# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Cytidine_(Rigaku_Master_for_Mo)
_database_code_depnum_ccdc_archive 'CCDC 2017521'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H20 N2 O2 S4'
_chemical_formula_moiety         'C20 H20 N2 O2 S4'
_chemical_formula_weight         448.63
_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                   5.868(4)
_cell_length_b                   9.531(6)
_cell_length_c                   10.618(6)
_cell_angle_alpha                107.56(5)
_cell_angle_beta                 93.87(6)
_cell_angle_gamma                106.20(6)
_cell_volume                     536.2(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    35
_cell_measurement_theta_min      15.05
_cell_measurement_theta_max      17.36
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             234.00
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.973

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

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            3667
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_theta_max         30.002
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_full        25.240
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        0.467
_reflns_number_total             3131
_reflns_number_gt                1646
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1255
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.0986
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     157
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0307P)²+0.1996P] 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         0.27
_refine_diff_density_min         -0.28
_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 0.0033 0.0016
;
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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
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 1.22780(11) 0.71790(7) 0.75321(7) 0.0457(2) Uani 1 1 d . . . . .
S2 S 1.71141(14) 0.85502(10) 0.91754(9) 0.0721(3) Uani 1 1 d . . . . .
O1 O 1.3097(4) 1.0433(2) 0.6063(2) 0.0735(7) Uani 1 1 d . . . . .
N1 N 1.5215(4) 0.9718(3) 0.7515(3) 0.0654(8) Uani 1 1 d . . . . .
C1 C 0.3108(4) 0.4894(3) 0.4095(3) 0.0450(7) Uani 1 1 d . . . . .
H1 H 0.1844 0.4829 0.3481 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5167(4) 0.6145(3) 0.4442(3) 0.0438(6) Uani 1 1 d . . . . .
H2 H 0.5264 0.6917 0.4062 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7116(4) 0.6282(3) 0.5350(2) 0.0366(5) Uani 1 1 d . . . . .
C4 C 0.9222(4) 0.7634(3) 0.5648(2) 0.0381(6) Uani 1 1 d . . . . .
H4 H 0.9117 0.8304 0.5182 0.046 Uiso 1 1 calc R U . . .
C5 C 1.1303(4) 0.8075(2) 0.6491(2) 0.0363(5) Uani 1 1 d . . . . .
C6 C 1.3198(4) 0.9520(3) 0.6631(3) 0.0490(7) Uani 1 1 d . . . . .
C7 C 1.5051(4) 0.8614(3) 0.8108(3) 0.0473(7) Uani 1 1 d . . . . .
C8A C 1.7615(8) 1.0835(5) 0.7482(5) 0.0487(15) Uani 0.661(9) 1 d . . P A 1
H8A H 1.8917 1.0458 0.7694 0.058 Uiso 0.661(9) 1 calc R U P A 1
H8B H 1.7654 1.0918 0.6595 0.058 Uiso 0.661(9) 1 calc R U P A 1
C9A C 1.7915(10) 1.2384(6) 0.8487(6) 0.0666(18) Uani 0.661(9) 1 d . . P A 1
H9A H 1.7914 1.2311 0.9379 0.080 Uiso 0.661(9) 1 calc R U P A 1
H9B H 1.6605 1.2759 0.8286 0.080 Uiso 0.661(9) 1 calc R U P A 1
C10A C 2.035(3) 1.350(3) 0.841(2) 0.100(6) Uani 0.661(9) 1 d . . P A 1
H10A H 2.0413 1.3458 0.7502 0.120 Uiso 0.661(9) 1 calc R U P A 1
H10B H 2.1642 1.3203 0.8735 0.120 Uiso 0.661(9) 1 calc R U P A 1
H10C H 2.0492 1.4541 0.8958 0.120 Uiso 0.661(9) 1 calc R U P A 1
C8B C 1.6784(14) 1.1448(9) 0.8375(9) 0.042(3) Uani 0.339(9) 1 d . . P A 2
H8C H 1.5935 1.2182 0.8354 0.050 Uiso 0.339(9) 1 calc R U P A 2
H8D H 1.7287 1.1552 0.9296 0.050 Uiso 0.339(9) 1 calc R U P A 2
C9B C 1.8849(18) 1.1627(11) 0.7631(10) 0.058(3) Uani 0.339(9) 1 d . . P A 2
H9C H 1.8291 1.1482 0.6706 0.070 Uiso 0.339(9) 1 calc R U P A 2
H9D H 1.9637 1.0861 0.7644 0.070 Uiso 0.339(9) 1 calc R U P A 2
C10B C 2.061(5) 1.327(4) 0.832(3) 0.074(7) Uani 0.339(9) 1 d . . P A 2
H10D H 2.1310 1.3359 0.9199 0.088 Uiso 0.339(9) 1 calc R U P A 2
H10E H 1.9769 1.4014 0.8402 0.088 Uiso 0.339(9) 1 calc R U P A 2
H10F H 2.1865 1.3465 0.7801 0.088 Uiso 0.339(9) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# 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 C7 1.736(3) . ?
S1 C5 1.743(2) . ?
S2 C7 1.629(3) . ?
O1 C6 1.211(3) . ?
N1 C7 1.365(3) . ?
N1 C6 1.392(3) . ?
N1 C8A 1.520(5) . ?
N1 C8B 1.591(8) . ?
C1 C2 1.375(3) . ?
C1 C3 1.395(3) 2_666 ?
C1 H1 0.9300 . ?
C2 C3 1.395(3) . ?
C2 H2 0.9300 . ?
C3 C1 1.395(3) 2_666 ?
C3 C4 1.450(3) . ?
C4 C5 1.344(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.468(3) . ?
C8A C9A 1.493(8) . ?
C8A H8A 0.9700 . ?
C8A H8B 0.9700 . ?
C9A C10A 1.548(17) . ?
C9A H9A 0.9700 . ?
C9A H9B 0.9700 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C8B C9B 1.489(15) . ?
C8B H8C 0.9700 . ?
C8B H8D 0.9700 . ?
C9B C10B 1.54(3) . ?
C9B H9C 0.9700 . ?
C9B H9D 0.9700 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?

