# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Claudio Pettinari' _publ_contact_author_email CLAUDIO.PETTINARI@UNICAM.IT _publ_section_title ; Crystal structure, supramolecular assembly and preliminary reactivity behaviour of new heteropolytopic ligands based on oxalate/malonate skeleton and azolate moieties ; loop_ _publ_author_name 'Claudio Pettinari' 'Federica Garau' 'Magda Monari' 'Luciano Pandolfo' 'Alfonso Venzo' # Attachment 'comp1a.cif' data_legpa _database_code_depnum_ccdc_archive 'CCDC 746838' #TrackingRef 'comp1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 N4 O2' _chemical_formula_weight 190.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 11.0178(5) _cell_length_b 7.5596(4) _cell_length_c 10.9232(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.5910(10) _cell_angle_gamma 90.00 _cell_volume 871.92(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11100 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 30.05 _reflns_number_total 2558 _reflns_number_gt 1827 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0697P)^2^+0.1266P] 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 2558 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N2 N 0.68554(12) 0.21799(16) 0.53893(10) 0.0358(3) Uani 1 1 d . . . N1 N 0.66698(10) 0.29356(15) 0.64688(10) 0.0296(3) Uani 1 1 d . . . O2 O 0.61880(11) 0.61523(15) 0.45373(10) 0.0461(3) Uani 1 1 d . . . C1 C 0.67343(13) 0.47547(18) 0.66009(12) 0.0323(3) Uani 1 1 d . . . O1 O 0.65261(12) 0.55378(15) 0.74771(10) 0.0489(3) Uani 1 1 d . . . N3 N 0.82633(12) 0.62158(16) 0.57010(12) 0.0391(3) Uani 1 1 d . . . C2 C 0.70080(14) 0.57347(18) 0.54747(13) 0.0328(3) Uani 1 1 d . . . C5 C 0.63530(14) 0.17042(19) 0.72457(13) 0.0354(3) Uani 1 1 d . . . H5 H 0.6182 0.1918 0.8018 0.042 Uiso 1 1 calc R . . C3 C 0.66431(16) 0.0485(2) 0.55255(14) 0.0409(3) Uani 1 1 d . . . H3 H 0.6689 -0.0376 0.4932 0.049 Uiso 1 1 calc R . . C4 C 0.63384(15) 0.0121(2) 0.66703(14) 0.0406(3) Uani 1 1 d . . . H4 H 0.6164 -0.0977 0.6966 0.049 Uiso 1 1 calc R . . N4 N 0.91133(13) 0.5755(2) 0.68431(14) 0.0536(4) Uani 1 1 d . . . C8 C 0.88253(18) 0.7176(2) 0.49392(18) 0.0516(4) Uani 1 1 d . . . H8 H 0.8433 0.7626 0.4130 0.062 Uiso 1 1 calc R . . C7 C 1.0049(2) 0.7333(3) 0.5595(2) 0.0703(6) Uani 1 1 d . . . H7 H 1.0680 0.7907 0.5335 0.084 Uiso 1 1 calc R . . C6 C 1.01841(19) 0.6443(3) 0.6766(2) 0.0713(6) Uani 1 1 d . . . H6 H 1.0945 0.6354 0.7409 0.086 Uiso 1 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 N2 0.0473(7) 0.0342(6) 0.0281(5) -0.0010(4) 0.0145(5) 0.0021(5) N1 0.0346(6) 0.0305(6) 0.0245(5) -0.0005(4) 0.0100(4) -0.0007(4) O2 0.0462(6) 0.0473(6) 0.0400(6) 0.0098(5) 0.0046(5) 0.0016(5) C1 0.0352(7) 0.0328(7) 0.0286(6) -0.0015(5) 0.0086(5) -0.0008(5) O1 0.0722(8) 0.0399(6) 0.0416(6) -0.0088(5) 0.0277(6) -0.0032(5) N3 0.0381(7) 0.0386(7) 0.0403(7) 0.0045(5) 0.0111(5) -0.0017(5) C2 0.0400(7) 0.0275(6) 0.0310(6) -0.0009(5) 0.0105(6) 0.0006(5) C5 0.0409(7) 0.0375(7) 0.0298(6) 0.0030(5) 0.0132(6) -0.0025(6) C3 0.0540(9) 0.0324(7) 0.0366(7) -0.0032(6) 0.0135(7) 0.0021(6) C4 0.0506(8) 0.0316(7) 0.0398(7) 0.0042(6) 0.0134(7) -0.0039(6) N4 0.0401(7) 0.0655(10) 0.0488(8) 0.0075(7) 0.0023(6) -0.0038(7) C8 0.0584(11) 0.0462(9) 0.0583(10) 0.0074(8) 0.0296(9) -0.0040(8) C7 0.0555(12) 0.0709(13) 0.0943(16) -0.0018(12) 0.0370(12) -0.0187(10) C6 0.0391(9) 0.0891(16) 0.0793(15) -0.0021(12) 0.0070(9) -0.0110(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 C3 1.3183(19) . ? N2 N1 1.3771(14) . ? N1 C5 1.3703(17) . ? N1 C1 1.3825(18) . ? O2 C2 1.1983(17) . ? C1 O1 1.2018(16) . ? C1 C2 1.5378(18) . ? N3 N4 1.3738(18) . ? N3 C8 1.377(2) . ? N3 C2 1.3824(19) . ? C5 C4 1.350(2) . ? C3 C4 1.411(2) . ? N4 C6 1.314(3) . ? C8 C7 1.339(3) . ? C7 C6 1.415(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 C3 N2 N1 103.41(11) . . ? C5 N1 N2 112.02(11) . . ? C5 N1 C1 128.73(11) . . ? N2 N1 C1 119.10(10) . . ? O1 C1 N1 123.87(12) . . ? O1 C1 C2 121.69(12) . . ? N1 C1 C2 114.31(10) . . ? N4 N3 C8 112.01(13) . . ? N4 N3 C2 118.92(12) . . ? C8 N3 C2 129.05(13) . . ? O2 C2 N3 123.72(13) . . ? O2 C2 C1 122.57(13) . . ? N3 C2 C1 113.47(12) . . ? C4 C5 N1 106.58(12) . . ? N2 C3 C4 112.61(13) . . ? C5 C4 C3 105.38(13) . . ? C6 N4 N3 103.50(16) . . ? C7 C8 N3 106.30(17) . . ? C8 C7 C6 105.76(16) . . ? N4 C6 C7 112.42(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C1 O1 -89.93(18) . . . . ? N1 C1 C2 N3 -99.32(14) . . . . ? O1 C1 C2 O2 -89.93(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.268 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.047 # Attachment 'comp1c.cif' data_ind_0m _database_code_depnum_ccdc_archive 'CCDC 746839' #TrackingRef 'comp1c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 N4 O2' _chemical_formula_weight 290.28 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3930(10) _cell_length_b 7.6748(11) _cell_length_c 12.1165(17) _cell_angle_alpha 75.374(2) _cell_angle_beta 83.368(2) _cell_angle_gamma 79.040(2) _cell_volume 651.43(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5408 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2908 _reflns_number_gt 2599 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0556P)^2^+0.1821P] 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 2908 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 C2 C 0.22486(15) 0.33673(15) 0.27997(9) 0.0160(2) Uani 1 1 d . . . C9 C 0.26854(15) 0.01842(15) 0.07960(9) 0.0165(2) Uani 1 1 d . . . C1 C 0.26188(15) 0.14989(15) 0.24971(9) 0.0167(2) Uani 1 1 d . . . C6 C 0.29044(17) -0.18662(18) -0.07794(11) 0.0249(3) Uani 1 1 d . . . H6 H 0.2985 -0.2588 -0.1301 0.030 Uiso 1 1 calc R . . C8 C 0.33929(16) -0.16687(15) 0.11369(10) 0.0190(2) Uani 1 1 d . . . H8 H 0.3785 -0.2200 0.1867 0.023 Uiso 1 1 calc R . . C4 C 0.21109(15) 0.10203(16) -0.03017(10) 0.0191(2) Uani 1 1 d . . . C7 C 0.34785(17) -0.26743(16) 0.03255(11) 0.0225(3) Uani 1 1 d . . . H7 H 0.3929 -0.3921 0.0518 0.027 Uiso 1 1 calc R . . C3 C 0.15009(16) 0.29075(16) -0.02963(10) 0.0213(2) Uani 1 1 d . . . H3 H 0.1040 0.3791 -0.0924 0.026 Uiso 1 1 calc R . . C5 C 0.22227(17) -0.00250(18) -0.11093(10) 0.0235(3) Uani 1 1 d . . . H5 H 0.1850 0.0505 -0.1844 0.028 Uiso 1 1 calc R . . C16 C -0.03489(15) 0.55068(15) 0.35192(9) 0.0161(2) Uani 1 1 d . . . C11 C -0.22372(16) 0.54295(16) 0.37155(9) 0.0189(2) Uani 1 1 d . . . C13 C -0.26982(19) 0.82223(17) 0.43058(10) 0.0261(3) Uani 1 1 d . . . H13 H -0.3471 0.9159 0.4571 0.031 Uiso 1 1 calc R . . C14 C -0.07993(18) 0.82630(16) 0.41143(10) 0.0232(3) Uani 1 1 d . . . H14 H -0.0345 0.9226 0.4260 0.028 Uiso 1 1 calc R . . C12 C -0.34460(17) 0.68222(17) 0.41092(10) 0.0238(3) Uani 1 1 d . . . H12 H -0.4708 0.6803 0.4233 0.029 Uiso 1 1 calc R . . C15 C 0.04239(16) 0.69109(15) 0.37143(9) 0.0189(2) Uani 1 1 d . . . H15 H 0.1683 0.6941 0.3584 0.023 Uiso 1 1 calc R . . C10 C -0.24398(16) 0.37661(16) 0.34398(10) 0.0213(2) Uani 1 1 d . . . H10 H -0.3563 0.3361 0.3497 0.026 Uiso 1 1 calc R . . O2 O 0.34912(11) 0.41859(11) 0.28045(7) 0.0211(2) Uani 1 1 d . . . O1 O 0.31768(12) 0.01183(11) 0.31909(7) 0.0220(2) Uani 1 1 d . . . N1 N 0.23911(13) 0.15782(12) 0.13781(8) 0.0168(2) Uani 1 1 d . . . N3 N 0.04442(13) 0.39427(12) 0.31377(8) 0.0161(2) Uani 1 1 d . . . N4 N -0.08696(13) 0.28868(13) 0.31005(8) 0.0196(2) Uani 1 1 d . . . N2 N 0.16646(13) 0.32481(13) 0.06861(8) 0.0196(2) 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 C2 0.0170(5) 0.0159(5) 0.0143(5) -0.0028(4) -0.0033(4) -0.0003(4) C9 0.0158(5) 0.0174(5) 0.0174(5) -0.0062(4) 0.0011(4) -0.0035(4) C1 0.0143(5) 0.0177(5) 0.0181(5) -0.0055(4) -0.0014(4) -0.0010(4) C6 0.0271(6) 0.0287(7) 0.0245(6) -0.0149(5) 0.0029(5) -0.0093(5) C8 0.0193(5) 0.0179(6) 0.0188(5) -0.0045(4) 0.0010(4) -0.0022(4) C4 0.0168(5) 0.0223(6) 0.0178(5) -0.0043(4) 0.0000(4) -0.0039(4) C7 0.0236(6) 0.0189(6) 0.0261(6) -0.0086(5) 0.0044(5) -0.0055(5) C3 0.0221(6) 0.0218(6) 0.0180(5) -0.0020(4) -0.0027(4) -0.0019(4) C5 0.0242(6) 0.0303(7) 0.0180(5) -0.0080(5) -0.0012(4) -0.0067(5) C16 0.0196(5) 0.0148(5) 0.0124(5) -0.0032(4) -0.0026(4) 0.0019(4) C11 0.0196(5) 0.0205(6) 0.0150(5) -0.0031(4) -0.0026(4) 0.0001(4) C13 0.0342(7) 0.0217(6) 0.0183(5) -0.0064(5) 0.0001(5) 0.0064(5) C14 0.0362(7) 0.0162(5) 0.0167(5) -0.0049(4) -0.0031(5) -0.0013(5) C12 0.0211(6) 0.0261(6) 0.0195(6) -0.0042(5) 0.0005(4) 0.0043(5) C15 0.0244(6) 0.0167(5) 0.0154(5) -0.0032(4) -0.0024(4) -0.0030(4) C10 0.0173(5) 0.0247(6) 0.0223(6) -0.0061(5) -0.0027(4) -0.0033(4) O2 0.0176(4) 0.0210(4) 0.0258(4) -0.0067(3) -0.0027(3) -0.0035(3) O1 0.0269(4) 0.0177(4) 0.0196(4) -0.0039(3) -0.0058(3) 0.0025(3) N1 0.0185(5) 0.0134(4) 0.0174(5) -0.0036(3) -0.0025(4) 0.0012(3) N3 0.0168(5) 0.0139(4) 0.0192(5) -0.0063(3) -0.0027(4) -0.0020(4) N4 0.0181(5) 0.0202(5) 0.0227(5) -0.0065(4) -0.0037(4) -0.0050(4) N2 0.0208(5) 0.0155(5) 0.0199(5) -0.0012(4) -0.0031(4) 0.0004(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 O2 1.2089(14) . ? C2 N3 1.3724(14) . ? C2 C1 1.5357(15) . ? C9 C8 1.3917(16) . ? C9 N1 1.3951(14) . ? C9 C4 1.3989(16) . ? C1 O1 1.2098(14) . ? C1 N1 1.3702(14) . ? C6 C5 1.3788(18) . ? C6 C7 1.4031(18) . ? C6 H6 0.9300 . ? C8 C7 1.3844(16) . ? C8 H8 0.9300 . ? C4 C5 1.4002(16) . ? C4 C3 1.4342(17) . ? C7 H7 0.9300 . ? C3 N2 1.3047(16) . