data_herges87 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 N4 O2' _chemical_formula_weight 300.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' _cell_length_a 5.1513(7) _cell_length_b 25.835(3) _cell_length_c 6.7094(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.501(17) _cell_angle_gamma 90.00 _cell_volume 880.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.077 _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 200(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-1' _diffrn_measurement_method 'Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2393 _diffrn_reflns_av_R_equivalents 0.1048 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 26.99 _reflns_number_total 983 _reflns_number_gt 714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS-1 program package' _computing_cell_refinement 'STOE IPDS-1 program package' _computing_data_reduction 'STOE IPDS-1 program package' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'XCIF in SHELXTL-PC' _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^)+(0.0641P)^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 SHELXL _refine_ls_extinction_coef 0.040(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(3) _refine_ls_number_reflns 983 _refine_ls_number_parameters 129 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.023 _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 0.9787(8) 0.94548(16) 0.2597(6) 0.0488(10) Uani 1 1 d . . . C2 C 1.1029(10) 0.94228(16) 0.4612(8) 0.0647(14) Uani 1 1 d . . . C3 C 1.0024(13) 0.90636(16) 0.5846(8) 0.0773(18) Uani 1 1 d . . . H3 H 1.0826 0.9035 0.7222 0.093 Uiso 1 1 calc R . . C4 C 0.7915(11) 0.87498(16) 0.5135(6) 0.0638(14) Uani 1 1 d . . . H4 H 0.7268 0.8512 0.6017 0.077 Uiso 1 1 calc R . . C5 C 0.6724(8) 0.87824(15) 0.3101(5) 0.0438(9) Uani 1 1 d . . . C6 C 0.7673(8) 0.91325(16) 0.1835(6) 0.0467(9) Uani 1 1 d . . . H6 H 0.6890 0.9154 0.0452 0.056 Uiso 1 1 calc R . . N1 N 1.0784(8) 0.97589(16) 0.1084(5) 0.0615(11) Uani 1 1 d . . . C7 C 1.3047(17) 0.9723(3) 0.6020(13) 0.0428(18) Uani 0.50 1 d P . 1 H7A H 1.2913 0.9610 0.7410 0.051 Uiso 0.50 1 calc PR . 1 H7B H 1.4797 0.9610 0.5758 0.051 Uiso 0.50 1 calc PR . 1 C7' C 1.3653(18) 0.9782(3) 0.4964(16) 0.050(2) Uani 0.50 1 d P . 2 H7C H 1.4673 0.9676 0.6283 0.060 Uiso 0.50 1 calc PR . 2 H7D H 1.4705 0.9676 0.3925 0.060 Uiso 0.50 1 calc PR . 2 N2 N 0.4540(7) 0.84528(12) 0.2489(4) 0.0460(8) Uani 1 1 d . . . H2 H 0.3760 0.8336 0.3470 0.055 Uiso 1 1 calc R . . C8 C 0.3488(7) 0.82934(13) 0.0618(5) 0.0401(8) Uani 1 1 d . . . C9 C 0.1064(8) 0.79698(16) 0.0494(6) 0.0484(10) Uani 1 1 d . . . H9A H -0.0467 0.8171 -0.0135 0.073 Uiso 1 1 calc R . . H9B H 0.0829 0.7865 0.1856 0.073 Uiso 1 1 calc R . . H9C H 0.1241 0.7661 -0.0322 0.073 Uiso 1 1 calc R . . O1 O 0.4450(6) 0.84050(10) -0.0898(4) 0.0462(7) Uani 1 1 d . . . O2 O 0.3191(6) 0.77684(10) -0.4245(3) 0.0500(7) Uani 1 1 d . . . H1O2 H 0.3473 0.7928 -0.3140 0.075 Uiso 1 1 d R . . H2O2 H 0.1706 0.7634 -0.4251 0.075 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 C1 0.043(2) 0.043(2) 0.061(2) -0.0183(17) 0.0121(17) 0.002(2) C2 0.060(3) 0.032(2) 0.089(3) -0.011(2) -0.026(2) 0.012(2) C3 0.113(5) 0.031(2) 0.068(2) -0.008(2) -0.044(3) 0.014(3) C4 0.096(4) 0.038(2) 0.049(2) -0.0036(16) -0.014(2) 0.012(2) C5 0.048(3) 0.038(2) 0.0434(18) -0.0074(14) 0.0033(16) 0.0074(18) C6 0.048(2) 0.046(2) 0.0470(17) -0.0120(16) 0.0096(15) 0.0001(19) N1 0.050(2) 0.087(3) 0.0520(17) -0.0221(16) 0.0215(15) -0.0051(18) C7 0.035(5) 0.040(4) 0.049(4) 0.001(4) -0.006(3) -0.002(4) C7' 0.043(6) 0.042(4) 0.062(5) -0.004(4) -0.003(4) 0.008(4) N2 0.057(2) 0.0451(19) 0.0362(14) -0.0037(13) 0.0074(13) 0.0033(17) C8 0.048(2) 0.0328(17) 0.0387(17) -0.0010(14) 0.0050(15) 0.0076(16) C9 0.049(3) 0.047(2) 0.0483(19) -0.0053(16) 0.0078(16) -0.002(2) O1 0.0540(17) 0.0463(15) 0.0374(11) -0.0038(11) 0.0051(10) -0.0013(14) O2 0.0616(18) 0.0475(15) 0.0414(12) -0.0019(12) 0.0101(12) 0.0018(15) _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 1.399(6) . ? C1 C6 1.399(6) . ? C1 N1 1.444(6) . ? C2 C3 1.399(9) . ? C2 C7 1.500(9) . ? C2 C7' 1.625(11) . ? C3 C4 1.376(7) . ? C4 C5 1.404(5) . ? C5 C6 1.384(6) . ? C5 N2 1.416(5) . ? N1 N1 1.246(8) 2_575 ? C7 C7 1.432(16) 2_575 ? C7' C7' 1.124(17) 2_575 ? N2 C8 1.347(5) . ? C8 O1 1.237(4) . ? C8 C9 1.493(6) . ? 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 C6 121.5(4) . . ? C2 C1 N1 123.6(4) . . ? C6 C1 N1 114.4(4) . . ? C3 C2 C1 117.2(4) . . ? C3 C2 C7 104.8(5) . . ? C1 C2 C7 137.5(6) . . ? C3 C2 C7' 132.3(5) . . ? C1 C2 C7' 110.1(6) . . ? C7 C2 C7' 30.6(4) . . ? C4 C3 C2 122.3(4) . . ? C3 C4 C5 119.7(5) . . ? C6 C5 C4 119.6(4) . . ? C6 C5 N2 124.0(3) . . ? C4 C5 N2 116.4(4) . . ? C5 C6 C1 119.8(4) . . ? N1 N1 C1 123.0(2) 2_575 . ? C7 C7 C2 121.1(3) 2_575 . ? C7' C7' C2 124.9(3) 2_575 . ? C8 N2 C5 129.2(3) . . ? O1 C8 N2 122.7(4) . . ? O1 C8 C9 122.0(3) . . ? N2 C8 C9 115.3(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.175 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.040