# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Richard Bonar-Law' 'Jamie Bickley' 'Tom McGrath' 'Nirmal Singh' 'Alexander Steiner' _publ_contact_author_name 'Dr Richard Bonar-Law' _publ_contact_author_address ; Department of Chemistry University of Liverpool Liverpool L69 7ZD UNITED KINGDOM ; _publ_contact_author_email BONARLAW@LIV.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Dirhodium (II) carboxylate complexes as building blocks. Cis-chelating dicarboxylic acids designed to bridge the dinuclear core. ; data_tmcg3 _database_code_CSD 220194 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H36 O12' _chemical_formula_weight 564.57 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_Int_Tables_number 15 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 18.591(2) _cell_length_b 10.9955(15) _cell_length_c 21.767(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.150(14) _cell_angle_gamma 90.00 _cell_volume 4379.8(10) _cell_formula_units_Z 6 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1800 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 11369 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 22.49 _reflns_number_total 2855 _reflns_number_gt 839 _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 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^)+(0.1822P)^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 2855 _refine_ls_number_parameters 257 _refine_ls_number_restraints 154 _refine_ls_R_factor_all 0.1291 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.3050 _refine_ls_wR_factor_gt 0.2529 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 1.164 _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 C1 C 0.1667(4) 0.0639(5) 0.2499(3) 0.0510(14) Uani 1 1 d . A . H1 H 0.1668 -0.0207 0.2500 0.061 Uiso 1 1 calc R . . C2 C 0.1191(3) 0.1250(6) 0.2052(3) 0.0515(17) Uani 1 1 d . . . C3 C 0.1189(3) 0.2513(6) 0.2047(3) 0.0553(18) Uani 1 1 d . B . H3 H 0.0873 0.2941 0.1745 0.066 Uiso 1 1 calc R . . C4 C 0.1667(4) 0.3116(5) 0.2500(4) 0.0615(16) Uani 1 1 d U . . H4 H 0.1668 0.3961 0.2500 0.074 Uiso 1 1 calc R B . C5 C 0.2142(3) 0.2511(6) 0.2952(3) 0.0552(18) Uani 1 1 d U A . H5 H 0.2458 0.2937 0.3256 0.066 Uiso 1 1 calc R . . C6 C 0.2140(3) 0.1256(5) 0.2946(3) 0.0504(17) Uani 1 1 d U . . C7 C 0.3232(6) 0.1197(12) 0.3814(5) 0.043(3) Uiso 0.56(2) 1 d PDU A 1 C8 C 0.2838(4) 0.1742(6) 0.4309(3) 0.0563(18) Uani 1 1 d U . . C9 C 0.3763(6) 0.1952(14) 0.3529(6) 0.063(4) Uiso 0.56(2) 1 d PDU A 1 H9A H 0.3498 0.2506 0.3231 0.095 Uiso 0.56(2) 1 calc PR A 1 H9B H 0.4059 0.1429 0.3323 0.095 Uiso 0.56(2) 1 calc PR A 1 H9C H 0.4070 0.2404 0.3850 0.095 Uiso 0.56(2) 1 calc PR A 1 C10 C 0.3609(7) 0.0069(12) 0.4155(6) 0.062(4) Uiso 0.56(2) 1 d PU A 1 H10A H 0.3903 -0.0325 0.3893 0.093 Uiso 0.56(2) 1 calc PR A 1 H10B H 0.3244 -0.0488 0.4246 0.093 Uiso 0.56(2) 1 calc PR A 1 H10C H 0.3914 0.0318 0.4537 0.093 Uiso 0.56(2) 1 calc PR A 1 O4 O 0.0833(5) 0.0423(8) 0.1619(4) 0.041(3) Uiso 0.55(2) 1 d PDU B 1 C11 C 0.0250(7) 0.0813(13) 0.1150(6) 0.058(4) Uiso 0.55(2) 1 d PDU B 1 C12 C 0.0496(4) 0.1739(6) 0.0692(3) 0.0552(18) Uani 1 1 d U B 1 C13 C -0.0356(7) 0.1430(16) 0.1439(6) 0.065(4) Uiso 0.55(2) 1 d PDU B 1 H13A H -0.0515 0.0888 0.1734 0.097 Uiso 0.55(2) 1 calc PR B 1 H13B H -0.0761 0.1623 0.1116 0.097 Uiso 0.55(2) 1 calc PR B 1 H13C H -0.0169 0.2163 0.1648 0.097 Uiso 0.55(2) 1 calc PR B 1 C14 C -0.0033(8) -0.0313(12) 0.0802(7) 0.066(4) Uiso 0.55(2) 1 d PDU B 1 H14A H -0.0036 -0.0971 0.1091 0.099 Uiso 0.55(2) 1 calc PR B 1 H14B H 0.0277 -0.0518 0.0508 0.099 Uiso 0.55(2) 1 calc PR B 1 H14C H -0.0521 -0.0170 0.0583 0.099 Uiso 0.55(2) 1 calc PR B 1 C15 C 0.0476(3) 0.6253(6) 0.2948(3) 0.0514(18) Uani 1 1 d DU . . C16 C 0.0476(3) 0.7513(6) 0.2951(3) 0.0571(19) Uani 1 1 d U C . H16 H 0.0793 0.7942 0.3254 0.069 Uiso 1 1 calc R . . C17 C 0.0000 0.8116(8) 0.2500 0.061(3) Uani 1 2 d SU . . H17 H 0.0000 0.8961 0.2500 0.073 Uiso 1 2 calc SR C . C18 C 0.0000 0.5633(8) 0.2500 0.052(2) Uani 1 2 d SU . . H18 H 0.0000 0.4788 0.2500 0.062 Uiso 1 2 calc SR . . C19 C 0.1563(5) 0.6188(11) 0.3801(5) 0.058(3) Uiso 0.606(17) 1 d PDU C 1 C20 C 0.1173(4) 0.6743(6) 0.4308(3) 0.0574(19) Uani 1 1 d DU . . C21 C 0.2099(6) 0.6954(14) 0.3539(6) 0.073(4) Uiso 0.606(17) 1 d PDU C 1 H21A H 0.2299 0.6495 0.3234 0.109 Uiso 0.606(17) 1 calc PR C 1 H21B H 0.2486 0.7196 0.3869 0.109 Uiso 0.606(17) 1 calc PR C 1 H21C H 0.1858 0.7665 0.3347 0.109 Uiso 0.606(17) 1 calc PR C 1 C22 C 0.1940(4) 0.5106(8) 0.4151(3) 0.069(4) Uiso 0.606(17) 1 d PDU C 1 H22A H 0.1589 0.4634 0.4323 0.103 Uiso 0.606(17) 1 calc PR C 1 H22B H 0.2313 0.5388 0.4483 0.103 Uiso 0.606(17) 1 calc PR C 1 H22C H 0.2157 0.4612 0.3869 0.103 Uiso 0.606(17) 1 calc PR C 1 O7' O 0.0756(4) 0.5286(8) 0.3376(3) 0.044(4) Uiso 0.394(17) 1 d PRDU C 2 C19' C 0.1425(4) 0.5827(8) 0.3862(3) 0.032(4) Uiso 0.394(17) 1 d PRDU C 2 C21' C 0.2044(4) 0.6376(8) 0.3563(3) 0.046(5) Uiso 0.394(17) 1 d PRDU C 2 H21D H 0.1875 0.7111 0.3347 0.068 Uiso 0.394(17) 1 d PR C 2 H21E H 0.2185 0.5804 0.3273 0.068 Uiso 0.394(17) 1 d PR C 2 H21F H 0.2456 0.6554 0.3882 0.068 Uiso 0.394(17) 1 d PR C 2 C7' C 0.3077(7) 0.0780(15) 0.3866(6) 0.042(4) Uiso 0.44(2) 1 d PDU A 2 C9' C 0.3691(8) 0.1352(17) 0.3568(7) 0.058(5) Uiso 0.44(2) 1 d PDU A 2 H9'1 H 0.3515 0.1493 0.3132 0.087 Uiso 0.44(2) 1 calc PR A 2 H9'2 H 0.4101 0.0808 0.3615 0.087 Uiso 0.44(2) 1 calc PR A 2 H9'3 H 0.3838 0.2110 0.3770 0.087 Uiso 0.44(2) 1 calc PR A 2 C10' C 0.3329(9) -0.0356(15) 0.4200(8) 0.060(5) Uiso 0.44(2) 1 d PU A 2 H10D H 0.3334 -0.1002 0.3904 0.091 Uiso 0.44(2) 1 calc PR A 2 H10E H 0.3003 -0.0564 0.4480 0.091 Uiso 0.44(2) 1 calc PR A 2 H10F H 0.3813 -0.0241 0.4433 0.091 Uiso 0.44(2) 1 calc PR A 2 O4' O 0.0615(7) 0.0672(11) 0.1663(5) 0.052(4) Uiso 0.45(2) 1 d PU B 2 C11' C 0.0114(6) 0.1194(12) 0.1196(6) 0.034(4) Uiso 0.45(2) 1 d PDU B 2 C13' C -0.0443(7) 0.2015(17) 0.1458(7) 0.053(4) Uiso 0.45(2) 1 d PDU B 2 H13D H -0.0184 0.2573 0.1757 0.080 Uiso 0.45(2) 1 calc PR B 2 H13E H -0.0759 0.1517 0.1656 0.080 Uiso 0.45(2) 1 calc PR B 2 H13F H -0.0729 0.2463 0.1122 0.080 Uiso 0.45(2) 1 calc PR B 2 C14' C -0.0301(8) 0.0113(13) 0.0856(7) 0.052(5) Uiso 0.45(2) 1 d PDU B 2 H14D H -0.0535 0.0362 0.0447 0.078 Uiso 0.45(2) 1 calc PR B 2 H14E H -0.0663 -0.0165 0.1088 0.078 Uiso 0.45(2) 1 calc PR B 2 H14F H 0.0036 -0.0534 0.0821 0.078 Uiso 0.45(2) 1 calc PR B 2 C22' C 0.1659(8) 