data_C16H17BrO3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 Br O3' _chemical_formula_sum 'C16 H17 Br O3' _chemical_formula_weight 337.21 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 '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+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.1590(3) _cell_length_b 9.1136(5) _cell_length_c 25.9848(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1458.54(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9609 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.41 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method none _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.823 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.5507 _exptl_absorpt_correction_T_max 0.8489 _exptl_absorpt_process_details ; Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA. ; _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 'Bruker Kappa DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26659 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.41 _reflns_number_total 3643 _reflns_number_gt 3536 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0205P)^2^+0.2764P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef na _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.018(6) _refine_ls_number_reflns 3643 _refine_ls_number_parameters 194 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0176 _refine_ls_R_factor_gt 0.0168 _refine_ls_wR_factor_ref 0.0455 _refine_ls_wR_factor_gt 0.0452 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _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 0.99612(2) -0.263566(14) 0.247200(4) 0.02069(4) Uani 1 1 d . . . O1 O 0.26480(15) 0.35954(10) 0.39216(4) 0.01890(19) Uani 1 1 d . . . O2 O 0.23888(17) -0.12683(11) 0.43465(4) 0.0230(2) Uani 1 1 d . . . O3 O 0.37963(15) -0.07699(10) 0.51236(3) 0.01875(19) Uani 1 1 d . . . C1 C 0.8198(2) -0.14680(14) 0.29093(5) 0.0154(2) Uani 1 1 d . . . C2 C 0.8992(2) -0.10382(14) 0.33827(5) 0.0162(2) Uani 1 1 d . . . H2 H 1.0402 -0.1330 0.3491 0.019 Uiso 1 1 calc R . . C3 C 0.7697(2) -0.01709(14) 0.36995(5) 0.0151(2) Uani 1 1 d . . . H3 H 0.8232 0.0130 0.4026 0.018 Uiso 1 1 calc R . . C4 C 0.56243(19) 0.02626(14) 0.35449(5) 0.0143(2) Uani 1 1 d . . . C5 C 0.4869(2) -0.01986(13) 0.30661(4) 0.0160(2) Uani 1 1 d . . . H5 H 0.3460 0.0089 0.2957 0.019 Uiso 1 1 calc R . . C6 C 0.6131(2) -0.10688(14) 0.27458(5) 0.0166(2) Uani 1 1 d . . . H6 H 0.5594 -0.1385 0.2422 0.020 Uiso 1 1 calc R . . C7 C 0.4186(2) 0.12356(14) 0.38796(5) 0.0132(2) Uani 1 1 d D . . H7 H 0.264(2) 0.1050(17) 0.3797(6) 0.016 Uiso 1 1 d D . . C8 C 0.44813(19) 0.28494(15) 0.37692(4) 0.0147(2) Uani 1 1 d . . . C9 C 0.6248(2) 0.34869(15) 0.35748(5) 0.0175(2) Uani 1 1 d D . . H9 H 0.747(2) 0.2903(17) 0.3508(6) 0.021 Uiso 1 1 d D . . C10 C 0.6390(2) 0.51005(16) 0.34710(6) 0.0225(3) Uani 1 1 d . . . H10A H 0.6918 0.5264 