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

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

data_jiso3
_database_code_depnum_ccdc_archive 'CCDC 1997034'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C8 H16 N6 O6 S2'
_chemical_formula_moiety         'C8 H16 N6 O6 S2'
_chemical_formula_weight         356.37
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.73165(19)
_cell_length_b                   7.0727(2)
_cell_length_c                   7.95197(18)
_cell_angle_alpha                86.2104(17)
_cell_angle_beta                 72.5954(18)
_cell_angle_gamma                85.649(2)
_cell_volume                     359.851(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1802
_cell_measurement_theta_min      5.84
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             186.00
_exptl_absorpt_coefficient_mu    3.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_T_max  0.687

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4160
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         5.837
_diffrn_reflns_theta_full        68.220
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1299
_reflns_number_gt                1210
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0971
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1299
_refine_ls_number_parameters     100
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0454P)²+0.3130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34781(8) 0.24517(7) 0.25787(6) 0.0152(2) Uani 1 1 d . . .
O1 O 0.1457(2) 0.3262(2) 0.2500(2) 0.0201(4) Uani 1 1 d . . .
O2 O 0.5057(2) 0.2424(2) 0.0862(2) 0.0191(4) Uani 1 1 d . . .
O3 O 0.3334(2) 0.0577(2) 0.3518(2) 0.0189(4) Uani 1 1 d . . .
C2 C 0.4346(3) 0.3926(3) 0.3906(3) 0.0152(5) Uani 1 1 d . . .
C3 C 0.3031(3) 0.5399(3) 0.4767(3) 0.0151(5) Uani 1 1 d . . .
H3 H 0.1723 0.5657 0.4606 0.018 Uiso 1 1 calc R . .
C4 C 0.6311(4) 0.3517(3) 0.4129(3) 0.0166(5) Uani 1 1 d . . .
H4 H 0.7175 0.2526 0.3544 0.020 Uiso 1 1 calc R . .
N1 N -0.0416(3) 0.2542(3) -0.0225(2) 0.0197(4) Uani 1 1 d . . .
H1A H 0.0008 0.2977 0.0585 0.024 Uiso 1 1 calc R . .
H1B H -0.1729 0.2522 -0.0093 0.024 Uiso 1 1 calc R . .
N2 N 0.0322(3) 0.1252(3) -0.2952(2) 0.0195(4) Uani 1 1 d . . .
H2A H -0.0988 0.1242 -0.2838 0.023 Uiso 1 1 calc R . .
H2B H 0.1223 0.0840 -0.3889 0.023 Uiso 1 1 calc R . .
N3 N 0.2980(3) 0.1940(3) -0.1870(2) 0.0188(4) Uani 1 1 d . . .
H3A H 0.3395 0.2376 -0.1056 0.023 Uiso 1 1 calc R . .
H3B H 0.3877 0.1527 -0.2809 0.023 Uiso 1 1 calc R . .
C1 C 0.0957(4) 0.1903(3) -0.1677(3) 0.0170(5) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4529(16) . ?
S1 O2 1.4580(16) . ?
S1 O3 1.4731(16) . ?
S1 C2 1.775(2) . ?
C2 C3 1.389(3) . ?
C2 C4 1.393(3) . ?
C3 C4 1.388(3) 2_666 ?
C3 H3 0.9300 . ?
C4 C3 1.388(3) 2_666 ?
C4 H4 0.9300 . ?
N1 C1 1.326(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C1 1.332(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C1 1.326(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

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 113.34(9) . . ?
O1 S1 O3 112.25(9) . . ?
O2 S1 O3 112.09(9) . . ?
O1 S1 C2 106.91(10) . . ?
O2 S1 C2 106.97(9) . . ?
O3 S1 C2 104.60(9) . . ?
C3 C2 C4 121.2(2) . . ?
C3 C2 S1 119.89(17) . . ?
C4 C2 S1 118.79(17) . . ?
C4 C3 C2 119.3(2) 2_666 . ?
C4 C3 H3 120.3 2_666 . ?
C2 C3 H3 120.3 . . ?
C3 C4 C2 119.4(2) 2_666 . ?
C3 C4 H4 120.3 2_666 . ?
C2 C4 H4 120.3 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N1 C1 N3 119.6(2) . . ?
N1 C1 N2 120.6(2) . . ?
N3 C1 N2 119.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C2 C3 6.2(2) . . . . ?
O2 S1 C2 C3 127.89(18) . . . . ?
O3 S1 C2 C3 -113.05(18) . . . . ?
O1 S1 C2 C4 -176.90(16) . . . . ?
O2 S1 C2 C4 -55.18(19) . . . . ?
O3 S1 C2 C4 63.88(18) . . . . ?
C4 C2 C3 C4 0.0(3) . . . 2_666 ?
S1 C2 C3 C4 176.84(16) . . . 2_666 ?
C3 C2 C4 C3 0.0(3) . . . 2_666 ?
S1 C2 C4 C3 -176.88(16) . . . 2_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 . . . 2.902(3) 0.860 2.066 163.6 no
N1 H1B O2 . . 1_455 2.915(3) 0.860 2.072 166.2 no
N2 H2A O3 . . 2_555 3.026(3) 0.860 2.314 140.3 no
N2 H2B O3 . . 1_554 2.974(2) 0.860 2.136 164.6 no
N3 H3A O2 . . . 2.963(3) 0.860 2.148 158.1 no
N3 H3B O3 . . 2_655 2.956(2) 0.860 2.261 137.9 no
####################################################################### 
# 
# 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_G2BDS-diox-171020
_database_code_depnum_ccdc_archive 'CCDC 1997035'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H40 N6 O12 S2'
_chemical_formula_moiety         'C20 H40 N6 O12 S2'
_chemical_formula_weight         620.69
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.6145(3)
_cell_length_b                   12.3230(5)
_cell_length_c                   15.6653(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.077(2)
_cell_angle_gamma                90.0000
_cell_volume                     1442.53(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5732
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      68.08
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660.00
_exptl_absorpt_coefficient_mu    2.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.796