0.4629(12) 0.4194(7) 0.044(4) Uiso 0.394(17) 1 d PDU C 2 H22D H 0.1805 0.4066 0.3902 0.066 Uiso 0.394(17) 1 calc PR C 2 H22E H 0.1257 0.4294 0.4360 0.066 Uiso 0.394(17) 1 calc PR C 2 H22F H 0.2062 0.4774 0.4527 0.066 Uiso 0.394(17) 1 calc PR C 2 O1 O 0.2684(5) 0.0640(8) 0.3341(4) 0.050(3) Uiso 0.56(2) 1 d PD A 1 O2 O 0.2222(3) 0.1484(4) 0.4414(2) 0.0684(15) Uani 1 1 d . A . O3 O 0.3252(3) 0.2542(5) 0.4610(2) 0.0788(17) Uani 1 1 d . A . H3A H 0.3071 0.2781 0.4906 0.118 Uiso 1 1 calc R . . O5 O 0.1114(2) 0.1484(4) 0.0586(2) 0.0688(15) Uani 1 1 d . . . O6 O 0.0083(3) 0.2539(5) 0.0391(3) 0.0785(16) Uani 1 1 d . . . H6 H 0.0257 0.2765 0.0090 0.118 Uiso 1 1 calc R B 1 O7 O 0.1006(4) 0.5629(6) 0.3359(3) 0.041(2) Uiso 0.606(17) 1 d PD C 1 O8 O 0.0556(3) 0.6482(4) 0.4414(2) 0.0691(15) Uani 1 1 d . C . O9 O 0.1587(3) 0.7544(5) 0.4610(2) 0.0778(16) Uani 1 1 d . C . H9 H 0.1400 0.7798 0.4899 0.117 Uiso 1 1 calc R . . O1' O 0.2465(6) 0.0377(10) 0.3384(4) 0.040(3) Uiso 0.44(2) 1 d P A 2 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 C1 0.075(3) 0.045(3) 0.036(3) -0.001(4) 0.019(3) 0.001(4) C2 0.059(4) 0.063(4) 0.035(4) 0.001(3) 0.014(3) -0.015(3) C3 0.063(4) 0.062(4) 0.039(4) 0.006(3) 0.001(3) -0.003(3) C4 0.085(4) 0.052(3) 0.046(4) -0.001(4) 0.007(3) -0.001(4) C5 0.062(4) 0.063(4) 0.037(4) -0.009(3) 0.001(3) 0.000(3) C6 0.062(4) 0.058(4) 0.032(4) -0.001(3) 0.012(3) 0.013(3) C8 0.055(4) 0.074(5) 0.037(4) 0.003(4) 0.000(3) 0.025(3) C12 0.058(4) 0.070(4) 0.034(4) -0.003(3) -0.001(3) -0.025(3) C15 0.061(4) 0.062(4) 0.033(4) -0.003(3) 0.015(3) 0.014(3) C16 0.064(4) 0.064(4) 0.042(4) -0.008(3) 0.003(3) 0.001(3) C17 0.080(6) 0.049(5) 0.051(6) 0.000 0.004(5) 0.000 C18 0.072(6) 0.049(5) 0.036(5) 0.000 0.017(5) 0.000 C20 0.055(4) 0.078(5) 0.038(4) 0.005(4) 0.005(3) 0.026(3) O2 0.065(3) 0.090(3) 0.049(3) -0.009(3) 0.009(2) 0.011(2) O3 0.072(3) 0.109(4) 0.057(4) -0.019(3) 0.015(3) 0.000(3) O5 0.063(3) 0.092(4) 0.051(3) 0.009(3) 0.010(3) -0.011(2) O6 0.073(3) 0.108(4) 0.057(4) 0.020(3) 0.017(3) -0.002(3) O8 0.066(3) 0.091(3) 0.050(3) -0.011(3) 0.010(3) 0.012(2) O9 0.071(3) 0.107(4) 0.057(4) -0.019(3) 0.014(3) -0.001(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 C1 C2 1.371(8) . ? C1 C6 1.371(8) . ? C2 C3 1.388(8) . ? C2 O4 1.391(9) . ? C2 O4' 1.396(11) . ? C3 C4 1.375(8) . ? C4 C5 1.373(8) . ? C5 C6 1.379(8) . ? C6 O1 1.384(9) . ? C6 O1' 1.417(11) . ? C7 O1 1.451(11) . ? C7 C9 1.504(13) . ? C7 C8 1.527(13) . ? C7 C10 1.548(15) . ? C8 O2 1.240(7) . ? C8 O3 1.272(7) . ? C8 C7' 1.548(14) . ? O4 C11 1.419(12) . ? C11 C14 1.497(13) . ? C11 C13 1.541(13) . ? C11 C12 1.549(14) . ? C12 O5 1.242(8) . ? C12 O6 1.272(7) . ? C12 C11' 1.530(14) . ? C15 C18 1.376(7) . ? C15 C16 1.386(9) . ? C15 O7 1.390(7) . ? C15 O7' 1.450(8) . ? C16 C17 1.372(7) . ? C17 C16 1.372(7) 2 ? C18 C15 1.376(7) 2 ? C19 O7 1.423(11) . ? C19 C21 1.494(12) . ? C19 C22 1.516(11) . ? C19 C20 1.547(10) . ? C20 O8 1.243(8) . ? C20 O9 1.273(7) . ? C20 C19' 1.528(8) . ? O7' C19' 1.5989 . ? C19' C22' 1.528(12) . ? C19' C21' 1.5410 . ? C7' O1' 1.473(15) . ? C7' C10' 1.480(19) . ? C7' C9' 1.542(14) . ? O4' C11' 1.377(15) . ? C11' C14' 1.533(13) . ? C11' C13' 1.556(14) . ? 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 C2 C1 C6 121.0(5) . . ? C1 C2 C3 119.7(6) . . ? C1 C2 O4 109.4(6) . . ? C3 C2 O4 130.4(7) . . ? C1 C2 O4' 122.5(7) . . ? C3 C2 O4' 116.8(7) . . ? O4 C2 O4' 21.2(5) . . ? C4 C3 C2 118.5(6) . . ? C5 C4 C3 122.2(5) . . ? C4 C5 C6 118.5(6) . . ? C1 C6 C5 120.2(5) . . ? C1 C6 O1 120.4(6) . . ? C5 C6 O1 118.9(6) . . ? C1 C6 O1' 106.5(7) . . ? C5 C6 O1' 132.5(7) . . ? O1 C6 O1' 21.4(5) . . ? O1 C7 C9 111.7(10) . . ? O1 C7 C8 107.5(8) . . ? C9 C7 C8 120.4(9) . . ? O1 C7 C10 101.7(9) . . ? C9 C7 C10 111.5(10) . . ? C8 C7 C10 102.1(9) . . ? O2 C8 O3 123.8(6) . . ? O2 C8 C7 127.9(7) . . ? O3 C8 C7 108.3(7) . . ? O2 C8 C7' 109.6(8) . . ? O3 C8 C7' 125.5(8) . . ? C7 C8 C7' 21.1(5) . . ? C2 O4 C11 120.2(8) . . ? O4 C11 C14 105.7(10) . . ? O4 C11 C13 111.1(10) . . ? C14 C11 C13 110.7(10) . . ? O4 C11 C12 112.7(8) . . ? C14 C11 C12 109.6(10) . . ? C13 C11 C12 107.1(10) . . ? O5 C12 O6 123.7(6) . . ? O5 C12 C11' 127.3(7) . . ? O6 C12 C11' 109.0(7) . . ? O5 C12 C11 111.0(8) . . ? O6 C12 C11 124.5(8) . . ? C11' C12 C11 19.0(5) . . ? C18 C15 C16 119.9(6) . . ? C18 C15 O7 120.4(6) . . ? C16 C15 O7 119.4(6) . . ? C18 C15 O7' 101.9(6) . . ? C16 C15 O7' 136.9(6) . . ? O7 C15 O7' 24.5(3) . . ? C17 C16 C15 118.6(6) . . ? C16 C17 C16 122.3(9) 2 . ? C15 C18 C15 120.6(8) 2 . ? O7 C19 C21 116.1(9) . . ? O7 C19 C22 102.6(7) . . ? C21 C19 C22 110.7(8) . . ? O7 C19 C20 106.1(7) . . ? C21 C19 C20 118.5(9) . . ? C22 C19 C20 100.6(7) . . ? O8 C20 O9 123.9(6) . . ? O8 C20 C19' 111.2(7) . . ? O9 C20 C19' 124.0(7) . . ? O8 C20 C19 127.2(7) . . ? O9 C20 C19 109.0(7) . . ? C19' C20 C19 18.8(4) . . ? C15 O7' C19' 107.6(4) . . ? C20 C19' C22' 111.2(7) . . ? C20 C19' C21' 110.2(5) . . ? C22' C19' C21' 111.5(5) . . ? C20 C19' O7' 112.1(4) . . ? C22' C19' O7' 96.6(5) . . ? C21' C19' O7' 114.7 . . ? O1' C7' C10' 103.5(11) . . ? O1' C7' C9' 111.1(10) . . ? C10' C7' C9' 111.0(11) . . ? O1' C7' C8 112.2(8) . . ? C10' C7' C8 111.8(11) . . ? C9' C7' C8 107.4(11) . . ? C11' O4' C2 127.2(10) . . ? O4' C11' C12 110.7(9) . . ? O4' C11' C14' 104.5(10) . . ? C12 C11' C14' 102.4(9) . . ? O4' C11' C13' 112.2(11) . . ? C12 C11' C13' 117.3(9) . . ? C14' C11' C13' 108.5(10) . . ? C6 O1 C7 125.4(8) . . ? C15 O7 C19 124.8(6) . . ? C6 O1' C7' 117.3(9) . . ? 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 C6 C1 C2 C3 0.4(10) . . . . ? C6 C1 C2 O4 173.3(7) . . . . ? C6 C1 C2 O4' -168.1(8) . . . . ? C1 C2 C3 C4 -0.6(10) . . . . ? O4 C2 C3 C4 -171.8(8) . . . . ? O4' C2 C3 C4 168.5(8) . . . . ? C2 C3 C4 C5 0.2(12) . . . . ? C3 C4 C5 C6 0.4(12) . . . . ? C2 C1 C6 C5 0.2(11) . . . . ? C2 C1 C6 O1 -171.2(7) . . . . ? C2 C1 C6 O1' 171.0(7) . . . . ? C4 C5 C6 C1 -0.6(10) . . . . ? C4 C5 C6 O1 170.9(7) . . . . ? C4 C5 C6 O1' -168.6(9) . . . . ? O1 C7 C8 O2 20.0(13) . . . . ? C9 C7 C8 O2 149.4(9) . . . . ? C10 C7 C8 O2 -86.6(10) . . . . ? O1 C7 C8 O3 -159.6(7) . . . . ? C9 C7 C8 O3 -30.3(11) . . . . ? C10 C7 C8 O3 93.7(9) . . . . ? O1 C7 C8 C7' 53.1(15) . . . . ? C9 C7 C8 C7' -178(2) . . . . ? C10 C7 C8 C7' -53.6(17) . . . . ? C1 C2 O4 C11 172.6(8) . . . . ? C3 C2 O4 C11 -15.5(13) . . . . ? O4' C2 O4 C11 40.6(17) . . . . ? C2 O4 C11 C14 -176.3(9) . . . . ? C2 O4 C11 C13 -56.1(12) . . . . ? C2 O4 C11 C12 64.1(12) . . . . ? O4 C11 C12 O5 37.1(11) . . . . ? C14 C11 C12 O5 -80.3(9) . . . . ? C13 C11 C12 O5 159.5(8) . . . . ? O4 C11 C12 O6 -153.0(8) . . . . ? C14 C11 C12 O6 89.6(11) . . . . ? C13 C11 C12 O6 -30.6(11) . . . . ? O4 C11 C12 C11' -114(2) . . . . ? C14 C11 C12 C11' 128(2) . . . . ? C13 C11 C12 C11' 8.0(16) . . . . ? C18 C15 C16 C17 -0.6(8) . . . . ? O7 C15 C16 C17 173.2(5) . . . . ? O7' C15 C16 C17 -164.7(7) . . . . ? C15 C16 C17 C16 0.3(4) . . . 