# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_compound2b
_database_code_depnum_ccdc_archive 'CCDC 1872721'
loop_
_audit_author_name
_audit_author_address
'Vincent Dorcet and Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2018-10-11 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H6 I N S2'
_chemical_formula_sum            'C9 H6 I N S2'
_chemical_formula_weight         319.17
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_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                   8.7777(10)
_cell_length_b                   11.1568(15)
_cell_length_c                   21.241(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.632(4)
_cell_angle_gamma                90
_cell_volume                     2066.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9107
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.53
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1216
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.454
_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  0.490
_exptl_absorpt_correction_T_max  0.617

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0274
_diffrn_reflns_av_uneti/neti     0.0285
_diffrn_reflns_number            8223
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.965
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             2344
_reflns_number_gt                2188
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            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    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+17.8269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0048(3)
_refine_ls_number_reflns         2344
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.659
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.244

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 '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'
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'

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
I1 I 0.51952(3) 0.24756(2) 0.39336(2) 0.02051(16) Uani 1 1 d . . . . .
S1 S 0.72871(13) 0.22405(10) 0.74470(5) 0.0199(3) Uani 1 1 d . . . . .
S2 S 0.53235(12) 0.07978(9) 0.64757(5) 0.0185(2) Uani 1 1 d . . . . .
C1 C 0.4499(4) 0.3194(3) 0.47687(17) 0.0143(7) Uani 1 1 d . . . . .
C2 C 0.3194(4) 0.3914(4) 0.47347(19) 0.0172(8) Uani 1 1 d . . . . .
H2 H 0.261354 0.407642 0.433829 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2759(4) 0.4391(4) 0.5292(2) 0.0179(8) Uani 1 1 d . . . . .
H3 H 0.187154 0.488234 0.527442 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3608(5) 0.4156(3) 0.58765(19) 0.0181(8) Uani 1 1 d . . . . .
H4 H 0.331531 0.449145 0.625568 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4881(4) 0.3428(3) 0.58910(17) 0.0132(7) Uani 1 1 d . . . . .
C6 C 0.5362(4) 0.2933(3) 0.53433(18) 0.0138(7) Uani 1 1 d . . . . .
H6 H 0.624620 0.243687 0.536255 0.017 Uiso 1 1 calc R U . . .
N7 N 0.5812(4) 0.3216(3) 0.64882(15) 0.0148(6) Uani 1 1 d . . . . .
C8 C 0.6589(5) 0.4146(4) 0.6829(2) 0.0234(9) Uani 1 1 d . . . . .
H8 H 0.651600 0.496155 0.669976 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7447(5) 0.3775(4) 0.73560(19) 0.0235(9) Uani 1 1 d . . . . .
H9 H 0.805880 0.428413 0.764067 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6059(4) 0.2102(4) 0.67503(18) 0.0130(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
I1 C1 2.101(4) . ?
S1 C9 1.730(5) . ?
S1 C10 1.734(4) . ?
S2 C10 1.670(4) . ?
C1 C6 1.391(5) . ?
C1 C2 1.394(5) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(5) . ?
C5 N7 1.447(5) . ?
C6 H6 0.9500 . ?
N7 C10 1.369(5) . ?
N7 C8 1.396(5) . ?
C8 C9 1.341(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C10 92.5(2) . . ?
C6 C1 C2 121.8(4) . . ?
C6 C1 I1 118.6(3) . . ?
C2 C1 I1 119.6(3) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.5(3) . . ?
C4 C5 N7 119.3(3) . . ?
C6 C5 N7 118.1(3) . . ?
C1 C6 C5 117.5(4) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C10 N7 C8 114.8(3) . . ?
C10 N7 C5 123.5(3) . . ?
C8 N7 C5 121.7(3) . . ?
C9 C8 N7 113.3(4) . . ?
C9 C8 H8 123.3 . . ?
N7 C8 H8 123.3 . . ?
C8 C9 S1 110.8(3) . . ?
C8 C9 H9 124.6 . . ?
S1 C9 H9 124.6 . . ?
N7 C10 S2 127.8(3) . . ?
N7 C10 S1 108.6(3) . . ?
S2 C10 S1 123.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(6) . . . . ?
I1 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C3 C4 C5 N7 177.4(3) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
I1 C1 C6 C5 179.6(3) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
N7 C5 C6 C1 -176.8(3) . . . . ?
C4 C5 N7 C10 120.0(4) . . . . ?
C6 C5 N7 C10 -63.4(5) . . . . ?
C4 C5 N7 C8 -62.9(5) . . . . ?
C6 C5 N7 C8 113.7(4) . . . . ?
C10 N7 C8 C9 0.1(6) . . . . ?
C5 N7 C8 C9 -177.2(4) . . . . ?
N7 C8 C9 S1 -0.8(5) . . . . ?
C10 S1 C9 C8 0.9(4) . . . . ?
C8 N7 C10 S2 179.9(3) . . . . ?
C5 N7 C10 S2 -2.8(6) . . . . ?
C8 N7 C10 S1 0.6(4) . . . . ?
C5 N7 C10 S1 177.9(3) . . . . ?
C9 S1 C10 N7 -0.8(3) . . . . ?
C9 S1 C10 S2 179.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 S2 0.95 2.94 3.797(4) 151.1 7_556
C6 H6 I1 0.95 3.31 4.048(4) 136.6 7_656
C9 H9 S2 0.95 2.79 3.737(4) 175.9 4_656
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_compound3a
_database_code_depnum_ccdc_archive 'CCDC 1872722'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Insitut des sciences chimiques de Rennes, Univ Rennes
France
;
_audit_update_record             
;
2019-01-14 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 I N O S4'
_chemical_formula_sum            'C10 H4 I N O S4'
_chemical_formula_weight         409.28
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.1078(7)
_cell_length_b                   24.675(5)
_cell_length_c                   13.943(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.785(7)
_cell_angle_gamma                90
_cell_volume                     1238.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    4435
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.21
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.195
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             784
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.238
_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  0.772
_exptl_absorpt_correction_T_max  0.968