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15727
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         4.599
_diffrn_reflns_theta_full        68.220
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2638
_reflns_number_gt                1948
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1418
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2638
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0798P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.48477(10) 0.44536(6) 0.19496(5) 0.0365(3) Uani 1 1 d . . .
O1 O 0.4761(2) 0.32837(15) 0.20095(12) 0.0386(5) Uani 1 1 d . . .
O2 O 0.3272(2) 0.49971(15) 0.21478(12) 0.0390(5) Uani 1 1 d . . .
O3 O 0.6516(3) 0.48981(15) 0.24482(12) 0.0399(5) Uani 1 1 d . . .
O4 O 0.1426(3) 0.23312(16) -0.09531(13) 0.0449(5) Uani 1 1 d . . .
O5 O -0.0747(3) 0.25730(15) 0.03128(13) 0.0429(5) Uani 1 1 d . . .
O6 O 0.3899(3) 0.00286(17) 0.06343(14) 0.0500(6) Uani 1 1 d . . .
N1 N 0.1459(3) 0.22744(19) 0.23481(16) 0.0412(6) Uani 1 1 d . . .
H1A H 0.1480 0.1563 0.2395 0.049 Uiso 1 1 calc R . .
H1B H 0.2429 0.2627 0.2282 0.049 Uiso 1 1 calc R . .
N2 N -0.1492(3) 0.22814(19) 0.24774(16) 0.0419(6) Uani 1 1 d . . .
H2A H -0.2484 0.2637 0.2503 0.050 Uiso 1 1 calc R . .
H2B H -0.1467 0.1569 0.2518 0.050 Uiso 1 1 calc R . .
N3 N -0.0057(3) 0.38901(18) 0.23148(16) 0.0419(6) Uani 1 1 d . . .
H3A H -0.1040 0.4253 0.2340 0.050 Uiso 1 1 calc R . .
H3B H 0.0917 0.4239 0.2249 0.050 Uiso 1 1 calc R . .
C1 C -0.0041(4) 0.2818(2) 0.23775(18) 0.0370(7) Uani 1 1 d . . .
C2 C 0.4902(4) 0.4751(2) 0.08528(18) 0.0348(7) Uani 1 1 d . . .
C3 C 0.5825(4) 0.4065(2) 0.0390(2) 0.0387(7) Uani 1 1 d . . .
H3 H 0.6383 0.3428 0.0656 0.046 Uiso 1 1 calc R . .
C4 C 0.4070(4) 0.5685(2) 0.04629(19) 0.0366(7) Uani 1 1 d . . .
H4 H 0.3434 0.6149 0.0781 0.044 Uiso 1 1 calc R . .
C5 C 0.0193(4) 0.1513(2) -0.0809(2) 0.0454(8) Uani 1 1 d . . .
H5A H 0.0650 0.0792 -0.0941 0.055 Uiso 1 1 calc R . .
H5B H -0.0970 0.1632 -0.1206 0.055 Uiso 1 1 calc R . .
C6 C -0.0079(4) 0.1529(2) 0.0118(2) 0.0411(7) Uani 1 1 d . . .
H6A H -0.0942 0.0957 0.0203 0.049 Uiso 1 1 calc R . .
H6B H 0.1070 0.1380 0.0517 0.049 Uiso 1 1 calc R . .
C7 C 0.0526(4) 0.3384(2) 0.0186(2) 0.0439(8) Uani 1 1 d . . .
H7A H 0.1679 0.3245 0.0585 0.053 Uiso 1 1 calc R . .
H7B H 0.0091 0.4108 0.0324 0.053 Uiso 1 1 calc R . .
C8 C 0.0807(4) 0.3374(2) -0.0742(2) 0.0429(8) Uani 1 1 d . . .
H8A H -0.0332 0.3547 -0.1140 0.052 Uiso 1 1 calc R . .
H8B H 0.1697 0.3934 -0.0817 0.052 Uiso 1 1 calc R . .
C9 C 0.4750(4) -0.0946(3) 0.0443(2) 0.0486(8) Uani 1 1 d . . .
H9A H 0.4001 -0.1576 0.0533 0.058 Uiso 1 1 calc R . .
H9B H 0.5919 -0.1019 0.0844 0.058 Uiso 1 1 calc R . .
C10 C 0.4966(5) 0.0940(3) 0.0485(2) 0.0509(8) Uani 1 1 d . . .
H10A H 0.6139 0.0907 0.0887 0.061 Uiso 1 1 calc R . .
H10B H 0.4362 0.1620 0.0603 0.061 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4469(19) . ?
S1 O2 1.4586(18) . ?
S1 O3 1.464(2) . ?
S1 C2 1.765(3) . ?
O4 C5 1.425(3) . ?
O4 C8 1.429(3) . ?
O5 C7 1.432(3) . ?
O5 C6 1.437(3) . ?
O6 C9 1.424(3) . ?
O6 C10 1.432(4) . ?
N1 C1 1.333(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.323(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C1 1.324(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C2 C3 1.390(4) . ?
C2 C4 1.397(4) . ?
C3 C4 1.388(4) 3_665 ?
C3 H3 0.9500 . ?
C4 C3 1.387(4) 3_665 ?
C4 H4 0.9500 . ?
C5 C6 1.506(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.508(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.509(4) 3_655 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C9 1.509(4) 3_655 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 113.22(11) . . ?
O1 S1 O3 112.57(11) . . ?
O2 S1 O3 112.30(11) . . ?
O1 S1 C2 106.24(12) . . ?
O2 S1 C2 106.62(12) . . ?
O3 S1 C2 105.17(13) . . ?
C5 O4 C8 110.0(2) . . ?
C7 O5 C6 108.6(2) . . ?
C9 O6 C10 109.4(2) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N2 C1 N3 120.8(3) . . ?
N2 C1 N1 119.6(3) . . ?
N3 C1 N1 119.7(3) . . ?
C3 C2 C4 120.4(3) . . ?
C3 C2 S1 119.4(2) . . ?
C4 C2 S1 120.2(2) . . ?
C4 C3 C2 119.8(3) 3_665 . ?
C4 C3 H3 120.1 3_665 . ?
C2 C3 H3 120.1 . . ?
C3 C4 C2 119.9(3) 3_665 . ?
C3 C4 H4 120.1 3_665 . ?
C2 C4 H4 120.1 . . ?
O4 C5 C6 111.1(2) . . ?
O4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
O4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O5 C6 C5 109.6(2) . . ?
O5 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
O5 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O5 C7 C8 110.7(2) . . ?
O5 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O4 C8 C7 110.2(2) . . ?
O4 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
O4 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O6 C9 C10 110.8(3) . 3_655 ?
O6 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 3_655 . ?
O6 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 3_655 . ?
H9A C9 H9B 108.1 . . ?
O6 C10 C9 110.6(3) . 3_655 ?
O6 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 3_655 . ?
O6 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 3_655 . ?
H10A C10 H10B 108.1 . . ?

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 C2 C3 -36.1(3) . . . . ?
O2 S1 C2 C3 -157.2(2) . . . . ?
O3 S1 C2 C3 83.4(2) . . . . ?
O1 S1 C2 C4 145.8(2) . . . . ?
O2 S1 C2 C4 24.8(3) . . . . ?
O3 S1 C2 C4 -94.6(2) . . . . ?
C4 C2 C3 C4 0.4(5) . . . 3_665 ?
S1 C2 C3 C4 -177.6(2) . . . 3_665 ?
C3 C2 C4 C3 -0.4(5) . . . 3_665 ?
S1 C2 C4 C3 177.6(2) . . . 3_665 ?
C8 O4 C5 C6 -57.5(3) . . . . ?
C7 O5 C6 C5 -59.5(3) . . . . ?
O4 C5 C6 O5 59.2(3) . . . . ?
C6 O5 C7 C8 59.9(3) . . . . ?
C5 O4 C8 C7 56.7(3) . . . . ?
O5 C7 C8 O4 -58.8(3) . . . . ?
C10 O6 C9 C10 -57.9(4) . . . 3_655 ?
C9 O6 C10 C9 57.8(3) . . . 3_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O2 . . 2_545 2.912(3) 0.880 2.054 164.6 no
N1 H1B O1 . . . 2.943(3) 0.880 2.069 172.0 no
N2 H2A O1 . . 1_455 3.065(3) 0.880 2.239 156.4 no
N2 H2B O3 . . 2_545 2.939(3) 0.880 2.060 176.8 no
N3 H3A O3 . . 1_455 2.934(3) 0.880 2.060 171.9 no
N3 H3B O2 . . . 2.934(3) 0.880 2.055 176.7 no
####################################################################### 
# 
# 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_200828_G2BDS_toluene
_database_code_depnum_ccdc_archive 'CCDC 2041223'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_200828_G2BDS_toluene 
;
PROBLEM: Short Inter D...A Contact  O5       ..O5       .       1.08 Ang.
RESPONSE: H2O molecule exist in the disorder with a half occupancy factor
;
# Added during the CSD deposition process: Thursday 29 October 2020 02:37 AM
# end Validation Reply Form


#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C8 H18 N6 O7 S2'
_chemical_formula_moiety         'C8 H18 N6 O7 S2'
_chemical_formula_weight         374.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
_space_group_IT_number           62
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,1/2-Z
3 -X,1/2+Y,-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,-1/2+Z
7 +X,-1/2-Y,+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   21.3840
_cell_length_b                   8.2026
_cell_length_c                   9.6041
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1684.5967
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11584
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      68.11
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784.00
_exptl_absorpt_coefficient_mu    3.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_T_max  0.968

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            17983
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_theta_max         68.180
_diffrn_reflns_theta_min         4.135
_diffrn_reflns_theta_full        68.180
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1654
_reflns_number_gt                1231
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.3067
_refine_ls_wR_factor_gt          0.2893
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1654
_refine_ls_number_parameters     142
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1715P)²+7.3660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.10
_refine_diff_density_min         -0.90
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32658(10) 0.2500 0.6712(2) 0.0342(7) Uani 1 2 d S . .
S2 S 0.62052(10) 0.2500 0.6908(3) 0.0355(7) Uani 1 2 d S . .
O1 O 0.3109(3) 0.2500 0.8200(7) 0.0369(15) Uani 1 2 d S . .
O2 O 0.30557(19) 0.1019(5) 0.6016(5) 0.0380(12) Uani 1 1 d . . .
O3 O 0.6337(3) 0.2500 0.8399(7) 0.0449(17) Uani 1 2 d S . .
O4 O 0.6424(2) 0.1015(5) 0.6252(5) 0.0399(12) Uani 1 1 d . . .
O5 O 0.4529(6) 0.6845(12) 0.9085(15) 0.077(4) Uani 0.50 1 d P . .
N1 N 0.3708(4) 0.2500 1.2921(9) 0.044(2) Uani 1 2 d S . .
H1A H 0.3749 0.1571 1.3370 0.053 Uiso 0.50 1 calc PR . .
H1B H 0.3754 0.3429 1.3367 0.053 Uiso 0.50 1 calc PR . .
N2 N 0.3501(2) 0.1099(7) 1.0861(6) 0.0434(15) Uani 1 1 d . . .
H2A H 0.3407 0.1111 0.9969 0.052 Uiso 1 1 calc R . .
H2B H 0.3546 0.0164 1.1299 0.052 Uiso 1 1 calc R . .
N3 N 0.2732(2) -0.1085(7) 0.8490(6) 0.0366(13) Uani 1 1 d . . .
H3A H 0.2813 -0.0156 0.8069 0.044 Uiso 1 1 calc R . .
H3B H 0.2571 -0.1086 0.9333 0.044 Uiso 1 1 calc R . .
N4 N 0.3096(4) -0.2500 0.6590(9) 0.041(2) Uani 1 2 d S . .
H4A H 0.3177 -0.3429 0.6169 0.049 Uiso 0.50 1 calc PR . .
H4B H 0.3177 -0.1571 0.6169 0.049 Uiso 0.50 1 calc PR . .
C1 C 0.4091(4) 0.2500 0.6666(10) 0.034(2) Uani 1 2 d S . .
C2 C 0.4394(5) 0.3787(17) 0.7345(14) 0.035(3) Uani 0.50 1 d P . .
C3 C 0.5053(6) 0.3808(17) 0.7417(16) 0.041(3) Uani 0.50 1 d P . .
C5 C 0.5384(4) 0.2500 0.6764(11) 0.039(2) Uani 1 2 d S . .
C6 C 0.4413(6) 0.1288(18) 0.5989(14) 0.040(3) Uani 0.50 1 d P . .
C7 C 0.3573(4) 0.2500 1.1551(10) 0.038(2) Uani 1 2 d S . .
C8 C 0.2855(4) -0.2500 0.7847(10) 0.035(2) Uani 1 2 d S . .
C9 C 0.5084(6) 0.1294(17) 0.6029(14) 0.038(3) Uani 0.50 1 d P . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.457(4) . ?
S1 O2 1.457(4) 7_565 ?
S1 O1 1.468(7) . ?
S1 C1 1.765(8) . ?
S2 O4 1.449(4) 7_565 ?
S2 O4 1.449(4) . ?
S2 O3 1.460(7) . ?
S2 C5 1.762(9) . ?
O5 O5 1.07(2) 7_575 ?
N1 C7 1.347(12) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C7 1.335(8) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C8 1.341(7) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C8 1.313(12) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C6 1.372(15) 7_565 ?
C1 C6 1.372(15) . ?
C1 C2 1.400(14) 7_565 ?
C1 C2 1.400(14) . ?
C2 C6 1.304(19) 7_565 ?
C2 C3 1.411(18) . ?
C2 C9 1.944(19) 7_565 ?
C3 C9 1.34(2) 7_565 ?
C3 C5 1.430(15) . ?
C3 C6 1.94(2) 7_565 ?
C5 C9 1.374(15) . ?
C5 C9 1.374(15) 7_565 ?
C5 C3 1.430(15) 7_565 ?
C6 C2 1.304(19) 7_565 ?
C6 C9 1.436(18) . ?
C6 C3 1.94(2) 7_565 ?
C6 C6 1.99(3) 7_565 ?
C7 N2 1.335(8) 7_565 ?
C8 N3 1.341(7) 7 ?
C9 C3 1.34(2) 7_565 ?
C9 C9 1.98(3) 7_565 ?
C9 C2 1.944(19) 7_565 ?

