# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20240714_wsq_1527_0m
_database_code_depnum_ccdc_archive 'CCDC 2386020'
loop_
_audit_author_name
_audit_author_address
'Shaoqing Wang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 N4 O2'
_chemical_formula_sum            'C2 H2 N4 O2'
_chemical_formula_weight         114.08
_chemical_absolute_configuration AD
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   6.8684(2)
_cell_length_b                   6.8684(2)
_cell_length_c                   19.1626(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     903.99(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5493
_cell_measurement_temperature    240.00
_cell_measurement_theta_max      57.084
_cell_measurement_theta_min      5.604
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1277 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.7606.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.141
_diffrn_reflns_theta_min         5.954
_diffrn_ambient_temperature      240.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.539
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                898
_reflns_number_total             931
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.21(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.0915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.32695(18) 0.59884(17) 0.66596(6) 0.0450(3) Uani 1 1 d . . . . .
O3 O 0.5461(2) 0.4760(2) 0.59859(7) 0.0710(5) Uani 1 1 d . . . . .
N3 N 0.4377(2) 0.4692(2) 0.64866(7) 0.0395(3) Uani 1 1 d . . . . .
N4 N 0.3248(2) 0.27301(19) 0.74672(7) 0.0364(4) Uani 1 1 d . . . . .
N5 N 0.5201(2) 0.0287(2) 0.73002(7) 0.0424(4) Uani 1 1 d . . . . .
H5 H 0.576130 -0.083537 0.736407 0.051 Uiso 1 1 calc R U . . .
N6 N 0.5649(2) 0.1542(2) 0.67835(7) 0.0448(4) Uani 1 1 d . . . . .
C9 C 0.4426(2) 0.2953(2) 0.69155(8) 0.0329(3) Uani 1 1 d . . . . .
C10 C 0.3794(3) 0.0995(3) 0.76963(8) 0.0396(4) Uani 1 1 d . . . . .
H10 H 0.325655 0.035767 0.808533 0.047 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
O2 N3 1.2172(17) . ?
O3 N3 1.2151(18) . ?
N3 C9 1.4502(19) . ?
N4 C9 1.340(2) . ?
N4 C10 1.324(2) . ?
N5 H5 0.8700 . ?
N5 N6 1.3488(19) . ?
N5 C10 1.322(2) . ?
N6 C9 1.307(2) . ?
C10 H10 0.9400 . ?

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 N3 C9 117.55(13) . . ?
O3 N3 O2 124.74(14) . . ?
O3 N3 C9 117.70(13) . . ?
C10 N4 C9 101.17(13) . . ?
N6 N5 H5 124.7 . . ?
C10 N5 H5 124.7 . . ?
C10 N5 N6 110.66(13) . . ?
C9 N6 N5 100.70(13) . . ?
N4 C9 N3 121.83(13) . . ?
N6 C9 N3 121.05(14) . . ?
N6 C9 N4 117.12(14) . . ?
N4 C10 H10 124.8 . . ?
N5 C10 N4 110.36(13) . . ?
N5 C10 H10 124.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C9 N4 2.6(2) . . . . ?
O2 N3 C9 N6 -176.48(16) . . . . ?
O3 N3 C9 N4 -178.27(16) . . . . ?
O3 N3 C9 N6 2.7(2) . . . . ?
N5 N6 C9 N3 179.46(14) . . . . ?
N5 N6 C9 N4 0.3(2) . . . . ?
N6 N5 C10 N4 -0.1(2) . . . . ?
C9 N4 C10 N5 0.31(18) . . . . ?
C10 N4 C9 N3 -179.53(15) . . . . ?
C10 N4 C9 N6 -0.4(2) . . . . ?
C10 N5 N6 C9 -0.11(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20240714_wsq_1531_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2386022'
loop_
_audit_author_name
_audit_author_address
'Shaoqing Wang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 N12 O4'
_chemical_formula_sum            'C4 H4 N12 O4'
_chemical_formula_weight         284.19
_chemical_absolute_configuration AD
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9463(4)
_cell_length_b                   6.6224(5)
_cell_length_c                   24.2123(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     953.45(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5679
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      56.79
_cell_measurement_theta_min      6.03
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.978
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1564 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.7885.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9578
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.049
_diffrn_reflns_theta_min         6.027
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1996566
_diffrn_source_voltage           69.81
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1588
_reflns_number_total             1940
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0988P)²+0.7837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1689
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 O3_$1-O2
 2.9 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 N8(H8), N10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0464(7) 0.6177(6) 0.11181(16) 0.0473(10) Uani 1 1 d . . . . .
O2 O -0.2222(6) 0.4967(6) 0.16380(14) 0.0456(10) Uani 1 1 d D . . . .
O3 O 1.2188(7) 0.7475(6) 0.43438(15) 0.0515(11) Uani 1 1 d . . . . .
O4 O 1.1364(7) 0.5792(7) 0.50630(16) 0.0503(11) Uani 1 1 d . . . . .