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? C16 C15 1.3919(16) . ? C16 N3 1.3959(14) . ? C16 C11 1.3988(16) . ? C11 C12 1.4016(16) . ? C11 C10 1.4365(17) . ? C13 C12 1.3793(19) . ? C13 C14 1.4013(19) . ? C13 H13 0.9300 . ? C14 C15 1.3876(16) . ? C14 H14 0.9300 . ? C12 H12 0.9300 . ? C15 H15 0.9300 . ? C10 N4 1.3054(15) . ? C10 H10 0.9300 . ? N1 N2 1.3905(13) . ? N3 N4 1.3892(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C2 N3 123.67(10) . . ? O2 C2 C1 121.44(10) . . ? N3 C2 C1 114.73(9) . . ? C8 C9 N1 131.56(10) . . ? C8 C9 C4 123.04(10) . . ? N1 C9 C4 105.40(10) . . ? O1 C1 N1 124.55(10) . . ? O1 C1 C2 121.09(10) . . ? N1 C1 C2 114.19(9) . . ? C5 C6 C7 121.45(11) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C7 C8 C9 116.08(11) . . ? C7 C8 H8 122.0 . . ? C9 C8 H8 122.0 . . ? C9 C4 C5 119.77(11) . . ? C9 C4 C3 105.14(10) . . ? C5 C4 C3 135.09(11) . . ? C8 C7 C6 121.87(11) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? N2 C3 C4 112.51(10) . . ? N2 C3 H3 123.7 . . ? C4 C3 H3 123.7 . . ? C6 C5 C4 117.79(11) . . ? C6 C5 H5 121.1 . . ? C4 C5 H5 121.1 . . ? C15 C16 N3 131.60(10) . . ? C15 C16 C11 122.95(10) . . ? N3 C16 C11 105.44(10) . . ? C16 C11 C12 119.98(11) . . ? C16 C11 C10 105.12(10) . . ? C12 C11 C10 134.90(11) . . ? C12 C13 C14 121.41(11) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 122.06(11) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C13 C12 C11 117.66(11) . . ? C13 C12 H12 121.2 . . ? C11 C12 H12 121.2 . . ? C14 C15 C16 115.94(11) . . ? C14 C15 H15 122.0 . . ? C16 C15 H15 122.0 . . ? N4 C10 C11 112.39(10) . . ? N4 C10 H10 123.8 . . ? C11 C10 H10 123.8 . . ? C1 N1 N2 118.42(9) . . ? C1 N1 C9 129.91(10) . . ? N2 N1 C9 111.58(9) . . ? C2 N3 N4 118.70(9) . . ? C2 N3 C16 129.74(10) . . ? N4 N3 C16 111.56(9) . . ? C10 N4 N3 105.49(9) . . ? C3 N2 N1 105.37(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 79.35(14) . . . . ? O1 C1 C2 O2 79.35(14) . . . . ? N1 C1 C2 O2 -96.18(13) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.259 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.049 # Attachment 'comp2a.cif' data_ligim _database_code_depnum_ccdc_archive 'CCDC 746840' #TrackingRef 'comp2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 N4 O2' _chemical_formula_weight 204.19 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 ? _symmetry_space_group_name_H-M ? 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 10.0116(4) _cell_length_b 9.8622(4) _cell_length_c 19.4872(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.4370(10) _cell_angle_gamma 90.00 _cell_volume 1863.34(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23968 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 30.05 _reflns_number_total 5432 _reflns_number_gt 3760 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0525P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5432 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N7 N 0.97913(11) 0.24720(11) 0.26006(6) 0.0175(2) Uani 1 1 d . . . N8 N 1.05436(12) 0.15707(12) 0.30841(6) 0.0216(3) Uani 1 1 d . . . N6 N 0.65727(11) 0.04119(11) 0.16328(6) 0.0186(2) Uani 1 1 d . . . N5 N 0.56783(11) 0.09754(11) 0.19821(6) 0.0172(2) Uani 1 1 d . . . O4 O 0.77294(10) 0.33879(9) 0.20611(5) 0.0220(2) Uani 1 1 d . . . O3 O 0.53635(10) 0.20273(11) 0.29600(5) 0.0295(3) Uani 1 1 d . . . C12 C 0.83593(13) 0.25722(13) 0.24839(7) 0.0172(3) Uani 1 1 d . . . C11 C 0.77172(13) 0.16329(13) 0.29182(7) 0.0188(3) Uani 1 1 d . . . H112 H 0.7954 0.1933 0.3408 0.023 Uiso 1 1 calc R . . H111 H 0.8086 0.0727 0.2903 0.023 Uiso 1 1 calc R . . C10 C 0.61675(14) 0.15950(13) 0.26454(7) 0.0192(3) Uani 1 1 d . . . C16 C 1.18249(15) 0.17610(14) 0.30403(8) 0.0240(3) Uani 1 1 d . . . H16 H 1.2578 0.1287 0.3310 0.029 Uiso 1 1 calc R . . C17 C 1.19236(14) 0.27661(14) 0.25380(7) 0.0221(3) Uani 1 1 d . . . H17 H 1.2718 0.3068 0.2420 0.027 Uiso 1 1 calc R . . C18 C 1.06163(14) 0.31931(13) 0.22660(7) 0.0194(3) Uani 1 1 d . . . H18 H 1.0330 0.3851 0.1918 0.023 Uiso 1 1 calc R . . C13 C 0.57561(14) -0.00549(13) 0.10400(7) 0.0197(3) Uani 1 1 d . . . H13 H 0.6073 -0.0499 0.0690 0.024 Uiso 1 1 calc R . . C14 C 0.43486(14) 0.01946(14) 0.09969(7) 0.0202(3) Uani 1 1 d . . . H14 H 0.3595 -0.0044 0.0631 0.024 Uiso 1 1 calc R . . C15 C 0.43320(13) 0.08554(13) 0.16031(7) 0.0190(3) Uani 1 1 d . . . H15 H 0.3557 0.1168 0.1737 0.023 Uiso 1 1 calc R . . N1 N -0.00980(11) 0.16437(11) 0.05416(6) 0.0176(2) Uani 1 1 d . . . O1 O -0.12670(11) 0.34636(11) -0.00024(6) 0.0327(3) Uani 1 1 d . . . O2 O 0.20313(10) 0.39679(10) 0.10402(5) 0.0237(2) Uani 1 1 d . . . N2 N 0.10675(11) 0.08587(11) 0.06720(6) 0.0202(3) Uani 1 1 d . . . N3 N 0.35322(11) 0.34951(11) 0.03750(6) 0.0172(2) Uani 1 1 d . . . N4 N 0.37740(12) 0.29925(11) -0.02405(6) 0.0193(2) Uani 1 1 d . . . C1 C -0.02128(14) 0.28133(14) 0.01232(7) 0.0203(3) Uani 1 1 d . . . C2 C 0.10428(14) 0.31560(14) -0.01367(7) 0.0205(3) Uani 1 1 d . . . H2A H 0.1317 0.2375 -0.0371 0.025 Uiso 1 1 calc R . . H2B H 0.0831 0.3893 -0.0476 0.025 Uiso 1 1 calc R . . C3 C 0.22029(14) 0.35665(12) 0.04818(7) 0.0176(3) Uani 1 1 d . . . C4 C 0.08187(14) -0.01035(14) 0.10927(7) 0.0224(3) Uani 1 1 d . . . H4 H 0.1432 -0.0803 0.1269 0.027 Uiso 1 1 calc R . . C5 C -0.04804(14) 0.00411(14) 0.12476(7) 0.0223(3) Uani 1 1 d . . . H5 H -0.0866 -0.0512 0.1534 0.027 Uiso 1 1 calc R . . C6 C -0.10409(14) 0.11677(14) 0.08859(7) 0.0202(3) Uani 1 1 d . . . H6 H -0.1898 0.1543 0.0874 0.024 Uiso 1 1 calc R . . C7 C 0.51249(14) 0.30860(13) -0.01362(7) 0.0208(3) Uani 1 1 d . . . H7 H 0.5599 0.2827 -0.0469 0.025 Uiso 1 1 calc R . . C8 C 0.57701(15) 0.36225(13) 0.05359(7) 0.0205(3) Uani 1 1 d . . . H8 H 0.6708 0.3773 0.0722 0.025 Uiso 1 1 calc R . . C9 C 0.47339(14) 0.38714(13) 0.08515(7) 0.0193(3) Uani 1 1 d . . . H9 H 0.4818 0.4227 0.1302 0.023 Uiso 1 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 N7 0.0195(6) 0.0174(6) 0.0152(5) 0.0012(4) 0.0036(4) 0.0003(4) N8 0.0220(6) 0.0237(6) 0.0179(6) 0.0057(5) 0.0029(5) 0.0028(5) N6 0.0202(6) 0.0186(5) 0.0184(6) -0.0007(5) 0.0073(5) 0.0017(4) N5 0.0168(5) 0.0184(5) 0.0164(6) -0.0017(4) 0.0041(4) 0.0007(4) O4 0.0233(5) 0.0184(5) 0.0212(5) 0.0014(4) -0.0004(4) 0.0011(4) O3 0.0247(5) 0.0395(6) 0.0255(6) -0.0127(5) 0.0084(4) 0.0003(5) C12 0.0191(6) 0.0166(6) 0.0147(6) -0.0050(5) 0.0018(5) -0.0011(5) C11 0.0187(6) 0.0202(7) 0.0159(6) -0.0002(5) 0.0014(5) -0.0020(5) C10 0.0211(7) 0.0192(7) 0.0168(7) -0.0007(5) 0.0039(5) -0.0016(5) C16 0.0210(7) 0.0264(7) 0.0237(7) 0.0025(6) 0.0036(6) 0.0028(6) C17 0.0244(7) 0.0217(7) 0.0226(7) -0.0036(6) 0.0102(6) -0.0036(6) C18 0.0245(7) 0.0189(7) 0.0157(6) -0.0006(5) 0.0068(5) -0.0029(5) C13 0.0240(7) 0.0191(6) 0.0171(6) -0.0015(5) 0.0072(5) -0.0009(5) C14 0.0196(7) 0.0214(7) 0.0178(7) -0.0013(5) 0.0014(5) -0.0028(5) C15 0.0149(6) 0.0211(7) 0.0206(7) -0.0009(5) 0.0035(5) -0.0006(5) N1 0.0152(5) 0.0184(5) 0.0195(6) 0.0003(4) 0.0050(4) 0.0000(4) O1 0.0265(6) 0.0284(6) 0.0454(7) 0.0131(5) 0.0130(5) 0.0076(5) O2 0.0301(6) 0.0233(5) 0.0205(5) -0.0025(4) 0.0119(4) -0.0046(4) N2 0.0165(6) 0.0210(6) 0.0222(6) -0.0006(5) 0.0030(5) 0.0027(4) N3 0.0214(6) 0.0175(5) 0.0126(5) -0.0014(4) 0.0044(4) -0.0020(4) N4 0.0244(6) 0.0193(6) 0.0152(6) -0.0015(4) 0.0070(5) -0.0011(5) C1 0.0211(7) 0.0195(7) 0.0204(7) 0.0005(5) 0.0052(5) -0.0015(5) C2 0.0226(7) 0.0219(7) 0.0173(7) 0.0023(5) 0.0055(5) -0.0028(5) C3 0.0230(7) 0.0129(6) 0.0182(7) 0.0014(5) 0.0073(5) -0.0014(5) C4 0.0236(7) 0.0192(7) 0.0230(7) 0.0015(6) 0.0033(6) 0.0019(5) C5 0.0253(7) 0.0208(7) 0.0213(7) 0.0003(6) 0.0071(6) -0.0035(6) C6 0.0196(7) 0.0202(7) 0.0227(7) -0.0023(6) 0.0088(5) -0.0021(5) C7 0.0237(7) 0.0188(7) 0.0214(7) 0.0010(5) 0.0083(6) 0.0001(5) C8 0.0207(7) 0.0173(6) 0.0227(7) 0.0023(5) 0.0035(6) -0.0006(5) C9 0.0234(7) 0.0179(6) 0.0149(6) 0.0001(5) 0.0015(5) -0.0025(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N7 C18 1.3718(17) . ? N7 N8 1.3753(15) . ? N7 C12 1.3980(17) . ? N8 C16 1.3201(18) . ? N6 C13 1.3207(17) . ? N6 N5 1.3702(15) . ? N5 C15 1.3711(16) . ? N5 C10 1.4030(17) . ? O4 C12 1.2102(16) . ? O3 C10 1.2049(16) . ? C12 C11 1.5030(18) . ? C11 C10 1.5099(19) . ? C16 C17 1.414(2) . ? C17 C18 1.3510(19) . ? C13 C14 1.4122(19) . ? C14 C15 1.3528(18) . ? N1 C6 1.3701(17) . ? N1 N2 1.3703(15) . ? N1 C1 1.4007(17) . ? O1 C1 1.2068(17) . ? O2 C3 1.2097(16) . ? N2 C4 1.3178(18) . ? N3 N4 1.3740(15) . ? N3 C9 1.3749(17) . ? N3 C3 1.3991(17) . ? N4 C7 1.3198(18) . ? C1 C2 1.5061(19) . ? C2 C3 1.5059(19) . ? C4 C5 1.414(2) . ? C5 C6 1.360(2) . ? C7 C8 1.411(2) . ? C8 C9 1.3537(19) . ? 