# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009



data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Junfa Wei'
'Jingjing Cao'
'Zhanguo Chen'
'Xianying Shi'
'Lihui Zhang'

_publ_contact_author_name        'Junfa Wei'
_publ_contact_author_email       WEIJF@SNNU.EDU.CN

_publ_section_title              
;
KI-catalyzed aminobromination of olefins with
TsNH2-NBS combination
;

# Attachment 'z.cif'

data_z
_database_code_depnum_ccdc_archive 'CCDC 723422'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 Br N O2 S'
_chemical_formula_sum            'C13 H18 Br N O2 S'
_chemical_formula_weight         332.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0140(14)
_cell_length_b                   9.4940(19)
_cell_length_c                   11.755(2)
_cell_angle_alpha                74.26(3)
_cell_angle_beta                 79.41(3)
_cell_angle_gamma                86.75(3)
_cell_volume                     740.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2730
_cell_measurement_theta_min      1.83
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    2.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7215
_exptl_absorpt_correction_T_max  0.8005
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4006
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2730
_reflns_number_gt                1701
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8537P] where P=(Fo^2^+2Fc^2^)/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         2730
_refine_ls_number_parameters     168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.12707(12) 0.92588(10) 0.15096(8) 0.1107(5) Uani 1 1 d . . .
C1 C 0.6821(7) 0.4083(5) 0.2714(4) 0.0455(12) Uani 1 1 d . . .
C2 C 0.4070(8) 0.3450(7) 0.2021(5) 0.0616(15) Uani 1 1 d . . .
H2 H 0.2738 0.3319 0.2130 0.074 Uiso 1 1 calc R . .
C3 C 0.7216(9) 0.3415(7) 0.0862(5) 0.0655(16) Uani 1 1 d . . .
H3 H 0.8021 0.3260 0.0184 0.079 Uiso 1 1 calc R . .
C4 C 0.4836(8) 0.3894(6) 0.2869(5) 0.0551(14) Uani 1 1 d . . .
H4 H 0.4025 0.4065 0.3540 0.066 Uiso 1 1 calc R . .
C5 C 0.8013(8) 0.3857(6) 0.1695(5) 0.0578(14) Uani 1 1 d . . .
H5 H 0.9343 0.4003 0.1576 0.069 Uiso 1 1 calc R . .
C6 C 0.8050(8) 0.7462(6) 0.2736(5) 0.0541(14) Uani 1 1 d . . .
H6 H 0.8419 0.7084 0.2028 0.065 Uiso 1 1 calc R . .
C7 C 0.9841(8) 0.7988(7) 0.3036(5) 0.0626(15) Uani 1 1 d . . .
H7 H 1.0657 0.7140 0.3323 0.075 Uiso 1 1 calc R . .
C8 C 0.6519(9) 0.8670(7) 0.2494(6) 0.0673(16) Uani 1 1 d . . .
H8A H 0.6975 0.9374 0.1735 0.081 Uiso 1 1 calc R . .
H8B H 0.5334 0.8244 0.2425 0.081 Uiso 1 1 calc R . .
C9 C 0.5246(9) 0.3198(6) 0.1014(5) 0.0594(15) Uani 1 1 d . . .
C10 C 0.6078(10) 0.9460(7) 0.3485(7) 0.082(2) Uani 1 1 d . . .
H10A H 0.5188 1.0266 0.3262 0.099 Uiso 1 1 calc R . .
H10B H 0.5454 0.8789 0.4222 0.099 Uiso 1 1 calc R . .
C11 C 0.9389(11) 0.8819(8) 0.3970(7) 0.081(2) Uani 1 1 d . . .
H11A H 1.0579 0.9236 0.4041 0.098 Uiso 1 1 calc R . .
H11B H 0.8903 0.8143 0.4738 0.098 Uiso 1 1 calc R . .
C12 C 0.7906(12) 1.0041(8) 0.3697(7) 0.090(2) Uani 1 1 d . . .
H12A H 0.7594 1.0479 0.4366 0.108 Uiso 1 1 calc R . .
H12B H 0.8453 1.0795 0.2990 0.108 Uiso 1 1 calc R . .
C13 C 0.4356(11) 0.2702(8) 0.0110(6) 0.084(2) Uani 1 1 d . . .
H13A H 0.4743 0.3351 -0.0674 0.126 Uiso 1 1 calc R . .
H13B H 0.2968 0.2714 0.0325 0.126 Uiso 1 1 calc R . .
H13C H 0.4793 0.1727 0.0105 0.126 Uiso 1 1 calc R . .
N1 N 0.7237(6) 0.6251(5) 0.3784(4) 0.0521(11) Uani 1 1 d D . .
O1 O 0.9897(5) 0.4479(4) 0.3516(3) 0.0593(10) Uani 1 1 d . . .
O2 O 0.6858(5) 0.3727(4) 0.4977(3) 0.0574(10) Uani 1 1 d . . .
S1 S 0.78245(18) 0.45698(14) 0.38282(12) 0.0470(4) Uani 1 1 d . . .
H1A H 0.597(2) 0.635(6) 0.408(5) 0.063(16) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0822(6) 0.1003(7) 0.1218(8) -0.0036(5) 0.0182(5) -0.0168(5)
C1 0.047(3) 0.035(3) 0.054(3) -0.015(2) -0.005(2) 0.006(2)
C2 0.045(3) 0.071(4) 0.073(4) -0.025(3) -0.014(3) 0.000(3)
C3 0.072(4) 0.067(4) 0.065(4) -0.035(3) -0.005(3) 0.005(3)
C4 0.049(3) 0.061(4) 0.057(3) -0.021(3) -0.006(2) 0.006(3)
C5 0.050(3) 0.064(4) 0.064(4) -0.029(3) -0.006(3) 0.005(3)
C6 0.054(3) 0.062(4) 0.055(3) -0.029(3) -0.010(3) 0.005(3)
C7 0.057(3) 0.056(4) 0.075(4) -0.014(3) -0.019(3) 0.005(3)
C8 0.063(4) 0.069(4) 0.076(4) -0.016(3) -0.036(3) 0.011(3)
C9 0.077(4) 0.048(3) 0.060(3) -0.020(3) -0.020(3) 0.001(3)
C10 0.084(5) 0.058(4) 0.102(5) -0.027(4) -0.009(4) 0.026(4)
C11 0.093(5) 0.079(5) 0.091(5) -0.038(4) -0.041(4) -0.005(4)
C12 0.118(6) 0.068(5) 0.097(5) -0.044(4) -0.016(5) 0.003(4)
C13 0.101(5) 0.082(5) 0.084(5) -0.035(4) -0.032(4) -0.006(4)
N1 0.049(3) 0.051(3) 0.060(3) -0.025(2) 0.000(2) 0.001(2)
O1 0.045(2) 0.064(2) 0.075(3) -0.029(2) -0.0135(18) 0.0104(17)
O2 0.059(2) 0.057(2) 0.055(2) -0.0138(18) -0.0137(18) 0.0086(18)
S1 0.0425(7) 0.0467(8) 0.0543(8) -0.0189(6) -0.0095(6) 0.0087(5)

