# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_TDZH_AdipAc
_database_code_depnum_ccdc_archive 'CCDC 2042290'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_date             2020-08-20T06:19:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H13 N3 O S, 0.5(C6 H10 O4)'
_chemical_formula_sum            'C14 H18 N3 O3 S'
_chemical_formula_weight         308.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.770(2)
_cell_length_b                   5.0916(4)
_cell_length_c                   22.201(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.637(9)
_cell_angle_gamma                90
_cell_volume                     1491.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6048
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      67.72

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             652
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54178   13.770    5.095   22.168   89.982  106.531   89.985
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_type   multi-scan
_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_correction_T_min  0.4021
_exptl_absorpt_correction_T_max  0.753
_shelx_estimated_absorpt_T_min   0.734
_shelx_estimated_absorpt_T_max   0.922

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_number            12113
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         6.046
_diffrn_reflns_theta_max         68.016
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.952
_reflns_Friedel_coverage         0
_reflns_number_total             2593
_reflns_number_gt                2344
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2593
_refine_ls_number_parameters     219
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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 0.59910(4) -0.26752(9) 0.54947(2) 0.0324(2) Uani 1 1 d . . . . .
O1 O 0.8650(2) -0.2714(5) 0.72376(14) 0.0635(8) Uani 0.69 1 d D U P A 1
H1 H 0.859115 -0.302482 0.679669 0.076 Uiso 0.69 1 d R U P A 1
C4 C 0.8532(3) -0.0028(10) 0.7262(2) 0.0416(12) Uani 0.69 1 d D U P A 1
H4A H 0.895689 0.085794 0.702441 0.05 Uiso 0.69 1 calc R U P A 1
C5 C 0.8928(3) 0.0687(10) 0.79598(17) 0.0554(10) Uani 0.69 1 d D U P A 1
H5A H 0.889776 0.259596 0.800847 0.083 Uiso 0.69 1 calc R U P A 1
H5B H 0.963116 0.009314 0.812546 0.083 Uiso 0.69 1 calc R U P A 1
H5C H 0.850824 -0.016942 0.819188 0.083 Uiso 0.69 1 calc R U P A 1
O1B O 0.8836(6) 0.2697(14) 0.7890(3) 0.0615(17) Uani 0.31 1 d D U P A 2
H1B H 0.877612 0.413712 0.768914 0.074 Uiso 0.31 1 d R U P A 2
C4B C 0.8512(6) 0.091(2) 0.7375(4) 0.044(3) Uani 0.31 1 d D U P A 2
H4BA H 0.855656 -0.080593 0.760221 0.052 Uiso 0.12 1 calc R U P A 2
H4BB H 0.88862 0.132893 0.708324 0.052 Uiso 0.19 1 d R U P A 3
C5B C 0.9258(10) 0.047(3) 0.7013(7) 0.034(4) Uiso 0.12 1 d D . P A 2
H5BA H 0.896994 0.108947 0.658017 0.051 Uiso 0.12 1 calc R U P A 2
H5BB H 0.941458 -0.140212 0.701022 0.051 Uiso 0.12 1 calc R U P A 2
H5BC H 0.988074 0.145392 0.721058 0.051 Uiso 0.12 1 calc R U P A 2
C5C C 0.8769(8) -0.167(2) 0.7581(6) 0.033(2) Uiso 0.19 1 d . . P B 3
H5CA H 0.854731 -0.285612 0.723246 0.049 Uiso 0.19 1 d R U P B 3
H5CB H 0.949112 -0.179422 0.775327 0.049 Uiso 0.19 1 d R U P B 3
H5CC H 0.844771 -0.211682 0.789766 0.049 Uiso 0.19 1 d R U P B 3
O2 O 0.84728(11) 0.5133(3) 0.59965(6) 0.0347(4) Uani 1 1 d . . . . .
H2 H 0.799933 0.389153 0.594504 0.042 Uiso 1 1 d R U . . .
O3 O 0.82127(10) 0.4877(3) 0.49586(6) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.63680(13) -0.2131(3) 0.62665(8) 0.0347(4) Uani 1 1 d . . . . .
N2 N 0.71618(11) 0.1165(3) 0.58688(7) 0.0264(4) Uani 1 1 d . . . . .
N3 N 0.67697(12) 0.0762(3) 0.47809(7) 0.0275(4) Uani 1 1 d . . . . .
H3C H 0.710149 0.224541 0.478928 0.033 Uiso 1 1 calc R U . . .
C1 C 0.69608(14) -0.0061(4) 0.63709(9) 0.0287(4) Uani 1 1 d D . . . .
C2 C 0.66786(13) -0.0054(4) 0.53376(9) 0.0249(4) Uani 1 1 d . . . . .
C3 C 0.74283(16) 0.0951(5) 0.70162(9) 0.0397(5) Uani 1 1 d D . . . .
H3A H 0.718919 0.272302 0.70146 0.048 Uiso 1 1 d R U . A .
H3B H 0.711827 -0.002728 0.728161 0.048 Uiso 1 1 d R U . . .
C6 C 0.64076(14) -0.0427(4) 0.41855(9) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.68251(16) 0.0449(4) 0.37192(9) 0.0347(5) Uani 1 1 d . . . . .
H7A H 0.73196 0.180548 0.380907 0.042 Uiso 1 1 calc R U . . .
C8 C 0.65210(17) -0.0651(5) 0.31283(10) 0.0414(5) Uani 1 1 d . . . . .
H8A H 0.681477 -0.005824 0.281421 0.05 Uiso 1 1 calc R U . . .
C9 C 0.57942(16) -0.2606(4) 0.29854(9) 0.0326(5) Uani 1 1 d . . . . .
H9A H 0.558747 -0.335932 0.257704 0.039 Uiso 1 1 calc R U . . .
C10 C 0.53769(16) -0.3437(4) 0.34444(10) 0.0347(5) Uani 1 1 d . . . . .
H10A H 0.487646 -0.477894 0.335136 0.042 Uiso 1 1 calc R U . . .
C11 C 0.56734(17) -0.2354(4) 0.40398(10) 0.0360(5) Uani 1 1 d . . . . .
H11A H 0.537007 -0.293849 0.435015 0.043 Uiso 1 1 calc R U . . .
C12 C 0.86396(13) 0.5852(4) 0.54638(9) 0.0262(4) Uani 1 1 d . . . . .
C13 C 0.94250(15) 0.7978(4) 0.55498(9) 0.0306(5) Uani 1 1 d . . . . .
H13A H 1.007965 0.729295 0.581704 0.037 Uiso 1 1 calc R U . . .
H13B H 0.922526 0.946495 0.577591 0.037 Uiso 1 1 calc R U . . .
C14 C 0.95754(14) 0.8991(4) 0.49405(9) 0.0276(4) Uani 1 1 d . . . . .
H14A H 0.893726 0.979932 0.46834 0.033 Uiso 1 1 calc R U . . .
H14B H 0.973783 0.749993 0.469981 0.033 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.6652(19) . ?
S1 C2 1.7289(19) . ?
O1 C4 1.380(5) . ?
O1 H1 0.9717 . ?
C4 C5 1.532(5) . ?
C4 C3 1.543(5) . ?
C4 H4A 1 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
O1B C4B 1.431(8) . ?
O1B H1B 0.85 . ?
C4B C3 1.477(7) . ?
C4B C5B 1.490(9) . ?
C4B H4BA 1 . ?
C5B H5BA 0.98 . ?
C5B H5BB 0.98 . ?
C5B H5BC 0.98 . ?
C5C H5CA 0.9599 . ?
C5C H5CB 0.9601 . ?
C5C H5CC 0.96 . ?
O2 C12 1.320(2) . ?
O2 H2 0.8917 . ?
O3 C12 1.213(2) . ?
N1 C1 1.312(3) . ?
N2 C2 1.330(2) . ?
N2 C1 1.373(2) . ?
N3 C2 1.343(2) . ?
N3 C6 1.409(2) . ?
N3 H3C 0.88 . ?
C1 C3 1.485(3) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C6 C11 1.379(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.377(3) . ?
C7 H7A 0.95 . ?
C8 C9 1.382(3) . ?
C8 H8A 0.95 . ?
C9 C10 1.372(3) . ?
C9 H9A 0.95 . ?
C10 C11 1.382(3) . ?
C10 H10A 0.95 . ?
C11 H11A 0.95 . ?
C12 C13 1.503(3) . ?
C13 C14 1.516(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C14 1.522(3) 3_776 ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C2 92.96(8) . . ?
C4 O1 H1 102.9 . . ?
O1 C4 C5 105.3(4) . . ?
O1 C4 C3 114.9(4) . . ?
C5 C4 C3 108.0(3) . . ?
O1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
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 . . ?
C4B O1B H1B 99.7 . . ?
O1B C4B C3 117.1(7) . . ?
O1B C4B C5B 114.8(9) . . ?
C3 C4B C5B 117.2(8) . . ?
O1B C4B H4BA 101.1 . . ?
C3 C4B H4BA 101.1 . . ?
C5B C4B H4BA 101.1 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
H5CA C5C H5CB 109.5 . . ?
H5CA C5C H5CC 109.5 . . ?
H5CB C5C H5CC 109.5 . . ?
C12 O2 H2 113 . . ?
C1 N1 S1 108.08(14) . . ?
C2 N2 C1 109.99(16) . . ?
C2 N3 C6 128.98(16) . . ?
C2 N3 H3C 115.5 . . ?
C6 N3 H3C 115.5 . . ?
N1 C1 N2 118.77(18) . . ?
N1 C1 C3 121.68(18) . . ?
N2 C1 C3 119.54(17) . . ?
N2 C2 N3 121.12(16) . . ?
N2 C2 S1 110.18(14) . . ?
N3 C2 S1 128.70(14) . . ?
C4B C3 C1 127.4(4) . . ?
C1 C3 C4 109.9(2) . . ?
C4B C3 H3A 108 . . ?
C1 C3 H3A 105.6 . . ?
C4 C3 H3A 127.4 . . ?
C4B C3 H3B 102.7 . . ?
C1 C3 H3B 105.4 . . ?
C4 C3 H3B 100.5 . . ?
H3A C3 H3B 106.1 . . ?
C11 C6 C7 118.96(18) . . ?
C11 C6 N3 124.37(17) . . ?
C7 C6 N3 116.67(17) . . ?
C8 C7 C6 119.99(19) . . ?
C8 C7 H7A 120 . . ?
C6 C7 H7A 120 . . ?
C7 C8 C9 120.95(19) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C10 C9 C8 118.78(19) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
C9 C10 C11 121.01(19) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C6 C11 C10 120.29(19) . . ?
C6 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
O3 C12 O2 123.53(17) . . ?
O3 C12 C13 123.55(17) . . ?
O2 C12 C13 112.92(16) . . ?
C12 C13 C14 114.12(16) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C14 111.66(19) . 3_776 ?
C13 C14 H14A 109.3 . . ?
C14 C14 H14A 109.3 3_776 . ?
C13 C14 H14B 109.3 . . ?
C14 C14 H14B 109.3 3_776 . ?
H14A C14 H14B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 N1 C1 0.83(15) . . . . ?
S1 N1 C1 N2 -0.9(2) . . . . ?
S1 N1 C1 C3 -179.95(16) . . . . ?
C2 N2 C1 N1 0.5(2) . . . . ?
C2 N2 C1 C3 179.52(17) . . . . ?
C1 N2 C2 N3 -178.99(17) . . . . ?
C1 N2 C2 S1 0.21(19) . . . . ?
C6 N3 C2 N2 172.65(17) . . . . ?
C6 N3 C2 S1 -6.4(3) . . . . ?
N1 S1 C2 N2 -0.61(15) . . . . ?
N1 S1 C2 N3 178.51(18) . . . . ?
O1B C4B C3 C1 160.2(6) . . . . ?
C5B C4B C3 C1 17.6(14) . . . . ?
N1 C1 C3 C4B 111.3(7) . . . . ?
N2 C1 C3 C4B -67.8(7) . . . . ?
N1 C1 C3 C4 98.9(3) . . . . ?
N2 C1 C3 C4 -80.1(3) . . . . ?
O1 C4 C3 C1 -54.0(5) . . . . ?
C5 C4 C3 C1 -171.2(3) . . . . ?
C2 N3 C6 C11 16.7(3) . . . . ?
C2 N3 C6 C7 -163.82(19) . . . . ?
C11 C6 C7 C8 -1.5(3) . . . . ?
N3 C6 C7 C8 178.95(19) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C7 C6 C11 C10 1.6(3) . . . . ?
N3 C6 C11 C10 -178.96(19) . . . . ?
C9 C10 C11 C6 -0.8(3) . . . . ?
O3 C12 C13 C14 5.3(3) . . . . ?
O2 C12 C13 C14 -175.57(16) . . . . ?
C12 C13 C14 C14 -176.35(19) . . . 3_776 ?

