# Electronic Supplementary Material (ESI) for ChemComm.
# 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_vd066
_database_code_depnum_ccdc_archive 'CCDC 1895418'
loop_
_audit_author_name
_audit_author_address
'Tullio Pilati'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-02-04 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 I2 O2 S'
_chemical_formula_sum            'C8 H8 I2 O2 S'
_chemical_formula_weight         422.00

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   19.0268(7)
_cell_length_b                   7.3586(3)
_cell_length_c                   8.0423(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1126.01(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9530
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      39.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.489
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    5.739
_shelx_estimated_absorpt_T_min   0.269
_shelx_estimated_absorpt_T_max   0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.2812
_exptl_absorpt_correction_T_max  0.4105

_exptl_special_details           
;
Experimental temperature controlled by a Bruker KRYOFLEX low 
temperature device.
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            61066
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.533
_diffrn_reflns_theta_max         39.807
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6641
_reflns_number_gt                6532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0085P)²+0.3143P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.002(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6641
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0145
_refine_ls_R_factor_gt           0.0139
_refine_ls_wR_factor_ref         0.0287
_refine_ls_wR_factor_gt          0.0286
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.66569(2) 0.50850(2) 0.68178(2) 0.01431(2) Uani 1 1 d . . . . .
I2 I 0.76433(2) 0.14202(2) 0.85559(2) 0.01979(3) Uani 1 1 d . . . . .
S1 S 0.63476(2) 0.07793(5) 0.61113(5) 0.01085(6) Uani 1 1 d . . . . .
O1 O 0.67011(7) -0.08754(16) 0.56308(18) 0.0175(2) Uani 1 1 d . . . . .
O2 O 0.58848(7) 0.07435(19) 0.75220(17) 0.0168(2) Uani 1 1 d . . . . .
C1 C 0.70400(8) 0.2391(2) 0.6493(2) 0.0119(2) Uani 1 1 d . . . . .
H1 H 0.7354 0.2393 0.5496 0.014 Uiso 1 1 calc R U . . .
C2 C 0.58898(8) 0.1619(2) 0.4389(2) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.61955(8) 0.1498(3) 0.2815(2) 0.0151(3) Uani 1 1 d . . . . .
H3 H 0.6668 0.1105 0.2692 0.018 Uiso 1 1 calc R U . . .
C4 C 0.57982(9) 0.1961(2) 0.1436(2) 0.0165(3) Uani 1 1 d . . . . .
H4 H 0.6004 0.1906 0.0362 0.020 Uiso 1 1 calc R U . . .
C5 C 0.50951(8) 0.2508(2) 0.1605(2) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.48113(8) 0.2674(2) 0.3198(2) 0.0158(3) Uani 1 1 d . . . . .
H6 H 0.4343 0.3097 0.3327 0.019 Uiso 1 1 calc R U . . .
C7 C 0.52020(8) 0.2234(2) 0.4596(2) 0.0140(3) Uani 1 1 d . . . . .
H7 H 0.5005 0.2348 0.5676 0.017 Uiso 1 1 calc R U . . .
C8 C 0.46497(10) 0.2854(3) 0.0096(2) 0.0212(3) Uani 1 1 d . . . . .
H8A H 0.4322 0.1840 -0.0060 0.032 Uiso 1 1 calc R U . . .
H8B H 0.4952 0.2964 -0.0885 0.032 Uiso 1 1 calc R U . . .
H8C H 0.4384 0.3983 0.0248 0.032 Uiso 1 1 calc R U . . .


_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 2.1282(15) . ?
I2 C1 2.1399(16) . ?
S1 O2 1.4364(13) . ?
S1 O1 1.4437(13) . ?
S1 C2 1.7495(16) . ?
S1 C1 1.7991(15) . ?
C1 H1 1.0000 . ?
C2 C7 1.395(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 C8 1.502(2) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.79(8) . . ?
O2 S1 C2 109.07(8) . . ?
O1 S1 C2 108.54(8) . . ?
O2 S1 C1 109.03(8) . . ?
O1 S1 C1 105.11(7) . . ?
C2 S1 C1 105.48(7) . . ?
S1 C1 I1 112.59(7) . . ?
S1 C1 I2 107.76(7) . . ?
I1 C1 I2 113.56(7) . . ?
S1 C1 H1 107.6 . . ?
I1 C1 H1 107.6 . . ?
I2 C1 H1 107.6 . . ?
C7 C2 C3 121.35(15) . . ?
C7 C2 S1 119.14(13) . . ?
C3 C2 S1 119.22(12) . . ?
C4 C3 C2 118.88(15) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.91(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.84(15) . . ?
C6 C5 C8 120.58(15) . . ?
C4 C5 C8 120.55(16) . . ?
C7 C6 C5 121.10(15) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 118.82(15) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 I1 -61.60(10) . . . . ?
O1 S1 C1 I1 170.02(8) . . . . ?
C2 S1 C1 I1 55.41(10) . . . . ?
O2 S1 C1 I2 64.40(9) . . . . ?
O1 S1 C1 I2 -63.97(9) . . . . ?
C2 S1 C1 I2 -178.59(7) . . . . ?
O2 S1 C2 C7 4.41(16) . . . . ?
O1 S1 C2 C7 135.21(13) . . . . ?
C1 S1 C2 C7 -112.58(14) . . . . ?
O2 S1 C2 C3 -169.48(14) . . . . ?
O1 S1 C2 C3 -38.69(16) . . . . ?
C1 S1 C2 C3 73.53(15) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
S1 C2 C3 C4 172.25(14) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 3.4(3) . . . . ?
C3 C4 C5 C8 -174.74(17) . . . . ?
C4 C5 C6 C7 -2.8(2) . . . . ?
C8 C5 C6 C7 175.31(17) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C3 C2 C7 C6 2.1(3) . . . . ?
S1 C2 C7 C6 -171.70(13) . . . . ?

_refine_diff_density_max         0.944
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.088

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_VD057
_database_code_depnum_ccdc_archive 'CCDC 1895420'
loop_
_audit_author_name
_audit_author_address
'Tullio Pilati'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-02-04 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, 2(C8 H8 O2 I2 S)'
_chemical_formula_sum            'C28 H26 I4 N2 O4 S2'
_chemical_formula_weight         1026.23

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1342(6)
_cell_length_b                   17.3124(10)
_cell_length_c                   19.0131(11)
_cell_angle_alpha                114.136(2)
_cell_angle_beta                 90.987(2)
_cell_angle_gamma                97.782(2)
_cell_volume                     3303.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9172
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.24
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.3530
_exptl_absorpt_correction_T_max  0.4426

_exptl_special_details           
;
In spite of a number of attempts, all crystals we analyzed were twins.
Bruker KRYOFLEX low temperature device.
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            217267
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.177
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.996
_reflns_number_total             15974
_reflns_number_gt                14207
_reflns_threshold_expression     'I > 2σ(I)'

