# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_20181226
_database_code_depnum_ccdc_archive 'CCDC 1912705'
loop_
_audit_author_name
_audit_author_address
'Dongho Yoo'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C16 H22 N2 S6'
_chemical_formula_moiety         'C16 H22 N2 S6'
_chemical_formula_weight         434.72
_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                   13.9523(4)
_cell_length_b                   5.01793(14)
_cell_length_c                   14.7127(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.3390(14)
_cell_angle_gamma                90.0000
_cell_volume                     1029.78(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1546
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      68.14
_cell_measurement_temperature    171
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456.00
_exptl_absorpt_coefficient_mu    6.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.832

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

_diffrn_ambient_temperature      171
_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            10930
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_theta_max         68.187
_diffrn_reflns_theta_min         3.168
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1870
_reflns_number_gt                1527
_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          0.0571
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1121
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1870
_refine_ls_number_parameters     109
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0502P)²+0.6155P] 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         0.45
_refine_diff_density_min         -0.32
_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)
;
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 0.41203(5) 0.79699(16) 0.57234(5) 0.0324(2) Uani 1 1 d . . . . .
S2 S 0.25653(6) 1.16904(19) 0.51564(7) 0.0466(3) Uani 1 1 d . . . . .
S3 S 0.44734(6) 0.47249(17) 0.30910(5) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.34914(17) 0.8270(5) 0.40573(17) 0.0320(6) Uani 1 1 d . . . . .
C1 C 0.46382(19) 0.5893(6) 0.49182(19) 0.0278(7) Uani 1 1 d . . . . .
C2 C 0.4189(2) 0.6328(6) 0.4020(2) 0.0302(7) Uani 1 1 d . . . . .
C3 C 0.3341(2) 0.9367(6) 0.4899(2) 0.0334(7) Uani 1 1 d . . . . .
C4 C 0.2951(2) 0.9148(6) 0.3233(2) 0.0351(7) Uani 1 1 d . . . . .
H4A H 0.338853 0.916156 0.271320 0.042 Uiso 1 1 calc R U . . .
H4B H 0.272540 1.099702 0.332604 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2094(2) 0.7399(7) 0.2996(2) 0.0399(8) Uani 1 1 d . . . . .
H5A H 0.163433 0.744121 0.349793 0.048 Uiso 1 1 calc R U . . .
H5B H 0.230792 0.553437 0.291496 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1606(2) 0.8392(7) 0.2122(2) 0.0398(8) Uani 1 1 d . . . . .
H6A H 0.139246 1.025111 0.221600 0.048 Uiso 1 1 calc R U . . .
H6B H 0.208206 0.840781 0.163374 0.048 Uiso 1 1 calc R U . . .
C7 C 0.0753(2) 0.6743(8) 0.1811(3) 0.0469(9) Uani 1 1 d . . . . .
H7A H 0.027818 0.670143 0.229984 0.056 Uiso 1 1 calc R U . . .
H7B H 0.096580 0.488968 0.170205 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0276(3) 0.7816(9) 0.0950(3) 0.0627(12) Uani 1 1 d . . . . .
H8A H -0.026996 0.668097 0.077754 0.075 Uiso 1 1 calc R U . . .
H8B H 0.005112 0.963684 0.105696 0.075 Uiso 1 1 calc R U . . .
H8C H 0.073890 0.782468 0.045903 0.075 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 2018/1 (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 C1 1.747(3) . ?
S1 C3 1.756(3) . ?
S2 C3 1.641(3) . ?
S3 C2 1.642(3) . ?
N1 C3 1.376(4) . ?
N1 C2 1.379(4) . ?
N1 C4 1.480(4) . ?
C1 C1 1.367(6) 3_666 ?
C1 C2 1.466(4) . ?
C4 C5 1.517(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.524(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.512(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.516(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C3 91.66(14) . . ?
C3 N1 C2 116.2(3) . . ?
C3 N1 C4 122.2(3) . . ?
C2 N1 C4 121.6(2) . . ?
C1 C1 C2 123.7(3) 3_666 . ?
C1 C1 S1 126.0(3) 3_666 . ?
C2 C1 S1 110.3(2) . . ?
N1 C2 C1 110.9(3) . . ?
N1 C2 S3 124.3(2) . . ?
C1 C2 S3 124.8(2) . . ?
N1 C3 S2 127.4(2) . . ?