2 ? C16 C15 C18 C15 0.3(4) . . . 2 ? O7 C15 C18 C15 -173.4(7) . . . 2 ? O7' C15 C18 C15 169.3(5) . . . 2 ? O7 C19 C20 O8 18.4(11) . . . . ? C21 C19 C20 O8 151.1(8) . . . . ? C22 C19 C20 O8 -88.2(8) . . . . ? O7 C19 C20 O9 -160.9(7) . . . . ? C21 C19 C20 O9 -28.2(10) . . . . ? C22 C19 C20 O9 92.5(7) . . . . ? O7 C19 C20 C19' 53.4(11) . . . . ? C21 C19 C20 C19' -173.9(18) . . . . ? C22 C19 C20 C19' -53.2(10) . . . . ? C18 C15 O7' C19' 170.1(2) . . . . ? C16 C15 O7' C19' -23.9(9) . . . . ? O7 C15 O7' C19' 28.3(8) . . . . ? O8 C20 C19' C22' -75.2(8) . . . . ? O9 C20 C19' C22' 94.1(8) . . . . ? C19 C20 C19' C22' 134.1(15) . . . . ? O8 C20 C19' C21' 160.7(4) . . . . ? O9 C20 C19' C21' -30.0(7) . . . . ? C19 C20 C19' C21' 10.0(12) . . . . ? O8 C20 C19' O7' 31.7(6) . . . . ? O9 C20 C19' O7' -159.0(5) . . . . ? C19 C20 C19' O7' -119.0(13) . . . . ? C15 O7' C19' C20 69.9(5) . . . . ? C15 O7' C19' C22' -174.0(8) . . . . ? C15 O7' C19' C21' -56.7(4) . . . . ? O2 C8 C7' O1' 38.0(12) . . . . ? O3 C8 C7' O1' -153.8(8) . . . . ? C7 C8 C7' O1' -115(2) . . . . ? O2 C8 C7' C10' -77.7(11) . . . . ? O3 C8 C7' C10' 90.4(13) . . . . ? C7 C8 C7' C10' 129(2) . . . . ? O2 C8 C7' C9' 160.3(9) . . . . ? O3 C8 C7' C9' -31.5(13) . . . . ? C7 C8 C7' C9' 7.5(15) . . . . ? C1 C2 O4' C11' -179.1(10) . . . . ? C3 C2 O4' C11' 12.1(17) . . . . ? O4 C2 O4' C11' -123(3) . . . . ? C2 O4' C11' C12 61.0(15) . . . . ? C2 O4' C11' C14' 170.6(11) . . . . ? C2 O4' C11' C13' -72.1(15) . . . . ? O5 C12 C11' O4' 20.4(13) . . . . ? O6 C12 C11' O4' -158.5(8) . . . . ? C11 C12 C11' O4' 54.5(17) . . . . ? O5 C12 C11' C14' -90.5(10) . . . . ? O6 C12 C11' C14' 90.7(9) . . . . ? C11 C12 C11' C14' -56.4(19) . . . . ? O5 C12 C11' C13' 150.9(9) . . . . ? O6 C12 C11' C13' -28.0(11) . . . . ? C11 C12 C11' C13' -175(3) . . . . ? C1 C6 O1 C7 177.5(8) . . . . ? C5 C6 O1 C7 6.0(13) . . . . ? O1' C6 O1 C7 -129(2) . . . . ? C9 C7 O1 C6 -68.1(13) . . . . ? C8 C7 O1 C6 66.0(12) . . . . ? C10 C7 O1 C6 172.9(9) . . . . ? C18 C15 O7 C19 174.3(6) . . . . ? C16 C15 O7 C19 0.6(11) . . . . ? O7' C15 O7 C19 -141.1(13) . . . . ? C21 C19 O7 C15 -63.4(11) . . . . ? C22 C19 O7 C15 175.8(6) . . . . ? C20 C19 O7 C15 70.6(10) . . . . ? C1 C6 O1' C7' 171.3(8) . . . . ? C5 C6 O1' C7' -19.5(14) . . . . ? O1 C6 O1' C7' 37.6(15) . . . . ? C10' C7' O1' C6 -174.9(10) . . . . ? C9' C7' O1' C6 -55.7(13) . . . . ? C8 C7' O1' C6 64.5(12) . . . . ? 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 O9 H9 O5 0.82 1.85 2.664(7) 170.9 6_566 O6 H6 O8 0.82 1.86 2.667(7) 170.0 6_565 O3 H3A O2 0.82 1.85 2.664(7) 170.7 7_556 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.372 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.048 data_tmcg14 _database_code_CSD 220195 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 O4 S2' _chemical_formula_weight 314.40 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_Int_Tables_number 14 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 10.5028(15) _cell_length_b 12.5327(14) _cell_length_c 12.1758(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.081(16) _cell_angle_gamma 90.00 _cell_volume 1601.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 9987 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.22 _reflns_number_total 2453 _reflns_number_gt 1772 _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 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^)+(0.0618P)^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 SHELXL _refine_ls_extinction_coef 0.0041(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2453 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 C1 C 0.7682(2) 0.40288(17) 0.26956(19) 0.0353(5) Uani 1 1 d . . . H1 H 0.6796 0.3978 0.2571 0.042 Uiso 1 1 calc R . . C2 C 0.8386(2) 0.31130(17) 0.29253(19) 0.0353(5) Uani 1 1 d . . . C3 C 0.9695(2) 0.31906(19) 0.3122(2) 0.0467(6) Uani 1 1 d . . . H3 H 1.0181 0.2575 0.3275 0.056 Uiso 1 1 calc R . . C4 C 1.0278(2) 0.4178(2) 0.3091(3) 0.0555(7) Uani 1 1 d . . . H4 H 1.1161 0.4232 0.3233 0.067 Uiso 1 1 calc R . . C5 C 0.9577(2) 0.5088(2) 0.2852(2) 0.0501(7) Uani 1 1 d . . . H5 H 0.9985 0.5755 0.2828 0.060 Uiso 1 1 calc R . . C6 C 0.8271(2) 0.50189(17) 0.2647(2) 0.0373(5) Uani 1 1 d . . . C7 C 0.6909(2) 0.67328(18) 0.3592(2) 0.0444(6) Uani 1 1 d . . . C8 C 0.6098(2) 0.59407(19) 0.4192(2) 0.0442(6) Uani 1 1 d . . . C9 C 0.8072(3) 0.7045(2) 0.4293(3) 0.0637(8) Uani 1 1 d . . . H9A H 0.7805 0.7323 0.4991 0.076 Uiso 1 1 calc R . . H9B H 0.8548 0.7587 0.3915 0.076 Uiso 1 1 calc R . . H9C H 0.8607 0.6423 0.4420 0.076 Uiso 1 1 calc R . . C10 C 0.6101(3) 0.7709(2) 0.3259(3) 0.0699(9) Uani 1 1 d . . . H10A H 0.5815 0.8064 0.3914 0.084 Uiso 1 1 calc R . . H10B H 0.5368 0.7480 0.2813 0.084 Uiso 1 1 calc R . . H10C H 0.6610 0.8198 0.2841 0.084 Uiso 1 1 calc R . . C11 C 0.7350(2) 0.15072(18) 0.4322(2) 0.0374(5) Uani 1 1 d . . . C12 C 0.7205(3) 0.2494(2) 0.5032(2) 0.0526(7) Uani 1 1 d . . . H12A H 0.7084 0.2280 0.5787 0.063 Uiso 1 1 calc R . . H12B H 0.6473 0.2902 0.4765 0.063 Uiso 1 1 calc R . . H12C H 0.7966 0.2930 0.4997 0.063 Uiso 1 1 calc R . . C13 C 0.6160(2) 0.0821(2) 0.4306(3) 0.0598(8) Uani 1 1 d . . . H13A H 0.5982 0.0604 0.5049 0.072 Uiso 1 1 calc R . . H13B H 0.6292 0.0193 0.3858 0.072 Uiso 1 1 calc R . . H13C H 0.5446 0.1227 0.3999 0.072 Uiso 1 1 calc R . . C14 C 0.8505(2) 0.08531(17) 0.4664(2) 0.0382(6) Uani 1 1 d . . . O1 O 0.6388(2) 0.5637(2) 0.5111(2) 0.0836(7) Uani 1 1 d . . . O2 O 0.5073(2) 0.5622(2) 0.36743(19) 0.0774(7) Uani 1 1 d . . . H22 H 0.466(3) 0.522(3) 0.408(3) 0.116 Uiso 1 1 calc R . . O3 O 0.94987(17) 0.13297(13) 0.50325(17) 0.0582(5) Uani 1 1 d . . . O4 O 0.84491(17) -0.01459(13) 0.45483(18) 0.0593(5) Uani 1 1 d . . . H44 H 0.9153 -0.0412 0.4717 0.089 Uiso 1 1 calc R . . S1 S 0.73621(6) 0.61618(4) 0.22646(5) 0.0431(2) Uani 1 1 d . . . S2 S 0.75881(6) 0.18644(4) 0.28703(5) 