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          
;
Due to the twinning a number of Io >> Ic were found; 48 reflections 
with very large Delta(F^2)/esd were omitted from the refinement 
(see the OMIT list in the _iucr_refine_instructions_details section 
above.)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0082P)²+20.6526P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15974
_refine_ls_number_parameters     721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.29890(2) 0.66629(2) 0.32915(2) 0.01296(5) Uani 1 1 d . . . . .
I2 I -0.40547(2) 0.83495(2) 0.29522(2) 0.01845(6) Uani 1 1 d . . . . .
S1 S -0.56566(8) 0.71324(6) 0.36279(5) 0.01204(17) Uani 1 1 d . . . . .
O1 O -0.6038(3) 0.62406(18) 0.34688(17) 0.0190(6) Uani 1 1 d . . . . .
O2 O -0.5174(3) 0.77198(18) 0.43913(16) 0.0182(6) Uani 1 1 d . . . . .
C1 C -0.4534(3) 0.7127(2) 0.2966(2) 0.0123(7) Uani 1 1 d . . . . .
H1 H -0.4874 0.6710 0.2435 0.015 Uiso 1 1 calc R U . . .
C2 C -0.6897(3) 0.7518(2) 0.3366(2) 0.0136(7) Uani 1 1 d . . . . .
C3 C -0.7527(3) 0.7064(3) 0.2639(2) 0.0170(8) Uani 1 1 d . . . . .
H3 H -0.7276 0.6557 0.2276 0.020 Uiso 1 1 calc R U . . .
C4 C -0.8519(4) 0.7365(3) 0.2457(2) 0.0192(8) Uani 1 1 d . . . . .
H4 H -0.8944 0.7065 0.1960 0.023 Uiso 1 1 calc R U . . .
C5 C -0.8913(4) 0.8105(3) 0.2990(3) 0.0194(8) Uani 1 1 d . . . . .
C6 C -0.8280(4) 0.8538(3) 0.3711(3) 0.0212(9) Uani 1 1 d . . . . .
H6 H -0.8545 0.9035 0.4080 0.025 Uiso 1 1 calc R U . . .
C7 C -0.7259(4) 0.8257(3) 0.3903(2) 0.0177(8) Uani 1 1 d . . . . .
H7 H -0.6819 0.8565 0.4394 0.021 Uiso 1 1 calc R U . . .
C8 C -1.0018(4) 0.8414(3) 0.2784(3) 0.0315(11) Uani 1 1 d . . . . .
H8A H -1.0345 0.8032 0.2255 0.047 Uiso 0.5 1 calc R U P . .
H8B H -0.9786 0.8997 0.2820 0.047 Uiso 0.5 1 calc R U P . .
H8C H -1.0639 0.8415 0.3143 0.047 Uiso 0.5 1 calc R U P . .
H8D H -1.0168 0.8931 0.3224 0.047 Uiso 0.5 1 calc R U P . .
H8E H -1.0727 0.7965 0.2659 0.047 Uiso 0.5 1 calc R U P . .
H8F H -0.9875 0.8547 0.2336 0.047 Uiso 0.5 1 calc R U P . .
N1 N -0.1126(3) 0.6079(2) 0.37507(19) 0.0166(7) Uani 1 1 d . . . . .
N2 N 0.5382(3) 0.3389(2) 0.43312(19) 0.0168(7) Uani 1 1 d . . . . .
C9 C -0.0606(4) 0.4919(3) 0.4011(3) 0.0204(8) Uani 1 1 d . . . . .
H9 H -0.0875 0.4429 0.4107 0.024 Uiso 1 1 calc R U . . .
C10 C -0.1432(4) 0.5385(3) 0.3894(3) 0.0207(9) Uani 1 1 d . . . . .
H10 H -0.2270 0.5204 0.3915 0.025 Uiso 1 1 calc R U . . .
C11 C 0.0060(4) 0.6319(2) 0.3726(2) 0.0158(8) Uani 1 1 d . . . . .
H11 H 0.0300 0.6808 0.3624 0.019 Uiso 1 1 calc R U . . .
C12 C 0.0956(3) 0.5893(2) 0.3842(2) 0.0152(8) Uani 1 1 d . . . . .
H12 H 0.1787 0.6093 0.3821 0.018 Uiso 1 1 calc R U . . .
C13 C 0.0637(3) 0.5173(3) 0.3988(2) 0.0152(8) Uani 1 1 d . . . . .
C14 C 0.1518(4) 0.4667(3) 0.4106(2) 0.0178(8) Uani 1 1 d . . . . .
H14 H 0.1209 0.4175 0.4189 0.021 Uiso 1 1 calc R U . . .
C15 C 0.2719(4) 0.4851(2) 0.4103(2) 0.0155(8) Uani 1 1 d . . . . .
H15 H 0.3025 0.5355 0.4039 0.019 Uiso 1 1 calc R U . . .
C16 C 0.3606(3) 0.4337(2) 0.4192(2) 0.0144(7) Uani 1 1 d . . . . .
C17 C 0.3342(4) 0.3702(3) 0.4468(2) 0.0175(8) Uani 1 1 d . . . . .
H17 H 0.2549 0.3578 0.4610 0.021 Uiso 1 1 calc R U . . .
C18 C 0.4258(4) 0.3254(2) 0.4531(2) 0.0170(8) Uani 1 1 d . . . . .
H18 H 0.4071 0.2832 0.4727 0.020 Uiso 1 1 calc R U . . .
C19 C 0.5621(4) 0.3986(3) 0.4062(2) 0.0193(8) Uani 1 1 d . . . . .
H19 H 0.6414 0.4080 0.3907 0.023 Uiso 1 1 calc R U . . .
C20 C 0.4785(4) 0.4481(3) 0.3994(2) 0.0171(8) Uani 1 1 d . . . . .
H20 H 0.5015 0.4914 0.3814 0.021 Uiso 1 1 calc R U . . .
I3 I 0.72297(2) 0.24927(2) 0.43250(2) 0.01493(5) Uani 1 1 d . . . . .
I4 I 0.80509(2) 0.04206(2) 0.39094(2) 0.02224(6) Uani 1 1 d . . . . .
S2 S 0.98357(9) 0.19871(6) 0.37517(6) 0.01686(19) Uani 1 1 d . . . . .
O3 O 1.0253(3) 0.28937(18) 0.41523(19) 0.0232(6) Uani 1 1 d . . . . .
O4 O 0.9386(3) 0.1634(2) 0.29547(18) 0.0268(7) Uani 1 1 d . . . . .
C21 C 0.8670(3) 0.1765(2) 0.4311(2) 0.0156(8) Uani 1 1 d . . . . .
H21 H 0.9031 0.1977 0.4855 0.019 Uiso 1 1 calc R U . . .
C22 C 1.1016(3) 0.1449(3) 0.3855(2) 0.0189(8) Uani 1 1 d . . . . .
C23 C 1.1355(4) 0.0791(3) 0.3213(3) 0.0250(9) Uani 1 1 d . . . . .
H23 H 1.0912 0.0592 0.2724 0.030 Uiso 1 1 calc R U . . .
C24 C 1.2358(4) 0.0428(3) 0.3299(3) 0.0272(10) Uani 1 1 d . . . . .
H24 H 1.2614 -0.0010 0.2860 0.033 Uiso 1 1 calc R U . . .
C25 C 1.2989(4) 0.0693(3) 0.4011(3) 0.0250(10) Uani 1 1 d . . . . .
C26 C 1.2591(4) 0.1320(3) 0.4658(3) 0.0253(10) Uani 1 1 d . . . . .
H26 H 1.2985 0.1480 0.5155 0.030 Uiso 1 1 calc R U . . .
C27 C 1.1620(4) 0.1711(3) 0.4578(3) 0.0220(9) Uani 1 1 d . . . . .
H27 H 1.1372 0.2156 0.5015 0.026 Uiso 1 1 calc R U . . .
C28 C 1.4121(4) 0.0340(3) 0.4099(4) 0.0383(13) Uani 1 1 d . . . . .
H28A H 1.4437 0.0603 0.4644 0.057 Uiso 0.5 1 calc R U P . .
H28B H 1.4738 0.0469 0.3785 0.057 Uiso 0.5 1 calc R U P . .
