# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Min Shi'
_publ_contact_author_email       MSHI@MAIL.SIOC.AC.CN

_publ_section_title              
;
Palladium(II)-Catalyzed Ring Enlargement of
2-(Arylmethylene)cyclopropylcarbinols: Strong Substituent Electronic
Nature on the Reaction Pathway
;
loop_
_publ_author_name
'Min Shi.'
'Guo-Qiang Tian.'
'Zhi-Liang Yuan.'
'Zhi-Bin Zhu.'

# Attachment 'cd27511.cif'

data_cd27511
_database_code_depnum_ccdc_archive 'CCDC 665100'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 O2'
_chemical_formula_weight         190.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(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                   46.33(2)
_cell_length_b                   5.461(3)
_cell_length_c                   8.220(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.926(11)
_cell_angle_gamma                90.00
_cell_volume                     2077.2(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1775
_cell_measurement_theta_min      4.402
_cell_measurement_theta_max      45.960

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.75341
_exptl_absorpt_correction_T_max  1.00000
_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            10802
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4047
_reflns_number_gt                2035
_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^)+(0.0960P)^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_number_reflns         4047
_refine_ls_number_parameters     257
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_restrained_S_all      0.915
_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
O1 O 0.46605(4) 0.4611(4) 0.0944(2) 0.0755(6) Uani 1 1 d . . .
O2 O 0.26476(5) 0.2642(5) 0.2647(3) 0.0954(8) Uani 1 1 d D . .
H2 H 0.2549 0.3447 0.3253 0.143 Uiso 1 1 calc RD . .
O3 O 0.03375(4) 0.4944(4) 0.5846(3) 0.0768(6) Uani 1 1 d . . .
O4 O 0.23977(5) 0.4961(5) 0.5149(2) 0.0908(8) Uani 1 1 d D . .
H4 H 0.2398 0.3713 0.4595 0.136 Uiso 1 1 calc RD . .
C1 C 0.32736(7) 0.6822(6) 0.1881(4) 0.0819(10) Uani 1 1 d . . .
H1 H 0.3265 0.8230 0.1244 0.098 Uiso 1 1 calc R . .
C2 C 0.30519(6) 0.5363(6) 0.2787(4) 0.0729(9) Uani 1 1 d . . .
H2A H 0.2978 0.6266 0.3708 0.088 Uiso 1 1 calc R . .
C3 C 0.33077(6) 0.3724(5) 0.3285(3) 0.0650(8) Uani 1 1 d . . .
H3A H 0.3355 0.3725 0.4448 0.078 Uiso 1 1 calc R . .
H3B H 0.3289 0.2064 0.2875 0.078 Uiso 1 1 calc R . .
C4 C 0.34944(6) 0.5208(5) 0.2384(3) 0.0569(7) Uani 1 1 d . . .
C5 C 0.37997(6) 0.5047(5) 0.2062(3) 0.0536(7) Uani 1 1 d . . .
C6 C 0.39280(6) 0.6732(5) 0.1076(3) 0.0617(7) Uani 1 1 d . . .
H6 H 0.3818 0.8014 0.0632 0.074 Uiso 1 1 calc R . .
C7 C 0.42135(7) 0.6558(5) 0.0737(3) 0.0631(8) Uani 1 1 d . . .
H7 H 0.4295 0.7717 0.0071 0.076 Uiso 1 1 calc R . .
C8 C 0.43795(6) 0.4667(5) 0.1382(3) 0.0549(7) Uani 1 1 d . . .
C9 C 0.42592(6) 0.2974(5) 0.2382(3) 0.0604(7) Uani 1 1 d . . .
H9 H 0.4371 0.1704 0.2832 0.072 Uiso 1 1 calc R . .
C10 C 0.39719(6) 0.3182(5) 0.2709(3) 0.0592(7) Uani 1 1 d . . .
H10 H 0.3891 0.2032 0.3385 0.071 Uiso 1 1 calc R . .
C11 C 0.28152(7) 0.4247(7) 0.1714(4) 0.0831(10) Uani 1 1 d . . .
H11A H 0.2693 0.5528 0.1240 0.100 Uiso 1 1 calc R . .
H11B H 0.2898 0.3346 0.0835 0.100 Uiso 1 1 calc R . .
