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_rds816
_chemical_name_systematic               ?
_chemical_name_common                   Py-Ts-Me-Br
_chemical_formula_moiety                'C12 H12 Br N O2 S'
_chemical_formula_sum                   'C12 H12 Br N O2 S'
_chemical_formula_iupac                 ?
_chemical_formula_weight                314.20

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21/c 1'
_space_group_name_Hall                  '-P 2ybc'
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                          13.1467(9)
_cell_length_b                          6.1735(4)
_cell_length_c                          15.7907(11)
_cell_angle_alpha                       90
_cell_angle_beta                        94.671(2)
_cell_angle_gamma                       90
_cell_volume                            1277.33(15)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           255
_cell_measurement_theta_min             2.5981
_cell_measurement_theta_max             29.5758
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              needle
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.418
_exptl_crystal_size_mid                 0.101
_exptl_crystal_size_min                 0.065
_exptl_crystal_density_diffrn           1.634
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    632

_exptl_absorpt_coefficient_mu           3.370
_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         0.51
_exptl_absorpt_correction_T_max         0.90

_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                   12231
_diffrn_reflns_av_R_equivalents         0.0362
_diffrn_reflns_av_unetI/netI            0.0360
_diffrn_reflns_theta_min                2.59
_diffrn_reflns_theta_max                28.30
_diffrn_reflns_theta_full               28.30
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full    0.997
_diffrn_reflns_limit_h_min              -17
_diffrn_reflns_limit_h_max              17
_diffrn_reflns_limit_k_min              -8
_diffrn_reflns_limit_k_max              8
_diffrn_reflns_limit_l_min              -18
_diffrn_reflns_limit_l_max              21

_refine_special_details                 
;
Methyl and bromo groups in beta position of ring are disordered. modeled in two
parts , with 70 percent occupancy of the major orientation.
SADI instructions and EADP needed to stabilize refinement of methyl group in
minor component.
;