H28C H 1.3925 -0.0283 0.3926 0.057 Uiso 0.5 1 calc R U P . .
H28D H 1.4297 -0.0076 0.3593 0.057 Uiso 0.5 1 calc R U P . .
H28E H 1.3995 0.0057 0.4452 0.057 Uiso 0.5 1 calc R U P . .
H28F H 1.4808 0.0809 0.4311 0.057 Uiso 0.5 1 calc R U P . .
I5 I -0.05537(2) 0.92405(2) 0.10220(2) 0.01848(6) Uani 1 1 d . . . . .
I6 I -0.17794(3) 1.08380(2) 0.06449(2) 0.02107(6) Uani 1 1 d . . . . .
S3 S -0.33495(9) 0.95056(6) 0.12251(6) 0.01546(19) Uani 1 1 d . . . . .
O5 O -0.3683(3) 0.89562(18) 0.04225(17) 0.0238(6) Uani 1 1 d . . . . .
O6 O -0.3295(3) 0.91208(19) 0.17645(19) 0.0255(7) Uani 1 1 d . . . . .
C29 C -0.1872(3) 1.0111(2) 0.1322(2) 0.0145(7) Uani 1 1 d . . . . .
H29 H -0.1686 1.0520 0.1877 0.017 Uiso 1 1 calc R U . . .
C30 C -0.4352(3) 1.0260(2) 0.1546(2) 0.0143(7) Uani 1 1 d . . . . .
C31 C -0.4269(4) 1.0826(3) 0.2322(2) 0.0246(9) Uani 1 1 d . . . . .
H31 H -0.3656 1.0821 0.2674 0.029 Uiso 1 1 calc R U . . .
C32 C -0.5094(4) 1.1398(3) 0.2576(3) 0.0277(10) Uani 1 1 d . . . . .
H32 H -0.5048 1.1781 0.3107 0.033 Uiso 1 1 calc R U . . .
C33 C -0.5986(4) 1.1416(3) 0.2065(2) 0.0202(8) Uani 1 1 d . . . . .
C34 C -0.6060(4) 1.0838(3) 0.1297(3) 0.0218(9) Uani 1 1 d . . . . .
H34 H -0.6679 1.0838 0.0947 0.026 Uiso 1 1 calc R U . . .
C35 C -0.5253(4) 1.0262(3) 0.1031(2) 0.0196(8) Uani 1 1 d . . . . .
H35 H -0.5311 0.9871 0.0502 0.024 Uiso 1 1 calc R U . . .
C36 C -0.6855(4) 1.2056(3) 0.2351(3) 0.0304(10) Uani 1 1 d . . . . .
H36A H -0.6663 1.2409 0.2905 0.046 Uiso 0.5 1 calc R U P . .
H36B H -0.7690 1.1751 0.2262 0.046 Uiso 0.5 1 calc R U P . .
H36C H -0.6777 1.2425 0.2072 0.046 Uiso 0.5 1 calc R U P . .
H36D H -0.7423 1.1981 0.1920 0.046 Uiso 0.5 1 calc R U P . .
H36E H -0.6396 1.2638 0.2564 0.046 Uiso 0.5 1 calc R U P . .
H36F H -0.7310 1.1965 0.2754 0.046 Uiso 0.5 1 calc R U P . .
N3 N 0.1298(3) 0.8217(2) 0.0702(2) 0.0244(8) Uani 1 1 d . . . . .
N4 N 0.7899(3) 0.5547(2) 0.1163(2) 0.0207(7) Uani 1 1 d . . . . .
C37 C 0.3324(4) 0.8121(3) 0.1072(3) 0.0229(9) Uani 1 1 d . . . . .
H37 H 0.4110 0.8411 0.1308 0.027 Uiso 1 1 calc R U . . .
C38 C 0.2409(4) 0.8582(3) 0.1039(3) 0.0244(9) Uani 1 1 d . . . . .
H38 H 0.2588 0.9190 0.1270 0.029 Uiso 1 1 calc R U . . .
C39 C 0.1058(4) 0.7362(3) 0.0392(3) 0.0273(10) Uani 1 1 d . . . . .
H39 H 0.0270 0.7091 0.0148 0.033 Uiso 1 1 calc R U . . .
C40 C 0.1906(4) 0.6850(3) 0.0408(2) 0.0230(9) Uani 1 1 d . . . . .
H40 H 0.1692 0.6244 0.0184 0.028 Uiso 1 1 calc R U . . .
C41 C 0.3073(4) 0.7229(3) 0.0755(2) 0.0171(8) Uani 1 1 d . . . . .
C42 C 0.3970(4) 0.6686(3) 0.0787(2) 0.0176(8) Uani 1 1 d . . . . .
H42 H 0.3677 0.6112 0.0705 0.021 Uiso 1 1 calc R U . . .
C43 C 0.5159(4) 0.6951(3) 0.0921(2) 0.0181(8) Uani 1 1 d . . . . .
H43 H 0.5445 0.7518 0.0979 0.022 Uiso 1 1 calc R U . . .
C44 C 0.6075(4) 0.6440(3) 0.0989(2) 0.0160(8) Uani 1 1 d . . . . .
C45 C 0.7293(4) 0.6810(3) 0.1145(2) 0.0201(8) Uani 1 1 d . . . . .
H45 H 0.7528 0.7383 0.1202 0.024 Uiso 1 1 calc R U . . .
C46 C 0.8156(4) 0.6343(3) 0.1217(3) 0.0236(9) Uani 1 1 d . . . . .
H46 H 0.8984 0.6604 0.1310 0.028 Uiso 1 1 calc R U . . .
C47 C 0.6726(4) 0.5184(3) 0.1019(2) 0.0201(8) Uani 1 1 d . . . . .
H47 H 0.6523 0.4615 0.0977 0.024 Uiso 1 1 calc R U . . .
C48 C 0.5797(4) 0.5603(3) 0.0929(2) 0.0183(8) Uani 1 1 d . . . . .
H48 H 0.4978 0.5322 0.0827 0.022 Uiso 1 1 calc R U . . .
I7 I 0.97453(2) 0.48810(2) 0.15712(2) 0.01674(5) Uani 1 1 d . . . . .
I8 I 1.06024(3) 0.31562(2) 0.19224(2) 0.02955(7) Uani 1 1 d . . . . .
S4 S 1.22971(9) 0.42361(6) 0.11395(6) 0.01714(19) Uani 1 1 d . . . . .
O7 O 1.2720(3) 0.5099(2) 0.12312(19) 0.0256(7) Uani 1 1 d . . . . .
O8 O 1.1725(3) 0.3613(2) 0.04068(17) 0.0284(7) Uani 1 1 d . . . . .
C49 C 1.1239(4) 0.4344(3) 0.1860(2) 0.0161(8) Uani 1 1 d . . . . .
H49 H 1.1647 0.4758 0.2375 0.019 Uiso 1 1 calc R U . . .
C50 C 1.3552(3) 0.3842(3) 0.1378(2) 0.0160(8) Uani 1 1 d . . . . .
C51 C 1.3773(4) 0.3029(3) 0.0898(2) 0.0183(8) Uani 1 1 d . . . . .
H51 H 1.3207 0.2660 0.0477 0.022 Uiso 1 1 calc R U . . .
C52 C 1.4838(4) 0.2763(3) 0.1044(3) 0.0212(9) Uani 1 1 d . . . . .
H52 H 1.4997 0.2208 0.0719 0.025 Uiso 1 1 calc R U . . .
C53 C 1.5677(4) 0.3301(3) 0.1661(3) 0.0196(8) Uani 1 1 d . . . . .
C54 C 1.5423(4) 0.4108(3) 0.2131(2) 0.0203(8) Uani 1 1 d . . . . .
H54 H 1.5982 0.4477 0.2557 0.024 Uiso 1 1 calc R U . . .
C55 C 1.4369(4) 0.4388(3) 0.1995(2) 0.0188(8) Uani 1 1 d . . . . .
H55 H 1.4211 0.4944 0.2319 0.023 Uiso 1 1 calc R U . . .
C56 C 1.6830(4) 0.3007(3) 0.1809(3) 0.0321(11) Uani 1 1 d . . . . .
H56A H 1.6852 0.2425 0.1421 0.048 Uiso 0.5 1 calc R U P . .
H56B H 1.6854 0.3010 0.2326 0.048 Uiso 0.5 1 calc R U P . .
H56C H 1.7534 0.3394 0.1778 0.048 Uiso 0.5 1 calc R U P . .
H56D H 1.7308 0.3461 0.2262 0.048 Uiso 0.5 1 calc R U P . .
H56E H 1.7306 0.2876 0.1357 0.048 Uiso 0.5 1 calc R U P . .
H56F H 1.6626 0.2491 0.1905 0.048 Uiso 0.5 1 calc R U P . .