0.3116 0.027 Uiso 1 1 calc R . . H10B H 0.7439 0.5555 0.3712 0.027 Uiso 1 1 calc R . . C11 C 0.4170(3) 0.58181(17) 0.35371(6) 0.0255(3) Uani 1 1 d . . . H11A H 0.4352 0.6885 0.3595 0.031 Uiso 1 1 calc R . . H11B H 0.3300 0.5680 0.3220 0.031 Uiso 1 1 calc R . . C12 C 0.2997(2) 0.51425(15) 0.39895(6) 0.0225(3) Uani 1 1 d . . . H12A H 0.3859 0.5305 0.4306 0.027 Uiso 1 1 calc R . . H12B H 0.1578 0.5637 0.4035 0.027 Uiso 1 1 calc R . . C13 C 0.44570(18) 0.09209(14) 0.44516(5) 0.0143(2) Uani 1 1 d . . . C14 C 0.5490(2) 0.17862(15) 0.47792(5) 0.0202(3) Uani 1 1 d D . . H14A H 0.620(3) 0.2660(16) 0.4657(6) 0.024 Uiso 1 1 d D . . H14B H 0.568(3) 0.1549(18) 0.5141(5) 0.024 Uiso 1 1 d D . . C15 C 0.34329(19) -0.04771(14) 0.46255(5) 0.0149(2) Uani 1 1 d . . . C16 C 0.2881(2) -0.21175(15) 0.53183(5) 0.0189(2) Uani 1 1 d . . . H16A H 0.1369 -0.1950 0.5420 0.028 Uiso 1 1 calc R . . H16B H 0.3718 -0.2447 0.5618 0.028 Uiso 1 1 calc R . . H16C H 0.2935 -0.2871 0.5049 0.028 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 0.01931(7) 0.02270(7) 0.02005(7) -0.00498(4) 0.00476(5) 0.00135(5) O1 0.0176(4) 0.0137(4) 0.0254(5) -0.0012(4) 0.0032(4) 0.0027(4) O2 0.0290(5) 0.0217(5) 0.0184(5) 0.0019(4) -0.0051(4) -0.0091(4) O3 0.0257(5) 0.0165(5) 0.0140(4) 0.0029(4) -0.0018(4) -0.0041(4) C1 0.0177(6) 0.0120(6) 0.0164(5) 0.0000(5) 0.0051(4) 0.0000(4) C2 0.0153(5) 0.0159(6) 0.0174(6) 0.0027(5) -0.0004(4) 0.0000(5) C3 0.0170(5) 0.0151(6) 0.0132(5) 0.0000(4) -0.0018(5) -0.0014(5) C4 0.0157(5) 0.0116(6) 0.0154(6) 0.0025(5) 0.0000(4) -0.0006(4) C5 0.0156(5) 0.0155(5) 0.0169(5) 0.0015(4) -0.0016(5) -0.0004(6) C6 0.0203(6) 0.0170(6) 0.0124(5) -0.0003(4) -0.0016(4) -0.0017(5) C7 0.0139(5) 0.0127(6) 0.0130(5) -0.0007(4) -0.0010(4) -0.0004(4) C8 0.0172(5) 0.0139(6) 0.0131(5) -0.0007(4) -0.0011(4) 0.0023(4) C9 0.0203(6) 0.0154(6) 0.0169(6) -0.0010(5) 0.0032(5) 0.0008(5) C10 0.0294(7) 0.0176(7) 0.0205(7) 0.0003(5) 0.0066(6) -0.0038(6) C11 0.0363(7) 0.0145(7) 0.0256(7) 0.0025(6) 0.0040(6) 0.0031(6) C12 0.0271(7) 0.0124(6) 0.0280(7) -0.0022(5) 0.0060(6) 0.0028(5) C13 0.0140(5) 0.0144(6) 0.0145(5) 0.0013(4) 0.0011(4) 0.0011(4) C14 0.0247(6) 0.0194(7) 0.0167(6) 0.0024(5) -0.0019(5) -0.0035(5) C15 0.0136(5) 0.0163(6) 0.0147(5) 0.0012(5) 0.0007(4) 0.0022(5) C16 0.0202(6) 0.0168(6) 0.0196(6) 0.0044(5) 0.0019(4) -0.0020(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 1.8983(12) . ? O1 C8 1.3761(15) . ? O1 C12 1.4372(16) . ? O2 C15 1.2079(16) . ? O3 C15 1.3404(14) . ? O3 C16 1.4428(16) . ? C1 C2 1.3806(17) . ? C1 C6 1.3905(17) . ? C2 C3 1.3925(17) . ? C2 H2 0.9500 . ? C3 C4 1.3955(17) . ? C3 H3 0.9500 . ? C4 C5 1.3930(16) . ? C4 C7 1.5256(18) . ? C5 C6 1.3877(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5094(18) . ? C7 C13 1.5228(17) . ? C7 H7 0.993(13) . ? C8 C9 1.3327(18) . ? C9 C10 1.4976(19) . ? C9 H9 0.937(13) . ? C10 C11 