# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/480 data_global _publ_contact_author ; Toupet Loic G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; _publ_contact_author_email 'loic.toupet@univ-rennes1.fr' _publ_contact_author_fax '(33) 2 99 28 67 17' _publ_contact_author_phone '(33) 2 99 28 60 65' _publ_requested_journal 'Organometallics ' _publ_requested_coeditor_name ? _publ_contact_letter ; ; data_compound_13(cis) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 Br O2' _chemical_formula_weight 339.26 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.698(2) _cell_length_b 9.275(4) _cell_length_c 14.006(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.880(10) _cell_angle_gamma 90.00 _cell_volume 1608.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.556 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 3351 _diffrn_reflns_av_R_equivalents 0.1102 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3221 _reflns_number_gt 2414 _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^)+(0.0836P)^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 SHELXL _refine_ls_extinction_coef 0.052(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3221 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.87649(2) 0.17360(4) 0.82970(2) 0.05087(19) Uani 1 1 d . . . O1 O 0.65045(17) 0.0664(2) 0.84605(15) 0.0412(5) Uani 1 1 d . . . O5 O 0.64280(16) 0.3023(2) 0.78504(15) 0.0348(5) Uani 1 1 d . . . C2 C 0.5686(3) 0.0957(4) 0.8983(3) 0.0482(8) Uani 1 1 d . . . H2A H 0.5810 0.0370 0.9570 0.058 Uiso 1 1 calc R . . H2B H 0.4988 0.0694 0.8580 0.058 Uiso 1 1 calc R . . C3 C 0.5667(3) 0.2543(4) 0.9267(2) 0.0448(8) Uani 1 1 d . . . C4 C 0.5572(3) 0.3403(3) 0.8325(3) 0.0429(8) Uani 1 1 d . . . H4A H 0.4879 0.3208 0.7888 0.051 Uiso 1 1 calc R . . H4B H 0.5607 0.4426 0.8474 0.051 Uiso 1 1 calc R . . C6 C 0.6452(2) 0.1543(3) 0.7617(2) 0.0335(6) Uani 1 1 d . . . C7 C 0.7489(2) 0.1256(3) 0.7278(2) 0.0343(6) Uani 1 1 d . . . H7 H 0.7517 0.0223 0.7140 0.041 Uiso 1 1 calc R . . C8 C 0.7533(2) 0.2064(3) 0.6349(2) 0.0381(7) Uani 1 1 d . . . H8A H 0.8203 0.1838 0.6157 0.046 Uiso 1 1 calc R . . H8B H 0.7519 0.3093 0.6468 0.046 Uiso 1 1 calc R . . C9 C 0.6570(2) 0.1648(3) 0.5519(2) 0.0395(7) Uani 1 1 d . . . H9 H 0.6619 0.0610 0.5403 0.047 Uiso 1 1 calc R . . C10 C 0.5520(2) 0.1915(4) 0.5846(2) 0.0477(8) Uani 1 1 d . . . H10A H 0.5440 0.2940 0.5950 0.057 Uiso 1 1 calc R . . H10B H 0.4914 0.1606 0.5335 0.057 Uiso 1 1 calc R . . C11 C 0.5503(3) 0.1107(4) 0.6786(2) 0.0443(7) Uani 1 1 d . . . H11A H 0.5536 0.0079 0.6670 0.053 Uiso 1 1 calc R . . H11B H 0.4830 0.1308 0.6979 0.053 Uiso 1 1 calc R . . C12 C 0.6624(2) 0.2416(4) 0.4581(2) 0.0404(7) Uani 1 1 d . . . C13 C 0.6653(3) 0.3909(4) 0.4515(2) 0.0526(9) Uani 1 1 d . . . H13 