N1 C3 S1 110.9(2) . . ?
S2 C3 S1 121.69(19) . . ?
N1 C4 C5 113.6(3) . . ?
N1 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 109.8(3) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 114.2(3) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 112.7(3) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 179.6(4) . . . 3_666 ?
C3 S1 C1 C2 -0.2(2) . . . . ?
C3 N1 C2 C1 -1.0(4) . . . . ?
C4 N1 C2 C1 178.0(2) . . . . ?
C3 N1 C2 S3 179.0(2) . . . . ?
C4 N1 C2 S3 -2.1(4) . . . . ?
C1 C1 C2 N1 -179.1(3) 3_666 . . . ?
S1 C1 C2 N1 0.6(3) . . . . ?
C1 C1 C2 S3 0.9(5) 3_666 . . . ?
S1 C1 C2 S3 -179.31(17) . . . . ?
C2 N1 C3 S2 -179.8(2) . . . . ?
C4 N1 C3 S2 1.2(4) . . . . ?
C2 N1 C3 S1 0.9(3) . . . . ?
C4 N1 C3 S1 -178.1(2) . . . . ?
C1 S1 C3 N1 -0.4(2) . . . . ?
C1 S1 C3 S2 -179.7(2) . . . . ?
C3 N1 C4 C5 -96.6(3) . . . . ?
C2 N1 C4 C5 84.5(3) . . . . ?
N1 C4 C5 C6 -177.9(3) . . . . ?
C4 C5 C6 C7 178.6(3) . . . . ?
C5 C6 C7 C8 179.0(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_Cytidine_(Rigaku_Master_for_Mo)
_database_code_depnum_ccdc_archive 'CCDC 1912706'
loop_
_audit_author_name
_audit_author_address
'Dongho Yoo'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C18 H26 N2 S6'
_chemical_formula_moiety         'C18 H26 N2 S6'
_chemical_formula_weight         462.78
_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                   14.970(8)
_cell_length_b                   5.028(4)
_cell_length_c                   15.075(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.05(4)
_cell_angle_gamma                90.0000
_cell_volume                     1134.6(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      15.12
_cell_measurement_theta_max      17.38
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488.00
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      298
_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            2984
_diffrn_reflns_av_unetI/netI     0.1362
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.702
_diffrn_reflns_theta_full        25.240
_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       -10
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -1.386
_reflns_number_total             2472
_reflns_number_gt                1147
_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          0.1824
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2494
_refine_ls_wR_factor_gt          0.1802
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2472
_refine_ls_number_parameters     119
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1397P)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         0.68
_refine_diff_density_min         -0.62
_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)
;
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 0.41692(10) 0.7904(3) 0.57335(10) 0.0434(5) Uani 1 1 d . . . . .
S2 S 0.45468(12) 0.4896(4) 0.31390(10) 0.0522(5) Uani 1 1 d . . . . .
S3 S 0.27331(13) 1.1643(4) 0.52156(15) 0.0689(7) Uani 1 1 d . . . . .
N1 N 0.3614(3) 0.8353(10) 0.4116(3) 0.0434(12) Uani 1 1 d . . . . .
C1 C 0.4264(4) 0.6401(11) 0.4059(4) 0.0386(14) Uani 1 1 d . . . . .
C2 C 0.4679(4) 0.5891(11) 0.4933(4) 0.0346(13) Uani 1 1 d . . . . .
C3 C 0.3466(4) 0.9381(13) 0.4943(4) 0.0482(16) Uani 1 1 d . . . . .
C4 C 0.1888(4) 0.8543(16) 0.2249(5) 0.0597(19) Uani 1 1 d . . . . .
H4A H 0.178877 1.044421 0.229645 0.072 Uiso 1 1 calc R U . . .
H4B H 0.231017 0.825583 0.177097 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3123(4) 0.9277(13) 0.3323(4) 0.0499(16) Uani 1 1 d . . . . .
H5A H 0.352400 0.926233 0.281826 0.060 Uiso 1 1 calc R U . . .
H5B H 0.293200 1.109856 0.341776 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1022(4) 0.7239(15) 0.2006(5) 0.0580(18) Uani 1 1 d . . . . .
H6A H 0.060171 0.750113 0.248682 0.070 Uiso 1 1 calc R U . . .
H6B H 0.112238 0.534134 0.194680 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2304(4) 0.7568(14) 0.3108(4) 0.0540(17) Uani 1 1 d . . . . .
