data_cd2754 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Br O2.50' _chemical_formula_weight 302.16 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 Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 45.814(7) _cell_length_b 9.4317(13) _cell_length_c 11.6643(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5040.2(12) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2457 _cell_measurement_theta_min 5.625 _cell_measurement_theta_max 48.006 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.503 _exptl_crystal_size_mid 0.483 _exptl_crystal_size_min 0.437 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 3.254 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.71194 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7284 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -59 _diffrn_reflns_limit_h_max 57 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2671 _reflns_number_gt 1979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0527P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.021(12) _chemical_absolute_configuration ad _refine_ls_number_reflns 2671 _refine_ls_number_parameters 167 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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 Br Br 0.107944(12) -0.16474(5) 0.30168(4) 0.05845(19) Uani 1 1 d . . . O1 O 0.00978(8) 0.7746(4) 0.1778(3) 0.0605(10) Uani 1 1 d . . . O2 O 0.06270(8) 0.4915(4) 0.4198(3) 0.0503(9) Uani 1 1 d . . . O3 O 0.0000 1.0000 0.3366(5) 0.0632(15) Uani 1 2 d SD . . C1 C 0.02781(11) 0.6795(5) 0.1897(4) 0.0397(11) Uani 1 1 d . . . C2 C 0.04442(13) 0.6227(6) 0.0893(4) 0.0523(14) Uani 1 1 d . . . H2A H 0.0606 0.6858 0.0730 0.063 Uiso 1 1 calc R . . H2B H 0.0317 0.6224 0.0227 0.063 Uiso 1 1 calc R . . C3 C 0.05633(12) 0.4725(5) 0.1075(4) 0.0461(12) Uani 1 1 d . . . H3A H 0.0401 0.4062 0.1092 0.055 Uiso 1 1 calc R . . H3B H 0.0687 0.4474 0.0431 0.055 Uiso 1 1 calc R . . C4 C 0.07386(10) 0.4578(5) 0.2184(4) 0.0358(10) Uani 1 1 d . . . C5 C 0.05628(8) 0.5246(4) 0.3120(4) 0.0330(9) Uani 1 1 d . . . C6 C 0.03501(8) 0.6215(4) 0.2999(4) 0.0351(8) Uani 1 1 d . . . C7 C 0.02430(13) 0.6654(5) 0.4156(5) 0.0514(14) Uani 1 1 d . . . H7A H 0.0039 0.6419 0.4259 0.062 Uiso 1 1 calc R . . H7B H 0.0271 0.7661 0.4282 0.062 Uiso 1 1 calc R . . C8 C 0.04372(14) 0.5776(6) 0.4939(4) 0.0602(15) Uani 1 1 d . . . H8A H 0.0554 0.6391 0.5423 0.072 Uiso 1 1 calc R . . H8B H 0.0319 0.5170 0.5425 0.072 Uiso 1 1 calc R . . C9 C 0.08245(9) 0.3068(4) 0.2410(3) 0.0318(9) Uani 1 1 d . . . C10 C 0.11061(9) 0.2612(5) 0.2238(4) 0.0393(10) Uani 1 1 d . . . H10 H 0.1246 0.3262 0.1997 0.047 Uiso 1 1 calc R . . C11 C 0.11875(10) 0.1228(5) 0.2410(4) 0.0437(11) Uani 1 1 d . . . H11 H 0.1379 0.0936 0.2290 0.052 Uiso 1 1 calc R . . C12 C 0.09754(9) 0.0280(4) 0.2768(3) 0.0359(10) Uani 1 1 d . . . C13 C 0.06937(9) 0.0685(4) 0.2951(4) 0.0364(9) Uani 1 1 d . . . H13 H 0.0554 0.0034 0.3192 0.044 Uiso 1 1 calc R . . C14 C 0.06207(9) 0.2079(5) 0.2772(4) 0.0375(10) Uani 1 1 d . . . H14 H 0.0429 0.2368 0.2896 0.045 Uiso 1 1 calc R . . H3 H 0.0070(17) 0.934(6) 0.287(5) 0.12(3) Uiso 1 1 d D . . H4 H 0.0919(9) 0.512(5) 0.211(3) 0.028(10) 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 Br 0.0698(3) 0.0339(2) 0.0716(3) 0.0045(3) -0.0069(3) 0.0087(2) O1 0.074(2) 0.057(2) 0.0508(19) 0.0022(18) -0.0055(19) 0.035(2) O2 0.073(2) 0.050(2) 0.0286(16) -0.0080(15) -0.0119(16) 0.0220(17) O3 0.057(3) 0.055(4) 0.078(4) 0.000 0.000 0.005(3) C1 0.045(3) 0.040(3) 0.034(3) -0.002(2) -0.005(2) 0.006(2) C2 0.074(3) 0.048(3) 0.035(3) 0.007(2) 0.006(2) 0.023(3) C3 0.068(3) 0.043(3) 0.027(2) -0.001(2) 0.009(2) 0.017(2) C4 0.038(2) 0.029(2) 0.040(3) -0.0006(19) 0.0050(19) 0.0049(19) C5 0.043(2) 0.033(2) 0.023(2) -0.0070(18) -0.0028(19) -0.0043(18) C6 0.041(2) 0.0334(18) 0.031(2) -0.004(2) 