690(3) 0.41799(10) 1.04347(17) 0.0178(4) Uani 1 1 d . . . . .
N1 N 0.5765(4) 0.53334(11) 0.0962(2) 0.0160(4) Uani 1 1 d . . . . .
H1B H 0.658(7) 0.495(2) 0.092(4) 0.024 Uiso 1 1 d . U . . .
H1A H 0.461(7) 0.5233(19) 0.138(4) 0.024 Uiso 1 1 d . U . . .
H1C H 0.512(7) 0.5445(19) 0.016(4) 0.024 Uiso 1 1 d . U . . .
N2 N 0.5679(4) 0.46257(12) 0.5518(2) 0.0165(4) Uani 1 1 d . . . . .
H2A H 0.692(7) 0.4692(19) 0.510(4) 0.025 Uiso 1 1 d . U . . .
H2B H 0.497(7) 0.504(2) 0.562(4) 0.025 Uiso 1 1 d . U . . .
H2C H 0.637(7) 0.4477(19) 0.632(4) 0.025 Uiso 1 1 d . U . . .
C1 C 0.8449(4) 0.56533(13) 0.3120(2) 0.0160(5) Uani 1 1 d . . . . .
C2 C 0.7241(4) 0.59173(12) 0.1691(3) 0.0164(5) Uani 1 1 d . . . . .
H2 H 0.852527 0.603298 0.115656 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5666(5) 0.65707(14) 0.1710(3) 0.0223(5) Uani 1 1 d . . . . .
H3A H 0.459478 0.661649 0.078740 0.027 Uiso 1 1 calc R U . . .
H3B H 0.463175 0.649635 0.240353 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7026(5) 0.72613(14) 0.2047(3) 0.0260(6) Uani 1 1 d . . . . .
H4A H 0.771794 0.726984 0.305503 0.031 Uiso 1 1 calc R U . . .
H4B H 0.585763 0.765211 0.185282 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7710(11) 0.7465(2) -0.0649(4) 0.0639(13) Uani 1 1 d . . . . .
H5A H 0.706689 0.699849 -0.093566 0.096 Uiso 1 1 calc R U . . .
H5B H 0.875240 0.762220 -0.127805 0.096 Uiso 1 1 calc R U . . .
H5C H 0.637800 0.779653 -0.068546 0.096 Uiso 1 1 calc R U . . .
C6 C 0.2877(4) 0.43297(13) 0.3376(2) 0.0164(5) Uani 1 1 d . . . . .
C7 C 0.3950(4) 0.40828(14) 0.4845(2) 0.0175(5) Uani 1 1 d . . . . .
H7 H 0.261329 0.405688 0.537612 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5113(5) 0.33574(14) 0.4897(3) 0.0213(5) Uani 1 1 d . . . . .
H8A H 0.574854 0.323379 0.588060 0.026 Uiso 1 1 calc R U . . .
H8B H 0.385992 0.300876 0.451993 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7149(5) 0.33029(14) 0.4088(3) 0.0247(5) Uani 1 1 d . . . . .
H9A H 0.658773 0.348184 0.313174 0.030 Uiso 1 1 calc R U . . .
H9B H 0.851402 0.359876 0.454191 0.030 Uiso 1 1 calc R U . . .
C10 C 0.7998(6) 0.25465(16) 0.4023(4) 0.0411(8) Uani 1 1 d . . . . .
H10A H 0.852233 0.236528 0.496877 0.062 Uiso 1 1 calc R U . . .
H10B H 0.934496 0.252999 0.352916 0.062 Uiso 1 1 calc R U . . .
H10C H 0.667266 0.225790 0.352757 0.062 Uiso 1 1 calc R U . . .
C11 C 0.0545(4) 0.58040(12) -0.2023(2) 0.0146(4) Uani 1 1 d . . . . .
C12 C 0.2844(4) 0.57866(12) -0.2664(2) 0.0136(4) Uani 1 1 d . . . . .
C13 C 1.0790(4) 0.41528(12) 0.8503(2) 0.0136(4) Uani 1 1 d . . . . .
C14 C 0.8496(4) 0.41551(12) 0.9148(2) 0.0136(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.803(5) . ?
S1 C4 1.812(3) . ?
O1 C1 1.309(3) . ?
O1 H1 0.96(4) . ?
O2 C1 1.213(3) . ?
O3 C6 1.306(3) . ?
O3 H3 0.88(4) . ?
O4 C6 1.216(3) . ?
O5 C11 1.314(3) . ?
O5 H5 0.88(4) . ?
O6 C11 1.214(3) . ?
O7 C12 1.254(3) . ?
O8 C12 1.247(3) . ?
O9 C13 1.311(3) . ?
O9 H9 0.74(4) . ?
O10 C13 1.210(3) . ?
O11 C14 1.253(3) . ?
O12 C14 1.245(3) . ?
N1 C2 1.488(3) . ?
N1 H1B 0.87(4) . ?
N1 H1A 0.86(4) . ?
N1 H1C 0.82(4) . ?
N2 C7 1.488(3) . ?
N2 H2A 0.89(4) . ?
N2 H2B 0.89(4) . ?
N2 H2C 0.85(4) . ?
C1 C2 1.520(3) . ?
C2 C3 1.534(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.525(3) . ?
C7 C8 1.528(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.525(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.552(3) . ?
C13 C14 1.552(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C4 100.0(2) . . ?
C1 O1 H1 113(2) . . ?
C6 O3 H3 114(3) . . ?
C11 O5 H5 110(2) . . ?
C13 O9 H9 112(3) . . ?
C2 N1 H1B 114(2) . . ?
C2 N1 H1A 110(2) . . ?
H1B N1 H1A 107(3) . . ?
C2 N1 H1C 111(3) . . ?
H1B N1 H1C 109(3) . . ?
H1A N1 H1C 106(3) . . ?
C7 N2 H2A 114(2) . . ?
C7 N2 H2B 113(2) . . ?
H2A N2 H2B 110(3) . . ?
C7 N2 H2C 109(2) . . ?
H2A N2 H2C 102(3) . . ?
H2B N2 H2C 109(3) . . ?
O2 C1 O1 125.1(2) . . ?
O2 C1 C2 122.6(2) . . ?
O1 C1 C2 112.3(2) . . ?
N1 C2 C1 107.80(19) . . ?
N1 C2 C3 109.8(2) . . ?
C1 C2 C3 114.6(2) . . ?
N1 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C4 C3 C2 115.5(2) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 S1 115.56(19) . . ?
C3 C4 H4A 108.4 . . ?
S1 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
S1 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 126.0(2) . . ?
O4 C6 C7 122.4(2) . . ?
O3 C6 C7 111.6(2) . . ?
N2 C7 C6 108.2(2) . . ?
N2 C7 C8 111.8(2) . . ?
C6 C7 C8 113.6(2) . . ?
N2 C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
C9 C8 C7 114.2(2) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 111.3(2) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 O5 125.8(2) . . ?
O6 C11 C12 120.9(2) . . ?
O5 C11 C12 113.3(2) . . ?
O8 C12 O7 125.9(2) . . ?
O8 C12 C11 119.0(2) . . ?
O7 C12 C11 115.1(2) . . ?
O10 C13 O9 125.9(2) . . ?
O10 C13 C14 120.7(2) . . ?
O9 C13 C14 113.30(19) . . ?
O12 C14 O11 125.4(2) . . ?
O12 C14 C13 119.8(2) . . ?
O11 C14 C13 114.77(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 5.9(3) . . . . ?
O1 C1 C2 N1 -175.1(2) . . . . ?
O2 C1 C2 C3 128.4(2) . . . . ?
O1 C1 C2 C3 -52.6(3) . . . . ?
N1 C2 C3 C4 -163.5(2) . . . . ?
C1 C2 C3 C4 75.0(3) . . . . ?
C2 C3 C4 S1 47.4(3) . . . . ?
C5 S1 C4 C3 63.4(2) . . . . ?
O4 C6 C7 N2 -12.1(3) . . . . ?
O3 C6 C7 N2 169.09(19) . . . . ?
O4 C6 C7 C8 -136.9(2) . . . . ?
O3 C6 C7 C8 44.3(3) . . . . ?
N2 C7 C8 C9 -63.8(3) . . . . ?
C6 C7 C8 C9 59.0(3) . . . . ?
C7 C8 C9 C10 -172.4(2) . . . . ?
O6 C11 C12 O8 165.6(2) . . . . ?
O5 C11 C12 O8 -12.8(3) . . . . ?
O6 C11 C12 O7 -12.7(3) . . . . ?
O5 C11 C12 O7 168.8(2) . . . . ?
O10 C13 C14 O12 -170.8(2) . . . . ?
O9 C13 C14 O12 6.0(3) . . . . ?
O10 C13 C14 O11 6.6(3) . . . . ?
O9 C13 C14 O11 -176.7(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 H1 O8 0.96(4) 1.63(4) 2.571(2) 166(4) 1_656 yes
O3 H3 O12 0.88(4) 1.72(4) 2.557(2) 158(4) 1_454 yes
O5 H5 O7 0.88(4) 1.73(4) 2.607(2) 174(4) 1_455 yes
O9 H9 O11 0.74(4) 1.86(4) 2.602(2) 177(4) 1_655 yes
N1 H1B O12 0.87(4) 2.00(4) 2.859(3) 166(3) 1_554 yes
N1 H1A O4 0.86(4) 2.00(4) 2.813(3) 156(3) . yes
N1 H1C O7 0.82(4) 2.03(4) 2.811(3) 159(3) . yes
N2 H2A O2 0.89(4) 2.02(4) 2.835(3) 151(3) . yes
N2 H2B O8 0.89(4) 1.98(4) 2.833(3) 160(3) 1_556 yes
N2 H2C O11 0.85(4) 2.00(4) 2.802(3) 156(3) . yes

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw06_a
_database_code_depnum_ccdc_archive 'CCDC 2017258'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2021-11-11 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         'C5 H12 N O2 S, C2 H O4'
_chemical_formula_sum            'C7 H13 N O6 S'
_chemical_formula_weight         239.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5359(8)
_cell_length_b                   9.4406(14)
_cell_length_c                   10.6027(15)
_cell_angle_alpha                90.156(6)
_cell_angle_beta                 103.956(6)
_cell_angle_gamma                103.969(6)
_cell_volume                     520.77(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5785
_cell_measurement_theta_min      4.84
_cell_measurement_theta_max      72.40
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.062
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_max          0.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    2.921
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.5734
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            6746
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.837
_diffrn_reflns_theta_max         72.395
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2029
_reflns_number_gt                1957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.2076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2029
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22611(7) 0.22628(4) 0.58884(3) 0.01739(14) Uani 1 1 d . . . . .
O1 O 0.36554(18) 0.54841(10) 0.11409(10) 0.0128(2) Uani 1 1 d . . . . .
H1 H 0.484(4) 0.624(2) 0.1064(19) 0.019 Uiso 1 1 d . U . . .
O2 O 0.70652(18) 0.46100(10) 0.20612(10) 0.0147(2) Uani 1 1 d . . . . .
O3 O -0.65046(18) -0.13823(10) 0.12286(10) 0.0123(2) Uani 1 1 d . . . . .
H3 H -0.781(4) -0.092(2) 0.1369(18) 0.018 Uiso 1 1 d . U . . .
O4 O -0.38447(18) 0.08405(10) 0.17909(10) 0.0148(2) Uani 1 1 d . . . . .
O5 O 0.00720(17) -0.01932(10) 0.14647(9) 0.0116(2) Uani 1 1 d . . . . .
O6 O -0.26022(18) -0.23869(10) 0.07818(9) 0.0108(2) Uani 1 1 d . . . . .
N1 N 0.0284(2) 0.29944(12) 0.12486(12) 0.0102(2) Uani 1 1 d . . . . .
H1A H -0.040(4) 0.375(2) 0.1333(18) 0.015 Uiso 1 1 d . U . . .
H1B H 0.040(4) 0.290(2) 0.046(2) 0.015 Uiso 1 1 d . U . . .
H1C H -0.079(4) 0.218(2) 0.1417(18) 0.015 Uiso 1 1 d . U . . .
C1 C 0.4773(3) 0.45093(13) 0.17565(13) 0.0101(3) Uani 1 1 d . . . . .
C2 C 0.2910(3) 0.32097(14) 0.21234(13) 0.0106(3) Uani 1 1 d . . . . .
H2 H 0.352522 0.231374 0.202086 0.013 Uiso 1 1 calc R U . . .
C3 C 0.2892(3) 0.34259(15) 0.35606(13) 0.0131(3) Uani 1 1 d . . . . .
H3A H 0.464160 0.393996 0.406307 0.016 Uiso 1 1 calc R U . . .
H3B H 0.172259 0.405319 0.362368 0.016 Uiso 1 1 calc R U . . .
C4 C 0.2031(3) 0.19806(15) 0.41654(13) 0.0155(3) Uani 1 1 d . . . . .
H4A H 0.311819 0.132235 0.404768 0.019 Uiso 1 1 calc R U . . .
H4B H 0.023114 0.150058 0.371021 0.019 Uiso 1 1 calc R U . . .
C5 C -0.0807(3) 0.2640(2) 0.58201(17) 0.0259(4) Uani 1 1 d . . . . .
H5A H -0.098721 0.347267 0.528646 0.039 Uiso 1 1 calc R U . . .
H5B H -0.091326 0.287519 0.670280 0.039 Uiso 1 1 calc R U . . .
H5C H -0.218694 0.177890 0.543382 0.039 Uiso 1 1 calc R U . . .
C6 C -0.4281(2) -0.04499(14) 0.14527(12) 0.0088(3) Uani 1 1 d . . . . .
C7 C -0.2096(2) -0.10916(14) 0.12117(12) 0.0089(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
S1 C5 1.8026(16) . ?
S1 C4 1.8148(14) . ?
O1 C1 1.3188(16) . ?
O1 H1 0.87(2) . ?
O2 C1 1.2114(17) . ?
O3 C6 1.2966(16) . ?
O3 H3 0.97(2) . ?
O4 C6 1.2186(17) . ?
O5 C7 1.2584(17) . ?
O6 C7 1.2456(17) . ?
N1 C2 1.4902(17) . ?
N1 H1A 0.90(2) . ?
N1 H1B 0.86(2) . ?
N1 H1C 0.90(2) . ?
C1 C2 1.5185(18) . ?
C2 C3 1.5395(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.5292(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.5485(17) . ?

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 C4 100.45(7) . . ?
C1 O1 H1 108.5(13) . . ?
C6 O3 H3 111.1(11) . . ?
C2 N1 H1A 112.1(12) . . ?
C2 N1 H1B 107.8(12) . . ?
H1A N1 H1B 109.6(17) . . ?
C2 N1 H1C 111.3(12) . . ?
H1A N1 H1C 107.5(17) . . ?
H1B N1 H1C 108.5(17) . . ?
O2 C1 O1 125.55(12) . . ?
O2 C1 C2 120.66(12) . . ?
O1 C1 C2 113.74(11) . . ?
N1 C2 C1 110.97(11) . . ?
N1 C2 C3 111.38(11) . . ?
C1 C2 C3 109.63(11) . . ?
N1 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C4 C3 C2 112.62(11) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 S1 111.49(10) . . ?
C3 C4 H4A 109.3 . . ?
S1 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
S1 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 125.60(11) . . ?
O4 C6 C7 120.09(11) . . ?
O3 C6 C7 114.28(11) . . ?
O6 C7 O5 126.49(11) . . ?
O6 C7 C6 119.45(11) . . ?
O5 C7 C6 114.05(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
O2 C1 C2 N1 -157.65(12) . . . . ?
O1 C1 C2 N1 24.53(15) . . . . ?
O2 C1 C2 C3 78.91(15) . . . . ?
O1 C1 C2 C3 -98.91(13) . . . . ?
N1 C2 C3 C4 80.96(14) . . . . ?
C1 C2 C3 C4 -155.84(11) . . . . ?
C2 C3 C4 S1 175.72(9) . . . . ?
C5 S1 C4 C3 86.10(12) . . . . ?
O4 C6 C7 O6 -175.17(12) . . . . ?
O3 C6 C7 O6 3.03(17) . . . . ?
O4 C6 C7 O5 3.65(17) . . . . ?
O3 C6 C7 O5 -178.15(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
O1 H1 O3 0.87(2) 2.543(19) 2.9827(14) 112.4(15) 1_665 yes
O1 H1 O6 0.87(2) 1.76(2) 2.6175(14) 171.7(19) 1_665 yes
O3 H3 O5 0.97(2) 1.52(2) 2.4837(13) 175.1(18) 1_455 yes
O3 H3 O6 0.97(2) 2.600(19) 3.1936(14) 119.8(14) 1_455 yes
N1 H1A O2 0.90(2) 2.07(2) 2.8790(15) 149.0(16) 1_455 yes
N1 H1B O3 0.86(2) 2.56(2) 3.0630(16) 118.5(15) 2_455 yes
N1 H1B O6 0.86(2) 2.12(2) 2.8796(15) 146.5(17) 2 yes
N1 H1C O4 0.90(2) 1.98(2) 2.8435(15) 161.8(17) . yes
N1 H1C O5 0.90(2) 2.403(19) 2.9948(15) 123.7(15) . yes


_refine_diff_density_max         0.452
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw37
_database_code_depnum_ccdc_archive 'CCDC 2051774'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-11-11 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         'C4 H10 N O2 S, C5 H12 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C13 H24 N2 O12 S'
_chemical_formula_weight         432.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6975(4)
_cell_length_b                   9.3292(8)
_cell_length_c                   9.9228(7)
_cell_angle_alpha                109.364(5)
_cell_angle_beta                 102.250(4)
_cell_angle_gamma                101.496(5)
_cell_volume                     465.00(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6743
_cell_measurement_theta_min      4.95
_cell_measurement_theta_max      68.47
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.024
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_max          0.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    2.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.2949
_exptl_absorpt_correction_T_max  0.5137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            9527
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.954
_diffrn_reflns_theta_max         68.466
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             3172
_reflns_number_gt                2836
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.867