C12 C 0.48302(7) 0.2583(7) 0.1459(4) 0.0855(10) Uani 1 1 d . . .
H12A H 0.4839 0.2494 0.2627 0.128 Uiso 1 1 calc R . .
H12B H 0.5022 0.2766 0.1086 0.128 Uiso 1 1 calc R . .
H12C H 0.4745 0.1109 0.1014 0.128 Uiso 1 1 calc R . .
C13 C 0.16569(6) 0.6597(6) 0.3285(4) 0.0680(8) Uani 1 1 d . . .
H13 H 0.1611 0.7936 0.2623 0.082 Uiso 1 1 calc R . .
C14 C 0.19321(6) 0.5183(5) 0.3694(3) 0.0624(8) Uani 1 1 d . . .
H14 H 0.1997 0.4281 0.2748 0.075 Uiso 1 1 calc R . .
C15 C 0.17461(6) 0.3598(5) 0.4744(4) 0.0691(8) Uani 1 1 d . . .
H15A H 0.1727 0.1918 0.4370 0.083 Uiso 1 1 calc R . .
H15B H 0.1802 0.3661 0.5896 0.083 Uiso 1 1 calc R . .
C16 C 0.14997(6) 0.5115(5) 0.4286(3) 0.0539(7) Uani 1 1 d . . .
C17 C 0.12012(6) 0.5039(4) 0.4714(3) 0.0507(7) Uani 1 1 d . . .
C18 C 0.10997(6) 0.3228(5) 0.5711(3) 0.0592(7) Uani 1 1 d . . .
H18 H 0.1228 0.2042 0.6119 0.071 Uiso 1 1 calc R . .
C19 C 0.08164(6) 0.3115(5) 0.6123(3) 0.0599(7) Uani 1 1 d . . .
H19 H 0.0755 0.1868 0.6793 0.072 Uiso 1 1 calc R . .
C20 C 0.06242(6) 0.4867(5) 0.5533(3) 0.0553(7) Uani 1 1 d . . .
C21 C 0.07204(6) 0.6710(5) 0.4536(3) 0.0628(8) Uani 1 1 d . . .
H21 H 0.0592 0.7895 0.4130 0.075 Uiso 1 1 calc R . .
C22 C 0.10008(6) 0.6791(5) 0.4152(3) 0.0584(7) Uani 1 1 d . . .
H22 H 0.1062 0.8055 0.3494 0.070 Uiso 1 1 calc R . .
C23 C 0.21750(6) 0.6525(6) 0.4554(4) 0.0750(9) Uani 1 1 d . . .
H23A H 0.2254 0.7697 0.3810 0.090 Uiso 1 1 calc R . .
H23B H 0.2101 0.7432 0.5457 0.090 Uiso 1 1 calc R . .
C24 C 0.02251(7) 0.2958(6) 0.6705(4) 0.0844(10) Uani 1 1 d . . .
H24A H 0.0267 0.1458 0.6157 0.127 Uiso 1 1 calc R . .
H24B H 0.0020 0.3142 0.6754 0.127 Uiso 1 1 calc R . .