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  ?
_diffrn_reflns_av_uneti/neti     0.1025
_diffrn_reflns_number            11687
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         27.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             11687
_reflns_number_gt                8472
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

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

_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.,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)+38.5204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11687
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.1758
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         4.004
_refine_diff_density_min         -4.063
_refine_diff_density_rms         0.300

#...............................................................................
# .RES SHELXL file: hklf5.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.009(3) 0.7152(4) 0.5876(9) 0.016(2) Uani 1 1 d . . . . .
C2 C -0.021(3) 0.6635(4) 0.4326(9) 0.017(3) Uani 1 1 d . . . . .
C3 C 0.120(4) 0.6350(5) 0.5279(10) 0.022(3) Uani 1 1 d . . . . .
C4 C 0.158(4) 0.5715(5) 0.3849(10) 0.025(3) Uani 1 1 d . . . . .
C5 C 0.328(3) 0.6422(4) 0.7246(8) 0.014(2) Uani 1 1 d . . . . .
C6 C 0.607(3) 0.6715(4) 0.8072(9) 0.017(2) Uani 1 1 d . . . . .
H6 H 0.671600 0.706286 0.792343 0.020 Uiso 1 1 calc R U . . .
C7 C 0.794(3) 0.6502(4) 0.9130(9) 0.015(3) Uani 1 1 d . . . . .
H7 H 0.984235 0.670451 0.970803 0.018 Uiso 1 1 calc R U . . .
C8 C 0.700(3) 0.5994(4) 0.9325(9) 0.014(2) Uani 1 1 d . . . . .
C9 C 0.419(3) 0.5699(5) 0.8494(9) 0.018(2) Uani 1 1 d . . . . .
H9 H 0.360026 0.534780 0.864403 0.022 Uiso 1 1 calc R U . . .
C10 C 0.222(3) 0.5911(4) 0.7444(9) 0.015(2) Uani 1 1 d . . . . .
H10 H 0.022039 0.571636 0.687919 0.018 Uiso 1 1 calc R U . . .
I1 I 0.9896(2) 0.56710(3) 1.09001(6) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.142(3) 0.6638(3) 0.6153(7) 0.015(2) Uani 1 1 d . . . . .
O1 O 0.218(3) 0.5343(4) 0.3419(7) 0.036(3) Uani 1 1 d . . . . .
S1 S -0.0618(9) 0.76145(11) 0.6647(2) 0.0172(6) Uani 1 1 d . . . . .
S2 S -0.1471(10) 0.72796(11) 0.4503(2) 0.0195(7) Uani 1 1 d . . . . .
S3 S -0.0480(10) 0.63360(12) 0.3166(2) 0.0231(7) Uani 1 1 d . . . . .
S4 S 0.2649(9) 0.56973(12) 0.5263(2) 0.0233(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
C1 N1 1.382(14) . ?
C1 S1 1.653(12) . ?
C1 S2 1.743(12) . ?
C2 C3 1.362(16) . ?
C2 S2 1.728(12) . ?
C2 S3 1.731(12) . ?
C3 N1 1.375(15) . ?
C3 S4 1.722(12) . ?
C4 O1 1.185(15) . ?
C4 S3 1.788(13) . ?
C4 S4 1.803(13) . ?
C5 C6 1.375(16) . ?
C5 C10 1.405(16) . ?
C5 N1 1.438(13) . ?
C6 C7 1.398(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(16) . ?
C8 I1 2.088(10) . ?
C9 C10 1.389(15) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 129.4(9) . . ?
N1 C1 S2 109.7(8) . . ?
S1 C1 S2 120.9(6) . . ?
C3 C2 S2 110.5(9) . . ?
C3 C2 S3 119.9(9) . . ?
S2 C2 S3 129.6(7) . . ?
C2 C3 N1 114.5(10) . . ?
C2 C3 S4 117.2(9) . . ?
N1 C3 S4 128.2(9) . . ?
O1 C4 S3 123.7(10) . . ?
O1 C4 S4 122.3(10) . . ?
S3 C4 S4 114.0(7) . . ?
C6 C5 C10 121.3(10) . . ?
C6 C5 N1 119.7(10) . . ?
C10 C5 N1 119.0(10) . . ?
C5 C6 C7 119.9(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.1(10) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.0(10) . . ?
C7 C8 I1 118.8(8) . . ?
C9 C8 I1 120.2(8) . . ?
C8 C9 C10 120.8(11) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 117.8(10) . . ?
C9 C10 H10 121.1 . . ?
C5 C10 H10 121.1 . . ?
C3 N1 C1 113.4(9) . . ?
C3 N1 C5 121.6(9) . . ?
C1 N1 C5 125.0(10) . . ?
C2 S2 C1 91.7(5) . . ?
C2 S3 C4 93.8(6) . . ?
C3 S4 C4 95.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C2 C3 N1 -2.3(15) . . . . ?
S3 C2 C3 N1 177.4(9) . . . . ?
S2 C2 C3 S4 -179.6(7) . . . . ?
S3 C2 C3 S4 0.1(16) . . . . ?
C10 C5 C6 C7 1.0(19) . . . . ?
N1 C5 C6 C7 -178.4(11) . . . . ?
C5 C6 C7 C8 1.1(19) . . . . ?
C6 C7 C8 C9 -1.2(19) . . . . ?
C6 C7 C8 I1 178.6(9) . . . . ?
C7 C8 C9 C10 -0.7(19) . . . . ?
I1 C8 C9 C10 179.5(9) . . . . ?
C8 C9 C10 C5 2.6(18) . . . . ?
C6 C5 C10 C9 -2.8(18) . . . . ?
N1 C5 C10 C9 176.6(11) . . . . ?
C2 C3 N1 C1 4.6(17) . . . . ?
S4 C3 N1 C1 -178.5(10) . . . . ?
C2 C3 N1 C5 -171.8(11) . . . . ?
S4 C3 N1 C5 5.1(19) . . . . ?
S1 C1 N1 C3 176.2(11) . . . . ?
S2 C1 N1 C3 -4.6(14) . . . . ?
S1 C1 N1 C5 -7.6(19) . . . . ?
S2 C1 N1 C5 171.6(9) . . . . ?
C6 C5 N1 C3 125.3(13) . . . . ?
C10 C5 N1 C3 -54.1(17) . . . . ?
C6 C5 N1 C1 -50.6(18) . . . . ?
C10 C5 N1 C1 130.0(13) . . . . ?
C3 C2 S2 C1 -0.3(11) . . . . ?
S3 C2 S2 C1 -180.0(10) . . . . ?
N1 C1 S2 C2 2.7(10) . . . . ?
S1 C1 S2 C2 -178.0(9) . . . . ?
C3 C2 S3 C4 -1.6(12) . . . . ?
S2 C2 S3 C4 178.1(10) . . . . ?
O1 C4 S3 C2 -178.3(14) . . . . ?
S4 C4 S3 C2 2.4(8) . . . . ?
C2 C3 S4 C4 1.4(12) . . . . ?
N1 C3 S4 C4 -175.5(13) . . . . ?
O1 C4 S4 C3 178.3(13) . . . . ?
S3 C4 S4 C3 -2.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 S1 0.95 2.84 3.651(12) 143.3 1_655 yes