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 O2 0.97 1.97 2.910(3) 161 1_545 yes
O2 H2 N2 0.89 1.78 2.670(2) 173.9 . yes
N3 H3C O3 0.88 1.99 2.836(2) 161.7 . yes
C11 H11A S1 0.95 2.44 3.137(2) 129.9 . yes
C11 H11A S1 0.95 3 3.753(2) 137.4 3_646 yes



# END of CIF
####################################################################### 
# 
# 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_TDZH_FumAc
_database_code_depnum_ccdc_archive 'CCDC 2042294'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_date             2020-08-01T10:24:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H13 N3 O S, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C13 H15 N3 O3 S'
_chemical_formula_weight         293.34

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.75080(10)
_cell_length_b                   8.5166(2)
_cell_length_c                   14.7464(3)
_cell_angle_alpha                84.8780(10)
_cell_angle_beta                 85.1150(10)
_cell_angle_gamma                74.3440(10)
_cell_volume                     691.26(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7881
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      78.19

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             308
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54182    5.752    8.517   14.745   84.872   85.127   74.350
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.193
_exptl_absorpt_correction_type   multi-scan
_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_correction_T_min  0.4964
_exptl_absorpt_correction_T_max  0.7542

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_number            10893
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         8.41
_diffrn_reflns_theta_max         78.882
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.948
_reflns_Friedel_coverage         0
_reflns_number_total             2831
_reflns_number_gt                2643
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2831
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.034

_refine_special_details          
;
 The R:S ratio of TDZH isomers 0.552:0.448 (3) is obtained by isotropic 
refinement and fixed Uiso=0.05 A2 for disordered atoms.
;

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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 0.96949(7) 0.58004(5) 0.13885(3) 0.05034(15) Uani 1 1 d . . . . .
N1 N 0.8822(3) 0.42122(17) 0.10854(9) 0.0526(3) Uani 1 1 d . . . . .
N2 N 0.6419(2) 0.49444(14) 0.23917(8) 0.0389(3) Uani 1 1 d . . . . .
N3 N 0.7326(2) 0.71466(15) 0.29640(8) 0.0426(3) Uani 1 1 d . . . . .
H3B H 0.61849 0.710325 0.337443 0.051 Uiso 1 1 calc R U . . .
C1 C 0.7127(3) 0.39550(17) 0.16835(9) 0.0397(3) Uani 1 1 d . . . . .
C2 C 0.7699(2) 0.60396(16) 0.23376(9) 0.0361(3) Uani 1 1 d . . . . .
C3 C 0.5938(3) 0.2603(2) 0.16271(11) 0.0506(4) Uani 1 1 d . . . . .
H3A H 0.420444 0.307337 0.161403 0.061 Uiso 0.55 1 calc R U P A 1
H3C H 0.622743 0.187842 0.217564 0.061 Uiso 0.55 1 calc R U P A 1
H3D H 0.443455 0.282354 0.200414 0.061 Uiso 0.45 1 calc R U P B 2
H3E H 0.698465 0.158317 0.18672 0.061 Uiso 0.45 1 calc R U P B 2
O1 O 0.6187(4) 0.0072(3) 0.09952(15) 0.0591(6) Uani 0.55 1 d . . P C 1
H1 H 0.636623 -0.045817 0.044667 0.071 Uiso 0.55 1 d R U P C 1
C4 C 0.6814(6) 0.1579(4) 0.07898(19) 0.0408(5) Uani 0.55 1 d . . P C 1
H4A H 0.857122 0.137577 0.067814 0.049 Uiso 0.55 1 calc R U P C 1
C5 C 0.5551(8) 0.2520(5) -0.0026(3) 0.0709(10) Uani 0.55 1 d . . P C 1
H5A H 0.600419 0.352709 -0.014792 0.106 Uiso 0.55 1 calc R U P C 1
H5B H 0.383131 0.27505 0.009998 0.106 Uiso 0.55 1 calc R U P C 1
H5C H 0.601491 0.187969 -0.054729 0.106 Uiso 0.55 1 calc R U P C 1
O1B O 0.3455(4) 0.1649(3) 0.06039(18) 0.0527(6) Uani 0.45 1 d . . P C 2
H1B H 0.219952 0.217359 0.071505 0.063 Uiso 0.45 1 d R U P C 2
C4B C 0.5387(8) 0.2407(5) 0.0613(3) 0.0466(8) Uani 0.45 1 d . . P C 2
H4BA H 0.5036 0.346265 0.025676 0.056 Uiso 0.45 1 calc R U P C 2
C5B C 0.7620(8) 0.1248(7) 0.0226(4) 0.0721(13) Uani 0.45 1 d . . P C 2
H5BA H 0.899906 0.165181 0.028902 0.108 Uiso 0.45 1 calc R U P C 2
H5BB H 0.745858 0.115362 -0.040813 0.108 Uiso 0.45 1 calc R U P C 2
H5BC H 0.78349 0.019354 0.054891 0.108 Uiso 0.45 1 calc R U P C 2
C6 C 0.8505(3) 0.83665(16) 0.30555(9) 0.0383(3) Uani 1 1 d . . . . .
C7 C 0.7603(3) 0.9384(2) 0.37633(11) 0.0498(4) Uani 1 1 d . . . . .
H7A H 0.628615 0.92398 0.414067 0.06 Uiso 1 1 calc R U . . .
C8 C 0.8665(4) 1.0609(2) 0.39058(13) 0.0615(5) Uani 1 1 d . . . . .
H8A H 0.805923 1.128494 0.438042 0.074 Uiso 1 1 calc R U . . .
C9 C 1.0621(4) 1.0837(2) 0.33486(13) 0.0607(5) Uani 1 1 d . . . . .
H9A H 1.132985 1.166307 0.344605 0.073 Uiso 1 1 calc R U . . .
C10 C 1.1510(3) 0.9831(2) 0.26481(12) 0.0528(4) Uani 1 1 d . . . . .
H10A H 1.282712 0.998071 0.227243 0.063 Uiso 1 1 calc R U . . .
C11 C 1.0464(3) 0.85974(18) 0.24964(11) 0.0459(3) Uani 1 1 d . . . . .
H11A H 1.107659 0.79259 0.202029 0.055 Uiso 1 1 calc R U . . .
O21 O 0.2894(2) 0.46411(14) 0.36400(7) 0.0527(3) Uani 1 1 d . . . . .
H21 H 0.408547 0.474062 0.322127 0.063 Uiso 1 1 d R U . . .
O22 O 0.3842(2) 0.65809(13) 0.43459(7) 0.0481(3) Uani 1 1 d . . . . .
C21 C 0.2641(3) 0.56164(17) 0.43018(9) 0.0403(3) Uani 1 1 d . . . . .
C22 C 0.0728(3) 0.54666(18) 0.50161(10) 0.0439(3) Uani 1 1 d . . . . .
H22A H 0.054952 0.607769 0.552179 0.053 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.6713(13) . ?
S1 C2 1.7229(14) . ?
N1 C1 1.3082(19) . ?
N2 C2 1.3287(17) . ?
N2 C1 1.3660(17) . ?
N3 C2 1.3419(17) . ?
N3 C6 1.4064(17) . ?
N3 H3B 0.86 . ?
C1 C3 1.5010(19) . ?
C3 C4 1.545(3) . ?
C3 C4B 1.587(4) . ?
C3 H3A 0.97 . ?
C3 H3C 0.97 . ?
C3 H3D 0.97 . ?
C3 H3E 0.97 . ?
O1 C4 1.425(3) . ?
O1 H1 0.9458 . ?
C4 C5 1.509(5) . ?
C4 H4A 0.98 . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
O1B C4B 1.429(4) . ?
O1B H1B 0.7527 . ?
C4B C5B 1.498(6) . ?
C4B H4BA 0.98 . ?
C5B H5BA 0.96 . ?
C5B H5BB 0.96 . ?
C5B H5BC 0.96 . ?
C6 C11 1.386(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.382(2) . ?
C7 H7A 0.93 . ?
C8 C9 1.382(3) . ?
C8 H8A 0.93 . ?
C9 C10 1.376(2) . ?
C9 H9A 0.93 . ?
C10 C11 1.386(2) . ?
C10 H10A 0.93 . ?
C11 H11A 0.93 . ?
O21 C21 1.3112(17) . ?
O21 H21 0.899 . ?
O22 C21 1.2163(17) . ?
C21 C22 1.4803(19) . ?
C22 C22 1.306(3) 2_566 ?
C22 H22A 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C2 92.53(6) . . ?
C1 N1 S1 108.08(10) . . ?
C2 N2 C1 109.88(11) . . ?
C2 N3 C6 130.22(12) . . ?
C2 N3 H3B 114.9 . . ?
C6 N3 H3B 114.9 . . ?
N1 C1 N2 118.92(12) . . ?
N1 C1 C3 122.52(13) . . ?
N2 C1 C3 118.55(12) . . ?
N2 C2 N3 120.70(12) . . ?
N2 C2 S1 110.57(10) . . ?
N3 C2 S1 128.73(11) . . ?
C1 C3 C4 114.68(15) . . ?
C1 C3 C4B 112.36(16) . . ?
C1 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C1 C3 H3C 108.6 . . ?
C4 C3 H3C 108.6 . . ?
H3A C3 H3C 107.6 . . ?
C1 C3 H3D 109.1 . . ?
C4B C3 H3D 109.1 . . ?
C1 C3 H3E 109.1 . . ?
C4B C3 H3E 109.1 . . ?
H3D C3 H3E 107.9 . . ?
C4 O1 H1 107.9 . . ?
O1 C4 C5 111.2(2) . . ?
O1 C4 C3 107.0(2) . . ?
C5 C4 C3 108.2(3) . . ?
O1 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
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 . . ?
C4B O1B H1B 116.4 . . ?
O1B C4B C5B 106.9(3) . . ?
O1B C4B C3 111.0(3) . . ?
C5B C4B C3 105.4(4) . . ?
O1B C4B H4BA 111.1 . . ?
C5B C4B H4BA 111.1 . . ?
C3 C4B H4BA 111.1 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
C11 C6 C7 119.41(13) . . ?
C11 C6 N3 124.37(13) . . ?
C7 C6 N3 116.22(13) . . ?
C8 C7 C6 120.03(15) . . ?
C8 C7 H7A 120 . . ?
C6 C7 H7A 120 . . ?
C9 C8 C7 120.51(15) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 119.44(15) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 120.73(15) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C6 C11 C10 119.88(14) . . ?
C6 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C21 O21 H21 112.7 . . ?
O22 C21 O21 124.40(13) . . ?
O22 C21 C22 121.17(13) . . ?
O21 C21 C22 114.43(12) . . ?
C22 C22 C21 124.39(17) 2_566 . ?
C22 C22 H22A 117.8 2_566 . ?
C21 C22 H22A 117.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 N1 C1 0.49(13) . . . . ?
S1 N1 C1 N2 0.05(19) . . . . ?
S1 N1 C1 C3 -179.40(12) . . . . ?
C2 N2 C1 N1 -0.8(2) . . . . ?
C2 N2 C1 C3 178.71(13) . . . . ?
C1 N2 C2 N3 -179.85(13) . . . . ?
C1 N2 C2 S1 1.07(15) . . . . ?
C6 N3 C2 N2 177.76(13) . . . . ?
C6 N3 C2 S1 -3.3(2) . . . . ?
N1 S1 C2 N2 -0.93(11) . . . . ?
N1 S1 C2 N3 -179.92(14) . . . . ?
N1 C1 C3 C4 -2.0(3) . . . . ?
N2 C1 C3 C4 178.55(18) . . . . ?
N1 C1 C3 C4B -41.1(3) . . . . ?
N2 C1 C3 C4B 139.4(2) . . . . ?
C1 C3 C4 O1 160.4(2) . . . . ?
C1 C3 C4 C5 -79.6(3) . . . . ?
C1 C3 C4B O1B -156.0(2) . . . . ?
C1 C3 C4B C5B 88.7(3) . . . . ?
C2 N3 C6 C11 -3.3(3) . . . . ?
C2 N3 C6 C7 176.98(15) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
N3 C6 C7 C8 179.57(15) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C7 C6 C11 C10 0.2(2) . . . . ?
N3 C6 C11 C10 -179.54(14) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
O22 C21 C22 C22 175.54(19) . . . 2_566 ?
O21 C21 C22 C22 -4.3(3) . . . 2_566 ?

