Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'J.Chem.Soc.,Dalton Trans.' loop_ _publ_author_name 'Natarajan, Srinivasan'' 'Rao, C. N. R.' 'Vaidhyanathan, R.' _publ_contact_author_name 'Prof C N R Rao' _publ_contact_author_address ; Prof C N R Rao Chemistry & Physics of Materials Unit Jawaharlal Nehru Centre for Advanced Scientific Research Jaakur P.O. Bangalore 560 064 INDIA ; _publ_contact_author_email 'raj@jncasr.ac.in' ********************************************************************* #compound I (monomer) data_test_compound_I_(monomer) _database_code_CSD 151822 _audit_creation_method SHELXL _chemical_name_systematic ; 'zinc oxalate monomer with guanidine' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C3 H8 N3 O5 Zn0.50' _chemical_formula_weight 198.81 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 '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 14.170(2) _cell_length_b 10.1285(12) _cell_length_c 11.3243(14) _cell_angle_alpha 90.00 _cell_angle_beta 115.397(2) _cell_angle_gamma 90.00 _cell_volume 1468.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method ? _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.739 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3002 _diffrn_reflns_av_R_equivalents 0.1036 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 23.26 _reflns_number_total 1053 _reflns_number_observed 916 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0282P)^2^+4.3311P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1051 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_obs 0.0443 _refine_ls_wR_factor_all 0.1089 _refine_ls_wR_factor_obs 0.0986 _refine_ls_goodness_of_fit_all 1.136 _refine_ls_goodness_of_fit_obs 1.126 _refine_ls_restrained_S_all 1.151 _refine_ls_restrained_S_obs 1.126 _refine_ls_shift/esd_max -3.654 _refine_ls_shift/esd_mean 0.033 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.5000 0.82872(7) 0.7500 0.0277(3) Uani 1 d S . O1 O 0.4236(3) 0.6782(3) 0.6183(3) 0.0333(8) Uani 1 d . . O2 O 0.5774(2) 0.9378(3) 0.9230(3) 0.0317(8) Uani 1 d . . O3 O 0.6303(3) 0.8452(4) 0.7005(4) 0.0320(9) Uani 1 d . . C1 C 0.3767(3) 0.7156(4) 0.5016(5) 0.0276(11) Uani 1 d . . O4 O 0.3273(3) 0.6400(3) 0.4070(3) 0.0383(9) Uani 1 d . . C2 C 0.6189(4) 0.8666(5) 1.0242(5) 0.0282(11) Uani 1 d . . O5 O 0.6552(3) 0.9039(3) 1.1393(3) 0.0407(9) Uani 1 d . . C10 C 0.3770(3) 0.3250(4) 0.6038(5) 0.0308(11) Uani 1 d . . N1 N 0.3937(3) 0.3563(4) 0.5011(4) 0.0436(11) Uani 1 d . . H1 H 0.3969(3) 0.4379(4) 0.4820(4) 0.052 Uiso 1 calc R . H2 H 0.4014(3) 0.2951(4) 0.4533(4) 0.052 Uiso 1 calc R . N2 N 0.3651(3) 0.4195(4) 0.6777(4) 0.0427(11) Uani 1 d . . H3 H 0.3683(3) 0.5011(4) 0.6587(4) 0.051 Uiso 1 calc R . H4 H 0.3543(3) 0.3991(4) 0.7446(4) 0.051 Uiso 1 calc R . N3 N 0.3694(3) 0.1996(4) 0.6331(4) 0.0431(11) Uani 1 d . . H5 H 0.3753(3) 0.1375(4) 0.5849(4) 0.052 Uiso 1 calc R . H6 H 0.3585(3) 0.1805(4) 0.7003(4) 0.052 Uiso 1 calc R . H10 H 0.6389(36) 0.9213(55) 0.6831(49) 0.030(14) Uiso 1 d . . H11 H 0.6801(49) 0.8335(55) 0.7521(63) 0.041(20) 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 Zn1 0.0347(5) 0.0253(5) 0.0167(5) 0.000 0.0050(4) 0.000 O1 0.046(2) 0.027(2) 0.017(2) -0.0019(14) 0.004(2) -0.006(2) O2 0.037(2) 0.026(2) 0.025(2) -0.0003(15) 0.006(2) -0.0003(15) O3 0.031(2) 0.034(2) 0.028(2) 0.005(2) 0.009(2) -0.001(2) C1 0.024(2) 0.031(2) 0.026(3) -0.002(2) 0.008(2) 0.000(2) O4 0.043(2) 0.038(2) 0.024(2) -0.004(2) 0.006(2) -0.006(2) C2 0.026(2) 0.033(3) 0.023(3) -0.001(2) 0.008(2) -0.003(2) O5 0.056(2) 0.036(2) 0.020(2) -0.006(2) 0.007(2) -0.002(2) C10 0.030(3) 0.031(2) 0.029(3) -0.004(2) 0.011(2) 0.003(2) N1 0.061(3) 0.040(2) 0.039(3) -0.006(2) 0.030(2) -0.004(2) N2 0.062(3) 0.035(2) 0.042(3) 0.000(2) 0.032(2) -0.001(2) N3 0.063(3) 0.028(2) 0.035(2) 0.004(2) 0.018(2) -0.001(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 Zn1 O1 2.082(3) . ? Zn1 O1 2.082(3) 2_656 ? Zn1 O2 2.102(3) 2_656 ? Zn1 O2 2.102(3) . ? Zn1 O3 2.154(4) . ? Zn1 O3 2.154(4) 2_656 ? O1 C1 1.256(5) . ? O2 C2 1.265(5) . ? O3 H10 0.82(5) . ? O3 H11 0.71(6) . ? C1 O4 1.257(5) . ? C1 C2 1.563(6) 2_656 ? C2 O5 1.238(6) . ? C2 C1 1.563(6) 2_656 ? C10 N1 1.321(6) . ? C10 N2 1.329(6) . ? C10 N3 1.329(6) . ? N1 H1 0.86 . ? N1 H2 0.86 . ? N2 H3 0.86 . ? N2 H4 0.86 . ? N3 H5 0.86 . ? N3 H6 0.86 . ? 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 Zn1 O1 85.9(2) . 2_656 ? O1 Zn1 O2 79.28(11) . 2_656 ? O1 Zn1 O2 162.86(12) 2_656 2_656 ? O1 Zn1 O2 162.86(12) . . ? O1 Zn1 O2 79.28(11) 2_656 . ? O2 Zn1 O2 116.6(2) 2_656 . ? O1 Zn1 O3 96.37(14) . . ? O1 Zn1 O3 90.2(2) 2_656 . ? O2 Zn1 O3 83.09(14) 2_656 . ? O2 Zn1 O3 92.22(13) . . ? O1 Zn1 O3 90.2(2) . 2_656 ? O1 Zn1 O3 96.36(14) 2_656 2_656 ? O2 Zn1 O3 92.22(13) 2_656 2_656 ? O2 Zn1 O3 83.09(14) . 2_656 ? O3 Zn1 O3 171.1(2) . 2_656 ? C1 O1 Zn1 114.3(3) . . ? C2 O2 Zn1 113.5(3) . . ? Zn1 O3 H10 111.6(33) . . ? Zn1 O3 H11 115.7(49) . . ? H10 O3 H11 99.2(57) . . ? O1 C1 O4 124.3(4) . . ? O1 C1 C2 116.4(4) . 2_656 ? O4 C1 C2 119.3(4) . 2_656 ? O5 C2 O2 127.0(4) . . ? O5 C2 C1 117.6(4) . 2_656 ? O2 C2 C1 115.4(4) . 2_656 ? N1 C10 N2 120.1(4) . . ? N1 C10 N3 120.9(4) . . ? N2 C10 N3 119.0(4) . . ? C10 N1 H1 120.0(3) . . ? C10 N1 H2 120.0(3) . . ? H1 N1 H2 120.0 . . ? C10 N2 H3 120.0(3) . . ? C10 N2 H4 120.0(3) . . ? H3 N2 H4 120.0 . . ? C10 N3 H5 120.0(3) . . ? C10 N3 H6 120.0(3) . . ? H5 N3 H6 120.0 . . ? _refine_diff_density_max 0.394 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.112 #Compound II (Dimer) data_try_Compound_II_(Dimer) _database_code_CSD 151823 _audit_creation_method SHELXL _chemical_name_systematic ; 'Zinc oxalate dimer with piperazine' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H18 N3 O14 Zn' _chemical_formula_weight 481.65 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 '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 13.7897(4) _cell_length_b 11.5242(3) _cell_length_c 25.4119(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.1930(10) _cell_angle_gamma 90.00 _cell_volume 3897.