# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       t-sawano@kuchem.kyoto-u.ac.jp
loop_
_publ_author_name
Nishimura
T.Sawano
K.Ou
T.Hayashi

data_compound6
_database_code_depnum_ccdc_archive 'CCDC 865189'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Br2 O'
_chemical_formula_weight         356.06
_chemical_absolute_configuration ad

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'
Br Br -0.6763 1.2805 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  P2ac2ab
_symmetry_Int_Tables_number      19

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

_cell_length_a                   6.96810(10)
_cell_length_b                   9.1696(2)
_cell_length_c                   20.5119(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1310.60(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11265
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      68.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    7.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1139
_exptl_absorpt_correction_T_max  0.2065
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK(J\(Ba
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       (J\(Bw
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12088
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         68.25
_reflns_number_total             2391
_reflns_number_gt                2293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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 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/[(J\(Bs^2^(Fo^2^)+(0.1000P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         2391
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_restrained_S_all      0.838
_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
C1 C 1.0179(8) 0.0960(5) 0.1115(2) 0.0216(11) Uani 1 1 d . . .
C2 C 0.8861(8) 0.0876(5) 0.1623(2) 0.0191(10) Uani 1 1 d . . .
C3 C 0.8248(6) 0.2259(5) 0.1853(2) 0.0194(9) Uani 1 1 d . . .
C4 C 0.8915(8) 0.3550(5) 0.1602(2) 0.0222(11) Uani 1 1 d . . .
C5 C 1.0317(8) 0.3615(5) 0.1110(2) 0.0196(10) Uani 1 1 d . . .
C6 C 1.0896(7) 0.2254(5) 0.0875(2) 0.0186(10) Uani 1 1 d . . .
C7 C 1.2402(8) 0.1810(5) 0.0376(2) 0.0216(11) Uani 1 1 d . . .
H7 H 1.2707 0.2562 0.0038 0.026 Uiso 1 1 calc R . .
C8 C 1.4149(8) 0.1219(5) 0.0761(2) 0.0238(11) Uani 1 1 d . . .
H8 H 1.5260 0.1043 0.0471 0.029 Uiso 1 1 calc R . .
H9 H 1.4533 0.1898 0.1113 0.029 Uiso 1 1 calc R . .
C9 C 1.3359(7) -0.0220(5) 0.1041(2) 0.0201(10) Uani 1 1 d . . .
H10 H 1.3314 -0.0172 0.1528 0.024 Uiso 1 1 calc R . .
C10 C 1.1268(7) -0.0200(5) 0.0753(2) 0.0194(9) Uani 1 1 d . . .
