# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _audit_creation_method 'SHELXL-97 plus manual editing' _journal_coden_Cambridge 0440 loop_ _publ_author_name 'William Jones' 'Andrew Bond' 'Ning Shan' _publ_contact_author_name 'William Jones' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UK ; _publ_contact_author_email wj10@cam.ac.uk _publ_contact_author_fax '(01223) 336362' _publ_contact_author_phone '(01223) 336468' _publ_section_comment ; For discussion of intermolecular distances and angles involving H atoms, the positions of the hydrogen atoms were normalised to standard neutron-derived distances (Allen et al. J. Chem. Soc. Perkin Trans. 1987, 2, S1.). ; _publ_section_title ; Supramolecular acrchitectures of cylcohexane acid:base complexes ; ########################################################## data_CTAAn _database_code_CSD 189057 _chemical_name_systematic ; cyclohexane-1,3cis,5cis-tricaboxylic acid--acetonitrile(1/1)' ; _chemical_name_common CTA/An _chemical_melting_point 'not measured' _chemical_formula_moiety 'C9 H12 O6, C2 H3 N1' _chemical_formula_sum 'C11 H15 N O6' _chemical_formula_weight 257.24 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 6.8309(5) _cell_length_b 16.0470(13) _cell_length_c 22.8001(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2499.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14900 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9768 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w nd \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 11013 _diffrn_reflns_av_R_equivalents 0.0813 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2180 _reflns_number_gt 1449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement ; HKL Scalepack (Otwinowski & Minor 1997) ; _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+1.3126P] 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 none _refine_ls_number_reflns 2180 _refine_ls_number_parameters 175 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.004 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0717(4) -0.10692(16) 0.16178(11) 0.0238(6) Uani 1 d . . . H1 H -0.0237 -0.1070 0.1285 0.029 Uiso 1 calc R . . C2 C 0.0410(4) -0.02834(16) 0.19825(11) 0.0263(6) Uani 1 d . . . H2A H 0.1245 -0.0310 0.2337 0.032 Uiso 1 calc R . . H2B H -0.0972 -0.0256 0.2112 0.032 Uiso 1 calc R . . C3 C 0.0910(4) 0.05042(16) 0.16333(11) 0.0248(6) Uani 1 d . . . H3 H -0.0021 0.0551 0.1297 0.030 Uiso 1 calc R . . C4 C 0.3004(4) 0.04629(16) 0.13910(11) 0.0252(6) Uani 1 d . . . H4A H 0.3268 0.0966 0.1153 0.030 Uiso 1 calc R . . H4B H 0.3945 0.0455 0.1721 0.030 Uiso 1 calc R . . C5 C 0.3294(4) -0.03100(16) 0.10155(11) 0.0252(6) Uani 1 d . . . H5 H 0.2390 -0.0279 0.0671 0.030 Uiso 1 calc R . . C6 C 0.2819(4) -0.11036(16) 0.13679(11) 0.0263(6) Uani 1 d . . . H6A H 0.3765 -0.1162 0.1694 0.032 Uiso 1 calc R . . H6B H 0.2952 -0.1597 0.1110 0.032 Uiso 1 calc R . . C7 C 0.0374(4) -0.18277(17) 0.19898(11) 0.0251(6) Uani 1 d D . . O1 O 0.0827(3) -0.18540(11) 0.25122(8) 0.0328(5) Uani 1 d . . . O2 O -0.0385(3) -0.24655(12) 0.17135(8) 0.0371(5) Uani 1 d D . . H2 H -0.061(4) -0.2871(15) 0.1941(12) 0.045 Uiso 1 d D . . C8 C 0.0686(4) 0.12620(16) 0.20158(12) 0.0249(6) Uani 1 d D . . O3 O 0.1113(3) 0.12739(11) 0.25374(8) 0.0340(5) Uani 1 d . . . O4 O 0.0010(3) 0.19217(12) 0.17392(8) 0.0388(5) Uani 1 d D . . H4 H -0.025(4) 0.2317(16) 0.1966(12) 0.047 Uiso 1 d D . . C9 C 0.5360(4) -0.03636(17) 0.07956(12) 0.0299(7) Uani 1 d D . . O5 O 0.6715(3) 0.00235(15) 0.09811(10) 0.0535(7) Uani 1 d . . . O6 O 0.5560(3) -0.09263(15) 0.03656(10) 0.0494(6) Uani 1 d D . . H6 H 0.677(4) -0.098(2) 0.0279(13) 0.059 Uiso 1 d D . . N1 N 0.0669(5) 0.12347(19) 0.00576(13) 0.0583(9) Uani 1 d . . . C10 C -0.0686(5) 0.1525(2) 0.02569(13) 0.0392(8) Uani 1 d . . . C11 C -0.2416(5) 0.1903(2) 0.05172(15) 0.0473(9) Uani 1 d . . . H11A H -0.2878 0.1555 0.0842 0.057 Uiso 1 calc R . . H11B H -0.3447 0.1948 0.0220 0.057 Uiso 1 calc R . . H11C H -0.2087 0.2459 0.0665 0.057 Uiso 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 C1 0.0277(15) 0.0195(15) 0.0243(13) 0.0016(10) -0.0016(11) -0.0004(11) C2 0.0240(15) 0.0230(15) 0.0319(15) -0.0005(11) 0.0038(12) -0.0022(12) C3 0.0251(15) 0.0218(15) 0.0276(14) -0.0022(11) -0.0007(11) 0.0005(11) C4 0.0277(16) 0.0223(15) 0.0255(14) -0.0002(11) -0.0008(11) -0.0034(11) C5 0.0267(15) 0.0235(15) 0.0254(14) 0.0004(11) -0.0001(11) -0.0004(12) C6 0.0319(16) 0.0205(15) 0.0265(14) -0.0016(11) 0.0020(12) 0.0022(12) C7 0.0244(15) 0.0225(16) 0.0285(16) -0.0026(11) 0.0017(12) -0.0028(12) O1 0.0445(12) 0.0229(10) 0.0308(11) 0.0020(9) -0.0040(9) -0.0068(9) O2 0.0541(13) 0.0223(11) 0.0349(11) 0.0009(9) -0.0013(9) -0.0136(10) C8 0.0213(15) 0.0208(15) 0.0325(16) 0.0014(12) 0.0030(11) 0.0014(12) O3 0.0458(13) 0.0266(11) 0.0295(11) -0.0026(9) -0.0038(9) 0.0042(9) O4 0.0600(14) 0.0207(11) 0.0358(11) -0.0014(9) -0.0001(10) 0.0101(10) C9 0.0330(18) 0.0273(16) 0.0296(15) 0.0026(13) 0.0018(13) 0.0018(14) O5 0.0299(13) 0.0645(16) 0.0660(16) -0.0194(13) 0.0059(11) -0.0084(12) O6 0.0394(13) 0.0545(15) 