_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 2.175(4) . ?
I2 C1 2.123(4) . ?
S1 O2 1.431(3) . ?
S1 O1 1.446(3) . ?
S1 C2 1.761(4) . ?
S1 C1 1.787(4) . ?
C1 H1 1.0000 . ?
C2 C7 1.388(5) . ?
C2 C3 1.396(5) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(6) . ?
C5 C8 1.512(6) . ?
C6 C7 1.395(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C8 H8F 0.9800 . ?
N1 C11 1.337(5) . ?
N1 C10 1.339(5) . ?
N2 C19 1.327(5) . ?
N2 C18 1.333(5) . ?
C9 C10 1.374(6) . ?
C9 C13 1.401(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.381(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.471(5) . ?
C14 C15 1.332(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.467(5) . ?
C15 H15 0.9500 . ?
C16 C20 1.390(5) . ?
C16 C17 1.400(5) . ?
C17 C18 1.393(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
I3 C21 2.163(4) . ?
I4 C21 2.137(4) . ?
S2 O4 1.433(3) . ?
S2 O3 1.440(3) . ?
S2 C22 1.762(4) . ?
S2 C21 1.792(4) . ?
C21 H21 1.0000 . ?
C22 C27 1.387(6) . ?
C22 C23 1.387(6) . ?
C23 C24 1.392(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(6) . ?
C25 C28 1.509(6) . ?
C26 C27 1.388(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 H28D 0.9800 . ?
C28 H28E 0.9800 . ?
C28 H28F 0.9800 . ?
I5 C29 2.163(4) . ?
I6 C29 2.132(4) . ?
S3 O6 1.438(3) . ?
S3 O5 1.438(3) . ?
S3 C30 1.758(4) . ?
S3 C29 1.790(4) . ?
C29 H29 1.0000 . ?
C30 C31 1.390(6) . ?
C30 C35 1.391(6) . ?
C31 C32 1.387(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(6) . ?
C33 C36 1.509(6) . ?
C34 C35 1.381(6) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C36 H36D 0.9800 . ?
C36 H36E 0.9800 . ?
C36 H36F 0.9800 . ?
N3 C38 1.331(6) . ?
N3 C39 1.336(6) . ?
N4 C46 1.329(6) . ?
N4 C47 1.342(6) . ?
C37 C38 1.391(6) . ?
C37 C41 1.394(6) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.388(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.393(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.477(5) . ?
C42 C43 1.325(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.474(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.391(6) . ?
C44 C48 1.398(6) . ?
C45 C46 1.376(6) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C48 1.387(6) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
I7 C49 2.177(4) . ?
I8 C49 2.133(4) . ?
S4 O8 1.437(3) . ?
S4 O7 1.442(3) . ?
S4 C50 1.764(4) . ?
S4 C49 1.790(4) . ?
C49 H49 1.0000 . ?
C50 C55 1.386(6) . ?
C50 C51 1.388(5) . ?
C51 C52 1.391(6) . ?
C51 H51 0.9500 . ?
C52 C53 1.396(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.387(6) . ?
C53 C56 1.507(6) . ?
C54 C55 1.387(6) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C56 H56D 0.9800 . ?
C56 H56E 0.9800 . ?
C56 H56F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.25(17) . . ?
O2 S1 C2 108.41(17) . . ?
O1 S1 C2 107.98(17) . . ?
O2 S1 C1 108.85(17) . . ?
O1 S1 C1 105.10(17) . . ?
C2 S1 C1 106.58(17) . . ?
S1 C1 I2 112.02(18) . . ?
S1 C1 I1 106.92(17) . . ?
I2 C1 I1 112.71(16) . . ?
S1 C1 H1 108.4 . . ?
I2 C1 H1 108.4 . . ?
I1 C1 H1 108.4 . . ?
C7 C2 C3 121.2(4) . . ?
C7 C2 S1 118.8(3) . . ?
C3 C2 S1 120.0(3) . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 C8 120.9(4) . . ?
C4 C5 C8 120.5(4) . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 118.9(4) . . ?
C2 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C8 H8D 109.5 . . ?
H8A C8 H8D 141.1 . . ?
H8B C8 H8D 56.3 . . ?
H8C C8 H8D 56.3 . . ?
C5 C8 H8E 109.5 . . ?
H8A C8 H8E 56.3 . . ?
H8B C8 H8E 141.1 . . ?
H8C C8 H8E 56.3 . . ?
H8D C8 H8E 109.5 . . ?
C5 C8 H8F 109.5 . . ?
H8A C8 H8F 56.3 . . ?
H8B C8 H8F 56.3 . . ?
H8C C8 H8F 141.1 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
C11 N1 C10 116.7(3) . . ?
C19 N2 C18 117.2(3) . . ?
C10 C9 C13 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C13 C9 H9 120.3 . . ?
N1 C10 C9 123.9(4) . . ?
N1 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N1 C11 C12 123.6(4) . . ?
N1 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C9 116.8(3) . . ?
C12 C13 C14 123.9(4) . . ?
C9 C13 C14 119.3(4) . . ?
C15 C14 C13 124.6(4) . . ?
C15 C14 H14 117.7 . . ?
C13 C14 H14 117.7 . . ?
C14 C15 C16 125.3(4) . . ?
C14 C15 H15 117.4 . . ?
C16 C15 H15 117.4 . . ?
C20 C16 C17 117.2(3) . . ?
C20 C16 C15 118.9(3) . . ?
C17 C16 C15 123.9(3) . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N2 C18 C17 123.3(4) . . ?
N2 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
N2 C19 C20 124.1(4) . . ?
N2 C19 H19 118.0 . . ?
C20 C19 H19 118.0 . . ?
C19 C20 C16 119.1(4) . . ?
C19 C20 H20 120.5 . . ?
C16 C20 H20 120.5 . . ?
O4 S2 O3 119.60(19) . . ?
O4 S2 C22 109.2(2) . . ?
O3 S2 C22 107.87(19) . . ?
O4 S2 C21 109.52(19) . . ?
O3 S2 C21 104.61(18) . . ?
C22 S2 C21 105.00(19) . . ?
S2 C21 I4 111.74(19) . . ?
S2 C21 I3 108.78(19) . . ?
I4 C21 I3 113.42(17) . . ?
S2 C21 H21 107.5 . . ?
I4 C21 H21 107.5 . . ?
I3 C21 H21 107.5 . . ?
C27 C22 C23 120.9(4) . . ?
C27 C22 S2 119.1(3) . . ?
C23 C22 S2 120.0(3) . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 121.3(4) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 119.1(4) . . ?
C24 C25 C28 121.5(4) . . ?
C26 C25 C28 119.3(4) . . ?
C27 C26 C25 120.3(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C22 C27 C26 119.5(4) . . ?
C22 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C28 H28D 109.5 . . ?
H28A C28 H28D 141.1 . . ?
H28B C28 H28D 56.3 . . ?
H28C C28 H28D 56.3 . . ?
C25 C28 H28E 109.5 . . ?
H28A C28 H28E 56.3 . . ?
H28B C28 H28E 141.1 . . ?
H28C C28 H28E 56.3 . . ?
H28D C28 H28E 109.5 . . ?
C25 C28 H28F 109.5 . . ?
H28A C28 H28F 56.3 . . ?
H28B C28 H28F 56.3 . . ?
H28C C28 H28F 141.1 . . ?
H28D C28 H28F 109.5 . . ?
H28E C28 H28F 109.5 . . ?
O6 S3 O5 118.55(19) . . ?
O6 S3 C30 108.10(18) . . ?
O5 S3 C30 108.71(18) . . ?
O6 S3 C29 105.51(19) . . ?
O5 S3 C29 109.38(18) . . ?
C30 S3 C29 105.87(18) . . ?
S3 C29 I6 112.33(19) . . ?
S3 C29 I5 108.47(18) . . ?
I6 C29 I5 111.71(17) . . ?
S3 C29 H29 108.1 . . ?
I6 C29 H29 108.1 . . ?
I5 C29 H29 108.1 . . ?
C31 C30 C35 120.6(4) . . ?
C31 C30 S3 119.5(3) . . ?
C35 C30 S3 119.8(3) . . ?
C32 C31 C30 119.1(4) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C31 C32 C33 120.9(4) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 118.8(4) . . ?
C34 C33 C36 121.2(4) . . ?
C32 C33 C36 120.0(4) . . ?
C35 C34 C33 121.3(4) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C30 119.2(4) . . ?
C34 C35 H35 120.4 . . ?
C30 C35 H35 120.4 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C36 H36D 109.5 . . ?
H36A C36 H36D 141.1 . . ?
H36B C36 H36D 56.3 . . ?
H36C C36 H36D 56.3 . . ?
C33 C36 H36E 109.5 . . ?
H36A C36 H36E 56.3 . . ?
H36B C36 H36E 141.1 . . ?
H36C C36 H36E 56.3 . . ?
H36D C36 H36E 109.5 . . ?
C33 C36 H36F 109.5 . . ?
