# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_shx97
_database_code_depnum_ccdc_archive 'CCDC 2157226'
loop_
_audit_author_name
_audit_author_address
wanghuifang
;Ningbo Universiyy
China
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N3 O4 S'
_chemical_formula_weight         279.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.3377(15)
_cell_length_b                   7.9190(16)
_cell_length_c                   11.426(2)
_cell_angle_alpha                96.73(3)
_cell_angle_beta                 99.02(3)
_cell_angle_gamma                109.40(3)
_cell_volume                     608.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4824
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.010
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_full        25.021
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2144
_reflns_number_gt                1453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0847P)²+0.9475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2144
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.2260
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01952(18) 0.58151(16) 0.31824(11) 0.0478(4) Uani 1 1 d . . . . .
N1 N 0.1285(6) 0.7507(5) 0.4335(3) 0.0455(10) Uani 1 1 d . . . . .
H1B H 0.070805 0.827770 0.445107 0.055 Uiso 1 1 calc R U . . .
N2 N 0.4283(6) 0.7092(5) 0.4729(4) 0.0492(10) Uani 1 1 d . . . . .
N3 N 0.2223(6) 0.9577(5) 0.6791(4) 0.0447(10) Uani 1 1 d . . . . .
O1 O 0.0527(5) 0.4212(4) 0.3484(3) 0.0576(10) Uani 1 1 d . . . . .
O2 O -0.1778(5) 0.5805(5) 0.2899(3) 0.0581(10) Uani 1 1 d . . . . .
O3 O 0.0978(6) 0.9880(5) 0.6078(3) 0.0593(10) Uani 1 1 d . . . . .
O4 O 0.2389(6) 0.9901(5) 0.7883(3) 0.0646(11) Uani 1 1 d . . . . .
C1 C 0.0556(8) 0.7293(7) 0.1169(5) 0.0616(15) Uani 1 1 d . . . . .
H1A H -0.054792 0.757809 0.127057 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1414(10) 0.7719(9) 0.0200(5) 0.0770(19) Uani 1 1 d . . . . .
H2A H 0.087429 0.827040 -0.036499 0.092 Uiso 1 1 calc R U . . .
C3 C 0.3062(12) 0.7329(9) 0.0073(6) 0.087(2) Uani 1 1 d . . . . .
H3A H 0.363683 0.762043 -0.058151 0.104 Uiso 1 1 calc R U . . .
C4 C 0.3878(10) 0.6515(9) 0.0897(6) 0.0764(18) Uani 1 1 d . . . . .
H4A H 0.501073 0.627581 0.080384 0.092 Uiso 1 1 calc R U . . .
C5 C 0.3026(8) 0.6048(7) 0.1863(5) 0.0595(14) Uani 1 1 d . . . . .
H5A H 0.356695 0.548388 0.241747 0.071 Uiso 1 1 calc R U . . .
C6 C 0.1351(8) 0.6435(7) 0.1993(4) 0.0509(12) Uani 1 1 d . . . . .
C7 C 0.3049(7) 0.7818(6) 0.5143(4) 0.0427(11) Uani 1 1 d . . . . .
C8 C 0.5985(7) 0.7294(7) 0.5472(5) 0.0561(14) Uani 1 1 d . . . . .
H8A H 0.683987 0.678827 0.518162 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6520(8) 0.8216(7) 0.6644(5) 0.0593(14) Uani 1 1 d . . . . .
H9A H 0.770963 0.833409 0.713437 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5252(7) 0.8956(7) 0.7071(5) 0.0508(12) Uani 1 1 d . . . . .
H10A H 0.556568 0.957867 0.786031 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3518(6) 0.8765(6) 0.6320(4) 0.0395(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.430(3) . ?
S1 O1 1.439(3) . ?
S1 N1 1.647(4) . ?
S1 C6 1.746(6) . ?
N1 C7 1.396(6) . ?
N1 H1B 0.8600 . ?
N2 C7 1.339(6) . ?