_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
Br1 C7 1.995(6) . ?
C1 C4 1.386(7) . ?
C1 C5 1.390(7) . ?
C1 S1 1.768(5) . ?
C2 C4 1.382(7) . ?
C2 C9 1.383(8) . ?
C2 H2 0.9300 . ?
C3 C5 1.378(7) . ?
C3 C9 1.380(8) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 N1 1.487(7) . ?
C6 C7 1.510(8) . ?
C6 C8 1.532(7) . ?
C6 H6 0.9800 . ?
C7 C11 1.498(8) . ?
C7 H7 0.9800 . ?
C8 C10 1.527(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.513(8) . ?
C10 C12 1.511(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.522(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 S1 1.615(4) . ?
N1 H1A 0.90(3) . ?
O1 S1 1.436(4) . ?
O2 S1 1.436(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C5 119.7(5) . . ?
C4 C1 S1 119.9(4) . . ?
C5 C1 S1 120.5(4) . . ?
C4 C2 C9 121.3(5) . . ?
C4 C2 H2 119.4 . . ?
C9 C2 H2 119.4 . . ?
C5 C3 C9 121.3(5) . . ?
C5 C3 H3 119.3 . . ?
C9 C3 H3 119.3 . . ?
C2 C4 C1 119.6(5) . . ?
C2 C4 H4 120.2 . . ?
C1 C4 H4 120.2 . . ?
C3 C5 C1 119.7(5) . . ?
C3 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
N1 C6 C7 106.8(4) . . ?
N1 C6 C8 109.6(5) . . ?
C7 C6 C8 112.6(5) . . ?
N1 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
C8 C6 H6 109.3 . . ?
C11 C7 C6 113.1(5) . . ?
C11 C7 Br1 110.2(5) . . ?
C6 C7 Br1 106.7(4) . . ?
C11 C7 H7 108.9 . . ?
C6 C7 H7 108.9 . . ?
Br1 C7 H7 108.9 . . ?
C10 C8 C6 112.3(5) . . ?
C10 C8 H8A 109.1 . . ?
C6 C8 H8A 109.1 . . ?
C10 C8 H8B 109.1 . . ?
C6 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C3 C9 C2 118.5(5) . . ?
C3 C9 C13 121.8(5) . . ?
C2 C9 C13 119.8(6) . . ?
C12 C10 C8 111.3(6) . . ?
C12 C10 H10A 109.4 . . ?
C8 C10 H10A 109.4 . . ?
C12 C10 H10B 109.4 . . ?
C8 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C7 C11 C12 113.6(5) . . ?
C7 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C7 C11 H11B 108.8 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C10 C12 C11 110.8(6) . . ?
C10 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 N1 S1 120.7(3) . . ?
C6 N1 H1A 115(4) . . ?
S1 N1 H1A 112(4) . . ?
O2 S1 O1 119.6(2) . . ?
O2 S1 N1 105.3(2) . . ?
O1 S1 N1 108.3(2) . . ?
O2 S1 C1 107.6(2) . . ?
O1 S1 C1 107.5(2) . . ?
N1 S1 C1 108.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.113
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.079