H 0.6641 0.4470 0.5063 0.063 Uiso 1 1 calc R . . C14 C 0.6700(3) 0.4565(5) 0.3642(3) 0.0609(10) Uani 1 1 d . . . H14 H 0.6717 0.5566 0.3609 0.073 Uiso 1 1 calc R . . C15 C 0.6722(3) 0.3773(6) 0.2824(3) 0.0656(11) Uani 1 1 d . . . H15 H 0.6751 0.4228 0.2239 0.079 Uiso 1 1 calc R . . C16 C 0.6699(3) 0.2300(5) 0.2878(3) 0.0646(11) Uani 1 1 d . . . H16 H 0.6710 0.1755 0.2323 0.077 Uiso 1 1 calc R . . C17 C 0.6659(3) 0.1609(4) 0.3743(2) 0.0505(9) Uani 1 1 d . . . H17 H 0.6654 0.0607 0.3769 0.061 Uiso 1 1 calc R . . C19 C 0.4674(3) 0.2818(4) 0.9690(4) 0.0687(12) Uani 1 1 d . . . H19A H 0.4035 0.2548 0.9217 0.082 Uiso 1 1 calc R . . H19B H 0.4639 0.3823 0.9844 0.082 Uiso 1 1 calc R . . H19C H 0.4726 0.2256 1.0274 0.082 Uiso 1 1 calc R . . C18 C 0.6697(3) 0.2945(4) 0.9996(3) 0.0600(10) Uani 1 1 d . . . H18A H 0.6671 0.3945 1.0167 0.072 Uiso 1 1 calc R . . H18B H 0.7306 0.2781 0.9709 0.072 Uiso 1 1 calc R . . H18C H 0.6766 0.2364 1.0574 0.072 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 0.0365(2) 0.0679(3) 0.0467(2) 0.00427(16) 0.00600(13) 0.00178(15) O1 0.0518(13) 0.0308(13) 0.0478(12) 0.0082(9) 0.0256(10) 0.0061(9) O5 0.0375(10) 0.0279(12) 0.0442(11) 0.0015(8) 0.0198(9) 0.0006(8) C2 0.056(2) 0.040(2) 0.059(2) 0.0102(16) 0.0350(16) 0.0036(15) C3 0.0505(18) 0.040(2) 0.0531(19) 0.0052(15) 0.0306(15) 0.0042(15) C4 0.0420(16) 0.0344(19) 0.0588(19) 0.0034(14) 0.0254(15) 0.0076(13) C6 0.0368(15) 0.0258(18) 0.0409(15) 0.0038(12) 0.0156(12) -0.0004(11) C7 0.0324(14) 0.0337(16) 0.0383(15) -0.0021(12) 0.0109(11) 0.0004(12) C8 0.0341(14) 0.0420(19) 0.0408(16) 0.0004(13) 0.0140(12) 0.0001(12) C9 0.0433(16) 0.0390(19) 0.0373(15) -0.0039(13) 0.0115(12) -0.0034(13) C10 0.0363(16) 0.059(2) 0.0476(18) -0.0009(15) 0.0093(13) -0.0048(14) C11 0.0393(16) 0.046(2) 0.0512(18) -0.0067(15) 0.0187(13) -0.0114(15) C12 0.0385(15) 0.046(2) 0.0370(15) -0.0049(14) 0.0085(12) -0.0062(14) C13 0.066(2) 0.052(2) 0.0391(17) -0.0045(16) 0.0091(15) -0.0045(18) C14 0.073(2) 0.057(2) 0.051(2) 0.0089(18) 0.0099(17) -0.0087(19) C15 0.069(3) 0.088(3) 0.0410(19) 0.0109(19) 0.0140(17) -0.004(2) C16 0.073(3) 0.085(3) 0.0381(18) -0.0087(19) 0.0171(17) -0.002(2) C17 0.0494(19) 0.061(2) 0.0414(17) -0.0094(15) 0.0103(14) -0.0059(16) C19 0.074(3) 0.057(3) 0.093(3) 0.002(2) 0.059(2) 0.007(2) C18 0.071(2) 0.065(3) 0.0478(19) -0.0079(17) 0.0224(18) 0.0004(19) _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 C7 1.957(3) . ? O1 C2 1.424(3) . ? O1 C6 1.424(3) . ? O5 C6 1.413(4) . ? O5 C4 1.439(3) . ? C2 C3 1.525(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C18 1.515(5) . ? C3 C4 1.523(5) . ? C3 C19 1.529(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 C7 1.519(4) . ? C6 C11 1.531(4) . ? C7 C8 1.513(4) . ? C7 H7 0.9800 . ? C8 C9 