data_b6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 Br O5' _chemical_formula_weight 397.26 _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' 0.0033 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' 'Br' 'Br' -0.2901 2.4595 '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 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 6.843(3) _cell_length_b 15.583(7) _cell_length_c 17.024(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1815.3(13) _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 needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 2.288 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.109 _exptl_absorpt_correction_T_max 0.397 _exptl_absorpt_process_details 'psi scan' _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 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11835 _diffrn_reflns_av_R_equivalents 0.2893 _diffrn_reflns_av_sigmaI/netI 0.4238 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.51 _reflns_number_total 3191 _reflns_number_gt 928 _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^)+(0.0502P)^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 0.0022(8) _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 0.02(3) _refine_ls_number_reflns 3191 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2654 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 0.756 _refine_ls_restrained_S_all 0.756 _refine_ls_shift/su_max 0.100 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br 1.0665(3) 0.63913(9) 0.35201(9) 0.0950(7) Uani 1 1 d . . . C1 C 0.787(2) 0.1634(9) 0.3753(7) 0.060(4) Uani 1 1 d . . . C2 C 0.6448(16) 0.2393(9) 0.3677(8) 0.057(4) Uani 1 1 d . . . H2 H 0.655(16) 0.276(7) 0.414(6) 0.068 Uiso 1 1 calc . . . C3 C 0.4457(17) 0.1952(6) 0.3661(7) 0.045(3) Uani 1 1 d . . . C4 C 0.4773(18) 0.1048(9) 0.3988(7) 0.059(4) Uani 1 1 d . . . C5 C 0.6664(18) 0.2932(8) 0.2925(7) 0.044(4) Uani 1 1 d . . . H5 H 0.758(13) 0.262(6) 0.259(5) 0.053 Uiso 1 1 calc . . . C6 C 0.4662(18) 0.2876(8) 0.2526(8) 0.055(4) Uani 1 1 d . . . H6 H 0.382(15) 0.332(6) 0.276(5) 0.066 Uiso 1 1 calc . . . C7 C 0.3923(17) 0.2005(7) 0.2801(6) 0.048(3) Uani 1 1 d . . . H7A H 0.2519 0.1962 0.2732 0.057 Uiso 1 1 calc R . . H7B H 0.4545 0.1546 0.2507 0.057 Uiso 1 1 calc R . . C8 C 0.7569(18) 0.3798(8) 0.3069(7) 0.048(3) Uani 1 1 d . . . C9 C 0.9331(19) 0.3985(7) 0.2715(6) 0.052(3) Uani 1 1 d . . . H9 H 0.9904 0.3587 0.2380 0.063 Uiso 1 1 calc R . . C10 C 1.0261(19) 0.4764(9) 0.2855(7) 0.066(4) Uani 1 1 d . . . H10 H 1.1486 0.4869 0.2639 0.079 Uiso 1 1 calc R . . C11 C 0.938(2) 0.5373(7) 