# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name P.Rey P.Brough R.Chiarelli J.Pecaut A.Rassat _publ_contact_author_name 'Dr Paul Rey' _publ_contact_author_address ; Fundamental Research CEA 17 rue des martyrs Grenoble F-38054 FRANCE ; _publ_contact_author_email PREY@CEA.FR _publ_section_title ; A Versatile Synthesis Of New Pyrmidinyl Nitronyl-Nitroxides ; data_struc _database_code_CSD 202737 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H19 N2 O2' _chemical_formula_weight 247.31 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2438(5) _cell_length_b 21.3603(17) _cell_length_c 9.9984(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.862(2) _cell_angle_gamma 90.00 _cell_volume 1323.93(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.084 _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 298(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 'CCD area detector' _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 6664 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.92 _reflns_number_total 3093 _reflns_number_gt 1835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^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 3093 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.23852(17) 0.04139(5) 0.64731(9) 0.0482(3) Uani 1 1 d . . . O2 O 0.66330(19) 0.21502(5) 0.70269(10) 0.0606(4) Uani 1 1 d . . . N1 N 0.30840(18) 0.09232(5) 0.59655(11) 0.0321(3) Uani 1 1 d . . . N2 N 0.51941(18) 0.18343(5) 0.62812(10) 0.0349(3) Uani 1 1 d . . . C1 C 0.4588(2) 0.12687(6) 0.67100(13) 0.0289(3) Uani 1 1 d . . . C2 C 0.2156(2) 0.10734(6) 0.45511(12) 0.0300(3) Uani 1 1 d . . . C3 C 0.3388(2) 0.16285(7) 0.40521(14) 0.0317(3) Uani 1 1 d . . . H3A H 0.252(2) 0.1811(6) 0.3311(14) 0.038(4) Uiso 1 1 d . . . H3B H 0.472(2) 0.1471(6) 0.3707(12) 0.034(4) Uiso 1 1 d . . . C4 C 0.4055(2) 0.21494(6) 0.50568(13) 0.0321(3) Uani 1 1 d . . . C5 C -0.0263(3) 0.11836(9) 0.45437(19) 0.0442(4) Uani 1 1 d . . . H5A H -0.096(3) 0.0809(9) 0.4754(17) 0.068(6) Uiso 1 1 d . . . H5B H -0.090(3) 0.1304(8) 0.3634(17) 0.060(5) Uiso 1 1 d . . . H5C H -0.053(3) 0.1514(8) 0.5230(17) 0.064(5) Uiso 1 1 d . . . C6 C 0.2495(3) 0.04965(8) 0.37026(17) 0.0449(4) Uani 1 1 d . . . H6A H 0.178(3) 0.0125(8) 0.4007(15) 0.061(5) Uiso 1 1 d . . . H6B H 0.408(3) 0.0414(7) 0.3740(14) 0.053(5) Uiso 1 1 d . . . H6C H 0.193(2) 0.0589(7) 0.2743(17) 0.051(4) Uiso 1 1 d . . . C7 C 0.2208(3) 0.25241(8) 0.55281(19) 0.0461(4) Uani 1 1 d . . . H7A H 0.134(3) 0.2711(8) 0.4781(16) 0.066(5) Uiso 1 1 d . . . H7B H 0.280(2) 0.2869(8) 0.6123(15) 0.058(5) Uiso 1 1 d . . . H7C H 0.128(3) 0.2263(8) 0.6053(15) 0.051(5) Uiso 1 1 d . . . C8 C 0.5630(3) 0.25855(8) 0.44746(18) 0.0424(4) Uani 1 1 d . . . H8A H 0.688(3) 0.2339(8) 0.4190(16) 0.065(5) Uiso 1 1 d . . . H8B H 0.614(3) 0.2895(8) 0.5099(15) 0.061(5) Uiso 1 1 d . . . H8C H 0.484(2) 0.2781(7) 0.3687(15) 0.045(4) Uiso 1 1 d . . . C9 C 0.5477(2) 0.10469(6) 0.80713(13) 0.0276(3) Uani 1 1 d . . . C10 C 0.7613(2) 0.08727(6) 0.83548(16) 0.0356(4) Uani 1 1 d . . . H10 H 0.855(2) 0.0882(6) 0.7651(15) 0.041(4) Uiso 1 1 d . . . C11 C 0.8400(3) 0.06796(7) 0.96421(17) 