# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1413982'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N S, I'
_chemical_formula_sum            'C6 H10 I N S'
_chemical_formula_weight         255.11

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'
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                   8.5748(2)
_cell_length_b                   7.6434(2)
_cell_length_c                   13.3454(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.1710(10)
_cell_angle_gamma                90
_cell_volume                     874.04(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9622
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      62.33

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.824
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_process_details   'SADABS; Bruker, 2014'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16440
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1997
_reflns_number_gt                1975
_reflns_threshold_expression     'I > 2σ(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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0400P)²+0.2902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1997
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_restrained_S_all      1.278
_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
C1 C 0.2110(2) 1.0691(3) 0.18778(15) 0.0202(4) Uani 1 1 d . . . . .
H1 H 0.130(3) 1.0620(4) 0.1448(15) 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3451(2) 1.1257(2) 0.33540(14) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.4627(2) 1.0655(2) 0.27993(13) 0.0173(3) Uani 1 1 d . . . . .
C21 C 0.0565(3) 1.1831(3) 0.32518(19) 0.0287(5) Uani 1 1 d . . . . .
H21A H -0.0284 1.1785 0.2740 0.043 Uiso 1 1 calc R U . . .
H21B H 0.0678 1.3030 0.3503 0.043 Uiso 1 1 calc R U . . .
H21C H 0.0324 1.1048 0.3807 0.043 Uiso 1 1 calc R U . . .
C31 C 0.3518(3) 1.1854(3) 0.44182(17) 0.0229(4) Uani 1 1 d . . . . .
H31A H 0.4598 1.1803 0.4683 0.034 Uiso 1 1 calc R U . . .
H31B H 0.2863 1.1091 0.4817 0.034 Uiso 1 1 calc R U . . .
H31C H 0.3135 1.3060 0.4454 0.034 Uiso 1 1 calc R U . . .
C41 C 0.6295(2) 1.0357(3) 0.31035(15) 0.0225(4) Uani 1 1 d . . . . .
H41A H 0.6584 1.1112 0.3674 0.034 Uiso 1 1 calc R U . . .
H41B H 0.6954 1.0634 0.2540 0.034 Uiso 1 1 calc R U . . .
H41C H 0.6446 0.9129 0.3296 0.034 Uiso 1 1 calc R U . . .
N N 0.2033(2) 1.1272(2) 0.28090(12) 0.0185(3) Uani 1 1 d . . . . .
S S 0.39355(6) 1.01038(7) 0.16051(3) 0.02096(12) Uani 1 1 d . . . . .
I I 0.18590(2) 0.69733(2) 0.44106(2) 0.02182(9) Uani 1 1 d . . . . .


_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 N 1.324(3) . ?
C1 S 1.681(2) . ?
C1 H1 0.89(3) . ?
C3 C4 1.355(3) . ?
C3 N 1.393(3) . ?
C3 C31 1.491(3) . ?
C4 C41 1.489(3) . ?
C4 S 1.7313(19) . ?
C21 N 1.474(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 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
N C1 S 111.90(15) . . ?
N C1 H1 124.0 . . ?
S C1 H1 124.0 . . ?
C4 C3 N 111.77(17) . . ?
C4 C3 C31 128.47(19) . . ?
N C3 C31 119.77(18) . . ?
C3 C4 C41 129.09(17) . . ?
C3 C4 S 110.45(15) . . ?
C41 C4 S 120.38(14) . . ?
N C21 H21A 109.5 . . ?
N C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C1 N C3 114.44(17) . . ?
C1 N C21 123.20(18) . . ?
C3 N C21 122.33(17) . . ?
C1 S C4 91.44(10) . . ?

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
N C3 C4 C41 -177.05(19) . . . . ?
C31 C3 C4 C41 2.5(3) . . . . ?
N C3 C4 S -0.3(2) . . . . ?
C31 C3 C4 S 179.24(16) . . . . ?
S C1 N C3 -0.5(2) . . . . ?
S C1 N C21 -178.41(16) . . . . ?
C4 C3 N C1 0.6(2) . . . . ?
C31 C3 N C1 -179.07(18) . . . . ?
C4 C3 N C21 178.48(19) . . . . ?
C31 C3 N C21 -1.1(3) . . . . ?
N C1 S C4 0.24(16) . . . . ?
C3 C4 S C1 0.07(16) . . . . ?
C41 C4 S C1 177.10(17) . . . . ?

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 I 0.89 3.08 3.881(2) 151.5 2
C21 H21A I 0.98 3.13 4.049(3) 157.1 2
C31 H31B I 0.98 3.30 3.992(2) 129.0 .
C31 H31C I 0.98 3.19 4.163(2) 176.1 1_565
C41 H41A I 0.98 3.19 4.157(2) 167.9 3_676
C41 H41B I 0.98 3.01 3.961(2) 163.7 2_655

_refine_diff_density_max         0.755
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.215

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1413983'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H12 N S, I'
_chemical_formula_sum            'C7 H12 I N S'
_chemical_formula_weight         269.14

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'
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                   7.2083(10)
_cell_length_b                   8.0237(11)
_cell_length_c                   8.8800(12)
_cell_angle_alpha                78.7720(10)
_cell_angle_beta                 82.5190(10)
_cell_angle_gamma                73.7020(10)
_cell_volume                     481.96(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4598
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.32

_exptl_crystal_description       blob
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    3.473
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.187
_exptl_absorpt_correction_T_max  0.249
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5441
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2144
_reflns_number_gt                2032
_reflns_threshold_expression     'I > 2σ(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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0232P)²+0.0704P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2144
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0472
_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
C1 C -0.1281(3) 0.3478(3) 0.3132(3) 0.0256(5) Uani 1 1 d . . . . .
H1 H -0.219(3) 0.3888(13) 0.391(2) 0.031 Uiso 1 1 calc R U . . .
N N 0.0602(3) 0.2884(2) 0.3287(2) 0.0226(4) Uani 1 1 d . . . . .
S S -0.18366(8) 0.34034(8) 0.13709(7) 0.02779(13) Uani 1 1 d . . . . .
C3 C 0.1699(3) 0.2347(3) 0.1976(3) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.0572(3) 0.2501(3) 0.0823(3) 0.0248(5) Uani 1 1 d . . . . .
C20 C 0.1439(3) 0.2725(3) 0.4766(3) 0.0266(5) Uani 1 1 d . . . . .
H20A H 0.0534(18) 0.3405(14) 0.5405(13) 0.032 Uiso 1 1 calc R U . . .
H20B H 0.253(2) 0.3162(9) 0.4577(4) 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1999(4) 0.0839(3) 0.5575(3) 0.0342(6) Uani 1 1 d . . . . .
H21A H 0.0826 0.0440 0.5931 0.051 Uiso 1 1 calc R U . . .
H21B H 0.2719 0.0759 0.6460 0.051 Uiso 1 1 calc R U . . .
H21C H 0.2814 0.0094 0.4859 0.051 Uiso 1 1 calc R U . . .
C31 C 0.3854(3) 0.1718(3) 0.1898(3) 0.0303(5) Uani 1 1 d . . . . .
H31A H 0.4240 0.0449 0.2280 0.046 Uiso 1 1 calc R U . . .
H31B H 0.4356 0.2336 0.2536 0.046 Uiso 1 1 calc R U . . .
H31C H 0.4383 0.1955 0.0828 0.046 Uiso 1 1 calc R U . . .
C41 C 0.1215(4) 0.1977(4) -0.0718(3) 0.0337(6) Uani 1 1 d . . . . .
H41A H 0.2319 0.2443 -0.1173 0.051 Uiso 1 1 calc R U . . .
H41B H 0.0146 0.2452 -0.1389 0.051 Uiso 1 1 calc R U . . .
H41C H 0.1605 0.0689 -0.0608 0.051 Uiso 1 1 calc R U . . .
I I 0.37362(2) 0.66638(2) 0.27089(2) 0.03061(7) Uani 1 1 d . . . . .