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
N3 H3B O22 0.86 1.99 2.8369(15) 169.8 . yes
O1 H1 O1 0.95 2.63 3.366(4) 134.7 2_655 yes
C5 H5C O1 0.96 2.51 3.149(4) 124.4 2_655 yes
O1B H1B N1 0.75 2.29 3.030(3) 167.1 1_455 yes
C11 H11A S1 0.93 2.45 3.1506(15) 132.6 . yes
O21 H21 N2 0.9 1.77 2.6698(15) 179.6 . yes



# END of CIF
####################################################################### 
# 
# 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_TDZH_GA
_database_code_depnum_ccdc_archive 'CCDC 2042293'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_date             2021-01-11T23:43:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H13 N3 O S, C7 H6 O5, 2.5(H2 O)'
_chemical_formula_sum            'C18 H24 N3 O8.50 S'
_chemical_formula_weight         450.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5188(12)
_cell_length_b                   9.9520(12)
_cell_length_c                   11.8041(15)
_cell_angle_alpha                97.589(4)
_cell_angle_beta                 113.069(4)
_cell_angle_gamma                93.795(4)
_cell_volume                     1011.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4844
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.46

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             474
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71104    9.532    9.957   11.822   97.659  113.043   93.806
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_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_correction_T_min  0.6637
_exptl_absorpt_correction_T_max  0.7461
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.962