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method ? _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 1.337 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7750 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 23.28 _reflns_number_total 2758 _reflns_number_observed 2421 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0575P)^2^+17.9514P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2757 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_obs 0.0417 _refine_ls_wR_factor_all 0.1242 _refine_ls_wR_factor_obs 0.1157 _refine_ls_goodness_of_fit_all 1.108 _refine_ls_goodness_of_fit_obs 1.112 _refine_ls_restrained_S_all 1.110 _refine_ls_restrained_S_obs 1.112 _refine_ls_shift/esd_max 0.006 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.11635(3) 1.09492(4) 0.85367(2) 0.0269(2) Uani 1 d . . O1 O 0.1770(2) 1.2488(3) 0.88640(12) 0.0391(8) Uani 1 d . . O2 O 0.0706(2) 0.9275(3) 0.83026(13) 0.0363(8) Uani 1 d . . O3 O 0.1310(3) 0.7523(3) 0.8211(2) 0.0651(12) Uani 1 d . . C1 C 0.1575(3) 1.2766(4) 0.9313(2) 0.0307(10) Uani 1 d . . C2 C 0.1413(3) 0.8564(4) 0.8341(2) 0.0358(11) Uani 1 d . . O4 O 0.0750(2) 1.0925(2) 0.92726(12) 0.0349(8) Uani 1 d . . O5 O 0.2557(2) 1.0100(3) 0.87156(12) 0.0362(8) Uani 1 d . . O6 O 0.0616(2) 1.2164(3) 0.99285(13) 0.0399(8) Uani 1 d . . O7 O 0.1849(3) 1.3662(3) 0.95750(14) 0.0470(9) Uani 1 d . . O8 O 0.3224(3) 0.8410(3) 0.8573(2) 0.0571(10) Uani 1 d . . C3 C 0.0922(3) 1.1879(4) 0.9529(2) 0.0280(10) Uani 1 d . . C4 C 0.2508(3) 0.9048(4) 0.8563(2) 0.0339(11) Uani 1 d . . O9 O -0.0345(2) 1.1474(3) 0.81167(11) 0.0300(7) Uani 1 d . . O10 O 0.1312(2) 1.1460(3) 0.77422(12) 0.0336(7) Uani 1 d . . C5 C -0.0478(3) 1.1469(3) 0.7604(2) 0.0256(9) Uani 1 d . . C6 C 0.8144(5) 1.0271(5) 0.8899(2) 0.057(2) Uani 1 d . . H1 H 0.7551(5) 1.0051(5) 0.9013(2) 0.069 Uiso 1 calc R . H2 H 0.8549(5) 1.0778(5) 0.9175(2) 0.069 Uiso 1 calc R . C7 C 0.7236(4) 1.0132(5) 0.7927(2) 0.0499(13) Uani 1 d . . H3 H 0.7066(4) 1.0552(5) 0.7584(2) 0.060 Uiso 1 calc R . H4 H 0.6616(4) 0.9909(5) 0.8012(2) 0.060 Uiso 1 calc R . N1 N 0.7837(3) 1.0898(3) 0.8369(2) 0.0488(12) Uani 1 d . . H5 H 0.8389(3) 1.1148(3) 0.8277(2) 0.059 Uiso 1 calc R . H6 H 0.7469(3) 1.1524(3) 0.8405(2) 0.059 Uiso 1 calc R . C8 C 0.7828(4) 0.9068(4) 0.7874(2) 0.0419(12) Uani 1 d . . H7 H 0.7417(4) 0.8557(4) 0.7601(2) 0.050 Uiso 1 calc R . H8 H 0.8412(4) 0.9289(4) 0.7752(2) 0.050 Uiso 1 calc R . C9 C 0.8734(4) 0.9212(5) 0.8847(2) 0.0494(14) Uani 1 d . . H9 H 0.9360(4) 0.9438(5) 0.8769(2) 0.059 Uiso 1 calc R . H10 H 0.8895(4) 0.8791(5) 0.9189(2) 0.059 Uiso 1 calc R . N2 N 0.8159(3) 0.8439(3) 0.8403(2) 0.0363(9) Uani 1 d . . H11 H 0.8547(3) 0.7834(3) 0.8365(2) 0.044 Uiso 1 calc R . H12 H 0.7616(3) 0.8159(3) 0.8495(2) 0.044 Uiso 1 calc R . C10 C 1.0143(4) 0.5663(5) 0.9543(2) 0.0421(12) Uani 1 d . . H14 H 1.0176(4) 0.6409(5) 0.9372(2) 0.051 Uiso 1 calc R . H13 H 1.0272(4) 0.5063(5) 0.9302(2) 0.051 Uiso 1 calc R . C11 C 0.9061(4) 0.4391(4) 0.9914(2) 0.0425(12) Uani 1 d . . H18 H 0.9151(4) 0.3744(4) 0.9688(2) 0.051 Uiso 1 calc R . H17 H 0.8399(4) 0.4326(4) 0.9977(2) 0.051 Uiso 1 calc R . N3 N 0.9133(3) 0.5498(3) 0.9627(2) 0.0384(10) Uani 1 d . . H15 H 0.8673(3) 0.5498(3) 0.9302(2) 0.046 Uiso 1 calc R . H16 H 0.8993(3) 0.6093(3) 0.9824(2) 0.046 Uiso 1 calc R . O100 O 0.1074(3) 0.8706(4) 0.9789(2) 0.0711(12) Uani 1 d . . O200 O 0.9409(3) 0.6771(4) 0.8146(3) 0.094(2) Uani 1 d . . O300 O 0.4780(4) 0.9326(4) 0.8114(3) 0.114(2) Uani 1 d . . O400 O 0.2210(9) 0.7184(10) 0.9433(4) 0.216(5) Uani 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 Zn1 0.0265(3) 0.0272(3) 0.0261(3) -0.0026(2) 0.0051(2) -0.0024(2) O1 0.052(2) 0.037(2) 0.036(2) -0.0111(15) 0.024(2) -0.019(2) O2 0.026(2) 0.032(2) 0.048(2) -0.0061(15) 0.0037(14) -0.0018(14) O3 0.038(2) 0.026(2) 0.119(4) -0.020(2) 0.000(2) 0.001(2) C1 0.030(2) 0.030(3) 0.033(3) -0.002(2) 0.011(2) -0.002(2) C2 0.029(2) 0.035(3) 0.040(3) 0.002(2) 0.002(2) 0.002(2) O4 0.047(2) 0.030(2) 0.030(2) -0.0021(14) 0.0144(15) -0.0103(14) O5 0.028(2) 0.034(2) 0.039(2) -0.0072(15) -0.0036(14) -0.0007(14) O6 0.052(2) 0.039(2) 0.037(2) -0.0024(15) 0.026(2) -0.002(2) O7 0.058(2) 0.036(2) 0.054(2) -0.019(2) 0.026(2) -0.017(2) O8 0.032(2) 0.048(2) 0.087(3) -0.011(2) 0.007(2) 0.009(2) C3 0.026(2) 0.027(2) 0.028(2) 0.003(2) 0.003(2) 0.000(2) C4 0.032(3) 0.031(3) 0.035(3) 0.001(2) 0.002(2) 0.002(2) O9 0.030(2) 0.037(2) 0.024(2) 0.0017(13) 0.0081(13) 0.0040(13) O10 0.022(2) 0.048(2) 0.030(2) -0.0006(14) 0.0058(14) -0.0014(14) C5 0.025(2) 0.019(2) 0.035(3) -0.001(2) 0.012(2) 0.001(2) C6 0.069(4) 0.060(4) 0.055(4) -0.023(3) 0.037(3) -0.023(3) C7 0.041(3) 0.046(3) 0.060(3) 0.017(3) 0.008(2) -0.001(2) N1 0.046(3) 0.027(2) 0.086(3) 0.000(2) 0.040(2) 0.002(2) C8 0.049(3) 0.041(3) 0.036(3) -0.002(2) 0.012(2) -0.011(2) C9 0.041(3) 0.069(4) 0.035(3) 0.015(3) 0.004(2) -0.011(3) N2 0.038(2) 0.029(2) 0.048(2) 0.007(2) 0.022(2) 0.004(2) C10 0.042(3) 0.044(3) 0.036(3) -0.005(2) 0.003(2) 0.002(2) C11 0.036(3) 0.042(3) 0.045(3) -0.008(2) 0.003(2) 0.000(2) N3 0.037(2) 0.040(2) 0.031(2) -0.011(2) -0.004(2) 0.009(2) O100 0.058(2) 0.068(3) 0.084(3) 0.027(2) 0.012(2) 0.003(2) O200 0.043(2) 0.045(2) 0.200(6) -0.032(3) 0.041(3) -0.002(2) O300 0.065(3) 0.058(3) 0.209(7) -0.006(4) 0.020(4) 0.001(2) O400 0.242(12) 0.223(12) 0.195(9) 0.009(8) 0.080(8) -0.029(9) _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 Zn1 O1 2.042(3) . ? Zn1 O2 2.069(3) . ? Zn1 O4 2.093(3) . ? Zn1 O5 2.097(3) . ? Zn1 O9 2.160(3) . ? Zn1 O10 2.164(3) . ? O1 C1 1.279(5) . ? O2 C2 1.257(5) . ? O3 C2 1.242(6) . ? C1 O7 1.233(5) . ? C1 C3 1.555(6) . ? C2 C4 1.569(6) . ? O4 C3 1.268(5) . ? O5 C4 1.269(5) . ? O6 C3 1.242(5) . ? O8 C4 1.226(6) . ? O9 C5 1.268(5) . ? O10 C5 1.252(5) 2_556 ? C5 O10 1.252(5) 2_556 ? C5 C5 1.544(8) 2_556 ? C6 N1 1.488(7) . ? C6 C9 1.491(8) . ? C6 H1 0.97 . ? C6 H2 0.97 . ? C7 N1 1.497(7) . ? C7 C8 1.498(7) . ? C7 H3 0.97 . ? C7 H4 0.97 . ? N1 H5 0.90 . ? N1 H6 0.90 . ? C8 N2 1.490(6) . ? C8 H7 0.97 . ? C8 H8 0.97 . ? C9 N2 1.492(6) . ? C9 H9 0.97 . ? C9 H10 0.97 . ? N2 H11 0.90 . ? N2 H12 0.90 . ? C10 N3 1.477(6) . ? C10 C11 1.522(7) 5_767 ? C10 H14 0.97 . ? C10 H13 0.97 . ? C11 N3 1.485(6) . ? C11 C10 1.522(6) 5_767 ? C11 H18 0.97 . ? C11 H17 0.97 . ? N3 H15 0.90 . ? N3 H16 0.90 . ? 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 Zn1 O2 171.33(13) . . ? O1 Zn1 O4 79.98(11) . . ? O2 Zn1 O4 96.35(12) . . ? O1 Zn1 O5 93.59(13) . . ? O2 Zn1 O5 79.64(12) . . ? O4 Zn1 O5 104.41(13) . . ? O1 Zn1 O9 101.35(13) . . ? O2 Zn1 O9 86.41(12) . . ? O4 Zn1 O9 89.57(12) . . ? O5 Zn1 O9 161.16(11) . . ? O1 Zn1 O10 90.85(12) . . ? O2 Zn1 O10 94.69(12) . . ? O4 Zn1 O10 162.13(12) . . ? O5 Zn1 O10 91.35(12) . . ? O9 Zn1 O10 77.14(10) . . ? C1 O1 Zn1 114.9(3) . . ? C2 O2 Zn1 114.5(3) . . ? O7 C1 O1 125.9(4) . . ? O7 C1 C3 118.9(4) . . ? O1 C1 C3 115.2(4) . . ? O3 C2 O2 125.2(4) . . ? O3 C2 C4 118.1(4) . . ? O2 C2 C4 116.7(4) . . ? C3 O4 Zn1 112.9(3) . . ? C4 O5 Zn1 114.0(3) . . ? O6 C3 O4 126.2(4) . . ? O6 C3 C1 117.9(4) . . ? O4 C3 C1 115.9(4) . . ? O8 C4 O5 126.0(4) . . ? O8 C4 C2 119.2(4) . . ? O5 C4 C2 114.8(4) . . ? C5 O9 Zn1 111.6(2) . . ? C5 O10 Zn1 111.3(3) 2_556 . ? O10 C5 O9 125.5(4) 2_556 . ? O10 C5 C5 118.0(5) 2_556 2_556 ? O9 C5 C5 116.4(5) . 2_556 ? N1 C6 C9 110.5(4) . . ? N1 C6 H1 109.5(3) . . ? C9 C6 H1 109.5(3) . . ? N1 C6 H2 109.5(3) . . ? C9 C6 H2 109.5(3) . . ? H1 C6 H2 108.1 . . ? N1 C7 C8 110.1(4) . . ? N1 C7 H3 109.6(3) . . ? C8 C7 H3 109.6(3) . . ? N1 C7 H4 109.6(3) . . ? C8 C7 H4 109.6(3) . . ? H3 C7 H4 108.2 . . ? C6 N1 C7 111.2(4) . . ? C6 N1 H5 109.4(3) . . ? C7 N1 H5 109.4(3) . . ? C6 N1 H6 109.4(3) . . ? C7 N1 H6 109.4(3) . . ? H5 N1 H6 108.0 . . ? N2 C8 C7 111.2(4) . . ? N2 C8 H7 109.4(2) . . ? C7 C8 H7 109.4(3) . . ? N2 C8 H8 109.4(2) . . ? C7 C8 H8 109.4(3) . . ? H7 C8 H8 108.0 . . ? N2 C9 C6 111.2(4) . . ? N2 C9 H9 109.4(3) . . ? C6 C9 H9 109.4(3) . . ? N2 C9 H10 109.4(2) . . ? C6 C9 H10 109.4(3) . . ? H9 C9 H10 108.0 . . ? C8 N2 C9 111.6(4) . . ? C8 N2 H11 109.3(2) . . ? C9 N2 H11 109.3(3) . . ? C8 N2 H12 109.3(2) . . ? C9 N2 H12 109.3(2) . . ? H11 N2 H12 108.0 . . ? N3 C10 C11 110.3(4) . 