# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sir
#TrackingRef 'C16H17IO3_RKPeddinti.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 I O3'
_chemical_formula_sum            'C16 H17 I O3'
_chemical_formula_weight         384.20

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.541(2)
_cell_length_b                   10.227(3)
_cell_length_c                   10.666(3)
_cell_angle_alpha                79.510(5)
_cell_angle_beta                 74.206(5)
_cell_angle_gamma                70.686(5)
_cell_volume                     743.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    2.159
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS; Sheldrick, 96'

_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  'Brucker APEX-CCD Area Detector'
_diffrn_measurement_method       SMART
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7163
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2619
_reflns_number_gt                2514
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0762P)²+0.6145P] 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         2619
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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
I1 I 0.12377(5) 0.37239(3) 0.37517(3) 0.05187(18) Uani 1 1 d . . .
O1 O -0.1474(4) 0.1148(3) 0.3665(3) 0.0407(7) Uani 1 1 d . . .
O2 O 0.0060(4) -0.0542(3) 0.2236(3) 0.0388(7) Uani 1 1 d . . .
O3 O -0.2681(5) 0.1559(4) 0.1131(4) 0.0566(9) Uani 1 1 d . . .
C1 C -0.0320(6) 0.0835(4) 0.2436(4) 0.0334(9) Uani 1 1 d . . .
C2 C -0.1253(6) 0.1676(5) 0.1313(4) 0.0352(9) Uani 1 1 d . . .
C3 C -0.0156(6) 0.2641(4) 0.0481(4) 0.0348(9) Uani 1 1 d . . .
C4 C -0.0015(6) 0.3524(4) 0.1395(4) 0.0351(9) Uani 1 1 d . . .
C5 C 0.0811(6) 0.2803(4) 0.2334(4) 0.0333(8) Uani 1 1 d . . .
C6 C 0.1481(6) 0.1257(4) 0.2331(4) 0.0295(8) Uani 1 1 d . . .
C7 C 0.2881(6) 0.0924(5) 0.1011(4) 0.0347(9) Uani 1 1 d . . .
C8 C 0.1910(6) 0.1719(4) -0.0105(4) 0.0343(9) Uani 1 1 d . . .
C9 C 0.2979(6) 0.2617(4) -0.1083(4) 0.0329(8) Uani 1 1 d . . .
C10 C 0.3927(7) 0.3388(5) -0.0727(5) 0.0392(9) Uani 1 1 d . . .
C11 C 0.4750(8) 0.4284(5) -0.1648(5) 0.0472(11) Uani 1 1 d . . .
C12 C 0.4653(7) 0.4415(6) -0.2918(5) 0.0504(12) Uani 1 1 d . . .
C13 C 0.3753(8) 0.3626(7) -0.3280(5) 0.0531(13) Uani 1 1 d . . .
C14 C 0.2926(7) 0.2745(5) -0.2375(5) 0.0441(10) Uani 1 1 d . . .
C15 C -0.3249(8) 0.0836(8) 0.4028(6) 0.0633(16) Uani 1 1 d . . .
H15A H -0.3915 0.1102 0.4891 0.095 Uiso 1 1 calc R . .
H15B H -0.3009 -0.0145 0.4024 0.095 Uiso 1 1 calc R . .
H15C H -0.4027 0.1340 0.3417 0.095 Uiso 1 1 calc R . .
C16 C 0.1144(8) -0.1542(5) 0.3077(6) 0.0541(13) Uani 1 1 d . . .
H16A H 0.1340 -0.2462 0.2871 0.081 Uiso 1 1 calc R . .
H16B H 0.0451 -0.1448 0.3972 0.081 Uiso 1 1 calc R . .
H16C H 0.2372 -0.1389 0.2955 0.081 Uiso 1 1 calc R . .
H6 H 0.189(6) 0.085(5) 0.302(5) 0.027(11) Uiso 1 1 d . . .
H7B H 0.391(6) 0.124(4) 0.109(4) 0.020(11) Uiso 1 1 d . . .
H14 H 0.216(9) 0.236(7) -0.262(6) 0.062(18) Uiso 1 1 d . . .
H3 H -0.084(7) 0.325(6) -0.023(5) 0.045(13) Uiso 1 1 d . . .
H7A H 0.321(7) 0.011(6) 0.099(5) 0.032(12) Uiso 1 1 d . . .