N2 C8 1.345(6) . ?
N3 O4 1.222(5) . ?
N3 O3 1.230(5) . ?
N3 C11 1.447(6) . ?
C1 C2 1.379(8) . ?
C1 C6 1.389(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.368(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(7) . ?
C5 H5A 0.9300 . ?
C7 C11 1.391(6) . ?
C8 C9 1.377(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.372(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.371(6) . ?
C10 H10A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.7(2) . . ?
O2 S1 N1 103.7(2) . . ?
O1 S1 N1 109.1(2) . . ?
O2 S1 C6 108.7(2) . . ?
O1 S1 C6 108.1(2) . . ?
N1 S1 C6 106.8(2) . . ?
C7 N1 S1 126.7(3) . . ?
C7 N1 H1B 116.7 . . ?
S1 N1 H1B 116.7 . . ?
C7 N2 C8 118.7(5) . . ?
O4 N3 O3 122.8(4) . . ?
O4 N3 C11 118.4(4) . . ?
O3 N3 C11 118.8(4) . . ?
C2 C1 C6 119.6(6) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C3 C2 C1 119.8(6) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 120.3(7) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 119.0(6) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 S1 120.3(4) . . ?
C1 C6 S1 119.3(4) . . ?
N2 C7 C11 120.6(4) . . ?
N2 C7 N1 115.6(4) . . ?
C11 C7 N1 123.7(4) . . ?
N2 C8 C9 123.0(5) . . ?
N2 C8 H8A 118.5 . . ?
C9 C8 H8A 118.5 . . ?
C10 C9 C8 118.3(5) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C11 C10 C9 119.2(5) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C7 120.1(5) . . ?
C10 C11 N3 117.9(4) . . ?
C7 C11 N3 122.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 162.7(4) . . . . ?
O1 S1 N1 C7 34.1(5) . . . . ?
C6 S1 N1 C7 -82.6(4) . . . . ?
C6 C1 C2 C3 -1.4(9) . . . . ?
C1 C2 C3 C4 0.1(10) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
C4 C5 C6 C1 -0.6(8) . . . . ?
C4 C5 C6 S1 178.4(4) . . . . ?
C2 C1 C6 C5 1.6(8) . . . . ?
C2 C1 C6 S1 -177.4(4) . . . . ?
O2 S1 C6 C5 -161.1(4) . . . . ?
O1 S1 C6 C5 -29.7(5) . . . . ?
N1 S1 C6 C5 87.6(4) . . . . ?
O2 S1 C6 C1 17.9(5) . . . . ?
O1 S1 C6 C1 149.4(4) . . . . ?
N1 S1 C6 C1 -93.4(4) . . . . ?
C8 N2 C7 C11 0.1(7) . . . . ?
C8 N2 C7 N1 -178.1(4) . . . . ?
S1 N1 C7 N2 24.3(6) . . . . ?
S1 N1 C7 C11 -153.8(4) . . . . ?
C7 N2 C8 C9 0.0(7) . . . . ?
N2 C8 C9 C10 0.2(8) . . . . ?
C8 C9 C10 C11 -0.5(7) . . . . ?
C9 C10 C11 C7 0.6(7) . . . . ?
C9 C10 C11 N3 -179.3(4) . . . . ?
N2 C7 C11 C10 -0.4(7) . . . . ?
N1 C7 C11 C10 177.6(4) . . . . ?
N2 C7 C11 N3 179.5(4) . . . . ?
N1 C7 C11 N3 -2.5(7) . . . . ?
O4 N3 C11 C10 -21.6(6) . . . . ?
O3 N3 C11 C10 159.8(4) . . . . ?
O4 N3 C11 C7 158.5(4) . . . . ?
