data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Br O2' _chemical_formula_sum 'C7 H7 Br O2' _chemical_formula_weight 203.04 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2049(12) _cell_length_b 5.3099(10) _cell_length_c 9.434(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.180(4) _cell_angle_gamma 90.00 _cell_volume 360.66(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7719 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description laths _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 5.629 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.431 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC-12 with Saturn 724+ CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7699 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1640 _reflns_number_gt 1624 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Flack H D (1983), Acta Cryst. A39, 876-881. Hooft, R. W. W., Straver, L. H. and Spek, A. L. (2008). J. Appl. Cryst., 41, 96-103. Determination of absolute structure using Bayesian statistics on Bijvoet differences. Sheldrick, G. M. (2008). SHELXL-97. Acta Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _chemical_absolute_configuration ad # syn absolute configuration from synthetic procedure # ad absolute configuration from anomalous dispersion effects # rm absolute configuration from reference to a chiral # reference molecule of known abs. conf. # Hooft, R. W. W., Straver, L. H. and Spek, A. L. (2008). J. Appl. Cryst., # 41, 96-103. Determination of absolute structure using Bayesian # statistics on Bijvoet differences. _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. The absolute configuration was determined by the method of Flack (1983). The Flack x parameter refined to 0.022(11). The assignment was corroborated by use of the Hooft y-parameter method (Hooft, Straver and Spek, 2008). The Hooft y-parameter refined to 0.023(8). ; _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^)+(0.0213P)^2^+0.0384P] 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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.022(11) _refine_ls_number_reflns 1640 _refine_ls_number_parameters 92 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0187 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0497 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 C1 C 0.5335(3) 0.6527(4) 0.8149(2) 0.0166(5) Uani 1 1 d . . . C2 C 0.2830(3) 0.7992(4) 0.8700(2) 0.0156(4) Uani 1 1 d . . . H2 H 0.2655 0.8826 0.9636 0.019 Uiso 1 1 calc R . . C3 C 0.1021(3) 0.7606(4) 0.7862(2) 0.0151(4) Uani 1 1 d . . . H3 H 0.0300 0.6223 0.8304 0.018 Uiso 1 1 calc R . . C4 C 0.1303(3) 0.6981(4) 0.6311(2) 0.0192(4) Uani 1 1 d . . . H4A H 0.1757 0.5227 0.6240 0.023 Uiso 1 1 calc R . . H4B H 0.0093 0.7087 0.5781 0.023 Uiso 1 1 calc R . . C5 C 0.2653(3) 0.8706(4) 0.5642(2) 0.0194(5) Uani 1 1 d . . . H5 H 0.2475 0.9101 0.4664 0.023 Uiso 1 1 calc R . . C6 C 0.4085(3) 0.9706(4) 0.6357(2) 0.0183(4) Uani 1 1 d . . . H6 H 0.4890 1.0822 0.5888 0.022 Uiso 1 1 calc R . . C7 C 0.4464(3) 0.9111(5) 0.7896(2) 0.0152(4) Uani 1 1 d . . . H7 H 0.5128 1.0493 0.8427 0.018 Uiso 1 1 calc R . . O1 O 0.38561(18) 0.5537(5) 0.88359(14) 0.0191(4) Uani 1 1 d . . . O2 O 0.67288(19) 0.5425(4) 0.78987(14) 0.0215(4) Uani 1 1 d . . . Br1 Br -0.03541(2) 1.07963(9) 0.800553(16) 0.01937(8) 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 C1 0.0184(10) 0.0210(13) 0.0101(9) 0.0002(7) -0.0032(7) 0.0002(8) C2 0.0160(10) 0.0183(11) 0.0125(9) -0.0002(8) 0.0025(7) 0.0023(8) C3 0.0124(9) 0.0106(9) 0.0224(10) -0.0012(8) 0.0024(7) 0.0016(8) C4 0.0172(10) 0.0202(11) 0.0199(10) -0.0058(8) -0.0047(8) 0.0032(9) C5 0.0237(11) 0.0220(11) 0.0127(9) 0.0026(8) 0.0018(8) 0.0103(9) C6 0.0180(10) 0.0184(10) 0.0190(10) 0.0070(8) 0.0075(7) 0.0029(8) C7 0.0125(10) 0.0156(12) 0.0176(10) -0.0015(7) -0.0002(8) -0.0005(7) O1 0.0174(6) 0.0204(10) 0.0193(6) 0.0065(7) 0.0003(5) 0.0027(8) O2 0.0164(7) 0.0265(12) 0.0213(6) -0.0002(7) -0.0008(5) 0.0055(8) Br1 0.01709(11) 0.01526(11) 0.02615(11) -0.00034(10) 0.00609(7) 0.00246(11) _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 C1 O2 1.193(3) . ? C1 O1 1.373(3) . ? C1 C7 1.524(3) . ? C2 O1 1.502(3) . ? C2 C3 1.512(3) . ? C2 C7 1.543(3) . ? C2 H2 1.0000 . ? C3 C4 1.521(3) . ? C3 Br1 1.970(2) . ? C3 H3 1.0000 . ? C4 C5 1.493(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.323(3) . ? C5 H5 0.9500 . ? C6 C7 1.501(3) . ? C6 H6 0.9500 . ? C7 H7 1.0000 . ? 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 125.4(2) . . ? O2 C1 C7 139.0(2) . . ? O1 C1 C7 95.51(19) . . ? O1 C2 C3 109.79(16) . . ? O1 C2 C7 89.64(15) . . ? C3 C2 C7 116.94(17) . . ? O1 C2 H2 112.8 . . ? C3 C2 H2 112.8 . . ? C7 C2 H2 112.8 . . ? C2 C3 C4 112.89(17) . . ? C2 C3 Br1 105.84(14) . . ? C4 C3 Br1 109.87(14) . . ? C2 C3 H3 109.4 . . ? C4 C3 H3 109.4 . . ? Br1 C3 H3 109.4 . . ? C5 C4 C3 112.65(18) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 122.62(18) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C7 121.2(2) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C1 113.57(18) . . ? C6 C7 C2 116.28(16) . . ? C1 C7 C2 83.92(17) . . ? C6 C7 H7 113.3 . . ? C1 C7 H7 113.3 . . ? C2 C7 H7 113.3 . . ? C1 O1 C2 90.90(18) . . ? 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 C2 C3 C4 -68.2(2) . . . . ? C7 C2 C3 C4 31.9(3) . . . . ? O1 C2 C3 Br1 171.62(12) . . . . ? C7 C2 C3 Br1 -88.29(19) . . . . ? C2 C3 C4 C5 -47.5(2) . . . . ? Br1 C3 C4 C5 70.34(19) . . . . ? C3 C4 C5 C6 32.5(3) . . . . ? C4 C5 C6 C7 1.3(3) . . . . ? C5 C6 C7 C1 76.8(3) . . . . ? C5 C6 C7 C2 -18.2(3) . . . . ? O2 C1 C7 C6 63.6(3) . . . . ? O1 C1 C7 C6 -114.83(18) . . . . ? O2 C1 C7 C2 179.7(3) . . . . ? O1 C1 C7 C2 1.23(14) . . . . ? O1 C2 C7 C6 112.2(2) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? O1 C2 C7 C1 -1.12(13) . . . . ? C3 C2 C7 C1 -113.24(18) . . . . ? O2 C1 O1 C2 -180.0(2) . . . . ? C7 C1 O1 C2 -1.25(14) . . . . ? C3 C2 O1 C1 119.87(17) . . . . ? C7 C2 O1 C1 1.23(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.358 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.060