# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/467
 
data_ova10m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22.50 H19 Br O1.50' 
_chemical_formula_weight          393.29 
 
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            Monoclinic 
_symmetry_space_group_name_H-M    C2 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z' 
 
_cell_length_a                    24.604(8) 
_cell_length_b                    5.8049(18) 
_cell_length_c                    14.597(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  111.784(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      1935.9(10) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     35 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.349 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              804 
_exptl_absorpt_coefficient_mu     2.132 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5672 
_exptl_absorpt_correction_T_max   0.8151 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4993 
_diffrn_reflns_av_R_equivalents   0.1182 
_diffrn_reflns_av_sigmaI/netI     0.1227 
_diffrn_reflns_limit_h_min        -30 
_diffrn_reflns_limit_h_max        31 
_diffrn_reflns_limit_k_min        -3 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          1.50 
_diffrn_reflns_theta_max          28.37 
_reflns_number_total              2740 
_reflns_number_gt                 1469 
_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/[\s^2^(Fo^2^)+(0.1155P)^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     mixed 
_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(3) 
_refine_ls_number_reflns          2740 
_refine_ls_number_parameters      221 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.1212 
_refine_ls_R_factor_gt            0.0658 
_refine_ls_wR_factor_ref          0.2006 
_refine_ls_wR_factor_gt           0.1733 
_refine_ls_goodness_of_fit_ref    0.929 
_refine_ls_restrained_S_all       0.929 
_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 0.19651(5) -0.2491(2) 0.12032(6) 0.0727(4) Uani 1 1 d . . . 
O1 O 0.1379(2) 0.2568(15) -0.3310(4) 0.0493(13) Uani 1 1 d . . . 
C1 C 0.1359(3) 0.0548(15) -0.3111(7) 0.043(2) Uani 1 1 d . . . 
C2 C 0.1202(4) -0.1320(15) -0.3860(5) 0.0392(19) Uani 1 1 d . . . 
H2 H 0.0925 -0.2504 -0.3791 0.047 Uiso 1 1 calc R . . 
C3 C 0.1653(3) -0.2211(18) -0.4270(5) 0.0370(17) Uani 1 1 d . . . 
H3 H 0.1609 -0.3890 -0.4435 0.044 Uiso 1 1 calc R . . 
C4 C 0.1144(3) -0.0797(14) -0.4908(6) 0.0394(19) Uani 1 1 d . . . 
H4 H 0.1248 0.0822 -0.5012 0.047 Uiso 1 1 calc R . . 
C5 C 0.0681(3) -0.1832(13) -0.5784(6) 0.039(2) Uani 1 1 d . . . 
C6 C 0.0439(4) -0.3980(17) -0.5741(8) 0.051(2) Uani 1 1 d . . . 
H6 H 0.0575 -0.4827 -0.5142 0.061 Uiso 1 1 calc R . . 
C7 C 0.0004(4) -0.4892(19) -0.6562(8) 0.055(3) Uani 1 1 d . . . 
H7 H -0.0168 -0.6333 -0.6519 0.066 Uiso 1 1 calc R . . 
C8 C -0.0181(4) -0.370(2) -0.7454(11) 0.068(4) Uani 1 1 d . . . 
H8 H -0.0462 -0.4366 -0.8029 0.082 Uiso 1 1 calc R . . 
C9 C 0.0040(4) -0.155(2) -0.7501(8) 0.065(3) Uani 1 1 d . . . 
H9 H -0.0104 -0.0694 -0.8097 0.078 Uiso 1 1 calc R . . 
C10 C 0.0492(4) -0.0605(18) -0.6641(7) 0.053(2) Uani 1 1 d . . . 
H10 H 0.0657 0.0860 -0.6671 0.063 Uiso 1 1 calc R . . 
C11 C 0.2281(4) -0.1436(15) -0.3857(6) 0.0384(18) Uani 1 1 d . . . 
C12 C 0.2681(3) -0.2904(16) -0.3229(6) 0.044(2) Uani 1 1 d . . . 
H12 H 0.2553 -0.4310 -0.3043 0.053 Uiso 1 1 calc R . . 
C13 C 0.3277(3) -0.236(2) -0.2857(6) 0.051(2) Uani 1 1 d . . . 
H13 H 0.3558 -0.3432 -0.2461 0.061 Uiso 1 1 calc R . . 
C14 C 0.3451(4) -0.0201(18) -0.3079(6) 0.050(2) Uani 1 1 d . . . 
H14 H 0.3851 0.0247 -0.2791 0.060 Uiso 1 1 calc R . . 
C15 C 0.3051(4) 0.1258(17) -0.3705(6) 0.048(2) Uani 1 1 d . . . 
H15 H 0.3175 0.2669 -0.3893 0.057 Uiso 1 1 calc R . . 
C16 C 0.2458(4) 0.0687(14) -0.4072(6) 0.040(2) Uani 1 1 d . . . 
H16 H 0.2177 0.1755 -0.4469 0.048 Uiso 1 1 calc R . . 
C17 C 0.1492(3) -0.0226(14) -0.2057(6) 0.0392(19) Uani 1 1 d . . . 
C18 C 0.1733(3) -0.244(2) -0.1747(5) 0.0413(16) Uani 1 1 d . . . 
H18 H 0.1793 -0.3483 -0.2203 0.050 Uiso 1 1 calc R . . 
C19 C 0.1881(4) -0.3066(14) -0.0763(6) 0.046(2) Uani 1 1 d . . . 
H19 H 0.2049 -0.4530 -0.0535 0.055 Uiso 1 1 calc R . . 
C20 C 0.1780(4) -0.1555(17) -0.0135(7) 0.048(2) Uani 1 1 d . . . 
C21 C 0.1559(4) 0.0662(18) -0.0421(7) 0.053(2) Uani 1 1 d . . . 
H21 H 0.1510 0.1706 0.0044 0.063 Uiso 1 1 calc R . . 
C22 C 0.1414(4) 0.1292(15) -0.1392(6) 0.045(2) Uani 1 1 d . . . 
H22 H 0.1260 0.2784 -0.1604 0.054 Uiso 1 1 calc R . . 
O1S O 0.5000 0.785(6) 0.0000 0.199(9) Uiso 1 2 d SD . . 
H1S H 0.5281 0.7384 -0.0120 0.298 Uiso 0.50 1 d PR . . 
C1S C 0.5000 1.049(7) 0.0000 0.24(2) Uiso 1 2 d SD . . 
H1S1 H 0.4704 1.1038 -0.0597 0.358 Uiso 0.50 1 d PR . . 
H1S2 H 0.5376 1.1038 0.0040 0.358 Uiso 0.50 1 d PR . . 
H1S3 H 0.4920 1.1038 0.0557 0.358 Uiso 0.50 1 d PR . . 
 
