# Supplementary Information (SI) for Chemical Science.
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 2393642'
loop_
_audit_author_name
_audit_author_address
'Jiachen Lu'
;Sogang University
South Korea
;
_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_audit_creation_date             2024-10-24
_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         'C5 H4 N O3 S, C5 H7 N2'
_chemical_formula_sum            'C10 H11 N3 O3 S'
_chemical_formula_weight         253.28
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.2257(4)
_cell_length_b                   13.4248(8)
_cell_length_c                   24.3820(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2365.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7231
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6341
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0906 before and 0.0829 after correction.
The Ratio of minimum to maximum transmission is 0.8503.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27477
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_min         3.035
_diffrn_ambient_temperature      303.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1994
_reflns_number_total             2963
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.209
_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)+(0.0250P)²+3.0444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1474
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
S001 S 0.87645(13) 0.54355(6) 0.60330(3) 0.0449(2) Uani 1 1 d . . . . .
O002 O 0.8662(4) 0.43600(16) 0.59924(10) 0.0551(7) Uani 1 1 d . . . . .
O003 O 1.0584(4) 0.5818(2) 0.59027(10) 0.0675(8) Uani 1 1 d . . . . .
O004 O 0.8032(5) 0.5805(2) 0.65481(9) 0.0716(9) Uani 1 1 d . . . . .
N005 N 0.6800(4) 0.6384(2) 0.45847(11) 0.0500(7) Uani 1 1 d . . . . .
N006 N 0.7627(5) 0.7094(3) 0.18075(12) 0.0578(9) Uani 1 1 d . . . . .
N007 N 0.7392(5) 0.6584(3) 0.34565(13) 0.0578(9) Uani 1 1 d . . . . .
C008 C 0.7257(5) 0.5898(2) 0.55174(12) 0.0393(7) Uani 1 1 d . . . . .
C009 C 0.7899(5) 0.6075(3) 0.49932(13) 0.0430(8) Uani 1 1 d . . . . .
C00A C 0.7531(5) 0.6924(3) 0.23475(12) 0.0443(8) Uani 1 1 d . . . . .
C00B C 0.7673(6) 0.5956(3) 0.25615(15) 0.0526(9) Uani 1 1 d . . . . .
C00C C 0.5395(6) 0.6041(3) 0.56234(16) 0.0542(10) Uani 1 1 d . . . . .
C00D C 0.7269(6) 0.7704(3) 0.27209(14) 0.0523(9) Uani 1 1 d . . . . .
C00E C 0.7615(6) 0.5812(3) 0.31105(16) 0.0590(10) Uani 1 1 d . . . . .
C00F C 0.5018(6) 0.6525(3) 0.46982(17) 0.0571(10) Uani 1 1 d . . . . .
C00G C 0.7200(6) 0.7507(3) 0.32669(15) 0.0579(10) Uani 1 1 d . . . . .
C00H C 0.4262(6) 0.6361(3) 0.52070(19) 0.0629(11) Uani 1 1 d . . . . .
H009 H 0.917(5) 0.599(3) 0.4904(13) 0.052(10) Uiso 1 1 d . . . . .
H00A H 0.782(5) 0.659(3) 0.1585(15) 0.062(12) Uiso 1 1 d . . . . .
H00B H 0.750(5) 0.771(3) 0.1679(15) 0.061(12) Uiso 1 1 d . . . . .
H00F H 0.425(6) 0.675(3) 0.4391(15) 0.072(12) Uiso 1 1 d . . . . .
H00C H 0.500(6) 0.589(3) 0.5983(16) 0.076(13) Uiso 1 1 d . . . . .
H00H H 0.300(6) 0.647(3) 0.5280(16) 0.079(13) Uiso 1 1 d . . . . .
H00G H 0.773(6) 0.515(3) 0.3296(16) 0.075(12) Uiso 1 1 d . . . . .
H00I H 0.702(5) 0.805(3) 0.3535(16) 0.075(13) Uiso 1 1 d . . . . .
H007 H 0.737(6) 0.647(3) 0.3813(17) 0.081(14) Uiso 1 1 d . . . . .
H00E H 0.712(6) 0.838(3) 0.2567(16) 0.076(13) Uiso 1 1 d . . . . .
