# 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 'Sethuraman Sankararaman' _publ_contact_author_email SANKA@IITM.AC.IN _publ_section_title ; Hydrogen-bond network in isomeric phenylene dipropynoic acids and their DABCO salts. Water mediated helical hydrogen bond motifs ; loop_ _publ_author_name 'Sethuraman Sankararaman' 'Rajendran Saravanakumar' 'Babu Varghese' # Attachment '12PPAnew.cif' #=========================================================================== data_12ppa _database_code_depnum_ccdc_archive 'CCDC 656598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H6 O4' _chemical_formula_sum 'C12 H6 O4' _chemical_formula_weight 214.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 3.7990(3) _cell_length_b 10.4652(9) _cell_length_c 12.4395(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.309(6) _cell_angle_gamma 90.00 _cell_volume 494.55(7) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2445 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.5 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8643 _exptl_absorpt_correction_T_max 0.9332 _exptl_absorpt_process_details 'SADABS(Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5954 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 26.40 _reflns_number_total 1016 _reflns_number_gt 761 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare etal., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 32 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The C-H hydrogens were fixed at chemically idealised positions and were given riding model refinement with C-H (0.930\%A)and U~iso~1.2 time U~eq~ of parent atom. The differnece map showed hydroxyl hydrogens disordered to both oxygens. Each hydrogen was assigned 50% occupancy. One of them (of O1) was restrained to ride over the parent oxygen (O-H 0.82\%A and C-O-H tetrahedral)and its isotropic thermal parameter was refined. The other hydrogen was given unrestrained isotropic refinement. ; _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^)+(0.0302P)^2^+0.9194P] 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 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1016 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1736 _refine_ls_wR_factor_gt 0.1602 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.191 _refine_ls_shift/su_max 0.002 _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 0.7144(10) 0.6544(3) 0.5955(3) 0.0447(9) Uani 1 1 d . . . C2 C 0.7758(10) 0.7859(4) 0.6206(3) 0.0449(9) Uani 1 1 d . . . C3 C 0.8350(9) 0.8913(3) 0.6512(3) 0.0402(8) Uani 1 1 d . . . C4 C 0.9178(8) 1.0120(3) 0.6988(3) 0.0361(8) Uani 1 1 d . . . C5 C 0.8400(9) 1.1274(3) 0.6491(3) 0.0432(9) Uani 1 1 d . . . H5 H 0.7339 1.1281 0.5815 0.052 Uiso 1 1 calc R . . C6 C 0.9207(10) 1.2419(3) 0.7002(3) 0.0491(10) Uani 1 1 d . . . H6 H 0.8672 1.3191 0.6667 0.059 Uiso 1 1 calc R . . O1 O 0.5450(8) 0.6261(3) 0.5119(2) 0.0590(9) Uani 1 1 d . . . H1 H 0.5237 0.5482 0.5080 0.07(3) Uiso 0.50 1 calc PR . . O2 O 0.8279(10) 0.5680(3) 0.6583(3) 0.0700(11) Uani 1 1 d . . . H2 H 0.98(3) 0.580(8) 0.703(6) 0.06(3) Uiso 0.50 1 d P . . 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 0.052(2) 0.041(2) 0.0408(19) -0.0035(16) -0.0127(17) -0.0030(16) C2 0.051(2) 0.044(2) 0.0394(19) -0.0027(16) -0.0096(16) -0.0009(17) C3 0.0412(19) 0.0406(19) 0.0388(18) -0.0037(15) -0.0036(14) -0.0018(15) C4 0.0377(17) 0.0335(18) 0.0370(17) -0.0014(14) -0.0018(14) 0.0007(14) C5 0.049(2) 0.042(2) 0.0379(18) 0.0013(16) -0.0089(15) 0.0002(17) C6 0.061(2) 0.0303(19) 0.056(2) 0.0058(16) -0.0075(18) 0.0042(16) O1 0.085(2) 0.0431(17) 0.0484(16) -0.0042(12) -0.0347(14) -0.0055(14) O2 0.103(3) 0.0475(17) 0.0589(19) 0.0081(15) -0.0421(19) -0.0080(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 C1 O1 1.256(4) . ? C1 O2 1.269(4) . ? C1 C2 1.430(5) . ? C2 C3 1.188(5) . ? C3 C4 1.430(5) . ? C4 C5 1.388(5) . ? C4 C4 1.415(6) 2_756 ? C5 C6 1.390(5) . ? C5 H5 0.9300 . ? C6 C6 1.375(7) 2_756 ? C6 H6 0.9300 . ? O1 H1 0.8200 . ? O2 H2 0.81(9) . ? 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 O1 C1 O2 120.8(3) . . ? O1 C1 C2 119.3(3) . . ? O2 C1 C2 119.8(3) . . ? C3 C2 C1 173.6(4) . . ? C2 C3 C4 173.8(4) . . ? C5 C4 C4 119.5(2) . 2_756 ? C5 C4 C3 122.6(3) . . ? C4 C4 C3 117.91(19) 2_756 . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C6 C6 C5 120.4(2) 2_756 . ? C6 C6 H6 119.8 2_756 . ? C5 C6 H6 119.8 . . ? C1 O1 H1 109.5 . . ? C1 O2 H2 124(6) . . ? 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 O1 C1 C2 C3 164(4) . . . . ? O2 C1 C2 C3 -15(4) . . . . ? C1 C2 C3 C4 4(7) . . . . ? C2 C3 C4 C5 -172(3) . . . . ? C2 C3 C4 C4 7(4) . . . 2_756 ? C4 C4 C5 C6 -0.6(6) 2_756 . . . ? C3 C4 C5 C6 178.8(4) . . . . ? C4 C5 C6 C6 0.3(7) . . . 2_756 ? 