0.3309(8) 0.063(4) Uani 1 1 d . . . C12 C 0.753(2) 0.5227(7) 0.3601(8) 0.060(4) Uani 1 1 d . . . H12 H 0.6879 0.5660 0.3870 0.072 Uiso 1 1 calc R . . C13 C 0.6632(16) 0.4435(8) 0.3494(7) 0.051(3) Uani 1 1 d . . . H13 H 0.5404 0.4333 0.3708 0.062 Uiso 1 1 calc R . . C14 C 0.467(2) 0.1033(7) 0.4865(7) 0.085(5) Uani 1 1 d . . . H14A H 0.3332 0.0976 0.5027 0.127 Uiso 1 1 calc R . . H14B H 0.5198 0.1558 0.5071 0.127 Uiso 1 1 calc R . . H14C H 0.5412 0.0556 0.5061 0.127 Uiso 1 1 calc R . . C15 C 0.3664(16) 0.0319(7) 0.3656(8) 0.070(4) Uani 1 1 d . . . H15A H 0.3799 0.0317 0.3095 0.106 Uiso 1 1 calc R . . H15B H 0.2308 0.0376 0.3792 0.106 Uiso 1 1 calc R . . H15C H 0.4164 -0.0209 0.3866 0.106 Uiso 1 1 calc R . . C16 C 0.465(2) 0.2996(8) 0.1687(8) 0.055(4) Uani 1 1 d . . . C17 C 0.2716(18) 0.3360(9) 0.0590(6) 0.076(5) Uani 1 1 d . . . H17A H 0.2678 0.2785 0.0372 0.091 Uiso 1 1 calc R . . H17B H 0.3783 0.3672 0.0347 0.091 Uiso 1 1 calc R . . C18 C 0.083(2) 0.3807(9) 0.0453(7) 0.098(5) Uani 1 1 d . . . H18A H -0.0145 0.3575 0.0798 0.147 Uiso 1 1 calc R . . H18B H 0.0436 0.3726 -0.0082 0.147 Uiso 1 1 calc R . . H18C H 0.0990 0.4409 0.0556 0.147 Uiso 1 1 calc R . . O1 O 0.6886(11) 0.0901(5) 0.3829(5) 0.060(3) Uani 1 1 d . . . O2 O 0.9597(13) 0.1675(5) 0.3701(5) 0.081(3) Uani 1 1 d . . . O3 O 0.3089(11) 0.2431(5) 0.4126(5) 0.058(2) Uani 1 1 d . . . H3 H 0.1994 0.2387 0.3934 0.087 Uiso 1 1 calc R . . O4 O 0.2970(12) 0.3329(4) 0.1447(6) 0.063(2) Uani 1 1 d . . . O5 O 0.5956(16) 0.2813(6) 0.1260(5) 0.090(3) 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 Br 0.1161(13) 0.0716(9) 0.0972(11) 0.0142(10) -0.0329(11) -0.0423(10) C1 0.042(9) 0.081(12) 0.057(11) 0.025(8) -0.002(8) 0.002(9) C2 0.031(8) 0.065(10) 0.074(12) 0.007(8) 0.010(8) -0.020(7) C3 0.029(7) 0.047(8) 0.060(10) -0.011(7) 0.011(8) 0.003(7) C4 0.036(9) 0.088(11) 0.053(9) 0.019(8) 0.005(7) 0.014(7) C5 0.043(9) 0.064(10) 0.025(8) 0.001(7) 0.007(6) 0.002(7) C6 0.036(9) 0.049(9) 0.080(11) -0.007(8) -0.021(8) 0.003(7) C7 0.032(8) 0.066(9) 0.045(8) 0.001(7) 0.001(7) -0.001(7) C8 0.033(8) 0.046(9) 0.065(9) 0.021(7) -0.008(7) -0.001(7) C9 0.034(8) 0.065(9) 0.058(8) 0.018(6) -0.009(8) 0.000(8) C10 0.041(9) 0.075(10) 0.082(11) 0.024(8) -0.014(8) -0.031(9) C11 0.071(11) 0.042(8) 0.075(11) 0.011(7) -0.033(10) -0.046(9) C12 0.077(10) 0.040(8) 0.063(9) 0.003(8) -0.009(10) -0.005(8) C13 0.037(8) 0.071(9) 0.046(8) 0.006(9) 0.006(8) 0.006(7) C14 0.085(12) 0.065(9) 0.104(12) 0.032(8) 0.023(9) 0.000(9) C15 0.057(9) 0.053(8) 0.102(11) -0.018(8) -0.015(8) -0.032(7) C16 0.047(11) 0.078(10) 0.039(11) 