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 0.1148(9) 0.0577(6) 0.0444(5) 0.0012(7) 0.0280(5) 0.0044(8) 
O1 0.071(3) 0.030(3) 0.049(3) 0.001(4) 0.025(3) -0.004(4) 
C1 0.038(4) 0.032(5) 0.057(6) -0.001(4) 0.015(4) -0.001(4) 
C2 0.055(5) 0.037(4) 0.034(4) -0.005(4) 0.025(4) -0.006(4) 
C3 0.043(4) 0.029(5) 0.040(4) 0.001(4) 0.017(3) 0.000(4) 
C4 0.049(5) 0.028(4) 0.044(5) -0.001(4) 0.021(4) -0.005(4) 
C5 0.042(4) 0.036(6) 0.039(4) -0.007(3) 0.014(4) 0.000(3) 
C6 0.053(5) 0.041(6) 0.062(6) -0.006(5) 0.026(5) 0.002(4) 
C7 0.054(6) 0.051(6) 0.065(7) -0.021(5) 0.026(5) -0.004(5) 
C8 0.038(5) 0.073(8) 0.095(9) -0.034(7) 0.026(6) -0.006(5) 
C9 0.054(6) 0.081(8) 0.048(6) 0.001(5) 0.005(5) 0.021(6) 
C10 0.050(5) 0.051(6) 0.056(6) 0.005(5) 0.019(5) 0.003(5) 
C11 0.045(4) 0.035(4) 0.043(5) -0.004(4) 0.025(4) 0.000(4) 
C12 0.048(5) 0.038(6) 0.050(5) 0.009(4) 0.022(4) 0.007(4) 
C13 0.047(4) 0.055(5) 0.055(5) 0.016(7) 0.025(4) 0.015(6) 
C14 0.041(5) 0.068(7) 0.042(5) -0.012(5) 0.017(4) -0.013(5) 
C15 0.057(5) 0.046(5) 0.044(5) 0.004(4) 0.023(4) 0.002(4) 
C16 0.046(5) 0.031(4) 0.041(5) 0.000(4) 0.015(4) 0.002(4) 
C17 0.040(4) 0.029(4) 0.048(5) -0.002(4) 0.016(4) -0.002(4) 
C18 0.051(4) 0.030(3) 0.043(4) -0.003(6) 0.018(3) 0.000(5) 
C19 0.061(5) 0.036(5) 0.042(5) -0.007(4) 0.019(4) -0.006(4) 
C20 0.044(5) 0.046(5) 0.049(5) -0.008(4) 0.012(4) -0.007(4) 
C21 0.068(6) 0.050(6) 0.049(6) -0.011(5) 0.032(5) -0.005(5) 
C22 0.062(5) 0.028(4) 0.051(6) -0.001(4) 0.027(4) 0.001(4) 
 