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 C18 N7 N8 111.65(11) . . ? C18 N7 C12 126.92(11) . . ? N8 N7 C12 121.43(11) . . ? C16 N8 N7 103.82(11) . . ? C13 N6 N5 103.72(11) . . ? N6 N5 C15 111.95(11) . . ? N6 N5 C10 120.87(11) . . ? C15 N5 C10 127.18(11) . . ? O4 C12 N7 119.80(12) . . ? O4 C12 C11 124.73(12) . . ? N7 C12 C11 115.47(11) . . ? C12 C11 C10 111.30(11) . . ? O3 C10 N5 119.93(12) . . ? O3 C10 C11 124.77(13) . . ? N5 C10 C11 115.29(11) . . ? N8 C16 C17 112.41(13) . . ? C18 C17 C16 105.20(12) . . ? C17 C18 N7 106.92(12) . . ? N6 C13 C14 112.47(12) . . ? C15 C14 C13 105.15(12) . . ? C14 C15 N5 106.70(12) . . ? C6 N1 N2 111.99(11) . . ? C6 N1 C1 126.92(12) . . ? N2 N1 C1 121.04(11) . . ? C4 N2 N1 103.76(11) . . ? N4 N3 C9 111.84(11) . . ? N4 N3 C3 121.95(11) . . ? C9 N3 C3 126.20(11) . . ? C7 N4 N3 103.72(11) . . ? O1 C1 N1 119.76(13) . . ? O1 C1 C2 125.00(13) . . ? N1 C1 C2 115.24(12) . . ? C3 C2 C1 109.45(11) . . ? O2 C3 N3 120.26(12) . . ? O2 C3 C2 123.63(13) . . ? N3 C3 C2 116.09(11) . . ? N2 C4 C5 112.76(12) . . ? C6 C5 C4 104.74(12) . . ? C5 C6 N1 106.74(12) . . ? N4 C7 C8 112.56(12) . . ? C9 C8 C7 105.33(13) . . ? C8 C9 N3 106.56(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -67.86(15) . . . . ? C1 C2 C3 N3 160.23(11) . . . . ? O1 C1 C3 O2 66.26(16) . . . . ? N5 C10 C11 C12 68.74(14) . . . . ? C10 C11 C12 N7 -167.55(11) . . . . ? O4 C12 C10 O3 -74.68(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.330 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.053 # Attachment 'comp2c.cif' data_panleg _database_code_depnum_ccdc_archive 'CCDC 746841' #TrackingRef 'comp2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 N4 O2' _chemical_formula_weight 304.31 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 ? _symmetry_space_group_name_H-M ? 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 7.6935(4) _cell_length_b 14.8559(8) _cell_length_c 12.8855(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.972(2) _cell_angle_gamma 90.00 _cell_volume 1415.88(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18297 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.02 _reflns_number_total 4133 _reflns_number_gt 2652 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^+0.1003P] 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 4133 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.12470(15) 0.02779(7) 0.40129(9) 0.0414(3) Uani 1 1 d . . . N2 N 0.12664(17) -0.06532(8) 0.38973(10) 0.0499(3) Uani 1 1 d . . . N3 N 0.02494(13) 0.10233(8) 0.07403(9) 0.0418(3) Uani 1 1 d . . . N4 N 0.19757(14) 0.07360(9) 0.12923(10) 0.0506(3) Uani 1 1 d . . . O1 O 0.03507(14) 0.16186(7) 0.32165(8) 0.0545(3) Uani 1 1 d . . . O2 O -0.26651(13) 0.11567(8) 0.07295(9) 0.0622(3) Uani 1 1 d . . . C1 C 0.03134(17) 0.08052(9) 0.31525(11) 0.0413(3) Uani 1 1 d . . . C2 C -0.07530(19) 0.02956(10) 0.21750(11) 0.0472(3) Uani 1 1 d . . . H2A H -0.0066 -0.0227 0.2069 0.057 Uiso 1 1 calc R . . H2B H -0.1871 0.0084 0.2300 0.057 Uiso 1 1 calc R . . C3 C -0.11857(18) 0.08632(10) 0.11714(11) 0.0434(3) Uani 1 1 d . . . C4 C 0.2405(2) -0.09464(9) 0.47761(12) 0.0515(4) Uani 1 1 d . . . H4 H 0.2680 -0.1552 0.4912 0.062 Uiso 1 1 calc R . . C5 C 0.31869(19) -0.02417(9) 0.55094(11) 0.0441(3) Uani 1 1 d . . . C6 C 0.4476(2) -0.01971(11) 0.65056(12) 0.0520(4) Uani 1 1 d . . . H6 H 0.5023 -0.0717 0.6847 0.062 Uiso 1 1 calc R . . C7 C 0.4919(2) 0.06284(12) 0.69697(12) 0.0565(4) Uani 1 1 d . . . H7 H 0.5790 0.0672 0.7631 0.068 Uiso 1 1 calc R . . C8 C 0.4084(2) 0.14061(11) 0.64665(12) 0.0542(4) Uani 1 1 d . . . H8 H 0.4397 0.1957 0.6809 0.065 Uiso 1 1 calc R . . C9 C 0.2810(2) 0.13853(9) 0.54779(11) 0.0471(3) Uani 1 1 d . . . H9 H 0.2255 0.1907 0.5147 0.057 Uiso 1 1 calc R . . C10 C 0.23973(16) 0.05443(9) 0.50013(10) 0.0390(3) Uani 1 1 d . . . C11 C 0.30177(19) 0.10007(11) 0.07073(12) 0.0529(4) Uani 1 1 d . . . H11 H 0.4257 0.0896 0.0891 0.064 Uiso 1 1 calc R . . C12 C 0.20574(18) 0.14686(9) -0.02454(11) 0.0446(3) Uani 1 1 d . . . C13 C 0.2521(2) 0.18680(10) -0.11137(13) 0.0562(4) Uani 1 1 d . . . H13 H 0.3713 0.1875 -0.1146 0.067 Uiso 1 1 calc R . . C14 C 0.1179(3) 0.22469(11) -0.19107(13) 0.0633(5) Uani 1 1 d . . . H14 H 0.1463 0.2514 -0.2496 0.076 Uiso 1 1 calc R . . C15 C -0.0609(2) 0.22418(10) -0.18668(12) 0.0585(4) Uani 1 1 d . . . H15 H -0.1491 0.2508 -0.2424 0.070 Uiso 1 1 calc R . . C16 C -0.1109(2) 0.18540(9) -0.10217(11) 0.0481(3) Uani 1 1 d . . . H16 H -0.2306 0.1848 -0.0997 0.058 Uiso 1 1 calc R . . C17 C 0.02610(17) 0.14734(8) -0.02099(10) 0.0397(3) 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 N1 0.0477(6) 0.0358(6) 0.0435(6) -0.0009(5) 0.0169(5) -0.0004(5) N2 0.0648(8) 0.0357(6) 0.0531(7) -0.0016(5) 0.0225(6) -0.0041(5) N3 0.0331(5) 0.0519(7) 0.0412(6) 0.0001(5) 0.0114(5) 0.0015(5) N4 0.0356(6) 0.0655(8) 0.0493(7) 0.0015(6) 0.0092(5) 0.0054(5) O1 0.0662(7) 0.0410(6) 0.0535(6) -0.0003(4) 0.0118(5) 0.0053(5) O2 0.0374(6) 0.0863(8) 0.0653(7) 0.0116(6) 0.0180(5) 0.0066(5) C1 0.0405(7) 0.0431(7) 0.0452(7) -0.0014(6) 