# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Lee Brammer' 'Christer B. Aakeroy' 'Eric A. Bruton' 'Destin S. Leinen' 'F. Christopher Pigge' _publ_contact_author_name 'Dr Lee Brammer' _publ_contact_author_address ; Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email LEE.BRAMMER@SHEFFIELD.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Aromatic and aliphatic dioximes in non-covalent synthesis: synthon robustness tests ; data_l6402sd _database_code_CSD 203661 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common E,E-isophthalaldoxime _chemical_melting_point '181 - 184 deg C' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 N2 O2' _chemical_formula_weight 164.16 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 10.1860(4) _cell_length_b 11.0510(3) _cell_length_c 7.6536(3) _cell_angle_alpha 90.00 _cell_angle_beta 119.445(2) _cell_angle_gamma 90.00 _cell_volume 750.25(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(5) _cell_measurement_reflns_used 2458 _cell_measurement_theta_min 2.945 _cell_measurement_theta_max 28.174 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5209 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 28.27 _reflns_number_total 930 _reflns_number_gt 795 _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(Sheldrick, 2001)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2001)' _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^)+(0.0771P)^2^+0.3136P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 930 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.0000 0.33975(15) 0.2500 0.0197(4) Uani 1 2 d S . . O2 O -0.23124(12) 0.39050(9) -0.44288(14) 0.0278(3) Uani 1 1 d . . . N1 N -0.17806(12) 0.30229(9) -0.28974(16) 0.0213(3) Uani 1 1 d . . . C2 C -0.06336(13) 0.27805(11) 0.06771(17) 0.0195(3) Uani 1 1 d . . . C5 C -0.12776(14) 0.35014(12) -0.11738(19) 0.0212(3) Uani 1 1 d . . . C4 C 0.0000 0.08951(16) 0.2500 0.0228(4) Uani 1 2 d S . . C3 C -0.06388(14) 0.15128(12) 0.06897(19) 0.0213(3) Uani 1 1 d . . . H3 H -0.1115(18) 0.1081(16) -0.053(3) 0.028(4) Uiso 1 1 d . . . H4 H 0.0000 0.002(2) 0.2500 0.028(6) Uiso 1 2 d S . . H1 H 0.0000 0.429(2) 0.2500 0.023(5) Uiso 1 2 d S . . H5 H -0.1266(18) 0.4344(19) -0.099(2) 0.035(4) Uiso 1 1 d . . . H1A H -0.275(2) 0.343(2) -0.573(3) 0.062(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0227(8) 0.0165(8) 0.0194(8) 0.000 0.0100(7) 0.000 O2 0.0408(6) 0.0202(5) 0.0174(5) 0.0048(3) 0.0105(4) 0.0019(4) N1 0.0258(6) 0.0202(5) 0.0158(5) 0.0044(4) 0.0085(4) 0.0020(4) C2 0.0202(6) 0.0211(6) 0.0171(6) 0.0005(4) 0.0090(5) 0.0004(4) C5 0.0247(6) 0.0190(6) 0.0189(6) 0.0006(4) 0.0100(5) 0.0000(5) C4 0.0256(9) 0.0174(8) 0.0256(9) 0.000 0.0127(8) 0.000 C3 0.0230(6) 0.0206(6) 0.0199(6) -0.0033(5) 0.0102(5) -0.0013(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 C1 C2 1.3938(14) . ? C1 C2 1.3938(14) 2 ? O2 N1 1.4118(13) . ? N1 C5 1.2719(16) . ? C2 C3 1.4011(19) . ? C2 C5 1.4690(16) . ? C4 C3 1.3866(15) . ? C4 C3 1.3866(15) 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 C1 C2 121.43(15) . 2 ? C5 N1 O2 111.62(10) . . ? C1 C2 C3 118.93(11) . . ? C1 C2 C5 117.88(11) . . ? C3 C2 C5 123.20(11) . . ? N1 C5 C2 122.41(11) . . ? C3 C4 C3 121.02(16) . 2 ? C4 C3 C2 119.85(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1A N1 1.01(2) 1.85(3) 2.7789(15) 150.6(18) 7_454 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.315 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.055 ####################################################### data_l9202q _database_code_CSD 203662 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,3-diacetylbenzemedioxime _chemical_melting_point '206 - 208 deg C' _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 P2(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 3.897(2) _cell_length_b 14.757(9) _cell_length_c 16.305(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.668(14) _cell_angle_gamma 90.00 _cell_volume 937.