# 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_C4INOS3
_database_code_depnum_ccdc_archive 'CCDC 1994381'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_date             2017-07-17T17:26:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C4 I N O S3'
_chemical_formula_moiety         'C4 I N O S3'
_chemical_formula_weight         301.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   9.017(3)
_cell_length_b                   9.118(3)
_cell_length_c                   9.594(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.676(13)
_cell_angle_gamma                90
_cell_volume                     784.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2531
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.18
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    2.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_T_max  0.825

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.2877  0.7455                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.076202
_diffrn_orient_matrix_ub_12      -0.072924
_diffrn_orient_matrix_ub_13      -0.024259
_diffrn_orient_matrix_ub_21      0.061602
_diffrn_orient_matrix_ub_22      0.081255
_diffrn_orient_matrix_ub_23      -0.034045
_diffrn_orient_matrix_ub_31      0.053107
_diffrn_orient_matrix_ub_32      0.010384
_diffrn_orient_matrix_ub_33      0.096041
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.063
_diffrn_reflns_number            4843
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.089
_diffrn_reflns_theta_max         28.209
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.942
_reflns_Friedel_coverage         0
_reflns_number_total             1819
_reflns_number_gt                1278
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+6.7839P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1819
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.435
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.184

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.0953(11) 0.4381(11) 0.8613(10) 0.055(2) Uani 1 1 d . . . . .
C2 C 0.0627(10) 0.1594(9) 0.8290(9) 0.0422(19) Uani 1 1 d . . . . .
C3 C -0.0348(10) 0.2198(8) 0.7272(9) 0.0384(17) Uani 1 1 d . . . . .
C4 C -0.0853(10) -0.0072(9) 0.6808(8) 0.0398(18) Uani 1 1 d . . . . .
N1 N -0.1170(8) 0.1270(8) 0.6421(7) 0.0426(16) Uani 1 1 d . . . . .
S1 S -0.0394(3) 0.4123(2) 0.7177(3) 0.0573(6) Uani 1 1 d . . . . .
S2 S 0.1696(3) 0.2754(3) 0.9427(3) 0.0556(6) Uani 1 1 d . . . . .
S3 S 0.0497(3) -0.0276(2) 0.8195(2) 0.0507(6) Uani 1 1 d . . . . .
I1 I -0.18933(7) -0.18892(6) 0.58141(7) 0.0523(3) Uani 1 1 d . . . . .
O1 O 0.1356(10) 0.5580(8) 0.9050(8) 0.077(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 O1 1.213(11) . ?
C1 S1 1.759(11) . ?
C1 S2 1.777(11) . ?
C2 C3 1.364(12) . ?
C2 S3 1.710(8) . ?
C2 S2 1.741(9) . ?
C3 N1 1.346(11) . ?
C3 S1 1.758(8) . ?
C4 N1 1.302(10) . ?
C4 S3 1.722(8) . ?
C4 I1 2.088(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 S1 123.4(9) . . ?
O1 C1 S2 120.9(9) . . ?
S1 C1 S2 115.7(5) . . ?
C3 C2 S3 109.2(6) . . ?
C3 C2 S2 118.7(6) . . ?
S3 C2 S2 132.0(5) . . ?
N1 C3 C2 117.2(7) . . ?
N1 C3 S1 126.0(6) . . ?
C2 C3 S1 116.8(7) . . ?
N1 C4 S3 116.1(6) . . ?
N1 C4 I1 122.7(6) . . ?
S3 C4 I1 121.2(4) . . ?
C4 N1 C3 109.0(7) . . ?
C3 S1 C1 94.7(4) . . ?
C2 S2 C1 94.0(4) . . ?
C2 S3 C4 88.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S3 C2 C3 N1 -0.7(10) . . . . ?
S2 C2 C3 N1 -179.2(6) . . . . ?
S3 C2 C3 S1 -179.8(5) . . . . ?
S2 C2 C3 S1 1.6(10) . . . . ?
S3 C4 N1 C3 -1.7(10) . . . . ?
I1 C4 N1 C3 178.7(6) . . . . ?
C2 C3 N1 C4 1.5(11) . . . . ?
S1 C3 N1 C4 -179.5(7) . . . . ?
N1 C3 S1 C1 179.7(8) . . . . ?
C2 C3 S1 C1 -1.2(8) . . . . ?
O1 C1 S1 C3 -178.8(9) . . . . ?
S2 C1 S1 C3 0.5(6) . . . . ?
C3 C2 S2 C1 -1.0(8) . . . . ?
S3 C2 S2 C1 -179.2(7) . . . . ?
O1 C1 S2 C2 179.4(9) . . . . ?
S1 C1 S2 C2 0.1(6) . . . . ?
C3 C2 S3 C4 -0.2(7) . . . . ?
S2 C2 S3 C4 178.1(7) . . . . ?
N1 C4 S3 C2 1.1(7) . . . . ?
I1 C4 S3 C2 -179.2(5) . . . . ?

####################################################################### 
# 
# 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_trans-Ni
_database_code_depnum_ccdc_archive 'CCDC 1994385'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_date             2019-04-29T15:31:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H36 I2 N3 Ni S6'
_chemical_formula_moiety         'C6 I2 N2 Ni S6, C16 H36 N'
_chemical_formula_weight         847.41

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.9488(17)
_cell_length_b                   12.5276(12)
_cell_length_c                   16.2505(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.452(6)
_cell_angle_gamma                90
_cell_volume                     3243.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2488
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.26
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1676

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.748

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5694  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.015896
_diffrn_orient_matrix_ub_12      -0.006296
_diffrn_orient_matrix_ub_13      -0.059999
_diffrn_orient_matrix_ub_21      0.053116
_diffrn_orient_matrix_ub_22      0.037089
_diffrn_orient_matrix_ub_23      -0.01379
_diffrn_orient_matrix_ub_31      0.029404
_diffrn_orient_matrix_ub_32      -0.070403
_diffrn_orient_matrix_ub_33      -0.001899
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_number            10918
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             3668
_reflns_number_gt                1765
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3668
_refine_ls_number_parameters     184
_refine_ls_number_restraints     64
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.118