H24C H 0.0312 0.2922 0.7790 0.127 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
O1 0.0577(14) 0.0872(15) 0.0818(15) 0.0074(12) 0.0067(11) -0.0066(11)
O2 0.0704(15) 0.146(2) 0.0720(15) -0.0251(15) 0.0205(12) -0.0125(14)
O3 0.0574(15) 0.0814(15) 0.0913(16) 0.0130(12) 0.0001(11) 0.0032(10)
O4 0.0619(15) 0.144(2) 0.0649(14) -0.0065(13) -0.0125(10) 0.0295(13)
C1 0.071(2) 0.074(2) 0.100(3) 0.0148(19) -0.0025(19) 0.0105(17)
C2 0.053(2) 0.096(2) 0.070(2) -0.0184(17) -0.0006(15) 0.0134(16)
C3 0.063(2) 0.076(2) 0.0560(17) -0.0073(15) 0.0003(14) 0.0046(15)
C4 0.0590(19) 0.0612(17) 0.0501(16) -0.0098(13) -0.0019(13) 0.0021(14)
C5 0.0617(19) 0.0535(16) 0.0451(15) -0.0055(12) -0.0027(12) -0.0030(13)
C6 0.070(2) 0.0536(17) 0.0608(18) 0.0058(14) -0.0055(14) 0.0015(14)
C7 0.071(2) 0.0561(18) 0.0617(18) 0.0073(14) 0.0017(15) -0.0122(15)
C8 0.0532(18) 0.0583(17) 0.0529(16) -0.0038(13) -0.0007(13) -0.0095(13)
C9 0.0587(19) 0.0575(17) 0.0649(18) 0.0079(14) 0.0027(14) 0.0053(13)
C10 0.067(2) 0.0535(16) 0.0580(17) 0.0078(13) 0.0095(14) -0.0016(14)
C11 0.059(2) 0.124(3) 0.066(2) -0.008(2) 0.0012(16) 0.0013(19)
C12 0.059(2) 0.099(2) 0.099(3) 0.005(2) 0.0063(17) 0.0071(17)
C13 0.062(2) 0.076(2) 0.0647(18) 0.0145(16) -0.0103(14) -0.0073(15)
C14 0.0564(19) 0.078(2) 0.0516(16) -0.0058(15) -0.0041(13) 0.0014(14)
C15 0.073(2) 0.0633(19) 0.070(2) -0.0044(15) -0.0008(16) 0.0051(15)
C16 0.0578(19) 0.0539(16) 0.0486(16) -0.0030(13) -0.0118(13) -0.0001(13)
C17 0.0561(18) 0.0490(15) 0.0456(15) -0.0019(12) -0.0116(12) -0.0027(12)
C18 0.0598(19) 0.0543(17) 0.0621(18) 0.0060(14) -0.0127(14) 0.0089(13)
C19 0.063(2) 0.0582(17) 0.0575(17) 0.0096(13) -0.0071(14) -0.0026(14)
C20 0.0510(19) 0.0551(17) 0.0582(17) -0.0049(13) -0.0109(13) 0.0004(13)
C21 0.0597(19) 0.0545(17) 0.0727(19) 0.0047(15) -0.0123(15) 0.0077(13)
C22 0.064(2) 0.0513(16) 0.0583(17) 0.0086(13) -0.0102(14) 0.0000(13)
C23 0.057(2) 0.104(3) 0.0625(19) -0.0075(18) -0.0091(15) 0.0055(17)
C24 0.064(2) 0.103(3) 0.087(2) 0.013(2) 0.0101(17) -0.0042(18)

_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
O1 C8 1.369(3) . ?
O1 C12 1.411(4) . ?
O2 C11 1.421(4) . ?
O2 H2 0.8200 . ?
O3 C20 1.367(3) . ?
O3 C24 1.408(3) . ?
O4 C23 1.408(4) . ?
O4 H4 0.8200 . ?
C1 C4 1.397(4) . ?
C1 C2 1.524(4) . ?
C1 H1 0.9300 . ?
C2 C11 1.501(4) . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9800 . ?
C3 C4 1.421(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.455(4) . ?
C5 C6 1.381(4) . ?
C5 C10 1.384(4) . ?
C6 C7 1.369(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(4) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C16 1.387(4) . ?
C13 C14 1.514(4) . ?
C13 H13 0.9300 . ?
C14 C23 1.490(4) . ?
C14 C15 1.521(4) . ?
C14 H14 0.9800 . ?
C15 C16 1.444(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.445(4) . ?
C17 C18 1.382(3) . ?
C17 C22 1.396(4) . ?
C18 C19 1.373(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(4) . ?
C21 C22 1.353(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C8 O1 C12 117.5(2) . . ?
C11 O2 H2 109.5 . . ?
C20 O3 C24 117.3(2) . . ?
C23 O4 H4 109.5 . . ?
C4 C1 C2 91.5(3) . . ?
C4 C1 H1 134.2 . . ?
C2 C1 H1 134.2 . . ?
C11 C2 C1 114.6(3) . . ?
C11 C2 C3 117.0(3) . . ?
C1 C2 C3 84.5(2) . . ?
C11 C2 H2A 112.6 . . ?
C1 C2 H2A 112.6 . . ?
C3 C2 H2A 112.6 . . ?
C4 C3 C2 90.6(2) . . ?