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR AC23                                                   #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_compound4c
_database_code_depnum_ccdc_archive 'CCDC 1872724'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel' 'Insitut des sciences chimiques de Rennes, Univ Rennes'
_audit_update_record             
;
2019-01-14 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
#                               VALIDATION REPLY FORM                          #
#------------------------------------------------------------------------------#

_vrf_PLAT084_ALERT_3_B           
;
PROBLEM:   High wR2 Value (i.e. > 0.25) .....       0.36 Report
RESPONSE: 
           The measured crystal was a really thin stick and a poor diffractor:
           as a consequence, Bragg reflections at high angle had small 
           intensities and their standart deviations of same level, leading 
           to provide high values of wR2.
;

_vrf_PLAT097_ALERT_2_B           
;
PROBLEM:   Large Reported Max.  (Positive) Residual Density       5.52 eA-3
RESPONSE:  This large residual density of is a refinement artefact due
           to weak diffraction below 0.95 A of resolution.
;

_vrf_PLAT250_ALERT_2_B           
;
PROBLEM:   Large U3/U1 Ratio for Average U(i,j) Tensor ....        5.0 Note 
RESPONSE:  The deviation of this ratio from 1.0 could be a consequence of
           the low quality of the data set, due to the poor diffraction
           power of the measured crystal.
;

_vrf_PLAT431_ALERT_2_B           
;
PROBLEM:   Short Inter HL..A Contact  I1       ..S16      .       3.39 Ang.  
RESPONSE:  This short intermolecular contact distance is due to halogen 
           bounding and is a structural feature of this kind of iodine 
           compounds.
;

#------------------------------------------------------------------------------#
#                         END OF VALIDATION REPLY FORM                         #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H8 I2 N2 S6'
_chemical_formula_sum            'C18 H8 I2 N2 S6'
_chemical_formula_weight         698.42
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.5260(18)
_cell_length_b                   14.352(2)
_cell_length_c                   14.522(2)
_cell_angle_alpha                117.141(4)
_cell_angle_beta                 95.478(5)
_cell_angle_gamma                100.638(5)
_cell_volume                     2234.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.43
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1328
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.384
_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  0.774
_exptl_absorpt_correction_T_max  0.935

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.1050
_diffrn_reflns_av_uneti/neti     0.0758
_diffrn_reflns_number            51086
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             10225
_reflns_number_gt                6098
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            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    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1722P)²+58.2156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10225
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1793
_refine_ls_R_factor_gt           0.1160
_refine_ls_wR_factor_ref         0.3626
_refine_ls_wR_factor_gt          0.3164
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         5.516
_refine_diff_density_min         -3.680
_refine_diff_density_rms         0.325

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 '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'
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'