N1 N 1.0965(7) 0.6398(7) 0.45965(18) 0.0385(10) Uani 1 1 d . . . . .
N2 N 0.8205(7) 0.6419(6) 0.38422(18) 0.0336(10) Uani 1 1 d . . . . .
N12 N 0.7649(7) 0.4363(7) 0.45806(17) 0.0361(10) Uani 1 1 d . . . . .
N4 N 0.5954(7) 0.4157(6) 0.42138(17) 0.0341(9) Uani 1 1 d . . . . .
N5 N 0.4134(9) 0.2904(8) 0.4317(2) 0.0445(12) Uani 1 1 d . . . . .
N6 N -0.0304(7) 0.5523(7) 0.15493(18) 0.0360(10) Uani 1 1 d . . . . .
N7 N 0.3167(7) 0.6480(7) 0.20142(18) 0.0339(10) Uani 1 1 d . . . . .
N8 N 0.0461(7) 0.4615(7) 0.24876(18) 0.0334(10) Uani 1 1 d . . . . .
H8 H -0.078476 0.394433 0.255712 0.040 Uiso 1 1 calc R U . . .
N9 N 0.4899(7) 0.5531(6) 0.33265(18) 0.0315(9) Uani 1 1 d . . . . .
N10 N 0.2897(7) 0.4621(7) 0.33191(18) 0.0347(10) Uani 1 1 d . . . . .
H10 H 0.220466 0.393598 0.358011 0.042 Uiso 1 1 calc R U . . .
N11 N 0.5594(7) 0.6491(6) 0.28623(17) 0.0336(10) Uani 1 1 d . . . . .
C1 C 0.1173(8) 0.5530(7) 0.20298(19) 0.0308(10) Uani 1 1 d . . . . .
C2 C 0.3838(8) 0.6129(7) 0.25329(19) 0.0285(10) Uani 1 1 d . . . . .
N3 N 0.2247(7) 0.5036(7) 0.28110(19) 0.0366(10) Uani 1 1 d . . . . .
C4 C 0.6326(8) 0.5395(7) 0.3785(2) 0.0325(11) Uani 1 1 d . . . . .
C5 C 0.8905(9) 0.5722(8) 0.4331(2) 0.0355(11) Uani 1 1 d . . . . .
H5A H 0.426(12) 0.212(10) 0.410(3) 0.04(2) Uiso 1 1 d . . . . .
H5B H 0.409(12) 0.218(10) 0.468(3) 0.059(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N6 1.219(5) . ?
O2 N6 1.217(6) . ?
O3 N1 1.188(5) . ?
O4 N1 1.222(6) . ?
N1 C5 1.454(7) . ?
N2 C4 1.315(6) . ?
N2 C5 1.336(7) . ?
N12 N4 1.351(6) . ?
N12 C5 1.317(7) . ?
N4 N5 1.386(6) . ?
N4 C4 1.340(6) . ?
N5 H5A 0.74(7) . ?
N5 H5B 1.00(7) . ?
N6 C1 1.458(6) . ?
N7 C1 1.343(6) . ?
N7 C2 1.338(6) . ?
N8 H8 0.8800 . ?
N8 C1 1.333(6) . ?
N8 N3 1.349(6) . ?
N9 N10 1.335(6) . ?
N9 N11 1.356(6) . ?
N9 C4 1.401(6) . ?
N10 H10 0.8800 . ?
N10 N3 1.318(6) . ?
N11 C2 1.336(6) . ?
C2 N3 1.368(6) . ?

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
O3 N1 O4 123.7(5) . . ?
O3 N1 C5 118.2(4) . . ?
O4 N1 C5 118.1(4) . . ?
C4 N2 C5 100.3(4) . . ?
C5 N12 N4 101.0(4) . . ?
N12 N4 N5 121.7(4) . . ?
C4 N4 N12 108.9(4) . . ?
C4 N4 N5 129.4(4) . . ?
N4 N5 H5A 102(6) . . ?
N4 N5 H5B 118(4) . . ?
H5A N5 H5B 107(6) . . ?
O1 N6 C1 117.2(4) . . ?
O2 N6 O1 127.5(5) . . ?
O2 N6 C1 115.1(4) . . ?
C2 N7 C1 99.0(4) . . ?
C1 N8 H8 131.0 . . ?
C1 N8 N3 98.0(4) . . ?
N3 N8 H8 131.0 . . ?
N10 N9 N11 118.2(4) . . ?
N10 N9 C4 121.4(4) . . ?
N11 N9 C4 120.2(4) . . ?
N9 N10 H10 129.8 . . ?
N3 N10 N9 100.4(4) . . ?
N3 N10 H10 129.8 . . ?
C2 N11 N9 99.9(4) . . ?
N7 C1 N6 120.7(4) . . ?
N8 C1 N6 118.1(4) . . ?
N8 C1 N7 121.1(4) . . ?
N7 C2 N3 110.3(4) . . ?
N11 C2 N7 139.7(5) . . ?
N11 C2 N3 110.0(4) . . ?