5_767 ? N3 C10 H14 109.6(3) . . ? C11 C10 H14 109.6(3) 5_767 . ? N3 C10 H13 109.6(2) . . ? C11 C10 H13 109.6(3) 5_767 . ? H14 C10 H13 108.1 . . ? N3 C11 C10 110.8(4) . 5_767 ? N3 C11 H18 109.5(2) . . ? C10 C11 H18 109.5(3) 5_767 . ? N3 C11 H17 109.5(2) . . ? C10 C11 H17 109.5(3) 5_767 . ? H18 C11 H17 108.1 . . ? C10 N3 C11 111.6(4) . . ? C10 N3 H15 109.3(2) . . ? C11 N3 H15 109.3(2) . . ? C10 N3 H16 109.3(2) . . ? C11 N3 H16 109.3(2) . . ? H15 N3 H16 108.0 . . ? _refine_diff_density_max 0.638 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.128 #Compound III (chain) data_sad_Compound_III_(chain) _database_code_CSD 151824 _audit_creation_method SHELXL _chemical_name_systematic ; 'Zinc oxalate chain with diazabicyclo[2.2.2]octane' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H20 N2 O11 Zn' _chemical_formula_weight 409.65 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 '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 2(1)/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 9.4328(8) _cell_length_b 16.8597(15) _cell_length_c 9.7878(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.3730(10) _cell_angle_gamma 90.00 _cell_volume 1556.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method ? _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.641 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6499 _diffrn_reflns_av_R_equivalents 0.0709 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 23.30 _reflns_number_total 2246 _reflns_number_observed 1366 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0633P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2236 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_obs 0.0482 _refine_ls_wR_factor_all 0.1293 _refine_ls_wR_factor_obs 0.1040 _refine_ls_goodness_of_fit_all 0.990 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 0.999 _refine_ls_restrained_S_obs 1.068 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.09927(7) 0.45422(4) 0.25142(7) 0.0357(3) Uani 1 d . . O1 O -0.0780(4) 0.4417(2) 0.3710(4) 0.0407(11) Uani 1 d . . O2 O 0.0441(4) 0.5568(2) 0.1437(4) 0.0368(10) Uani 1 d . . O3 O 0.3119(4) 0.4614(2) 0.1978(4) 0.0394(11) Uani 1 d . . O4 O 0.1712(4) 0.3416(2) 0.3144(4) 0.0419(11) Uani 1 d . . O5 O 0.0293(4) 0.4046(2) 0.0634(4) 0.0376(10) Uani 1 d . . O6 O 0.1604(4) 0.5239(2) 0.4250(4) 0.0425(11) Uani 1 d . . C1 C -0.0682(6) 0.4758(4) 0.4844(6) 0.0341(15) Uani 1 d . . C2 C 0.3768(7) 0.3983(4) 0.2159(6) 0.041(2) Uani 1 d . . C3 C 0.2945(7) 0.3275(4) 0.2764(6) 0.039(2) Uani 1 d . . C4 C -0.0039(6) 0.4562(4) -0.0237(6) 0.0304(14) Uani 1 d . . O7 O 0.3554(5) 0.2618(3) 0.2802(5) 0.0667(15) Uani 1 d . . O8 O 0.5035(5) 0.3863(3) 0.1887(6) 0.076(2) Uani 1 d . . O100 O 0.4397(8) 0.5834(6) 0.4865(10) 0.086(2) Uani 1 d . . O200 O 0.1533(7) 0.1396(5) 0.3152(8) 0.067(2) Uani 1 d . . O300 O 0.6779(7) 0.5027(4) 0.0873(7) 0.077(2) Uani 1 d . . N2 N -0.1201(5) 0.1749(3) 0.2341(5) 0.0420(13) Uani 1 d . . H6 H -0.0391(5) 0.1456(3) 0.2383(5) 0.050 Uiso 1 calc R . N1 N -0.3396(5) 0.2545(3) 0.2220(5) 0.0439(14) Uani 1 d . . H1 H -0.4202(5) 0.2841(3) 0.2177(5) 0.053 Uiso 1 calc R . C10 C -0.2237(7) 0.2990(4) 0.1552(7) 0.046(2) Uani 1 d . . H3 H -0.1979(7) 0.3452(4) 0.2092(7) 0.056 Uiso 1 calc R . H2 H -0.2551(7) 0.3166(4) 0.0651(7) 0.056 Uiso 1 calc R . C9 C -0.0983(7) 0.2448(4) 0.1436(7) 0.050(2) Uani 1 d . . H5 H -0.0892(7) 0.2276(4) 0.0497(7) 0.060 Uiso 1 calc R . H4 H -0.0122(7) 0.2726(4) 0.1711(7) 0.060 Uiso 1 calc R . C8 C -0.2383(7) 0.1251(4) 0.1736(7) 0.047(2) Uani 1 d . . H8 H -0.2610(7) 0.0822(4) 0.2354(7) 0.056 Uiso 1 calc R . H7 H -0.2095(7) 0.1022(4) 0.0876(7) 0.056 Uiso 1 calc R . C7 C -0.3660(7) 0.1777(4) 0.1507(6) 0.046(2) Uani 1 d . . H9 H -0.3819(7) 0.1867(4) 0.0537(6) 0.055 Uiso 1 calc R . H10 H -0.4497(7) 0.1524(4) 0.1865(6) 0.055 Uiso 1 calc R . C6 C -0.1553(8) 0.2004(5) 0.3715(6) 0.060(2) Uani 1 d . . H12 H -0.0846(8) 0.2377(5) 0.4056(6) 0.072 Uiso 1 calc R . H11 H -0.1555(8) 0.1550(5) 0.4324(6) 0.072 Uiso 1 calc R . C5 C -0.3007(7) 0.2394(5) 0.3682(6) 0.055(2) Uani 1 d . . H14 H -0.3699(7) 0.2047(5) 0.4091(6) 0.066 Uiso 1 calc R . H13 H -0.2978(7) 0.2888(5) 0.4188(6) 0.066 Uiso 1 calc R . H301 H 0.5849(118) 0.4811(62) 0.1507(100) 0.159(40) Uiso 1 d . . H302 H 0.6851(78) 0.5057(45) 0.0125(70) 0.055(27) Uiso 1 d . . H101 H 0.4483(90) 0.5331(51) 0.4831(94) 0.086(39) Uiso 1 d . . H102 H 0.3997(112) 0.5834(69) 0.5529(101) 0.125(57) Uiso 1 d . . H201 H 0.1752(106) 0.1093(60) 0.2877(105) 0.093(51) Uiso 1 d . . H202 H 0.2296(123) 0.1794(70) 0.2991(107) 0.165(50) 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 Zn1 0.0334(4) 0.0378(5) 0.0361(4) -0.0004(4) 0.0036(3) 0.0008(4) O1 0.031(2) 0.053(3) 0.039(3) -0.010(2) 0.006(2) -0.006(2) O2 0.042(3) 0.034(3) 0.035(2) -0.004(2) -0.006(2) 0.004(2) O3 0.036(2) 0.033(3) 0.050(3) 0.008(2) 0.010(2) 0.006(2) O4 0.032(2) 0.042(3) 0.052(3) 0.005(2) 0.007(2) 0.001(2) O5 0.044(3) 0.030(3) 0.039(2) 0.004(2) 0.000(2) 0.000(2) O6 0.032(2) 0.056(3) 0.040(2) -0.006(2) 0.009(2) -0.007(2) C1 0.027(3) 0.040(4) 0.036(4) 0.006(3) 0.000(3) 0.004(3) C2 0.038(4) 0.041(5) 0.045(4) 0.006(3) 0.007(3) 0.002(3) C3 0.039(4) 0.039(4) 0.039(4) 0.010(3) -0.003(3) 0.007(4) C4 0.023(3) 0.034(4) 0.035(4) -0.002(3) 0.009(3) 0.003(3) O7 0.046(3) 0.042(3) 0.112(4) 0.018(3) 0.013(3) 0.014(3) O8 0.042(3) 0.054(4) 0.133(5) 0.028(3) 0.034(3) 0.013(3) O100 0.067(4) 0.080(6) 0.113(7) -0.006(5) 0.004(4) -0.014(4) O200 0.045(3) 0.055(4) 0.100(5) 0.003(4) -0.006(3) 0.010(3) O300 0.100(5) 0.078(4) 0.054(4) -0.001(4) 0.010(4) -0.035(4) N2 0.037(3) 0.033(3) 0.056(4) 0.001(3) -0.005(3) 0.011(3) N1 0.033(3) 0.038(3) 0.061(4) -0.005(3) 0.004(3) 0.003(3) C10 0.046(4) 0.034(4) 0.059(4) 0.012(3) 0.005(3) -0.001(3) C9 0.042(4) 0.035(4) 0.072(5) 0.010(4) 0.007(4) -0.010(3) C8 0.052(4) 0.035(4) 0.054(4) 0.000(3) 0.005(3) -0.009(4) C7 0.044(4) 0.051(5) 0.044(4) -0.008(3) 0.006(3) -0.007(4) C6 0.077(6) 0.066(5) 0.037(4) 0.002(4) -0.013(4) 0.008(4) C5 0.063(5) 0.067(5) 0.034(4) -0.004(4) 0.009(4) -0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.074(4) . ? Zn1 O2 2.085(4) . ? Zn1 O3 2.089(4) . ? Zn1 O4 2.103(4) . ? Zn1 O5 2.112(4) . ? Zn1 O6 2.134(4) . ? O1 C1 1.253(7) . ? O2 C4 1.245(6) 3_565 ? O3 C2 1.238(7) . ? O4 C3 1.252(6) . ? O5 C4 1.252(7) . ? O6 C1 1.257(7) 3_566 ? C1 O6 1.257(7) 3_566 ? C1 C1 1.546(11) 3_566 ? C2 O8 1.248(7) . ? C2 C3 1.549(9) . ? C3 O7 1.248(7) . ? C4 O2 1.245(6) 3_565 ? C4 C4 1.550(12) 3_565 ? O100 H101 0.85(8) . ? O100 H102 0.76(9) . ? O200 H201 0.62(9) . ? O200 H202 1.00(12) . ? O300 H301 1.15(11) . ? O300 H302 0.74(7) . ? N2 C6 1.457(7) . ? N2 C9 1.492(7) . ? N2 C8 1.506(7) . ? N2 H6 0.91 . ? N1 C7 1.489(8) . ? N1 C10 1.490(7) . ? N1 C5 1.490(8) . ? N1 H1 0.91 . ? C10 C9 1.500(8) . ? C10 H3 0.97 . ? C10 H2 0.97 . ? C9 H5 0.97 . ? C9 H4 0.97 . ? C8 C7 1.509(8) . ? C8 H8 0.97 . ? C8 H7 0.97 . ? C7 H9 0.97 . ? C7 H10 0.97 . ? C6 C5 1.521(9) . ? C6 H12 0.97 . ? C6 H11 0.97 . ? C5 H14 0.97 . ? C5 H13 0.97 . ? 