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX3 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_number            11729
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3973
_reflns_number_gt                3289
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3973
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.142
_refine_ls_wR_factor_gt          0.136
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.05397(8) 0.19234(7) 0.48408(7) 0.0221(2) Uani 1 1 d . . . . .
O2 O 0.3028(2) 0.42068(19) 0.30580(18) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.249889 0.381091 0.33555 0.031 Uiso 1 1 d R U . . .
O3 O 0.3460(2) 0.58078(19) 0.47241(17) 0.0234(4) Uani 1 1 d . . . . .
O4 O 0.5695(2) 0.63032(19) 0.06662(17) 0.0258(5) Uani 1 1 d . . . . .
H31 H 0.607342 0.685151 0.04198 0.031 Uiso 0.5 1 d R U P . .
H32 H 0.522642 0.550051 0.02868 0.031 Uiso 0.5 1 d R U P . .
O5 O 0.7173(2) 0.87361(19) 0.20662(18) 0.0278(5) Uani 1 1 d . . . . .
H4 H 0.770966 0.945442 0.258318 0.033 Uiso 1 1 d R U . . .
O6 O 0.6888(2) 0.96576(19) 0.42548(18) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.693191 0.979923 0.503989 0.032 Uiso 1 1 d R U . . .
O7 O 0.5170(4) 0.1805(3) 0.3191(3) 0.0413(8) Uani 0.75 1 d . . P A 1
H11 H 0.586097 0.122926 0.341405 0.05 Uiso 0.75 1 d R U P A 1
H12 H 0.558797 0.250426 0.377305 0.05 Uiso 0.75 1 d R U P A 1
O7B O 0.4867(14) 0.1065(13) 0.2372(13) 0.068(3) Uiso 0.25 1 d . . P B 2
H11B H 0.444196 0.162487 0.183745 0.081 Uiso 0.25 1 d R U P B 2
H12B H 0.496466 0.040337 0.178805 0.081 Uiso 0.25 1 d R U P B 2
N1 N -0.0671(3) 0.0969(2) 0.3521(2) 0.0239(5) Uani 1 1 d . . . . .
N2 N 0.1201(2) 0.2750(2) 0.3839(2) 0.0183(5) Uani 1 1 d . . . . .
N3 N 0.1569(3) 0.4273(2) 0.5644(2) 0.0210(5) Uani 1 1 d . . . . .
H3A H 0.221355 0.478015 0.545775 0.025 Uiso 1 1 calc R U . . .
C1 C 0.0314(3) 0.1550(3) 0.3149(3) 0.0204(6) Uani 1 1 d . . . . .
C2 C 0.0864(3) 0.3116(3) 0.4822(2) 0.0170(5) Uani 1 1 d . . . . .
C3 C 0.0527(4) 0.0849(3) 0.2037(3) 0.0306(7) Uani 1 1 d . . . . .
H3D H 0.110487 0.149534 0.175531 0.037 Uiso 0.75 1 calc R U P C 1
H3E H -0.048811 0.05208 0.134149 0.037 Uiso 0.75 1 calc R U P C 1
H3B H -0.047118 0.029213 0.149389 0.037 Uiso 0.25 1 calc R U P D 2
H3C H 0.066091 0.157948 0.158046 0.037 Uiso 0.25 1 calc R U P D 2
O1 O 0.2892(5) 0.0039(5) 0.3479(4) 0.0312(10) Uani 0.75 1 d . . P E 1
H1 H 0.331206 0.055446 0.322035 0.037 Uiso 0.75 1 d R U P E 1
C4 C 0.1438(5) -0.0384(4) 0.2418(4) 0.0287(10) Uani 0.75 1 d . . P E 1
H4A H 0.080268 -0.102004 0.267419 0.034 Uiso 0.75 1 calc R U P E 1
C5 C 0.1669(6) -0.1172(5) 0.1337(4) 0.0431(12) Uani 0.75 1 d . . P E 1
H5A H 0.067021 -0.144875 0.06288 0.065 Uiso 0.75 1 calc R U P E 1
H5B H 0.233723 -0.059251 0.109197 0.065 Uiso 0.75 1 calc R U P E 1
H5C H 0.214997 -0.198649 0.158713 0.065 Uiso 0.75 1 calc R U P E 1
O1B O 0.2837(18) 0.0299(14) 0.3200(12) 0.025(4) Uiso 0.25 1 d . . P E 2
H1B H 0.341337 0.075286 0.299466 0.03 Uiso 0.25 1 d R U P E 2
C4B C 0.165(2) 0.0012(18) 0.2078(17) 0.044(5) Uiso 0.25 1 d . . P E 2
H4BA H 0.197713 0.003486 0.137073 0.09(6) Uiso 0.25 1 calc R . P E 2
C5B C 0.0861(18) -0.1431(15) 0.2052(14) 0.046(4) Uiso 0.25 1 d . . P E 2
H5BA H -0.002821 -0.171719 0.125144 0.069 Uiso 0.25 1 calc R U P E 2
H5BB H 0.159905 -0.209375 0.215171 0.069 Uiso 0.25 1 calc R U P E 2
H5BC H 0.051714 -0.138271 0.273593 0.069 Uiso 0.25 1 calc R U P E 2
C6 C 0.1428(3) 0.4791(3) 0.6754(3) 0.0225(6) Uani 1 1 d . . . . .
C7 C 0.2356(3) 0.6014(3) 0.7447(3) 0.0277(7) Uani 1 1 d . . . . .
H7A H 0.30318 0.645587 0.71558 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2288(4) 0.6580(3) 0.8561(3) 0.0386(8) Uani 1 1 d . . . . .
H8A H 0.292722 0.740529 0.903176 0.046 Uiso 1 1 calc R U . . .
C9 C 0.1301(4) 0.5957(4) 0.8995(3) 0.0443(9) Uani 1 1 d . . . . .
H9A H 0.125506 0.635203 0.97552 0.053 Uiso 1 1 calc R U . . .
C10 C 0.0386(4) 0.4755(4) 0.8307(3) 0.0421(9) Uani 1 1 d . . . . .
H10A H -0.028951 0.431832 0.860234 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0435(4) 0.4175(3) 0.7192(3) 0.0327(7) Uani 1 1 d . . . . .
H11A H -0.021377 0.335165 0.672551 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3625(3) 0.5428(3) 0.3751(2) 0.0194(6) Uani 1 1 d . . . . .
C13 C 0.4504(3) 0.6295(3) 0.3266(2) 0.0177(6) Uani 1 1 d . . . . .
C14 C 0.4636(3) 0.5875(3) 0.2139(2) 0.0187(6) Uani 1 1 d . . . . .
H14A H 0.411834 0.50176 0.163918 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5520(3) 0.6708(3) 0.1748(2) 0.0186(6) Uani 1 1 d . . . . .
C16 C 0.6290(3) 0.7975(3) 0.2482(2) 0.0194(6) Uani 1 1 d . . . . .
C17 C 0.6126(3) 0.8400(3) 0.3591(2) 0.0192(6) Uani 1 1 d . . . . .
C18 C 0.5245(3) 0.7567(3) 0.3983(3) 0.0197(6) Uani 1 1 d . . . . .
H18A H 0.514487 0.786235 0.474382 0.024 Uiso 1 1 calc R U . . .
O101 O 0.5336(11) 1.0030(14) -0.0058(11) 0.074(3) Uiso 0.4 1 d . . P F 1
O102 O 0.7232(9) 0.7607(8) -0.0588(7) 0.072(2) Uiso 0.44 1 d . . P G 1
O201 O 0.6468(8) 0.8232(7) -0.0581(6) 0.0712(18) Uiso 0.48 1 d . . P H 2
O202 O 0.473(3) 1.061(3) 0.040(2) 0.093(8) Uiso 0.18 1 d . . P I 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.669(2) . ?
S1 C2 1.736(3) . ?
O2 C12 1.323(3) . ?
O2 H2 0.825 . ?
O3 C12 1.234(3) . ?
O4 C15 1.365(3) . ?
O4 H31 0.7809 . ?
O4 H32 0.86 . ?
O5 C16 1.363(3) . ?
O5 H4 0.8583 . ?
O6 C17 1.372(3) . ?
O6 H5 0.9027 . ?
O7 H11 0.8855 . ?
O7 H12 0.859 . ?
O7B H11B 0.8912 . ?
O7B H12B 0.9249 . ?
N1 C1 1.314(3) . ?
N2 C2 1.334(3) . ?
N2 C1 1.368(3) . ?
N3 C2 1.345(3) . ?
N3 C6 1.403(3) . ?
N3 H3A 0.88 . ?
C1 C3 1.494(4) . ?
C3 C4B 1.390(17) . ?
C3 C4 1.563(5) . ?
C3 H3D 0.99 . ?
C3 H3E 0.99 . ?
C3 H3B 0.99 . ?
C3 H3C 0.99 . ?
O1 C4 1.444(6) . ?
O1 H1 0.791 . ?
C4 C5 1.507(6) . ?
C4 H4A 1 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
O1B C4B 1.34(2) . ?
O1B H1B 0.815 . ?
C4B C5B 1.57(2) . ?
C4B H4BA 1 . ?
C5B H5BA 0.98 . ?
C5B H5BB 0.98 . ?
C5B H5BC 0.98 . ?
C6 C11 1.389(4) . ?
C6 C7 1.399(4) . ?
C7 C8 1.388(4) . ?
C7 H7A 0.95 . ?
C8 C9 1.382(5) . ?
C8 H8A 0.95 . ?
C9 C10 1.379(5) . ?
C9 H9A 0.95 . ?
C10 C11 1.385(4) . ?
C10 H10A 0.95 . ?
C11 H11A 0.95 . ?
C12 C13 1.478(4) . ?
C13 C18 1.395(4) . ?
C13 C14 1.397(4) . ?
C14 C15 1.386(4) . ?
C14 H14A 0.95 . ?
C15 C16 1.403(4) . ?
C16 C17 1.393(4) . ?
C17 C18 1.386(4) . ?
C18 H18A 0.95 . ?
O101 O101 0.704(18) 2_675 ?
O201 O202 1.72(2) 2_675 ?
O202 O202 1.68(5) 2_675 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C2 92.21(12) . . ?
C12 O2 H2 108.9 . . ?
C15 O4 H31 117.4 . . ?
C15 O4 H32 113.3 . . ?
H31 O4 H32 128.4 . . ?
C16 O5 H4 114.7 . . ?
C17 O6 H5 112.7 . . ?
H11 O7 H12 102.3 . . ?
H11B O7B H12B 95.7 . . ?
C1 N1 S1 108.50(18) . . ?
C2 N2 C1 109.6(2) . . ?
C2 N3 C6 129.6(2) . . ?
C2 N3 H3A 115.2 . . ?
C6 N3 H3A 115.2 . . ?
N1 C1 N2 119.0(2) . . ?
N1 C1 C3 119.8(2) . . ?
N2 C1 C3 121.1(2) . . ?
N2 C2 N3 121.3(2) . . ?
N2 C2 S1 110.75(18) . . ?
N3 C2 S1 128.0(2) . . ?
C4B C3 C1 125.4(8) . . ?
C1 C3 C4 108.4(3) . . ?
C1 C3 H3D 110 . . ?
C4 C3 H3D 110 . . ?
C1 C3 H3E 110 . . ?
C4 C3 H3E 110 . . ?
H3D C3 H3E 108.4 . . ?
C4B C3 H3B 106 . . ?
C1 C3 H3B 106 . . ?
C4B C3 H3C 106 . . ?
C1 C3 H3C 106 . . ?
H3B C3 H3C 106.3 . . ?
C4 O1 H1 101.7 . . ?
O1 C4 C5 110.8(4) . . ?
O1 C4 C3 111.9(3) . . ?
C5 C4 C3 111.8(4) . . ?
O1 C4 H4A 107.3 . . ?
C5 C4 H4A 107.3 . . ?
C3 C4 H4A 107.3 . . ?
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 . . ?
C4B O1B H1B 97.1 . . ?
O1B C4B C3 110.2(14) . . ?
O1B C4B C5B 104.4(14) . . ?
C3 C4B C5B 102.8(13) . . ?
O1B C4B H4BA 112.9 . . ?
C3 C4B H4BA 112.9 . . ?
C5B C4B H4BA 112.9 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
C11 C6 C7 118.9(3) . . ?
C11 C6 N3 124.3(3) . . ?
C7 C6 N3 116.8(3) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7A 120 . . ?
C6 C7 H7A 120 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C10 C11 C6 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
O3 C12 O2 122.5(2) . . ?
O3 C12 C13 122.8(2) . . ?
O2 C12 C13 114.7(2) . . ?
C18 C13 C14 119.6(2) . . ?
C18 C13 C12 118.0(2) . . ?
C14 C13 C12 122.4(2) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14A 120 . . ?
C13 C14 H14A 120 . . ?
O4 C15 C14 121.0(2) . . ?
O4 C15 C16 118.6(2) . . ?
C14 C15 C16 120.3(2) . . ?
O5 C16 C17 123.0(2) . . ?
O5 C16 C15 117.8(2) . . ?
C17 C16 C15 119.3(2) . . ?
O6 C17 C18 123.1(2) . . ?
O6 C17 C16 116.4(2) . . ?
C18 C17 C16 120.5(2) . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18A 119.9 . . ?
C13 C18 H18A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 N1 C1 0.8(2) . . . . ?
S1 N1 C1 N2 -0.6(3) . . . . ?
S1 N1 C1 C3 175.2(2) . . . . ?
C2 N2 C1 N1 0.0(3) . . . . ?
C2 N2 C1 C3 -175.8(2) . . . . ?
C1 N2 C2 N3 -179.3(2) . . . . ?
C1 N2 C2 S1 0.6(3) . . . . ?
C6 N3 C2 N2 -176.5(3) . . . . ?
C6 N3 C2 S1 3.6(4) . . . . ?
N1 S1 C2 N2 -0.8(2) . . . . ?
N1 S1 C2 N3 179.0(2) . . . . ?
N1 C1 C3 C4B -94.5(10) . . . . ?
N2 C1 C3 C4B 81.2(10) . . . . ?
N1 C1 C3 C4 -73.0(4) . . . . ?
N2 C1 C3 C4 102.7(3) . . . . ?
C1 C3 C4 O1 -56.4(5) . . . . ?
C1 C3 C4 C5 178.6(3) . . . . ?
C1 C3 C4B O1B -22.7(18) . . . . ?
C1 C3 C4B C5B 88.1(11) . . . . ?
C2 N3 C6 C11 -2.4(5) . . . . ?
C2 N3 C6 C7 177.9(3) . . . . ?
C11 C6 C7 C8 0.9(4) . . . . ?
N3 C6 C7 C8 -179.4(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C6 0.8(5) . . . . ?
C7 C6 C11 C10 -0.9(5) . . . . ?
N3 C6 C11 C10 179.4(3) . . . . ?
O3 C12 C13 C18 3.6(4) . . . . ?
O2 C12 C13 C18 -176.3(2) . . . . ?
O3 C12 C13 C14 -177.6(3) . . . . ?
O2 C12 C13 C14 2.6(4) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
C12 C13 C14 C15 -177.7(2) . . . . ?
C13 C14 C15 O4 178.4(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
O4 C15 C16 O5 0.2(4) . . . . ?
C14 C15 C16 O5 178.4(2) . . . . ?
O4 C15 C16 C17 -179.8(2) . . . . ?
C14 C15 C16 C17 -1.5(4) . . . . ?
O5 C16 C17 O6 1.1(4) . . . . ?
C15 C16 C17 O6 -179.0(2) . . . . ?
O5 C16 C17 C18 -178.3(2) . . . . ?
C15 C16 C17 C18 1.7(4) . . . . ?
O6 C17 C18 C13 -179.7(2) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C14 C13 C18 C17 -1.0(4) . . . . ?
C12 C13 C18 C17 177.9(2) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_TDZH_VA
_database_code_depnum_ccdc_archive 'CCDC 2042291'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_date             2021-01-14T08:28:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H13 N3 O S, C8 H8 O4'
_chemical_formula_sum            'C19 H21 N3 O5 S'
_chemical_formula_weight         403.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.4199(5)
_cell_length_b                   21.9195(10)
_cell_length_c                   13.5946(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.160(3)
_cell_angle_gamma                90
_cell_volume                     3923.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      69.94

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1696
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54186   13.426   21.927   13.585   89.991  101.127   90.004
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.78
_exptl_absorpt_correction_type   multi-scan
_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_correction_T_min  0.4156
_exptl_absorpt_correction_T_max  0.7533
_shelx_estimated_absorpt_T_min   0.536
_shelx_estimated_absorpt_T_max   0.901