0.0542(14) -0.0203(12) 0.0135(11) -0.0002(11) N1 0.055(2) 0.064(2) 0.0557(19) 0.0045(15) 0.0195(15) 0.0112(17) C10 0.048(2) 0.0356(18) 0.0335(17) 0.0059(14) -0.0010(15) 0.0000(16) C11 0.0392(19) 0.046(2) 0.057(2) -0.0082(16) -0.0007(15) 0.0070(16) _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 C7 1.502(4) . ? C1 C2 1.525(4) . ? C1 C6 1.545(4) . ? C1 H1 1.0000 . ? C2 C3 1.532(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.504(4) . ? C3 C4 1.535(4) . ? C3 H3 1.0000 . ? C4 C5 1.520(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C9 1.500(4) . ? C5 C6 1.540(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O1 1.231(3) . ? C7 O2 1.309(3) . ? O2 H2 0.85(2) . ? C8 O3 1.225(3) . ? C8 O4 1.316(3) . ? O4 H4 0.84(2) . ? C9 O5 1.192(3) . ? C9 O6 1.340(3) . ? O6 H6 0.85(3) . ? N1 C10 1.132(4) . ? C10 C11 1.454(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 C1 C2 109.9(2) . . ? C7 C1 C6 108.9(2) . . ? C2 C1 C6 111.0(2) . . ? C7 C1 H1 109.0 . . ? C2 C1 H1 109.0 . . ? C6 C1 H1 109.0 . . ? C1 C2 C3 111.6(2) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C8 C3 C2 110.1(2) . . ? C8 C3 C4 109.8(2) . . ? C2 C3 C4 111.1(2) . . ? C8 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? C4 C3 H3 108.6 . . ? C5 C4 C3 111.1(2) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C9 C5 C4 111.0(2) . . ? C9 C5 C6 109.0(2) . . ? C4 C5 C6 110.7(2) . . ? C9 C5 H5 108.7 . . ? C4 C5 H5 108.7 . . ? C6 C5 H5 108.7 . . ? C5 C6 C1 111.0(2) . . ? C5 C6 H6A 109.4 . . ? C1 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C1 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O1 C7 O2 122.6(2) . . ? O1 C7 C1 122.3(2) . . ? O2 C7 C1 115.1(2) . . ? C7 O2 H2 112.1(18) . . ? O3 C8 O4 122.4(2) . . ? O3 C8 C3 123.5(2) . . ? O4 C8 C3 114.1(2) . . ? C8 O4 H4 112.9(19) . . ? O5 C9 O6 122.1(3) . . ? O5 C9 C5 125.6(3) . . ? O6 C9 C5 112.3(2) . . ? C9 O6 H6 109.7(19) . . ? N1 C10 C11 179.4(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 C7 C1 C2 C3 175.3(2) . . . . ? C6 C1 C2 C3 54.7(3) . . . . ? C1 C2 C3 C8 -177.2(2) . . . . ? C1 C2 C3 C4 -55.4(3) . . . . ? C8 C3 C4 C5 178.4(2) . . . . ? C2 C3 C4 C5 56.5(3) . . . . ? C3 C4 C5 C9 -178.1(2) . . . . ? C3 C4 C5 C6 -57.0(3) . . . . ? C9 C5 C6 C1 178.6(2) . . . . ? C4 C5 C6 C1 56.3(3) . . . . ? C7 C1 C6 C5 -176.2(2) . . . . ? C2 C1 C6 C5 -55.1(3) . . . . ? C2 C1 C7 O1 -35.5(3) . . . . ? C6 C1 C7 O1 86.3(3) . . . . ? C2 C1 C7 O2 146.5(2) . . . . ? C6 C1 C7 O2 -91.7(3) . . . . ? C2 C3 C8 O3 36.8(3) . . . . ? C4 C3 C8 O3 -85.8(3) . . . . ? C2 C3 C8 O4 -144.1(2) . . . . ? C4 C3 C8 O4 93.4(3) . . . . ? C4 C5 C9 O5 15.5(4) . . . . ? C6 C5 C9 O5 -106.6(3) . . . . ? C4 C5 C9 O6 -166.3(2) . . . . ? C6 C5 C9 O6 71.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.859 _refine_diff_density_max 0.266 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.051 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 1.02 1.68 2.694(3) 177.4 3_545 O4 H4 O1 1.02 1.65 2.665(3) 177.1 3 O6 H6 N1 1.02 1.79 2.95(4) 167.0 5_655 C11 H11A O5 1.08 2.44 3.250(4) 132.6 1_455 #===END ########################################################## data_CTAoPh2MeOH _database_code_CSD 189058 _chemical_name_systematic ; cyclohexane-1,3cis,5cis-tricaboxylic acid-- 1,10-phenathroline--methonal(1/1/2)' ; _chemical_name_common CTA/oPh/2MeOH _chemical_formula_moiety 'C9 H12 O6, C12 H8 N2, C2 H8 O2' _chemical_formula_sum 'C23 H28 N2 O8' _chemical_formula_weight 460.47 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8501(5) _cell_length_b 11.0316(8) _cell_length_c 11.8635(7) _cell_angle_alpha 90.185(3) _cell_angle_beta 95.174(4) _cell_angle_gamma 92.475(4) _cell_volume 1152.42(13) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9056 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9860 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 9137 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4035 _reflns_number_gt 3216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement ; HKL Scalepack (Otwinowski & Minor 1997) ; _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.3619P] 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 none _refine_ls_number_reflns 4035 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.118 _refine_ls_shift/su_mean 0.003 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.55433(14) 0.36406(12) 0.46001(10) 0.0377(3) Uani 1 d . . . O2 O 0.58341(14) 0.45091(12) 0.63106(10) 0.0355(3) Uani 1 d . . . H2O H 0.535(3) 0.518(3) 0.591(2) 0.081(8) Uiso 1 d . . . O3 O 0.49231(15) 0.11361(13) 0.91011(11) 0.0450(4) Uani 1 d . . . O4 O 0.64657(17) -0.03960(13) 0.91761(11) 0.0480(4) Uani 1 d . . . H4O H 0.592(4) -0.063(3) 0.983(3) 0.116(11) Uiso 1 d . . . O5 O 0.74602(17) -0.06308(14) 0.41608(11) 0.0510(4) Uani 1 d . . . O6 O 0.90415(16) -0.12999(13) 0.55749(11) 0.0427(3) Uani 1 d . . . H6O H 0.916(3) -0.198(3) 0.507(2) 0.068(7) Uiso 1 d . . . C1 C 0.67743(18) 0.25570(15) 0.61538(13) 0.0257(4) Uani 1 d . . . H1A H 0.7807 0.2859 0.6472 0.031 Uiso 1 calc R . . C2 C 0.59133(18) 0.20955(16) 0.71511(13) 0.0274(4) Uani 1 d . . . H2A H 0.5847 0.2763 