data_global
_audit_creation_method                  'APEX3 v2018.1-0'

_publ_requested_journal                 tbd

_publ_contact_author_name               'Jonathon S. Lindsey'
_publ_contact_author_address            
;

Department of Chemistry
NC State University
2620 Yarbrough Drive
Box 8204
Raleigh, NC 27695
;
_publ_contact_author_email              jslindse@ncsu.edu
_publ_contact_author_fax                919-515-2830
_publ_contact_author_phone              919-515-6406
loop_
    _publ_author_name
    _publ_author_address
    _publ_author_id_orcid
    'PengZhi Wang' 
;
Department of Chemistry
NC State University
2620 Yarbrough Drive
Box 8204
Raleigh, NC 27695
;
?
    'Roger D. Sommer' 
;
North Carolina State University
Molecular Education, Technology, and Research Innovation Center
2620 Yarbrough Dr.
Raleigh, NC 27695
;
0000-0003-1422-5967

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_rds815
_chemical_name_systematic               ?
_chemical_name_common                   Py-Ts-Me-I
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C11.99 H11.96 I1.01 N O2 S'
_chemical_formula_iupac                 ?
_chemical_formula_weight                362.83

_chemical_melting_point                 ?

_space_group_crystal_system             orthorhombic
_space_group_name_H-M_alt               'P b c a'
_space_group_name_Hall                  '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'

_cell_length_a                          6.3705(3)
_cell_length_b                          16.0873(7)
_cell_length_c                          25.9006(11)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            2654.4(2)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           9942
_cell_measurement_theta_min             2.5328
_cell_measurement_theta_max             27.8710
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              rod
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.198
_exptl_crystal_size_mid                 0.065
_exptl_crystal_size_min                 0.050
_exptl_crystal_density_diffrn           1.816
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1413

_exptl_absorpt_coefficient_mu           2.594
_exptl_absorpt_correction_type          'Numerical'
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.67
_exptl_absorpt_correction_T_max         0.88

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'fine-focus sealed tube'
_diffrn_source_type                     ?

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         graphite

_diffrn_measurement_device_type         'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method              'phi and omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   61299
_diffrn_reflns_av_R_equivalents         0.0726
_diffrn_reflns_av_unetI/netI            0.0278
_diffrn_reflns_theta_min                2.53
_diffrn_reflns_theta_max                28.27
_diffrn_reflns_theta_full               28.27
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full    1.000
_diffrn_reflns_limit_h_min              -8
_diffrn_reflns_limit_h_max              8
_diffrn_reflns_limit_k_min              -21
_diffrn_reflns_limit_k_max              21
_diffrn_reflns_limit_l_min              -34
_diffrn_reflns_limit_l_max              34

_refine_special_details                 
;
Large residual peak near methyl group C5 may represent the presence of a small
 impurity in the specimen, where both beta positions on the ring have I. 
Modeled as disorder, 99:1 methyl:I. Disorder does not appear to arise from
rotation about N-S bond. 

;

_reflns_number_total                    3295
_reflns_number_gt                       2611
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0625
_refine_ls_R_factor_gt                  0.0450
_refine_ls_wR_factor_gt                 0.0805
_refine_ls_wR_factor_ref                0.0850
_refine_ls_goodness_of_fit_ref          1.218
_refine_ls_restrained_S_all             1.218
_refine_ls_number_reflns                3295
_refine_ls_number_parameters            166
_refine_ls_number_restraints            13
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+20.1574P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.837
_refine_diff_density_min                -1.046
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              
    'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement              'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction               'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution           ?
_computing_structure_refinement         'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics           'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material         ?

