# Electronic Supplementary material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jubaraj Baruah' _publ_contact_author_email JUBA@IITG.ERNET.IN _publ_section_title ; Crystal packing in some flexible carboxylic acids and esters attached to naphthalene ring ; loop_ _publ_author_name 'Jubaraj Baruah' 'Anirban Karmakar' 'Pallab Mondal' 'W Marjit Singh' # Attachment '13diacid-c.cif' data_13diacid _database_code_depnum_ccdc_archive 'CCDC 677172' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 O6' _chemical_formula_weight 276.24 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.0505(6) _cell_length_b 5.1175(2) _cell_length_c 18.2405(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.243(2) _cell_angle_gamma 90.00 _cell_volume 1214.87(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6530 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.48 _exptl_crystal_description Blocks _exptl_crystal_colour Red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16164 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2498 _reflns_number_gt 2141 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.4062P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2498 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C8 C 0.27645(10) 0.1017(3) 0.16489(7) 0.0309(3) Uani 1 1 d . . . H8 H 0.3448 0.1031 0.1835 0.037 Uiso 1 1 calc R . . C5 C 0.07047(10) 0.1063(3) 0.10856(7) 0.0314(3) Uani 1 1 d . . . C10 C 0.10326(10) -0.0770(2) 0.16346(7) 0.0288(3) Uani 1 1 d . . . C9 C 0.20846(10) -0.0715(2) 0.19126(7) 0.0291(3) Uani 1 1 d . . . C13 C 0.29040(10) 0.6186(3) 0.02953(7) 0.0340(3) Uani 1 1 d . . . H13A H 0.2340 0.7286 0.0424 0.041 Uiso 1 1 calc R . . H13B H 0.2690 0.5235 -0.0150 0.041 Uiso 1 1 calc R . . C7 C 0.24148(10) 0.2791(3) 0.10890(7) 0.0308(3) Uani 1 1 d . . . C12 C 0.37936(11) -0.0922(3) 0.32321(7) 0.0349(3) Uani 1 1 d . . . C6 C 0.14214(10) 0.2842(3) 0.08109(7) 0.0340(3) Uani 1 1 d . . . H6 H 0.1211 0.4030 0.0444 0.041 Uiso 1 1 calc R . . C14 C 0.38346(10) 0.7826(3) 0.01780(7) 0.0330(3) Uani 1 1 d . . . C3 C -0.10198(11) -0.0689(3) 0.10845(8) 0.0440(4) Uani 1 1 d . . . H3 H -0.1708 -0.0640 0.0911 0.053 Uiso 1 1 calc R . . C1 C 0.03182(11) -0.2588(3) 0.18830(8) 0.0361(3) Uani 1 1 d . . . H1 H 0.0533 -0.3822 0.2236 0.043 Uiso 1 1 calc R . . C11 C 0.33658(11) -0.2932(3) 0.26872(8) 0.0377(3) Uani 1 1 d . . . H11A H 0.3768 -0.2908 0.2261 0.045 Uiso 1 1 calc R . . H11B H 0.3438 -0.4650 0.2909 0.045 Uiso 1 1 calc R . . C4 C -0.03424(11) 0.1064(3) 0.08249(8) 0.0416(4) Uani 1 1 d . . . H4 H -0.0575 0.2276 0.0471 0.050 Uiso 1 1 calc R . . C2 C -0.06861(11) -0.2547(3) 0.16083(8) 0.0418(4) Uani 1 1 d . . . H2 H -0.1148 -0.3763 0.1771 0.050 Uiso 1 1 calc R . . O4 O 0.31807(7) 0.4427(2) 0.08719(5) 0.0386(3) Uani 1 1 d . . . O5 O 0.36392(8) 0.9577(2) -0.03352(6) 0.0457(3) Uani 1 1 d . . . H5O H 0.4160 1.0427 -0.0391 0.069 Uiso 1 1 calc R . . O6 O 0.46610(8) 0.7548(2) 0.05205(6) 0.0466(3) Uani 1 1 d . . . O1 O 0.23236(7) -0.2518(2) 0.24536(5) 0.0391(3) Uani 1 1 d . . . O2 O 0.33174(9) 0.0764(2) 0.35089(6) 0.0523(3) Uani 1 1 d . . . O3 O 0.47934(8) -0.1335(3) 0.33803(7) 0.0542(3) Uani 1 1 d . . . H3O H 0.5020 -0.0282 0.3690 0.081 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 C8 0.0250(6) 0.0354(7) 0.0316(6) 0.0017(5) -0.0026(5) -0.0027(5) C5 0.0289(7) 0.0330(7) 0.0318(6) -0.0011(5) 0.0001(5) -0.0023(5) C10 0.0293(7) 0.0290(7) 0.0283(6) -0.0033(5) 0.0028(5) -0.0032(5) C9 0.0318(7) 0.0285(7) 0.0267(6) 0.0007(5) 0.0010(5) -0.0007(5) C13 0.0326(7) 0.0362(7) 0.0326(7) 0.0059(6) -0.0008(5) -0.0069(6) C7 0.0299(7) 0.0307(7) 0.0321(7) 0.0011(5) 0.0033(5) -0.0067(5) C12 0.0336(7) 0.0381(8) 0.0329(7) 0.0056(6) 0.0017(5) 0.0018(6) C6 0.0338(7) 0.0342(7) 0.0333(7) 0.0074(6) -0.0023(5) -0.0030(6) C14 0.0331(7) 0.0343(7) 0.0319(7) 0.0034(5) 0.0029(5) -0.0041(5) C3 0.0259(7) 0.0573(10) 0.0480(8) -0.0024(7) -0.0023(6) -0.0072(6) C1 0.0365(8) 0.0365(7) 0.0356(7) 0.0023(6) 0.0041(6) -0.0069(6) C11 0.0376(8) 0.0338(7) 0.0406(8) 0.0051(6) -0.0041(6) 0.0041(6) C4 0.0319(7) 0.0481(9) 0.0437(8) 0.0070(7) -0.0056(6) -0.0020(6) C2 0.0342(8) 0.0464(9) 0.0454(8) -0.0032(7) 0.0081(6) -0.0144(6) O4 0.0312(5) 0.0424(6) 0.0415(5) 0.0149(4) -0.0034(4) -0.0110(4) O5 0.0380(6) 0.0481(6) 0.0501(6) 0.0201(5) -0.0029(5) -0.0121(5) O6 0.0318(6) 0.0508(6) 0.0559(6) 0.0217(5) -0.0056(5) -0.0110(5) O1 0.0336(5) 0.0409(6) 0.0415(5) 0.0141(4) -0.0053(4) -0.0052(4) O2 0.0504(7) 0.0515(7) 0.0542(7) -0.0112(5) -0.0018(5) 0.0123(5) O3 0.0334(6) 0.0685(8) 0.0595(7) -0.0186(6) -0.0051(5) 0.0021(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 C8 C9 1.3667(18) . ? C8 C7 1.4165(18) . ? C5 C4 1.4133(19) . ? C5 C10 1.4149(18) . ? C5 C6 1.4229(18) . ? C10 C1 1.4153(18) . ? C10 C9 1.4281(18) . ? C9 O1 1.3697(15) . ? C13 O4 1.4108(16) . ? C13 C14 1.5045(18) . ? C7 C6 1.3570(18) . ? C7 O4 1.3841(15) . ? C12 O2 1.1967(17) . ? C12 O3 1.3297(17) . ? C12 C11 1.508(2) . ? C14 O6 1.2142(16) . ? C14 O5 1.3075(16) . ? C3 C4 1.368(2) . ? C3 C2 1.395(2) . ? C1 C2 1.368(2) . ? C11 O1 1.4108(17) . ? 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 C9 C8 C7 119.11(12) . . ? C4 C5 C10 118.21(12) . . ? C4 C5 C6 121.72(13) . . ? C10 C5 C6 120.07(12) . . ? C5 C10 C1 119.37(12) . . ? C5 C10 C9 118.10(11) . . ? C1 C10 C9 122.53(12) . . ? C8 C9 O1 124.83(12) . . ? C8 C9 C10 121.31(11) . . ? O1 C9 C10 113.86(11) . . ? O4 C13 C14 107.28(10) . . ? C6 C7 O4 124.85(12) . . ? C6 C7 C8 122.00(12) . . ? O4 C7 C8 113.14(11) . . ? O2 C12 O3 124.15(14) . . ? O2 C12 C11 126.24(13) . . ? O3 C12 C11 109.59(12) . . ? C7 C6 C5 119.39(12) . . ? O6 C14 O5 124.57(12) . . ? O6 C14 C13 123.86(12) . . ? O5 C14 C13 111.57(11) . . ? C4 C3 C2 120.47(13) . . ? C2 C1 C10 120.57(13) . . ? O1 C11 C12 113.47(12) . . ? C3 C4 C5 121.11(14) . . ? C1 C2 C3 120.22(13) . . ? C7 O4 C13 116.67(10) . . ? C9 O1 C11 118.80(10) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.200 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.044 # Attachment '15diester2-c.cif' data_15diester2 _database_code_depnum_ccdc_archive 'CCDC 677173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 O6' _chemical_formula_weight 304.29 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 7.0661(4) _cell_length_b 7.4816(5) _cell_length_c 8.0748(5) _cell_angle_alpha 67.837(4) _cell_angle_beta 72.069(4) _cell_angle_gamma 74.951(4) _cell_volume 371.12(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1652 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 