0.0199(6) -0.0003(6) C2 0.0469(7) 0.0501(8) 0.0469(8) -0.0021(6) 0.0168(6) -0.0092(6) C3 0.0382(7) 0.0490(8) 0.0446(7) -0.0063(6) 0.0142(6) -0.0044(6) C4 0.0679(10) 0.0362(7) 0.0544(9) 0.0061(6) 0.0237(7) 0.0029(7) C5 0.0494(8) 0.0436(7) 0.0456(7) 0.0051(6) 0.0238(6) 0.0017(6) C6 0.0546(8) 0.0566(9) 0.0478(8) 0.0117(7) 0.0193(7) 0.0063(7) C7 0.0560(9) 0.0675(11) 0.0451(8) 0.0018(7) 0.0123(7) -0.0044(7) C8 0.0614(9) 0.0526(9) 0.0503(8) -0.0074(7) 0.0182(7) -0.0102(7) C9 0.0549(8) 0.0415(7) 0.0480(8) -0.0005(6) 0.0192(7) 0.0004(6) C10 0.0404(7) 0.0420(7) 0.0395(7) 0.0000(5) 0.0189(5) -0.0010(5) C11 0.0344(7) 0.0679(10) 0.0572(9) -0.0074(7) 0.0137(6) 0.0006(7) C12 0.0434(7) 0.0439(7) 0.0502(8) -0.0114(6) 0.0193(6) -0.0065(6) C13 0.0635(10) 0.0532(9) 0.0625(10) -0.0116(7) 0.0349(8) -0.0130(7) C14 0.0932(13) 0.0512(9) 0.0562(10) -0.0025(7) 0.0383(10) -0.0090(9) C15 0.0785(11) 0.0507(9) 0.0461(8) 0.0020(7) 0.0170(8) 0.0051(8) C16 0.0495(8) 0.0491(8) 0.0450(7) -0.0040(6) 0.0117(6) 0.0037(6) C17 0.0429(7) 0.0385(7) 0.0396(7) -0.0063(5) 0.0145(6) -0.0024(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3858(17) . ? N1 N2 1.3917(15) . ? N1 C10 1.3934(17) . ? N2 C4 1.3012(19) . ? N3 C3 1.3862(16) . ? N3 N4 1.3900(15) . ? N3 C17 1.3974(16) . ? N4 C11 1.3032(18) . ? O1 C1 1.2110(16) . ? O2 C3 1.2055(16) . ? C1 C2 1.5047(19) . ? C2 C3 1.502(2) . ? C4 C5 1.428(2) . ? C5 C6 1.391(2) . ? C5 C10 1.3937(18) . ? C6 C7 1.366(2) . ? C7 C8 1.392(2) . ? C8 C9 1.377(2) . ? C9 C10 1.3897(19) . ? C11 C12 1.427(2) . ? C12 C17 1.3953(18) . ? C12 C13 1.397(2) . ? C13 C14 1.361(2) . ? C14 C15 1.393(2) . ? C15 C16 1.377(2) . ? C16 C17 1.3850(19) . ? 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 N2 119.65(11) . . ? C1 N1 C10 129.02(11) . . ? N2 N1 C10 110.94(10) . . ? C4 N2 N1 105.31(11) . . ? C3 N3 N4 119.77(11) . . ? C3 N3 C17 129.13(11) . . ? N4 N3 C17 111.08(10) . . ? C11 N4 N3 105.34(12) . . ? O1 C1 N1 120.81(12) . . ? O1 C1 C2 123.80(13) . . ? N1 C1 C2 115.37(12) . . ? C3 C2 C1 112.26(12) . . ? O2 C3 N3 120.09(13) . . ? O2 C3 C2 124.49(12) . . ? N3 C3 C2 115.40(12) . . ? N2 C4 C5 113.00(13) . . ? C6 C5 C10 120.10(13) . . ? C6 C5 C4 135.18(14) . . ? C10 C5 C4 104.69(13) . . ? C7 C6 C5 118.39(14) . . ? C6 C7 C8 120.91(14) . . ? C9 C8 C7 122.12(14) . . ? C8 C9 C10 116.54(13) . . ? C9 C10 N1 132.05(12) . . ? C9 C10 C5 121.90(13) . . ? N1 C10 C5 106.05(11) . . ? N4 C11 C12 112.91(12) . . ? C17 C12 C13 119.83(14) . . ? C17 C12 C11 104.91(12) . . ? C13 C12 C11 135.25(14) . . ? C14 C13 C12 118.19(14) . . ? C13 C14 C15 121.30(15) . . ? C16 C15 C14 121.90(15) . . ? C15 C16 C17 116.61(14) . . ? C16 C17 C12 122.16(13) . . ? C16 C17 N3 132.08(12) . . ? C12 C17 N3 105.75(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -160.21(11) . . . . ? C1 C2 C3 N3 74.44(15) . . . . ? O1 C1 C3 O2 -64.23(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.168 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.037 # Attachment 'comp3.cif' data_comp(3) _database_code_depnum_ccdc_archive 'CCDC 746842' #TrackingRef 'comp3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 Cu N8 O8' _chemical_formula_weight 570.03 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' Cu Cu 0.3201 1.2651 '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 10.3247(4) _cell_length_b 15.4035(7) _cell_length_c 8.3413(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.0560(10) _cell_angle_gamma 90.00 _cell_volume 1313.48(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 0.30 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_absorpt_coefficient_mu 0.890 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.947 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _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 16930 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.06 _reflns_number_total 3853 _reflns_number_gt 2640 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.1015P)^2^+0.0647P] 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 3853 _refine_ls_number_parameters 169 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1711 _refine_ls_wR_factor_gt 0.1567 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.094 _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 Cu1 Cu 0.5000 0.0000 0.5000 0.03870(17) Uani 1 2 d S . . O1 O 0.64574(18) 0.11865(15) 0.5151(3) 0.0567(6) Uani 1 1 d . . . N1 N 0.4432(2) 0.03772(17) 0.2711(3) 0.0442(5) Uani 1 1 d . . . N4 N 0.2375(2) 0.06635(16) 0.5579(3) 0.0506(6) Uani 1 1 d D . . H4N H 0.2007 0.0192 0.5198 0.061 Uiso 1 1 calc RD . . N3 N 0.3666(2) 