data_turk14s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 Br2 O' _chemical_formula_weight 400.15 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 ? _space_group_crystal_system monoclinic _symmetry_space_group_name_H-M 'P2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.254(11) _cell_length_b 6.962(8) _cell_length_c 11.580(13) _cell_angle_alpha 90.00 _cell_angle_beta 110.196(16) _cell_angle_gamma 90.00 _cell_volume 775.9(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 25.20 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 5.218 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1885 _exptl_absorpt_correction_T_max 0.4218 _exptl_absorpt_process_details ; absorption corrections were made based on correspondance of equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 6969 _diffrn_reflns_av_R_equivalents 0.0992 _diffrn_reflns_av_sigmaI/netI 0.1399 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2725 _reflns_number_gt 1729 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1369P)^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 ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(4) _refine_ls_number_reflns 2725 _refine_ls_number_parameters 183 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1242 _refine_ls_R_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.2237 _refine_ls_wR_factor_gt 0.2063 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.004 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 -0.03715(16) 0.6213(3) 0.28784(16) 0.0386(5) Uani 1 1 d . . . Br2 Br 0.32828(17) 0.3790(3) 0.60582(15) 0.0411(5) Uani 1 1 d . . . C1 C 0.1439(17) 0.500(3) 0.3785(16) 0.033(4) Uani 1 1 d . . . C2 C 0.1791(17) 0.543(3) 0.5102(16) 0.033(4) Uani 1 1 d . . . H2 H 0.0958 0.5164 0.5338 0.040 Uiso 1 1 calc R . . C3 C 0.220(2) 0.756(3) 0.5369(18) 0.043(5) Uani 1 1 d . . . H3A H 0.1351 0.8353 0.5054 0.051 Uiso 1 1 calc R . . H3B H 0.2593 0.7743 0.6272 0.051 Uiso 1 1 calc R . . C4 C 0.3231(17) 0.827(2) 0.4818(16) 0.039(4) Uani 1 1 d . . . H4A H 0.4154 0.7715 0.5275 0.047 Uiso 1 1 calc R . . H4B H 0.3308 0.9686 0.4909 0.047 Uiso 1 1 calc R . . C5 C 0.2827(18) 0.776(2) 0.3465(18) 0.043(5) Uani 1 1 d . . . H5A H 0.1988 0.8489 0.2984 0.052 Uiso 1 1 calc R . . H5B H 0.3589 0.8121 0.3167 0.052 Uiso 1 1 calc R . . C6 C 0.2544(17) 0.566(2) 0.3267(15) 0.029(4) Uani 1 1 d . . . H6 H 0.3421 0.4989 0.3767 0.035 Uiso 1 1 calc R . . C7 C 0.1148(19) 0.294(3) 0.3300(18) 0.039(5) Uani 1 1 d . . . C8 C 0.1709(19) 0.274(2) 0.2246(16) 0.035(4) Uani 1 1 d . . . H8 H 0.2580 0.1960 0.2553 0.041 Uiso 1 1 calc R . . C9 C 0.0705(17) 0.169(2) 0.1169(15) 0.036(4) Uani 1 1 d . . . H9A H 0.0453 0.0459 0.1449 0.054 Uiso 1 1 calc R . . H9B H 0.1140 0.1451 0.0550 0.054 Uiso 1 1 calc R . . H9C