data_choromaleciacid _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H3 Cl O4' _chemical_formula_weight 150.51 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.558(2) _cell_length_b 4.9822(14) _cell_length_c 16.015(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.395(6) _cell_angle_gamma 90.00 _cell_volume 602.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2591 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.0 cm. Coverage of the unique set is over 97% complete to at least 26\% in \q. Crystal decay was found to be negligible by by repeating the initial frames at t data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for met atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 3681 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 29.01 _reflns_number_total 1480 _reflns_number_gt 1153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1994)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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^)+(0.0444P)^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_number_reflns 1480 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 -0.34924(16) 0.2749(2) 0.33058(7) 0.0313(3) Uani 1 1 d . . . H1 H -0.444(3) 0.324(4) 0.2983(13) 0.050(6) Uiso 1 1 d . . . O2 O -0.35459(14) -0.1116(2) 0.25848(7) 0.0270(3) Uani 1 1 d . . . C2 C -0.29410(19) 0.0334(3) 0.31292(9) 0.0202(3) Uani 1 1 d . . . Cl3 Cl 0.05987(5) 0.09388(9) 0.33191(3) 0.03278(14) Uani 1 1 d . . . C3 C -0.13231(18) -0.0470(3) 0.36593(9) 0.0209(3) Uani 1 1 d . . . C4 C -0.13065(19) -0.2147(3) 0.43012(9) 0.0236(3) Uani 1 1 d . . . H4 H -0.0204 -0.2610 0.4570 0.028 Uiso 1 1 calc R . . C5 C -0.2945(2) -0.3318(3) 0.46110(9) 0.0221(3) Uani 1 1 d . . . O5 O -0.44230(13) -0.2454(2) 0.43703(6) 0.0276(3) Uani 1 1 d . . . O6 O -0.26878(16) -0.5257(2) 0.51418(7) 0.0304(3) Uani 1 1 d . . . H6 H -0.368(3) -0.597(5) 0.5303(16) 0.080(9) 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 O1 0.0332(7) 0.0215(6) 0.0376(7) -0.0050(5) -0.0164(5) 0.0072(5) O2 0.0232(6) 0.0268(6) 0.0304(6) -0.0081(5) -0.0078(4) 0.0017(4) C2 0.0178(7) 0.0198(7) 0.0228(7) 0.0011(6) -0.0005(5) -0.0015(6) Cl3 0.0200(2) 0.0376(2) 0.0403(3) 0.00950(18) -0.00332(15) -0.00856(16) C3 0.0153(7) 0.0198(7) 0.0273(8) -0.0020(6) -0.0026(5) -0.0015(5) C4 0.0183(7) 0.0232(8) 0.0287(8) 0.0008(6) -0.0047(6) 0.0006(6) C5 0.0216(7) 0.0221(7) 0.0224(7) -0.0010(6) -0.0025(5) 0.0010(6) O5 0.0193(5) 0.0291(6) 0.0346(6) 0.0050(5) 0.0023(4) 0.0056(4) O6 0.0244(6) 0.0349(7) 0.0315(6) 0.0127(5) -0.0030(5) -0.0019(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 O1 C2 1.3078(18) . ? O2 C2 1.2073(17) . ? C2 C3 1.5131(19) . ? Cl3 C3 1.7221(15) . ? C3 C4 1.324(2) . ? C4 C5 1.474(2) . ? C5 O5 1.2429(17) . ? C5 O6 1.2962(18) . ? 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 C2 O1 126.29(13) . . ? O2 C2 C3 121.29(13) . . ? O1 C2 C3 112.31(12) . . ? C4 C3 C2 125.72(13) . . ? C4 C3 Cl3 121.46(11) . . ? C2 C3 Cl3 112.77(11) . . ? C3 C4 C5 122.01(13) . . ? O5 C5 O6 124.74(14) . . ? O5 C5 C4 121.03(13) . . ? O6 C5 C4 114.23(13) . . ? 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 O1 H1 O2 0.90(2) 1.77(2) 2.6643(15) 173(2) 2_455 O6 H6 O5 0.88(3) 1.74(3) 2.6118(17) 177(2) 3_446 C4 H4 O6 0.95 2.46 3.370(2) 161.2 3_546 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.261 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.057