0.0401(2) Uani 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 C1 0.0355(12) 0.0380(12) 0.0326(14) -0.0002(10) 0.0029(9) -0.0002(10) C2 0.0395(13) 0.0346(12) 0.0319(14) 0.0009(9) 0.0050(10) 0.0028(9) C3 0.0415(14) 0.0442(14) 0.0548(18) 0.0071(12) 0.0072(11) 0.0080(11) C4 0.0315(12) 0.0597(17) 0.075(2) 0.0094(14) 0.0050(12) -0.0013(12) C5 0.0403(14) 0.0442(14) 0.066(2) 0.0070(12) 0.0103(12) -0.0075(11) C6 0.0391(13) 0.0363(12) 0.0370(15) 0.0036(10) 0.0069(10) -0.0003(10) C7 0.0476(14) 0.0344(13) 0.0516(17) -0.0038(11) 0.0106(12) -0.0062(10) C8 0.0424(14) 0.0405(13) 0.0501(19) -0.0041(11) 0.0066(12) -0.0035(11) C9 0.0634(18) 0.0688(19) 0.059(2) -0.0154(14) 0.0100(14) -0.0285(14) C10 0.075(2) 0.0376(15) 0.099(3) 0.0007(15) 0.0246(18) 0.0076(13) C11 0.0375(12) 0.0373(12) 0.0375(15) 0.0046(10) 0.0019(10) 0.0017(10) C12 0.0700(18) 0.0516(15) 0.0367(16) -0.0013(12) 0.0097(12) 0.0131(13) C13 0.0413(14) 0.0580(17) 0.080(2) 0.0188(15) 0.0020(13) -0.0039(12) C14 0.0444(13) 0.0338(13) 0.0363(15) 0.0078(10) -0.0014(10) -0.0014(10) O1 0.0733(14) 0.1108(19) 0.0659(17) 0.0267(14) -0.0073(12) -0.0419(13) O2 0.0609(13) 0.0979(17) 0.0727(16) 0.0234(12) -0.0067(11) -0.0368(12) O3 0.0521(11) 0.0426(10) 0.0781(15) 0.0011(9) -0.0224(9) -0.0047(8) O4 0.0504(11) 0.0333(10) 0.0931(16) 0.0078(9) -0.0129(10) 0.0026(8) S1 0.0499(4) 0.0344(3) 0.0452(4) 0.0066(3) 0.0036(3) 0.0012(3) S2 0.0529(4) 0.0319(3) 0.0352(4) -0.0013(2) -0.0019(3) 0.0014(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 C1 C2 1.388(3) . ? C1 C6 1.389(3) . ? C2 C3 1.391(3) . ? C2 S2 1.775(2) . ? C3 C4 1.382(4) . ? C4 C5 1.383(4) . ? C5 C6 1.388(3) . ? C6 S1 1.774(2) . ? C7 C8 1.513(3) . ? C7 C9 1.516(4) . ? C7 C10 1.535(4) . ? C7 S1 1.846(3) . ? C8 O1 1.210(3) . ? C8 O2 1.290(3) . ? C11 C14 1.509(3) . ? C11 C13 1.517(3) . ? C11 C12 1.520(3) . ? C11 S2 1.849(2) . ? C14 O4 1.261(3) . ? C14 O3 1.270(3) . ? 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 C2 C1 C6 120.8(2) . . ? C1 C2 C3 119.5(2) . . ? C1 C2 S2 118.29(17) . . ? C3 C2 S2 122.05(17) . . ? C4 C3 C2 119.6(2) . . ? C3 C4 C5 120.8(2) . . ? C4 C5 C6 120.1(2) . . ? C5 C6 C1 119.1(2) . . ? C5 C6 S1 121.03(17) . . ? C1 C6 S1 119.77(17) . . ? C8 C7 C9 110.7(2) . . ? C8 C7 C10 109.6(2) . . ? C9 C7 C10 111.7(2) . . ? C8 C7 S1 109.62(16) . . ? C9 C7 S1 111.37(18) . . ? C10 C7 S1 103.61(19) . . ? O1 C8 O2 122.1(2) . . ? O1 C8 C7 121.7(2) . . ? O2 C8 C7 116.2(3) . . ? C14 C11 C13 110.43(19) . . ? C14 C11 C12 112.4(2) . . ? C13 C11 C12 111.7(2) . . ? C14 C11 S2 105.09(16) . . ? C13 C11 S2 105.33(17) . . ? C12 C11 S2 111.50(17) . . ? O4 C14 O3 122.7(2) . . ? O4 C14 C11 118.3(2) . . ? O3 C14 C11 118.92(19) . . ? C6 S1 C7 103.68(11) . . ? C2 S2 C11 104.91(11) . . ? 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 C6 C1 C2 C3 0.7(3) . . . . ? C6 C1 C2 S2 -175.26(18) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? S2 C2 C3 C4 176.1(2) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? C4 C5 C6 S1 -176.5(2) . . . . ? C2 C1 C6 C5 -1.2(3) . . . . ? C2 C1 C6 S1 175.93(18) . . . . ? C9 C7 C8 O1 0.6(4) . . . . ? C10 C7 C8 O1 -123.0(3) . . . . ? S1 C7 C8 O1 123.9(3) . . . . ? C9 C7 C8 O2 179.6(2) . . . . ? C10 C7 C8 O2 55.9(3) . . . . ? S1 C7 C8 O2 -57.1(3) . . . . ? C13 C11 C14 O4 22.0(3) . . . . ? C12 C11 C14 O4 147.4(2) . . . . ? S2 C11 C14 O4 -91.1(2) . . . . ? C13 C11 C14 O3 -159.6(2) . . . . ? C12 C11 C14 O3 -34.2(3) . . . . ? S2 C11 C14 O3 87.3(2) . . . . ? C5 C6 S1 C7 -88.7(2) . . . . ? C1 C6 S1 C7 94.2(2) . . . . ? C8 C7 S1 C6 -62.05(19) . . . . ? C9 C7 S1 C6 60.9(2) . . . . ? C10 C7 S1 C6 -178.93(17) . . . . ? C1 C2 S2 C11 -102.31(19) . . . . ? C3 C2 S2 C11 81.8(2) . . . . ? C14 C11 S2 C2 -91.72(16) . . . . ? C13 C11 S2 C2 151.62(16) . . . . ? C12 C11 S2 C2 30.32(19) . . . . ? 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 O2 H22 O1 0.84 1.85 2.684(3) 174.0 3_666 O4 H44 O3 0.83 1.84 2.651(2) 164.7 3_756 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 24.22 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.228 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.046 data_tmcg27 _database_code_CSD 220196 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 O6' _chemical_formula_weight 226.18 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7348(15) _cell_length_b 7.0518(15) _cell_length_c 11.256(2) _cell_angle_alpha 75.30(3) _cell_angle_beta 73.98(3) _cell_angle_gamma 71.04(3) _cell_volume 477.94(18) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 ? _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 3015 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.10 _reflns_number_total 1399 _reflns_number_gt 1128 _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 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^)+(0.0569P)^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 1399 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 C1 C 1.1159(2) 0.1887(2) 0.04097(14) 0.0166(3) Uani 1 1 d . . . C2 C 1.2069(2) 0.3298(2) 0.07605(14) 0.0196(4) Uani 1 1 d . . . H2A H 1.3274 0.2520 0.1170 0.024 Uiso 1 1 calc R . . H2B H 1.2583 0.4220 0.0011 0.024 Uiso 1 1 calc R . . C3 C 1.0832(2) 0.5655(2) 0.21976(14) 0.0186(4) Uani 1 1 d . . . C4 C 1.2646(2) 0.6343(2) 0.18395(15) 0.0206(4) Uani 1 1 d . . . H4 H 1.3745 0.5921 0.1159 0.025 Uiso 1 1 calc R . . C5 C 1.2810(2) 0.7678(2) 0.25109(15) 0.0194(4) Uani 1 1 d . . . H5 H 1.4036 0.8160 0.2275 0.023 Uiso 1 1 calc R . . C6 C 1.1211(2) 0.8307(2) 0.35140(14) 0.0190(4) Uani 1 1 d . . . H6 H 1.1334 0.9222 0.3952 0.023 Uiso 1 1 calc R . . C7 C 0.9413(2) 0.7566(2) 0.38676(14) 0.0159(3) Uani 1 1 d . . . C8 C 0.9208(2) 0.6252(2) 0.32117(14) 0.0193(4) Uani 1 1 d . . . H8 H 0.7984 0.5767 0.3449 0.023 Uiso 1 1 calc R . . C9 C 0.6168(2) 0.7290(2) 0.53054(14) 0.0182(4) Uani 1 1 d . . . H9A H 0.6743 0.5803 0.5445 0.022 Uiso 1 1 calc R . . H9B H 0.5316 0.7690 0.4658 0.022 Uiso 1 1 calc R . . C10 C 0.4767(2) 0.7944(2) 0.65015(14) 0.0177(4) Uani 1 1 d . . . O1 O 1.25204(16) 0.08919(16) -0.04555(10) 0.0245(3) Uani 1 1 d . . . H1 H 1.1966 0.0122 -0.0619 0.037 Uiso 1 1 calc R . . O2 O 0.93547(16) 0.16928(16) 0.08820(10) 0.0216(3) Uani 1 1 d . . . O3 O 1.03913(17) 0.44115(17) 0.15907(11) 0.0266(3) Uani 1 1 d . . . O4 O 0.78854(15) 0.82110(15) 0.48914(9) 0.0193(3) Uani 1 1 d . . . O5 O 0.31339(17) 0.71243(16) 0.68370(10) 0.0266(3) Uani 1 1 d . . . H5A H 0.2360 0.7454 0.7508 0.040 