data_y264-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N3 O4' _chemical_formula_weight 298.28 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.285(4) _cell_length_b 9.374(5) _cell_length_c 11.100(6) _cell_angle_alpha 108.94(4) _cell_angle_beta 92.81(4) _cell_angle_gamma 97.68(4) _cell_volume 707.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 706 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 20.24 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max .30 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4765 _diffrn_reflns_av_R_equivalents 0.1568 _diffrn_reflns_av_sigmaI/netI 0.4307 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2350 _reflns_number_gt 418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0390P)^2^] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2350 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2853 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 0.603 _refine_ls_restrained_S_all 0.603 _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 0.1311(11) 0.0488(9) -0.0832(8) 0.0598(9) Uani 1 1 d . . . C2 C 0.1697(11) 0.1984(9) 0.0291(9) 0.0598(9) Uani 1 1 d . . . C3 C 0.2563(10) 0.2032(9) 0.1391(8) 0.0598(9) Uani 1 1 d . . . C4 C 0.3341(11) 0.0781(9) 0.1673(9) 0.0598(9) Uani 1 1 d . . . C5 C 0.3031(10) -0.0610(8) 0.0585(8) 0.0598(9) Uani 1 1 d . . . C6 C 0.2124(10) -0.0765(8) -0.0535(8) 0.0598(9) Uani 1 1 d . . . C7 C 0.1029(11) 0.3487(9) -0.1081(9) 0.075(3) Uani 1 1 d . . . H7A H 0.0523 0.4427 -0.1005 0.112 Uiso 1 1 calc R . . H7B H 0.0240 0.2620 -0.1726 0.112 Uiso 1 1 calc R . . H7C H 0.2294 0.3581 -0.1340 0.112 Uiso 1 1 calc R . . C8 C 0.3811(11) 0.4754(8) 0.2319(8) 0.0819(13) Uani 1 1 d . . . H8A H 0.4266 0.4750 0.1530 0.098 Uiso 1 1 calc R . . C9 C 0.4063(12) 0.6084(9) 0.3408(8) 0.0819(13) Uani 1 1 d . . . H9A H 0.4745 0.7003 0.3370 0.098 Uiso 1 1 calc R . . C10 C 0.3366(11) 0.6071(9) 0.4479(8) 0.0819(13) Uani 1 1 d . . . H10A H 0.3510 0.7004 0.5175 0.098 Uiso 1 1 calc R . . C11 C 0.2436(12) 0.4769(8) 0.4644(8) 0.0819(13) Uani 1 1 d . . . H11A H 0.2013 0.4776 0.5442 0.098 Uiso 1 1 calc R . . C12 C 0.2158(12) 0.3458(9) 0.3582(8) 0.0819(13) Uani 1 1 d . . . H12A H 0.1466 0.2548 0.3629 0.098 Uiso 1 1 calc R . . C13 C 0.3791(11) -0.1883(9) 0.0727(9) 0.0598(9) Uani 1 1 d . . . C14 C 0.1966(10) -0.2140(8) -0.1664(8) 0.0598(9) Uani 1 1 d . . . N1 N 0.2859(10) 0.3456(7) 0.2475(7) 0.0819(13) Uani 1 1 d . . . N2 N 0.4425(9) -0.2894(7) 0.0833(7) 0.075(3) Uani 1 1 d . . . N3 N 0.1886(9) -0.3306(7) -0.2448(7) 0.089(3) Uani 1 1 d . . . O1 O 0.0335(7) 0.0340(5) -0.1845(6) 0.0667(19) Uani 1 1 d . . . O2 O 0.1075(7) 0.3240(6) 0.0146(6) 0.0665(18) Uani 1 1 d . . . O3 O 0.4200(8) 0.0960(6) 0.2718(5) 0.076(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 C1 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C2 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C3 