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
I1 I 0.66254(10) 0.30737(10) 0.80221(10) 0.0514(4) Uani 1 1 d . . . . .
I2 I 0.10613(16) 0.38873(19) 0.62823(16) 0.1068(8) Uani 1 1 d . . . . .
S1 S 0.7235(3) 0.6109(3) 1.1115(3) 0.0326(8) Uani 1 1 d . . . . .
S2 S 0.5329(2) 0.6180(3) 0.9793(3) 0.0247(7) Uani 1 1 d . . . . .
S3 S 0.6752(3) 0.5229(5) 0.7089(3) 0.0546(13) Uani 1 1 d . . . . .
S4 S 0.4639(3) 0.5598(5) 0.6510(3) 0.0580(15) Uani 1 1 d . . . . .
S5 S 0.3163(3) 0.6485(3) 0.9185(3) 0.0309(8) Uani 1 1 d . . . . .
S6 S 0.2841(6) 0.5889(11) 0.5258(4) 0.144(5) Uani 1 1 d . . . . .
C1 C 0.8094(6) 0.4265(8) 0.8522(10) 0.0480(18) Uani 1 1 d G . . . .
C2 C 0.9094(8) 0.3980(7) 0.8404(9) 0.0480(18) Uani 1 1 d G . . . .
H2 H 0.910105 0.323805 0.808091 0.058 Uiso 1 1 calc R U . . .
C3 C 1.0083(6) 0.4780(8) 0.8759(9) 0.0480(18) Uani 1 1 d G . . . .
H3 H 1.076609 0.458512 0.867888 0.058 Uiso 1 1 calc R U . . .
C4 C 1.0072(6) 0.5865(7) 0.9232(9) 0.0480(18) Uani 1 1 d G . . . .
H4 H 1.074771 0.641229 0.947514 0.058 Uiso 1 1 calc R U . . .
C5 C 0.9072(8) 0.6151(7) 0.9350(9) 0.0480(18) Uani 1 1 d G . . . .
H5 H 0.906429 0.689240 0.967344 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8083(6) 0.5350(8) 0.8995(10) 0.0480(18) Uani 1 1 d G . . . .
N7 N 0.7058(8) 0.5656(10) 0.9090(9) 0.030(3) Uani 1 1 d . . . . .
C8 C 0.6649(10) 0.5962(11) 0.9994(11) 0.027(3) Uani 1 1 d . . . . .
C9 C 0.6404(11) 0.5599(13) 0.8234(11) 0.033(3) Uani 1 1 d . . . . .
C10 C 0.5378(10) 0.5882(12) 0.8504(11) 0.029(3) Uani 1 1 d . . . . .
C11 C 0.4563(11) 0.5911(13) 0.7829(11) 0.033(3) Uani 1 1 d . . . . .
C12 C 0.3540(11) 0.6186(12) 0.8057(10) 0.030(3) Uani 1 1 d . . . . .
N13 N 0.2923(10) 0.6185(14) 0.7226(10) 0.050(4) Uani 1 1 d . . . . .
C14 C 0.3361(14) 0.591(2) 0.6318(11) 0.068(7) Uani 1 1 d . . . . .
C16 C 0.1840(6) 0.6346(11) 0.7234(10) 0.062(2) Uani 1 1 d G . . . .
C17 C 0.1735(7) 0.7401(10) 0.7631(10) 0.062(2) Uani 1 1 d G . . . .
H17 H 0.237933 0.798849 0.790065 0.075 Uiso 1 1 calc R U . . .
C18 C 0.0689(9) 0.7595(9) 0.7633(10) 0.062(2) Uani 1 1 d G . . . .
H18 H 0.061733 0.831615 0.790412 0.075 Uiso 1 1 calc R U . . .
C19 C -0.0253(6) 0.6735(11) 0.7238(10) 0.062(2) Uani 1 1 d G . . . .
H19 H -0.096861 0.686844 0.723956 0.075 Uiso 1 1 calc R U . . .
C20 C -0.0149(7) 0.5681(10) 0.6841(10) 0.062(2) Uani 1 1 d G . . . .
H20 H -0.079257 0.509307 0.657154 0.075 Uiso 1 1 calc R U . . .
C21 C 0.0898(9) 0.5486(9) 0.6839(10) 0.062(2) Uani 1 1 d G . . . .
I11 I 0.78443(11) 0.12401(11) -0.06532(11) 0.0568(4) Uani 1 1 d . . . . .
I12 I 0.75952(18) 0.13747(16) 0.47459(16) 0.0921(6) Uani 1 1 d . . . . .
S11 S 0.4901(3) -0.1376(4) -0.2142(3) 0.0396(9) Uani 1 1 d . . . . .
S12 S 0.8918(3) -0.1056(4) -0.0214(3) 0.0371(9) Uani 1 1 d . . . . .
S13 S 0.5543(3) -0.1165(3) -0.0025(3) 0.0265(7) Uani 1 1 d . . . . .
S14 S 0.8655(3) -0.1083(3) 0.1777(3) 0.0283(7) Uani 1 1 d . . . . .
S15 S 0.9221(3) -0.1229(4) 0.3722(3) 0.0445(10) Uani 1 1 d . . . . .
S16 S 0.5312(3) -0.1066(3) 0.2004(3) 0.0317(8) Uani 1 1 d . . . . .
C51 C 0.7901(9) -0.0150(9) -0.1957(7) 0.054(2) Uani 1 1 d G . . . .
C52 C 0.8378(8) -0.0096(9) -0.2763(8) 0.054(2) Uani 1 1 d G . . . .
H52 H 0.870777 0.058758 -0.269847 0.065 Uiso 1 1 calc R U . . .
C53 C 0.8372(9) -0.1044(10) -0.3663(7) 0.054(2) Uani 1 1 d G . . . .
H53 H 0.869822 -0.100781 -0.421442 0.065 Uiso 1 1 calc R U . . .
C54 C 0.7889(9) -0.2045(9) -0.3758(7) 0.054(2) Uani 1 1 d G . . . .
H54 H 0.788558 -0.269279 -0.437313 0.065 Uiso 1 1 calc R U . . .
C55 C 0.7412(8) -0.2098(9) -0.2951(8) 0.054(2) Uani 1 1 d G . . . .
H55 H 0.708248 -0.278240 -0.301589 0.065 Uiso 1 1 calc R U . . .
C56 C 0.7418(8) -0.1151(10) -0.2051(7) 0.054(2) Uani 1 1 d G . . . .
N57 N 0.6958(9) -0.1190(11) -0.1214(9) 0.030(3) Uani 1 1 d . . . . .
C58 C 0.5840(10) -0.1277(12) -0.1211(10) 0.027(3) Uani 1 1 d . . . . .
C59 C 0.7591(10) -0.1130(11) -0.0342(10) 0.025(3) Uani 1 1 d . . . . .
C60 C 0.6908(10) -0.1118(11) 0.0416(10) 0.023(3) Uani 1 1 d . . . . .
C61 C 0.7305(10) -0.1088(11) 0.1356(9) 0.022(3) Uani 1 1 d . . . . .
C62 C 0.6606(11) -0.1106(11) 0.2103(10) 0.025(3) Uani 1 1 d . . . . .
N63 N 0.7218(9) -0.1130(10) 0.2937(8) 0.026(2) Uani 1 1 d . . . . .
C64 C 0.8323(10) -0.1152(12) 0.2897(10) 0.029(3) Uani 1 1 d . . . . .
C65 C 0.6755(9) -0.1138(11) 0.3771(7) 0.055(2) Uani 1 1 d G . . . .
C66 C 0.6222(10) -0.2118(9) 0.3696(7) 0.055(2) Uani 1 1 d G . . . .
H66 H 0.621529 -0.278114 0.309723 0.066 Uiso 1 1 calc R U . . .
C67 C 0.5700(9) -0.2126(9) 0.4495(8) 0.055(2) Uani 1 1 d G . . . .
H67 H 0.533649 -0.279555 0.444376 0.066 Uiso 1 1 calc R U . . .
C68 C 0.5711(9) -0.1155(10) 0.5371(7) 0.055(2) Uani 1 1 d G . . . .
H68 H 0.535387 -0.116109 0.591747 0.066 Uiso 1 1 calc R U . . .
C69 C 0.6243(9) -0.0176(9) 0.5446(7) 0.055(2) Uani 1 1 d G . . . .
H69 H 0.625005 0.048779 0.604467 0.066 Uiso 1 1 calc R U . . .
C70 C 0.6765(9) -0.0167(9) 0.4647(9) 0.055(2) Uani 1 1 d G . . . .