1.537(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C12 1.509(4) . ? C9 C10 1.525(4) . ? C9 H9 0.9800 . ? C10 C11 1.519(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.390(6) . ? C12 C17 1.401(5) . ? C13 C14 1.379(5) . ? C13 H13 0.9300 . ? C14 C15 1.366(6) . ? C14 H14 0.9300 . ? C15 C16 1.369(7) . ? C15 H15 0.9300 . ? C16 C17 1.382(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C2 O1 C6 114.4(2) . . ? C6 O5 C4 113.7(2) . . ? O1 C2 C3 112.0(3) . . ? O1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? O1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C18 C3 C4 110.2(3) . . ? C18 C3 C19 111.1(3) . . ? C4 C3 C19 109.5(3) . . ? C18 C3 C2 110.6(3) . . ? C4 C3 C2 106.4(3) . . ? C19 C3 C2 108.9(3) . . ? O5 C4 C3 110.4(2) . . ? O5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? O5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O5 C6 O1 111.3(2) . . ? O5 C6 C7 107.9(2) . . ? O1 C6 C7 106.0(2) . . ? O5 C6 C11 112.2(3) . . ? O1 C6 C11 111.3(2) . . ? C7 C6 C11 107.8(2) . . ? C8 C7 C6 112.5(2) . . ? C8 C7 Br1 109.3(2) . . ? C6 C7 Br1 111.51(19) . . ? C8 C7 H7 107.8 . . ? C6 C7 H7 107.8 . . ? Br1 C7 H7 107.8 . . ? C7 C8 C9 110.5(2) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C12 C9 C10 113.4(3) . . ? C12 C9 C8 110.9(2) . . ? C10 C9 C8 109.4(2) . . ? C12 C9 H9 107.6 . . ? C10 C9 H9 107.6 . . ? C8 C9 H9 107.6 . . ? C11 C10 C9 111.3(3) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C6 111.6(3) . . ? C10 C11 H11A 109.3 . . ? C6 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C6 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C17 118.0(3) . . ? C13 C12 C9 122.4(3) . . ? C17 C12 C9 119.5(3) . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 121.3(4) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 119.1(4) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C15 C16 C17 121.1(4) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C12 120.1(4) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? C3 C19 H19A 109.5 . . ? C3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C3 C18 H18A 109.5 . . ? C3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C6 O1 C2 C3 -54.6(4) . . . . ? O1 C2 C3 C18 -65.7(4) . . . . ? O1 C2 C3 C4 53.9(4) . . . . ? O1 C2 C3 C19 171.9(3) . . . . ? C6 O5 C4 C3 58.3(4) . . . . ? C18 C3 C4 O5 64.7(4) . . . . ? C19 C3 C4 O5 -172.8(3) . . . . ? C2 C3 C4 O5 -55.2(3) . . . . ? C4 O5 C6 O1 -55.1(3) . . . . ? C4 O5 C6 C7 -170.9(2) . . . . ? C4 O5 C6 C11 70.4(3) . . . . ? C2 O1 C6 O5 53.1(3) . . . . ? C2 O1 C6 C7 170.1(3) . . . . ? C2 O1 C6 C11 -72.9(3) . . . . ? O5 C6 C7 C8 -63.5(3) . . . . ? O1 C6 C7 C8 177.2(2) . . . . ? C11 C6 C7 C8 58.0(3) . . . . ? O5 C6 C7 Br1 59.8(3) . . . . ? O1 C6 C7 Br1 -59.5(3) . . . . ? C11 C6 C7 Br1 -178.8(2) . . . . ? C6 C7 C8 C9 -58.5(3) . . . . ? Br1 