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 Zn1 O2 100.1(2) . . ? O1 Zn1 O3 159.9(2) . . ? O2 Zn1 O3 93.1(2) . . ? O1 Zn1 O4 90.1(2) . . ? O2 Zn1 O4 166.33(15) . . ? O3 Zn1 O4 79.7(2) . . ? O1 Zn1 O5 102.2(2) . . ? O2 Zn1 O5 79.57(15) . . ? O3 Zn1 O5 94.9(2) . . ? O4 Zn1 O5 89.4(2) . . ? O1 Zn1 O6 79.2(2) . . ? O2 Zn1 O6 90.3(2) . . ? O3 Zn1 O6 85.71(15) . . ? O4 Zn1 O6 100.6(2) . . ? O5 Zn1 O6 169.9(2) . . ? C1 O1 Zn1 114.2(4) . . ? C4 O2 Zn1 113.4(4) 3_565 . ? C2 O3 Zn1 112.9(4) . . ? C3 O4 Zn1 112.3(4) . . ? C4 O5 Zn1 112.7(3) . . ? C1 O6 Zn1 112.6(4) 3_566 . ? O1 C1 O6 126.1(5) . 3_566 ? O1 C1 C1 117.4(7) . 3_566 ? O6 C1 C1 116.5(7) 3_566 3_566 ? O3 C2 O8 125.6(6) . . ? O3 C2 C3 117.8(6) . . ? O8 C2 C3 116.6(6) . . ? O7 C3 O4 126.2(6) . . ? O7 C3 C2 117.4(6) . . ? O4 C3 C2 116.4(6) . . ? O2 C4 O5 125.9(5) 3_565 . ? O2 C4 C4 117.5(7) 3_565 3_565 ? O5 C4 C4 116.6(6) . 3_565 ? H101 O100 H102 94.8(100) . . ? H201 O200 H202 103.7(100) . . ? H301 O300 H302 130.4(80) . . ? C6 N2 C9 110.7(5) . . ? C6 N2 C8 110.2(5) . . ? C9 N2 C8 108.6(5) . . ? C6 N2 H6 109.1(3) . . ? C9 N2 H6 109.1(3) . . ? C8 N2 H6 109.1(3) . . ? C7 N1 C10 110.4(5) . . ? C7 N1 C5 109.6(5) . . ? C10 N1 C5 110.0(5) . . ? C7 N1 H1 108.9(3) . . ? C10 N1 H1 108.9(3) . . ? C5 N1 H1 108.9(3) . . ? N1 C10 C9 108.4(5) . . ? N1 C10 H3 110.0(3) . . ? C9 C10 H3 110.0(4) . . ? N1 C10 H2 110.0(3) . . ? C9 C10 H2 110.0(4) . . ? H3 C10 H2 108.4 . . ? N2 C9 C10 108.4(5) . . ? N2 C9 H5 110.0(3) . . ? C10 C9 H5 110.0(4) . . ? N2 C9 H4 110.0(3) . . ? C10 C9 H4 110.0(4) . . ? H5 C9 H4 108.4 . . ? N2 C8 C7 108.1(5) . . ? N2 C8 H8 110.1(3) . . ? C7 C8 H8 110.1(4) . . ? N2 C8 H7 110.1(3) . . ? C7 C8 H7 110.1(3) . . ? H8 C8 H7 108.4 . . ? N1 C7 C8 108.5(5) . . ? N1 C7 H9 110.0(3) . . ? C8 C7 H9 110.0(3) . . ? N1 C7 H10 110.0(3) . . ? C8 C7 H10 110.0(3) . . ? H9 C7 H10 108.4 . . ? N2 C6 C5 109.4(5) . . ? N2 C6 H12 109.8(4) . . ? C5 C6 H12 109.8(4) . . ? N2 C6 H11 109.8(3) . . ? C5 C6 H11 109.8(4) . . ? H12 C6 H11 108.2 . . ? N1 C5 C6 107.2(5) . . ? N1 C5 H14 110.3(3) . . ? C6 C5 H14 110.3(4) . . ? N1 C5 H13 110.3(4) . . ? C6 C5 H13 110.3(4) . . ? H14 C5 H13 108.5 . . ? _refine_diff_density_max 0.695 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.119 #Compound IV (layer) data_sad_Compound_IV_(layer) _database_code_CSD 151825 _audit_creation_method SHELXL _chemical_name_systematic ; 'layered zinc oxalate with piperazine' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H48 N8 O32 Zn4' _chemical_formula_weight 1270.22 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/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 16.7253(6) _cell_length_b 9.2540(3) _cell_length_c 31.2982(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.59 _cell_angle_gamma 90.00 _cell_volume 4789.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method ? _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 2.087 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9600 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 23.29 _reflns_number_total 3439 _reflns_number_observed 2403 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0757P)^2^+26.3797P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3439 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_obs 0.0539 _refine_ls_wR_factor_all 0.1615 _refine_ls_wR_factor_obs 0.1349 _refine_ls_goodness_of_fit_all 1.065 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.065 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max 0.027 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.47695(5) 0.13449(9) 0.36116(3) 0.0302(3) Uani 1 d . . Zn2 Zn 0.65134(5) -0.36406(9) 0.35957(3) 0.0285(3) Uani 1 d . . O1 O 0.3911(3) 0.0692(5) 0.3988(2) 0.0331(12) Uani 1 d . . O2 O 0.3709(3) 0.1950(6) 0.3210(2) 0.0342(13) Uani 1 d . . O3 O 0.5736(3) 0.0245(6) 0.3978(2) 0.0380(13) Uani 1 d . . O4 O 0.5003(3) 0.3267(5) 0.3967(2) 0.0360(13) Uani 1 d . . O5 O 0.5519(3) 0.2440(5) 0.3234(2) 0.0372(13) Uani 1 d . . O6 O 0.4793(3) -0.0575(5) 0.3243(2) 0.0339(13) Uani 1 d . . O7 O 0.6467(3) -0.1768(5) 0.3955(2) 0.0346(13) Uani 1 d . . O8 O 0.7570(3) -0.4337(6) 0.3977(2) 0.0341(13) Uani 1 d . . O9 O 0.6252(3) -0.5545(5) 0.3239(2) 0.0328(12) Uani 1 d . . O10 O 0.7371(3) -0.2969(6) 0.3211(2) 0.0331(12) Uani 1 d . . O11 O 0.5580(3) -0.2504(5) 0.3199(2) 0.0333(13) Uani 1 d . . O12 O 0.5724(3) -0.4700(5) 0.3968(2) 0.0329(12) Uani 1 d . . C1 C 0.8198(4) -0.4028(7) 0.3821(2) 0.028(2) Uani 1 d . . C2 C 0.8078(5) -0.3263(7) 0.3379(2) 0.026(2) Uani 1 d . . C3 C 0.5913(4) -0.0921(8) 0.3809(2) 0.030(2) Uani 1 d . . C4 C 0.5472(4) 0.4104(8) 0.3816(2) 0.027(2) Uani 1 d . . C5 C 0.5779(4) 0.3628(8) 0.3395(2) 0.029(2) Uani 1 d . . C6 C 0.5384(4) -0.1364(8) 0.3378(2) 0.028(2) Uani 1 d . . O100 O 0.3702(4) 0.0693(7) 0.2321(2) 0.059(2) Uani 1 d . . O200 O 0.6663(4) -0.5685(9) 0.0905(2) 0.078(2) Uani 1 d . . O300 O 0.5125(9) 0.1270(19) 0.4940(8) 0.296(12) Uani 1 d . . O400 O 0.4874(8) -0.3950(14) 0.4677(4) 0.173(5) Uani 1 d . . C7 C 0.6203(5) -0.4450(9) 0.1891(3) 0.042(2) Uani 1 d . . H2 H 0.6139(5) -0.5489(9) 0.1909(3) 0.050 Uiso 1 calc R . H1 H 0.5743(5) -0.4076(9) 0.1698(3) 0.050 Uiso 1 calc R . C8 C 0.6204(5) -0.3811(9) 0.2331(3) 0.042(2) Uani 1 d . . H4 H 0.5685(5) -0.3984(9) 0.2425(3) 0.050 Uiso 1 calc R . H3 H 0.6617(5) -0.4276(9) 0.2536(3) 0.050 Uiso 1 calc R . C9 C 0.7109(5) -0.1903(9) 0.2140(3) 0.044(2) Uani 1 d . . H8 H 0.7576(5) -0.2276(9) 0.2329(3) 0.052 Uiso 1 calc R . H7 H 0.7171(5) -0.0865(9) 0.2117(3) 0.052 Uiso 1 calc R . C10 C 0.7060(6) -0.2580(10) 0.1701(3) 0.052(2) Uani 1 d . . H10 H 0.6617(6) -0.2145(10) 0.1509(3) 0.062 Uiso 1 calc R . H9 H 0.7556(6) -0.2379(10) 0.1586(3) 0.062 Uiso 1 calc R . C11 C 0.6879(7) -0.3585(10) 0.4950(3) 0.066(3) Uani 1 d . . H14 H 0.6461(7) -0.4114(10) 0.5067(3) 0.079 Uiso 1 calc R . H13 H 0.6878(7) -0.3902(10) 0.4654(3) 0.079 Uiso 1 calc R . C12 C 0.7368(5) -0.1110(8) 0.4806(2) 0.033(2) Uani 1 d . . H18 H 0.7389(5) -0.1339(8) 0.4505(2) 0.040 Uiso 1 calc R . H17 H 0.7259(5) -0.0084(8) 0.4825(2) 0.040 Uiso 1 calc R . C13 C 0.6984(9) 0.2203(14) 0.5313(4) 0.092(4) Uani 1 d . . H20 H 0.6794(9) 0.1536(14) 0.5514(4) 0.111 Uiso 1 calc R . H19 H 0.6705(9) 0.3116(14) 0.5328(4) 0.111 Uiso 1 calc R . C14 C 0.7124(9) 0.2578(13) 0.4572(4) 0.095(4) Uani 1 d . . H24 H 0.6851(9) 0.3504(13) 0.4566(4) 0.114 Uiso 1 calc R . H23 H 0.7007(9) 0.2153(13) 0.4286(4) 0.114 Uiso 1 calc R . N1 N 0.6362(4) -0.2232(7) 0.2326(2) 0.036(2) Uani 1 d . . H6 H 0.6412(4) -0.1887(7) 0.2598(2) 0.044 Uiso 1 calc R . H5 H 0.5938(4) -0.1786(7) 0.2169(2) 0.044 Uiso 1 calc R . N2 N 