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C4 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C5 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C6 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C7 0.077(7) 0.067(6) 0.082(8) 0.018(6) 0.033(6) 0.026(5) C8 0.101(3) 0.055(2) 0.070(3) -0.007(2) 0.020(2) 0.0113(18) C9 0.101(3) 0.055(2) 0.070(3) -0.007(2) 0.020(2) 0.0113(18) C10 0.101(3) 0.055(2) 0.070(3) -0.007(2) 0.020(2) 0.0113(18) C11 0.101(3) 0.055(2) 0.070(3) -0.007(2) 0.020(2) 0.0113(18) C12 0.101(3) 0.055(2) 0.070(3) -0.007(2) 0.020(2) 0.0113(18) C13 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) C14 0.0591(17) 0.0437(12) 0.0592(18) -0.0059(16) 0.0180(13) 0.0022(12) N1 0.101(3) 0.055(2) 0.070(3) -0.007(2) 0.020(2) 0.0113(18) N2 0.069(5) 0.054(4) 0.093(6) 0.011(4) 0.019(4) 0.008(4) N3 0.105(6) 0.048(4) 0.080(6) -0.022(4) 0.029(5) 0.004(4) O1 0.078(4) 0.042(3) 0.070(4) 0.009(3) 0.018(3) -0.006(3) O2 0.082(4) 0.049(4) 0.057(4) 0.006(3) 0.004(3) 0.004(3) O3 0.099(5) 0.047(3) 0.059(4) -0.009(3) -0.004(3) 0.004(3) _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 O1 1.259(9) . ? C1 C6 1.501(11) . ? C1 C2 1.525(9) . ? C2 C3 1.331(11) . ? C2 O2 1.369(9) . ? C3 N1 1.460(8) . ? C3 C4 1.482(12) . ? C4 O3 1.240(10) . ? C4 C5 1.442(9) . ? C5 C6 1.335(11) . ? C5 C13 1.430(11) . ? C6 C14 1.464(9) . ? C7 O2 1.453(9) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N1 1.384(10) . ? C8 C9 1.410(9) . ? C8 H8A 0.9500 . ? C9 C10 1.319(11) . ? C9 H9A 0.9500 . ? C10 C11 1.385(10) . ? C10 H10A 0.9500 . ? C11 C12 1.382(9) . ? C11 H11A 0.9500 . ? C12 N1 1.353(11) . ? C12 H12A 0.9500 . ? C13 N2 1.144(10) . ? C14 N3 1.147(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 125.6(7) . . ? O1 C1 C2 122.5(9) . . ? C6 C1 C2 111.9(8) . . ? C3 C2 O2 121.7(7) . . ? C3 C2 C1 119.9(9) . . ? O2 C2 C1 118.3(8) . . ? C2 C3 N1 119.4(8) . . ? C2 C3 C4 127.5(8) . . ? N1 C3 C4 113.1(8) . . ? O3 C4 C5 125.6(9) . . ? O3 C4 C3 122.6(7) . . ? C5 C4 C3 111.8(9) . . ? C6 C5 C13 118.8(7) . . ? C6 C5 C4 124.3(9) . . ? C13 C5 C4 116.9(9) . . ? C5 C6 C14 123.5(9) . . ? C5 C6 C1 124.5(8) . . ? C14 C6 C1 111.8(8) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 115.6(8) . . ? N1 C8 H8A 122.2 . . ? C9 C8 H8A 122.2 . . ? C10 C9 C8 121.0(9) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C11 123.5(8) . . ? C9 C10 H10A 118.2 . . ? C11 C10 H10A 118.2 . . ? C12 C11 C10 116.2(9) . . ? C12 C11 H11A 121.9 . . ? C10 C11 H11A 121.9 . . ? N1 C12 C11 120.8(9) . . ? N1 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? N2 C13 C5 178.9(10) . . ? N3 C14 C6 171.9(10) . . ? C12 N1 C8 122.8(7) . . ? C12 N1 C3 118.6(8) . . ? C8 N1 C3 118.6(7) . . ? C2 O2 C7 121.1(6) . . ? 