C7 C8 C9 177.0(2) . . . . ? C7 C8 C9 C12 -178.4(3) . . . . ? C7 C8 C9 C10 55.7(3) . . . . ? C12 C9 C10 C11 179.4(3) . . . . ? C8 C9 C10 C11 -56.1(4) . . . . ? C9 C10 C11 C6 58.4(4) . . . . ? O5 C6 C11 C10 61.3(3) . . . . ? O1 C6 C11 C10 -173.2(2) . . . . ? C7 C6 C11 C10 -57.3(4) . . . . ? C10 C9 C12 C13 65.8(4) . . . . ? C8 C9 C12 C13 -57.8(4) . . . . ? C10 C9 C12 C17 -114.9(3) . . . . ? C8 C9 C12 C17 121.5(3) . . . . ? C17 C12 C13 C14 0.8(5) . . . . ? C9 C12 C13 C14 -179.9(3) . . . . ? C12 C13 C14 C15 -0.1(6) . . . . ? C13 C14 C15 C16 -0.2(6) . . . . ? C14 C15 C16 C17 -0.2(6) . . . . ? C15 C16 C17 C12 1.0(6) . . . . ? C13 C12 C17 C16 -1.2(5) . . . . ? C9 C12 C17 C16 179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.731 _refine_diff_density_min -1.009 _refine_diff_density_rms 0.109 #===END # 1. SUBMISSION DETAILS COMPOUND 3apf6 data_compound_15 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H21 Br O2' _chemical_formula_weight 277.20 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' '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 P21/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 12.232(2) _cell_length_b 9.1020(10) _cell_length_c 12.322(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.32(3) _cell_angle_gamma 90.00 _cell_volume 1316.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 3.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 2862 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 26.96 _reflns_number_total 2742 _reflns_number_gt 1783 _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^)+(0.0491P)^2^+1.0049P] 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 SHELXL _refine_ls_extinction_coef 0.0071(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2742 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.002 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.76417(4) 0.79861(5) 0.11750(5) 0.0901(3) Uani 1 1 d . . . O1 O 0.64201(17) 0.5048(2) 0.11165(18) 0.0474(5) Uani 1 1 d . . . O5 O 0.80197(17) 0.3550(2) 0.17392(19) 0.0440(5) Uani 1 1 d . . . C2 C 0.5692(3) 0.3939(4) 0.1360(3) 0.0467(8) Uani 1 1 d . . . C3 C 0.6145(3) 0.2408(4) 0.1261(3) 0.0463(8) Uani 1 1 d . . . C4 C 0.7364(3) 0.2382(4) 0.2016(3) 0.0479(8) Uani 1 1 d . . . C6 C 0.7556(2) 0.4967(3) 0.1808(3) 0.0395(7) Uani 1 1 d . . . C7 C 0.8282(3) 0.5966(4) 0.1264(3) 0.0541(9) Uani 1 1 d . . . C8 C 0.9511(3) 0.6033(5) 0.2028(4) 0.0639(11) Uani 1 1 d . . . C9 C 0.9624(4) 0.6385(5) 0.3244(4) 0.0703(12) Uani 1 1 d . . . C10 C 0.8910(3) 0.5383(5) 0.3736(4) 0.0629(10) Uani 1 1 d . . . C11 C 0.7672(3) 0.5391(4) 0.3027(3) 0.0473(8) Uani 1 1 d . . . C12 C 0.8206(4) 0.5527(5) 0.0006(3) 0.0686(11) Uani 1 1 d . . . H12A H 0.8514 0.4559 -0.0007 0.047(9) Uiso 1 1 calc R . . H12B H 0.8634 0.6216 -0.0301 