N8 N3 C2 111.6(4) . . ?
N10 N3 N8 136.8(4) . . ?
N10 N3 C2 111.5(4) . . ?
N2 C4 N4 112.0(4) . . ?
N2 C4 N9 124.4(4) . . ?
N4 C4 N9 123.6(4) . . ?
N2 C5 N1 123.2(5) . . ?
N12 C5 N1 119.0(4) . . ?
N12 C5 N2 117.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N6 C1 N7 9.3(7) . . . . ?
O1 N6 C1 N8 -172.4(4) . . . . ?
O2 N6 C1 N7 -166.5(4) . . . . ?
O2 N6 C1 N8 11.7(6) . . . . ?
O3 N1 C5 N2 -7.4(7) . . . . ?
O3 N1 C5 N12 172.9(5) . . . . ?
O4 N1 C5 N2 174.2(5) . . . . ?
O4 N1 C5 N12 -5.6(7) . . . . ?
N12 N4 C4 N2 0.6(6) . . . . ?
N12 N4 C4 N9 179.0(4) . . . . ?
N4 N12 C5 N1 179.8(4) . . . . ?
N4 N12 C5 N2 0.1(6) . . . . ?
N5 N4 C4 N2 177.2(5) . . . . ?
N5 N4 C4 N9 -4.4(8) . . . . ?
N7 C2 N3 N8 0.1(6) . . . . ?
N7 C2 N3 N10 178.2(4) . . . . ?
N9 N10 N3 N8 178.1(5) . . . . ?
N9 N10 N3 C2 0.7(5) . . . . ?
N9 N11 C2 N7 -178.2(6) . . . . ?
N9 N11 C2 N3 0.6(5) . . . . ?
N10 N9 N11 C2 -0.2(5) . . . . ?
N10 N9 C4 N2 -172.7(4) . . . . ?
N10 N9 C4 N4 9.1(7) . . . . ?
N11 N9 N10 N3 -0.3(5) . . . . ?
N11 N9 C4 N2 11.7(7) . . . . ?
N11 N9 C4 N4 -166.5(4) . . . . ?
N11 C2 N3 N8 -179.0(4) . . . . ?
N11 C2 N3 N10 -0.9(6) . . . . ?
C1 N7 C2 N11 178.7(6) . . . . ?
C1 N7 C2 N3 -0.1(5) . . . . ?
C1 N8 N3 N10 -177.5(6) . . . . ?
C1 N8 N3 C2 -0.1(5) . . . . ?
C2 N7 C1 N6 178.3(4) . . . . ?
C2 N7 C1 N8 0.1(6) . . . . ?
N3 N8 C1 N6 -178.3(4) . . . . ?
N3 N8 C1 N7 0.0(6) . . . . ?
C4 N2 C5 N1 -179.4(5) . . . . ?
C4 N2 C5 N12 0.3(6) . . . . ?
C4 N9 N10 N3 -176.1(4) . . . . ?
C4 N9 N11 C2 175.6(4) . . . . ?
C5 N2 C4 N4 -0.5(5) . . . . ?
C5 N2 C4 N9 -178.9(5) . . . . ?
C5 N12 N4 N5 -177.3(5) . . . . ?
C5 N12 N4 C4 -0.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_716wsq920_0m_4_tw_tw
_database_code_depnum_ccdc_archive 'CCDC 2386021'
loop_
_audit_author_name
_audit_author_address
'Shaoqing Wang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;
_audit_creation_date             2023-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C2 H6 O S), 2(C4 H4 N10 O4)'
_chemical_formula_sum            'C16 H32 N20 O12 S4'
_chemical_formula_weight         824.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.1210(9)
_cell_length_b                   12.4040(10)
_cell_length_c                   12.4946(9)
_cell_angle_alpha                86.939(2)
_cell_angle_beta                 86.578(3)
_cell_angle_gamma                88.148(3)
_cell_volume                     1717.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4374
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1224
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7040
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.476
_diffrn_reflns_theta_min         2.259
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4479
_reflns_number_total             7040
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    ?