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 C3 172.6(8) . . . . ? C6 C1 C2 C3 -3.8(10) . . . . ? O1 C1 C2 O2 -5.2(12) . . . . ? C6 C1 C2 O2 178.4(7) . . . . ? O2 C2 C3 N1 0.1(12) . . . . ? C1 C2 C3 N1 -177.6(7) . . . . ? O2 C2 C3 C4 -178.5(7) . . . . ? C1 C2 C3 C4 3.8(13) . . . . ? C2 C3 C4 O3 176.7(9) . . . . ? N1 C3 C4 O3 -2.0(11) . . . . ? C2 C3 C4 C5 -1.2(12) . . . . ? N1 C3 C4 C5 -179.9(7) . . . . ? O3 C4 C5 C6 -179.0(8) . . . . ? C3 C4 C5 C6 -1.1(11) . . . . ? O3 C4 C5 C13 -0.4(12) . . . . ? C3 C4 C5 C13 177.4(7) . . . . ? C13 C5 C6 C14 -4.2(12) . . . . ? C4 C5 C6 C14 174.3(7) . . . . ? C13 C5 C6 C1 -177.9(7) . . . . ? C4 C5 C6 C1 0.7(12) . . . . ? O1 C1 C6 C5 -174.5(8) . . . . ? C2 C1 C6 C5 1.8(11) . . . . ? O1 C1 C6 C14 11.2(11) . . . . ? C2 C1 C6 C14 -172.6(6) . . . . ? N1 C8 C9 C10 -2.2(13) . . . . ? C8 C9 C10 C11 3.4(15) . . . . ? C9 C10 C11 C12 -3.9(14) . . . . ? C10 C11 C12 N1 3.6(14) . . . . ? C6 C5 C13 N2 88(56) . . . . ? C4 C5 C13 N2 -90(56) . . . . ? C5 C6 C14 N3 22(6) . . . . ? C1 C6 C14 N3 -164(6) . . . . ? C11 C12 N1 C8 -2.8(14) . . . . ? C11 C12 N1 C3 178.5(8) . . . . ? C9 C8 N1 C12 2.0(13) . . . . ? C9 C8 N1 C3 -179.4(7) . . . . ? C2 C3 N1 C12 122.1(10) . . . . ? C4 C3 N1 C12 -59.1(10) . . . . ? C2 C3 N1 C8 -56.6(11) . . . . ? C4 C3 N1 C8 122.2(8) . . . . ? C3 C2 O2 C7 148.0(8) . . . . ? C1 C2 O2 C7 -34.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.186 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.048 # start Validation Reply Form _vrf_CHEMW03_y264-2 ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: Pronounced disorder was found in co-crystallised solvent molecules. Therefore, the SQUEEZE option in PLATON was used to calculate the potential solvent accessible volume; 133 Å3 were calculated containing about 40 electrons. Two methane molecules (2 x 18 electrons) per unit cell were included in all further calculations. ; _vrf_PLAT026_y264-2 ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 18 Perc. RESPONSE: The crystal was small and weakly diffracting. Nevertheless the structure is refined with a parameter/reflection ratio of 1:4 and reasonable standard uncertainties. ; _vrf_PLAT043_y264-2 ; PROBLEM: Check Reported Molecular Weight ................ 298.28 RESPONSE: Pronounced disorder was found in co-crystallised solvent molecules. Therefore, the SQUEEZE option in PLATON was used to calculate the potential solvent accessible volume; 133 Å3 were calculated containing about 40 electrons. Two methane molecules (2 x 18 electrons) per unit cell were included in all further calculations. ; _vrf_PLAT044_y264-2 ; PROBLEM: Calculated and Reported Dx Differ .............. ? RESPONSE: Pronounced disorder was found in co-crystallised solvent molecules. Therefore, the SQUEEZE option in PLATON was used to calculate the potential solvent accessible volume; 133 Å3 were calculated containing about 40 electrons. Two methane molecules (2 x 18 electrons) per unit cell were included in all further calculations. ; # end Validation Reply Form