28.03 _exptl_crystal_description Blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2773 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1315 _reflns_number_gt 1124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1063P)^2^+0.0362P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1315 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 O2 O 0.40816(18) 0.55445(19) 0.19966(15) 0.0558(4) Uani 1 1 d . . . O3 O 0.2885(2) 0.64505(19) 0.45110(16) 0.0648(5) Uani 1 1 d . . . O1 O 0.15586(17) 0.30042(16) 0.64570(14) 0.0479(4) Uani 1 1 d . . . C7 C 0.3162(2) 0.5287(2) 0.3752(2) 0.0433(4) Uani 1 1 d . . . C6 C 0.2582(3) 0.3282(2) 0.4594(2) 0.0472(5) Uani 1 1 d . . . H6A H 0.1714 0.3155 0.3932 0.057 Uiso 1 1 calc R . . H6B H 0.3779 0.2297 0.4517 0.057 Uiso 1 1 calc R . . C4 C 0.1149(2) 0.1154(2) 0.7507(2) 0.0401(4) Uani 1 1 d . . . C3 C 0.1558(2) -0.0391(2) 0.6863(2) 0.0480(5) Uani 1 1 d . . . H3 H 0.2138 -0.0225 0.5624 0.058 Uiso 1 1 calc R . . C2 C 0.1096(2) -0.2226(2) 0.8082(2) 0.0494(5) Uani 1 1 d . . . H2 H 0.1387 -0.3270 0.7636 0.059 Uiso 1 1 calc R . . C1 C 0.0231(2) -0.2510(2) 0.9902(2) 0.0441(4) Uani 1 1 d . . . H1 H -0.0053 -0.3739 1.0687 0.053 Uiso 1 1 calc R . . C5 C 0.0233(2) 0.0928(2) 0.9405(2) 0.0372(4) Uani 1 1 d . . . C8 C 0.4829(3) 0.7369(3) 0.0952(2) 0.0646(6) Uani 1 1 d . . . H8A H 0.3740 0.8440 0.1007 0.097 Uiso 1 1 calc R . . H8B H 0.5395 0.7419 -0.0305 0.097 Uiso 1 1 calc R . . H8C H 0.5849 0.7461 0.1461 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 O2 0.0674(8) 0.0595(8) 0.0350(7) -0.0107(6) 0.0011(5) -0.0242(6) O3 0.0871(10) 0.0541(8) 0.0514(8) -0.0224(6) 0.0020(7) -0.0225(7) O1 0.0640(7) 0.0388(7) 0.0347(7) -0.0109(5) 0.0013(5) -0.0151(5) C7 0.0453(8) 0.0460(9) 0.0361(8) -0.0119(7) -0.0066(6) -0.0089(7) C6 0.0571(9) 0.0461(10) 0.0339(8) -0.0120(7) -0.0017(7) -0.0131(7) C4 0.0442(8) 0.0379(9) 0.0357(8) -0.0104(7) -0.0052(6) -0.0095(6) C3 0.0591(9) 0.0467(9) 0.0356(8) -0.0158(7) -0.0016(7) -0.0121(7) C2 0.0623(9) 0.0421(9) 0.0459(10) -0.0213(7) -0.0022(7) -0.0138(7) C1 0.0521(8) 0.0351(8) 0.0439(9) -0.0131(7) -0.0046(6) -0.0127(6) C5 0.0368(7) 0.0378(8) 0.0364(8) -0.0130(7) -0.0050(6) -0.0081(6) C8 0.0683(11) 0.0678(12) 0.0494(11) -0.0016(10) -0.0052(9) -0.0339(10) _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 O2 C7 1.3270(18) . ? O2 C8 1.444(2) . ? O3 C7 1.188(2) . ? O1 C4 1.3748(19) . ? O1 C6 1.4144(18) . ? C7 C6 1.503(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C4 C3 1.370(2) . ? C4 C5 1.431(2) . ? C3 C2 1.405(2) . ? C3 H3 0.9300 . ? C2 C1 1.363(2) . ? C2 H2 0.9300 . ? C1 C5 1.417(2) 2_557 ? C1 H1 0.9300 . ? C5 C5 1.412(3) 2_557 ? C5 C1 1.417(2) 2_557 ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 C7 O2 C8 116.95(14) . . ? C4 O1 C6 116.69(12) . . ? O3 C7 O2 124.96(15) . . ? O3 C7 C6 126.71(15) . . ? O2 C7 C6 108.33(13) . . ? O1 C6 C7 108.92(13) . . ? O1 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? O1 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C3 C4 O1 125.03(14) . . ? C3 C4 C5 120.75(15) . . ? O1 C4 C5 114.22(13) . . ? C4 C3 C2 119.74(14) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C1 C2 C3 121.51(14) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C1 C5 119.76(15) . 2_557 ? C2 C1 H1 120.1 . . ? C5 C1 H1 120.1 2_557 . ? C5 C5 C1 119.97(17) 2_557 2_557 ? C5 C5 C4 118.27(17) 2_557 . ? C1 C5 C4 121.75(15) 2_557 . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.316 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.105 # Attachment '16diester.cif' data_16diester _database_code_depnum_ccdc_archive 'CCDC 677174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 O6' _chemical_formula_weight 304.29 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.5782(2) _cell_length_b 9.95720(10) _cell_length_c 8.62060(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.7140(10) _cell_angle_gamma 90.00 _cell_volume 1495.21(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3758 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 23.65 _exptl_crystal_description Blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21190 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3688 _reflns_number_gt 2329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.1616P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3688 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C10 C 0.28228(8) 0.99944(13) 0.56805(15) 0.0465(3) Uani 1 1 d . . . C3 C 0.15735(8) 0.83261(14) 0.46527(15) 0.0490(3) Uani 1 1 d . . . C4 C 0.15100(8) 0.92299(14) 0.58193(15) 0.0503(3) Uani 1 1 d . . . H4 H 0.1055 0.9290 0.6256 0.060 Uiso 1 1 calc R . . C5 C 0.21378(8) 1.00759(14) 0.63640(15) 0.0488(3) Uani 1 1 d . . . C9 C 0.34450(9) 1.08695(14) 0.62324(16) 0.0509(4) Uani 1 1 d . . . C2 C 0.22581(9) 0.82257(15) 0.39793(16) 0.0532(4) Uani 1 1 d . . . H2 H 0.2297 0.7599 0.3194 0.064 Uiso 1 1 calc R . . C1 C 0.28625(9) 0.90438(15) 0.44758(16) 0.0521(4) Uani 1 1 d . . . H1 H 0.3310 0.8976 0.4014 0.063 Uiso 1 1 calc R . . C12 C -0.02154(9) 0.64521(17) 0.38250(17) 0.0561(4) Uani 1 1 d . . . C15 C 0.51675(9) 1.06715(15) 0.73958(17) 0.0547(4) Uani 1 1 d . . . C8 C 0.33920(10) 1.17284(16) 0.74452(18) 0.0630(4) Uani 1 1 d . . . H8 H 0.3803 1.2280 0.7816 0.076 Uiso 1 1 calc R . . C14 C 0.47574(9) 1.14337(15) 0.60222(18) 0.0587(4) Uani 1 1 d . . . H14A H 0.4642 1.2334 0.6351 0.070 Uiso 1 1 calc R . . H14B H 0.5089 1.1507 0.5213 0.070 Uiso 1 1 calc R . . C6 C 0.20938(10) 1.09941(17) 0.76099(17) 0.0635(4) Uani 1 1 d . . . H6 H 0.1646 1.1062 0.8068 0.076 Uiso 1 1 calc R . . C11 C 0.02913(9) 0.75405(16) 0.45999(18) 0.0591(4) Uani 1 1 d . . . H11A H 0.0061 0.8414 0.4355 0.071 Uiso 1 1 calc R . . H11B H 0.0359 0.7424 0.5727 0.071 Uiso 1 1 calc R . . C7 C 0.27118(11) 1.17730(17) 0.81285(18) 0.0696(5) Uani 1 1 d . . . H7 H 0.2682 1.2354 0.8963 0.084 Uiso 1 1 calc R . . C13 C -0.14729(10) 0.5610(2) 0.3539(2) 0.0802(5) Uani 1 1 d . . . H13A H -0.1475 0.5591 0.2425 0.120 Uiso 1 1 calc R . . H13B H -0.1973 0.5862 0.3771 0.120 Uiso 1 1 calc R . . H13C H -0.1343 0.4737 0.3965 0.120 Uiso 1 1 calc R . . C16 C 0.62523(11) 1.0699(2) 0.9335(2) 0.0867(6) Uani 1 1 d . . . H16A H 0.5979 1.0593 1.0219 0.130 Uiso 1 1 calc R . . H16B H 0.6705 1.1228 0.9633 0.130 Uiso 1 1 calc R . . H16C H 0.6396 0.9832 0.8983 0.130 Uiso 1 1 calc R . . O1 O 0.10080(6) 0.74514(11) 0.40300(12) 0.0605(3) Uani 1 1 d . . . O4 O 0.40632(6) 1.07763(10) 0.54027(12) 0.0587(3) Uani 1 1 d . . . O5 O 0.57622(6) 1.13729(11) 0.80752(12) 