Uiso 1 1 calc R . . O6 O 0.50647(17) 0.90195(16) 0.70782(10) 0.0235(3) Uani 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 C1 0.0172(8) 0.0187(7) 0.0129(8) -0.0045(7) -0.0031(7) -0.0025(6) C2 0.0170(8) 0.0246(8) 0.0193(9) -0.0114(7) -0.0006(6) -0.0055(6) C3 0.0198(8) 0.0204(8) 0.0195(9) -0.0082(7) -0.0051(7) -0.0063(6) C4 0.0176(8) 0.0253(8) 0.0179(9) -0.0072(7) 0.0001(6) -0.0051(6) C5 0.0169(7) 0.0219(8) 0.0222(8) -0.0055(7) -0.0027(6) -0.0091(6) C6 0.0211(8) 0.0186(7) 0.0204(9) -0.0066(7) -0.0065(7) -0.0055(6) C7 0.0165(7) 0.0169(7) 0.0144(8) -0.0055(7) -0.0029(6) -0.0029(6) C8 0.0163(8) 0.0239(8) 0.0205(9) -0.0075(7) -0.0014(7) -0.0083(6) C9 0.0196(8) 0.0193(8) 0.0186(9) -0.0080(7) -0.0022(6) -0.0073(6) C10 0.0179(8) 0.0160(7) 0.0188(8) -0.0028(7) -0.0063(6) -0.0026(6) O1 0.0221(6) 0.0306(6) 0.0254(7) -0.0194(5) 0.0017(5) -0.0078(5) O2 0.0199(6) 0.0266(6) 0.0214(6) -0.0126(5) 0.0004(5) -0.0079(4) O3 0.0206(6) 0.0384(6) 0.0297(7) -0.0268(6) 0.0053(5) -0.0127(5) O4 0.0191(5) 0.0241(6) 0.0188(6) -0.0130(5) 0.0024(5) -0.0096(4) O5 0.0230(6) 0.0345(7) 0.0254(7) -0.0163(6) 0.0080(5) -0.0146(5) O6 0.0262(6) 0.0264(6) 0.0218(6) -0.0116(5) -0.0036(5) -0.0083(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 C1 O2 1.2219(18) . ? C1 O1 1.3104(19) . ? C1 C2 1.501(2) . ? C2 O3 1.4069(19) . ? C3 C4 1.380(2) . ? C3 O3 1.3816(19) . ? C3 C8 1.390(2) . ? C4 C5 1.395(2) . ? C5 C6 1.380(2) . ? C6 C7 1.392(2) . ? C7 O4 1.3787(19) . ? C7 C8 1.382(2) . ? C9 O4 1.4191(17) . ? C9 C10 1.499(2) . ? C10 O6 1.2071(18) . ? C10 O5 1.3267(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 C1 O1 124.16(14) . . ? O2 C1 C2 123.56(14) . . ? O1 C1 C2 112.28(12) . . ? O3 C2 C1 106.45(12) . . ? C4 C3 O3 125.20(14) . . ? C4 C3 C8 121.20(14) . . ? O3 C3 C8 113.56(12) . . ? C3 C4 C5 118.47(14) . . ? C6 C5 C4 121.44(14) . . ? C5 C6 C7 118.91(14) . . ? O4 C7 C8 122.78(13) . . ? O4 C7 C6 116.54(13) . . ? C8 C7 C6 120.69(14) . . ? C7 C8 C3 119.28(13) . . ? O4 C9 C10 109.97(12) . . ? O6 C10 O5 125.11(14) . . ? O6 C10 C9 126.37(13) . . ? O5 C10 C9 108.52(12) . . ? C3 O3 C2 119.34(11) . . ? C7 O4 C9 115.48(11) . . ? 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 O2 C1 C2 O3 -5.96(18) . . . . ? O1 C1 C2 O3 174.14(11) . . . . ? O3 C3 C4 C5 176.73(12) . . . . ? C8 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C4 C5 C6 C7 0.8(2) . . . . ? C5 C6 C7 O4 178.72(12) . . . . ? C5 C6 C7 C8 -1.2(2) . . . . ? O4 C7 C8 C3 -179.28(12) . . . . ? C6 C7 C8 C3 0.7(2) . . . . ? C4 C3 C8 C7 0.3(2) . . . . ? O3 C3 C8 C7 -177.40(12) . . . . ? O4 C9 C10 O6 -3.00(19) . . . . ? O4 C9 C10 O5 177.56(10) . . . . ? C4 C3 O3 C2 17.9(2) . . . . ? C8 C3 O3 C2 -164.49(12) . . . . ? C1 C2 O3 C3 171.83(12) . . . . ? C8 C7 O4 C9 5.58(18) . . . . ? C6 C7 O4 C9 -174.37(12) . . . . ? C10 C9 O4 C7 173.63(11) . . . . ? 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 0.83 1.90 2.7243(15) 176.3 2_755 O5 H5A O2 0.83 1.98 2.8107(17) 176.6 2_666 O5 H5A O3 0.83 2.46 2.8844(17) 112.6 2_666 _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 24.10 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.172 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.043 data_tmcg10 _database_code_CSD 220197 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 O6' _chemical_formula_weight 338.39 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 19.461(3) _cell_length_b 5.7894(7) _cell_length_c 32.412(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.33(2) _cell_angle_gamma 90.00 _cell_volume 3641.3(10) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 ? _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 10575 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 22.48 _reflns_number_total 2273 _reflns_number_gt 1698 _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 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^)+(0.0578P)^2^+5.1491P] 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 2273 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.9623(2) -0.2465(6) 0.52887(9) 0.0469(8) Uani 1 1 d . . . C2 C 0.92388(17) -0.0602(6) 0.54964(11) 0.0535(9) Uani 1 1 d . . . H2A H 0.8959 0.0275 0.5286 0.064 Uiso 1 1 calc R . . H2B H 0.8926 -0.1310 0.5683 0.064 Uiso 1 1 calc R . . C3 C 0.93819(15) 0.2341(5) 0.60018(8) 0.0365(7) Uani 1 1 d . . . C4 C 0.97892(15) 0.3147(5) 0.63435(8) 0.0347(7) Uani 1 1 d . . . C5 C 0.94487(16) 0.4559(5) 0.66094(8) 0.0367(7) Uani 1 1 d . . . H5 H 0.9716 0.5166 0.6838 0.044 Uiso 1 1 calc R . . C6 C 0.87535(15) 0.5169(4) 0.65731(8) 0.0335(7) Uani 1 1 d . . . C7 C 0.83749(16) 0.4255(5) 0.62265(9) 0.0365(7) Uani 1 1 d . . . C8 C 0.86952(16) 0.2930(5) 0.59424(9) 0.0403(8) Uani 1 1 d . . . H8 H 0.8438 0.2418 0.5703 0.048 Uiso 1 1 calc R . . C9 C 1.05549(15) 0.2508(5) 0.64248(9) 0.0402(7) Uani 1 1 d . . . C10 C 1.06363(19) -0.0122(6) 0.64649(11) 0.0568(9) Uani 1 1 d . . . H10A H 1.1121 -0.0505 0.6515 0.068 Uiso 1 1 calc R . . H10B H 1.0452 -0.0856 0.6211 0.068 Uiso 1 1 calc R . . H10C H 1.0387 -0.0667 0.6694 0.068 Uiso 1 1 calc R . . C11 C 1.09692(17) 0.3395(6) 0.60707(11) 0.0532(9) Uani 1 1 d . . . H11A H 1.1451 0.2983 0.6126 0.064 Uiso 1 1 calc R . . H11B H 1.0927 0.5061 0.6051 0.064 Uiso 1 1 calc R . . H11C H 1.0792 0.2700 0.5812 0.064 Uiso 1 1 calc R . . C12 C 1.08697(19) 0.3552(7) 0.68282(11) 0.0618(10) Uani 1 1 d . . . H12A H 1.1352 0.3121 0.6868 0.074 Uiso 1 1 calc R . . H12B H 1.0626 0.2978 0.7058 0.074 Uiso 1 1 calc R . . H12C H 1.0831 0.5222 0.6815 0.074 Uiso 1 1 calc R . . C13 C 0.84256(17) 0.6667(5) 0.68984(9) 0.0405(8) Uani 1 1 d . . . C14 C 0.8963(2) 0.7578(7) 0.72257(10) 0.0642(10) Uani 1 1 d . . . H14A H 0.8738 0.8510 0.7424 0.077 Uiso 1 1 calc R . . H14B H 0.9297 0.8515 0.7094 0.077 Uiso 1 1 calc R . . H14C H 0.9196 0.6289 0.7367 0.077 Uiso 1 1 calc R . . C15 C 0.8068(2) 0.8779(5) 0.66950(11) 0.0588(10) Uani 1 1 d . . . H15A H 0.7863 0.9694 0.6904 0.071 Uiso 1 1 calc R . . H15B H 0.7711 0.8274 0.6490 0.071 Uiso 1 1 calc R . . H15C H 0.8403 0.9706 0.6563 0.071 Uiso 1 1 calc R . . C16 C 0.7910(2) 0.5205(6) 0.71213(11) 0.0626(10) Uani 1 1 d . . . H16A H 0.7702 0.6148 0.7325 0.075 Uiso 1 1 calc R . . H16B H 0.8149 0.3913 0.7258 0.075 Uiso 1 1 calc R . . H16C H 0.7555 0.4631 0.6921 0.075 Uiso 1 1 calc R . . C17 C 0.72884(17) 0.3982(6) 0.58252(10) 0.0529(9) Uani 1 1 d . . . H17A H 0.6798 0.3951 0.5874 0.063 Uiso 1 1 calc R . . H17B H 0.7425 0.2412 0.5753 