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 O2 112.9(4) . 7_565 ?
O2 S1 O1 112.1(2) . . ?
O2 S1 O1 112.1(2) 7_565 . ?
O2 S1 C1 107.3(2) . . ?
O2 S1 C1 107.3(2) 7_565 . ?
O1 S1 C1 104.7(4) . . ?
O4 S2 O4 114.3(4) 7_565 . ?
O4 S2 O3 111.4(2) 7_565 . ?
O4 S2 O3 111.4(2) . . ?
O4 S2 C5 106.8(2) 7_565 . ?
O4 S2 C5 106.8(3) . . ?
O3 S2 C5 105.6(4) . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C6 C1 C6 92.9(13) 7_565 . ?
C6 C1 C2 122.4(9) 7_565 7_565 ?
C6 C1 C2 56.1(8) . 7_565 ?
C6 C1 C2 56.1(8) 7_565 . ?
C6 C1 C2 122.4(9) . . ?
C2 C1 C2 97.9(12) 7_565 . ?
C6 C1 S1 120.8(7) 7_565 . ?
C6 C1 S1 120.8(7) . . ?
C2 C1 S1 116.8(6) 7_565 . ?
C2 C1 S1 116.8(6) . . ?
C6 C2 C1 60.9(9) 7_565 . ?
C6 C2 C3 91.1(11) 7_565 . ?
C1 C2 C3 119.6(11) . . ?
C6 C2 C9 47.6(8) 7_565 7_565 ?
C1 C2 C9 91.3(9) . 7_565 ?
C3 C2 C9 43.4(8) . 7_565 ?
C9 C3 C2 90.0(12) 7_565 . ?
C9 C3 C5 59.4(9) 7_565 . ?
C2 C3 C5 117.6(11) . . ?
C9 C3 C6 47.8(8) 7_565 7_565 ?
C2 C3 C6 42.2(8) . 7_565 ?
C5 C3 C6 90.5(9) . 7_565 ?
C9 C5 C9 92.2(13) . 7_565 ?
C9 C5 C3 122.3(10) . . ?
C9 C5 C3 56.9(9) 7_565 . ?
C9 C5 C3 56.9(9) . 7_565 ?
C9 C5 C3 122.3(10) 7_565 7_565 ?
C3 C5 C3 97.2(12) . 7_565 ?
C9 C5 S2 120.4(7) . . ?
C9 C5 S2 120.4(7) 7_565 . ?
C3 C5 S2 117.3(7) . . ?
C3 C5 S2 117.3(7) 7_565 . ?
C2 C6 C1 63.0(9) 7_565 . ?
C2 C6 C9 90.2(11) 7_565 . ?
C1 C6 C9 119.0(12) . . ?
C2 C6 C3 46.7(8) 7_565 7_565 ?
C1 C6 C3 92.8(9) . 7_565 ?
C9 C6 C3 43.6(8) . 7_565 ?
C2 C6 C6 92.7(9) 7_565 7_565 ?
C1 C6 C6 43.6(6) . 7_565 ?
C9 C6 C6 89.8(8) . 7_565 ?
C3 C6 C6 92.3(6) 7_565 7_565 ?
N2 C7 N2 118.7(9) . 7_565 ?
N2 C7 N1 120.6(5) . . ?
N2 C7 N1 120.6(5) 7_565 . ?
N4 C8 N3 120.0(4) . 7 ?
N4 C8 N3 120.0(4) . . ?
N3 C8 N3 119.9(8) 7 . ?
C3 C9 C5 63.7(9) 7_565 . ?
C3 C9 C6 88.7(11) 7_565 . ?
C5 C9 C6 118.9(12) . . ?
C3 C9 C9 93.6(8) 7_565 7_565 ?
C5 C9 C9 43.9(6) . 7_565 ?
C6 C9 C9 90.2(8) . 7_565 ?
C3 C9 C2 46.5(8) 7_565 7_565 ?
C5 C9 C2 92.6(9) . 7_565 ?
C6 C9 C2 42.1(7) . 7_565 ?
C9 C9 C2 92.0(6) 7_565 7_565 ?