0.0671(3) Uani 1 1 d . . . O2 O -0.09116(6) 0.65791(12) 0.42260(13) 0.0701(3) Uani 1 1 d . . . O6 O 0.50009(7) 0.95709(12) 0.77797(15) 0.0768(4) Uani 1 1 d . . . O3 O -0.00272(7) 0.55948(13) 0.29922(15) 0.0824(4) 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 C10 0.0497(9) 0.0416(7) 0.0452(7) 0.0036(6) -0.0046(6) 0.0016(6) C3 0.0469(9) 0.0493(8) 0.0490(7) 0.0000(6) -0.0004(6) -0.0054(7) C4 0.0481(9) 0.0554(9) 0.0469(7) 0.0014(6) 0.0045(6) 0.0022(7) C5 0.0551(9) 0.0454(8) 0.0435(7) 0.0015(6) -0.0027(6) 0.0054(7) C9 0.0531(9) 0.0429(8) 0.0522(7) 0.0042(6) -0.0093(6) 0.0008(7) C2 0.0502(9) 0.0528(9) 0.0561(8) -0.0112(6) 0.0055(6) -0.0035(7) C1 0.0469(9) 0.0536(9) 0.0551(8) -0.0040(6) 0.0037(6) 0.0003(7) C12 0.0485(9) 0.0649(10) 0.0553(8) 0.0002(7) 0.0084(7) -0.0069(8) C15 0.0498(9) 0.0450(9) 0.0669(9) -0.0003(7) -0.0012(7) -0.0053(7) C8 0.0675(11) 0.0517(9) 0.0639(9) -0.0078(7) -0.0129(8) -0.0032(8) C14 0.0543(9) 0.0443(8) 0.0732(9) 0.0041(7) -0.0073(7) -0.0107(7) C6 0.0673(11) 0.0667(11) 0.0547(8) -0.0121(7) 0.0018(7) 0.0067(8) C11 0.0507(9) 0.0653(10) 0.0623(8) -0.0085(7) 0.0108(7) -0.0059(8) C7 0.0814(13) 0.0642(11) 0.0588(9) -0.0194(8) -0.0070(8) 0.0057(9) C13 0.0552(11) 0.0903(14) 0.0942(12) -0.0095(10) 0.0062(9) -0.0219(10) C16 0.0708(13) 0.0972(15) 0.0830(12) 0.0069(11) -0.0234(10) -0.0026(11) O1 0.0485(6) 0.0681(7) 0.0661(6) -0.0174(5) 0.0116(5) -0.0134(5) O4 0.0500(6) 0.0567(6) 0.0661(6) -0.0030(5) -0.0045(5) -0.0097(5) O5 0.0591(7) 0.0606(7) 0.0751(7) 0.0024(5) -0.0144(5) -0.0115(5) O2 0.0478(7) 0.0833(8) 0.0799(7) -0.0134(6) 0.0108(5) -0.0098(6) O6 0.0760(8) 0.0508(7) 0.0976(8) 0.0187(6) -0.0109(6) -0.0112(6) O3 0.0671(8) 0.0866(9) 0.0983(9) -0.0348(7) 0.0285(7) -0.0201(7) _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 C10 C5 1.412(2) . ? C10 C1 1.4138(19) . ? C10 C9 1.429(2) . ? C3 C4 1.3653(19) . ? C3 O1 1.3754(16) . ? C3 C2 1.408(2) . ? C4 C5 1.417(2) . ? C5 C6 1.421(2) . ? C9 C8 1.364(2) . ? C9 O4 1.3819(18) . ? C2 C1 1.361(2) . ? C12 O3 1.1904(18) . ? C12 O2 1.3216(18) . ? C12 C11 1.501(2) . ? C15 O6 1.1925(17) . ? C15 O5 1.3265(17) . ? C15 C14 1.506(2) . ? C8 C7 1.403(2) . ? C14 O4 1.4241(17) . ? C6 C7 1.360(2) . ? C11 O1 1.4152(17) . ? C13 O2 1.448(2) . ? C16 O5 1.4561(19) . ? 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 C5 C10 C1 118.29(13) . . ? C5 C10 C9 118.91(13) . . ? C1 C10 C9 122.80(14) . . ? C4 C3 O1 125.36(13) . . ? C4 C3 C2 120.62(13) . . ? O1 C3 C2 114.02(12) . . ? C3 C4 C5 119.93(13) . . ? C10 C5 C4 119.81(12) . . ? C10 C5 C6 119.24(14) . . ? C4 C5 C6 120.94(14) . . ? C8 C9 O4 125.34(14) . . ? C8 C9 C10 120.64(15) . . ? O4 C9 C10 113.99(12) . . ? C1 C2 C3 120.13(13) . . ? C2 C1 C10 121.21(14) . . ? O3 C12 O2 124.64(15) . . ? O3 C12 C11 126.13(15) . . ? O2 C12 C11 109.23(13) . . ? O6 C15 O5 124.73(14) . . ? O6 C15 C14 124.88(14) . . ? O5 C15 C14 110.33(13) . . ? C9 C8 C7 119.45(15) . . ? O4 C14 C15 111.02(12) . . ? C7 C6 C5 119.56(16) . . ? O1 C11 C12 107.63(12) . . ? C6 C7 C8 122.14(15) . . ? C3 O1 C11 117.08(11) . . ? C9 O4 C14 117.96(12) . . ? C15 O5 C16 116.04(13) . . ? C12 O2 C13 115.67(13) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.117 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.029 # Attachment '27dicarboxydmso_0m.cif' data_27dicarboxydmso_0m _database_code_depnum_ccdc_archive 'CCDC 677175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 O6' _chemical_formula_weight 276.24 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.95750(10) _cell_length_b 6.92300(10) _cell_length_c 23.3344(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.6670(10) _cell_angle_gamma 90.00 _cell_volume 1224.86(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3117 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 26.91 _exptl_crystal_description Blocks _exptl_crystal_colour Brown _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15934 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3027 _reflns_number_gt 1975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.1707P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3027 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1322 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 O3 O 0.10929(13) 0.20323(16) 0.02607(4) 0.0442(3) Uani 1 1 d . . . O2 O 0.20649(15) -0.10067(16) 0.04445(5) 0.0541(4) Uani 1 1 d . . . H2O H 0.1123 -0.1262 0.0192 0.081 Uiso 1 1 calc R . . O1 O 0.39584(13) 0.34374(15) 0.10361(4) 0.0425(3) Uani 1 1 d . . . O6 O 1.41464(13) 0.20624(16) 0.46527(4) 0.0424(3) Uani 1 1 d . . . O5 O 1.28757(14) -0.08613(16) 0.45598(5) 0.0489(3) Uani 1 1 d . . . H5O H 1.3772 -0.1150 0.4830 0.073 Uiso 1 1 calc R . . O4 O 1.13283(13) 0.35496(15) 0.38449(4) 0.0443(3) Uani 1 1 d . . . C12 C 0.22144(18) 0.0852(2) 0.05144(6) 0.0354(4) Uani 1 1 d . . . C11 C 0.39377(19) 0.1411(2) 0.09677(6) 0.0393(4) Uani 1 1 d . . . H11A H 0.4052 0.0788 0.1350 0.047 Uiso 1 1 calc R . . H11B H 0.4915 0.1004 0.0829 0.047 Uiso 1 1 calc R . . C2 C 0.51250(18) 0.4232(2) 0.15392(6) 0.0335(3) Uani 1 1 d . . . C3 C 0.48322(19) 0.6211(2) 0.16093(6) 0.0389(4) Uani 1 1 d . . . H3 H 0.3910 0.6844 0.1330 0.047 Uiso 1 1 calc R . . C4 C 0.58984(19) 0.7198(2) 0.20862(6) 0.0371(4) Uani 1 1 d . . . H4 H 0.5703 0.8508 0.2127 0.045 Uiso 1 1 calc R . . C5 C 0.73031(17) 0.6263(2) 0.25218(5) 0.0312(3) Uani 1 1 d . . . C6 C 0.84393(19) 0.7259(2) 0.30212(6) 0.0363(4) Uani 1 1 d . . . H6 H 0.8280 0.8577 0.3063 0.044 Uiso 1 1 calc R . . C7 C 0.97587(19) 0.6324(2) 0.34404(6) 0.0359(4) Uani 1 1 d . . . H7 H 1.0501 0.7002 0.3763 0.043 Uiso 1 1 calc R . . C8 C 0.99927(18) 0.4327(2) 0.33834(6) 0.0332(3) Uani 1 1 d . . . C9 C 0.89453(18) 0.3308(2) 0.29013(6) 0.0344(4) Uani 1 1 d . . . H9 H 0.9129 0.1992 0.2867 0.041 Uiso 1 1 calc R . . C10 C 0.75798(16) 0.4272(2) 0.24550(5) 0.0291(3) Uani 1 1 d . . . C1 C 0.64730(18) 0.3264(2) 0.19483(6) 0.0328(3) Uani 1 1 d . . . H1 H 0.6661 0.1959 0.1895 0.039 Uiso 1 1 calc R . . C13 C 1.13387(19) 0.1527(2) 0.39162(6) 0.0374(4) Uani 1 1 d . . . H13A H 1.1363 0.0901 0.3547 0.045 Uiso 1 1 calc R . . H13B H 1.0279 0.1119 0.4005 0.045 Uiso 1 1 calc R . . C14 C 1.29411(19) 0.0955(2) 0.44225(6) 0.0349(4) 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 O3 0.0344(6) 0.0440(7) 0.0412(6) 0.0053(5) -0.0081(5) -0.0014(5) O2 0.0433(7) 0.0417(7) 0.0558(8) -0.0051(5) -0.0171(5) -0.0036(5) O1 0.0394(6) 0.0368(7) 0.0350(5) 0.0041(4) -0.0132(5) -0.0039(5) O6 0.0340(6) 0.0443(7) 0.0372(6) -0.0007(5) -0.0068(5) 0.0016(5) O5 0.0430(7) 