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
C7 S1 C5 93.12(13) . . ?
C7 N1 C6 116.6(2) . . ?
C7 N1 C8A 122.3(3) . . ?
C6 N1 C8A 118.9(3) . . ?
C7 N1 C8B 117.1(4) . . ?
C6 N1 C8B 117.3(4) . . ?
C2 C1 C3 121.1(2) . 2_666 ?
C2 C1 H1 119.5 . . ?
C3 C1 H1 119.5 2_666 . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C1 117.5(2) . 2_666 ?
C2 C3 C4 117.7(2) . . ?
C1 C3 C4 124.8(2) 2_666 . ?
C5 C4 C3 130.4(2) . . ?
C5 C4 H4 114.8 . . ?
C3 C4 H4 114.8 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 S1 130.35(18) . . ?
C6 C5 S1 109.16(17) . . ?
O1 C6 N1 123.0(2) . . ?
O1 C6 C5 126.3(2) . . ?
N1 C6 C5 110.7(2) . . ?
N1 C7 S2 127.13(19) . . ?
N1 C7 S1 110.44(18) . . ?
S2 C7 S1 122.40(16) . . ?
C9A C8A N1 108.6(4) . . ?
C9A C8A H8A 110.0 . . ?
N1 C8A H8A 110.0 . . ?
C9A C8A H8B 110.0 . . ?
N1 C8A H8B 110.0 . . ?
H8A C8A H8B 108.4 . . ?
C8A C9A C10A 107.4(11) . . ?
C8A C9A H9A 110.2 . . ?
C10A C9A H9A 110.2 . . ?
C8A C9A H9B 110.2 . . ?
C10A C9A H9B 110.2 . . ?
H9A C9A H9B 108.5 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9B C8B N1 99.6(7) . . ?
C9B C8B H8C 111.8 . . ?
N1 C8B H8C 111.8 . . ?
C9B C8B H8D 111.8 . . ?
N1 C8B H8D 111.8 . . ?
H8C C8B H8D 109.6 . . ?
C8B C9B C10B 107.6(16) . . ?
C8B C9B H9C 110.2 . . ?
C10B C9B H9C 110.2 . . ?
C8B C9B H9D 110.2 . . ?
C10B C9B H9D 110.2 . . ?
H9C C9B H9D 108.5 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C3 0.6(5) 2_666 . . . ?
C1 C2 C3 C1 -0.5(5) . . . 2_666 ?
C1 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 C5 178.4(3) . . . . ?
C1 C3 C4 C5 -1.5(5) 2_666 . . . ?
C3 C4 C5 C6 -179.7(3) . . . . ?
C3 C4 C5 S1 0.9(5) . . . . ?
C7 S1 C5 C4 178.9(3) . . . . ?
C7 S1 C5 C6 -0.7(2) . . . . ?
C7 N1 C6 O1 178.4(3) . . . . ?
C8A N1 C6 O1 -18.1(5) . . . . ?
C8B N1 C6 O1 32.2(6) . . . . ?
C7 N1 C6 C5 -2.3(4) . . . . ?
C8A N1 C6 C5 161.2(3) . . . . ?
C8B N1 C6 C5 -148.5(4) . . . . ?
C4 C5 C6 O1 1.4(5) . . . . ?
S1 C5 C6 O1 -179.0(3) . . . . ?
C4 C5 C6 N1 -177.9(3) . . . . ?
S1 C5 C6 N1 1.7(3) . . . . ?
C6 N1 C7 S2 180.0(2) . . . . ?
C8A N1 C7 S2 17.1(5) . . . . ?
C8B N1 C7 S2 -33.8(6) . . . . ?
C6 N1 C7 S1 1.8(4) . . . . ?
C8A N1 C7 S1 -161.2(3) . . . . ?
C8B N1 C7 S1 148.0(4) . . . . ?
C5 S1 C7 N1 -0.6(2) . . . . ?
C5 S1 C7 S2 -178.9(2) . . . . ?
C7 N1 C8A C9A -104.2(4) . . . . ?
C6 N1 C8A C9A 93.2(4) . . . . ?
N1 C8A C9A C10A -179.0(9) . . . . ?
C7 N1 C8B C9B 110.3(6) . . . . ?
C6 N1 C8B C9B -103.7(6) . . . . ?
N1 C8B C9B C10B 179.9(14) . . . . ?

#==============================================================================

#==============================================================================
# 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_Cytidine_(Rigaku_Master_for_Mo)_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2017525'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C9 H8 N2 O2 S4'
_chemical_formula_moiety         'C9 H8 N2 O2 S4'
_chemical_formula_weight         304.41
_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                   11.429(4)
_cell_length_b                   7.888(3)
_cell_length_c                   7.254(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.20(3)
_cell_angle_gamma                90.0000
_cell_volume                     645.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    32
_cell_measurement_theta_min      15.19
_cell_measurement_theta_max      17.38
_cell_measurement_temperature    297
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312.00
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.865

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

_diffrn_ambient_temperature      297
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            1461
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_full        24.994
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -4.354
_reflns_number_total             1144
_reflns_number_gt                675
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1078
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1445
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1144
_refine_ls_number_parameters     93
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0645P)²+0.4333P] 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         0.32
_refine_diff_density_min         -0.27
_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 0.0033 0.0016
;
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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
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 0.54261(13) 0.39907(16) 0.28640(17) 0.0742(5) Uani 1 1 d . . . . .
S2 S 0.75990(19) 0.3909(2) 0.5638(2) 0.1119(8) Uani 1 1 d . . . . .
O1 O 0.6869(3) 0.6465(5) -0.0608(5) 0.0814(11) Uani 1 1 d . . . . .
N1 N 0.7395(4) 0.5391(5) 0.2272(6) 0.0689(11) Uani 1 1 d . . . . .
C1 C 0.5466(4) 0.4965(5) 0.0700(6) 0.0562(11) Uani 1 1 d . . . . .
C2 C 0.6636(5) 0.5732(5) 0.0580(8) 0.0656(13) Uani 1 1 d . . . . .
C3 C 0.6920(5) 0.4497(6) 0.3567(7) 0.0701(14) Uani 1 1 d . . . . .
C4 C 0.850(3) 0.605(5) 0.251(6) 0.079(8) Uani 0.5 1 d . . P A 1
H4A H 0.878807 0.616421 0.383861 0.095 Uiso 0.5 1 calc R U P A 1
H4B H 0.846769 0.717359 0.196302 0.095 Uiso 0.5 1 calc R U P A 1
C5 C 0.9306(10) 0.501(2) 0.168(3) 0.118(5) Uani 0.5 1 d . . P A 1
H5A H 0.903980 0.493824 0.035734 0.177 Uiso 0.5 1 calc R U P A 1
H5B H 0.933654 0.390022 0.221622 0.177 Uiso 0.5 1 calc R U P A 1
H5C H 1.008203 0.551328 0.190504 0.177 Uiso 0.5 1 calc R U P A 1
C24 C 0.883(3) 0.594(5) 0.262(5) 0.075(9) Uani 0.5 1 d . . P A 2
H24A H 0.931007 0.494102 0.270748 0.113 Uiso 0.5 1 calc R U P A 2
H24B H 0.900585 0.658326 0.375207 0.113 Uiso 0.5 1 calc R U P A 2
H24C H 0.898819 0.662151 0.158711 0.113 Uiso 0.5 1 calc R U P A 2