_refine_diff_density_max         0.854
_refine_diff_density_min         -1.283
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         7040
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.1035
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2501
_refine_ls_wR_factor_ref         0.2779
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5(0.026) H15(0.028) H13(0.029) H9(0.028) H10(0.028) H2(0.026)
 H1(0.028) H7(0.029) H17(0.05) H20(0.05) H21(0.05) H18(0.046) H19(0.046)
 H22(0.046) H31A(0.05) H31B(0.05) H31C(0.05) H32A(0.062) H32B(0.062)
 H32C(0.062) H29(0.055) H31(0.055) H34(0.055) H30(0.056) H32(0.056) H33(0.056)
 H35(0.055) H37(0.055) H38(0.055) H36(0.056) H39(0.056) H40(0.056)
 Fixed X: H5(0.230218) H15(0.721802) H13(0.854476) H9(0.642122) H10(0.770171)
 H2(0.355509) H1(0.142628) H7(0.274573) H17(0.650402) H20(0.647118)
 H21(0.647363) H18(0.47068) H19(0.457729) H22(0.34196) H31A(1.147754)
 H31B(1.128872) H31C(1.080535) H32A(0.795165) H32B(0.845215) H32C(0.893552)
 H29(0.62833) H31(0.649364) H34(0.635315) H30(0.317555) H32(0.443235)
 H33(0.430337) H35(-0.129702) H37(-0.146871) H38(-0.131128) H36(0.182099)
 H39(0.053251) H40(0.072812)
 Fixed Y: H5(0.390636) H15(0.10492) H13(0.039912) H9(0.031777) H10(0.129004)
 H2(0.467609) H1(0.469577) H7(0.38113) H17(0.953317) H20(0.874759)
 H21(0.825335) H18(0.70745) H19(0.751773) H22(0.748903) H31A(0.139362)
 H31B(0.169211) H31C(0.250563) H32A(0.107477) H32B(0.227162) H32C(0.14581)
 H29(0.30006) H31(0.425056) H34(0.342108) H30(0.252641) H32(0.199928)
 H33(0.246402) H35(0.322252) H37(0.449355) H38(0.368629) H36(0.253825)
 H39(0.211185) H40(0.256089)
 Fixed Z: H5(0.197908) H15(0.694325) H13(0.440873) H9(0.563658) H10(0.311499)
 H2(-0.059881) H1(0.063374) H7(-0.182964) H17(0.128352) H20(0.031112)
 H21(0.152062) H18(0.125045) H19(0.003502) H22(0.085963) H31A(0.15418)
 H31B(0.030001) H31C(0.119136) H32A(0.062301) H32B(0.059764) H32C(-0.029371)
 H29(0.661919) H31(0.630385) H34(0.538432) H30(0.592241) H32(0.627684)
 H33(0.506817) H35(0.363331) H37(0.377709) H38(0.480502) H36(0.426036)
 H39(0.400072) H40(0.515295)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45849(12) 0.89331(10) 0.11535(10) 0.0246(3) Uani 1 1 d . . . . .
S3 S 0.45112(12) 0.38573(11) 0.61868(10) 0.0263(4) Uani 1 1 d . . . . .
S4 S 0.05161(12) 0.39661(11) 0.38994(10) 0.0274(4) Uani 1 1 d . . . . .
O1 O -0.0981(3) 0.3408(3) -0.3322(3) 0.0303(9) Uani 1 1 d . . . . .
O2 O 0.6058(3) 0.3552(3) 0.3519(3) 0.0272(8) Uani 1 1 d . . . . .
O3 O 0.3985(3) 0.1553(3) 0.1504(3) 0.0296(9) Uani 1 1 d . . . . .
O4 O 1.1881(3) 0.0954(3) 0.6977(3) 0.0271(8) Uani 1 1 d . . . . .
O5 O 0.4277(3) 0.8950(3) 0.2352(3) 0.0285(8) Uani 1 1 d . . . . .
O6 O 0.9187(3) 0.1503(3) 0.2486(3) 0.0345(10) Uani 1 1 d . . . . .
O7 O 0.4198(3) 0.3906(3) 0.7379(3) 0.0277(8) Uani 1 1 d . . . . .
O8 O 1.0942(3) 0.1169(3) 0.8538(3) 0.0346(10) Uani 1 1 d . . . . .
O9 O 0.3042(3) 0.1200(3) 0.3052(3) 0.0258(8) Uani 1 1 d . . . . .
O10 O 0.6969(3) 0.3872(3) 0.1942(3) 0.0272(8) Uani 1 1 d . . . . .
O11 O -0.1928(3) 0.3749(3) -0.1797(3) 0.0269(8) Uani 1 1 d . . . . .
O12 O 0.0810(3) 0.3996(3) 0.2695(3) 0.0314(9) Uani 1 1 d . . . . .
N1 N 1.0976(4) 0.1031(4) 0.7566(3) 0.0267(10) Uani 1 1 d . . . . .
N2 N 0.6070(4) 0.3778(3) 0.2542(3) 0.0240(10) Uani 1 1 d . . . . .
N3 N 0.9802(4) 0.0698(3) 0.6044(3) 0.0224(9) Uani 1 1 d . . . . .
N4 N 0.3902(4) 0.3737(3) 0.2644(3) 0.0240(10) Uani 1 1 d . . . . .
N5 N 0.3089(4) 0.3952(3) 0.1872(3) 0.0214(9) Uani 1 1 d . . . . .
H5 H 0.230218 0.390636 0.197908 0.026 Uiso 1 1 d R U . . .
N6 N 0.8805(4) 0.1133(4) 0.7613(3) 0.0258(10) Uani 1 1 d . . . . .
N7 N 0.8007(4) 0.0981(3) 0.6850(3) 0.0237(10) Uani 1 1 d . . . . .
H15 H 0.721802 0.104920 0.694325 0.028 Uiso 1 1 d R U . . .