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 C1 C6 118.3(8) . . . 7_565 ?
O2 S1 C1 C6 -3.2(9) 7_565 . . 7_565 ?
O1 S1 C1 C6 -122.4(9) . . . 7_565 ?
O2 S1 C1 C6 3.2(9) . . . . ?
O2 S1 C1 C6 -118.3(8) 7_565 . . . ?
O1 S1 C1 C6 122.4(9) . . . . ?
O2 S1 C1 C2 -61.6(9) . . . 7_565 ?
O2 S1 C1 C2 176.9(8) 7_565 . . 7_565 ?
O1 S1 C1 C2 57.7(8) . . . 7_565 ?
O2 S1 C1 C2 -176.9(8) . . . . ?
O2 S1 C1 C2 61.6(9) 7_565 . . . ?
O1 S1 C1 C2 -57.7(8) . . . . ?
C6 C1 C2 C6 69.2(14) . . . 7_565 ?
C2 C1 C2 C6 123.9(10) 7_565 . . 7_565 ?
S1 C1 C2 C6 -110.6(9) . . . 7_565 ?
C6 C1 C2 C3 -73.1(13) 7_565 . . . ?
C6 C1 C2 C3 -3.8(18) . . . . ?
C2 C1 C2 C3 50.8(17) 7_565 . . . ?
S1 C1 C2 C3 176.3(10) . . . . ?
C6 C1 C2 C9 -38.4(8) 7_565 . . 7_565 ?
C6 C1 C2 C9 30.9(12) . . . 7_565 ?
C2 C1 C2 C9 85.5(10) 7_565 . . 7_565 ?
S1 C1 C2 C9 -149.0(6) . . . 7_565 ?
C6 C2 C3 C9 -0.9(13) 7_565 . . 7_565 ?
C1 C2 C3 C9 55.8(14) . . . 7_565 ?
C6 C2 C3 C5 -55.9(15) 7_565 . . . ?
C1 C2 C3 C5 0.9(19) . . . . ?
C9 C2 C3 C5 -55.0(11) 7_565 . . . ?
C1 C2 C3 C6 56.7(11) . . . 7_565 ?
C9 C2 C3 C6 0.9(13) 7_565 . . 7_565 ?
C9 C3 C5 C9 -68.9(13) 7_565 . . . ?
C2 C3 C5 C9 3.1(18) . . . . ?
C6 C3 C5 C9 -30.7(13) 7_565 . . . ?
C2 C3 C5 C9 72.0(14) . . . 7_565 ?
C6 C3 C5 C9 38.2(9) 7_565 . . 7_565 ?
C9 C3 C5 C3 -124.1(10) 7_565 . . 7_565 ?
C2 C3 C5 C3 -52.1(18) . . . 7_565 ?
C6 C3 C5 C3 -85.9(11) 7_565 . . 7_565 ?
C9 C3 C5 S2 110.0(9) 7_565 . . . ?
C2 C3 C5 S2 -178.0(10) . . . . ?
C6 C3 C5 S2 148.2(7) 7_565 . . . ?
O4 S2 C5 C9 117.9(8) 7_565 . . . ?
O4 S2 C5 C9 -4.8(10) . . . . ?
O3 S2 C5 C9 -123.4(9) . . . . ?
O4 S2 C5 C9 4.8(10) 7_565 . . 7_565 ?
O4 S2 C5 C9 -117.9(8) . . . 7_565 ?
O3 S2 C5 C9 123.4(9) . . . 7_565 ?
O4 S2 C5 C3 -61.1(9) 7_565 . . . ?
O4 S2 C5 C3 176.3(8) . . . . ?
O3 S2 C5 C3 57.6(9) . . . . ?
O4 S2 C5 C3 -176.3(8) 7_565 . . 7_565 ?
O4 S2 C5 C3 61.1(9) . . . 7_565 ?
O3 S2 C5 C3 -57.6(9) . . . 7_565 ?
C6 C1 C6 C2 127.8(9) 7_565 . . 7_565 ?
C2 C1 C6 C2 76.8(13) . . . 7_565 ?
S1 C1 C6 C2 -103.4(9) . . . 7_565 ?
C6 C1 C6 C9 53.9(16) 7_565 . . . ?
C2 C1 C6 C9 -73.9(12) 7_565 . . . ?
C2 C1 C6 C9 2.9(18) . . . . ?
S1 C1 C6 C9 -177.2(9) . . . . ?
C6 C1 C6 C3 90.4(9) 7_565 . . 7_565 ?
C2 C1 C6 C3 -37.3(8) 7_565 . . 7_565 ?
C2 C1 C6 C3 39.5(12) . . . 7_565 ?
S1 C1 C6 C3 -140.7(7) . . . 7_565 ?
C2 C1 C6 C6 -127.8(9) 7_565 . . 7_565 ?
C2 C1 C6 C6 -51.0(9) . . . 7_565 ?
S1 C1 C6 C6 128.9(12) . . . 7_565 ?
C9 C5 C9 C3 -127.9(9) 7_565 . . 7_565 ?
C3 C5 C9 C3 -76.4(14) . . . 7_565 ?
S2 C5 C9 C3 104.6(9) . . . 7_565 ?
C9 C5 C9 C6 -55.5(16) 7_565 . . . ?
C3 C5 C9 C6 -4.0(18) . . . . ?
C3 C5 C9 C6 72.4(13) 7_565 . . . ?
S2 C5 C9 C6 177.0(9) . . . . ?
C3 C5 C9 C9 51.5(9) . . . 7_565 ?
C3 C5 C9 C9 127.9(9) 7_565 . . 7_565 ?
S2 C5 C9 C9 -127.5(12) . . . 7_565 ?
C9 C5 C9 C2 -90.1(9) 7_565 . . 7_565 ?
C3 C5 C9 C2 -38.7(13) . . . 7_565 ?
C3 C5 C9 C2 37.8(8) 7_565 . . 7_565 ?
S2 C5 C9 C2 142.4(7) . . . 7_565 ?
C2 C6 C9 C3 0.9(12) 7_565 . . 7_565 ?
C1 C6 C9 C3 59.7(14) . . . 7_565 ?
C6 C6 C9 C3 93.6(8) 7_565 . . 7_565 ?
C2 C6 C9 C5 -57.8(15) 7_565 . . . ?
C1 C6 C9 C5 1.0(19) . . . . ?
C3 C6 C9 C5 -58.7(11) 7_565 . . . ?
C6 C6 C9 C5 34.9(11) 7_565 . . . ?
C2 C6 C9 C9 -92.7(9) 7_565 . . 7_565 ?
C1 C6 C9 C9 -33.8(11) . . . 7_565 ?
C3 C6 C9 C9 -93.6(8) 7_565 . . 7_565 ?
C6 C6 C9 C9 0.0 7_565 . . 7_565 ?
C1 C6 C9 C2 58.9(11) . . . 7_565 ?
C3 C6 C9 C2 -0.9(12) 7_565 . . 7_565 ?
C6 C6 C9 C2 92.7(9) 7_565 . . 7_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O4 . . 5_657 3.004(5) 0.880 2.184 154.9 no
N1 H1A O4 . 7_565 3_657 3.004(5) 0.880 2.184 154.9 no
N1 H1B O4 . . 3_657 3.004(5) 0.880 2.186 154.5 no
N1 H1B O4 . 7_565 5_657 3.004(5) 0.880 2.186 154.5 no
N2 H2A O1 . . . 2.925(9) 0.880 2.143 147.7 no
N2 H2B O3 . . 3_647 3.057(6) 0.880 2.219 159.0 no
N3 H3A O1 . . . 3.062(6) 0.880 2.272 149.3 no
N3 H3A O2 . . . 3.017(7) 0.880 2.256 144.8 no
N3 H3B O2 . . 4_555 2.954(7) 0.880 2.100 163.4 no
N4 H4A O2 . . 7_555 2.940(5) 0.880 2.146 149.9 no
N4 H4A O2 . 7_555 . 2.940(5) 0.880 2.146 149.9 no
N4 H4B O2 . . . 2.940(5) 0.880 2.146 149.9 no
N4 H4B O2 . 7_555 7_555 2.940(5) 0.880 2.146 149.9 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

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

data_201007_G2BDS_PhNH2
_database_code_depnum_ccdc_archive 'CCDC 2041224'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H37 N9 O6 S2'
_chemical_formula_moiety         'C26 H37 N9 O6 S2'
_chemical_formula_weight         635.76
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5488(2)
_cell_length_b                   18.0321(6)
_cell_length_c                   11.5759(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.052(6)
_cell_angle_gamma                90.0000
_cell_volume                     1575.45(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12519
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      68.35
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672.00
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_T_max  0.905

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            17391
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_theta_max         68.253
_diffrn_reflns_theta_min         3.819
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5566
_reflns_number_gt                4340
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.933