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C3 1.748(6) . ?
S1 C1 1.755(4) . ?
S2 C3 1.644(5) . ?
O1 C2 1.105(6) . ?
N1 C4 1.35(4) . ?
N1 C3 1.355(7) . ?
N1 C2 1.412(6) . ?
N1 C24 1.67(4) . ?
C1 C1 1.351(9) 3_665 ?
C1 C2 1.482(8) . ?
C4 C5 1.44(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C3 S1 C1 89.8(2) . . ?
C4 N1 C3 125.5(19) . . ?
C4 N1 C2 118.1(19) . . ?
C3 N1 C2 116.3(4) . . ?
C3 N1 C24 121.5(13) . . ?
C2 N1 C24 122.1(13) . . ?
C1 C1 C2 123.4(5) 3_665 . ?
C1 C1 S1 124.0(5) 3_665 . ?
C2 C1 S1 112.6(3) . . ?
O1 C2 N1 125.9(5) . . ?
O1 C2 C1 126.3(5) . . ?
N1 C2 C1 107.8(5) . . ?
N1 C3 S2 126.7(4) . . ?
N1 C3 S1 113.4(4) . . ?
S2 C3 S1 119.9(3) . . ?
N1 C4 C5 112(3) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C1 C1 178.7(5) . . . 3_665 ?
C3 S1 C1 C2 -2.2(3) . . . . ?
C4 N1 C2 O1 2.2(19) . . . . ?
C3 N1 C2 O1 178.5(5) . . . . ?
C24 N1 C2 O1 -5.4(16) . . . . ?
C4 N1 C2 C1 -176.6(18) . . . . ?
C3 N1 C2 C1 -0.3(6) . . . . ?
C24 N1 C2 C1 175.8(15) . . . . ?
C1 C1 C2 O1 2.2(8) 3_665 . . . ?
S1 C1 C2 O1 -177.0(4) . . . . ?
C1 C1 C2 N1 -179.1(5) 3_665 . . . ?
S1 C1 C2 N1 1.8(4) . . . . ?
C4 N1 C3 S2 -5(2) . . . . ?
C2 N1 C3 S2 179.4(4) . . . . ?
C24 N1 C3 S2 3.3(16) . . . . ?
C4 N1 C3 S1 174.6(19) . . . . ?
C2 N1 C3 S1 -1.4(5) . . . . ?
C24 N1 C3 S1 -177.5(15) . . . . ?
C1 S1 C3 N1 2.0(4) . . . . ?
C1 S1 C3 S2 -178.7(3) . . . . ?
C3 N1 C4 C5 100(3) . . . . ?
C2 N1 C4 C5 -84(3) . . . . ?


#==============================================================================
# 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_20180131
_database_code_depnum_ccdc_archive 'CCDC 2017522'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C26 H16 N2 O2 S4'
_chemical_formula_moiety         'C26 H16 N2 O2 S4'
_chemical_formula_weight         516.66
_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                   12.6138(4)
_cell_length_b                   5.52905(16)
_cell_length_c                   16.8453(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.8682(15)
_cell_angle_gamma                90.0000
_cell_volume                     1153.76(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3266
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      68.06
_cell_measurement_temperature    274
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.024
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532.00
_exptl_absorpt_coefficient_mu    4.017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.908

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

_diffrn_ambient_temperature      274
_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            12276
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         4.035
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_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             2098
_reflns_number_gt                1033
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1625
_refine_ls_R_factor_gt           0.1024
_refine_ls_wR_factor_ref         0.3367
_refine_ls_wR_factor_gt          0.2524
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2098
_refine_ls_number_parameters     154
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1400P)²+0.6754P] 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         0.48
_refine_diff_density_min         -0.61
_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_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 0.29421(16) 0.9696(4) 0.54830(12) 0.0785(9) Uani 1 1 d . . . . .
S2 S 0.48670(19) 1.2809(5) 0.57792(14) 0.0926(10) Uani 1 1 d . . . . .
O1 O 0.3683(4) 0.6400(10) 0.7503(3) 0.0712(15) Uani 1 1 d . . . . .
N1 N 0.4366(5) 0.9385(11) 0.6792(3) 0.0611(17) Uani 1 1 d . . . . .
C1 C 0.0581(6) 0.7070(14) 0.4933(4) 0.062(2) Uani 1 1 d . . . . .
H1 H 0.096891 0.847182 0.488062 0.075 Uiso 1 1 calc R U . . .
C2 C 0.0376(6) 0.3375(15) 0.5612(4) 0.062(2) Uani 1 1 d . . . . .
H2 H 0.061947 0.225815 0.601786 0.074 Uiso 1 1 calc R U . . .
C3 C 0.0968(6) 0.5452(15) 0.5558(4) 0.064(2) Uani 1 1 d . . . . .
C4 C 0.1932(5) 0.5894(14) 0.6162(4) 0.060(2) Uani 1 1 d . . . . .
H4 H 0.201595 0.487562 0.660925 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2719(5) 0.7525(14) 0.6182(4) 0.059(2) Uani 1 1 d . . . . .
C6 C 0.3596(6) 0.7590(14) 0.6902(5) 0.0601(19) Uani 1 1 d . . . . .
C7 C 0.4141(5) 1.0651(15) 0.6079(4) 0.066(2) Uani 1 1 d . . . . .
C8 C 0.5325(5) 0.9776(14) 0.7415(4) 0.0572(19) Uani 1 1 d . . . . .
C9 C 0.6108(6) 0.8024(14) 0.7510(5) 0.065(2) Uani 1 1 d . . . . .
H9 H 0.603560 0.666052 0.718124 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7026(6) 0.8349(17) 0.8122(5) 0.076(2) Uani 1 1 d . . . . .
H10 H 0.757579 0.720276 0.819411 0.091 Uiso 1 1 calc R U . . .
C11 C 0.7112(6) 1.0323(17) 0.8606(5) 0.073(2) Uani 1 1 d . . . . .
H11 H 0.770824 1.050828 0.902032 0.088 Uiso 1 1 calc R U . . .
C12 C 0.6306(7) 1.2068(17) 0.8481(5) 0.077(3) Uani 1 1 d . . . . .
H12 H 0.637685 1.343433 0.880944 0.093 Uiso 1 1 calc R U . . .
C13 C 0.5404(6) 1.1821(14) 0.7882(4) 0.064(2) Uani 1 1 d . . . . .
H13 H 0.486791 1.299912 0.779855 0.077 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    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.732(7) . ?
S1 C5 1.741(8) . ?
S2 C7 1.641(8) . ?
O1 C6 1.196(8) . ?
N1 C7 1.373(9) . ?
N1 C6 1.425(9) . ?
N1 C8 1.460(8) . ?
C1 C2 1.394(9) 3_566 ?
C1 C3 1.397(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.452(9) . ?
C4 C5 1.336(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.480(9) . ?
C8 C9 1.372(9) . ?
C8 C13 1.371(10) . ?
C9 C10 1.409(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C5 93.0(3) . . ?
C7 N1 C6 115.8(6) . . ?
C7 N1 C8 124.0(6) . . ?
C6 N1 C8 120.2(6) . . ?
C2 C1 C3 121.3(7) 3_566 . ?
C2 C1 H1 119.4 3_566 . ?
C3 C1 H1 119.4 . . ?
C3 C2 C1 121.0(7) . 3_566 ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 3_566 . ?
C2 C3 C1 117.7(6) . . ?
C2 C3 C4 119.0(7) . . ?
C1 C3 C4 123.2(7) . . ?
C5 C4 C3 130.6(7) . . ?
C5 C4 H4 114.7 . . ?
C3 C4 H4 114.7 . . ?
C4 C5 C6 118.3(7) . . ?
C4 C5 S1 131.5(5) . . ?
C6 C5 S1 110.2(5) . . ?
O1 C6 N1 122.5(6) . . ?
O1 C6 C5 128.0(7) . . ?
N1 C6 C5 109.5(6) . . ?
N1 C7 S2 127.2(5) . . ?
N1 C7 S1 111.4(5) . . ?
S2 C7 S1 121.3(4) . . ?
C9 C8 C13 122.8(7) . . ?
C9 C8 N1 117.4(6) . . ?
C13 C8 N1 119.7(7) . . ?
C8 C9 C10 118.1(7) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C11 C10 C9 120.3(8) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.7(8) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 121.5(8) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C8 C13 C12 117.6(8) . . ?
C8 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?