_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 N 1.322(3) . ?
C1 S 1.680(2) . ?
C1 H1 0.93(3) . ?
N C3 1.390(3) . ?
N C20 1.484(3) . ?
S C4 1.728(2) . ?
C3 C4 1.354(3) . ?
C3 C31 1.489(3) . ?
C4 C41 1.489(3) . ?
C20 C21 1.510(3) . ?
C20 H20A 0.932(18) . ?
C20 H20B 0.932(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 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
N C1 S 112.21(18) . . ?
N C1 H1 123.9 . . ?
S C1 H1 123.9 . . ?
C1 N C3 114.2(2) . . ?
C1 N C20 122.31(19) . . ?
C3 N C20 123.41(19) . . ?
C1 S C4 91.16(11) . . ?
C4 C3 N 111.7(2) . . ?
C4 C3 C31 126.0(2) . . ?
N C3 C31 122.2(2) . . ?
C3 C4 C41 127.2(2) . . ?
C3 C4 S 110.63(17) . . ?
C41 C4 S 122.18(18) . . ?
N C20 C21 111.74(19) . . ?
N C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 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
S C1 N C3 0.4(2) . . . . ?
S C1 N C20 -176.54(16) . . . . ?
N C1 S C4 0.88(18) . . . . ?
C1 N C3 C4 -2.0(3) . . . . ?
C20 N C3 C4 175.0(2) . . . . ?
C1 N C3 C31 177.1(2) . . . . ?
C20 N C3 C31 -6.0(3) . . . . ?
N C3 C4 C41 -176.8(2) . . . . ?
C31 C3 C4 C41 4.2(4) . . . . ?
N C3 C4 S 2.5(2) . . . . ?
C31 C3 C4 S -176.46(19) . . . . ?
C1 S C4 C3 -1.97(18) . . . . ?
C1 S C4 C41 177.4(2) . . . . ?
C1 N C20 C21 103.6(2) . . . . ?
C3 N C20 C21 -73.1(3) . . . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1413984'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N S, I'
_chemical_formula_sum            'C8 H14 I N S'
_chemical_formula_weight         283.16

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'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   12.0281(14)
_cell_length_b                   7.7753(9)
_cell_length_c                   11.5619(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1081.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7067
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    3.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_T_max  0.538
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11622
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         28.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1386
_reflns_number_gt                1261
_reflns_threshold_expression     'I > 2σ(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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0220P)²+1.0142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1386
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0521
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
C1 C 0.2031(3) 0.2500 0.6331(3) 0.0414(10) Uani 1 2 d S T P . .
N N 0.2741(2) 0.2500 0.5467(2) 0.0292(6) Uani 1 2 d S T P . .
S S 0.07033(7) 0.2500 0.58936(8) 0.0402(2) Uani 1 2 d S T P . .
C3 C 0.2230(3) 0.2500 0.4383(3) 0.0246(6) Uani 1 2 d S T P . .
C4 C 0.1110(3) 0.2500 0.4467(3) 0.0262(7) Uani 1 2 d S T P . .
C20 C 0.3967(3) 0.2500 0.5680(3) 0.0325(8) Uani 1 2 d S T P . .
C21 C 0.4293(2) 0.0887(4) 0.6325(2) 0.0397(6) Uani 1 1 d . . . . .
H21A H 0.3979 0.0920 0.7106 0.059 Uiso 1 1 calc R U . . .
H21B H 0.5106 0.0817 0.6374 0.059 Uiso 1 1 calc R U . . .
H21C H 0.4008 -0.0122 0.5913 0.059 Uiso 1 1 calc R U . . .
C31 C 0.2911(3) 0.2500 0.3312(3) 0.0356(8) Uani 1 2 d S T P . .
H31A H 0.3319 0.1412 0.3253 0.053 Uiso 0.5 1 calc R U P . .
H31B H 0.3440 0.3458 0.3337 0.053 Uiso 0.5 1 calc R U P . .
H31C H 0.2424 0.2630 0.2638 0.053 Uiso 0.5 1 calc R U P . .
C41 C 0.0265(3) 0.2500 0.3525(3) 0.0345(8) Uani 1 2 d S T P . .
H41A H 0.0603 0.2069 0.2810 0.052 Uiso 0.5 1 calc R U P . .
H41B H -0.0006 0.3675 0.3402 0.052 Uiso 0.5 1 calc R U P . .
H41C H -0.0359 0.1756 0.3744 0.052 Uiso 0.5 1 calc R U P . .
H20 H 0.433(3) 0.2500 0.487(4) 0.041(11) Uiso 1 2 d S . P . .
H1 H 0.221(3) 0.2500 0.707(4) 0.040(12) Uiso 1 2 d S . P . .
I I 0.26044(2) 0.2500 0.95317(2) 0.03314(9) Uani 1 2 d S T 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
C1 N 1.314(5) . ?
C1 S 1.675(4) . ?
C1 H1 0.88(4) . ?
N C3 1.396(4) . ?
N C20 1.495(4) . ?
S C4 1.720(3) . ?
C3 C4 1.350(5) . ?
C3 C31 1.485(4) . ?
C4 C41 1.490(4) . ?
C20 C21 1.511(3) . ?
C20 C21 1.511(3) 8_565 ?
C20 H20 1.03(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 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
N C1 S 113.0(3) . . ?
N C1 H1 125(3) . . ?
S C1 H1 122(3) . . ?
C1 N C3 113.3(3) . . ?
C1 N C20 121.1(3) . . ?
C3 N C20 125.6(3) . . ?
C1 S C4 91.04(18) . . ?
C4 C3 N 112.0(3) . . ?
C4 C3 C31 127.6(3) . . ?
N C3 C31 120.4(3) . . ?
C3 C4 C41 128.9(3) . . ?
C3 C4 S 110.6(2) . . ?
C41 C4 S 120.4(3) . . ?
N C20 C21 109.72(18) . . ?
N C20 C21 109.72(18) . 8_565 ?
C21 C20 C21 112.2(3) . 8_565 ?
N C20 H20 106(2) . . ?
C21 C20 H20 109.7(11) . . ?
C21 C20 H20 109.7(11) 8_565 . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?