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1095P)²+0.0197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3172
_refine_ls_number_parameters     285
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.3488(3) 0.9068(2) 0.76859(19) 0.0303(4) Uani 1 1 d . . . . .
O1 O 0.6864(8) 0.7627(6) 0.5329(5) 0.0273(10) Uani 1 1 d D . . . .
H1 H 0.608(15) 0.723(10) 0.440(4) 0.041 Uiso 1 1 d D U . . .
O2 O 0.7234(7) 0.5158(6) 0.4774(5) 0.0263(10) Uani 1 1 d . . . . .
O3 O 0.2730(8) 0.2377(6) 0.4619(5) 0.0310(11) Uani 1 1 d D . . . .
H3 H 0.365(16) 0.283(11) 0.554(5) 0.046 Uiso 1 1 d D U . . .
O4 O 0.2247(8) 0.4822(6) 0.5221(5) 0.0248(10) Uani 1 1 d . . . . .
O5 O 1.7828(8) 0.7056(6) 1.1919(5) 0.0254(10) Uani 1 1 d D . . . .
H5 H 1.901(12) 0.702(11) 1.153(10) 0.038 Uiso 1 1 d D U . . .
O6 O 1.5461(8) 0.6645(6) 0.9626(5) 0.0285(11) Uani 1 1 d . . . . .
O7 O 1.1540(8) 0.6949(6) 1.0734(5) 0.0243(9) Uani 1 1 d . . . . .
O8 O 1.3597(7) 0.6678(5) 1.2755(5) 0.0251(10) Uani 1 1 d . . . . .
O9 O -0.8131(7) 0.2886(6) -0.1934(5) 0.0268(10) Uani 1 1 d D . . . .
H9 H -0.920(14) 0.312(11) -0.147(10) 0.040 Uiso 1 1 d D U . . .
O10 O -0.5754(8) 0.3348(6) 0.0358(5) 0.0258(10) Uani 1 1 d . . . . .
O11 O -0.1751(7) 0.3200(6) -0.0703(5) 0.0259(10) Uani 1 1 d . . . . .
O12 O -0.3962(7) 0.3228(6) -0.2828(5) 0.0257(10) Uani 1 1 d . . . . .
N1 N 1.0050(10) 0.5850(7) 0.7575(6) 0.0255(12) Uani 1 1 d D . . . .
H1A H 1.072(15) 0.629(10) 0.852(4) 0.038 Uiso 1 1 d D U . . .
H1B H 0.889(13) 0.497(6) 0.726(10) 0.038 Uiso 1 1 d D U . . .
H1C H 1.111(14) 0.571(11) 0.708(10) 0.038 Uiso 1 1 d D U . . .
N2 N -0.0496(10) 0.4211(7) 0.2443(6) 0.0226(11) Uani 1 1 d D . . . .
H2A H -0.148(13) 0.395(9) 0.157(5) 0.034 Uiso 1 1 d D U . . .
H2B H 0.066(12) 0.509(6) 0.275(9) 0.034 Uiso 1 1 d D U . . .
H2C H -0.156(14) 0.431(11) 0.293(9) 0.034 Uiso 1 1 d D U . . .
C1 C 0.7576(10) 0.6493(8) 0.5660(7) 0.0226(13) Uani 1 1 d . . . . .
C2 C 0.8776(11) 0.7035(9) 0.7336(7) 0.0251(14) Uani 1 1 d . . . . .
H2 H 0.738157 0.698264 0.779987 0.030 Uiso 1 1 calc R U . . .
C3 C 1.0538(12) 0.8719(8) 0.8126(7) 0.0269(14) Uani 1 1 d . . . . .
H3A H 1.092616 0.900830 0.922022 0.032 Uiso 1 1 calc R U . . .
H3B H 0.963597 0.944526 0.787760 0.032 Uiso 1 1 calc R U . . .
C4 C 1.2574(12) 0.9243(8) 0.5912(7) 0.0279(14) Uani 1 1 d . . . . .
H4A H 1.167460 0.818907 0.512413 0.042 Uiso 1 1 calc R U . . .
H4B H 1.407457 0.970466 0.569051 0.042 Uiso 1 1 calc R U . . .
H4C H 1.147480 0.993195 0.595495 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1969(10) 0.3512(8) 0.4331(7) 0.0229(13) Uani 1 1 d . . . . .
C6 C 0.0764(11) 0.2994(8) 0.2642(7) 0.0244(13) Uani 1 1 d . . . . .
H6 H 0.216784 0.307134 0.218782 0.029 Uiso 1 1 calc R U . . .
C7 C -0.1002(12) 0.1318(8) 0.1793(7) 0.0270(14) Uani 1 1 d . . . . .
H7A H -0.007647 0.056893 0.195828 0.032 Uiso 1 1 calc R U . . .
H7B H -0.144450 0.110217 0.070967 0.032 Uiso 1 1 calc R U . . .
C8 C -0.3480(12) 0.0946(8) 0.2199(8) 0.0262(13) Uani 1 1 d . . . . .
H8A H -0.425523 0.181181 0.223039 0.031 Uiso 1 1 calc R U . . .
H8B H -0.466041 -0.004770 0.139739 0.031 Uiso 1 1 calc R U . . .
C9 C -0.3134(13) 0.0763(9) 0.3684(9) 0.0337(15) Uani 1 1 d . . . . .
H9A H -0.206681 0.006907 0.374658 0.051 Uiso 1 1 calc R U . . .
H9B H -0.477438 0.029467 0.376108 0.051 Uiso 1 1 calc R U . . .
H9C H -0.233563 0.180835 0.450539 0.051 Uiso 1 1 calc R U . . .
C10 C 1.5720(10) 0.6839(7) 1.0916(7) 0.0216(12) Uani 1 1 d . . . . .
C11 C 1.3440(10) 0.6832(8) 1.1549(7) 0.0210(12) Uani 1 1 d . . . . .
C12 C -0.6004(11) 0.3132(8) -0.0934(7) 0.0220(13) Uani 1 1 d . . . . .
C13 C -0.3730(11) 0.3178(7) -0.1567(7) 0.0212(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.798(7) . ?
S1 C3 1.820(6) . ?
O1 C1 1.318(8) . ?
O1 H1 0.85(3) . ?
O2 C1 1.211(9) . ?
O3 C5 1.312(8) . ?
O3 H3 0.86(3) . ?
O4 C5 1.202(8) . ?
O5 C10 1.318(7) . ?
O5 H5 0.85(3) . ?
O6 C10 1.203(8) . ?
O7 C11 1.254(7) . ?
O8 C11 1.238(7) . ?
O9 C12 1.316(7) . ?
O9 H9 0.86(3) . ?
O10 C12 1.201(8) . ?
O11 C13 1.255(7) . ?
O12 C13 1.247(8) . ?
N1 C2 1.492(9) . ?
N1 H1A 0.85(3) . ?
N1 H1B 0.86(3) . ?
N1 H1C 0.86(3) . ?
N2 C6 1.502(8) . ?
N2 H2A 0.85(3) . ?
N2 H2B 0.86(3) . ?
N2 H2C 0.85(3) . ?
C1 C2 1.520(9) . ?
C2 C3 1.520(10) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.535(9) . ?
C6 C7 1.519(10) . ?
C6 H6 1.0000 . ?
C7 C8 1.554(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.558(7) . ?
C12 C13 1.555(8) . ?

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 C3 102.7(3) . . ?
C1 O1 H1 107(6) . . ?
C5 O3 H3 105(7) . . ?
C10 O5 H5 111(7) . . ?
C12 O9 H9 108(7) . . ?
C2 N1 H1A 100(6) . . ?
C2 N1 H1B 106(7) . . ?
H1A N1 H1B 115(9) . . ?
C2 N1 H1C 113(7) . . ?
H1A N1 H1C 114(9) . . ?
H1B N1 H1C 108(9) . . ?
C6 N2 H2A 115(5) . . ?
C6 N2 H2B 107(6) . . ?
H2A N2 H2B 114(8) . . ?
C6 N2 H2C 111(6) . . ?
H2A N2 H2C 98(9) . . ?
H2B N2 H2C 111(8) . . ?
O2 C1 O1 125.5(6) . . ?
O2 C1 C2 123.1(6) . . ?
O1 C1 C2 111.3(6) . . ?
N1 C2 C3 111.6(5) . . ?
N1 C2 C1 107.6(5) . . ?
C3 C2 C1 115.8(5) . . ?
N1 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C2 C3 S1 116.2(5) . . ?
C2 C3 H3A 108.2 . . ?
S1 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
S1 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
S1 C4 H4A 109.5 . . ?
S1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 O3 126.7(6) . . ?
O4 C5 C6 122.5(6) . . ?
O3 C5 C6 110.8(5) . . ?
N2 C6 C7 111.6(5) . . ?
N2 C6 C5 107.1(5) . . ?
C7 C6 C5 117.1(5) . . ?
N2 C6 H6 106.8 . . ?
C7 C6 H6 106.8 . . ?
C5 C6 H6 106.8 . . ?
C6 C7 C8 116.7(5) . . ?
C6 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
C6 C7 H7B 108.1 . . ?
C8 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C7 114.0(6) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C10 O5 126.2(5) . . ?
O6 C10 C11 120.7(5) . . ?
O5 C10 C11 113.1(5) . . ?
O8 C11 O7 125.6(5) . . ?
O8 C11 C10 119.5(5) . . ?
O7 C11 C10 114.8(5) . . ?
O10 C12 O9 125.2(5) . . ?
O10 C12 C13 121.4(5) . . ?
O9 C12 C13 113.3(5) . . ?
O12 C13 O11 125.6(5) . . ?
O12 C13 C12 119.7(5) . . ?
O11 C13 C12 114.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 16.2(8) . . . . ?
O1 C1 C2 N1 -166.9(4) . . . . ?
O2 C1 C2 C3 141.9(6) . . . . ?
O1 C1 C2 C3 -41.3(7) . . . . ?
N1 C2 C3 S1 54.4(6) . . . . ?
C1 C2 C3 S1 -69.2(7) . . . . ?
C4 S1 C3 C2 79.3(5) . . . . ?
O4 C5 C6 N2 -14.3(7) . . . . ?
O3 C5 C6 N2 169.0(5) . . . . ?
O4 C5 C6 C7 -140.4(6) . . . . ?
O3 C5 C6 C7 42.9(7) . . . . ?
N2 C6 C7 C8 -58.2(7) . . . . ?
C5 C6 C7 C8 65.6(7) . . . . ?
C6 C7 C8 C9 -74.5(8) . . . . ?
O6 C10 C11 O8 164.0(6) . . . . ?
O5 C10 C11 O8 -15.4(8) . . . . ?
O6 C10 C11 O7 -14.3(9) . . . . ?
O5 C10 C11 O7 166.4(6) . . . . ?
O10 C12 C13 O12 -167.5(6) . . . . ?
O9 C12 C13 O12 10.7(9) . . . . ?
O10 C12 C13 O11 10.8(9) . . . . ?
O9 C12 C13 O11 -171.0(6) . . . . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.103


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_20kaw39
_database_code_depnum_ccdc_archive 'CCDC 2017250'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2021-11-11 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         ?
_chemical_formula_sum            'C15 H28 N2 O12 S'
_chemical_formula_weight         460.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6972(2)
_cell_length_b                   9.4773(3)
_cell_length_c                   10.1212(4)
_cell_angle_alpha                90.857(2)
_cell_angle_beta                 104.853(2)
_cell_angle_gamma                97.275(2)
_cell_volume                     523.33(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8373
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      72.33
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.046
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_max          0.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.974
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_reflns_number            12515
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.525
_diffrn_reflns_theta_max         72.419
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3899
_reflns_number_gt                3624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.895
_reflns_Friedel_fraction_full    0.923

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1591 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.089(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     304
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38480(18) 0.12266(10) 0.06346(10) 0.0273(2) Uani 1 1 d . . . . .
O1 O 0.8158(5) 0.5430(3) 0.2995(3) 0.0231(6) Uani 1 1 d D . . . .
H1 H 0.905(8) 0.620(4) 0.335(5) 0.035 Uiso 1 1 d D U . . .
O2 O 0.7518(4) 0.5174(2) 0.5088(3) 0.0163(5) Uani 1 1 d . . . . .
O3 O 0.1845(5) 0.4571(3) 0.7538(3) 0.0202(5) Uani 1 1 d D . . . .
H3 H 0.088(8) 0.380(4) 0.725(5) 0.030 Uiso 1 1 d D U . . .
O4 O 0.2541(4) 0.4805(3) 0.5459(3) 0.0184(5) Uani 1 1 d . . . . .
O5 O -0.2922(5) -0.1364(3) 0.3529(3) 0.0182(5) Uani 1 1 d D . . . .
H5 H -0.414(7) -0.092(5) 0.353(5) 0.027 Uiso 1 1 d D U . . .
O6 O -0.0948(5) 0.0869(2) 0.3763(3) 0.0203(5) Uani 1 1 d . . . . .
O7 O 0.3197(4) -0.0203(2) 0.3640(3) 0.0177(5) Uani 1 1 d . . . . .
O8 O 0.1378(4) -0.2379(2) 0.3846(3) 0.0166(5) Uani 1 1 d . . . . .
O9 O 1.2875(4) 1.1361(3) 0.6818(3) 0.0168(5) Uani 1 1 d D . . . .
H9 H 1.408(7) 1.100(5) 0.672(5) 0.025 Uiso 1 1 d D U . . .
O10 O 1.0964(4) 0.9114(2) 0.6694(3) 0.0179(5) Uani 1 1 d . . . . .
O11 O 0.6799(4) 1.0179(2) 0.6817(3) 0.0176(5) Uani 1 1 d . . . . .
O12 O 0.8637(5) 1.2366(2) 0.6721(3) 0.0195(5) Uani 1 1 d . . . . .
N1 N 0.4613(6) 0.2688(3) 0.4374(3) 0.0170(6) Uani 1 1 d D . . . .
H1A H 0.393(8) 0.183(3) 0.414(5) 0.025 Uiso 1 1 d D U . . .
H1B H 0.588(7) 0.262(5) 0.505(4) 0.025 Uiso 1 1 d D U . . .
H1C H 0.358(8) 0.314(5) 0.468(5) 0.025 Uiso 1 1 d D U . . .
N2 N 0.5417(6) 0.7289(3) 0.6149(3) 0.0161(6) Uani 1 1 d D . . . .
H2A H 0.628(8) 0.813(3) 0.640(5) 0.024 Uiso 1 1 d D U . . .
H2B H 0.427(7) 0.733(5) 0.540(3) 0.024 Uiso 1 1 d D U . . .
H2C H 0.646(7) 0.683(5) 0.591(5) 0.024 Uiso 1 1 d D U . . .
C1 C 0.7187(6) 0.4782(4) 0.3904(4) 0.0160(7) Uani 1 1 d . . . . .
C2 C 0.5537(7) 0.3408(4) 0.3278(4) 0.0181(7) Uani 1 1 d . . . . .
H2 H 0.654271 0.277073 0.293232 0.022 Uiso 1 1 calc R U . . .
C3 C 0.3446(7) 0.3716(4) 0.2083(4) 0.0213(8) Uani 1 1 d . . . . .
H3A H 0.413202 0.437130 0.148174 0.026 Uiso 1 1 calc R U . . .
H3B H 0.230229 0.421493 0.244739 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1997(7) 0.2400(4) 0.1219(4) 0.0255(8) Uani 1 1 d . . . . .
H4A H 0.083493 0.271702 0.040922 0.031 Uiso 1 1 calc R U . . .
H4B H 0.101915 0.184867 0.176412 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5578(7) 0.2478(4) -0.0190(4) 0.0273(8) Uani 1 1 d . . . . .
H5A H 0.445533 0.299307 -0.084692 0.041 Uiso 1 1 calc R U . . .
H5B H 0.652861 0.196699 -0.067202 0.041 Uiso 1 1 calc R U . . .
H5C H 0.669502 0.315663 0.049936 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2861(6) 0.5214(4) 0.6645(4) 0.0160(7) Uani 1 1 d . . . . .
C7 C 0.4537(6) 0.6561(4) 0.7269(4) 0.0156(7) Uani 1 1 d . . . . .
H7 H 0.359056 0.720088 0.765960 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6699(6) 0.6197(4) 0.8413(4) 0.0164(7) Uani 1 1 d . . . . .
H8A H 0.602923 0.564891 0.909063 0.020 Uiso 1 1 calc R U . . .
H8B H 0.761899 0.556576 0.801002 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8511(7) 0.7469(4) 0.9175(4) 0.0192(7) Uani 1 1 d . . . . .
H9A H 0.918067 0.802785 0.849098 0.023 Uiso 1 1 calc R U . . .
C10 C 0.7311(8) 0.8445(4) 0.9914(4) 0.0283(8) Uani 1 1 d . . . . .
H10A H 0.663388 0.791159 1.058443 0.043 Uiso 1 1 calc R U . . .
H10B H 0.598901 0.882145 0.925089 0.043 Uiso 1 1 calc R U . . .
H10C H 0.853167 0.923625 1.038545 0.043 Uiso 1 1 calc R U . . .
C11 C 1.0634(7) 0.6905(4) 1.0185(4) 0.0262(8) Uani 1 1 d . . . . .
H11A H 1.001044 0.636376 1.086963 0.039 Uiso 1 1 calc R U . . .
H11B H 1.184463 0.770700 1.064188 0.039 Uiso 1 1 calc R U . . .
H11C H 1.140587 0.628393 0.969046 0.039 Uiso 1 1 calc R U . . .
C12 C -0.0989(6) -0.0412(3) 0.3653(3) 0.0136(7) Uani 1 1 d . . . . .
C13 C 0.1383(6) -0.1070(4) 0.3702(4) 0.0143(7) Uani 1 1 d . . . . .
C14 C 1.0979(6) 1.0391(4) 0.6770(3) 0.0127(6) Uani 1 1 d . . . . .
C15 C 0.8631(6) 1.1050(4) 0.6785(4) 0.0138(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.797(4) . ?
S1 C4 1.815(4) . ?
O1 C1 1.312(5) . ?
O1 H1 0.85(3) . ?
O2 C1 1.210(5) . ?
O3 C6 1.311(5) . ?
O3 H3 0.85(3) . ?
O4 C6 1.216(5) . ?
O5 C12 1.310(4) . ?
O5 H5 0.85(3) . ?
O6 C12 1.215(4) . ?
O7 C13 1.252(5) . ?
O8 C13 1.251(4) . ?
O9 C14 1.317(4) . ?
O9 H9 0.83(3) . ?
O10 C14 1.210(4) . ?
O11 C15 1.253(4) . ?
O12 C15 1.250(4) . ?
N1 C2 1.484(5) . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.87(3) . ?
N1 H1C 0.88(3) . ?
N2 C7 1.496(5) . ?
N2 H2A 0.88(3) . ?
N2 H2B 0.87(3) . ?
N2 H2C 0.86(3) . ?
C1 C2 1.530(5) . ?
C2 C3 1.526(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.530(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.516(5) . ?
C7 C8 1.538(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.537(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.512(5) . ?
C9 C11 1.530(5) . ?
C9 H9A 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.548(5) . ?
C14 C15 1.550(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C4 100.00(19) . . ?
C1 O1 H1 110(4) . . ?
C6 O3 H3 116(3) . . ?
C12 O5 H5 108(3) . . ?
C14 O9 H9 112(3) . . ?
C2 N1 H1A 113(3) . . ?
C2 N1 H1B 107(3) . . ?
H1A N1 H1B 105(4) . . ?
C2 N1 H1C 115(3) . . ?
H1A N1 H1C 108(5) . . ?
H1B N1 H1C 109(4) . . ?
C7 N2 H2A 114(3) . . ?
C7 N2 H2B 114(3) . . ?
H2A N2 H2B 111(4) . . ?
C7 N2 H2C 110(3) . . ?
H2A N2 H2C 102(5) . . ?
H2B N2 H2C 105(4) . . ?
O2 C1 O1 126.4(3) . . ?
O2 C1 C2 122.6(3) . . ?
O1 C1 C2 111.0(3) . . ?
N1 C2 C3 111.8(3) . . ?
N1 C2 C1 108.2(3) . . ?
C3 C2 C1 111.0(3) . . ?
N1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C2 C3 C4 114.7(3) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 S1 114.9(3) . . ?
C3 C4 H4A 108.5 . . ?
S1 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
S1 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 125.6(3) . . ?
O4 C6 C7 122.8(3) . . ?
O3 C6 C7 111.6(3) . . ?
N2 C7 C6 107.7(3) . . ?
N2 C7 C8 111.1(3) . . ?
C6 C7 C8 110.2(3) . . ?
N2 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C9 C8 C7 116.0(3) . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C11 110.4(3) . . ?
C10 C9 C8 112.3(3) . . ?
C11 C9 C8 108.8(3) . . ?
C10 C9 H9A 108.4 . . ?
C11 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O5 125.6(3) . . ?
O6 C12 C13 120.9(3) . . ?
O5 C12 C13 113.5(3) . . ?
O8 C13 O7 125.5(3) . . ?
O8 C13 C12 119.1(3) . . ?
O7 C13 C12 115.3(3) . . ?
O10 C14 O9 126.0(3) . . ?
O10 C14 C15 121.3(3) . . ?
O9 C14 C15 112.7(3) . . ?
O12 C15 O11 124.5(3) . . ?
O12 C15 C14 119.8(3) . . ?
O11 C15 C14 115.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 -2.6(5) . . . . ?
O1 C1 C2 N1 176.8(3) . . . . ?
O2 C1 C2 C3 120.4(4) . . . . ?
O1 C1 C2 C3 -60.2(4) . . . . ?
N1 C2 C3 C4 -70.4(4) . . . . ?
C1 C2 C3 C4 168.6(3) . . . . ?
C2 C3 C4 S1 -51.1(4) . . . . ?
C5 S1 C4 C3 -54.1(3) . . . . ?
O4 C6 C7 N2 5.5(4) . . . . ?
O3 C6 C7 N2 -174.7(3) . . . . ?
O4 C6 C7 C8 -115.9(4) . . . . ?
O3 C6 C7 C8 63.9(4) . . . . ?
N2 C7 C8 C9 62.7(4) . . . . ?
C6 C7 C8 C9 -178.0(3) . . . . ?
C7 C8 C9 C10 62.1(4) . . . . ?
C7 C8 C9 C11 -175.4(3) . . . . ?
O6 C12 C13 O8 166.6(3) . . . . ?
O5 C12 C13 O8 -11.4(4) . . . . ?
O6 C12 C13 O7 -11.0(5) . . . . ?
O5 C12 C13 O7 171.1(3) . . . . ?
O10 C14 C15 O12 -172.6(3) . . . . ?
O9 C14 C15 O12 6.1(4) . . . . ?
O10 C14 C15 O11 5.1(5) . . . . ?
O9 C14 C15 O11 -176.2(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 H1 O8 0.85(3) 1.74(3) 2.568(4) 166(5) 1_665 yes
O3 H3 O12 0.85(3) 1.72(3) 2.568(4) 172(5) 1_445 yes
O5 H5 O7 0.85(3) 1.77(3) 2.618(3) 173(5) 1_455 yes
O9 H9 O11 0.83(3) 1.80(3) 2.624(3) 170(5) 1_655 yes
N1 H1A O7 0.86(3) 1.95(3) 2.790(4) 166(5) . yes
N1 H1B O12 0.87(3) 2.03(3) 2.899(4) 174(5) 1_545 yes
N1 H1C O4 0.88(3) 1.98(3) 2.797(4) 154(5) . yes
N2 H2A O11 0.88(3) 1.95(3) 2.776(4) 156(4) . yes
N2 H2B O8 0.87(3) 2.02(3) 2.878(4) 171(4) 1_565 yes
N2 H2C O2 0.86(3) 1.99(3) 2.795(4) 155(5) . yes