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
C1 C2 C3 C1 -0.7(12) 3_566 . . . ?
C1 C2 C3 C4 177.1(7) 3_566 . . . ?
C2 C1 C3 C2 0.7(12) 3_566 . . . ?
C2 C1 C3 C4 -177.0(7) 3_566 . . . ?
C2 C3 C4 C5 168.7(8) . . . . ?
C1 C3 C4 C5 -13.7(13) . . . . ?
C3 C4 C5 C6 178.2(8) . . . . ?
C3 C4 C5 S1 -2.9(13) . . . . ?
C7 S1 C5 C4 -178.1(8) . . . . ?
C7 S1 C5 C6 1.0(6) . . . . ?
C7 N1 C6 O1 -178.3(7) . . . . ?
C8 N1 C6 O1 2.0(11) . . . . ?
C7 N1 C6 C5 0.8(9) . . . . ?
C8 N1 C6 C5 -178.9(6) . . . . ?
C4 C5 C6 O1 -3.0(13) . . . . ?
S1 C5 C6 O1 177.9(7) . . . . ?
C4 C5 C6 N1 178.0(6) . . . . ?
S1 C5 C6 N1 -1.2(8) . . . . ?
C6 N1 C7 S2 -179.9(6) . . . . ?
C8 N1 C7 S2 -0.2(12) . . . . ?
C6 N1 C7 S1 -0.1(9) . . . . ?
C8 N1 C7 S1 179.6(5) . . . . ?
C5 S1 C7 N1 -0.5(6) . . . . ?
C5 S1 C7 S2 179.3(6) . . . . ?
C7 N1 C8 C9 -108.3(9) . . . . ?
C6 N1 C8 C9 71.4(9) . . . . ?
C7 N1 C8 C13 72.6(10) . . . . ?
C6 N1 C8 C13 -107.7(8) . . . . ?
C13 C8 C9 C10 0.5(12) . . . . ?
N1 C8 C9 C10 -178.5(7) . . . . ?
C8 C9 C10 C11 1.2(12) . . . . ?
C9 C10 C11 C12 -2.0(13) . . . . ?
C10 C11 C12 C13 1.2(12) . . . . ?
C9 C8 C13 C12 -1.3(12) . . . . ?
N1 C8 C13 C12 177.7(7) . . . . ?
C11 C12 C13 C8 0.4(12) . . . . ?

#==============================================================================

#==============================================================================
# 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_20190111
_database_code_depnum_ccdc_archive 'CCDC 2017523'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C18 H10 N2 O2 S4'
_chemical_formula_moiety         'C18 H10 N2 O2 S4'
_chemical_formula_weight         414.53
_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                   4.8107(4)
_cell_length_b                   9.0732(6)
_cell_length_c                   11.0382(6)
_cell_angle_alpha                108.240(3)
_cell_angle_beta                 98.143(4)
_cell_angle_gamma                96.693(4)
_cell_volume                     446.30(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    463
_cell_measurement_theta_min      8.45
_cell_measurement_theta_max      67.19
_cell_measurement_temperature    274
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212.00
_exptl_absorpt_coefficient_mu    5.030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.258
_exptl_absorpt_correction_T_max  0.904

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

_diffrn_ambient_temperature      274
_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            4892
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         4.295
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_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             1611
_reflns_number_gt                805
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1228
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2371
_refine_ls_wR_factor_gt          0.1775
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     118
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0912P)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         0.57
_refine_diff_density_min         -0.55
_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_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 0.2252(4) 0.36041(17) 0.35498(13) 0.0566(6) Uani 1 1 d . . . . .
S2 S 0.5145(4) 0.42599(19) 0.15354(14) 0.0678(7) Uani 1 1 d . . . . .
O1 O 0.0062(10) 0.7668(5) 0.4693(4) 0.0614(13) Uani 1 1 d . . . . .
N1 N 0.2485(11) 0.6264(5) 0.3117(4) 0.0499(14) Uani 1 1 d . . . . .
C1 C 0.0697(14) 0.5045(7) 0.4510(5) 0.0518(17) Uani 1 1 d . . . . .
C2 C 0.3314(14) 0.4841(7) 0.2692(5) 0.0555(19) Uani 1 1 d . . . . .
C3 C 0.1020(13) 0.6498(7) 0.4148(5) 0.0478(15) Uani 1 1 d . . . . .
C4 C 0.2889(15) 0.7503(7) 0.2555(5) 0.0529(17) Uani 1 1 d . . . . .
C5 C 0.4979(17) 0.8761(8) 0.3136(6) 0.072(2) Uani 1 1 d . . . . .
H5 H 0.614707 0.885344 0.391235 0.086 Uiso 1 1 calc R U . . .
C6 C 0.5379(16) 0.9914(7) 0.2571(6) 0.069(2) Uani 1 1 d . . . . .
H6 H 0.682343 1.078216 0.296369 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3654(17) 0.9771(8) 0.1440(7) 0.070(2) Uani 1 1 d . . . . .
H7 H 0.390443 1.055012 0.106372 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1537(17) 0.8477(8) 0.0847(6) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.036433 0.838625 0.007227 0.085 Uiso 1 1 calc R U . . .
C9 C 0.1151(16) 0.7327(7) 0.1393(6) 0.073(2) Uani 1 1 d . . . . .
H9 H -0.025523 0.644203 0.098966 0.087 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    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.726(6) . ?
S1 C2 1.757(6) . ?
S2 C2 1.640(7) . ?
O1 C3 1.223(7) . ?
N1 C2 1.357(6) . ?
N1 C3 1.395(7) . ?
N1 C4 1.452(7) . ?
C1 C1 1.370(12) 2_566 ?
C1 C3 1.490(8) . ?
C4 C5 1.348(8) . ?
C4 C9 1.380(7) . ?
C5 C6 1.384(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C2 91.1(3) . . ?
C2 N1 C3 115.8(5) . . ?
C2 N1 C4 125.5(5) . . ?
C3 N1 C4 118.6(5) . . ?
C1 C1 C3 121.2(7) 2_566 . ?
C1 C1 S1 127.4(6) 2_566 . ?
C3 C1 S1 111.3(4) . . ?
N1 C2 S2 126.6(5) . . ?
N1 C2 S1 112.4(5) . . ?
S2 C2 S1 121.0(3) . . ?
O1 C3 N1 128.0(6) . . ?
O1 C3 C1 122.7(5) . . ?
N1 C3 C1 109.3(5) . . ?
C5 C4 C9 121.3(6) . . ?
C5 C4 N1 120.4(5) . . ?
C9 C4 N1 118.3(5) . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.3(6) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 118.7(6) . . ?
C8 C9 H9 120.6 . . ?
C4 C9 H9 120.6 . . ?