_refine_diff_density_max         0.662
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1413985'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N S, I'
_chemical_formula_sum            'C9 H10 I N S'
_chemical_formula_weight         291.14

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'
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                   7.3740(9)
_cell_length_b                   16.650(2)
_cell_length_c                   8.6559(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.4220(10)
_cell_angle_gamma                90
_cell_volume                     1033.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8330
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      28.09

_exptl_crystal_description       prism
_exptl_crystal_colour            pale
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    3.247
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.286
_exptl_absorpt_correction_T_max  0.378
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11380
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         28.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2402
_reflns_number_gt                2263
_reflns_threshold_expression     'I > 2σ(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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0175P)²+1.9850P] 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         2402
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_restrained_S_all      1.295
_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
C1 C 1.3047(6) 0.3306(3) 1.0474(5) 0.0333(9) Uani 1 1 d . . . . .
H1 H 1.3776 0.2973 0.9963 0.040 Uiso 1 1 calc R U . . .
N N 1.1244(4) 0.33987(19) 0.9938(4) 0.0262(6) Uani 1 1 d . . . . .
S S 1.39665(14) 0.38270(7) 1.21489(12) 0.0364(2) Uani 1 1 d . . . . .
C2 C 1.0452(5) 0.3930(2) 1.0848(4) 0.0243(7) Uani 1 1 d . . . . .
C3 C 0.8606(5) 0.4185(2) 1.0545(4) 0.0271(7) Uani 1 1 d . . . . .
H3 H 0.7693 0.3983 0.9671 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8163(5) 0.4743(2) 1.1570(5) 0.0294(8) Uani 1 1 d . . . . .
H4 H 0.6916 0.4931 1.1395 0.035 Uiso 1 1 calc R U . . .
C5 C 0.9496(6) 0.5040(2) 1.2860(4) 0.0297(8) Uani 1 1 d . . . . .
H5 H 0.9133 0.5423 1.3544 0.036 Uiso 1 1 calc R U . . .
C6 C 1.1328(5) 0.4791(2) 1.3163(4) 0.0283(8) Uani 1 1 d . . . . .
H6 H 1.2234 0.4996 1.4040 0.034 Uiso 1 1 calc R U . . .
C7 C 1.1794(5) 0.4231(2) 1.2135(4) 0.0258(7) Uani 1 1 d . . . . .
C21 C 1.0144(6) 0.2952(2) 0.8564(4) 0.0336(9) Uani 1 1 d . . . . .
H21A H 1.0974 0.2774 0.7880 0.040 Uiso 1 1 calc R U . . .
H21B H 0.9184 0.3311 0.7928 0.040 Uiso 1 1 calc R U . . .
C22 C 0.9210(6) 0.2228(3) 0.9097(5) 0.0378(9) Uani 1 1 d . . . . .
H22A H 0.8490 0.1942 0.8164 0.057 Uiso 1 1 calc R U . . .
H22B H 1.0161 0.1868 0.9711 0.057 Uiso 1 1 calc R U . . .
H22C H 0.8373 0.2404 0.9760 0.057 Uiso 1 1 calc R U . . .
I I 0.47481(4) 0.36268(2) 0.66931(3) 0.03291(9) Uani 1 1 d . . . . .


_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 N 1.312(5) . ?
C1 S 1.690(4) . ?
C1 H1 0.9500 . ?
N C2 1.399(5) . ?
N C21 1.475(5) . ?
S C7 1.735(4) . ?
C2 C3 1.392(5) . ?
C2 C7 1.400(5) . ?
C3 C4 1.375(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9500 . ?
C21 C22 1.513(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
N C1 S 114.5(3) . . ?
N C1 H1 122.7 . . ?
S C1 H1 122.7 . . ?
C1 N C2 113.3(3) . . ?
C1 N C21 123.2(3) . . ?
C2 N C21 123.3(3) . . ?
C1 S C7 90.41(19) . . ?
C3 C2 N 127.2(3) . . ?
C3 C2 C7 121.4(3) . . ?
N C2 C7 111.4(3) . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.8(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 117.2(3) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 S 128.5(3) . . ?
C2 C7 S 110.3(3) . . ?
N C21 C22 111.1(3) . . ?
N C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1413986'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 N S, I'
_chemical_formula_sum            'C11 H14 I N S'
_chemical_formula_weight         319.19

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'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.471(3)
_cell_length_b                   13.112(2)
_cell_length_c                   5.2955(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1213.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5645
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.775
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.343
_exptl_absorpt_correction_T_max  0.574
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12749
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2730
_reflns_number_gt                2163
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.963
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0340P)²+2.5893P] 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 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2730
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_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
C1 C 0.1326(6) 0.9540(7) 0.780(2) 0.022(3) Uani 1 1 d . . . . .
H1 H 0.1503 1.0035 0.6627 0.027 Uiso 1 1 calc R U . . .
N N 0.1787(5) 0.9018(7) 0.9244(16) 0.023(2) Uani 1 1 d . . . . .
S S 0.03847(15) 0.9263(2) 0.8181(5) 0.0266(6) Uani 1 1 d . . . . .
C2 C 0.0612(6) 0.8428(8) 1.0611(19) 0.023(2) Uani 1 1 d . . . . .
C3 C 0.0125(5) 0.7869(8) 1.217(4) 0.031(2) Uani 1 1 d . . . . .
H3 H -0.0415 0.7897 1.1964 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0454(7) 0.7276(9) 1.400(2) 0.032(3) Uani 1 1 d . . . . .
H4 H 0.0130 0.6901 1.5105 0.038 Uiso 1 1 calc R U . . .
C5 C 0.1242(7) 0.7204(9) 1.431(2) 0.030(3) Uani 1 1 d . . . . .
H5 H 0.1448 0.6777 1.5591 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1727(6) 0.7750(7) 1.277(3) 0.024(3) Uani 1 1 d . . . . .
H6 H 0.2266 0.7703 1.2961 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1412(6) 0.8364(8) 1.0933(19) 0.020(2) Uani 1 1 d . . . . .
C21 C 0.2628(6) 0.9154(9) 0.932(2) 0.025(2) Uani 1 1 d . . . . .
H21A H 0.2873 0.8482 0.9587 0.030 Uiso 1 1 calc R U . . .
H21B H 0.2761 0.9593 1.0778 0.030 Uiso 1 1 calc R U . . .
C22 C 0.2944(6) 0.9627(9) 0.694(2) 0.029(3) Uani 1 1 d . . . . .
H22A H 0.2742 1.0329 0.6751 0.035 Uiso 1 1 calc R U . . .
H22B H 0.2780 0.9223 0.5458 0.035 Uiso 1 1 calc R U . . .
C23 C 0.3813(6) 0.9655(8) 0.708(3) 0.029(3) Uani 1 1 d . . . . .
H23A H 0.3972 1.0056 0.8570 0.034 Uiso 1 1 calc R U . . .
H23B H 0.4010 0.8952 0.7285 0.034 Uiso 1 1 calc R U . . .
C24 C 0.4159(7) 1.0121(12) 0.473(2) 0.045(3) Uani 1 1 d . . . . .
H24A H 0.4718 1.0126 0.4881 0.067 Uiso 1 1 calc R U . . .
H24B H 0.4011 0.9718 0.3249 0.067 Uiso 1 1 calc R U . . .
H24C H 0.3973 1.0822 0.4533 0.067 Uiso 1 1 calc R U . . .
I I 0.16274(3) 0.14916(4) 0.2384(2) 0.02864(19) Uani 1 1 d . . . . .