0.7701 0.033 Uiso 1 calc R . . H2B H 0.4868 0.1817 0.6871 0.033 Uiso 1 calc R . . C3 C 0.67407(18) 0.10500(15) 0.77300(13) 0.0263(4) Uani 1 d . . . H3A H 0.7771 0.1377 0.8030 0.032 Uiso 1 calc R . . C4 C 0.6974(2) 0.00167(16) 0.69026(14) 0.0303(4) Uani 1 d . . . H4A H 0.5977 -0.0354 0.6609 0.036 Uiso 1 calc R . . H4B H 0.7567 -0.0618 0.7302 0.036 Uiso 1 calc R . . C5 C 0.78243(18) 0.05089(15) 0.59102(13) 0.0270(4) Uani 1 d . . . H5A H 0.8845 0.0840 0.6227 0.032 Uiso 1 calc R . . C6 C 0.69878(19) 0.15397(16) 0.53148(13) 0.0304(4) Uani 1 d . . . H6A H 0.5984 0.1229 0.4971 0.036 Uiso 1 calc R . . H6B H 0.7575 0.1860 0.4701 0.036 Uiso 1 calc R . . C7 C 0.59917(18) 0.36113(16) 0.56111(13) 0.0270(4) Uani 1 d . . . C8 C 0.59523(19) 0.05927(15) 0.87243(14) 0.0285(4) Uani 1 d . . . C9 C 0.80646(19) -0.05179(17) 0.51110(14) 0.0317(4) Uani 1 d . . . N1 N 0.86166(19) 0.26172(15) 1.01022(13) 0.0410(4) Uani 1 d . . . N2 N 0.88679(17) 0.44455(14) 0.85679(12) 0.0352(4) Uani 1 d . . . C10 C 0.8508(3) 0.1759(2) 1.08710(17) 0.0523(6) Uani 1 d . . . H10A H 0.8996 0.1023 1.0759 0.063 Uiso 1 calc R . . C11 C 0.7723(3) 0.1860(2) 1.18364(18) 0.0573(6) Uani 1 d . . . H11A H 0.7684 0.1211 1.2360 0.069 Uiso 1 calc R . . C12 C 0.7019(3) 0.2905(2) 1.20090(17) 0.0517(6) Uani 1 d . . . H12A H 0.6471 0.2992 1.2655 0.062 Uiso 1 calc R . . C13 C 0.7104(2) 0.38574(19) 1.12306(15) 0.0400(5) Uani 1 d . . . C14 C 0.7929(2) 0.36644(17) 1.02798(14) 0.0342(4) Uani 1 d . . . C15 C 0.6407(2) 0.4989(2) 1.13647(17) 0.0459(5) Uani 1 d . . . H15A H 0.5855 0.5112 1.2003 0.055 Uiso 1 calc R . . C16 C 0.6520(2) 0.5883(2) 1.06035(17) 0.0455(5) Uani 1 d . . . H16A H 0.6046 0.6626 1.0713 0.055 Uiso 1 calc R . . C17 C 0.7348(2) 0.57315(18) 0.96277(16) 0.0374(4) Uani 1 d . . . C18 C 0.7486(2) 0.66425(19) 0.88145(17) 0.0462(5) Uani 1 d . . . H18A H 0.7013 0.7392 0.8890 0.055 Uiso 1 calc R . . C19 C 0.8304(2) 0.64434(19) 0.79147(17) 0.0462(5) Uani 1 d . . . H19A H 0.8412 0.7049 0.7357 0.055 Uiso 1 calc R . . C20 C 0.8975(2) 0.53367(18) 0.78335(16) 0.0408(5) Uani 1 d . . . H20A H 0.9549 0.5211 0.7208 0.049 Uiso 1 calc R . . C21 C 0.80515(19) 0.46334(17) 0.94651(14) 0.0315(4) Uani 1 d . . . O7 O 1.05665(14) 0.31907(12) 0.57035(12) 0.0385(3) Uani 1 d . . . H7O H 1.052(3) 0.294(2) 0.648(2) 0.068(7) Uiso 1 d . . . C22 C 1.1775(3) 0.4062(2) 0.5624(2) 0.0590(6) Uani 1 d . . . H22A H 1.1621 0.4768 0.6097 0.088 Uiso 1 calc R . . H22B H 1.1802 0.4316 0.4835 0.088 Uiso 1 calc R . . H22C H 1.2738 0.3705 0.5885 0.088 Uiso 1 calc R . . O8 O 1.03793(16) 0.25149(13) 0.78076(11) 0.0433(4) Uani 1 d . . . H8O H 0.992(3) 0.303(3) 0.826(2) 0.081(9) Uiso 1 d . . . C23 C 1.1057(2) 0.1530(2) 0.83799(18) 0.0480(5) Uani 1 d . . . H23A H 1.1503 0.1798 0.9130 0.072 Uiso 1 calc R . . H23B H 1.1854 0.1227 0.7945 0.072 Uiso 1 calc R . . H23C H 1.0285 0.0880 0.8462 0.072 Uiso 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 0.0519(8) 0.0382(8) 0.0240(6) 0.0054(5) 0.0021(5) 0.0144(6) O2 0.0486(8) 0.0306(7) 0.0280(6) 0.0027(5) 0.0030(5) 0.0102(6) O3 0.0529(8) 0.0492(9) 0.0389(7) 0.0195(6) 0.0255(6) 0.0266(7) O4 0.0701(9) 0.0404(8) 0.0406(7) 0.0195(6) 0.0313(7) 0.0261(7) O5 0.0617(9) 0.0551(10) 0.0361(8) -0.0151(7) -0.0020(7) 0.0144(7) O6 0.0588(9) 0.0370(8) 0.0344(7) -0.0027(6) 0.0087(6) 0.0167(7) C1 0.0265(8) 0.0287(9) 0.0225(8) 0.0043(7) 0.0052(6) 0.0033(7) C2 0.0304(8) 0.0289(9) 0.0242(8) 0.0042(7) 0.0080(7) 0.0056(7) C3 0.0291(8) 0.0274(9) 0.0238(8) 0.0040(7) 0.0075(7) 0.0059(7) C4 0.0369(9) 0.0285(9) 0.0270(8) 0.0026(7) 0.0095(7) 0.0037(7) C5 0.0305(8) 0.0283(9) 0.0232(8) 0.0012(7) 0.0073(7) 0.0032(7) C6 0.0338(9) 0.0357(10) 0.0226(8) 0.0025(7) 0.0060(7) 0.0046(8) C7 0.0270(8) 0.0299(9) 0.0251(9) 0.0053(7) 0.0081(7) 0.0015(7) C8 0.0365(9) 0.0253(9) 0.0250(8) 0.0048(7) 0.0066(7) 0.0065(7) C9 0.0339(9) 0.0331(10) 0.0294(9) 0.0001(7) 0.0101(8) 0.0018(8) N1 0.0536(10) 0.0372(9) 0.0327(8) 0.0007(7) 0.0032(7) 0.0074(8) N2 0.0368(8) 0.0375(9) 0.0316(8) -0.0006(7) 0.0036(6) 0.0050(7) C10 0.0765(15) 0.0408(12) 0.0397(11) 0.0040(9) 0.0033(10) 0.0078(11) C11 0.0837(17) 0.0525(15) 0.0359(11) 0.0084(10) 0.0089(11) -0.0034(12) C12 0.0639(14) 0.0583(15) 0.0334(10) -0.0030(10) 0.0116(10) -0.0060(11) C13 0.0407(10) 0.0481(12) 0.0310(9) -0.0087(9) 0.0045(8) -0.0029(9) C14 0.0365(9) 0.0377(11) 0.0280(9) -0.0056(8) 0.0015(7) 0.0005(8) C15 0.0461(11) 0.0545(14) 0.0385(11) -0.0158(10) 0.0106(9) 0.0032(10) C16 0.0456(11) 0.0444(12) 0.0473(12) -0.0161(10) 0.0061(9) 0.0098(9) C17 0.0372(10) 0.0361(11) 0.0383(10) -0.0090(8) -0.0003(8) 0.0038(8) C18 0.0567(12) 0.0316(11) 0.0497(12) -0.0071(9) -0.0012(10) 0.0069(9) C19 0.0593(13) 0.0363(11) 0.0422(11) 0.0032(9) -0.0003(10) 0.0010(10) C20 0.0460(11) 0.0415(12) 0.0352(10) 0.0015(9) 0.0055(8) 0.0013(9) C21 0.0298(9) 0.0351(10) 0.0290(9) -0.0060(8) 0.0003(7) 0.0015(7) O7 0.0399(7) 0.0366(8) 0.0405(8) -0.0023(6) 0.0128(6) -0.0005(6) C22 0.0549(13) 0.0662(16) 0.0567(13) -0.0052(12) 0.0211(11) -0.0194(12) O8 0.0537(8) 0.0395(8) 0.0394(7) 0.0017(6) 0.0136(6) 0.0150(7) C23 0.0467(11) 0.0506(13) 0.0473(12) 0.0007(10) -0.0001(9) 