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
C2 S1 C1 C1 179.9(8) . . . 2_566 ?
C2 S1 C1 C3 0.0(4) . . . . ?
C3 N1 C2 S2 -177.9(4) . . . . ?
C4 N1 C2 S2 5.0(9) . . . . ?
C3 N1 C2 S1 1.1(7) . . . . ?
C4 N1 C2 S1 -176.1(4) . . . . ?
C1 S1 C2 N1 -0.6(5) . . . . ?
C1 S1 C2 S2 178.4(4) . . . . ?
C2 N1 C3 O1 -179.8(6) . . . . ?
C4 N1 C3 O1 -2.5(9) . . . . ?
C2 N1 C3 C1 -1.0(7) . . . . ?
C4 N1 C3 C1 176.3(5) . . . . ?
C1 C1 C3 O1 -0.4(10) 2_566 . . . ?
S1 C1 C3 O1 179.4(5) . . . . ?
C1 C1 C3 N1 -179.3(7) 2_566 . . . ?
S1 C1 C3 N1 0.5(6) . . . . ?
C2 N1 C4 C5 -102.6(8) . . . . ?
C3 N1 C4 C5 80.3(8) . . . . ?
C2 N1 C4 C9 75.0(9) . . . . ?
C3 N1 C4 C9 -102.0(7) . . . . ?
C9 C4 C5 C6 0.9(11) . . . . ?
N1 C4 C5 C6 178.5(6) . . . . ?
C4 C5 C6 C7 0.3(11) . . . . ?
C5 C6 C7 C8 -0.8(11) . . . . ?
C6 C7 C8 C9 0.1(11) . . . . ?
C7 C8 C9 C4 1.1(11) . . . . ?
C5 C4 C9 C8 -1.6(11) . . . . ?
N1 C4 C9 C8 -179.2(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_Cytidine_(Rigaku_Master_for_Mo)_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2017527'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C11 H12 N2 O2 S4'
_chemical_formula_moiety         'C11 H12 N2 O2 S4'
_chemical_formula_weight         332.47
_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                   25.445(6)
_cell_length_b                   8.045(4)
_cell_length_c                   7.101(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.45(2)
_cell_angle_gamma                90.0000
_cell_volume                     1451.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28
_cell_measurement_theta_min      15.21
_cell_measurement_theta_max      17.40
_cell_measurement_temperature    297
#------------------------------------------------------------------------------
_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.937

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

_diffrn_ambient_temperature      297
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω
_diffrn_reflns_number            3177
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.656
_diffrn_reflns_theta_full        25.023
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -5.062
_reflns_number_total             2572
_reflns_number_gt                1445
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1038
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1170
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2572
_refine_ls_number_parameters     174
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0561P)²+0.2800P] 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         0.28
_refine_diff_density_min         -0.26
_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 0.0033 0.0016
;
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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
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 0.74256(4) 0.39386(14) 0.52956(14) 0.0460(3) Uani 1 1 d . . . . .
S2 S 0.78386(4) 0.60428(14) -0.01518(14) 0.0471(3) Uani 1 1 d . . . . .
S3 S 0.64511(5) 0.39123(17) 0.73509(16) 0.0642(4) Uani 1 1 d . . . . .
S4 S 0.88062(5) 0.60664(18) -0.22408(18) 0.0701(4) Uani 1 1 d . . . . .
O1 O 0.68234(10) 0.6566(4) 0.1262(4) 0.0534(8) Uani 1 1 d . . . . .
O2 O 0.84537(10) 0.3438(4) 0.3882(4) 0.0555(8) Uani 1 1 d . . . . .
N1 N 0.65756(11) 0.5413(4) 0.4033(4) 0.0395(8) Uani 1 1 d . . . . .
N2 N 0.86949(12) 0.4593(4) 0.1106(4) 0.0426(8) Uani 1 1 d . . . . .
C1 C 0.67669(15) 0.4478(5) 0.5523(5) 0.0431(10) Uani 1 1 d . . . . .
C2 C 0.69243(14) 0.5750(5) 0.2648(5) 0.0400(9) Uani 1 1 d . . . . .
C3 C 0.74336(14) 0.4944(4) 0.3147(5) 0.0367(9) Uani 1 1 d . . . . .
C4 C 0.78398(15) 0.5050(4) 0.2004(5) 0.0384(9) Uani 1 1 d . . . . .
C5 C 0.83501(14) 0.4251(5) 0.2499(5) 0.0416(9) Uani 1 1 d . . . . .
C6 C 0.85007(15) 0.5512(5) -0.0390(6) 0.0454(10) Uani 1 1 d . . . . .