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1494
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5566
_refine_ls_number_parameters     388
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0937P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.511(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.33686(18) 0.33633(7) 1.26833(11) 0.0238(3) Uani 1 1 d . . . . .
S2 S 0.18321(18) 0.67703(7) 1.23827(11) 0.0227(3) Uani 1 1 d . . . . .
O3 O 0.1799(5) 0.3079(2) 1.2065(3) 0.0270(10) Uani 1 1 d . . . . .
O4 O 0.0196(5) 0.6895(2) 1.3008(3) 0.0263(9) Uani 1 1 d . . . . .
O14 O 0.3320(5) 0.7166(2) 1.2921(3) 0.0275(10) Uani 1 1 d . . . . .
O35 O 0.1662(5) 0.6941(2) 1.1156(3) 0.0273(10) Uani 1 1 d . . . . .
O48 O 0.3404(5) 0.3137(2) 1.3889(3) 0.0281(10) Uani 1 1 d . . . . .
O65 O 0.5009(5) 0.3201(2) 1.2089(3) 0.0258(9) Uani 1 1 d . . . . .
N5 N 0.4635(6) 0.2814(3) 0.9635(4) 0.0311(12) Uani 1 1 d . . . . .
N6 N -0.0061(6) 0.2665(3) 1.4810(4) 0.0305(12) Uani 1 1 d . . . . .
N7 N -0.1541(6) 0.3113(3) 1.3196(4) 0.0283(11) Uani 1 1 d . . . . .
N9 N -0.2646(7) 0.3711(3) 0.8398(5) 0.0364(13) Uani 1 1 d . . . . .
N10 N -0.3109(6) 0.2662(3) 1.4740(4) 0.0286(12) Uani 1 1 d . . . . .
N15 N 0.3166(6) 0.2328(3) 0.8041(4) 0.0284(12) Uani 1 1 d . . . . .
N21 N 0.1704(7) 0.2451(3) 0.9771(4) 0.0277(11) Uani 1 1 d . . . . .
N30 N -0.1801(7) 0.6359(3) 0.7127(4) 0.0375(14) Uani 1 1 d . . . . .
N42 N 0.2105(8) 0.6479(3) 0.8616(4) 0.0413(14) Uani 1 1 d . . . . .
C8 C 0.3180(8) 0.2535(3) 0.9156(5) 0.0267(13) Uani 1 1 d . . . . .
C11 C 0.3321(8) 0.5491(3) 1.1662(5) 0.0260(13) Uani 1 1 d . . . . .
H11 H 0.375380 0.577765 1.103963 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2142(8) 0.4667(3) 1.3527(5) 0.0248(13) Uani 1 1 d . . . . .
H12 H 0.177200 0.438734 1.417455 0.030 Uiso 1 1 calc R U . . .
C13 C -0.1570(8) 0.2812(3) 1.4243(5) 0.0249(12) Uani 1 1 d . . . . .
C16 C 0.1723(8) 0.5423(3) 1.3442(5) 0.0234(13) Uani 1 1 d . . . . .
H16 H 0.105183 0.565870 1.402362 0.028 Uiso 1 1 calc R U . . .
C17 C -0.1405(8) 0.5185(3) 0.6160(5) 0.0275(13) Uani 1 1 d . . . . .
H17 H -0.070623 0.501292 0.679630 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3707(8) 0.4738(3) 1.1739(5) 0.0258(13) Uani 1 1 d . . . . .
H18 H 0.438683 0.450284 1.116161 0.031 Uiso 1 1 calc R U . . .
C19 C -0.1270(8) 0.4635(4) 1.1128(5) 0.0314(14) Uani 1 1 d . . . . .
H19 H -0.064497 0.451514 1.182287 0.038 Uiso 1 1 calc R U . . .
C20 C -0.3035(8) 0.4976(3) 0.9095(5) 0.0261(13) Uani 1 1 d . . . . .
H20 H -0.365404 0.509471 0.839802 0.031 Uiso 1 1 calc R U . . .
C22 C -0.3384(8) 0.5685(4) 0.4265(5) 0.0329(15) Uani 1 1 d . . . . .
H22 H -0.403695 0.586316 0.361277 0.039 Uiso 1 1 calc R U . . .
C23 C -0.2047(8) 0.5911(3) 0.6152(5) 0.0264(13) Uani 1 1 d . . . . .
C24 C 0.3088(7) 0.4333(3) 1.2672(4) 0.0231(13) Uani 1 1 d . . . . .
C25 C -0.2372(7) 0.4268(3) 0.9256(5) 0.0253(13) Uani 1 1 d . . . . .
C26 C -0.2769(8) 0.4954(4) 0.4286(5) 0.0349(15) Uani 1 1 d . . . . .
H26 H -0.301843 0.462841 0.365873 0.042 Uiso 1 1 calc R U . . .
C27 C 0.2298(8) 0.5818(3) 1.2505(4) 0.0237(12) Uani 1 1 d . . . . .
C28 C -0.1787(9) 0.4712(4) 0.5237(5) 0.0329(15) Uani 1 1 d . . . . .
H28 H -0.136819 0.421499 0.526012 0.039 Uiso 1 1 calc R U . . .
C29 C -0.3038(8) 0.6154(4) 0.5207(5) 0.0302(14) Uani 1 1 d . . . . .
H29 H -0.348962 0.664618 0.519799 0.036 Uiso 1 1 calc R U . . .
C31 C -0.1912(8) 0.5338(4) 1.0968(5) 0.0323(15) Uani 1 1 d . . . . .
H31 H -0.175152 0.570332 1.155128 0.039 Uiso 1 1 calc R U . . .
C32 C -0.2809(8) 0.5510(4) 0.9932(5) 0.0318(14) Uani 1 1 d . . . . .
H32 H -0.325981 0.599607 0.980780 0.038 Uiso 1 1 calc R U . . .
C33 C 0.3293(8) 0.5705(4) 0.7087(5) 0.0331(15) Uani 1 1 d . . . . .
H33 H 0.365323 0.613897 0.668826 0.040 Uiso 1 1 calc R U . . .
C34 C -0.1519(8) 0.4094(3) 1.0286(5) 0.0286(13) Uani 1 1 d . . . . .
H34 H -0.110338 0.360342 1.041988 0.034 Uiso 1 1 calc R U . . .
C36 C 0.2480(8) 0.5771(4) 0.8136(5) 0.0329(14) Uani 1 1 d . . . . .
C37 C 0.3023(8) 0.4374(4) 0.7145(6) 0.0379(16) Uani 1 1 d . . . . .
H37 H 0.320833 0.390131 0.680552 0.045 Uiso 1 1 calc R U . . .
C38 C 0.2180(8) 0.4435(4) 0.8189(6) 0.0345(15) Uani 1 1 d . . . . .
H38 H 0.179078 0.400048 0.857387 0.041 Uiso 1 1 calc R U . . .
C39 C 0.3593(8) 0.5010(4) 0.6602(5) 0.0348(15) Uani 1 1 d . . . . .
H39 H 0.419605 0.497377 0.589052 0.042 Uiso 1 1 calc R U . . .
C40 C 0.1899(8) 0.5122(4) 0.8679(5) 0.0351(16) Uani 1 1 d . . . . .
H40 H 0.130491 0.515637 0.939378 0.042 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O48 1.454(4) . ?
S1 O65 1.457(4) . ?
S1 O3 1.465(4) . ?
S1 C24 1.760(6) . ?
S2 O35 1.456(4) . ?
S2 O4 1.460(4) . ?
S2 O14 1.461(4) . ?
S2 C27 1.758(6) . ?
N5 C8 1.321(7) . ?
N6 C13 1.331(7) . ?
N7 C13 1.330(7) . ?
N9 C25 1.425(7) . ?
N10 C13 1.333(7) . ?
N15 C8 1.344(7) . ?
N21 C8 1.342(7) . ?
N30 C23 1.397(7) . ?
N42 C36 1.423(9) . ?
C11 C27 1.387(7) . ?
C11 C18 1.391(8) . ?
C11 H11 0.9500 . ?
C12 C24 1.371(7) . ?
C12 C16 1.403(8) . ?
C12 H12 0.9500 . ?
C16 C27 1.375(7) . ?
C16 H16 0.9500 . ?
C17 C28 1.393(8) . ?
C17 C23 1.396(8) . ?
C17 H17 0.9500 . ?
C18 C24 1.391(7) . ?
C18 H18 0.9500 . ?
C19 C31 1.368(9) . ?
C19 C34 1.389(8) . ?
C19 H19 0.9500 . ?
C20 C32 1.374(8) . ?
C20 C25 1.382(8) . ?
C20 H20 0.9500 . ?
C22 C26 1.398(9) . ?
C22 C29 1.402(8) . ?
C22 H22 0.9500 . ?
C23 C29 1.385(8) . ?
C25 C34 1.381(8) . ?
C26 C28 1.386(9) . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C31 C32 1.402(8) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C36 1.376(8) . ?
C33 C39 1.394(9) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C36 C40 1.402(9) . ?
C37 C38 1.381(9) . ?
C37 C39 1.381(9) . ?
C37 H37 0.9500 . ?
C38 C40 1.382(10) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?

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
O48 S1 O65 113.3(2) . . ?
O48 S1 O3 111.8(2) . . ?
O65 S1 O3 112.7(2) . . ?
O48 S1 C24 106.6(2) . . ?
O65 S1 C24 107.4(3) . . ?
O3 S1 C24 104.3(3) . . ?
O35 S2 O4 113.0(2) . . ?
O35 S2 O14 111.4(2) . . ?
O4 S2 O14 111.3(2) . . ?
O35 S2 C27 107.4(2) . . ?
O4 S2 C27 106.3(3) . . ?
O14 S2 C27 107.0(3) . . ?
N5 C8 N21 120.8(5) . . ?
N5 C8 N15 120.1(6) . . ?
N21 C8 N15 119.1(6) . . ?
C27 C11 C18 119.3(6) . . ?
C27 C11 H11 120.4 . . ?
C18 C11 H11 120.4 . . ?
C24 C12 C16 119.8(5) . . ?
C24 C12 H12 120.1 . . ?
C16 C12 H12 120.1 . . ?
N7 C13 N6 120.2(5) . . ?
N7 C13 N10 120.4(5) . . ?
N6 C13 N10 119.5(5) . . ?
C27 C16 C12 119.0(5) . . ?
C27 C16 H16 120.5 . . ?
C12 C16 H16 120.5 . . ?
C28 C17 C23 120.1(6) . . ?
C28 C17 H17 119.9 . . ?
C23 C17 H17 119.9 . . ?
C24 C18 C11 119.3(6) . . ?
C24 C18 H18 120.4 . . ?
C11 C18 H18 120.4 . . ?
C31 C19 C34 120.8(6) . . ?
C31 C19 H19 119.6 . . ?
C34 C19 H19 119.6 . . ?
C32 C20 C25 120.8(5) . . ?
C32 C20 H20 119.6 . . ?
C25 C20 H20 119.6 . . ?
C26 C22 C29 119.9(6) . . ?
C26 C22 H22 120.0 . . ?
C29 C22 H22 120.0 . . ?
C29 C23 C17 119.0(5) . . ?
C29 C23 N30 121.1(6) . . ?
C17 C23 N30 119.7(5) . . ?
C12 C24 C18 121.1(6) . . ?
C12 C24 S1 119.7(4) . . ?
C18 C24 S1 119.0(4) . . ?
C34 C25 C20 119.2(5) . . ?
C34 C25 N9 120.0(5) . . ?
C20 C25 N9 120.7(5) . . ?
C28 C26 C22 118.9(6) . . ?
C28 C26 H26 120.5 . . ?
C22 C26 H26 120.5 . . ?
C16 C27 C11 121.5(6) . . ?
C16 C27 S2 120.2(4) . . ?
C11 C27 S2 118.2(4) . . ?
C26 C28 C17 121.1(6) . . ?
C26 C28 H28 119.5 . . ?
C17 C28 H28 119.5 . . ?
C23 C29 C22 120.9(6) . . ?
C23 C29 H29 119.6 . . ?
C22 C29 H29 119.6 . . ?
C19 C31 C32 119.1(6) . . ?
C19 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C20 C32 C31 119.9(6) . . ?
C20 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C36 C33 C39 120.8(6) . . ?
C36 C33 H33 119.6 . . ?
C39 C33 H33 119.6 . . ?
C25 C34 C19 120.1(6) . . ?
C25 C34 H34 120.0 . . ?
C19 C34 H34 120.0 . . ?
C33 C36 C40 118.2(6) . . ?
C33 C36 N42 121.1(6) . . ?
C40 C36 N42 120.4(6) . . ?
C38 C37 C39 119.0(6) . . ?
C38 C37 H37 120.5 . . ?
C39 C37 H37 120.5 . . ?
C37 C38 C40 120.5(6) . . ?
C37 C38 H38 119.8 . . ?
C40 C38 H38 119.8 . . ?
C37 C39 C33 120.6(6) . . ?
C37 C39 H39 119.7 . . ?
C33 C39 H39 119.7 . . ?
C38 C40 C36 120.8(6) . . ?
C38 C40 H40 119.6 . . ?
C36 C40 H40 119.6 . . ?