N8 N 0.8106(4) 0.0521(3) 0.5002(3) 0.0241(10) Uani 1 1 d . . . . .
H13 H 0.854476 0.039912 0.440873 0.029 Uiso 1 1 d R U . . .
N9 N 0.6851(4) 0.0514(3) 0.5048(3) 0.0236(10) Uani 1 1 d . . . . .
H9 H 0.642122 0.031777 0.563658 0.028 Uiso 1 1 d R U . . .
N10 N 0.5153(4) 0.0822(3) 0.4002(3) 0.0209(9) Uani 1 1 d . . . . .
N11 N 0.6112(4) 0.1431(3) 0.2440(3) 0.0246(10) Uani 1 1 d . . . . .
N12 N 0.6919(4) 0.1205(3) 0.3204(3) 0.0230(10) Uani 1 1 d . . . . .
H10 H 0.770171 0.129004 0.311499 0.028 Uiso 1 1 d R U . . .
N13 N 0.3955(4) 0.1321(3) 0.2466(3) 0.0232(9) Uani 1 1 d . . . . .
N14 N 0.4856(4) 0.4215(3) 0.1033(3) 0.0223(9) Uani 1 1 d . . . . .
N15 N 0.3133(4) 0.4508(3) 0.0002(3) 0.0215(9) Uani 1 1 d . . . . .
H2 H 0.355509 0.467609 -0.059881 0.026 Uiso 1 1 d R U . . .
N16 N 0.1861(4) 0.4494(3) 0.0063(3) 0.0232(10) Uani 1 1 d . . . . .
H1 H 0.142628 0.469577 0.063374 0.028 Uiso 1 1 d R U . . .
N17 N 0.0160(4) 0.4115(3) -0.0909(3) 0.0239(10) Uani 1 1 d . . . . .
N18 N 0.1155(4) 0.3580(3) -0.2455(3) 0.0237(10) Uani 1 1 d . . . . .
N19 N 0.1956(4) 0.3843(3) -0.1724(3) 0.0238(10) Uani 1 1 d . . . . .
H7 H 0.274573 0.381130 -0.182964 0.029 Uiso 1 1 d R U . . .
N20 N -0.1009(4) 0.3627(3) -0.2381(3) 0.0240(10) Uani 1 1 d . . . . .
C1 C 0.9827(5) 0.0945(4) 0.7081(4) 0.0225(11) Uani 1 1 d . . . . .
C3 C 0.8610(5) 0.0722(4) 0.5940(4) 0.0239(11) Uani 1 1 d . . . . .
C4 C 0.0134(5) 0.3770(4) -0.1901(4) 0.0221(11) Uani 1 1 d . . . . .
C5 C 0.6337(4) 0.0834(4) 0.4111(4) 0.0201(11) Uani 1 1 d . . . . .
C6 C 0.5099(5) 0.1193(4) 0.2964(4) 0.0206(11) Uani 1 1 d . . . . .
C7 C 0.1353(5) 0.4164(4) -0.0823(4) 0.0214(11) Uani 1 1 d . . . . .
C8 C 0.4909(4) 0.3906(4) 0.2068(4) 0.0210(11) Uani 1 1 d . . . . .
C9 C 0.3660(5) 0.4241(4) 0.0937(4) 0.0216(11) Uani 1 1 d . . . . .
C29 C 0.6189(5) 0.8858(5) 0.1056(4) 0.0333(13) Uani 1 1 d . . . . .
H17 H 0.650402 0.953317 0.128352 0.050 Uiso 1 1 calc R U . . .
H20 H 0.647118 0.874759 0.031112 0.050 Uiso 1 1 calc R U . . .
H21 H 0.647363 0.825335 0.152062 0.050 Uiso 1 1 calc R U . . .
C30 C 0.4289(5) 0.7604(4) 0.0783(4) 0.0307(13) Uani 1 1 d . . . . .
H18 H 0.470680 0.707450 0.125045 0.046 Uiso 1 1 calc R U . . .
H19 H 0.457729 0.751773 0.003502 0.046 Uiso 1 1 calc R U . . .
H22 H 0.341960 0.748903 0.085963 0.046 Uiso 1 1 calc R U . . .
C31 C 1.0932(5) 0.1744(5) 0.1033(4) 0.0331(13) Uani 1 1 d . . . . .
H31A H 1.147754 0.139362 0.154180 0.050 Uiso 1 1 calc R U . A 1
H31B H 1.128872 0.169211 0.030001 0.050 Uiso 1 1 calc R U . A 1
H31C H 1.080535 0.250563 0.119136 0.050 Uiso 1 1 calc R U . A 1
C32 C 0.8662(5) 0.1516(6) 0.0462(4) 0.0415(16) Uani 1 1 d . . . . .
H32A H 0.795165 0.107477 0.062301 0.062 Uiso 1 1 calc R U . B 1
H32B H 0.845215 0.227162 0.059764 0.062 Uiso 1 1 calc R U . B 1
H32C H 0.893552 0.145810 -0.029371 0.062 Uiso 1 1 calc R U . B 1
C33 C 0.6086(5) 0.3604(5) 0.6116(4) 0.0364(14) Uani 1 1 d . . . . .