H10 H 0.404(8) 0.330(6) 0.015(6) 0.047(14) Uiso 1 1 d . . .
H8 H 0.184(6) 0.121(5) -0.055(5) 0.025(11) Uiso 1 1 d . . .
H4 H -0.050(8) 0.452(6) 0.119(6) 0.049(15) Uiso 1 1 d . . .
H12 H 0.529(8) 0.506(6) -0.367(6) 0.055(16) Uiso 1 1 d . . .
H13 H 0.363(8) 0.370(6) -0.406(6) 0.045(14) Uiso 1 1 d . . .
H11 H 0.536(7) 0.475(5) -0.145(5) 0.034(12) Uiso 1 1 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
I1 0.0645(3) 0.0532(3) 0.0538(3) -0.01832(16) -0.01639(17) -0.02911(18)
O1 0.0371(16) 0.0445(17) 0.0436(17) -0.0098(13) -0.0029(13) -0.0185(13)
O2 0.0424(16) 0.0276(14) 0.0515(18) -0.0066(12) -0.0108(13) -0.0157(12)
O3 0.047(2) 0.070(2) 0.066(2) 0.0035(19) -0.0241(17) -0.0321(18)
C1 0.034(2) 0.030(2) 0.039(2) -0.0052(16) -0.0079(16) -0.0138(16)
C2 0.033(2) 0.039(2) 0.041(2) -0.0073(17) -0.0110(17) -0.0151(17)
C3 0.034(2) 0.035(2) 0.039(2) -0.0006(17) -0.0145(17) -0.0122(17)
C4 0.032(2) 0.028(2) 0.044(2) -0.0043(17) -0.0047(17) -0.0095(16)
C5 0.035(2) 0.031(2) 0.039(2) -0.0083(16) -0.0070(17) -0.0158(16)
C6 0.0301(19) 0.0277(19) 0.034(2) -0.0012(16) -0.0100(16) -0.0115(15)
C7 0.031(2) 0.029(2) 0.044(2) -0.0065(17) -0.0061(17) -0.0107(17)
C8 0.040(2) 0.031(2) 0.038(2) -0.0097(18) -0.0089(17) -0.0164(18)
C9 0.033(2) 0.033(2) 0.034(2) -0.0079(16) -0.0061(16) -0.0113(16)
C10 0.044(2) 0.043(2) 0.038(2) -0.0061(18) -0.0109(18) -0.0218(19)
C11 0.050(3) 0.043(3) 0.059(3) -0.002(2) -0.012(2) -0.028(2)
C12 0.048(3) 0.052(3) 0.047(3) 0.010(2) -0.007(2) -0.021(2)
C13 0.057(3) 0.070(4) 0.035(3) 0.004(2) -0.014(2) -0.024(3)
C14 0.046(3) 0.056(3) 0.040(2) -0.007(2) -0.0131(19) -0.023(2)
C15 0.042(3) 0.085(4) 0.064(4) -0.013(3) 0.006(2) -0.033(3)
C16 0.057(3) 0.032(2) 0.075(4) 0.002(2) -0.021(3) -0.016(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C5 2.064(4) . ?
O1 C1 1.388(5) . ?
O1 C15 1.414(6) . ?
O2 C1 1.385(5) . ?
O2 C16 1.425(6) . ?
O3 C2 1.190(5) . ?
C1 C6 1.527(5) . ?
C1 C2 1.534(6) . ?
C2 C3 1.506(6) . ?
C3 C4 1.490(6) . ?
C3 C8 1.556(6) . ?
C3 H3 1.03(5) . ?
C4 C5 1.305(6) . ?
C4 H4 0.97(6) . ?
C5 C6 1.493(6) . ?
C6 C7 1.529(6) . ?
C6 H6 0.86(5) . ?
C7 C8 1.532(6) . ?
C7 H7B 0.97(4) . ?
C7 H7A 0.79(6) . ?
C8 C9 1.505(6) . ?
C8 H8 0.78(6) . ?
C9 C14 1.371(6) . ?
C9 C10 1.381(6) . ?
C10 C11 1.380(6) . ?
C10 H10 0.94(6) . ?
C11 C12 1.356(8) . ?
C11 H11 0.84(6) . ?
C12 C13 1.371(9) . ?
C12 H12 1.06(6) . ?
C13 C14 1.363(7) . ?