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6546(4) 0.4108(5) 0.0994(4) 0.0527(18) Uani 1 1 d . . . . .
C2 C 0.7354(5) 0.4378(5) 0.1166(4) 0.0482(17) Uani 1 1 d . . . . .
C3 C 0.6778(5) 0.5555(5) 0.1962(4) 0.059(2) Uani 1 1 d . . . . .
C4 C 0.9230(5) 0.6822(6) 0.2306(5) 0.070(2) Uani 1 1 d . . . . .
H4A H 0.8777 0.6336 0.215 0.084 Uiso 1 1 calc R U . . .
H4B H 0.9075 0.7184 0.2805 0.084 Uiso 1 1 calc R U . . .
C5 C 0.9294(6) 0.7635(7) 0.1643(5) 0.082(3) Uani 1 1 d . . . . .
H5A H 0.9518 0.7292 0.1164 0.099 Uiso 1 1 calc R U . . .
H5B H 0.9693 0.8177 0.1829 0.099 Uiso 1 1 calc R U . . .
C6 C 0.8484(6) 0.8174(7) 0.1385(6) 0.089(3) Uani 1 1 d . . . . .
H6A H 0.8077 0.7631 0.122 0.106 Uiso 1 1 calc R U . . .
H6B H 0.8272 0.8545 0.1857 0.106 Uiso 1 1 calc R U . . .
C7 C 0.8552(6) 0.8946(8) 0.0702(7) 0.111(3) Uani 1 1 d . . . . .
H7A H 0.8011 0.9256 0.0573 0.166 Uiso 1 1 calc R U . . .
H7B H 0.8942 0.9499 0.0863 0.166 Uiso 1 1 calc R U . . .
H7C H 0.8746 0.8585 0.0225 0.166 Uiso 1 1 calc R U . . .
C8 C 0.9839(6) 0.5456(7) 0.3257(5) 0.083(3) Uani 0.60(2) 1 d D . P A 1
H8A H 1.0349 0.5056 0.3383 0.099 Uiso 0.60(2) 1 calc R U P A 1
H8B H 0.9752 0.5921 0.3724 0.099 Uiso 0.60(2) 1 calc R U P A 1
C9 C 0.9120(18) 0.467(2) 0.3206(16) 0.123(6) Uani 0.60(2) 1 d . U P A 1
H9A H 0.9232 0.4149 0.2782 0.148 Uiso 0.60(2) 1 calc R U P A 1
H9B H 0.8613 0.5051 0.3032 0.148 Uiso 0.60(2) 1 calc R U P A 1
C10 C 0.8953(16) 0.4069(18) 0.4008(18) 0.134(6) Uani 0.60(2) 1 d D U P A 1
H10A H 0.9004 0.4553 0.4473 0.161 Uiso 0.60(2) 1 calc R U P A 1
H10B H 0.839 0.3775 0.3983 0.161 Uiso 0.60(2) 1 calc R U P A 1
C11 C 0.9559(16) 0.3227(19) 0.410(2) 0.163(9) Uani 0.60(2) 1 d D U P A 1
H11A H 0.9466 0.2841 0.46 0.245 Uiso 0.60(2) 1 calc R U P A 1
H11B H 0.9503 0.2751 0.364 0.245 Uiso 0.60(2) 1 calc R U P A 1
H11C H 1.0114 0.3526 0.4129 0.245 Uiso 0.60(2) 1 calc R U P A 1
C8A C 0.9839(6) 0.5456(7) 0.3257(5) 0.083(3) Uani 0.40(2) 1 d . . P A 2
H8AA H 1.0366 0.5219 0.3514 0.099 Uiso 0.40(2) 1 calc R U P A 2
H8AB H 0.9529 0.5845 0.3662 0.099 Uiso 0.40(2) 1 calc R U P A 2
C9B C 0.934(3) 0.453(3) 0.294(2) 0.136(8) Uani 0.40(2) 1 d D U P A 2
H9B1 H 0.8966 0.4712 0.2475 0.163 Uiso 0.40(2) 1 calc R U P A 2
H9B2 H 0.9691 0.3926 0.2798 0.163 Uiso 0.40(2) 1 calc R U P A 2
C10B C 0.889(3) 0.435(3) 0.371(2) 0.140(7) Uani 0.40(2) 1 d D U P A 2
H10C H 0.8791 0.5067 0.3905 0.167 Uiso 0.40(2) 1 calc R U P A 2
H10D H 0.8346 0.4089 0.351 0.167 Uiso 0.40(2) 1 calc R U P A 2
C11B C 0.906(3) 0.373(4) 0.447(2) 0.155(10) Uani 0.40(2) 1 d D U P A 2
H11D H 0.8606 0.3825 0.4831 0.232 Uiso 0.40(2) 1 calc R U P A 2
H11E H 0.9119 0.2992 0.4338 0.232 Uiso 0.40(2) 1 calc R U P A 2
H11F H 0.9572 0.3986 0.4739 0.232 Uiso 0.40(2) 1 calc R U P A 2
N1 N 0.7489(4) 0.5220(4) 0.1713(4) 0.0591(16) Uani 1 1 d . . . . .
N6 N 1 0.6180(6) 0.25 0.058(2) Uani 1 2 d S T P . .
S1 S 0.62730(12) 0.30648(15) 0.03475(12) 0.0635(6) Uani 1 1 d . . . . .
S2 S 0.81708(12) 0.37191(14) 0.07081(12) 0.0591(5) Uani 1 1 d . . . . .
S3 S 0.58989(13) 0.49267(17) 0.15397(13) 0.0720(6) Uani 1 1 d . . . . .
I1 I 0.66892(4) 0.67162(4) 0.28749(4) 0.0823(3) Uani 1 1 d . . . . .
Ni1 Ni 0.75 0.25 0 0.0481(4) Uani 1 2 d S . P . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.351(9) . ?
C1 S1 1.720(7) . ?
C1 S3 1.727(7) . ?
C2 N1 1.389(8) . ?
C2 S2 1.737(7) . ?
C3 N1 1.290(9) . ?
C3 S3 1.725(8) . ?
C3 I1 2.086(7) . ?
C4 C5 1.489(10) . ?
C4 N6 1.491(9) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C6 1.502(12) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 C7 1.481(12) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 C9 1.51(2) . ?
C8 N6 1.559(9) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.54(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.434(17) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C8A C9B 1.490(19) . ?
C8A N6 1.559(9) . ?
C8A H8AA 0.97 . ?
C8A H8AB 0.97 . ?
C9B C10B 1.484(19) . ?
C9B H9B1 0.97 . ?
C9B H9B2 0.97 . ?
C10B C11B 1.476(19) . ?
C10B H10C 0.97 . ?
C10B H10D 0.97 . ?
C11B H11D 0.96 . ?
C11B H11E 0.96 . ?
C11B H11F 0.96 . ?
N6 C4 1.491(9) 2_755 ?
N6 C8A 1.559(9) 2_755 ?
N6 C8 1.559(9) 2_755 ?
S1 Ni1 2.178(2) . ?
S2 Ni1 2.1670(18) . ?
Ni1 S2 2.1670(18) 7_655 ?
Ni1 S1 2.178(2) 7_655 ?