H29 H 0.628330 0.300060 0.661919 0.055 Uiso 1 1 calc R U . . .
H31 H 0.649364 0.425056 0.630385 0.055 Uiso 1 1 calc R U . . .
H34 H 0.635315 0.342108 0.538432 0.055 Uiso 1 1 calc R U . . .
C34 C 0.4054(5) 0.2566(5) 0.5822(4) 0.0373(14) Uani 1 1 d . . . . .
H30 H 0.317555 0.252641 0.592241 0.056 Uiso 1 1 calc R U . . .
H32 H 0.443235 0.199928 0.627684 0.056 Uiso 1 1 calc R U . . .
H33 H 0.430337 0.246402 0.506817 0.056 Uiso 1 1 calc R U . . .
C35 C -0.1067(5) 0.3827(5) 0.4045(4) 0.0369(14) Uani 1 1 d . . . . .
H35 H -0.129702 0.322252 0.363331 0.055 Uiso 1 1 calc R U . . .
H37 H -0.146871 0.449355 0.377709 0.055 Uiso 1 1 calc R U . . .
H38 H -0.131128 0.368629 0.480502 0.055 Uiso 1 1 calc R U . . .
C36 C 0.0948(5) 0.2646(5) 0.4382(4) 0.0375(14) Uani 1 1 d . . . . .
H36 H 0.182099 0.253825 0.426036 0.056 Uiso 1 1 calc R U . . .
H39 H 0.053251 0.211185 0.400072 0.056 Uiso 1 1 calc R U . . .
H40 H 0.072812 0.256089 0.515295 0.056 Uiso 1 1 calc R U . . .
S2A S 0.9620(18) 0.1134(16) 0.1142(17) 0.028(4) Uani 0.068(4) 1 d . U P C 1
S2 S 0.94418(12) 0.21752(11) 0.14432(11) 0.0256(4) Uani 0.932(4) 1 d . U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.517(3) . ?
S1 C29 1.780(5) . ?
S1 C30 1.782(5) . ?
S3 O7 1.514(3) . ?
S3 C33 1.767(5) . ?
S3 C34 1.786(6) . ?
S4 O12 1.519(3) . ?
S4 C35 1.772(6) . ?
S4 C36 1.775(5) . ?
O1 N20 1.219(5) . ?
O2 N2 1.237(5) . ?
O3 N13 1.219(5) . ?
O4 N1 1.215(5) . ?
O6 S2A 1.80(2) . ?
O6 S2 1.525(4) . ?
O8 N1 1.233(5) . ?
O9 N13 1.225(5) . ?
O10 N2 1.219(5) . ?
O11 N20 1.229(5) . ?
N1 C1 1.456(6) . ?
N2 C8 1.452(6) . ?
N3 C1 1.348(6) . ?
N3 C3 1.339(7) . ?
N4 N5 1.371(5) . ?
N4 C8 1.311(6) . ?
N5 H5 0.8800 . ?
N5 C9 1.334(6) . ?
N6 N7 1.364(5) . ?
N6 C1 1.303(6) . ?
N7 H15 0.8800 . ?
N7 C3 1.335(6) . ?
N8 H13 0.8801 . ?
N8 N9 1.394(6) . ?
N8 C3 1.367(6) . ?
N9 H9 0.8800 . ?
N9 C5 1.368(6) . ?
N10 C5 1.333(6) . ?
N10 C6 1.356(6) . ?
N11 N12 1.361(5) . ?
N11 C6 1.303(6) . ?
N12 H10 0.8799 . ?
N12 C5 1.338(6) . ?
N13 C6 1.450(6) . ?
N14 C8 1.333(6) . ?
N14 C9 1.341(6) . ?
N15 H2 0.8800 . ?
N15 N16 1.413(6) . ?
N15 C9 1.360(6) . ?
N16 H1 0.8800 . ?
N16 C7 1.360(6) . ?
N17 C4 1.335(6) . ?
N17 C7 1.341(6) . ?
N18 N19 1.372(5) . ?
N18 C4 1.315(6) . ?
N19 H7 0.8799 . ?
N19 C7 1.348(6) . ?
N20 C4 1.458(6) . ?
C29 H17 0.9800 . ?
C29 H20 0.9800 . ?
C29 H21 0.9800 . ?
C30 H18 0.9800 . ?
C30 H19 0.9800 . ?
C30 H22 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31 S2A 1.66(2) . ?
C31 S2 1.780(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C32 S2A 1.45(2) . ?
C32 S2 1.790(6) . ?
C33 H29 0.9800 . ?
C33 H31 0.9800 . ?
C33 H34 0.9800 . ?
C34 H30 0.9800 . ?
C34 H32 0.9800 . ?
C34 H33 0.9800 . ?
C35 H35 0.9800 . ?
C35 H37 0.9800 . ?
C35 H38 0.9800 . ?
