# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Jinxing Ye.'

_publ_contact_author_name        'Jinxing Ye'
_publ_contact_author_email       yejx@ecust.edu.cn

_publ_section_title              
;
Multifunctional Catalytic Asymmetric Vinylogous
Michael Reaction of \^I+-, \^I^2^-Unsaturated Ketones with \^I^3^-Butenolide
;

# Attachment 'cd20181.cif.txt'

data_cd20181
_database_code_depnum_ccdc_archive 'CCDC 774478'
#TrackingRef 'cd20181.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Br O3'
_chemical_formula_weight         309.15

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'
O O 0.0106 0.0060 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.5631(11)
_cell_length_b                   7.7659(12)
_cell_length_c                   27.286(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1390.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2128
_cell_measurement_theta_min      5.454
_cell_measurement_theta_max      45.581

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    2.953
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8391
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3168
_reflns_number_gt                1826
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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^)+(0.0429P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0309(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.036(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_restrained_S_all      0.847
_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 0.93450(9) 1.09931(6) -0.069873(16) 0.0830(2) Uani 1 1 d . . .
O1 O 0.8262(5) 0.5554(4) 0.21425(11) 0.0726(9) Uani 1 1 d . . .
O2 O 1.4229(4) 1.1606(3) 0.16193(10) 0.0618(7) Uani 1 1 d . . .
O3 O 1.2042(3) 0.9439(3) 0.16963(9) 0.0447(6) Uani 1 1 d . . .
C1 C 0.8985(5) 0.7999(5) 0.13980(13) 0.0449(9) Uani 1 1 d . . .
H1 H 0.9828 0.6957 0.1402 0.054 Uiso 1 1 calc R . .
C2 C 0.6833(6) 0.7466(5) 0.15521(14) 0.0503(10) Uani 1 1 d . . .
H2A H 0.6088 0.8490 0.1649 0.060 Uiso 1 1 calc R . .
H2B H 0.6143 0.6978 0.1270 0.060 Uiso 1 1 calc R . .
C3 C 0.6748(7) 0.6181(5) 0.19664(13) 0.0524(10) Uani 1 1 d . . .
C4 C 0.4654(6) 0.5714(6) 0.21405(16) 0.0745(13) Uani 1 1 d . . .
H4A H 0.4753 0.4849 0.2391 0.112 Uiso 1 1 calc R . .
H4B H 0.3872 0.5275 0.1871 0.112 Uiso 1 1 calc R . .
H4C H 0.3997 0.6718 0.2271 0.112 Uiso 1 1 calc R . .
C5 C 0.9068(6) 0.8721(4) 0.08823(12) 0.0447(9) Uani 1 1 d . . .
C6 C 1.0710(6) 0.8385(5) 0.05820(13) 0.0581(11) Uani 1 1 d . . .
H6 H 1.1769 0.7697 0.0696 0.070 Uiso 1 1 calc R . .
C7 C 1.0802(7) 0.9061(6) 0.01110(15) 0.0701(11) Uani 1 1 d . . .
H7 H 1.1911 0.8827 -0.0090 0.084 Uiso 1 1 calc R . .
C8 C 0.9260(8) 1.0062(5) -0.00508(13) 0.0610(10) Uani 1 1 d . . .
C9 C 0.7600(7) 1.0403(5) 0.02339(16) 0.0643(12) Uani 1 1 d . . .
H9 H 0.6525 1.1054 0.0111 0.077 Uiso 1 1 calc R . .
C10 C 0.7536(6) 0.9778(5) 0.06991(15) 0.0611(11) Uani 1 1 d . . .
H10 H 0.6442 1.0064 0.0900 0.073 Uiso 1 1 calc R . .
C11 C 0.9883(4) 0.9238(5) 0.17745(12) 0.0406(9) Uani 1 1 d . . .
H11 H 0.9670 0.8754 0.2102 0.049 Uiso 1 1 calc R . .
C12 C 0.9101(5) 1.1036(5) 0.17708(12) 0.0485(9) Uani 1 1 d . . .
H12 H 0.7741 1.1352 0.1805 0.058 Uiso 1 1 calc R . .
C13 C 1.0608(6) 1.2092(5) 0.17127(14) 0.0519(10) Uani 1 1 d . . .
H13 H 1.0490 1.3285 0.1700 0.062 Uiso 1 1 calc R . .
C14 C 1.2505(6) 1.1150(5) 0.16693(12) 0.0447(9) Uani 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
Br1 0.1412(5) 0.0652(3) 0.0424(2) 0.0023(2) 0.0073(3) -0.0116(3)
O1 0.078(2) 0.070(2) 0.0697(19) 0.0174(17) -0.0012(17) 0.0179(17)
O2 0.0293(14) 0.0801(19) 0.0759(19) 0.0066(14) -0.0019(14) -0.0003(15)
O3 0.0311(13) 0.0514(18) 0.0515(15) 0.0020(12) -0.0049(11) 0.0112(12)
C1 0.045(2) 0.044(2) 0.046(2) -0.0036(17) 0.0025(18) 0.0063(19)
C2 0.058(2) 0.041(2) 0.051(2) -0.0027(19) -0.0104(19) -0.0015(19)
C3 0.072(3) 0.040(2) 0.045(2) -0.010(2) -0.002(2) 0.002(2)
C4 0.083(3) 0.071(3) 0.070(3) 0.009(3) 0.005(2) -0.022(3)
C5 0.052(2) 0.042(2) 0.0401(18) -0.0061(16) 0.0017(18) 0.004(2)
C6 0.061(3) 0.063(3) 0.050(3) 0.0018(18) 0.000(2) 0.018(2)
C7 0.074(3) 0.081(3) 0.056(3) -0.011(3) 0.021(2) 0.002(3)
C8 0.092(3) 0.051(2) 0.041(2) -0.0053(18) 0.003(3) -0.007(3)
C9 0.080(3) 0.059(3) 0.053(3) 0.005(2) -0.006(2) 0.021(2)
C10 0.071(3) 0.070(3) 0.043(2) 0.004(2) 0.012(2) 0.025(2)
C11 0.033(2) 0.051(2) 0.0378(18) 0.0012(18) -0.0010(14) 0.0066(16)
C12 0.0344(19) 0.061(2) 0.050(2) -0.011(2) 0.0025(17) 0.007(2)
C13 0.043(2) 0.044(2) 0.069(3) -0.0053(19) -0.008(2) 0.009(2)
C14 0.039(2) 0.056(3) 0.0394(19) 0.000(2) -0.0012(16) 0.006(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 C8 1.911(4) . ?
O1 C3 1.207(5) . ?
O2 C14 1.194(4) . ?
O3 C14 1.365(4) . ?
O3 C11 1.441(4) . ?
C1 C5 1.516(5) . ?
C1 C11 1.526(5) . ?
C1 C2 1.531(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.509(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.498(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.379(5) . ?
C5 C10 1.391(5) . ?
C6 C7 1.390(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.350(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(6) . ?
C9 C10 1.359(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.487(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.295(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.448(5) . ?
C13 H13 0.9300 . ?