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 O1 0.82 1.86 2.677(5) 175.1 3_666 O2 H2 O2 0.80(8) 1.88(8) 2.623(6) 154(9) 2_756 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.225 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.055 # Attachment '12PPAdabco_new.cif' #=========================================================================== data_ssr2 _database_code_depnum_ccdc_archive 'CCDC 656599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N2 O6' _chemical_formula_weight 362.38 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' N N 0.0061 0.0033 '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 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 8.5222(4) _cell_length_b 9.1871(5) _cell_length_c 23.0730(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.067(2) _cell_angle_gamma 90.00 _cell_volume 1792.76(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6322 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.0 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9212 _exptl_absorpt_correction_T_max 0.9657 _exptl_absorpt_process_details 'SADABS(Buker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 30271 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.89 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3147 _reflns_number_gt 2408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. In DABCO, both nitrogens are protonated. The oxygens of one of the carboxylate groups are disordered. The disordered oxygens pairs(O1, O1'; O2, O2') are refined such that sum of their ocuppancies is constrained to 1.00(1). All the hydrogens appeared in the difference Fourier map. However, the C-H hydrogens were fixed at chemically meaningfull positions and riding model refinement was performed ( C-H (aromatic) = 0.93\%A; C-H (secondary -CH2-) = 0.97\%A; Uis0 = 1.2U~eq~ of the parent atom). The N-H hydrogenS were isotropically refined. The N-H distance(0.95(1)\%A) was restrained to be in the vicinity of corresponding difference Fourier peak. Similarly, the water hydrogens were restrained (O-H = 0.95(1)\%A and H...H 1.55(1)\%A during refinement. All the donor-acceptor distances are well with in the hydrogen bonding interaction range. ; _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^)+(0.0597P)^2^+3.7519P] 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 0.0016(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3147 _refine_ls_number_parameters 268 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.2269 _refine_ls_wR_factor_gt 0.2051 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.111 _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 C1 C 0.3357(6) 0.9826(7) 0.1655(2) 0.0703(14) Uani 1 1 d . . . C2 C 0.3120(5) 0.9731(5) 0.10189(18) 0.0535(11) Uani 1 1 d . A . C3 C 0.2905(5) 0.9618(4) 0.05037(17) 0.0475(10) Uani 1 1 d . . . C4 C 0.2645(5) 0.9465(4) -0.01196(16) 0.0438(9) Uani 1 1 d . A . C5 C 0.1584(5) 1.0376(5) -0.04503(19) 0.0580(11) Uani 1 1 d . . . H5 H 0.1031 1.1077 -0.0267 0.070 Uiso 1 1 calc R A . C6 C 0.1346(6) 1.0242(6) -0.10523(19) 0.0632(12) Uani 1 1 d . A . H6 H 0.0637 1.0857 -0.1272 0.076 Uiso 1 1 calc R . . C7 C 0.2147(6) 0.9212(6) -0.13261(18) 0.0613(12) Uani 1 1 d . . . H7 H 0.1987 0.9131 -0.1731 0.074 Uiso 1 1 calc R A . C8 C 0.3182(5) 0.8300(5) -0.10061(17) 0.0555(11) Uani 1 1 d . A . H8 H 0.3708 0.7593 -0.1197 0.067 Uiso 1 1 calc R . . C9 C 0.3467(4) 0.8406(4) -0.04007(16) 0.0433(9) Uani 1 1 d . . . C10 C 0.4622(5) 0.7504(5) -0.00770(16) 0.0478(10) Uani 1 1 d . A . C11 C 0.5628(5) 0.6768(5) 0.01796(16) 0.0492(10) Uani 1 1 d . . . C12 C 0.6965(5) 0.5958(5) 0.04821(16) 0.0483(10) Uani 1 1 d . A . C13 C 0.6653(5) 0.5816(6) -0.13181(18) 0.0612(12) Uani 1 1 d . . . H13A H 0.6389 0.6834 -0.1276 0.073 Uiso 1 1 calc R . . H13B H 0.5777 0.5231 -0.1219 0.073 Uiso 1 1 calc R . . C14 C 0.6951(5) 0.5506(7) -0.19391(19) 0.0691(14) Uani 1 1 d . . . H14A H 0.6305 0.4692 -0.2094 0.083 Uiso 1 1 calc R . . H14B H 0.6670 0.6349 -0.2183 0.083 Uiso 1 1 calc R . . C15 C 0.9399(5) 0.6482(5) -0.10386(18) 0.0553(11) Uani 1 1 d . . . H15A H 1.0371 0.6245 -0.0792 0.066 Uiso 1 1 calc R . . H15B H 0.9100 0.7470 -0.0953 0.066 Uiso 1 1 calc R . . C16 C 0.9637(6) 0.6350(7) -0.1674(2) 0.0754(16) Uani 1 1 d . . . H16A H 0.9349 0.7257 -0.1875 0.091 Uiso 1 1 calc R . . H16B H 1.0741 0.6153 -0.1707 0.091 Uiso 1 1 calc R . . C17 C 0.8597(6) 0.3936(5) -0.10185(19) 0.0649(13) Uani 1 1 d . . . H17A H 0.7725 0.3284 -0.0973 0.078 Uiso 1 1 calc R . . H17B H 0.9481 0.3673 -0.0732 0.078 Uiso 1 1 calc R . . C18 C 0.9065(7) 0.3793(7) -0.1626(2) 0.0835(17) Uani 1 1 d . . . H18A H 1.0193 0.3619 -0.1606 0.100 Uiso 1 1 calc R . . H18B H 0.8513 0.2981 -0.1827 0.100 Uiso 1 1 calc R . . N1 N 0.8122(4) 0.5450(4) -0.09241(13) 0.0492(9) Uani 1 1 d D . . N2 N 0.8646(5) 0.5157(5) -0.19431(15) 0.0674(12) Uani 1 1 d D . . O1 O 0.3384(15) 1.0911(17) 0.1912(5) 0.095(3) Uani 0.601(11) 1 d P A 1 O2 O 0.3657(12) 0.8506(11) 0.1908(4) 0.075(2) Uani 0.601(11) 1 d P A 1 O1' O 0.249(2) 1.096(3) 0.1848(9) 0.095(3) Uani 0.399(11) 1 d P A 2 O2' O 0.417(2) 0.9187(17) 0.1959(6) 0.075(2) Uani 0.399(11) 1 d P A 2 O3 O 0.8024(3) 0.5570(4) 0.01825(12) 0.0648(9) Uani 1 1 d . . . O4 O 0.6992(4) 0.5706(4) 0.10084(12) 