# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Ashwini Nangia' _publ_contact_author_email ASHWINI.NANGIA@GMAIL.COM _publ_section_title ; Molecular networks. Design and serendipity ; loop_ _publ_author_name 'Ashwini Nangia' 'Balakrishna R. Bhogala' 'Shreekanth K. Chandran' 'L. Sreenivas Reddy' # Attachment '34PyrU hydrate_2.cif' data_3,4PyrUhydrate _database_code_depnum_ccdc_archive 'CCDC 689570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 N4 O, (H2 O)' _chemical_formula_sum 'C11 H12 N4 O2' _chemical_formula_weight 232.25 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.0172(14) _cell_length_b 10.343(2) _cell_length_c 15.516(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1126.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 886 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 21.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6456 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.17 _reflns_number_total 1317 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.1916P] 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 1317 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.329 _refine_ls_restrained_S_all 1.329 _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 0.4047(6) 0.7356(4) 0.3654(2) 0.0196(9) Uani 1 1 d . . . H1 H 0.3569 0.7932 0.4061 0.024 Uiso 1 1 calc R . . C2 C 0.5841(6) 0.6858(4) 0.3793(2) 0.0189(9) Uani 1 1 d . . . H2 H 0.6548 0.7095 0.4275 0.023 Uiso 1 1 calc R . . C3 C 0.6563(5) 0.5991(4) 0.3192(2) 0.0177(9) Uani 1 1 d . . . C4 C 0.5425(6) 0.5681(4) 0.2480(3) 0.0187(9) Uani 1 1 d . . . H4 H 0.5857 0.5105 0.2063 0.022 Uiso 1 1 calc R . . C5 C 0.3667(6) 0.6240(4) 0.2411(2) 0.0187(9) Uani 1 1 d . . . H5 H 0.2923 0.6027 0.1936 0.022 Uiso 1 1 calc R . . C6 C 0.9527(5) 0.5389(4) 0.3949(2) 0.0190(9) Uani 1 1 d . . . C7 C 1.2574(5) 0.4379(4) 0.4350(2) 0.0143(8) Uani 1 1 d . . . C8 C 1.2831(6) 0.4990(4) 0.5140(2) 0.0197(9) Uani 1 1 d . . . H8 H 1.1869 0.5530 0.5341 0.024 Uiso 1 1 calc R . . C9 C 1.5739(6) 0.4062(4) 0.5334(3) 0.0260(10) Uani 1 1 d . . . H9 H 1.6834 0.3959 0.5664 0.031 Uiso 1 1 calc R . . C10 C 1.5607(6) 0.3392(4) 0.4565(3) 0.0244(10) Uani 1 1 d . . . H10 H 1.6579 0.2841 0.4389 0.029 Uiso 1 1 calc R . . C11 C 1.4013(6) 0.3560(4) 0.4068(2) 0.0190(9) Uani 1 1 d . . . H11 H 1.3895 0.3129 0.3545 0.023 Uiso 1 1 calc R . . H1A H 0.925(10) 0.309(7) 0.206(4) 0.09(2) Uiso 1 1 d . . . H1B H 1.039(6) 0.401(4) 0.163(3) 0.018(11) Uiso 1 1 d . . . H2N H 0.867(5) 0.492(3) 0.280(2) 0.004(9) Uiso 1 1 d . . . H3N H 1.102(5) 0.415(4) 0.331(2) 0.009(10) Uiso 1 1 d . . . N1 N 0.2950(5) 0.7075(3) 0.2983(2) 0.0180(8) Uani 1 1 d . . . N2 N 0.8300(5) 0.5378(3) 0.3253(2) 0.0185(8) Uani 1 1 d . . . N3 N 1.0977(5) 0.4531(3) 0.3828(2) 0.0171(7) Uani 1 1 d . . . N4 N 1.4386(5) 0.4844(3) 0.5624(2) 0.0217(8) Uani 1 1 d . . . O1 O 1.0227(4) 0.3629(3) 0.2132(2) 0.0221(7) Uani 1 1 d . . . O2 O 0.9318(4) 0.6051(3) 0.45827(17) 0.0271(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(2) 0.015(2) 0.021(2) -0.0050(16) 