C13 H13 0.85(6) . ?
C14 H14 0.91(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 O1 C15 117.2(4) . . ?
C1 O2 C16 115.1(4) . . ?
O2 C1 O1 112.7(3) . . ?
O2 C1 C6 114.0(3) . . ?
O1 C1 C6 105.4(3) . . ?
O2 C1 C2 104.3(4) . . ?
O1 C1 C2 113.1(3) . . ?
C6 C1 C2 107.3(3) . . ?
O3 C2 C3 124.7(4) . . ?
O3 C2 C1 122.9(4) . . ?
C3 C2 C1 112.4(3) . . ?
C4 C3 C2 106.0(4) . . ?
C4 C3 C8 108.6(3) . . ?
C2 C3 C8 107.1(3) . . ?
C4 C3 H3 110(3) . . ?
C2 C3 H3 112(3) . . ?
C8 C3 H3 113(3) . . ?
C5 C4 C3 113.2(4) . . ?
C5 C4 H4 131(4) . . ?
C3 C4 H4 116(4) . . ?
C4 C5 C6 116.8(4) . . ?
C4 C5 I1 122.6(3) . . ?
C6 C5 I1 120.7(3) . . ?
C5 C6 C1 105.7(3) . . ?
C5 C6 C7 107.3(3) . . ?
C1 C6 C7 109.7(4) . . ?
C5 C6 H6 111(3) . . ?
C1 C6 H6 105(3) . . ?
C7 C6 H6 117(3) . . ?
C6 C7 C8 109.9(3) . . ?
C6 C7 H7B 100(2) . . ?
C8 C7 H7B 114(2) . . ?
C6 C7 H7A 108(3) . . ?
C8 C7 H7A 113(4) . . ?
H7B C7 H7A 112(4) . . ?
C9 C8 C7 115.3(4) . . ?
C9 C8 C3 108.9(3) . . ?
C7 C8 C3 109.2(4) . . ?
C9 C8 H8 102(3) . . ?
C7 C8 H8 112(3) . . ?
C3 C8 H8 109(3) . . ?
C14 C9 C10 118.1(4) . . ?
C14 C9 C8 119.0(4) . . ?
C10 C9 C8 122.8(4) . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119(3) . . ?
C9 C10 H10 120(3) . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 118(3) . . ?
C10 C11 H11 121(3) . . ?
C11 C12 C13 119.0(5) . . ?
C11 C12 H12 124(3) . . ?
C13 C12 H12 117(3) . . ?
C14 C13 C12 120.8(5) . . ?
C14 C13 H13 117(4) . . ?
C12 C13 H13 122(4) . . ?
C13 C14 C9 121.0(5) . . ?
C13 C14 H14 118(4) . . ?
C9 C14 H14 120(4) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.683
_refine_diff_density_min         -1.612
_refine_diff_density_rms         0.153


_database_code_depnum_ccdc_archive 'CCDC 815225'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sir
#TrackingRef '- 14e_Br_SPh.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Br O3 S'
_chemical_formula_sum            'C16 H17 Br O3 S'
_chemical_formula_weight         369.27

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 2(1)/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                   10.6073(17)
_cell_length_b                   7.7726(13)
_cell_length_c                   21.494(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.150(6)
_cell_angle_gamma                90.00
_cell_volume                     1547.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    240
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS; Sheldrick, 96'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      240
_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  'Brucker APEX-CCD Area Detector'
_diffrn_measurement_method       SMART
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7467
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2717
_reflns_number_gt                2011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0306P)²+0.0000P] 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         2717
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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 0.24711(4) 0.57157(4) -0.41896(2) 0.05492(16) Uani 1 1 d . . .
S2 S 0.17438(11) 0.01821(12) -0.27692(5) 0.0476(3) Uani 1 1 d . . .
O1 O 0.4476(2) 0.2017(3) -0.45168(11) 0.0388(6) Uani 1 1 d . . .
O2 O 0.5447(2) 0.0200(3) -0.35233(11) 0.0391(6) Uani 1 1 d . . .
O3 O 0.2620(2) -0.0775(3) -0.48538(12) 0.0415(6) Uani 1 1 d . . .
C1 C 0.4287(3) 0.1254(4) -0.39786(17) 0.0333(8) Uani 1 1 d . . .