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_number            30859
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.694
_diffrn_reflns_theta_max         70.196
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             7358
_reflns_number_gt                5736
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7358
_refine_ls_number_parameters     537
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.21
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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 0.26735(6) 0.46505(5) 0.87783(7) 0.0396(3) Uani 1 1 d . . . . .
O1 O 0.3612(3) 0.64529(17) 0.7133(3) 0.0783(11) Uani 1 1 d . . . . .
H1 H 0.386378 0.610828 0.703056 0.094 Uiso 1 1 d R U . . .
O3 O 1.07699(18) 0.60269(14) 0.8737(2) 0.0445(7) Uani 1 1 d . . . . .
H3 H 1.11749 0.570148 0.869337 0.053 Uiso 1 1 d R U . . .
O4 O 0.61363(17) 0.56469(12) 0.8721(2) 0.0372(6) Uani 1 1 d . . . . .
H4 H 0.546839 0.54883 0.865152 0.045 Uiso 1 1 d R U . . .
O5 O 0.65776(19) 0.46657(13) 0.8676(2) 0.0408(7) Uani 1 1 d . . . . .
O6 O 1.03950(18) 0.47998(13) 0.8703(2) 0.0379(6) Uani 1 1 d . . . . .
O7 O 0.97234(17) 0.59544(12) 0.37467(19) 0.0350(6) Uani 1 1 d . . . . .
H5 H 1.018615 0.570156 0.372518 0.042 Uiso 1 1 d R U . . .
O8 O 0.50947(18) 0.55465(12) 0.3756(2) 0.0440(7) Uani 1 1 d . . . . .
H6 H 0.457559 0.538272 0.378506 0.053 Uiso 1 1 d R U . . .
O9 O 0.55408(19) 0.45794(12) 0.3691(2) 0.0466(7) Uani 1 1 d . . . . .
O10 O 0.93847(17) 0.47358(12) 0.3775(2) 0.0347(6) Uani 1 1 d . . . . .
N1 N 0.2545(2) 0.54056(17) 0.8786(2) 0.0410(8) Uani 1 1 d . . . . .
N2 N 0.4260(2) 0.52856(15) 0.8846(2) 0.0348(7) Uani 1 1 d . . . . .
N3 N 0.4616(2) 0.42438(15) 0.8791(2) 0.0358(7) Uani 1 1 d . . . . .
H7 H 0.526565 0.433432 0.887186 0.043 Uiso 1 1 calc R U . . .
C1 C 0.3441(3) 0.5658(2) 0.8831(3) 0.0394(9) Uani 1 1 d . . . . .
C2 C 0.3966(2) 0.47075(18) 0.8819(3) 0.0311(8) Uani 1 1 d . . . . .
C3 C 0.3565(3) 0.6334(2) 0.8875(3) 0.0519(12) Uani 1 1 d . . . . .
H3A H 0.394654 0.644652 0.954914 0.062 Uiso 1 1 calc R U . . .
H3B H 0.288373 0.65232 0.879359 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4111(3) 0.6605(2) 0.8091(4) 0.0598(14) Uani 1 1 d . . . . .
H4A H 0.481139 0.642851 0.819817 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4202(5) 0.7292(3) 0.8172(6) 0.094(2) Uani 1 1 d . . . . .
H5A H 0.455504 0.740283 0.884847 0.141 Uiso 1 1 calc R U . . .
H5B H 0.458808 0.744299 0.767981 0.141 Uiso 1 1 calc R U . . .
H5C H 0.352261 0.747382 0.804058 0.141 Uiso 1 1 calc R U . . .
C6 C 0.4343(3) 0.36255(19) 0.8644(3) 0.0396(9) Uani 1 1 d . . . . .
C7 C 0.4836(4) 0.3277(2) 0.8051(4) 0.0589(13) Uani 1 1 d . . . . .
H7A H 0.538215 0.344177 0.778434 0.071 Uiso 1 1 calc R U . . .
C8 C 0.4522(6) 0.2672(3) 0.7844(6) 0.093(2) Uani 1 1 d . . . . .
H8A H 0.484606 0.242651 0.742393 0.112 Uiso 1 1 calc R U . . .
C9 C 0.3741(6) 0.2436(3) 0.8251(7) 0.110(3) Uani 1 1 d . . . . .
H9A H 0.351778 0.202989 0.809844 0.132 Uiso 1 1 calc R U . . .
C10 C 0.3292(5) 0.2780(3) 0.8868(8) 0.116(3) Uani 1 1 d . . . . .
H10A H 0.276389 0.260833 0.915518 0.139 Uiso 1 1 calc R U . . .
C11 C 0.3584(4) 0.3366(3) 0.9081(5) 0.0695(15) Uani 1 1 d . . . . .
H11A H 0.327214 0.359938 0.952754 0.083 Uiso 1 1 calc R U . . .
S2 S 0.1629(3) 0.45358(11) 0.3804(3) 0.0244(14) Uani 0.65 1 d . . P A 1
N4 N 0.1501(9) 0.5288(6) 0.3664(3) 0.0269(14) Uani 0.65 1 d . . P A 1
N5 N 0.3190(6) 0.5135(4) 0.3640(3) 0.0284(14) Uani 0.65 1 d . . P A 1
N6 N 0.3591(9) 0.4069(6) 0.3830(5) 0.029(3) Uani 0.65 1 d . . P A 1
H8 H 0.423916 0.419575 0.383973 0.035 Uiso 0.65 1 d R U P A 1
C12 C 0.2387(5) 0.5530(3) 0.3590(3) 0.0267(13) Uani 0.65 1 d D . P A 1
C13 C 0.2868(10) 0.4527(5) 0.3767(3) 0.029(3) Uani 0.65 1 d . . P A 1
O2 O 0.2664(4) 0.6511(3) 0.5155(4) 0.0407(12) Uiso 0.5 1 d D . P A 1
H2 H 0.297532 0.649098 0.580294 0.049 Uiso 0.5 1 d R U P A 1
C14 C 0.2522(4) 0.6184(3) 0.3459(4) 0.0304(12) Uiso 0.5 1 d D . P A 1
H14A H 0.221134 0.639755 0.286186 0.036 Uiso 0.5 1 d R U P A 1
H14B H 0.221134 0.639755 0.286186 0.036 Uiso 0.5 1 d R U P A 1
C15 C 0.3210(5) 0.6516(3) 0.4346(5) 0.0310(15) Uiso 0.5 1 d D . P A 1
H15A H 0.386571 0.629038 0.454713 0.037 Uiso 0.5 1 calc R U P A 1
C16 C 0.3413(8) 0.7164(4) 0.4103(8) 0.060(3) Uiso 0.5 1 d D . P A 1
H16A H 0.378617 0.717402 0.355055 0.09 Uiso 0.5 1 calc R U P A 1
H16B H 0.276702 0.738107 0.390364 0.09 Uiso 0.5 1 calc R U P A 1
H16C H 0.381851 0.736106 0.46942 0.09 Uiso 0.5 1 calc R U P A 1
C17 C 0.3390(10) 0.3472(7) 0.3979(4) 0.037(4) Uiso 0.65 1 d . . P A 1
C18 C 0.4274(6) 0.3117(4) 0.4253(4) 0.0542(18) Uiso 0.65 1 d . . P A 1
H18A H 0.492583 0.329777 0.431122 0.065 Uiso 0.65 1 calc R U P A 1
C19 C 0.4179(7) 0.2497(4) 0.4438(5) 0.071(2) Uiso 0.65 1 d . . P A 1
H19A H 0.4775 0.225554 0.461408 0.085 Uiso 0.65 1 calc R U P A 1
C20 C 0.3255(8) 0.2228(6) 0.4373(6) 0.071(3) Uiso 0.65 1 d . . P A 1
H20A H 0.32047 0.18063 0.451985 0.085 Uiso 0.65 1 calc R U P A 1
C21 C 0.2336(11) 0.2601(7) 0.4070(7) 0.062(4) Uiso 0.65 1 d . . P A 1
H21A H 0.167783 0.242674 0.400202 0.075 Uiso 0.65 1 calc R U P A 1
C22 C 0.2461(8) 0.3205(5) 0.3892(6) 0.048(3) Uiso 0.65 1 d . . P A 1
H22A H 0.187316 0.345115 0.369786 0.058 Uiso 0.65 1 calc R U P A 1
S2B S 0.1614(5) 0.4536(3) 0.3803(5) 0.044(4) Uani 0.35 1 d . . P B 2
N4B N 0.151(2) 0.5292(13) 0.3871(6) 0.033(3) Uiso 0.35 1 d . . P B 2
N5B N 0.3232(12) 0.5153(8) 0.3898(6) 0.018(2) Uiso 0.35 1 d . . P B 2
N6B N 0.3492(18) 0.4160(12) 0.3812(9) 0.023(5) Uiso 0.35 1 d . . P B 2
H8B H 0.417927 0.426361 0.389575 0.028 Uiso 0.35 1 d R U P B 2
C12B C 0.2418(12) 0.5509(7) 0.3912(5) 0.028(3) Uiso 0.35 1 d . . P B 2
C13B C 0.2968(16) 0.4630(10) 0.3843(6) 0.012(4) Uiso 0.35 1 d . . P B 2
C14B C 0.2515(13) 0.6186(8) 0.3980(9) 0.073(4) Uiso 0.35 1 d D . P B 2
H14C H 0.18213 0.635998 0.382515 0.087 Uiso 0.35 1 calc R U P B 2
H14D H 0.280367 0.629007 0.468609 0.087 Uiso 0.35 1 calc R U P B 2
O2B O 0.2752(10) 0.6320(6) 0.2359(9) 0.093(4) Uiso 0.35 1 d D . P B 2
H2B H 0.295813 0.602389 0.204873 0.112 Uiso 0.35 1 d R U P B 2
C15B C 0.3110(15) 0.6495(8) 0.3363(12) 0.093(6) Uiso 0.35 1 d D . P B 2
H15B H 0.383855 0.637379 0.357096 0.112 Uiso 0.35 1 calc R U P B 2
C16B C 0.3004(14) 0.7192(7) 0.3508(13) 0.072(4) Uiso 0.35 1 d D . P B 2
H16D H 0.325895 0.729694 0.42123 0.108 Uiso 0.35 1 calc R U P B 2
H16E H 0.339784 0.741017 0.30837 0.108 Uiso 0.35 1 calc R U P B 2
H16F H 0.228695 0.730816 0.332 0.108 Uiso 0.35 1 calc R U P B 2
C17B C 0.3427(19) 0.3477(13) 0.3882(7) 0.031(6) Uiso 0.35 1 d . . P B 2
C18B C 0.4173(9) 0.3098(6) 0.3726(7) 0.040(3) Uiso 0.35 1 d . . P B 2
H18B H 0.477616 0.326097 0.356252 0.048 Uiso 0.35 1 calc R U P B 2
C19B C 0.4064(11) 0.2462(7) 0.3803(8) 0.059(4) Uiso 0.35 1 d . . P B 2
H19B H 0.45976 0.220023 0.369703 0.071 Uiso 0.35 1 calc R U P B 2
C20B C 0.3176(13) 0.2211(9) 0.4035(9) 0.061(4) Uiso 0.35 1 d . . P B 2
H20B H 0.309428 0.178212 0.407179 0.073 Uiso 0.35 1 calc R U P B 2
C21B C 0.2485(15) 0.2572(10) 0.4195(9) 0.039(5) Uiso 0.35 1 d . . P B 2
H21B H 0.189818 0.239591 0.437269 0.047 Uiso 0.35 1 calc R U P B 2
C22B C 0.2517(12) 0.3214(8) 0.4130(9) 0.036(4) Uiso 0.35 1 d . . P B 2
H22B H 0.196917 0.346108 0.424333 0.043 Uiso 0.35 1 calc R U P B 2
C14C C 0.2522(4) 0.6184(3) 0.3459(4) 0.0304(12) Uiso 0.15 1 d D . P C 3
H14E H 0.219404 0.640566 0.284079 0.036 Uiso 0.15 1 d R U P C 3
H14F H 0.219404 0.640566 0.284079 0.036 Uiso 0.15 1 d R U P C 3
O2C O 0.3286(11) 0.6426(7) 0.5094(10) 0.024(3) Uiso 0.15 1 d D . P C 3