_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 N 1.306(13) . ?
C1 S 1.695(11) . ?
C1 H1 0.9500 . ?
N C7 1.402(14) . ?
N C21 1.480(13) . ?
S C2 1.736(11) . ?
C2 C3 1.393(17) . ?
C2 C7 1.411(14) . ?
C3 C4 1.370(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(15) . ?
C6 H6 0.9500 . ?
C21 C22 1.509(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.521(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.512(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
N C1 S 114.7(8) . . ?
N C1 H1 122.7 . . ?
S C1 H1 122.7 . . ?
C1 N C7 113.9(9) . . ?
C1 N C21 124.5(9) . . ?
C7 N C21 121.4(9) . . ?
C1 S C2 90.1(5) . . ?
C3 C2 C7 120.1(10) . . ?
C3 C2 S 129.1(9) . . ?
C7 C2 S 110.7(8) . . ?
C4 C3 C2 117.6(9) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 122.4(11) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 120.3(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 118.5(10) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 N 128.4(9) . . ?
C6 C7 C2 121.1(10) . . ?
N C7 C2 110.5(9) . . ?
N C21 C22 112.9(9) . . ?
N C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 C23 109.7(10) . . ?
C21 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C22 111.8(10) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S C1 N C7 -3.1(12) . . . . ?
S C1 N C21 -177.4(8) . . . . ?
N C1 S C2 3.5(9) . . . . ?
C1 S C2 C3 176.4(11) . . . . ?
C1 S C2 C7 -2.9(8) . . . . ?
C7 C2 C3 C4 0.7(17) . . . . ?
S C2 C3 C4 -178.5(9) . . . . ?
C2 C3 C4 C5 -1.3(19) . . . . ?
C3 C4 C5 C6 0.9(18) . . . . ?
C4 C5 C6 C7 0.2(17) . . . . ?
C5 C6 C7 N 176.7(10) . . . . ?
C5 C6 C7 C2 -0.8(16) . . . . ?
C1 N C7 C6 -176.9(11) . . . . ?
C21 N C7 C6 -2.4(16) . . . . ?
C1 N C7 C2 0.8(12) . . . . ?
C21 N C7 C2 175.3(9) . . . . ?
C3 C2 C7 C6 0.3(16) . . . . ?
S C2 C7 C6 179.7(9) . . . . ?
C3 C2 C7 N -177.6(10) . . . . ?
S C2 C7 N 1.8(11) . . . . ?
C1 N C21 C22 -23.0(15) . . . . ?
C7 N C21 C22 163.1(9) . . . . ?
N C21 C22 C23 -175.0(9) . . . . ?
C21 C22 C23 C24 179.9(11) . . . . ?

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 I 0.95 2.96 3.880(11) 164.1 1_565
C3 H3 I 0.95 3.32 4.062(14) 136.6 2_565
C21 H21A I 0.99 2.99 3.865(11) 148.1 3
C21 H21B I 0.99 3.29 3.883(11) 119.9 1_566

_refine_diff_density_max         1.999
_refine_diff_density_min         -0.921
_refine_diff_density_rms         0.167

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1413987'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 S2'
_chemical_formula_sum            'C18 H18 N2 S2'
_chemical_formula_weight         326.46

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.4609(10)
_cell_length_b                   9.3845(11)
_cell_length_c                   20.267(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1609.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7124
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.10

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_process_details   'SADABS; Bruker, 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18137
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3648
_reflns_number_gt                3247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.983
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0473P)²+0.0949P] 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 1248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3648
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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
C11 C 0.7849(3) 0.0796(3) 0.04563(13) 0.0217(6) Uani 1 1 d . . . . .
C12 C 0.8980(3) -0.1512(3) 0.00369(13) 0.0243(6) Uani 1 1 d . . . . .
C13 C 0.9602(4) -0.2834(3) -0.00919(15) 0.0321(7) Uani 1 1 d . . . . .
H13 H 1.0178 -0.3331 0.0238 0.039 Uiso 1 1 calc R U . . .
C14 C 0.9378(4) -0.3435(3) -0.07093(15) 0.0365(7) Uani 1 1 d . . . . .
H14 H 0.9803 -0.4348 -0.0806 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8537(4) -0.2700(4) -0.11831(16) 0.0375(8) Uani 1 1 d . . . . .
H15 H 0.8391 -0.3116 -0.1606 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7898(4) -0.1365(4) -0.10550(14) 0.0316(7) Uani 1 1 d . . . . .
H16 H 0.7333 -0.0864 -0.1387 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8099(3) -0.0777(3) -0.04347(13) 0.0247(6) Uani 1 1 d . . . . .
C21 C 0.7439(3) 0.1905(3) 0.08325(14) 0.0239(6) Uani 1 1 d . . . . .
C22 C 0.7438(3) 0.4400(3) 0.12620(14) 0.0261(6) Uani 1 1 d . . . . .
C23 C 0.7490(4) 0.5842(3) 0.13857(16) 0.0317(7) Uani 1 1 d . . . . .
H23 H 0.7060 0.6504 0.1080 0.038 Uiso 1 1 calc R U . . .
C24 C 0.8182(4) 0.6305(4) 0.19659(16) 0.0364(7) Uani 1 1 d . . . . .
H24 H 0.8235 0.7296 0.2059 0.044 Uiso 1 1 calc R U . . .
C25 C 0.8799(4) 0.5337(3) 0.24103(15) 0.0353(7) Uani 1 1 d . . . . .
H25 H 0.9266 0.5671 0.2807 0.042 Uiso 1 1 calc R U . . .
C26 C 0.8745(4) 0.3884(3) 0.22851(14) 0.0301(7) Uani 1 1 d . . . . .
H26 H 0.9168 0.3224 0.2593 0.036 Uiso 1 1 calc R U . . .
C27 C 0.8065(3) 0.3413(3) 0.17041(14) 0.0258(6) Uani 1 1 d . . . . .
C121 C 0.6295(3) 0.1274(3) -0.05807(13) 0.0268(6) Uani 1 1 d . . . . .
H12A H 0.5579 0.1788 -0.0276 0.032 Uiso 1 1 calc R U . . .
H12B H 0.5646 0.0599 -0.0840 0.032 Uiso 1 1 calc R U . . .
C122 C 0.7040(4) 0.2337(4) -0.10453(17) 0.0406(8) Uani 1 1 d . . . . .
H12C H 0.6210 0.2840 -0.1289 0.061 Uiso 1 1 calc R U . . .
H12D H 0.7664 0.3026 -0.0792 0.061 Uiso 1 1 calc R U . . .
H12E H 0.7730 0.1836 -0.1357 0.061 Uiso 1 1 calc R U . . .
C221 C 0.7122(4) 0.1021(3) 0.19803(15) 0.0303(7) Uani 1 1 d . . . . .
H22A H 0.7677 0.1073 0.2410 0.036 Uiso 1 1 calc R U . . .
H22B H 0.7211 0.0028 0.1819 0.036 Uiso 1 1 calc R U . . .
C222 C 0.5399(4) 0.1354(4) 0.20908(16) 0.0400(8) Uani 1 1 d . . . . .
H22C H 0.4956 0.0676 0.2409 0.060 Uiso 1 1 calc R U . . .
H22D H 0.5295 0.2325 0.2264 0.060 Uiso 1 1 calc R U . . .
H22E H 0.4828 0.1278 0.1672 0.060 Uiso 1 1 calc R U . . .
N1 N 0.7434(3) 0.0472(3) -0.01951(11) 0.0243(5) Uani 1 1 d . . . . .
N2 N 0.7937(3) 0.1968(2) 0.15093(11) 0.0236(5) Uani 1 1 d . . . . .
S1 S 0.90676(9) -0.05689(7) 0.07815(3) 0.02685(18) Uani 1 1 d . . . . .
S2 S 0.65919(9) 0.35546(8) 0.05718(4) 0.03085(19) Uani 1 1 d . . . . .