H -0.0133 0.2467 0.0806 0.054 Uiso 1 1 calc R . . C10 C 0.2116(16) 0.478(2) 0.1996(14) 0.026(4) Uani 1 1 d . . . H10 H 0.1267 0.5456 0.1450 0.031 Uiso 1 1 calc R . . C11 C 0.3169(15) 0.474(3) 0.1375(16) 0.032(4) Uani 1 1 d . . . C12 C 0.2784(18) 0.467(2) 0.0136(17) 0.037(4) Uani 1 1 d . . . H12 H 0.1824 0.4613 -0.0344 0.045 Uiso 1 1 calc R . . C13 C 0.3747(17) 0.467(3) -0.0451(16) 0.036(4) Uani 1 1 d . . . H13 H 0.3435 0.4646 -0.1325 0.043 Uiso 1 1 calc R . . C14 C 0.5125(18) 0.471(2) 0.0189(16) 0.035(4) Uani 1 1 d . . . C15 C 0.5541(17) 0.476(3) 0.1444(17) 0.038(4) Uani 1 1 d . . . H15 H 0.6507 0.4765 0.1910 0.045 Uiso 1 1 calc R . . C16 C 0.4598(16) 0.480(2) 0.2052(16) 0.030(4) Uani 1 1 d . . . H16 H 0.4914 0.4875 0.2925 0.037 Uiso 1 1 calc R . . C17 C 0.6172(19) 0.476(2) -0.0451(16) 0.040(5) Uani 1 1 d . . . H17A H 0.7109 0.4637 0.0159 0.060 Uiso 1 1 calc R . . H17B H 0.6094 0.5974 -0.0895 0.060 Uiso 1 1 calc R . . H17C H 0.5997 0.3686 -0.1035 0.060 Uiso 1 1 calc R . . O1 O 0.0620(12) 0.1752(15) 0.3710(11) 0.039(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 Br1 0.0289(9) 0.0425(10) 0.0545(12) 0.0002(10) 0.0273(8) 0.0039(9) Br2 0.0396(10) 0.0501(11) 0.0440(11) 0.0032(9) 0.0276(8) 0.0058(9) C1 0.028(10) 0.040(11) 0.045(12) -0.004(8) 0.029(9) -0.006(8) C2 0.019(8) 0.055(11) 0.036(10) -0.003(8) 0.024(8) -0.003(7) C3 0.039(12) 0.047(12) 0.051(13) -0.002(9) 0.027(10) 0.003(9) C4 0.043(11) 0.032(10) 0.053(11) 0.003(8) 0.033(9) 0.007(8) C5 0.035(11) 0.035(10) 0.083(15) -0.023(10) 0.050(11) -0.014(8) C6 0.027(9) 0.030(10) 0.033(9) -0.008(7) 0.015(7) -0.012(7) C7 0.039(11) 0.037(10) 0.056(12) -0.002(9) 0.036(10) -0.004(8) C8 0.051(11) 0.023(9) 0.046(11) -0.007(8) 0.037(10) -0.002(8) C9 0.038(10) 0.030(11) 0.047(11) -0.013(8) 0.024(9) -0.012(7) C10 0.026(9) 0.030(9) 0.027(9) 0.005(7) 0.016(7) 0.008(7) C11 0.017(8) 0.043(10) 0.043(11) 0.009(8) 0.021(8) 0.008(7) C12 0.028(10) 0.040(10) 0.048(12) -0.006(8) 0.018(9) 0.013(8) C13 0.032(10) 0.051(11) 0.028(10) 0.010(8) 0.016(8) 0.000(8) C14 0.035(10) 0.044(10) 0.029(10) 0.015(8) 0.017(8) 0.003(8) C15 0.026(9) 0.048(11) 0.049(12) -0.012(9) 0.025(9) -0.005(8) C16 0.026(9) 0.033(9) 0.036(10) 0.005(7) 0.015(8) 0.003(7) C17 0.061(13) 0.025(9) 0.045(11) -0.002(8) 0.034(10) -0.012(9) O1 0.040(7) 0.034(8) 0.057(8) -0.001(6) 0.035(7) -0.001(5) _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 C1 1.977(18) . ? Br2 C2 1.922(18) . ? C1 C2 1.47(2) . ? C1 C6 1.52(2) . ? C1 C7 1.54(2) . ? C2 C3 1.54(2) . ? C3 C4 1.49(2) . ? C4 C5 1.52(2) . ? C5 C6 1.49(2) . ? C6 C10 1.51(2) . ? C7 O1 1.174(19) . ? C7 C8 1.53(2) . ? C8 C9 1.51(2) . ? C8 C10 1.53(2) . ? C10 C11 1.49(2) . ? C11 C12 1.35(2) . ? C11 C16 1.40(2) . ? C12 C13 1.38(2) . ? C13 C14 1.35(2) . ? C14 C15 