0.0000(19) -0.0028(18) C2 0.017(2) 0.019(2) 0.020(2) -0.0010(17) -0.0026(18) -0.0040(18) C3 0.016(2) 0.017(2) 0.020(2) 0.0042(17) 0.0016(16) -0.0043(16) C4 0.020(2) 0.017(2) 0.0197(19) -0.0014(17) 0.0011(18) -0.0007(17) C5 0.019(2) 0.020(2) 0.017(2) 0.0019(17) -0.0018(16) -0.0073(17) C6 0.015(2) 0.024(2) 0.018(2) -0.0032(18) 0.0038(18) -0.0046(18) C7 0.014(2) 0.013(2) 0.0162(19) 0.0043(16) 0.0050(16) -0.0033(16) C8 0.020(2) 0.019(2) 0.020(2) 0.0021(17) 0.0015(18) -0.0003(18) C9 0.019(2) 0.034(3) 0.024(2) 0.0085(19) -0.0066(19) -0.004(2) C10 0.020(2) 0.025(2) 0.028(2) 0.0037(19) -0.001(2) 0.0069(19) C11 0.022(2) 0.017(2) 0.0184(19) -0.0010(17) 0.0008(18) -0.0026(18) N1 0.0188(17) 0.0175(18) 0.0176(18) -0.0001(14) 0.0015(16) 0.0005(15) N2 0.0177(18) 0.0242(19) 0.0136(17) -0.0058(16) -0.0003(14) 0.0012(15) N3 0.0168(18) 0.0222(18) 0.0124(16) -0.0057(15) -0.0014(15) 0.0001(14) N4 0.0188(17) 0.028(2) 0.0187(17) 0.0036(15) -0.0028(15) 0.0044(16) O1 0.0196(17) 0.0299(18) 0.0168(15) -0.0036(14) 0.0009(12) -0.0027(14) O2 0.0208(16) 0.0394(19) 0.0212(15) -0.0146(14) -0.0042(13) 0.0076(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.327(5) . ? C1 C2 1.377(6) . ? C1 H1 0.9300 . ? C2 C3 1.390(6) . ? C2 H2 0.9300 . ? C3 N2 1.377(5) . ? C3 C4 1.401(5) . ? C4 C5 1.367(6) . ? C4 H4 0.9300 . ? C5 N1 1.337(5) . ? C5 H5 0.9300 . ? C6 O2 1.206(4) . ? C6 N3 1.364(5) . ? C6 N2 1.381(5) . ? C7 C11 1.389(5) . ? C7 C8 1.390(5) . ? C7 N3 1.392(5) . ? C8 N4 1.333(5) . ? C8 H8 0.9300 . ? C9 N4 1.326(5) . ? C9 C10 1.383(6) . ? C9 H9 0.9300 . ? C10 C11 1.369(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N2 H2N 0.89(3) . ? N3 H3N 0.89(4) . ? O1 H1A 0.89(7) . ? O1 H1B 0.87(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.9(4) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? C1 C2 C3 118.0(4) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? N2 C3 C2 125.0(4) . . ? N2 C3 C4 117.0(4) . . ? C2 C3 C4 118.0(4) . . ? C5 C4 C3 118.6(4) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 124.1(4) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? O2 C6 N3 124.9(4) . . ? O2 C6 N2 124.5(4) . . ? N3 C6 N2 110.6(3) . . ? C11 C7 C8 117.4(4) . . ? C11 C7 N3 118.0(3) . . ? C8 C7 N3 124.5(4) . . ? N4 C8 C7 123.5(4) . . ? N4 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? N4 C9 C10 123.4(4) . . ? N4 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C11 C10 C9 118.5(4) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C7 119.6(4) . . ? C10 C11 H11 120.2 . . ? C7 C11 H11 120.2 . . ? C1 N1 C5 116.4(3) . . ? C3 N2 C6 127.0(3) . . ? C3 N2 H2N 117(2) . . ? C6 N2 H2N 116(2) . . ? C6 N3 C7 126.4(3) . . ? C6 N3 H3N 116(2) . . ? C7 N3 H3N 116(3) . . ? C9 N4 C8 117.6(3) . . ? H1A O1 H1B 106(5) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.266 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.059 # Attachment 'H3CTA.3H-pyr.cif' data_H3CTA.