_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
C11 C21 1.336(4) . ?
C11 N1 1.399(3) . ?
C11 S1 1.771(3) . ?
C12 C13 1.373(4) . ?
C12 C17 1.394(4) . ?
C12 S1 1.751(3) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 N1 1.388(4) . ?
C21 N2 1.436(4) . ?
C21 S2 1.786(3) . ?
C22 C23 1.377(4) . ?
C22 C27 1.394(4) . ?
C22 S2 1.760(3) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(4) . ?
C26 H26 0.9500 . ?
C27 N2 1.416(4) . ?
C121 N1 1.451(3) . ?
C121 C122 1.510(4) . ?
C121 H12A 0.9900 . ?
C121 H12B 0.9900 . ?
C122 H12C 0.9800 . ?
C122 H12D 0.9800 . ?
C122 H12E 0.9800 . ?
C221 N2 1.475(4) . ?
C221 C222 1.508(4) . ?
C221 H22A 0.9900 . ?
C221 H22B 0.9900 . ?
C222 H22C 0.9800 . ?
C222 H22D 0.9800 . ?
C222 H22E 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
C21 C11 N1 130.0(2) . . ?
C21 C11 S1 120.1(2) . . ?
N1 C11 S1 109.9(2) . . ?
C13 C12 C17 121.4(3) . . ?
C13 C12 S1 127.2(2) . . ?
C17 C12 S1 111.3(2) . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 N1 127.2(3) . . ?
C16 C17 C12 119.4(3) . . ?
N1 C17 C12 113.2(2) . . ?
C11 C21 N2 120.1(2) . . ?
C11 C21 S2 127.6(2) . . ?
N2 C21 S2 111.39(19) . . ?
C23 C22 C27 121.6(3) . . ?
C23 C22 S2 126.9(2) . . ?
C27 C22 S2 111.5(2) . . ?
C22 C23 C24 118.5(3) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C27 C26 C25 118.9(3) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C22 119.6(3) . . ?
C26 C27 N2 125.1(3) . . ?
C22 C27 N2 115.3(2) . . ?
N1 C121 C122 113.7(2) . . ?
N1 C121 H12A 108.8 . . ?
C122 C121 H12A 108.8 . . ?
N1 C121 H12B 108.8 . . ?
C122 C121 H12B 108.8 . . ?
H12A C121 H12B 107.7 . . ?
C121 C122 H12C 109.5 . . ?
C121 C122 H12D 109.5 . . ?
H12C C122 H12D 109.5 . . ?
C121 C122 H12E 109.5 . . ?
H12C C122 H12E 109.5 . . ?
H12D C122 H12E 109.5 . . ?
N2 C221 C222 115.0(3) . . ?
N2 C221 H22A 108.5 . . ?
C222 C221 H22A 108.5 . . ?
N2 C221 H22B 108.5 . . ?
C222 C221 H22B 108.5 . . ?
H22A C221 H22B 107.5 . . ?
C221 C222 H22C 109.5 . . ?
C221 C222 H22D 109.5 . . ?
H22C C222 H22D 109.5 . . ?
C221 C222 H22E 109.5 . . ?
H22C C222 H22E 109.5 . . ?
H22D C222 H22E 109.5 . . ?
C17 N1 C11 114.3(2) . . ?
C17 N1 C121 121.3(2) . . ?
C11 N1 C121 124.2(2) . . ?
C27 N2 C21 109.1(2) . . ?
C27 N2 C221 115.6(2) . . ?
C21 N2 C221 117.1(2) . . ?
C12 S1 C11 91.16(13) . . ?
C22 S2 C21 89.57(14) . . ?

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
C17 C12 C13 C14 1.5(4) . . . . ?
S1 C12 C13 C14 178.3(2) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 N1 -173.7(3) . . . . ?
C15 C16 C17 C12 2.2(4) . . . . ?
C13 C12 C17 C16 -2.6(4) . . . . ?
S1 C12 C17 C16 -179.8(2) . . . . ?
C13 C12 C17 N1 173.8(3) . . . . ?
S1 C12 C17 N1 -3.4(3) . . . . ?
N1 C11 C21 N2 176.1(3) . . . . ?
S1 C11 C21 N2 -2.3(4) . . . . ?
N1 C11 C21 S2 -15.8(5) . . . . ?
S1 C11 C21 S2 165.77(17) . . . . ?
C27 C22 C23 C24 -0.2(4) . . . . ?
S2 C22 C23 C24 178.7(2) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C24 C25 C26 C27 0.2(5) . . . . ?
C25 C26 C27 C22 -0.6(4) . . . . ?
C25 C26 C27 N2 179.6(3) . . . . ?
C23 C22 C27 C26 0.6(4) . . . . ?
S2 C22 C27 C26 -178.4(2) . . . . ?
C23 C22 C27 N2 -179.5(3) . . . . ?
S2 C22 C27 N2 1.4(3) . . . . ?
C16 C17 N1 C11 179.7(3) . . . . ?
C12 C17 N1 C11 3.6(3) . . . . ?
C16 C17 N1 C121 5.1(4) . . . . ?
C12 C17 N1 C121 -171.0(2) . . . . ?
C21 C11 N1 C17 179.3(3) . . . . ?
S1 C11 N1 C17 -2.1(3) . . . . ?
C21 C11 N1 C121 -6.2(5) . . . . ?
S1 C11 N1 C121 172.3(2) . . . . ?
C122 C121 N1 C17 -87.3(3) . . . . ?
C122 C121 N1 C11 98.7(3) . . . . ?
C26 C27 N2 C21 -169.4(3) . . . . ?
C22 C27 N2 C21 10.8(3) . . . . ?
C26 C27 N2 C221 56.0(4) . . . . ?
C22 C27 N2 C221 -123.8(3) . . . . ?
C11 C21 N2 C27 151.8(3) . . . . ?
S2 C21 N2 C27 -18.0(3) . . . . ?
C11 C21 N2 C221 -74.4(3) . . . . ?
S2 C21 N2 C221 115.7(2) . . . . ?
C222 C221 N2 C27 64.7(3) . . . . ?
C222 C221 N2 C21 -66.1(3) . . . . ?
C13 C12 S1 C11 -175.2(3) . . . . ?
C17 C12 S1 C11 1.8(2) . . . . ?
C21 C11 S1 C12 178.8(2) . . . . ?
N1 C11 S1 C12 0.1(2) . . . . ?
C23 C22 S2 C21 171.0(3) . . . . ?
C27 C22 S2 C21 -10.0(2) . . . . ?
C11 C21 S2 C22 -152.7(3) . . . . ?
N2 C21 S2 C22 16.2(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
C121 H12A S2 0.99 2.54 3.178(3) 122.3 .
C122 H12D S2 0.98 2.95 3.491(4) 115.9 .
C221 H22B S1 0.99 2.68 3.292(3) 120.0 .