0.063 Uiso 1 1 calc R . . C18 C 0.73936(17) 0.5564(7) 0.54696(10) 0.0516(9) Uani 1 1 d . . . O1 O 0.96876(11) 0.0910(4) 0.57221(6) 0.0473(6) Uani 1 1 d . . . O2 O 1.02426(14) -0.2638(4) 0.53044(7) 0.0586(7) Uani 1 1 d . . . O3 O 0.91882(13) -0.3826(4) 0.50792(8) 0.0668(8) Uani 1 1 d . . . H3O H 0.9404 -0.4792 0.4951 0.100 Uiso 1 1 calc R . . O4 O 0.76718(11) 0.4669(4) 0.61916(6) 0.0475(6) Uani 1 1 d . . . O5 O 0.71683(16) 0.4777(5) 0.51160(8) 0.0780(9) Uani 1 1 d . . . H5O H 0.7227 0.5757 0.4935 0.117 Uiso 1 1 calc R . . O6 O 0.76511(13) 0.7501(5) 0.55222(7) 0.0673(7) Uani 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 C1 0.049(2) 0.051(2) 0.0409(18) -0.0130(16) 0.0062(15) 0.0025(18) C2 0.045(2) 0.056(2) 0.060(2) -0.0282(17) 0.0043(16) 0.0034(16) C3 0.038(2) 0.0355(16) 0.0375(16) -0.0086(13) 0.0098(13) 0.0067(14) C4 0.038(2) 0.0290(16) 0.0371(16) -0.0036(12) 0.0052(13) 0.0063(12) C5 0.046(2) 0.0291(16) 0.0345(16) -0.0030(12) 0.0011(13) 0.0028(13) C6 0.040(2) 0.0245(15) 0.0367(16) 0.0019(12) 0.0095(13) 0.0056(12) C7 0.040(2) 0.0302(16) 0.0399(17) -0.0006(13) 0.0073(13) 0.0072(13) C8 0.039(2) 0.0443(19) 0.0367(16) -0.0104(14) 0.0008(13) 0.0069(14) C9 0.039(2) 0.0342(16) 0.0470(18) -0.0048(13) -0.0004(13) 0.0104(14) C10 0.053(2) 0.046(2) 0.072(2) 0.0026(17) 0.0060(17) 0.0121(16) C11 0.037(2) 0.052(2) 0.071(2) -0.0006(17) 0.0083(16) 0.0050(15) C12 0.049(2) 0.069(2) 0.065(2) -0.0123(19) -0.0128(17) 0.0173(18) C13 0.052(2) 0.0299(16) 0.0412(17) -0.0051(13) 0.0169(14) 0.0075(14) C14 0.076(3) 0.065(2) 0.053(2) -0.0229(18) 0.0131(18) 0.010(2) C15 0.078(3) 0.0319(18) 0.069(2) -0.0012(16) 0.0171(19) 0.0175(17) C16 0.084(3) 0.050(2) 0.059(2) -0.0039(17) 0.0380(19) 0.0036(19) C17 0.035(2) 0.056(2) 0.067(2) -0.0144(18) 0.0032(16) 0.0057(15) C18 0.037(2) 0.062(2) 0.054(2) -0.0121(19) -0.0059(15) 0.0096(17) O1 0.0376(14) 0.0528(14) 0.0519(13) -0.0257(11) 0.0063(10) 0.0067(10) O2 0.0488(18) 0.0626(16) 0.0646(16) -0.0229(12) 0.0055(11) 0.0109(12) O3 0.0600(18) 0.0639(16) 0.0772(17) -0.0396(14) 0.0098(13) 0.0004(13) O4 0.0335(15) 0.0578(14) 0.0516(13) -0.0116(11) 0.0063(10) 0.0121(10) O5 0.094(2) 0.0694(18) 0.0665(18) -0.0121(14) -0.0209(16) -0.0034(16) O6 0.0679(19) 0.0667(17) 0.0651(16) -0.0098(13) -0.0083(12) -0.0132(14) _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 C1 O2 1.207(4) . ? C1 O3 1.308(4) . ? C1 C2 1.501(4) . ? C2 O1 1.403(4) . ? C3 C8 1.379(4) . ? C3 C4 1.393(4) . ? C3 O1 1.394(3) . ? C4 C5 1.392(4) . ? C4 C9 1.538(4) . ? C5 C6 1.394(4) . ? C6 C7 1.400(4) . ? C6 C13 1.540(4) . ? C7 C8 1.383(4) . ? C7 O4 1.385(4) . ? C9 C12 1.526(4) . ? C9 C10 1.535(4) . ? C9 C11 1.540(5) . ? C13 C14 1.526(5) . ? C13 C15 1.531(4) . ? C13 C16 1.534(5) . ? C17 O4 1.412(4) . ? C17 C18 1.498(5) . ? C18 O6 1.234(4) . ? C18 O5 1.280(4) . ? 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 C1 O3 125.3(3) . . ? O2 C1 C2 124.8(3) . . ? O3 C1 C2 109.9(3) . . ? O1 C2 C1 111.8(3) . . ? C8 C3 C4 121.0(3) . . ? C8 C3 O1 120.9(3) . . ? C4 C3 O1 118.1(3) . . ? C5 C4 C3 114.8(3) . . ? C5 C4 C9 122.4(3) . . ? C3 C4 C9 122.8(2) . . ? C4 C5 C6 126.9(3) . . ? C5 C6 C7 114.9(3) . . ? C5 C6 C13 122.3(3) . . ? C7 C6 C13 122.8(3) . . ? C8 C7 O4 122.3(3) . . ? C8 C7 C6 120.5(3) . . ? O4 C7 C6 117.2(2) . . ? C3 C8 C7 121.7(3) . . ? C12 C9 C10 106.7(3) . . ? C12 C9 C4 111.9(2) . . ? C10 C9 C4 110.2(3) . . ? C12 C9 C11 107.9(3) . . ? C10 C9 C11 109.7(3) . . ? C4 C9 C11 110.3(2) . . ? C14 C13 C15 106.8(3) . . ? C14 C13 C16 107.5(3) . . ? C15 C13 C16 110.6(3) . . ? C14 C13 C6 111.9(3) . . ? C15 C13 C6 110.7(2) . . ? C16 C13 C6 109.3(2) . . ? O4 C17 C18 112.4(3) . . ? O6 C18 O5 123.7(3) . . ? O6 C18 C17 121.8(3) . . ? O5 C18 C17 114.4(3) . . ? C3 O1 C2 115.5(2) . . ? C7 O4 C17 118.4(2) . . ? 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 H3O O3 0.83 2.86 3.513(5) 136.7 5_746 O3 H3O O2 0.83 1.86 2.678(3) 168.7 5_746 O5 H5O O6 0.83 1.82 2.645(4) 170.4 7_666 O3 H3O O2 0.83 1.86 2.678(3) 168.7 5_746 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.203 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.042 data_tmcg4 _database_code_CSD 220198 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Br2 O6' _chemical_formula_weight 412.04 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.694(2) _cell_length_b 9.240(3) _cell_length_c 9.899(3) _cell_angle_alpha 110.10(3) _cell_angle_beta 98.04(3) _cell_angle_gamma 98.76(3) _cell_volume 722.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 5.634 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 4629 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 24.27 _reflns_number_total 2155 _reflns_number_gt 1587 _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 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^)+(0.0988P)^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 SHELXL _refine_ls_extinction_coef 0.026(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2155 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1481 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 C1 C 0.0192(8) 0.6306(7) 0.2130(7) 0.0327(14) Uani 1 1 d . . . H1 H 0.0498 0.5820 0.2786 0.039 Uiso 1 1 calc R . . C2 C -0.1402(9) 0.6400(7) 0.1783(7) 0.0337(15) Uani 1 1 d . . . C3 C -0.1860(9) 0.7081(7) 0.0764(7) 0.0349(15) Uani 1 1 d . . . C4 C -0.0730(8) 0.7688(7) 0.0160(7) 0.0364(16) Uani 1 1 d . . . H4 H -0.1031 0.8161 -0.0509 0.044 Uiso 1 1 calc R . . C5 C 0.0819(9) 0.7622(7) 0.0505(7) 0.0346(15) Uani 1 1 d . . . C6 C 0.1298(8) 0.6927(7) 0.1508(6) 0.0311(14) Uani 1 1 d . . . C7 C 0.3505(10) 0.6292(9) 0.2815(8) 0.0468(18) Uani 1 1 d . . . H7A H 0.4500 0.5993 0.2589 0.056 Uiso 1 1 calc R . . H7B H 0.2758 0.5337 0.2720 0.056 Uiso 1 1 calc R . . C8 C 0.3817(13) 0.7434(15) 0.4347(11) 0.081(3) Uani 1 1 d . B . C9 C -0.2222(10) 0.5245(8) 0.3481(8) 0.0422(17) Uani 1 1 d . . . H9A H -0.1487 0.4541 0.3197 0.051 Uiso 1 1 calc R . . H9B H -0.3200 0.4609 0.3544 0.051 Uiso 1 1 calc R . . C10 C -0.1492(9) 0.6472(8) 0.4980(8) 0.0431(18) Uani 1 1 d . A . C11 C -0.030(4) 0.9214(19) 0.6377(18) 0.050(7) Uiso 0.49(6) 1 d P A 1 H11A H -0.0780 0.9244 0.7209 0.075 Uiso 0.49(6) 1 calc PR A 1 H11B H -0.0218 1.0222 0.6262 0.075 Uiso 0.49(6) 1 calc PR A 1 H11C H 0.0759 0.9003 0.6545 0.075 Uiso 0.49(6) 1 calc PR A 1 C11' C -0.105(5) 0.916(2) 0.647(2) 0.067(7) Uiso 0.51(6) 1 d P A 2 H11D H -0.1878 0.8898 0.6963 0.100 Uiso 0.51(6) 1 calc PR A 2 H11E