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
C24 C12 C16 C27 -1.0(8) . . . . ?
C27 C11 C18 C24 -1.3(8) . . . . ?
C28 C17 C23 C29 -1.1(9) . . . . ?
C28 C17 C23 N30 174.0(5) . . . . ?
C16 C12 C24 C18 2.7(8) . . . . ?
C16 C12 C24 S1 -171.9(4) . . . . ?
C11 C18 C24 C12 -1.6(9) . . . . ?
C11 C18 C24 S1 173.0(4) . . . . ?
O48 S1 C24 C12 -31.4(5) . . . . ?
O65 S1 C24 C12 -153.2(4) . . . . ?
O3 S1 C24 C12 87.0(5) . . . . ?
O48 S1 C24 C18 153.9(4) . . . . ?
O65 S1 C24 C18 32.2(5) . . . . ?
O3 S1 C24 C18 -87.7(5) . . . . ?
C32 C20 C25 C34 1.9(9) . . . . ?
C32 C20 C25 N9 178.5(5) . . . . ?
C29 C22 C26 C28 -1.4(9) . . . . ?
C12 C16 C27 C11 -1.8(8) . . . . ?
C12 C16 C27 S2 -178.8(4) . . . . ?
C18 C11 C27 C16 3.0(9) . . . . ?
C18 C11 C27 S2 -180.0(4) . . . . ?
O35 S2 C27 C16 -148.8(5) . . . . ?
O4 S2 C27 C16 -27.6(5) . . . . ?
O14 S2 C27 C16 91.5(5) . . . . ?
O35 S2 C27 C11 34.1(5) . . . . ?
O4 S2 C27 C11 155.3(4) . . . . ?
O14 S2 C27 C11 -85.6(5) . . . . ?
C22 C26 C28 C17 -0.3(9) . . . . ?
C23 C17 C28 C26 1.5(9) . . . . ?
C17 C23 C29 C22 -0.6(9) . . . . ?
N30 C23 C29 C22 -175.6(5) . . . . ?
C26 C22 C29 C23 1.8(10) . . . . ?
C34 C19 C31 C32 -0.9(9) . . . . ?
C25 C20 C32 C31 -0.6(9) . . . . ?
C19 C31 C32 C20 0.1(9) . . . . ?
C20 C25 C34 C19 -2.7(9) . . . . ?
N9 C25 C34 C19 -179.3(5) . . . . ?
C31 C19 C34 C25 2.2(9) . . . . ?
C39 C33 C36 C40 -2.5(9) . . . . ?
C39 C33 C36 N42 -177.5(6) . . . . ?
C39 C37 C38 C40 0.5(9) . . . . ?
C38 C37 C39 C33 -1.3(9) . . . . ?
C36 C33 C39 C37 2.3(9) . . . . ?
C37 C38 C40 C36 -0.7(9) . . . . ?
C33 C36 C40 C38 1.7(9) . . . . ?
N42 C36 C40 C38 176.8(6) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


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

data_p21n_sq
_database_code_depnum_ccdc_archive 'CCDC 2041226'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C H6 N3)+, (C6 H4 O6 S2)2-, 3(C4 H5 N)'
_chemical_formula_sum            'C20 H31 N9 O6 S2'
_chemical_formula_weight         557.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.4854(5)
_cell_length_b                   12.0766(7)
_cell_length_c                   16.8284(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.093(6)
_cell_angle_gamma                90
_cell_volume                     1521.25(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9442
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      67.99

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.990
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            17294
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.660
_diffrn_reflns_theta_max         68.164
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2776
_reflns_number_gt                1857
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'RAPID AUTO (Rigaku, 2011)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (CCDC, 2016)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.1099
_refine_ls_wR_factor_ref         0.3472
_refine_ls_wR_factor_gt          0.3154
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_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 0.0081(3) 0.53313(11) 0.31497(9) 0.0619(5) Uani 1 1 d . . . . .
O1 O 0.0029(7) 0.4217(3) 0.2801(2) 0.0675(12) Uani 1 1 d . . . . .
O2 O 0.1646(6) 0.5955(4) 0.2957(3) 0.0603(13) Uani 1 1 d . . . . .
O3 O -0.1555(6) 0.5942(4) 0.2963(3) 0.0716(15) Uani 1 1 d . . . . .
N1 N 0.5036(10) 0.4825(4) 0.2805(3) 0.0678(14) Uani 1 1 d . . . . .
H1 H 0.401341 0.517281 0.286841 0.081 Uiso 1 1 calc R U . . .
H2 H 0.604952 0.517969 0.287873 0.081 Uiso 1 1 calc R U . . .
N2 N 0.3509(8) 0.3262(5) 0.2495(3) 0.0649(17) Uani 1 1 d . . . . .
H3 H 0.249915 0.362373 0.256106 0.078 Uiso 1 1 calc R U . . .
H4 H 0.349145 0.255857 0.235871 0.078 Uiso 1 1 calc R U . . .
N3 N 0.6611(9) 0.3239(5) 0.2476(3) 0.0690(18) Uani 1 1 d . . . . .
H5 H 0.763024 0.359386 0.253082 0.083 Uiso 1 1 calc R U . . .
H6 H 0.660686 0.253542 0.233983 0.083 Uiso 1 1 calc R U . . .
C1 C 0.0115(12) 0.5164(5) 0.4189(3) 0.0565(14) Uani 1 1 d . . . . .
C2 C 0.1178(12) 0.5743(7) 0.4685(5) 0.084(2) Uani 1 1 d . . . . .
H7 H 0.195439 0.628575 0.446693 0.101 Uiso 1 1 calc R U . . .
C3 C -0.1186(11) 0.4416(6) 0.4512(5) 0.082(2) Uani 1 1 d . . . . .
H8 H -0.202154 0.404709 0.417871 0.098 Uiso 1 1 calc R U . . .
C4 C 0.5050(12) 0.3775(5) 0.2602(3) 0.0617(15) 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 1.431(5) . ?
S1 O3 1.463(5) . ?
S1 O1 1.468(4) . ?
S1 C1 1.761(5) . ?
N1 C4 1.314(7) . ?
N1 H1 0.8800 . ?
N1 H2 0.8800 . ?
N2 C4 1.321(9) . ?
N2 H3 0.8800 . ?
N2 H4 0.8800 . ?
N3 C4 1.352(9) . ?
N3 H5 0.8800 . ?
N3 H6 0.8800 . ?
C1 C2 1.348(10) . ?
C1 C3 1.435(10) . ?
C2 C3 1.365(11) 3_566 ?
C2 H7 0.9500 . ?
C3 H8 0.9500 . ?

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 O3 111.8(2) . . ?
O2 S1 O1 114.4(3) . . ?
O3 S1 O1 110.8(3) . . ?
O2 S1 C1 106.0(4) . . ?
O3 S1 C1 106.4(4) . . ?
O1 S1 C1 107.0(3) . . ?
C4 N1 H1 120.0 . . ?
C4 N1 H2 120.0 . . ?
H1 N1 H2 120.0 . . ?
C4 N2 H3 120.0 . . ?
C4 N2 H4 120.0 . . ?
H3 N2 H4 120.0 . . ?
C4 N3 H5 120.0 . . ?
C4 N3 H6 120.0 . . ?
H5 N3 H6 120.0 . . ?
C2 C1 C3 119.5(6) . . ?
C2 C1 S1 124.3(6) . . ?
C3 C1 S1 116.0(6) . . ?
C1 C2 C3 122.8(7) . 3_566 ?
C1 C2 H7 118.6 . . ?
C3 C2 H7 118.6 3_566 . ?
C2 C3 C1 117.5(7) 3_566 . ?
C2 C3 H8 121.3 3_566 . ?
C1 C3 H8 121.3 . . ?
N1 C4 N2 118.7(8) . . ?
N1 C4 N3 120.6(8) . . ?
N2 C4 N3 120.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 14.1(8) . . . . ?
O3 S1 C1 C2 -105.0(8) . . . . ?
O1 S1 C1 C2 136.6(8) . . . . ?
O2 S1 C1 C3 -170.8(5) . . . . ?
O3 S1 C1 C3 70.1(6) . . . . ?
O1 S1 C1 C3 -48.4(7) . . . . ?
C3 C1 C2 C3 5.9(15) . . . 3_566 ?
S1 C1 C2 C3 -179.2(7) . . . 3_566 ?
C2 C1 C3 C2 -5.6(14) . . . 3_566 ?
S1 C1 C3 C2 179.1(6) . . . 3_566 ?