H11 H 1.0621 -0.1173 0.0736 0.023 Uiso 1 1 calc R . .
C11 C 0.8241(7) -0.0557(5) 0.1907(2) 0.0243(11) Uani 1 1 d . . .
H1 H 0.8868 -0.1355 0.1671 0.036 Uiso 1 1 calc R . .
H2 H 0.6845 -0.0655 0.1867 0.036 Uiso 1 1 calc R . .
H3 H 0.8604 -0.0598 0.2368 0.036 Uiso 1 1 calc R . .
C12 C 1.1189(10) 0.5017(5) 0.0874(3) 0.0310(13) Uani 1 1 d . . .
H4 H 1.2366 0.4805 0.0630 0.047 Uiso 1 1 calc R . .
H5 H 1.1496 0.5639 0.1248 0.047 Uiso 1 1 calc R . .
H6 H 1.0275 0.5522 0.0589 0.047 Uiso 1 1 calc R . .
C13 C 1.4427(8) -0.1543(6) 0.0827(2) 0.0248(11) Uani 1 1 d . . .
C14 C 1.5269(8) -0.2571(6) 0.0659(2) 0.0269(11) Uani 1 1 d . . .
H12 H 1.5957 -0.3412 0.0521 0.032 Uiso 1 1 calc R . .
Br1 Br 0.63880(8) 0.22326(6) 0.25362(2) 0.03173(19) Uani 1 1 d . . .
O1 O 1.1574(5) 0.0474(3) 0.01307(15) 0.0211(7) Uani 1 1 d . . .
Br2 Br 0.79306(9) 0.53502(5) 0.19166(3) 0.03168(19) 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
C1 0.032(3) 0.013(2) 0.020(3) 0.0000(19) -0.006(2) 0.0026(19)
C2 0.028(2) 0.012(2) 0.017(2) -0.0043(17) 0.000(2) -0.0029(19)
C3 0.020(2) 0.023(2) 0.015(2) -0.0039(19) 0.0046(18) 0.0001(19)
C4 0.035(3) 0.010(2) 0.021(2) -0.0081(18) -0.003(2) 0.009(2)
C5 0.032(3) 0.007(2) 0.020(2) -0.0004(18) -0.008(2) 0.0033(19)
C6 0.026(2) 0.014(2) 0.016(2) 0.0019(17) -0.0014(18) 0.001(2)
C7 0.031(3) 0.015(2) 0.018(2) -0.0019(17) -0.0006(19) 0.003(2)
C8 0.030(3) 0.017(3) 0.025(3) 0.000(2) 0.005(2) 0.002(2)
C9 0.029(3) 0.015(2) 0.016(2) -0.0040(18) -0.0008(19) 0.008(2)
C10 0.026(2) 0.013(2) 0.019(2) -0.0004(18) 0.0021(19) 0.000(2)
C11 0.024(3) 0.024(2) 0.025(3) 0.006(2) -0.002(2) -0.009(2)
C12 0.053(4) 0.012(3) 0.027(3) 0.0027(18) -0.003(3) 0.001(2)
C13 0.034(3) 0.025(3) 0.016(2) 0.0027(19) -0.005(2) 0.001(3)
C14 0.037(3) 0.021(3) 0.023(2) -0.0029(19) 0.000(2) 0.007(2)
Br1 0.0329(3) 0.0350(3) 0.0272(3) -0.0058(2) 0.0097(2) 0.0012(2)
O1 0.0352(19) 0.0131(16) 0.0151(15) -0.0020(12) 0.0012(14) 0.0014(16)
Br2 0.0471(4) 0.0189(3) 0.0291(3) -0.0051(2) -0.0013(2) 0.0144(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
C1 C6 1.378(7) . ?
C1 C2 1.391(7) . ?
C1 C10 1.503(7) . ?
C2 C3 1.420(6) . ?
C2 C11 1.501(6) . ?
C3 C4 1.372(7) . ?
C3 Br1 1.909(4) . ?
C4 C5 1.406(7) . ?
C4 Br2 1.901(4) . ?
C5 C6 1.398(7) . ?
C5 C12 1.502(7) . ?
C6 C7 1.522(7) . ?
C7 O1 1.445(6) . ?
C7 C8 1.550(7) . ?
C7 H7 1.0000 . ?
C8 C9 1.540(7) . ?
C8 H8 0.9900 . ?
C8 H9 0.9900 . ?
C9 C13 1.490(7) . ?
C9 C10 1.573(7) . ?
C9 H10 1.0000 . ?
C10 O1 1.435(5) . ?
C10 H11 1.0000 . ?
C11 H1 0.9800 . ?
C11 H2 0.9800 . ?
C11 H3 0.9800 . ?
C12 H4 0.9800 . ?
C12 H5 0.9800 . ?
C12 H6 0.9800 . ?
C13 C14 1.163(8) . ?
C14 H12 0.9500 . ?