C36 H36 0.9800 . ?
C36 H39 0.9800 . ?
C36 H40 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 C29 103.7(2) . . ?
O5 S1 C30 106.1(2) . . ?
C29 S1 C30 99.2(3) . . ?
O7 S3 C33 103.5(2) . . ?
O7 S3 C34 106.0(2) . . ?
C33 S3 C34 98.4(3) . . ?
O12 S4 C35 104.7(2) . . ?
O12 S4 C36 105.6(2) . . ?
C35 S4 C36 98.1(3) . . ?
O4 N1 O8 126.0(5) . . ?
O4 N1 C1 117.0(4) . . ?
O8 N1 C1 117.1(4) . . ?
O2 N2 C8 116.9(4) . . ?
O10 N2 O2 125.6(4) . . ?
O10 N2 C8 117.5(4) . . ?
C3 N3 C1 100.0(4) . . ?
C8 N4 N5 99.8(4) . . ?
N4 N5 H5 124.8 . . ?
C9 N5 N4 110.2(4) . . ?
C9 N5 H5 124.9 . . ?
C1 N6 N7 101.1(4) . . ?
N6 N7 H15 125.3 . . ?
C3 N7 N6 109.4(4) . . ?
C3 N7 H15 125.3 . . ?
N9 N8 H13 122.1 . . ?
C3 N8 H13 122.2 . . ?
C3 N8 N9 115.6(4) . . ?
N8 N9 H9 122.4 . . ?
C5 N9 N8 115.0(4) . . ?
C5 N9 H9 122.6 . . ?
C5 N10 C6 100.5(4) . . ?
C6 N11 N12 101.6(4) . . ?
N11 N12 H10 125.3 . . ?
C5 N12 N11 109.4(4) . . ?
C5 N12 H10 125.3 . . ?
O3 N13 O9 125.7(4) . . ?
O3 N13 C6 117.3(4) . . ?
O9 N13 C6 117.0(4) . . ?
C8 N14 C9 100.5(4) . . ?
N16 N15 H2 122.5 . . ?
C9 N15 H2 122.3 . . ?
C9 N15 N16 115.2(4) . . ?
N15 N16 H1 122.1 . . ?
C7 N16 N15 115.6(4) . . ?
C7 N16 H1 122.3 . . ?
C4 N17 C7 100.3(4) . . ?
C4 N18 N19 99.9(4) . . ?
N18 N19 H7 125.1 . . ?
C7 N19 N18 109.8(4) . . ?
C7 N19 H7 125.1 . . ?
O1 N20 O11 125.4(4) . . ?
O1 N20 C4 117.9(4) . . ?
O11 N20 C4 116.7(4) . . ?
N3 C1 N1 120.1(5) . . ?
N6 C1 N1 121.7(4) . . ?
N6 C1 N3 118.2(5) . . ?
N3 C3 N8 123.0(4) . . ?
N7 C3 N3 111.3(5) . . ?
N7 C3 N8 125.7(5) . . ?
N17 C4 N20 120.7(5) . . ?
N18 C4 N17 119.3(5) . . ?
N18 C4 N20 120.0(4) . . ?
N10 C5 N9 122.7(4) . . ?
N10 C5 N12 111.2(4) . . ?
N12 C5 N9 126.2(4) . . ?
N10 C6 N13 121.0(4) . . ?
N11 C6 N10 117.4(5) . . ?
N11 C6 N13 121.7(4) . . ?
N17 C7 N16 123.6(4) . . ?
N17 C7 N19 110.7(4) . . ?
N19 C7 N16 125.7(5) . . ?
N4 C8 N2 121.2(4) . . ?
N4 C8 N14 118.9(5) . . ?
N14 C8 N2 119.8(5) . . ?
N5 C9 N14 110.5(4) . . ?
N5 C9 N15 125.9(4) . . ?
N14 C9 N15 123.6(4) . . ?
S1 C29 H17 109.5 . . ?
S1 C29 H20 109.5 . . ?
S1 C29 H21 109.5 . . ?
H17 C29 H20 109.5 . . ?
H17 C29 H21 109.5 . . ?
H20 C29 H21 109.5 . . ?
S1 C30 H18 109.5 . . ?
S1 C30 H19 109.5 . . ?
S1 C30 H22 109.5 . . ?
H18 C30 H19 109.5 . . ?
H18 C30 H22 109.5 . . ?
H19 C30 H22 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
S2A C31 H31A 109.5 . . ?
S2A C31 H31B 109.5 . . ?
S2A C31 H31C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
S2A C32 H32A 109.5 . . ?
S2A C32 H32B 109.5 . . ?
S2A C32 H32C 109.5 . . ?
S3 C33 H29 109.5 . . ?
S3 C33 H31 109.5 . . ?
S3 C33 H34 109.5 . . ?
H29 C33 H31 109.5 . . ?
H29 C33 H34 109.5 . . ?
H31 C33 H34 109.5 . . ?
S3 C34 H30 109.5 . . ?