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 148(5) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9697 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 148(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffrcatometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8752 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.34 _reflns_number_total 2237 _reflns_number_gt 1611 _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, 1997)' _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^)+(0.0838P)^2^+0.3582P] 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 2237 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0902 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1185(5) 0.43342(9) 0.07626(10) 0.0279(4) Uani 1 1 d . . . O2 O 0.8361(5) 0.95486(11) -0.08330(9) 0.0303(4) Uani 1 1 d . . . N1 N 0.1924(5) 0.52713(11) 0.07555(11) 0.0214(4) Uani 1 1 d . . . N2 N 0.7937(5) 0.91362(11) -0.00559(11) 0.0234(4) Uani 1 1 d . . . C1 C 0.4467(5) 0.65219(13) 0.14153(12) 0.0190(4) Uani 1 1 d . . . C3 C 0.5660(5) 0.79217(13) 0.06896(12) 0.0190(4) Uani 1 1 d . . . C4 C 0.5940(6) 0.83736(14) 0.14437(13) 0.0244(5) Uani 1 1 d . . . C8 C 0.6197(5) 0.83956(13) -0.00996(12) 0.0196(5) Uani 1 1 d . . . C7 C 0.3620(5) 0.55398(13) 0.13960(12) 0.0190(5) Uani 1 1 d . . . C2 C 0.4912(5) 0.69998(13) 0.06827(13) 0.0189(4) Uani 1 1 d . . . C6 C 0.4830(6) 0.69772(14) 0.21599(13) 0.0228(5) Uani 1 1 d . . . C10 C 0.4791(6) 0.79980(16) -0.08888(14) 0.0257(5) Uani 1 1 d . . . C5 C 0.5533(6) 0.79016(15) 0.21675(14) 0.0274(5) Uani 1 1 d . . . C9 C 0.4714(7) 0.49404(16) 0.20942(16) 0.0274(5) Uani 1 1 d . . . H2 H 0.479(6) 0.6661(15) 0.0189(14) 0.022(6) Uiso 1 1 d . . . H6 H 0.452(6) 0.6662(17) 0.2676(15) 0.029(6) Uiso 1 1 d . . . H5 H 0.571(7) 0.8233(18) 0.2674(16) 0.037(7) Uiso 1 1 d . . . H10C H 0.252(7) 0.7732(17) -0.0803(15) 0.028(7) Uiso 1 1 d . . . H4 H 0.644(6) 0.8988(17) 0.1481(15) 0.028(6) Uiso 1 1 d . . . H9C H 0.676(8) 0.514(2) 0.2338(18) 0.049(8) Uiso 1 1 d . . . H10B H 0.627(8) 0.7538(19) -0.1094(18) 0.044(8) Uiso 1 1 d . . . H10A H 0.456(8) 0.847(2) -0.1298(18) 0.049(8) Uiso 1 1 d . . . H2A H 0.965(8) 1.008(2) -0.0643(19) 0.062(10) Uiso 1 1 d . . . H9B H 0.469(8) 0.433(2) 0.1954(19) 0.058(9) Uiso 1 1 d . . . H1A H 0.015(9) 0.430(2) 0.028(2) 0.060(10) Uiso 1 1 d . . . H9A H 0.330(10) 0.501(3) 0.254(2) 0.078(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 O1 0.0428(10) 0.0118(7) 0.0287(9) 0.0006(6) -0.0041(7) -0.0059(6) O2 0.0456(11) 0.0231(8) 0.0223(9) 0.0051(6) 0.0025(7) -0.0091(7) N1 0.0299(10) 0.0113(8) 0.0229(10) -0.0008(7) 0.0009(7) -0.0027(7) N2 0.0309(11) 0.0180(8) 0.0215(10) 0.0030(7) 0.0025(8) -0.0032(7) C1 0.0179(10) 0.0172(9) 0.0216(11) -0.0012(8) -0.0019(8) 0.0004(8) C3 0.0172(10) 0.0184(9) 0.0216(11) 0.0001(8) 0.0017(8) -0.0009(7) C4 0.0322(13) 0.0166(10) 0.0243(11) -0.0037(9) -0.0010(9) -0.0053(9) C8 0.0195(10) 0.0164(9) 0.0231(11) -0.0003(8) 0.0018(8) 0.0007(8) C7 0.0194(11) 0.0173(9) 0.0205(10) 0.0000(8) 0.0019(8) 0.0008(7) C2 0.0204(11) 0.0176(10) 0.0187(11) -0.0030(8) 0.0000(8) -0.0002(8) C6 0.0257(11) 0.0234(10) 0.0193(11) 0.0018(9) 0.0007(8) -0.0038(9) C10 0.0305(13) 0.0258(11) 0.0205(11) 0.0012(9) -0.0011(9) -0.0045(10) C5 0.0367(14) 0.0256(11) 0.0199(12) -0.0064(9) -0.0003(9) -0.0053(9) C9 0.0361(14) 0.0211(11) 0.0247(12) 0.0068(9) -0.0054(10) -0.0019(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.413(2) . ? O2 N2 1.420(2) . ? N1 C7 1.282(3) . ? N2 C8 1.287(3) . ? C1 C6 1.391(3) . ? C1 C2 1.402(3) . ? C1 C7 1.486(3) . ? C3 C2 1.391(3) . ? C3 C4 1.400(3) . ? C3 