C4 C3 H3A 113.5 . . ?
C2 C3 H3A 113.5 . . ?
C4 C3 H3B 113.5 . . ?
C2 C3 H3B 113.5 . . ?
H3A C3 H3B 110.8 . . ?
C1 C4 C3 93.3(3) . . ?
C1 C4 C5 133.5(3) . . ?
C3 C4 C5 133.2(2) . . ?
C6 C5 C10 117.3(3) . . ?
C6 C5 C4 121.2(2) . . ?
C10 C5 C4 121.4(2) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C9 124.2(3) . . ?
O1 C8 C7 115.8(2) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
O2 C11 C2 109.7(3) . . ?
O2 C11 H11A 109.7 . . ?
C2 C11 H11A 109.7 . . ?
O2 C11 H11B 109.7 . . ?
C2 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C13 C14 91.9(2) . . ?
C16 C13 H13 134.1 . . ?
C14 C13 H13 134.1 . . ?
C23 C14 C13 117.5(3) . . ?
C23 C14 C15 116.5(2) . . ?
C13 C14 C15 85.5(2) . . ?
C23 C14 H14 111.7 . . ?
C13 C14 H14 111.7 . . ?
C15 C14 H14 111.7 . . ?
C16 C15 C14 89.4(2) . . ?
C16 C15 H15A 113.8 . . ?
C14 C15 H15A 113.8 . . ?
C16 C15 H15B 113.8 . . ?
C14 C15 H15B 113.8 . . ?
H15A C15 H15B 111.0 . . ?
C13 C16 C15 93.3(2) . . ?
C13 C16 C17 134.4(2) . . ?
C15 C16 C17 132.3(2) . . ?
C18 C17 C22 116.5(3) . . ?
C18 C17 C16 121.6(2) . . ?
C22 C17 C16 121.9(2) . . ?
C19 C18 C17 122.5(2) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
O3 C20 C19 124.9(3) . . ?
O3 C20 C21 115.7(2) . . ?
C19 C20 C21 119.4(3) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 122.1(3) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
O4 C23 C14 112.9(3) . . ?
O4 C23 H23A 109.0 . . ?
C14 C23 H23A 109.0 . . ?
O4 C23 H23B 109.0 . . ?
C14 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C4 C1 C2 C11 -116.7(3) . . . . ?
C4 C1 C2 C3 0.5(2) . . . . ?
C11 C2 C3 C4 114.3(3) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C1 C4 C3 -0.6(2) . . . . ?
C2 C1 C4 C5 177.5(3) . . . . ?
C2 C3 C4 C1 0.6(2) . . . . ?
C2 C3 C4 C5 -177.5(3) . . . . ?
C1 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 C6 177.7(3) . . . . ?
C1 C4 C5 C10 -178.6(3) . . . . ?
C3 C4 C5 C10 -1.3(4) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C12 O1 C8 C9 4.9(4) . . . . ?
C12 O1 C8 C7 -174.4(3) . . . . ?
C6 C7 C8 O1 178.5(2) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
O1 C8 C9 C10 -178.5(2) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
C6 C5 C10 C9 -0.6(4) . . . . ?
C4 C5 C10 C9 178.4(2) . . . . ?
C1 C2 C11 O2 171.3(3) . . . . ?
C3 C2 C11 O2 74.7(3) . . . . ?
C16 C13 C14 C23 -116.6(3) . . . . ?
C16 C13 C14 C15 1.0(2) . . . . ?
C23 C14 C15 C16 117.6(3) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C14 C13 C16 C15 -1.1(2) . . . . ?
C14 C13 C16 C17 179.9(3) . . . . ?
C14 C15 C16 C13 1.1(2) . . . . ?
C14 C15 C16 C17 -179.9(3) . . . . ?
C13 C16 C17 C18 176.7(3) . . . . ?
C15 C16 C17 C18 -2.0(4) . . . . ?
C13 C16 C17 C22 -3.7(4) . . . . ?
C15 C16 C17 C22 177.6(3) . . . . ?
C22 C17 C18 C19 0.8(4) . . . . ?
C16 C17 C18 C19 -179.6(2) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C24 O3 C20 C19 -6.4(4) . . . . ?