1.525(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.511(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.3235(18) . ? C13 C15 1.4918(17) . ? C14 H14A 0.962(13) . ? C14 H14B 0.971(13) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 113.41(11) . . ? C15 O3 C16 116.28(10) . . ? C2 C1 C6 121.51(12) . . ? C2 C1 Br1 119.31(9) . . ? C6 C1 Br1 119.18(9) . . ? C1 C2 C3 118.99(11) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.97(12) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.51(12) . . ? C5 C4 C7 119.39(11) . . ? C3 C4 C7 122.10(11) . . ? C6 C5 C4 121.40(12) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 118.62(11) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C8 C7 C13 110.84(10) . . ? C8 C7 C4 112.84(10) . . ? C13 C7 C4 112.55(10) . . ? C8 C7 H7 103.9(9) . . ? C13 C7 H7 106.5(9) . . ? C4 C7 H7 109.6(9) . . ? C9 C8 O1 124.29(12) . . ? C9 C8 C7 126.52(12) . . ? O1 C8 C7 109.14(10) . . ? C8 C9 C10 122.96(13) . . ? C8 C9 H9 118.5(10) . . ? C10 C9 H9 118.5(10) . . ? C9 C10 C11 110.39(12) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 109.96(12) . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O1 C12 C11 112.07(12) . . ? O1 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? O1 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C15 121.16(11) . . ? C14 C13 C7 124.62(12) . . ? C15 C13 C7 114.22(10) . . ? C13 C14 H14A 119.9(10) . . ? C13 C14 H14B 123.3(10) . . ? H14A C14 H14B 116.7(14) . . ? O2 C15 O3 123.34(12) . . ? O2 C15 C13 123.58(11) . . ? O3 C15 C13 113.08(11) . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C1 C2 C3 -0.76(19) . . . . ? Br1 C1 C2 C3 179.44(9) . . . . ? C1 C2 C3 C4 0.05(19) . . . . ? C2 C3 C4 C5 0.35(19) . . . . ? C2 C3 C4 C7 -178.85(12) . . . . ? C3 C4 C5 C6 -0.04(18) . . . . ? C7 C4 C5 C6 179.17(11) . . . . ? C4 C5 C6 C1 -0.64(19) . . . . ? C2 C1 C6 C5 1.05(19) . . . . ? Br1 C1 C6 C5 -179.14(9) . . . . ? C5 C4 C7 C8 -88.14(13) . . . . ? C3 C4 C7 C8 91.04(14) . . . . ? C5 C4 C7 C13 145.49(11) . . . . ? C3 C4 C7 C13 -35.32(16) . . . . ? C12 O1 C8 C9 -16.48(17) . . . . ? C12 O1 C8 C7 161.12(11) . . . . ? C13 C7 C8 C9 101.60(14) . . . . ? C4 C7 C8 C9 -25.67(17) . . . . ? C13 C7 C8 O1 -75.94(12) . . . . ? C4 C7 C8 O1 156.79(10) . . . . ? O1 C8 C9 C10 -3.6(2) . . . . ? C7 C8 C9 C10 179.20(12) . . . . ? C8 C9 C10 C11 -8.96(19) . . . . ? C9 C10 C11 C12 38.75(16) . . . . ? C8 O1 C12 C11 48.46(15) . . . . ? C10 C11 C12 O1 -60.51(16) . . . . ? C8 C7 C13 C14 -20.91(17) . . . . ? C4 C7 C13 C14 106.52(14) . . . . ? C8 C7 C13 C15 158.81(10) . . . . ? C4 C7 C13 C15 -73.76(13) . . . . ? C16 O3 C15 O2 0.64(18) . . . . ? C16 O3 C15 C13 -179.13(10) . . . . ? C14 C13 C15 O2 176.47(13) . . . . ? C7 C13 C15 O2 -3.27(17) . . . . ? C14 C13 C15 O3 -3.76(17) . . . . ? C7 C13 C15 O3 176.50(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.312 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.047