H00D H 0.781(5) 0.544(3) 0.2343(14) 0.062(12) 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
S001 O002 1.449(2) . ?
S001 O003 1.447(3) . ?
S001 O004 1.450(2) . ?
S001 C008 1.776(3) . ?
N005 C009 1.340(4) . ?
N005 C00F 1.330(5) . ?
N006 C00A 1.338(4) . ?
N006 H00A 0.87(4) . ?
N006 H00B 0.88(4) . ?
N007 C00E 1.347(5) . ?
N007 C00G 1.329(5) . ?
N007 H007 0.88(4) . ?
C008 C009 1.381(4) . ?
C008 C00C 1.383(5) . ?
C009 H009 0.95(4) . ?
C00A C00B 1.405(5) . ?
C00A C00D 1.400(5) . ?
C00B C00E 1.353(5) . ?
C00B H00D 0.88(4) . ?
C00C C00H 1.373(6) . ?
C00C H00C 0.94(4) . ?
C00D C00G 1.358(5) . ?
C00D H00E 0.99(4) . ?
C00E H00G 1.00(4) . ?
C00F C00H 1.374(6) . ?
C00F H00F 0.98(4) . ?
C00G H00I 0.99(4) . ?
C00H H00H 0.94(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S001 O004 112.41(16) . . ?
O002 S001 C008 105.59(15) . . ?
O003 S001 O002 112.66(17) . . ?
O003 S001 O004 113.59(18) . . ?
O003 S001 C008 106.13(15) . . ?
O004 S001 C008 105.65(16) . . ?
C00F N005 C009 117.6(3) . . ?
C00A N006 H00A 119(2) . . ?
C00A N006 H00B 120(2) . . ?
H00A N006 H00B 121(3) . . ?
C00E N007 H007 119(3) . . ?
C00G N007 C00E 120.8(3) . . ?
C00G N007 H007 120(3) . . ?
C009 C008 S001 120.6(3) . . ?
C009 C008 C00C 118.4(3) . . ?
C00C C008 S001 120.9(3) . . ?
N005 C009 C008 122.9(3) . . ?
N005 C009 H009 116(2) . . ?
C008 C009 H009 121(2) . . ?
N006 C00A C00B 121.3(3) . . ?
N006 C00A C00D 121.3(3) . . ?
C00D C00A C00B 117.4(3) . . ?
C00A C00B H00D 121(2) . . ?
C00E C00B C00A 119.8(4) . . ?
C00E C00B H00D 119(2) . . ?
C008 C00C H00C 116(3) . . ?
C00H C00C C008 119.0(4) . . ?
C00H C00C H00C 125(3) . . ?
C00A C00D H00E 117(2) . . ?
C00G C00D C00A 119.8(4) . . ?
C00G C00D H00E 123(2) . . ?
N007 C00E C00B 120.9(4) . . ?
N007 C00E H00G 114(2) . . ?
C00B C00E H00G 125(2) . . ?
N005 C00F C00H 123.4(4) . . ?
N005 C00F H00F 116(2) . . ?
C00H C00F H00F 121(2) . . ?
N007 C00G C00D 121.2(4) . . ?
N007 C00G H00I 118(2) . . ?
C00D C00G H00I 120(2) . . ?
C00C C00H C00F 118.7(4) . . ?
C00C C00H H00H 119(3) . . ?
C00F C00H H00H 122(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
S001 C008 C009 N005 177.1(3) . . . . ?
S001 C008 C00C C00H -177.3(3) . . . . ?
O002 S001 C008 C009 -89.2(3) . . . . ?
O002 S001 C008 C00C 87.5(3) . . . . ?
O003 S001 C008 C009 30.6(3) . . . . ?
O003 S001 C008 C00C -152.7(3) . . . . ?
O004 S001 C008 C009 151.5(3) . . . . ?
O004 S001 C008 C00C -31.8(3) . . . . ?
N005 C00F C00H C00C 0.5(6) . . . . ?
N006 C00A C00B C00E 178.4(4) . . . . ?
N006 C00A C00D C00G -179.2(4) . . . . ?
C008 C00C C00H C00F 0.1(6) . . . . ?
C009 N005 C00F C00H -0.7(6) . . . . ?
C009 C008 C00C C00H -0.5(5) . . . . ?