H7A H 0.248070 0.572064 0.304657 0.065 Uiso 1 1 calc R U . . .
H7B H 0.187297 0.769173 0.358585 0.065 Uiso 1 1 calc R U . . .
C8 C 0.0607(5) 0.8260(18) 0.1157(5) 0.071(2) Uani 1 1 d . . . . .
H8A H 0.099610 0.781205 0.066500 0.085 Uiso 1 1 calc R U . . .
H8B H 0.056957 1.018373 0.118797 0.085 Uiso 1 1 calc R U . . .
C9 C -0.0317(5) 0.716(2) 0.0969(5) 0.087(3) Uani 1 1 d . . . . .
H9A H -0.071514 0.765238 0.144049 0.105 Uiso 1 1 calc R U . . .
H9B H -0.028748 0.525283 0.093034 0.105 Uiso 1 1 calc R U . . .
H9C H -0.053463 0.786628 0.041879 0.105 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/1 (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 C2 1.751(6) . ?
S1 C3 1.755(7) . ?
S2 C1 1.636(6) . ?
S3 C3 1.633(7) . ?
N1 C3 1.367(8) . ?
N1 C1 1.385(7) . ?
N1 C5 1.477(8) . ?
C1 C2 1.478(8) . ?
C2 C2 1.329(11) 3_666 ?
C4 C6 1.497(9) . ?
C4 C7 1.518(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.531(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.512(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.517(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C2 S1 C3 92.2(3) . . ?
C3 N1 C1 116.0(5) . . ?
C3 N1 C5 122.5(5) . . ?
C1 N1 C5 121.5(5) . . ?
N1 C1 C2 111.3(5) . . ?
N1 C1 S2 124.2(5) . . ?
C2 C1 S2 124.5(4) . . ?
C2 C2 C1 123.8(7) 3_666 . ?
C2 C2 S1 126.9(6) 3_666 . ?
C1 C2 S1 109.3(4) . . ?
N1 C3 S3 127.1(5) . . ?
N1 C3 S1 111.2(5) . . ?
S3 C3 S1 121.7(4) . . ?
C6 C4 C7 115.0(6) . . ?
C6 C4 H4A 108.5 . . ?
C7 C4 H4A 108.5 . . ?
C6 C4 H4B 108.5 . . ?
C7 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
N1 C5 C7 113.1(5) . . ?
N1 C5 H5A 109.0 . . ?
C7 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C7 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C4 C6 C8 114.5(6) . . ?
C4 C6 H6A 108.6 . . ?
C8 C6 H6A 108.6 . . ?
C4 C6 H6B 108.6 . . ?
C8 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C4 C7 C5 109.1(6) . . ?
C4 C7 H7A 109.9 . . ?
C5 C7 H7A 109.9 . . ?
C4 C7 H7B 109.9 . . ?
C5 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C6 C8 C9 114.1(7) . . ?
C6 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C6 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
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 . . ?

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 C2 -1.3(7) . . . . ?
C5 N1 C1 C2 178.0(5) . . . . ?
C3 N1 C1 S2 179.8(4) . . . . ?
C5 N1 C1 S2 -1.0(8) . . . . ?
N1 C1 C2 C2 179.9(7) . . . 3_666 ?
S2 C1 C2 C2 -1.2(10) . . . 3_666 ?
N1 C1 C2 S1 1.6(6) . . . . ?
S2 C1 C2 S1 -179.5(3) . . . . ?
C3 S1 C2 C2 -179.4(7) . . . 3_666 ?
C3 S1 C2 C1 -1.2(4) . . . . ?
C1 N1 C3 S3 -178.6(5) . . . . ?
C5 N1 C3 S3 2.1(9) . . . . ?
C1 N1 C3 S1 0.3(7) . . . . ?
C5 N1 C3 S1 -178.9(4) . . . . ?
C2 S1 C3 N1 0.6(5) . . . . ?
C2 S1 C3 S3 179.6(4) . . . . ?
C3 N1 C5 C7 -94.7(7) . . . . ?
C1 N1 C5 C7 86.1(7) . . . . ?
C7 C4 C6 C8 179.0(7) . . . . ?
C6 C4 C7 C5 -173.8(6) . . . . ?
N1 C5 C7 C4 -175.8(6) . . . . ?
C4 C6 C8 C9 -173.5(7) . . . . ?


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