C8 1.485(3) . ? C4 C5 1.383(3) . ? C8 C10 1.503(3) . ? C7 C9 1.494(3) . ? C6 C5 1.391(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 O1 113.34(16) . . ? C8 N2 O2 112.92(17) . . ? C6 C1 C2 119.24(18) . . ? C6 C1 C7 120.41(18) . . ? C2 C1 C7 120.35(18) . . ? C2 C3 C4 118.93(19) . . ? C2 C3 C8 119.24(18) . . ? C4 C3 C8 121.82(18) . . ? C5 C4 C3 120.09(19) . . ? N2 C8 C3 116.06(18) . . ? N2 C8 C10 123.87(19) . . ? C3 C8 C10 120.06(18) . . ? N1 C7 C1 115.30(17) . . ? N1 C7 C9 124.51(19) . . ? C1 C7 C9 120.19(18) . . ? C3 C2 C1 121.07(18) . . ? C1 C6 C5 119.7(2) . . ? C4 C5 C6 120.9(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N1 0.88(3) 1.95(3) 2.785(3) 157(3) 3_565 O1 H1A O1 0.88(3) 2.68(3) 3.281(3) 127(3) 3_565 O2 H2A N2 0.98(3) 1.86(3) 2.798(3) 160(3) 3_775 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.307 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.064 ####################################################### data_l15302q _database_code_CSD 203663 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common E,E-1,3-benzenediamidioxime _chemical_melting_point '180 - 181 deg C' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N4 O2' _chemical_formula_weight 194.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 13.1956(15) _cell_length_b 12.1099(17) _cell_length_c 11.8156(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.412(8) _cell_angle_gamma 90.00 _cell_volume 1850.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 123(5) _cell_measurement_reflns_used 1377 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 26.23 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7314 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0872 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2145 _reflns_number_gt 1258 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2001)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2001)' _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^)+(0.0523P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2145 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1146 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.92571(10) 0.52481(13) 0.36165(13) 0.0274(4) Uani 1 1 d . . . H1 H 0.961(2) 0.591(2) 0.359(3) 0.065(9) Uiso 1 1 d . . . N1 N 0.86217(11) 0.51381(13) 0.25068(15) 0.0203(4) Uani 1 1 d . . . C1 C 0.73592(14) 0.39673(15) 0.13843(19) 0.0190(5) Uani 1 1 d . . . O2 O 0.34595(9) 0.18721(11) 0.10705(13) 0.0219(4) Uani 1 1 d . . . H2 H 0.3515(17) 0.124(2) 0.157(2) 0.052(8) Uiso 1 1 d . . . C2 C 0.63674(14) 0.35828(15) 0.1429(2) 0.0194(5) Uani 1 1 d . . . H2C H 0.6158(15) 0.3509(16) 0.218(2) 0.023(6) Uiso 1 1 d . . . N2 N 0.81485(16) 0.35464(16) 0.33708(19) 0.0343(5) Uani 1 1 d . . . H2A H 0.8582(17) 0.3678(19) 0.403(2) 0.034(7) Uiso 1 1 d . . . H2B H 0.7798(19) 0.291(2) 0.334(2) 0.054(8) Uiso 1 1 d . . . N3 N 0.45220(11) 0.21124(13) 0.10624(15) 0.0201(4) Uani 1 1 d . . . C3 C 0.56632(14) 0.33599(15) 0.04117(19) 0.0192(5) Uani 1 1 d . . . C4 C 0.59529(16) 0.34931(16) -0.0646(2) 0.0238(5) Uani 1 1 d . . . H4 H 0.5467(15) 0.3340(16) -0.1333(19) 0.022(6) Uiso 1 1 d . . . N4 N 0.37945(14) 0.35975(15) -0.01028(18) 0.0275(5) Uani 1 1 d . . . H4A H 0.3147(17) 0.3478(17) 0.004(2) 0.033(7) Uiso 1 1 d . . . H4B H 0.3928(15) 0.4266(19) -0.0310(19) 0.027(6) Uiso 1 1 d . . . C5 C 0.69488(16) 0.38464(17) -0.0687(2) 0.0249(5) Uani 1 1 d . . . H5 H 0.7135(16) 0.3923(19) -0.145(2) 0.043(7) Uiso 1 1 d . . . C6 C 0.76458(16) 0.40829(15) 0.0319(2) 0.0208(5) Uani 1 1 d . . . H6 H 0.8340(15) 0.4315(16) 0.0300(19) 0.028(6) Uiso 1 1 d . . . C7 C 0.80888(14) 0.42338(16) 0.24713(19) 0.0197(5) Uani 1 1 d . . . C8 C 0.45984(14) 0.29945(15) 0.04805(19) 0.0188(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0248(8) 