O3 N3 C11 C7 -20.1(6) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_shx97_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2158131'
loop_
_audit_author_name
_audit_author_address
'Junfei Luo'
;Ningbo University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N3 O4 S'
_chemical_formula_weight         293.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0582(16)
_cell_length_b                   8.8182(18)
_cell_length_c                   18.340(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.59(3)
_cell_angle_gamma                90
_cell_volume                     1297.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9935
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.212
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.022
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2288
_reflns_number_gt                1604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0118P)²+1.6611P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2288
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.96264(11) 0.41934(9) 0.11707(5) 0.0402(3) Uani 1 1 d . . . . .
O1 O 0.8528(3) 0.4233(3) 0.17306(13) 0.0493(6) Uani 1 1 d . . . . .
O2 O 0.9908(3) 0.5567(2) 0.07780(13) 0.0482(6) Uani 1 1 d . . . . .
O3 O 0.5695(5) -0.3413(3) 0.04803(19) 0.0845(11) Uani 1 1 d . . . . .
O4 O 0.6179(4) -0.2987(3) 0.16404(19) 0.0778(10) Uani 1 1 d . . . . .
N1 N 0.8920(4) 0.3016(3) 0.05132(15) 0.0447(7) Uani 1 1 d . . . . .
H1B H 0.892351 0.333390 0.007002 0.054 Uiso 1 1 calc R U . . .
N2 N 0.8293(4) 0.1091(3) 0.13029(16) 0.0485(8) Uani 1 1 d . . . . .
N3 N 0.6246(4) -0.2635(3) 0.0996(2) 0.0569(9) Uani 1 1 d . . . . .
C1 C 1.1651(5) 0.2554(4) 0.21427(19) 0.0486(9) Uani 1 1 d . . . . .
H1A H 1.069344 0.229052 0.235826 0.058 Uiso 1 1 calc R U . . .
C2 C 1.3200(6) 0.2038(5) 0.2431(2) 0.0636(11) Uani 1 1 d . . . . .
H2A H 1.328601 0.142104 0.284467 0.076 Uiso 1 1 calc R U . . .
C3 C 1.4613(5) 0.2432(5) 0.2110(3) 0.0641(11) Uani 1 1 d . . . . .
H3A H 1.564623 0.207404 0.230683 0.077 Uiso 1 1 calc R U . . .
C4 C 1.4511(5) 0.3346(5) 0.1503(3) 0.0619(11) Uani 1 1 d . . . . .
H4A H 1.547430 0.361194 0.129180 0.074 Uiso 1 1 calc R U . . .
C5 C 1.2977(5) 0.3875(4) 0.1203(2) 0.0488(9) Uani 1 1 d . . . . .
H5A H 1.289960 0.449198 0.078995 0.059 Uiso 1 1 calc R U . . .
C6 C 1.1553(4) 0.3470(4) 0.15274(18) 0.0380(8) Uani 1 1 d . . . . .
C7 C 0.8315(4) 0.1545(4) 0.06094(18) 0.0398(8) Uani 1 1 d . . . . .
C8 C 0.7785(4) 0.0669(4) -0.0012(2) 0.0432(8) Uani 1 1 d . . . . .
C9 C 0.7914(5) 0.1223(4) -0.0778(2) 0.0568(10) Uani 1 1 d . . . . .
H9A H 0.747994 0.046686 -0.112108 0.085 Uiso 1 1 calc R U . . .
H9B H 0.906200 0.141640 -0.084448 0.085 Uiso 1 1 calc R U . . .
H9C H 0.728363 0.214237 -0.085696 0.085 Uiso 1 1 calc R U . . .
C10 C 0.7106(5) -0.0724(4) 0.0130(2) 0.0473(9) Uani 1 1 d . . . . .
H10A H 0.670384 -0.135260 -0.025494 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7026(5) -0.1183(4) 0.0849(2) 0.0473(9) Uani 1 1 d . . . . .
C12 C 0.7628(5) -0.0270(4) 0.1416(2) 0.0509(9) Uani 1 1 d . . . . .
H12A H 0.757472 -0.060389 0.189423 0.061 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.420(2) . ?
S1 O2 1.438(2) . ?
S1 N1 1.650(3) . ?
S1 C6 1.746(4) . ?