#------------------------------------------------------------------------------#
#                              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
I1 C1 2.070(8) . ?
I2 C21 2.115(11) . ?
S1 C8 1.623(14) . ?
S2 C10 1.730(14) . ?
S2 C8 1.761(13) . ?
S3 C9 1.629(14) . ?
S4 C14 1.772(16) . ?
S4 C11 1.775(15) . ?
S5 C12 1.635(14) . ?
S6 C14 1.597(18) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 N7 1.430(11) . ?
N7 C8 1.365(17) . ?
N7 C9 1.382(19) . ?
C9 C10 1.454(16) . ?
C10 C11 1.366(19) . ?
C11 C12 1.434(18) . ?
C12 N13 1.368(19) . ?
N13 C14 1.393(19) . ?
N13 C16 1.418(13) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
I11 C51 2.049(9) . ?
I12 C70 2.198(10) . ?
S11 C58 1.641(13) . ?
S12 C59 1.632(13) . ?
S13 C58 1.737(14) . ?
S13 C60 1.747(12) . ?
S14 C61 1.739(13) . ?
S14 C64 1.759(15) . ?
S15 C64 1.619(13) . ?
S16 C62 1.629(13) . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C52 C53 1.3900 . ?
C52 H52 0.9500 . ?
C53 C54 1.3900 . ?
C53 H53 0.9500 . ?
C54 C55 1.3900 . ?
C54 H54 0.9500 . ?
C55 C56 1.3900 . ?
C55 H55 0.9500 . ?
C56 N57 1.413(12) . ?
N57 C58 1.384(15) . ?
N57 C59 1.388(16) . ?
C59 C60 1.453(17) . ?
C60 C61 1.386(18) . ?
C61 C62 1.464(17) . ?
C62 N63 1.387(16) . ?
N63 C64 1.395(16) . ?
N63 C65 1.397(13) . ?
C65 C66 1.3900 . ?
C65 C70 1.3900 . ?
C66 C67 1.3900 . ?
C66 H66 0.9500 . ?
C67 C68 1.3900 . ?
C67 H67 0.9500 . ?
C68 C69 1.3900 . ?
C68 H68 0.9500 . ?
C69 C70 1.3900 . ?
C69 H69 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S2 C8 91.7(6) . . ?
C14 S4 C11 91.5(7) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 I1 119.9(5) . . ?
C6 C1 I1 120.1(5) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 N7 119.3(8) . . ?
C1 C6 N7 120.7(8) . . ?
C8 N7 C9 116.8(10) . . ?
C8 N7 C6 122.7(11) . . ?
C9 N7 C6 120.5(11) . . ?
N7 C8 S1 127.5(10) . . ?
N7 C8 S2 110.2(10) . . ?
S1 C8 S2 122.3(7) . . ?
N7 C9 C10 110.3(11) . . ?
N7 C9 S3 123.4(9) . . ?
C10 C9 S3 126.3(11) . . ?
C11 C10 C9 124.5(13) . . ?
C11 C10 S2 124.5(10) . . ?
C9 C10 S2 111.0(10) . . ?
C10 C11 C12 126.6(13) . . ?
C10 C11 S4 123.4(10) . . ?
C12 C11 S4 110.0(10) . . ?
N13 C12 C11 112.2(12) . . ?
N13 C12 S5 123.9(10) . . ?
C11 C12 S5 123.9(11) . . ?
C12 N13 C14 116.9(12) . . ?
C12 N13 C16 122.4(12) . . ?
C14 N13 C16 120.5(12) . . ?
N13 C14 S6 127.2(12) . . ?
N13 C14 S4 109.3(11) . . ?
S6 C14 S4 123.5(9) . . ?
C17 C16 C21 120.0 . . ?
C17 C16 N13 118.0(11) . . ?
C21 C16 N13 122.0(10) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 I2 120.1(6) . . ?
C16 C21 I2 119.9(6) . . ?
C58 S13 C60 91.4(6) . . ?
C61 S14 C64 92.0(6) . . ?
C52 C51 C56 120.0 . . ?
C52 C51 I11 120.4(6) . . ?
C56 C51 I11 119.5(6) . . ?
C51 C52 C53 120.0 . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 C54 120.0 . . ?
C56 C55 H55 120.0 . . ?
C54 C55 H55 120.0 . . ?
C55 C56 C51 120.0 . . ?
C55 C56 N57 120.8(9) . . ?
C51 C56 N57 119.2(9) . . ?
C58 N57 C59 115.7(11) . . ?
C58 N57 C56 121.7(10) . . ?
C59 N57 C56 122.6(10) . . ?
N57 C58 S11 126.0(10) . . ?
N57 C58 S13 111.3(9) . . ?
S11 C58 S13 122.5(7) . . ?
N57 C59 C60 110.2(10) . . ?
N57 C59 S12 123.1(10) . . ?
C60 C59 S12 126.7(10) . . ?
C61 C60 C59 123.5(11) . . ?
C61 C60 S13 125.4(9) . . ?
C59 C60 S13 111.2(9) . . ?
C60 C61 C62 123.2(11) . . ?
C60 C61 S14 125.3(9) . . ?
C62 C61 S14 111.4(9) . . ?
N63 C62 C61 110.0(11) . . ?
N63 C62 S16 124.3(10) . . ?
C61 C62 S16 125.6(9) . . ?
C62 N63 C64 116.6(11) . . ?
C62 N63 C65 121.9(10) . . ?
C64 N63 C65 121.5(10) . . ?
N63 C64 S15 127.9(11) . . ?
N63 C64 S14 110.0(9) . . ?
S15 C64 S14 122.1(8) . . ?
C66 C65 C70 120.0 . . ?
C66 C65 N63 119.8(9) . . ?
C70 C65 N63 120.1(9) . . ?
C65 C66 C67 120.0 . . ?
C65 C66 H66 120.0 . . ?
C67 C66 H66 120.0 . . ?
C68 C67 C66 120.0 . . ?
C68 C67 H67 120.0 . . ?
C66 C67 H67 120.0 . . ?
C69 C68 C67 120.0 . . ?
C69 C68 H68 120.0 . . ?
C67 C68 H68 120.0 . . ?
C70 C69 C68 120.0 . . ?
C70 C69 H69 120.0 . . ?
C68 C69 H69 120.0 . . ?
C69 C70 C65 120.0 . . ?
C69 C70 I12 120.5(6) . . ?
C65 C70 I12 119.5(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0 . . . . ?
I1 C1 C2 C3 -178.7(9) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 N7 -177.9(12) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
I1 C1 C6 C5 178.7(9) . . . . ?
C2 C1 C6 N7 177.9(12) . . . . ?
I1 C1 C6 N7 -3.5(11) . . . . ?
C5 C6 N7 C8 -84.5(15) . . . . ?
C1 C6 N7 C8 97.7(14) . . . . ?
C5 C6 N7 C9 98.9(14) . . . . ?
C1 C6 N7 C9 -79.0(15) . . . . ?
C9 N7 C8 S1 -179.4(12) . . . . ?
C6 N7 C8 S1 4(2) . . . . ?
C9 N7 C8 S2 1.3(17) . . . . ?
C6 N7 C8 S2 -175.5(10) . . . . ?
C10 S2 C8 N7 -1.3(11) . . . . ?
C10 S2 C8 S1 179.3(10) . . . . ?