0.010(7) -0.017(8) -0.007(9) C17 0.069(11) 0.130(14) 0.028(9) 0.019(8) -0.013(7) 0.010(11) C18 0.061(10) 0.117(13) 0.116(12) 0.023(9) -0.039(10) 0.028(11) O1 0.035(6) 0.046(5) 0.100(8) 0.013(5) -0.004(5) 0.001(5) O2 0.023(5) 0.095(7) 0.125(8) 0.014(6) -0.002(6) 0.011(5) O3 0.035(5) 0.064(6) 0.075(7) -0.010(5) 0.011(5) -0.003(5) O4 0.041(5) 0.084(6) 0.065(6) 0.006(6) -0.008(5) 0.018(4) O5 0.070(8) 0.118(9) 0.081(8) -0.001(6) 0.018(6) 0.029(7) _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 Br C11 1.849(11) . ? C1 O2 1.188(13) . ? C1 O1 1.332(14) . ? C1 C2 1.536(17) . ? C2 C3 1.526(14) . ? C2 C5 1.539(16) . ? C2 H2 0.97(10) . ? C3 O3 1.435(12) . ? C3 C7 1.512(14) . ? C3 C4 1.530(14) . ? C4 C15 1.479(14) . ? C4 O1 1.489(12) . ? C4 C14 1.494(14) . ? C5 C8 1.505(15) . ? C5 C6 1.531(14) . ? C5 H5 0.98(9) . ? C6 C16 1.441(15) . ? C6 C7 1.522(14) . ? C6 H6 0.98(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.380(15) . ? C8 C13 1.386(14) . ? C9 C10 1.390(14) . ? C9 H9 0.9300 . ? C10 C11 1.365(16) . ? C10 H10 0.9300 . ? C11 C12 1.379(18) . ? C12 C13 1.390(14) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O5 1.189(14) . ? C16 O4 1.323(14) . ? C17 O4 1.470(13) . ? C17 C18 1.483(16) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O3 H3 0.8200 . ? 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 O2 C1 O1 123.7(13) . . ? O2 C1 C2 125.7(13) . . ? O1 C1 C2 110.4(11) . . ? C3 C2 C1 102.7(10) . . ? C3 C2 C5 108.5(10) . . ? C1 C2 C5 115.4(10) . . ? C3 C2 H2 110(7) . . ? C1 C2 H2 110(6) . . ? C5 C2 H2 110(6) . . ? O3 C3 C7 110.4(9) . . ? O3 C3 C2 109.7(9) . . ? C7 C3 C2 102.0(10) . . ? O3 C3 C4 111.8(9) . . ? C7 C3 C4 116.0(9) . . ? C2 C3 C4 106.3(10) . . ? C15 C4 O1 108.1(11) . . ? C15 C4 C14 110.2(11) . . ? O1 C4 C14 103.0(10) . . ? C15 C4 C3 119.7(10) . . ? O1 C4 C3 102.3(10) . . ? C14 C4 C3 111.8(10) . . ? C8 C5 C6 119.5(11) . . ? C8 C5 C2 113.1(10) . . ? C6 C5 C2 104.6(10) . . ? C8 C5 H5 106(6) . . ? C6 C5 H5 106(6) . . ? C2 C5 H5 107(6) . . ? C16 C6 C7 114.7(10) . . ? C16 C6 C5 116.1(11) . . ? C7 C6 C5 102.3(10) . . ? C16 C6 H6 108(6) . . ? C7 C6 H6 108(6) . . ? C5 C6 H6 107(6) . . ? C3 C7 C6 105.4(9) . . ? C3 C7 H7A 110.7 . . ? C6 C7 H7A 110.7 . . ? C3 C7 H7B 110.7 . . ? C6 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? C9 C8 C13 118.7(11) . . ? C9 C8 C5 118.6(12) . . ? C13 C8 C5 122.5(12) . . ? C8 C9 C10 120.7(12) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.1(12) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.6(11) . . ? C10 C11 Br 119.8(12) . . ? C12 C11 Br 120.6(12) . . ? C11 C12 C13 