0.0423(7) 0.0441(7) 0.0070(5) -0.0130(5) 0.0025(5) O4 0.0397(6) 0.0372(7) 0.0376(6) -0.0010(5) -0.0158(5) 0.0038(5) C12 0.0304(8) 0.0399(9) 0.0290(7) 0.0006(6) -0.0015(6) -0.0030(7) C11 0.0324(8) 0.0395(10) 0.0353(8) 0.0009(6) -0.0059(6) -0.0021(7) C2 0.0276(7) 0.0374(9) 0.0279(7) 0.0032(6) -0.0029(6) -0.0050(6) C3 0.0316(8) 0.0406(10) 0.0357(8) 0.0088(6) -0.0031(6) 0.0064(7) C4 0.0378(8) 0.0295(8) 0.0381(8) 0.0041(6) 0.0025(7) 0.0046(7) C5 0.0284(7) 0.0325(9) 0.0285(7) 0.0024(5) 0.0024(6) -0.0002(6) C6 0.0404(9) 0.0285(8) 0.0357(8) -0.0011(6) 0.0052(7) -0.0009(7) C7 0.0351(8) 0.0360(9) 0.0296(7) -0.0040(6) -0.0006(6) -0.0033(7) C8 0.0275(7) 0.0360(9) 0.0292(7) 0.0019(6) -0.0016(6) 0.0018(6) C9 0.0320(8) 0.0318(9) 0.0311(7) 0.0002(6) -0.0028(6) 0.0018(6) C10 0.0254(7) 0.0304(8) 0.0272(7) 0.0021(5) 0.0016(5) -0.0007(6) C1 0.0305(7) 0.0298(8) 0.0311(7) 0.0016(6) -0.0011(6) -0.0008(6) C13 0.0338(8) 0.0360(9) 0.0320(7) -0.0003(6) -0.0056(6) 0.0045(7) C14 0.0313(8) 0.0397(9) 0.0268(7) -0.0006(6) -0.0017(6) 0.0053(7) _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 O3 C12 1.2225(17) . ? O2 C12 1.2977(18) . ? O2 H2O 0.8200 . ? O1 C2 1.3716(15) . ? O1 C11 1.4116(18) . ? O6 C14 1.2178(17) . ? O5 C14 1.3028(18) . ? O5 H5O 0.8200 . ? O4 C8 1.3726(15) . ? O4 C13 1.4101(18) . ? C12 C11 1.5063(18) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C2 C1 1.3748(18) . ? C2 C3 1.408(2) . ? C3 C4 1.3609(19) . ? C3 H3 0.9300 . ? C4 C5 1.4184(18) . ? C4 H4 0.9300 . ? C5 C10 1.412(2) . ? C5 C6 1.4182(18) . ? C6 C7 1.3620(19) . ? C6 H6 0.9300 . ? C7 C8 1.407(2) . ? C7 H7 0.9300 . ? C8 C9 1.3745(18) . ? C9 C10 1.4227(17) . ? C9 H9 0.9300 . ? C10 C1 1.4244(17) . ? C1 H1 0.9300 . ? C13 C14 1.5046(18) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? 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 C12 O2 H2O 109.5 . . ? C2 O1 C11 118.50(11) . . ? C14 O5 H5O 109.5 . . ? C8 O4 C13 117.23(11) . . ? O3 C12 O2 125.20(13) . . ? O3 C12 C11 122.92(14) . . ? O2 C12 C11 111.86(12) . . ? O1 C11 C12 108.17(12) . . ? O1 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? O1 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? O1 C2 C1 125.54(14) . . ? O1 C2 C3 113.39(12) . . ? C1 C2 C3 121.07(13) . . ? C4 C3 C2 119.97(13) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.14(14) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C10 C5 C6 118.92(12) . . ? C10 C5 C4 118.79(12) . . ? C6 C5 C4 122.29(14) . . ? C7 C6 C5 121.28(14) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 119.64(13) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? O4 C8 C9 124.99(13) . . ? O4 C8 C7 113.86(12) . . ? C9 C8 C7 121.15(13) . . ? C8 C9 C10 119.80(14) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C5 C10 C9 119.16(12) . . ? C5 C10 C1 119.49(12) . . ? C9 C10 C1 121.34(14) . . ? C2 C1 C10 119.52(14) . . ? C2 C1 H1 120.2 . . ? C10 C1 H1 120.2 . . ? O4 C13 C14 109.09(12) . . ? O4 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? O4 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? O6 C14 O5 125.73(13) . . ? O6 C14 C13 123.17(14) . . ? O5 C14 C13 111.06(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.234 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.046 # Attachment 'tgadiol_0m-c.cif' data_tgadiol_0m _database_code_depnum_ccdc_archive 'CCDC 679649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 O6 S2' _chemical_formula_weight 340.36 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.5518(4) _cell_length_b 19.8748(14) _cell_length_c 39.870(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4399.3(5) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2619 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46463 _diffrn_reflns_av_R_equivalents 0.1071 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 25.49 _reflns_number_total 4037 _reflns_number_gt 2819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+2.8005P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4037 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6567(5) 0.18523(14) 0.04764(8) 0.0643(8) Uani 1 1 d . . . H1O H 0.6807 0.2259 0.0484 0.096 Uiso 1 1 calc R . . S2 S 0.39827(18) 0.06074(5) 0.02905(3) 0.0503(3) Uani 1 1 d . . . S1 S -0.07958(16) 0.03499(5) 0.07639(2) 0.0450(3) Uani 1 1 d . . . S3 S 0.72006(18) 1.05863(5) 0.22219(2) 0.0469(3) Uani 1 1 d . . . C6 C 0.0930(7) 0.13894(18) 0.11319(10) 0.0439(9) Uani 1 1 d . . . C7 C 0.1320(6) 0.09874(17) 0.08592(9) 0.0389(8) Uani 1 1 d . . . C14 C 0.2437(7) -0.06902(18) 0.08558(10) 0.0449(9) Uani 1 1 d . . . C10 C 0.4400(7) 0.20919(18) 0.09813(10) 0.0467(10) Uani 1 1 d . . . C5 C 0.2452(7) 0.19521(18) 0.12020(10) 0.0466(9) Uani 1 1 d . . . C8 C 0.3259(6) 0.11383(18) 0.06328(9) 0.0408(8) Uani 1 1 d . . . C9 C 0.4721(7) 0.16835(19) 0.06959(10) 0.0462(9) Uani 1 1 d . . . C13 C 0.0219(7) -0.03843(19) 0.09980(10) 0.0469(9) Uani 1 1 d . . . H13A H 0.0526 -0.0254 0.1229 0.056 Uiso 1 1 calc R . . H13B H -0.1054 -0.0719 0.0999 0.056 Uiso 1 1 calc R . . C1 C 0.5966(8) 0.2636(2) 0.10617(12) 0.0631(12) Uani 1 1 d . . . H1A H 0.7267 0.2735 0.0923 0.076 Uiso 1 1 calc R . . C11 C 0.1759(7) 0.0840(2) -0.00176(10) 0.0519(10) Uani 1 1 d . . . H11A H 0.1753 0.0510 -0.0197 0.062 Uiso 1 1 calc R . . H11B H 0.0177 0.0840 0.0086 0.062 Uiso 1 1 calc R . . C4 C 0.2067(8) 0.2367(2) 0.14861(11) 0.0604(11) Uani 1 1 d . . . H4 H 0.0782 0.2281 0.1629 0.072 Uiso 1 1 calc R . . C3 C 0.3589(10) 0.2894(2) 0.15495(12) 0.0704(14) Uani 1 1 d . . . H3 H 0.3301 0.3173 0.1732 0.084 Uiso 1 1 calc R . . C12 C 0.2266(9) 0.1531(2) -0.01633(11) 0.0610(12) Uani 1 1 d . . . C2 C 0.5551(10) 0.3015(2) 0.13439(14) 0.0717(15) Uani 1 1 d . . . H2 H 0.6611 0.3361 0.1398 0.086 Uiso 1 1 calc R . . O5 O 0.4443(5) -0.05976(15) 0.09680(8) 0.0637(8) Uani 1 1 d . . . O6 O 0.2060(5) -0.10679(15) 0.05904(8) 0.0615(8) Uani 1 1 d . . . H6O H 0.3297 -0.1273 0.0544 0.092 Uiso 1 1 calc R . . O3 O 0.0634(6) 0.19654(16) -0.00883(9) 0.0803(10) Uani 1 1 d . . . H3O H 0.0980 0.2330 -0.0172 0.120 Uiso 1 1 calc R . . O4 O 0.3999(7) 0.16618(18) -0.03310(9) 0.0840(11) Uani 1 1 d . . . O2 O -0.0864(5) 0.12886(14) 0.13578(7) 0.0573(7) Uani 1 1 d . . . H2O H -0.1591 0.0942 0.1311 0.086 Uiso 1 1 calc R . . C19 C 0.5977(6) 0.98305(16) 0.23813(8) 0.0372(8) Uani 1 1 d . . . C18 C 0.6931(7) 0.92348(18) 0.22739(9) 0.0434(9) Uani 1 1 d . . . C17 C 0.5987(7) 0.86105(18) 0.23883(9) 0.0450(9) Uani 1 1 d . . . C16 C 0.6949(9) 0.7988(2) 0.22862(12) 0.0692(14) Uani 1 1 d . . . H16 H 0.8271 0.7980 