0.0744(11) Uani 1 1 d . . . O5 O 0.8683(9) 0.8463(10) 0.2678(3) 0.173(3) Uani 1 1 d D . . O6 O 0.8685(6) 0.1860(6) 0.29715(17) 0.1008(14) Uani 1 1 d D . . H1 H 0.798(6) 0.555(5) -0.0524(7) 0.074(14) Uiso 1 1 d D . . H2 H 0.875(7) 0.487(6) -0.2333(10) 0.11(2) Uiso 1 1 d D . . H5A H 0.84(2) 0.763(11) 0.244(7) 0.41(7) Uiso 1 1 d D . . H5B H 0.797(19) 0.924(13) 0.256(8) 0.41(7) Uiso 1 1 d D . . H6A H 0.969(5) 0.232(8) 0.302(2) 0.15(3) Uiso 1 1 d D . . H6B H 0.836(6) 0.169(7) 0.3343(11) 0.11(2) Uiso 1 1 d 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 0.078(3) 0.098(4) 0.037(2) -0.005(3) 0.016(2) -0.013(3) C2 0.064(3) 0.055(3) 0.043(2) 0.0017(19) 0.0118(19) 0.001(2) C3 0.057(2) 0.043(2) 0.043(2) 0.0041(17) 0.0089(17) 0.0010(19) C4 0.048(2) 0.044(2) 0.0394(19) 0.0053(17) 0.0070(16) -0.0048(18) C5 0.065(3) 0.051(3) 0.058(3) 0.005(2) 0.006(2) 0.011(2) C6 0.068(3) 0.065(3) 0.053(3) 0.015(2) -0.006(2) 0.008(2) C7 0.067(3) 0.076(3) 0.040(2) 0.006(2) 0.0020(19) -0.003(3) C8 0.055(2) 0.070(3) 0.041(2) -0.006(2) 0.0043(18) 0.007(2) C9 0.041(2) 0.049(2) 0.0397(19) 0.0016(17) 0.0037(15) -0.0007(18) C10 0.046(2) 0.058(3) 0.039(2) -0.0018(19) 0.0047(17) 0.000(2) C11 0.048(2) 0.061(3) 0.038(2) -0.0010(19) 0.0067(17) 0.002(2) C12 0.050(2) 0.058(3) 0.036(2) 0.0032(18) 0.0026(17) 0.006(2) C13 0.047(2) 0.090(4) 0.047(2) 0.006(2) 0.0088(18) 0.007(2) C14 0.052(3) 0.109(4) 0.045(2) 0.003(3) -0.0008(19) 0.009(3) C15 0.058(3) 0.056(3) 0.051(2) 0.007(2) 0.0040(19) -0.005(2) C16 0.061(3) 0.113(5) 0.054(3) 0.021(3) 0.010(2) -0.010(3) C17 0.081(3) 0.056(3) 0.054(3) 0.004(2) -0.003(2) 0.000(2) C18 0.101(4) 0.085(4) 0.062(3) -0.012(3) 0.000(3) 0.031(3) N1 0.055(2) 0.060(2) 0.0336(16) 0.0041(16) 0.0077(14) 0.0000(17) N2 0.061(2) 0.107(3) 0.0349(18) 0.001(2) 0.0082(16) 0.019(2) O1 0.149(11) 0.091(3) 0.049(3) -0.017(3) 0.026(7) -0.018(10) O2 0.094(6) 0.086(7) 0.046(2) 0.015(4) 0.017(3) 0.011(4) O1' 0.149(11) 0.091(3) 0.049(3) -0.017(3) 0.026(7) -0.018(10) O2' 0.094(6) 0.086(7) 0.046(2) 0.015(4) 0.017(3) 0.011(4) O3 0.0522(17) 0.103(3) 0.0396(15) 0.0069(16) 0.0080(13) 0.0196(17) O4 0.085(2) 0.104(3) 0.0359(15) 0.0148(17) 0.0125(14) 0.029(2) O5 0.143(5) 0.211(7) 0.151(5) 0.044(5) -0.043(4) -0.054(5) O6 0.105(3) 0.127(4) 0.073(3) 0.030(3) 0.021(2) 0.005(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 O2' 1.092(16) . ? C1 O1 1.157(15) . ? C1 O2 1.357(12) . ? C1 O1' 1.38(3) . ? C1 C2 1.460(6) . ? C2 C3 1.185(5) . ? C3 C4 1.435(5) . ? C4 C5 1.390(6) . ? C4 C9 1.404(5) . ? C5 C6 1.384(6) . ? C5 H5 0.9300 . ? C6 C7 1.367(7) . ? C6 H6 0.9300 . ? C7 C8 1.365(6) . ? C7 H7 0.9300 . ? C8 C9 1.391(5) . ? C8 H8 0.9300 . ? C9 C10 1.426(6) . ? C10 C11 1.190(6) . ? C11 C12 1.464(6) . ? C12 O4 1.234(4) . ? C12 O3 1.254(5) . ? C13 N1 1.492(5) . ? C13 C14 1.512(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.481(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N1 1.490(5) . ? C15 C16 1.510(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N2 1.474(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N1 1.472(6) . ? C17 C18 1.510(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N2 1.473(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N1 H1 0.949(10) . ? N2 H2 0.952(10) . ? O5 H5A 0.96(11) . ? O5 H5B 0.96(13) . ? O6 H6A 0.950(10) . ? O6 H6B 0.946(10) . ? 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 99.4(10) . . ? O2' C1 O2 34.1(8) . . ? O1 C1 O2 123.9(9) . . ? O2' C1 O1' 121.2(12) . . ? O1 C1 O1' 33.2(9) . . ? O2 C1 O1' 128.1(11) . . ? O2' C1 C2 127.7(10) . . ? O1 C1 C2 123.9(9) . . ? O2 C1 C2 112.0(6) . . ? O1' C1 C2 110.8(10) . . ? C3 C2 C1 178.1(5) . . ? C2 C3 C4 179.4(5) . . ? C5 C4 C9 119.5(4) . . ? C5 C4 C3 120.1(4) . . ? C9 C4 C3 120.5(4) . . ? C6 C5 C4 120.2(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 121.4(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 118.5(4) . . ? C8 C9 C10 120.6(4) . . ? C4 C9 C10 120.8(3) . . ? C11 C10 C9 177.5(4) . . ? C10 C11 C12 175.0(5) . . ? O4 C12 O3 124.2(4) . . ? O4 C12 C11 118.9(4) . . ? O3 C12 C11 116.9(3) . . ? N1 C13 C14 108.0(3) . . ? N1 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N1 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? N2 C14 C13 108.9(3) . . ? N2 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? N2 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? N1 C15 C16 108.1(4) . . ? N1 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? N1 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? N2 C16 C15 109.2(4) . . ? N2 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N2 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? N1 C17 C18 109.2(4) . . ? N1 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? N1 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.3 . . ? N2 C18 C17 108.1(4) . . ? N2 C18 H18A 110.1 . . ? C17 C18 H18A 110.1 . . ? N2 C18 H18B 110.1 . . ? C17 C18 H18B 110.1 . . ? H18A C18 H18B 108.4 . . ? C17 N1 C15 110.8(4) . . ? C17 N1 C13 110.3(4) . . ? C15 N1 C13 109.0(3) . . ? C17 N1 H1 108(3) . . ? C15 N1 H1 107(3) . . ? C13 N1 H1 112(3) . . ? C18 N2 C16 109.4(4) . . ? C18 N2 C14 111.0(4) . . ? C16 N2 C14 110.2(4) . . ? C18 N2 H2 101(4) . . ? C16 N2 H2 119(4) . . ? C14 N2 H2 106(4) . . ? H5A O5 H5B 109(12) . . ? H6A O6 H6B 109.6(16) . . ? 