1.37(2) . ? C14 C17 1.50(2) . ? C15 C16 1.38(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 C2 C1 C6 113.5(14) . . ? C2 C1 C7 120.9(16) . . ? C6 C1 C7 102.2(13) . . ? C2 C1 Br1 108.4(11) . . ? C6 C1 Br1 110.8(12) . . ? C7 C1 Br1 100.1(12) . . ? C1 C2 C3 110.6(15) . . ? C1 C2 Br2 109.9(11) . . ? C3 C2 Br2 110.3(13) . . ? C4 C3 C2 114.7(15) . . ? C3 C4 C5 112.4(14) . . ? C6 C5 C4 111.0(16) . . ? C5 C6 C10 121.4(14) . . ? C5 C6 C1 111.3(14) . . ? C10 C6 C1 104.9(12) . . ? O1 C7 C8 127.9(16) . . ? O1 C7 C1 124.8(16) . . ? C8 C7 C1 107.3(13) . . ? C9 C8 C7 111.6(14) . . ? C9 C8 C10 116.5(15) . . ? C7 C8 C10 105.6(12) . . ? C11 C10 C6 117.5(14) . . ? C11 C10 C8 111.3(13) . . ? C6 C10 C8 101.4(12) . . ? C12 C11 C16 117.4(15) . . ? C12 C11 C10 121.2(15) . . ? C16 C11 C10 121.4(15) . . ? C11 C12 C13 121.8(17) . . ? C14 C13 C12 121.4(17) . . ? C13 C14 C15 117.9(16) . . ? C13 C14 C17 121.4(16) . . ? C15 C14 C17 120.7(16) . . ? C14 C15 C16 121.8(17) . . ? C15 C16 C11 119.7(17) . . ? 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 51.4(19) . . . . ? C7 C1 C2 C3 173.4(15) . . . . ? Br1 C1 C2 C3 -72.1(15) . . . . ? C6 C1 C2 Br2 -70.7(16) . . . . ? C7 C1 C2 Br2 51.3(18) . . . . ? Br1 C1 C2 Br2 165.8(8) . . . . ? C1 C2 C3 C4 -48(2) . . . . ? Br2 C2 C3 C4 73.6(18) . . . . ? C2 C3 C4 C5 49(2) . . . . ? C3 C4 C5 C6 -52(2) . . . . ? C4 C5 C6 C10 179.8(13) . . . . ? C4 C5 C6 C1 55.6(19) . . . . ? C2 C1 C6 C5 -57(2) . . . . ? C7 C1 C6 C5 171.1(16) . . . . ? Br1 C1 C6 C5 65.1(18) . . . . ? C2 C1 C6 C10 169.9(13) . . . . ? C7 C1 C6 C10 38.1(17) . . . . ? Br1 C1 C6 C10 -67.9(14) . . . . ? C2 C1 C7 O1 33(3) . . . . ? C6 C1 C7 O1 160.6(19) . . . . ? Br1 C1 C7 O1 -85(2) . . . . ? C2 C1 C7 C8 -144.8(15) . . . . ? C6 C1 C7 C8 -17.6(19) . . . . ? Br1 C1 C7 C8 96.5(14) . . . . ? O1 C7 C8 C9 46(3) . . . . ? C1 C7 C8 C9 -136.2(16) . . . . ? O1 C7 C8 C10 173(2) . . . . ? C1 C7 C8 C10 -9(2) . . . . ? C5 C6 C10 C11 68(2) . . . . ? C1 C6 C10 C11 -164.9(14) . . . . ? C5 C6 C10 C8 -170.5(15) . . . . ? C1 C6 C10 C8 -43.5(16) . . . . ? C9 C8 C10 C11 -78.3(19) . . . . ? C7 C8 C10 C11 157.1(15) . . . . ? C9 C8 C10 C6 155.9(14) . . . . ? C7 C8 C10 C6 31.4(17) . . . . ? C6 C10 C11 C12 -155.3(16) . . . . ? C8 C10 C11 C12 89(2) . . . . ? C6 C10 C11 C16 24(2) . . . . ? C8 C10 C11 C16 -92.5(19) . . . . ? C16 C11 C12 C13 0(3) . . . . ? C10 C11 C12 C13 178.5(16) . . . . ? C11 C12 C13 C14 1(3) . . . . ? C12 C13 C14 C15 0(3) . . . . ? C12 C13 C14 C17 -178.8(16) . . . . ? C13 C14 C15 C16 -1(3) . . . . ? C17 C14 C15 C16 177.3(16) . . . . ? C14 C15 C16 C11 2(3) . . . . ? C12 C11 C16 C15 -1(2) . . . . ? C10 C11 C16 C15 179.9(15) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.749 _refine_diff_density_min -0.805 _refine_diff_density_rms 0.159