0.6938(4) -0.4138(8) 0.1711(2) 0.045(2) Uani 1 d . . H12 H 0.6896(4) -0.4498(8) 0.1441(2) 0.053 Uiso 1 calc R . H11 H 0.7364(4) -0.4559(8) 0.1873(2) 0.053 Uiso 1 calc R . N3 N 0.6690(7) -0.1940(12) 0.4954(3) 0.109(4) Uani 1 d . . H16 H 0.6225(7) -0.1756(12) 0.4777(3) 0.130 Uiso 1 calc R . H15 H 0.6630(7) -0.1662(12) 0.5222(3) 0.130 Uiso 1 calc R . N4 N 0.6820(6) 0.1633(10) 0.4884(3) 0.083(3) Uani 1 d . . H22 H 0.6282(6) 0.1522(10) 0.4810(3) 0.100 Uiso 1 calc R . H21 H 0.7052(6) 0.0758(10) 0.4878(3) 0.100 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 Zn1 0.0245(5) 0.0257(5) 0.0402(6) -0.0021(4) 0.0038(4) 0.0004(4) Zn2 0.0252(5) 0.0255(5) 0.0343(5) 0.0008(4) 0.0028(4) 0.0013(4) O1 0.026(3) 0.036(3) 0.036(3) 0.012(2) 0.002(2) 0.006(2) O2 0.026(3) 0.036(3) 0.041(3) 0.007(2) 0.006(3) 0.000(2) O3 0.039(3) 0.029(3) 0.041(3) -0.011(3) -0.007(3) 0.004(3) O4 0.040(3) 0.030(3) 0.040(3) -0.006(2) 0.013(3) -0.008(3) O5 0.043(3) 0.027(3) 0.044(3) -0.008(3) 0.015(3) -0.006(3) O6 0.028(3) 0.026(3) 0.045(3) -0.004(2) -0.005(2) 0.002(2) O7 0.030(3) 0.032(3) 0.037(3) -0.009(2) -0.009(2) 0.007(2) O8 0.025(3) 0.040(3) 0.037(3) 0.008(2) 0.006(2) 0.002(2) O9 0.033(3) 0.030(3) 0.037(3) -0.003(2) 0.009(2) -0.005(2) O10 0.027(3) 0.038(3) 0.034(3) 0.009(2) 0.002(2) 0.001(2) O11 0.033(3) 0.027(3) 0.038(3) -0.006(2) -0.003(2) 0.004(2) O12 0.033(3) 0.030(3) 0.036(3) -0.007(2) 0.007(2) -0.008(2) C1 0.027(4) 0.022(4) 0.034(4) -0.003(3) 0.003(4) 0.007(3) C2 0.029(5) 0.024(4) 0.025(4) -0.004(3) -0.001(4) 0.002(3) C3 0.028(4) 0.027(5) 0.035(4) -0.002(4) 0.005(3) -0.008(4) C4 0.024(4) 0.022(4) 0.032(4) 0.003(4) -0.001(3) 0.005(3) C5 0.021(4) 0.025(4) 0.040(5) -0.001(4) 0.001(3) 0.005(4) C6 0.026(4) 0.025(4) 0.035(4) 0.002(4) 0.006(3) -0.005(4) O100 0.061(4) 0.058(4) 0.058(4) 0.019(3) 0.010(3) 0.002(3) O200 0.068(5) 0.108(6) 0.060(4) -0.021(4) 0.017(4) -0.003(4) O300 0.166(14) 0.244(18) 0.515(31) -0.174(21) 0.172(18) -0.014(12) O400 0.180(12) 0.163(11) 0.201(12) -0.033(9) 0.108(10) 0.012(9) C7 0.043(5) 0.032(5) 0.050(5) -0.005(4) 0.004(4) -0.001(4) C8 0.044(5) 0.038(5) 0.044(5) 0.003(4) 0.009(4) -0.004(4) C9 0.045(5) 0.036(5) 0.049(5) 0.001(4) 0.005(4) -0.005(4) C10 0.050(6) 0.057(6) 0.053(6) -0.001(5) 0.021(5) -0.011(5) C11 0.087(8) 0.049(6) 0.064(7) -0.002(5) 0.017(6) -0.004(6) C12 0.053(5) 0.018(4) 0.025(4) 0.005(3) -0.004(4) -0.013(4) C13 0.128(12) 0.086(9) 0.065(8) 0.021(7) 0.019(8) 0.005(9) C14 0.135(13) 0.062(8) 0.070(8) 0.012(6) -0.038(8) -0.006(8) N1 0.042(4) 0.031(4) 0.032(4) -0.006(3) -0.006(3) 0.006(3) N2 0.038(4) 0.052(5) 0.045(4) -0.012(4) 0.008(3) 0.008(4) N3 0.132(10) 0.111(9) 0.076(7) -0.011(6) -0.009(7) 0.013(8) N4 0.079(7) 0.063(6) 0.100(8) 0.009(6) -0.013(6) -0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.079(5) . ? Zn1 O2 2.092(5) . ? Zn1 O3 2.100(5) . ? Zn1 O4 2.103(5) . ? Zn1 O5 2.108(5) . ? Zn1 O6 2.123(5) . ? Zn2 O7 2.074(5) . ? Zn2 O8 2.082(5) . ? Zn2 O9 2.097(5) . ? Zn2 O10 2.100(5) . ? Zn2 O11 2.123(5) . ? Zn2 O12 2.126(5) . ? O1 C1 1.257(8) 3_455 ? O2 C2 1.264(8) 3_455 ? O3 C3 1.256(9) . ? O4 C4 1.244(8) . ? O5 C5 1.259(9) . ? O6 C6 1.251(8) . ? O7 C3 1.248(9) . ? O8 C1 1.257(8) . ? O9 C5 1.250(9) 1_545 ? O10 C2 1.251(8) . ? O11 C6 1.259(8) . ? O12 C4 1.253(8) 1_545 ? C1 O1 1.257(8) 3_545 ? C1 C2 1.540(11) . ? C2 O2 1.264(8) 3_545 ? C3 C6 1.554(10) . ? C4 O12 1.253(8) 1_565 ? C4 C5 1.548(10) . ? C5 O9 1.250(9) 1_565 ? C7 N2 1.456(10) . ? C7 C8 1.499(11) . ? C7 H2 0.97 . ? C7 H1 0.97 . ? C8 N1 1.485(10) . ? C8 H4 0.97 . ? C8 H3 0.97 . ? C9 N1 1.487(10) . ? C9 C10 1.501(11) . ? C9 H8 0.97 . ? C9 H7 0.97 . ? C10 N2 1.457(11) . ? C10 H10 0.97 . ? C10 H9 0.97 . ? C11 C12 1.401(12) 7_646 ? C11 N3 1.555(14) . ? C11 H14 0.97 . ? C11 H13 0.97 . ? C12 C11 1.401(12) 7_646 ? C12 N3 1.498(13) . ? C12 H18 0.97 . ? C12 H17 0.97 . ? C13 N4 1.429(14) . ? C13 C14 1.50(2) 7_656 ? C13 H20 0.97 . ? C13 H19 0.97 . ? C14 N4 1.458(14) . ? C14 C13 1.50(2) 7_656 ? C14 H24 0.97 . ? C14 H23 0.97 . ? N1 H6 0.90 . ? N1 H5 0.90 . ? N2 H12 0.90 . ? N2 H11 0.90 . ? N3 H16 0.90 . ? N3 H15 0.90 . ? N4 H22 0.90 . ? N4 H21 0.90 . ? 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 Zn1 O2 79.8(2) . . ? O1 Zn1 O3 95.1(2) . . ? O2 Zn1 O3 166.5(2) . . ? O1 Zn1 O4 92.0(2) . . ? O2 Zn1 O4 99.5(2) . . ? O3 Zn1 O4 93.1(2) . . ? O1 Zn1 O5 167.8(2) . . ? O2 Zn1 O5 93.2(2) . . ? O3 Zn1 O5 93.8(2) . . ? O4 Zn1 O5 79.1(2) . . ? O1 Zn1 O6 97.8(2) . . ? O2 Zn1 O6 88.9(2) . . ? O3 Zn1 O6 79.4(2) . . ? O4 Zn1 O6 168.1(2) . . ? O5 Zn1 O6 92.1(2) . . ? O7 Zn2 O8 92.6(2) . . ? O7 Zn2 O9 165.8(2) . . ? O8 Zn2 O9 97.9(2) . . ? O7 Zn2 O10 98.5(2) . . ? O8 Zn2 O10 80.1(2) . . ? O9 Zn2 O10 92.8(2) . . ? O7 Zn2 O11 79.6(2) . . ? O8 Zn2 O11 167.4(2) . . ? O9 Zn2 O11 91.6(2) . . ? O10 Zn2 O11 91.3(2) . . ? O7 Zn2 O12 90.6(2) . . ? O8 Zn2 O12 94.9(2) . . ? O9 Zn2 O12 78.9(2) . . ? O10 Zn2 O12 169.7(2) . . ? O11 Zn2 O12 94.9(2) . . ? C1 O1 Zn1 113.3(5) 3_455 . ? C2 O2 Zn1 113.1(4) 3_455 . ? C3 O3 Zn1 113.4(5) . . ? C4 O4 Zn1 113.8(5) . . ? C5 O5 Zn1 113.2(5) . . ? C6 O6 Zn1 112.5(4) . . ? C3 O7 Zn2 114.3(5) . . ? C1 O8 Zn2 113.1(4) . . ? C5 O9 Zn2 113.6(5) 1_545 . ? C2 O10 Zn2 112.2(4) . . ? C6 O11 Zn2 111.9(4) . . ? C4 O12 Zn2 113.6(5) 1_545 . ? O1 C1 O8 125.9(7) 3_545 . ? O1 C1 C2 117.2(7) 3_545 . ? O8 C1 C2 116.8(6) . . ? O10 C2 O2 125.8(7) . 3_545 ? O10 C2 C1 117.8(7) . . ? O2 C2 C1 116.3(6) 3_545 . ? O7 C3 O3 126.4(7) . . ? O7 C3 C6 116.6(7) . . ? O3 C3 C6 117.0(7) . . ? O4 C4 O12 126.9(7) . 1_565 ? O4 C4 C5 117.1(6) . . ? O12 C4 C5 116.0(6) 1_565 . ? O9 C5 O5 125.4(7) 1_565 . ? O9 C5 C4 117.9(7) 1_565 . ? O5 C5 C4 116.7(7) . . ? O6 C6 O11 125.7(7) . . ? O6 C6 C3 117.2(7) . . ? O11 C6 C3 117.1(6) . . ? N2 C7 C8 113.2(7) . . ? N2 C7 H2 108.9(4) . . ? C8 C7 H2 108.9(5) . . ? N2 C7 H1 108.9(4) . . ? C8 C7 H1 108.9(5) . . ? H2 C7 H1 107.8 . . ? N1 C8 C7 110.7(7) . . ? N1 C8 H4 109.5(4) . . ? C7 C8 H4 109.5(5) . . ? N1 C8 H3 109.5(4) . . ? C7 C8 H3 109.5(5) . . ? H4 C8 H3 108.1 . . ? N1 C9 C10 109.8(7) . . ? N1 C9 H8 109.7(4) . . ? C10 C9 H8 109.7(5) . . ? N1 C9 H7 109.7(4) . . ? C10 C9 H7 109.7(5) . . ? H8 C9 H7 108.2 . . ? N2 C10 C9 112.5(7) . . ? N2 C10 H10 109.1(5) . . ? C9 C10 H10 109.1(5) . . ? N2 C10 H9 109.1(4) . . ? C9 C10 H9 109.1(5) . . ? H10 C10 H9 107.8 . . ? C12 C11 N3 111.1(8) 7_646 . ? C12 C11 H14 109.4(5) 7_646 . ? N3 C11 H14 109.4(6) . . ? C12 C11 H13 109.4(5) 7_646 . ? N3 C11 H13 109.4(5) . . ? H14 C11 H13 108.0 . . ? C11 C12 N3 112.9(7) 7_646 . ? C11 C12 H18 109.0(5) 7_646 . ? N3 C12 H18 109.0(5) . . ? C11 C12 H17 109.0(5) 7_646 . ? N3 C12 H17 109.0(5) . . ? H18 C12 H17 107.8 . . ? N4 C13 C14 108.8(11) . 7_656 ? N4 C13 H20 109.9(7) . . ? C14 C13 H20 109.9(6) 7_656 . ? N4 C13 H19 109.9(7) . . ? C14 C13 H19 109.9(7) 7_656 . ? H20 C13 H19 108.3 . . ? N4 C14 C13 110.7(9) . 