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 C1 S1 122.1(5) . . ?
C2 C1 S3 109.2(5) . . ?
S1 C1 S3 128.6(4) . . ?
C1 C2 N1 116.3(6) . . ?
C1 C2 S2 121.2(5) . . ?
N1 C2 S2 122.4(6) . . ?
N1 C3 S3 115.9(5) . . ?
N1 C3 I1 122.5(5) . . ?
S3 C3 I1 121.5(4) . . ?
C5 C4 N6 116.1(7) . . ?
C5 C4 H4A 108.3 . . ?
N6 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
N6 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 C6 115.1(8) . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 114.4(8) . . ?
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 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N6 119.1(13) . . ?
C9 C8 H8A 107.6 . . ?
N6 C8 H8A 107.6 . . ?
C9 C8 H8B 107.6 . . ?
N6 C8 H8B 107.6 . . ?
H8A C8 H8B 107 . . ?
C8 C9 C10 115(2) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 108(2) . . ?
C11 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
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 . . ?
C9B C8A N6 106.5(18) . . ?
C9B C8A H8AA 110.4 . . ?
N6 C8A H8AA 110.4 . . ?
C9B C8A H8AB 110.4 . . ?
N6 C8A H8AB 110.4 . . ?
H8AA C8A H8AB 108.6 . . ?
C10B C9B C8A 95(3) . . ?
C10B C9B H9B1 112.7 . . ?
C8A C9B H9B1 112.7 . . ?
C10B C9B H9B2 112.7 . . ?
C8A C9B H9B2 112.7 . . ?
H9B1 C9B H9B2 110.1 . . ?
C11B C10B C9B 135(5) . . ?
C11B C10B H10C 103.4 . . ?
C9B C10B H10C 103.4 . . ?
C11B C10B H10D 103.4 . . ?
C9B C10B H10D 103.4 . . ?
H10C C10B H10D 105.2 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C3 N1 C2 109.5(6) . . ?
C4 N6 C4 114.6(8) . 2_755 ?
C4 N6 C8A 108.0(4) . 2_755 ?
C4 N6 C8A 108.6(5) 2_755 2_755 ?
C4 N6 C8 108.0(4) . 2_755 ?
C4 N6 C8 108.6(5) 2_755 2_755 ?
C4 N6 C8A 108.6(5) . . ?
C4 N6 C8A 108.0(4) 2_755 . ?
C8A N6 C8A 108.9(8) 2_755 . ?
C4 N6 C8 108.6(5) . . ?
C4 N6 C8 108.0(4) 2_755 . ?
C8 N6 C8 108.9(8) 2_755 . ?
C1 S1 Ni1 101.4(2) . . ?
C2 S2 Ni1 101.6(2) . . ?
C3 S3 C1 89.0(4) . . ?
S2 Ni1 S2 180 . 7_655 ?
S2 Ni1 S1 93.56(7) . . ?
S2 Ni1 S1 86.44(7) 7_655 . ?
S2 Ni1 S1 86.44(7) . 7_655 ?
S2 Ni1 S1 93.56(7) 7_655 7_655 ?
S1 Ni1 S1 180 . 7_655 ?

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
S1 C1 C2 N1 -178.5(5) . . . . ?
S3 C1 C2 N1 -0.5(7) . . . . ?
S1 C1 C2 S2 2.7(8) . . . . ?
S3 C1 C2 S2 -179.2(4) . . . . ?
N6 C4 C5 C6 172.6(7) . . . . ?
C4 C5 C6 C7 -177.6(8) . . . . ?
N6 C8 C9 C10 -174.2(17) . . . . ?
C8 C9 C10 C11 -79(3) . . . . ?
N6 C8A C9B C10B -150(3) . . . . ?
C8A C9B C10B C11B -88(6) . . . . ?
S3 C3 N1 C2 -2.1(8) . . . . ?
I1 C3 N1 C2 174.1(4) . . . . ?
C1 C2 N1 C3 1.6(8) . . . . ?
S2 C2 N1 C3 -179.6(5) . . . . ?
C5 C4 N6 C4 53.9(6) . . . 2_755 ?
C5 C4 N6 C8A -67.3(8) . . . 2_755 ?
C5 C4 N6 C8 -67.3(8) . . . 2_755 ?
C5 C4 N6 C8A 174.7(7) . . . . ?
C5 C4 N6 C8 174.7(7) . . . . ?
C9B C8A N6 C4 80(2) . . . . ?
C9B C8A N6 C4 -155(2) . . . 2_755 ?
C9B C8A N6 C8A -38(2) . . . 2_755 ?
C9 C8 N6 C4 58.7(16) . . . . ?
C9 C8 N6 C4 -176.4(15) . . . 2_755 ?
C9 C8 N6 C8 -58.7(15) . . . 2_755 ?
C2 C1 S1 Ni1 -0.2(6) . . . . ?
S3 C1 S1 Ni1 -177.8(4) . . . . ?
C1 C2 S2 Ni1 -3.6(6) . . . . ?
N1 C2 S2 Ni1 177.7(5) . . . . ?
N1 C3 S3 C1 1.6(6) . . . . ?
I1 C3 S3 C1 -174.6(4) . . . . ?
C2 C1 S3 C3 -0.6(5) . . . . ?
S1 C1 S3 C3 177.3(5) . . . . ?