0.105(16) Uiso 1 1 calc R . . H12C H 0.7424 0.5540 -0.0440 0.067(12) Uiso 1 1 calc R . . C13 C 0.6106(4) 0.2080(5) 0.0034(3) 0.0758(13) Uani 1 1 d . . . H13A H 0.6320 0.1076 -0.0029 0.085(14) Uiso 1 1 calc R . . H13B H 0.6625 0.2718 -0.0195 0.104(17) Uiso 1 1 calc R . . H13C H 0.5347 0.2240 -0.0443 0.101(17) Uiso 1 1 calc R . . C14 C 0.5438(3) 0.1291(4) 0.1689(4) 0.0671(11) Uani 1 1 d . . . H14A H 0.5688 0.0317 0.1580 0.085(14) Uiso 1 1 calc R . . H14B H 0.4650 0.1399 0.1279 0.087(14) Uiso 1 1 calc R . . H14C H 0.5531 0.1453 0.2480 0.110(18) Uiso 1 1 calc R . . H2A H 0.558(3) 0.403(4) 0.213(3) 0.045 Uiso 1 1 d . . . H2B H 0.500(3) 0.407(4) 0.082(3) 0.045 Uiso 1 1 d . . . H4A H 0.772(3) 0.158(4) 0.196(3) 0.048 Uiso 1 1 d . . . H4B H 0.737(3) 0.239(4) 0.283(3) 0.048 Uiso 1 1 d . . . H8A H 0.985(3) 0.670(4) 0.172(3) 0.059 Uiso 1 1 d . . . H8B H 0.984(3) 0.515(4) 0.197(3) 0.059 Uiso 1 1 d . . . H9A H 0.944(3) 0.728(4) 0.328(3) 0.053 Uiso 1 1 d . . . H9B H 1.040(3) 0.628(4) 0.364(3) 0.053 Uiso 1 1 d . . . H10A H 0.896(3) 0.566(4) 0.446(3) 0.055 Uiso 1 1 d . . . H10B H 0.920(3) 0.441(4) 0.377(3) 0.055 Uiso 1 1 d . . . H11A H 0.734(2) 0.637(4) 0.304(2) 0.039 Uiso 1 1 d . . . H11B H 0.723(3) 0.475(4) 0.335(2) 0.039 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 Br1 0.0914(4) 0.0454(3) 0.1358(5) 0.0243(2) 0.0356(3) 0.0034(2) O1 0.0384(11) 0.0427(12) 0.0554(13) 0.0079(10) 0.0039(10) 0.0001(9) O5 0.0390(11) 0.0337(11) 0.0632(14) -0.0019(10) 0.0209(10) 0.0007(9) C2 0.0320(15) 0.0508(19) 0.054(2) -0.0017(16) 0.0065(15) -0.0023(14) C3 0.0488(18) 0.0421(17) 0.0488(19) -0.0081(14) 0.0148(15) -0.0117(14) C4 0.0480(19) 0.0328(16) 0.065(2) 0.0036(15) 0.0189(17) 0.0014(14) C6 0.0360(15) 0.0359(16) 0.0467(17) 0.0002(14) 0.0117(13) 0.0014(12) C7 0.059(2) 0.0365(18) 0.073(2) 0.0063(17) 0.0274(18) -0.0036(16) C8 0.047(2) 0.056(2) 0.097(3) 0.001(2) 0.033(2) -0.0117(18) C9 0.045(2) 0.072(3) 0.089(3) -0.017(2) 0.010(2) -0.015(2) C10 0.049(2) 0.077(3) 0.057(2) -0.013(2) 0.0064(18) -0.0091(19) C11 0.0411(17) 0.0476(19) 0.055(2) -0.0077(16) 0.0170(15) -0.0054(15) C12 0.083(3) 0.067(3) 0.068(3) 0.003(2) 0.042(2) -0.019(2) C13 0.089(3) 0.082(3) 0.062(3) -0.027(2) 0.029(2) -0.024(3) C14 0.062(2) 0.057(2) 0.087(3) -0.006(2) 0.030(2) -0.0212(19) _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 C7 1.990(3) . ? O1 C6 1.413(3) . ? O1 C2 1.432(4) . ? O5 C6 1.421(4) . ? O5 C4 1.430(4) . ? C2 C3 1.517(5) . ? C2 H2A 1.00(3) . ? C2 H2B 0.92(3) . ? C3 C4 1.520(5) . ? C3 C14 1.523(5) . ? C3 C13 1.528(5) . ? C4 H4A 0.86(3) . ? C4 H4B 1.01(3) . ? C6 C11 1.519(5) . ? C6 C7 1.549(4) . ? C7 C8 1.534(5) . ? C7 C12 1.578(5) . ? C8 C9 1.500(6) . ? C8 H8A 0.88(4) . ? C8 H8B 0.91(4) . ? C9 C10 1.503(6) . ? C9 H9A 0.85(4) . ? C9 H9B 0.95(4) . ? C10 C11 1.521(5) . ? C10 