C24 O3 C20 C21 173.2(3) . . . . ?
C18 C19 C20 O3 179.6(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
O3 C20 C21 C22 -179.9(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C17 0.9(4) . . . . ?
C18 C17 C22 C21 -1.1(4) . . . . ?
C16 C17 C22 C21 179.3(2) . . . . ?
C13 C14 C23 O4 168.6(2) . . . . ?
C15 C14 C23 O4 69.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.82 2.11 2.724(3) 132.1 .
O2 H2 O4 0.82 1.93 2.724(3) 163.3 .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.049


# Attachment 'cd2823.cif'

data_cd2823
_database_code_depnum_ccdc_archive 'CCDC 674227'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 Br2 O'
_chemical_formula_weight         318.01

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   6.0931(9)
_cell_length_b                   13.8466(19)
_cell_length_c                   26.311(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2219.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1562
_cell_measurement_theta_min      5.498
_cell_measurement_theta_max      40.351

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    7.267
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2448
_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            10890
_diffrn_reflns_av_R_equivalents  0.1919
_diffrn_reflns_av_sigmaI/netI    0.1273
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2117
_reflns_number_gt                1173
_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^)+(0.1311P)^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       0.0025(7)
_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   -10(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2117
_refine_ls_number_parameters     254
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.2064
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.910
_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 1.1144(5) 0.65727(19) -0.15836(9) 0.0793(10) Uani 1 1 d . . .
Br2 Br 1.0909(5) 0.35012(15) 0.10702(9) 0.0655(9) Uani 1 1 d . . .
Br3 Br 0.3735(5) 0.35584(19) 0.98152(9) 0.0751(10) Uani 1 1 d . . .
Br4 Br 0.4015(5) 0.64811(15) 0.71705(8) 0.0659(9) Uani 1 1 d . . .
O1 O 0.825(3) 0.6648(9) 0.0887(7) 0.070(5) Uani 1 1 d . . .
O2 O 0.681(3) 0.3295(10) 0.7314(7) 0.067(5) Uani 1 1 d . . .
C1 C 0.626(4) 0.6375(15) 0.1148(11) 0.063(7) Uani 1 1 d . . .
H1A H 0.4997 0.6689 0.0996 0.075 Uiso 1 1 calc R . .
H1B H 0.6335 0.6550 0.1504 0.075 Uiso 1 1 calc R . .
C2 C 0.611(3) 0.5326(12) 0.1089(8) 0.048(5) Uani 1 1 d . . .
H2 H 0.4997 0.4934 0.1214 0.057 Uiso 1 1 calc R . .
C3 C 0.791(3) 0.5021(12) 0.0817(6) 0.046(5) Uani 1 1 d . . .
C4 C 0.937(3) 0.5859(10) 0.0673(9) 0.049(6) Uani 1 1 d . . .
H4 H 1.0782 0.5786 0.0845 0.059 Uiso 1 1 calc R . .
C5 C 0.977(2) 0.5974(10) 0.0123(7) 0.033(4) Uani 1 1 d D . .
C6 C 1.173(3) 0.6335(16) -0.0045(7) 0.066(6) Uani 1 1 d D . .
H6 H 1.2815 0.6444 0.0198 0.079 Uiso 1 1 calc R . .
C7 C 1.222(3) 0.6542(14) -0.0526(7) 0.074(7) Uani 1 1 d D . .
H7 H 1.3571 0.6797 -0.0622 0.088 Uiso 1 1 calc R . .
C8 C 1.057(3) 0.6349(13) -0.0873(5) 0.043(5) Uani 1 1 d D . .
C9 C 0.848(3) 0.6046(19) -0.0731(8) 0.080(8) Uani 1 1 d D . .
H9 H 0.7367 0.5967 -0.0969 0.097 Uiso 1 1 calc R . .
C10 C 0.815(4) 0.587(2) -0.0223(7) 0.086(8) Uani 1 1 d D . .
H10 H 0.6766 0.5669 -0.0114 0.104 Uiso 1 1 calc R . .
C11 C 0.837(3) 0.4005(12) 0.0670(10) 0.064(7) Uani 1 1 d . . .
H11A H 0.8708 0.3974 0.0310 0.077 Uiso 1 1 calc R . .