_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 C20 1.912(10) . ? 
O1 C1 1.214(12) . ? 
C1 C2 1.486(12) . ? 
C1 C17 1.517(13) . ? 
C2 C4 1.514(11) . ? 
C2 C3 1.532(11) . ? 
C3 C4 1.499(11) . ? 
C3 C11 1.504(11) . ? 
C4 C5 1.487(11) . ? 
C5 C10 1.362(12) . ? 
C5 C6 1.393(13) . ? 
C6 C7 1.382(13) . ? 
C7 C8 1.394(17) . ? 
C8 C9 1.370(17) . ? 
C9 C10 1.442(14) . ? 
C11 C12 1.366(11) . ? 
C11 C16 1.381(12) . ? 
C12 C13 1.397(12) . ? 
C13 C14 1.401(15) . ? 
C14 C15 1.363(13) . ? 
C15 C16 1.393(12) . ? 
C17 C22 1.377(12) . ? 
C17 C18 1.418(14) . ? 
C18 C19 1.393(11) . ? 
C19 C20 1.356(12) . ? 
C20 C21 1.400(14) . ? 
C21 C22 1.377(13) . ? 
O1S C1S 1.53(2) . ? 
 
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 
O1 C1 C2 123.5(8) . . ? 
O1 C1 C17 121.1(8) . . ? 
C2 C1 C17 115.4(7) . . ? 
C1 C2 C4 119.9(7) . . ? 
C1 C2 C3 120.4(7) . . ? 
C4 C2 C3 58.9(5) . . ? 
C4 C3 C11 125.7(8) . . ? 
C4 C3 C2 59.9(5) . . ? 
C11 C3 C2 121.8(7) . . ? 
C5 C4 C3 120.7(7) . . ? 
C5 C4 C2 122.9(7) . . ? 
C3 C4 C2 61.1(5) . . ? 
C10 C5 C6 120.2(8) . . ? 
C10 C5 C4 118.0(8) . . ? 
C6 C5 C4 121.8(8) . . ? 
C7 C6 C5 120.7(10) . . ? 
C6 C7 C8 119.9(10) . . ? 
C9 C8 C7 120.0(11) . . ? 
C8 C9 C10 119.7(12) . . ? 
C5 C10 C9 119.3(10) . . ? 
C12 C11 C16 119.9(8) . . ? 
C12 C11 C3 117.4(8) . . ? 
C16 C11 C3 122.7(8) . . ? 
C11 C12 C13 120.7(9) . . ? 
C12 C13 C14 118.7(9) . . ? 
C15 C14 C13 120.2(8) . . ? 
C14 C15 C16 120.2(9) . . ? 
C11 C16 C15 119.9(8) . . ? 
C22 C17 C18 120.4(8) . . ? 
C22 C17 C1 119.4(7) . . ? 
C18 C17 C1 120.0(7) . . ? 
C19 C18 C17 119.0(8) . . ? 
C20 C19 C18 119.0(9) . . ? 
C19 C20 C21 122.8(8) . . ? 
C19 C20 Br1 118.2(7) . . ? 
C21 C20 Br1 119.0(7) . . ? 
C22 C21 C20 118.3(9) . . ? 
C17 C22 C21 120.4(8) . . ? 
 