0.0453(4) Uani 1 1 d . . . H11 H 0.988(3) 0.0559(7) 0.9792(16) 0.054(5) Uiso 1 1 d . . . C12 C 0.7060(3) 0.06610(7) 1.06394(17) 0.0511(5) Uani 1 1 d . . . H12 H 0.762(2) 0.0522(8) 1.1497(16) 0.056(5) Uiso 1 1 d . . . C13 C 0.4960(3) 0.08417(8) 1.03607(16) 0.0509(5) Uani 1 1 d . . . H13 H 0.400(3) 0.0839(8) 1.1046(19) 0.067(6) Uiso 1 1 d . . . C14 C 0.4155(3) 0.10357(7) 0.90849(15) 0.0399(4) Uani 1 1 d . . . H14 H 0.275(3) 0.1158(7) 0.8916(15) 0.051(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0579(7) 0.0416(6) 0.0423(6) 0.0128(5) -0.0054(5) -0.0224(5) O2 0.0812(9) 0.0430(7) 0.0483(7) 0.0099(5) -0.0298(6) -0.0259(6) N1 0.0331(7) 0.0323(7) 0.0297(6) 0.0039(5) -0.0005(5) -0.0042(5) N2 0.0415(7) 0.0284(6) 0.0317(6) 0.0046(5) -0.0083(5) -0.0065(5) C1 0.0307(8) 0.0276(7) 0.0282(7) 0.0012(6) 0.0026(6) -0.0007(6) C2 0.0312(8) 0.0338(8) 0.0239(7) 0.0017(6) -0.0012(6) -0.0046(6) C3 0.0317(8) 0.0356(8) 0.0271(8) 0.0043(6) 0.0003(6) -0.0017(7) C4 0.0357(8) 0.0286(7) 0.0302(7) 0.0061(6) -0.0028(6) -0.0011(6) C5 0.0308(9) 0.0502(11) 0.0498(11) 0.0058(9) -0.0026(8) -0.0062(8) C6 0.0594(12) 0.0385(9) 0.0379(10) -0.0038(7) 0.0103(9) -0.0083(9) C7 0.0512(11) 0.0371(9) 0.0491(11) -0.0008(9) 0.0026(9) 0.0044(8) C8 0.0448(10) 0.0363(9) 0.0435(10) 0.0124(8) -0.0057(8) -0.0096(8) C9 0.0299(8) 0.0256(7) 0.0266(7) 0.0000(5) -0.0001(6) -0.0010(6) C10 0.0355(9) 0.0331(8) 0.0379(9) 0.0027(6) 0.0035(7) 0.0008(6) C11 0.0414(10) 0.0360(9) 0.0538(11) 0.0101(7) -0.0142(8) 0.0001(7) C12 0.0724(13) 0.0448(10) 0.0306(9) 0.0118(7) -0.0157(9) -0.0162(9) C13 0.0642(12) 0.0585(11) 0.0312(9) 0.0007(8) 0.0105(9) -0.0157(9) C14 0.0370(10) 0.0454(9) 0.0378(9) -0.0007(7) 0.0069(8) -0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.2979(14) . ? O2 N2 1.2877(13) . ? N1 C1 1.3465(16) . ? N1 C2 1.4975(16) . ? N2 C1 1.3511(17) . ? N2 C4 1.4997(16) . ? C1 C9 1.4849(17) . ? C2 C6 1.525(2) . ? C2 C5 1.528(2) . ? C2 C3 1.5291(19) . ? C3 C4 1.5234(19) . ? C4 C8 1.520(2) . ? C4 C7 1.524(2) . ? C9 C10 1.3812(19) . ? C9 C14 1.382(2) . ? C10 C11 1.385(2) . ? C11 C12 1.377(3) . ? C12 C13 1.363(3) . ? C13 C14 1.378(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 C1 119.21(10) . . ? O1 N1 C2 116.02(10) . . ? C1 N1 C2 124.75(11) . . ? O2 N2 C1 119.17(10) . . ? O2 N2 C4 117.87(10) . . ? C1 N2 C4 122.47(10) . . ? N1 C1 N2 121.20(11) . . ? N1 C1 C9 119.44(11) . . ? N2 C1 C9 119.20(11) . . ? N1 C2 C6 106.77(12) . . ? N1 C2 C5 107.95(12) . . ? C6 C2 C5 108.93(13) . . ? N1 C2 C3 108.75(10) . . ? C6 C2 C3 109.67(12) . . ? C5 C2 C3 114.49(12) . . ? C4 C3 C2 117.37(12) . . ? N2 C4 C8 108.80(11) . . ? N2 C4 C3 106.02(11) . . ? C8 C4 C3 109.48(13) . . ? N2 C4 C7 106.60(12) . . ? C8 C4 C7 110.17(13) . . ? C3 C4 C7 115.47(12) . . ? C10 C9 C14 119.46(13) . . ? C10 C9 C1 121.35(13) . . ? C14 C9 C1 119.15(13) . . ? C9 C10 C11 119.86(16) . . ? C12 C11 C10 120.18(16) . . ? C13 C12 C11 119.79(15) . . ? C12 C13 C14 120.68(18) . . ? C13 C14 C9 120.01(16) . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 28.92 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.193 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.034