####################################################################### 
# 
# 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_trans-Au
_database_code_depnum_ccdc_archive 'CCDC 1994384'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_date             2020-03-24T15:22:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H36 Au I2 N3 S6'
_chemical_formula_moiety         'C6 Au I2 N2 S6, C16 H36 N'
_chemical_formula_weight         985.66

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.6439(10)
_cell_length_b                   12.2704(8)
_cell_length_c                   16.6152(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.368(3)
_cell_angle_gamma                90
_cell_volume                     3183.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1880

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.351
_exptl_absorpt_correction_T_max  0.465

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6027  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_radiation_source                'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.024427
_diffrn_orient_matrix_ub_12      0.033224
_diffrn_orient_matrix_ub_13      0.051283
_diffrn_orient_matrix_ub_21      -0.025989
_diffrn_orient_matrix_ub_22      0.071736
_diffrn_orient_matrix_ub_23      -0.016238
_diffrn_orient_matrix_ub_31      -0.05318
_diffrn_orient_matrix_ub_32      -0.019796
_diffrn_orient_matrix_ub_33      0.027227
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_number            14081
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3641
_reflns_number_gt                3197
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0752P)²+126.5711P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3641
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.791
_refine_diff_density_min         -2.895
_refine_diff_density_rms         0.242

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Au1 Au 0.75 0.25 0.5 0.0459(2) Uani 1 2 d S . P . .
I1 I 0.83539(6) 0.69059(6) 0.21948(4) 0.0574(3) Uani 1 1 d . . . . .
S1 S 0.8833(2) 0.3170(3) 0.4682(2) 0.0616(9) Uani 1 1 d . . . . .
S2 S 0.6789(2) 0.3829(2) 0.42251(18) 0.0536(7) Uani 1 1 d . . . . .
S3 S 0.9153(2) 0.5087(3) 0.3528(2) 0.0651(9) Uani 1 1 d . . . . .
N1 N 0.7535(7) 0.5343(7) 0.3276(5) 0.046(2) Uani 1 1 d . . . . .
C1 C 0.8481(8) 0.4215(9) 0.4035(6) 0.050(3) Uani 1 1 d . . . . .
C2 C 0.7658(8) 0.4479(8) 0.3828(6) 0.047(3) Uani 1 1 d . . . . .
C3 C 0.8261(9) 0.5699(9) 0.3072(6) 0.050(3) Uani 1 1 d . . . . .
C4 C 0.9216(9) 0.1964(13) 0.2314(9) 0.068(4) Uani 1 1 d . . . . .
H4A H 0.9077 0.238 0.28 0.082 Uiso 1 1 calc R U . . .
H4B H 0.874 0.1447 0.2191 0.082 Uiso 1 1 calc R U . . .
N2 N 1 0.1339(16) 0.25 0.062(4) Uani 1 2 d S T P . .
C5 C 0.9257(11) 0.2729(13) 0.1637(10) 0.071(4) Uani 1 1 d . . . . .
H5A H 0.9421 0.2312 0.1159 0.086 Uiso 1 1 calc R U . . .
H5B H 0.9724 0.3255 0.1771 0.086 Uiso 1 1 calc R U . . .
C6 C 0.8436(11) 0.3387(13) 0.1392(11) 0.075(4) Uani 1 1 d . . . . .
H6A H 0.7961 0.2863 0.1289 0.09 Uiso 1 1 calc R U . . .
H6B H 0.8292 0.3839 0.1859 0.09 Uiso 1 1 calc R U . . .
C8 C 1.0200(8) 0.0521(11) 0.1731(8) 0.058(3) Uani 1 1 d . . . . .
H8A H 0.9666 0.0128 0.1565 0.07 Uiso 1 1 calc R U . . .
H8B H 1.0352 0.0979 0.1271 0.07 Uiso 1 1 calc R U . . .
C7 C 0.8462(12) 0.4053(19) 0.0737(12) 0.097(6) Uani 1 1 d . . . . .
H7A H 0.9055 0.4274 0.0667 0.145 Uiso 1 1 calc R U . . .
H7B H 0.8111 0.4701 0.0819 0.145 Uiso 1 1 calc R U . . .
H7C H 0.8238 0.3663 0.0255 0.145 Uiso 1 1 calc R U . . .
C11 C 1.0577(19) -0.144(2) 0.0707(15) 0.157(14) Uani 1 1 d . . . . .
H11A H 1.0119 -0.17 0.1034 0.235 Uiso 1 1 calc R U . . .
H11B H 1.0927 -0.2054 0.0548 0.235 Uiso 1 1 calc R U . . .
H11C H 1.0326 -0.1073 0.0224 0.235 Uiso 1 1 calc R U . . .
C9 C 1.0854(14) -0.0254(17) 0.1880(13) 0.106(7) Uani 1 1 d . . . . .
H9A H 1.1357 0.0099 0.2161 0.127 Uiso 1 1 calc R U . . .
H9B H 1.0651 -0.0838 0.2233 0.127 Uiso 1 1 calc R U . . .
C10 C 1.1089(13) -0.0700(17) 0.1156(12) 0.090(5) Uiso 1 1 d . . . . .
H10A H 1.1648 -0.1062 0.1271 0.109 Uiso 1 1 calc R U . . .
H10B H 1.1195 -0.008 0.0794 0.109 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
Au1 S2 2.321(2) . ?
Au1 S2 2.321(2) 7_656 ?
Au1 S1 2.331(4) 7_656 ?
Au1 S1 2.331(4) . ?
I1 C3 2.089(11) . ?
S1 C1 1.742(10) . ?
S2 C2 1.738(14) . ?
S3 C3 1.721(12) . ?
S3 C1 1.751(14) . ?
N1 C3 1.281(17) . ?
N1 C2 1.408(13) . ?
C1 C2 1.352(16) . ?
C4 N2 1.465(17) . ?
C4 C5 1.47(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
N2 C4 1.465(17) 2_755 ?
N2 C8 1.668(19) . ?
N2 C8 1.668(19) 2_755 ?
C5 C6 1.55(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.36(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C8 C9 1.41(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C11 C10 1.39(3) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C9 C10 1.39(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?