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw27
_database_code_depnum_ccdc_archive 'CCDC 2054514'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2021-01-07 deposited with the CCDC.	2021-11-11 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         'C5 H12 N O2 S, C6 H14 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C15 H28 N2 O12 S'
_chemical_formula_weight         460.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   5.6805(3)
_cell_length_b                   19.7087(9)
_cell_length_c                   9.7095(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.848(3)
_cell_angle_gamma                90
_cell_volume                     1071.01(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3189
_cell_measurement_theta_min      6.45
_cell_measurement_theta_max      71.82

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.061
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_max          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.929
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            12103
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.487
_diffrn_reflns_theta_max         68.303
_diffrn_reflns_theta_full        67.679
_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 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3885
_reflns_number_gt                3599
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.972

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0768P)²+2.3185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.100(13)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3885
_refine_ls_number_parameters     304
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5060(3) 0.67087(9) 0.47788(19) 0.0278(4) Uani 1 1 d . . . . .
O1 O -0.0861(9) 0.6092(3) 0.3084(5) 0.0253(11) Uani 1 1 d D . . . .
H1 H -0.136(14) 0.589(4) 0.232(6) 0.038 Uiso 1 1 d D U . . .
O2 O 0.0662(9) 0.5043(3) 0.3455(5) 0.0250(11) Uani 1 1 d . . . . .
O3 O 0.7471(10) 0.3810(3) 0.4297(5) 0.0288(12) Uani 1 1 d D . . . .
H3 H 0.831(16) 0.396(5) 0.504(7) 0.043 Uiso 1 1 d D U . . .
O4 O 0.5855(9) 0.4851(3) 0.3952(5) 0.0244(11) Uani 1 1 d . . . . .
O5 O -0.3925(9) 0.5692(2) 0.0951(5) 0.0213(10) Uani 1 1 d . . . . .
O6 O -0.6000(8) 0.5788(3) -0.1198(5) 0.0210(10) Uani 1 1 d D . . . .
H6 H -0.742(8) 0.579(5) -0.095(9) 0.031 Uiso 1 1 d D U . . .
O7 O -0.1876(9) 0.5712(3) -0.2226(5) 0.0256(11) Uani 1 1 d . . . . .
O8 O 0.0193(8) 0.5848(3) -0.0055(5) 0.0221(10) Uani 1 1 d . . . . .
O9 O 0.6008(8) 0.4171(3) 0.7487(5) 0.0238(11) Uani 1 1 d . . . . .
O10 O 0.8038(9) 0.4258(3) 0.9670(5) 0.0250(11) Uani 1 1 d . . . . .
O11 O 1.2198(8) 0.4193(3) 0.8663(5) 0.0233(10) Uani 1 1 d D . . . .
H11 H 1.360(8) 0.421(6) 0.843(9) 0.035 Uiso 1 1 d D U . . .
O12 O 1.0215(8) 0.4259(3) 0.6500(5) 0.0244(10) Uani 1 1 d . . . . .
N1 N 0.3136(10) 0.5359(3) 0.5960(6) 0.0203(12) Uani 1 1 d D . . . .
H1C H 0.254(16) 0.497(5) 0.606(9) 0.031 Uiso 1 1 d . U . . .
H1A H 0.367(16) 0.547(5) 0.680(4) 0.031 Uiso 1 1 d D U . . .
H1B H 0.444(10) 0.534(5) 0.562(9) 0.031 Uiso 1 1 d D U . . .
N2 N 0.3263(11) 0.4535(3) 0.1479(6) 0.0218(12) Uani 1 1 d D . . . .
H2A H 0.206(11) 0.466(5) 0.185(9) 0.033 Uiso 1 1 d D U . . .
H2C H 0.432(17) 0.486(5) 0.136(9) 0.033 Uiso 1 1 d . U . . .
H2B H 0.262(15) 0.442(5) 0.065(5) 0.033 Uiso 1 1 d D U . . .
C1 C 0.0375(11) 0.5621(4) 0.3830(7) 0.0192(14) Uani 1 1 d . . . . .
C2 C 0.1327(12) 0.5856(4) 0.5312(7) 0.0225(14) Uani 1 1 d . . . . .
H2 H -0.003275 0.583489 0.584225 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2313(13) 0.6570(4) 0.5467(7) 0.0266(16) Uani 1 1 d . . . . .
H3A H 0.260649 0.668939 0.647208 0.032 Uiso 1 1 calc R U . . .
H3B H 0.108016 0.688506 0.498833 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4018(14) 0.6904(4) 0.2946(8) 0.0299(17) Uani 1 1 d . . . . .
H4A H 0.542506 0.698924 0.249299 0.036 Uiso 1 1 calc R U . . .
H4B H 0.317919 0.650148 0.249076 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2367(17) 0.7507(4) 0.2684(9) 0.0376(19) Uani 1 1 d . . . . .
H5A H 0.083301 0.739488 0.296107 0.056 Uiso 1 1 calc R U . . .
H5B H 0.210828 0.762220 0.168749 0.056 Uiso 1 1 calc R U . . .
H5C H 0.308549 0.789455 0.323223 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6081(12) 0.4269(4) 0.3592(7) 0.0218(14) Uani 1 1 d . . . . .
C7 C 0.4706(12) 0.3973(4) 0.2248(7) 0.0212(14) Uani 1 1 d . . . . .
H7 H 0.585821 0.379553 0.166391 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3082(13) 0.3395(4) 0.2572(8) 0.0233(15) Uani 1 1 d . . . . .
H8A H 0.188746 0.358614 0.309634 0.028 Uiso 1 1 calc R U . . .
H8B H 0.406885 0.306848 0.319734 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1744(12) 0.3002(3) 0.1312(7) 0.0221(14) Uani 1 1 d . . . . .
H9 H 0.075584 0.333029 0.067295 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0069(14) 0.2497(4) 0.1848(9) 0.0303(16) Uani 1 1 d . . . . .
H10A H -0.084465 0.225005 0.105654 0.045 Uiso 1 1 calc R U . . .
H10B H -0.103190 0.274185 0.234487 0.045 Uiso 1 1 calc R U . . .
H10C H 0.101115 0.217459 0.248676 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3431(14) 0.2642(4) 0.0500(8) 0.0292(16) Uani 1 1 d . . . . .
H11A H 0.442458 0.297821 0.012475 0.044 Uiso 1 1 calc R U . . .
H11B H 0.250206 0.238557 -0.027113 0.044 Uiso 1 1 calc R U . . .
H11C H 0.445519 0.233100 0.112299 0.044 Uiso 1 1 calc R U . . .
C12 C -0.4070(12) 0.5758(3) -0.0330(7) 0.0182(13) Uani 1 1 d . . . . .
C13 C -0.1788(10) 0.5776(3) -0.0988(7) 0.0156(12) Uani 1 1 d . . . . .
C14 C 1.0302(12) 0.4213(3) 0.7781(7) 0.0218(14) Uani 1 1 d . . . . .
C15 C 0.7972(11) 0.4216(3) 0.8437(7) 0.0185(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.818(8) . ?
S1 C3 1.820(8) . ?
O1 C1 1.306(9) . ?
O2 C1 1.216(9) . ?
O3 C6 1.313(9) . ?
O4 C6 1.213(9) . ?
O5 C12 1.239(8) . ?
O6 C12 1.265(8) . ?
O7 C13 1.201(8) . ?
O8 C13 1.326(8) . ?
O9 C15 1.323(8) . ?
O10 C15 1.194(8) . ?
O11 C14 1.257(8) . ?
O12 C14 1.240(9) . ?
N1 C2 1.481(9) . ?
N2 C7 1.498(9) . ?
C1 C2 1.520(9) . ?
C2 C3 1.512(10) . ?
C4 C5 1.508(12) . ?
C6 C7 1.518(10) . ?
C7 C8 1.532(10) . ?
C8 C9 1.535(10) . ?
C9 C11 1.517(10) . ?
C9 C10 1.528(10) . ?
C12 C13 1.541(9) . ?
C14 C15 1.564(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C3 103.6(4) . . ?
O2 C1 O1 125.9(6) . . ?
O2 C1 C2 121.7(6) . . ?
O1 C1 C2 112.3(6) . . ?
N1 C2 C3 110.8(6) . . ?
N1 C2 C1 108.0(6) . . ?
C3 C2 C1 116.3(6) . . ?
C2 C3 S1 115.4(5) . . ?
C5 C4 S1 114.9(6) . . ?
O4 C6 O3 125.8(6) . . ?
O4 C6 C7 123.1(6) . . ?
O3 C6 C7 111.1(6) . . ?
N2 C7 C6 107.6(6) . . ?
N2 C7 C8 110.8(6) . . ?
C6 C7 C8 110.4(6) . . ?
C7 C8 C9 116.4(6) . . ?
C11 C9 C10 111.0(6) . . ?
C11 C9 C8 112.3(6) . . ?
C10 C9 C8 108.0(6) . . ?
O5 C12 O6 125.1(6) . . ?
O5 C12 C13 120.2(6) . . ?
O6 C12 C13 114.7(6) . . ?
O7 C13 O8 125.5(6) . . ?
O7 C13 C12 121.3(6) . . ?
O8 C13 C12 113.2(5) . . ?
O12 C14 O11 124.6(7) . . ?
O12 C14 C15 121.1(6) . . ?
O11 C14 C15 114.1(6) . . ?
O10 C15 O9 125.6(6) . . ?
O10 C15 C14 121.7(6) . . ?
O9 C15 C14 112.8(6) . . ?

_refine_diff_density_max         1.001
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_20kaw50
_database_code_depnum_ccdc_archive 'CCDC 2051775'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-11-11 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         ?
_chemical_formula_sum            'C15 H28 N2 O12 S'
_chemical_formula_weight         460.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   5.6798(3)
_cell_length_b                   19.5782(9)
_cell_length_c                   9.7982(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.642(2)
_cell_angle_gamma                90
_cell_volume                     1067.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      4.52
_cell_measurement_theta_max      72.43
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.042
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_max          0.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.936
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            17194
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.517
_diffrn_reflns_theta_max         72.418
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4135
_reflns_number_gt                4021
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.988

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and
 assigned Uiso = 1.5xUeqiv.

 Both oxalates exhibit two part disorder with the carboxylate
 oxygen atoms (O7, O8, O11, O12) located over two positions.  Refinement of
 the occupancy factors gave a 60:40 ratio of these disordered 
 components.  Both RIGU and ISOR commands were applied.    
;

_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+0.4632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1840 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.144(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4135
_refine_ls_number_parameters     340
_refine_ls_number_restraints     253
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54650(15) 0.66491(5) 0.46342(10) 0.0330(2) Uani 1 1 d . . . . .
O1 O -0.0257(4) 0.60811(13) 0.2934(2) 0.0250(5) Uani 1 1 d D . . . .
H1 H -0.100(8) 0.595(2) 0.212(3) 0.038 Uiso 1 1 d D U . . .
O2 O 0.1034(4) 0.50007(12) 0.3309(2) 0.0218(5) Uani 1 1 d . . . . .
O3 O 0.7686(4) 0.37209(14) 0.4244(2) 0.0277(5) Uani 1 1 d D . . . .
H3 H 0.847(9) 0.389(2) 0.500(4) 0.042 Uiso 1 1 d D U . . .
O4 O 0.6307(4) 0.47972(12) 0.3968(2) 0.0241(5) Uani 1 1 d . . . . .
O5 O 1.0692(4) 0.57912(12) 0.9795(2) 0.0190(4) Uani 1 1 d D . . . .
H5 H 1.189(6) 0.574(2) 0.941(4) 0.028 Uiso 1 1 d D U . . .
O6 O 0.8537(4) 0.56624(13) 0.7624(2) 0.0229(5) Uani 1 1 d . . . . .
O7 O 0.446(2) 0.5813(8) 0.8638(11) 0.0165(18) Uani 0.61(5) 1 d . U P A 1
O8 O 0.665(2) 0.5663(7) 1.0804(12) 0.0151(19) Uani 0.61(5) 1 d . U P A 1
O9 O -0.3303(4) 0.40392(12) -0.2562(2) 0.0223(5) Uani 1 1 d D . . . .
H9 H -0.450(7) 0.405(2) -0.215(4) 0.034 Uiso 1 1 d D U . . .
O10 O -0.1163(4) 0.42405(12) -0.0414(2) 0.0217(5) Uani 1 1 d . . . . .
O11 O 0.2928(19) 0.4103(8) -0.1407(11) 0.0152(18) Uani 0.61(5) 1 d . U P A 1
O12 O 0.0736(19) 0.4183(8) -0.3587(11) 0.0162(18) Uani 0.61(5) 1 d . U P A 1
N1 N 0.3526(5) 0.52791(16) 0.5869(3) 0.0214(5) Uani 1 1 d D . . . .
H1B H 0.469(6) 0.523(2) 0.546(4) 0.032 Uiso 1 1 d D U . . .
H1C H 0.401(8) 0.538(2) 0.670(3) 0.032 Uiso 1 1 d D U . . .
H1A H 0.290(8) 0.4891(16) 0.588(5) 0.032 Uiso 1 1 d D U . . .
N2 N 0.3840(5) 0.45840(15) 0.1382(3) 0.0197(5) Uani 1 1 d D . . . .
H2A H 0.467(7) 0.4951(17) 0.133(5) 0.029 Uiso 1 1 d D U . . .
H2B H 0.311(8) 0.447(2) 0.056(3) 0.029 Uiso 1 1 d D U . . .
H2C H 0.273(6) 0.468(2) 0.183(4) 0.029 Uiso 1 1 d D U . . .
C1 C 0.0842(5) 0.55834(17) 0.3698(3) 0.0198(6) Uani 1 1 d . . . . .
C2 C 0.1766(6) 0.58017(18) 0.5200(3) 0.0211(6) Uani 1 1 d . . . . .
H2 H 0.037465 0.578873 0.568218 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2832(6) 0.65189(17) 0.5387(3) 0.0239(7) Uani 1 1 d . . . . .
H3A H 0.326587 0.662073 0.639608 0.029 Uiso 1 1 calc R U . . .
H3B H 0.157954 0.685002 0.496165 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4259(9) 0.7074(3) 0.3011(5) 0.0578(14) Uani 1 1 d . . . . .
H4A H 0.356439 0.673001 0.230347 0.069 Uiso 1 1 calc R U . . .
H4B H 0.295045 0.738582 0.314385 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6134(8) 0.7472(2) 0.2496(5) 0.0438(10) Uani 1 1 d . . . . .
H5A H 0.675194 0.783207 0.316750 0.066 Uiso 1 1 calc R U . . .
H5B H 0.543280 0.767824 0.159465 0.066 Uiso 1 1 calc R U . . .
H5C H 0.745159 0.716684 0.238735 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6511(5) 0.42256(18) 0.3537(3) 0.0201(6) Uani 1 1 d . . . . .
C7 C 0.5469(6) 0.40247(18) 0.2037(3) 0.0215(7) Uani 1 1 d . . . . .
H7 H 0.683550 0.400152 0.153538 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4188(6) 0.33327(18) 0.1848(4) 0.0260(7) Uani 1 1 d . . . . .
H8A H 0.360333 0.325070 0.083919 0.031 Uiso 1 1 calc R U . . .
H8B H 0.536906 0.297038 0.220344 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2081(7) 0.32714(19) 0.2578(4) 0.0295(8) Uani 1 1 d . . . . .
H9A H 0.096340 0.365716 0.229138 0.035 Uiso 1 1 calc R U . . .
H9B H 0.267961 0.330446 0.359727 0.035 Uiso 1 1 calc R U . . .
C10 C 0.0711(7) 0.2598(2) 0.2245(5) 0.0389(9) Uani 1 1 d . . . . .
H10A H 0.185915 0.221481 0.248033 0.047 Uiso 1 1 calc R U . . .
H10B H -0.048759 0.255885 0.284749 0.047 Uiso 1 1 calc R U . . .
C11 C -0.0562(8) 0.2526(2) 0.0749(5) 0.0441(10) Uani 1 1 d . . . . .
H11A H -0.147860 0.294294 0.045214 0.066 Uiso 1 1 calc R U . . .
H11B H -0.165978 0.213511 0.065804 0.066 Uiso 1 1 calc R U . . .
H11C H 0.062326 0.245358 0.016185 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8683(5) 0.57307(16) 0.8863(3) 0.0158(6) Uani 1 1 d . . . . .
C13 C 0.6407(5) 0.57376(16) 0.9509(3) 0.0152(6) Uani 1 1 d . . . . .
C14 C -0.1310(5) 0.41394(15) -0.1642(3) 0.0167(6) Uani 1 1 d . . . . .
C15 C 0.0972(5) 0.41370(16) -0.2293(3) 0.0174(6) Uani 1 1 d . . . . .
O7A O 0.444(3) 0.5659(10) 0.8652(16) 0.010(3) Uani 0.39(5) 1 d . U P A 2
O8A O 0.662(3) 0.5803(10) 1.0791(19) 0.012(3) Uani 0.39(5) 1 d . U P A 2
O11A O 0.294(3) 0.4256(10) -0.1447(16) 0.010(3) Uani 0.39(5) 1 d . U P A 2
O12A O 0.077(3) 0.4032(10) -0.3566(17) 0.012(3) Uani 0.39(5) 1 d . U P A 2


_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 1.803(5) . ?
S1 C3 1.814(4) . ?
O1 C1 1.308(4) . ?
O1 H1 0.86(3) . ?
O2 C1 1.215(4) . ?
O3 C6 1.309(4) . ?
O3 H3 0.85(3) . ?
O4 C6 1.210(4) . ?
O5 C12 1.315(3) . ?
O5 H5 0.85(3) . ?
O6 C12 1.207(4) . ?
O7 C13 1.261(11) . ?
O8 C13 1.257(13) . ?
O9 C14 1.312(4) . ?
O9 H9 0.86(3) . ?
O10 C14 1.206(4) . ?
O11 C15 1.266(10) . ?
O12 C15 1.252(12) . ?
N1 C2 1.487(4) . ?
N1 H1B 0.85(3) . ?
N1 H1C 0.83(3) . ?
N1 H1A 0.84(3) . ?
N2 C7 1.492(4) . ?
N2 H2A 0.87(3) . ?
N2 H2B 0.85(3) . ?
N2 H2C 0.86(3) . ?
C1 C2 1.520(4) . ?
C2 C3 1.525(5) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.487(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.522(4) . ?
C7 C8 1.531(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.518(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.532(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.505(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.550(4) . ?
C13 O8A 1.244(19) . ?
C13 O7A 1.266(15) . ?
C14 C15 1.555(4) . ?
C15 O12A 1.247(17) . ?
C15 O11A 1.271(15) . ?

