data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Nagatoshi Nishiwaki' _publ_contact_author_name 'Nagatoshi Nishiwaki' _publ_contact_author_email NISHIWAKI@ANAN-NCT.AC.JP _publ_section_title ; Formylnitroenamines: Useful Building Blocks for Nitrated Pyridones and Aminopyridines with Functional Groups ; # Attachment '9brsc_2.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 700909' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9b _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 N4 O2' _chemical_formula_sum 'C9 H10 N4 O2' _chemical_formula_weight 206.21 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' 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' H H 0.0000 0.0000 '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 4.5625(6) _cell_length_b 10.2315(19) _cell_length_c 11.4327(17) _cell_angle_alpha 107.479(5) _cell_angle_beta 100.889(8) _cell_angle_gamma 101.507(5) _cell_volume 480.82(13) _cell_formula_units_Z 2 _cell_measurement_temperature 113.2 _cell_measurement_reflns_used 5873 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 113.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.400 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details ? _exptl_special_details ; '(Higashi, 1995)' ; _diffrn_ambient_temperature 113.2 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7811 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2180 _reflns_number_gt 1946 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 2.0' _computing_structure_solution SAPI91 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'teXsan Ver. 2.0' _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^)+(0.0653P)^2^+0.0933P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2180 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.31102(18) 0.15802(8) 0.31553(7) 0.0250(2) Uani 1 1 d . . . O2 O 0.27832(18) 0.04305(8) 0.11832(7) 0.0268(2) Uani 1 1 d . . . N1 N 1.0682(2) 0.46486(9) 0.35091(8) 0.0175(2) Uani 1 1 d . . . N2 N 0.4021(2) 0.14305(9) 0.21883(8) 0.0186(2) Uani 1 1 d . . . N3 N 1.2220(2) 0.36871(10) -0.06673(8) 0.0262(2) Uani 1 1 d . . . N4 N 1.4100(2) 0.57171(9) 0.26107(8) 0.0173(2) Uani 1 1 d . . . C1 C 0.8246(2) 0.36119(10) 0.33865(9) 0.0177(2) Uani 1 1 d . . . C2 C 0.6683(2) 0.25159(10) 0.22395(9) 0.0164(2) Uani 1 1 d . . . C3 C 0.7641(2) 0.24668(10) 0.11502(9) 0.0168(2) Uani 1 1 d . . . C4 C 1.0140(2) 0.35473(10) 0.12518(9) 0.0164(2) Uani 1 1 d . . . C5 C 1.1667(2) 0.46520(10) 0.24620(9) 0.0156(2) Uani 1 1 d . . . C6 C 1.1242(2) 0.35901(10) 0.01650(9) 0.0189(2) Uani 1 1 d . . . C7 C 1.5730(2) 0.68204(10) 0.38567(9) 0.0181(2) Uani 1 1 d . . . C8 C 1.8041(2) 0.80149(11) 0.37121(10) 0.0221(2) Uani 1 1 d . . . C9 C 1.6501(3) 0.88945(12) 0.30643(12) 0.0298(3) Uani 1 1 d . . . H1 H 0.7762 0.3728 0.4179 0.033 Uiso 1 1 d . . . H2 H 0.6714 0.1773 0.0369 0.033 Uiso 1 1 d . . . H3 H 1.4805 0.5660 0.1913 0.033 Uiso 1 1 d . . . H4 H 1.4251 0.7197 0.4241 0.022 Uiso 1 1 d . . . H5 H 1.6784 0.6403 0.4387 0.022 Uiso 1 1 d . . . H6 H 1.9322 0.7607 0.3224 0.026 Uiso 1 1 d . . . H7 H 1.9312 0.8626 0.4537 0.026 Uiso 1 1 d . . . H8 H 1.5214 0.9310 0.3548 0.035 Uiso 1 1 d . . . H9 H 1.8020 0.9626 0.2995 0.035 Uiso 1 1 d . . . H10 H 1.5235 0.8294 0.2235 0.035 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 0.0266(4) 0.0242(4) 0.0227(4) 0.0065(3) 0.0119(3) 0.0017(3) O2 0.0277(4) 0.0195(4) 0.0221(4) -0.0008(3) 0.0040(3) -0.0031(3) N1 0.0194(4) 0.0173(4) 0.0138(4) 0.0036(3) 0.0047(3) 0.0035(3) N2 0.0194(4) 0.0160(4) 0.0187(4) 0.0045(3) 0.0051(3) 0.0037(3) N3 0.0297(5) 0.0260(5) 0.0177(5) 0.0040(4) 0.0075(4) 0.0008(4) N4 0.0190(4) 0.0172(4) 0.0128(4) 0.0033(3) 0.0040(3) 0.0020(3) C1 0.0201(5) 0.0171(5) 0.0154(5) 0.0047(4) 0.0054(4) 0.0048(4) C2 0.0164(5) 0.0147(4) 0.0172(5) 0.0048(4) 0.0047(4) 0.0036(4) C3 0.0191(5) 0.0152(5) 0.0135(5) 0.0023(4) 0.0021(4) 0.0051(4) C4 0.0183(5) 0.0171(4) 0.0134(4) 0.0043(4) 0.0043(3) 0.0054(4) C5 0.0169(5) 0.0152(4) 0.0144(5) 0.0046(4) 0.0031(4) 0.0056(4) C6 0.0199(5) 0.0170(5) 0.0150(5) 0.0020(4) 0.0029(4) 0.0019(4) C7 0.0194(5) 0.0166(4) 0.0149(5) 0.0029(4) 0.0032(4) 0.0028(4) C8 0.0184(5) 0.0206(5) 0.0213(5) 0.0031(4) 0.0039(4) 0.0002(4) C9 0.0300(6) 0.0215(5) 0.0371(6) 0.0127(5) 0.0083(5) 0.0018(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N2 1.2312(11) . ? O2 N2 1.2265(11) . ? N1 C1 1.3273(13) . ? N1 C5 1.3564(13) . ? N2 C2 1.4516(12) . ? N3 C6 1.1462(14) . ? N4 C5 1.3353(13) . ? N4 C7 1.4682(12) . ? C1 C2 1.3893(13) . ? C2 C3 1.3863(14) . ? C3 C4 1.3804(14) . ? C4 C5 1.4350(13) . ? C4 C6 1.4347(13) . ? C7 C8 1.5185(14) . ? C8 C9 1.5191(16) . ? 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 C5 118.54(8) . . ? O2 N2 O1 123.77(9) . . ? O2 N2 C2 118.35(8) . . ? O1 N2 C2 117.87(8) . . ? C5 N4 C7 122.03(8) . . ? N1 C1 C2 123.10(9) . . ? C3 C2 C1 120.22(9) . . ? C3 C2 N2 120.29(9) . . ? C1 C2 N2 119.49(9) . . ? C4 C3 C2 117.63(9) . . ? C3 C4 C5 119.70(9) . . ? C3 C4 C6 121.14(9) . . ? C5 C4 C6 119.16(9) . . ? N4 C5 N1 117.22(8) . . ? N4 C5 C4 122.00(9) . . ? N1 C5 C4 120.78(9) . . ? N3 C6 C4 176.70(10) . . ? N4 C7 C8 110.54(8) . . ? C9 C8 C7 113.12(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 C5 N1 C1 C2 1.05(15) . . . . ? N1 C1 C2 C3 -0.07(16) . . . . ? N1 C1 C2 N2 -179.51(8) . . . . ? O2 N2 C2 C3 4.55(14) . . . . ? O1 N2 C2 C3 -174.40(9) . . . . ? O2 N2 C2 C1 -176.01(9) . . . . ? O1 N2 C2 C1 5.04(14) . . . . ? C1 C2 C3 C4 -0.96(15) . . . . ? N2 C2 C3 C4 178.48(8) . . . . ? C2 C3 C4 C5 0.99(14) . . . . ? C2 C3 C4 C6 -178.82(9) . . . . ? C7 N4 C5 N1 1.96(14) . . . . ? C7 N4 C5 C4 -177.83(8) . . . . ? C1 N1 C5 N4 179.21(8) . . . . ? C1 N1 C5 C4 -0.98(14) . . . . ? C3 C4 C5 N4 179.76(8) . . . . ? C6 C4 C5 N4 -0.43(14) . . . . ? C3 C4 C5 N1 -0.04(15) . . . . ? C6 C4 C5 N1 179.78(9) . . . . ? C3 C4 C6 N3 174.1(19) . . . . ? C5 C4 C6 N3 -6(2) . . . . ? C5 N4 C7 C8 -170.86(8) . . . . ? N4 C7 C8 C9 69.11(11) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.323 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.060