C00A C00B C00E N007 1.0(6) . . . . ?
C00A C00D C00G N007 0.6(6) . . . . ?
C00B C00A C00D C00G 1.3(6) . . . . ?
C00C C008 C009 N005 0.3(5) . . . . ?
C00D C00A C00B C00E -2.1(6) . . . . ?
C00E N007 C00G C00D -1.7(6) . . . . ?
C00F N005 C009 C008 0.3(5) . . . . ?
C00G N007 C00E C00B 0.9(6) . . . . ?

_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_x_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2393748'
loop_
_audit_author_name
_audit_author_address
'Jiachen Lu'
;Sogang University
South Korea
;
_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H4 N O3 S, C5 H5 N O, C5 H6 N O'
_chemical_formula_sum            'C15 H15 N3 O5 S'
_chemical_formula_weight         349.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.5972(5)
_cell_length_b                   7.0455(2)
_cell_length_c                   12.8268(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.8810(10)
_cell_angle_gamma                90
_cell_volume                     1590.09(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0774 after correction.
The Ratio of minimum to maximum transmission is 0.8753.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29324
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.315
_diffrn_ambient_temperature      303.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2385
_reflns_number_total             2795
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.114
_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)+(0.0343P)²+0.9257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
S001 S 0.34845(3) 0.12184(8) 0.43635(4) 0.03868(17) Uani 1 1 d . . . . .
O002 O 0.34251(9) 0.1404(3) 0.54887(12) 0.0546(4) Uani 1 1 d . . . . .
O003 O 0.37622(9) -0.0618(2) 0.40476(14) 0.0577(5) Uani 1 1 d . . . . .
O004 O 0.27962(8) 0.1786(3) 0.38227(13) 0.0585(5) Uani 1 1 d . . . . .
N006 N 0.54935(9) 0.3830(3) 0.40543(14) 0.0403(4) Uani 1 1 d . . . . .
O007 O 0.96454(8) 0.3286(3) 0.17501(13) 0.0684(6) Uani 1 1 d . . . . .
N008 N 0.70858(11) 0.3430(3) 0.42057(16) 0.0469(5) Uani 1 1 d . . . . .
N009 N 1.18834(11) 0.3354(3) 0.10674(16) 0.0488(5) Uani 1 1 d . . . . .
C00A C 0.41913(11) 0.2870(3) 0.39841(15) 0.0336(4) Uani 1 1 d . . . . .
C00B C 0.49403(11) 0.2627(3) 0.43060(16) 0.0366(5) Uani 1 1 d . . . . .
C00C C 0.53082(13) 0.5332(3) 0.34741(17) 0.0458(5) Uani 1 1 d . . . . .
C00D C 0.40132(13) 0.4428(4) 0.33733(18) 0.0476(6) Uani 1 1 d . . . . .
C00E C 0.86174(11) 0.3337(3) 0.37753(17) 0.0410(5) Uani 1 1 d . . . . .
C00F C 0.73159(13) 0.3630(3) 0.32192(19) 0.0478(6) Uani 1 1 d . . . . .
C00G C 0.80642(12) 0.3598(3) 0.29819(19) 0.0450(5) Uani 1 1 d . . . . .
C00H C 0.83520(13) 0.3156(4) 0.47963(19) 0.0455(5) Uani 1 1 d . . . . .
C00I C 1.09317(13) 0.3437(4) 0.2324(2) 0.0515(6) Uani 1 1 d . . . . .
C00J C 1.06124(13) 0.3182(4) 0.05097(19) 0.0525(6) Uani 1 1 d . . . . .
C00K C 0.75942(13) 0.3197(4) 0.49855(19) 0.0486(6) Uani 1 1 d . . . . .
C00L C 1.03669(12) 0.3299(4) 0.15440(18) 0.0482(6) Uani 1 1 d . . . . .
C00M C 1.16760(13) 0.3445(4) 0.2061(2) 0.0537(6) Uani 1 1 d . . . . .
C00N C 0.45812(15) 0.5675(4) 0.3120(2) 0.0544(6) Uani 1 1 d . . . . .
C00O C 1.13602(13) 0.3228(4) 0.0299(2) 0.0512(6) Uani 1 1 d . . . . .