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 C3 103.0(2) . . ?
C1 O1 H1 113(3) . . ?
C6 O3 H3 107(4) . . ?
C12 O5 H5 110(3) . . ?
C14 O9 H9 109(3) . . ?
C2 N1 H1B 113(3) . . ?
C2 N1 H1C 109(3) . . ?
H1B N1 H1C 111(4) . . ?
C2 N1 H1A 112(3) . . ?
H1B N1 H1A 106(5) . . ?
H1C N1 H1A 105(4) . . ?
C7 N2 H2A 110(3) . . ?
C7 N2 H2B 111(3) . . ?
H2A N2 H2B 109(4) . . ?
C7 N2 H2C 113(3) . . ?
H2A N2 H2C 108(4) . . ?
H2B N2 H2C 105(4) . . ?
O2 C1 O1 125.6(3) . . ?
O2 C1 C2 122.2(3) . . ?
O1 C1 C2 112.1(3) . . ?
N1 C2 C1 107.7(3) . . ?
N1 C2 C3 111.4(3) . . ?
C1 C2 C3 115.2(3) . . ?
N1 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C2 C3 S1 114.8(2) . . ?
C2 C3 H3A 108.6 . . ?
S1 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
S1 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 S1 111.7(3) . . ?
C5 C4 H4A 109.3 . . ?
S1 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
S1 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 126.0(3) . . ?
O4 C6 C7 122.0(3) . . ?
O3 C6 C7 111.9(3) . . ?
N2 C7 C6 108.2(3) . . ?
N2 C7 C8 111.0(3) . . ?
C6 C7 C8 115.4(3) . . ?
N2 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C9 C8 C7 114.4(3) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 112.5(3) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.3(3) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O5 125.6(3) . . ?
O6 C12 C13 121.2(2) . . ?
O5 C12 C13 113.2(2) . . ?
O8 C13 O7 126.7(8) . . ?
O8A C13 O7A 125.0(12) . . ?
O8A C13 C12 119.7(9) . . ?
O8 C13 C12 118.8(6) . . ?
O7 C13 C12 114.5(6) . . ?
O7A C13 C12 115.3(8) . . ?
O10 C14 O9 125.9(3) . . ?
O10 C14 C15 120.9(3) . . ?
O9 C14 C15 113.1(2) . . ?
O12 C15 O11 126.7(8) . . ?
O12A C15 O11A 125.0(11) . . ?
O12A C15 C14 119.7(8) . . ?
O12 C15 C14 119.2(6) . . ?
O11 C15 C14 114.1(6) . . ?
O11A C15 C14 115.3(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
O2 C1 C2 N1 18.6(4) . . . . ?
O1 C1 C2 N1 -164.7(3) . . . . ?
O2 C1 C2 C3 143.6(3) . . . . ?
O1 C1 C2 C3 -39.6(4) . . . . ?
N1 C2 C3 S1 60.7(3) . . . . ?
C1 C2 C3 S1 -62.4(3) . . . . ?
C4 S1 C3 C2 100.0(3) . . . . ?
C3 S1 C4 C5 157.1(4) . . . . ?
O4 C6 C7 N2 -11.6(4) . . . . ?
O3 C6 C7 N2 170.8(2) . . . . ?
O4 C6 C7 C8 -136.6(3) . . . . ?
O3 C6 C7 C8 45.8(4) . . . . ?
N2 C7 C8 C9 -64.4(4) . . . . ?
C6 C7 C8 C9 59.1(4) . . . . ?
C7 C8 C9 C10 174.5(3) . . . . ?
C8 C9 C10 C11 -66.2(4) . . . . ?
O6 C12 C13 O8A 179.4(11) . . . . ?
O5 C12 C13 O8A 0.7(11) . . . . ?
O6 C12 C13 O8 164.9(8) . . . . ?
O5 C12 C13 O8 -13.8(9) . . . . ?
O6 C12 C13 O7 -14.3(9) . . . . ?
O5 C12 C13 O7 167.0(8) . . . . ?
O6 C12 C13 O7A 0.8(11) . . . . ?
O5 C12 C13 O7A -177.9(10) . . . . ?
O10 C14 C15 O12A -179.9(11) . . . . ?
O9 C14 C15 O12A -1.4(11) . . . . ?
O10 C14 C15 O12 -164.3(8) . . . . ?
O9 C14 C15 O12 14.2(9) . . . . ?
O10 C14 C15 O11 14.1(8) . . . . ?
O9 C14 C15 O11 -167.4(8) . . . . ?
O10 C14 C15 O11A -0.8(11) . . . . ?
O9 C14 C15 O11A 177.7(10) . . . . ?

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 H1 O8 0.86(3) 1.75(3) 2.576(12) 159(5) 1_454 yes
O1 H1 O8A 0.86(3) 1.70(4) 2.521(17) 157(5) 1_454 yes
O3 H3 O12 0.85(3) 1.79(3) 2.617(11) 166(5) 1_656 yes
O3 H3 O12A 0.85(3) 1.74(3) 2.555(15) 161(5) 1_656 yes
O5 H5 O7 0.85(3) 1.78(3) 2.617(12) 169(5) 1_655 yes
O5 H5 O7A 0.85(3) 1.76(3) 2.608(17) 178(5) 1_655 yes
O9 H9 O11 0.86(3) 1.76(3) 2.619(12) 176(5) 1_455 yes
O9 H9 O11A 0.86(3) 1.77(3) 2.621(17) 168(5) 1_455 yes
N1 H1B O4 0.85(3) 2.06(3) 2.836(4) 153(4) . yes
N1 H1C O7 0.83(3) 2.04(3) 2.856(12) 165(4) . yes
N1 H1C O7A 0.83(3) 1.95(3) 2.773(16) 168(5) . yes
N1 H1A O12 0.84(3) 1.99(3) 2.782(14) 157(5) 1_556 yes
N1 H1A O12A 0.84(3) 2.20(3) 3.010(19) 162(4) 1_556 yes
N2 H2A O8 0.87(3) 1.92(3) 2.773(14) 166(4) 1_554 yes
N2 H2A O8A 0.87(3) 2.13(3) 2.981(19) 169(4) 1_554 yes
N2 H2B O11 0.85(3) 2.05(3) 2.838(11) 154(4) . yes
N2 H2B O11A 0.85(3) 2.00(3) 2.790(16) 154(4) . yes
N2 H2C O2 0.86(3) 2.00(3) 2.825(4) 162(4) . yes

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_wheeler111
_database_code_depnum_ccdc_archive 'CCDC 2017260'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 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         'C5 H12 N O2 S, C6 H14 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C15 H28 N2 O12 S'
_chemical_formula_weight         460.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6692(2)
_cell_length_b                   9.4991(3)
_cell_length_c                   10.2324(3)
_cell_angle_alpha                93.406(2)
_cell_angle_beta                 101.269(2)
_cell_angle_gamma                97.714(2)
_cell_volume                     533.44(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3444
_cell_measurement_theta_min      17.16
_cell_measurement_theta_max      68.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.937
_shelx_estimated_absorpt_T_min   0.604
_shelx_estimated_absorpt_T_max   0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_detector_area_resol_mean 8.1
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            13001
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.716
_diffrn_reflns_theta_max         68.333
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             3684
_reflns_number_gt                3654
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.928

_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       'APEX2 (Bruker, 2015)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.0820P] 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 1769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     281
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44218(12) 0.12947(7) 0.04509(7) 0.03077(17) Uani 1 1 d . . . . .
O1 O 0.8375(3) 0.53574(17) 0.29311(16) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.925279 0.611909 0.328865 0.027 Uiso 1 1 calc R U . . .
O2 O 0.7593(3) 0.51704(16) 0.49852(15) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.4740(3) 0.26489(19) 0.43082(18) 0.0137(4) Uani 1 1 d . . . . .
H1A H 0.402(3) 0.1754(17) 0.4005(7) 0.016 Uiso 1 1 calc R U . . .
H1B H 0.364(3) 0.3149(13) 0.4571(12) 0.016 Uiso 1 1 calc R U . . .
H1C H 0.597(2) 0.2619(15) 0.5008(14) 0.016 Uiso 1 1 calc R U . . .
C1 C 0.7332(4) 0.4733(2) 0.3819(2) 0.0128(4) Uani 1 1 d . . . . .
C2 C 0.5710(4) 0.3349(2) 0.3222(2) 0.0129(4) Uani 1 1 d . . . . .
H2 H 0.672533 0.270728 0.284975 0.015 Uiso 1 1 calc R U . . .
C3 C 0.3650(4) 0.3603(2) 0.2086(2) 0.0166(4) Uani 1 1 d . . . . .
H3A H 0.241121 0.402229 0.247865 0.020 Uiso 1 1 calc R U . . .
H3B H 0.431615 0.430597 0.152557 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2416(4) 0.2258(3) 0.1194(2) 0.0231(5) Uani 1 1 d . . . . .
H4A H 0.117079 0.252568 0.046897 0.028 Uiso 1 1 calc R U . . .
H4B H 0.156161 0.161049 0.173249 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5832(5) 0.2696(3) -0.0391(3) 0.0319(6) Uani 1 1 d . . . . .
H5A H 0.681431 0.229043 -0.096386 0.048 Uiso 1 1 calc R U . . .
H5B H 0.687643 0.341540 0.027478 0.048 Uiso 1 1 calc R U . . .
H5C H 0.456826 0.314135 -0.094077 0.048 Uiso 1 1 calc R U . . .
O5 O 0.7249(2) 0.85707(17) 0.34709(15) 0.0150(3) Uani 1 1 d . . . . .
H5 H 0.603062 0.897460 0.350762 0.022 Uiso 1 1 calc R U . . .
O6 O 0.9233(3) 1.08168(16) 0.37019(15) 0.0152(3) Uani 1 1 d . . . . .
O7 O 1.1541(3) 0.75858(15) 0.37884(14) 0.0133(3) Uani 1 1 d . . . . .
O8 O 1.3389(3) 0.97465(16) 0.35520(16) 0.0140(3) Uani 1 1 d . . . . .
C14 C 0.9188(3) 0.9540(2) 0.35957(19) 0.0107(4) Uani 1 1 d . . . . .
C15 C 1.1560(3) 0.8878(2) 0.3639(2) 0.0104(4) Uani 1 1 d . . . . .
O3 O 0.1720(3) 0.46461(17) 0.74117(16) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.088388 0.386899 0.706323 0.028 Uiso 1 1 calc R U . . .
O4 O 0.2576(3) 0.47973(16) 0.53722(15) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.5365(3) 0.73274(19) 0.60116(18) 0.0133(4) Uani 1 1 d . . . . .
H2A H 0.424(2) 0.7346(16) 0.5331(14) 0.016 Uiso 1 1 calc R U . . .
H2B H 0.640(3) 0.6829(13) 0.5803(12) 0.016 Uiso 1 1 calc R U . . .
H2C H 0.607(3) 0.8172(17) 0.6279(7) 0.016 Uiso 1 1 calc R U . . .
C6 C 0.2773(4) 0.5265(2) 0.6522(2) 0.0136(4) Uani 1 1 d . . . . .
C7 C 0.4303(4) 0.6689(2) 0.7098(2) 0.0128(4) Uani 1 1 d . . . . .
H7 H 0.320554 0.733345 0.738423 0.015 Uiso 1 1 calc R U . . .
C8 C 0.6271(4) 0.6527(2) 0.8317(2) 0.0153(4) Uani 1 1 d . . . . .
H8A H 0.551027 0.597998 0.895995 0.018 Uiso 1 1 calc R U . . .
H8B H 0.746767 0.597473 0.802641 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7604(4) 0.7960(2) 0.9024(2) 0.0175(5) Uani 1 1 d . . . . .
H9A H 0.639209 0.858951 0.914571 0.021 Uiso 1 1 calc R U . . .
H9B H 0.864189 0.841865 0.844882 0.021 Uiso 1 1 calc R U . . .
C10 C 0.9189(4) 0.7815(3) 1.0389(2) 0.0199(5) Uani 1 1 d . . . . .
H10A H 0.981290 0.878059 1.084412 0.024 Uiso 1 1 calc R U . . .
H10B H 0.816418 0.730317 1.094263 0.024 Uiso 1 1 calc R U . . .
C11 C 1.1330(5) 0.7030(3) 1.0315(3) 0.0327(6) Uani 1 1 d . . . . .
H11A H 1.234895 0.752355 0.976192 0.049 Uiso 1 1 calc R U . . .
H11B H 1.072828 0.605247 0.991741 0.049 Uiso 1 1 calc R U . . .
H11C H 1.229322 0.700828 1.121792 0.049 Uiso 1 1 calc R U . . .
O9 O 0.2741(2) 0.14265(16) 0.67106(15) 0.0138(3) Uani 1 1 d . . . . .
H9 H 0.397043 0.102210 0.670909 0.021 Uiso 1 1 calc R U . . .
O10 O 0.0786(3) -0.08164(16) 0.65591(15) 0.0153(3) Uani 1 1 d . . . . .
O11 O -0.3403(3) 0.02498(16) 0.66336(16) 0.0145(3) Uani 1 1 d . . . . .
O12 O -0.1481(2) 0.24317(15) 0.65921(15) 0.0150(3) Uani 1 1 d . . . . .
C12 C 0.0827(4) 0.0462(2) 0.6641(2) 0.0109(4) Uani 1 1 d . . . . .
C13 C -0.1543(4) 0.1121(2) 0.6633(2) 0.0109(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.801(3) . ?
S1 C5 1.809(3) . ?
O1 C1 1.307(3) . ?
O1 H1 0.8400 . ?
O2 C1 1.214(3) . ?
N1 C2 1.486(3) . ?
N1 H1A 0.901(16) . ?
N1 H1B 0.901(16) . ?
N1 H1C 0.901(16) . ?
C1 C2 1.520(3) . ?
C2 C3 1.533(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O5 C14 1.316(3) . ?
O5 H5 0.8400 . ?
O6 C14 1.208(3) . ?
O7 C15 1.245(3) . ?
O8 C15 1.256(3) . ?
C14 C15 1.553(3) . ?
O3 C6 1.308(3) . ?
O3 H3 0.8400 . ?
O4 C6 1.212(3) . ?
N2 C7 1.486(3) . ?
N2 H2A 0.850(16) . ?
N2 H2B 0.850(16) . ?
N2 H2C 0.850(16) . ?
C6 C7 1.523(3) . ?
C7 C8 1.533(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.529(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.531(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.519(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O9 C12 1.311(3) . ?
O9 H9 0.8400 . ?
O10 C12 1.209(3) . ?
O11 C13 1.250(3) . ?
O12 C13 1.245(3) . ?
C12 C13 1.555(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C5 100.00(13) . . ?
C1 O1 H1 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O2 C1 O1 125.8(2) . . ?
O2 C1 C2 122.6(2) . . ?
O1 C1 C2 111.65(17) . . ?
N1 C2 C1 108.54(17) . . ?
N1 C2 C3 111.35(17) . . ?
C1 C2 C3 111.67(17) . . ?
N1 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C4 C3 C2 113.95(18) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 S1 115.16(17) . . ?
C3 C4 H4A 108.5 . . ?
S1 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
S1 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C14 O5 H5 109.5 . . ?
O6 C14 O5 126.15(18) . . ?
O6 C14 C15 121.06(18) . . ?
O5 C14 C15 112.77(17) . . ?
O7 C15 O8 125.61(18) . . ?
O7 C15 C14 119.52(18) . . ?
O8 C15 C14 114.83(18) . . ?
C6 O3 H3 109.5 . . ?
C7 N2 H2A 109.5 . . ?
C7 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C7 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O4 C6 O3 125.6(2) . . ?
O4 C6 C7 122.7(2) . . ?
O3 C6 C7 111.76(18) . . ?
N2 C7 C6 107.88(17) . . ?
N2 C7 C8 111.81(16) . . ?
C6 C7 C8 112.03(18) . . ?
N2 C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C9 C8 C7 112.89(18) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 112.94(19) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 113.91(19) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O9 H9 109.5 . . ?
O10 C12 O9 126.20(18) . . ?
O10 C12 C13 120.88(18) . . ?
O9 C12 C13 112.90(18) . . ?
O12 C13 O11 125.23(19) . . ?
O12 C13 C12 119.25(18) . . ?
O11 C13 C12 115.50(18) . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw41
_database_code_depnum_ccdc_archive 'CCDC 2017252'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 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         '3(C5 H11 N O2 S), 3(C5 H11 N O2 S)'
_chemical_formula_sum            'C10 H22 N2 O4 S2'
_chemical_formula_weight         298.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   16.4457(10)
_cell_length_b                   4.6941(3)
_cell_length_c                   29.1646(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.877(3)
_cell_angle_gamma                90
_cell_volume                     2176.0(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9031
_cell_measurement_theta_min      6.30
_cell_measurement_theta_max      68.42
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.042
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_max          0.424
_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    3.423
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.5616
_exptl_absorpt_correction_T_max  0.7531

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            37344
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         68.521
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             7845
_reflns_number_gt                7334
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.961

