 
data_liu20120430e 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H16 Cl2 O3' 
_chemical_formula_weight          303.17 
 
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     P2(1)2(1)2(1)
 
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' 
 
_cell_length_a                    5.2508(5) 
_cell_length_b                    14.2668(12) 
_cell_length_c                    19.7267(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1477.8(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used   1659
_cell_measurement_theta_min     2.8497
_cell_measurement_theta_max     28.6773
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.02 
_exptl_crystal_size_mid           0.01 
_exptl_crystal_size_min           0.01 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.363 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     0.440 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   0.9913 
_exptl_absorpt_correction_T_max   0.9956 
_exptl_absorpt_process_details    sadabs 
 
_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   'Xcalibur, Eos, Gemini'
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             8650 
_diffrn_reflns_av_R_equivalents   0.0356 
_diffrn_reflns_av_sigmaI/netI     0.0409 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.86 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              2612 
_reflns_number_gt                 1915 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1608P)²+0.9020P] where P=(Fo²+2Fc²)/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    -0.01(17) 
_refine_ls_number_reflns          2612 
_refine_ls_number_parameters      175 
_refine_ls_number_restraints      432 
_refine_ls_R_factor_all           0.0756 
_refine_ls_R_factor_gt            0.0548 
_refine_ls_wR_factor_ref          0.1984 
_refine_ls_wR_factor_gt           0.1668 
_refine_ls_goodness_of_fit_ref    0.791 
_refine_ls_restrained_S_all       0.881 
_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 
Cl1 Cl 1.3563(4) 1.25409(13) -0.14511(11) 0.1020(7) Uani 1 1 d U . . 
Cl2 Cl 0.7226(4) 0.96780(13) -0.19877(7) 0.0956(7) Uani 1 1 d U . . 
O1 O 0.3533(8) 0.8912(3) 0.17068(17) 0.0617(8) Uani 1 1 d U . . 
O2 O 0.3588(7) 0.7900(3) 0.00531(19) 0.0640(9) Uani 1 1 d U . . 
H2 H 0.2331 0.7663 -0.0124 0.096 Uiso 1 1 calc R . . 
O3 O 0.6233(7) 0.7785(3) 0.12292(18) 0.0626(8) Uani 1 1 d U . . 
C1 C 1.1382(12) 1.1716(4) -0.1168(3) 0.0637(10) Uani 1 1 d U . . 
C2 C 1.0322(12) 1.1098(4) -0.1629(3) 0.0632(10) Uani 1 1 d U . . 
H2A H 1.0751 1.1128 -0.2086 0.076 Uiso 1 1 calc R . . 
C3 C 0.8620(11) 1.0437(4) -0.1397(3) 0.0595(9) Uani 1 1 d U . . 
C4 C 0.7954(11) 1.0350(4) -0.0715(2) 0.0559(9) Uani 1 1 d U . . 
C5 C 0.9020(11) 1.0996(4) -0.0278(3) 0.0584(9) Uani 1 1 d U . . 
H5 H 0.8578 1.0975 0.0179 0.070 Uiso 1 1 calc R . . 
C6 C 1.0718(12) 1.1674(4) -0.0494(3) 0.0637(10) Uani 1 1 d U . . 
H6 H 1.1407 1.2097 -0.0186 0.076 Uiso 1 1 calc R . . 
C7 C 0.6146(12) 0.9594(4) -0.0480(3) 0.0624(9) Uani 1 1 d U . . 
H7 H 0.5113 0.9231 -0.0759 0.075 Uiso 1 1 calc R . . 
O4 O 0.6286(7) 0.9530(3) 0.02451(16) 0.0590(7) Uani 1 1 d U . . 
C9 C 0.3876(10) 0.9452(4) 0.0572(2) 0.0552(9) Uani 1 1 d U . . 
H9 H 0.2637 0.9871 0.0358 0.066 Uiso 1 1 calc R . . 
C10 C 0.2822(10) 0.8458(4) 0.0608(3) 0.0571(9) Uani 1 1 d U . . 
H10 H 0.0958 0.8489 0.0614 0.069 Uiso 1 1 calc R . . 
C11 C 0.3743(11) 0.8123(4) 0.1296(2) 0.0578(9) Uani 1 1 d U . . 
H11 H 0.2626 0.7624 0.1465 0.069 Uiso 1 1 calc R . . 
C12 C 0.4247(11) 0.9721(4) 0.1322(2) 0.0587(9) Uani 1 1 d U . . 
H12 H 0.6049 0.9861 0.1403 0.070 Uiso 1 1 calc R . . 
C13 C 0.2654(14) 1.0538(4) 0.1553(3) 0.0784(14) Uani 1 1 d U . . 
H13A H 0.2854 1.0620 0.2033 0.118 Uiso 1 1 calc R . . 
H13B H 0.0896 1.0418 0.1452 0.118 Uiso 1 1 calc R . . 
H13C H 0.3195 1.1095 0.1322 0.118 Uiso 1 1 calc R . . 
C14 C 0.7209(13) 0.7401(5) 0.1845(3) 0.0872(17) Uani 1 1 d U . . 
H14A H 0.5832 0.7150 0.2108 0.131 Uiso 1 1 calc R . . 
H14B H 0.8051 0.7885 0.2098 0.131 Uiso 1 1 calc R . . 
H14C H 0.8401 0.6911 0.1742 0.131 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 
Cl1 0.1234(15) 0.0912(12) 0.0912(12) -0.0003(10) 0.0266(11) -0.0456(11) 
Cl2 0.1385(15) 0.1074(12) 0.0408(7) -0.0101(8) 0.0046(8) -0.0482(12) 
O1 0.0715(16) 0.0719(16) 0.0416(14) -0.0018(13) 0.0042(13) 0.0082(15) 
O2 0.0609(18) 0.075(2) 0.0562(19) -0.0241(17) -0.0018(16) -0.0052(17) 
O3 0.0625(15) 0.0727(16) 0.0526(16) 0.0072(14) 0.0053(14) 0.0092(15) 
C1 0.079(2) 0.061(2) 0.051(2) 0.0020(17) 0.0069(19) -0.008(2) 
C2 0.083(2) 0.063(2) 0.0435(19) 0.0024(18) 0.0081(19) -0.0078(19) 
C3 0.0779(19) 0.0624(18) 0.0382(16) -0.0009(16) 0.0029(17) -0.0089(18) 
C4 0.0723(18) 0.0601(17) 0.0354(15) 0.0016(15) 0.0021(16) -0.0037(17) 
C5 0.0750(19) 0.0597(18) 0.0406(17) 0.0000(16) 0.0025(17) -0.0023(18) 
C6 0.081(2) 0.061(2) 0.049(2) -0.0011(18) 0.0033(19) -0.008(2) 
C7 0.0800(19) 0.0694(18) 0.0378(16) -0.0002(16) 0.0019(16) -0.0115(18) 
O4 0.0695(14) 0.0696(14) 0.0380(13) 0.0040(12) 0.0020(12) -0.0053(14) 
C9 0.0637(17) 0.0626(17) 0.0394(16) -0.0006(15) 0.0001(15) 0.0062(16) 
C10 0.0590(17) 0.0680(18) 0.0443(17) -0.0042(16) 0.0025(16) 0.0036(17) 
C11 0.0601(18) 0.0656(19) 0.0477(18) 0.0016(16) 0.0045(17) 0.0020(17) 
C12 0.0678(18) 0.0656(18) 0.0427(17) -0.0050(16) -0.0014(16) 0.0021(17) 
C13 0.095(3) 0.077(3) 0.063(3) -0.014(2) 0.004(3) 0.011(3) 
C14 0.080(3) 0.105(4) 0.077(3) 0.030(3) 0.003(3) 0.016(3) 
 