O3 N3 1.217(4) . ?
O4 N3 1.228(4) . ?
N1 C7 1.403(4) . ?
N1 H1B 0.8600 . ?
N2 C7 1.335(4) . ?
N2 C12 1.339(4) . ?
N3 C11 1.463(4) . ?
C1 C2 1.384(6) . ?
C1 C6 1.384(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.377(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.409(5) . ?
C8 C10 1.380(5) . ?
C8 C9 1.499(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.387(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.367(5) . ?
C12 H12A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.76(15) . . ?
O1 S1 N1 110.44(15) . . ?
O2 S1 N1 102.94(14) . . ?
O1 S1 C6 109.42(16) . . ?
O2 S1 C6 108.48(15) . . ?
N1 S1 C6 105.96(15) . . ?
C7 N1 S1 126.1(2) . . ?
C7 N1 H1B 116.9 . . ?
S1 N1 H1B 116.9 . . ?
C7 N2 C12 117.3(3) . . ?
O3 N3 O4 123.9(3) . . ?
O3 N3 C11 118.7(3) . . ?
O4 N3 C11 117.3(4) . . ?
C2 C1 C6 118.8(4) . . ?
C2 C1 H1A 120.6 . . ?
C6 C1 H1A 120.6 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C1 C6 C5 121.0(3) . . ?
C1 C6 S1 119.8(3) . . ?
C5 C6 S1 119.2(3) . . ?
N2 C7 N1 115.7(3) . . ?
N2 C7 C8 125.1(3) . . ?
N1 C7 C8 119.2(3) . . ?
C10 C8 C7 115.5(3) . . ?
C10 C8 C9 122.2(3) . . ?
C7 C8 C9 122.4(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 119.7(3) . . ?
C8 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 N3 120.1(3) . . ?
C10 C11 N3 119.4(4) . . ?
N2 C12 C11 121.8(3) . . ?
N2 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C7 -46.4(3) . . . . ?
O2 S1 N1 C7 -174.1(3) . . . . ?
C6 S1 N1 C7 72.1(3) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C6 S1 -177.7(3) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C4 C5 C6 S1 177.6(3) . . . . ?
O1 S1 C6 C1 23.6(3) . . . . ?
O2 S1 C6 C1 154.5(3) . . . . ?
N1 S1 C6 C1 -95.5(3) . . . . ?
O1 S1 C6 C5 -154.0(3) . . . . ?
O2 S1 C6 C5 -23.0(3) . . . . ?
N1 S1 C6 C5 86.9(3) . . . . ?
C12 N2 C7 N1 176.0(3) . . . . ?
C12 N2 C7 C8 -4.0(5) . . . . ?
S1 N1 C7 N2 1.3(5) . . . . ?
S1 N1 C7 C8 -178.8(3) . . . . ?
N2 C7 C8 C10 4.1(5) . . . . ?
N1 C7 C8 C10 -175.9(3) . . . . ?
N2 C7 C8 C9 -177.2(3) . . . . ?
N1 C7 C8 C9 2.8(5) . . . . ?
C7 C8 C10 C11 -1.6(5) . . . . ?
C9 C8 C10 C11 179.6(4) . . . . ?
C8 C10 C11 C12 -0.6(6) . . . . ?
C8 C10 C11 N3 177.6(3) . . . . ?
O3 N3 C11 C12 178.7(4) . . . . ?
O4 N3 C11 C12 -0.7(5) . . . . ?
O3 N3 C11 C10 0.5(5) . . . . ?
O4 N3 C11 C10 -178.9(4) . . . . ?
C7 N2 C12 C11 1.4(5) . . . . ?
C10 C11 C12 N2 0.7(6) . . . . ?