H2C H 0.338824 0.643229 0.573102 0.029 Uiso 0.15 1 d R U P C 3
C15C C 0.251(2) 0.6622(10) 0.4313(16) 0.087(12) Uiso 0.15 1 d D . P C 3
H15C H 0.183981 0.661432 0.452567 0.104 Uiso 0.15 1 calc R U P C 3
C16C C 0.277(2) 0.7263(10) 0.403(2) 0.042(6) Uiso 0.15 1 d D . P C 3
H16G H 0.224429 0.741258 0.348389 0.063 Uiso 0.15 1 calc R U P C 3
H16H H 0.281804 0.753187 0.461332 0.063 Uiso 0.15 1 calc R U P C 3
H16I H 0.342794 0.725897 0.381156 0.063 Uiso 0.15 1 calc R U P C 3
C23 C 0.7841(3) 0.54281(18) 0.8693(3) 0.0308(8) Uani 1 1 d . . . . .
C24 C 0.8615(3) 0.50009(18) 0.8711(3) 0.0310(8) Uani 1 1 d . . . . .
H24A H 0.846383 0.457803 0.872815 0.037 Uiso 1 1 calc R U . . .
C25 C 0.9596(3) 0.51850(18) 0.8704(3) 0.0309(8) Uani 1 1 d . . . . .
C26 C 0.9821(3) 0.58087(18) 0.8707(3) 0.0327(8) Uani 1 1 d . . . . .
C27 C 0.9046(3) 0.62324(18) 0.8680(3) 0.0342(8) Uani 1 1 d . . . . .
H27A H 0.919386 0.665576 0.866566 0.041 Uiso 1 1 calc R U . . .
C28 C 0.8064(3) 0.60445(18) 0.8675(3) 0.0320(8) Uani 1 1 d . . . . .
H28A H 0.754096 0.633819 0.865886 0.038 Uiso 1 1 calc R U . . .
C29 C 0.6800(3) 0.52062(18) 0.8694(3) 0.0322(8) Uani 1 1 d . . . . .
C30 C 1.0180(3) 0.41608(19) 0.8669(3) 0.0391(9) Uani 1 1 d . . . . .
H30A H 1.080791 0.393208 0.867102 0.059 Uiso 1 1 calc R U . . .
H30B H 0.98978 0.404577 0.925558 0.059 Uiso 1 1 calc R U . . .
H30C H 0.968699 0.40664 0.805644 0.059 Uiso 1 1 calc R U . . .
C31 C 0.6803(2) 0.53463(16) 0.3727(2) 0.0271(7) Uani 1 1 d . . . . .
C32 C 0.7581(2) 0.49205(17) 0.3743(2) 0.0278(7) Uani 1 1 d . . . . .
H32A H 0.743485 0.449667 0.37516 0.033 Uiso 1 1 calc R U . . .
C33 C 0.8564(2) 0.51132(17) 0.3746(2) 0.0276(7) Uani 1 1 d . . . . .
C34 C 0.8782(2) 0.57406(17) 0.3733(2) 0.0275(7) Uani 1 1 d . . . . .
C35 C 0.8001(3) 0.61580(17) 0.3713(3) 0.0307(8) Uani 1 1 d . . . . .
H35A H 0.814236 0.658229 0.369976 0.037 Uiso 1 1 calc R U . . .
C36 C 0.7015(3) 0.59629(17) 0.3711(2) 0.0298(8) Uani 1 1 d . . . . .
H36A H 0.648682 0.625326 0.369795 0.036 Uiso 1 1 calc R U . . .
C37 C 0.5769(3) 0.51172(17) 0.3724(3) 0.0305(8) Uani 1 1 d . . . . .
C38 C 0.9169(3) 0.40951(18) 0.3758(3) 0.0390(9) Uani 1 1 d . . . . .
H38A H 0.979939 0.386508 0.378141 0.059 Uiso 1 1 calc R U . . .
H38B H 0.887293 0.398822 0.43401 0.059 Uiso 1 1 calc R U . . .
H38C H 0.868745 0.399395 0.31413 0.059 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.665(4) . ?
S1 C2 1.729(3) . ?
O1 C4 1.386(6) . ?
O1 H1 0.8499 . ?
O3 C26 1.353(4) . ?
O3 H3 0.9057 . ?
O4 C29 1.319(4) . ?
O4 H4 0.9489 . ?
O5 C29 1.221(5) . ?
O6 C25 1.365(4) . ?
O6 C30 1.429(5) . ?
O7 C34 1.345(4) . ?
O7 H5 0.837 . ?
O8 C37 1.312(4) . ?
O8 H6 0.7914 . ?
O9 C37 1.216(5) . ?
O10 C33 1.372(4) . ?
O10 C38 1.433(5) . ?
N1 C1 1.314(5) . ?
N2 C2 1.326(5) . ?
N2 C1 1.366(5) . ?
N3 C2 1.345(5) . ?
N3 C6 1.408(5) . ?
N3 H7 0.88 . ?
C1 C3 1.493(6) . ?
C3 C4 1.525(7) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.513(7) . ?
C4 H4A 1 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.371(6) . ?
C6 C11 1.396(6) . ?
C7 C8 1.402(8) . ?
C7 H7A 0.95 . ?
C8 C9 1.376(10) . ?
C8 H8A 0.95 . ?
C9 C10 1.352(12) . ?
C9 H9A 0.95 . ?
C10 C11 1.359(9) . ?
C10 H10A 0.95 . ?
C11 H11A 0.95 . ?
S2 N4 1.666(13) . ?
S2 C13 1.673(14) . ?
N4 C12 1.322(14) . ?
N5 C12 1.373(11) . ?
N5 C13 1.422(14) . ?
N6 C17 1.36(2) . ?
N6 C13 1.388(19) . ?
N6 H8 0.9106 . ?
C12 C14 1.461(9) . ?
O2 C15 1.435(8) . ?
O2 H2 0.8999 . ?
C14 C15 1.550(8) . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C15 C16 1.496(10) . ?
C15 H15A 1 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C22 1.361(17) . ?
C17 C18 1.407(16) . ?
C18 C19 1.392(12) . ?
C18 H18A 0.95 . ?
C19 C20 1.360(14) . ?
C19 H19A 0.95 . ?
C20 C21 1.471(18) . ?
C20 H20A 0.95 . ?
C21 C22 1.362(18) . ?
C21 H21A 0.95 . ?
C22 H22A 0.95 . ?
S2B N4B 1.67(3) . ?
S2B C13B 1.82(2) . ?
N4B C12B 1.30(3) . ?
N5B C13B 1.20(3) . ?
N5B C12B 1.35(2) . ?
N6B C13B 1.25(4) . ?
N6B C17B 1.50(4) . ?
N6B H8B 0.9346 . ?
C12B C14B 1.49(2) . ?
C14B C15B 1.434(16) . ?
C14B H14C 0.99 . ?
C14B H14D 0.99 . ?
O2B C15B 1.409(15) . ?
O2B H2B 0.8501 . ?
C15B C16B 1.550(16) . ?
C15B H15B 1 . ?
C16B H16D 0.98 . ?
C16B H16E 0.98 . ?
C16B H16F 0.98 . ?
C17B C18B 1.35(3) . ?
C17B C22B 1.45(3) . ?
C18B C19B 1.406(19) . ?
C18B H18B 0.95 . ?
C19B C20B 1.40(2) . ?
C19B H19B 0.95 . ?
C20B C21B 1.27(3) . ?
C20B H20B 0.95 . ?
C21B C22B 1.41(3) . ?
C21B H21B 0.95 . ?
C22B H22B 0.95 . ?
C14C C15C 1.508(19) . ?
C14C H14E 0.9968 . ?
C14C H14F 0.9968 . ?
O2C C15C 1.401(19) . ?
O2C H2C 0.85 . ?
C15C C16C 1.516(19) . ?
C15C H15C 1 . ?
C16C H16G 0.98 . ?
C16C H16H 0.98 . ?
C16C H16I 0.98 . ?
C23 C28 1.385(5) . ?
C23 C24 1.395(5) . ?
C23 C29 1.479(5) . ?
C24 C25 1.379(5) . ?
C24 H24A 0.95 . ?
C25 C26 1.400(6) . ?
C26 C27 1.390(5) . ?
C27 C28 1.379(5) . ?
C27 H27A 0.95 . ?
C28 H28A 0.95 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 C36 1.382(5) . ?
C31 C32 1.398(5) . ?
C31 C37 1.475(5) . ?
C32 C33 1.384(5) . ?
C32 H32A 0.95 . ?
C33 C34 1.407(5) . ?
C34 C35 1.387(5) . ?
C35 C36 1.391(5) . ?
C35 H35A 0.95 . ?
C36 H36A 0.95 . ?
C38 H38A 0.98 . ?
C38 H38B 0.98 . ?
C38 H38C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C2 91.86(18) . . ?
C4 O1 H1 103.4 . . ?
C26 O3 H3 107 . . ?
C29 O4 H4 111 . . ?
C25 O6 C30 116.9(3) . . ?
C34 O7 H5 118.1 . . ?
C37 O8 H6 107.2 . . ?
C33 O10 C38 115.6(3) . . ?
C1 N1 S1 108.9(3) . . ?
C2 N2 C1 109.6(3) . . ?
C2 N3 C6 125.4(3) . . ?
C2 N3 H7 117.3 . . ?
C6 N3 H7 117.3 . . ?
N1 C1 N2 118.4(4) . . ?
N1 C1 C3 120.9(4) . . ?
N2 C1 C3 120.7(4) . . ?
N2 C2 N3 122.1(3) . . ?
N2 C2 S1 111.2(3) . . ?
N3 C2 S1 126.6(3) . . ?
C1 C3 C4 115.0(4) . . ?
C1 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
O1 C4 C5 109.0(5) . . ?
O1 C4 C3 110.7(4) . . ?
C5 C4 C3 112.3(5) . . ?
O1 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 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 . . ?
C7 C6 C11 119.9(5) . . ?
C7 C6 N3 118.6(4) . . ?
C11 C6 N3 121.5(4) . . ?
C6 C7 C8 119.0(5) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C10 C9 C8 120.4(6) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.9(7) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C10 C11 C6 119.9(6) . . ?
C10 C11 H11A 120.1 . . ?
C6 C11 H11A 120.1 . . ?
N4 S2 C13 95.1(6) . . ?
C12 N4 S2 109.3(8) . . ?
C12 N5 C13 110.0(8) . . ?
C17 N6 C13 123.3(10) . . ?
C17 N6 H8 120.6 . . ?
C13 N6 H8 115.7 . . ?
N4 C12 N5 116.9(8) . . ?
N4 C12 C14 122.4(7) . . ?
N5 C12 C14 120.6(6) . . ?
N6 C13 N5 117.4(10) . . ?
N6 C13 S2 133.9(9) . . ?
N5 C13 S2 108.7(9) . . ?
C15 O2 H2 122.7 . . ?
C12 C14 C15 115.8(4) . . ?
C12 C14 H14A 122.5 . . ?
C15 C14 H14A 121.7 . . ?
C12 C14 H14B 122.5 . . ?
C15 C14 H14B 121.7 . . ?
H14A C14 H14B 0 . . ?
O2 C15 C16 108.6(6) . . ?
O2 C15 C14 106.1(5) . . ?
C16 C15 C14 112.3(6) . . ?
O2 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N6 C17 C22 127.3(12) . . ?
N6 C17 C18 112.9(11) . . ?
C22 C17 C18 119.8(13) . . ?
C19 C18 C17 119.0(10) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
C20 C19 C18 121.7(9) . . ?
C20 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
C19 C20 C21 118.8(11) . . ?
C19 C20 H20A 120.6 . . ?
C21 C20 H20A 120.6 . . ?
C22 C21 C20 117.7(13) . . ?
C22 C21 H21A 121.2 . . ?
C20 C21 H21A 121.2 . . ?
C17 C22 C21 123.0(12) . . ?
C17 C22 H22A 118.5 . . ?
C21 C22 H22A 118.5 . . ?
N4B S2B C13B 88.9(13) . . ?
C12B N4B S2B 106(2) . . ?
C13B N5B C12B 109.0(17) . . ?
C13B N6B C17B 141(2) . . ?
C13B N6B H8B 110.2 . . ?
C17B N6B H8B 107.5 . . ?
N4B C12B N5B 123.0(19) . . ?