0.000(2) 0.0037(16) C7 0.074(4) 0.043(3) 0.037(3) -0.007(2) 0.006(3) 0.012(2) C8 0.097(4) 0.057(3) 0.026(2) -0.013(2) 0.005(3) 0.013(3) C9 0.040(2) 0.034(2) 0.0221(19) -0.0011(17) 0.0008(17) 0.0043(18) C10 0.037(2) 0.038(2) 0.043(2) -0.002(2) 0.0082(19) -0.0026(19) C11 0.037(2) 0.043(3) 0.051(3) 0.006(2) 0.004(2) 0.010(2) C12 0.051(2) 0.027(2) 0.030(2) 0.0017(18) -0.0027(18) 0.0013(18) C13 0.044(2) 0.036(2) 0.030(2) 0.007(2) 0.003(2) -0.0055(17) C14 0.035(2) 0.041(2) 0.036(3) -0.0003(18) 0.0029(18) 0.0018(18) _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 C12 1.901(4) . ? O1 C1 1.227(5) . ? O2 C5 1.329(5) . ? O2 C8 1.471(6) . ? O3 H3 0.91(2) . ? C1 C6 1.436(7) . ? C1 C2 1.496(7) . ? C2 C3 1.533(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.529(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.496(6) . ? C4 C9 1.502(6) . ? C4 H4 0.98(4) . ? C5 C6 1.343(6) . ? C6 C7 1.494(7) . ? C7 C8 1.520(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.375(6) . ? C9 C14 1.385(6) . ? C10 C11 1.373(7) . ? C10 H10 0.9300 . ? C11 C12 1.385(7) . ? C11 H11 0.9300 . ? C12 C13 1.363(6) . ? C13 C14 1.373(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 C5 O2 C8 107.2(4) . . ? O1 C1 C6 122.3(5) . . ? O1 C1 C2 121.1(5) . . ? C6 C1 C2 116.6(4) . . ? C1 C2 C3 113.8(4) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 112.8(4) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C9 114.3(4) . . ? C5 C4 C3 107.3(3) . . ? C9 C4 C3 111.8(4) . . ? C5 C4 H4 107(2) . . ? C9 C4 H4 107(2) . . ? C3 C4 H4 109(2) . . ? O2 C5 C6 114.8(4) . . ? O2 C5 C4 118.2(4) . . ? C6 C5 C4 126.9(4) . . ? C5 C6 C1 121.3(4) . . ? C5 C6 C7 109.4(4) . . ? C1 C6 C7 128.8(4) . . ? C6 C7 C8 101.5(4) . . ? C6 C7 H7A 111.5 . . ? C8 C7 H7A 111.5 . . ? C6 C7 H7B 111.5 . . ? C8 C7 H7B 111.5 . . ? H7A C7 H7B 109.3 . . ? O2 C8 C7 107.1(4) . . ? O2 C8 H8A 110.3 . . ? C7 C8 H8A 110.3 . . ? O2 C8 H8B 110.3 . . ? C7 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C10 C9 C14 117.8(4) . . ? C10 C9 C4 121.1(4) . . ? C14 C9 C4 121.0(4) . . ? C11 C10 C9 122.1(4) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 117.9(4) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C13 C12 C11 122.0(4) . . ? C13 C12 Br 118.8(3) . . ? C11 C12 Br 119.2(3) . . ? C12 C13 C14 118.4(4) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C13 C14 C9 121.8(4) . . ? C13 C14 H14 119.1 . . ? C9 C14 H14 119.1 . . ? 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 C1 C2 C3 -157.2(5) . . . . ? C6 C1 C2 C3 25.4(7) . . . . ? C1 C2 C3 C4 -52.0(6) . . . . ? C2 C3 C4 C5 47.5(5) . . . . ? C2 C3 C4 C9 173.6(4) . . . . ? C8 O2 C5 C6 -0.8(5) . . . . ? C8 O2 C5 C4 176.4(4) . . . . ? C9 C4 C5 O2 36.9(5) . . . . ? C3 C4 C5 O2 161.5(4) . . . . ? C9 C4 C5 C6 -146.4(4) . . . . ? C3 C4 C5 C6 -21.7(6) . . . . ? O2 C5 C6 C1 173.1(4) . . . . ? C4 C5 C6 C1 -3.8(7) . . . . ? O2 C5 C6 C7 -0.1(5) . . . . ? C4 C5 C6 C7 -177.0(4) . . . . ? O1 C1 C6 C5 -175.2(5) . . . . ? C2 C1 C6 C5 2.2(7) . . . . ? O1 C1 C6 C7 -3.4(8) . . . . ? C2 C1 C6 C7 173.9(5) . . . . ? C5 C6 C7 C8 0.9(5) . . . . ? C1 C6 C7 C8 -171.7(5) . . . . ? C5 O2 C8 C7 1.3(5) . . . . ? C6 C7 C8 O2 -1.3(5) . . . . ? C5 C4 C9 C10 -132.9(4) . . . . ? C3 C4 C9 C10 105.0(5) . . . . ? C5 C4 C9 C14 48.8(5) . . . . ? C3 C4 C9 C14 -73.4(5) . . . . ? C14 C9 C10 C11 0.2(7) . . . . ? C4 C9 C10 C11 -178.2(4) . . . . ? C9 C10 C11 C12 0.0(7) . . . . ? C10 C11 C12 C13 -0.1(7) . . . . ? C10 C11 C12 Br -180.0(4) . . . . ? C11 C12 C13 C14 0.1(7) . . . . ? Br C12 C13 C14 179.9(3) . . . . ? C12 C13 C14 C9 0.1(7) . . . . ? C10 C9 C14 C13 -0.3(6) . . . . ? C4 C9 C14 C13 178.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.91(2) 1.97(3) 2.855(5) 163(8) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.425 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.085