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+1.3330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 2941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.093(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7845
_refine_ls_number_parameters     565
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.42360(7) 0.2929(3) 0.29906(3) 0.0320(3) Uani 1 1 d . . . . .
S2A S 0.66805(6) 0.2306(3) -0.11783(3) 0.0273(2) Uani 1 1 d . . . . .
O1A O 0.50332(17) 0.3204(6) 0.11645(9) 0.0243(6) Uani 1 1 d . . . . .
O2A O 0.60284(16) 0.0464(6) 0.16232(9) 0.0209(6) Uani 1 1 d . . . . .
O3A O 0.67801(17) 0.4156(6) 0.04575(9) 0.0232(6) Uani 1 1 d . . . . .
O4A O 0.57599(16) 0.7028(6) 0.00524(8) 0.0208(5) Uani 1 1 d . . . . .
N1A N 0.6427(2) 0.4517(8) 0.22918(11) 0.0191(7) Uani 1 1 d . . . . .
N2A N 0.5270(2) 0.3186(8) -0.06529(11) 0.0191(7) Uani 1 1 d . . . . .
C1A C 0.5548(2) 0.2562(9) 0.15520(11) 0.0183(7) Uani 1 1 d . . . . .
C2A C 0.5550(2) 0.4456(8) 0.19806(12) 0.0183(7) Uani 1 1 d . . . . .
H2A H 0.537003 0.638874 0.187376 0.022 Uiso 1 1 calc R U . . .
C3A C 0.4946(2) 0.3186(9) 0.22462(12) 0.0198(8) Uani 1 1 d . . . . .
H3A1 H 0.507170 0.117544 0.229972 0.024 Uiso 1 1 calc R U . . .
H3A2 H 0.437607 0.334462 0.204806 0.024 Uiso 1 1 calc R U . . .
C4A C 0.4992(2) 0.4616(9) 0.27229(13) 0.0225(8) Uani 1 1 d . . . . .
H4A1 H 0.486544 0.662959 0.267596 0.027 Uiso 1 1 calc R U . . .
H4A2 H 0.555409 0.442243 0.292981 0.027 Uiso 1 1 calc R U . . .
C5A C 0.4538(3) 0.4520(12) 0.35729(14) 0.0348(10) Uani 1 1 d . . . . .
H5A1 H 0.511571 0.407830 0.372026 0.052 Uiso 1 1 calc R U . . .
H5A2 H 0.418860 0.378054 0.376307 0.052 Uiso 1 1 calc R U . . .
H5A3 H 0.446936 0.654939 0.354504 0.052 Uiso 1 1 calc R U . . .
C6A C 0.6226(2) 0.4910(8) 0.00908(12) 0.0172(7) Uani 1 1 d . . . . .
C7A C 0.6158(2) 0.3082(8) -0.03546(12) 0.0191(8) Uani 1 1 d . . . . .
H7A H 0.631157 0.110890 -0.026130 0.023 Uiso 1 1 calc R U . . .
C8A C 0.6763(2) 0.4277(10) -0.06305(13) 0.0239(8) Uani 1 1 d . . . . .
H8A1 H 0.733586 0.416397 -0.043431 0.029 Uiso 1 1 calc R U . . .
H8A2 H 0.663294 0.626693 -0.070438 0.029 Uiso 1 1 calc R U . . .
C9A C 0.7447(3) 0.4282(11) -0.14038(15) 0.0331(10) Uani 1 1 d . . . . .
H9A1 H 0.732995 0.630631 -0.140219 0.040 Uiso 1 1 calc R U . . .
H9A2 H 0.800842 0.394832 -0.120362 0.040 Uiso 1 1 calc R U . . .
C10A C 0.7394(3) 0.3286(12) -0.19115(15) 0.0388(11) Uani 1 1 d . . . . .
H10A H 0.750553 0.127823 -0.191069 0.058 Uiso 1 1 calc R U . . .
H10B H 0.780299 0.429325 -0.203244 0.058 Uiso 1 1 calc R U . . .
H10C H 0.684121 0.366367 -0.210906 0.058 Uiso 1 1 calc R U . . .
H11A H 0.643(4) 0.578(16) 0.246(2) 0.047(18) Uiso 1 1 d . . . . .
H12C H 0.973(3) 0.282(7) 0.5772(15) 0.024(11) Uiso 1 1 d D . . . .
H11C H 0.965(4) 0.592(15) 0.583(2) 0.050(17) Uiso 1 1 d . . . . .
H13C H 1.001(3) 0.479(10) 0.5482(16) 0.016(11) Uiso 1 1 d . . . . .
H12A H 0.653(3) 0.298(12) 0.2452(17) 0.024(12) Uiso 1 1 d . . . . .
H13B H 0.692(3) 0.760(14) 0.0876(17) 0.024(12) Uiso 1 1 d . . . . .
H13A H 0.681(3) 0.473(11) 0.2122(18) 0.025(12) Uiso 1 1 d . . . . .
H11B H 0.662(3) 0.939(11) 0.1195(18) 0.024(12) Uiso 1 1 d . . . . .
H16B H 0.826(3) 1.021(13) 0.4090(18) 0.029(13) Uiso 1 1 d . . . . .
H14B H 0.849(3) 0.822(12) 0.3791(19) 0.035(15) Uiso 1 1 d . . . . .
H14A H 0.494(3) 0.287(10) -0.0478(15) 0.016(10) Uiso 1 1 d . . . . .
H16C H 0.884(3) 0.190(12) 0.2462(17) 0.018(11) Uiso 1 1 d . . . . .
H15A H 0.518(3) 0.485(13) -0.0796(19) 0.029(13) Uiso 1 1 d . . . . .
H15C H 0.881(3) 0.505(10) 0.2499(15) 0.010(9) Uiso 1 1 d . . . . .
H15B H 0.823(3) 0.715(13) 0.4183(18) 0.027(12) Uiso 1 1 d . . . . .
H12B H 0.690(3) 1.027(12) 0.0792(19) 0.020(12) Uiso 1 1 d . . . . .
H16A H 0.521(3) 0.182(10) -0.0887(16) 0.014(10) Uiso 1 1 d . . . . .
S1B S 0.91256(7) 0.7871(3) 0.02475(3) 0.0338(3) Uani 1 1 d . . . . .
S2B S 0.67003(6) 0.7405(2) 0.44299(3) 0.0254(2) Uani 1 1 d . . . . .
O1B O 0.75320(16) 0.5510(6) 0.17319(9) 0.0217(6) Uani 1 1 d . . . . .
O2B O 0.86074(17) 0.8325(6) 0.20918(8) 0.0245(6) Uani 1 1 d . . . . .
O3B O 0.77473(16) 1.2099(6) 0.32150(8) 0.0217(5) Uani 1 1 d . . . . .
O4B O 0.66315(17) 0.9516(6) 0.28340(9) 0.0233(6) Uani 1 1 d . . . . .
N1B N 0.6988(2) 0.9170(8) 0.10097(12) 0.0185(7) Uani 1 1 d . . . . .
N2B N 0.8160(2) 0.8448(8) 0.39450(11) 0.0188(7) Uani 1 1 d . . . . .
C1B C 0.8002(2) 0.7609(9) 0.17489(11) 0.0185(7) Uani 1 1 d . . . . .
C2B C 0.7883(2) 0.9394(9) 0.12923(12) 0.0183(7) Uani 1 1 d . . . . .
H2B H 0.802548 1.138975 0.137338 0.022 Uiso 1 1 calc R U . . .
C3B C 0.8472(2) 0.8171(9) 0.10085(13) 0.0220(8) Uani 1 1 d . . . . .
H3B1 H 0.904959 0.842007 0.119218 0.026 Uiso 1 1 calc R U . . .
H3B2 H 0.836932 0.614070 0.096662 0.026 Uiso 1 1 calc R U . . .
C4B C 0.8372(2) 0.9529(9) 0.05229(13) 0.0237(8) Uani 1 1 d . . . . .
H4B1 H 0.847515 1.156209 0.055641 0.028 Uiso 1 1 calc R U . . .
H4B2 H 0.780386 0.923597 0.032809 0.028 Uiso 1 1 calc R U . . .
C5B C 0.8828(3) 0.9526(12) -0.03283(15) 0.0353(10) Uani 1 1 d . . . . .
H5B1 H 0.825044 0.908668 -0.047852 0.053 Uiso 1 1 calc R U . . .
H5B2 H 0.917924 0.882112 -0.051978 0.053 Uiso 1 1 calc R U . . .
H5B3 H 0.889396 1.155281 -0.029378 0.053 Uiso 1 1 calc R U . . .
C6B C 0.7232(2) 1.0117(8) 0.31883(12) 0.0187(7) Uani 1 1 d . . . . .
C7B C 0.7290(2) 0.8270(8) 0.36310(12) 0.0176(7) Uani 1 1 d . . . . .
H7B H 0.715858 0.628703 0.353555 0.021 Uiso 1 1 calc R U . . .
C8B C 0.6647(2) 0.9396(9) 0.38881(13) 0.0231(8) Uani 1 1 d . . . . .
H8B1 H 0.608534 0.924137 0.367947 0.028 Uiso 1 1 calc R U . . .
H8B2 H 0.675815 1.139268 0.396476 0.028 Uiso 1 1 calc R U . . .
C9B C 0.5912(3) 0.9344(10) 0.46412(13) 0.0251(8) Uani 1 1 d . . . . .
H9B1 H 0.601853 1.137600 0.463974 0.030 Uiso 1 1 calc R U . . .
H9B2 H 0.535557 0.897302 0.443754 0.030 Uiso 1 1 calc R U . . .
C10B C 0.5965(3) 0.8321(11) 0.51495(13) 0.0305(10) Uani 1 1 d . . . . .
H10D H 0.589545 0.629068 0.514977 0.046 Uiso 1 1 calc R U . . .
H10E H 0.552938 0.921437 0.526318 0.046 Uiso 1 1 calc R U . . .
H10F H 0.650417 0.882009 0.535252 0.046 Uiso 1 1 calc R U . . .
S1C S 0.72805(6) 0.2802(3) 0.61957(3) 0.0306(3) Uani 1 1 d . . . . .
S2C S 1.07079(6) 0.2204(3) 0.23571(3) 0.0280(2) Uani 1 1 d . . . . .
H14C H 0.846(3) 0.309(11) 0.2793(16) 0.021(11) Uiso 1 1 d . . . . .
O1C O 0.83945(17) 0.3436(6) 0.44586(8) 0.0227(6) Uani 1 1 d . . . . .
O2C O 0.92975(16) 0.0524(6) 0.49400(9) 0.0196(6) Uani 1 1 d . . . . .
O3C O 1.01831(17) 0.4460(6) 0.38258(9) 0.0231(6) Uani 1 1 d . . . . .
O4C O 0.91861(15) 0.7140(6) 0.33537(8) 0.0206(5) Uani 1 1 d . . . . .
N1C N 0.9639(2) 0.4475(8) 0.56307(11) 0.0179(6) Uani 1 1 d D . . . .
N2C N 0.8879(2) 0.3269(8) 0.26538(11) 0.0213(7) Uani 1 1 d . . . . .
C1C C 0.8842(2) 0.2678(8) 0.48585(11) 0.0164(7) Uani 1 1 d . . . . .
C2C C 0.8789(2) 0.4483(8) 0.52877(12) 0.0183(7) Uani 1 1 d . . . . .
H2C H 0.862666 0.643778 0.518636 0.022 Uiso 1 1 calc R U . . .
C3C C 0.8132(2) 0.3163(9) 0.55132(12) 0.0202(8) Uani 1 1 d . . . . .
H3C1 H 0.758036 0.335841 0.529436 0.024 Uiso 1 1 calc R U . . .
H3C2 H 0.824789 0.114341 0.556129 0.024 Uiso 1 1 calc R U . . .
C4C C 0.8112(2) 0.4510(9) 0.59876(13) 0.0233(8) Uani 1 1 d . . . . .
H4C1 H 0.800391 0.653835 0.594765 0.028 Uiso 1 1 calc R U . . .
H4C2 H 0.864928 0.424328 0.621695 0.028 Uiso 1 1 calc R U . . .
C5C C 0.7516(3) 0.4147(12) 0.67942(15) 0.0339(10) Uani 1 1 d . . . . .
H5C1 H 0.807173 0.356250 0.696213 0.051 Uiso 1 1 calc R U . . .
H5C2 H 0.711493 0.340583 0.695165 0.051 Uiso 1 1 calc R U . . .
H5C3 H 0.748543 0.618962 0.678755 0.051 Uiso 1 1 calc R U . . .
C6C C 0.9677(2) 0.5065(8) 0.34352(12) 0.0183(7) Uani 1 1 d . . . . .
C7C C 0.9712(2) 0.3170(9) 0.30138(11) 0.0184(7) Uani 1 1 d . . . . .
H7C H 0.983126 0.120526 0.312398 0.022 Uiso 1 1 calc R U . . .
C8C C 1.0433(2) 0.4266(9) 0.28182(13) 0.0236(8) Uani 1 1 d . . . . .
H8C1 H 1.093044 0.442068 0.308116 0.028 Uiso 1 1 calc R U . . .
H8C2 H 1.028966 0.617473 0.269688 0.028 Uiso 1 1 calc R U . . .
C9C C 1.0030(3) 0.3746(11) 0.18208(13) 0.0317(10) Uani 1 1 d . . . . .
H9C1 H 0.946911 0.294692 0.176273 0.038 Uiso 1 1 calc R U . . .
H9C2 H 0.999097 0.579103 0.185784 0.038 Uiso 1 1 calc R U . . .
C10C C 1.0401(3) 0.3090(13) 0.14056(14) 0.0389(12) Uani 1 1 d . . . . .
H10G H 1.094725 0.395072 0.145973 0.058 Uiso 1 1 calc R U . . .
H10H H 1.003941 0.384049 0.111895 0.058 Uiso 1 1 calc R U . . .
H10I H 1.045131 0.106490 0.137598 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C5A 1.804(4) . ?
S1A C4A 1.811(4) . ?
S2A C9A 1.819(4) . ?
S2A C8A 1.821(4) . ?
O1A C1A 1.263(4) . ?
O2A C1A 1.246(5) . ?
O3A C6A 1.265(5) . ?
O4A C6A 1.243(5) . ?
N1A C2A 1.495(5) . ?
N1A H11A 0.78(7) . ?
N1A H12A 0.85(6) . ?
N1A H13A 0.91(5) . ?
N2A C7A 1.497(4) . ?
N2A H14A 0.84(5) . ?
N2A H15A 0.88(6) . ?
N2A H16A 0.92(5) . ?
C1A C2A 1.533(5) . ?
C2A C3A 1.528(5) . ?
C2A H2A 0.9800 . ?
C3A C4A 1.528(5) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A H5A1 0.9600 . ?
C5A H5A2 0.9600 . ?
C5A H5A3 0.9600 . ?
C6A C7A 1.537(5) . ?
C7A C8A 1.537(5) . ?
C7A H7A 0.9800 . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A C10A 1.534(6) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
S1B C5B 1.801(4) . ?
S1B C4B 1.817(4) . ?
S2B C9B 1.817(4) . ?
S2B C8B 1.818(4) . ?
O1B C1B 1.246(5) . ?
O2B C1B 1.262(4) . ?
O3B C6B 1.248(5) . ?
O4B C6B 1.264(4) . ?
N1B C2B 1.494(5) . ?
N1B H13B 0.83(6) . ?
N1B H11B 0.91(5) . ?
N1B H12B 0.80(6) . ?
N2B C7B 1.489(4) . ?
N2B H16B 0.92(6) . ?
N2B H14B 0.79(6) . ?
N2B H15B 0.91(6) . ?
C1B C2B 1.542(5) . ?
C2B C3B 1.539(5) . ?
C2B H2B 0.9800 . ?
C3B C4B 1.523(5) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B H5B1 0.9600 . ?
C5B H5B2 0.9600 . ?
C5B H5B3 0.9600 . ?
C6B C7B 1.537(5) . ?
C7B C8B 1.538(5) . ?
C7B H7B 0.9800 . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C9B C10B 1.539(5) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
S1C C5C 1.802(4) . ?
S1C C4C 1.818(4) . ?
S2C C8C 1.806(4) . ?
S2C C9C 1.821(4) . ?
O1C C1C 1.260(4) . ?
O2C C1C 1.244(5) . ?
O3C C6C 1.259(4) . ?
O4C C6C 1.248(5) . ?
N1C C2C 1.495(5) . ?
N1C H12C 0.88(3) . ?
N1C H11C 0.89(7) . ?
N1C H13C 0.84(5) . ?
N2C C7C 1.497(4) . ?
N2C H16C 0.84(6) . ?
N2C H15C 0.94(5) . ?
N2C H14C 0.88(5) . ?
C1C C2C 1.532(5) . ?
C2C C3C 1.533(5) . ?
C2C H2C 0.9800 . ?
C3C C4C 1.529(5) . ?
C3C H3C1 0.9700 . ?
C3C H3C2 0.9700 . ?
C4C H4C1 0.9700 . ?
C4C H4C2 0.9700 . ?
C5C H5C1 0.9600 . ?
C5C H5C2 0.9600 . ?
C5C H5C3 0.9600 . ?
C6C C7C 1.530(5) . ?
C7C C8C 1.531(5) . ?
C7C H7C 0.9800 . ?
C8C H8C1 0.9700 . ?
C8C H8C2 0.9700 . ?
C9C C10C 1.521(6) . ?
C9C H9C1 0.9700 . ?
C9C H9C2 0.9700 . ?
C10C H10G 0.9600 . ?
C10C H10H 0.9600 . ?
C10C H10I 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
C5A S1A C4A 99.9(2) . . ?
C9A S2A C8A 98.9(2) . . ?
C2A N1A H11A 105(5) . . ?
C2A N1A H12A 110(3) . . ?
H11A N1A H12A 109(6) . . ?
C2A N1A H13A 112(3) . . ?
H11A N1A H13A 112(6) . . ?
H12A N1A H13A 109(4) . . ?
C7A N2A H14A 109(3) . . ?
C7A N2A H15A 109(3) . . ?
H14A N2A H15A 113(5) . . ?
C7A N2A H16A 108(3) . . ?
H14A N2A H16A 111(4) . . ?
H15A N2A H16A 107(4) . . ?
O2A C1A O1A 126.1(3) . . ?
O2A C1A C2A 117.0(3) . . ?
O1A C1A C2A 116.8(3) . . ?
N1A C2A C3A 110.5(3) . . ?
N1A C2A C1A 107.8(3) . . ?
C3A C2A C1A 108.8(3) . . ?
N1A C2A H2A 109.9 . . ?
C3A C2A H2A 109.9 . . ?
C1A C2A H2A 109.9 . . ?
C2A C3A C4A 113.8(3) . . ?
C2A C3A H3A1 108.8 . . ?
C4A C3A H3A1 108.8 . . ?
C2A C3A H3A2 108.8 . . ?
C4A C3A H3A2 108.8 . . ?
H3A1 C3A H3A2 107.7 . . ?
C3A C4A S1A 108.8(3) . . ?
C3A C4A H4A1 109.9 . . ?
S1A C4A H4A1 109.9 . . ?
C3A C4A H4A2 109.9 . . ?
S1A C4A H4A2 109.9 . . ?
H4A1 C4A H4A2 108.3 . . ?
S1A C5A H5A1 109.5 . . ?
S1A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
S1A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
O4A C6A O3A 126.4(3) . . ?
O4A C6A C7A 117.5(3) . . ?
O3A C6A C7A 116.0(3) . . ?
N2A C7A C6A 108.7(3) . . ?
N2A C7A C8A 110.5(3) . . ?
C6A C7A C8A 108.8(3) . . ?
N2A C7A H7A 109.6 . . ?
C6A C7A H7A 109.6 . . ?
C8A C7A H7A 109.6 . . ?
C7A C8A S2A 111.2(3) . . ?
C7A C8A H8A1 109.4 . . ?
S2A C8A H8A1 109.4 . . ?
C7A C8A H8A2 109.4 . . ?
S2A C8A H8A2 109.4 . . ?
H8A1 C8A H8A2 108.0 . . ?
C10A C9A S2A 108.7(3) . . ?
C10A C9A H9A1 109.9 . . ?
S2A C9A H9A1 109.9 . . ?
C10A C9A H9A2 109.9 . . ?
S2A C9A H9A2 109.9 . . ?
H9A1 C9A H9A2 108.3 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C5B S1B C4B 100.0(2) . . ?
C9B S2B C8B 99.11(19) . . ?
C2B N1B H13B 109(3) . . ?
C2B N1B H11B 112(3) . . ?
H13B N1B H11B 110(5) . . ?
C2B N1B H12B 110(3) . . ?
H13B N1B H12B 103(5) . . ?
H11B N1B H12B 112(5) . . ?
C7B N2B H16B 111(3) . . ?
C7B N2B H14B 109(4) . . ?
H16B N2B H14B 109(5) . . ?
C7B N2B H15B 110(3) . . ?
H16B N2B H15B 106(5) . . ?
H14B N2B H15B 112(5) . . ?
O1B C1B O2B 126.7(3) . . ?
O1B C1B C2B 117.1(3) . . ?
O2B C1B C2B 116.1(3) . . ?
N1B C2B C3B 110.1(3) . . ?
N1B C2B C1B 109.1(3) . . ?
C3B C2B C1B 107.7(3) . . ?
N1B C2B H2B 110.0 . . ?
C3B C2B H2B 110.0 . . ?
C1B C2B H2B 110.0 . . ?
C4B C3B C2B 114.3(3) . . ?
C4B C3B H3B1 108.7 . . ?
C2B C3B H3B1 108.7 . . ?
C4B C3B H3B2 108.7 . . ?
C2B C3B H3B2 108.7 . . ?
H3B1 C3B H3B2 107.6 . . ?
C3B C4B S1B 107.9(3) . . ?
C3B C4B H4B1 110.1 . . ?
S1B C4B H4B1 110.1 . . ?
C3B C4B H4B2 110.1 . . ?
S1B C4B H4B2 110.1 . . ?
H4B1 C4B H4B2 108.4 . . ?
S1B C5B H5B1 109.5 . . ?
S1B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
S1B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
O3B C6B O4B 126.4(3) . . ?
O3B C6B C7B 118.2(3) . . ?
O4B C6B C7B 115.4(3) . . ?
N2B C7B C6B 109.2(3) . . ?
N2B C7B C8B 110.7(3) . . ?
C6B C7B C8B 108.2(3) . . ?
N2B C7B H7B 109.6 . . ?
C6B C7B H7B 109.6 . . ?
C8B C7B H7B 109.6 . . ?
C7B C8B S2B 111.2(3) . . ?
C7B C8B H8B1 109.4 . . ?
S2B C8B H8B1 109.4 . . ?
C7B C8B H8B2 109.4 . . ?
S2B C8B H8B2 109.4 . . ?
H8B1 C8B H8B2 108.0 . . ?
C10B C9B S2B 107.5(3) . . ?
C10B C9B H9B1 110.2 . . ?
S2B C9B H9B1 110.2 . . ?
C10B C9B H9B2 110.2 . . ?
S2B C9B H9B2 110.2 . . ?
H9B1 C9B H9B2 108.5 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C5C S1C C4C 100.1(2) . . ?
C8C S2C C9C 102.2(2) . . ?
C2C N1C H12C 110(3) . . ?
C2C N1C H11C 107(4) . . ?
H12C N1C H11C 113(5) . . ?
C2C N1C H13C 109(3) . . ?
H12C N1C H13C 109(4) . . ?
H11C N1C H13C 108(5) . . ?
C7C N2C H16C 110(3) . . ?
C7C N2C H15C 110(3) . . ?
H16C N2C H15C 112(4) . . ?
C7C N2C H14C 111(3) . . ?
H16C N2C H14C 108(4) . . ?
H15C N2C H14C 107(4) . . ?
O2C C1C O1C 125.9(3) . . ?
O2C C1C C2C 116.8(3) . . ?
O1C C1C C2C 117.2(3) . . ?
N1C C2C C1C 107.8(3) . . ?
N1C C2C C3C 110.7(3) . . ?
C1C C2C C3C 108.7(3) . . ?
N1C C2C H2C 109.9 . . ?
C1C C2C H2C 109.9 . . ?
C3C C2C H2C 109.9 . . ?
C4C C3C C2C 113.7(3) . . ?
C4C C3C H3C1 108.8 . . ?
C2C C3C H3C1 108.8 . . ?
C4C C3C H3C2 108.8 . . ?
C2C C3C H3C2 108.8 . . ?
H3C1 C3C H3C2 107.7 . . ?
C3C C4C S1C 108.2(3) . . ?
C3C C4C H4C1 110.1 . . ?
S1C C4C H4C1 110.1 . . ?
C3C C4C H4C2 110.1 . . ?
S1C C4C H4C2 110.1 . . ?
H4C1 C4C H4C2 108.4 . . ?
S1C C5C H5C1 109.5 . . ?
S1C C5C H5C2 109.5 . . ?
H5C1 C5C H5C2 109.5 . . ?
S1C C5C H5C3 109.5 . . ?
H5C1 C5C H5C3 109.5 . . ?
H5C2 C5C H5C3 109.5 . . ?
O4C C6C O3C 126.4(3) . . ?
O4C C6C C7C 117.2(3) . . ?
O3C C6C C7C 116.3(3) . . ?
N2C C7C C6C 109.2(3) . . ?
N2C C7C C8C 112.6(3) . . ?
C6C C7C C8C 107.3(3) . . ?
N2C C7C H7C 109.2 . . ?
C6C C7C H7C 109.2 . . ?
C8C C7C H7C 109.2 . . ?
C7C C8C S2C 117.6(3) . . ?
C7C C8C H8C1 107.9 . . ?
S2C C8C H8C1 107.9 . . ?
C7C C8C H8C2 107.9 . . ?
S2C C8C H8C2 107.9 . . ?
H8C1 C8C H8C2 107.2 . . ?
C10C C9C S2C 108.7(3) . . ?
C10C C9C H9C1 109.9 . . ?
S2C C9C H9C1 109.9 . . ?
C10C C9C H9C2 109.9 . . ?
S2C C9C H9C2 109.9 . . ?
H9C1 C9C H9C2 108.3 . . ?
C9C C10C H10G 109.5 . . ?
C9C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
C9C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 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
O2A C1A C2A N1A 34.9(5) . . . . ?
O1A C1A C2A N1A -148.2(3) . . . . ?
O2A C1A C2A C3A -85.0(4) . . . . ?
O1A C1A C2A C3A 91.9(4) . . . . ?
N1A C2A C3A C4A 52.9(4) . . . . ?
C1A C2A C3A C4A 171.1(3) . . . . ?
C2A C3A C4A S1A 179.2(3) . . . . ?
C5A S1A C4A C3A 170.6(3) . . . . ?
O4A C6A C7A N2A -31.8(4) . . . . ?
O3A C6A C7A N2A 150.9(3) . . . . ?
O4A C6A C7A C8A 88.6(4) . . . . ?
O3A C6A C7A C8A -88.7(4) . . . . ?
N2A C7A C8A S2A -58.1(4) . . . . ?
C6A C7A C8A S2A -177.4(3) . . . . ?
C9A S2A C8A C7A 179.3(3) . . . . ?
C8A S2A C9A C10A -171.3(3) . . . . ?
O1B C1B C2B N1B 28.4(5) . . . . ?
O2B C1B C2B N1B -156.2(3) . . . . ?
O1B C1B C2B C3B -91.1(4) . . . . ?
O2B C1B C2B C3B 84.3(4) . . . . ?
N1B C2B C3B C4B 55.8(4) . . . . ?
C1B C2B C3B C4B 174.6(3) . . . . ?
C2B C3B C4B S1B 179.0(3) . . . . ?
C5B S1B C4B C3B 174.8(3) . . . . ?
O3B C6B C7B N2B -23.2(5) . . . . ?
O4B C6B C7B N2B 159.5(3) . . . . ?
O3B C6B C7B C8B 97.3(4) . . . . ?
O4B C6B C7B C8B -80.0(4) . . . . ?
N2B C7B C8B S2B -58.4(4) . . . . ?
C6B C7B C8B S2B -178.0(2) . . . . ?
C9B S2B C8B C7B 178.0(3) . . . . ?
C8B S2B C9B C10B -170.2(3) . . . . ?
O2C C1C C2C N1C 36.7(4) . . . . ?
O1C C1C C2C N1C -146.2(3) . . . . ?
O2C C1C C2C C3C -83.3(4) . . . . ?
O1C C1C C2C C3C 93.8(4) . . . . ?
N1C C2C C3C C4C 53.2(4) . . . . ?
C1C C2C C3C C4C 171.5(3) . . . . ?
C2C C3C C4C S1C 178.0(3) . . . . ?
C5C S1C C4C C3C 168.7(3) . . . . ?
O4C C6C C7C N2C -28.5(5) . . . . ?
O3C C6C C7C N2C 155.3(3) . . . . ?
O4C C6C C7C C8C 93.8(4) . . . . ?
O3C C6C C7C C8C -82.3(4) . . . . ?
N2C C7C C8C S2C -66.6(4) . . . . ?
C6C C7C C8C S2C 173.2(3) . . . . ?
C9C S2C C8C C7C 89.6(3) . . . . ?
C8C S2C C9C C10C 158.6(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
N1A H11A O4B 0.78(7) 2.04(8) 2.802(5) 167(7) . yes
N1C H12C O3C 0.88(3) 1.95(3) 2.811(4) 168(4) 2_746 yes
N1C H11C O3C 0.89(7) 1.92(7) 2.800(4) 167(6) 2_756 yes
N1C H13C O2C 0.84(5) 1.92(5) 2.751(4) 171(4) 2_756 yes
N1A H12A O4B 0.85(6) 1.95(6) 2.802(5) 173(4) 1_545 yes
N1B H13B O3A 0.83(6) 2.00(6) 2.822(5) 170(5) . yes
N1A H13A O1B 0.91(5) 1.87(5) 2.776(4) 173(5) . yes
N1B H11B O2A 0.91(5) 1.84(5) 2.741(4) 168(5) 1_565 yes
N2B H16B O1C 0.92(6) 1.84(6) 2.753(4) 171(5) 1_565 yes
N2B H14B O4C 0.79(6) 1.99(6) 2.774(4) 171(6) . yes
N2A H14A O4A 0.84(5) 1.94(5) 2.785(4) 177(4) 2_645 yes
N2C H16C O2B 0.84(6) 1.98(6) 2.810(5) 168(4) 1_545 yes
N2A H15A O1A 0.88(6) 1.89(6) 2.764(4) 174(5) 2_655 yes
N2C H15C O2B 0.94(5) 1.92(5) 2.853(5) 171(4) . yes
N2B H15B O1C 0.91(6) 1.91(6) 2.762(4) 156(5) . yes
N1B H12B O3A 0.80(6) 2.05(6) 2.812(5) 158(5) 1_565 yes
N2A H16A O1A 0.92(5) 1.88(5) 2.750(4) 157(4) 2_645 yes
N2C H14C O3B 0.88(5) 1.96(5) 2.831(4) 166(4) 1_545 yes