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_mo_jb187_0m
_database_code_depnum_ccdc_archive 'CCDC 1413988'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_audit_creation_date             2015-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H22 N2 P S2, I'
_chemical_formula_sum            'C14 H22 I N2 P S2'
_chemical_formula_weight         440.32
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.6665(7)
_cell_length_b                   10.2797(5)
_cell_length_c                   13.4062(7)
_cell_angle_alpha                90
_cell_angle_beta                 118.4096(18)
_cell_angle_gamma                90
_cell_volume                     1777.80(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9143
_cell_measurement_temperature    173.19
_cell_measurement_theta_max      30.33
_cell_measurement_theta_min      3.16
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.810
_exptl_absorpt_coefficient_mu    2.119
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0615 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9354.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear reddish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.046
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.556
_diffrn_reflns_theta_min         3.158
_diffrn_ambient_temperature      173.19
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2352
_reflns_number_total             2726
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²+1.4287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0455
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B)
2.b Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C41(H41A,H41B,H41C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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 0.5000 0.61786(2) 0.2500 0.02640(5) Uani 1 2 d S T P . .
S2 S 0.42589(3) -0.04456(4) 0.12666(3) 0.01764(8) Uani 1 1 d . . . . .
P1 P 0.5000 0.22908(6) 0.2500 0.02028(12) Uani 1 2 d S T P . .
C1 C 0.44825(11) 0.11997(14) 0.13207(12) 0.0157(3) Uani 1 1 d . . . . .
C52 C 0.33134(15) 0.38594(18) -0.02385(18) 0.0342(4) Uani 1 1 d . . . . .
H52A H 0.2703 0.3489 -0.0886 0.051 Uiso 1 1 calc GR . . . .
H52B H 0.3427 0.4748 -0.0421 0.051 Uiso 1 1 calc GR . . . .
H52C H 0.3201 0.3875 0.0426 0.051 Uiso 1 1 calc GR . . . .
C41 C 0.31080(14) 0.11214(19) -0.18351(14) 0.0291(4) Uani 1 1 d . . . . .
H41A H 0.2448 0.1549 -0.2027 0.044 Uiso 1 1 calc GR . . . .
H41B H 0.2979 0.0344 -0.2307 0.044 Uiso 1 1 calc GR . . . .
H41C H 0.3555 0.1722 -0.1973 0.044 Uiso 1 1 calc GR . . . .
N5 N 0.41256(10) 0.16616(13) 0.02508(10) 0.0174(2) Uani 1 1 d . . . . .
C51 C 0.42540(13) 0.30348(16) 0.00161(14) 0.0224(3) Uani 1 1 d . . . . .
H51A H 0.4391 0.3072 -0.0639 0.027 Uiso 1 1 calc R . . . .
H51B H 0.4865 0.3403 0.0681 0.027 Uiso 1 1 calc R . . . .
C31 C 0.31942(13) -0.17007(18) -0.08385(15) 0.0275(4) Uani 1 1 d . . . . .
H31A H 0.3431 -0.2436 -0.0310 0.041 Uiso 1 1 calc GR . . . .
H31B H 0.3418 -0.1825 -0.1414 0.041 Uiso 1 1 calc GR . . . .
H31C H 0.2436 -0.1650 -0.1208 0.041 Uiso 1 1 calc GR . . . .
C3 C 0.36499(12) -0.04639(16) -0.02018(13) 0.0189(3) Uani 1 1 d . . . . .
C4 C 0.36320(12) 0.07362(16) -0.06084(13) 0.0193(3) Uani 1 1 d . . . . .


_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
S2 C1 1.7177(15) . ?
S2 C3 1.7322(15) . ?
P1 C1 1.7866(15) . ?
P1 C1 1.7866(15) 2_655 ?
C1 N5 1.3573(18) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C52 C51 1.513(2) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C41 C4 1.500(2) . ?
N5 C51 1.478(2) . ?
N5 C4 1.401(2) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31 C3 1.500(2) . ?
C3 C4 1.344(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S2 C3 92.49(7) . . ?
C1 P1 C1 102.23(10) . 2_655 ?
S2 C1 P1 130.36(9) . . ?
N5 C1 S2 109.27(11) . . ?
N5 C1 P1 120.23(11) . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
C1 N5 C51 122.34(13) . . ?
C1 N5 C4 114.83(13) . . ?
C4 N5 C51 122.82(13) . . ?
C52 C51 H51A 109.0 . . ?
C52 C51 H51B 109.0 . . ?
N5 C51 C52 112.85(14) . . ?
N5 C51 H51A 109.0 . . ?
N5 C51 H51B 109.0 . . ?
H51A C51 H51B 107.8 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
C31 C3 S2 120.35(13) . . ?
C4 C3 S2 110.55(12) . . ?
C4 C3 C31 129.05(15) . . ?
N5 C4 C41 121.14(15) . . ?
C3 C4 C41 126.02(15) . . ?
C3 C4 N5 112.78(13) . . ?