N3 C11 C12 N2 -177.4(3) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_shx97_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2158133'
loop_
_audit_author_name
_audit_author_address
'Junfei Luo'
;Ningbo University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N3 O4 S'
_chemical_formula_weight         293.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9073(14)
_cell_length_b                   17.475(4)
_cell_length_c                   11.142(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.86(3)
_cell_angle_gamma                90
_cell_volume                     1335.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10056
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2360
_reflns_number_gt                1771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.1342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2360
_refine_ls_number_parameters     181
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31024(9) 0.53403(4) 0.25112(6) 0.0556(3) Uani 1 1 d . . . . .
O1 O 0.2216(3) 0.60808(10) 0.26528(18) 0.0725(6) Uani 1 1 d . . . . .
O2 O 0.5174(3) 0.52746(11) 0.26890(19) 0.0747(6) Uani 1 1 d . . . . .
O3 O 0.5611(4) 0.22435(14) -0.1597(3) 0.1160(9) Uani 1 1 d . U . . .
O4 O 0.2814(5) 0.24854(14) -0.2559(3) 0.1193(10) Uani 1 1 d . U . . .
N1 N 0.2302(3) 0.50815(12) 0.11259(19) 0.0549(6) Uani 1 1 d . . . . .
H1B H 0.144934 0.537502 0.073345 0.066 Uiso 1 1 calc R U . . .
N2 N 0.1573(3) 0.42309(12) -0.0434(2) 0.0544(6) Uani 1 1 d . . . . .
N3 N 0.4101(5) 0.26100(15) -0.1752(3) 0.0812(8) Uani 1 1 d . U . . .
C1 C 0.3322(4) 0.42553(15) 0.4294(2) 0.0568(7) Uani 1 1 d . . . . .
H1A H 0.466463 0.432665 0.436037 0.068 Uiso 1 1 calc R U . . .
C2 C 0.2520(5) 0.37380(16) 0.5051(3) 0.0683(8) Uani 1 1 d . . . . .
H2A H 0.333151 0.346918 0.563045 0.082 Uiso 1 1 calc R U . . .
C3 C 0.0566(5) 0.36254(17) 0.4947(3) 0.0753(9) Uani 1 1 d . . . . .
H3A H 0.004072 0.327577 0.544770 0.090 Uiso 1 1 calc R U . . .
C4 C -0.0645(4) 0.40294(19) 0.4097(3) 0.0837(10) Uani 1 1 d . . . . .
H4A H -0.198476 0.394932 0.402941 0.100 Uiso 1 1 calc R U . . .
C5 C 0.0112(4) 0.45535(16) 0.3341(3) 0.0692(8) Uani 1 1 d . . . . .
H5A H -0.070874 0.482828 0.277463 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2113(3) 0.46600(13) 0.3447(2) 0.0479(6) Uani 1 1 d . . . . .
C7 C 0.2865(4) 0.44278(14) 0.0510(2) 0.0502(6) Uani 1 1 d . . . . .
C8 C 0.4590(4) 0.40263(15) 0.0811(3) 0.0615(7) Uani 1 1 d . . . . .
H8A H 0.542457 0.417052 0.149049 0.074 Uiso 1 1 calc R U . . .
C9 C 0.5098(4) 0.34098(15) 0.0112(3) 0.0652(8) Uani 1 1 d . . . . .
C10 C 0.7024(4) 0.3003(2) 0.0490(4) 0.1043(13) Uani 1 1 d . . . . .
H10B H 0.767450 0.324131 0.120312 0.156 Uiso 1 1 calc R U . . .
H10C H 0.677887 0.247511 0.065546 0.156 Uiso 1 1 calc R U . . .
H10D H 0.783312 0.303652 -0.015154 0.156 Uiso 1 1 calc R U . . .
C11 C 0.3760(4) 0.32296(14) -0.0871(3) 0.0641(8) Uani 1 1 d . . . . .
C12 C 0.2048(4) 0.36378(14) -0.1114(3) 0.0630(7) Uani 1 1 d . . . . .
H12A H 0.117915 0.349656 -0.178012 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4255(19) . ?
S1 O1 1.4483(19) . ?
S1 N1 1.640(2) . ?
S1 C6 1.771(2) . ?