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
S2 Au1 S2 180 . 7_656 ?
S2 Au1 S1 88.16(11) . 7_656 ?
S2 Au1 S1 91.84(11) 7_656 7_656 ?
S2 Au1 S1 91.84(11) . . ?
S2 Au1 S1 88.16(11) 7_656 . ?
S1 Au1 S1 180 7_656 . ?
C1 S1 Au1 98.3(5) . . ?
C2 S2 Au1 100.0(3) . . ?
C3 S3 C1 89.1(6) . . ?
C3 N1 C2 109.8(9) . . ?
C2 C1 S1 126.6(11) . . ?
C2 C1 S3 108.7(8) . . ?
S1 C1 S3 124.7(7) . . ?
C1 C2 N1 116.0(12) . . ?
C1 C2 S2 123.2(9) . . ?
N1 C2 S2 120.8(9) . . ?
N1 C3 S3 116.4(8) . . ?
N1 C3 I1 121.6(8) . . ?
S3 C3 I1 121.9(8) . . ?
N2 C4 C5 115.0(13) . . ?
N2 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
N2 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C4 N2 C4 116.8(18) . 2_755 ?
C4 N2 C8 110.2(7) . . ?
C4 N2 C8 106.5(8) 2_755 . ?
C4 N2 C8 106.5(8) . 2_755 ?
C4 N2 C8 110.2(7) 2_755 2_755 ?
C8 N2 C8 106.0(14) . 2_755 ?
C4 C5 C6 117.3(14) . . ?
C4 C5 H5A 108 . . ?
C6 C5 H5A 108 . . ?
C4 C5 H5B 108 . . ?
C6 C5 H5B 108 . . ?
H5A C5 H5B 107.2 . . ?
C7 C6 C5 117.3(15) . . ?
C7 C6 H6A 108 . . ?
C5 C6 H6A 108 . . ?
C7 C6 H6B 108 . . ?
C5 C6 H6B 108 . . ?
H6A C6 H6B 107.2 . . ?
C9 C8 N2 116.0(11) . . ?
C9 C8 H8A 108.3 . . ?
N2 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
N2 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 . . ?
C10 C9 C8 109.9(18) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 C11 123(2) . . ?
C9 C10 H10A 106.6 . . ?
C11 C10 H10A 106.6 . . ?
C9 C10 H10B 106.6 . . ?
C11 C10 H10B 106.6 . . ?
H10A C10 H10B 106.5 . . ?

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
Au1 S1 C1 C2 0.1(10) . . . . ?
Au1 S1 C1 S3 -178.6(6) . . . . ?
C3 S3 C1 C2 -1.2(8) . . . . ?
C3 S3 C1 S1 177.7(8) . . . . ?
S1 C1 C2 N1 -178.4(7) . . . . ?
S3 C1 C2 N1 0.4(11) . . . . ?
S1 C1 C2 S2 3.1(14) . . . . ?
S3 C1 C2 S2 -178.1(6) . . . . ?
C3 N1 C2 C1 0.9(13) . . . . ?
C3 N1 C2 S2 179.4(8) . . . . ?
Au1 S2 C2 C1 -4.2(9) . . . . ?
Au1 S2 C2 N1 177.4(7) . . . . ?
C2 N1 C3 S3 -1.9(12) . . . . ?
C2 N1 C3 I1 175.3(7) . . . . ?
C1 S3 C3 N1 1.8(9) . . . . ?
C1 S3 C3 I1 -175.4(7) . . . . ?
C5 C4 N2 C4 57.3(12) . . . 2_755 ?
C5 C4 N2 C8 -64.5(17) . . . . ?
C5 C4 N2 C8 -179.1(12) . . . 2_755 ?
N2 C4 C5 C6 178.0(13) . . . . ?
C4 C5 C6 C7 -176.6(17) . . . . ?
C4 N2 C8 C9 -170.0(16) . . . . ?
C4 N2 C8 C9 62.3(18) 2_755 . . . ?
C8 N2 C8 C9 -55.1(14) 2_755 . . . ?
N2 C8 C9 C10 -166.2(15) . . . . ?
C8 C9 C10 C11 -73(3) . . . . ?

####################################################################### 
# 
# 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_cis-Au
_database_code_depnum_ccdc_archive 'CCDC 1994383'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_date             2018-02-01T14:30:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H36 Au I2 N3 S6'
_chemical_formula_moiety         '	C6 Au I2 N2 S6, C16 H36 N'
_chemical_formula_weight         985.66

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1817(5)
_cell_length_b                   13.2215(5)
_cell_length_c                   11.5412(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.649(2)
_cell_angle_gamma                90
_cell_volume                     1705.53(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5042
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.75
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             940

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_T_max  0.634

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4854  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.021427
_diffrn_orient_matrix_ub_12      -0.064787
_diffrn_orient_matrix_ub_13      0.039006
_diffrn_orient_matrix_ub_21      0.082168
_diffrn_orient_matrix_ub_22      -0.003566
_diffrn_orient_matrix_ub_23      0.03633
_diffrn_orient_matrix_ub_31      -0.028179
_diffrn_orient_matrix_ub_32      0.038865
_diffrn_orient_matrix_ub_33      0.068355
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_number            12067
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_coverage         0.918
_reflns_number_total             7227
_reflns_number_gt                5252
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.0961P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7227
_refine_ls_number_parameters     312
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.009(11)
_refine_diff_density_max         1.734
_refine_diff_density_min         -1.025
_refine_diff_density_rms         0.159