0.2143 0.083 Uiso 1 1 calc R . . C15 C 0.5975(11) 0.7401(2) 0.23937(14) 0.0908(19) Uani 1 1 d . . . H15 H 0.6631 0.6994 0.2323 0.109 Uiso 1 1 calc R . . O7 O 0.8772(5) 0.91773(14) 0.20480(8) 0.0639(8) Uani 1 1 d . . . H7O H 0.9321 0.9551 0.2007 0.096 Uiso 1 1 calc R . . C21 C 0.4062(7) 1.0347(2) 0.17044(10) 0.0497(10) Uani 1 1 d . . . C20 C 0.4778(8) 1.0877(2) 0.19491(10) 0.0532(10) Uani 1 1 d . . . H20A H 0.3395 1.0999 0.2085 0.064 Uiso 1 1 calc R . . H20B H 0.5303 1.1274 0.1828 0.064 Uiso 1 1 calc R . . O9 O 0.5549(5) 1.02975(17) 0.14445(7) 0.0658(9) Uani 1 1 d . . . H9O H 0.5075 1.0001 0.1318 0.099 Uiso 1 1 calc R . . O8 O 0.2365(6) 0.99829(17) 0.17369(8) 0.0729(9) 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 O1 0.0603(17) 0.0542(18) 0.078(2) 0.0164(17) 0.0111(15) -0.0102(14) S2 0.0581(6) 0.0483(6) 0.0446(6) 0.0004(5) 0.0002(4) 0.0104(4) S1 0.0439(5) 0.0434(5) 0.0477(6) -0.0028(4) -0.0092(4) -0.0024(4) S3 0.0599(6) 0.0362(5) 0.0446(6) 0.0024(4) 0.0001(4) -0.0113(4) C6 0.049(2) 0.043(2) 0.040(2) 0.0026(18) -0.0029(17) 0.0013(16) C7 0.046(2) 0.0335(19) 0.038(2) 0.0010(17) -0.0051(15) -0.0025(15) C14 0.048(2) 0.038(2) 0.049(2) 0.0044(18) -0.0072(18) -0.0074(16) C10 0.056(2) 0.035(2) 0.049(2) 0.0071(18) -0.0124(18) -0.0049(16) C5 0.055(2) 0.040(2) 0.045(2) -0.0008(18) -0.0108(18) 0.0031(17) C8 0.049(2) 0.036(2) 0.038(2) 0.0030(16) -0.0025(16) 0.0023(15) C9 0.049(2) 0.040(2) 0.050(2) 0.0100(19) -0.0020(18) 0.0001(16) C13 0.044(2) 0.044(2) 0.053(3) 0.0043(18) -0.0049(17) -0.0059(16) C1 0.073(3) 0.043(3) 0.073(3) 0.011(2) -0.017(2) -0.013(2) C11 0.063(3) 0.049(2) 0.044(2) -0.0033(19) -0.0096(18) 0.0020(19) C4 0.077(3) 0.054(3) 0.050(3) -0.007(2) -0.010(2) 0.002(2) C3 0.105(4) 0.047(3) 0.059(3) -0.011(2) -0.026(3) 0.003(3) C12 0.065(3) 0.068(3) 0.050(3) -0.006(2) -0.012(2) 0.012(2) C2 0.095(4) 0.038(2) 0.082(4) 0.001(3) -0.039(3) -0.013(2) O5 0.0412(16) 0.078(2) 0.072(2) -0.0176(16) -0.0068(13) -0.0040(13) O6 0.0564(17) 0.0598(19) 0.068(2) -0.0187(16) -0.0112(15) 0.0035(14) O3 0.089(2) 0.061(2) 0.091(3) -0.0062(18) 0.0005(19) 0.0205(17) O4 0.090(3) 0.077(2) 0.085(3) 0.0210(19) 0.020(2) 0.0105(19) O2 0.0647(18) 0.0548(18) 0.0522(17) -0.0097(14) 0.0115(14) -0.0098(14) C19 0.048(2) 0.0304(19) 0.033(2) -0.0002(15) -0.0026(14) -0.0053(14) C18 0.051(2) 0.036(2) 0.043(2) -0.0004(17) 0.0082(16) -0.0021(15) C17 0.061(2) 0.032(2) 0.042(2) -0.0012(17) 0.0078(17) 0.0012(16) C16 0.091(3) 0.039(2) 0.077(3) -0.007(2) 0.033(3) 0.010(2) C15 0.141(5) 0.032(3) 0.099(5) 0.000(2) 0.044(3) 0.014(3) O7 0.0710(19) 0.0456(16) 0.075(2) -0.0029(16) 0.0364(16) -0.0030(14) C21 0.051(2) 0.061(3) 0.038(2) 0.010(2) -0.0022(17) -0.0011(19) C20 0.073(3) 0.045(2) 0.041(2) 0.0080(19) 0.0036(19) 0.008(2) O9 0.0599(18) 0.087(2) 0.0508(18) -0.0185(16) 0.0126(14) -0.0261(15) O8 0.0628(19) 0.101(3) 0.0547(19) 0.0014(18) 0.0082(15) -0.0291(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.389(4) . ? S2 C8 1.771(4) . ? S2 C11 1.802(4) . ? S1 C7 1.769(3) . ? S1 C13 1.822(4) . ? S3 C19 1.767(3) . ? S3 C20 1.823(4) . ? C6 O2 1.358(4) . ? C6 C7 1.367(5) . ? C6 C5 1.429(5) . ? C7 C8 1.437(5) . ? C14 O5 1.214(4) . ? C14 O6 1.314(4) . ? C14 C13 1.486(5) . ? C10 C9 1.409(5) . ? C10 C5 1.422(5) . ? C10 C1 1.424(5) . ? C5 C4 1.417(6) . ? C8 C9 1.377(5) . ? C1 C2 1.374(7) . ? C11 C12 1.517(6) . ? C4 C3 1.369(6) . ? C3 C2 1.385(7) . ? C12 O4 1.200(5) . ? C12 O3 1.287(5) . ? C19 C18 1.366(5) . ? C19 C19 1.440(7) 3_655 ? C18 O7 1.367(4) . ? C18 C17 1.422(5) . ? C17 C16 1.407(5) . ? C17 C17 1.412(7) 3_655 ? C16 C15 1.356(6) . ? C15 C15 1.375(10) 3_655 ? C21 O8 1.195(5) . ? C21 O9 1.328(5) . ? C21 C20 1.489(6) . ? 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 C8 S2 C11 102.54(18) . . ? C7 S1 C13 104.96(17) . . ? C19 S3 C20 101.53(18) . . ? O2 C6 C7 123.9(3) . . ? O2 C6 C5 114.8(3) . . ? C7 C6 C5 121.3(3) . . ? C6 C7 C8 119.8(3) . . ? C6 C7 S1 119.0(3) . . ? C8 C7 S1 120.8(3) . . ? O5 C14 O6 122.0(4) . . ? O5 C14 C13 123.9(4) . . ? O6 C14 C13 114.1(3) . . ? C9 C10 C5 118.9(3) . . ? C9 C10 C1 122.8(4) . . ? C5 C10 C1 118.3(4) . . ? C4 C5 C10 119.7(4) . . ? C4 C5 C6 121.5(4) . . ? C10 C5 C6 118.8(3) . . ? C9 C8 C7 119.4(3) . . ? C9 C8 S2 118.4(3) . . ? C7 C8 S2 122.0(3) . . ? C8 C9 O1 120.6(4) . . ? C8 C9 C10 121.8(4) . . ? O1 C9 C10 117.6(3) . . ? C14 C13 S1 112.9(3) . . ? C2 C1 C10 119.9(5) . . ? C12 C11 S2 111.5(3) . . ? C3 C4 C5 120.0(4) . . ? C4 C3 C2 120.6(4) . . ? O4 C12 O3 123.3(5) . . ? O4 C12 C11 123.9(4) . . ? O3 C12 C11 112.8(4) . . ? C1 C2 C3 121.4(4) . . ? C18 C19 C19 119.9(2) . 3_655 ? C18 C19 S3 118.4(3) . . ? C19 C19 S3 121.74(12) 3_655 . ? C19 C18 O7 124.7(3) . . ? C19 C18 C17 120.9(3) . . ? O7 C18 C17 114.5(3) . . ? C16 C17 C17 118.5(2) . 3_655 ? C16 C17 C18 122.3(4) . . ? C17 C17 C18 119.2(2) 3_655 . ? C15 C16 C17 120.9(4) . . ? C16 C15 C15 120.6(3) . 3_655 ? O8 C21 O9 122.0(4) . . ? O8 C21 C20 124.6(4) . . ? O9 C21 C20 113.4(3) . . ? C21 C20 S3 111.3(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.391 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.096 # Attachment '13diester_2.cif' data_13diester_2 _database_code_depnum_ccdc_archive 'CCDC 684223' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 O6' _chemical_formula_weight 304.29 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 Orthorhombic _symmetry_space_group_name_H-M Cmca 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' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x, -y-1/2, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y, z-1/2' _cell_length_a 6.7148(3) _cell_length_b 16.6214(6) _cell_length_c 27.1596(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3031.