# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Hugenberg, Verena'
'Frohlich, Roland'
'Haufe, Guenter'

_publ_contact_author_name        'Hugenberg, Verena'
_publ_contact_author_email       haufe@uni-muenster.de

_publ_section_title              
;
Oxidative Desulfurization-Fluorination of Thioethers.
Application for the Synthesis of Fluorinated Nitrogen
Containing Building Blocks
;

# Attachment '- HAF5170.CIF'

data_haf5170
_database_code_depnum_ccdc_archive 'CCDC 788179'
#TrackingRef '- HAF5170.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 Br2 F2 N O3'
_chemical_formula_weight         399.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   13.5963(9)
_cell_length_b                   7.1431(5)
_cell_length_c                   13.1021(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.214(3)
_cell_angle_gamma                90.00
_cell_volume                     1269.03(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2088
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    8.408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1339
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7604
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.53
_diffrn_reflns_theta_max         67.41
_reflns_number_total             2197
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0983P)^2^+2.7099P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.83107(4) 0.13780(7) 0.63027(4) 0.0379(2) Uani 1 1 d . . .
Br2 Br 0.92433(4) 0.44584(9) 0.78177(5) 0.0471(3) Uani 1 1 d . . .
F1 F 0.7382(2) 0.2244(5) 0.8626(2) 0.0434(7) Uani 1 1 d . . .
F2 F 0.7311(2) 0.5221(5) 0.8876(2) 0.0451(8) Uani 1 1 d . . .
O1 O 0.8011(3) 0.7035(6) 0.6101(4) 0.0545(11) Uani 1 1 d . . .
O2 O 0.8728(3) 0.4797(5) 0.5188(3) 0.0410(9) Uani 1 1 d . . .
O3 O 0.6398(3) 0.4248(5) 0.5601(3) 0.0391(8) Uani 1 1 d . . .
N1 N 0.7215(3) 0.4159(6) 0.7210(3) 0.0317(9) Uani 1 1 d . . .
C1 C 0.8274(4) 0.5459(7) 0.5975(4) 0.0366(11) Uani 1 1 d . . .
C2 C 0.8156(4) 0.3943(7) 0.6808(4) 0.0313(10) Uani 1 1 d . . .
C3 C 0.6364(4) 0.4148(7) 0.6518(4) 0.0317(10) Uani 1 1 d . . .
C4 C 0.5510(4) 0.3979(7) 0.7152(4) 0.0303(10) Uani 1 1 d . . .
C5 C 0.4509(4) 0.3990(8) 0.6855(4) 0.0363(11) Uani 1 1 d . . .
H5 H 0.4276 0.4104 0.6164 0.044 Uiso 1 1 calc R . .
C6 C 0.3866(4) 0.3825(8) 0.7630(4) 0.0394(12) Uani 1 1 d . . .
H6 H 0.3182 0.3832 0.7463 0.047 Uiso 1 1 calc R . .
C7 C 0.4222(4) 0.3649(7) 0.8643(4) 0.0393(12) Uani 1 1 d . . .
H7 H 0.3770 0.3541 0.9150 0.047 Uiso 1 1 calc R . .
C8 C 0.5220(4) 0.3627(7) 0.8933(4) 0.0376(12) Uani 1 1 d . . .
H8 H 0.5456 0.3516 0.9622 0.045 Uiso 1 1 calc R . .
C9 C 0.5857(4) 0.3777(6) 0.8155(4) 0.0314(10) Uani 1 1 d . . .
C10 C 0.6966(4) 0.3824(7) 0.8241(4) 0.0318(10) Uani 1 1 d . . .
C11 C 0.8874(5) 0.6169(10) 0.4399(6) 0.0592(18) Uani 1 1 d . . .
H11A H 0.8252 0.6780 0.4201 0.089 Uiso 1 1 calc R . .
H11B H 0.9117 0.5550 0.3809 0.089 Uiso 1 1 calc R . .
H11C H 0.9350 0.7096 0.4659 0.089 Uiso 1 1 calc R . .