H36A C36 H36F 56.3 . . ?
H36B C36 H36F 56.3 . . ?
H36C C36 H36F 141.1 . . ?
H36D C36 H36F 109.5 . . ?
H36E C36 H36F 109.5 . . ?
C38 N3 C39 117.3(4) . . ?
C46 N4 C47 117.2(4) . . ?
C38 C37 C41 119.3(4) . . ?
C38 C37 H37 120.4 . . ?
C41 C37 H37 120.4 . . ?
N3 C38 C37 123.6(4) . . ?
N3 C38 H38 118.2 . . ?
C37 C38 H38 118.2 . . ?
N3 C39 C40 123.1(4) . . ?
N3 C39 H39 118.4 . . ?
C40 C39 H39 118.4 . . ?
C39 C40 C41 119.8(4) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C40 C41 C37 116.9(4) . . ?
C40 C41 C42 119.8(4) . . ?
C37 C41 C42 123.2(4) . . ?
C43 C42 C41 124.0(4) . . ?
C43 C42 H42 118.0 . . ?
C41 C42 H42 118.0 . . ?
C42 C43 C44 125.5(4) . . ?
C42 C43 H43 117.3 . . ?
C44 C43 H43 117.3 . . ?
C45 C44 C48 116.9(4) . . ?
C45 C44 C43 119.0(4) . . ?
C48 C44 C43 124.1(4) . . ?
C46 C45 C44 119.6(4) . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
N4 C46 C45 123.9(4) . . ?
N4 C46 H46 118.1 . . ?
C45 C46 H46 118.1 . . ?
N4 C47 C48 122.9(4) . . ?
N4 C47 H47 118.6 . . ?
C48 C47 H47 118.6 . . ?
C47 C48 C44 119.5(4) . . ?
C47 C48 H48 120.2 . . ?
C44 C48 H48 120.2 . . ?
O8 S4 O7 119.3(2) . . ?
O8 S4 C50 108.20(19) . . ?
O7 S4 C50 107.32(18) . . ?
O8 S4 C49 108.54(19) . . ?
O7 S4 C49 105.04(18) . . ?
C50 S4 C49 107.92(18) . . ?
S4 C49 I8 112.59(19) . . ?
S4 C49 I7 106.66(19) . . ?
I8 C49 I7 111.23(17) . . ?
S4 C49 H49 108.8 . . ?
I8 C49 H49 108.8 . . ?
I7 C49 H49 108.8 . . ?
C55 C50 C51 121.2(4) . . ?
C55 C50 S4 118.9(3) . . ?
C51 C50 S4 119.5(3) . . ?
C50 C51 C52 118.9(4) . . ?
C50 C51 H51 120.6 . . ?
C52 C51 H51 120.6 . . ?
C51 C52 C53 121.0(4) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
C54 C53 C52 118.5(4) . . ?
C54 C53 C56 121.1(4) . . ?
C52 C53 C56 120.4(4) . . ?
C53 C54 C55 121.5(4) . . ?
C53 C54 H54 119.3 . . ?
C55 C54 H54 119.3 . . ?
C50 C55 C54 118.9(4) . . ?
C50 C55 H55 120.6 . . ?
C54 C55 H55 120.6 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C53 C56 H56D 109.5 . . ?
H56A C56 H56D 141.1 . . ?
H56B C56 H56D 56.3 . . ?
H56C C56 H56D 56.3 . . ?
C53 C56 H56E 109.5 . . ?
H56A C56 H56E 56.3 . . ?
H56B C56 H56E 141.1 . . ?
H56C C56 H56E 56.3 . . ?
H56D C56 H56E 109.5 . . ?
C53 C56 H56F 109.5 . . ?
H56A C56 H56F 56.3 . . ?
H56B C56 H56F 56.3 . . ?
H56C C56 H56F 141.1 . . ?
H56D C56 H56F 109.5 . . ?
H56E C56 H56F 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
O2 S1 C1 I2 -61.2(2) . . . . ?
O1 S1 C1 I2 169.97(18) . . . . ?
C2 S1 C1 I2 55.5(2) . . . . ?
O2 S1 C1 I1 62.7(2) . . . . ?
O1 S1 C1 I1 -66.1(2) . . . . ?
C2 S1 C1 I1 179.46(17) . . . . ?
O2 S1 C2 C7 -3.2(4) . . . . ?
O1 S1 C2 C7 127.3(3) . . . . ?
C1 S1 C2 C7 -120.2(3) . . . . ?
O2 S1 C2 C3 179.3(3) . . . . ?
O1 S1 C2 C3 -50.2(4) . . . . ?
C1 S1 C2 C3 62.3(3) . . . . ?
C7 C2 C3 C4 0.5(6) . . . . ?
S1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 C8 -178.8(4) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C8 C5 C6 C7 -179.9(4) . . . . ?
C3 C2 C7 C6 0.8(6) . . . . ?
S1 C2 C7 C6 -176.7(3) . . . . ?
C5 C6 C7 C2 -1.5(6) . . . . ?
C11 N1 C10 C9 -0.2(6) . . . . ?
C13 C9 C10 N1 0.4(7) . . . . ?
C10 N1 C11 C12 -0.2(6) . . . . ?
N1 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C9 -0.1(6) . . . . ?
C11 C12 C13 C14 178.9(4) . . . . ?
C10 C9 C13 C12 -0.2(6) . . . . ?
C10 C9 C13 C14 -179.4(4) . . . . ?
C12 C13 C14 C15 1.6(7) . . . . ?
C9 C13 C14 C15 -179.4(4) . . . . ?
C13 C14 C15 C16 -177.7(4) . . . . ?
C14 C15 C16 C20 164.6(4) . . . . ?
C14 C15 C16 C17 -15.6(6) . . . . ?
C20 C16 C17 C18 0.1(6) . . . . ?
C15 C16 C17 C18 -179.7(4) . . . . ?
C19 N2 C18 C17 0.3(6) . . . . ?
C16 C17 C18 N2 -1.0(6) . . . . ?
C18 N2 C19 C20 1.3(6) . . . . ?
N2 C19 C20 C16 -2.2(6) . . . . ?
C17 C16 C20 C19 1.3(6) . . . . ?
C15 C16 C20 C19 -178.8(4) . . . . ?
O4 S2 C21 I4 57.7(2) . . . . ?
O3 S2 C21 I4 -172.91(18) . . . . ?
C22 S2 C21 I4 -59.4(2) . . . . ?
O4 S2 C21 I3 -68.2(2) . . . . ?
O3 S2 C21 I3 61.1(2) . . . . ?
C22 S2 C21 I3 174.57(19) . . . . ?
O4 S2 C22 C27 177.4(3) . . . . ?
O3 S2 C22 C27 45.9(4) . . . . ?
C21 S2 C22 C27 -65.3(4) . . . . ?
O4 S2 C22 C23 -0.5(4) . . . . ?
O3 S2 C22 C23 -131.9(4) . . . . ?
C21 S2 C22 C23 116.9(4) . . . . ?
C27 C22 C23 C24 -3.4(7) . . . . ?
S2 C22 C23 C24 174.4(3) . . . . ?
C22 C23 C24 C25 2.0(7) . . . . ?
C23 C24 C25 C26 1.7(7) . . . . ?
C23 C24 C25 C28 -176.2(4) . . . . ?
C24 C25 C26 C27 -4.0(7) . . . . ?
C28 C25 C26 C27 173.9(4) . . . . ?
C23 C22 C27 C26 1.0(7) . . . . ?
S2 C22 C27 C26 -176.8(3) . . . . ?
C25 C26 C27 C22 2.7(7) . . . . ?
O6 S3 C29 I6 -174.81(18) . . . . ?
O5 S3 C29 I6 56.6(2) . . . . ?
C30 S3 C29 I6 -60.3(2) . . . . ?
O6 S3 C29 I5 61.2(2) . . . . ?
O5 S3 C29 I5 -67.3(2) . . . . ?
C30 S3 C29 I5 175.69(18) . . . . ?
O6 S3 C30 C31 45.5(4) . . . . ?
O5 S3 C30 C31 175.4(3) . . . . ?
C29 S3 C30 C31 -67.2(4) . . . . ?
O6 S3 C30 C35 -131.8(3) . . . . ?
O5 S3 C30 C35 -1.9(4) . . . . ?
C29 S3 C30 C35 115.5(3) . . . . ?
C35 C30 C31 C32 -0.4(7) . . . . ?
S3 C30 C31 C32 -177.6(4) . . . . ?
C30 C31 C32 C33 -0.7(7) . . . . ?
C31 C32 C33 C34 1.6(7) . . . . ?
C31 C32 C33 C36 -178.7(5) . . . . ?
C32 C33 C34 C35 -1.4(7) . . . . ?
C36 C33 C34 C35 178.8(4) . . . . ?
C33 C34 C35 C30 0.4(6) . . . . ?
C31 C30 C35 C34 0.5(6) . . . . ?
S3 C30 C35 C34 177.8(3) . . . . ?
C39 N3 C38 C37 1.0(7) . . . . ?
C41 C37 C38 N3 -1.7(7) . . . . ?
C38 N3 C39 C40 0.1(7) . . . . ?
N3 C39 C40 C41 -0.6(7) . . . . ?
C39 C40 C41 C37 -0.1(6) . . . . ?
C39 C40 C41 C42 178.9(4) . . . . ?
C38 C37 C41 C40 1.1(6) . . . . ?
C38 C37 C41 C42 -177.8(4) . . . . ?
C40 C41 C42 C43 162.4(4) . . . . ?
C37 C41 C42 C43 -18.8(6) . . . . ?
C41 C42 C43 C44 177.3(4) . . . . ?
C42 C43 C44 C45 -178.9(4) . . . . ?
C42 C43 C44 C48 -0.9(7) . . . . ?
C48 C44 C45 C46 1.3(6) . . . . ?
C43 C44 C45 C46 179.5(4) . . . . ?
C47 N4 C46 C45 1.0(6) . . . . ?
C44 C45 C46 N4 -1.6(7) . . . . ?
C46 N4 C47 C48 -0.1(6) . . . . ?
N4 C47 C48 C44 -0.1(6) . . . . ?
C45 C44 C48 C47 -0.5(6) . . . . ?
C43 C44 C48 C47 -178.6(4) . . . . ?
O8 S4 C49 I8 57.0(2) . . . . ?
O7 S4 C49 I8 -174.33(19) . . . . ?
C50 S4 C49 I8 -60.1(2) . . . . ?
O8 S4 C49 I7 -65.3(2) . . . . ?
O7 S4 C49 I7 63.4(2) . . . . ?
C50 S4 C49 I7 177.66(18) . . . . ?
O8 S4 C50 C55 169.4(3) . . . . ?
O7 S4 C50 C55 39.4(4) . . . . ?
C49 S4 C50 C55 -73.4(4) . . . . ?
O8 S4 C50 C51 -3.7(4) . . . . ?
O7 S4 C50 C51 -133.7(3) . . . . ?
C49 S4 C50 C51 113.5(3) . . . . ?
C55 C50 C51 C52 -0.1(6) . . . . ?
S4 C50 C51 C52 172.9(3) . . . . ?
C50 C51 C52 C53 -0.1(6) . . . . ?
C51 C52 C53 C54 0.5(6) . . . . ?
C51 C52 C53 C56 -179.7(4) . . . . ?
C52 C53 C54 C55 -0.8(6) . . . . ?
C56 C53 C54 C55 179.4(4) . . . . ?
C51 C50 C55 C54 -0.2(6) . . . . ?
S4 C50 C55 C54 -173.2(3) . . . . ?
C53 C54 C55 C50 0.6(6) . . . . ?