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 C3 75(16) . . . . ? O1 C1 C2 C3 -144(16) . . . . ? O2 C1 C2 C3 40(16) . . . . ? O1' C1 C2 C3 -110(16) . . . . ? C1 C2 C3 C4 -37(54) . . . . ? C2 C3 C4 C5 144(43) . . . . ? C2 C3 C4 C9 -37(44) . . . . ? C9 C4 C5 C6 -0.3(7) . . . . ? C3 C4 C5 C6 179.2(4) . . . . ? C4 C5 C6 C7 0.2(7) . . . . ? C5 C6 C7 C8 0.4(8) . . . . ? C6 C7 C8 C9 -1.0(7) . . . . ? C7 C8 C9 C4 1.0(7) . . . . ? C7 C8 C9 C10 -176.2(4) . . . . ? C5 C4 C9 C8 -0.3(6) . . . . ? C3 C4 C9 C8 -179.8(4) . . . . ? C5 C4 C9 C10 176.8(4) . . . . ? C3 C4 C9 C10 -2.6(6) . . . . ? C8 C9 C10 C11 53(11) . . . . ? C4 C9 C10 C11 -124(10) . . . . ? C9 C10 C11 C12 29(14) . . . . ? C10 C11 C12 O4 121(5) . . . . ? C10 C11 C12 O3 -59(5) . . . . ? N1 C13 C14 N2 -8.0(6) . . . . ? N1 C15 C16 N2 -5.5(5) . . . . ? N1 C17 C18 N2 -8.8(6) . . . . ? C18 C17 N1 C15 -54.9(5) . . . . ? C18 C17 N1 C13 65.8(5) . . . . ? C16 C15 N1 C17 63.2(5) . . . . ? C16 C15 N1 C13 -58.4(5) . . . . ? C14 C13 N1 C17 -55.4(5) . . . . ? C14 C13 N1 C15 66.4(5) . . . . ? C17 C18 N2 C16 66.6(5) . . . . ? C17 C18 N2 C14 -55.2(6) . . . . ? C15 C16 N2 C18 -58.1(5) . . . . ? C15 C16 N2 C14 64.2(5) . . . . ? C13 C14 N2 C18 65.4(6) . . . . ? C13 C14 N2 C16 -56.0(6) . . . . ? 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 N2 H2 O1 0.952(10) 1.88(2) 2.802(14) 163(6) 4_675 N1 H1 O3 0.949(10) 1.626(14) 2.567(4) 170(5) . O5 H5A O6 0.96(11) 2.03(14) 2.783(8) 135(15) 2_655 O6 H6A O2 0.950(10) 1.77(2) 2.709(11) 169(8) 2_645 O5 H5B O6 0.96(13) 2.64(16) 3.193(11) 118(13) 1_565 O6 H6B O4 0.946(10) 1.81(3) 2.707(5) 158(6) 2_645 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.360 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.071 # Attachment '13PPA.cif' data_13pp _database_code_depnum_ccdc_archive 'CCDC 656600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 O12' _chemical_formula_sum 'C24 H20 O12' _chemical_formula_weight 500.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 56.173(5) _cell_length_b 3.777(5) _cell_length_c 11.660(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 96.062(5) _cell_angle_gamma 90.000(5) _cell_volume 2460(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3180 _cell_measurement_theta_min 5.832 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9122 _exptl_absorpt_correction_T_max 0.9512 _exptl_absorpt_process_details 'Bruker(SADABS, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11518 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -65 _diffrn_reflns_limit_h_max 66 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2167 _reflns_number_gt 1752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All the hydrogens could be located in difference Fourier map. However, the C-H and carboxylic hydrogens were fixed (C-H= 0.93\%A, U=1.2U~iso~C and O-H=0.820\%A, U=1.5U~iso~O) chemically meaningful positions and were given riding model refinement. Water hydrogens were refined with restraints (O-H= 0.920(1)\%A, H...H=1.48\%A,).Thermal parameters of water hydrogens were refined isotropically. The restraints were applied to keep the hydrogens in the vicinity of the Fourier peak position after refinement. All the donor-acceptor distances are with in the hydrogen bonding interaction range. ; _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^)+(0.1117P)^2^+0.3936P] 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 0.0016(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2167 _refine_ls_number_parameters 180 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1783 _refine_ls_wR_factor_gt 0.1659 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.172 _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 C1 C 0.95303(4) -0.7835(7) 0.1188(2) 0.0605(6) Uani 1 1 d . . . C2 C 0.93230(4) -0.6397(7) 0.0493(2) 0.0597(6) Uani 1 1 d . . . C3 C 0.91507(3) -0.5243(6) -0.00628(18) 0.0521(6) Uani 1 1 d . . . C4 C 0.89349(3) -0.3884(5) -0.06766(16) 0.0424(5) Uani 1 1 d . . . C5 C 0.87265(3) -0.3943(5) -0.01459(15) 0.0397(5) Uani 1 1 d . . . H5 H 0.8728 -0.4865 0.0595 0.048 Uiso 1 1 calc R . . C6 C 0.85141(3) -0.2641(5) -0.07060(16) 0.0398(5) Uani 1 1 d . . . C7 C 0.85108(4) -0.1282(5) -0.18193(16) 0.0459(5) Uani 1 1 d . . . H7 H 0.8369 -0.0425 -0.2207 0.055 Uiso 1 1 calc R . . C8 C 0.87194(4) -0.1228(6) -0.23363(17) 0.0507(5) Uani 1 1 d . . . H8 H 0.8718 -0.0300 -0.3076 0.061 Uiso 1 1 calc R . . C9 C 0.89302(4) -0.2508(6) -0.17883(18) 0.0495(5) Uani 1 1 d . . . H9 H 0.9069 -0.2458 -0.2157 0.059 Uiso 1 1 calc R . . C10 C 0.83032(4) -0.2602(5) -0.01139(17) 0.0473(5) Uani 1 1 d . . . C11 C 0.81343(4) -0.2524(6) 0.04298(19) 0.0524(6) Uani 1 1 d . . . C12 C 0.79338(4) -0.2129(6) 0.10980(18) 0.0479(5) Uani 1 1 d . . . O1 O 