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_20kaw32
_database_code_depnum_ccdc_archive 'CCDC 2017248'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 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         ?
_chemical_formula_sum            'C14 H26 N2 O12 S'
_chemical_formula_weight         446.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6937(3)
_cell_length_b                   9.8104(5)
_cell_length_c                   10.3950(5)
_cell_angle_alpha                66.609(2)
_cell_angle_beta                 87.445(2)
_cell_angle_gamma                78.329(2)
_cell_volume                     521.49(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      4.64
_cell_measurement_theta_max      72.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.964
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.4116
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            12781
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.638
_diffrn_reflns_theta_max         72.322
_diffrn_reflns_theta_full        67.679
_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 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             3907
_reflns_number_gt                3831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.901
_reflns_Friedel_fraction_full    0.922

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.

 Refined as a 2-component inversion 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)+(0.0502P)²+0.0766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.088(19)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3907
_refine_ls_number_parameters     295
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69776(12) 0.23668(8) 0.84637(8) 0.02914(19) Uani 1 1 d . . . . .
O1 O 0.0966(3) 0.4630(2) 0.7170(2) 0.0217(4) Uani 1 1 d . . . . .
H5 H 1.317(7) -0.155(5) 0.661(4) 0.032 Uiso 1 1 d . U . . .
H8 H -0.326(8) 1.156(4) 0.311(4) 0.032 Uiso 1 1 d . U . . .
H1 H 0.025(8) 0.541(5) 0.686(4) 0.032 Uiso 1 1 d . U . . .
H3 H 0.957(7) 0.440(5) 0.282(4) 0.032 Uiso 1 1 d . U . . .
O2 O 0.2390(3) 0.52216(19) 0.50066(19) 0.0185(4) Uani 1 1 d . . . . .
O3 O 0.8787(3) 0.5408(2) 0.2448(2) 0.0218(4) Uani 1 1 d . . . . .
O4 O 0.7568(3) 0.48111(19) 0.46559(19) 0.0195(4) Uani 1 1 d . . . . .
O5 O 1.2098(3) -0.1966(2) 0.66656(19) 0.0166(4) Uani 1 1 d . . . . .
O6 O 0.9940(3) 0.03234(19) 0.6387(2) 0.0212(4) Uani 1 1 d . . . . .
O7 O 0.5866(3) -0.07697(19) 0.6594(2) 0.0192(4) Uani 1 1 d . . . . .
O8 O 0.8011(3) -0.28287(18) 0.63897(18) 0.0173(4) Uani 1 1 d . . . . .
O9 O -0.2130(3) 1.1935(2) 0.3119(2) 0.0195(4) Uani 1 1 d . . . . .
O10 O 0.0069(3) 0.9682(2) 0.3323(2) 0.0211(4) Uani 1 1 d . . . . .
O11 O 0.4115(3) 1.07325(19) 0.3292(2) 0.0195(4) Uani 1 1 d . . . . .
O12 O 0.1912(3) 1.28779(18) 0.3306(2) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.4950(4) 0.2428(3) 0.5615(3) 0.0177(4) Uani 1 1 d . . . . .
H1A H 0.416(7) 0.279(4) 0.487(4) 0.027 Uiso 1 1 d . U . . .
H1C H 0.607(7) 0.300(4) 0.546(4) 0.027 Uiso 1 1 d . U . . .
H1B H 0.560(7) 0.160(5) 0.583(4) 0.027 Uiso 1 1 d . U . . .
N2 N 0.4996(4) 0.7584(2) 0.4122(2) 0.0161(4) Uani 1 1 d . . . . .
H2A H 0.589(7) 0.732(4) 0.494(4) 0.024 Uiso 1 1 d . U . . .
H2B H 0.430(7) 0.851(4) 0.389(4) 0.024 Uiso 1 1 d . U . . .
H2C H 0.394(7) 0.708(4) 0.427(4) 0.024 Uiso 1 1 d . U . . .
C1 C 0.2151(4) 0.4319(3) 0.6189(3) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.3180(4) 0.2632(3) 0.6653(3) 0.0177(5) Uani 1 1 d . . . . .
H2 H 0.185956 0.214953 0.660115 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4261(5) 0.1829(3) 0.8150(3) 0.0218(5) Uani 1 1 d . . . . .
H3A H 0.460563 0.074559 0.838832 0.026 Uiso 1 1 calc R U . . .
H3B H 0.306284 0.202611 0.878118 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5922(6) 0.4084(4) 0.8746(3) 0.0333(6) Uani 1 1 d . . . . .
H4A H 0.730619 0.443201 0.892058 0.040 Uiso 1 1 calc R U . . .
H4B H 0.511118 0.485445 0.788738 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4258(7) 0.3969(5) 0.9922(4) 0.0444(8) Uani 1 1 d . . . . .
H5A H 0.275740 0.380229 0.968949 0.067 Uiso 1 1 calc R U . . .
H5B H 0.398875 0.489315 1.006996 0.067 Uiso 1 1 calc R U . . .
H5C H 0.495968 0.313693 1.076232 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7677(4) 0.5717(3) 0.3464(3) 0.0166(5) Uani 1 1 d . . . . .
C7 C 0.6556(4) 0.7393(3) 0.2991(3) 0.0166(5) Uani 1 1 d . . . . .
H7 H 0.785939 0.793533 0.291294 0.020 Uiso 1 1 calc R U . . .
C8 C 0.5191(4) 0.8098(3) 0.1576(3) 0.0181(5) Uani 1 1 d . . . . .
H8A H 0.631178 0.804541 0.085824 0.022 Uiso 1 1 calc R U . . .
H8B H 0.455050 0.916116 0.136635 0.022 Uiso 1 1 calc R U . . .
C9 C 0.3134(5) 0.7348(3) 0.1495(3) 0.0206(5) Uani 1 1 d . . . . .
H9A H 0.375483 0.628003 0.171764 0.025 Uiso 1 1 calc R U . . .
H9B H 0.197636 0.742564 0.218863 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1886(5) 0.8074(4) 0.0053(3) 0.0317(6) Uani 1 1 d . . . . .
H10A H 0.115293 0.910968 -0.013891 0.048 Uiso 1 1 calc R U . . .
H10B H 0.067533 0.753101 0.002575 0.048 Uiso 1 1 calc R U . . .
H10C H 0.304018 0.804028 -0.064167 0.048 Uiso 1 1 calc R U . . .
C11 C 1.0094(4) -0.0975(3) 0.6533(2) 0.0135(5) Uani 1 1 d . . . . .
C12 C 0.7796(4) -0.1600(3) 0.6521(2) 0.0135(5) Uani 1 1 d . . . . .
C13 C -0.0113(4) 1.0966(3) 0.3231(2) 0.0145(5) Uani 1 1 d . . . . .
C14 C 0.2152(4) 1.1605(3) 0.3271(3) 0.0148(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.804(3) . ?
S1 C3 1.813(3) . ?
O1 C1 1.301(3) . ?
O1 H1 0.74(4) . ?
O2 C1 1.218(3) . ?
O3 C6 1.313(3) . ?
O3 H3 0.93(4) . ?
O4 C6 1.212(3) . ?
O5 C11 1.313(3) . ?
O5 H5 0.79(4) . ?
O6 C11 1.206(3) . ?
O7 C12 1.247(3) . ?
O8 C12 1.248(3) . ?
O9 C13 1.311(3) . ?
O9 H8 0.80(4) . ?
O10 C13 1.208(3) . ?
O11 C14 1.258(3) . ?
O12 C14 1.244(3) . ?
N1 C2 1.488(3) . ?
N1 H1A 0.82(4) . ?
N1 H1C 0.90(4) . ?
N1 H1B 0.77(4) . ?
N2 C7 1.490(3) . ?
N2 H2A 0.93(4) . ?
N2 H2B 0.85(4) . ?
N2 H2C 0.82(4) . ?
C1 C2 1.521(3) . ?
C2 C3 1.529(4) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.495(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.521(3) . ?
C7 C8 1.524(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.518(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.556(3) . ?
C13 C14 1.552(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C3 104.32(13) . . ?
C1 O1 H1 109(3) . . ?
C6 O3 H3 108(2) . . ?
C11 O5 H5 107(3) . . ?
C13 O9 H8 111(3) . . ?
C2 N1 H1A 104(3) . . ?
C2 N1 H1C 113(2) . . ?
H1A N1 H1C 105(3) . . ?
C2 N1 H1B 112(3) . . ?
H1A N1 H1B 115(4) . . ?
H1C N1 H1B 108(4) . . ?
C7 N2 H2A 111(2) . . ?
C7 N2 H2B 111(2) . . ?
H2A N2 H2B 106(3) . . ?
C7 N2 H2C 111(2) . . ?
H2A N2 H2C 110(3) . . ?
H2B N2 H2C 107(3) . . ?
O2 C1 O1 126.2(2) . . ?
O2 C1 C2 121.6(2) . . ?
O1 C1 C2 112.1(2) . . ?
N1 C2 C1 108.1(2) . . ?
N1 C2 C3 111.5(2) . . ?
C1 C2 C3 115.4(2) . . ?
N1 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C2 C3 S1 115.73(19) . . ?
C2 C3 H3A 108.3 . . ?
S1 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
S1 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 S1 116.1(2) . . ?
C5 C4 H4A 108.3 . . ?
S1 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
S1 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 125.6(2) . . ?
O4 C6 C7 122.4(2) . . ?
O3 C6 C7 112.0(2) . . ?
N2 C7 C6 107.8(2) . . ?
N2 C7 C8 111.51(19) . . ?
C6 C7 C8 114.8(2) . . ?
N2 C7 H7 107.5 . . ?
C6 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C7 C8 C9 114.5(2) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 112.0(2) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 O5 125.9(2) . . ?
O6 C11 C12 120.4(2) . . ?
O5 C11 C12 113.69(18) . . ?
O7 C12 O8 125.9(2) . . ?
O7 C12 C11 115.41(19) . . ?
O8 C12 C11 118.67(19) . . ?
O10 C13 O9 125.8(2) . . ?
O10 C13 C14 120.7(2) . . ?
O9 C13 C14 113.46(19) . . ?
O12 C14 O11 125.8(2) . . ?
O12 C14 C13 119.4(2) . . ?
O11 C14 C13 114.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 15.4(3) . . . . ?
O1 C1 C2 N1 -166.9(2) . . . . ?
O2 C1 C2 C3 140.9(2) . . . . ?
O1 C1 C2 C3 -41.3(3) . . . . ?
N1 C2 C3 S1 56.0(2) . . . . ?
C1 C2 C3 S1 -67.8(3) . . . . ?
C4 S1 C3 C2 82.5(2) . . . . ?
C3 S1 C4 C5 58.1(3) . . . . ?
O4 C6 C7 N2 -11.2(3) . . . . ?
O3 C6 C7 N2 170.22(19) . . . . ?
O4 C6 C7 C8 -136.2(2) . . . . ?
O3 C6 C7 C8 45.3(3) . . . . ?
N2 C7 C8 C9 -64.5(3) . . . . ?
C6 C7 C8 C9 58.5(3) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
O6 C11 C12 O7 -11.6(3) . . . . ?
O5 C11 C12 O7 170.4(2) . . . . ?
O6 C11 C12 O8 165.8(2) . . . . ?
O5 C11 C12 O8 -12.2(3) . . . . ?
O10 C13 C14 O12 -173.4(2) . . . . ?
O9 C13 C14 O12 5.5(3) . . . . ?
O10 C13 C14 O11 5.3(3) . . . . ?
O9 C13 C14 O11 -175.8(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
N1 H1C O4 0.90(4) 1.99(4) 2.847(3) 159(3) . yes
N2 H2A O8 0.93(4) 1.91(4) 2.827(3) 167(3) 1_565 yes
N2 H2C O2 0.82(4) 2.05(4) 2.827(3) 159(3) . yes
N1 H1B O7 0.77(4) 2.11(4) 2.829(3) 155(4) . yes
N2 H2B O11 0.85(4) 2.00(4) 2.799(3) 156(3) . yes
N1 H1A O12 0.82(4) 2.08(4) 2.858(3) 159(4) 1_545 yes
O5 H5 O7 0.79(4) 1.84(4) 2.631(2) 174(4) 1_655 yes
O9 H8 O11 0.80(4) 1.81(4) 2.610(2) 174(4) 1_455 yes
O1 H1 O8 0.74(4) 1.83(4) 2.554(2) 167(4) 1_465 yes
O3 H3 O12 0.93(4) 1.71(4) 2.592(2) 158(4) 1_645 yes