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 0.0370(4) 0.0318(4) 0.0447(4) -0.0031(2) 0.0023(2) 0.0024(2)
Br2 0.0301(3) 0.0608(5) 0.0494(4) -0.0124(3) -0.0044(3) -0.0035(2)
F1 0.0395(16) 0.0476(18) 0.0424(16) 0.0106(14) -0.0021(13) 0.0066(14)
F2 0.0405(17) 0.0543(19) 0.0398(17) -0.0146(14) -0.0007(13) -0.0091(14)
O1 0.058(2) 0.033(2) 0.075(3) 0.005(2) 0.026(2) 0.0081(19)
O2 0.039(2) 0.044(2) 0.041(2) 0.0110(16) 0.0120(16) 0.0090(16)
O3 0.0390(19) 0.049(2) 0.0293(18) 0.0008(15) 0.0026(15) 0.0048(16)
N1 0.0255(19) 0.037(2) 0.032(2) -0.0003(17) 0.0021(16) -0.0013(17)
C1 0.026(2) 0.037(3) 0.047(3) 0.002(2) 0.008(2) -0.0026(19)
C2 0.029(2) 0.028(2) 0.036(3) -0.005(2) -0.0031(19) -0.0001(19)
C3 0.030(2) 0.030(2) 0.035(3) -0.0016(19) -0.001(2) 0.0001(19)
C4 0.029(2) 0.028(2) 0.035(3) 0.0000(19) 0.0045(19) -0.0022(19)
C5 0.031(2) 0.037(3) 0.041(3) -0.001(2) 0.002(2) -0.002(2)
C6 0.030(3) 0.038(3) 0.050(3) 0.003(2) 0.004(2) -0.001(2)
C7 0.041(3) 0.030(3) 0.049(3) 0.002(2) 0.014(2) 0.000(2)
C8 0.046(3) 0.035(3) 0.032(3) 0.001(2) 0.007(2) 0.001(2)
C9 0.031(2) 0.027(2) 0.037(3) -0.0004(19) 0.002(2) 0.0011(19)
C10 0.033(2) 0.032(2) 0.030(2) 0.0003(19) -0.0022(19) -0.005(2)
C11 0.049(3) 0.068(4) 0.063(4) 0.024(3) 0.019(3) 0.011(3)

_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 C2 1.965(5) . ?
Br2 C2 1.945(5) . ?
F1 C10 1.344(6) . ?
F2 C10 1.360(6) . ?
O1 C1 1.197(7) . ?
O2 C1 1.327(7) . ?
O2 C11 1.449(7) . ?
O3 C3 1.208(6) . ?
N1 C3 1.416(6) . ?
N1 C2 1.428(6) . ?
N1 C10 1.437(6) . ?
C1 C2 1.555(7) . ?
C3 C4 1.482(7) . ?
C4 C9 1.372(7) . ?
C4 C5 1.388(7) . ?
C5 C6 1.393(8) . ?
C5 H5 0.9400 . ?
C6 C7 1.385(8) . ?
C6 H6 0.9400 . ?
C7 C8 1.382(8) . ?
C7 H7 0.9400 . ?
C8 C9 1.389(7) . ?
C8 H8 0.9400 . ?
C9 C10 1.504(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?