S3 C34 H32 109.5 . . ?
S3 C34 H33 109.5 . . ?
H30 C34 H32 109.5 . . ?
H30 C34 H33 109.5 . . ?
H32 C34 H33 109.5 . . ?
S4 C35 H35 109.5 . . ?
S4 C35 H37 109.5 . . ?
S4 C35 H38 109.5 . . ?
H35 C35 H37 109.5 . . ?
H35 C35 H38 109.5 . . ?
H37 C35 H38 109.5 . . ?
S4 C36 H36 109.5 . . ?
S4 C36 H39 109.5 . . ?
S4 C36 H40 109.5 . . ?
H36 C36 H39 109.5 . . ?
H36 C36 H40 109.5 . . ?
H39 C36 H40 109.5 . . ?
C31 S2A O6 97.0(11) . . ?
C32 S2A O6 107.3(12) . . ?
C32 S2A C31 119.4(12) . . ?
O6 S2 C31 103.0(2) . . ?
O6 S2 C32 104.6(3) . . ?
C31 S2 C32 97.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N20 C4 N17 173.2(4) . . . . ?
O1 N20 C4 N18 -5.3(7) . . . . ?
O2 N2 C8 N4 -3.2(7) . . . . ?
O2 N2 C8 N14 175.8(4) . . . . ?
O3 N13 C6 N10 -172.7(4) . . . . ?
O3 N13 C6 N11 7.5(7) . . . . ?
O4 N1 C1 N3 5.5(7) . . . . ?
O4 N1 C1 N6 -172.3(5) . . . . ?
O8 N1 C1 N3 -174.2(4) . . . . ?
O8 N1 C1 N6 8.0(7) . . . . ?
O9 N13 C6 N10 8.2(7) . . . . ?
O9 N13 C6 N11 -171.6(4) . . . . ?
O10 N2 C8 N4 174.8(4) . . . . ?
O10 N2 C8 N14 -6.1(7) . . . . ?
O11 N20 C4 N17 -6.1(7) . . . . ?
O11 N20 C4 N18 175.4(4) . . . . ?
N4 N5 C9 N14 1.1(6) . . . . ?
N4 N5 C9 N15 179.9(4) . . . . ?
N5 N4 C8 N2 -180.0(4) . . . . ?
N5 N4 C8 N14 0.9(6) . . . . ?
N6 N7 C3 N3 -0.5(6) . . . . ?
N6 N7 C3 N8 -179.4(4) . . . . ?
N7 N6 C1 N1 178.8(4) . . . . ?
N7 N6 C1 N3 0.9(6) . . . . ?
N8 N9 C5 N10 176.5(4) . . . . ?
N8 N9 C5 N12 -4.3(7) . . . . ?
N9 N8 C3 N3 176.2(4) . . . . ?
N9 N8 C3 N7 -5.0(7) . . . . ?
N11 N12 C5 N9 179.3(4) . . . . ?
N11 N12 C5 N10 -1.5(5) . . . . ?
N12 N11 C6 N10 -0.5(5) . . . . ?
N12 N11 C6 N13 179.3(4) . . . . ?
N15 N16 C7 N17 -179.1(4) . . . . ?
N15 N16 C7 N19 1.1(7) . . . . ?
N16 N15 C9 N5 1.6(7) . . . . ?
N16 N15 C9 N14 -179.7(4) . . . . ?
N18 N19 C7 N16 -179.3(4) . . . . ?
N18 N19 C7 N17 0.9(6) . . . . ?
N19 N18 C4 N17 -0.3(6) . . . . ?
N19 N18 C4 N20 178.3(4) . . . . ?
C1 N3 C3 N7 0.9(5) . . . . ?
C1 N3 C3 N8 179.9(4) . . . . ?
C1 N6 N7 C3 -0.2(5) . . . . ?
C3 N3 C1 N1 -179.1(4) . . . . ?
C3 N3 C1 N6 -1.2(6) . . . . ?
C3 N8 N9 C5 149.7(4) . . . . ?
C4 N17 C7 N16 179.2(5) . . . . ?
C4 N17 C7 N19 -0.9(5) . . . . ?
C4 N18 N19 C7 -0.3(5) . . . . ?
C5 N10 C6 N11 -0.3(5) . . . . ?
C5 N10 C6 N13 179.9(4) . . . . ?
C6 N10 C5 N9 -179.7(4) . . . . ?
C6 N10 C5 N12 1.0(5) . . . . ?
C6 N11 N12 C5 1.2(5) . . . . ?
C7 N17 C4 N18 0.8(6) . . . . ?
C7 N17 C4 N20 -177.8(4) . . . . ?
C8 N4 N5 C9 -1.1(5) . . . . ?
C8 N14 C9 N5 -0.5(5) . . . . ?
C8 N14 C9 N15 -179.3(5) . . . . ?
C9 N14 C8 N2 -179.4(4) . . . . ?
C9 N14 C8 N4 -0.3(6) . . . . ?
C9 N15 N16 C7 -145.0(4) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