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3697 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description Blocks _exptl_crystal_colour Brown _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10265 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1485 _reflns_number_gt 919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+8.2933P] 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 1485 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.2404 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0000 0.1919(2) 0.14662(12) 0.0562(11) Uani 1 2 d S . . O2 O 0.0000 -0.0073(2) 0.10314(14) 0.0772(15) Uani 1 2 d S . . O3 O 0.0000 0.1085(2) 0.06116(15) 0.0824(16) Uani 1 2 d S . . O4 O 0.0000 0.2042(2) 0.32137(12) 0.0548(11) Uani 1 2 d S . . O5 O 0.0000 0.2357(2) 0.44968(14) 0.0751(14) Uani 1 2 d S . . O6 O 0.0000 0.1213(3) 0.40713(16) 0.0942(19) Uani 1 2 d S . . C1 C 0.0000 0.3574(3) 0.1381(2) 0.0536(15) Uani 1 2 d S . . H1 H 0.0000 0.3269 0.1094 0.064 Uiso 1 2 calc SR . . C2 C 0.0000 0.4391(4) 0.1349(2) 0.0667(17) Uani 1 2 d S . . H2 H 0.0000 0.4636 0.1041 0.080 Uiso 1 2 calc SR . . C3 C 0.0000 0.4865(3) 0.1774(2) 0.0604(16) Uani 1 2 d S . . H3 H 0.0000 0.5423 0.1749 0.073 Uiso 1 2 calc SR . . C4 C 0.0000 0.4505(4) 0.2228(2) 0.0593(16) Uani 1 2 d S . . H4 H 0.0000 0.4826 0.2508 0.071 Uiso 1 2 d SR . . C5 C 0.0000 0.3656(3) 0.22793(18) 0.0433(13) Uani 1 2 d S . . C6 C 0.0000 0.3288(3) 0.27508(19) 0.0498(14) Uani 1 2 d S . . H6 H 0.0000 0.3602 0.3034 0.060 Uiso 1 2 calc SR . . C7 C 0.0000 0.2475(3) 0.27826(17) 0.0422(12) Uani 1 2 d S . . C8 C 0.0000 0.1986(3) 0.23545(17) 0.0457(13) Uani 1 2 d S . . H8 H 0.0000 0.1428 0.2382 0.055 Uiso 1 2 calc SR . . C9 C 0.0000 0.2340(3) 0.19028(17) 0.0422(12) Uani 1 2 d S . . C10 C 0.0000 0.3181(3) 0.18457(18) 0.0465(13) Uani 1 2 d S . . C11 C 0.0000 0.1081(3) 0.1497(2) 0.0521(15) Uani 1 2 d S . . C12 C 0.0000 0.0722(4) 0.0990(2) 0.0603(16) Uani 1 2 d S . . C13 C 0.0000 -0.0498(6) 0.0569(3) 0.141(5) Uani 1 2 d S . . C14 C 0.0000 0.2489(3) 0.3656(2) 0.0490(14) Uani 1 2 d S . . C15 C 0.0000 0.1924(4) 0.40839(19) 0.0601(16) Uani 1 2 d S . . C16 C 0.0000 0.1926(7) 0.4955(3) 0.116(4) Uani 1 2 d S . . H14A H 0.112(5) 0.279(2) 0.3681(12) 0.049(10) Uiso 1 1 d . . . H11A H -0.112(6) 0.088(2) 0.1659(14) 0.060(12) Uiso 1 1 d . . . H16A H 0.0000 0.236(4) 0.524(3) 0.09(2) Uiso 1 2 d S . . H17A H 0.071(9) 0.144(4) 0.495(2) 0.13(3) Uiso 1 1 d . . . H13A H 0.057(9) -0.104(3) 0.0607(17) 0.12(2) Uiso 1 1 d . . . H13B H 0.0000 -0.016(8) 0.027(4) 0.20(6) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.084(3) 0.047(2) 0.038(2) -0.0041(16) 0.000 0.000 O2 0.153(5) 0.035(2) 0.044(2) -0.0023(18) 0.000 0.000 O3 0.158(5) 0.045(3) 0.045(3) -0.001(2) 0.000 0.000 O4 0.088(3) 0.045(2) 0.0321(19) -0.0036(16) 0.000 0.000 O5 0.135(4) 0.051(3) 0.039(2) -0.0005(19) 0.000 0.000 O6 0.187(6) 0.038(3) 0.058(3) 0.000(2) 0.000 0.000 C1 0.067(4) 0.049(3) 0.045(3) 0.004(3) 0.000 0.000 C2 0.086(5) 0.060(4) 0.053(4) 0.014(3) 0.000 0.000 C3 0.073(4) 0.032(3) 0.077(4) 0.008(3) 0.000 0.000 C4 0.068(4) 0.054(4) 0.056(4) -0.002(3) 0.000 0.000 C5 0.047(3) 0.035(3) 0.048(3) -0.001(2) 0.000 0.000 C6 0.055(4) 0.051(3) 0.044(3) -0.008(2) 0.000 0.000 C7 0.049(3) 0.036(3) 0.041(3) -0.003(2) 0.000 0.000 C8 0.054(3) 0.042(3) 0.041(3) -0.004(2) 0.000 0.000 C9 0.048(3) 0.040(3) 0.039(3) -0.005(2) 0.000 0.000 C10 0.044(3) 0.055(3) 0.040(3) 0.004(2) 0.000 0.000 C11 0.079(4) 0.031(3) 0.046(3) -0.002(2) 0.000 0.000 C12 0.088(5) 0.053(4) 0.039(3) 0.001(3) 0.000 0.000 C13 0.319(17) 0.047(5) 0.057(5) -0.017(4) 0.000 0.000 C14 0.060(4) 0.044(3) 0.042(3) -0.004(2) 0.000 0.000 C15 0.082(4) 0.062(4) 0.037(3) -0.001(3) 0.000 0.000 C16 0.231(13) 0.077(6) 0.039(4) 0.010(4) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.377(6) . ? O1 C11 1.395(6) . ? O2 C12 1.327(7) . ? O2 C13 1.440(8) . ? O3 C12 1.191(7) . ? O4 C7 1.375(6) . ? O4 C14 1.412(6) . ? O5 C15 1.333(7) . ? O5 C16 1.435(9) . ? O6 C15 1.182(7) . ? C1 C2 1.359(8) . ? C1 C10 1.422(7) . ? C1 H1 0.9300 . ? C2 C3 1.398(8) . ? C2 H2 0.9300 . ? C3 C4 1.371(8) . ? C3 H3 0.9300 . ? C4 C5 1.417(8) . ? C4 H4 0.9300 . ? C5 C10 1.418(7) . ? C5 C6 1.419(7) . ? C6 C7 1.354(8) . ? C6 H6 0.9300 . ? C7 C8 1.419(7) . ? C8 C9 1.361(7) . ? C8 H8 0.9300 . ? C9 C10 1.408(7) . ? C11 C12 1.500(8) . ? C11 H11A 0.94(4) . ? C13 H13A 0.99(5) . ? C13 H13B 0.99(10) . ? C14 C15 1.495(8) . ? C14 H14A 0.90(4) . ? C16 H16A 1.06(7) . ? C16 H17A 0.93(6) . ? 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 C9 O1 C11 117.1(4) . . ? C12 O2 C13 114.5(5) . . ? C7 O4 C14 116.6(4) . . ? C15 O5 C16 117.3(6) . . ? C2 C1 C10 121.0(5) . . ? C2 C1 H1 119.5 . . ? C10 C1 H1 119.5 . . ? C1 C2 C3 120.7(6) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.7(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.6(5) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.4 . . ? C4 C5 C10 118.2(5) . . ? C4 C5 C6 121.2(5) . . ? C10 C5 C6 120.6(5) . . ? C7 C6 C5 119.2(5) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 O4 125.3(4) . . ? C6 C7 C8 121.3(5) . . ? O4 C7 C8 113.4(4) . . ? C9 C8 C7 119.4(5) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 O1 123.8(5) . . ? C8 C9 C10 121.9(5) . . ? O1 C9 C10 114.2(4) . . ? C9 C10 C5 117.5(4) . . ? C9 C10 C1 123.7(5) . . ? C5 C10 C1 118.8(5) . . ? O1 C11 C12 110.0(5) . . ? O1 C11 H11A 113(3) . . ? C12 C11 H11A 107(2) . . ? O3 C12 O2 125.3(5) . . ? O3 C12 C11 126.1(6) . . ? O2 C12 C11 108.5(5) . . ? O2 C13 H13A 111(3) . . ? O2 C13 H13B 116(7) . . ? H13A C13 H13B 127(7) . . ? O4 C14 C15 109.3(5) . . ? O4 C14 H14A 111(2) . . ? C15 C14 H14A 107(2) . . ? O6 C15 O5 124.3(5) . . ? O6 C15 C14 127.3(5) . . ? O5 C15 C14 108.4(5) . . ? O5 C16 H16A 108(4) . . ? O5 C16 H17A 114(4) . . ? H16A C16 H17A 127(5) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.244 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.060 # Attachment '16diacid-c.cif' data_16diacid _database_code_depnum_ccdc_archive 'CCDC 684224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 O6' _chemical_formula_weight 276.24 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 4.9808(3) _cell_length_b 10.8072(8) _cell_length_c 12.2998(8) _cell_angle_alpha 68.554(4) _cell_angle_beta 79.210(4) _cell_angle_gamma 80.026(4) _cell_volume 601.36(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2675 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 28.02 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6288 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2342 _reflns_number_gt 1917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.0781P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2342 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C9 C 1.1043(3) 0.23713(13) 0.15606(12) 0.0336(3) Uani 1 1 d . . . C10 C 0.9437(3) 0.12775(13) 0.21206(12) 0.0306(3) Uani 1 1 d . . . C3 C 0.6225(3) -0.08493(13) 0.31331(12) 0.0327(3) Uani 1 1 d . . . C2 C 0.7502(3) -0.04338(14) 0.38522(12) 0.0368(3) Uani 1 1 d . . . H2 H 0.7275 -0.0866 0.4665 0.044 Uiso 1 1 calc R . . C5 C 0.8132(3) 0.08595(13) 0.14021(12) 0.0321(3) Uani 1 1 d . . . C4 C 0.6522(3) -0.02267(13) 0.19406(12) 0.0348(3) Uani 1 1 d . . . H4 H 0.5668 -0.0513 0.1478 0.042 Uiso 1 1 calc R . . C1 C 0.9068(3) 0.06002(14) 0.33562(12) 0.0357(3) Uani 1 1 d . . . H1 