0.08188(15) 0.5721(3) 0.0435(5) Uani 1 1 d . . . N2 N 0.5033(2) 0.10216(17) 0.2060(3) 0.0521(6) Uani 1 1 d D . . H2N H 0.5692 0.1301 0.2552 0.063 Uiso 1 1 calc RD . . O2 O 0.8575(2) 0.08828(16) 0.5872(4) 0.0756(8) Uani 1 1 d . . . C1 C 0.7606(3) 0.1370(2) 0.5710(4) 0.0524(7) Uani 1 1 d . . . C8 C 0.3826(3) 0.15988(19) 0.6342(4) 0.0530(7) Uani 1 1 d . . . H8 H 0.4630 0.1878 0.6571 0.064 Uiso 1 1 calc R . . C10 C 0.1738(3) 0.1336(2) 0.6105(4) 0.0583(8) Uani 1 1 d . . . H10 H 0.0841 0.1375 0.6121 0.070 Uiso 1 1 calc R . . C9 C 0.2642(3) 0.1955(2) 0.6614(4) 0.0624(8) Uani 1 1 d . . . H9 H 0.2499 0.2497 0.7048 0.075 Uiso 1 1 calc R . . C5 C 0.4481(4) 0.1182(2) 0.0535(4) 0.0633(9) Uani 1 1 d . . . H5 H 0.4735 0.1608 -0.0146 0.076 Uiso 1 1 calc R . . C6 C 0.3500(4) 0.0616(2) 0.0172(4) 0.0660(9) Uani 1 1 d . . . H6 H 0.2948 0.0561 -0.0804 0.079 Uiso 1 1 calc R . . C7 C 0.3485(4) 0.0128(2) 0.1572(5) 0.0627(9) Uani 1 1 d . . . H7 H 0.2890 -0.0313 0.1690 0.075 Uiso 1 1 calc R . . C2 C 0.7820(3) 0.2283(2) 0.6363(5) 0.0703(10) Uani 1 1 d . . . O3 O 0.7040(3) 0.2649(2) 0.7051(6) 0.1367(17) Uani 1 1 d . . . O4 O 0.8901(3) 0.26240(19) 0.6088(5) 0.1143(13) Uani 1 1 d D . . C3 C 0.9176(8) 0.3476(4) 0.6858(11) 0.186(4) Uani 1 1 d D . . H3A H 0.8366 0.3791 0.6882 0.223 Uiso 1 1 calc R . . H3B H 0.9599 0.3401 0.7963 0.223 Uiso 1 1 calc R . . C4 C 0.9973(8) 0.3929(5) 0.5991(13) 0.227(5) Uani 1 1 d D . . H4A H 1.0162 0.4487 0.6482 0.341 Uiso 1 1 calc R . . H4B H 0.9546 0.4005 0.4902 0.341 Uiso 1 1 calc R . . H4C H 1.0774 0.3614 0.5977 0.341 Uiso 1 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 Cu1 0.0307(2) 0.0453(3) 0.0407(3) 0.00233(18) 0.00730(16) 0.00511(17) O1 0.0382(10) 0.0610(13) 0.0704(14) -0.0018(10) 0.0053(9) -0.0098(9) N1 0.0402(11) 0.0504(13) 0.0420(12) 0.0048(10) 0.0059(9) 0.0043(10) N4 0.0331(11) 0.0530(14) 0.0655(16) -0.0055(11) 0.0066(10) 0.0010(9) N3 0.0333(10) 0.0486(12) 0.0496(13) 0.0010(10) 0.0095(9) 0.0036(9) N2 0.0558(14) 0.0485(13) 0.0520(14) 0.0046(10) 0.0068(11) -0.0018(11) O2 0.0400(11) 0.0593(14) 0.126(2) -0.0209(14) 0.0073(12) 0.0019(10) C1 0.0392(14) 0.0539(17) 0.0656(19) -0.0066(14) 0.0125(13) -0.0049(12) C8 0.0444(15) 0.0462(15) 0.0686(19) 0.0000(14) 0.0082(13) 0.0043(12) C10 0.0397(14) 0.0636(19) 0.073(2) 0.0009(15) 0.0138(14) 0.0166(13) C9 0.0521(17) 0.0535(18) 0.083(2) -0.0045(16) 0.0156(16) 0.0148(14) C5 0.080(2) 0.0581(19) 0.0525(18) 0.0126(14) 0.0129(17) 0.0111(17) C6 0.076(2) 0.073(2) 0.0459(17) 0.0025(15) -0.0030(15) 0.0072(18) C7 0.0554(19) 0.073(2) 0.0565(19) 0.0059(15) -0.0041(15) -0.0110(15) C2 0.0455(16) 0.059(2) 0.105(3) -0.0251(19) 0.0063(17) 0.0008(14) O3 0.080(2) 0.117(3) 0.217(5) -0.092(3) 0.035(3) 0.006(2) O4 0.087(2) 0.0701(18) 0.193(4) -0.041(2) 0.045(2) -0.0381(16) C3 0.181(7) 0.100(4) 0.295(11) -0.089(6) 0.100(7) -0.078(5) C4 0.163(8) 0.076(4) 0.442(17) -0.011(8) 0.038(8) -0.023(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cu1 N1 2.003(2) 3_656 ? Cu1 N1 2.003(2) . ? Cu1 N3 2.021(2) 3_656 ? Cu1 N3 2.021(2) . ? Cu1 O1 2.359(2) . ? Cu1 O1 2.359(2) 3_656 ? O1 C1 1.244(3) . ? N1 C7 1.322(4) . ? N1 N2 1.327(3) . ? N4 C10 1.334(4) . ? N4 N3 1.343(3) . ? N3 C8 1.310(4) . ? N2 C5 1.341(4) . ? O2 C1 1.243(4) . ? C1 C2 1.513(5) . ? C8 C9 1.387(4) . ? C10 C9 1.360(5) . ? C5 C6 1.339(5) . ? C6 C7 1.391(5) . ? C2 O3 1.194(4) . ? C2 O4 1.283(4) . ? O4 C3 1.471(6) . ? C3 C4 1.362(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 3_656 . ? N1 Cu1 N3 88.96(9) 3_656 3_656 ? N1 Cu1 N3 91.04(9) . 3_656 ? N1 Cu1 N3 91.04(9) 3_656 . ? N1 Cu1 N3 88.96(9) . . ? N3 Cu1 N3 180.00(12) 3_656 . ? N1 Cu1 O1 94.27(9) 3_656 . ? N1 Cu1 O1 85.73(9) . . ? N3 Cu1 O1 92.46(8) 3_656 . ? N3 Cu1 O1 87.54(8) . . ? N1 Cu1 O1 85.73(9) 3_656 3_656 ? N1 Cu1 O1 94.27(9) . 3_656 ? N3 Cu1 O1 87.54(8) 3_656 3_656 ? N3 Cu1 O1 92.46(8) . 3_656 ? O1 Cu1 O1 180.00(13) . 3_656 ? C1 O1 Cu1 139.7(2) . . ? C7 N1 N2 105.3(3) . . ? C7 N1 Cu1 133.6(2) . . ? N2 N1 Cu1 121.08(19) . . ? C10 N4 N3 111.2(3) . . ? C8 N3 N4 105.5(2) . . ? C8 N3 Cu1 129.52(19) . . ? N4 N3 Cu1 124.89(19) . . ? N1 N2 C5 111.4(3) . . ? O2 C1 O1 127.9(3) . . ? O2 C1 C2 116.5(3) . . ? O1 C1 C2 115.4(3) . . ? N3 C8 C9 111.2(3) . . ? N4 C10 C9 107.3(3) . . ? C10 C9 C8 104.8(3) . . ? C6 C5 N2 107.6(3) . . ? C5 C6 C7 105.0(3) . . ? N1 C7 C6 110.6(3) . . ? O3 C2 O4 123.8(3) . . ? O3 C2 C1 122.5(3) . . ? O4 C2 C1 113.8(3) . . ? C2 O4 C3 114.0(4) . . ? C4 C3 O4 108.6(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.746 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.091 #===END # Attachment 'comp6.cif' data_comp(6) _database_code_depnum_ccdc_archive 'CCDC 746843' #TrackingRef 'comp6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H26 Cu N4 O5' _chemical_formula_weight 405.94 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.6709(13) _cell_length_b 10.8951(9) _cell_length_c 11.3147(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1931.