O4 O 0.93374(8) 0.3267(3) 0.35987(13) 0.0576(5) Uani 1 1 d . . . . .
H4 H 0.940743 0.332894 0.296906 0.086 Uiso 1 1 calc R U . . .
H00K H 0.7408(15) 0.307(4) 0.565(2) 0.062(7) Uiso 1 1 d . . . . .
H00B H 0.5094(14) 0.151(4) 0.4762(19) 0.057(7) Uiso 1 1 d . . . . .
H00D H 0.3507(15) 0.460(4) 0.3133(19) 0.058(7) Uiso 1 1 d . . . . .
H00C H 0.5725(14) 0.620(3) 0.3302(19) 0.054(7) Uiso 1 1 d . . . . .
H00I H 1.0793(15) 0.351(4) 0.300(2) 0.060(8) Uiso 1 1 d . . . . .
H009 H 1.2348(19) 0.337(4) 0.090(2) 0.078(9) Uiso 1 1 d . . . . .
H00N H 0.4458(14) 0.671(4) 0.275(2) 0.060(8) Uiso 1 1 d . . . . .
H00G H 0.8210(15) 0.371(4) 0.234(2) 0.060(8) Uiso 1 1 d . . . . .
H00J H 1.0253(17) 0.308(4) -0.002(2) 0.076(9) Uiso 1 1 d . . . . .
H00O H 1.1563(15) 0.318(4) -0.038(2) 0.067(8) Uiso 1 1 d . . . . .
H00H H 0.8676(14) 0.299(3) 0.532(2) 0.053(7) Uiso 1 1 d . . . . .
H00F H 0.6944(15) 0.383(4) 0.270(2) 0.061(7) Uiso 1 1 d . . . . .
H00M H 1.2079(18) 0.355(4) 0.253(2) 0.079(9) Uiso 1 1 d . . . . .
H008 H 0.6611(17) 0.347(4) 0.433(2) 0.066(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O002 1.4546(16) . ?
S001 O003 1.4434(17) . ?
S001 O004 1.4430(16) . ?
S001 C00A 1.777(2) . ?
N006 C00B 1.334(3) . ?
N006 C00C 1.331(3) . ?
O007 C00L 1.301(3) . ?
N008 C00F 1.342(3) . ?
N008 C00K 1.342(3) . ?
N008 H008 0.85(3) . ?
N009 C00M 1.332(3) . ?
N009 C00O 1.341(3) . ?
N009 H009 0.85(3) . ?
C00A C00B 1.386(3) . ?
C00A C00D 1.382(3) . ?
C00B H00B 1.01(3) . ?
C00C C00N 1.373(3) . ?
C00C H00C 0.98(3) . ?
C00D C00N 1.374(3) . ?
C00D H00D 0.95(3) . ?
C00E C00G 1.409(3) . ?
C00E C00H 1.403(3) . ?
C00E O4 1.291(3) . ?
C00F C00G 1.356(3) . ?
C00F H00F 0.94(3) . ?
C00G H00G 0.87(3) . ?
C00H C00K 1.359(3) . ?
C00H H00H 0.88(3) . ?
C00I C00L 1.402(3) . ?
C00I C00M 1.358(3) . ?
C00I H00I 0.90(3) . ?
C00J C00L 1.404(3) . ?
C00J C00O 1.348(3) . ?
C00J H00J 0.92(3) . ?
C00K H00K 0.93(3) . ?
C00M H00M 0.93(3) . ?
C00N H00N 0.89(3) . ?
C00O H00O 0.95(3) . ?
O4 H4 0.8200 . ?

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
O002 S001 C00A 105.91(9) . . ?
O003 S001 O002 112.88(11) . . ?
O003 S001 C00A 105.60(9) . . ?
O004 S001 O002 112.30(10) . . ?
O004 S001 O003 113.50(11) . . ?
O004 S001 C00A 105.83(10) . . ?
C00C N006 C00B 117.82(19) . . ?
C00F N008 H008 118.7(19) . . ?
C00K N008 C00F 120.6(2) . . ?
C00K N008 H008 120.7(19) . . ?
C00M N009 C00O 120.7(2) . . ?
C00M N009 H009 122(2) . . ?
C00O N009 H009 118(2) . . ?
C00B C00A S001 120.26(16) . . ?