0.0316(8) 0.0240(10) -0.0018(7) 0.0006(7) -0.0105(6) N1 0.0174(8) 0.0233(9) 0.0192(11) -0.0007(8) 0.0009(7) -0.0026(7) C1 0.0183(10) 0.0160(9) 0.0225(13) 0.0015(9) 0.0039(9) 0.0021(7) O2 0.0162(7) 0.0220(7) 0.0267(10) 0.0028(7) 0.0027(6) -0.0024(6) C2 0.0205(10) 0.0190(10) 0.0191(13) 0.0027(10) 0.0050(9) 0.0006(8) N2 0.0383(11) 0.0318(11) 0.0263(13) 0.0110(10) -0.0093(10) -0.0157(9) N3 0.0144(8) 0.0230(9) 0.0226(11) 0.0017(8) 0.0032(7) -0.0024(6) C3 0.0181(10) 0.0164(10) 0.0234(13) -0.0002(9) 0.0047(9) 0.0010(7) C4 0.0267(12) 0.0239(11) 0.0197(13) -0.0009(10) 0.0024(10) -0.0023(9) N4 0.0188(10) 0.0205(10) 0.0412(14) 0.0096(9) 0.0009(8) -0.0015(7) C5 0.0277(11) 0.0272(11) 0.0215(14) 0.0020(11) 0.0092(10) 0.0003(9) C6 0.0191(10) 0.0185(10) 0.0257(14) 0.0013(9) 0.0062(9) 0.0003(8) C7 0.0168(9) 0.0191(10) 0.0235(13) 0.0011(9) 0.0047(9) -0.0010(8) C8 0.0189(10) 0.0177(10) 0.0188(12) -0.0022(9) 0.0010(9) 0.0008(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 O1 N1 1.416(2) . ? N1 C7 1.298(2) . ? C1 C6 1.391(3) . ? C1 C2 1.400(3) . ? C1 C7 1.480(3) . ? O2 N3 1.4338(19) . ? C2 C3 1.392(3) . ? N2 C7 1.340(3) . ? N3 C8 1.285(2) . ? C3 C4 1.386(3) . ? C3 C8 1.491(3) . ? C4 C5 1.392(3) . ? N4 C8 1.358(2) . ? C5 C6 1.381(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 O1 109.10(17) . . ? C6 C1 C2 119.40(19) . . ? C6 C1 C7 121.09(18) . . ? C2 C1 C7 119.5(2) . . ? C3 C2 C1 120.1(2) . . ? C8 N3 O2 110.65(14) . . ? C4 C3 C2 119.95(18) . . ? C4 C3 C8 120.97(18) . . ? C2 C3 C8 119.1(2) . . ? C3 C4 C5 119.9(2) . . ? C6 C5 C4 120.4(2) . . ? C5 C6 C1 120.2(2) . . ? N1 C7 N2 123.5(2) . . ? N1 C7 C1 117.86(18) . . ? N2 C7 C1 118.60(17) . . ? N3 C8 N4 125.62(18) . . ? N3 C8 C3 116.77(16) . . ? N4 C8 C3 117.57(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 N1 0.96(3) 1.72(3) 2.682(2) 177(2) 3_445 O1 H1 N3 0.92(3) 1.85(3) 2.756(2) 165(3) 4_655 N4 H4A O2 0.91(2) 2.30(2) 3.022(2) 135.6(19) 7 N2 H2B O2 0.90(3) 2.29(3) 3.099(2) 149(2) 2_655 N2 H2A O2 0.88(2) 2.54(3) 3.175(3) 129.4(18) 8_556 N2 H2A N3 0.88(2) 2.66(3) 3.428(3) 146.7(19) 8_556 N2 H2B N4 0.90(3) 2.73(3) 3.180(3) 111.9(18) 8_556 N2 H2B O2 0.90(3) 2.29(3) 3.099(2) 149(2) 2_655 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.231 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.056 ###################################################### data_l1802f _database_code_CSD 203664 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common E,E-terephathalaldoxime _chemical_melting_point '219-220 deg C' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 N2 O2' _chemical_formula_weight 164.16 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 13.6142(8) _cell_length_b 4.5032(3) _cell_length_c 13.1697(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.263(4) _cell_angle_gamma 90.00 _cell_volume 771.03(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(5) _cell_measurement_reflns_used 1126 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 26.317 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4984 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 28.28 _reflns_number_total 945 _reflns_number_gt 620 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2001)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2001)' _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^)+(0.0549P)^2^+0.3755P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 945 _refine_ls_number_parameters 71 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.27326(9) 0.2438(3) 0.15499(10) 0.0267(4) Uani 1 1 d . . . N1 N 0.19903(11) 0.4653(3) 0.15030(11) 0.0224(4) Uani 1 1 d . . . C1 C 0.04855(14) 0.9062(4) -0.07278(14) 0.0235(4) Uani 1 1 d . . . C2 C 0.07954(13) 0.7881(4) 0.02996(13) 0.0211(4) Uani 1 1 d . . . C3 C 0.02937(13) 0.8856(4) 