7_656 ? N4 C14 H24 109.5(7) . . ? C13 C14 H24 109.5(7) 7_656 . ? N4 C14 H23 109.5(6) . . ? C13 C14 H23 109.5(7) 7_656 . ? H24 C14 H23 108.1 . . ? C8 N1 C9 111.5(6) . . ? C8 N1 H6 109.3(4) . . ? C9 N1 H6 109.3(4) . . ? C8 N1 H5 109.3(4) . . ? C9 N1 H5 109.3(4) . . ? H6 N1 H5 108.0 . . ? C7 N2 C10 109.5(6) . . ? C7 N2 H12 109.8(4) . . ? C10 N2 H12 109.8(4) . . ? C7 N2 H11 109.8(4) . . ? C10 N2 H11 109.8(5) . . ? H12 N2 H11 108.2 . . ? C12 N3 C11 109.6(9) . . ? C12 N3 H16 109.8(5) . . ? C11 N3 H16 109.8(6) . . ? C12 N3 H15 109.8(5) . . ? C11 N3 H15 109.8(6) . . ? H16 N3 H15 108.2 . . ? C13 N4 C14 111.8(9) . . ? C13 N4 H22 109.3(7) . . ? C14 N4 H22 109.3(7) . . ? C13 N4 H21 109.3(6) . . ? C14 N4 H21 109.3(7) . . ? H22 N4 H21 107.9 . . ? _refine_diff_density_max 1.251 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.153 data_sad_Guanidinium oxalate _database_code_CSD 151827 _audit_creation_method SHELXL _chemical_name_systematic ; 'Guanidinium oxalate' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C3 H9 N3 O5' _chemical_formula_weight 167.13 _chemical_melting_point ? _chemical_compound_source ? 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 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6991(9) _cell_length_b 10.5524(14) _cell_length_c 10.2243(13) _cell_angle_alpha 90.00 _cell_angle_beta 103.766(2) _cell_angle_gamma 90.00 _cell_volume 702.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method ? _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2813 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 23.30 _reflns_number_total 1012 _reflns_number_observed 663 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.1528P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0472(157) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1012 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_obs 0.0792 _refine_ls_wR_factor_all 0.2365 _refine_ls_wR_factor_obs 0.2181 _refine_ls_goodness_of_fit_all 1.089 _refine_ls_goodness_of_fit_obs 1.270 _refine_ls_restrained_S_all 1.089 _refine_ls_restrained_S_obs 1.270 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.3588(5) 0.4770(3) 0.1258(3) 0.0435(10) Uani 1 d . . O2 O 0.1849(5) 0.4244(3) -0.0799(3) 0.0466(11) Uani 1 d . . O3 O 0.1445(5) 0.6676(3) -0.1503(3) 0.0476(11) Uani 1 d . . H7 H 0.1510(64) 0.7435(8) -0.1662(16) 0.071 Uiso 1 calc R . O4 O 0.3202(5) 0.7240(3) 0.0540(3) 0.0515(11) Uani 1 d . . C1 C 0.2634(6) 0.5020(4) 0.0085(5) 0.0329(12) Uani 1 d . . C2 C 0.2456(6) 0.6447(4) -0.0272(4) 0.0344(12) Uani 1 d . . O100 O 0.8684(6) 0.0846(3) 0.2002(3) 0.0423(11) Uani 1 d . . N1 N 0.6806(6) 0.4973(3) 0.3818(4) 0.0504(13) Uani 1 d . . H2 H 0.7294(6) 0.4409(3) 0.4416(4) 0.061 Uiso 1 calc R . H1 H 0.6159(6) 0.4745(3) 0.3022(4) 0.061 Uiso 1 calc R . N2 N 0.8034(6) 0.6546(4) 0.5333(4) 0.0475(12) Uani 1 d . . H4 H 0.8211(6) 0.7338(4) 0.5520(4) 0.057 Uiso 1 calc R . H3 H 0.8501(6) 0.5986(4) 0.5940(4) 0.057 Uiso 1 calc R . N3 N 0.6328(6) 0.7045(3) 0.3187(4) 0.0434(12) Uani 1 d . . H6 H 0.6503(6) 0.7839(3) 0.3370(4) 0.052 Uiso 1 calc R . H5 H 0.5683(6) 0.6809(3) 0.2393(4) 0.052 Uiso 1 calc R . C3 C 0.7049(6) 0.6190(4) 0.4121(4) 0.0352(12) Uani 1 d . . H100 H 0.7648(82) 0.0634(55) 0.2428(61) 0.079(20) Uiso 1 d . . H101 H 0.9765(85) 0.0669(56) 0.2499(64) 0.066(19) 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 0.058(2) 0.034(2) 0.033(2) 0.0033(14) 0.000(2) 0.004(2) O2 0.065(2) 0.030(2) 0.036(2) -0.0026(15) -0.004(2) 0.000(2) O3 0.073(2) 0.028(2) 0.033(2) 0.0042(14) -0.006(2) 0.001(2) O4 0.077(2) 0.028(2) 0.039(2) -0.005(2) -0.007(2) -0.002(2) C1 0.040(2) 0.028(3) 0.028(3) 0.000(2) 0.000(2) 0.000(2) C2 0.039(2) 0.034(3) 0.027(3) -0.001(2) 0.001(2) -0.001(2) O100 0.049(2) 0.041(2) 0.032(2) 0.0049(14) 0.000(2) 0.001(2) N1 0.075(3) 0.031(2) 0.039(3) -0.001(2) 0.001(2) 0.000(2) N2 0.069(3) 0.030(2) 0.035(2) 0.000(2) -0.006(2) 0.001(2) N3 0.064(3) 0.027(2) 0.033(2) -0.001(2) -0.002(2) 0.002(2) C3 0.043(3) 0.023(2) 0.038(3) 0.000(2) 0.005(2) 0.000(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 O1 C1 1.246(5) . ? O2 C1 1.239(5) . ? O3 C2 1.302(5) . ? O3 H7 0.82 . ? O4 C2 1.201(5) . ? C1 C2 1.548(6) . ? O100 H100 0.93(6) . ? O100 H101 0.80(6) . ? N1 C3 1.323(6) . ? N1 H2 0.86 . ? N1 H1 0.86 . ? N2 C3 1.312(5) . ? N2 H4 0.86 . ? N2 H3 0.86 . ? N3 C3 1.319(5) . ? N3 H6 0.86 . ? N3 H5 0.86 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O3 H7 109.5(2) . . ? O2 C1 O1 126.4(4) . . ? O2 C1 C2 118.4(4) . . ? O1 C1 C2 115.2(4) . . ? O4 C2 O3 125.0(4) . . ? O4 C2 C1 121.3(4) . . ? O3 C2 C1 113.7(4) . . ? H100 O100 H101 108.0(57) . . ? C3 N1 H2 120.0(3) . . ? C3 N1 H1 120.0(3) . . ? H2 N1 H1 120.0 . . ? C3 N2 H4 120.0(2) . . ? C3 N2 H3 120.0(2) . . ? H4 N2 H3 120.0 . . ? C3 N3 H6 120.0(2) . . ? C3 N3 H5 120.0(2) . . ? H6 N3 H5 120.0 . . ? N2 C3 N3 120.2(4) . . ? N2 C3 N1 120.4(4) . . ? N3 C3 N1 119.4(4) . . ? _refine_diff_density_max 0.450 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.108 #PIPO data_PIPO _database_code_CSD 151828 _audit_creation_method SHELXL _chemical_name_systematic ; 'Piperazinium oxalate' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H14 N2 O8' _chemical_formula_weight 266.21 _chemical_melting_point ? _chemical_compound_source ? 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 'C 2/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 15.9626(6) _cell_length_b 5.7156(2) _cell_length_c 12.354 _cell_angle_alpha 90.00 _cell_angle_beta 108.074(2) _cell_angle_gamma 90.00 _cell_volume 1071.48(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method ? _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2069 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 23.21 _reflns_number_total 760 _reflns_number_observed 686 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0383P)^2^+0.6089P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0094(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 756 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_obs 0.0291 _refine_ls_wR_factor_all 0.0805 _refine_ls_wR_factor_obs 0.0761 _refine_ls_goodness_of_fit_all 1.112 _refine_ls_goodness_of_fit_obs 1.132 _refine_ls_restrained_S_all 1.127 _refine_ls_restrained_S_obs 1.132 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.42872(10) -0.4833(3) 0.89576(12) 0.0267(4) Uani 1 d . . C2 C 0.50409(12) -0.6451(3) 0.9056(2) 0.0294(5) Uani 1 d . . C1 C 0.45713(13) -0.2761(3) 0.9723(2) 0.0315(5) Uani 1 d . . O1 O 0.11062(8) -1.5513(2) 0.78862(12) 0.0429(4) Uani 1 d . . O2 O 0.24363(7) -1.4005(2) 0.88137(10) 0.0291(4) Uani 1 d . . O3 O 0.18001(7) -1.9882(2) 0.83253(10) 0.0282(4) Uani 1 d . . O4 O 0.31250(7) -1.8282(2) 0.91937(10) 0.0284(4) Uani 1 d . . C11 C 0.18804(10) -1.5728(3) 0.84174(13) 0.0231(4) Uani 1 d . . C10 C 0.23206(11) -1.8178(3) 0.86772(13) 0.0212(4) Uani 1 d . . H10 H 0.2164(16) -1.2486(45) 0.8665(20) 0.066(7) Uiso 1 d . . H6 H 0.5470(13) -0.5608(35) 0.8808(15) 0.037(5) Uiso 1 d . . H5 H 0.4821(12) -0.7834(35) 0.8573(15) 0.034(5) Uiso 1 d . . H4 H 0.3847(14) -0.5656(39) 0.9119(17) 0.044(6) Uiso 1 d . . H3 H 0.4035(14) -0.4355(40) 0.8184(21) 