C7 C 0.60449(14) 0.6133(5) 0.3866(6) 0.0481(10) Uani 1 1 d . . . . .
H7A H 0.606325 0.723910 0.333035 0.058 Uiso 1 1 calc R U . . .
H7B H 0.591293 0.623686 0.511402 0.058 Uiso 1 1 calc R U . . .
C8 C 0.56681(16) 0.5097(6) 0.2652(7) 0.0605(12) Uani 1 1 d . . . . .
H8A H 0.563699 0.400336 0.320882 0.073 Uiso 1 1 calc R U . . .
H8B H 0.580292 0.496274 0.141240 0.073 Uiso 1 1 calc R U . . .
C9 C 0.51292(17) 0.5917(8) 0.2462(8) 0.0850(17) Uani 1 1 d . . . . .
H9A H 0.516020 0.699791 0.190786 0.128 Uiso 1 1 calc R U . . .
H9B H 0.499224 0.602402 0.368697 0.128 Uiso 1 1 calc R U . . .
H9C H 0.489482 0.524568 0.167230 0.128 Uiso 1 1 calc R U . . .
C10 C 0.92323(14) 0.3914(6) 0.1271(6) 0.0542(11) Uani 1 1 d . . . . .
H10A H 0.936239 0.379761 0.002178 0.065 Uiso 1 1 calc R U . . .
H10B H 0.922483 0.281776 0.183764 0.065 Uiso 1 1 calc R U . . .
C11 C 0.96027(18) 0.5016(7) 0.2455(9) 0.095(2) Uani 1 1 d . . . . .
H11A H 0.948096 0.510612 0.370476 0.142 Uiso 1 1 calc R U . . .
H11B H 0.961284 0.610013 0.189391 0.142 Uiso 1 1 calc R U . . .
H11C H 0.994944 0.454124 0.251879 0.142 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C3 1.728(4) . ?
S1 C1 1.748(4) . ?
S2 C4 1.726(4) . ?
S2 C6 1.756(4) . ?
S3 C1 1.632(4) . ?
S4 C6 1.629(4) . ?
O1 C2 1.198(4) . ?
O2 C5 1.196(4) . ?
N1 C1 1.364(5) . ?
N1 C2 1.390(5) . ?
N1 C7 1.467(4) . ?
N2 C6 1.362(5) . ?
N2 C5 1.389(5) . ?
N2 C10 1.471(5) . ?
C2 C3 1.473(5) . ?
C3 C4 1.355(5) . ?
C4 C5 1.473(5) . ?
C7 C8 1.502(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.520(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.512(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C3 S1 C1 91.58(18) . . ?
C4 S2 C6 91.29(18) . . ?
C1 N1 C2 116.3(3) . . ?
C1 N1 C7 124.3(3) . . ?
C2 N1 C7 119.3(3) . . ?
C6 N2 C5 116.6(3) . . ?
C6 N2 C10 123.8(3) . . ?
C5 N2 C10 119.6(3) . . ?
N1 C1 S3 126.9(3) . . ?
N1 C1 S1 111.4(3) . . ?
S3 C1 S1 121.7(2) . . ?
O1 C2 N1 125.0(3) . . ?
O1 C2 C3 125.5(4) . . ?
N1 C2 C3 109.5(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 S1 127.5(3) . . ?
C2 C3 S1 111.2(3) . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 S2 126.9(3) . . ?
C5 C4 S2 111.6(3) . . ?
O2 C5 N2 125.2(3) . . ?
O2 C5 C4 125.6(4) . . ?
N2 C5 C4 109.2(3) . . ?
N2 C6 S4 127.5(3) . . ?
N2 C6 S2 111.2(3) . . ?
S4 C6 S2 121.2(2) . . ?
N1 C7 C8 112.3(3) . . ?
N1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 110.6(4) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 111.9(4) . . ?
N2 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 S3 179.3(3) . . . . ?
C7 N1 C1 S3 2.4(5) . . . . ?
C2 N1 C1 S1 0.3(4) . . . . ?
C7 N1 C1 S1 -176.5(3) . . . . ?
C3 S1 C1 N1 -1.4(3) . . . . ?
C3 S1 C1 S3 179.6(3) . . . . ?
C1 N1 C2 O1 -179.1(4) . . . . ?
C7 N1 C2 O1 -2.1(6) . . . . ?
C1 N1 C2 C3 1.2(4) . . . . ?
C7 N1 C2 C3 178.2(3) . . . . ?
O1 C2 C3 C4 -1.2(6) . . . . ?
N1 C2 C3 C4 178.5(3) . . . . ?
O1 C2 C3 S1 178.1(3) . . . . ?
N1 C2 C3 S1 -2.2(4) . . . . ?
C1 S1 C3 C4 -178.7(3) . . . . ?
C1 S1 C3 C2 2.0(3) . . . . ?
C2 C3 C4 C5 179.8(4) . . . . ?
S1 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 S2 -1.5(5) . . . . ?
S1 C3 C4 S2 179.3(2) . . . . ?
C6 S2 C4 C3 179.0(3) . . . . ?
C6 S2 C4 C5 -2.2(3) . . . . ?
C6 N2 C5 O2 178.5(4) . . . . ?
C10 N2 C5 O2 0.7(6) . . . . ?
C6 N2 C5 C4 -1.6(5) . . . . ?
C10 N2 C5 C4 -179.4(3) . . . . ?
C3 C4 C5 O2 1.2(6) . . . . ?
S2 C4 C5 O2 -177.6(3) . . . . ?
C3 C4 C5 N2 -178.6(3) . . . . ?
S2 C4 C5 N2 2.6(4) . . . . ?
C5 N2 C6 S4 -178.5(3) . . . . ?
C10 N2 C6 S4 -0.8(6) . . . . ?
C5 N2 C6 S2 0.0(4) . . . . ?
C10 N2 C6 S2 177.7(3) . . . . ?
C4 S2 C6 N2 1.3(3) . . . . ?
C4 S2 C6 S4 180.0(3) . . . . ?
C1 N1 C7 C8 -98.3(4) . . . . ?
C2 N1 C7 C8 84.9(4) . . . . ?
N1 C7 C8 C9 -178.0(4) . . . . ?
C6 N2 C10 C11 96.9(5) . . . . ?
C5 N2 C10 C11 -85.4(5) . . . . ?