C2 C 0.2892(3) 0.0168(4) -0.43558(18) 0.0333(8) Uani 1 1 d . . .
C3 C 0.1919(3) 0.0450(4) -0.40337(17) 0.0337(8) Uani 1 1 d . . .
H3 H 0.1077 -0.0312 -0.4247 0.040 Uiso 1 1 calc R . .
C4 C 0.1491(4) 0.2308(4) -0.42210(18) 0.0376(8) Uani 1 1 d . . .
H4 H 0.0539 0.2675 -0.4487 0.045 Uiso 1 1 calc R . .
C5 C 0.2606(4) 0.3353(4) -0.39676(17) 0.0352(8) Uani 1 1 d . . .
C6 C 0.4064(3) 0.2558(4) -0.35023(17) 0.0336(8) Uani 1 1 d . . .
H6 H 0.4828 0.3430 -0.3315 0.040 Uiso 1 1 calc R . .
C7 C 0.3964(3) 0.1610(4) -0.28960(17) 0.0377(8) Uani 1 1 d . . .
H7A H 0.4894 0.1115 -0.2568 0.045 Uiso 1 1 calc R . .
H7B H 0.3699 0.2416 -0.2635 0.045 Uiso 1 1 calc R . .
C8 C 0.2820(3) 0.0178(4) -0.32179(17) 0.0352(8) Uani 1 1 d . . .
H8 H 0.3317 -0.0931 -0.3129 0.042 Uiso 1 1 calc R . .
C9 C 0.0773(3) -0.1790(4) -0.31040(18) 0.0356(8) Uani 1 1 d . . .
C10 C 0.1370(4) -0.3320(4) -0.27660(19) 0.0429(9) Uani 1 1 d . . .
H10 H 0.2266 -0.3321 -0.2355 0.051 Uiso 1 1 calc R . .
C11 C 0.0652(4) -0.4844(5) -0.3032(2) 0.0495(10) Uani 1 1 d . . .
H11 H 0.1061 -0.5874 -0.2801 0.059 Uiso 1 1 calc R . .
C12 C -0.0674(4) -0.4846(5) -0.3641(2) 0.0551(11) Uani 1 1 d . . .
H12 H -0.1157 -0.5877 -0.3827 0.066 Uiso 1 1 calc R . .
C13 C -0.1277(4) -0.3319(6) -0.3971(2) 0.0552(11) Uani 1 1 d . . .
H13 H -0.2177 -0.3319 -0.4379 0.066 Uiso 1 1 calc R . .
C14 C -0.0567(4) -0.1790(5) -0.3706(2) 0.0474(10) Uani 1 1 d . . .
H14 H -0.0989 -0.0759 -0.3931 0.057 Uiso 1 1 calc R . .
C15 C 0.5878(4) -0.1103(5) -0.3859(2) 0.0541(11) Uani 1 1 d . . .
H15A H 0.5204 -0.2041 -0.4008 0.081 Uiso 1 1 calc R . .
H15B H 0.6824 -0.1516 -0.3527 0.081 Uiso 1 1 calc R . .
H15C H 0.5892 -0.0622 -0.4267 0.081 Uiso 1 1 calc R . .
C16 C 0.5745(4) 0.3064(5) -0.4280(2) 0.0556(11) Uani 1 1 d . . .
H16A H 0.5899 0.3309 -0.4676 0.083 Uiso 1 1 calc R . .
H16B H 0.6566 0.2459 -0.3920 0.083 Uiso 1 1 calc R . .