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 O2 C11 114.1(5) . . ?
C3 N1 C2 118.4(4) . . ?
C3 N1 C10 111.3(4) . . ?
C2 N1 C10 127.4(4) . . ?
O1 C1 O2 127.2(5) . . ?
O1 C1 C2 120.7(5) . . ?
O2 C1 C2 112.0(4) . . ?
N1 C2 C1 109.0(4) . . ?
N1 C2 Br2 112.7(3) . . ?
C1 C2 Br2 103.5(3) . . ?
N1 C2 Br1 110.2(3) . . ?
C1 C2 Br1 113.2(3) . . ?
Br2 C2 Br1 108.1(2) . . ?
O3 C3 N1 123.2(5) . . ?
O3 C3 C4 130.6(5) . . ?
N1 C3 C4 106.2(4) . . ?
C9 C4 C5 122.1(5) . . ?
C9 C4 C3 108.5(4) . . ?
C5 C4 C3 129.4(5) . . ?
C6 C5 C4 116.7(5) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C7 C6 C5 120.9(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 122.1(5) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 116.8(5) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 H8 121.6 . . ?
C4 C9 C8 121.4(5) . . ?
C4 C9 C10 110.0(4) . . ?
C8 C9 C10 128.5(5) . . ?
F1 C10 F2 105.6(4) . . ?
F1 C10 N1 111.8(4) . . ?
F2 C10 N1 111.0(4) . . ?
F1 C10 C9 113.7(4) . . ?
F2 C10 C9 111.2(4) . . ?
N1 C10 C9 103.7(4) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C11 O2 C1 O1 -2.3(8) . . . . ?
C11 O2 C1 C2 -178.8(5) . . . . ?
C3 N1 C2 C1 54.9(6) . . . . ?
C10 N1 C2 C1 -146.0(5) . . . . ?
C3 N1 C2 Br2 169.2(3) . . . . ?
C10 N1 C2 Br2 -31.7(6) . . . . ?
C3 N1 C2 Br1 -69.9(5) . . . . ?
C10 N1 C2 Br1 89.2(5) . . . . ?
O1 C1 C2 N1 42.0(7) . . . . ?
O2 C1 C2 N1 -141.3(4) . . . . ?
O1 C1 C2 Br2 -78.2(6) . . . . ?
O2 C1 C2 Br2 98.6(4) . . . . ?
O1 C1 C2 Br1 165.0(4) . . . . ?
O2 C1 C2 Br1 -18.2(5) . . . . ?
C2 N1 C3 O3 -11.5(7) . . . . ?
C10 N1 C3 O3 -173.9(5) . . . . ?
C2 N1 C3 C4 168.0(4) . . . . ?
C10 N1 C3 C4 5.7(5) . . . . ?
O3 C3 C4 C9 175.7(5) . . . . ?
N1 C3 C4 C9 -3.8(5) . . . . ?
O3 C3 C4 C5 -3.8(9) . . . . ?
N1 C3 C4 C5 176.7(5) . . . . ?
C9 C4 C5 C6 1.3(8) . . . . ?
C3 C4 C5 C6 -179.3(5) . . . . ?
C4 C5 C6 C7 -0.3(8) . . . . ?
C5 C6 C7 C8 -0.1(8) . . . . ?
C6 C7 C8 C9 -0.4(8) . . . . ?
C5 C4 C9 C8 -1.9(8) . . . . ?
C3 C4 C9 C8 178.6(5) . . . . ?
C5 C4 C9 C10 -179.8(5) . . . . ?
C3 C4 C9 C10 0.7(5) . . . . ?
C7 C8 C9 C4 1.4(7) . . . . ?
C7 C8 C9 C10 178.9(5) . . . . ?
C3 N1 C10 F1 117.7(4) . . . . ?
C2 N1 C10 F1 -42.7(6) . . . . ?
C3 N1 C10 F2 -124.6(4) . . . . ?
C2 N1 C10 F2 75.0(6) . . . . ?
C3 N1 C10 C9 -5.2(5) . . . . ?
C2 N1 C10 C9 -165.5(4) . . . . ?
C4 C9 C10 F1 -118.9(5) . . . . ?
C8 C9 C10 F1 63.3(7) . . . . ?
C4 C9 C10 F2 122.0(4) . . . . ?
C8 C9 C10 F2 -55.8(7) . . . . ?
C4 C9 C10 N1 2.7(5) . . . . ?
C8 C9 C10 N1 -175.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        67.41
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.142