0.10258(13) 0.0232(4) Uani 1 1 d . . . C4 C 0.16054(13) 0.5627(4) 0.05576(13) 0.0220(4) Uani 1 1 d . . . H1A H 0.283(2) 0.158(7) 0.225(3) 0.097(11) Uiso 1 1 d . . . H1 H 0.0829(15) 0.846(4) -0.1238(16) 0.029(5) Uiso 1 1 d . . . H3 H 0.0460(15) 0.806(4) 0.1753(17) 0.033(5) Uiso 1 1 d . . . H4 H 0.1833(14) 0.480(4) -0.0029(15) 0.026(5) 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 O1 0.0283(7) 0.0275(7) 0.0243(7) 0.0028(6) 0.0078(5) 0.0067(6) N1 0.0234(8) 0.0201(8) 0.0228(8) -0.0011(6) 0.0056(6) 0.0012(7) C1 0.0244(9) 0.0244(10) 0.0226(9) -0.0023(7) 0.0083(7) -0.0014(8) C2 0.0204(8) 0.0186(9) 0.0232(9) -0.0020(7) 0.0048(7) -0.0042(7) C3 0.0242(9) 0.0244(10) 0.0200(9) 0.0014(7) 0.0051(7) -0.0023(8) C4 0.0245(9) 0.0204(9) 0.0214(9) -0.0016(7) 0.0073(7) -0.0036(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 O1 N1 1.4083(18) . ? N1 C4 1.277(2) . ? C1 C3 1.382(3) 5_575 ? C1 C2 1.397(2) . ? C2 C3 1.401(2) . ? C2 C4 1.463(2) . ? C3 C1 1.382(3) 5_575 ? 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 C4 N1 O1 111.56(14) . . ? C3 C1 C2 121.24(16) 5_575 . ? C1 C2 C3 118.26(16) . . ? C1 C2 C4 118.63(15) . . ? C3 C2 C4 123.09(15) . . ? C1 C3 C2 120.50(16) 5_575 . ? N1 C4 C2 121.85(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N1 0.97(4) 1.81(4) 2.7777(19) 175(3) 4_545 C4 H4 O1 0.99(2) 2.47(2) 3.450(2) 175.4(15) 7 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.213 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.052 ################################################## data_Compound_5 _database_code_CSD 203665 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,4-diacetylbenzenedioxime _chemical_melting_point '170 deg C (dec)' _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1553(14) _cell_length_b 14.208(3) _cell_length_c 8.5134(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.525(4) _cell_angle_gamma 90.00 _cell_volume 935.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9828 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker SMART 1000 CCD diffractometer' ; _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 6388 _diffrn_reflns_av_R_equivalents 0.1587 _diffrn_reflns_av_sigmaI/netI 0.3008 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2152 _reflns_number_gt 426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1304P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap/geom _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2152 _refine_ls_number_parameters 57 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3456 _refine_ls_R_factor_gt 0.1139 _refine_ls_wR_factor_ref 0.3258 _refine_ls_wR_factor_gt 0.2412 _refine_ls_goodness_of_fit_ref 0.782 _refine_ls_restrained_S_all 0.782 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O7 O 1.2371(8) 0.2396(4) 1.4802(9) 0.0302(18) Uiso 1 1 d . . . H7 H 1.2997 0.1942 1.5721 0.036 Uiso 1 1 d R . . O9 O 0.2536(8) 0.0126(4) 0.5211(8) 0.0301(19) Uiso 1 1 d . . . H9 H 0.2003 0.0546 0.4268 0.036 Uiso 1 1 d R . . N7 N 1.1116(10) 0.1824(6) 1.3634(10) 0.025(2) Uiso 1 1 d . . . N9 N 0.3743(10) 0.0698(6) 0.6383(10) 0.023(2) Uiso 1 1 d . . . C1 C 0.8761(12) 0.1771(7) 1.1211(13) 0.020(2) Uiso 1 1 d . . . C2 C 0.8854(12) 0.0788(6) 1.1088(12) 0.026(2) Uiso 1 1 d . . . H2 H 0.9771 0.0453 1.1857 0.032 Uiso 1 1 calc R . . C3 C 0.7622(12) 0.0302(6) 0.9858(12) 0.023(2) Uiso 1 1 d . . . H3 H 0.7742 -0.0359 0.9779 0.027 Uiso 1 1 calc R . . C4 C 0.6234(13) 0.0740(7) 0.8749(13) 0.022(2) Uiso 1 1 d . . . C5 C 0.6096(11) 0.1721(6) 0.8906(11) 0.027(2) Uiso 1 1 d . . . H5 H 0.5129 0.2046 0.8188 0.032 Uiso 1 1 calc R . . C6 C 0.7341(12) 0.2209(7) 1.0082(12) 0.030(3) Uiso 1 1 d . . . H6 H 0.7234 0.2873 1.0131 0.036 Uiso 1 1 calc R . . C7 C 1.0098(9) 0.2332(8) 1.2506(9) 0.020(3) Uiso 1 1 d . . . C8 C 1.0130(9) 