120.4(13) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 120.0(12) . . ? C8 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C4 C15 H15A 109.5 . . ? C4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 O4 124.0(12) . . ? O5 C16 C6 124.6(13) . . ? O4 C16 C6 111.4(13) . . ? O4 C17 C18 105.9(9) . . ? O4 C17 H17A 110.6 . . ? C18 C17 H17A 110.6 . . ? O4 C17 H17B 110.6 . . ? C18 C17 H17B 110.6 . . ? H17A C17 H17B 108.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 O1 C4 112.0(10) . . ? C3 O3 H3 109.5 . . ? C16 O4 C17 115.0(9) . . ? 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 O2 C1 C2 C3 171.3(13) . . . . ? O1 C1 C2 C3 -4.2(14) . . . . ? O2 C1 C2 C5 53.5(17) . . . . ? O1 C1 C2 C5 -122.0(11) . . . . ? C1 C2 C3 O3 139.0(10) . . . . ? C5 C2 C3 O3 -98.4(12) . . . . ? C1 C2 C3 C7 -104.0(10) . . . . ? C5 C2 C3 C7 18.6(12) . . . . ? C1 C2 C3 C4 18.0(13) . . . . ? C5 C2 C3 C4 140.6(10) . . . . ? O3 C3 C4 C15 96.6(12) . . . . ? C7 C3 C4 C15 -31.1(15) . . . . ? C2 C3 C4 C15 -143.7(12) . . . . ? O3 C3 C4 O1 -144.1(10) . . . . ? C7 C3 C4 O1 88.3(11) . . . . ? C2 C3 C4 O1 -24.3(12) . . . . ? O3 C3 C4 C14 -34.4(14) . . . . ? C7 C3 C4 C14 -162.1(10) . . . . ? C2 C3 C4 C14 85.3(13) . . . . ? C3 C2 C5 C8 138.1(11) . . . . ? C1 C2 C5 C8 -107.3(12) . . . . ? C3 C2 C5 C6 6.6(13) . . . . ? C1 C2 C5 C6 121.1(11) . . . . ? C8 C5 C6 C16 77.7(15) . . . . ? C2 C5 C6 C16 -154.5(11) . . . . ? C8 C5 C6 C7 -156.7(10) . . . . ? C2 C5 C6 C7 -28.9(12) . . . . ? O3 C3 C7 C6 79.1(11) . . . . ? C2 C3 C7 C6 -37.5(11) . . . . ? C4 C3 C7 C6 -152.5(10) . . . . ? C16 C6 C7 C3 168.6(11) . . . . ? C5 C6 C7 C3 42.1(12) . . . . ? C6 C5 C8 C9 -118.6(12) . . . . ? C2 C5 C8 C9 117.7(11) . . . . ? C6 C5 C8 C13 56.5(16) . . . . ? C2 C5 C8 C13 -67.3(14) . . . . ? C13 C8 C9 C10 7.3(16) . . . . ? C5 C8 C9 C10 -177.5(10) . . . . ? C8 C9 C10 C11 -3.9(17) . . . . ? C9 C10 C11 C12 -2.7(18) . . . . ? C9 C10 C11 Br 177.8(8) . . . . ? C10 C11 C12 C13 6(2) . . . . ? Br C11 C12 C13 -174.8(9) . . . . ? C9 C8 C13 C12 -4.2(18) . . . . ? C5 C8 C13 C12 -179.2(11) . . . . ? C11 C12 C13 C8 -2(2) . . . . ? C7 C6 C16 O5 -89.0(16) . . . . ? C5 C6 C16 O5 30.0(19) . . . . ? C7 C6 C16 O4 90.3(13) . . . . ? C5 C6 C16 O4 -150.7(11) . . . . ? O2 C1 O1 C4 172.3(12) . . . . ? C2 C1 O1 C4 -12.1(14) . . . . ? C15 C4 O1 C1 150.2(11) . . . . ? C14 C4 O1 C1 -93.2(11) . . . . ? C3 C4 O1 C1 23.0(13) . . . . ? O5 C16 O4 C17 7.5(18) . . . . ? C6 C16 O4 C17 -171.7(9) . . . . ? C18 C17 O4 C16 -176.0(10) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.465 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.086