0.0167(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 O1 C7 1.230(2) . ? O2 C7 1.310(2) . ? O2 H2O 0.97(3) . ? O3 C8 1.228(2) . ? O4 C8 1.298(2) . ? O4 H4O 0.98(4) . ? O5 C9 1.207(2) . ? O6 C9 1.333(2) . ? O6 H6O 0.97(3) . ? C1 C7 1.497(2) . ? C1 C6 1.527(2) . ? C1 C2 1.540(2) . ? C1 H1A 1.0000 . ? C2 C3 1.525(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.502(2) . ? C3 C4 1.535(2) . ? C3 H3A 1.0000 . ? C4 C5 1.541(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C9 1.509(2) . ? C5 C6 1.524(2) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N1 C10 1.323(3) . ? N1 C14 1.353(2) . ? N2 C20 1.322(2) . ? N2 C21 1.360(2) . ? C10 C11 1.398(3) . ? C10 H10A 0.9500 . ? C11 C12 1.357(3) . ? C11 H11A 0.9500 . ? C12 C13 1.405(3) . ? C12 H12A 0.9500 . ? C13 C14 1.418(3) . ? C13 C15 1.431(3) . ? C14 C21 1.451(3) . ? C15 C16 1.346(3) . ? C15 H15A 0.9500 . ? C16 C17 1.438(3) . ? C16 H16A 0.9500 . ? C17 C18 1.404(3) . ? C17 C21 1.406(3) . ? C18 C19 1.365(3) . ? C18 H18A 0.9500 . ? C19 C20 1.387(3) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? O7 C22 1.417(2) . ? O7 H7O 0.96(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O8 C23 1.410(2) . ? O8 H8O 0.92(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 H2O 110.6(16) . . ? C8 O4 H4O 111(2) . . ? C9 O6 H6O 111.5(15) . . ? C7 C1 C6 112.87(13) . . ? C7 C1 C2 109.75(13) . . ? C6 C1 C2 111.68(14) . . ? C7 C1 H1A 107.4 . . ? C6 C1 H1A 107.4 . . ? C2 C1 H1A 107.4 . . ? C3 C2 C1 109.77(13) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C8 C3 C2 111.34(13) . . ? C8 C3 C4 111.32(14) . . ? C2 C3 C4 112.33(13) . . ? C8 C3 H3A 107.2 . . ? C2 C3 H3A 107.2 . . ? C4 C3 H3A 107.2 . . ? C3 C4 C5 110.03(14) . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C9 C5 C6 112.25(14) . . ? C9 C5 C4 109.52(14) . . ? C6 C5 C4 111.14(13) . . ? C9 C5 H5A 107.9 . . ? C6 C5 H5A 107.9 . . ? C4 C5 H5A 107.9 . . ? C5 C6 C1 110.40(13) . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C1 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O1 C7 O2 122.78(16) . . ? O1 C7 C1 123.35(15) . . ? O2 C7 C1 113.87(14) . . ? O3 C8 O4 122.49(15) . . ? O3 C8 C3 122.19(15) . . ? O4 C8 C3 115.29(14) . . ? O5 C9 O6 123.13(17) . . ? O5 C9 C5 124.91(17) . . ? O6 C9 C5 111.96(15) . . ? C10 N1 C14 117.03(17) . . ? C20 N2 C21 117.53(17) . . ? N1 C10 C11 124.5(2) . . ? N1 C10 H10A 117.7 . . ? C11 C10 H10A 117.7 . . ? C12 C11 C10 118.5(2) . . ? C12 C11 H11A 120.8 . . ? C10 C11 H11A 120.8 . . ? C11 C12 C13 119.88(19) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C12 C13 C14 117.21(19) . . ? C12 C13 C15 122.97(18) . . ? C14 C13 C15 119.82(18) . . ? N1 C14 C13 122.86(17) . . ? N1 C14 C21 118.47(15) . . ? C13 C14 C21 118.66(17) . . ? C16 C15 C13 121.23(18) . . ? C16 C15 H15A 119.4 . . ? C13 C15 H15A 119.4 . . ? C15 C16 C17 121.00(19) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C18 C17 C21 117.85(17) . . ? C18 C17 C16 122.57(19) . . ? C21 C17 C16 119.58(18) . . ? C19 C18 C17 119.52(19) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? C18 C19 C20 118.50(19) . . ? C18 C19 H19A 120.7 . . ? C20 C19 H19A 120.7 . . ? N2 C20 C19 124.42(18) . . ? N2 C20 H20A 117.8 . . ? C19 C20 H20A 117.8 . . ? N2 C21 C17 122.16(17) . . ? N2 C21 C14 118.12(16) . . ? C17 C21 C14 119.71(16) . . ? C22 O7 H7O 110.4(15) . . ? O7 C22 H22A 109.5 . . ? O7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 O8 H8O 114.2(17) . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C7 C1 C2 C3 -178.03(13) . . . . ? C6 C1 C2 C3 56.02(18) . . . . ? C1 C2 C3 C8 178.76(14) . . . . ? C1 C2 C3 C4 -55.62(18) . . . . ? C8 C3 C4 C5 -178.43(14) . . . . ? C2 C3 C4 C5 55.94(18) . . . . ? C3 C4 C5 C9 179.27(14) . . . . ? C3 C4 C5 C6 -56.12(18) . . . . ? C9 C5 C6 C1 -179.86(13) . . . . ? C4 C5 C6 C1 57.09(18) . . . . ? C7 C1 C6 C5 178.56(13) . . . . ? C2 C1 C6 C5 -57.22(17) . . . . ? C6 C1 C7 O1 1.4(2) . . . . ? C2 C1 C7 O1 -123.91(17) . . . . ? C6 C1 C7 O2 -178.23(13) . . . . ? C2 C1 C7 O2 56.50(18) . . . . ? C2 C3 C8 O3 -10.5(2) . . . . ? C4 C3 C8 O3 -136.68(18) . . . . ? C2 C3 C8 O4 171.44(15) . . . . ? C4 C3 C8 O4 45.3(2) . . . . ? C6 C5 C9 O5 -11.9(2) . . . . ? C4 C5 C9 O5 112.02(19) . . . . ? C6 C5 C9 O6 167.77(14) . . . . ? C4 C5 C9 O6 -68.27(18) . . . . ? C14 N1 C10 C11 0.7(3) . . . . ? N1 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C11 C12 C13 C15 -179.2(2) . . . . ? C10 N1 C14 C13 -0.8(3) . . . . ? C10 N1 C14 C21 178.81(17) . . . . ? C12 C13 C14 N1 0.2(3) . . . . ? C15 C13 C14 N1 179.91(17) . . . . ? C12 C13 C14 C21 -179.40(17) . . . . ? C15 C13 C14 C21 0.3(3) . . . . ? C12 C13 C15 C16 179.6(2) . . . . ? C14 C13 C15 C16 -0.1(3) . . . . ? C13 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 179.81(19) . . . . ? C15 C16 C17 C21 0.0(3) . . . . ? C21 C17 C18 C19 -0.9(3) . . . . ? C16 C17 C18 C19 179.21(19) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C21 N2 C20 C19 -0.4(3) . . . . ? C18 C19 C20 N2 0.6(3) . . . . ? C20 N2 C21 C17 -0.5(3) . . . . ? C20 N2 C21 C14 -179.81(16) . . . . ? C18 C17 C21 N2 1.2(3) . . . . ? C16 C17 C21 N2 -178.97(16) . . . . ? C18 C17 C21 C14 -179.57(16) . . . . ? C16 C17 C21 C14 0.3(3) . . . . ? N1 C14 C21 N2 -0.7(2) . . . . ? C13 C14 C21 N2 178.86(16) . . . . ? N1 C14 C21 C17 179.97(16) . . . . ? C13 C14 C21 C17 -0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.261 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.043 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 H2o O1 1.02 1.60 2.610(2) 172.1 3_666 O4 H4o O3 1.02 1.58 2.595(2) 174.8 3_607 O6 H6o O7 1.02 1.61 2.628(2) 175.4 3_706 O7 H7o O8 0.98 1.65 2.625(2) 178.1 . O8 H8o N1 0.98 2.55 3.261(2) 129.3 . O8 H8o N2 0.98 1.85 2.755(2) 153.5 . #===END ########################################################## data_CTAAPY _database_code_CSD 189059 _chemical_name_systematic ; cyclohexane-1,3cis,5cis-tricaboxylic acid-- 2-aminopyrimidine (1/1) ; _chemical_name_common CTA/APY _chemical_formula_moiety 'C4 H5 N3, C9 H12 O6' _chemical_formula_sum 'C13 H17 N3 O6' _chemical_formula_weight 311.30 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 'P 21/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 5.6250(2) _cell_length_b 23.8851(18) _cell_length_c 11.2217(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.109(5) _cell_angle_gamma 90.00 _cell_volume 1484.27(17) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5738 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 20.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9856 _exptl_absorpt_correction_T_max 0.9922 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 7803 _diffrn_reflns_av_R_equivalents 0.1362 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 20.77 _reflns_number_total 1447 _reflns_number_gt 1081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement ; HKL Scalepack (Otwinowski & Minor 1997) ; _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.2886P] 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 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1447 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6926(4) 0.64205(9) 0.2251(2) 0.0298(7) Uani 1 d . . . O2 O 0.3160(4) 0.64581(9) 0.1035(2) 0.0282(7) Uani 1 d . . . O3 O 0.7074(5) 0.88883(11) 0.3906(2) 0.0477(8) Uani 1 d . . . O4 O 1.0555(5) 0.83685(10) 0.3825(3) 0.0487(9) Uani 1 d . . . O5 O 0.0098(4) 0.87644(10) -0.0133(2) 0.0341(7) Uani 1 d . . . O6 O 0.1408(4) 0.82814(9) -0.1615(2) 0.0279(7) Uani 1 d . . . C1 C 0.5732(5) 0.73023(12) 0.1310(3) 0.0223(9) Uani 1 d . . . H1 H 0.7076 0.7318 0.0834 0.027 Uiso 1 calc R . . C2 C 0.6541(6) 0.76275(12) 0.2493(3) 0.0269(9) Uani 1 d . . . H2A H 0.8002 0.7449 0.2959 0.032 Uiso 1 calc R . . H2B H 0.5251 0.7611 0.2990 0.032 Uiso 1 calc R . . C3 C 0.7099(6) 0.82468(13) 0.2249(3) 0.0245(9) Uani 1 d . . . H3 H 0.8355 0.8250 0.1719 0.029 Uiso 1 calc R . . C4 C 0.4755(5) 0.85232(13) 0.1512(3) 0.0228(9) Uani 1 d . . . H4A H 0.3443 0.8510 0.1995 0.027 Uiso 1 calc R . . H4B H 0.5078 0.8921 0.1348 0.027 Uiso 1 calc R . . C5 C 0.3965(6) 0.82134(12) 0.0318(3) 0.0216(9) Uani 1 d . . . H5 H 0.5312 0.8234 -0.0156 0.026 Uiso 1 calc R . . C6 C 0.3441(6) 0.75919(13) 0.0529(3) 0.0250(9) Uani 1 d . . . H6A H 0.3018 0.7398 -0.0260 0.030 Uiso 1 calc R . . H6B H 0.2049 0.7561 0.0956 0.030 Uiso 1 calc R . . C7 C 0.5238(6) 0.66867(13) 0.1548(3) 0.0219(9) Uani 1 d . . . C8 C 0.8158(6) 0.85390(15) 0.3414(3) 0.0282(9) Uani 1 d . . . C9 C 0.1654(6) 0.84554(14) -0.0479(3) 0.0227(9) Uani 1 d . . . N1 N 0.2098(5) 0.49044(11) 0.3731(3) 0.0294(8) Uani 1 d . . . H3A H 0.601(7) 0.5873(17) 0.337(4) 0.062(6) Uiso 1 d . . . H3B H 0.613(7) 0.5410(17) 0.445(4) 0.062(6) Uiso 1 d . . . N2 N 0.1884(5) 0.55525(12) 0.2128(3) 0.0267(8) Uani 1 d . . . N3 N 0.5213(5) 0.55873(13) 0.3773(3) 0.0313(9) Uani 1 d . . . C10 C 0.3064(6) 0.53473(14) 0.3213(3) 0.0251(9) Uani 1 d . . . C11 C -0.0305(6) 0.53193(14) 0.1532(3) 0.0315(10) Uani 1 d . . . H11 H -0.1092 0.5477 0.0790 0.038 Uiso 1 calc R . . C12 C -0.1320(6) 0.48659(14) 0.2009(3) 0.0350(11) Uani 1 d . . . H12 H -0.2769 0.4693 0.1617 0.042 Uiso 1 calc R . . C13 C -0.0027(6) 0.46791(14) 0.3132(4) 0.0337(10) Uani 1 d . . . H13 H -0.0681 0.4372 0.3504 0.040 Uiso 1 calc R . . H100 H 0.269(7) 0.5882(17) 0.173(4) 0.062(6) Uiso 1 d . . . H101 H 1.137(7) 0.8497(16) 0.460(4) 0.062(6) Uiso 1 d . . . H102 H -0.029(7) 0.8396(15) -0.202(4) 0.062(6) Uiso 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 0.0315(15) 0.0258(14) 0.0268(15) 0.0048(12) -0.0098(12) 0.0014(11) O2 0.0330(15) 0.0275(14) 0.0202(15) 0.0038(11) -0.0062(12) -0.0055(11) O3 0.0451(18) 0.0577(19) 0.0370(19) -0.0206(15) -0.0024(14) 0.0080(14) O4 0.055(2) 0.0462(17) 0.0337(19) -0.0134(14) -0.0230(15) 0.0136(13) O5 0.0344(16) 0.0381(15) 0.0267(17) -0.0056(12) -0.0029(13) 0.0100(12) O6 0.0322(15) 0.0322(14) 0.0152(16) 0.0000(12) -0.0067(12) 0.0019(11) C1 0.025(2) 0.023(2) 0.016(2) -0.0001(16) -0.0028(17) -0.0019(14) C2 0.038(2) 0.022(2) 0.019(2) 0.0016(17) -0.0014(18) 0.0001(15) C3 0.031(2) 0.026(2) 0.015(2) -0.0019(17) 0.0005(17) 0.0004(15) C4 0.025(2) 0.0195(19) 0.023(2) 0.0035(17) 0.0005(16) -0.0014(14) C5 0.028(2) 0.021(2) 0.014(2) 0.0001(16) -0.0014(17) -0.0019(14) C6 0.027(2) 0.028(2) 