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
C3 H3 O7 0.95 2.49 3.412(5) 163.0 1_355
C12 H12 O1 0.95 2.53 3.457(5) 164.8 1_655
C17 H17 O3 0.95 2.64 3.477(5) 147.5 1_455
C18 H18 O2 0.95 2.60 3.361(5) 137.0 2_566
C29 H29 O4 1.00 2.32 3.272(5) 157.8 1_465
C31 H31 I3 0.95 3.30 3.886(4) 121.8 1_465
C39 H39 O8 0.95 2.38 3.329(5) 176.8 2_665

_refine_diff_density_max         4.637
_refine_diff_density_min         -2.621
_refine_diff_density_rms         0.137


####################################################################### 
# 
# 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_vd027b
_database_code_depnum_ccdc_archive 'CCDC 1895421'
loop_
_audit_author_name
_audit_author_address
'Tullio Pilati'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-02-04 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 I2 O2 S, C10 H8 N2'
_chemical_formula_sum            'C18 H16 I2 N2 O2 S'
_chemical_formula_weight         578.19

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6591(8)
_cell_length_b                   9.7178(8)
_cell_length_c                   13.0375(15)
_cell_angle_alpha                93.590(5)
_cell_angle_beta                 96.031(5)
_cell_angle_gamma                114.648(5)
_cell_volume                     984.70(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5666
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      32.70

_exptl_crystal_description       wedge
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.313
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.4751
_exptl_absorpt_correction_T_max  0.5297

_exptl_special_details           
; 
Bruker KRYOFLEX low temperature device.   
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            15401
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.699
_diffrn_reflns_theta_max         33.976
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6968
_reflns_number_gt                5426
_reflns_threshold_expression     'I > 2σ(I)'

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0254P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6968
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0600
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.04255(2) 0.22456(2) 0.25394(2) 0.01718(5) Uani 1 1 d . . . . .
I2 I 0.76170(2) 0.33566(2) 0.39335(2) 0.01741(5) Uani 1 1 d . . . . .
S1 S 0.99478(8) 0.53642(7) 0.23363(5) 0.01347(12) Uani 1 1 d . . . . .
O1 O 0.8708(2) 0.4546(2) 0.14377(15) 0.0172(4) Uani 1 1 d . . . . .
O2 O 0.9781(2) 0.6606(2) 0.29034(16) 0.0199(4) Uani 1 1 d . . . . .
C1 C 0.9956(3) 0.4057(3) 0.3249(2) 0.0162(5) Uani 1 1 d . . . . .
H1 H 1.0933 0.4634 0.3818 0.019 Uiso 1 1 calc R U . . .
C2 C 1.2019(3) 0.6062(3) 0.1980(2) 0.0147(5) Uani 1 1 d . . . . .
C3 C 1.2275(3) 0.5507(3) 0.1038(2) 0.0154(5) Uani 1 1 d . . . . .
H3 H 1.1337 0.4756 0.0576 0.018 Uiso 1 1 calc R U . . .
C4 C 1.3919(3) 0.6063(3) 0.0782(2) 0.0196(6) Uani 1 1 d . . . . .
H4 H 1.4101 0.5698 0.0134 0.023 Uiso 1 1 calc R U . . .
C5 C 1.5314(3) 0.7148(3) 0.1456(2) 0.0196(6) Uani 1 1 d . . . . .
C6 C 1.5017(3) 0.7704(3) 0.2383(2) 0.0225(6) Uani 1 1 d . . . . .
H6 H 1.5954 0.8466 0.2838 0.027 Uiso 1 1 calc R U . . .
C7 C 1.3380(3) 0.7172(3) 0.2663(2) 0.0199(6) Uani 1 1 d . . . . .
H7 H 1.3193 0.7555 0.3303 0.024 Uiso 1 1 calc R U . . .
C8 C 1.7119(3) 0.7702(4) 0.1195(3) 0.0281(7) Uani 1 1 d . . . . .
H8A H 1.7724 0.8809 0.1377 0.042 Uiso 1 1 calc R U . . .
H8B H 1.7075 0.7451 0.0450 0.042 Uiso 1 1 calc R U . . .
H8C H 1.7728 0.7206 0.1589 0.042 Uiso 1 1 calc R U . . .
N1 N 1.2010(3) 0.0492(3) 0.15002(19) 0.0203(5) Uani 1 1 d . . . . .
C9 C 1.4379(3) 0.0093(3) 0.0325(2) 0.0124(5) Uani 1 1 d . . . . .
C10 C 1.2662(3) -0.0958(3) 0.0194(2) 0.0163(5) Uani 1 1 d . . . . .
H10 H 1.2257 -0.1837 -0.0300 0.020 Uiso 1 1 calc R U . . .
C12 C 1.3660(4) 0.1477(4) 0.1637(2) 0.0239(6) Uani 1 1 d . . . . .
H12 H 1.4026 0.2335 0.2146 0.029 Uiso 1 1 calc R U . . .
C11 C 1.1545(3) -0.0711(3) 0.0793(2) 0.0202(6) Uani 1 1 d . . . . .
H11 H 1.0380 -0.1443 0.0691 0.024 Uiso 1 1 calc R U . . .
C13 C 1.4882(3) 0.1333(3) 0.1082(2) 0.0208(6) Uani 1 1 d . . . . .
H13 H 1.6044 0.2070 0.1218 0.025 Uiso 1 1 calc R U . . .
N2 N 0.4360(3) 0.2192(3) 0.4693(2) 0.0209(5) Uani 1 1 d . . . . .
C14 C 0.3507(4) 0.0761(3) 0.4309(3) 0.0308(8) Uani 1 1 d . . . . .
H14 H 0.4099 0.0312 0.3936 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1825(4) -0.0149(3) 0.4400(3) 0.0297(8) Uani 1 1 d . . . . .
H15 H 0.1293 -0.1182 0.4096 0.036 Uiso 1 1 calc R U . . .
C16 C 0.0918(3) 0.0458(3) 0.4941(2) 0.0154(5) Uani 1 1 d . . . . .
C17 C 0.1804(3) 0.1985(3) 0.5358(2) 0.0215(6) Uani 1 1 d . . . . .
H17 H 0.1252 0.2468 0.5739 0.026 Uiso 1 1 calc R U . . .
C18 C 0.3504(4) 0.2792(3) 0.5209(2) 0.0239(6) Uani 1 1 d . . . . .
H18 H 0.4084 0.3832 0.5494 0.029 Uiso 1 1 calc R U . . .