0.94859(3) -0.8663(7) 0.22133(17) 0.0950(8) Uani 1 1 d . . . H1 H 0.9607 -0.9476 0.2572 0.142 Uiso 1 1 calc R . . O2 O 0.97194(3) -0.8237(7) 0.08257(16) 0.0871(7) Uani 1 1 d . . . O3 O 0.79762(3) -0.3400(5) 0.21371(13) 0.0636(5) Uani 1 1 d . . . H3 H 0.7858 -0.3123 0.2483 0.095 Uiso 1 1 calc R . . O4 O 0.77504(3) -0.0701(5) 0.07135(13) 0.0636(5) Uani 1 1 d . . . O5 O 0.73513(3) 0.2923(6) 0.15677(15) 0.0737(6) Uani 1 1 d D . . O6 O 0.98249(4) -1.1529(8) 0.35093(18) 0.1027(9) Uani 1 1 d D . . H5A H 0.7487(4) 0.164(8) 0.147(2) 0.126(14) Uiso 1 1 d D . . H5B H 0.7297(5) 0.391(8) 0.0868(13) 0.100(10) Uiso 1 1 d D . . H6A H 0.9789(5) -1.187(11) 0.4253(10) 0.117(13) Uiso 1 1 d D . . H6B H 0.99883(13) -1.130(19) 0.353(3) 0.22(3) Uiso 1 1 d 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 0.0372(12) 0.0821(17) 0.0606(14) -0.0113(11) -0.0013(9) 0.0064(10) C2 0.0387(12) 0.0722(16) 0.0668(14) -0.0101(11) -0.0016(10) 0.0057(10) C3 0.0387(11) 0.0563(13) 0.0603(12) -0.0097(10) 0.0013(9) 0.0017(9) C4 0.0378(10) 0.0426(11) 0.0460(10) -0.0083(8) 0.0003(8) 0.0006(7) C5 0.0436(10) 0.0403(10) 0.0350(9) -0.0027(7) 0.0036(7) 0.0039(7) C6 0.0393(10) 0.0372(10) 0.0427(10) -0.0057(7) 0.0034(7) 0.0007(7) C7 0.0504(11) 0.0427(11) 0.0428(10) -0.0012(8) -0.0038(8) 0.0062(8) C8 0.0680(14) 0.0476(12) 0.0366(10) 0.0028(8) 0.0064(9) -0.0004(9) C9 0.0501(12) 0.0492(12) 0.0516(12) -0.0057(9) 0.0162(9) -0.0041(8) C10 0.0406(11) 0.0484(12) 0.0531(11) -0.0035(9) 0.0059(9) 0.0033(8) C11 0.0416(11) 0.0609(14) 0.0546(12) -0.0019(10) 0.0049(9) 0.0041(9) C12 0.0373(10) 0.0590(13) 0.0471(11) -0.0047(9) 0.0036(8) -0.0014(8) O1 0.0481(10) 0.172(2) 0.0647(12) 0.0116(12) 0.0039(8) 0.0200(11) O2 0.0413(10) 0.150(2) 0.0690(11) 0.0004(11) 0.0040(8) 0.0246(10) O3 0.0451(9) 0.0938(13) 0.0519(9) 0.0084(8) 0.0060(7) 0.0073(7) O4 0.0417(9) 0.0981(13) 0.0519(9) 0.0058(8) 0.0089(6) 0.0156(8) O5 0.0594(11) 0.1089(15) 0.0557(10) 0.0117(9) 0.0192(8) 0.0230(9) O6 0.0563(12) 0.181(3) 0.0687(13) 0.0164(14) -0.0047(9) -0.0034(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 C1 O2 1.193(3) . ? C1 O1 1.286(3) . ? C1 C2 1.452(3) . ? C2 C3 1.189(3) . ? C3 C4 1.436(3) . ? C4 C5 1.381(3) . ? C4 C9 1.394(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.394(3) . ? C6 C10 1.433(3) . ? C7 C8 1.374(3) . ? C7 H7 0.9300 . ? C8 C9 1.372(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.196(3) . ? C11 C12 1.443(3) . ? C12 O4 1.207(3) . ? C12 O3 1.301(3) . ? O1 H1 0.8200 . ? O3 H3 0.8200 . ? O5 H5A 0.92(2) . ? O5 H5B 0.92(2) . ? O6 H6A 0.920(15) . ? O6 H6B 0.920(13) . ? 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 124.4(2) . . ? O2 C1 C2 122.8(2) . . ? O1 C1 C2 112.7(2) . . ? C3 C2 C1 178.9(3) . . ? C2 C3 C4 176.6(2) . . ? C5 C4 C9 119.25(17) . . ? C5 C4 C3 118.82(18) . . ? C9 C4 C3 121.94(18) . . ? C4 C5 C6 120.71(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C7 119.64(18) . . ? C5 C6 C10 119.36(17) . . ? C7 C6 C10 120.96(17) . . ? C8 C7 C6 119.09(18) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 121.63(18) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C9 C4 119.68(19) . . ? C8 C9 H9 120.2 . . ? C4 C9 H9 120.2 . . ? C11 C10 C6 176.7(2) . . ? C10 C11 C12 175.4(2) . . ? O4 C12 O3 125.15(19) . . ? O4 C12 C11 121.99(19) . . ? O3 C12 C11 112.85(18) . . ? C1 O1 H1 109.5 . . ? C12 O3 H3 109.5 . . ? H5A O5 H5B 108(2) . . ? H6A O6 H6B 108(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 O2 C1 C2 C3 160(14) . . . . ? O1 C1 C2 C3 -19(14) . . . . ? C1 C2 C3 C4 18(17) . . . . ? C2 C3 C4 C5 -4(4) . . . . ? C2 C3 C4 C9 176(4) . . . . ? C9 C4 C5 C6 -0.2(3) . . . . ? C3 C4 C5 C6 179.72(18) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C4 C5 C6 C10 -177.36(17) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C10 C6 C7 C8 177.12(18) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C5 C4 C9 C8 0.2(3) . . . . ? C3 C4 C9 C8 -179.7(2) . . . . ? C5 C6 C10 C11 38(4) . . . . ? C7 C6 C10 C11 -140(4) . . . . ? C6 C10 C11 C12 65(5) . . . . ? C10 C11 C12 O4 73(3) . . . . ? C10 C11 C12 O3 -106(3) . . . . ? 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 O6 0.82 1.74 2.545(3) 168.8 . O3 H3 O5 0.82 1.74 2.550(2) 167.8 4_645 O5 H5A O4 0.92(2) 2.009(10) 2.892(2) 161(3) . O5 H5B O4 0.92(2) 1.955(7) 2.860(3) 167(3) 7_655 O6 H6A O2 0.920(15) 1.915(7) 2.827(3) 171(4) 6_536 O6 H6B O2 0.920(13) 2.08(4) 2.878(3) 144(6) 2_755 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.206 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.040 # end Validation Reply Form # Attachment '14PPA.cif' data_saran1 _database_code_depnum_ccdc_archive 'CCDC 656601' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O6' _chemical_formula_sum 'C12 H10 O6' _chemical_formula_weight 250.20 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 3.7812(3) _cell_length_b 6.1345(5) _cell_length_c 13.3677(11) _cell_angle_alpha 101.929(5) _cell_angle_beta 93.522(5) _cell_angle_gamma 93.507(5) _cell_volume 301.94(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1570 