H11B H 0.7088 0.3610 0.0733 0.077 Uiso 1 1 calc R . .
C12 C 0.871(4) 0.3655(18) 0.7074(13) 0.074(8) Uani 1 1 d . . .
H12A H 0.8678 0.3510 0.6714 0.089 Uiso 1 1 calc R . .
H12B H 1.0012 0.3366 0.7221 0.089 Uiso 1 1 calc R . .
C13 C 0.871(4) 0.4716(16) 0.7158(8) 0.065(7) Uani 1 1 d . . .
H13 H 0.9804 0.5132 0.7047 0.078 Uiso 1 1 calc R . .
C14 C 0.705(3) 0.4974(12) 0.7396(8) 0.049(5) Uani 1 1 d . . .
C15 C 0.552(4) 0.4109(14) 0.7528(8) 0.055(6) Uani 1 1 d . . .
H15 H 0.4117 0.4172 0.7350 0.066 Uiso 1 1 calc R . .
C16 C 0.515(3) 0.3927(13) 0.8075(8) 0.058(6) Uani 1 1 d D . .
C17 C 0.317(3) 0.4178(16) 0.8287(8) 0.075(7) Uani 1 1 d D . .
H17 H 0.2111 0.4442 0.8073 0.090 Uiso 1 1 calc R . .
C18 C 0.264(3) 0.4072(15) 0.8780(7) 0.068(6) Uani 1 1 d D . .
H18 H 0.1240 0.4222 0.8896 0.081 Uiso 1 1 calc R . .
C19 C 0.426(3) 0.3729(15) 0.9118(10) 0.081(9) Uani 1 1 d D . .
C20 C 0.626(4) 0.3508(18) 0.8919(8) 0.089(9) Uani 1 1 d D . .
H20 H 0.7304 0.3203 0.9123 0.107 Uiso 1 1 calc R . .
C21 C 0.678(4) 0.373(3) 0.8420(8) 0.119(12) Uani 1 1 d D . .
H21 H 0.8242 0.3742 0.8318 0.143 Uiso 1 1 calc R . .
C22 C 0.650(4) 0.5979(14) 0.7572(8) 0.061(6) Uani 1 1 d . . .
H22A H 0.7769 0.6396 0.7528 0.073 Uiso 1 1 calc R . .
H22B H 0.6119 0.5971 0.7929 0.073 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 0.075(2) 0.100(2) 0.063(2) 0.0149(14) 0.0060(15) -0.0072(13)
Br2 0.075(2) 0.0472(13) 0.074(2) 0.0005(11) -0.0123(17) 0.0149(10)
Br3 0.079(2) 0.0853(18) 0.0612(19) 0.0027(13) 0.0088(15) -0.0142(13)
Br4 0.073(2) 0.0557(15) 0.069(2) 0.0047(11) -0.0063(16) 0.0160(11)
O1 0.094(14) 0.040(8) 0.076(11) -0.006(7) 0.017(10) -0.004(8)
O2 0.085(13) 0.036(7) 0.081(11) -0.023(7) 0.024(10) -0.009(8)
C1 0.065(18) 0.063(13) 0.060(15) -0.001(11) 0.020(14) 0.018(12)
C2 0.045(13) 0.052(11) 0.046(12) 0.016(10) -0.005(10) 0.018(8)
C3 0.061(15) 0.040(11) 0.037(11) 0.008(9) -0.003(10) -0.009(10)
C4 0.048(13) 0.016(8) 0.084(16) -0.011(9) -0.006(11) 0.002(8)
C5 0.030(10) 0.016(8) 0.052(11) 0.008(7) 0.002(8) -0.002(7)
C6 0.028(9) 0.094(16) 0.074(14) 0.013(12) -0.003(9) -0.021(10)
C7 0.039(12) 0.088(16) 0.094(17) 0.023(13) 0.015(11) -0.018(11)
C8 0.040(12) 0.074(12) 0.014(7) 0.014(8) -0.001(7) -0.006(9)
C9 0.032(11) 0.14(2) 0.066(15) 0.029(15) -0.004(10) -0.025(13)
C10 0.079(18) 0.15(2) 0.034(12) -0.009(15) -0.006(12) 0.001(15)
C11 0.053(14) 0.029(10) 0.11(2) -0.005(11) 0.012(14) 0.000(9)
C12 0.044(15) 0.086(17) 0.09(2) 0.017(14) 0.007(15) -0.009(13)
C13 0.069(17) 0.073(15) 0.053(14) -0.009(12) 0.020(12) -0.035(12)
C14 0.031(11) 0.033(10) 0.082(15) 0.008(10) -0.011(11) -0.010(8)
C15 0.058(15) 0.060(13) 0.048(13) 0.019(10) -0.008(11) -0.027(11)
C16 0.042(14) 0.033(10) 0.100(18) -0.006(10) 0.009(13) -0.020(9)