0.3367(8) 1.2355(9) 0.025(3) Uiso 1 1 d . . . H8A H 1.1089 0.3623 1.3265 0.030 Uiso 1 1 calc R . . H8B H 0.9036 0.3629 1.2404 0.030 Uiso 1 1 calc R . . H8C H 1.0287 0.3534 1.1295 0.030 Uiso 1 1 calc R . . C9 C 0.4888(10) 0.0235(8) 0.7400(10) 0.024(3) Uiso 1 1 d . . . C10 C 0.4963(10) -0.0848(9) 0.7387(10) 0.030(3) Uiso 1 1 d . . . H10A H 0.4047 -0.1089 0.6423 0.036 Uiso 1 1 calc R . . H10B H 0.4799 -0.1094 0.8403 0.036 Uiso 1 1 calc R . . H10C H 0.6091 -0.1050 0.7329 0.036 Uiso 1 1 calc R . . _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 O7 N7 1.431(11) . ? O9 N9 1.415(11) . ? N7 C7 1.275(12) . ? N9 C9 1.242(12) . ? C1 C6 1.395(15) . ? C1 C2 1.405(12) . ? C1 C7 1.508(13) . ? C2 C3 1.383(13) . ? C3 C4 1.371(15) . ? C4 C5 1.408(12) . ? C4 C9 1.496(13) . ? C5 C6 1.367(13) . ? C7 C8 1.477(16) . ? C9 C10 1.539(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N7 O7 110.7(9) . . ? C9 N9 O9 112.8(9) . . ? C6 C1 C2 116.4(10) . . ? C6 C1 C7 121.2(10) . . ? C2 C1 C7 122.4(10) . . ? C3 C2 C1 120.6(10) . . ? C4 C3 C2 122.5(10) . . ? C3 C4 C5 117.2(10) . . ? C3 C4 C9 123.7(10) . . ? C5 C4 C9 119.1(10) . . ? C6 C5 C4 120.6(10) . . ? C5 C6 C1 122.6(10) . . ? N7 C7 C8 127.1(9) . . ? N7 C7 C1 113.5(12) . . ? C8 C7 C1 119.4(8) . . ? N9 C9 C4 119.1(12) . . ? N9 C9 C10 123.2(9) . . ? C4 C9 C10 117.6(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 N9 1.02 1.89 2.815(11) 148.8 1_656 O7 H7 O9 1.02 2.62 3.243(6) 119.1 1_656 O9 H9 N7 0.98 1.97 2.824(11) 144.4 1_454 _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.570 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.093 ############################################ data_l13702q _database_code_CSD 203666 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,4-benzenediamidioxime _chemical_melting_point '210 deg C (dec.)' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N4 O2' _chemical_formula_weight 194.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.401(6) _cell_length_b 4.985(5) _cell_length_c 10.714(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.41(7) _cell_angle_gamma 90.00 _cell_volume 428.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 133(5) _cell_measurement_reflns_used 1391 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.05 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5153 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1052 _reflns_number_gt 715 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL 2001' _computing_publication_material 'Bruker SHELXTL 2001' _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^)+(0.0611P)^2^+0.0220P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1052 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.50243(13) 0.1871(2) 0.12520(12) 0.0220(3) Uani 1 1 d . . . N1 N 0.63830(15) 0.1947(2) 0.06929(13) 0.0176(3) Uani 1 1 d . . . C1 C 0.72001(18) 0.4186(3) 0.09973(15) 0.0154(4) Uani 1 1 d . . . N2 N 0.68641(17) 0.6056(3) 0.18049(13) 0.0190(4) Uani 1 1 d . . . C3 C 0.86297(18) 0.4610(3) 0.04817(15) 0.0156(4) Uani 1 1 d . . . C4 C 0.8753(2) 0.3224(3) -0.06159(17) 0.0239(4) Uani 1 1 d . . . C2 C 0.9909(2) 0.6399(3) 0.10888(18) 0.0224(4) Uani 1 1 d . . . H6 H 0.590(2) 0.589(4) 0.201(2) 0.031(5) Uiso 1 1 d . . . H5 H 0.718(2) 0.772(4) 0.172(2) 0.036(6) Uiso 1 1 d . . . H4 H 0.788(2) 0.207(4) -0.106(2) 0.043(6) Uiso 1 1 d . . . H2 H 0.982(2) 0.739(4) 0.180(2) 0.032(5) Uiso 1 1 d . . . H1 H 0.431(3) 0.062(5) 0.067(2) 0.067(8) 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 O1 0.0214(6) 0.0230(6) 0.0256(7) -0.0011(5) 0.0131(5) -0.0046(5) N1 0.0162(6) 0.0187(7) 0.0214(8) -0.0003(5) 0.0111(6) -0.0023(5) C1 0.0164(7) 0.0156(7) 0.0139(7) 0.0028(6) 0.0042(6) 0.0016(6) N2 0.0225(7) 0.0162(7) 0.0213(8) -0.0021(6) 0.0111(6) -0.0017(6) C3 0.0166(7) 0.0141(7) 0.0170(8) 0.0019(6) 0.0063(6) 0.0007(6) C4 0.0231(8) 0.0246(9) 0.0252(9) -0.0087(7) 0.0090(7) -0.0102(6) C2 0.0247(8) 0.0244(9) 0.0217(9) -0.0082(7) 0.0121(7) -0.0069(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.4396(19) . ? N1 C1 1.300(2) . ? C1 N2 1.358(2) . ? C1 C3 1.480(2) . ? C3 C4 1.394(2) . ? C3 C2 1.398(2) . ? C4 C2 1.377(3) 3_765 ? C2 C4 1.377(3) 3_765 ? 