N4B C12B C14B 115.9(18) . . ?
N5B C12B C14B 121.1(15) . . ?
N5B C13B N6B 129(2) . . ?
N5B C13B S2B 113.0(17) . . ?
N6B C13B S2B 118.1(19) . . ?
C15B C14B C12B 119.0(13) . . ?
C15B C14B H14C 107.6 . . ?
C12B C14B H14C 107.6 . . ?
C15B C14B H14D 107.6 . . ?
C12B C14B H14D 107.6 . . ?
H14C C14B H14D 107 . . ?
C15B O2B H2B 127.3 . . ?
O2B C15B C14B 108.3(13) . . ?
O2B C15B C16B 111.6(14) . . ?
C14B C15B C16B 108.3(14) . . ?
O2B C15B H15B 109.5 . . ?
C14B C15B H15B 109.5 . . ?
C16B C15B H15B 109.5 . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C18B C17B C22B 118(2) . . ?
C18B C17B N6B 123(2) . . ?
C22B C17B N6B 118(2) . . ?
C17B C18B C19B 120.5(16) . . ?
C17B C18B H18B 119.7 . . ?
C19B C18B H18B 119.7 . . ?
C20B C19B C18B 120.6(15) . . ?
C20B C19B H19B 119.7 . . ?
C18B C19B H19B 119.7 . . ?
C21B C20B C19B 118.4(19) . . ?
C21B C20B H20B 120.8 . . ?
C19B C20B H20B 120.8 . . ?
C20B C21B C22B 125.3(19) . . ?
C20B C21B H21B 117.3 . . ?
C22B C21B H21B 117.3 . . ?
C21B C22B C17B 116.7(18) . . ?
C21B C22B H22B 121.6 . . ?
C17B C22B H22B 121.6 . . ?
C15C C14C H14E 105.7 . . ?
C15C C14C H14F 105.7 . . ?
H14E C14C H14F 0 . . ?
C15C O2C H2C 135.8 . . ?
O2C C15C C14C 105.8(16) . . ?
O2C C15C C16C 108(2) . . ?
C14C C15C C16C 111.0(19) . . ?
O2C C15C H15C 110.8 . . ?
C14C C15C H15C 110.8 . . ?
C16C C15C H15C 110.8 . . ?
C15C C16C H16G 109.5 . . ?
C15C C16C H16H 109.5 . . ?
H16G C16C H16H 109.5 . . ?
C15C C16C H16I 109.5 . . ?
H16G C16C H16I 109.5 . . ?
H16H C16C H16I 109.5 . . ?
C28 C23 C24 119.4(3) . . ?
C28 C23 C29 121.9(3) . . ?
C24 C23 C29 118.6(3) . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24A 119.6 . . ?
C23 C24 H24A 119.6 . . ?
O6 C25 C24 124.8(4) . . ?
O6 C25 C26 115.8(3) . . ?
C24 C25 C26 119.5(3) . . ?
O3 C26 C27 117.4(4) . . ?
O3 C26 C25 123.1(3) . . ?
C27 C26 C25 119.5(3) . . ?
C28 C27 C26 120.7(4) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C27 C28 C23 120.1(3) . . ?
C27 C28 H28A 120 . . ?
C23 C28 H28A 120 . . ?
O5 C29 O4 123.2(3) . . ?
O5 C29 C23 123.1(3) . . ?
O4 C29 C23 113.7(3) . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 119.9(3) . . ?
C36 C31 C37 122.0(3) . . ?
C32 C31 C37 118.2(3) . . ?
C33 C32 C31 120.3(3) . . ?
C33 C32 H32A 119.8 . . ?
C31 C32 H32A 119.8 . . ?
O10 C33 C32 125.1(3) . . ?
O10 C33 C34 115.0(3) . . ?
C32 C33 C34 119.9(3) . . ?
O7 C34 C35 118.3(3) . . ?
O7 C34 C33 122.5(3) . . ?
C35 C34 C33 119.1(3) . . ?
C34 C35 C36 120.8(3) . . ?
C34 C35 H35A 119.6 . . ?
C36 C35 H35A 119.6 . . ?
C31 C36 C35 119.9(3) . . ?
C31 C36 H36A 120 . . ?
C35 C36 H36A 120 . . ?
O9 C37 O8 121.7(3) . . ?
O9 C37 C31 124.0(3) . . ?
O8 C37 C31 114.2(3) . . ?
O10 C38 H38A 109.5 . . ?
O10 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O10 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 N1 C1 -0.8(3) . . . . ?
S1 N1 C1 N2 1.0(4) . . . . ?
S1 N1 C1 C3 -178.4(3) . . . . ?
C2 N2 C1 N1 -0.6(5) . . . . ?
C2 N2 C1 C3 178.8(4) . . . . ?
C1 N2 C2 N3 177.6(3) . . . . ?
C1 N2 C2 S1 -0.1(4) . . . . ?
C6 N3 C2 N2 -172.1(3) . . . . ?
C6 N3 C2 S1 5.3(5) . . . . ?
N1 S1 C2 N2 0.5(3) . . . . ?
N1 S1 C2 N3 -177.1(3) . . . . ?
N1 C1 C3 C4 -127.5(4) . . . . ?
N2 C1 C3 C4 53.2(5) . . . . ?
C1 C3 C4 O1 57.5(5) . . . . ?
C1 C3 C4 C5 179.5(4) . . . . ?
C2 N3 C6 C7 140.3(4) . . . . ?
C2 N3 C6 C11 -39.3(6) . . . . ?
C11 C6 C7 C8 3.9(7) . . . . ?
N3 C6 C7 C8 -175.6(5) . . . . ?
C6 C7 C8 C9 -1.2(9) . . . . ?
C7 C8 C9 C10 -1.5(12) . . . . ?
C8 C9 C10 C11 1.4(13) . . . . ?
C9 C10 C11 C6 1.4(11) . . . . ?
C7 C6 C11 C10 -4.1(8) . . . . ?
N3 C6 C11 C10 175.5(5) . . . . ?
C13 S2 N4 C12 0.02(15) . . . . ?
S2 N4 C12 N5 0.0(2) . . . . ?
S2 N4 C12 C14 179.93(19) . . . . ?
C13 N5 C12 N4 -0.1(3) . . . . ?
C13 N5 C12 C14 -180.0(2) . . . . ?
C17 N6 C13 N5 178.2(3) . . . . ?
C17 N6 C13 S2 -2.1(5) . . . . ?
C12 N5 C13 N6 179.9(2) . . . . ?
C12 N5 C13 S2 0.1(2) . . . . ?
N4 S2 C13 N6 -179.8(3) . . . . ?
N4 S2 C13 N5 -0.05(15) . . . . ?
N4 C12 C14 C15 113.5(5) . . . . ?
N5 C12 C14 C15 -66.6(5) . . . . ?
C12 C14 C15 O2 -68.7(7) . . . . ?
C12 C14 C15 C16 172.9(6) . . . . ?
C13 N6 C17 C22 14.1(5) . . . . ?
C13 N6 C17 C18 -165.7(4) . . . . ?
N6 C17 C18 C19 179.4(3) . . . . ?
C22 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C21 1.8(6) . . . . ?
C19 C20 C21 C22 -1.4(7) . . . . ?
N6 C17 C22 C21 -179.1(5) . . . . ?
C18 C17 C22 C21 0.7(6) . . . . ?
C20 C21 C22 C17 0.2(8) . . . . ?
C13B S2B N4B C12B 0.06(15) . . . . ?
S2B N4B C12B N5B -0.1(2) . . . . ?
S2B N4B C12B C14B -179.85(18) . . . . ?
C13B N5B C12B N4B 0.1(3) . . . . ?
C13B N5B C12B C14B 179.9(2) . . . . ?
C12B N5B C13B N6B -180.0(3) . . . . ?
C12B N5B C13B S2B -0.1(2) . . . . ?
C17B N6B C13B N5B 169.0(8) . . . . ?
C17B N6B C13B S2B -10.9(8) . . . . ?
N4B S2B C13B N5B 0.02(17) . . . . ?
N4B S2B C13B N6B 179.9(2) . . . . ?
N4B C12B C14B C15B -135.3(13) . . . . ?
N5B C12B C14B C15B 44.9(14) . . . . ?
C12B C14B C15B O2B 53.7(19) . . . . ?
C12B C14B C15B C16B 174.9(13) . . . . ?
C13B N6B C17B C18B 174.4(9) . . . . ?
C13B N6B C17B C22B -5.6(10) . . . . ?
C22B C17B C18B C19B 0.0(3) . . . . ?
N6B C17B C18B C19B -180.0(3) . . . . ?
C17B C18B C19B C20B 0.5(3) . . . . ?
C18B C19B C20B C21B -1.5(7) . . . . ?
C19B C20B C21B C22B 2.0(10) . . . . ?
C20B C21B C22B C17B -1.5(9) . . . . ?
C18B C17B C22B C21B 0.3(6) . . . . ?
N6B C17B C22B C21B -179.7(5) . . . . ?
C28 C23 C24 C25 -0.5(5) . . . . ?
C29 C23 C24 C25 179.6(3) . . . . ?
C30 O6 C25 C24 2.4(5) . . . . ?
C30 O6 C25 C26 -178.1(3) . . . . ?
C23 C24 C25 O6 -178.8(3) . . . . ?
C23 C24 C25 C26 1.8(5) . . . . ?
O6 C25 C26 O3 -2.0(5) . . . . ?
C24 C25 C26 O3 177.5(3) . . . . ?
O6 C25 C26 C27 178.2(3) . . . . ?
C24 C25 C26 C27 -2.3(5) . . . . ?
O3 C26 C27 C28 -178.3(3) . . . . ?
C25 C26 C27 C28 1.5(5) . . . . ?
C26 C27 C28 C23 -0.2(5) . . . . ?
C24 C23 C28 C27 -0.3(5) . . . . ?
C29 C23 C28 C27 179.6(3) . . . . ?
C28 C23 C29 O5 177.5(3) . . . . ?
C24 C23 C29 O5 -2.5(5) . . . . ?
C28 C23 C29 O4 -2.8(5) . . . . ?
C24 C23 C29 O4 177.1(3) . . . . ?
C36 C31 C32 C33 0.2(5) . . . . ?
C37 C31 C32 C33 180.0(3) . . . . ?
C38 O10 C33 C32 2.7(5) . . . . ?
C38 O10 C33 C34 -178.2(3) . . . . ?
C31 C32 C33 O10 179.0(3) . . . . ?
C31 C32 C33 C34 0.0(5) . . . . ?
O10 C33 C34 O7 0.1(5) . . . . ?
C32 C33 C34 O7 179.2(3) . . . . ?
O10 C33 C34 C35 -179.4(3) . . . . ?
C32 C33 C34 C35 -0.3(5) . . . . ?
O7 C34 C35 C36 -179.2(3) . . . . ?
C33 C34 C35 C36 0.4(5) . . . . ?
C32 C31 C36 C35 -0.2(5) . . . . ?
C37 C31 C36 C35 -179.9(3) . . . . ?
C34 C35 C36 C31 -0.1(5) . . . . ?
C36 C31 C37 O9 176.5(4) . . . . ?
C32 C31 C37 O9 -3.3(5) . . . . ?
C36 C31 C37 O8 -3.3(5) . . . . ?
C32 C31 C37 O8 177.0(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 O9 0.85 2.04 2.857(5) 159.9 3_666 yes
O3 H3 O6 0.91 2.24 2.735(4) 114.1 . yes
O3 H3 N1 0.91 1.93 2.733(4) 146.8 1_655 yes
O4 H4 N2 0.95 1.75 2.676(4) 164.4 . yes
O7 H5 N4 0.84 2 2.818(12) 165.5 1_655 yes
O7 H5 N4B 0.84 1.96 2.78(3) 163.9 1_655 yes
O8 H6 N5 0.79 1.91 2.686(8) 166.5 . yes
O8 H6 N5B 0.79 1.91 2.687(17) 168.2 . yes
N3 H7 O5 0.88 1.97 2.823(4) 163 . yes
C4 H4A O4 1 2.47 3.409(5) 155.9 . yes
C7 H7A O2B 0.95 2.6 3.503(14) 158.4 3_666 yes
C11 H11A S1 0.95 2.58 3.065(6) 111.7 . yes
N6 H8 O9 0.91 1.98 2.885(13) 170.1 . yes
O2 H2 O1 0.9 1.85 2.746(7) 179.7 . yes
C22 H22A S2 0.95 2.41 3.118(11) 131.3 . yes
N6B H8B O9 0.93 2.02 2.93(3) 164.1 . yes
O2B H2B O5 0.85 1.97 2.820(13) 179.4 3_666 yes
C18B H18B O1 0.95 2.6 3.538(13) 169.3 3_666 yes
C22B H22B S2B 0.95 2.45 3.139(18) 128.9 . yes
O2C H2C O1 0.85 1.87 2.722(14) 179.6 . yes