C17 0.055(14) 0.087(16) 0.083(16) 0.014(13) -0.008(12) 0.003(12)
C18 0.046(13) 0.071(14) 0.085(16) 0.011(12) 0.015(11) -0.010(11)
C19 0.050(16) 0.039(10) 0.15(3) 0.011(14) 0.043(17) -0.003(10)
C20 0.058(17) 0.14(3) 0.069(15) 0.039(14) -0.022(12) 0.014(14)
C21 0.030(12) 0.26(4) 0.063(18) 0.03(2) 0.019(12) 0.014(17)
C22 0.065(16) 0.059(13) 0.059(14) -0.001(10) -0.034(12) -0.015(11)

_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 1.926(14) . ?
Br2 C11 2.00(2) . ?
Br3 C19 1.88(3) . ?
Br4 C22 1.97(2) . ?
O1 C4 1.40(2) . ?
O1 C1 1.45(3) . ?
O2 C12 1.41(3) . ?
O2 C15 1.49(3) . ?
C1 C2 1.46(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.38(2) . ?
C2 H2 0.9300 . ?
C3 C11 1.49(2) . ?
C3 C4 1.51(2) . ?
C4 C5 1.47(3) . ?
C4 H4 0.9800 . ?
C5 C10 1.35(3) . ?
C5 C6 1.370(16) . ?
C6 C7 1.333(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(16) . ?
C9 C10 1.376(17) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.49(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.24(2) . ?
C13 H13 0.9300 . ?
C14 C22 1.50(3) . ?
C14 C15 1.55(2) . ?
C15 C16 1.48(3) . ?
C15 H15 0.9800 . ?
C16 C21 1.374(18) . ?
C16 C17 1.375(17) . ?
C17 C18 1.345(17) . ?
C17 H17 0.9300 . ?
C18 C19 1.409(18) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(18) . ?
C20 C21 1.385(18) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 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
C4 O1 C1 113.2(15) . . ?
C12 O2 C15 109.6(17) . . ?
O1 C1 C2 105.1(16) . . ?
O1 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
O1 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C3 C2 C1 108.1(17) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
C2 C3 C11 125.2(17) . . ?
C2 C3 C4 111.3(16) . . ?
C11 C3 C4 123.5(17) . . ?
O1 C4 C5 112.9(15) . . ?
O1 C4 C3 102.3(18) . . ?
C5 C4 C3 115.3(15) . . ?
O1 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
C10 C5 C6 117.5(18) . . ?
C10 C5 C4 121.8(16) . . ?
C6 C5 C4 120.0(17) . . ?
C7 C6 C5 125.4(18) . . ?
C7 C6 H6 117.3 . . ?
C5 C6 H6 117.3 . . ?
C6 C7 C8 115.0(16) . . ?
C6 C7 H7 122.5 . . ?
C8 C7 H7 122.5 . . ?
C7 C8 C9 123.1(16) . . ?
C7 C8 Br1 118.4(12) . . ?
C9 C8 Br1 118.4(12) . . ?
C10 C9 C8 117(2) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C5 C10 C9 122(2) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C3 C11 Br2 109.8(14) . . ?
C3 C11 H11A 109.7 . . ?
Br2 C11 H11A 109.7 . . ?
C3 C11 H11B 109.7 . . ?
Br2 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O2 C12 C13 106(2) . . ?
O2 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O2 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C14 C13 C12 111.1(19) . . ?
C14 C13 H13 124.5 . . ?
C12 C13 H13 124.5 . . ?
C13 C14 C22 127(2) . . ?
C13 C14 C15 112.2(18) . . ?