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 C1 N1 O1 110.06(13) . . ? N1 C1 N2 123.68(15) . . ? N1 C1 C3 117.12(14) . . ? N2 C1 C3 119.11(14) . . ? C4 C3 C2 117.88(15) . . ? C4 C3 C1 121.16(14) . . ? C2 C3 C1 120.95(15) . . ? C2 C4 C3 121.16(16) 3_765 . ? C4 C2 C3 120.96(16) 3_765 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.96(3) 1.90(3) 2.809(3) 158.4(19) 3_655 N2 H6 O1 0.903(19) 2.28(2) 2.999(3) 136.9(16) 2_655 N2 H5 N1 0.88(2) 2.38(2) 3.150(4) 145.6(17) 1_565 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.209 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.059 ################################################### data_Compound_2 _database_code_CSD 203667 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Fumaramidioxime _chemical_melting_point '213 deg C (dec.)' _chemical_formula_moiety ? _chemical_formula_sum 'C4 H8 N4 O2' _chemical_formula_weight 144.14 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 16.6296(17) _cell_length_b 3.6679(3) _cell_length_c 10.0529(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 613.18(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 4.74 _cell_measurement_theta_max 12.50 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9678 _exptl_absorpt_correction_T_max 0.9726 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 741 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.49 _reflns_number_total 741 _reflns_number_gt 672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0523P)^2^+0.2036P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_ls_number_reflns 741 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.15229(10) -0.6186(6) -0.1364(2) 0.0210(5) Uani 1 1 d . . . H1A H 0.1102 -0.6950 -0.0933 0.025 Uiso 1 1 d R . . O3 O 0.59316(10) 0.0958(5) 0.1284(2) 0.0205(5) Uani 1 1 d . . . H3A H 0.6404 0.1914 0.0805 0.025 Uiso 1 1 d R . . N1 N 0.20408(13) -0.4786(7) -0.0354(2) 0.0176(5) Uani 1 1 d . . . N2 N 0.29777(14) -0.5910(7) -0.2041(2) 0.0212(5) Uani 1 1 d . . . H2A H 0.2490 -0.7272 -0.2580 0.025 Uiso 1 1 d R . . H2B H 0.3500 -0.6694 -0.2242 0.025 Uiso 1 1 d R . . N3 N 0.54244(13) -0.0491(6) 0.0270(2) 0.0179(5) Uani 1 1 d . . . N4 N 0.45760(14) -0.1390(7) 0.2102(2) 0.0234(6) Uani 1 1 d . . . H4A H 0.4094 -0.2366 0.2430 0.028 Uiso 1 1 d R . . H4B H 0.4899 -0.0182 0.2614 0.028 Uiso 1 1 d R . . C1 C 0.27722(14) -0.4803(8) -0.0794(3) 0.0160(5) Uani 1 1 d . . . C2 C 0.33775(15) -0.3423(7) 0.0128(3) 0.0175(5) Uani 1 1 d . . . H2 H 0.3097 -0.2710 0.0942 0.021 Uiso 1 1 d R . . C3 C 0.41662(14) -0.3079(7) -0.0143(3) 0.0174(6) Uani 1 1 d . . . H3 H 0.4292 -0.3670 -0.1028 0.021 Uiso 1 1 d R . . C4 C 0.47560(15) -0.1631(7) 0.0796(3) 0.0154(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0135(9) 0.0332(12) 0.0164(9) -0.0002(9) -0.0024(8) -0.0048(8) O3 0.0167(9) 0.0276(11) 0.0172(9) -0.0009(9) -0.0029(9) -0.0054(8) N1 0.0150(11) 0.0236(12) 0.0142(11) -0.0012(10) -0.0023(9) -0.0029(10) N2 0.0160(11) 0.0316(13) 0.0162(12) -0.0038(11) 0.0010(10) -0.0019(10) N3 0.0150(10) 0.0217(11) 0.0172(12) -0.0019(10) -0.0014(9) -0.0015(9) N4 0.0192(12) 0.0343(13) 0.0166(12) -0.0052(11) 0.0030(10) -0.0063(10) C1 0.0141(11) 0.0171(11) 0.0168(12) 0.0034(11) 0.0003(11) -0.0003(9) C2 0.0164(11) 0.0197(12) 0.0165(12) -0.0010(11) -0.0001(11) 0.0010(10) C3 0.0177(12) 0.0186(12) 0.0157(13) -0.0008(11) -0.0001(10) -0.0018(10) C4 0.0162(12) 0.0158(12) 0.0141(12) 0.0012(11) 0.0001(11) 0.0019(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.427(3) . ? O3 N3 1.426(3) . ? N1 C1 1.294(3) . ? N2 C1 1.361(4) . ? N3 C4 1.300(3) . ? N4 C4 1.349(4) . ? C1 C2 1.459(4) . ? C2 C3 1.346(3) . ? C3 C4 1.462(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 C1 N1 O1 108.8(2) . . ? C4 N3 O3 109.6(2) . . ? N1 C1 N2 123.5(3) . . ? N1 C1 C2 115.4(2) . . ? N2 C1 C2 121.0(2) . . ? C3 C2 C1 125.2(2) . . ? C2 C3 C4 123.9(2) . . ? N3 C4 N4 124.4(3) . . ? N3 C4 C3 115.3(2) . . ? N4 C4 C3 120.