#==============================================================================
# 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_20190906
_database_code_depnum_ccdc_archive 'CCDC 2017524'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C10 H10 N2 O2 S4'
_chemical_formula_moiety         'C10 H10 N2 O2 S4'
_chemical_formula_weight         318.44
_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                   14.3245(9)
_cell_length_b                   4.9698(3)
_cell_length_c                   19.9041(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.595(3)
_cell_angle_gamma                90.0000
_cell_volume                     1357.94(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5457
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    274
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.00
_exptl_absorpt_coefficient_mu    6.401
_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  0.938

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

_diffrn_ambient_temperature      274
_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            13966
_diffrn_reflns_av_unetI/netI     0.1834
_diffrn_reflns_av_R_equivalents  0.1548
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_full        66.596
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2393
_reflns_number_gt                968
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1507
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2123
_refine_ls_wR_factor_gt          0.1579
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     164
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0947P)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         0.48
_refine_diff_density_min         -0.48
_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_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 0.49357(12) 0.7426(3) 0.42559(8) 0.0756(6) Uani 1 1 d . . . . .
S2 S 0.67930(12) 0.3769(3) 0.45264(8) 0.0727(6) Uani 1 1 d . . . . .
S3 S 0.31791(15) 1.0873(4) 0.39930(10) 0.0985(7) Uani 1 1 d . . . . .
S4 S 0.84918(14) 0.0125(3) 0.47326(10) 0.0901(7) Uani 1 1 d . . . . .
O1 O 0.5714(3) 1.0611(7) 0.2744(2) 0.0746(13) Uani 1 1 d . . . . .
O2 O 0.7252(3) 0.7125(9) 0.2910(2) 0.0857(15) Uani 1 1 d . . . . .
N1 N 0.4505(4) 1.0899(8) 0.3279(3) 0.0698(15) Uani 1 1 d . . . . .
H1 H 0.420889 1.218462 0.301287 0.084 Uiso 1 1 calc R U . . .
N2 N 0.7901(4) 0.3818(9) 0.3715(3) 0.0713(15) Uani 1 1 d . . . . .
C1 C 0.4137(5) 0.9905(11) 0.3800(3) 0.0691(18) Uani 1 1 d . . . . .
C2 C 0.5343(5) 0.9832(11) 0.3186(3) 0.0639(17) Uani 1 1 d . . . . .
C3 C 0.5721(4) 0.7674(10) 0.3726(3) 0.0643(17) Uani 1 1 d . . . . .
C4 C 0.6508(5) 0.6065(10) 0.3834(3) 0.0658(18) Uani 1 1 d . . . . .
C5 C 0.7220(5) 0.5852(12) 0.3409(4) 0.0730(19) Uani 1 1 d . . . . .
C6 C 0.7796(4) 0.2519(11) 0.4299(3) 0.0697(17) Uani 1 1 d . . . . .
C7 C 0.8657(5) 0.3157(13) 0.3376(4) 0.094(2) Uani 1 1 d . . . . .
H7A H 0.842000 0.357420 0.288027 0.113 Uiso 1 1 calc R U . . .
H7B H 0.879288 0.124333 0.342224 0.113 Uiso 1 1 calc R U . . .
C8 C 0.9596(6) 0.4721(13) 0.3699(4) 0.113(3) Uani 1 1 d . . . . .
H8A H 0.946621 0.663594 0.364448 0.136 Uiso 1 1 calc R U . . .
H8B H 0.982983 0.433092 0.419694 0.136 Uiso 1 1 calc R U . . .
C9 C 1.0364(6) 0.3973(15) 0.3354(5) 0.138(3) Uani 1 1 d . . . . .
H9A H 1.056160 0.212758 0.347691 0.166 Uiso 1 1 calc R U . . .
H9B H 1.007925 0.404302 0.284996 0.166 Uiso 1 1 calc R U . . .
C10 C 1.1204(6) 0.5618(15) 0.3534(5) 0.148(3) Uani 1 1 d . . . . .
H10A H 1.152579 0.544820 0.402625 0.221 Uiso 1 1 calc R U . . .
H10B H 1.101821 0.745959 0.342638 0.221 Uiso 1 1 calc R U . . .
H10C H 1.163850 0.506466 0.327152 0.221 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    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_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 C1 1.749(6) . ?
S1 C3 1.752(6) . ?
S2 C6 1.739(6) . ?
S2 C4 1.746(6) . ?
S3 C1 1.601(7) . ?
S4 C6 1.632(6) . ?
O1 C2 1.214(6) . ?
O2 C5 1.190(7) . ?
N1 C2 1.373(7) . ?
N1 C1 1.382(6) . ?
N1 H1 0.8600 . ?
N2 C6 1.375(6) . ?
N2 C5 1.417(7) . ?
N2 C7 1.467(7) . ?
C2 C3 1.506(7) . ?
C3 C4 1.349(8) . ?
C4 C5 1.501(8) . ?
C7 C8 1.528(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.501(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.413(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C1 S1 C3 94.3(3) . . ?
C6 S2 C4 93.0(3) . . ?
C2 N1 C1 119.9(5) . . ?
C2 N1 H1 120.0 . . ?
C1 N1 H1 120.0 . . ?
C6 N2 C5 118.0(6) . . ?
C6 N2 C7 123.9(5) . . ?
C5 N2 C7 118.1(6) . . ?
N1 C1 S3 127.6(5) . . ?
N1 C1 S1 108.0(4) . . ?
S3 C1 S1 124.4(4) . . ?
O1 C2 N1 123.7(6) . . ?
O1 C2 C3 127.1(6) . . ?
N1 C2 C3 109.2(6) . . ?
C4 C3 C2 130.5(6) . . ?
C4 C3 S1 121.0(5) . . ?
C2 C3 S1 108.6(5) . . ?
C3 C4 C5 128.6(6) . . ?
C3 C4 S2 120.6(5) . . ?
C5 C4 S2 110.8(5) . . ?
O2 C5 N2 123.5(7) . . ?
O2 C5 C4 128.8(6) . . ?
N2 C5 C4 107.7(6) . . ?
N2 C6 S4 126.2(5) . . ?
N2 C6 S2 110.5(4) . . ?
S4 C6 S2 123.2(4) . . ?
N2 C7 C8 111.7(6) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.7(7) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 115.0(8) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 S3 179.8(5) . . . . ?
C2 N1 C1 S1 2.2(7) . . . . ?
C3 S1 C1 N1 -1.9(4) . . . . ?
C3 S1 C1 S3 -179.6(4) . . . . ?
C1 N1 C2 O1 -179.4(5) . . . . ?
C1 N1 C2 C3 -1.3(7) . . . . ?
O1 C2 C3 C4 -2.8(10) . . . . ?
N1 C2 C3 C4 179.1(6) . . . . ?
O1 C2 C3 S1 177.7(5) . . . . ?
N1 C2 C3 S1 -0.3(6) . . . . ?
C1 S1 C3 C4 -178.2(5) . . . . ?
C1 S1 C3 C2 1.3(4) . . . . ?
C2 C3 C4 C5 -3.9(10) . . . . ?
S1 C3 C4 C5 175.5(4) . . . . ?
C2 C3 C4 S2 178.2(4) . . . . ?
S1 C3 C4 S2 -2.4(7) . . . . ?
C6 S2 C4 C3 178.2(5) . . . . ?
C6 S2 C4 C5 0.0(4) . . . . ?
C6 N2 C5 O2 178.9(6) . . . . ?
C7 N2 C5 O2 -3.2(9) . . . . ?
C6 N2 C5 C4 -0.1(7) . . . . ?
C7 N2 C5 C4 177.8(5) . . . . ?
C3 C4 C5 O2 3.0(11) . . . . ?
S2 C4 C5 O2 -178.9(6) . . . . ?
C3 C4 C5 N2 -178.0(5) . . . . ?
S2 C4 C5 N2 0.1(6) . . . . ?
C5 N2 C6 S4 179.9(4) . . . . ?
C7 N2 C6 S4 2.1(9) . . . . ?
C5 N2 C6 S2 0.1(6) . . . . ?
C7 N2 C6 S2 -177.6(5) . . . . ?
C4 S2 C6 N2 -0.1(4) . . . . ?
C4 S2 C6 S4 -179.8(4) . . . . ?
C6 N2 C7 C8 -88.0(7) . . . . ?
C5 N2 C7 C8 94.2(7) . . . . ?
N2 C7 C8 C9 178.9(6) . . . . ?
C7 C8 C9 C10 170.0(8) . . . . ?

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 H1 O1 . . 2_655 3.059(6) 0.860 2.297 147.8 no
N1 H1 O2 . . 2_655 2.983(6) 0.860 2.358 129.9 no

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


####################################################################### 
# 
# 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_Cytidine_(Rigaku_Master_for_Mo)_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2017526'
loop_
_audit_author_name
_audit_author_address
'Tadashi Kawamoto'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C11 H12 N2 O2 S4'
_chemical_formula_moiety         'C11 H12 N2 O2 S4'
_chemical_formula_weight         332.47
_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                   26.578(7)
_cell_length_b                   7.813(3)
_cell_length_c                   7.2475(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.773(17)
_cell_angle_gamma                90.0000
_cell_volume                     1501.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      15.09
_cell_measurement_theta_max      17.48
_cell_measurement_temperature    297
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.939