(3H-pyr)2 _database_code_depnum_ccdc_archive 'CCDC 689571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - [4(3H)-pyrimidone]2 ; _chemical_melting_point ? _chemical_formula_moiety (C9H12O6),2(C4H4N2O) _chemical_formula_sum 'C17 H20 N4 O8' _chemical_formula_weight 408.37 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' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3218(14) _cell_length_b 5.7554(6) _cell_length_c 24.093(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.508(2) _cell_angle_gamma 90.00 _cell_volume 1847.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1644 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 22.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9676 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9509 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3603 _reflns_number_gt 2305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3603 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 O11 O 0.38604(13) -0.1179(3) 0.20120(7) 0.0560(5) Uani 1 1 d . . . O12 O 0.11401(13) 0.4020(3) 0.31813(7) 0.0485(5) Uani 1 1 d . . . O10 O 0.33007(14) -0.2311(3) 0.11873(7) 0.0525(5) Uani 1 1 d . . . O14 O 0.02529(14) 0.5769(3) 0.06643(7) 0.0556(5) Uani 1 1 d . . . O15 O 0.05560(14) 0.2431(3) 0.02429(7) 0.0583(5) Uani 1 1 d . . . C6 C 0.19604(17) 0.1484(4) 0.11322(9) 0.0368(6) Uani 1 1 d . . . H6A H 0.1922 0.0308 0.0844 0.044 Uiso 1 1 calc R . . H6B H 0.2447 0.2644 0.1021 0.044 Uiso 1 1 calc R . . N25 N 0.25702(16) 0.4323(4) 0.90593(8) 0.0436(5) Uani 1 1 d . . . C1 C 0.22921(17) 0.0374(4) 0.16784(9) 0.0378(6) Uani 1 1 d . . . H1 H 0.1760 -0.0730 0.1772 0.045 Uiso 1 1 calc R . . C8 C 0.13335(18) 0.4930(4) 0.26930(9) 0.0400(6) Uani 1 1 d . . . C7 C 0.32428(17) -0.1062(4) 0.16432(9) 0.0378(6) Uani 1 1 d . . . N23 N 0.16768(15) 0.7790(4) 0.89825(8) 0.0446(5) Uani 1 1 d . . . C9 C 0.05674(17) 0.3733(5) 0.06726(9) 0.0385(6) Uani 1 1 d . . . C2 C 0.23217(17) 0.2097(4) 0.21507(9) 0.0380(6) Uani 1 1 d . . . H2A H 0.2811 0.3299 0.2073 0.046 Uiso 1 1 calc R . . H2B H 0.2525 0.1315 0.2490 0.046 Uiso 1 1 calc R . . C24 C 0.20131(18) 0.5866(4) 0.87785(10) 0.0428(6) Uani 1 1 d . . . H24 H 0.1856 0.5531 0.8410 0.051 Uiso 1 1 calc R . . O13 O 0.1548(2) 0.6928(3) 0.26378(7) 0.0839(8) Uani 1 1 d . . . C4 C 0.09209(18) 0.4312(4) 0.16891(9) 0.0406(6) Uani 1 1 d . . . H4A H 0.0244 0.4890 0.1739 0.049 Uiso 1 1 calc R . . H4B H 0.1348 0.5627 0.1604 0.049 Uiso 1 1 calc R . . C5 C 0.09285(17) 0.2625(4) 0.12043(9) 0.0385(6) Uani 1 1 d . . . H5 H 0.0454 0.1380 0.1292 0.046 Uiso 1 1 calc R . . C3 C 0.12834(18) 0.3201(4) 0.22269(9) 0.0398(6) Uani 1 1 d . . . H3 H 0.0809 0.1974 0.2328 0.048 Uiso 1 1 calc R . . C26 C 0.2865(2) 0.4644(5) 0.96065(10) 0.0494(7) Uani 1 1 d . . . O29 O 0.33992(16) 0.3200(4) 0.98382(8) 0.0764(7) Uani 1 1 d . . . C28 C 0.1930(2) 0.8199(5) 0.95243(10) 0.0489(7) Uani 1 1 d . . . H28 H 0.1707 0.9568 0.9687 0.059 Uiso 1 1 calc R . . C27 C 0.2481(2) 0.6741(5) 0.98347(10) 0.0544(7) Uani 1 1 d . . . H27 H 0.2615 0.7103 1.0204 0.065 Uiso 1 1 calc R . . O22 O 0.34486(13) 0.4042(3) 0.33598(7) 0.0539(5) Uani 1 1 d . . . C19 C 0.39915(17) 0.5668(4) 0.35020(10) 