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 C1 N5 C51 -176.69(11) . . . . ?
S2 C1 N5 C4 3.08(16) . . . . ?
S2 C3 C4 C41 -175.54(13) . . . . ?
S2 C3 C4 N5 1.47(17) . . . . ?
P1 C1 N5 C51 7.22(19) . . . . ?
P1 C1 N5 C4 -173.01(10) . . . . ?
C1 S2 C3 C31 -177.35(13) . . . . ?
C1 S2 C3 C4 0.21(13) . . . . ?
C1 P1 C1 S2 12.94(7) 2_655 . . . ?
C1 P1 C1 N5 -171.91(15) 2_655 . . . ?
C1 N5 C51 C52 -95.78(18) . . . . ?
C1 N5 C4 C41 174.14(14) . . . . ?
C1 N5 C4 C3 -3.04(19) . . . . ?
C51 N5 C4 C41 -6.1(2) . . . . ?
C51 N5 C4 C3 176.73(14) . . . . ?
C31 C3 C4 C41 1.8(3) . . . . ?
C31 C3 C4 N5 178.77(15) . . . . ?
C3 S2 C1 P1 173.71(11) . . . . ?
C3 S2 C1 N5 -1.85(11) . . . . ?
C4 N5 C51 C52 84.47(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jb208s2
_database_code_depnum_ccdc_archive 'CCDC 1413989'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_audit_creation_date             2015-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H22 N2 P S4, I'
_chemical_formula_sum            'C14 H22 I N2 P S4'
_chemical_formula_weight         504.44
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.8142(7)
_cell_length_b                   7.1440(4)
_cell_length_c                   24.3816(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.289(2)
_cell_angle_gamma                90
_cell_volume                     2002.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9760
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      38.52
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.828
_shelx_estimated_absorpt_T_min   0.672
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0572 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.094
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            94035
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         38.653
_diffrn_reflns_theta_min         2.978
_diffrn_ambient_temperature      173.2
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9058
_reflns_number_total             11356
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.440
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         11356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²+1.5227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C151(H15A,H15B), C251(H25A,H25B)
2.b Idealised Me refined as rotating group:
 C141(H14A,H14B,H14C), C231(H23A,H23B,H23C), C241(H24A,H24B,H24C), C131(H13A,
 H13B,H13C), C252(H25C,H25D,H25E), C152(H15C,H15D,H15E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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
S22 S -0.14057(3) 0.82160(5) 0.65363(2) 0.01873(6) Uani 1 1 d . . . . .
P1 P 0.01093(3) 0.50857(5) 0.61992(2) 0.01340(5) Uani 1 1 d . . . . .
S12 S -0.05502(3) 0.76076(5) 0.51680(2) 0.01655(6) Uani 1 1 d . . . . .
S2 S 0.16162(3) 0.59799(5) 0.61053(2) 0.01999(6) Uani 1 1 d . . . . .
S1 S -0.01649(3) 0.24609(5) 0.63486(2) 0.02112(6) Uani 1 1 d . . . . .
N25 N 0.01323(10) 0.66856(15) 0.72800(4) 0.01605(18) Uani 1 1 d . . . . .
C141 C -0.39618(12) 0.6579(2) 0.47165(6) 0.0225(3) Uani 1 1 d . . . . .
H14A H -0.4129 0.5379 0.4520 0.034 Uiso 1 1 calc GR . . . .
H14B H -0.4217 0.7605 0.4450 0.034 Uiso 1 1 calc GR . . . .
H14C H -0.4378 0.6646 0.5020 0.034 Uiso 1 1 calc GR . . . .
N15 N -0.21289(9) 0.56688(15) 0.54164(4) 0.01384(17) Uani 1 1 d . . . . .
C11 C -0.09803(11) 0.59844(17) 0.55841(5) 0.01399(19) Uani 1 1 d . . . . .
C21 C -0.03356(11) 0.66113(17) 0.67255(5) 0.01469(19) Uani 1 1 d . . . . .
C14 C -0.26905(11) 0.67403(17) 0.49583(5) 0.01502(19) Uani 1 1 d . . . . .
C13 C -0.19365(11) 0.78931(18) 0.47711(5) 0.0157(2) Uani 1 1 d . . . . .
C151 C -0.27672(12) 0.42620(19) 0.56789(6) 0.0186(2) Uani 1 1 d . . . . .
H15A H -0.3544 0.4761 0.5689 0.022 Uiso 1 1 calc R . . . .
H15B H -0.2337 0.4028 0.6072 0.022 Uiso 1 1 calc R . . . .
C23 C -0.12060(13) 0.90418(19) 0.72143(6) 0.0198(2) Uani 1 1 d . . . . .
C24 C -0.03396(13) 0.80714(18) 0.75639(6) 0.0192(2) Uani 1 1 d . . . . .
C251 C 0.10590(13) 0.5389(2) 0.75747(6) 0.0215(2) Uani 1 1 d . . . . .
H25A H 0.1046 0.4243 0.7345 0.026 Uiso 1 1 calc R . . . .
H25B H 0.0896 0.5017 0.7940 0.026 Uiso 1 1 calc R . . . .
C231 C -0.19404(16) 1.0598(2) 0.73507(7) 0.0304(3) Uani 1 1 d . . . . .
H23A H -0.2004 1.1587 0.7067 0.046 Uiso 1 1 calc GR . . . .
H23B H -0.1582 1.1107 0.7723 0.046 Uiso 1 1 calc GR . . . .
H23C H -0.2717 1.0120 0.7351 0.046 Uiso 1 1 calc GR . . . .
C241 C 0.00896(17) 0.8360(2) 0.81835(6) 0.0290(3) Uani 1 1 d . . . . .
H24A H 0.0009 0.7192 0.8382 0.044 Uiso 1 1 calc GR . . . .
H24B H -0.0369 0.9345 0.8310 0.044 Uiso 1 1 calc GR . . . .
H24C H 0.0910 0.8731 0.8265 0.044 Uiso 1 1 calc GR . . . .
C131 C -0.22009(13) 0.9185(2) 0.42782(6) 0.0223(3) Uani 1 1 d . . . . .
H13A H -0.1602 1.0159 0.4325 0.033 Uiso 1 1 calc GR . . . .
H13B H -0.2963 0.9767 0.4253 0.033 Uiso 1 1 calc GR . . . .
H13C H -0.2212 0.8478 0.3933 0.033 Uiso 1 1 calc GR . . . .
C252 C 0.22586(14) 0.6262(3) 0.76789(7) 0.0319(3) Uani 1 1 d . . . . .
H25C H 0.2446 0.6555 0.7317 0.048 Uiso 1 1 calc GR . . . .
H25D H 0.2834 0.5381 0.7889 0.048 Uiso 1 1 calc GR . . . .
H25E H 0.2271 0.7414 0.7898 0.048 Uiso 1 1 calc GR . . . .
I1 I -0.45913(2) 0.83875(2) 0.61789(2) 0.02427(3) Uani 1 1 d . . . . .
C152 C -0.29075(15) 0.2437(2) 0.53526(7) 0.0279(3) Uani 1 1 d . . . . .
H15C H -0.3335 0.2666 0.4964 0.042 Uiso 1 1 calc GR . . . .
H15D H -0.3339 0.1541 0.5531 0.042 Uiso 1 1 calc GR . . . .
H15E H -0.2139 0.1923 0.5352 0.042 Uiso 1 1 calc GR . . . .