O3 N3 1.219(3) . ?
O4 N3 1.206(3) . ?
N1 C7 1.411(3) . ?
N1 H1B 0.8600 . ?
N2 C7 1.341(3) . ?
N2 C12 1.347(3) . ?
N3 C11 1.498(4) . ?
C1 C6 1.378(3) . ?
C1 C2 1.395(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.355(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9300 . ?
C7 C8 1.389(3) . ?
C8 C9 1.398(4) . ?
C8 H8A 0.9300 . ?
C9 C11 1.383(4) . ?
C9 C10 1.523(4) . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 H10D 0.9600 . ?
C11 C12 1.380(4) . ?
C12 H12A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.16(12) . . ?
O2 S1 N1 109.18(12) . . ?
O1 S1 N1 104.45(11) . . ?
O2 S1 C6 108.39(12) . . ?
O1 S1 C6 109.74(12) . . ?
N1 S1 C6 104.98(11) . . ?
C7 N1 S1 126.83(18) . . ?
C7 N1 H1B 116.6 . . ?
S1 N1 H1B 116.6 . . ?
C7 N2 C12 117.0(2) . . ?
O4 N3 O3 123.5(3) . . ?
O4 N3 C11 117.4(3) . . ?
O3 N3 C11 119.1(3) . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 S1 120.19(18) . . ?
C5 C6 S1 119.4(2) . . ?
N2 C7 C8 122.1(2) . . ?
N2 C7 N1 113.1(2) . . ?
C8 C7 N1 124.8(3) . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 H8A 119.3 . . ?
C9 C8 H8A 119.3 . . ?
C11 C9 C8 115.4(2) . . ?
C11 C9 C10 126.3(3) . . ?
C8 C9 C10 118.4(3) . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10 H10D 109.5 . . ?
H10B C10 H10D 109.5 . . ?
H10C C10 H10D 109.5 . . ?
C12 C11 C9 120.9(2) . . ?
C12 C11 N3 116.3(3) . . ?
C9 C11 N3 122.8(3) . . ?
N2 C12 C11 123.2(3) . . ?
N2 C12 H12A 118.4 . . ?
C11 C12 H12A 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 46.0(2) . . . . ?
O1 S1 N1 C7 174.5(2) . . . . ?
C6 S1 N1 C7 -70.0(2) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 S1 178.0(2) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 S1 -178.7(2) . . . . ?
O2 S1 C6 C1 8.6(2) . . . . ?
O1 S1 C6 C1 -123.0(2) . . . . ?
N1 S1 C6 C1 125.2(2) . . . . ?
O2 S1 C6 C5 -173.1(2) . . . . ?
O1 S1 C6 C5 55.3(2) . . . . ?
N1 S1 C6 C5 -56.5(2) . . . . ?
C12 N2 C7 C8 -2.3(4) . . . . ?
C12 N2 C7 N1 176.4(2) . . . . ?
S1 N1 C7 N2 160.05(18) . . . . ?
S1 N1 C7 C8 -21.3(4) . . . . ?
N2 C7 C8 C9 2.3(4) . . . . ?
N1 C7 C8 C9 -176.2(2) . . . . ?
C7 C8 C9 C11 -0.8(4) . . . . ?
C7 C8 C9 C10 179.3(2) . . . . ?
C8 C9 C11 C12 -0.6(4) . . . . ?
C10 C9 C11 C12 179.3(3) . . . . ?
C8 C9 C11 N3 177.1(2) . . . . ?
C10 C9 C11 N3 -3.0(4) . . . . ?
O4 N3 C11 C12 -4.2(4) . . . . ?
O3 N3 C11 C12 178.3(3) . . . . ?
O4 N3 C11 C9 177.9(3) . . . . ?
O3 N3 C11 C9 0.5(4) . . . . ?
C7 N2 C12 C11 0.9(4) . . . . ?
C9 C11 C12 N2 0.6(4) . . . . ?
N3 C11 C12 N2 -177.3(2) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.044