0.0396(6) Uani 1 1 d . . . N16 N 0.52507(15) 0.9498(4) 0.37231(8) 0.0491(6) Uani 1 1 d . . . N18 N 0.41502(15) 0.7513(4) 0.31412(8) 0.0435(5) Uani 1 1 d . . . C20 C 0.45050(18) 0.5942(4) 0.40175(10) 0.0446(6) Uani 1 1 d . . . H20 H 0.4424 0.4841 0.4296 0.054 Uiso 1 1 calc R . . C21 C 0.51068(19) 0.7781(5) 0.41053(10) 0.0497(7) Uani 1 1 d . . . H21 H 0.5443 0.7891 0.4444 0.060 Uiso 1 1 calc R . . C17 C 0.47661(18) 0.9290(5) 0.32582(10) 0.0461(6) Uani 1 1 d . . . H17 H 0.4850 1.0437 0.2991 0.055 Uiso 1 1 calc R . . H18 H 0.3853(17) 0.742(4) 0.2787(10) 0.042(6) Uiso 1 1 d . . . H25 H 0.2840(19) 0.304(5) 0.8868(11) 0.055(8) Uiso 1 1 d . . . H12 H 0.135(2) 0.514(5) 0.3464(13) 0.084(10) Uiso 1 1 d . . . H10 H 0.385(2) -0.341(6) 0.1231(12) 0.084(10) Uiso 1 1 d . . . H15 H 0.018(3) 0.338(7) -0.0198(17) 0.134(13) 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 O11 0.0492(11) 0.0799(14) 0.0386(9) -0.0074(9) -0.0104(8) 0.0209(10) O12 0.0575(11) 0.0565(12) 0.0316(9) -0.0029(9) 0.0041(8) -0.0110(9) O10 0.0572(12) 0.0586(12) 0.0416(10) -0.0122(9) -0.0105(8) 0.0275(10) O14 0.0767(13) 0.0503(12) 0.0395(10) 0.0005(9) -0.0111(9) 0.0184(10) O15 0.0734(13) 0.0665(13) 0.0349(10) -0.0094(9) -0.0141(9) 0.0267(10) C6 0.0386(13) 0.0414(14) 0.0304(11) -0.0022(11) -0.0019(9) 0.0073(11) N25 0.0513(13) 0.0438(13) 0.0355(11) -0.0025(10) -0.0026(9) 0.0075(11) C1 0.0401(14) 0.0401(14) 0.0333(12) 0.0011(10) -0.0029(10) 0.0052(11) C8 0.0492(15) 0.0367(15) 0.0339(13) 0.0003(11) -0.0047(11) 0.0035(12) C7 0.0430(14) 0.0416(14) 0.0287(12) 0.0037(11) -0.0015(10) 0.0054(11) N23 0.0473(13) 0.0466(13) 0.0398(11) 0.0019(10) 0.0025(9) 0.0055(10) C9 0.0350(13) 0.0463(16) 0.0342(13) -0.0041(11) -0.0025(10) 0.0082(11) C2 0.0435(14) 0.0427(14) 0.0277(11) 0.0022(10) -0.0044(10) 0.0012(11) C24 0.0487(15) 0.0474(16) 0.0323(12) 0.0019(11) -0.0014(11) 0.0017(13) O13 0.176(3) 0.0406(13) 0.0353(11) -0.0003(9) -0.0049(12) -0.0152(13) C4 0.0448(14) 0.0433(15) 0.0337(12) -0.0039(11) -0.0037(10) 0.0083(11) C5 0.0400(14) 0.0436(14) 0.0318(12) -0.0007(11) -0.0022(10) 0.0042(11) C3 0.0439(14) 0.0435(15) 0.0320(12) -0.0019(11) -0.0001(10) 0.0010(11) C26 0.0540(16) 0.0558(17) 0.0381(14) 0.0034(13) -0.0060(12) 0.0026(14) O29 0.0951(17) 0.0753(15) 0.0584(13) 0.0018(11) -0.0281(11) 0.0256(13) C28 0.0563(16) 0.0489(16) 0.0415(14) -0.0062(12) 0.0062(12) 0.0056(13) C27 0.0681(19) 0.0636(19) 0.0316(13) -0.0080(13) -0.0048(12) 0.0039(15) O22 0.0556(12) 0.0508(12) 0.0550(11) 0.0024(9) -0.0099(9) -0.0165(9) C19 0.0355(13) 0.0415(15) 0.0419(13) 0.0025(11) -0.0002(10) -0.0030(11) N16 0.0474(13) 0.0533(14) 0.0465(12) 0.0034(11) -0.0036(10) -0.0164(11) N18 0.0476(13) 0.0455(13) 0.0371(11) 0.0028(10) -0.0082(9) -0.0049(10) C20 0.0445(15) 0.0491(16) 0.0403(13) 0.0091(12) -0.0029(11) -0.0067(12) C21 0.0492(16) 0.0607(18) 0.0389(14) 0.0035(13) -0.0100(11) -0.0105(14) C17 0.0478(15) 0.0466(16) 0.0440(14) 0.0069(12) 0.0030(11) -0.0099(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 O11 C7 1.207(2) . ? O12 C8 1.315(3) . ? O12 H12 