_reflns_number_total                    3172
_reflns_number_gt                       2424
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0545
_refine_ls_R_factor_gt                  0.0315
_refine_ls_wR_factor_gt                 0.0639
_refine_ls_wR_factor_ref                0.0707
_refine_ls_goodness_of_fit_ref          1.041
_refine_ls_restrained_S_all             1.044
_refine_ls_number_reflns                3172
_refine_ls_number_parameters            170
_refine_ls_number_restraints            8
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0296P)²+0.6908P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.598
_refine_diff_density_min                -0.442
_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'
    Br Br -0.2901 2.4595
     'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              
    'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement              'APEX3 v2018.1-0 (Bruker AXS)'
_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
    S S1 0.77849(4) 0.19464(10) 0.89763(4) 0.01999(14) Uani d . . . 1.0 . .
    O O1 0.82387(13) 0.0835(3) 0.97040(11) 0.0276(4) Uani d . . . 1.0 . .
    O O2 0.77934(12) 0.4258(3) 0.89270(11) 0.0261(4) Uani d . . . 1.0 . .
    N N6 0.65610(14) 0.1241(3) 0.89063(12) 0.0192(4) Uani d . . . 1.0 . .
    C C1 0.57748(16) 0.2446(4) 0.85009(15) 0.0192(5) Uani d . . . 1.0 . .
    H H1 0.582617 0.384556 0.825825 0.023 Uiso calc U . R 1.0 . .
    C C2 0.49188(16) 0.1230(4) 0.85197(14) 0.0180(5) Uani d . . D 1.0 . .
    C C3 0.51576(17) -0.0785(4) 0.89247(15) 0.0193(5) Uani d . . D 1.0 . .
    C C4 0.61784(18) -0.0751(4) 0.91500(15) 0.0206(5) Uani d . . . 1.0 . .
    H H4 0.656387 -0.188758 0.942562 0.025 Uiso calc U . R 1.0 . .
    C C6 0.82651(16) 0.0868(4) 0.80628(15) 0.0183(5) Uani d . . . 1.0 . .
    C C7 0.86981(16) -0.1185(4) 0.80901(15) 0.0198(5) Uani d . . . 1.0 . .
    H H7 0.875607 -0.199196 0.860389 0.024 Uiso calc U . R 1.0 . .
    C C8 0.90434(17) -0.2031(4) 0.73555(15) 0.0216(5) Uani d . . . 1.0 . .
    H H8 0.93482 -0.34272 0.737106 0.026 Uiso calc U . R 1.0 . .
    C C9 0.89552(17) -0.0887(4) 0.65937(16) 0.0220(5) Uani d . . . 1.0 . .
    C C10 0.85185(17) 0.1174(4) 0.65871(16) 0.0224(5) Uani d . . . 1.0 . .
    H H10 0.845827 0.198377 0.607379 0.027 Uiso calc U . R 1.0 . .
    C C11 0.81724(16) 0.2056(4) 0.73143(15) 0.0203(5) Uani d . . . 1.0 . .
    H H11 0.787455 0.345899 0.730239 0.024 Uiso calc U . R 1.0 . .