C8 N7 C9 C10 -0.5(19) . . . . ?
C6 N7 C9 C10 176.3(12) . . . . ?
C8 N7 C9 S3 -178.9(12) . . . . ?
C6 N7 C9 S3 -2(2) . . . . ?
N7 C9 C10 C11 179.4(15) . . . . ?
S3 C9 C10 C11 -2(2) . . . . ?
N7 C9 C10 S2 -0.5(17) . . . . ?
S3 C9 C10 S2 177.9(10) . . . . ?
C8 S2 C10 C11 -178.9(15) . . . . ?
C8 S2 C10 C9 1.0(12) . . . . ?
C9 C10 C11 C12 -179.9(15) . . . . ?
S2 C10 C11 C12 0(2) . . . . ?
C9 C10 C11 S4 0(2) . . . . ?
S2 C10 C11 S4 -179.9(9) . . . . ?
C14 S4 C11 C10 -177.0(16) . . . . ?
C14 S4 C11 C12 3.1(14) . . . . ?
C10 C11 C12 N13 177.3(16) . . . . ?
S4 C11 C12 N13 -2.8(18) . . . . ?
C10 C11 C12 S5 -2(2) . . . . ?
S4 C11 C12 S5 178.0(9) . . . . ?
C11 C12 N13 C14 1(2) . . . . ?
S5 C12 N13 C14 -180.0(16) . . . . ?
C11 C12 N13 C16 174.7(15) . . . . ?
S5 C12 N13 C16 -6(2) . . . . ?
C12 N13 C14 S6 -177.5(19) . . . . ?
C16 N13 C14 S6 9(3) . . . . ?
C12 N13 C14 S4 1(3) . . . . ?
C16 N13 C14 S4 -172.5(14) . . . . ?
C11 S4 C14 N13 -2.6(18) . . . . ?
C11 S4 C14 S6 176.5(19) . . . . ?
C12 N13 C16 C17 90.1(18) . . . . ?
C14 N13 C16 C17 -96.3(19) . . . . ?
C12 N13 C16 C21 -91.3(17) . . . . ?
C14 N13 C16 C21 82(2) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
N13 C16 C17 C18 178.6(12) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C19 C20 C21 I2 178.0(9) . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
N13 C16 C21 C20 -178.5(13) . . . . ?
C17 C16 C21 I2 -178.0(9) . . . . ?
N13 C16 C21 I2 3.5(12) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
I11 C51 C52 C53 -177.4(7) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C54 C55 C56 N57 -178.7(10) . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
I11 C51 C56 C55 177.4(7) . . . . ?
C52 C51 C56 N57 178.7(10) . . . . ?
I11 C51 C56 N57 -3.9(9) . . . . ?
C55 C56 N57 C58 -86.2(14) . . . . ?
C51 C56 N57 C58 95.1(14) . . . . ?
C55 C56 N57 C59 94.5(14) . . . . ?
C51 C56 N57 C59 -84.2(14) . . . . ?
C59 N57 C58 S11 -179.2(11) . . . . ?
C56 N57 C58 S11 1(2) . . . . ?
C59 N57 C58 S13 5.5(17) . . . . ?
C56 N57 C58 S13 -173.8(11) . . . . ?
C60 S13 C58 N57 -4.9(11) . . . . ?
C60 S13 C58 S11 179.7(10) . . . . ?
C58 N57 C59 C60 -3.0(18) . . . . ?
C56 N57 C59 C60 176.2(12) . . . . ?
C58 N57 C59 S12 178.3(11) . . . . ?
C56 N57 C59 S12 -2(2) . . . . ?
N57 C59 C60 C61 178.5(13) . . . . ?
S12 C59 C60 C61 -3(2) . . . . ?
N57 C59 C60 S13 -0.8(15) . . . . ?
S12 C59 C60 S13 177.8(9) . . . . ?
C58 S13 C60 C61 -176.0(13) . . . . ?
C58 S13 C60 C59 3.2(11) . . . . ?
C59 C60 C61 C62 -178.3(13) . . . . ?
S13 C60 C61 C62 1(2) . . . . ?
C59 C60 C61 S14 -1(2) . . . . ?
S13 C60 C61 S14 178.0(8) . . . . ?
C64 S14 C61 C60 -175.5(13) . . . . ?
C64 S14 C61 C62 1.9(11) . . . . ?
C60 C61 C62 N63 176.6(13) . . . . ?
S14 C61 C62 N63 -0.9(14) . . . . ?
C60 C61 C62 S16 -5(2) . . . . ?
S14 C61 C62 S16 177.3(9) . . . . ?
C61 C62 N63 C64 -1.1(17) . . . . ?
S16 C62 N63 C64 -179.3(11) . . . . ?
C61 C62 N63 C65 179.2(12) . . . . ?
S16 C62 N63 C65 1.0(19) . . . . ?
C62 N63 C64 S15 -177.4(11) . . . . ?
C65 N63 C64 S15 2(2) . . . . ?
C62 N63 C64 S14 2.5(16) . . . . ?
C65 N63 C64 S14 -177.8(10) . . . . ?
C61 S14 C64 N63 -2.5(11) . . . . ?
C61 S14 C64 S15 177.5(10) . . . . ?
C62 N63 C65 C66 88.1(14) . . . . ?
C64 N63 C65 C66 -91.6(13) . . . . ?
C62 N63 C65 C70 -88.0(13) . . . . ?
C64 N63 C65 C70 92.4(13) . . . . ?
C70 C65 C66 C67 0.0 . . . . ?
N63 C65 C66 C67 -176.0(10) . . . . ?
C65 C66 C67 C68 0.0 . . . . ?
C66 C67 C68 C69 0.0 . . . . ?
C67 C68 C69 C70 0.0 . . . . ?
C68 C69 C70 C65 0.0 . . . . ?
C68 C69 C70 I12 179.3(8) . . . . ?
C66 C65 C70 C69 0.0 . . . . ?
N63 C65 C70 C69 176.0(10) . . . . ?
C66 C65 C70 I12 -179.4(8) . . . . ?
N63 C65 C70 I12 -3.3(9) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR AC49_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_compound3c
_database_code_depnum_ccdc_archive 'CCDC 1872723'
loop_
_audit_author_name
_audit_author_address
'Vincent Dorcet and Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2018-10-11 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 I N O S4'
_chemical_formula_sum            'C10 H4 I N O S4'
_chemical_formula_weight         409.28
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1394(7)
_cell_length_b                   6.9798(7)
_cell_length_c                   22.487(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.788(3)
_cell_angle_gamma                90
_cell_volume                     1273.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             784
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.151
_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  0.520
_exptl_absorpt_correction_T_max  0.753