H 0.9909 0.0866 0.3836 0.043 Uiso 1 1 calc R . . C8 C 1.1299(3) 0.30127(14) 0.03644(13) 0.0383(3) Uani 1 1 d . . . H8 H 1.2331 0.3732 0.0012 0.046 Uiso 1 1 calc R . . C6 C 0.8451(3) 0.15365(14) 0.01662(12) 0.0395(4) Uani 1 1 d . . . H6 H 0.7603 0.1268 -0.0310 0.047 Uiso 1 1 calc R . . C7 C 0.9991(3) 0.25772(15) -0.03268(13) 0.0412(4) Uani 1 1 d . . . H7 H 1.0184 0.3011 -0.1139 0.049 Uiso 1 1 calc R . . C11 C 1.3781(3) 0.38063(14) 0.18152(13) 0.0376(3) Uani 1 1 d . . . H11A H 1.2560 0.4603 0.1467 0.045 Uiso 1 1 calc R . . H11B H 1.5173 0.3667 0.1192 0.045 Uiso 1 1 calc R . . C13 C 0.3400(3) -0.23838(14) 0.30731(12) 0.0363(3) Uani 1 1 d . . . H13A H 0.4745 -0.2692 0.2519 0.044 Uiso 1 1 calc R . . H13B H 0.2119 -0.1676 0.2634 0.044 Uiso 1 1 calc R . . C12 C 1.5143(3) 0.40158(14) 0.27161(13) 0.0380(3) Uani 1 1 d . . . C14 C 0.1897(3) -0.35165(14) 0.39275(12) 0.0350(3) Uani 1 1 d . . . O4 O 0.4721(2) -0.19088(10) 0.37416(8) 0.0409(3) Uani 1 1 d . . . O1 O 1.2259(2) 0.26927(10) 0.23199(9) 0.0407(3) Uani 1 1 d . . . O6 O 0.2134(2) -0.39949(11) 0.49695(9) 0.0479(3) Uani 1 1 d . . . O5 O 0.0352(2) -0.39293(11) 0.34097(9) 0.0478(3) Uani 1 1 d . . . H5O H -0.0433 -0.4551 0.3897 0.072 Uiso 1 1 calc R . . O2 O 1.6587(3) 0.48999(11) 0.24301(10) 0.0550(3) Uani 1 1 d . . . O3 O 1.4617(3) 0.31818(11) 0.37914(9) 0.0521(3) Uani 1 1 d . . . H3O H 1.5448 0.3345 0.4230 0.078 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 C9 0.0341(7) 0.0332(7) 0.0350(7) -0.0096(6) -0.0064(6) -0.0108(6) C10 0.0313(7) 0.0298(7) 0.0310(7) -0.0083(6) -0.0039(6) -0.0095(5) C3 0.0339(7) 0.0303(7) 0.0349(7) -0.0086(6) -0.0029(6) -0.0136(6) C2 0.0441(8) 0.0395(8) 0.0284(7) -0.0078(6) -0.0049(6) -0.0173(6) C5 0.0342(7) 0.0319(7) 0.0319(7) -0.0103(6) -0.0041(6) -0.0097(6) C4 0.0384(8) 0.0379(7) 0.0337(7) -0.0125(6) -0.0078(6) -0.0154(6) C1 0.0407(8) 0.0376(7) 0.0331(7) -0.0109(6) -0.0071(6) -0.0157(6) C8 0.0418(8) 0.0359(7) 0.0349(8) -0.0049(6) -0.0027(6) -0.0173(6) C6 0.0485(9) 0.0439(8) 0.0306(7) -0.0122(6) -0.0083(6) -0.0155(7) C7 0.0497(9) 0.0429(8) 0.0278(7) -0.0051(6) -0.0041(6) -0.0140(7) C11 0.0430(8) 0.0316(7) 0.0383(8) -0.0058(6) -0.0054(6) -0.0184(6) C13 0.0403(8) 0.0364(7) 0.0351(8) -0.0095(6) -0.0053(6) -0.0182(6) C12 0.0418(8) 0.0331(7) 0.0403(8) -0.0104(6) -0.0037(7) -0.0141(6) C14 0.0360(8) 0.0358(7) 0.0359(8) -0.0109(6) -0.0051(6) -0.0141(6) O4 0.0504(6) 0.0422(6) 0.0340(5) -0.0069(4) -0.0065(5) -0.0285(5) O1 0.0505(6) 0.0396(6) 0.0351(5) -0.0057(4) -0.0085(5) -0.0264(5) O6 0.0607(7) 0.0505(6) 0.0359(6) -0.0048(5) -0.0099(5) -0.0340(5) O5 0.0575(7) 0.0506(7) 0.0395(6) -0.0058(5) -0.0107(5) -0.0342(5) O2 0.0672(8) 0.0517(7) 0.0534(7) -0.0121(5) -0.0090(6) -0.0383(6) O3 0.0707(8) 0.0498(6) 0.0396(6) -0.0049(5) -0.0144(6) -0.0327(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C9 C8 1.370(2) . ? C9 O1 1.3714(16) . ? C9 C10 1.4274(18) . ? C10 C1 1.4169(19) . ? C10 C5 1.4201(18) . ? C3 C4 1.3629(19) . ? C3 O4 1.3760(15) . ? C3 C2 1.4102(18) . ? C2 C1 1.3618(19) . ? C2 H2 0.9300 . ? C5 C6 1.4171(19) . ? C5 C4 1.4208(18) . ? C4 H4 0.9300 . ? C1 H1 0.9300 . ? C8 C7 1.4052(19) . ? C8 H8 0.9300 . ? C6 C7 1.3590(19) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C11 O1 1.4148(16) . ? C11 C12 1.5026(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 O4 1.4145(15) . ? C13 C14 1.4983(18) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C12 O2 1.2048(17) . ? C12 O3 1.3080(18) . ? C14 O6 1.2144(16) . ? C14 O5 1.3067(16) . ? O5 H5O 0.8200 . ? O3 H3O 0.8200 . ? 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 C8 C9 O1 124.74(12) . . ? C8 C9 C10 121.08(13) . . ? O1 C9 C10 114.17(12) . . ? C1 C10 C5 118.66(12) . . ? C1 C10 C9 123.14(12) . . ? C5 C10 C9 118.20(12) . . ? C4 C3 O4 124.82(12) . . ? C4 C3 C2 120.97(12) . . ? O4 C3 C2 114.21(12) . . ? C1 C2 C3 119.99(13) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C6 C5 C10 119.41(12) . . ? C6 C5 C4 121.42(12) . . ? C10 C5 C4 119.17(12) . . ? C3 C4 C5 120.14(12) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C2 C1 C10 121.07(13) . . ? C2 C1 H1 119.5 . . ? C10 C1 H1 119.5 . . ? C9 C8 C7 119.58(13) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C7 C6 C5 120.27(13) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 121.45(13) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? O1 C11 C12 111.67(11) . . ? O1 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? O1 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? O4 C13 C14 106.98(11) . . ? O4 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? O4 C13 H13B 110.3 . . ? C14 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? O2 C12 O3 124.71(14) . . ? O2 C12 C11 120.46(13) . . ? O3 C12 C11 114.83(12) . . ? O6 C14 O5 124.73(13) . . ? O6 C14 C13 123.52(12) . . ? O5 C14 C13 111.74(11) . . ? C3 O4 C13 117.19(10) . . ? C9 O1 C11 116.42(11) . . ? C14 O5 H5O 109.5 . . ? C12 O3 H3O 109.5 . . ? 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 C8 C9 C10 C1 -178.72(13) . . . . ? O1 C9 C10 C1 1.5(2) . . . . ? C8 C9 C10 C5 0.7(2) . . . . ? O1 C9 C10 C5 -179.08(11) . . . . ? C4 C3 C2 C1 -0.3(2) . . . . ? O4 C3 C2 C1 179.54(12) . . . . ? C1 C10 C5 C6 179.22(13) . . . . ? C9 C10 C5 C6 -0.3(2) . . . . ? C1 C10 C5 C4 -0.5(2) . . . . ? C9 C10 C5 C4 -179.95(12) . . . . ? O4 C3 C4 C5 -179.87(12) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C6 C5 C4 C3 -179.24(13) . . . . ? C10 C5 C4 C3 0.5(2) . . . . ? C3 C2 C1 C10 0.2(2) . . . . ? C5 C10 C1 C2 0.1(2) . . . . ? C9 C10 C1 C2 179.58(13) . . . . ? O1 C9 C8 C7 178.90(13) . . . . ? C10 C9 C8 C7 -0.9(2) . . . . ? C10 C5 C6 C7 0.0(2) . . . . ? C4 C5 C6 C7 179.66(14) . . . . ? C5 C6 C7 C8 -0.1(2) . . . . ? C9 C8 C7 C6 0.6(2) . . . . ? O1 C11 C12 O2 177.92(14) . . . . ? O1 C11 C12 O3 -2.28(19) . . . . ? O4 C13 C14 O6 -8.1(2) . . . . ? O4 C13 C14 O5 172.81(12) . . . . ? C4 C3 O4 C13 0.3(2) . . . . ? C2 C3 O4 C13 -179.54(12) . . . . ? C14 C13 O4 C3 -179.53(11) . . . . ? C8 C9 O1 C11 2.8(2) . . . . ? C10 C9 O1 C11 -177.45(11) . . . . ? C12 C11 O1 C9 -176.82(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.148 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.061 # Attachment '27diester_1.cif' data_27diester_1 _database_code_depnum_ccdc_archive 'CCDC 684225' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 O6' _chemical_formula_weight 304.29 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 27.3847(10) _cell_length_b 6.7513(3) _cell_length_c 