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 28.1 _exptl_crystal_description prisamatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 130 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8811 _exptl_absorpt_correction_T_max 0.9627 _exptl_absorpt_process_details 'Bruker(SADABS, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD diffractometer' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3209 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1051 _reflns_number_gt 884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All the hydrogens could be located in difference Fourier map. However, the C-H and carboxylic hydrogens were fixed (C-H= 0.93\%A, U=1.2U~iso~C and O-H=0.820\%A) chemically meaningful positions and were given riding model refinement. Water hydrogens were refined with restraints (O-H= 0.930(1)\%A, H...H=1.50\%A). Thermal parameters of water and O-H hydrogens were refined isotropically. The restraints were applied The restraints were applied to keep the hydrogens in the vicinity of the Fourier peak position after refinement. All the donor-acceptor distances are well with in the hydrogen bonding interaction range. ; _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^)+(0.0666P)^2^+0.0799P] 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 1051 _refine_ls_number_parameters 91 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.087 _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 0.5992(5) 0.6609(3) 0.31298(13) 0.0470(5) Uani 1 1 d . . . C2 C 0.4417(5) 0.4889(3) 0.22885(14) 0.0506(5) Uani 1 1 d . . . C3 C 0.3139(4) 0.3445(3) 0.16003(13) 0.0471(5) Uani 1 1 d . . . C4 C 0.1562(4) 0.1696(3) 0.07825(12) 0.0416(4) Uani 1 1 d . . . C5 C 0.1247(5) 0.2003(3) -0.02198(13) 0.0482(5) Uani 1 1 d . . . H5 H 0.2095 0.3349 -0.0366 0.058 Uiso 1 1 calc R . . C6 C 0.0310(5) -0.0328(3) 0.09952(13) 0.0488(5) Uani 1 1 d . . . H6 H 0.0529 -0.0546 0.1664 0.059 Uiso 1 1 calc R . . O1 O 0.7510(5) 0.6188(2) 0.38734(11) 0.0768(6) Uani 1 1 d . . . O2 O 0.5609(5) 0.8593(2) 0.29870(11) 0.0713(5) Uani 1 1 d . . . H2 H 0.6681 0.9507 0.3460 0.108(10) Uiso 1 1 calc R . . O3 O 0.8554(7) 1.1901(3) 0.42513(16) 0.1173(9) Uani 1 1 d D . . H3A H 0.965(11) 1.208(5) 0.4909(13) 0.193(18) Uiso 1 1 d D . . H3B H 0.794(10) 1.330(2) 0.416(2) 0.153(14) Uiso 1 1 d 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 0.0523(10) 0.0428(10) 0.0395(9) -0.0012(7) -0.0085(8) 0.0000(8) C2 0.0507(11) 0.0489(11) 0.0459(10) -0.0005(8) -0.0077(8) 0.0011(8) C3 0.0434(10) 0.0470(11) 0.0440(10) -0.0033(8) -0.0063(8) 0.0020(8) C4 0.0354(8) 0.0408(9) 0.0415(9) -0.0047(7) -0.0062(7) 0.0032(7) C5 0.0509(10) 0.0414(10) 0.0480(10) 0.0044(7) -0.0056(8) -0.0033(7) C6 0.0537(11) 0.0507(11) 0.0374(9) 0.0031(7) -0.0071(8) -0.0004(8) O1 0.1163(14) 0.0462(9) 0.0566(9) -0.0001(6) -0.0413(9) 0.0029(8) O2 0.1057(13) 0.0436(8) 0.0557(9) 0.0041(6) -0.0325(8) -0.0051(7) O3 0.185(2) 0.0488(11) 0.0983(14) -0.0002(9) -0.0785(15) -0.0014(12) _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 O1 1.199(2) . ? C1 O2 1.286(2) . ? C1 C2 1.443(2) . ? C2 C3 1.192(2) . ? C3 C4 1.435(2) . ? C4 C5 1.390(2) . ? C4 C6 1.391(3) . ? C5 C6 1.374(2) 2 ? C5 H5 0.9300 . ? C6 C5 1.374(2) 2 ? C6 H6 0.9300 . ? O2 H2 0.8200 . ? O3 H3A 0.93(2) . ? O3 H3B 0.933(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 O1 C1 O2 124.67(17) . . ? O1 C1 C2 122.35(17) . . ? O2 C1 C2 112.97(15) . . ? C3 C2 C1 179.0(2) . . ? C2 C3 C4 179.08(19) . . ? C5 C4 C6 119.55(15) . . ? C5 C4 C3 120.78(16) . . ? C6 C4 C3 119.66(15) . . ? C6 C5 C4 120.32(17) 2 . ? C6 C5 H5 119.8 2 . ? C4 C5 H5 119.8 . . ? C5 C6 C4 120.13(16) 2 . ? C5 C6 H6 119.9 2 . ? C4 C6 H6 119.9 . . ? C1 O2 H2 109.5 . . ? H3A O3 H3B 108(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 O1 C1 C2 C3 -8(12) . . . . ? O2 C1 C2 C3 172(100) . . . . ? C1 C2 C3 C4 72(19) . . . . ? C2 C3 C4 C5 145(13) . . . . ? C2 C3 C4 C6 -35(13) . . . . ? C6 C4 C5 C6 0.5(3) . . . 2 ? C3 C4 C5 C6 -179.14(15) . . . 2 ? C5 C4 C6 C5 -0.4(3) . . . 2 ? C3 C4 C6 C5 179.15(15) . . . 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 O2 H2 O3 0.82 1.71 2.508(2) 164.6 . O3 H3A O1 0.93(2) 1.965(16) 2.826(2) 153(3) 2_776 O3 H3B O1 0.933(17) 1.906(8) 2.825(2) 169(4) 1_565 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.362 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.036 # Attachment '14PPAdabco.cif' data_saro _database_code_depnum_ccdc_archive 'CCDC 656602' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 N2 O4' _chemical_formula_sum 'C18 H18 N2 O4' _chemical_formula_weight 326.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 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 9.5230(18) _cell_length_b 17.603(5) _cell_length_c 9.8656(17) _cell_angle_alpha 90.000(18) _cell_angle_beta 103.425(13) _cell_angle_gamma 90.000(19) _cell_volume 1608.