_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 2.143(3) . ?
I2 C1 2.160(2) . ?
S1 O1 1.437(2) . ?
S1 O2 1.4421(19) . ?
S1 C2 1.758(2) . ?
S1 C1 1.796(3) . ?
C2 C3 1.387(4) . ?
C2 C7 1.394(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.385(4) . ?
C5 C8 1.510(4) . ?
C6 C7 1.389(4) . ?
N1 C11 1.331(4) . ?
N1 C12 1.332(4) . ?
C9 C13 1.393(4) . ?
C9 C10 1.393(3) . ?
C9 C9 1.497(5) 2_855 ?
C10 C11 1.390(3) . ?
C12 C13 1.390(4) . ?
N2 C14 1.306(4) . ?
N2 C18 1.327(3) . ?
C14 C15 1.376(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.395(4) . ?
C16 C16 1.495(5) 2_556 ?
C17 C18 1.391(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
O1 S1 O2 118.47(11) . . ?
O1 S1 C2 109.09(12) . . ?
O2 S1 C2 108.11(12) . . ?
O1 S1 C1 109.40(12) . . ?
O2 S1 C1 106.77(12) . . ?
C2 S1 C1 104.03(12) . . ?
S1 C1 I1 110.78(13) . . ?
S1 C1 I2 108.27(12) . . ?
I1 C1 I2 115.57(12) . . ?
C3 C2 C7 121.3(2) . . ?
C3 C2 S1 120.1(2) . . ?
C7 C2 S1 118.6(2) . . ?
C4 C3 C2 118.9(3) . . ?
C3 C4 C5 121.4(3) . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 C8 120.2(3) . . ?
C4 C5 C8 121.2(3) . . ?
C5 C6 C7 121.6(3) . . ?
C6 C7 C2 118.4(3) . . ?
C11 N1 C12 116.4(2) . . ?
C13 C9 C10 116.8(2) . . ?
C13 C9 C9 121.6(3) . 2_855 ?
C10 C9 C9 121.6(3) . 2_855 ?
C11 C10 C9 119.5(3) . . ?
N1 C12 C13 124.3(3) . . ?
N1 C11 C10 123.9(3) . . ?
C12 C13 C9 119.1(3) . . ?
C14 N2 C18 116.0(2) . . ?
N2 C14 C15 125.5(3) . . ?
C14 C15 C16 119.1(3) . . ?
C15 C16 C17 116.4(2) . . ?
C15 C16 C16 122.0(3) . 2_556 ?
C17 C16 C16 121.6(3) . 2_556 ?
C18 C17 C16 119.2(3) . . ?
N2 C18 C17 123.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 I1 55.77(15) . . . . ?
O2 S1 C1 I1 -174.88(12) . . . . ?
C2 S1 C1 I1 -60.68(16) . . . . ?
O1 S1 C1 I2 -71.92(15) . . . . ?
O2 S1 C1 I2 57.43(15) . . . . ?
C2 S1 C1 I2 171.63(13) . . . . ?
O1 S1 C2 C3 -14.6(2) . . . . ?
O2 S1 C2 C3 -144.7(2) . . . . ?
C1 S1 C2 C3 102.1(2) . . . . ?
O1 S1 C2 C7 165.6(2) . . . . ?
O2 S1 C2 C7 35.5(2) . . . . ?
C1 S1 C2 C7 -77.8(2) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
S1 C2 C3 C4 -179.30(19) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -2.1(4) . . . . ?
C3 C4 C5 C8 177.3(2) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C8 C5 C6 C7 -177.4(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C3 C2 C7 C6 -0.7(4) . . . . ?
S1 C2 C7 C6 179.1(2) . . . . ?
C13 C9 C10 C11 1.5(4) . . . . ?
C9 C9 C10 C11 -177.9(3) 2_855 . . . ?
C11 N1 C12 C13 1.1(4) . . . . ?
C12 N1 C11 C10 -1.4(4) . . . . ?
C9 C10 C11 N1 0.1(4) . . . . ?
N1 C12 C13 C9 0.5(5) . . . . ?
C10 C9 C13 C12 -1.7(4) . . . . ?
C9 C9 C13 C12 177.7(3) 2_855 . . . ?
C18 N2 C14 C15 -0.1(5) . . . . ?
N2 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C14 C15 C16 C16 179.3(3) . . . 2_556 ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C16 C17 C18 -178.9(3) 2_556 . . . ?
C14 N2 C18 C17 0.4(5) . . . . ?
C16 C17 C18 N2 -0.5(5) . . . . ?

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
C10 H10 O1 0.95 2.69 3.631(3) 170.2 2_755
C13 H13 O1 0.95 2.52 3.437(3) 162.8 1_655
C15 H15 O2 0.95 2.36 3.276(4) 162.4 1_445
C17 H17 O2 0.95 2.36 3.276(3) 162.9 2_666
C8 H8C O2 0.98 2.61 3.561(4) 164.8 1_655

_refine_diff_density_max         1.286
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.149

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_vd061
_database_code_depnum_ccdc_archive 'CCDC 1895419'
loop_
_audit_author_name
_audit_author_address
'Tullio Pilati'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-02-04 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2, 2(C8 H8 I2 O2 S)'
_chemical_formula_sum            'C28 H28 I4 N2 O4 S2'
_chemical_formula_weight         1028.24

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.4024(9)
_cell_length_b                   5.6825(4)
_cell_length_c                   19.6574(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.993(2)
_cell_angle_gamma                90
_cell_volume                     1673.89(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6947
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.50
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_F_000             972
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.882
_shelx_estimated_absorpt_T_min   0.335
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.2935
_exptl_absorpt_correction_T_max  0.3984

_exptl_special_details           
; 
Bruker KRYOFLEX low temperature device. 
The crystals are always multi-twinned. At the end we collected data on crystal
diffracting at high angle, in spite of it was impossible to determine all
its components. Notwithstanding, the integration was quite satisfying, the 
structure resolution and the refinement easy.  
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            18384
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.118
_diffrn_reflns_theta_max         27.749
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3783
_reflns_number_gt                2878
_reflns_threshold_expression     'I > 2σ(I)'

_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.
;