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Au1 Au 1.68378(4) 0.10008(5) 0.81744(4) 0.04673(16) Uani 1 1 d . . . . .
I1 I 1.42359(11) -0.32763(7) 0.49919(9) 0.0673(3) Uani 1 1 d . . . . .
I2 I 2.00103(11) 0.54180(9) 1.04742(13) 0.0857(4) Uani 1 1 d . . . . .
S4 S 1.6425(4) 0.1965(3) 0.9789(4) 0.0671(12) Uani 1 1 d . . . . .
S3 S 1.7270(4) -0.0006(3) 0.6589(3) 0.0568(10) Uani 1 1 d . . . . .
S1 S 1.5226(4) -0.0011(3) 0.8653(4) 0.0670(12) Uani 1 1 d . . . . .
S6 S 1.8423(4) 0.2043(3) 0.7688(4) 0.0600(11) Uani 1 1 d . . . . .
S2 S 1.4220(5) -0.1801(4) 0.7260(4) 0.0773(14) Uani 1 1 d . . . . .
S5 S 1.7783(5) 0.3849(4) 1.0646(5) 0.0826(17) Uani 1 1 d . . . . .
N1 N 1.5934(12) -0.1602(10) 0.5788(10) 0.056(3) Uani 1 1 d . . . . .
N2 N 1.9199(10) 0.3697(9) 0.8895(12) 0.053(3) Uani 1 1 d . . . . .
N3 N 1.2936(12) 0.3553(11) 0.7867(12) 0.065(4) Uani 1 1 d . . . . .
C3 C 1.4952(15) -0.2124(11) 0.6022(13) 0.055(4) Uani 1 1 d . . . . .
C4 C 1.7536(14) 0.2855(12) 0.9662(14) 0.055(4) Uani 1 1 d . . . . .
C5 C 1.8359(13) 0.2901(11) 0.8850(14) 0.050(4) Uani 1 1 d . . . . .
C12 C 1.2755(18) 0.2676(15) 0.9885(17) 0.079(5) Uani 1 1 d . . . . .
H12A H 1.2671 0.1998 0.9574 0.094 Uiso 1 1 calc R U . . .
H12B H 1.3597 0.2796 1.0061 0.094 Uiso 1 1 calc R U . . .
C2 C 1.6045(13) -0.0860(10) 0.6660(12) 0.046(3) Uani 1 1 d . . . . .
C1 C 1.5267(15) -0.0844(11) 0.7511(14) 0.053(4) Uani 1 1 d . . . . .
C18 C 1.6960(19) 0.4725(17) 0.648(2) 0.104(7) Uani 1 1 d . . . . .
H18A H 1.7153 0.4061 0.6201 0.156 Uiso 1 1 calc R U . . .
H18B H 1.7677 0.5055 0.6756 0.156 Uiso 1 1 calc R U . . .
H18C H 1.6606 0.5113 0.5851 0.156 Uiso 1 1 calc R U . . .
C17 C 1.6103(17) 0.4643(18) 0.7428(19) 0.091(6) Uani 1 1 d . . . . .
H17A H 1.6484 0.4267 0.8058 0.109 Uiso 1 1 calc R U . . .
H17B H 1.5944 0.5319 0.7713 0.109 Uiso 1 1 calc R U . . .
C20 C 1.2027(18) 0.5272(15) 0.7371(17) 0.082(6) Uani 1 1 d . . . . .
H20A H 1.183 0.5312 0.8182 0.098 Uiso 1 1 calc R U . . .
H20B H 1.2777 0.5627 0.7273 0.098 Uiso 1 1 calc R U . . .
C11 C 1.2306(18) 0.3431(17) 0.9003(19) 0.086(6) Uani 1 1 d . . . . .
H11A H 1.2305 0.4088 0.9378 0.103 Uiso 1 1 calc R U . . .
H11B H 1.1478 0.3264 0.8817 0.103 Uiso 1 1 calc R U . . .
C7 C 1.3109(15) 0.2507(14) 0.7295(17) 0.075(5) Uani 1 1 d . . . . .
H7A H 1.354 0.2602 0.6586 0.09 Uiso 1 1 calc R U . . .
H7B H 1.3608 0.2097 0.7812 0.09 Uiso 1 1 calc R U . . .
C8 C 1.1995(18) 0.1936(15) 0.7012(18) 0.085(6) Uani 1 1 d . . . . .
H8A H 1.1534 0.1864 0.7707 0.102 Uiso 1 1 calc R U . . .
H8B H 1.1515 0.2314 0.6448 0.102 Uiso 1 1 calc R U . . .
C9 C 1.2248(18) 0.094(2) 0.655(2) 0.118(8) Uani 1 1 d . . . . .
H9A H 1.2716 0.0577 0.7136 0.142 Uiso 1 1 calc R U . . .
H9B H 1.2761 0.1033 0.5893 0.142 Uiso 1 1 calc R U . . .
C13 C 1.206(2) 0.2767(15) 1.0961(18) 0.091(6) Uani 1 1 d . . . . .
H13A H 1.218 0.344 1.128 0.109 Uiso 1 1 calc R U . . .
H13B H 1.1219 0.2688 1.0767 0.109 Uiso 1 1 calc R U . . .
C21 C 1.108(2) 0.5780(19) 0.667(2) 0.119(9) Uani 1 1 d . . . . .
H21A H 1.0329 0.5442 0.6816 0.143 Uiso 1 1 calc R U . . .
H21B H 1.1249 0.5675 0.5859 0.143 Uiso 1 1 calc R U . . .
C10 C 1.126(2) 0.026(2) 0.616(2) 0.126(9) Uani 1 1 d . . . . .
H10A H 1.0791 0.0081 0.6813 0.189 Uiso 1 1 calc R U . . .
H10B H 1.1586 -0.0339 0.5824 0.189 Uiso 1 1 calc R U . . .
H10C H 1.0763 0.0604 0.5594 0.189 Uiso 1 1 calc R U . . .
C16 C 1.4968(18) 0.4165(17) 0.7136(17) 0.084(6) Uani 1 1 d . . . . .
H16A H 1.5125 0.3511 0.679 0.1 Uiso 1 1 calc R U . . .
H16B H 1.4551 0.4573 0.6555 0.1 Uiso 1 1 calc R U . . .
C6 C 1.8965(13) 0.4221(12) 0.9827(15) 0.058(4) Uani 1 1 d . . . . .
C19 C 1.2184(17) 0.4191(16) 0.7047(17) 0.084(6) Uani 1 1 d . . . . .
H19A H 1.254 0.4168 0.629 0.101 Uiso 1 1 calc R U . . .
H19B H 1.1398 0.3885 0.6969 0.101 Uiso 1 1 calc R U . . .
C14 C 1.240(2) 0.2039(18) 1.182(2) 0.113(8) Uani 1 1 d . . . . .
H14A H 1.3167 0.176 1.1653 0.169 Uiso 1 1 calc R U . . .
H14B H 1.1814 0.1507 1.183 0.169 Uiso 1 1 calc R U . . .
H14C H 1.2441 0.236 1.2571 0.169 Uiso 1 1 calc R U . . .
C15 C 1.4161(16) 0.4013(16) 0.8128(18) 0.081(6) Uani 1 1 d . . . . .
H15A H 1.4042 0.4665 0.8493 0.098 Uiso 1 1 calc R U . . .
H15B H 1.4574 0.3585 0.8693 0.098 Uiso 1 1 calc R U . . .
C22 C 1.090(3) 0.688(2) 0.685(4) 0.181(17) Uani 1 1 d . . . . .
H22A H 1.0656 0.6997 0.7631 0.271 Uiso 1 1 calc R U . . .
H22B H 1.0302 0.7127 0.6315 0.271 Uiso 1 1 calc R U . . .
H22C H 1.1644 0.723 0.6731 0.271 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
Au1 S4 2.315(4) . ?
Au1 S1 2.324(4) . ?
Au1 S3 2.325(4) . ?
Au1 S6 2.327(4) . ?
I1 C3 2.079(16) . ?
I2 C6 2.093(15) . ?
S4 C4 1.720(17) . ?
S3 C2 1.778(14) . ?
S1 C1 1.719(16) . ?
S6 C5 1.760(15) . ?
S2 C3 1.721(16) . ?
S2 C1 1.742(16) . ?
S5 C6 1.719(17) . ?
S5 C4 1.754(17) . ?
N1 C3 1.330(19) . ?
N1 C2 1.409(18) . ?
N2 C6 1.312(19) . ?
N2 C5 1.410(19) . ?
N3 C19 1.51(2) . ?
N3 C11 1.52(2) . ?
N3 C15 1.52(2) . ?
N3 C7 1.55(2) . ?
C4 C5 1.33(2) . ?
C12 C13 1.49(3) . ?
C12 C11 1.50(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C2 C1 1.33(2) . ?
C18 C17 1.48(3) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C17 C16 1.45(3) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C20 C21 1.47(3) . ?
C20 C19 1.49(3) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C7 C8 1.48(2) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.45(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.48(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C13 C14 1.43(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C21 C22 1.49(3) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C16 C15 1.49(2) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?