H10A 0.91(3) . ? C10 H10B 0.95(4) . ? C11 H11A 0.98(3) . ? C11 H11B 0.95(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 C6 O1 C2 113.7(2) . . ? C6 O5 C4 113.6(2) . . ? O1 C2 C3 111.6(3) . . ? O1 C2 H2A 113.5(18) . . ? C3 C2 H2A 107.8(19) . . ? O1 C2 H2B 105(2) . . ? C3 C2 H2B 110(2) . . ? H2A C2 H2B 109(3) . . ? C2 C3 C4 106.4(3) . . ? C2 C3 C14 109.3(3) . . ? C4 C3 C14 109.4(3) . . ? C2 C3 C13 110.4(3) . . ? C4 C3 C13 110.8(3) . . ? C14 C3 C13 110.5(3) . . ? O5 C4 C3 111.2(3) . . ? O5 C4 H4A 106(2) . . ? C3 C4 H4A 113(2) . . ? O5 C4 H4B 112(2) . . ? C3 C4 H4B 110.3(19) . . ? H4A C4 H4B 103(3) . . ? O1 C6 O5 110.6(2) . . ? O1 C6 C11 112.7(2) . . ? O5 C6 C11 111.2(3) . . ? O1 C6 C7 107.2(2) . . ? O5 C6 C7 102.7(2) . . ? C11 C6 C7 111.9(3) . . ? C8 C7 C6 109.9(3) . . ? C8 C7 C12 112.9(3) . . ? C6 C7 C12 113.2(3) . . ? C8 C7 Br1 107.5(3) . . ? C6 C7 Br1 107.5(2) . . ? C12 C7 Br1 105.4(2) . . ? C9 C8 C7 114.9(3) . . ? C9 C8 H8A 111(2) . . ? C7 C8 H8A 106(2) . . ? C9 C8 H8B 110(2) . . ? C7 C8 H8B 107(2) . . ? H8A C8 H8B 108(3) . . ? C8 C9 C10 111.9(3) . . ? C8 C9 H9A 108(3) . . ? C10 C9 H9A 112(3) . . ? C8 C9 H9B 107(2) . . ? C10 C9 H9B 110(2) . . ? H9A C9 H9B 108(3) . . ? C9 C10 C11 111.3(4) . . ? C9 C10 H10A 110(2) . . ? C11 C10 H10A 110(2) . . ? C9 C10 H10B 109(2) . . ? C11 C10 H10B 109(2) . . ? H10A C10 H10B 107(3) . . ? C6 C11 C10 111.6(3) . . ? C6 C11 H11A 108.9(18) . . ? C10 C11 H11A 110.4(17) . . ? C6 C11 H11B 110.6(18) . . ? C10 C11 H11B 110.1(18) . . ? H11A C11 H11B 105(3) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C14 H14A 109.5 . . ? C3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C6 O1 C2 C3 -56.8(4) . . . . ? O1 C2 C3 C4 53.9(4) . . . . ? O1 C2 C3 C14 171.9(3) . . . . ? O1 C2 C3 C13 -66.4(4) . . . . ? C6 O5 C4 C3 57.3(4) . . . . ? C2 C3 C4 O5 -54.1(4) . . . . ? C14 C3 C4 O5 -172.0(3) . . . . ? C13 C3 C4 O5 65.9(4) . . . . ? C2 O1 C6 O5 55.4(3) . . . . ? C2 O1 C6 C11 -69.7(3) . . . . ? C2 O1 C6 C7 166.7(3) . . . . ? C4 O5 C6 O1 -55.8(3) . . . . ? C4 O5 C6 C11 70.2(3) . . . . ? C4 O5 C6 C7 -169.9(3) . . . . ? O1 C6 C7 C8 175.2(3) . . . . ? O5 C6 C7 C8 -68.2(3) . . . . ? C11 C6 C7 C8 51.2(4) . . . . ? O1 C6 C7 C12 -57.5(4) . . . . ? O5 C6 C7 C12 59.1(3) . . . . ? C11 C6 C7 C12 178.5(3) . . . . ? O1 C6 C7 Br1 58.5(3) . . . . ? O5 C6 C7 Br1 175.16(19) . . . . ? C11 C6 C7 Br1 -65.5(3) . . . . ? C6 C7 C8 C9 -50.2(5) . . . . ? C12 C7 C8 C9 -177.6(3) . . . . ? Br1 C7 C8 C9 66.5(4) . . . . ? C7 C8 C9 C10 52.5(5) . . . . ? C8 C9 C10 C11 -54.3(5) . . . . ? O1 C6 C11 C10 -176.6(3) . . . . ? O5 C6 C11 C10 58.5(4) . . . . ? C7 C6 C11 C10 -55.7(4) . . . . ? C9 C10 C11 C6 56.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.359 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.055 #===END