0.056(6) Uiso 1 d . . H2 H 0.5018(14) -0.1969(35) 0.9449(16) 0.036(5) Uiso 1 d . . H1 H 0.4056(15) -0.1808(38) 0.9618(17) 0.043(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 N1 0.0202(8) 0.0283(9) 0.0279(9) 0.0017(7) 0.0023(7) -0.0004(6) C2 0.0253(10) 0.0297(11) 0.0321(10) -0.0084(8) 0.0072(8) -0.0017(8) C1 0.0267(11) 0.0228(10) 0.0409(11) -0.0007(8) 0.0045(8) 0.0034(9) O1 0.0236(8) 0.0321(8) 0.0607(9) 0.0044(7) -0.0049(6) 0.0033(6) O2 0.0256(7) 0.0186(8) 0.0398(7) -0.0010(6) 0.0057(5) 0.0000(6) O3 0.0284(7) 0.0194(7) 0.0326(7) -0.0016(5) 0.0031(5) -0.0042(5) O4 0.0207(7) 0.0232(7) 0.0377(7) 0.0027(5) 0.0037(5) 0.0019(5) C11 0.0224(10) 0.0221(9) 0.0241(9) 0.0002(7) 0.0063(7) -0.0007(8) C10 0.0234(10) 0.0226(10) 0.0183(8) 0.0010(7) 0.0074(7) -0.0004(8) _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 N1 C2 1.492(2) . ? N1 C1 1.495(2) . ? N1 H4 0.92(2) . ? N1 H3 0.95(2) . ? C2 C1 1.511(3) 5_647 ? C2 H6 0.96(2) . ? C2 H5 0.99(2) . ? C1 C2 1.511(3) 5_647 ? C1 H2 0.99(2) . ? C1 H1 0.96(2) . ? O1 C11 1.212(2) . ? O2 C11 1.314(2) . ? O2 H10 0.96(3) . ? O3 C10 1.266(2) . ? O4 C10 1.245(2) . ? C11 C10 1.555(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 111.14(13) . . ? C2 N1 H4 108.5(13) . . ? C1 N1 H4 111.8(13) . . ? C2 N1 H3 109.8(13) . . ? C1 N1 H3 110.9(14) . . ? H4 N1 H3 104.5(18) . . ? N1 C2 C1 109.65(15) . 5_647 ? N1 C2 H6 107.4(11) . . ? C1 C2 H6 110.8(11) 5_647 . ? N1 C2 H5 108.7(11) . . ? C1 C2 H5 108.9(10) 5_647 . ? H6 C2 H5 111.3(16) . . ? N1 C1 C2 110.20(15) . 5_647 ? N1 C1 H2 104.8(11) . . ? C2 C1 H2 111.3(11) 5_647 . ? N1 C1 H1 106.5(12) . . ? C2 C1 H1 111.8(12) 5_647 . ? H2 C1 H1 111.9(17) . . ? C11 O2 H10 113.1(14) . . ? O1 C11 O2 125.6(2) . . ? O1 C11 C10 121.50(15) . . ? O2 C11 C10 112.85(13) . . ? O4 C10 O3 126.99(15) . . ? O4 C10 C11 118.48(14) . . ? O3 C10 C11 114.54(13) . . ? _refine_diff_density_max 0.148 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.041 #DABCO-O data_sad_DABCO-O _database_code_CSD 151829 _audit_creation_method SHELXL _chemical_name_systematic ; 'Diazabicyclo[2.2.2]octanium oxalate' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H16 N2 O8' _chemical_formula_weight 292.25 _chemical_melting_point ? _chemical_compound_source ? 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 6.9710(7) _cell_length_b 9.6065(10) _cell_length_c 10.6328(11) _cell_angle_alpha 91.2490(10) _cell_angle_beta 107.5120(10) _cell_angle_gamma 109.3540(10) _cell_volume 634.80(11) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method ? _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2667 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 23.31 _reflns_number_total 1781 _reflns_number_observed 1436 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0783P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.1375(172) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1781 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_obs 0.0492 _refine_ls_wR_factor_all 0.1451 _refine_ls_wR_factor_obs 0.1391 _refine_ls_goodness_of_fit_all 1.062 _refine_ls_goodness_of_fit_obs 1.148 _refine_ls_restrained_S_all 1.062 _refine_ls_restrained_S_obs 1.148 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2374(3) 0.3233(2) 0.4916(2) 0.0547(5) Uani 1 d . . O2 O 0.0894(3) 0.3177(2) 0.6492(2) 0.0570(5) Uani 1 d . . C7 C 0.1811(3) 0.2701(2) 0.5855(2) 0.0389(6) Uani 1 d . . O3 O 0.1934(3) 0.0851(2) 0.7360(2) 0.0648(6) Uani 1 d . . H20 H 0.1506(56) 0.1428(22) 0.7678(20) 0.097 Uiso 1 calc R . O4 O 0.3043(4) 0.0662(2) 0.5651(2) 0.0783(7) Uani 1 d . . C8 C 0.2322(4) 0.1301(3) 0.6270(2) 0.0489(6) Uani 1 d . . O5 O -0.3319(4) 0.3684(3) -0.0900(2) 0.1012(10) Uani 1 d . . O6 O -0.1790(4) 0.3635(3) -0.2422(2) 0.0796(8) Uani 1 d . . H30 H -0.0858(46) 0.3342(40) -0.2519(19) 0.119 Uiso 1 calc R . C9 C -0.2086(4) 0.3311(3) -0.1286(2) 0.0545(7) Uani 1 d . . O7 O 0.0432(3) 0.2089(2) -0.0969(2) 0.0576(6) Uani 1 d . . O8 O -0.1135(3) 0.2101(2) 0.0569(2) 0.0614(6) Uani 1 d . . C10 C -0.0804(3) 0.2411(3) -0.0491(2) 0.0403(6) Uani 1 d . . N1 N -0.5707(3) 0.2549(2) 0.3351(2) 0.0407(5) Uani 1 d . . H1 H -0.6396(3) 0.2523(2) 0.3959(2) 0.049 Uiso 1 calc R . N2 N -0.3834(3) 0.2619(2) 0.1694(2) 0.0397(5) Uani 1 d . . H14 H -0.3142(3) 0.2644(2) 0.1088(2) 0.048 Uiso 1 calc R . C1 C -0.5951(4) 0.3756(3) 0.2529(2) 0.0431(6) Uani 1 d . . H2 H -0.5343(4) 0.4706(3) 0.3096(2) 0.052 Uiso 1 calc R . H3 H -0.7464(4) 0.3566(3) 0.2074(2) 0.052 Uiso 1 calc R . C2 C -0.4795(4) 0.3807(3) 0.1519(2) 0.0438(6) Uani 1 d . . H4 H -0.5801(4) 0.3647(3) 0.0625(2) 0.053 Uiso 1 calc R . H5 H -0.3674(4) 0.4775(3) 0.1652(2) 0.053 Uiso 1 calc R . C3 C -0.2254(4) 0.2868(3) 0.3063(2) 0.0471(6) Uani 1 d . . H6 H -0.1105(4) 0.3824(3) 0.3206(2) 0.057 Uiso 1 calc R . H7 H -0.1625(4) 0.2098(3) 0.3164(2) 0.057 Uiso 1 calc R . C4 C -0.3398(4) 0.2831(3) 0.4065(2) 0.0494(6) Uani 1 d . . H8 H -0.3260(4) 0.2051(3) 0.4610(2) 0.059 Uiso 1 calc R . H9 H -0.2757(4) 0.3775(3) 0.4644(2) 0.059 Uiso 1 calc R . C5 C -0.6708(4) 0.1092(3) 0.2475(2) 0.0509(7) Uani 1 d . . H10 H -0.8223(4) 0.0900(3) 0.2026(2) 0.061 Uiso 1 calc R . H11 H -0.6585(4) 0.0297(3) 0.3004(2) 0.061 Uiso 1 calc R . C6 C -0.5569(4) 0.1140(3) 0.1460(2) 0.0472(6) Uani 1 d . . H12 H -0.4958(4) 0.0361(3) 0.1542(2) 0.057 Uiso 1 calc R . H13 H -0.6585(4) 0.0977(3) 0.0568(2) 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 O1 0.0718(12) 0.0676(12) 0.0503(10) 0.0204(8) 0.0372(9) 0.0408(9) O2 0.0725(12) 0.0701(12) 0.0583(11) 0.0209(9) 0.0425(10) 0.0432(10) C7 0.0385(12) 0.0492(13) 0.0355(12) 0.0048(9) 0.0167(10) 0.0195(10) O3 0.0956(15) 0.0673(13) 0.0681(12) 0.0311(10) 0.0515(11) 0.0513(11) O4 0.121(2) 0.0735(14) 0.0906(15) 0.0299(11) 0.0713(14) 0.0642(14) C8 0.0578(15) 0.0535(15) 0.0499(14) 0.0115(11) 0.0293(12) 0.0273(12) O5 0.142(2) 0.163(2) 0.098(2) 0.080(2) 0.091(2) 0.128(2) O6 0.112(2) 0.127(2) 0.0676(13) 0.0549(13) 0.0615(13) 0.095(2) C9 0.065(2) 0.077(2) 0.0521(15) 0.0245(12) 0.0383(13) 0.0462(14) O7 0.0642(12) 0.0888(14) 0.0457(10) 0.0159(9) 0.0278(9) 0.0505(10) O8 0.0684(12) 0.0987(15) 0.0475(10) 0.0291(10) 0.0336(9) 0.0537(11) C10 0.0397(12) 0.0504(14) 0.0350(12) 0.0016(9) 0.0155(10) 0.0185(10) N1 0.0472(11) 0.0482(11) 0.0403(11) 0.0120(8) 0.0243(9) 0.0244(9) N2 0.0410(10) 0.0524(12) 0.0384(10) 0.0095(8) 0.0211(8) 0.0253(9) C1 0.0488(13) 0.0490(14) 0.0451(13) 0.0131(10) 0.0200(10) 0.0300(11) C2 0.0503(13) 0.0520(14) 0.0416(13) 0.0122(10) 0.0188(10) 0.0300(11) C3 0.0394(13) 0.0587(15) 0.0463(14) 0.0086(10) 0.0103(10) 0.0244(11) C4 0.0495(14) 0.068(2) 0.0373(12) 0.0069(10) 0.0099(10) 0.0328(12) C5 0.0512(14) 0.0433(14) 0.061(2) 0.0036(11) 0.0250(12) 0.0136(11) C6 0.0505(14) 0.0471(14) 0.0461(13) -0.0016(10) 0.0162(11) 0.0199(11) _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 1.239(3) . ? O2 C7 1.232(3) . ? C7 C8 1.542(3) . ? O3 C8 1.318(3) . ? O3 H20 0.82 . ? O4 C8 1.204(3) . ? O5 C9 1.202(3) . ? O6 C9 1.313(3) . ? O6 H30 0.82 . ? C9 C10 1.533(3) . ? O7 C10 1.237(3) . ? O8 C10 1.241(3) . ? N1 C4 1.486(3) . ? N1 C5 1.490(3) . ? N1 C1 1.491(3) . ? N1 H1 0.91 . ? N2 C6 1.486(3) . ? N2 C2 1.492(3) . ? N2 C3 1.495(3) . ? N2 H14 0.91 . ? C1 C2 1.517(3) . ? C1 H2 0.97 . ? C1 H3 0.97 . ? C2 H4 0.97 . ? C2 H5 0.97 . ? C3 C4 1.506(3) . ? C3 H6 0.97 . ? C3 H7 0.97 . ? C4 H8 0.97 . ? C4 H9 0.97 . ? C5 C6 1.513(3) . ? C5 H10 0.97 . ? C5 H11 0.97 . ? C6 H12 0.97 . ? C6 H13 0.97 . ? 