data_solve _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H9 Cl O7' _chemical_formula_weight 324.66 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 C2/c _symmetry_space_group_name_hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.0510(8) _cell_length_b 5.5590(8) _cell_length_c 30.980(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.99(2) _cell_angle_gamma 90.00 _cell_volume 2743.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode generator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Delft instruments FAST area detector' _diffrn_measurement_method 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)' _diffrn_standards_number 'None' _diffrn_standards_interval_count 'N/A' _diffrn_standards_interval_time 'N/A' _diffrn_standards_decay_% 'N/A' _diffrn_reflns_number 1922 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0961 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1922 _reflns_number_gt 1158 _reflns_threshold_expression >2\s(I) _computing_data_collection 'MADNES (Pflugrath & Messerschmidt, 1989)' _computing_cell_refinement REFINE _computing_data_reduction 'ABSURD (Karaulov, 1992)' _computing_structure_solution 'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^ > 2\s(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^)+(0.1647P)^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 0 _refine_ls_number_reflns 1922 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.2499 _refine_ls_wR_factor_gt 0.2277 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.89333(8) -0.1670(3) 0.23082(5) 0.0309(5) Uani 1 1 d . . . O6 O 0.6542(4) 0.6771(9) 0.10473(18) 0.0618(15) Uani 1 1 d . . . O4 O 0.4913(4) 0.5677(10) 0.1029(2) 0.0661(16) Uani 1 1 d . . . O3 O 0.5529(3) -0.1244(9) 0.19030(19) 0.0589(15) Uani 1 1 d . . . H1 H 0.5930 -0.2087 0.2019 0.088 Uiso 1 1 calc R . . O5 O 0.4791(7) 0.3524(16) 0.0430(3) 0.150(5) Uani 1 1 d . . . C5 C 0.5239(5) 0.2090(13) 0.1447(3) 0.0518(19) Uani 1 1 d . . . H2 H 0.4660 0.1697 0.1429 0.062 Uiso 1 1 calc R . . C14 C 0.4135(7) 0.7423(17) 0.0424(3) 0.082(3) Uani 1 1 d . . . H3 H 0.4514 0.8739 0.0369 0.124 Uiso 1 1 calc R . . H4 H 0.3752 0.7965 0.0627 0.124 Uiso 1 1 calc R . . H5 H 0.3810 0.6934 0.0150 0.124 Uiso 1 1 calc R . . O2 O 0.8139(4) 0.5557(10) 0.13455(19) 0.0667(17) Uani 1 1 d . . . O1 O 0.7094(3) -0.2176(10) 0.21673(18) 0.0610(15) Uani 1 1 d . . . C8 C 0.6962(4) 0.3219(13) 0.1483(2) 0.0453(17) Uani 1 1 d . . . C4 C 0.5838(5) 0.0649(13) 0.1689(2) 0.0481(19) Uani 1 1 d . . . C13 C 0.4632(6) 0.5352(15) 0.0614(3) 0.063(2) Uani 1 1 d . . . C10 C 0.8469(5) 0.2143(13) 0.1772(3) 0.052(2) Uani 1 1 d . . . H6 H 0.9054 0.2455 0.1789 0.063 Uiso 1 1 calc R . . C3 C 0.6690(4) 0.1157(13) 0.1712(2) 0.0440(18) Uani 1 1 d . . . C1 C 0.8195(5) 0.0247(14) 0.1978(2) 0.0492(19) Uani 1 1 d . . . C2 C 0.7311(5) -0.0366(14) 0.1969(2) 0.0482(18) Uani 1 1 d . . . C6 C 0.5494(5) 0.4073(13) 0.1235(2) 0.0494(19) Uani 1 1 d . . . C9 C 0.7870(5) 0.3745(14) 0.1521(2) 0.0530(19) Uani 1 1 d . . . C7 C 0.6359(5) 0.4646(13) 0.1256(2) 0.0482(19) Uani 1 1 d . . . O7 O 0.7041(4) 0.4789(10) 0.05037(18) 0.0687(17) Uani 1 1 d . . . C11 C 0.6902(5) 0.6580(16) 0.0667(2) 0.056(2) Uani 1 1 d . . . C12 C 0.7112(9) 0.9077(18) 0.0528(4) 0.115(5) Uani 1 1 d . . . H7 H 0.7597 0.9683 0.0720 0.173 Uiso 1 1 calc R . . H8 H 0.6630 1.0138 0.0546 0.173 Uiso 1 1 calc R . . H9 H 0.7246 0.9038 0.0228 0.173 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 