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0404
_diffrn_reflns_av_uneti/neti     0.0321
_diffrn_reflns_number            14751
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2904
_reflns_number_gt                2675
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            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    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+3.3590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2904
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.915
_refine_diff_density_min         -1.574
_refine_diff_density_rms         0.134

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.3610(4) 0.7015(4) 0.55976(14) 0.0160(6) Uani 1 1 d . . . . .
C2 C 0.3281(5) 0.7903(5) 0.50491(15) 0.0222(7) Uani 1 1 d . . . . .
H2 H 0.415824 0.836134 0.483482 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1661(5) 0.8115(5) 0.48161(15) 0.0254(8) Uani 1 1 d . . . . .
H3 H 0.143254 0.872796 0.444108 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0367(4) 0.7445(5) 0.51231(15) 0.0226(7) Uani 1 1 d . . . . .
H4 H -0.073979 0.760838 0.496060 0.027 Uiso 1 1 calc R U . . .
C5 C 0.0697(4) 0.6536(5) 0.56683(14) 0.0177(6) Uani 1 1 d . . . . .
H5 H -0.018235 0.605844 0.587834 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2311(4) 0.6326(4) 0.59052(13) 0.0126(5) Uani 1 1 d . . . . .
N7 N 0.2610(3) 0.5437(3) 0.64816(11) 0.0113(5) Uani 1 1 d . . . . .
C8 C 0.3073(4) 0.3563(4) 0.65623(13) 0.0135(6) Uani 1 1 d . . . . .
C9 C 0.2432(4) 0.6429(4) 0.70066(13) 0.0127(5) Uani 1 1 d . . . . .
C10 C 0.2809(4) 0.5410(4) 0.75067(13) 0.0154(6) Uani 1 1 d . . . . .
C11 C 0.1553(4) 0.8585(5) 0.78498(14) 0.0167(6) Uani 1 1 d . . . . .
O12 O 0.1037(3) 0.9872(4) 0.81358(11) 0.0257(5) Uani 1 1 d . . . . .
I1 I 0.60356(3) 0.67508(3) 0.59781(2) 0.02559(10) Uani 1 1 d . . . . .
S1 S 0.33171(11) 0.19402(11) 0.60436(3) 0.01934(18) Uani 1 1 d . . . . .
S2 S 0.33830(11) 0.30915(11) 0.73319(3) 0.01777(17) Uani 1 1 d . . . . .
S3 S 0.24400(10) 0.64547(11) 0.81816(3) 0.01812(17) Uani 1 1 d . . . . .
S4 S 0.16143(10) 0.87055(11) 0.70598(3) 0.01690(16) 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 C2 1.386(5) . ?
C1 C6 1.397(4) . ?
C1 I1 2.093(3) . ?
C2 C3 1.386(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 N7 1.440(4) . ?
N7 C8 1.369(4) . ?
N7 C9 1.387(4) . ?
C8 S1 1.650(3) . ?
C8 S2 1.759(3) . ?
C9 C10 1.344(4) . ?
C9 S4 1.731(3) . ?
C10 S3 1.733(3) . ?
C10 S2 1.738(3) . ?
C11 O12 1.201(4) . ?
C11 S4 1.783(3) . ?
C11 S3 1.789(3) . ?