# END of CIF
####################################################################### 
# 
# 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_TDZH_OxAc
_database_code_depnum_ccdc_archive 'CCDC 2042292'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_date             2020-08-20T05:19:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H13 N3 O S, 0.5(C2 H2 O4)'
_chemical_formula_sum            'C12 H14 N3 O3 S'
_chemical_formula_weight         280.32

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.3570(19)
_cell_length_b                   4.8081(5)
_cell_length_c                   20.166(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.286(10)
_cell_angle_gamma                90
_cell_volume                     1354.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1363
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      56.12

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             588
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54184   14.332    4.811   20.145   89.965  103.194   90.078
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_type   multi-scan
_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_correction_T_min  0.3558
_exptl_absorpt_correction_T_max  0.7523

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_number            8414
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.506
_diffrn_reflns_theta_max         63.067
_diffrn_reflns_theta_full        63.067
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_coverage         0
_reflns_number_total             2128
_reflns_number_gt                1241
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2128
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0848
_refine_ls_wR_factor_ref         0.2075
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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 0.67756(13) 0.0353(3) 0.70173(9) 0.0661(6) Uani 1 1 d . . . . .
O1 O 0.7662(4) 0.0333(11) 0.4929(3) 0.109(2) Uani 1 1 d . . . . .
H1 H 0.719133 -0.02404 0.510166 0.131 Uiso 1 1 d R U . . .
O2 O 0.6068(3) 0.8278(8) 0.5340(2) 0.0691(13) Uani 1 1 d . . . . .
H2 H 0.626788 0.691529 0.560283 0.083 Uiso 1 1 d R U . . .
O3 O 0.4585(3) 0.7523(9) 0.5495(2) 0.0715(14) Uani 1 1 d . . . . .
N1 N 0.7716(4) 0.0730(9) 0.6663(3) 0.0619(15) Uani 1 1 d . . . . .
N2 N 0.6662(4) 0.4126(10) 0.6142(3) 0.0598(14) Uani 1 1 d . . . . .
N3 N 0.5254(4) 0.3767(11) 0.6543(3) 0.0683(16) Uani 1 1 d . . . . .
H3C H 0.49909 0.513904 0.627588 0.082 Uiso 1 1 calc R U . . .
C1 C 0.7537(5) 0.2824(12) 0.6234(3) 0.0605(18) Uani 1 1 d . . . . .
C2 C 0.6134(5) 0.3041(13) 0.6534(4) 0.0629(18) Uani 1 1 d . . . . .
C3 C 0.8223(5) 0.3753(14) 0.5823(4) 0.072(2) Uani 1 1 d . . . . .
H3A H 0.883759 0.276868 0.599093 0.086 Uiso 1 1 calc R U . . .
H3B H 0.834485 0.576563 0.59026 0.086 Uiso 1 1 calc R U . . .
C4 C 0.7887(6) 0.3254(15) 0.5050(4) 0.081(2) Uani 1 1 d . . . . .
H4A H 0.729252 0.436402 0.487448 0.098 Uiso 1 1 calc R U . . .
C5 C 0.8609(6) 0.412(2) 0.4690(4) 0.117(3) Uani 1 1 d . . . . .
H5A H 0.875267 0.610128 0.477752 0.175 Uiso 1 1 calc R U . . .
H5B H 0.919315 0.302887 0.485115 0.175 Uiso 1 1 calc R U . . .
H5C H 0.83677 0.382769 0.419998 0.175 Uiso 1 1 calc R U . . .
C6 C 0.4705(5) 0.2476(13) 0.6955(4) 0.0643(18) Uani 1 1 d . . . . .
C11 C 0.5027(5) 0.2454(15) 0.7652(4) 0.077(2) Uani 1 1 d . . . . .
H11A H 0.561384 0.333134 0.786064 0.093 Uiso 1 1 calc R U . . .
C10 C 0.4486(6) 0.1141(18) 0.8049(4) 0.092(3) Uani 1 1 d . . . . .
H10A H 0.470373 0.112237 0.853122 0.111 Uiso 1 1 calc R U . . .
C9 C 0.3630(6) -0.0144(16) 0.7745(5) 0.091(3) Uani 1 1 d . . . . .
H9A H 0.326573 -0.108695 0.80135 0.11 Uiso 1 1 calc R U . . .
C8 C 0.3315(6) -0.0026(18) 0.7039(5) 0.094(3) Uani 1 1 d . . . . .
H8A H 0.271915 -0.084606 0.682545 0.113 Uiso 1 1 calc R U . . .
C7 C 0.3846(5) 0.1244(15) 0.6654(4) 0.080(2) Uani 1 1 d . . . . .
H7A H 0.362533 0.128489 0.6172 0.096 Uiso 1 1 calc R U . . .
C12 C 0.5169(5) 0.8734(13) 0.5254(3) 0.0612(18) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.676(6) . ?
S1 C2 1.748(7) . ?
O1 C4 1.450(8) . ?
O1 H1 0.872 . ?
O2 C12 1.281(7) . ?
O2 H2 0.8504 . ?
O3 C12 1.211(8) . ?
N1 C1 1.315(8) . ?
N2 C2 1.322(8) . ?
N2 C1 1.377(8) . ?
N3 C2 1.315(8) . ?
N3 C6 1.414(8) . ?
N3 H3C 0.88 . ?
C1 C3 1.493(9) . ?
C3 C4 1.542(9) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.457(10) . ?
C4 H4A 1 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C11 1.375(9) . ?
C6 C7 1.378(9) . ?
C11 C10 1.388(10) . ?
C11 H11A 0.95 . ?
C10 C9 1.386(10) . ?
C10 H10A 0.95 . ?
C9 C8 1.393(11) . ?
C9 H9A 0.95 . ?
C8 C7 1.353(10) . ?
C8 H8A 0.95 . ?
C7 H7A 0.95 . ?
C12 C12 1.592(13) 3_676 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C2 93.2(3) . . ?
C4 O1 H1 113.8 . . ?
C12 O2 H2 113.7 . . ?
C1 N1 S1 108.0(5) . . ?
C2 N2 C1 111.8(6) . . ?
C2 N3 C6 124.0(6) . . ?
C2 N3 H3C 118 . . ?
C6 N3 H3C 118 . . ?
N1 C1 N2 118.1(7) . . ?
N1 C1 C3 122.7(6) . . ?
N2 C1 C3 119.1(6) . . ?
N3 C2 N2 126.0(6) . . ?
N3 C2 S1 125.0(6) . . ?
N2 C2 S1 108.9(5) . . ?
C1 C3 C4 114.9(6) . . ?
C1 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
O1 C4 C5 110.6(7) . . ?
O1 C4 C3 109.0(6) . . ?
C5 C4 C3 111.5(7) . . ?
O1 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4A 108.5 . . ?
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 . . ?
C11 C6 C7 120.3(7) . . ?
C11 C6 N3 120.2(6) . . ?
C7 C6 N3 119.5(7) . . ?
C6 C11 C10 119.5(7) . . ?
C6 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C9 C10 C11 120.2(8) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C9 C8 118.8(8) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
C7 C8 C9 120.8(8) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C8 C7 C6 120.4(8) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
O3 C12 O2 129.2(6) . . ?
O3 C12 C12 119.2(8) . 3_676 ?
O2 C12 C12 111.6(8) . 3_676 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 N1 C1 2.1(4) . . . . ?
S1 N1 C1 N2 -2.6(6) . . . . ?
S1 N1 C1 C3 -179.9(5) . . . . ?
C2 N2 C1 N1 1.7(8) . . . . ?
C2 N2 C1 C3 179.1(5) . . . . ?
C6 N3 C2 N2 177.7(6) . . . . ?
C6 N3 C2 S1 0.7(9) . . . . ?
C1 N2 C2 N3 -177.3(6) . . . . ?
C1 N2 C2 S1 0.1(6) . . . . ?
N1 S1 C2 N3 176.1(5) . . . . ?
N1 S1 C2 N2 -1.3(5) . . . . ?
N1 C1 C3 C4 112.2(7) . . . . ?
N2 C1 C3 C4 -65.1(8) . . . . ?
C1 C3 C4 O1 -55.5(8) . . . . ?
C1 C3 C4 C5 -178.0(7) . . . . ?
C2 N3 C6 C11 59.2(9) . . . . ?
C2 N3 C6 C7 -120.8(7) . . . . ?
C7 C6 C11 C10 1.0(11) . . . . ?
N3 C6 C11 C10 -179.0(7) . . . . ?
C6 C11 C10 C9 0.1(12) . . . . ?
C11 C10 C9 C8 -1.6(12) . . . . ?
C10 C9 C8 C7 2.0(13) . . . . ?
C9 C8 C7 C6 -0.9(12) . . . . ?
C11 C6 C7 C8 -0.7(11) . . . . ?
N3 C6 C7 C8 179.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.87 1.92 2.787(8) 170.9 1_545 yes
O2 H2 N2 0.85 1.74 2.587(6) 179.3 . yes
N3 H3C O3 0.88 1.93 2.778(7) 162.3 . yes
C5 H5A O1 0.98 2.63 3.361(12) 131.7 1_565 yes
C11 H11A N1 0.95 2.63 3.582(9) 175.1 2_656 yes
C7 H7A O1 0.95 2.66 3.503(9) 148.5 3_656 yes



# END of CIF