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.095



####################################################################### 
# 
# 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_201008_G2BDS_pyrazine
_database_code_depnum_ccdc_archive 'CCDC 2041222'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H20 N8 O6 S2'
_chemical_formula_moiety         'C12 H20 N8 O6 S2'
_chemical_formula_weight         436.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.94009(17)
_cell_length_b                   7.4700(2)
_cell_length_c                   20.0860(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.581(6)
_cell_angle_gamma                90.0000
_cell_volume                     891.22(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7877
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456.00
_exptl_absorpt_coefficient_mu    3.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_T_max  0.852

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9589
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         4.403
_diffrn_reflns_theta_full        68.230
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1621
_reflns_number_gt                1434
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1555
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1621
_refine_ls_number_parameters     127
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1118P)²+0.0798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13351(10) 0.02629(8) 0.34814(3) 0.0242(3) Uani 1 1 d . . .
O1 O 0.0389(3) 0.1938(2) 0.32444(8) 0.0287(5) Uani 1 1 d . . .
O2 O 0.0363(3) -0.1298(2) 0.31599(8) 0.0283(5) Uani 1 1 d . . .
O3 O 0.3783(3) 0.0252(2) 0.34710(8) 0.0279(5) Uani 1 1 d . . .
N1 N 0.2813(4) 0.5363(3) 0.29165(11) 0.0285(6) Uani 1 1 d . . .
H1A H 0.2132 0.6402 0.2870 0.034 Uiso 1 1 calc R . .
H1B H 0.2078 0.4364 0.2832 0.034 Uiso 1 1 calc R . .
N2 N 0.6049(3) 0.6813(3) 0.32400(10) 0.0298(5) Uani 1 1 d . . .
H2A H 0.5364 0.7851 0.3193 0.036 Uiso 1 1 calc R . .
H2B H 0.7466 0.6775 0.3371 0.036 Uiso 1 1 calc R . .
N3 N 0.5967(3) 0.3732(3) 0.31946(10) 0.0292(5) Uani 1 1 d . . .
H3A H 0.5227 0.2731 0.3117 0.035 Uiso 1 1 calc R . .
H3B H 0.7384 0.3694 0.3326 0.035 Uiso 1 1 calc R . .
N4 N -0.0506(4) 0.5253(3) 0.43219(11) 0.0326(6) Uani 1 1 d . . .
C1 C -0.1554(4) 0.0626(3) 0.45329(12) 0.0260(6) Uani 1 1 d . . .
H1 H -0.2616 0.1044 0.4212 0.031 Uiso 1 1 calc R . .
C2 C 0.0590(4) 0.0108(3) 0.43344(12) 0.0239(6) Uani 1 1 d . . .
C3 C 0.2135(4) -0.0530(3) 0.48033(13) 0.0268(6) Uani 1 1 d . . .
H2 H 0.3589 -0.0900 0.4667 0.032 Uiso 1 1 calc R . .
C4 C 0.4941(4) 0.5303(3) 0.31133(12) 0.0240(6) Uani 1 1 d . . .
C5 C 0.1438(5) 0.4550(3) 0.45295(13) 0.0318(6) Uani 1 1 d . . .
H3 H 0.2519 0.4207 0.4208 0.038 Uiso 1 1 calc R . .
C6 C -0.1938(4) 0.5698(4) 0.47992(12) 0.0313(6) Uani 1 1 d . . .
H4 H -0.3350 0.6204 0.4677 0.038 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4500(16) . ?
S1 O2 1.4500(17) . ?
S1 O3 1.4546(18) . ?
S1 C2 1.778(3) . ?
N1 C4 1.321(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C4 1.329(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C4 1.331(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C6 1.330(3) . ?
N4 C5 1.332(3) . ?
C1 C3 1.383(3) 3_556 ?
C1 C2 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(4) . ?
C3 C1 1.383(3) 3_556 ?
C3 H2 0.9500 . ?
C5 C6 1.390(3) 3_566 ?
C5 H3 0.9500 . ?
C6 C5 1.390(3) 3_566 ?
C6 H4 0.9500 . ?

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 113.37(10) . . ?
O1 S1 O3 112.60(10) . . ?
O2 S1 O3 112.50(10) . . ?
O1 S1 C2 105.84(10) . . ?
O2 S1 C2 105.96(10) . . ?
O3 S1 C2 105.80(11) . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C6 N4 C5 115.6(2) . . ?
C3 C1 C2 120.0(2) 3_556 . ?
C3 C1 H1 120.0 3_556 . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 S1 119.68(19) . . ?
C3 C2 S1 120.3(2) . . ?
C1 C3 C2 120.0(2) 3_556 . ?
C1 C3 H2 120.0 3_556 . ?
C2 C3 H2 120.0 . . ?
N1 C4 N2 119.9(2) . . ?
N1 C4 N3 120.1(2) . . ?
N2 C4 N3 120.0(2) . . ?
N4 C5 C6 122.1(2) . 3_566 ?
N4 C5 H3 118.9 . . ?
C6 C5 H3 118.9 3_566 . ?
N4 C6 C5 122.3(2) . 3_566 ?
N4 C6 H4 118.9 . . ?
C5 C6 H4 118.9 3_566 . ?

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
C3 C1 C2 C3 0.9(4) 3_556 . . . ?
C3 C1 C2 S1 -179.18(18) 3_556 . . . ?
O1 S1 C2 C1 40.8(2) . . . . ?
O2 S1 C2 C1 -79.9(2) . . . . ?
O3 S1 C2 C1 160.46(19) . . . . ?
O1 S1 C2 C3 -139.4(2) . . . . ?
O2 S1 C2 C3 100.0(2) . . . . ?
O3 S1 C2 C3 -19.7(2) . . . . ?
C1 C2 C3 C1 -0.9(4) . . . 3_556 ?
S1 C2 C3 C1 179.18(18) . . . 3_556 ?
C6 N4 C5 C6 -0.1(4) . . . 3_566 ?
C5 N4 C6 C5 0.1(4) . . . 3_566 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O2 . . 1_565 2.931(3) 0.880 2.099 157.3 no
N1 H1B O1 . . . 3.012(3) 0.880 2.234 147.2 no
N2 H2A O3 . . 1_565 2.939(3) 0.880 2.103 158.4 no
N2 H2B O2 . . 1_665 2.932(3) 0.880 2.287 130.1 no
N3 H3A O3 . . . 2.960(3) 0.880 2.164 150.2 no
N3 H3B O1 . . 1_655 2.950(3) 0.880 2.223 139.8 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

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

data_jiso3-py
_database_code_depnum_ccdc_archive 'CCDC 1997210'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H30 N8 O8 S2'
_chemical_formula_moiety         'C18 H30 N8 O8 S2'
_chemical_formula_weight         550.60
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.3886(2)
_cell_length_b                   7.34813(19)
_cell_length_c                   17.1099(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.3380(13)
_cell_angle_gamma                90.0000
_cell_volume                     1270.88(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5954
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580.00
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  0.886

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13862
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         4.374
_diffrn_reflns_theta_full        68.230
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2329
_reflns_number_gt                2097
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0996
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2329
_refine_ls_number_parameters     171
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0507P)²+0.7763P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30193(4) 0.92871(6) 0.50723(2) 0.01812(16) Uani 1 1 d . . .
O1 O 0.36675(12) 1.08536(16) 0.55265(7) 0.0211(3) Uani 1 1 d . . .
O2 O 0.33719(12) 0.75713(17) 0.54824(7) 0.0229(3) Uani 1 1 d . . .
O3 O 0.31584(12) 0.92879(16) 0.42424(7) 0.0217(3) Uani 1 1 d . . .
C2 C 0.13058(17) 0.9635(2) 0.50156(10) 0.0180(4) Uani 1 1 d . . .
C3 C 0.07784(18) 0.9064(2) 0.56501(11) 0.0204(4) Uani 1 1 d . . .
H3 H 0.1313 0.8426 0.6090 0.025 Uiso 1 1 calc R . .
C4 C 0.05373(18) 1.0567(2) 0.43649(11) 0.0201(4) Uani 1 1 d . . .
H4 H 0.0910 1.0949 0.3934 0.024 Uiso 1 1 calc R . .
O4 O 0.47835(15) 0.42079(18) 0.22080(9) 0.0257(3) Uani 1 1 d . . .
H10 H 0.565(3) 0.429(4) 0.2315(17) 0.055(8) Uiso 1 1 d . . .
H11 H 0.449(2) 0.429(3) 0.1723(17) 0.034(7) Uiso 1 1 d . . .
N1 N 0.34463(16) 0.4224(2) 0.46187(9) 0.0229(4) Uani 1 1 d . . .
H1A H 0.3277 0.3184 0.4830 0.028 Uiso 1 1 calc R . .
H1B H 0.3449 0.5243 0.4889 0.028 Uiso 1 1 calc R . .
N2 N 0.39071(17) 0.5833(2) 0.35615(10) 0.0255(4) Uani 1 1 d . . .
H2A H 0.4044 0.5859 0.3073 0.031 Uiso 1 1 calc R . .
H2B H 0.3910 0.6853 0.3832 0.031 Uiso 1 1 calc R . .
N3 N 0.36949(15) 0.2726(2) 0.34784(9) 0.0231(3) Uani 1 1 d . . .
H3A H 0.3832 0.2761 0.2990 0.028 Uiso 1 1 calc R . .
H3B H 0.3556 0.1677 0.3693 0.028 Uiso 1 1 calc R . .
C1 C 0.36970(18) 0.4256(2) 0.38911(11) 0.0207(4) Uani 1 1 d . . .
N4 N 0.24466(15) 0.5427(2) 0.72108(9) 0.0240(4) Uani 1 1 d . . .
C5 C 0.13520(19) 0.5966(3) 0.74382(11) 0.0255(4) Uani 1 1 d . . .
H5 H 0.1453 0.6657 0.7918 0.031 Uiso 1 1 calc R . .
C6 C 0.0088(2) 0.5563(3) 0.70097(12) 0.0289(5) Uani 1 1 d . . .
H6 H -0.0660 0.5968 0.7192 0.035 Uiso 1 1 calc R . .
C7 C -0.0069(2) 0.4561(3) 0.63096(13) 0.0309(5) Uani 1 1 d . . .
H7 H -0.0928 0.4265 0.6003 0.037 Uiso 1 1 calc R . .
C8 C 0.1044(2) 0.3997(3) 0.60649(12) 0.0300(5) Uani 1 1 d . . .
H8 H 0.0968 0.3309 0.5586 0.036 Uiso 1 1 calc R . .
C9 C 0.2273(2) 0.4457(3) 0.65329(11) 0.0255(4) Uani 1 1 d . . .
H9 H 0.3036 0.4062 0.6364 0.031 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4483(13) . ?
S1 O3 1.4602(13) . ?
S1 O1 1.4631(13) . ?
S1 C2 1.7787(17) . ?
C2 C3 1.389(2) . ?
C2 C4 1.392(2) . ?
C3 C4 1.388(3) 3_576 ?
C3 H3 0.9500 . ?
C4 C3 1.388(3) 3_576 ?
C4 H4 0.9500 . ?
O4 H10 0.88(3) . ?
O4 H11 0.82(3) . ?
N1 C1 1.329(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.329(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C1 1.327(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C9 1.338(2) . ?
N4 C5 1.344(2) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?