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_factor_muR 0.000 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9992 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'cad4 diffractometer' _diffrn_measurement_method 'omega twotheta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '1 hour' _diffrn_standards_decay_% 0 _diffrn_reflns_number 3111 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.77 _diffrn_reflns_theta_max 67.92 _reflns_number_total 2928 _reflns_number_gt 1921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cad4 system software' _computing_cell_refinement 'cad4 system software' _computing_data_reduction 'xcad4(Harms et al., 1995)' _computing_structure_solution 'sir92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3(Farrugia et al., 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogens of DABCO nitrogens were located in difference Fourier map and refined isotropically. All other hydrogens were fixed at chemically meaningful positions and were given riding model refinement. All the donor-acceptor distances are well with in the hydrogen bonding interaction range. ; _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^)+(0.1344P)^2^+1.7104P] 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 0.0009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2928 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.2783 _refine_ls_wR_factor_gt 0.2672 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 0.2809(4) 0.6400(2) 0.3003(3) 0.0486(9) Uani 1 1 d . . . C2 C 0.1957(4) 0.6318(2) 0.1565(4) 0.0489(9) Uani 1 1 d . . . C3 C 0.1316(4) 0.6283(2) 0.0376(3) 0.0498(10) Uani 1 1 d . . . C4 C 0.0582(4) 0.6246(2) -0.1075(3) 0.0476(9) Uani 1 1 d . . . C5 C 0.0274(4) 0.5554(2) -0.1744(3) 0.0458(9) Uani 1 1 d . . . H5 H 0.0526 0.5105 -0.1250 0.055 Uiso 1 1 calc R . . C6 C -0.0405(4) 0.5526(2) -0.3142(3) 0.0483(9) Uani 1 1 d . . . H6 H -0.0604 0.5060 -0.3589 0.058 Uiso 1 1 calc R . . C7 C -0.0792(3) 0.6198(2) -0.3880(3) 0.0434(9) Uani 1 1 d . . . C8 C -0.0493(4) 0.6890(2) -0.3213(3) 0.0516(10) Uani 1 1 d . . . H8 H -0.0753 0.7338 -0.3706 0.062 Uiso 1 1 calc R . . C9 C 0.0192(4) 0.6919(2) -0.1815(3) 0.0489(9) Uani 1 1 d . . . H9 H 0.0391 0.7385 -0.1369 0.059 Uiso 1 1 calc R . . C10 C -0.1526(4) 0.6167(2) -0.5342(3) 0.0478(9) Uani 1 1 d . . . C11 C -0.2145(4) 0.6142(2) -0.6532(3) 0.0489(9) Uani 1 1 d . . . C12 C -0.2907(4) 0.6085(2) -0.8010(3) 0.0462(9) Uani 1 1 d . . . C13 C 0.4610(4) 0.4459(2) 0.3347(4) 0.0556(10) Uani 1 1 d . . . H13A H 0.5165 0.4926 0.3442 0.067 Uiso 1 1 calc R . . H13B H 0.3949 0.4488 0.3960 0.067 Uiso 1 1 calc R . . C14 C 0.3768(4) 0.4364(2) 0.1850(4) 0.0535(10) Uani 1 1 d . . . H14A H 0.2743 0.4333 0.1815 0.064 Uiso 1 1 calc R . . H14B H 0.3932 0.4797 0.1299 0.064 Uiso 1 1 calc R . . C15 C 0.5817(4) 0.3710(2) 0.1333(4) 0.0458(9) Uani 1 1 d . . . H15A H 0.6004 0.4152 0.0815 0.055 Uiso 1 1 calc R . . H15B H 0.6133 0.3262 0.0914 0.055 Uiso 1 1 calc R . . C16 C 0.6640(4) 0.3776(2) 0.2846(4) 0.0519(10) Uani 1 1 d . . . H16A H 0.7277 0.3343 0.3098 0.062 Uiso 1 1 calc R . . H16B H 0.7223 0.4234 0.2975 0.062 Uiso 1 1 calc R . . C17 C 0.3961(4) 0.2984(2) 0.2097(3) 0.0543(10) Uani 1 1 d . . . H17A H 0.4287 0.2523 0.1728 0.065 Uiso 1 1 calc R . . H17B H 0.2931 0.2940 0.2029 0.065 Uiso 1 1 calc R . . C18 C 0.4752(5) 0.3089(2) 0.3609(4) 0.0592(11) Uani 1 1 d . . . H18A H 0.4064 0.3111 0.4195 0.071 Uiso 1 1 calc R . . H18B H 0.5394 0.2662 0.3909 0.071 Uiso 1 1 calc R . . N1 N 0.4260(3) 0.36550(16) 0.1279(3) 0.0408(7) Uani 1 1 d . . . N2 N 0.5592(3) 0.38024(17) 0.3740(3) 0.0467(8) Uani 1 1 d . . . O1 O 0.3363(7) 0.6993(3) 0.3329(4) 0.177(3) Uani 1 1 d . . . O2 O 0.2865(5) 0.5877(2) 0.3786(3) 0.1027(15) Uani 1 1 d . . . O3 O -0.2853(3) 0.66476(16) -0.8755(2) 0.0613(9) Uani 1 1 d . . . O4 O -0.3524(4) 0.54906(18) -0.8408(3) 0.0936(14) Uani 1 1 d . . . H1 H 0.375(4) 0.361(2) 0.033(4) 0.054(11) Uiso 1 1 d . . . H2 H 0.616(5) 0.384(2) 0.466(5) 0.077(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.057(2) 0.051(2) 0.0274(17) 0.0009(15) -0.0116(15) -0.0092(17) C2 0.051(2) 0.059(2) 0.0287(18) 0.0050(15) -0.0075(15) 0.0002(17) C3 0.045(2) 0.072(3) 0.0258(18) -0.0005(15) -0.0050(14) 0.0010(17) C4 0.0355(18) 0.076(3) 0.0248(16) 0.0011(16) -0.0053(13) 0.0022(16) C5 0.0408(18) 0.064(2) 0.0278(16) 0.0113(15) -0.0029(14) 0.0039(16) C6 0.0415(19) 0.066(2) 0.0308(17) -0.0006(16) -0.0056(14) 0.0015(16) C7 0.0350(17) 0.069(2) 0.0212(15) 0.0019(14) -0.0035(12) 0.0060(16) C8 0.051(2) 0.065(2) 0.0315(17) 0.0038(16) -0.0053(15) 0.0148(18) C9 0.046(2) 0.064(2) 0.0301(17) -0.0005(15) -0.0050(14) 0.0032(17) C10 0.0453(19) 0.069(2) 0.0221(17) 0.0023(15) -0.0056(14) 0.0055(17) C11 0.052(2) 0.059(2) 0.0281(18) 0.0033(15) -0.0062(15) 0.0031(17) C12 0.050(2) 0.049(2) 0.0308(18) 0.0019(15) -0.0093(14) -0.0001(16) C13 0.062(2) 0.066(3) 0.0356(19) -0.0094(17) 0.0057(17) -0.0021(19) C14 0.056(2) 0.059(2) 0.0395(19) -0.0021(16) -0.0008(16) 0.0169(18) C15 0.0453(19) 0.056(2) 0.0359(18) -0.0034(15) 0.0090(14) -0.0018(16) C16 0.0385(19) 0.069(3) 0.042(2) 0.0014(17) -0.0031(15) -0.0042(17) C17 0.064(2) 