0.98(3) . ? O10 C7 1.316(3) . ? O10 H10 0.98(3) . ? O14 C9 1.245(3) . ? O15 C9 1.278(3) . ? O15 H15 1.29(4) . ? C6 C1 1.525(3) . ? C6 C5 1.535(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N25 C24 1.337(3) . ? N25 C26 1.385(3) . ? N25 H25 0.94(3) . ? C1 C2 1.510(3) . ? C1 C7 1.515(3) . ? C1 H1 0.9800 . ? C8 O13 1.193(3) . ? C8 C3 1.502(3) . ? N23 C24 1.293(3) . ? N23 C28 1.366(3) . ? C9 C5 1.506(3) . ? C2 C3 1.535(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C24 H24 0.9300 . ? C4 C5 1.519(3) . ? C4 C3 1.520(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5 0.9800 . ? C3 H3 0.9800 . ? C26 O29 1.225(3) . ? C26 C27 1.423(4) . ? C28 C27 1.339(4) . ? C28 H28 0.9300 . ? C27 H27 0.9300 . ? O22 C19 1.229(3) . ? C19 N18 1.390(3) . ? C19 C20 1.421(3) . ? N16 C17 1.293(3) . ? N16 C21 1.365(3) . ? N18 C17 1.340(3) . ? N18 H18 0.94(2) . ? C20 C21 1.343(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C17 H17 0.9300 . ? 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 O12 H12 107.5(18) . . ? C7 O10 H10 108.3(17) . . ? C9 O15 H15 115.0(17) . . ? C1 C6 C5 109.55(18) . . ? C1 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C1 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C24 N25 C26 123.0(2) . . ? C24 N25 H25 119.0(15) . . ? C26 N25 H25 117.6(15) . . ? C2 C1 C7 112.60(18) . . ? C2 C1 C6 112.37(19) . . ? C7 C1 C6 114.59(19) . . ? C2 C1 H1 105.4 . . ? C7 C1 H1 105.4 . . ? C6 C1 H1 105.4 . . ? O13 C8 O12 122.2(2) . . ? O13 C8 C3 124.4(2) . . ? O12 C8 C3 113.4(2) . . ? O11 C7 O10 122.6(2) . . ? O11 C7 C1 123.6(2) . . ? O10 C7 C1 113.57(18) . . ? C24 N23 C28 115.3(2) . . ? O14 C9 O15 122.5(2) . . ? O14 C9 C5 121.1(2) . . ? O15 C9 C5 116.3(2) . . ? C1 C2 C3 110.16(18) . . ? 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 . . ? N23 C24 N25 124.7(2) . . ? N23 C24 H24 117.7 . . ? N25 C24 H24 117.7 . . ? C5 C4 C3 112.47(19) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C9 C5 C4 112.29(19) . . ? C9 C5 C6 111.38(18) . . ? C4 C5 C6 111.88(18) . . ? C9 C5 H5 107.0 . . ? C4 C5 H5 107.0 . . ? C6 C5 H5 107.0 . . ? C8 C3 C4 111.7(2) . . ? C8 C3 C2 109.25(18) . . ? C4 C3 C2 110.61(19) . . ? C8 C3 H3 108.4 . . ? C4 C3 H3 108.4 . . ? C2 C3 H3 108.4 . . ? O29 C26 N25 120.1(3) . . ? O29 C26 C27 127.5(2) . . ? N25 C26 C27 112.4(2) . . ? C27 C28 N23 123.7(2) . . ? C27 C28 H28 118.1 . . ? N23 C28 H28 118.1 . . ? C28 C27 C26 120.8(2) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? O22 C19 N18 120.0(2) . . ? O22 C19 C20 127.3(2) . . ? N18 C19 C20 112.8(2) . . ? C17 N16 C21 116.4(2) . . ? C17 N18 C19 123.2(2) . . ? C17 N18 H18 119.1(14) . . ? C19 N18 H18 117.5(14) . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 N16 123.4(2) . . ? C20 C21 H21 118.3 . . ? N16 C21 H21 118.3 . . ? N16 C17 N18 123.6(2) . . ? N16 C17 H17 118.2 . . ? N18 C17 H17 118.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.245 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.054 _chemical_name_common ;cis,cis-1,3,5-cyclohexanetricarboxylic acid - (4(3H)- pyrimidone)2 ;