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
C6 C1 C2 123.7(5) . . ?
C6 C1 C10 104.5(4) . . ?
C2 C1 C10 131.6(4) . . ?
C1 C2 C3 113.5(4) . . ?
C1 C2 C11 122.0(4) . . ?
C3 C2 C11 124.5(4) . . ?
C4 C3 C2 122.9(4) . . ?
C4 C3 Br1 121.1(3) . . ?
C2 C3 Br1 115.9(3) . . ?
C3 C4 C5 122.8(4) . . ?
C3 C4 Br2 119.9(4) . . ?
C5 C4 Br2 117.2(4) . . ?
C6 C5 C4 114.2(4) . . ?
C6 C5 C12 122.5(5) . . ?
C4 C5 C12 123.3(4) . . ?
C1 C6 C5 122.8(4) . . ?
C1 C6 C7 105.1(4) . . ?
C5 C6 C7 132.0(4) . . ?
O1 C7 C6 100.7(4) . . ?
O1 C7 C8 101.2(4) . . ?
C6 C7 C8 106.9(4) . . ?
O1 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
C8 C7 H7 115.4 . . ?
C9 C8 C7 102.1(4) . . ?
C9 C8 H8 111.4 . . ?
C7 C8 H8 111.4 . . ?
C9 C8 H9 111.4 . . ?
C7 C8 H9 111.4 . . ?
H8 C8 H9 109.2 . . ?
C13 C9 C8 114.1(4) . . ?
C13 C9 C10 111.2(4) . . ?
C8 C9 C10 100.5(4) . . ?
C13 C9 H10 110.2 . . ?
C8 C9 H10 110.2 . . ?
C10 C9 H10 110.2 . . ?
O1 C10 C1 102.1(4) . . ?
O1 C10 C9 101.6(4) . . ?
C1 C10 C9 106.9(4) . . ?
O1 C10 H11 114.9 . . ?
C1 C10 H11 114.9 . . ?
C9 C10 H11 114.9 . . ?
C2 C11 H1 109.5 . . ?
C2 C11 H2 109.5 . . ?
H1 C11 H2 109.5 . . ?
C2 C11 H3 109.5 . . ?
H1 C11 H3 109.5 . . ?
H2 C11 H3 109.5 . . ?
C5 C12 H4 109.5 . . ?
C5 C12 H5 109.5 . . ?
H4 C12 H5 109.5 . . ?
C5 C12 H6 109.5 . . ?
H4 C12 H6 109.5 . . ?
H5 C12 H6 109.5 . . ?
C14 C13 C9 179.7(7) . . ?
C13 C14 H12 180.0 . . ?
C10 O1 C7 96.6(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
C6 C1 C2 C3 2.9(7) . . . . ?
C10 C1 C2 C3 176.3(5) . . . . ?
C6 C1 C2 C11 -174.8(5) . . . . ?
C10 C1 C2 C11 -1.3(9) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C11 C2 C3 C4 176.8(5) . . . . ?
C1 C2 C3 Br1 178.5(4) . . . . ?
C11 C2 C3 Br1 -4.0(6) . . . . ?
C2 C3 C4 C5 -2.4(8) . . . . ?
Br1 C3 C4 C5 178.5(4) . . . . ?
C2 C3 C4 Br2 177.4(4) . . . . ?
Br1 C3 C4 Br2 -1.8(6) . . . . ?
C3 C4 C5 C6 3.2(7) . . . . ?
Br2 C4 C5 C6 -176.5(4) . . . . ?
C3 C4 C5 C12 -174.2(5) . . . . ?
Br2 C4 C5 C12 6.1(7) . . . . ?
C2 C1 C6 C5 -2.0(8) . . . . ?
C10 C1 C6 C5 -176.9(5) . . . . ?
C2 C1 C6 C7 174.9(5) . . . . ?
C10 C1 C6 C7 -0.1(5) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C12 C5 C6 C1 176.3(5) . . . . ?
C4 C5 C6 C7 -177.1(5) . . . . ?
C12 C5 C6 C7 0.4(8) . . . . ?
C1 C6 C7 O1 32.6(5) . . . . ?
C5 C6 C7 O1 -151.0(5) . . . . ?
C1 C6 C7 C8 -72.7(5) . . . . ?
C5 C6 C7 C8 103.7(6) . . . . ?
O1 C7 C8 C9 -35.6(4) . . . . ?
C6 C7 C8 C9 69.4(4) . . . . ?
C7 C8 C9 C13 119.6(5) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C6 C1 C10 O1 -32.9(5) . . . . ?
C2 C1 C10 O1 152.7(5) . . . . ?
C6 C1 C10 C9 73.4(5) . . . . ?
C2 C1 C10 C9 -101.0(6) . . . . ?
C13 C9 C10 O1 -86.3(5) . . . . ?
C8 C9 C10 O1 34.8(4) . . . . ?
C13 C9 C10 C1 167.1(4) . . . . ?
C8 C9 C10 C1 -71.8(4) . . . . ?
C8 C9 C13 C14 28(83) . . . . ?
C10 C9 C13 C14 141(100) . . . . ?
C1 C10 O1 C7 52.3(4) . . . . ?
C9 C10 O1 C7 -58.1(4) . . . . ?
C6 C7 O1 C10 -51.5(4) . . . . ?
C8 C7 O1 C10 58.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.129