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

_diffrn_ambient_temperature      297
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω
_diffrn_reflns_number            3359
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_full        25.240
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -1.244
_reflns_number_total             2727
_reflns_number_gt                1475
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1071
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1140
_refine_ls_number_restraints     12
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2727
_refine_ls_number_parameters     174
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0595P)²+0.4815P] 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         0.26
_refine_diff_density_min         -0.23
_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 0.0033 0.0016
;
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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
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 0.41746(5) 0.38426(16) -0.06669(17) 0.0860(4) Uani 1 1 d . . . . .
S2 S 0.32411(4) 0.39878(13) 0.13058(13) 0.0621(3) Uani 1 1 d . . . . .
S3 S 0.28722(4) 0.60029(12) 0.67309(13) 0.0628(3) Uani 1 1 d . . . . .
S4 S 0.19467(5) 0.60125(15) 0.87600(16) 0.0828(4) Uani 1 1 d . . . . .
O1 O 0.38618(10) 0.6472(3) 0.5377(4) 0.0730(8) Uani 1 1 d . . . . .
O2 O 0.22655(10) 0.3507(3) 0.2651(3) 0.0690(8) Uani 1 1 d . . . . .
N1 N 0.40769(12) 0.5359(4) 0.2609(4) 0.0589(8) Uani 1 1 d . . . . .
N2 N 0.20438(12) 0.4597(4) 0.5429(4) 0.0566(8) Uani 1 1 d . . . . .
C1 C 0.38785(15) 0.4451(5) 0.1105(5) 0.0604(10) Uani 1 1 d . . . . .
C2 C 0.45995(15) 0.5960(5) 0.2781(6) 0.0755(12) Uani 1 1 d . . . . .
H2A H 0.468779 0.642939 0.162174 0.113 Uiso 1 1 calc R U . . .
H2B H 0.481904 0.501758 0.311342 0.113 Uiso 1 1 calc R U . . .
H2C H 0.463457 0.682548 0.372042 0.113 Uiso 1 1 calc R U . . .
C3 C 0.37485(15) 0.5690(4) 0.3971(5) 0.0567(10) Uani 1 1 d . . . . .
C4 C 0.32526(15) 0.4961(4) 0.3467(5) 0.0522(9) Uani 1 1 d . . . . .
C5 C 0.28692(15) 0.5059(4) 0.4564(5) 0.0532(9) Uani 1 1 d . . . . .
C6 C 0.23717(15) 0.4298(4) 0.4061(5) 0.0579(10) Uani 1 1 d . . . . .
C7 C 0.22368(15) 0.5485(4) 0.6944(5) 0.0592(10) Uani 1 1 d . . . . .
C8 C 0.15332(15) 0.3920(5) 0.5240(6) 0.0708(12) Uani 1 1 d . . . . .
H8A H 0.139877 0.384831 0.645005 0.085 Uiso 1 1 calc R U . . .
H8B H 0.153926 0.277372 0.472737 0.085 Uiso 1 1 calc R U . . .
C9 C 0.11887(19) 0.5068(7) 0.3972(8) 0.1120(19) Uani 1 1 d . . . . .
H9A H 0.116683 0.619076 0.453208 0.134 Uiso 1 1 calc R U . . .
H9B H 0.133884 0.520714 0.279673 0.134 Uiso 1 1 calc R U . . .
C10 C 0.0685(2) 0.4377(9) 0.3641(10) 0.155(3) Uani 1 1 d . . . . .
H10A H 0.052474 0.427650 0.480159 0.186 Uiso 1 1 calc R U . . .
H10B H 0.070142 0.324619 0.309623 0.186 Uiso 1 1 calc R U . . .
C11 C 0.0373(3) 0.5587(13) 0.2315(12) 0.240(5) Uani 1 1 d . . . . .
H11A H 0.010536 0.495296 0.167639 0.360 Uiso 1 1 calc R U . . .
H11B H 0.058749 0.606501 0.143332 0.360 Uiso 1 1 calc R U . . .
H11C H 0.023228 0.649256 0.301402 0.360 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_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 C1 1.621(4) . ?
S2 C4 1.740(4) . ?
S2 C1 1.748(4) . ?
S3 C5 1.735(4) . ?
S3 C7 1.753(4) . ?
S4 C7 1.622(4) . ?
O1 C3 1.209(4) . ?
O2 C6 1.211(4) . ?
N1 C1 1.376(4) . ?
N1 C3 1.384(5) . ?
N1 C2 1.464(5) . ?
N2 C7 1.370(4) . ?
N2 C6 1.382(5) . ?
N2 C8 1.455(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.460(5) . ?
C4 C5 1.335(5) . ?
C5 C6 1.474(5) . ?
C8 C9 1.542(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.449(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.549(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C4 S2 C1 91.41(18) . . ?
C5 S3 C7 91.98(18) . . ?
C1 N1 C3 115.7(3) . . ?
C1 N1 C2 123.0(4) . . ?
C3 N1 C2 121.3(3) . . ?
C7 N2 C6 116.1(3) . . ?
C7 N2 C8 123.9(3) . . ?
C6 N2 C8 120.0(3) . . ?
N1 C1 S1 126.7(3) . . ?
N1 C1 S2 111.3(3) . . ?
S1 C1 S2 121.9(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 N1 124.1(4) . . ?
O1 C3 C4 125.4(4) . . ?
N1 C3 C4 110.5(3) . . ?
C5 C4 C3 122.7(3) . . ?
C5 C4 S2 126.3(3) . . ?
C3 C4 S2 111.0(3) . . ?
C4 C5 C6 122.5(3) . . ?
C4 C5 S3 127.2(3) . . ?
C6 C5 S3 110.3(3) . . ?
O2 C6 N2 124.6(4) . . ?
O2 C6 C5 124.8(4) . . ?
N2 C6 C5 110.6(3) . . ?
N2 C7 S4 127.3(3) . . ?
N2 C7 S3 111.0(3) . . ?
S4 C7 S3 121.7(2) . . ?
N2 C8 C9 111.0(3) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 112.8(5) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 109.0(6) . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 S1 -178.5(3) . . . . ?
C2 N1 C1 S1 1.9(5) . . . . ?
C3 N1 C1 S2 1.4(4) . . . . ?
C2 N1 C1 S2 -178.2(3) . . . . ?
C4 S2 C1 N1 -2.0(3) . . . . ?
C4 S2 C1 S1 177.9(3) . . . . ?
C1 N1 C3 O1 -179.9(3) . . . . ?
C2 N1 C3 O1 -0.3(6) . . . . ?
C1 N1 C3 C4 0.3(4) . . . . ?
C2 N1 C3 C4 179.9(3) . . . . ?
O1 C3 C4 C5 -1.6(6) . . . . ?
N1 C3 C4 C5 178.3(3) . . . . ?
O1 C3 C4 S2 178.4(3) . . . . ?
N1 C3 C4 S2 -1.8(4) . . . . ?
C1 S2 C4 C5 -177.9(3) . . . . ?
C1 S2 C4 C3 2.2(3) . . . . ?
C3 C4 C5 C6 -179.1(3) . . . . ?
S2 C4 C5 C6 1.0(5) . . . . ?
C3 C4 C5 S3 -0.7(5) . . . . ?
S2 C4 C5 S3 179.3(2) . . . . ?
C7 S3 C5 C4 179.7(3) . . . . ?
C7 S3 C5 C6 -1.8(3) . . . . ?
C7 N2 C6 O2 178.5(3) . . . . ?
C8 N2 C6 O2 1.0(5) . . . . ?
C7 N2 C6 C5 -0.9(4) . . . . ?
C8 N2 C6 C5 -178.5(3) . . . . ?
C4 C5 C6 O2 1.0(6) . . . . ?
S3 C5 C6 O2 -177.6(3) . . . . ?
C4 C5 C6 N2 -179.5(3) . . . . ?
S3 C5 C6 N2 1.9(4) . . . . ?
C6 N2 C7 S4 -179.6(3) . . . . ?
C8 N2 C7 S4 -2.1(5) . . . . ?
C6 N2 C7 S3 -0.5(4) . . . . ?
C8 N2 C7 S3 177.0(3) . . . . ?
C5 S3 C7 N2 1.4(3) . . . . ?
C5 S3 C7 S4 -179.5(2) . . . . ?
C7 N2 C8 C9 101.9(4) . . . . ?
C6 N2 C8 C9 -80.7(5) . . . . ?
N2 C8 C9 C10 176.0(5) . . . . ?
C8 C9 C10 C11 -178.4(5) . . . . ?


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


