data_ef1300m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl2 O4' _chemical_formula_weight 315.14 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M Pbca 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' '-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 17.6881(9) _cell_length_b 5.8655(3) _cell_length_c 27.0846(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2810.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(1) _cell_measurement_reflns_used 6214 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 30.02 _exptl_crystal_description 'Needle plate fragment' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type 'Integration' _exptl_absorpt_correction_T_min 0.852 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details 'Face-indexed analytical' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(1) _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 APEX' _diffrn_measurement_method 'Omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19179 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3480 _reflns_number_gt 3051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART' _computing_cell_refinement 'SAINT' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXTL' _computing_structure_refinement 'SHELXTL' _computing_molecular_graphics 'SHELXTL' _computing_publication_material '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^)+(0.0180P)^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 ? _refine_ls_number_reflns 3480 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.907 _refine_ls_restrained_S_all 1.907 _refine_ls_shift/su_max 0.000 _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 O1 O -0.21393(5) 0.08827(15) 0.48541(3) 0.0252(2) Uani 1 1 d . . . C2 C -0.14077(7) 0.1010(2) 0.50919(5) 0.0251(3) Uani 1 1 d . . . O3 O -0.09143(5) -0.06698(15) 0.48731(3) 0.0268(2) Uani 1 1 d . . . C4 C -0.08635(7) -0.0768(2) 0.43775(5) 0.0244(3) Uani 1 1 d . . . C5 C -0.14472(7) 0.0536(2) 0.40970(5) 0.0211(3) Uani 1 1 d . . . C6 C -0.21815(7) 0.0835(2) 0.43571(5) 0.0217(3) Uani 1 1 d . . . C7 C -0.15350(8) 0.0235(3) 0.56144(5) 0.0349(3) Uani 1 1 d . . . H7X H -0.1731 -0.1328 0.5613 0.052 Uiso 1 1 calc R . . H7Y H -0.1901 0.1246 0.5775 0.052 Uiso 1 1 calc R . . H7Z H -0.1056 0.0281 0.5796 0.052 Uiso 1 1 calc R . . C8 C -0.10796(8) 0.3377(2) 0.50486(5) 0.0299(3) Uani 1 1 d . . . H8X H -0.0589 0.3429 0.5216 0.045 Uiso 1 1 calc R . . H8Y H -0.1424 0.4477 0.5203 0.045 Uiso 1 1 calc R . . H8Z H -0.1013 0.3763 0.4699 0.045 Uiso 1 1 calc R . . O9 O -0.03907(5) -0.19672(16) 0.41914(3) 0.0328(2) Uani 1 1 d . . . O10 O -0.27963(5) 0.09719(15) 0.41676(3) 0.0261(2) Uani 1 1 d . . . C11 C -0.13081(7) 0.1348(2) 0.36425(5) 0.0233(3) Uani 1 1 d . . . C12 C -0.05291(7) 0.1273(2) 0.34268(5) 0.0238(3) Uani 1 1 d . . . C13 C -0.00162(7) 0.2955(2) 0.35549(5) 0.0268(3) Uani 1 1 d . . . H13 H -0.0156 0.4108 0.3784 0.032 Uiso 1 1 calc R . . C14 C 0.07032(7) 0.2953(2) 0.33482(5) 0.0268(3) Uani 1 1 d . . . C15 C 0.09080(7) 0.1276(2) 0.30148(5) 0.0287(3) Uani 1 1 d . . . C16 C 0.03882(8) -0.0374(3) 0.28788(5) 0.0333(3) Uani 1 1 d . . . H16 H 0.0525 -0.1510 0.2645 0.040 Uiso 1 1 calc R . . C17 C -0.03259(8) -0.0372(2) 0.30811(5) 0.0310(3) Uani 1 1 d . . . H17 H -0.0682 -0.1499 0.2984 0.037 Uiso 1 1 calc