_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 
Cl1 C1 1.734(6) . ? 
Cl2 C3 1.750(5) . ? 
O1 C11 1.392(6) . ? 
O1 C12 1.431(6) . ? 
O2 C10 1.411(6) . ? 
O3 C11 1.399(7) . ? 
O3 C14 1.427(7) . ? 
C1 C2 1.384(8) . ? 
C1 C6 1.376(8) . ? 
C2 C3 1.377(8) . ? 
C3 C4 1.396(7) . ? 
C4 C5 1.382(7) . ? 
C4 C7 1.509(8) . ? 
C5 C6 1.383(8) . ? 
C7 O4 1.436(6) . ? 
O4 C9 1.425(7) . ? 
C9 C10 1.524(7) . ? 
C9 C12 1.541(7) . ? 
C10 C11 1.518(7) . ? 
C12 C13 1.505(8) . ? 
 
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 
C11 O1 C12 108.8(4) . . ? 
C11 O3 C14 112.8(4) . . ? 
C2 C1 C6 120.3(5) . . ? 
C2 C1 Cl1 119.1(4) . . ? 
C6 C1 Cl1 120.6(4) . . ? 
C1 C2 C3 118.7(5) . . ? 
C4 C3 C2 122.9(5) . . ? 
C4 C3 Cl2 118.8(4) . . ? 
C2 C3 Cl2 118.3(4) . . ? 
C5 C4 C3 116.2(5) . . ? 
C5 C4 C7 122.7(4) . . ? 
C3 C4 C7 121.2(4) . . ? 
C6 C5 C4 122.4(5) . . ? 
C5 C6 C1 119.5(5) . . ? 
O4 C7 C4 108.6(4) . . ? 
C9 O4 C7 114.3(4) . . ? 
O4 C9 C10 114.6(4) . . ? 
O4 C9 C12 107.6(4) . . ? 
C10 C9 C12 103.5(4) . . ? 
O2 C10 C9 112.6(4) . . ? 
O2 C10 C11 115.2(4) . . ? 
C9 C10 C11 102.6(4) . . ? 
O1 C11 O3 114.0(5) . . ? 
O1 C11 C10 103.9(4) . . ? 
O3 C11 C10 108.8(4) . . ? 
O1 C12 C13 108.5(5) . . ? 
O1 C12 C9 106.0(4) . . ? 
C13 C12 C9 114.4(5) . . ? 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.326 
_refine_diff_density_min   -0.255 
_refine_diff_density_rms    0.048 