C00D C00A S001 121.47(16) . . ?
C00D C00A C00B 118.27(19) . . ?
N006 C00B C00A 122.9(2) . . ?
N006 C00B H00B 116.3(14) . . ?
C00A C00B H00B 120.8(14) . . ?
N006 C00C C00N 123.0(2) . . ?
N006 C00C H00C 116.3(14) . . ?
C00N C00C H00C 120.7(14) . . ?
C00A C00D H00D 119.4(16) . . ?
C00N C00D C00A 118.9(2) . . ?
C00N C00D H00D 121.7(15) . . ?
C00H C00E C00G 116.7(2) . . ?
O4 C00E C00G 123.2(2) . . ?
O4 C00E C00H 120.1(2) . . ?
N008 C00F C00G 121.2(2) . . ?
N008 C00F H00F 118.1(16) . . ?
C00G C00F H00F 120.7(16) . . ?
C00E C00G H00G 118.9(18) . . ?
C00F C00G C00E 120.2(2) . . ?
C00F C00G H00G 121.0(18) . . ?
C00E C00H H00H 120.1(16) . . ?
C00K C00H C00E 120.4(2) . . ?
C00K C00H H00H 119.5(16) . . ?
C00L C00I H00I 119.1(17) . . ?
C00M C00I C00L 119.9(2) . . ?
C00M C00I H00I 121.0(17) . . ?
C00L C00J H00J 118.8(18) . . ?
C00O C00J C00L 120.2(2) . . ?
C00O C00J H00J 121.0(18) . . ?
N008 C00K C00H 120.9(2) . . ?
N008 C00K H00K 117.4(16) . . ?
C00H C00K H00K 121.7(17) . . ?
O007 C00L C00I 122.6(2) . . ?
O007 C00L C00J 120.5(2) . . ?
C00I C00L C00J 116.9(2) . . ?
N009 C00M C00I 121.2(2) . . ?
N009 C00M H00M 114.3(19) . . ?
C00I C00M H00M 124.5(19) . . ?
C00C C00N C00D 119.1(2) . . ?
C00C C00N H00N 122.5(17) . . ?
C00D C00N H00N 118.4(17) . . ?
N009 C00O C00J 121.0(2) . . ?
N009 C00O H00O 114.4(16) . . ?
C00J C00O H00O 124.5(16) . . ?
C00E O4 H4 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
S001 C00A C00B N006 -179.33(16) . . . . ?
S001 C00A C00D C00N 178.87(18) . . . . ?
O002 S001 C00A C00B 65.82(19) . . . . ?
O002 S001 C00A C00D -113.64(19) . . . . ?
O003 S001 C00A C00B -54.14(19) . . . . ?
O003 S001 C00A C00D 126.40(19) . . . . ?
O004 S001 C00A C00B -174.77(17) . . . . ?
O004 S001 C00A C00D 5.8(2) . . . . ?
N006 C00C C00N C00D 0.3(4) . . . . ?
N008 C00F C00G C00E 0.5(4) . . . . ?
C00A C00D C00N C00C 0.4(4) . . . . ?
C00B N006 C00C C00N -0.7(3) . . . . ?
C00B C00A C00D C00N -0.6(3) . . . . ?
C00C N006 C00B C00A 0.5(3) . . . . ?
C00D C00A C00B N006 0.2(3) . . . . ?
C00E C00H C00K N008 -0.7(4) . . . . ?
C00F N008 C00K C00H -0.1(4) . . . . ?
C00G C00E C00H C00K 1.3(4) . . . . ?
C00H C00E C00G C00F -1.2(3) . . . . ?
C00K N008 C00F C00G 0.1(4) . . . . ?
C00L C00I C00M N009 1.1(4) . . . . ?
C00L C00J C00O N009 1.1(4) . . . . ?
C00M N009 C00O C00J -0.3(4) . . . . ?
C00M C00I C00L O007 -180.0(3) . . . . ?
C00M C00I C00L C00J -0.3(4) . . . . ?
C00O N009 C00M C00I -0.8(4) . . . . ?
C00O C00J C00L O007 178.9(3) . . . . ?
C00O C00J C00L C00I -0.8(4) . . . . ?
O4 C00E C00G C00F 179.0(2) . . . . ?
O4 C00E C00H C00K -178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