    C C12 0.9326(2) -0.1814(5) 0.58016(17) 0.0320(6) Uani d . . . 1.0 . .
    H H12A 0.998652 -0.116621 0.570121 0.048 Uiso calc U . R 1.0 . .
    H H12B 0.88318 -0.149763 0.531925 0.048 Uiso calc U . R 1.0 . .
    H H12C 0.940463 -0.338566 0.586436 0.048 Uiso calc U . R 1.0 . .
    Br Br1 0.36011(2) 0.20807(5) 0.81109(2) 0.02483(10) Uani d . P D
     0.9131(12) A 1
    C C5 0.4419(7) -0.2562(16) 0.9062(7) 0.0238(18) Uani d . P D 0.9131(12) A
     1
    H H5A 0.384894 -0.198529 0.935545 0.036 Uiso calc U P R 0.9131(12) A 1
    H H5B 0.476335 -0.370359 0.940807 0.036 Uiso calc U P R 0.9131(12) A 1
    H H5C 0.416018 -0.316367 0.851158 0.036 Uiso calc U P R 0.9131(12) A 1
    Br Br1A 0.4215(9) -0.279(2) 0.9065(9) 0.0295(17) Uani d . P D 0.0869(12) A
     2
    C C5A 0.391(2) 0.189(7) 0.813(3) 0.02483(10) Uani d U P D 0.0869(12) A 2
    H H5AA 0.364433 0.077816 0.772734 0.037 Uiso calc U P R 0.0869(12) A 2
    H H5AB 0.397148 0.326787 0.782681 0.037 Uiso calc U P R 0.0869(12) A 2
    H H5AC 0.343561 0.207659 0.857309 0.037 Uiso calc U P R 0.0869(12) A 2

loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0166(3) 0.0204(3) 0.0227(3) -0.0014(2) -0.0004(2) 0.0003(3)
    O1 0.0248(9) 0.0350(10) 0.0220(10) 0.0009(8) -0.0039(7) 0.0013(8)
    O2 0.0254(9) 0.0188(9) 0.0341(11) -0.0048(7) 0.0030(8) -0.0033(8)
    N6 0.0165(9) 0.0187(9) 0.0226(11) -0.0010(8) 0.0024(8) 0.0030(8)
    C1 0.0182(11) 0.0163(11) 0.0235(12) 0.0003(8) 0.0037(9) 0.0004(9)
    C2 0.0159(11) 0.0166(10) 0.0215(12) 0.0005(9) 0.0010(9) -0.0025(9)
    C3 0.0219(12) 0.0172(11) 0.0192(12) -0.0004(9) 0.0042(9) -0.0049(9)
    C4 0.0243(12) 0.0173(11) 0.0204(12) -0.0007(9) 0.0025(9) 0.0019(10)
    C6 0.0131(10) 0.0169(11) 0.0247(13) -0.0018(8) 0.0000(9) 0.0033(9)
    C7 0.0179(11) 0.0170(10) 0.0241(13) -0.0009(9) -0.0009(9) 0.0057(10)
    C8 0.0181(11) 0.0156(10) 0.0305(13) -0.0023(10) -0.0016(9) 0.0013(11)
    C9 0.0124(10) 0.0261(13) 0.0268(13) -0.0049(9) -0.0019(9) -0.0027(11)
    C10 0.0182(11) 0.0245(12) 0.0235(13) -0.0012(10) -0.0037(9) 0.0055(10)
    C11 0.0170(11) 0.0173(10) 0.0260(13) -0.0002(9) -0.0014(9) 0.0044(11)
    C12 0.0297(14) 0.0362(16) 0.0294(15) 0.0043(12) -0.0025(11) -0.0050(12)
    Br1 0.01607(14) 0.01595(14) 0.04133(18) 0.00092(14) -0.00452(13)
     -0.00456(13)
    C5 0.032(5) 0.014(3) 0.027(2) -0.005(2) 0.011(3) -0.0012(18)
    Br1A 0.026(3) 0.019(2) 0.044(3) -0.010(2) 0.007(2) 0.005(2)
    C5A 0.01607(14) 0.01595(14) 0.04133(18) 0.00092(14) -0.00452(13)
     -0.00456(13)