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 O3 113.63(7) . . ?
O2 S1 O1 113.18(7) . . ?
O3 S1 O1 112.30(7) . . ?
O2 S1 C2 106.83(8) . . ?
O3 S1 C2 105.61(8) . . ?
O1 S1 C2 104.37(8) . . ?
C3 C2 C4 121.14(16) . . ?
C3 C2 S1 118.96(13) . . ?
C4 C2 S1 119.78(14) . . ?
C4 C3 C2 119.41(17) 3_576 . ?
C4 C3 H3 120.3 3_576 . ?
C2 C3 H3 120.3 . . ?
C3 C4 C2 119.46(17) 3_576 . ?
C3 C4 H4 120.3 3_576 . ?
C2 C4 H4 120.3 . . ?
H10 O4 H11 110(2) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N3 C1 N2 119.55(17) . . ?
N3 C1 N1 120.44(16) . . ?
N2 C1 N1 119.96(16) . . ?
C9 N4 C5 117.03(17) . . ?
N4 C5 C6 123.24(18) . . ?
N4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C5 C6 C7 118.82(19) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 118.82(19) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 118.47(19) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
N4 C9 C8 123.62(19) . . ?
N4 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C2 C3 35.64(16) . . . . ?
O3 S1 C2 C3 156.93(14) . . . . ?
O1 S1 C2 C3 -84.49(15) . . . . ?
O2 S1 C2 C4 -148.30(14) . . . . ?
O3 S1 C2 C4 -27.01(16) . . . . ?
O1 S1 C2 C4 91.57(15) . . . . ?
C4 C2 C3 C4 -0.1(3) . . . 3_576 ?
S1 C2 C3 C4 175.90(13) . . . 3_576 ?
C3 C2 C4 C3 0.1(3) . . . 3_576 ?
S1 C2 C4 C3 -175.87(13) . . . 3_576 ?
C9 N4 C5 C6 0.1(3) . . . . ?
N4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C5 N4 C9 C8 0.2(3) . . . . ?
C7 C8 C9 N4 -0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H10 N4 . . 3_666 2.832(2) 0.88(3) 1.96(3) 168(3) no
O4 H11 O1 . . 4_575 2.8433(18) 0.82(3) 2.03(3) 172(2) no
N1 H1A O1 . . 1_545 2.9041(19) 0.880 2.072 157.3 no
N1 H1B O2 . . . 2.880(2) 0.880 2.000 177.5 no
N2 H2A O4 . . . 2.931(2) 0.880 2.186 142.2 no
N2 H2B O3 . . . 2.970(2) 0.880 2.135 158.3 no
N3 H3A O4 . . . 2.885(2) 0.880 2.123 144.5 no
N3 H3B O3 . . 1_545 2.956(2) 0.880 2.077 176.4 no
####################################################################### 
# 
# 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_p21n_sq_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2041225'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C H6 N3)+, (C6 H4 O6 S2)2-, 3(C4 H4 S)'
_chemical_formula_sum            'C20 H28 N6 O6 S5'
_chemical_formula_weight         608.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.6230(3)
_cell_length_b                   16.8745(8)
_cell_length_c                   11.8090(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.488(6)
_cell_angle_gamma                90
_cell_volume                     1518.99(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10020
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      68.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.888
_shelx_estimated_absorpt_T_min   0.697
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5831
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            16375
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.570
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2751
_reflns_number_gt                2043
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'RAPID AUTO (Rigaku, 2011)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (CCDC, 2016)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_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)+(0.1849P)²+1.1864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2751
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0950
_refine_ls_wR_factor_ref         0.3084
_refine_ls_wR_factor_gt          0.2899
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.46946(15) 0.18512(7) 0.01995(10) 0.0567(4) Uani 1 1 d . . . . .
O1 O 0.4665(4) 0.2162(2) -0.0946(3) 0.0608(8) Uani 1 1 d . . . . .
O2 O 0.6264(4) 0.2084(2) 0.0826(3) 0.0603(9) Uani 1 1 d . . . . .
O3 O 0.3101(4) 0.2019(2) 0.0813(3) 0.0606(9) Uani 1 1 d . . . . .
N1 N 0.4676(5) 0.2778(2) 0.4809(3) 0.0587(10) Uani 1 1 d . . . . .
H1 H 0.567968 0.284881 0.516852 0.070 Uiso 1 1 calc R U . . .
H2 H 0.368034 0.283974 0.517081 0.070 Uiso 1 1 calc R U . . .
N2 N 0.6166(5) 0.2485(2) 0.3175(4) 0.0656(11) Uani 1 1 d . . . . .
H3 H 0.717064 0.255561 0.353363 0.079 Uiso 1 1 calc R U . . .
H4 H 0.615749 0.235246 0.245382 0.079 Uiso 1 1 calc R U . . .
N3 N 0.3136(5) 0.2448(2) 0.3188(4) 0.0616(11) Uani 1 1 d . . . . .
H5 H 0.214401 0.249406 0.355725 0.074 Uiso 1 1 calc R U . . .
H6 H 0.312371 0.231502 0.246693 0.074 Uiso 1 1 calc R U . . .
C1 C 0.4082(6) 0.0335(3) 0.0920(4) 0.0594(12) Uani 1 1 d . . . . .
H7 H 0.346613 0.056781 0.153167 0.071 Uiso 1 1 calc R U . . .
C2 C 0.5720(6) 0.0479(3) -0.0845(4) 0.0582(12) Uani 1 1 d . . . . .
H8 H 0.619853 0.081184 -0.141319 0.070 Uiso 1 1 calc R U . . .
C3 C 0.4823(5) 0.0811(3) 0.0058(4) 0.0523(11) Uani 1 1 d . . . . .
C4 C 0.4663(6) 0.2578(3) 0.3721(4) 0.0543(11) 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 O3 1.448(3) . ?
S1 O1 1.451(4) . ?
S1 O2 1.455(4) . ?
S1 C3 1.766(5) . ?
N1 C4 1.328(6) . ?
N1 H1 0.8800 . ?
N1 H2 0.8800 . ?
N2 C4 1.330(6) . ?
N2 H3 0.8800 . ?
N2 H4 0.8800 . ?
N3 C4 1.337(6) . ?
N3 H5 0.8800 . ?
N3 H6 0.8800 . ?
C1 C2 1.385(7) 3_655 ?
C1 C3 1.419(6) . ?
C1 H7 0.9500 . ?
C2 C3 1.389(6) . ?
C2 H8 0.9500 . ?

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 S1 O1 112.9(2) . . ?
O3 S1 O2 112.5(2) . . ?
O1 S1 O2 112.5(2) . . ?
O3 S1 C3 106.8(2) . . ?
O1 S1 C3 105.7(2) . . ?
O2 S1 C3 105.7(2) . . ?
C4 N1 H1 120.0 . . ?
C4 N1 H2 120.0 . . ?
H1 N1 H2 120.0 . . ?
C4 N2 H3 120.0 . . ?
C4 N2 H4 120.0 . . ?
H3 N2 H4 120.0 . . ?
C4 N3 H5 120.0 . . ?
C4 N3 H6 120.0 . . ?
H5 N3 H6 120.0 . . ?
C2 C1 C3 118.1(4) 3_655 . ?
C2 C1 H7 120.9 3_655 . ?
C3 C1 H7 120.9 . . ?
C1 C2 C3 120.2(4) 3_655 . ?
C1 C2 H8 119.9 3_655 . ?
C3 C2 H8 119.9 . . ?
C2 C3 C1 121.6(5) . . ?
C2 C3 S1 120.1(4) . . ?
C1 C3 S1 118.2(4) . . ?
N1 C4 N2 120.0(4) . . ?
N1 C4 N3 119.8(4) . . ?
N2 C4 N3 120.1(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
C1 C2 C3 C1 -0.3(8) 3_655 . . . ?
C1 C2 C3 S1 175.9(4) 3_655 . . . ?
C2 C1 C3 C2 0.3(8) 3_655 . . . ?
C2 C1 C3 S1 -176.0(4) 3_655 . . . ?
O3 S1 C3 C2 153.1(4) . . . . ?
O1 S1 C3 C2 32.5(4) . . . . ?
O2 S1 C3 C2 -86.9(4) . . . . ?
O3 S1 C3 C1 -30.6(4) . . . . ?
O1 S1 C3 C1 -151.1(4) . . . . ?
O2 S1 C3 C1 89.4(4) . . . . ?

_refine_diff_density_max         0.668
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.092