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
S4 Au1 S1 87.23(14) . . ?
S4 Au1 S3 178.32(18) . . ?
S1 Au1 S3 92.17(14) . . ?
S4 Au1 S6 92.24(14) . . ?
S1 Au1 S6 178.73(18) . . ?
S3 Au1 S6 88.40(14) . . ?
C4 S4 Au1 98.5(5) . . ?
C2 S3 Au1 98.6(5) . . ?
C1 S1 Au1 98.5(6) . . ?
C5 S6 Au1 98.6(5) . . ?
C3 S2 C1 89.1(8) . . ?
C6 S5 C4 88.1(8) . . ?
C3 N1 C2 105.8(12) . . ?
C6 N2 C5 106.0(12) . . ?
C19 N3 C11 109.8(15) . . ?
C19 N3 C15 112.5(14) . . ?
C11 N3 C15 108.0(15) . . ?
C19 N3 C7 107.9(14) . . ?
C11 N3 C7 109.9(14) . . ?
C15 N3 C7 108.6(14) . . ?
N1 C3 S2 117.1(12) . . ?
N1 C3 I1 124.8(11) . . ?
S2 C3 I1 118.1(9) . . ?
C5 C4 S4 127.3(13) . . ?
C5 C4 S5 108.8(12) . . ?
S4 C4 S5 123.9(9) . . ?
C4 C5 N2 118.7(14) . . ?
C4 C5 S6 123.4(12) . . ?
N2 C5 S6 117.8(11) . . ?
C13 C12 C11 109.9(16) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C1 C2 N1 119.5(13) . . ?
C1 C2 S3 123.0(12) . . ?
N1 C2 S3 117.5(11) . . ?
C2 C1 S1 127.5(12) . . ?
C2 C1 S2 108.4(11) . . ?
S1 C1 S2 124.1(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C17 C18 116.1(19) . . ?
C16 C17 H17A 108.3 . . ?
C18 C17 H17A 108.3 . . ?
C16 C17 H17B 108.3 . . ?
C18 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C21 C20 C19 113(2) . . ?
C21 C20 H20A 109 . . ?
C19 C20 H20A 109 . . ?
C21 C20 H20B 109 . . ?
C19 C20 H20B 109 . . ?
H20A C20 H20B 107.8 . . ?
C12 C11 N3 120.1(17) . . ?
C12 C11 H11A 107.3 . . ?
N3 C11 H11A 107.3 . . ?
C12 C11 H11B 107.3 . . ?
N3 C11 H11B 107.3 . . ?
H11A C11 H11B 106.9 . . ?
C8 C7 N3 115.7(15) . . ?
C8 C7 H7A 108.3 . . ?
N3 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
N3 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C7 111.8(17) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 121(2) . . ?
C8 C9 H9A 107.2 . . ?
C10 C9 H9A 107.2 . . ?
C8 C9 H9B 107.2 . . ?
C10 C9 H9B 107.2 . . ?
H9A C9 H9B 106.8 . . ?
C14 C13 C12 113(2) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C20 C21 C22 118(3) . . ?
C20 C21 H21A 107.9 . . ?
C22 C21 H21A 107.9 . . ?
C20 C21 H21B 107.9 . . ?
C22 C21 H21B 107.9 . . ?
H21A C21 H21B 107.2 . . ?
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 . . ?
C17 C16 C15 115.2(18) . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
N2 C6 S5 118.3(11) . . ?
N2 C6 I2 124.7(11) . . ?
S5 C6 I2 116.8(9) . . ?
C20 C19 N3 116.6(16) . . ?
C20 C19 H19A 108.1 . . ?
N3 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
N3 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N3 117.5(16) . . ?
C16 C15 H15A 107.9 . . ?
N3 C15 H15A 107.9 . . ?
C16 C15 H15B 107.9 . . ?
N3 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C3 S2 -3.1(16) . . . . ?
C2 N1 C3 I1 176.0(10) . . . . ?
C1 S2 C3 N1 1.9(13) . . . . ?
C1 S2 C3 I1 -177.3(9) . . . . ?
Au1 S4 C4 C5 -0.8(16) . . . . ?
Au1 S4 C4 S5 -178.8(10) . . . . ?
C6 S5 C4 C5 0.7(13) . . . . ?
C6 S5 C4 S4 179.1(12) . . . . ?
S4 C4 C5 N2 179.9(11) . . . . ?
S5 C4 C5 N2 -1.8(19) . . . . ?
S4 C4 C5 S6 2(2) . . . . ?
S5 C4 C5 S6 -179.5(9) . . . . ?
C6 N2 C5 C4 2.1(19) . . . . ?
C6 N2 C5 S6 180.0(11) . . . . ?
Au1 S6 C5 C4 -2.1(14) . . . . ?
Au1 S6 C5 N2 -179.8(10) . . . . ?
C3 N1 C2 C1 3.2(19) . . . . ?
C3 N1 C2 S3 -178.9(11) . . . . ?
Au1 S3 C2 C1 -4.8(14) . . . . ?
Au1 S3 C2 N1 177.4(10) . . . . ?
N1 C2 C1 S1 -179.7(11) . . . . ?
S3 C2 C1 S1 3(2) . . . . ?
N1 C2 C1 S2 -2.0(18) . . . . ?
S3 C2 C1 S2 -179.6(8) . . . . ?
Au1 S1 C1 C2 1.4(16) . . . . ?
Au1 S1 C1 S2 -176.0(9) . . . . ?
C3 S2 C1 C2 0.1(12) . . . . ?
C3 S2 C1 S1 177.9(11) . . . . ?
C13 C12 C11 N3 174.7(17) . . . . ?
C19 N3 C11 C12 168.8(17) . . . . ?
C15 N3 C11 C12 -68(2) . . . . ?
C7 N3 C11 C12 50(2) . . . . ?
C19 N3 C7 C8 -59(2) . . . . ?
C11 N3 C7 C8 60(2) . . . . ?
C15 N3 C7 C8 178.3(17) . . . . ?
N3 C7 C8 C9 -176.3(18) . . . . ?
C7 C8 C9 C10 -177(2) . . . . ?
C11 C12 C13 C14 177.1(19) . . . . ?
C19 C20 C21 C22 -175(2) . . . . ?
C18 C17 C16 C15 175(2) . . . . ?
C5 N2 C6 S5 -1.5(17) . . . . ?
C5 N2 C6 I2 173.4(11) . . . . ?
C4 S5 C6 N2 0.5(14) . . . . ?
C4 S5 C6 I2 -174.8(9) . . . . ?
C21 C20 C19 N3 -167.5(16) . . . . ?
C11 N3 C19 C20 67(2) . . . . ?
C15 N3 C19 C20 -53(2) . . . . ?
C7 N3 C19 C20 -173.2(15) . . . . ?
C17 C16 C15 N3 177.6(18) . . . . ?
C19 N3 C15 C16 -61(2) . . . . ?
C11 N3 C15 C16 177.6(18) . . . . ?
C7 N3 C15 C16 58(2) . . . . ?