_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
    S1 O1 . 1.4265(17) ?
    S1 O2 . 1.4291(17) ?
    S1 N6 . 1.6618(19) ?
    S1 C6 . 1.752(2) ?
    N6 C1 . 1.387(3) ?
    N6 C4 . 1.395(3) ?
    C1 C2 . 1.355(3) ?
    C1 H1 . 0.95 ?
    C2 C3 . 1.422(3) ?
    C2 C5A . 1.478(19) ?
    C2 Br1 . 1.874(2) ?
    C3 C4 . 1.360(3) ?
    C3 C5 . 1.492(8) ?
    C3 Br1A . 1.776(11) ?
    C4 H4 . 0.95 ?
    C6 C11 . 1.388(3) ?
    C6 C7 . 1.388(3) ?
    C7 C8 . 1.382(3) ?
    C7 H7 . 0.95 ?
    C8 C9 . 1.391(3) ?
    C8 H8 . 0.95 ?
    C9 C10 . 1.396(3) ?
    C9 C12 . 1.493(4) ?
    C10 C11 . 1.381(3) ?
    C10 H10 . 0.95 ?
    C11 H11 . 0.95 ?
    C12 H12A . 0.98 ?
    C12 H12B . 0.98 ?
    C12 H12C . 0.98 ?
    C5 H5A . 0.98 ?
    C5 H5B . 0.98 ?
    C5 H5C . 0.98 ?
    C5A H5AA . 0.98 ?
    C5A H5AB . 0.98 ?
    C5A H5AC . 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
    O1 S1 O2 . . 121.29(11) ?
    O1 S1 N6 . . 105.47(10) ?
    O2 S1 N6 . . 105.65(10) ?
    O1 S1 C6 . . 108.98(11) ?
    O2 S1 C6 . . 109.25(11) ?
    N6 S1 C6 . . 104.91(10) ?
    C1 N6 C4 . . 109.16(18) ?
    C1 N6 S1 . . 124.85(16) ?
    C4 N6 S1 . . 125.57(16) ?
    C2 C1 N6 . . 106.4(2) ?
    C2 C1 H1 . . 126.8 ?
    N6 C1 H1 . . 126.8 ?
    C1 C2 C3 . . 109.9(2) ?
    C1 C2 C5A . . 123.9(18) ?
    C3 C2 C5A . . 126.1(18) ?
    C1 C2 Br1 . . 125.69(18) ?
    C3 C2 Br1 . . 124.35(17) ?
    C4 C3 C2 . . 106.3(2) ?
    C4 C3 C5 . . 127.8(5) ?
    C2 C3 C5 . . 125.9(5) ?
    C4 C3 Br1A . . 131.4(5) ?
    C2 C3 Br1A . . 122.2(5) ?
    C3 C4 N6 . . 108.2(2) ?
    C3 C4 H4 . . 125.9 ?
    N6 C4 H4 . . 125.9 ?
    C11 C6 C7 . . 121.1(2) ?
    C11 C6 S1 . . 119.18(18) ?
    C7 C6 S1 . . 119.71(18) ?
    C8 C7 C6 . . 118.7(2) ?
    C8 C7 H7 . . 120.6 ?
    C6 C7 H7 . . 120.6 ?
    C7 C8 C9 . . 121.6(2) ?
    C7 C8 H8 . . 119.2 ?
    C9 C8 H8 . . 119.2 ?
    C8 C9 C10 . . 118.3(2) ?
    C8 C9 C12 . . 121.3(2) ?
    C10 C9 C12 . . 120.3(2) ?
    C11 C10 C9 . . 121.1(2) ?
    C11 C10 H10 . . 119.5 ?
    C9 C10 H10 . . 119.5 ?
    C10 C11 C6 . . 119.2(2) ?
    C10 C11 H11 . . 120.4 ?
    C6 C11 H11 . . 120.4 ?
    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 ?
    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 ?
    C2 C5A H5AA . . 109.5 ?
    C2 C5A H5AB . . 109.5 ?
    H5AA C5A H5AB . . 109.5 ?
    C2 C5A H5AC . . 109.5 ?
    H5AA C5A H5AC . . 109.5 ?
    H5AB C5A H5AC . . 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
    O1 S1 N6 C1 . . . . 156.30(19) ?
    O2 S1 N6 C1 . . . . 26.7(2) ?
    C6 S1 N6 C1 . . . . -88.7(2) ?
    O1 S1 N6 C4 . . . . -32.0(2) ?
    O2 S1 N6 C4 . . . . -161.58(19) ?
    C6 S1 N6 C4 . . . . 83.0(2) ?
    C4 N6 C1 C2 . . . . 1.7(3) ?
    S1 N6 C1 C2 . . . . 174.60(17) ?
    N6 C1 C2 C3 . . . . -1.1(3) ?
    N6 C1 C2 C5A . . . . -178.(2) ?
    N6 C1 C2 Br1 . . . . 176.93(16) ?
    C1 C2 C3 C4 . . . . 0.1(3) ?
    C5A C2 C3 C4 . . . . 177.(2) ?
    Br1 C2 C3 C4 . . . . -178.01(17) ?
    C1 C2 C3 C5 . . . . -179.6(6) ?
    Br1 C2 C3 C5 . . . . 2.3(6) ?
    C1 C2 C3 Br1A . . . . 179.8(6) ?
    C5A C2 C3 Br1A . . . . -3.(2) ?
    C2 C3 C4 N6 . . . . 1.0(3) ?
    C5 C3 C4 N6 . . . . -179.3(6) ?
    Br1A C3 C4 N6 . . . . -178.7(6) ?
    C1 N6 C4 C3 . . . . -1.7(3) ?
    S1 N6 C4 C3 . . . . -174.54(16) ?
    O1 S1 C6 C11 . . . . -161.59(18) ?
    O2 S1 C6 C11 . . . . -27.0(2) ?
    N6 S1 C6 C11 . . . . 85.85(19) ?
    O1 S1 C6 C7 . . . . 20.7(2) ?
    O2 S1 C6 C7 . . . . 155.23(18) ?
    N6 S1 C6 C7 . . . . -91.90(19) ?
    C11 C6 C7 C8 . . . . 0.3(3) ?
    S1 C6 C7 C8 . . . . 178.02(17) ?
    C6 C7 C8 C9 . . . . -0.8(3) ?
    C7 C8 C9 C10 . . . . 0.9(3) ?
    C7 C8 C9 C12 . . . . -179.8(2) ?
    C8 C9 C10 C11 . . . . -0.6(3) ?
    C12 C9 C10 C11 . . . . -179.9(2) ?
    C9 C10 C11 C6 . . . . 0.2(3) ?
    C7 C6 C11 C10 . . . . 0.0(3) ?
    S1 C6 C11 C10 . . . . -177.75(17) ?