8.0896(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.669(3) _cell_angle_gamma 90.00 _cell_volume 1495.52(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 21.45 _exptl_crystal_description Blocks _exptl_crystal_colour Brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16525 _diffrn_reflns_av_R_equivalents 0.0882 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3623 _reflns_number_gt 1531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.0650P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3623 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1758 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1796 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.13773(6) 0.3502(3) 0.0053(2) 0.0564(5) Uani 1 1 d . . . O4 O 0.36509(6) 0.3413(3) 0.4951(2) 0.0638(6) Uani 1 1 d . . . O6 O 0.42164(8) -0.1174(4) 0.5647(3) 0.0897(8) Uani 1 1 d . . . O5 O 0.44100(9) 0.1847(4) 0.6567(3) 0.1009(9) Uani 1 1 d . . . O2 O 0.06278(8) 0.2011(3) -0.1697(3) 0.0829(7) Uani 1 1 d . . . O3 O 0.07574(7) -0.1003(3) -0.0612(2) 0.0677(6) Uani 1 1 d . . . C2 C 0.17394(9) 0.4294(4) 0.1044(3) 0.0452(7) Uani 1 1 d . . . C3 C 0.16648(10) 0.6290(4) 0.1463(3) 0.0508(7) Uani 1 1 d . . . H3 H 0.1391 0.6959 0.1061 0.061 Uiso 1 1 calc R . . C4 C 0.19932(10) 0.7242(4) 0.2459(3) 0.0512(7) Uani 1 1 d . . . H4 H 0.1941 0.8561 0.2737 0.061 Uiso 1 1 calc R . . C5 C 0.24127(9) 0.6252(4) 0.3076(3) 0.0463(7) Uani 1 1 d . . . C6 C 0.27578(10) 0.7177(4) 0.4140(3) 0.0560(8) Uani 1 1 d . . . H6 H 0.2710 0.8488 0.4450 0.067 Uiso 1 1 calc R . . C7 C 0.31573(11) 0.6197(4) 0.4720(4) 0.0598(8) Uani 1 1 d . . . H7 H 0.3379 0.6835 0.5419 0.072 Uiso 1 1 calc R . . C8 C 0.32348(9) 0.4225(4) 0.4262(3) 0.0504(7) Uani 1 1 d . . . C9 C 0.29128(9) 0.3244(4) 0.3244(3) 0.0460(7) Uani 1 1 d . . . H9 H 0.2971 0.1934 0.2951 0.055 Uiso 1 1 calc R . . C10 C 0.24902(9) 0.4240(3) 0.2638(3) 0.0428(6) Uani 1 1 d . . . C1 C 0.21409(9) 0.3285(4) 0.1612(3) 0.0467(7) Uani 1 1 d . . . H1 H 0.2184 0.1964 0.1322 0.056 Uiso 1 1 calc R . . C14 C 0.37339(10) 0.1370(4) 0.4705(4) 0.0595(8) Uani 1 1 d . . . H14A H 0.3802 0.1112 0.3551 0.071 Uiso 1 1 calc R . . H14B H 0.3447 0.0616 0.5010 0.071 Uiso 1 1 calc R . . C15 C 0.41620(11) 0.0778(5) 0.5764(4) 0.0637(8) Uani 1 1 d . . . C16 C 0.46017(14) -0.2091(7) 0.6614(6) 0.1224(16) Uani 1 1 d . . . H16A H 0.4911 -0.1567 0.6283 0.184 Uiso 1 1 calc R . . H16B H 0.4597 -0.3497 0.6435 0.184 Uiso 1 1 calc R . . H16C H 0.4553 -0.1819 0.7765 0.184 Uiso 1 1 calc R . . C12 C 0.08553(10) 0.0909(5) -0.0827(3) 0.0532(7) Uani 1 1 d . . . C13 C 0.03617(12) -0.1854(6) -0.1571(5) 0.0933(12) Uani 1 1 d . . . H13A H 0.0056 -0.1342 -0.1185 0.140 Uiso 1 1 calc R . . H13B H 0.0366 -0.3268 -0.1449 0.140 Uiso 1 1 calc R . . H13C H 0.0400 -0.1517 -0.2715 0.140 Uiso 1 1 calc R . . C11 C 0.13030(9) 0.1440(4) 0.0160(3) 0.0487(7) Uani 1 1 d . . . H11A H 0.1262 0.1056 0.1306 0.058 Uiso 1 1 calc R . . H11B H 0.1584 0.0743 -0.0269 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0561(12) 0.0472(11) 0.0656(12) 0.0066(9) -0.0203(10) 0.0001(9) O4 0.0525(12) 0.0538(12) 0.0846(15) -0.0061(10) -0.0205(11) -0.0030(10) O6 0.0716(15) 0.0821(17) 0.115(2) 0.0158(14) -0.0349(14) 0.0084(13) O5 0.0745(16) 0.111(2) 0.116(2) -0.0168(16) -0.0451(15) 0.0001(14) O2 0.0667(14) 0.0870(17) 0.0940(17) 0.0200(13) -0.0328(13) 0.0001(12) O3 0.0574(12) 0.0657(14) 0.0797(15) -0.0062(11) -0.0172(11) -0.0096(10) C2 0.0481(16) 0.0427(15) 0.0448(16) 0.0041(12) -0.0028(13) 0.0016(13) C3 0.0512(16) 0.0439(16) 0.0572(18) 0.0091(13) 0.0008(14) 0.0072(13) C4 0.0610(18) 0.0336(14) 0.0591(19) 0.0033(12) 0.0044(15) 0.0035(13) C5 0.0496(16) 0.0391(15) 0.0503(17) 0.0023(12) 0.0057(13) -0.0045(12) C6 0.0648(19) 0.0377(15) 0.065(2) -0.0032(13) -0.0023(16) -0.0078(14) C7 0.0638(19) 0.0496(18) 0.066(2) -0.0094(14) -0.0093(16) -0.0154(15) C8 0.0443(16) 0.0508(17) 0.0559(18) 0.0021(13) -0.0067(14) -0.0036(13) C9 0.0458(16) 0.0409(16) 0.0512(17) -0.0002(11) -0.0006(14) -0.0029(12) C10 0.0460(14) 0.0383(13) 0.0443(15) 0.0026(12) 0.0048(12) -0.0026(13) C1 0.0504(17) 0.0405(16) 0.0492(17) -0.0033(11) -0.0030(14) 0.0033(12) C14 0.0499(17) 0.0582(19) 0.070(2) -0.0008(15) -0.0139(15) -0.0031(14) C15 0.0477(18) 0.074(2) 0.069(2) 0.0048(17) -0.0076(16) -0.0007(17) C16 0.088(3) 0.132(4) 0.146(4) 0.049(3) -0.037(3) 0.019(3) C12 0.0424(16) 0.064(2) 0.0526(18) -0.0017(14) -0.0034(14) 0.0024(15) C13 0.064(2) 0.115(3) 0.100(3) -0.027(2) -0.019(2) -0.026(2) C11 0.0467(16) 0.0495(17) 0.0497(16) -0.0013(13) -0.0055(13) 0.0043(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.376(3) . ? O1 C11 1.410(3) . ? O4 C8 1.376(3) . ? O4 C14 1.413(3) . ? O6 C15 1.330(4) . ? O6 C16 1.445(4) . ? O5 C15 1.181(3) . ? O2 C12 1.194(3) . ? O3 C12 1.330(3) . ? O3 C13 1.445(3) . ? C2 C1 1.368(3) . ? C2 C3 1.405(3) . ? C3 C4 1.361(4) . ? C3 H3 0.9300 . ? C4 C5 1.415(3) . ? C4 H4 0.9300 . ? C5 C6 1.416(3) . ? C5 C10 1.420(3) . ? C6 C7 1.357(4) . ? C6 H6 0.9300 . ? C7 C8 1.399(4) . ? C7 H7 0.9300 . ? C8 C9 1.370(3) . ? C9 C10 1.421(3) . ? C9 H9 0.9300 . ? C10 C1 1.415(3) . ? C1 H1 0.9300 . ? C14 C15 1.499(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C12 C11 1.499(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 O1 C11 116.84(19) . . ? C8 O4 C14 117.7(2) . . ? C15 O6 C16 117.9(3) . . ? C12 O3 C13 117.8(3) . . ? C1 C2 O1 124.9(2) . . ? C1 C2 C3 121.0(2) . . ? O1 C2 C3 114.1(2) . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 122.7(2) . . ? C6 C5 C10 118.2(2) . . ? C4 C5 C10 119.1(2) . . ? C7 C6 C5 121.7(3) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 119.8(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 O4 125.1(3) . . ? C9 C8 C7 121.4(3) . . ? O4 C8 C7 113.5(2) . . ? C8 C9 C10 119.7(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C1 C10 C5 118.7(2) . . ? C1 C10 C9 122.0(2) . . ? C5 C10 C9 119.3(2) . . ? C2 C1 C10 120.3(2) . . ? C2 C1 H1 119.8 . . ? C10 C1 H1 119.8 . . ? O4 C14 C15 107.8(2) . . ? O4 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? O4 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.5 . . ? O5 C15 O6 125.5(3) . . ? O5 C15 C14 126.4(3) . . ? O6 C15 C14 108.1(3) . . ? O6 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C12 O3 125.2(3) . . ? O2 C12 C11 125.7(3) . . ? O3 C12 C11 109.1(2) . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C11 C12 108.7(2) . . ? O1 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O1 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.157 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.045