_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
S22 C21 1.6903(13) . ?
S22 C23 1.7197(14) . ?
P1 S2 1.9538(5) . ?
P1 S1 1.9514(5) . ?
P1 C11 1.8522(12) . ?
P1 C21 1.8494(13) . ?
S12 C11 1.6939(13) . ?
S12 C13 1.7122(13) . ?
N25 C21 1.3390(16) . ?
N25 C24 1.3955(17) . ?
N25 C251 1.4872(18) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C141 C14 1.4864(18) . ?
N15 C11 1.3433(16) . ?
N15 C14 1.3904(16) . ?
N15 C151 1.4866(16) . ?
C14 C13 1.3665(18) . ?
C13 C131 1.4903(18) . ?
C151 H15A 0.9900 . ?
C151 H15B 0.9900 . ?
C151 C152 1.517(2) . ?
C23 C24 1.361(2) . ?
C23 C231 1.494(2) . ?
C24 C241 1.4932(19) . ?
C251 H25A 0.9900 . ?
C251 H25B 0.9900 . ?
C251 C252 1.515(2) . ?
C231 H23A 0.9800 . ?
C231 H23B 0.9800 . ?
C231 H23C 0.9800 . ?
C241 H24A 0.9800 . ?
C241 H24B 0.9800 . ?
C241 H24C 0.9800 . ?
C131 H13A 0.9800 . ?
C131 H13B 0.9800 . ?
C131 H13C 0.9800 . ?
C252 H25C 0.9800 . ?
C252 H25D 0.9800 . ?
C252 H25E 0.9800 . ?
C152 H15C 0.9800 . ?
C152 H15D 0.9800 . ?
C152 H15E 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
C21 S22 C23 92.38(6) . . ?
S1 P1 S2 122.06(2) . . ?
C11 P1 S2 105.91(4) . . ?
C11 P1 S1 111.72(4) . . ?
C21 P1 S2 107.49(4) . . ?
C21 P1 S1 110.55(4) . . ?
C21 P1 C11 95.86(6) . . ?
C11 S12 C13 92.32(6) . . ?
C21 N25 C24 114.18(11) . . ?
C21 N25 C251 123.39(11) . . ?
C24 N25 C251 122.42(11) . . ?
H14A C141 H14B 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
C11 N15 C14 114.47(10) . . ?
C11 N15 C151 124.01(11) . . ?
C14 N15 C151 121.49(10) . . ?
S12 C11 P1 118.29(7) . . ?
N15 C11 P1 130.82(9) . . ?
N15 C11 S12 110.71(9) . . ?
S22 C21 P1 121.62(7) . . ?
N25 C21 S22 110.98(9) . . ?
N25 C21 P1 127.35(10) . . ?
N15 C14 C141 121.87(11) . . ?
C13 C14 C141 126.24(12) . . ?
C13 C14 N15 111.89(11) . . ?
C14 C13 S12 110.59(9) . . ?
C14 C13 C131 127.64(12) . . ?
C131 C13 S12 121.71(10) . . ?
N15 C151 H15A 109.4 . . ?
N15 C151 H15B 109.4 . . ?
N15 C151 C152 111.14(11) . . ?
H15A C151 H15B 108.0 . . ?
C152 C151 H15A 109.4 . . ?
C152 C151 H15B 109.4 . . ?
C24 C23 S22 110.15(10) . . ?
C24 C23 C231 129.13(13) . . ?
C231 C23 S22 120.72(11) . . ?
N25 C24 C241 121.21(13) . . ?
C23 C24 N25 112.29(12) . . ?
C23 C24 C241 126.50(13) . . ?
N25 C251 H25A 109.1 . . ?
N25 C251 H25B 109.1 . . ?
N25 C251 C252 112.39(13) . . ?
H25A C251 H25B 107.9 . . ?
C252 C251 H25A 109.1 . . ?
C252 C251 H25B 109.1 . . ?
C23 C231 H23A 109.5 . . ?
C23 C231 H23B 109.5 . . ?
C23 C231 H23C 109.5 . . ?
H23A C231 H23B 109.5 . . ?
H23A C231 H23C 109.5 . . ?
H23B C231 H23C 109.5 . . ?
C24 C241 H24A 109.5 . . ?
C24 C241 H24B 109.5 . . ?
C24 C241 H24C 109.5 . . ?
H24A C241 H24B 109.5 . . ?
H24A C241 H24C 109.5 . . ?
H24B C241 H24C 109.5 . . ?
C13 C131 H13A 109.5 . . ?
C13 C131 H13B 109.5 . . ?
C13 C131 H13C 109.5 . . ?
H13A C131 H13B 109.5 . . ?
H13A C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
C251 C252 H25C 109.5 . . ?
C251 C252 H25D 109.5 . . ?
C251 C252 H25E 109.5 . . ?
H25C C252 H25D 109.5 . . ?
H25C C252 H25E 109.5 . . ?
H25D C252 H25E 109.5 . . ?
C151 C152 H15C 109.5 . . ?
C151 C152 H15D 109.5 . . ?
C151 C152 H15E 109.5 . . ?
H15C C152 H15D 109.5 . . ?
H15C C152 H15E 109.5 . . ?
H15D C152 H15E 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
S22 C23 C24 N25 -0.50(16) . . . . ?
S22 C23 C24 C241 -179.66(13) . . . . ?
S2 P1 C11 S12 -11.16(8) . . . . ?
S2 P1 C11 N15 174.13(11) . . . . ?
S2 P1 C21 S22 106.68(7) . . . . ?
S2 P1 C21 N25 -70.53(12) . . . . ?
S1 P1 C11 S12 -146.20(6) . . . . ?
S1 P1 C11 N15 39.09(13) . . . . ?
S1 P1 C21 S22 -117.88(7) . . . . ?
S1 P1 C21 N25 64.91(12) . . . . ?
C141 C14 C13 S12 -179.34(11) . . . . ?
C141 C14 C13 C131 -2.2(2) . . . . ?
N15 C14 C13 S12 0.20(14) . . . . ?
N15 C14 C13 C131 177.32(13) . . . . ?
C11 P1 C21 S22 -2.05(9) . . . . ?
C11 P1 C21 N25 -179.26(12) . . . . ?
C11 S12 C13 C14 -0.66(10) . . . . ?
C11 S12 C13 C131 -177.97(12) . . . . ?
C11 N15 C14 C141 -179.89(12) . . . . ?
C11 N15 C14 C13 0.54(16) . . . . ?
C11 N15 C151 C152 -96.18(15) . . . . ?
C21 S22 C23 C24 -0.32(12) . . . . ?
C21 S22 C23 C231 -179.76(14) . . . . ?
C21 P1 C11 S12 98.93(8) . . . . ?
C21 P1 C11 N15 -75.78(13) . . . . ?
C21 N25 C24 C23 1.37(17) . . . . ?
C21 N25 C24 C241 -179.42(14) . . . . ?
C21 N25 C251 C252 99.63(15) . . . . ?
C14 N15 C11 P1 174.00(10) . . . . ?
C14 N15 C11 S12 -1.03(14) . . . . ?
C14 N15 C151 C152 81.99(15) . . . . ?
C13 S12 C11 P1 -174.77(8) . . . . ?
C13 S12 C11 N15 0.96(10) . . . . ?
C151 N15 C11 P1 -7.72(19) . . . . ?
C151 N15 C11 S12 177.26(10) . . . . ?
C151 N15 C14 C141 1.77(18) . . . . ?
C151 N15 C14 C13 -177.80(11) . . . . ?
C23 S22 C21 P1 -176.54(9) . . . . ?
C23 S22 C21 N25 1.09(10) . . . . ?
C24 N25 C21 S22 -1.59(14) . . . . ?
C24 N25 C21 P1 175.87(10) . . . . ?
C24 N25 C251 C252 -81.57(17) . . . . ?
C251 N25 C21 S22 177.30(10) . . . . ?
C251 N25 C21 P1 -5.25(19) . . . . ?
C251 N25 C24 C23 -177.53(13) . . . . ?
C251 N25 C24 C241 1.7(2) . . . . ?
C231 C23 C24 N25 178.88(15) . . . . ?
C231 C23 C24 C241 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