R . . Cl18 Cl 0.13392(2) 0.50499(7) 0.351755(16) 0.04410(12) Uani 1 1 d . . . Cl19 Cl 0.18098(2) 0.12185(8) 0.276897(15) 0.04913(13) Uani 1 1 d . . . C20 C -0.18680(8) 0.2508(3) 0.33127(5) 0.0328(3) Uani 1 1 d . . . H20X H -0.2364 0.2535 0.3474 0.049 Uiso 1 1 calc R . . H20Y H -0.1905 0.1675 0.3000 0.049 Uiso 1 1 calc R . . H20Z H -0.1702 0.4074 0.3248 0.049 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 O1 0.0206(5) 0.0279(5) 0.0270(5) -0.0005(4) 0.0016(4) -0.0013(4) C2 0.0229(7) 0.0248(7) 0.0275(7) 0.0000(5) -0.0018(5) 0.0028(5) O3 0.0273(5) 0.0259(5) 0.0274(5) 0.0029(4) -0.0014(4) 0.0066(4) C4 0.0211(7) 0.0229(6) 0.0293(7) 0.0022(5) -0.0002(5) -0.0010(5) C5 0.0175(6) 0.0203(6) 0.0255(6) -0.0009(5) -0.0014(5) 0.0002(5) C6 0.0218(7) 0.0151(6) 0.0281(7) 0.0013(5) 0.0010(5) -0.0013(5) C7 0.0407(8) 0.0370(8) 0.0271(8) 0.0020(6) 0.0013(6) 0.0012(7) C8 0.0291(7) 0.0253(7) 0.0352(8) -0.0005(6) -0.0076(6) -0.0011(6) O9 0.0269(5) 0.0358(5) 0.0357(5) 0.0012(4) 0.0020(4) 0.0117(4) O10 0.0190(5) 0.0246(5) 0.0348(5) 0.0013(4) -0.0015(4) -0.0001(4) C11 0.0214(7) 0.0217(6) 0.0268(7) -0.0029(5) -0.0007(5) -0.0002(5) C12 0.0241(7) 0.0261(7) 0.0213(6) 0.0021(5) 0.0010(5) 0.0015(5) C13 0.0285(7) 0.0258(7) 0.0260(7) -0.0038(5) 0.0030(5) 0.0011(6) C14 0.0254(7) 0.0281(7) 0.0270(7) 0.0002(6) -0.0018(5) -0.0029(5) C15 0.0224(7) 0.0375(8) 0.0262(7) 0.0004(6) 0.0039(5) 0.0035(6) C16 0.0338(8) 0.0358(8) 0.0303(7) -0.0113(6) 0.0043(6) 0.0020(6) C17 0.0304(8) 0.0309(7) 0.0316(7) -0.0072(6) 0.0020(6) -0.0036(6) Cl18 0.0340(2) 0.0432(2) 0.0551(3) -0.01213(19) 0.00435(16) -0.01302(16) Cl19 0.0271(2) 0.0692(3) 0.0510(3) -0.0180(2) 0.01215(17) -0.00045(18) C20 0.0314(8) 0.0400(8) 0.0270(7) 0.0052(6) -0.0008(6) 0.0065(6) _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 O1 C6 1.3486(15) . ? O1 C2 1.4473(15) . ? C2 O3 1.4433(15) . ? C2 C7 1.5034(19) . ? C2 C8 1.5097(18) . ? O3 C4 1.3466(15) . ? C4 O9 1.2035(15) . ? C4 C5 1.4927(17) . ? C5 C11 1.3427(18) . ? C5 C6 1.4880(17) . ? C6 O10 1.2052(14) . ? C11 C12 1.4972(17) . ? C11 C20 1.4972(18) . ? C12 C13 1.3843(18) . ? C12 C17 1.3916(18) . ? C13 C14 1.3902(18) . ? C14 C15 1.3834(19) . ? C14 Cl18 1.7288(14) . ? C15 C16 1.385(2) . ? C15 Cl19 1.7288(14) . ? C16 C17 1.377(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 C6 O1 C2 119.65(10) . . ? O3 C2 O1 108.83(10) . . ? O3 C2 C7 105.70(10) . . ? O1 C2 C7 105.62(11) . . ? O3 C2 C8 111.32(11) . . ? O1 C2 C8 110.89(11) . . ? C7 C2 C8 114.14(12) . . ? C4 O3 C2 118.60(10) . . ? O9 C4 O3 119.27(12) . . ? O9 C4 C5 124.54(12) . . ? O3 C4 C5 116.06(11) . . ? C11 C5 C6 123.52(11) . . ? C11 C5 C4 121.45(11) . . ? C6 C5 C4 115.03(11) . . ? O10 C6 O1 118.28(11) . . ? O10 C6 C5 126.43(12) . . ? O1 C6 C5 115.26(10) . . ? C5 C11 C12 121.06(11) . . ? C5 C11 C20 125.94(12) . . ? C12 C11 C20 112.92(11) . . ? C13 C12 C17 119.56(12) . . ? C13 C12 C11 118.97(11) . . ? C17 C12 C11 121.37(12) . . ? C12 C13 C14 119.89(12) . . ? C15 C14 C13 120.20(12) . . ? C15 C14 Cl18 120.57(10) . . ? C13 C14 Cl18 119.22(10) . . ? C14 C15 C16 119.77(12) . . ? C14 C15 Cl19 120.46(11) . . ? C16 C15 Cl19 119.77(11) . . ? C17 C16 C15 120.18(13) . . ? C16 C17 C12 120.35(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.304 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.048