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour light-blue _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 1.162 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _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 23562 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 30.11 _reflns_number_total 2838 _reflns_number_gt 1964 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0487P)^2^+0.8875P] 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 2838 _refine_ls_number_parameters 126 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.0000 0.58099(3) 0.2500 0.02752(10) Uani 1 2 d S . . O1 O -0.08045(9) 0.71302(13) 0.30246(12) 0.0368(3) Uani 1 1 d . . . O2 O -0.01039(10) 0.65054(17) 0.45799(14) 0.0513(4) Uani 1 1 d . . . N1 N 0.09104(10) 0.45472(15) 0.23564(13) 0.0308(3) Uani 1 1 d . . . N2 N 0.08688(10) 0.35952(15) 0.15813(14) 0.0348(4) Uani 1 1 d D . . H2N H 0.0453(12) 0.358(2) 0.1060(18) 0.042 Uiso 1 1 d D . . C3 C 0.16636(12) 0.44395(18) 0.29029(18) 0.0344(4) Uani 1 1 d . . . C1 C 0.15823(13) 0.29154(18) 0.16118(18) 0.0396(4) Uani 1 1 d . . . C6 C -0.06338(12) 0.72037(18) 0.41168(17) 0.0349(4) Uani 1 1 d . . . C5 C 0.19227(15) 0.5319(2) 0.3846(2) 0.0517(6) Uani 1 1 d . . . H5A H 0.1705 0.5043 0.4593 0.078 Uiso 1 1 calc R . . H5B H 0.1696 0.6117 0.3671 0.078 Uiso 1 1 calc R . . H5C H 0.2534 0.5362 0.3881 0.078 Uiso 1 1 calc R . . C4 C 0.17004(19) 0.1825(2) 0.0823(3) 0.0633(7) Uani 1 1 d . . . H4A H 0.1182 0.1671 0.0397 0.095 Uiso 1 1 calc R . . H4B H 0.1842 0.1120 0.1292 0.095 Uiso 1 1 calc R . . H4C H 0.2154 0.1985 0.0273 0.095 Uiso 1 1 calc R . . C7 C -0.10816(17) 0.8168(2) 0.4837(2) 0.0561(6) Uani 1 1 d . . . H7A H -0.0685 0.8805 0.5042 0.084 Uiso 1 1 calc R . . H7B H -0.1305 0.7804 0.5545 0.084 Uiso 1 1 calc R . . H7C H -0.1541 0.8512 0.4384 0.084 Uiso 1 1 calc R . . C2 C 0.21023(13) 0.3427(2) 0.24548(19) 0.0417(5) Uani 1 1 d . . . H2 H 0.2640 0.3152 0.2682 0.050 Uiso 1 1 calc R . . O5 O -0.0612(4) 0.9546(4) 0.1956(5) 0.112(2) Uani 0.564(8) 1 d P A -1 H10 H -0.0580 0.8804 0.2068 0.168 Uiso 0.564(8) 1 calc PR A -1 C8 C 0.0000 1.0088(6) 0.2500 0.0959(18) Uani 1 2 d S . . 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 Cu 0.02702(16) 0.02679(16) 0.02874(16) 0.000 -0.00378(12) 0.000 O1 0.0407(7) 0.0346(7) 0.0349(7) -0.0012(6) -0.0047(6) 0.0087(6) O2 0.0556(10) 0.0601(10) 0.0384(8) 0.0011(7) -0.0107(7) 0.0158(8) N1 0.0304(8) 0.0304(7) 0.0315(8) -0.0033(6) -0.0032(6) 0.0011(6) N2 0.0340(8) 0.0359(8) 0.0343(8) -0.0058(7) -0.0022(7) -0.0006(7) C3 0.0315(9) 0.0376(10) 0.0341(9) 0.0016(8) -0.0046(8) 0.0005(8) C1 0.0431(11) 0.0360(10) 0.0398(10) -0.0012(8) 0.0087(9) 0.0056(9) C6 0.0361(10) 0.0340(10) 0.0346(9) -0.0006(8) 0.0026(8) -0.0001(8) C5 0.0474(12) 0.0535(13) 0.0542(13) -0.0092(11) -0.0215(10) 0.0030(11) C4 0.0727(17) 0.0499(14) 0.0672(17) -0.0184(12) 0.0135(14) 0.0085(13) C7 0.0637(16) 0.0564(14) 0.0481(13) -0.0110(11) 0.0108(11) 0.0113(12) C2 0.0338(10) 0.0452(11) 0.0460(11) 0.0035(10) -0.0007(9) 0.0092(8) O5 0.142(5) 0.071(3) 0.123(5) 0.038(3) -0.008(4) 0.013(3) C8 0.095(4) 0.066(3) 0.127(5) 0.000 0.006(4) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cu N1 1.9886(16) 3 ? Cu N1 1.9886(16) . ? Cu O1 2.0027(13) . ? Cu O1 2.0027(14) 3 ? O1 C6 1.267(2) . ? O2 C6 1.242(2) . ? N1 C3 1.338(2) . ? N1 N2 1.360(2) . ? N2 C1 1.342(3) . ? C3 C2 1.396(3) . ? C3 C5 1.490(3) . ? C1 C2 1.373(3) . ? C1 C4 1.498(3) . ? C6 C7 1.504(3) . ? O5 C8 1.284(6) . ? C8 O5 1.284(6) 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 N1 Cu N1 92.45(9) 3 . ? N1 Cu O1 91.21(6) 3 . ? N1 Cu O1 166.59(6) . . ? N1 Cu O1 166.59(6) 3 3 ? N1 Cu O1 91.21(6) . 3 ? O1 Cu O1 88.18(8) . 3 ? C6 O1 Cu 101.63(12) . . ? C3 N1 N2 105.88(16) . . ? C3 N1 Cu 130.99(14) . . ? N2 N1 Cu 123.09(12) . . ? C1 N2 N1 111.38(16) . . ? N1 C3 C2 109.64(18) . . ? N1 C3 C5 121.00(18) . . ? C2 C3 C5 129.35(19) . . ? N2 C1 C2 106.77(17) . . ? N2 C1 C4 121.7(2) . . ? C2 C1 C4 131.5(2) . . ? O2 C6 O1 120.93(19) . . ? O2 C6 C7 120.76(19) . . ? O1 C6 C7 118.31(19) . . ? C1 C2 C3 106.31(18) . . ? O5 C8 O5 125.2(6) . 3 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.350 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.059 #===END