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
C14 O3 C11 109.4(3) . . ?
C5 C1 C11 112.2(3) . . ?
C5 C1 C2 112.8(3) . . ?
C11 C1 C2 110.0(3) . . ?
C5 C1 H1 107.2 . . ?
C11 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
C3 C2 C1 114.7(3) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
O1 C3 C4 122.1(4) . . ?
O1 C3 C2 122.3(4) . . ?
C4 C3 C2 115.6(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 117.6(3) . . ?
C6 C5 C1 120.6(3) . . ?
C10 C5 C1 121.7(3) . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 Br1 119.9(3) . . ?
C9 C8 Br1 118.5(3) . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C5 121.6(4) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
O3 C11 C12 103.7(3) . . ?
O3 C11 C1 110.4(3) . . ?
C12 C11 C1 117.0(3) . . ?
O3 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C1 C11 H11 108.5 . . ?
C13 C12 C11 109.4(3) . . ?
C13 C12 H12 125.3 . . ?
C11 C12 H12 125.3 . . ?
C12 C13 C14 110.3(3) . . ?
C12 C13 H13 124.9 . . ?
C14 C13 H13 124.9 . . ?
O2 C14 O3 120.4(3) . . ?
O2 C14 C13 132.4(4) . . ?
O3 C14 C13 107.2(3) . . ?

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
C5 C1 C2 C3 158.6(3) . . . . ?
C11 C1 C2 C3 -75.3(4) . . . . ?
C1 C2 C3 O1 -4.0(5) . . . . ?
C1 C2 C3 C4 176.9(3) . . . . ?
C11 C1 C5 C6 91.8(4) . . . . ?
C2 C1 C5 C6 -143.3(3) . . . . ?
C11 C1 C5 C10 -86.4(4) . . . . ?
C2 C1 C5 C10 38.5(5) . . . . ?
C10 C5 C6 C7 -1.0(5) . . . . ?
C1 C5 C6 C7 -179.3(4) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
C6 C7 C8 C9 -1.1(6) . . . . ?
C6 C7 C8 Br1 -179.6(3) . . . . ?
C7 C8 C9 C10 2.8(6) . . . . ?
Br1 C8 C9 C10 -178.7(3) . . . . ?
C8 C9 C10 C5 -3.6(6) . . . . ?
C6 C5 C10 C9 2.7(6) . . . . ?
C1 C5 C10 C9 -179.0(4) . . . . ?
C14 O3 C11 C12 2.2(4) . . . . ?
C14 O3 C11 C1 128.3(3) . . . . ?
C5 C1 C11 O3 -66.6(4) . . . . ?
C2 C1 C11 O3 166.9(3) . . . . ?
C5 C1 C11 C12 51.6(4) . . . . ?
C2 C1 C11 C12 -74.9(4) . . . . ?
O3 C11 C12 C13 -1.5(4) . . . . ?
C1 C11 C12 C13 -123.3(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C11 O3 C14 O2 177.9(3) . . . . ?
C11 O3 C14 C13 -2.1(4) . . . . ?
C12 C13 C14 O2 -178.8(4) . . . . ?
C12 C13 C14 O3 1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.058