0.019(2) -0.0008(16) -0.0005(17) -0.0013(15) C7 0.028(2) 0.027(2) 0.010(2) -0.0025(17) 0.0024(18) -0.0009(18) C8 0.030(2) 0.029(2) 0.022(2) 0.003(2) -0.0056(19) -0.0008(18) C9 0.025(2) 0.022(2) 0.019(3) 0.0019(18) -0.0033(18) -0.0056(17) N1 0.035(2) 0.0273(18) 0.024(2) 0.0043(15) 0.0021(16) -0.0041(14) N2 0.035(2) 0.0234(17) 0.0184(19) 0.0012(15) -0.0044(15) -0.0003(14) N3 0.040(2) 0.0245(18) 0.028(2) 0.0041(16) 0.0009(17) -0.0013(15) C10 0.029(2) 0.023(2) 0.023(3) -0.0033(18) 0.004(2) 0.0018(18) C11 0.038(2) 0.028(2) 0.028(2) -0.0012(19) 0.002(2) 0.0058(18) C12 0.035(2) 0.028(2) 0.036(3) -0.0022(19) -0.006(2) -0.0050(17) C13 0.040(2) 0.026(2) 0.034(3) 0.0048(19) 0.003(2) -0.0006(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 C7 1.290(4) . ? O2 C7 1.327(4) . ? O3 C8 1.221(4) . ? O4 C8 1.407(4) . ? O4 H101 0.96(4) . ? O5 C9 1.257(4) . ? O6 C9 1.325(4) . ? O6 H102 1.02(4) . ? C1 C7 1.529(4) . ? C1 C2 1.536(4) . ? C1 C6 1.585(4) . ? C1 H1 1.0000 . ? C2 C3 1.547(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.510(5) . ? C3 C4 1.574(4) . ? C3 H3 1.0000 . ? C4 C5 1.527(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.540(4) . ? C5 C9 1.554(4) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N1 C10 1.365(4) . ? N1 C13 1.374(4) . ? N2 C10 1.371(4) . ? N2 C11 1.409(4) . ? N2 H100 1.05(4) . ? N3 C10 1.385(4) . ? N3 H3A 0.97(4) . ? N3 H3B 0.94(4) . ? C11 C12 1.376(5) . ? C11 H11 0.9500 . ? C12 C13 1.412(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 O4 H101 119(2) . . ? C9 O6 H102 106(2) . . ? C7 C1 C2 111.8(3) . . ? C7 C1 C6 111.2(3) . . ? C2 C1 C6 110.3(3) . . ? C7 C1 H1 107.8 . . ? C2 C1 H1 107.8 . . ? C6 C1 H1 107.8 . . ? C1 C2 C3 111.6(3) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C8 C3 C2 110.5(3) . . ? C8 C3 C4 115.3(3) . . ? C2 C3 C4 108.5(3) . . ? C8 C3 H3 107.4 . . ? C2 C3 H3 107.4 . . ? C4 C3 H3 107.4 . . ? C5 C4 C3 110.2(3) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 111.5(3) . . ? C4 C5 C9 114.2(3) . . ? C6 C5 C9 106.5(2) . . ? C4 C5 H5 108.2 . . ? C6 C5 H5 108.2 . . ? C9 C5 H5 108.2 . . ? C5 C6 C1 110.3(2) . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C1 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O1 C7 O2 124.1(3) . . ? O1 C7 C1 116.4(3) . . ? O2 C7 C1 119.6(3) . . ? O3 C8 O4 125.2(3) . . ? O3 C8 C3 123.7(3) . . ? O4 C8 C3 111.1(3) . . ? O5 C9 O6 121.4(3) . . ? O5 C9 C5 126.7(3) . . ? O6 C9 C5 111.8(3) . . ? C10 N1 C13 118.2(3) . . ? C10 N2 C11 121.8(3) . . ? C10 N2 H100 118(2) . . ? C11 N2 H100 120(2) . . ? C10 N3 H3A 121(2) . . ? C10 N3 H3B 120(2) . . ? H3A N3 H3B 117(3) . . ? N1 C10 N2 119.2(3) . . ? N1 C10 N3 120.6(3) . . ? N2 C10 N3 120.2(3) . . ? C12 C11 N2 121.0(3) . . ? C12 C11 H11 119.5 . . ? N2 C11 H11 119.5 . . ? C11 C12 C13 114.3(3) . . ? C11 C12 H12 122.8 . . ? C13 C12 H12 122.8 . . ? N1 C13 C12 125.5(3) . . ? N1 C13 H13 117.2 . . ? C12 C13 H13 117.2 . . ? 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 C7 C1 C2 C3 178.6(3) . . . . ? C6 C1 C2 C3 -57.2(4) . . . . ? C1 C2 C3 C8 -173.5(3) . . . . ? C1 C2 C3 C4 59.1(4) . . . . ? C8 C3 C4 C5 176.2(3) . . . . ? C2 C3 C4 C5 -59.3(3) . . . . ? C3 C4 C5 C6 59.2(3) . . . . ? C3 C4 C5 C9 180.0(3) . . . . ? C4 C5 C6 C1 -56.3(4) . . . . ? C9 C5 C6 C1 178.6(3) . . . . ? C7 C1 C6 C5 179.1(3) . . . . ? C2 C1 C6 C5 54.6(4) . . . . ? C2 C1 C7 O1 -51.5(4) . . . . ? C6 C1 C7 O1 -175.2(3) . . . . ? C2 C1 C7 O2 128.7(3) . . . . ? C6 C1 C7 O2 5.0(4) . . . . ? C2 C3 C8 O3 -108.4(4) . . . . ? C4 C3 C8 O3 15.0(5) . . . . ? C2 C3 C8 O4 73.5(4) . . . . ? C4 C3 C8 O4 -163.0(3) . . . . ? C4 C5 C9 O5 -19.4(5) . . . . ? C6 C5 C9 O5 104.0(4) . . . . ? C4 C5 C9 O6 162.9(3) . . . . ? C6 C5 C9 O6 -73.7(3) . . . . ? C13 N1 C10 N2 0.5(4) . . . . ? C13 N1 C10 N3 -179.4(3) . . . . ? C11 N2 C10 N1 0.1(5) . . . . ? C11 N2 C10 N3 -180.0(3) . . . . ? C10 N2 C11 C12 -1.4(5) . . . . ? N2 C11 C12 C13 1.9(5) . . . . ? C10 N1 C13 C12 0.2(5) . . . . ? C11 C12 C13 N1 -1.3(5) . . . . ? 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 N3 H3A O1 1.01 1.91 2.895(4) 165.7 . N3 H3B N1 1.01 2.17 3.166(4) 168.4 3_666 N2 H100 O2 1.01 1.66 2.647(4) 164.1 . O4 H101 O2 1.02 1.69 2.682(3) 163.6 4_676 O6 H102 O1 1.02 1.69 2.712(3) 177.6 4_475 #===END ########################################################## data_CTAHMTA _database_code_CSD 189060 _chemical_name_systematic ; cyclohexane-1,3cis,5cis-tricaboxylic acid-- hexamethylenetetramine(1/1) ; _chemical_name_common CTA/HMTA _chemical_melting_point 'not measured' _chemical_formula_moiety 'C9 H12 O6, C6 H12 N4' _chemical_formula_sum 'C15 H24 N4 O6' _chemical_formula_weight 356.38 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 'P 21/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 10.9547(4) _cell_length_b 14.4867(6) _cell_length_c 10.4289(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.987(2) _cell_angle_gamma 90.00 _cell_volume 1651.03(11) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4803 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9748 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 9159 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3723 _reflns_number_gt 2908 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement ; HKL Scalepack (Otwinowski & Minor 1997) ; _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.1486P] 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 3723 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.003 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.03834(9) -0.68507(8) -0.09206(10) 0.0324(3) Uani 1 d . . . O2 O 0.00437(10) -0.64132(7) 0.11135(10) 0.0259(3) Uani 1 d . . . H2O H -0.082(2) -0.6402(16) 0.116(2) 0.066(7) Uiso 1 d . . . O3 O 0.37024(13) -0.69623(9) -0.37427(11) 0.0457(4) Uani 1 d . . . O4 O 0.47137(12) -0.78561(9) -0.23214(12) 0.0436(3) Uani 1 d . . . H4O H 0.503(2) -0.8120(17) -0.302(2) 0.064(7) Uiso 1 d . . . O5 O 0.23228(9) -0.35621(7) -0.13822(11) 0.0300(3) Uani 1 d . . . O6 O 0.43059(9) -0.37108(7) -0.08299(10) 0.0325(3) Uani 1 d . . . C1 C 0.16750(12) -0.63776(9) -0.02543(13) 0.0191(3) Uani 1 d . . . H1A H 0.2174 -0.6522 0.0561 0.023 Uiso 1 calc R . . C2 C 0.21749(13) -0.69276(9) -0.13459(14) 0.0227(3) Uani 1 d . . . H2A H 0.1681 -0.6798 -0.2157 0.027 Uiso 1 calc R . . H2B H 0.2116 -0.7596 -0.1163 0.027 Uiso 1 calc R . . C3 C 0.35140(12) -0.66672(9) -0.14962(13) 0.0198(3) Uani 1 d . . . H3A H 0.4017 -0.6860 -0.0704 0.024 Uiso 1 calc R . . C4 C 0.36716(12) -0.56224(9) -0.16897(13) 0.0193(3) Uani 1 d . . . H4A H 0.4555 -0.5476 -0.1679 0.023 Uiso 1 calc R . . H4B H 0.3289 -0.5445 -0.2542 0.023 Uiso 1 calc R . . C5 C 0.30923(12) -0.50547(9) -0.06446(12) 0.0180(3) Uani 1 d . . . H5A H 0.3558 -0.5183 0.0195 0.022 Uiso 1 calc R . . C6 C 0.17680(12) -0.53375(9) -0.05272(13) 0.0191(3) Uani 1 d . . . H6A H 0.1280 -0.5188 -0.1335 0.023 Uiso 1 calc R . . H6B H 0.1426 -0.4986 0.0178 0.023 Uiso 1 calc R . . C7 C 0.03509(12) -0.65867(9) -0.00688(13) 0.0206(3) Uani 1 d . . . C8 C 0.39701(12) -0.71707(9) -0.26377(13) 0.0218(3) Uani 1 d . . . C9 C 0.32518(12) -0.40346(9) -0.09639(12) 0.0196(3) Uani 1 d . . . N1 N 0.11305(12) -0.04626(10) -0.07960(13) 0.0336(3) Uani 1 d . . . N2 N 0.32234(12) -0.04273(9) 0.01521(12) 0.0282(3) Uani 1 d . . . N3 N 0.25224(12) -0.17064(9) -0.11871(13) 0.0281(3) Uani 1 d . . . H3N H 0.2556(17) -0.2357(15) -0.1333(18) 0.046(5) Uiso 1 d . . . N4 N 0.28123(12) -0.02210(9) -0.21571(12) 0.0314(3) Uani 1 d . . . C10 C 0.29088(14) -0.12019(11) -0.23515(14) 0.0286(3) Uani 1 d . . . H10A H 0.3764 -0.1365 -0.2504 0.034 Uiso 1 calc R . . H10B H 0.2380 -0.1388 -0.3117 0.034 Uiso 1 calc R . . C11 C 0.12153(14) -0.14411(12) -0.09739(15) 0.0328(4) Uani 1 d . . . H11A H 0.0671 -0.1631 -0.1725 0.039 Uiso 1 calc R . . H11B H 0.0946 -0.1764 -0.0206 0.039 Uiso 1 calc R . . C12 C 0.15418(16) 0.00013(11) -0.19323(16) 0.0359(4) Uani 1 d . . . H12A H 0.1462 0.0677 -0.1824 0.043 Uiso 1 calc R . . H12B H 0.1007 -0.0183 -0.2694 0.043 Uiso 1 calc R . . C13 C 0.19434(15) -0.01910(13) 0.03230(15) 0.0363(4) Uani 1 d . . . H13A H 0.1876 0.0483 0.0458 0.044 Uiso 1 calc R . . H13B H 0.1678 -0.0505 0.1099 0.044 Uiso 1 calc R . . C14 C 0.35979(16) 0.00417(12) -0.10054(15) 0.0347(4) Uani 1 d . . . H14A H 0.4458 -0.0119 -0.1140 0.042 Uiso 1 calc R . . H14B H 0.3553 0.0718 -0.0880 0.042 Uiso 1 calc R . . C15 C 0.33352(16) -0.14092(11) -0.00185(16) 0.0347(4) Uani 1 d . . . H15A H 0.3086 -0.1735 0.0756 0.042 Uiso 1 calc R . . H15B H 0.4197 -0.1571 -0.0142 0.042 Uiso 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 0.0232(6) 0.0430(7) 0.0304(6) 0.0021(5) -0.0014(4) -0.0081(5) O2 0.0204(6) 0.0271(5) 0.0310(6) -0.0050(4) 0.0079(4) -0.0045(4) O3 0.0687(9) 0.0426(7) 0.0255(6) -0.0052(5) 0.0012(5) 0.0272(6) O4 0.0548(8) 0.0425(7) 0.0335(7) -0.0037(6) 0.0021(6) 0.0314(6) O5 0.0216(5) 0.0171(5) 0.0524(7) 0.0034(5) 0.0096(5) 0.0004(4) O6 0.0254(6) 0.0305(6) 0.0410(6) 0.0097(5) -0.0020(5) -0.0129(5) C1 0.0175(7) 0.0160(6) 0.0242(7) 0.0027(6) 0.0034(5) -0.0012(5) C2 0.0207(7) 0.0168(7) 0.0309(8) -0.0025(6) 0.0044(5) -0.0019(5) C3 0.0186(7) 0.0184(7) 0.0224(7) -0.0010(6) 0.0017(5) 0.0019(5) C4 0.0175(7) 0.0190(7) 0.0219(7) -0.0013(6) 0.0049(5) -0.0007(5) C5 0.0174(7) 0.0169(6) 0.0200(6) 0.0001(6) 0.0039(5) -0.0023(5) C6 0.0177(7) 0.0156(6) 0.0248(7) -0.0004(5) 0.0062(5) -0.0007(5) C7 0.0207(7) 0.0140(6) 0.0272(7) 0.0044(6) 0.0024(5) 0.0001(5) C8 0.0199(7) 0.0184(7) 0.0271(8) -0.0028(6) 0.0021(5) 0.0009(5) C9 0.0203(7) 0.0189(7) 0.0204(7) -0.0017(6) 0.0069(5) -0.0036(5) N1 0.0255(7) 0.0435(8) 0.0315(7) -0.0128(6) 0.0011(5) 0.0073(6) N2 0.0301(7) 0.0267(7) 0.0269(6) -0.0042(5) -0.0040(5) -0.0009(5) N3 0.0332(7) 0.0158(6) 0.0343(7) -0.0003(5) -0.0048(5) 0.0006(5) N4 0.0374(8) 0.0285(7) 0.0280(7) 0.0043(6) -0.0006(5) -0.0110(6) C10 0.0232(8) 0.0348(9) 0.0283(8) -0.0085(7) 0.0044(6) -0.0012(6) C11 0.0300(9) 0.0389(9) 0.0299(8) -0.0009(7) 0.0052(6) -0.0120(7) C12 0.0457(10) 0.0242(8) 0.0358(9) -0.0012(7) -0.0113(7) 0.0100(7) C13 0.0342(9) 0.0446(10) 0.0299(8) -0.0135(7) 0.0008(6) 0.0024(7) C14 0.0377(9) 0.0310(8) 0.0351(9) -0.0011(7) -0.0008(7) -0.0136(7) C15 0.0375(9) 0.0290(8) 0.0354(9) 0.0028(7) -0.0122(7) 0.0036(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 