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
The final results were quite good, in spite of the twinning, and also if 
we needed to omit 25 reflections with very high Delta(F^2)/esd (look at 
the OMIT list in the _shelx_res_file section above).
The twinning is probably responsable of the large value of the second
constant in the weigthing scheme (see below).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0136P)²+16.9765P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3783
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.70032(2) 0.66853(7) -0.26902(2) 0.01441(10) Uani 1 1 d . . . . .
I2 I 0.91235(2) 0.67152(10) -0.28208(2) 0.02564(12) Uani 1 1 d . . . . .
C1 C 0.7717(3) 0.6636(11) -0.3407(3) 0.0125(11) Uani 1 1 d . . . . .
H1 H 0.7536 0.8064 -0.3731 0.015 Uiso 1 1 calc R U . . .
S1 S 0.73484(10) 0.4113(3) -0.39931(8) 0.0148(3) Uani 1 1 d . . . . .
O1 O 0.7595(3) 0.2011(8) -0.3542(2) 0.0259(11) Uani 1 1 d . . . . .
O2 O 0.6421(3) 0.4520(8) -0.4452(2) 0.0224(10) Uani 1 1 d . . . . .
C2 C 0.7936(4) 0.4122(11) -0.4574(3) 0.0163(13) Uani 1 1 d . . . . .
C3 C 0.8523(4) 0.2306(12) -0.4508(4) 0.0245(15) Uani 1 1 d . . . . .
H3 H 0.8654 0.1163 -0.4125 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8920(5) 0.2182(13) -0.5014(4) 0.0291(16) Uani 1 1 d . . . . .
H4 H 0.9321 0.0934 -0.4975 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8740(4) 0.3837(13) -0.5570(3) 0.0250(16) Uani 1 1 d . . . . .
C6 C 0.8160(4) 0.5675(13) -0.5614(3) 0.0227(15) Uani 1 1 d . . . . .
H6 H 0.8046 0.6853 -0.5984 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7746(4) 0.5810(12) -0.5125(3) 0.0191(13) Uani 1 1 d . . . . .
H7 H 0.7338 0.7044 -0.5167 0.023 Uiso 1 1 calc R U . . .
C8 C 0.9156(5) 0.3659(17) -0.6127(4) 0.044(2) Uani 1 1 d . . . . .
H8A H 0.9284 0.2006 -0.6186 0.066 Uiso 1 1 calc R U . . .
H8B H 0.9712 0.4567 -0.5948 0.066 Uiso 1 1 calc R U . . .
H8C H 0.8741 0.4288 -0.6607 0.066 Uiso 1 1 calc R U . . .
N1 N 0.6146(3) 0.6330(9) -0.1777(2) 0.0154(11) Uani 1 1 d . . . . .
C9 C 0.4771(4) 0.4435(11) -0.0392(3) 0.0159(13) Uani 1 1 d . . . . .
H9A H 0.4772 0.2701 -0.0343 0.019 Uiso 1 1 calc R U . . .
H9B H 0.4143 0.4967 -0.0630 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5248(4) 0.5100(11) -0.0879(3) 0.0133(12) Uani 1 1 d . . . . .
C11 C 0.5079(4) 0.7210(11) -0.1270(3) 0.0173(13) Uani 1 1 d . . . . .
H11 H 0.4651 0.8278 -0.1238 0.021 Uiso 1 1 calc R U . . .
C12 C 0.5536(4) 0.7749(11) -0.1705(3) 0.0180(13) Uani 1 1 d . . . . .
H12 H 0.5410 0.9203 -0.1966 0.022 Uiso 1 1 calc R U . . .
C13 C 0.6309(4) 0.4308(12) -0.1399(3) 0.0195(14) Uani 1 1 d . . . . .
H13 H 0.6745 0.3282 -0.1439 0.023 Uiso 1 1 calc R U . . .
C14 C 0.5881(4) 0.3615(11) -0.0953(3) 0.0164(13) Uani 1 1 d . . . . .
H14 H 0.6017 0.2145 -0.0701 0.020 Uiso 1 1 calc R U . . .


_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 2.167(5) . ?
I2 C1 2.119(5) . ?
C1 S1 1.784(6) . ?
C1 H1 1.0000 . ?
S1 O2 1.437(4) . ?
S1 O1 1.444(5) . ?
S1 C2 1.769(6) . ?
C2 C3 1.381(9) . ?
C2 C7 1.384(9) . ?
C3 C4 1.394(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(9) . ?
C5 C8 1.509(8) . ?
C6 C7 1.386(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 C13 1.335(8) . ?
N1 C12 1.338(8) . ?
C9 C10 1.510(7) . ?
C9 C9 1.554(11) 3_665 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.389(9) . ?
C10 C14 1.390(8) . ?
C11 C12 1.381(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.385(8) . ?
C13 H13 0.9500 . ?
C14 H14 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
S1 C1 I2 112.1(3) . . ?
S1 C1 I1 107.4(3) . . ?
I2 C1 I1 113.8(2) . . ?
S1 C1 H1 107.8 . . ?
I2 C1 H1 107.8 . . ?
I1 C1 H1 107.8 . . ?
O2 S1 O1 118.7(3) . . ?
O2 S1 C2 108.0(3) . . ?
O1 S1 C2 107.9(3) . . ?
O2 S1 C1 105.7(3) . . ?
O1 S1 C1 109.4(3) . . ?
C2 S1 C1 106.5(3) . . ?
C3 C2 C7 121.2(5) . . ?
C3 C2 S1 118.6(5) . . ?
C7 C2 S1 119.9(5) . . ?
C2 C3 C4 118.7(6) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 C8 121.0(7) . . ?
C6 C5 C8 120.3(6) . . ?
C7 C6 C5 120.9(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C2 C7 C6 119.1(6) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 N1 C12 116.7(5) . . ?
C10 C9 C9 111.1(6) . 3_665 ?
C10 C9 H9A 109.4 . . ?
C9 C9 H9A 109.4 3_665 . ?
C10 C9 H9B 109.4 . . ?
C9 C9 H9B 109.4 3_665 . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C14 117.1(5) . . ?
C11 C10 C9 121.9(5) . . ?
C14 C10 C9 121.0(6) . . ?
C12 C11 C10 119.8(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C12 C11 123.3(6) . . ?
N1 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
N1 C13 C14 124.0(6) . . ?
N1 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C13 C14 C10 119.1(6) . . ?
C13 C14 H14 120.5 . . ?
C10 C14 H14 120.5 . . ?

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
I2 C1 S1 O2 -169.3(3) . . . . ?
I1 C1 S1 O2 65.0(3) . . . . ?
I2 C1 S1 O1 61.8(3) . . . . ?
I1 C1 S1 O1 -63.9(3) . . . . ?
I2 C1 S1 C2 -54.6(4) . . . . ?
I1 C1 S1 C2 179.7(3) . . . . ?
O2 S1 C2 C3 -131.3(5) . . . . ?
O1 S1 C2 C3 -1.8(6) . . . . ?
C1 S1 C2 C3 115.6(5) . . . . ?
O2 S1 C2 C7 43.1(6) . . . . ?
O1 S1 C2 C7 172.6(5) . . . . ?
C1 S1 C2 C7 -70.0(6) . . . . ?
C7 C2 C3 C4 -0.6(10) . . . . ?
S1 C2 C3 C4 173.7(5) . . . . ?
C2 C3 C4 C5 0.4(11) . . . . ?
C3 C4 C5 C6 0.9(11) . . . . ?
C3 C4 C5 C8 -178.6(7) . . . . ?
C4 C5 C6 C7 -2.0(10) . . . . ?
C8 C5 C6 C7 177.4(7) . . . . ?
C3 C2 C7 C6 -0.5(10) . . . . ?
S1 C2 C7 C6 -174.7(5) . . . . ?
C5 C6 C7 C2 1.8(10) . . . . ?
C9 C9 C10 C11 -83.4(8) 3_665 . . . ?
C9 C9 C10 C14 96.4(8) 3_665 . . . ?
C14 C10 C11 C12 -0.2(9) . . . . ?
C9 C10 C11 C12 179.6(5) . . . . ?
C13 N1 C12 C11 -0.3(9) . . . . ?
C10 C11 C12 N1 0.1(9) . . . . ?
C12 N1 C13 C14 0.7(9) . . . . ?
N1 C13 C14 C10 -0.8(9) . . . . ?
C11 C10 C14 C13 0.6(8) . . . . ?
C9 C10 C14 C13 -179.3(5) . . . . ?

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
C1 H1 O1 1.00 2.27 3.065(8) 135.7 1_565
C11 H11 I1 0.95 3.30 4.079(6) 140.4 2_654
C14 H14 O2 0.95 2.46 3.246(7) 140.3 4_566

_refine_diff_density_max         1.442
_refine_diff_density_min         -1.932
_refine_diff_density_rms         0.183

_shelxl_version_number           2013-2