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 
O1 C1 C2 C4 8.8(12) . . . . ? 
C17 C1 C2 C4 -171.4(7) . . . . ? 
O1 C1 C2 C3 78.2(11) . . . . ? 
C17 C1 C2 C3 -102.1(9) . . . . ? 
C1 C2 C3 C4 -108.8(9) . . . . ? 
C1 C2 C3 C11 6.9(12) . . . . ? 
C4 C2 C3 C11 115.7(10) . . . . ? 
C11 C3 C4 C5 137.3(8) . . . . ? 
C2 C3 C4 C5 -113.2(8) . . . . ? 
C11 C3 C4 C2 -109.5(9) . . . . ? 
C1 C2 C4 C5 -140.6(8) . . . . ? 
C3 C2 C4 C5 109.8(9) . . . . ? 
C1 C2 C4 C3 109.6(8) . . . . ? 
C3 C4 C5 C10 -135.2(8) . . . . ? 
C2 C4 C5 C10 151.3(8) . . . . ? 
C3 C4 C5 C6 45.2(11) . . . . ? 
C2 C4 C5 C6 -28.3(12) . . . . ? 
C10 C5 C6 C7 -0.3(13) . . . . ? 
C4 C5 C6 C7 179.2(8) . . . . ? 
C5 C6 C7 C8 2.3(14) . . . . ? 
C6 C7 C8 C9 -4.2(15) . . . . ? 
C7 C8 C9 C10 3.9(15) . . . . ? 
C6 C5 C10 C9 0.1(13) . . . . ? 
C4 C5 C10 C9 -179.5(8) . . . . ? 
C8 C9 C10 C5 -1.9(15) . . . . ? 
C4 C3 C11 C12 175.3(8) . . . . ? 
C2 C3 C11 C12 101.6(10) . . . . ? 
C4 C3 C11 C16 -3.3(12) . . . . ? 
C2 C3 C11 C16 -76.9(10) . . . . ? 
C16 C11 C12 C13 -4.9(13) . . . . ? 
C3 C11 C12 C13 176.5(8) . . . . ? 
C11 C12 C13 C14 4.9(13) . . . . ? 
C12 C13 C14 C15 -4.8(13) . . . . ? 
C13 C14 C15 C16 4.8(14) . . . . ? 
C12 C11 C16 C15 4.7(12) . . . . ? 
C3 C11 C16 C15 -176.8(8) . . . . ? 
C14 C15 C16 C11 -4.7(13) . . . . ? 
O1 C1 C17 C22 25.3(12) . . . . ? 
C2 C1 C17 C22 -154.5(8) . . . . ? 
O1 C1 C17 C18 -150.4(8) . . . . ? 
C2 C1 C17 C18 29.8(11) . . . . ? 
C22 C17 C18 C19 1.0(12) . . . . ? 
C1 C17 C18 C19 176.6(7) . . . . ? 
C17 C18 C19 C20 1.1(12) . . . . ? 
C18 C19 C20 C21 -3.1(14) . . . . ? 
C18 C19 C20 Br1 178.1(6) . . . . ? 
C19 C20 C21 C22 2.8(14) . . . . ? 
Br1 C20 C21 C22 -178.4(7) . . . . ? 
C18 C17 C22 C21 -1.3(13) . . . . ? 
C1 C17 C22 C21 -176.9(8) . . . . ? 
C20 C21 C22 C17 -0.6(14) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.918 
_diffrn_reflns_theta_full              28.37 
_diffrn_measured_fraction_theta_full   0.918 
_refine_diff_density_max    1.025 
_refine_diff_density_min   -0.548 
_refine_diff_density_rms    0.138