0.059(2) 0.0321(18) 0.0007(16) -0.0036(16) -0.0208(19) C18 0.075(3) 0.063(2) 0.0328(18) 0.0072(17) -0.0014(17) -0.019(2) N1 0.0428(16) 0.0548(17) 0.0192(13) 0.0004(11) -0.0042(11) -0.0010(13) N2 0.0509(18) 0.0598(19) 0.0203(14) 0.0034(12) -0.0102(12) -0.0089(14) O1 0.269(6) 0.112(3) 0.086(3) 0.030(3) -0.090(4) -0.104(4) O2 0.151(3) 0.087(2) 0.0398(16) 0.0140(17) -0.0390(19) -0.044(2) O3 0.083(2) 0.0590(17) 0.0273(12) 0.0058(11) -0.0159(12) -0.0149(14) O4 0.144(3) 0.067(2) 0.0444(17) 0.0092(14) -0.0281(18) -0.038(2) _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 O1 1.179(5) . ? C1 O2 1.195(5) . ? C1 C2 1.469(4) . ? C2 C3 1.191(5) . ? C3 C4 1.441(4) . ? C4 C5 1.385(5) . ? C4 C9 1.395(5) . ? C5 C6 1.381(4) . ? C5 H5 0.9300 . ? C6 C7 1.393(5) . ? C6 H6 0.9300 . ? C7 C8 1.383(5) . ? C7 C10 1.450(4) . ? C8 C9 1.382(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.186(5) . ? C11 C12 1.474(4) . ? C12 O4 1.219(4) . ? C12 O3 1.242(4) . ? C13 N2 1.481(5) . ? C13 C14 1.517(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N1 1.489(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N1 1.475(4) . ? C15 C16 1.521(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N2 1.478(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N1 1.495(4) . ? C17 C18 1.518(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N2 1.479(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N1 H1 0.96(4) . ? N2 H2 0.94(5) . ? 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 O1 C1 O2 123.7(4) . . ? O1 C1 C2 117.5(4) . . ? O2 C1 C2 118.7(3) . . ? C3 C2 C1 176.2(4) . . ? C2 C3 C4 178.2(4) . . ? C5 C4 C9 119.7(3) . . ? C5 C4 C3 120.9(3) . . ? C9 C4 C3 119.4(3) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.8(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 C10 120.4(3) . . ? C6 C7 C10 119.7(3) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C4 119.9(4) . . ? C8 C9 H9 120.1 . . ? C4 C9 H9 120.1 . . ? C11 C10 C7 179.0(4) . . ? C10 C11 C12 178.2(4) . . ? O4 C12 O3 125.2(3) . . ? O4 C12 C11 117.8(3) . . ? O3 C12 C11 116.9(3) . . ? N2 C13 C14 109.1(3) . . ? N2 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? N2 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? N1 C14 C13 108.6(3) . . ? N1 C14 H14A 110.0 . . ? C13 C14 H14A 110.0 . . ? N1 C14 H14B 110.0 . . ? C13 C14 H14B 110.0 . . ? H14A C14 H14B 108.3 . . ? N1 C15 C16 109.0(3) . . ? N1 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? N1 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? N2 C16 C15 108.8(3) . . ? N2 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? N2 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? N1 C17 C18 108.7(3) . . ? N1 C17 H17A 109.9 . . ? C18 C17 H17A 109.9 . . ? N1 C17 H17B 109.9 . . ? C18 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? N2 C18 C17 108.9(3) . . ? N2 C18 H18A 109.9 . . ? C17 C18 H18A 109.9 . . ? N2 C18 H18B 109.9 . . ? C17 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C15 N1 C14 109.4(3) . . ? C15 N1 C17 110.4(3) . . ? C14 N1 C17 110.0(3) . . ? C15 N1 H1 109(2) . . ? C14 N1 H1 108(2) . . ? C17 N1 H1 110(2) . . ? C16 N2 C18 110.3(3) . . ? C16 N2 C13 110.0(3) . . ? C18 N2 C13 110.1(3) . . ? C16 N2 H2 105(3) . . ? C18 N2 H2 109(3) . . ? C13 N2 H2 112(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 O1 C1 C2 C3 27(7) . . . . ? O2 C1 C2 C3 -155(6) . . . . ? C1 C2 C3 C4 31(18) . . . . ? C2 C3 C4 C5 102(14) . . . . ? C2 C3 C4 C9 -77(14) . . . . ? C9 C4 C5 C6 0.6(5) . . . . ? C3 C4 C5 C6 -178.8(3) . . . . ? C4 C5 C6 C7 -0.4(5) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C5 C6 C7 C10 -179.0(3) . . . . ? C6 C7 C8 C9 0.1(6) . . . . ? C10 C7 C8 C9 179.2(3) . . . . ? C7 C8 C9 C4 0.0(6) . . . . ? C5 C4 C9 C8 -0.3(6) . . . . ? C3 C4 C9 C8 179.0(3) . . . . ? C8 C7 C10 C11 -88(23) . . . . ? C6 C7 C10 C11 91(23) . . . . ? C7 C10 C11 C12 -99(26) . . . . ? C10 C11 C12 O4 29(14) . . . . ? C10 C11 C12 O3 -150(14) . . . . ? N2 C13 C14 N1 -1.9(4) . . . . ? N1 C15 C16 N2 -2.9(4) . . . . ? N1 C17 C18 N2 -2.3(5) . . . . ? C16 C15 N1 C14 62.8(4) . . . . ? C16 C15 N1 C17 -58.5(4) . . . . ? C13 C14 N1 C15 -59.9(4) . . . . ? C13 C14 N1 C17 61.6(4) . . . . ? C18 C17 N1 C15 61.7(4) . . . . ? C18 C17 N1 C14 -59.2(4) . . . . ? C15 C16 N2 C18 62.6(4) . . . . ? C15 C16 N2 C13 -59.0(4) . . . . ? C17 C18 N2 C16 -59.3(4) . . . . ? C17 C18 N2 C13 62.3(4) . . . . ? C14 C13 N2 C16 61.9(4) . . . . ? C14 C13 N2 C18 -59.9(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 N1 H1 O3 0.96(4) 1.65(4) 2.594(3) 169(4) 3_564 N2 H2 O2 0.94(5) 1.68(5) 2.602(4) 167(4) 3_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.92 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.271 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.062 _vrf_PLAT242_saro ; PROBLEM: Check Low Ueq as Compared to Neighbors for C1 RESPONSE: There might be a mild unresolved disorder for the oxygens of one of the carboxylate groups which makes the thermal parameters of C1 less than the neighbouring oxygens. ;