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw59
_database_code_depnum_ccdc_archive 'CCDC 2051776'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-11-11 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         'C5 H11 N O2 S, C6 H13 N O2'
_chemical_formula_sum            'C11 H24 N2 O4 S'
_chemical_formula_weight         280.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.1451(4)
_cell_length_b                   10.0555(7)
_cell_length_c                   13.4606(10)
_cell_angle_alpha                85.184(2)
_cell_angle_beta                 86.278(2)
_cell_angle_gamma                84.585(2)
_cell_volume                     689.71(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      5.32
_cell_measurement_theta_max      72.06

_exptl_crystal_description       rhomboid
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.138
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_max          0.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    2.185
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6099
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            17337
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.430
_diffrn_reflns_theta_max         72.307
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             5137
_reflns_number_gt                5071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.882
_reflns_Friedel_fraction_full    0.904

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.0396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 2335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5137
_refine_ls_number_parameters     365
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.29099(6) 0.37894(3) 0.82947(2) 0.01358(12) Uani 1 1 d . . . . .
O1A O 0.1407(2) 0.61182(11) 0.60632(9) 0.0115(2) Uani 1 1 d . . . . .
O2A O -0.2627(2) 0.54449(11) 0.62601(9) 0.0117(2) Uani 1 1 d . . . . .
O3A O 0.7469(2) 0.38586(10) 0.42241(8) 0.0113(2) Uani 1 1 d . . . . .
O4A O 1.1421(2) 0.46274(11) 0.39942(9) 0.0122(2) Uani 1 1 d . . . . .
N1A N 0.3687(3) 0.36164(14) 0.59555(10) 0.0095(3) Uani 1 1 d . . . . .
H1A H 0.443(5) 0.275(2) 0.6080(16) 0.014 Uiso 1 1 d . U . . .
H2A H 0.377(4) 0.380(2) 0.5296(19) 0.014 Uiso 1 1 d . U . . .
H3A H 0.472(5) 0.415(2) 0.6218(16) 0.014 Uiso 1 1 d . U . . .
N2A N 0.5145(3) 0.63795(14) 0.43546(10) 0.0097(3) Uani 1 1 d . . . . .
H4A H 0.945(5) -0.225(2) 0.6055(16) 0.015 Uiso 1 1 d . U . . .
H5A H 0.967(5) -0.084(2) 0.6199(16) 0.015 Uiso 1 1 d . U . . .
H6A H 0.879(4) -0.121(2) 0.5274(19) 0.015 Uiso 1 1 d . U . . .
C1A C -0.0179(3) 0.52332(16) 0.62154(11) 0.0090(3) Uani 1 1 d . . . . .
C2A C 0.0936(3) 0.37645(15) 0.63716(11) 0.0091(3) Uani 1 1 d . . . . .
H1 H -0.010590 0.322305 0.598112 0.011 Uiso 1 1 calc R U . . .
C3A C 0.0713(3) 0.32018(16) 0.74650(12) 0.0118(3) Uani 1 1 d . . . . .
H3A1 H 0.101672 0.221328 0.748320 0.014 Uiso 1 1 calc R U . . .
H3A2 H -0.110320 0.342057 0.773012 0.014 Uiso 1 1 calc R U . . .
C4A C 0.1311(3) 0.54150(17) 0.85815(13) 0.0164(3) Uani 1 1 d . . . . .
H4A1 H 0.132178 0.604076 0.797313 0.020 Uiso 1 1 calc R U . . .
H4A2 H -0.053034 0.532267 0.881836 0.020 Uiso 1 1 calc R U . . .
C5A C 0.2752(4) 0.59612(17) 0.93833(13) 0.0207(3) Uani 1 1 d . . . . .
H5A1 H 0.271357 0.534381 0.998638 0.031 Uiso 1 1 calc R U . . .
H5A2 H 0.190324 0.683940 0.953847 0.031 Uiso 1 1 calc R U . . .
H5A3 H 0.457031 0.605362 0.914359 0.031 Uiso 1 1 calc R U . . .
C6A C 0.8970(3) 0.47771(15) 0.40130(11) 0.0085(3) Uani 1 1 d . . . . .
C7A C 0.7629(3) 0.61810(15) 0.37305(12) 0.0103(3) Uani 1 1 d . . . . .
H7A H 0.881005 0.687985 0.384807 0.012 Uiso 1 1 calc R U . . .
C8A C 0.6950(3) 0.63084(17) 0.26312(12) 0.0145(3) Uani 1 1 d . . . . .
H8A1 H 0.602104 0.552658 0.250357 0.017 Uiso 1 1 calc R U . . .
H8A2 H 0.573409 0.712169 0.251220 0.017 Uiso 1 1 calc R U . . .
C9A C 0.9312(3) 0.63908(17) 0.18849(13) 0.0178(3) Uani 1 1 d . . . . .
H9A1 H 0.880959 0.616046 0.122700 0.021 Uiso 1 1 calc R U . . .
H9A2 H 1.072319 0.571501 0.210794 0.021 Uiso 1 1 calc R U . . .
C10A C 1.0379(4) 0.77740(18) 0.17597(14) 0.0207(3) Uani 1 1 d . . . . .
H10A H 1.066907 0.806017 0.242672 0.025 Uiso 1 1 calc R U . . .
H10B H 1.208885 0.770407 0.137692 0.025 Uiso 1 1 calc R U . . .
C11A C 0.8537(4) 0.88341(18) 0.12232(15) 0.0265(4) Uani 1 1 d . . . . .
H11A H 0.819621 0.854290 0.057085 0.040 Uiso 1 1 calc R U . . .
H11B H 0.934511 0.968351 0.112959 0.040 Uiso 1 1 calc R U . . .
H11C H 0.688581 0.895733 0.162431 0.040 Uiso 1 1 calc R U . . .
S1B S 0.77331(6) -0.13389(3) 0.82709(2) 0.01272(11) Uani 1 1 d . . . . .
O1B O 0.6389(2) 0.11058(11) 0.60701(9) 0.0111(2) Uani 1 1 d . . . . .
O2B O 0.2346(2) 0.04406(11) 0.62913(9) 0.0116(2) Uani 1 1 d . . . . .
O3B O 1.2515(2) -0.10974(10) 0.41652(9) 0.0119(2) Uani 1 1 d . . . . .
O4B O 1.6531(2) -0.04040(11) 0.39578(8) 0.0117(2) Uani 1 1 d . . . . .
N1B N 0.8661(3) -0.13856(14) 0.59240(10) 0.0092(3) Uani 1 1 d . . . . .
H7B H 0.442(5) 0.719(3) 0.4250(16) 0.014 Uiso 1 1 d . U . . .
H9B H 0.396(5) 0.588(2) 0.4188(16) 0.014 Uiso 1 1 d . U . . .
H8B H 0.538(4) 0.619(2) 0.5005(19) 0.014 Uiso 1 1 d . U . . .
N2B N 1.0213(3) 0.13685(14) 0.43588(10) 0.0092(3) Uani 1 1 d . . . . .
H2 H 0.941(5) 0.217(3) 0.4257(16) 0.014 Uiso 1 1 d . U . . .
H3 H 1.028(4) 0.115(2) 0.5025(19) 0.014 Uiso 1 1 d . U . . .
H12B H 0.913(5) 0.087(2) 0.4132(16) 0.014 Uiso 1 1 d . U . . .
C1B C 0.4790(3) 0.02237(16) 0.62184(11) 0.0088(3) Uani 1 1 d . . . . .
C2B C 0.5896(3) -0.12502(15) 0.63239(11) 0.0084(3) Uani 1 1 d . . . . .
H2B H 0.486821 -0.175593 0.590140 0.010 Uiso 1 1 calc R U . . .
C3B C 0.5604(3) -0.18805(15) 0.73974(11) 0.0104(3) Uani 1 1 d . . . . .
H3B1 H 0.592438 -0.286534 0.738338 0.013 Uiso 1 1 calc R U . . .
H3B2 H 0.377107 -0.168118 0.765128 0.013 Uiso 1 1 calc R U . . .
C4B C 0.6111(3) 0.02579(17) 0.86181(12) 0.0151(3) Uani 1 1 d . . . . .
H4B1 H 0.724034 0.066477 0.905472 0.018 Uiso 1 1 calc R U . . .
H4B2 H 0.589946 0.086943 0.800728 0.018 Uiso 1 1 calc R U . . .
C5B C 0.3445(4) 0.01352(18) 0.91568(14) 0.0220(3) Uani 1 1 d . . . . .
H5B1 H 0.227457 -0.020772 0.871226 0.033 Uiso 1 1 calc R U . . .
H5B2 H 0.271195 0.101777 0.934997 0.033 Uiso 1 1 calc R U . . .
H5B3 H 0.363039 -0.048362 0.975558 0.033 Uiso 1 1 calc R U . . .
C6B C 1.4084(3) -0.02013(15) 0.40070(11) 0.0083(3) Uani 1 1 d . . . . .
C7B C 1.2868(3) 0.12550(15) 0.38477(11) 0.0091(3) Uani 1 1 d . . . . .
H4 H 1.398447 0.185295 0.415491 0.011 Uiso 1 1 calc R U . . .
C8B C 1.2697(3) 0.17133(16) 0.27374(12) 0.0125(3) Uani 1 1 d . . . . .
H8B1 H 1.208500 0.098414 0.238706 0.015 Uiso 1 1 calc R U . . .
H8B2 H 1.138700 0.249698 0.266580 0.015 Uiso 1 1 calc R U . . .
C9B C 1.5314(3) 0.20920(17) 0.22403(12) 0.0142(3) Uani 1 1 d . . . . .
H9B1 H 1.591564 0.283285 0.258092 0.017 Uiso 1 1 calc R U . . .
H9B2 H 1.663480 0.131369 0.231800 0.017 Uiso 1 1 calc R U . . .
C10B C 1.5110(3) 0.25232(19) 0.11354(13) 0.0207(3) Uani 1 1 d . . . . .
H10C H 1.372930 0.327380 0.106054 0.025 Uiso 1 1 calc R U . . .
H10D H 1.456972 0.176768 0.079451 0.025 Uiso 1 1 calc R U . . .
C11B C 1.7651(4) 0.29619(19) 0.06231(14) 0.0233(3) Uani 1 1 d . . . . .
H11D H 1.817832 0.372592 0.094387 0.035 Uiso 1 1 calc R U . . .
H11E H 1.738909 0.322414 -0.008361 0.035 Uiso 1 1 calc R U . . .
H11F H 1.902180 0.221790 0.067927 0.035 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 1.8097(16) . ?
S1A C4A 1.8190(17) . ?
O1A C1A 1.259(2) . ?
O2A C1A 1.256(2) . ?
O3A C6A 1.2620(19) . ?
O4A C6A 1.255(2) . ?
N1A C2A 1.4870(19) . ?
N2A C7A 1.490(2) . ?
C1A C2A 1.536(2) . ?
C2A C3A 1.533(2) . ?
C4A C5A 1.515(3) . ?
C6A C7A 1.541(2) . ?
C7A C8A 1.535(2) . ?
C8A C9A 1.530(2) . ?
C9A C10A 1.535(2) . ?
C10A C11A 1.525(2) . ?
S1B C3B 1.8075(16) . ?
S1B C4B 1.8208(17) . ?
O1B C1B 1.261(2) . ?
O2B C1B 1.254(2) . ?
O3B C6B 1.2615(19) . ?
O4B C6B 1.255(2) . ?
N1B C2B 1.4863(19) . ?
N2B C7B 1.488(2) . ?
C1B C2B 1.535(2) . ?
C2B C3B 1.532(2) . ?
C4B C5B 1.520(2) . ?
C6B C7B 1.541(2) . ?
C7B C8B 1.532(2) . ?
C8B C9B 1.531(2) . ?
C9B C10B 1.521(2) . ?
C10B C11B 1.523(2) . ?

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 C4A 102.93(8) . . ?
O2A C1A O1A 125.56(15) . . ?
O2A C1A C2A 116.36(13) . . ?
O1A C1A C2A 118.08(14) . . ?
N1A C2A C3A 111.33(13) . . ?
N1A C2A C1A 109.83(12) . . ?
C3A C2A C1A 113.15(13) . . ?
C2A C3A S1A 116.38(11) . . ?
C5A C4A S1A 109.12(12) . . ?
O4A C6A O3A 125.44(14) . . ?
O4A C6A C7A 118.54(13) . . ?
O3A C6A C7A 116.00(13) . . ?
N2A C7A C8A 107.96(13) . . ?
N2A C7A C6A 109.03(12) . . ?
C8A C7A C6A 110.43(13) . . ?
C9A C8A C7A 114.39(13) . . ?
C8A C9A C10A 113.81(13) . . ?
C11A C10A C9A 112.62(14) . . ?
C3B S1B C4B 103.75(8) . . ?
O2B C1B O1B 125.72(15) . . ?
O2B C1B C2B 116.36(13) . . ?
O1B C1B C2B 117.92(14) . . ?
N1B C2B C3B 111.58(13) . . ?
N1B C2B C1B 110.19(12) . . ?
C3B C2B C1B 112.78(12) . . ?
C2B C3B S1B 115.92(11) . . ?
C5B C4B S1B 113.41(11) . . ?
O4B C6B O3B 125.36(14) . . ?
O4B C6B C7B 117.91(13) . . ?
O3B C6B C7B 116.72(13) . . ?
N2B C7B C8B 109.86(12) . . ?
N2B C7B C6B 109.15(12) . . ?
C8B C7B C6B 111.91(12) . . ?
C9B C8B C7B 112.88(12) . . ?
C10B C9B C8B 112.01(12) . . ?
C9B C10B C11B 113.58(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1B 0.92(2) 1.86(3) 2.7620(17) 167(2) . yes
N1A H2A O3A 0.89(2) 2.32(2) 2.9464(17) 127.7(19) . yes
N1A H2A O4A 0.89(2) 2.25(2) 3.0146(18) 144(2) 1_455 yes
N1A H3A O2A 0.90(2) 1.98(2) 2.8339(18) 158.6(19) 1_655 yes
N1B H4A O1A 0.93(2) 1.84(3) 2.7599(17) 168(2) 1_645 yes
N1B H5A O2B 0.90(2) 1.99(2) 2.8536(18) 159(2) 1_655 yes
N1B H6A O3B 0.88(2) 2.36(2) 3.0007(17) 130.6(19) . yes
N1B H6A O4B 0.88(2) 2.24(2) 2.9857(18) 143(2) 1_455 yes
N2A H7B O3B 0.87(3) 1.90(3) 2.7605(18) 173(2) 1_465 yes
N2A H9B O4A 0.87(2) 1.94(2) 2.8125(18) 172(2) 1_455 yes
N2A H8B O1A 0.89(3) 2.42(2) 2.9116(17) 115.0(18) . yes
N2A H8B O2A 0.89(3) 2.08(3) 2.9241(19) 157(2) 1_655 yes
N2B H2 O3A 0.88(3) 1.88(3) 2.7542(18) 172(2) . yes
N2B H3 O1B 0.91(2) 2.37(2) 2.9420(17) 120.7(18) . yes
N2B H3 O2B 0.91(2) 2.11(3) 2.9345(19) 151(2) 1_655 yes
N2B H12B O4B 0.87(2) 1.98(2) 2.8265(18) 166(2) 1_455 yes
C3B H3B1 O2A 0.99 2.40 3.2332(19) 141.0 1_645 yes
C5B H5B1 S1B 0.98 2.81 3.7190(19) 154.4 1_455 yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_20kaw09
_database_code_depnum_ccdc_archive 'CCDC 2017246'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 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         'C5 H12 N O2 S, C5 H12 N O2 S, 2 C2 H O4'
_chemical_formula_sum            'C14 H26 N2 O12 S2'
_chemical_formula_weight         478.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   5.6622(2)
_cell_length_b                   19.4329(7)
_cell_length_c                   9.8324(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.810(2)
_cell_angle_gamma                90
_cell_volume                     1058.99(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5135
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      74.48

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.035
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_max          0.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.872
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5527
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            15724
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.551
_diffrn_reflns_theta_max         74.496
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4222
_reflns_number_gt                3484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.978