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.21662(5) 0.83019(2) 0.06624(2) 0.02419(10) Uani d . . D 1.0 . .
    S S1 0.22594(19) 0.86933(7) -0.15371(4) 0.0154(2) Uani d . . . 1.0 . .
    O O1 0.4479(5) 0.8583(2) -0.15234(13) 0.0207(8) Uani d . . . 1.0 . .
    O O2 0.1321(6) 0.9351(2) -0.18189(13) 0.0211(8) Uani d . . . 1.0 . .
    N N1 0.1554(6) 0.8835(3) -0.09240(15) 0.0162(8) Uani d . . . 1.0 . .
    C C1 0.2625(7) 0.8506(3) -0.05033(17) 0.0150(9) Uani d . . . 1.0 . .
    H H1 0.398698 0.826537 -0.050651 0.018 Uiso calc U . R 1.0 . .
    C C2 0.1341(7) 0.8597(3) -0.00838(18) 0.0166(10) Uani d . . D 1.0 . .
    C C3 -0.0601(7) 0.8967(3) -0.02466(19) 0.0159(10) Uani d . . D 1.0 . .
    C C4 -0.0432(8) 0.9095(3) -0.07625(19) 0.0195(11) Uani d . . . 1.0 . .
    H H4 -0.148929 0.932438 -0.097834 0.023 Uiso calc U . R 1.0 . .
    C C5 -0.2443(9) 0.9155(4) 0.0100(3) 0.0216(12) Uani d U P . 0.9853(18) A 1
    H H5A -0.301064 0.8635 0.023906 0.032 Uiso calc U P R 0.9853(18) A 1
    H H5B -0.353353 0.944227 -0.00983 0.032 Uiso calc U P R 0.9853(18) A 1
    H H5C -0.198163 0.951126 0.038568 0.032 Uiso calc U P R 0.9853(18) A 1
    C C6 0.1062(7) 0.7751(3) -0.17101(17) 0.0125(9) Uani d . . . 1.0 . .
    C C7 0.2087(8) 0.7002(3) -0.16069(17) 0.0160(9) Uani d . . . 1.0 . .
    H H7 0.3459 0.700403 -0.146302 0.019 Uiso calc U . R 1.0 . .
    C C8 0.1100(8) 0.6262(3) -0.17147(18) 0.0180(10) Uani d . . . 1.0 . .
    H H8 0.179337 0.575046 -0.164663 0.022 Uiso calc U . R 1.0 . .
    C C9 -0.0927(8) 0.6260(3) -0.19248(17) 0.0174(10) Uani d . . . 1.0 . .
    C C10 -0.1906(7) 0.7012(3) -0.20290(17) 0.0179(10) Uani d . . . 1.0 . .
    H H10 -0.326836 0.701055 -0.217786 0.021 Uiso calc U . R 1.0 . .
    C C11 -0.0951(7) 0.7762(3) -0.19219(17) 0.0166(10) Uani d . . . 1.0 . .
    H H11 -0.164578 0.827228 -0.199068 0.02 Uiso calc U . R 1.0 . .
    C C12 -0.2022(9) 0.5453(3) -0.2031(2) 0.0253(11) Uani d . . . 1.0 . .
    H H12A -0.351068 0.55039 -0.194134 0.038 Uiso calc U . R 1.0 . .
    H H12B -0.138175 0.501094 -0.182373 0.038 Uiso calc U . R 1.0 . .
    H H12C -0.188936 0.531543 -0.239855 0.038 Uiso calc U . R 1.0 . .
    I I2 -0.264(4) 0.9029(16) 0.0328(8) 0.016(8) Uani d U P D 0.0147(18) A 2