H -0.1082 1.0163 0.6379 0.100 Uiso 0.51(6) 1 calc PR A 2 H11F H -0.0020 0.9217 0.7036 0.100 Uiso 0.51(6) 1 calc PR A 2 O1 O -0.2596(6) 0.5834(5) 0.2343(5) 0.0420(11) Uani 1 1 d . . . O2 O -0.1170(8) 0.6133(7) 0.6033(6) 0.0633(17) Uani 1 1 d . . . O3 O -0.1301(8) 0.7933(5) 0.5009(5) 0.0626(17) Uani 1 1 d . . . O4 O 0.2856(6) 0.6918(6) 0.1770(5) 0.0438(12) Uani 1 1 d . . . O5 O 0.4712(10) 0.7111(10) 0.5268(7) 0.093(2) Uani 1 1 d . . . O6 O 0.3216(10) 0.8622(10) 0.4683(7) 0.091(2) Uani 1 1 d . . . Br1 Br -0.39837(9) 0.72543(9) 0.03252(9) 0.0496(3) Uani 1 1 d . . . Br2 Br 0.23542(9) 0.85579(9) -0.02906(8) 0.0492(3) Uani 1 1 d . . . C12 C 0.375(4) 0.945(3) 0.629(3) 0.106(10) Uiso 0.49(2) 1 d P B 1 H12A H 0.3404 0.8746 0.6776 0.159 Uiso 0.49(2) 1 calc PR B 1 H12B H 0.3296 1.0374 0.6609 0.159 Uiso 0.49(2) 1 calc PR B 1 H12C H 0.4901 0.9766 0.6534 0.159 Uiso 0.49(2) 1 calc PR B 1 C12' C 0.509(3) 0.846(2) 0.678(2) 0.084(7) Uiso 0.51(2) 1 d P B 2 H12D H 0.5836 0.9347 0.6768 0.126 Uiso 0.51(2) 1 calc PR B 2 H12E H 0.5559 0.8099 0.7525 0.126 Uiso 0.51(2) 1 calc PR B 2 H12F H 0.4119 0.8784 0.7015 0.126 Uiso 0.51(2) 1 calc PR B 2 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 C1 0.031(4) 0.034(3) 0.035(3) 0.018(3) 0.001(3) 0.005(3) C2 0.037(5) 0.028(3) 0.035(3) 0.012(3) 0.006(3) 0.004(3) C3 0.031(4) 0.036(3) 0.041(3) 0.020(3) 0.001(3) 0.011(3) C4 0.037(5) 0.042(4) 0.036(3) 0.020(3) 0.008(3) 0.012(3) C5 0.036(5) 0.033(3) 0.038(3) 0.017(3) 0.009(3) 0.007(3) C6 0.026(4) 0.031(3) 0.035(3) 0.013(3) 0.000(3) 0.006(3) C7 0.038(5) 0.062(4) 0.057(4) 0.039(4) 0.006(4) 0.019(4) C8 0.052(7) 0.119(9) 0.053(5) 0.029(6) 0.011(5) -0.023(6) C9 0.040(5) 0.042(4) 0.054(4) 0.031(3) 0.010(3) 0.007(3) C10 0.047(5) 0.048(4) 0.048(4) 0.031(3) 0.013(4) 0.016(4) O1 0.031(3) 0.051(3) 0.051(3) 0.032(2) 0.004(2) 0.003(2) O2 0.076(5) 0.068(4) 0.058(3) 0.043(3) 0.004(3) 0.017(3) O3 0.104(5) 0.039(3) 0.046(3) 0.019(2) 0.009(3) 0.018(3) O4 0.029(3) 0.064(3) 0.053(3) 0.036(2) 0.009(2) 0.018(2) O5 0.074(6) 0.138(6) 0.058(4) 0.050(4) -0.015(4) -0.011(5) O6 0.074(6) 0.101(5) 0.065(4) -0.004(4) 0.005(4) 0.010(5) Br1 0.0284(6) 0.0633(5) 0.0693(6) 0.0410(4) 0.0049(4) 0.0121(4) Br2 0.0399(6) 0.0626(5) 0.0631(5) 0.0415(4) 0.0176(4) 0.0141(4) _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 C1 C6 1.369(9) . ? C1 C2 1.403(10) . ? C2 O1 1.362(8) . ? C2 C3 1.405(9) . ? C3 C4 1.364(9) . ? C3 Br1 1.881(7) . ? C4 C5 1.358(10) . ? C5 C6 1.406(9) . ? C5 Br2 1.886(6) . ? C6 O4 1.345(8) . ? C7 O4 1.439(8) . ? C7 C8 1.478(13) . ? C8 O6 1.249(14) . ? C8 O5 1.260(14) . ? C9 O1 1.430(8) . ? C9 C10 1.500(10) . ? C10 O2 1.197(8) . ? C10 O3 1.324(8) . ? C11 O3 1.500(19) . ? C11' O3 1.458(19) . ? O5 C12' 1.54(2) . ? O6 C12 1.47(3) . ? 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 C1 C2 119.6(6) . . ? O1 C2 C1 124.6(6) . . ? O1 C2 C3 115.5(6) . . ? C1 C2 C3 119.8(6) . . ? C4 C3 C2 119.1(7) . . ? C4 C3 Br1 120.6(5) . . ? C2 C3 Br1 120.1(5) . . ? C5 C4 C3 121.4(6) . . ? C4 C5 C6 120.3(6) . . ? C4 C5 Br2 119.9(5) . . ? C6 C5 Br2 119.7(6) . . ? O4 C6 C1 124.8(6) . . ? O4 C6 C5 115.6(6) . . ? C1 C6 C5 119.6(7) . . ? O4 C7 C8 112.4(8) . . ? O6 C8 O5 123.3(10) . . ? O6 C8 C7 121.5(10) . . ? O5 C8 C7 115.1(12) . . ? O1 C9 C10 115.6(5) . . ? O2 C10 O3 124.7(7) . . ? O2 C10 C9 122.1(6) . . ? O3 C10 C9 113.2(6) . . ? C2 O1 C9 119.4(6) . . ? C10 O3 C11' 114.9(9) . . ? C10 O3 C11 116.8(8) . . ? C11' O3 C11 26.1(10) . . ? C6 O4 C7 120.9(5) . . ? C8 O5 C12' 110.5(13) . . ? C8 O6 C12 106.2(14) . . ? 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 C6 C1 C2 O1 -179.5(5) . . . . ? C6 C1 C2 C3 2.1(9) . . . . ? O1 C2 C3 C4 179.5(5) . . . . ? C1 C2 C3 C4 -2.0(9) . . . . ? O1 C2 C3 Br1 2.9(8) . . . . ? C1 C2 C3 Br1 -178.6(4) . . . . ? C2 C3 C4 C5 1.1(9) . . . . ? Br1 C3 C4 C5 177.7(5) . . . . ? C3 C4 C5 C6 -0.3(9) . . . . ? C3 C4 C5 Br2 -177.2(5) . . . . ? C2 C1 C6 O4 179.3(5) . . . . ? C2 C1 C6 C5 -1.3(9) . . . . ? C4 C5 C6 O4 179.8(6) . . . . ? Br2 C5 C6 O4 -3.3(7) . . . . ? C4 C5 C6 C1 0.4(9) . . . . ? Br2 C5 C6 C1 177.3(5) . . . . ? O4 C7 C8 O6 16.3(12) . . . . ? O4 C7 C8 O5 -164.1(8) . . . . ? O1 C9 C10 O2 177.7(7) . . . . ? O1 C9 C10 O3 -0.3(10) . . . . ? C1 C2 O1 C9 7.0(9) . . . . ? C3 C2 O1 C9 -174.6(6) . . . . ? C10 C9 O1 C2 75.0(8) . . . . ? O2 C10 O3 C11' -15(2) . . . . ? C9 C10 O3 C11' 162.7(19) . . . . ? O2 C10 O3 C11 13.7(18) . . . . ? C9 C10 O3 C11 -168.3(15) . . . . ? C1 C6 O4 C7 -2.9(9) . . . . ? C5 C6 O4 C7 177.7(6) . . . . ? C8 C7 O4 C6 -81.2(9) . . . . ? O6 C8 O5 C12' -6.4(15) . . . . ? C7 C8 O5 C12' 174.1(11) . . . . ? O5 C8 O6 C12 -1.1(17) . . . . ? C7 C8 O6 C12 178.4(13) . . . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 24.27 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 1.044 _refine_diff_density_min -1.576 _refine_diff_density_rms 0.197 data_tmcg9 _database_code_CSD 220199 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Br2 O6' _chemical_formula_weight 440.09 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.2340(13) _cell_length_b 7.4699(11) _cell_length_c 20.184(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.541(13) _cell_angle_gamma 90.00 _cell_volume 1682.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 4.841 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 2491 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 24.16 _reflns_number_total 2491 _reflns_number_gt 1722 _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 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^)+(0.0380P)^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 2491 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0615 _refine_ls_wR_factor_gt 0.0598 _refine_ls_goodness_of_fit_ref 0.797 _refine_ls_restrained_S_all 0.797 _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 Br1 Br 0.40104(4) 0.27462(6) 0.22954(2) 0.04572(15) Uani 1 1 d . . . Br2 Br -0.09439(4) 0.32019(6) 0.14583(2) 0.05229(15) Uani 1 1 d . . . C1 C 0.2419(3) 0.2688(4) 0.25040(18) 0.0267(8) Uani 1 1 d . . . C2 C 0.1497(3) 0.2934(5) 0.20053(18) 0.0322(9) Uani 1 1 d . . . H2 H 0.1664 0.3144 0.1571 0.039 Uiso 1 1 calc R . . C3 C 0.0317(3) 0.2871(5) 0.21446(18) 0.0300(9) Uani 1 1 d . . . C4 C 0.0067(3) 0.2559(5) 0.27975(18) 0.0294(9) Uani 1 1 d . A . C5 C 0.0994(3) 0.2314(5) 0.32906(18) 0.0337(9) Uani 1 1 d . . . H5 H 0.0827 0.2097 0.3724 0.040 Uiso 1 1 calc R . . C6 C 0.2188(3) 0.2383(4) 