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 C6 119.7(3) . . ?
C2 C1 I1 120.6(2) . . ?
C6 C1 I1 119.7(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 N7 118.4(3) . . ?
C1 C6 N7 121.1(3) . . ?
C8 N7 C9 114.3(2) . . ?
C8 N7 C6 123.7(2) . . ?
C9 N7 C6 122.0(2) . . ?
N7 C8 S1 127.6(2) . . ?
N7 C8 S2 108.9(2) . . ?
S1 C8 S2 123.47(18) . . ?
C10 C9 N7 114.5(3) . . ?
C10 C9 S4 119.3(2) . . ?
N7 C9 S4 125.8(2) . . ?
C9 C10 S3 117.8(2) . . ?
C9 C10 S2 110.5(2) . . ?
S3 C10 S2 131.25(19) . . ?
O12 C11 S4 122.6(3) . . ?
O12 C11 S3 123.1(3) . . ?
S4 C11 S3 114.26(17) . . ?
C10 S2 C8 91.67(14) . . ?
C10 S3 C11 94.47(15) . . ?
C9 S4 C11 93.93(15) . . ?

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
C6 C1 C2 C3 0.8(5) . . . . ?
I1 C1 C2 C3 -177.9(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C4 C5 C6 N7 177.8(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
I1 C1 C6 C5 178.2(2) . . . . ?
C2 C1 C6 N7 -178.6(3) . . . . ?
I1 C1 C6 N7 0.1(4) . . . . ?
C5 C6 N7 C8 100.2(3) . . . . ?
C1 C6 N7 C8 -81.6(4) . . . . ?
C5 C6 N7 C9 -79.1(4) . . . . ?
C1 C6 N7 C9 99.0(3) . . . . ?
C9 N7 C8 S1 177.0(2) . . . . ?
C6 N7 C8 S1 -2.4(4) . . . . ?
C9 N7 C8 S2 -2.8(3) . . . . ?
C6 N7 C8 S2 177.8(2) . . . . ?
C8 N7 C9 C10 2.6(4) . . . . ?
C6 N7 C9 C10 -178.0(3) . . . . ?
C8 N7 C9 S4 -171.2(2) . . . . ?
C6 N7 C9 S4 8.2(4) . . . . ?
N7 C9 C10 S3 -174.1(2) . . . . ?
S4 C9 C10 S3 0.2(4) . . . . ?
N7 C9 C10 S2 -1.1(4) . . . . ?
S4 C9 C10 S2 173.23(17) . . . . ?
C9 C10 S2 C8 -0.5(3) . . . . ?
S3 C10 S2 C8 171.3(3) . . . . ?
N7 C8 S2 C10 1.9(2) . . . . ?
S1 C8 S2 C10 -178.0(2) . . . . ?
C9 C10 S3 C11 2.6(3) . . . . ?
S2 C10 S3 C11 -168.7(2) . . . . ?
O12 C11 S3 C10 179.2(3) . . . . ?
S4 C11 S3 C10 -4.5(2) . . . . ?
C10 C9 S4 C11 -2.9(3) . . . . ?
N7 C9 S4 C11 170.7(3) . . . . ?
O12 C11 S4 C9 -179.2(3) . . . . ?
S3 C11 S4 C9 4.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 S1 0.95 2.97 3.854(3) 154.6 3_666
C5 H5 O12 0.95 2.52 3.347(4) 145.9 2_546
C5 H5 I1 0.95 3.14 3.917(3) 139.9 1_455