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C2 . 2.058(5) ?
    S1 O2 . 1.418(4) ?
    S1 O1 . 1.425(4) ?
    S1 N1 . 1.666(4) ?
    S1 C6 . 1.755(5) ?
    N1 C1 . 1.390(6) ?
    N1 C4 . 1.397(6) ?
    C1 C2 . 1.368(6) ?
    C1 H1 . 0.95 ?
    C2 C3 . 1.436(7) ?
    C3 C4 . 1.356(7) ?
    C3 C5 . 1.509(7) ?
    C3 I2 . 1.978(17) ?
    C4 H4 . 0.95 ?
    C5 H5A . 0.98 ?
    C5 H5B . 0.98 ?
    C5 H5C . 0.98 ?
    C6 C11 . 1.395(6) ?
    C6 C7 . 1.396(6) ?
    C7 C8 . 1.376(7) ?
    C7 H7 . 0.95 ?
    C8 C9 . 1.401(7) ?
    C8 H8 . 0.95 ?
    C9 C10 . 1.387(7) ?
    C9 C12 . 1.500(7) ?
    C10 C11 . 1.379(7) ?
    C10 H10 . 0.95 ?
    C11 H11 . 0.95 ?
    C12 H12A . 0.98 ?
    C12 H12B . 0.98 ?
    C12 H12C . 0.98 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 121.6(2) ?
    O2 S1 N1 . . 106.0(2) ?
    O1 S1 N1 . . 105.1(2) ?
    O2 S1 C6 . . 109.3(2) ?
    O1 S1 C6 . . 109.3(2) ?
    N1 S1 C6 . . 104.1(2) ?
    C1 N1 C4 . . 108.9(4) ?
    C1 N1 S1 . . 124.3(3) ?
    C4 N1 S1 . . 124.8(3) ?
    C2 C1 N1 . . 106.8(4) ?
    C2 C1 H1 . . 126.6 ?
    N1 C1 H1 . . 126.6 ?
    C1 C2 C3 . . 109.0(4) ?
    C1 C2 I1 . . 124.6(4) ?
    C3 C2 I1 . . 126.3(3) ?
    C4 C3 C2 . . 106.5(4) ?
    C4 C3 C5 . . 128.2(5) ?
    C2 C3 C5 . . 125.3(4) ?
    C4 C3 I2 . . 141.8(9) ?
    C2 C3 I2 . . 111.4(9) ?
    C3 C4 N1 . . 108.7(4) ?
    C3 C4 H4 . . 125.6 ?
    N1 C4 H4 . . 125.6 ?
    C3 C5 H5A . . 109.5 ?
    C3 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C3 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C11 C6 C7 . . 121.1(4) ?
    C11 C6 S1 . . 119.3(4) ?
    C7 C6 S1 . . 119.5(3) ?
    C8 C7 C6 . . 119.6(4) ?
    C8 C7 H7 . . 120.2 ?
    C6 C7 H7 . . 120.2 ?
    C7 C8 C9 . . 120.1(5) ?
    C7 C8 H8 . . 119.9 ?
    C9 C8 H8 . . 119.9 ?
    C10 C9 C8 . . 119.2(5) ?
    C10 C9 C12 . . 120.7(4) ?
    C8 C9 C12 . . 120.1(5) ?
    C11 C10 C9 . . 121.7(4) ?
    C11 C10 H10 . . 119.2 ?
    C9 C10 H10 . . 119.2 ?
    C10 C11 C6 . . 118.3(5) ?
    C10 C11 H11 . . 120.9 ?
    C6 C11 H11 . . 120.9 ?
    C9 C12 H12A . . 109.5 ?
    C9 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C9 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2 S1 N1 C1 . . . . -158.5(4) ?
    O1 S1 N1 C1 . . . . -28.6(4) ?
    C6 S1 N1 C1 . . . . 86.3(4) ?
    O2 S1 N1 C4 . . . . 39.6(5) ?
    O1 S1 N1 C4 . . . . 169.5(4) ?
    C6 S1 N1 C4 . . . . -75.6(4) ?
    C4 N1 C1 C2 . . . . -2.5(5) ?
    S1 N1 C1 C2 . . . . -166.8(4) ?
    N1 C1 C2 C3 . . . . 1.7(5) ?
    N1 C1 C2 I1 . . . . -175.3(3) ?
    C1 C2 C3 C4 . . . . -0.4(6) ?
    I1 C2 C3 C4 . . . . 176.6(4) ?
    C1 C2 C3 C5 . . . . 178.9(5) ?
    I1 C2 C3 C5 . . . . -4.1(7) ?
    C1 C2 C3 I2 . . . . 175.1(8) ?
    I1 C2 C3 I2 . . . . -7.9(9) ?
    C2 C3 C4 N1 . . . . -1.2(6) ?
    C5 C3 C4 N1 . . . . 179.5(5) ?
    I2 C3 C4 N1 . . . . -174.4(13) ?
    C1 N1 C4 C3 . . . . 2.3(6) ?
    S1 N1 C4 C3 . . . . 166.5(4) ?
    O2 S1 C6 C11 . . . . -22.5(4) ?
    O1 S1 C6 C11 . . . . -157.7(4) ?
    N1 S1 C6 C11 . . . . 90.4(4) ?
    O2 S1 C6 C7 . . . . 161.1(4) ?
    O1 S1 C6 C7 . . . . 25.9(4) ?
    N1 S1 C6 C7 . . . . -86.0(4) ?
    C11 C6 C7 C8 . . . . -0.1(7) ?
    S1 C6 C7 C8 . . . . 176.2(4) ?
    C6 C7 C8 C9 . . . . -0.3(7) ?
    C7 C8 C9 C10 . . . . 0.9(7) ?
    C7 C8 C9 C12 . . . . -178.6(4) ?
    C8 C9 C10 C11 . . . . -1.3(7) ?
    C12 C9 C10 C11 . . . . 178.3(5) ?
    C9 C10 C11 C6 . . . . 0.9(7) ?
    C7 C6 C11 C10 . . . . -0.2(7) ?
    S1 C6 C11 C10 . . . . -176.5(3) ?