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 C7 O1 126.8(2) . . ? O2 C7 C8 116.7(2) . . ? O1 C7 C8 116.5(2) . . ? C8 O3 H20 109.47(13) . . ? O4 C8 O3 121.8(2) . . ? O4 C8 C7 122.6(2) . . ? O3 C8 C7 115.6(2) . . ? C9 O6 H30 109.47(13) . . ? O5 C9 O6 121.7(2) . . ? O5 C9 C10 121.9(2) . . ? O6 C9 C10 116.4(2) . . ? O7 C10 O8 127.9(2) . . ? O7 C10 C9 117.0(2) . . ? O8 C10 C9 115.2(2) . . ? C4 N1 C5 110.1(2) . . ? C4 N1 C1 110.6(2) . . ? C5 N1 C1 109.3(2) . . ? C4 N1 H1 108.93(11) . . ? C5 N1 H1 108.93(11) . . ? C1 N1 H1 108.93(10) . . ? C6 N2 C2 109.5(2) . . ? C6 N2 C3 110.0(2) . . ? C2 N2 C3 110.4(2) . . ? C6 N2 H14 108.94(11) . . ? C2 N2 H14 108.94(11) . . ? C3 N2 H14 108.94(10) . . ? N1 C1 C2 109.0(2) . . ? N1 C1 H2 109.88(11) . . ? C2 C1 H2 109.88(13) . . ? N1 C1 H3 109.88(11) . . ? C2 C1 H3 109.88(12) . . ? H2 C1 H3 108.3 . . ? N2 C2 C1 108.6(2) . . ? N2 C2 H4 109.96(11) . . ? C1 C2 H4 109.96(12) . . ? N2 C2 H5 109.96(12) . . ? C1 C2 H5 109.96(13) . . ? H4 C2 H5 108.3 . . ? N2 C3 C4 109.0(2) . . ? N2 C3 H6 109.89(11) . . ? C4 C3 H6 109.89(14) . . ? N2 C3 H7 109.89(11) . . ? C4 C3 H7 109.89(12) . . ? H6 C3 H7 108.3 . . ? N1 C4 C3 109.1(2) . . ? N1 C4 H8 109.85(12) . . ? C3 C4 H8 109.85(12) . . ? N1 C4 H9 109.85(12) . . ? C3 C4 H9 109.85(13) . . ? H8 C4 H9 108.3 . . ? N1 C5 C6 108.9(2) . . ? N1 C5 H10 109.91(12) . . ? C6 C5 H10 109.91(13) . . ? N1 C5 H11 109.91(12) . . ? C6 C5 H11 109.91(13) . . ? H10 C5 H11 108.3 . . ? N2 C6 C5 109.0(2) . . ? N2 C6 H12 109.88(11) . . ? C5 C6 H12 109.88(13) . . ? N2 C6 H13 109.88(11) . . ? C5 C6 H13 109.88(13) . . ? H12 C6 H13 108.3 . . ? _refine_diff_density_max 0.253 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.048 #PRO data_sad_PRO _database_code_CSD 151830 _audit_creation_method SHELXL _chemical_name_systematic ; 'Propylaminium Oxalate' ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H24 N2 O9' _chemical_formula_weight 316.31 _chemical_melting_point ? _chemical_compound_source ? 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 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 21.6428(9) _cell_length_b 5.6737(2) _cell_length_c 14.3086(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.6300(10) _cell_angle_gamma 90.00 _cell_volume 1584.14(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method ? _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3082 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 23.23 _reflns_number_total 1134 _reflns_number_observed 970 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0909P)^2^+0.3052P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0595(55) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1134 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_obs 0.0434 _refine_ls_wR_factor_all 0.1366 _refine_ls_wR_factor_obs 0.1171 _refine_ls_goodness_of_fit_all 1.119 _refine_ls_goodness_of_fit_obs 1.044 _refine_ls_restrained_S_all 1.119 _refine_ls_restrained_S_obs 1.044 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O100 O 0.0000 0.0774(4) 0.2500 0.0435(6) Uani 1 d S . O4 O -0.08313(8) -0.7193(2) -0.04283(11) 0.0589(6) Uani 1 d . . O3 O -0.09418(8) -0.2802(3) -0.12027(10) 0.0564(5) Uani 1 d . . O2 O -0.07710(9) -0.1354(3) 0.03330(11) 0.0584(6) Uani 1 d . . O1 O -0.06434(8) -0.5672(3) 0.10991(10) 0.0556(5) Uani 1 d . . C11 C -0.07645(9) -0.5521(3) 0.01770(14) 0.0379(6) Uani 1 d . . C10 C -0.08344(9) -0.3052(3) -0.03125(13) 0.0370(5) Uani 1 d . . N1 N -0.09037(8) -0.2754(3) 0.25224(12) 0.0453(6) Uani 1 d . . H10 H -0.05837(8) -0.1686(3) 0.26007(12) 0.068 Uiso 1 calc R . H9 H -0.08775(8) -0.3933(3) 0.21310(12) 0.068 Uiso 1 calc R . H8 H -0.08376(8) -0.3307(3) 0.31406(12) 0.068 Uiso 1 calc R . C2 C -0.21657(12) -0.3324(5) 0.1849(2) 0.0728(8) Uani 1 d . . H5 H -0.20893(12) -0.4001(5) 0.2513(2) 0.087 Uiso 1 calc R . H4 H -0.25901(12) -0.2437(5) 0.1598(2) 0.087 Uiso 1 calc R . C3 C -0.15895(10) -0.1647(4) 0.2015(2) 0.0548(6) Uani 1 d . . H7 H -0.16526(10) -0.1015(4) 0.1349(2) 0.066 Uiso 1 calc R . H6 H -0.16096(10) -0.0340(4) 0.2438(2) 0.066 Uiso 1 calc R . C1 C -0.22505(15) -0.5279(6) 0.1109(2) 0.0841(9) Uani 1 d . . H3 H -0.26273(15) -0.6259(6) 0.1049(2) 0.126 Uiso 1 calc R . H2 H -0.18385(15) -0.6203(6) 0.1358(2) 0.126 Uiso 1 calc R . H1 H -0.23403(15) -0.4635(6) 0.0442(2) 0.126 Uiso 1 calc R . H11 H -0.0796(13) -0.0037(59) 0.0072(20) 0.076(9) Uiso 1 d . . H100 H 0.0191(11) 0.1651(46) 0.2965(17) 0.056(7) 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 O100 0.0606(12) 0.0300(12) 0.0337(12) 0.000 0.0147(9) 0.000 O4 0.1093(13) 0.0253(9) 0.0440(9) -0.0009(7) 0.0351(8) 0.0019(8) O3 0.0974(12) 0.0350(10) 0.0358(9) 0.0039(6) 0.0278(7) 0.0020(7) O2 0.1119(13) 0.0242(10) 0.0443(10) -0.0004(7) 0.0385(8) 0.0025(8) O1 0.0990(12) 0.0343(9) 0.0401(9) 0.0088(6) 0.0362(7) 0.0178(7) C11 0.0516(11) 0.0292(12) 0.0351(11) 0.0014(8) 0.0209(8) 0.0051(8) C10 0.0491(11) 0.0285(11) 0.0330(11) -0.0010(8) 0.0173(8) 0.0017(8) N1 0.0573(10) 0.0406(10) 0.0414(10) -0.0019(7) 0.0245(8) -0.0040(8) C2 0.0595(13) 0.085(2) 0.069(2) -0.0073(14) 0.0235(11) -0.0037(13) C3 0.0633(13) 0.0462(14) 0.0500(12) -0.0034(10) 0.0200(10) 0.0064(10) C1 0.083(2) 0.066(2) 0.089(2) -0.0100(14) 0.0235(14) -0.0176(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 O100 H100 0.79(2) . ? O4 C11 1.250(2) . ? O3 C10 1.200(2) . ? O2 C10 1.300(2) . ? O2 H11 0.83(3) . ? O1 C11 1.232(2) . ? C11 C10 1.544(3) . ? N1 C3 1.481(3) . ? N1 H10 0.89 . ? N1 H9 0.89 . ? N1 H8 0.89 . ? C2 C1 1.489(4) . ? C2 C3 1.504(4) . ? C2 H5 0.97 . ? C2 H4 0.97 . ? C3 H7 0.97 . ? C3 H6 0.97 . ? C1 H3 0.96 . ? C1 H2 0.96 . ? C1 H1 0.96 . ? 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 C10 O2 H11 112.5(19) . . ? O1 C11 O4 126.6(2) . . ? O1 C11 C10 118.9(2) . . ? O4 C11 C10 114.5(2) . . ? O3 C10 O2 125.4(2) . . ? O3 C10 C11 121.6(2) . . ? O2 C10 C11 113.0(2) . . ? C3 N1 H10 109.47(11) . . ? C3 N1 H9 109.47(11) . . ? H10 N1 H9 109.5 . . ? C3 N1 H8 109.47(11) . . ? H10 N1 H8 109.5 . . ? H9 N1 H8 109.5 . . ? C1 C2 C3 115.0(2) . . ? C1 C2 H5 108.5(2) . . ? C3 C2 H5 108.53(13) . . ? C1 C2 H4 108.5(2) . . ? C3 C2 H4 108.53(14) . . ? H5 C2 H4 107.5 . . ? N1 C3 C2 113.3(2) . . ? N1 C3 H7 108.91(11) . . ? C2 C3 H7 108.91(13) . . ? N1 C3 H6 108.91(10) . . ? C2 C3 H6 108.91(14) . . ? H7 C3 H6 107.7 . . ? C2 C1 H3 109.5(2) . . ? C2 C1 H2 109.5(2) . . ? H3 C1 H2 109.5 . . ? C2 C1 H1 109.5(2) . . ? H3 C1 H1 109.5 . . ? H2 C1 H1 109.5 . . ? _refine_diff_density_max 0.280 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.106