O1 C7 1.2177(17) . ? O2 C7 1.3246(17) . ? O2 H2O 0.95(2) . ? O3 C8 1.2075(17) . ? O4 C8 1.3118(18) . ? O4 H4O 0.91(2) . ? O5 C9 1.2777(17) . ? O6 C9 1.2452(16) . ? C1 C7 1.5073(18) . ? C1 C2 1.5223(19) . ? C1 C6 1.5382(18) . ? C1 H1A 1.0000 . ? C2 C3 1.5332(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.5104(19) . ? C3 C4 1.5383(18) . ? C3 H3A 1.0000 . ? C4 C5 1.5372(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5206(18) . ? C5 C9 1.5276(18) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N1 C11 1.433(2) . ? N1 C12 1.461(2) . ? N1 C13 1.472(2) . ? N2 C15 1.440(2) . ? N2 C13 1.466(2) . ? N2 C14 1.468(2) . ? N3 C10 1.503(2) . ? N3 C11 1.514(2) . ? N3 C15 1.5207(19) . ? N3 H3N 0.96(2) . ? N4 C10 1.440(2) . ? N4 C12 1.463(2) . ? N4 C14 1.4780(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 H2O 111.4(13) . . ? C8 O4 H4O 112.3(14) . . ? C7 C1 C2 112.97(11) . . ? C7 C1 C6 107.30(11) . . ? C2 C1 C6 110.02(11) . . ? C7 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? C6 C1 H1A 108.8 . . ? C1 C2 C3 110.14(11) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C8 C3 C2 109.46(11) . . ? C8 C3 C4 108.99(11) . . ? C2 C3 C4 111.86(11) . . ? C8 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C5 C4 C3 112.19(11) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C9 113.72(11) . . ? C6 C5 C4 110.86(10) . . ? C9 C5 C4 107.69(10) . . ? C6 C5 H5A 108.1 . . ? C9 C5 H5A 108.1 . . ? C4 C5 H5A 108.1 . . ? C5 C6 C1 110.77(11) . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O1 C7 O2 122.74(13) . . ? O1 C7 C1 124.21(13) . . ? O2 C7 C1 112.97(11) . . ? O3 C8 O4 122.31(13) . . ? O3 C8 C3 124.04(13) . . ? O4 C8 C3 113.64(12) . . ? O6 C9 O5 123.15(12) . . ? O6 C9 C5 117.33(12) . . ? O5 C9 C5 119.49(11) . . ? C11 N1 C12 108.88(12) . . ? C11 N1 C13 109.03(13) . . ? C12 N1 C13 108.46(13) . . ? C15 N2 C13 109.63(13) . . ? C15 N2 C14 108.94(13) . . ? C13 N2 C14 108.42(12) . . ? C10 N3 C11 108.52(11) . . ? C10 N3 C15 109.13(12) . . ? C11 N3 C15 108.51(12) . . ? C10 N3 H3N 109.6(11) . . ? C11 N3 H3N 108.7(11) . . ? C15 N3 H3N 112.3(12) . . ? C10 N4 C12 108.64(12) . . ? C10 N4 C14 108.92(12) . . ? C12 N4 C14 108.65(12) . . ? N4 C10 N3 109.78(11) . . ? N4 C10 H10A 109.7 . . ? N3 C10 H10A 109.7 . . ? N4 C10 H10B 109.7 . . ? N3 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N1 C11 N3 109.91(12) . . ? N1 C11 H11A 109.7 . . ? N3 C11 H11A 109.7 . . ? N1 C11 H11B 109.7 . . ? N3 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N1 C12 N4 112.29(12) . . ? N1 C12 H12A 109.1 . . ? N4 C12 H12A 109.1 . . ? N1 C12 H12B 109.1 . . ? N4 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? N2 C13 N1 111.86(12) . . ? N2 C13 H13A 109.2 . . ? N1 C13 H13A 109.2 . . ? N2 C13 H13B 109.2 . . ? N1 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? N2 C14 N4 111.64(12) . . ? N2 C14 H14A 109.3 . . ? N4 C14 H14A 109.3 . . ? N2 C14 H14B 109.3 . . ? N4 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N2 C15 N3 109.19(12) . . ? N2 C15 H15A 109.8 . . ? N3 C15 H15A 109.8 . . ? N2 C15 H15B 109.8 . . ? N3 C15 H15B 109.8 . . ? H15A C15 H15B 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 C7 C1 C2 C3 178.90(11) . . . . ? C6 C1 C2 C3 59.02(14) . . . . ? C1 C2 C3 C8 -176.25(11) . . . . ? C1 C2 C3 C4 -55.34(15) . . . . ? C8 C3 C4 C5 173.38(11) . . . . ? C2 C3 C4 C5 52.21(15) . . . . ? C3 C4 C5 C6 -52.51(14) . . . . ? C3 C4 C5 C9 -177.51(11) . . . . ? C9 C5 C6 C1 177.94(11) . . . . ? C4 C5 C6 C1 56.42(14) . . . . ? C7 C1 C6 C5 176.46(10) . . . . ? C2 C1 C6 C5 -60.28(14) . . . . ? C2 C1 C7 O1 -27.48(18) . . . . ? C6 C1 C7 O1 93.95(16) . . . . ? C2 C1 C7 O2 155.44(11) . . . . ? C6 C1 C7 O2 -83.13(13) . . . . ? C2 C3 C8 O3 75.33(18) . . . . ? C4 C3 C8 O3 -47.31(19) . . . . ? C2 C3 C8 O4 -105.88(14) . . . . ? C4 C3 C8 O4 131.49(13) . . . . ? C6 C5 C9 O6 166.32(12) . . . . ? C4 C5 C9 O6 -70.41(15) . . . . ? C6 C5 C9 O5 -15.49(17) . . . . ? C4 C5 C9 O5 107.77(14) . . . . ? C12 N4 C10 N3 -59.32(15) . . . . ? C14 N4 C10 N3 58.87(15) . . . . ? C11 N3 C10 N4 59.11(15) . . . . ? C15 N3 C10 N4 -58.96(15) . . . . ? C12 N1 C11 N3 58.80(15) . . . . ? C13 N1 C11 N3 -59.36(16) . . . . ? C10 N3 C11 N1 -58.94(15) . . . . ? C15 N3 C11 N1 59.52(15) . . . . ? C11 N1 C12 N4 -60.43(16) . . . . ? C13 N1 C12 N4 58.08(16) . . . . ? C10 N4 C12 N1 60.55(16) . . . . ? C14 N4 C12 N1 -57.81(16) . . . . ? C15 N2 C13 N1 -60.13(17) . . . . ? C14 N2 C13 N1 58.69(17) . . . . ? C11 N1 C13 N2 59.96(18) . . . . ? C12 N1 C13 N2 -58.46(17) . . . . ? C15 N2 C14 N4 61.11(17) . . . . ? C13 N2 C14 N4 -58.15(17) . . . . ? C10 N4 C14 N2 -60.50(17) . . . . ? C12 N4 C14 N2 57.67(17) . . . . ? C13 N2 C15 N3 58.97(17) . . . . ? C14 N2 C15 N3 -59.53(17) . . . . ? C10 N3 C15 N2 59.19(16) . . . . ? C11 N3 C15 N2 -58.89(17) . . . . ? 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 H2O O5 1.02 1.69 2.6271(14) 174.0 3_545 O4 H4O O6 1.02 1.57 2.5868(16) 171.9 2_644 N3 H3N O5 1.01 1.71 2.7036(16) 166.2 . _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.325 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.093 #===END