H16C H 0.5619 0.4122 -0.4087 0.083 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 0.0722(3) 0.0294(2) 0.0628(3) 0.00394(19) 0.0327(2) 0.00471(19)
S2 0.0668(7) 0.0406(5) 0.0527(6) -0.0053(5) 0.0427(5) -0.0059(5)
O1 0.0406(14) 0.0461(14) 0.0315(14) 0.0026(11) 0.0191(11) -0.0060(11)
O2 0.0369(13) 0.0450(14) 0.0327(14) -0.0016(11) 0.0148(11) 0.0063(11)
O3 0.0482(14) 0.0375(14) 0.0383(15) -0.0045(12) 0.0206(12) -0.0008(11)
C1 0.034(2) 0.0338(18) 0.031(2) 0.0014(15) 0.0149(16) 0.0033(15)
C2 0.040(2) 0.0278(18) 0.0275(19) 0.0032(15) 0.0130(16) 0.0027(15)
C3 0.0309(18) 0.035(2) 0.035(2) -0.0030(15) 0.0155(16) -0.0063(15)
C4 0.035(2) 0.038(2) 0.040(2) -0.0009(17) 0.0183(16) 0.0052(17)
C5 0.050(2) 0.0261(18) 0.034(2) 0.0012(15) 0.0242(17) 0.0051(17)
C6 0.037(2) 0.0301(18) 0.033(2) -0.0028(15) 0.0165(16) -0.0049(15)
C7 0.045(2) 0.038(2) 0.031(2) -0.0025(16) 0.0198(16) -0.0004(17)
C8 0.043(2) 0.0301(18) 0.037(2) -0.0027(15) 0.0237(17) -0.0008(15)
C9 0.038(2) 0.040(2) 0.041(2) 0.0052(17) 0.0282(18) 0.0035(17)
C10 0.037(2) 0.049(2) 0.038(2) 0.0059(18) 0.0145(17) 0.0020(18)
C11 0.051(2) 0.042(2) 0.063(3) 0.007(2) 0.034(2) 0.0054(19)
C12 0.052(3) 0.057(3) 0.068(3) -0.018(2) 0.038(2) -0.018(2)
C13 0.032(2) 0.082(3) 0.048(3) -0.004(2) 0.0170(18) -0.008(2)
C14 0.038(2) 0.058(3) 0.052(3) 0.013(2) 0.027(2) 0.0103(19)
C15 0.047(2) 0.058(3) 0.057(3) 0.000(2) 0.025(2) 0.0162(19)
C16 0.056(3) 0.062(3) 0.057(3) 0.001(2) 0.034(2) -0.017(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.885(3) . ?
S2 C9 1.790(3) . ?
S2 C8 1.818(3) . ?
O1 C1 1.399(4) . ?
O1 C16 1.437(4) . ?
O2 C1 1.403(4) . ?
O2 C15 1.442(4) . ?
O3 C2 1.211(4) . ?
C1 C6 1.538(4) . ?
C1 C2 1.546(4) . ?
C2 C3 1.512(4) . ?
C3 C4 1.509(4) . ?
C3 C8 1.549(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.315(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.505(4) . ?
C6 C7 1.545(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.540(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C9 C10 1.377(4) . ?
C9 C14 1.379(5) . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C9 S2 C8 99.91(15) . . ?
C1 O1 C16 115.8(2) . . ?
C1 O2 C15 116.4(2) . . ?
O1 C1 O2 113.2(2) . . ?
O1 C1 C6 113.7(3) . . ?
O2 C1 C6 106.7(2) . . ?
O1 C1 C2 106.5(3) . . ?
O2 C1 C2 109.7(2) . . ?
C6 C1 C2 106.9(3) . . ?
O3 C2 C3 124.8(3) . . ?
O3 C2 C1 123.3(3) . . ?
C3 C2 C1 111.9(3) . . ?
C4 C3 C2 101.6(3) . . ?
C4 C3 C8 111.9(3) . . ?
C2 C3 C8 108.5(2) . . ?
C4 C3 H3 111.5 . . ?
C2 C3 H3 111.5 . . ?
C8 C3 H3 111.5 . . ?
C5 C4 C3 112.8(3) . . ?
C5 C4 H4 123.6 . . ?
C3 C4 H4 123.6 . . ?
C4 C5 C6 116.6(3) . . ?
C4 C5 Br1 123.7(3) . . ?
C6 C5 Br1 119.7(2) . . ?
C5 C6 C1 105.6(3) . . ?
C5 C6 C7 106.6(3) . . ?
C1 C6 C7 110.1(3) . . ?
C5 C6 H6 111.4 . . ?
C1 C6 H6 111.4 . . ?
C7 C6 H6 111.4 . . ?
C8 C7 C6 109.2(3) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 C3 109.0(3) . . ?
C7 C8 S2 108.8(2) . . ?
C3 C8 S2 113.6(2) . . ?
C7 C8 H8 108.4 . . ?
C3 C8 H8 108.4 . . ?
S2 C8 H8 108.4 . . ?
C10 C9 C14 119.6(3) . . ?
C10 C9 S2 120.0(3) . . ?
C14 C9 S2 120.4(3) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 119.7(3) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 900005'