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N3 0.87 1.90 2.743(3) 162.4 3_445 O3 H3A N1 0.99 1.89 2.843(3) 160.7 3 N2 H2B O3 0.94 2.35 3.091(3) 135.4 2_644 N4 H4A O1 0.94 2.12 2.968(3) 150.2 4 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.228 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.051 ############################################# data_Compound_1 _database_code_CSD 203668 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common succinamidioxime _chemical_melting_point '173-176 deg C' _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 N4 O2' _chemical_formula_weight 146.16 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 P2(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 4.8552(5) _cell_length_b 5.1714(2) _cell_length_c 13.2126(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.205(6) _cell_angle_gamma 90.00 _cell_volume 326.50(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 4.24 _cell_measurement_theta_max 16.34 _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 156 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9144 _exptl_absorpt_correction_T_max 0.9514 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 488 _diffrn_reflns_av_R_equivalents 0.0079 _diffrn_reflns_av_sigmaI/netI 0.0044 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 22.49 _reflns_number_total 429 _reflns_number_gt 414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0738P)^2^+0.3828P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 429 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_restrained_S_all 1.224 _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 N1 N -0.1138(4) 0.1991(4) 0.05877(16) 0.0177(7) Uani 1 1 d . . . N2 N -0.0976(5) 0.4479(4) 0.20805(16) 0.0215(7) Uani 1 1 d . . . H2A H 0.0999 0.3795 0.2392 0.026 Uiso 1 1 d R . . H2B H -0.1482 0.6287 0.2392 0.026 Uiso 1 1 d R . . O1 O 0.1190(4) 0.0705(4) 0.12066(14) 0.0231(7) Uani 1 1 d . . . H1 H 0.1696 -0.0709 0.0802 0.028 Uiso 1 1 d R . . C1 C -0.2020(5) 0.3867(5) 0.10803(19) 0.0148(8) Uani 1 1 d . . . C2 C -0.4454(5) 0.5434(5) 0.0548(2) 0.0166(8) Uani 1 1 d . . . H2C H -0.6053 0.5389 0.1011 0.020 Uiso 1 1 d R . . H2D H -0.3906 0.7289 0.0611 0.020 Uiso 1 1 d 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 N1 0.0166(12) 0.0187(13) 0.0159(13) 0.0019(10) -0.0028(9) 0.0067(9) N2 0.0236(13) 0.0241(13) 0.0148(14) -0.0037(10) -0.0022(10) 0.0050(10) O1 0.0215(12) 0.0239(12) 0.0203(12) -0.0008(8) -0.0058(8) 0.0123(8) C1 0.0149(13) 0.0147(14) 0.0146(15) 0.0006(11) 0.0021(11) -0.0026(11) C2 0.0172(15) 0.0137(14) 0.0179(15) -0.0011(11) -0.0001(11) 0.0029(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 N1 C1 1.284(3) . ? N1 O1 1.435(3) . ? N2 C1 1.366(3) . ? C1 C2 1.501(4) . ? C2 C2 1.519(5) 3_465 ? 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 C1 N1 O1 111.2(2) . . ? N1 C1 N2 124.4(2) . . ? N1 C1 C2 118.5(2) . . ? N2 C1 C2 117.0(2) . . ? C1 C2 C2 113.6(3) . 3_465 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O1 1.04 2.32 3.010(3) 123.0 2 N2 H2B N2 1.07 2.24 3.269(3) 160.1 2_455 O1 H1 N1 0.96 1.93 2.747(3) 141.6 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.339 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.150 ###END