C22 C14 C15 120.9(19) . . ?
C16 C15 O2 108.8(16) . . ?
C16 C15 C14 116.1(17) . . ?
O2 C15 C14 100.6(18) . . ?
C16 C15 H15 110.3 . . ?
O2 C15 H15 110.3 . . ?
C14 C15 H15 110.3 . . ?
C21 C16 C17 115(2) . . ?
C21 C16 C15 124.5(18) . . ?
C17 C16 C15 119.1(19) . . ?
C18 C17 C16 125(2) . . ?
C18 C17 H17 117.5 . . ?
C16 C17 H17 117.5 . . ?
C17 C18 C19 119(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 117(2) . . ?
C20 C19 Br3 119.9(18) . . ?
C18 C19 Br3 122.8(15) . . ?
C19 C20 C21 121(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C16 C21 C20 120(2) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C14 C22 Br4 109.3(12) . . ?
C14 C22 H22A 109.8 . . ?
Br4 C22 H22A 109.8 . . ?
C14 C22 H22B 109.8 . . ?
Br4 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?

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
C4 O1 C1 C2 0(3) . . . . ?
O1 C1 C2 C3 1(2) . . . . ?
C1 C2 C3 C11 -179.2(19) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C1 O1 C4 C5 124.5(19) . . . . ?
C1 O1 C4 C3 0(2) . . . . ?
C2 C3 C4 O1 0(2) . . . . ?
C11 C3 C4 O1 179.0(18) . . . . ?
C2 C3 C4 C5 -122.5(16) . . . . ?
C11 C3 C4 C5 56(3) . . . . ?
O1 C4 C5 C10 -75(3) . . . . ?
C3 C4 C5 C10 42(3) . . . . ?
O1 C4 C5 C6 95(2) . . . . ?
C3 C4 C5 C6 -147.5(18) . . . . ?
C10 C5 C6 C7 -4(3) . . . . ?
C4 C5 C6 C7 -174(2) . . . . ?
C5 C6 C7 C8 -1(3) . . . . ?
C6 C7 C8 C9 6(3) . . . . ?
C6 C7 C8 Br1 -177.5(16) . . . . ?
C7 C8 C9 C10 -5(4) . . . . ?
Br1 C8 C9 C10 178(2) . . . . ?
C6 C5 C10 C9 5(3) . . . . ?
C4 C5 C10 C9 175(2) . . . . ?
C8 C9 C10 C5 -1(4) . . . . ?
C2 C3 C11 Br2 -109.4(18) . . . . ?
C4 C3 C11 Br2 72(2) . . . . ?
C15 O2 C12 C13 3(3) . . . . ?
O2 C12 C13 C14 -2(3) . . . . ?
C12 C13 C14 C22 177(2) . . . . ?
C12 C13 C14 C15 0(3) . . . . ?
C12 O2 C15 C16 -125(2) . . . . ?
C12 O2 C15 C14 -3(2) . . . . ?
C13 C14 C15 C16 119(2) . . . . ?
C22 C14 C15 C16 -59(3) . . . . ?
C13 C14 C15 O2 2(2) . . . . ?
C22 C14 C15 O2 -175.9(17) . . . . ?
O2 C15 C16 C21 53(3) . . . . ?
C14 C15 C16 C21 -59(3) . . . . ?
O2 C15 C16 C17 -142.2(19) . . . . ?
C14 C15 C16 C17 105(2) . . . . ?
C21 C16 C17 C18 -13(3) . . . . ?
C15 C16 C17 C18 -178(2) . . . . ?
C16 C17 C18 C19 4(4) . . . . ?
C17 C18 C19 C20 -1(3) . . . . ?
C17 C18 C19 Br3 179.5(18) . . . . ?
C18 C19 C20 C21 8(4) . . . . ?
Br3 C19 C20 C21 -173(2) . . . . ?
C17 C16 C21 C20 19(4) . . . . ?
C15 C16 C21 C20 -176(2) . . . . ?
C19 C20 C21 C16 -18(5) . . . . ?
C13 C14 C22 Br4 110(2) . . . . ?
C15 C14 C22 Br4 -73(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.574
_refine_diff_density_min         -1.169
_refine_diff_density_rms         0.282