0.31568(19) 0.0294(9) Uani 1 1 d . . . C7 C -0.1624(3) 0.3181(5) 0.3444(2) 0.0406(10) Uani 1 1 d . A . C8 C -0.1107(4) 0.5003(5) 0.3635(2) 0.0546(13) Uani 1 1 d . . . H8A H -0.0262 0.4893 0.3769 0.082 Uiso 1 1 calc R . . H8B H -0.1491 0.5476 0.3999 0.082 Uiso 1 1 calc R . . H8C H -0.1239 0.5796 0.3260 0.082 Uiso 1 1 calc R . . C9 C -0.2965(4) 0.3288(6) 0.3190(3) 0.0634(14) Uani 1 1 d . . . H9A H -0.3076 0.4036 0.2801 0.095 Uiso 1 1 calc R . . H9B H -0.3394 0.3786 0.3532 0.095 Uiso 1 1 calc R . . H9C H -0.3264 0.2109 0.3079 0.095 Uiso 1 1 calc R . . C10 C -0.1515(4) 0.1897(5) 0.4024(2) 0.0421(11) Uani 1 1 d . . . C11 C 0.3187(3) 0.2658(5) 0.42935(19) 0.0356(10) Uani 1 1 d . . . C12 C 0.4504(4) 0.2435(7) 0.4562(2) 0.0568(13) Uani 1 1 d . . . H12A H 0.4756 0.1236 0.4480 0.085 Uiso 1 1 calc R . . H12B H 0.4605 0.2664 0.5033 0.085 Uiso 1 1 calc R . . H12C H 0.4979 0.3267 0.4342 0.085 Uiso 1 1 calc R . . C13 C 0.2780(4) 0.4569(5) 0.4353(2) 0.0529(12) Uani 1 1 d . . . H13A H 0.3232 0.5332 0.4092 0.079 Uiso 1 1 calc R . . H13B H 0.2904 0.4933 0.4812 0.079 Uiso 1 1 calc R . . H13C H 0.1944 0.4659 0.4193 0.079 Uiso 1 1 calc R . . C14 C 0.2474(3) 0.1349(5) 0.46786(18) 0.0333(9) Uani 1 1 d . . . O1 O -0.1127(2) 0.2393(4) 0.28781(13) 0.0443(7) Uani 1 1 d . . . O2 O -0.1519(10) 0.2393(8) 0.4625(4) 0.049(3) Uiso 0.53(2) 1 d P A 1 O2' O -0.2103(11) 0.2459(8) 0.4490(4) 0.042(3) Uiso 0.47(2) 1 d P A 2 O3 O -0.1189(3) 0.0307(4) 0.39292(16) 0.0562(9) Uani 1 1 d . A . H3 H -0.1266 -0.0296 0.4261 0.084 Uiso 1 1 calc R . . O4 O 0.3164(2) 0.2087(3) 0.36107(12) 0.0373(6) Uani 1 1 d . . . O5 O 0.1902(3) 0.1884(4) 0.51228(14) 0.0522(8) Uani 1 1 d . . . O6 O 0.2566(3) -0.0305(4) 0.45251(16) 0.0649(10) Uani 1 1 d . . . H6 H 0.2214 -0.0920 0.4777 0.097 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 Br1 0.0356(2) 0.0574(3) 0.0480(3) 0.0107(2) 0.0214(2) 0.0068(2) Br2 0.0453(3) 0.0752(3) 0.0347(3) 0.0104(2) -0.0029(2) -0.0022(2) C1 0.0285(19) 0.0255(19) 0.028(2) 0.0020(15) 0.0120(18) 0.0019(15) C2 0.044(2) 0.030(2) 0.026(2) 0.0012(16) 0.017(2) 0.0038(17) C3 0.033(2) 0.032(2) 0.025(2) -0.0020(16) 0.0016(18) 0.0007(16) C4 0.0306(19) 0.032(2) 0.027(2) 0.0015(16) 0.0092(19) 0.0014(16) C5 0.034(2) 0.047(2) 0.022(2) 0.0038(17) 0.014(2) -0.0002(18) C6 0.035(2) 0.027(2) 0.027(2) -0.0007(16) 0.0049(19) 0.0016(16) C7 0.040(2) 0.043(3) 0.043(3) 0.0064(19) 0.023(2) 0.0049(19) C8 0.056(3) 0.044(3) 0.070(3) 0.006(2) 0.030(3) 0.001(2) C9 0.031(2) 0.078(4) 0.083(4) 0.020(3) 0.015(2) 0.010(2) C10 0.048(3) 0.041(3) 0.041(3) -0.004(2) 0.024(2) -0.001(2) C11 0.038(2) 0.046(2) 0.024(2) -0.0002(18) 0.0036(19) -0.0040(18) C12 0.042(2) 0.091(4) 0.035(3) 0.004(2) -0.005(2) -0.012(2) C13 0.069(3) 0.047(3) 0.043(3) -0.002(2) 0.010(3) -0.008(2) C14 0.036(2) 0.040(3) 0.023(2) 0.0008(17) 0.0024(19) 0.0024(18) O1 0.0297(14) 0.0690(19) 0.0361(17) 0.0005(14) 0.0120(14) -0.0055(13) O3 0.0560(19) 0.0481(19) 0.070(2) 0.0200(15) 0.0304(18) 0.0080(15) O4 0.0313(14) 0.0608(18) 0.0206(15) 0.0035(12) 0.0052(13) 0.0077(13) O5 0.066(2) 0.0480(18) 0.0479(19) 0.0059(14) 0.0308(17) 0.0065(14) O6 0.108(3) 0.0425(19) 0.052(2) -0.0008(15) 0.043(2) -0.0078(17) _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 Br1 C1 1.883(3) . ? Br2 C3 1.881(4) . ? C1 C2 1.372(5) . ? C1 C6 1.390(5) . ? C2 C3 1.387(5) . ? C3 C4 1.398(5) . ? C4 C5 1.368(5) . ? C4 O1 1.376(4) . ? C5 C6 1.399(5) . ? C6 O4 1.364(4) . ? C7 O1 1.452(4) . ? C7 C10 1.508(6) . ? C7 C8 1.512(6) . ? C7 C9 1.537(6) . ? C10 O3 1.263(4) . ? C10 O2 1.269(7) . ? C10 O2' 1.280(8) . ? C11 O4 1.440(4) . ? C11 C13 1.508(5) . ? C11 C12 1.526(6) . ? C11 C14 1.531(5) . ? C14 O5 1.228(4) . ? C14 O6 1.280(4) . ? 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 C2 C1 C6 120.7(3) . . ? C2 C1 Br1 119.3(2) . . ? C6 C1 Br1 120.0(3) . . ? C1 C2 C3 120.4(3) . . ? C2 C3 C4 119.7(4) . . ? C2 C3 Br2 120.2(3) . . ? C4 C3 Br2 120.1(3) . . ? C5 C4 O1 125.0(3) . . ? C5 C4 C3 119.4(3) . . ? O1 C4 C3 115.5(3) . . ? C4 C5 C6 121.4(3) . . ? O4 C6 C1 116.1(3) . . ? O4 C6 C5 125.4(3) . . ? C1 C6 C5 118.4(3) . . ? O1 C7 C10 110.4(3) . . ? O1 C7 C8 113.3(3) . . ? C10 C7 C8 112.3(4) . . ? O1 C7 C9 102.0(4) . . ? C10 C7 C9 106.4(3) . . ? C8 C7 C9 111.8(3) . . ? O3 C10 O2 116.9(5) . . ? O3 C10 O2' 127.1(4) . . ? O2 C10 O2' 31.1(3) . . ? O3 C10 C7 118.6(3) . . ? O2 C10 C7 123.2(4) . . ? O2' C10 C7 111.0(5) . . ? O4 C11 C13 112.6(3) . . ? O4 C11 C12 102.6(3) . . ? C13 C11 C12 111.4(4) . . ? O4 C11 C14 110.1(3) . . ? C13 C11 C14 112.5(3) . . ? C12 C11 C14 107.0(3) . . ? O5 C14 O6 123.6(3) . . ? O5 C14 C11 120.7(3) . . ? O6 C14 C11 115.6(3) . . ? C4 O1 C7 121.6(3) . . ? C6 O4 C11 121.3(3) . . ? 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 C6 C1 C2 C3 -0.4(5) . . . . ? Br1 C1 C2 C3 179.1(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C1 C2 C3 Br2 -179.8(3) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? Br2 C3 C4 C5 179.8(3) . . . . ? C2 C3 C4 O1 -175.5(3) . . . . ? Br2 C3 C4 O1 4.4(4) . . . . ? O1 C4 C5 C6 175.4(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C2 C1 C6 O4 177.6(3) . . . . ? Br1 C1 C6 O4 -1.9(4) . . . . ? C2 C1 C6 C5 0.7(5) . . . . ? Br1 C1 C6 C5 -178.8(3) . . . . ? C4 C5 C6 O4 -177.3(3) . . . . ? C4 C5 C6 C1 -0.8(5) . . . . ? O1 C7 C10 O3 -9.5(5) . . . . ? C8 C7 C10 O3 -136.9(4) . . . . ? C9 C7 C10 O3 100.5(4) . . . . ? O1 C7 C10 O2 157.3(7) . . . . ? C8 C7 C10 O2 29.9(8) . . . . ? C9 C7 C10 O2 -92.8(7) . . . . ? O1 C7 C10 O2' -170.4(6) . . . . ? C8 C7 C10 O2' 62.2(7) . . . . ? C9 C7 C10 O2' -60.4(7) . . . . ? O4 C11 C14 O5 -145.6(4) . . . . ? C13 C11 C14 O5 -19.1(5) . . . . ? C12 C11 C14 O5 103.7(4) . . . . ? O4 C11 C14 O6 37.4(5) . . . . ? C13 C11 C14 O6 163.9(4) . . . . ? C12 C11 C14 O6 -73.4(4) . . . . ? C5 C4 O1 C7 45.4(5) . . . . ? C3 C4 O1 C7 -139.6(3) . . . . ? C10 C7 O1 C4 -88.0(4) . . . . ? C8 C7 O1 C4 38.8(5) . . . . ? C9 C7 O1 C4 159.2(3) . . . . ? C1 C6 O4 C11 147.2(3) . . . . ? C5 C6 O4 C11 -36.2(5) . . . . ? C13 C11 O4 C6 -48.0(4) . . . . ? C12 C11 O4 C6 -167.9(3) . . . . ? C14 C11 O4 C6 78.5(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 O6 H6 O2' 0.82 1.89 2.655(7) 155.0 3_556 O6 H6 O2 0.82 1.87 2.686(6) 175.9 3_556 O3 H3 O5 0.82 1.91 2.708(4) 162.4 3_556 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 24.16 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.488 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.067