####################################################################### 
# 
# 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_C4HNOS3
_database_code_depnum_ccdc_archive 'CCDC 1994382'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_date             2017-09-13T15:37:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C4 H N O S3'
_chemical_formula_moiety         'C4 H N O S3'
_chemical_formula_weight         175.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.9123(2)
_cell_length_b                   16.5922(11)
_cell_length_c                   9.7464(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.329(3)
_cell_angle_gamma                90
_cell_volume                     626.00(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1811
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.3
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12

_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_T_max  0.878

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6384  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------# 

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.246507
_diffrn_orient_matrix_ub_12      0.013522
_diffrn_orient_matrix_ub_13      -0.005958
_diffrn_orient_matrix_ub_21      -0.070828
_diffrn_orient_matrix_ub_22      0.055471
_diffrn_orient_matrix_ub_23      -0.032721
_diffrn_orient_matrix_ub_31      0.030867
_diffrn_orient_matrix_ub_32      0.019301
_diffrn_orient_matrix_ub_33      0.098218
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_number            4310
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             1415
_reflns_number_gt                1183
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.5735P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1415
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S3 S 0.63824(19) 0.29933(4) 0.17622(7) 0.03342(19) Uani 1 1 d . . . . .
S1 S 0.66015(19) 0.11366(4) 0.12178(7) 0.0361(2) Uani 1 1 d . . . . .
S2 S 0.4437(2) 0.09471(4) 0.40205(7) 0.0367(2) Uani 1 1 d . . . . .
N1 N 0.4460(6) 0.26182(13) 0.4102(2) 0.0316(5) Uani 1 1 d . . . . .
C4 C 0.5129(7) 0.32217(17) 0.3335(3) 0.0338(6) Uani 1 1 d . . . . .
H4 H 0.4939 0.3752 0.3623 0.041 Uiso 1 1 calc R U . . .
O1 O 0.5589(7) -0.02547(13) 0.2382(2) 0.0646(7) Uani 1 1 d . . . . .
C3 C 0.4955(6) 0.19193(14) 0.3414(2) 0.0266(5) Uani 1 1 d . . . . .
C2 C 0.5962(7) 0.19970(15) 0.2140(3) 0.0283(5) Uani 1 1 d . . . . .
C1 C 0.5556(8) 0.04663(18) 0.2517(3) 0.0396(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
S3 C2 1.707(3) . ?
S3 C4 1.718(3) . ?
S1 C2 1.725(3) . ?
S1 C1 1.777(3) . ?
S2 C3 1.740(2) . ?
S2 C1 1.777(3) . ?
N1 C4 1.299(3) . ?
N1 C3 1.367(3) . ?
C4 H4 0.93 . ?
O1 C1 1.204(3) . ?
C3 C2 1.362(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S3 C4 88.39(12) . . ?
C2 S1 C1 94.62(12) . . ?
C3 S2 C1 94.67(13) . . ?
C4 N1 C3 108.5(2) . . ?
N1 C4 S3 116.8(2) . . ?
N1 C4 H4 121.6 . . ?
S3 C4 H4 121.6 . . ?
C2 C3 N1 116.6(2) . . ?
C2 C3 S2 117.43(19) . . ?
N1 C3 S2 126.01(18) . . ?
C3 C2 S3 109.77(18) . . ?
C3 C2 S1 118.69(19) . . ?
S3 C2 S1 131.54(15) . . ?
O1 C1 S1 122.4(2) . . ?
O1 C1 S2 123.0(2) . . ?
S1 C1 S2 114.59(16) . . ?

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 C4 S3 -0.1(3) . . . . ?
C2 S3 C4 N1 0.4(2) . . . . ?
C4 N1 C3 C2 -0.4(3) . . . . ?
C4 N1 C3 S2 179.2(2) . . . . ?
C1 S2 C3 C2 -0.5(2) . . . . ?
C1 S2 C3 N1 179.8(2) . . . . ?
N1 C3 C2 S3 0.7(3) . . . . ?
S2 C3 C2 S3 -178.97(13) . . . . ?
N1 C3 C2 S1 -179.60(18) . . . . ?
S2 C3 C2 S1 0.7(3) . . . . ?
C4 S3 C2 C3 -0.6(2) . . . . ?
C4 S3 C2 S1 179.8(2) . . . . ?
C1 S1 C2 C3 -0.4(2) . . . . ?
C1 S1 C2 S3 179.1(2) . . . . ?
C2 S1 C1 O1 179.7(3) . . . . ?
C2 S1 C1 S2 0.07(18) . . . . ?
C3 S2 C1 O1 -179.4(3) . . . . ?
C3 S2 C1 S1 0.21(18) . . . . ?