_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to oxygen and nitrogen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.053(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4222
_refine_ls_number_parameters     303
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.9062(3) 0.24542(7) 0.79861(16) 0.0285(3) Uani 1 1 d . . . . .
S2 S 0.4415(3) 0.67585(7) 0.51782(15) 0.0288(3) Uani 1 1 d . . . . .
O1 O 0.2168(7) 0.3792(2) 0.5735(4) 0.0265(9) Uani 1 1 d D . . . .
H20 H 0.140(12) 0.399(3) 0.499(5) 0.032 Uiso 1 1 d D U . . .
O2 O 0.3574(7) 0.48762(19) 0.5999(4) 0.0228(8) Uani 1 1 d . . . . .
O3 O 1.0182(7) 0.6160(2) 0.7029(4) 0.0249(8) Uani 1 1 d D . . . .
H25 H 1.081(12) 0.601(3) 0.784(4) 0.030 Uiso 1 1 d D U . . .
O4 O 0.8841(7) 0.50755(19) 0.6669(4) 0.0220(8) Uani 1 1 d . . . . .
O7 O 1.3172(7) 0.40726(19) 1.2506(4) 0.0202(8) Uani 1 1 d D . . . .
O8 O 1.1021(7) 0.43150(18) 1.0375(4) 0.0195(8) Uani 1 1 d . . . . .
O9 O 0.6925(7) 0.42076(19) 1.1382(4) 0.0210(8) Uani 1 1 d . . . . .
H7 H 1.445(8) 0.409(3) 1.220(7) 0.025 Uiso 1 1 d D U . . .
O10 O 0.9125(7) 0.41802(18) 1.3536(4) 0.0193(8) Uani 1 1 d . . . . .
O11 O -0.0785(6) 0.59044(19) 0.0216(4) 0.0184(7) Uani 1 1 d D . . . .
H11 H -0.201(8) 0.591(3) 0.058(6) 0.022 Uiso 1 1 d D U . . .
O12 O 0.1366(7) 0.56469(18) 0.2347(4) 0.0191(8) Uani 1 1 d . . . . .
O13 O 0.5466(6) 0.5803(2) 0.1349(4) 0.0209(8) Uani 1 1 d . . . . .
O14 O 0.3251(6) 0.58107(19) -0.0805(4) 0.0191(7) Uani 1 1 d . . . . .
N1 N 0.6023(8) 0.4661(2) 0.8594(5) 0.0193(9) Uani 1 1 d . . . . .
H1A H 0.691(12) 0.454(3) 0.948(7) 0.023 Uiso 1 1 d . U . . .
H1B H 0.510(12) 0.504(3) 0.874(6) 0.023 Uiso 1 1 d . U . . .
H1C H 0.732(12) 0.474(3) 0.811(7) 0.023 Uiso 1 1 d . U . . .
N2 N 0.6382(9) 0.5353(3) 0.4094(5) 0.0193(9) Uani 1 1 d . . . . .
H2B H 0.700(13) 0.502(4) 0.414(7) 0.023 Uiso 1 1 d . U . . .
H2C H 0.539(13) 0.532(4) 0.451(7) 0.023 Uiso 1 1 d . U . . .
H2A H 0.591(12) 0.544(3) 0.310(7) 0.023 Uiso 1 1 d . U . . .
C1 C 0.3340(9) 0.4302(3) 0.6438(6) 0.0192(11) Uani 1 1 d . . . . .
C2 C 0.4327(10) 0.4110(3) 0.7950(6) 0.0196(11) Uani 1 1 d . . . . .
H2 H 0.293302 0.411731 0.843054 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5451(10) 0.3397(3) 0.8180(6) 0.0204(11) Uani 1 1 d . . . . .
H3A H 0.419632 0.305170 0.781593 0.025 Uiso 1 1 calc R U . . .
H3B H 0.596184 0.331947 0.919278 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7628(10) 0.3272(3) 0.7504(6) 0.0235(12) Uani 1 1 d . . . . .
H4A H 0.882137 0.364474 0.778289 0.028 Uiso 1 1 calc R U . . .
H4B H 0.709012 0.329028 0.648096 0.028 Uiso 1 1 calc R U . . .
C5 C 1.0553(11) 0.2631(3) 0.9765(6) 0.0296(13) Uani 1 1 d . . . . .
H5A H 1.161246 0.303109 0.978597 0.044 Uiso 1 1 calc R U . . .
H5B H 1.151376 0.223008 1.014817 0.044 Uiso 1 1 calc R U . . .
H5C H 0.933934 0.272649 1.032113 0.044 Uiso 1 1 calc R U . . .
C6 C 0.9068(9) 0.5662(3) 0.6272(6) 0.0187(11) Uani 1 1 d . . . . .
C7 C 0.8187(10) 0.5870(3) 0.4773(6) 0.0207(11) Uani 1 1 d . . . . .
H7A H 0.959731 0.584170 0.430713 0.025 Uiso 1 1 calc R U . . .
C8 C 0.7136(10) 0.6600(3) 0.4526(6) 0.0236(12) Uani 1 1 d . . . . .
H8A H 0.678655 0.669192 0.351400 0.028 Uiso 1 1 calc R U . . .
H8B H 0.838275 0.693325 0.496663 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5562(12) 0.7083(4) 0.6914(7) 0.0375(15) Uani 1 1 d . . . . .
H9A H 0.592820 0.669417 0.757416 0.045 Uiso 1 1 calc R U . . .
H9B H 0.707115 0.734367 0.693440 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3689(11) 0.7548(4) 0.7339(7) 0.0371(15) Uani 1 1 d . . . . .
H10A H 0.337314 0.794015 0.670012 0.056 Uiso 1 1 calc R U . . .
H10B H 0.429020 0.771555 0.828633 0.056 Uiso 1 1 calc R U . . .
H10C H 0.219193 0.728940 0.730361 0.056 Uiso 1 1 calc R U . . .
C11 C 1.1159(9) 0.4196(2) 1.1598(5) 0.0162(10) Uani 1 1 d . . . . .
C12 C 0.8897(9) 0.4190(2) 1.2257(6) 0.0171(11) Uani 1 1 d . . . . .
C13 C 0.1217(9) 0.5783(2) 0.1129(5) 0.0165(10) Uani 1 1 d . . . . .
C14 C 0.3507(9) 0.5814(3) 0.0493(6) 0.0170(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.804(6) . ?
S1 C5 1.812(6) . ?
S2 C9 1.811(6) . ?
S2 C8 1.812(6) . ?
O1 C1 1.309(7) . ?
O1 H20 0.86(3) . ?
O2 C1 1.214(7) . ?
O3 C6 1.303(7) . ?
O3 H25 0.86(3) . ?
O4 C6 1.219(6) . ?
O7 C11 1.318(7) . ?
O7 H7 0.84(3) . ?
O8 C11 1.211(6) . ?
O9 C12 1.263(7) . ?
O10 C12 1.238(6) . ?
O11 C13 1.315(6) . ?
O11 H11 0.84(3) . ?
O12 C13 1.212(6) . ?
O13 C14 1.248(7) . ?
O14 C14 1.254(6) . ?
N1 C2 1.491(7) . ?
N1 H1A 0.94(7) . ?
N1 H1B 0.93(7) . ?
N1 H1C 0.96(7) . ?
N2 C7 1.490(7) . ?
N2 H2B 0.73(7) . ?
N2 H2C 0.76(7) . ?
N2 H2A 0.97(7) . ?
C1 C2 1.524(8) . ?
C2 C3 1.521(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.535(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.512(8) . ?
C7 C8 1.539(8) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.550(7) . ?
C13 C14 1.552(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C5 100.5(3) . . ?
C9 S2 C8 103.1(3) . . ?
C1 O1 H20 103(5) . . ?
C6 O3 H25 110(5) . . ?
C11 O7 H7 116(5) . . ?
C13 O11 H11 112(4) . . ?
C2 N1 H1A 113(4) . . ?
C2 N1 H1B 108(4) . . ?
H1A N1 H1B 105(5) . . ?
C2 N1 H1C 113(4) . . ?
H1A N1 H1C 100(5) . . ?
H1B N1 H1C 117(5) . . ?
C7 N2 H2B 107(6) . . ?
C7 N2 H2C 110(5) . . ?
H2B N2 H2C 107(7) . . ?
C7 N2 H2A 111(4) . . ?
H2B N2 H2A 104(7) . . ?
H2C N2 H2A 118(6) . . ?
O2 C1 O1 126.1(5) . . ?
O2 C1 C2 121.8(5) . . ?
O1 C1 C2 112.0(4) . . ?
N1 C2 C3 112.2(4) . . ?
N1 C2 C1 108.3(4) . . ?
C3 C2 C1 115.3(4) . . ?
N1 C2 H2 106.9 . . ?
C3 C2 H2 106.9 . . ?
C1 C2 H2 106.9 . . ?
C2 C3 C4 115.4(4) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 S1 112.6(4) . . ?
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 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 125.6(5) . . ?
O4 C6 C7 121.7(5) . . ?
O3 C6 C7 112.5(4) . . ?
N2 C7 C6 108.4(4) . . ?
N2 C7 C8 110.1(5) . . ?
C6 C7 C8 116.1(4) . . ?
N2 C7 H7A 107.3 . . ?
C6 C7 H7A 107.3 . . ?
C8 C7 H7A 107.3 . . ?
C7 C8 S2 115.5(4) . . ?
C7 C8 H8A 108.4 . . ?
S2 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
S2 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 S2 109.3(5) . . ?
C10 C9 H9A 109.8 . . ?
S2 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
S2 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O8 C11 O7 125.4(5) . . ?
O8 C11 C12 121.7(5) . . ?
O7 C11 C12 112.9(4) . . ?
O10 C12 O9 125.9(5) . . ?
O10 C12 C11 120.1(5) . . ?
O9 C12 C11 114.0(4) . . ?
O12 C13 O11 126.1(4) . . ?
O12 C13 C14 120.8(4) . . ?
O11 C13 C14 113.1(4) . . ?
O13 C14 O14 126.0(4) . . ?
O13 C14 C13 115.3(4) . . ?
O14 C14 C13 118.6(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
O2 C1 C2 N1 -13.8(7) . . . . ?
O1 C1 C2 N1 169.0(4) . . . . ?
O2 C1 C2 C3 -140.4(5) . . . . ?
O1 C1 C2 C3 42.4(6) . . . . ?
N1 C2 C3 C4 -63.9(6) . . . . ?
C1 C2 C3 C4 60.7(6) . . . . ?
C2 C3 C4 S1 173.4(4) . . . . ?
C5 S1 C4 C3 -73.3(4) . . . . ?
O4 C6 C7 N2 19.5(7) . . . . ?
O3 C6 C7 N2 -164.3(4) . . . . ?
O4 C6 C7 C8 144.0(5) . . . . ?
O3 C6 C7 C8 -39.8(6) . . . . ?
N2 C7 C8 S2 59.6(5) . . . . ?
C6 C7 C8 S2 -64.1(6) . . . . ?
C9 S2 C8 C7 91.5(5) . . . . ?
C8 S2 C9 C10 152.8(5) . . . . ?
O8 C11 C12 O10 -168.0(5) . . . . ?
O7 C11 C12 O10 10.8(6) . . . . ?
O8 C11 C12 O9 10.8(7) . . . . ?
O7 C11 C12 O9 -170.3(4) . . . . ?
O12 C13 C14 O13 -11.1(7) . . . . ?
O11 C13 C14 O13 169.9(5) . . . . ?
O12 C13 C14 O14 165.1(5) . . . . ?
O11 C13 C14 O14 -13.8(6) . . . . ?

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 H20 O10 0.86(3) 1.76(4) 2.586(5) 160(7) 1_454 yes
O3 H25 O14 0.86(3) 1.75(4) 2.550(5) 154(7) 1_656 yes
O7 H7 O9 0.84(3) 1.77(3) 2.601(5) 171(7) 1_655 yes
O11 H11 O13 0.84(3) 1.76(3) 2.599(5) 172(7) 1_455 yes
N1 H1A O9 0.94(7) 1.98(7) 2.825(6) 148(6) . yes
N1 H1B O14 0.93(7) 1.93(7) 2.860(6) 176(6) 1_556 yes
N1 H1C O4 0.96(7) 1.92(7) 2.831(6) 157(6) . yes
N2 H2B O10 0.73(7) 2.18(7) 2.873(6) 159(7) 1_554 yes
N2 H2C O2 0.76(7) 2.14(7) 2.849(6) 156(7) . yes
N2 H2A O13 0.97(7) 1.83(7) 2.783(6) 166(6) . yes

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.076


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw66
_database_code_depnum_ccdc_archive 'CCDC 2051777'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-11-11 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         'C5 H11 N O2 S, C5 H11 N O2'
_chemical_formula_sum            'C10 H22 N2 O4 S'
_chemical_formula_weight         266.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.9251(9)
_cell_length_b                   4.7178(4)
_cell_length_c                   14.9823(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.286(4)
_cell_angle_gamma                90
_cell_volume                     676.72(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      72.28

_exptl_crystal_description       rods
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.066
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_max          0.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    2.200
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_reflns_number            27007
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.058
_diffrn_reflns_theta_max         72.880
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2664
_reflns_number_gt                2590
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0811P)²+0.2645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.129(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2664
_refine_ls_number_parameters     174
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.96697(8) 0.8777(2) 0.15500(5) 0.0299(2) Uani 1 1 d . . . . .
O1 O 0.9220(2) 0.3843(5) 0.43541(14) 0.0221(4) Uani 1 1 d . . . . .
N1 N 1.0955(3) 0.7581(6) 0.38575(19) 0.0206(5) Uani 1 1 d D . . . .
H1A H 1.138(4) 0.890(8) 0.363(3) 0.031 Uiso 1 1 d D U . . .
H1B H 1.109(5) 0.777(10) 0.4450(18) 0.031 Uiso 1 1 d D U . . .
H1C H 1.125(4) 0.591(6) 0.377(3) 0.031 Uiso 1 1 d D U . . .
C1 C 0.8613(3) 0.5908(6) 0.3903(2) 0.0192(6) Uani 1 1 d . . . . .
O2 O 0.7355(2) 0.6590(5) 0.37863(16) 0.0251(5) Uani 1 1 d . . . . .
N2 N 0.5994(3) 0.1592(6) 0.40188(18) 0.0200(5) Uani 1 1 d D . . . .
H2A H 0.640(4) 0.321(7) 0.397(3) 0.030 Uiso 1 1 d D U . . .
H2B H 0.596(4) 0.116(10) 0.4576(19) 0.030 Uiso 1 1 d D U . . .
H2C H 0.656(4) 0.021(8) 0.392(3) 0.030 Uiso 1 1 d D U . . .
C2 C 0.9438(3) 0.7726(7) 0.3382(2) 0.0204(6) Uani 1 1 d . . . . .
H2 H 0.911924 0.973880 0.337596 0.024 Uiso 1 1 calc R U . . .
O3 O 0.4064(2) 0.5416(5) 0.41910(15) 0.0226(5) Uani 1 1 d . . . . .
C3 C 0.9105(3) 0.6628(8) 0.2388(2) 0.0243(6) Uani 1 1 d . . . . .
H3A H 0.808016 0.638081 0.216384 0.029 Uiso 1 1 calc R U . . .
H3B H 0.953190 0.472730 0.239882 0.029 Uiso 1 1 calc R U . . .
O4 O 0.2303(2) 0.2563(5) 0.34777(17) 0.0258(5) Uani 1 1 d . . . . .
C4 C 1.1405(4) 0.7369(9) 0.1631(3) 0.0345(8) Uani 1 1 d . . . . .
H4A H 1.207914 0.813271 0.218813 0.041 Uiso 1 1 calc R U . . .
H4B H 1.139584 0.527780 0.168318 0.041 Uiso 1 1 calc R U . . .
C5 C 1.1846(4) 0.8224(11) 0.0761(3) 0.0441(11) Uani 1 1 d . . . . .
H5A H 1.118237 0.743908 0.021312 0.066 Uiso 1 1 calc R U . . .
H5B H 1.278260 0.748275 0.080096 0.066 Uiso 1 1 calc R U . . .
H5C H 1.185538 1.029497 0.071440 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3569(3) 0.3280(6) 0.3720(2) 0.0195(6) Uani 1 1 d . . . . .
C7 C 0.4592(3) 0.1484(7) 0.3352(2) 0.0188(6) Uani 1 1 d . . . . .
H7 H 0.425775 -0.052339 0.327559 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4662(3) 0.2666(7) 0.2413(2) 0.0217(6) Uani 1 1 d . . . . .
H8A H 0.372426 0.249925 0.197562 0.026 Uiso 1 1 calc R U . . .
H8B H 0.489297 0.470860 0.248698 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5723(3) 0.1212(8) 0.1987(2) 0.0263(7) Uani 1 1 d . . . . .
H9A H 0.552516 -0.084647 0.193183 0.032 Uiso 1 1 calc R U . . .
H9B H 0.667359 0.147159 0.239968 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5669(4) 0.2427(9) 0.1028(2) 0.0337(8) Uani 1 1 d . . . . .
H10A H 0.474159 0.209081 0.060965 0.050 Uiso 1 1 calc R U . . .
H10B H 0.637764 0.149635 0.078184 0.050 Uiso 1 1 calc R U . . .
H10C H 0.585226 0.446963 0.107950 0.050 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 1.814(3) . ?
S1 C4 1.820(4) . ?
O1 C1 1.247(4) . ?
N1 C2 1.488(4) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.87(2) . ?
N1 H1C 0.86(2) . ?
C1 O2 1.256(4) . ?
C1 C2 1.534(4) . ?
N2 C7 1.484(4) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.87(2) . ?
N2 H2C 0.90(2) . ?
C2 C3 1.529(4) . ?
C2 H2 1.0000 . ?
O3 C6 1.253(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O4 C6 1.259(4) . ?
C4 C5 1.533(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.533(4) . ?
C7 C8 1.531(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.531(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.535(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C3 S1 C4 102.12(16) . . ?
C2 N1 H1A 108(3) . . ?
C2 N1 H1B 110(3) . . ?
H1A N1 H1B 111(4) . . ?
C2 N1 H1C 108(3) . . ?
H1A N1 H1C 112(4) . . ?
H1B N1 H1C 106(4) . . ?
O1 C1 O2 126.6(3) . . ?
O1 C1 C2 117.8(3) . . ?
O2 C1 C2 115.5(3) . . ?
C7 N2 H2A 110(3) . . ?
C7 N2 H2B 112(3) . . ?
H2A N2 H2B 115(4) . . ?
C7 N2 H2C 112(3) . . ?
H2A N2 H2C 107(4) . . ?
H2B N2 H2C 100(4) . . ?
N1 C2 C3 112.5(2) . . ?
N1 C2 C1 109.9(2) . . ?
C3 C2 C1 107.4(3) . . ?
N1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C2 C3 S1 117.3(2) . . ?
C2 C3 H3A 108.0 . . ?
S1 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
S1 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
C5 C4 S1 108.9(3) . . ?
C5 C4 H4A 109.9 . . ?
S1 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
S1 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 126.3(3) . . ?
O3 C6 C7 116.6(3) . . ?
O4 C6 C7 116.9(3) . . ?
N2 C7 C8 110.1(2) . . ?
N2 C7 C6 109.3(2) . . ?
C8 C7 C6 108.9(3) . . ?
N2 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C6 C7 H7 109.5 . . ?
C9 C8 C7 115.0(3) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 111.4(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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 C2 N1 -27.6(4) . . . . ?
O2 C1 C2 N1 156.0(3) . . . . ?
O1 C1 C2 C3 95.0(3) . . . . ?
O2 C1 C2 C3 -81.4(3) . . . . ?
N1 C2 C3 S1 -70.3(3) . . . . ?
C1 C2 C3 S1 168.7(2) . . . . ?
C4 S1 C3 C2 90.3(3) . . . . ?
C3 S1 C4 C5 161.4(3) . . . . ?
O3 C6 C7 N2 32.2(4) . . . . ?
O4 C6 C7 N2 -151.7(3) . . . . ?
O3 C6 C7 C8 -88.2(3) . . . . ?
O4 C6 C7 C8 87.9(3) . . . . ?
N2 C7 C8 C9 56.0(4) . . . . ?
C6 C7 C8 C9 175.9(3) . . . . ?
C7 C8 C9 C10 177.1(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
N1 H1A O4 0.87(2) 2.00(3) 2.836(4) 162(4) 1_665 yes
N1 H1B O1 0.87(2) 1.96(3) 2.795(3) 161(4) 2_756 yes
N1 H1C O4 0.86(2) 2.00(3) 2.849(4) 166(4) 1_655 yes
N2 H2A O2 0.88(2) 1.91(3) 2.785(4) 175(4) . yes
N2 H2B O3 0.87(2) 1.89(2) 2.754(3) 177(5) 2_646 yes
N2 H2C O2 0.90(2) 1.92(3) 2.787(4) 164(4) 1_545 yes
C2 H2 O1 1.00 2.41 3.265(4) 142.5 1_565 yes
C7 H7 O3 1.00 2.39 3.224(4) 140.1 1_545 yes

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.076


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