0.0202(8) 0.0433(11) 0.0282(8) 0.0049(6) -0.0008(5) 0.0086(6) O6 0.079(4) 0.044(3) 0.067(4) 0.000(3) 0.024(3) 0.002(3) O4 0.063(4) 0.065(4) 0.065(4) -0.007(3) -0.013(3) 0.012(3) O3 0.045(3) 0.061(4) 0.070(4) 0.010(3) 0.006(3) -0.014(3) O5 0.229(11) 0.116(7) 0.086(6) -0.046(5) -0.057(6) 0.092(7) C5 0.045(5) 0.050(5) 0.059(5) -0.009(4) 0.002(4) -0.007(4) C14 0.090(7) 0.081(7) 0.071(6) 0.000(5) -0.013(5) 0.023(5) O2 0.062(4) 0.070(4) 0.067(4) 0.009(3) 0.008(3) -0.029(3) O1 0.055(3) 0.067(4) 0.063(4) 0.010(3) 0.012(3) -0.004(3) C8 0.046(4) 0.050(5) 0.041(4) -0.008(3) 0.010(3) -0.003(4) C4 0.052(5) 0.052(5) 0.042(4) -0.003(3) 0.009(3) -0.005(4) C13 0.081(6) 0.048(5) 0.056(5) -0.006(4) -0.008(4) 0.008(4) C10 0.035(4) 0.057(5) 0.066(5) -0.001(4) 0.009(4) -0.008(3) C3 0.039(4) 0.039(4) 0.055(5) -0.002(3) 0.006(3) -0.001(3) C1 0.045(4) 0.062(5) 0.042(4) -0.005(3) 0.009(3) -0.006(4) C2 0.048(5) 0.055(5) 0.041(4) 0.000(3) 0.003(3) -0.012(4) C6 0.051(5) 0.044(5) 0.051(5) 0.000(3) -0.001(3) 0.004(3) C9 0.046(4) 0.061(5) 0.052(5) 0.000(4) 0.010(3) -0.017(4) C7 0.059(5) 0.041(5) 0.045(4) -0.006(3) 0.009(3) 0.001(3) O7 0.100(5) 0.053(4) 0.056(4) -0.008(3) 0.020(3) 0.003(3) C11 0.068(5) 0.057(6) 0.043(5) 0.005(4) 0.007(4) 0.005(4) C12 0.179(14) 0.049(6) 0.133(11) 0.015(6) 0.082(10) 0.007(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.814(8) . ? O6 C11 1.378(10) . ? O6 C7 1.395(9) . ? O4 C13 1.322(10) . ? O4 C6 1.388(9) . ? O3 C4 1.368(9) . ? O3 H1 0.8400 . ? O5 C13 1.207(10) . ? C5 C6 1.370(11) . ? C5 C4 1.397(11) . ? C5 H2 0.9500 . ? C14 C13 1.481(12) . ? C14 H3 0.9800 . ? C14 H4 0.9800 . ? C14 H5 0.9800 . ? O2 C9 1.246(9) . ? O1 C2 1.250(9) . ? C8 C7 1.377(10) . ? C8 C3 1.443(10) . ? C8 C9 1.477(11) . ? C4 C3 1.390(10) . ? C10 C1 1.333(10) . ? C10 C9 1.464(11) . ? C10 H6 0.9500 . ? C3 C2 1.467(10) . ? C1 C2 1.457(10) . ? C6 C7 1.418(11) . ? O7 C11 1.151(9) . ? C11 C12 1.503(13) . ? C12 H7 0.9800 . ? C12 H8 0.9800 . ? C12 H9 0.9800 . ? 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 O6 C7 117.7(6) . . ? C13 O4 C6 119.4(6) . . ? C4 O3 H1 109.5 . . ? C6 C5 C4 119.5(7) . . ? C6 C5 H2 120.2 . . ? C4 C5 H2 120.2 . . ? C13 C14 H3 109.5 . . ? C13 C14 H4 109.5 . . ? H3 C14 H4 109.5 . . ? C13 C14 H5 109.5 . . ? H3 C14 H5 109.5 . . ? H4 C14 H5 109.5 . . ? C7 C8 C3 118.2(7) . . ? C7 C8 C9 123.5(7) . . ? C3 C8 C9 118.2(7) . . ? O3 C4 C3 122.9(7) . . ? O3 C4 C5 115.8(7) . . ? C3 C4 C5 121.2(7) . . ? O5 C13 O4 120.4(8) . . ? O5 C13 C14 127.0(8) . . ? O4 C13 C14 112.6(7) . . ? C1 C10 C9 120.1(7) . . ? C1 C10 H6 120.0 . . ? C9 C10 H6 120.0 . . ? C4 C3 C8 119.4(7) . . ? C4 C3 C2 120.6(7) . . ? C8 C3 C2 119.9(6) . . ? C10 C1 C2 123.6(7) . . ? C10 C1 Cl1 120.2(6) . . ? C2 C1 Cl1 116.2(6) . . ? O1 C2 C1 120.6(7) . . ? O1 C2 C3 121.3(7) . . ? C1 C2 C3 118.1(7) . . ? C5 C6 O4 120.9(7) . . ? C5 C6 C7 120.4(7) . . ? O4 C6 C7 118.4(7) . . ? O2 C9 C10 119.0(7) . . ? O2 C9 C8 121.1(7) . . ? C10 C9 C8 120.0(7) . . ? C8 C7 O6 123.3(7) . . ? C8 C7 C6 121.2(7) . . ? O6 C7 C6 115.5(7) . . ? O7 C11 O6 124.5(8) . . ? O7 C11 C12 127.7(8) . . ? O6 C11 C12 107.8(8) . . ? C11 C12 H7 109.5 . . ? C11 C12 H8 109.5 . . ? H7 C12 H8 109.5 . . ? C11 C12 H9 109.5 . . ? H7 C12 H9 109.5 . . ? H8 C12 H9 109.5 . . ? _diffrn_measured_fraction_theta_max 0.794 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.794 _refine_diff_density_max 1.302 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.117