data_1819 _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; piperidine-1-oxyl-4-methylene acetic acid methyl ester ; _chemical_name_common nitroxide _chemical_formula_moiety 'C12 H20 N O3' _chemical_formula_sum 'C12 H20 N O3' _chemical_formula_weight 226.29 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 P21/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 7.7657(7) _cell_length_b 15.5387(14) _cell_length_c 11.2639(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.5925(10) _cell_angle_gamma 90.00 _cell_volume 1280.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 5154 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.5 _exptl_crystal_description bulk _exptl_crystal_colour orange _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method ? _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.914 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 250(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 'three-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 11.198 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9232 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2268 _reflns_number_gt 1909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material SHELXL-97 _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 'w=1/[\s^2^(Fo^2^)+(0.005P)^2^+0.9535P], P=(max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2268 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.6610(2) 0.38706(11) 0.89383(14) 0.0741(5) Uani 1 1 d . . . N1 N 0.5555(2) 0.35818(10) 0.78880(14) 0.0468(4) Uani 1 1 d . . . C2 C 0.3837(2) 0.40869(12) 0.72710(19) 0.0484(5) Uani 1 1 d . . . C2A C 0.4312(3) 0.49318(14) 0.6750(2) 0.0685(7) Uani 1 1 d . . . H2A1 H 0.5193 0.5250 0.7425 0.075(6) Uiso 0.93(3) 1 calc PR . . H2A2 H 0.3213 0.5274 0.6399 0.075(6) Uiso 0.93(3) 1 calc PR . . H2A3 H 0.4832 0.4807 0.6097 0.075(6) Uiso 0.93(3) 1 calc PR . . H2A4 H 0.3633 0.4970 0.5856 0.075(6) Uiso 0.07(3) 1 calc PR . . H2A5 H 0.5612 0.4946 0.6882 0.075(6) Uiso 0.07(3) 1 calc PR . . H2A6 H 0.3993 0.5413 0.7184 0.075(6) Uiso 0.07(3) 1 calc PR . . C2B C 0.2963(3) 0.42736(15) 0.8258(2) 0.0652(6) Uani 1 1 d . . . H2B1 H 0.2718 0.3736 0.8610 0.060(5) Uiso 0.86(2) 1 calc PR . . H2B2 H 0.1826 0.4582 0.7874 0.060(5) Uiso 0.86(2) 1 calc PR . . H2B3 H 0.3785 0.4622 0.8923 0.060(5) Uiso 0.86(2) 1 calc PR . . H2B4 H 0.2834 0.4891 0.8328 0.060(5) Uiso 0.14(2) 1 calc PR . . H2B5 H 0.3727 0.4045 0.9064 0.060(5) Uiso 0.14(2) 1 calc PR . . H2B6 H 0.1767 0.4005 0.8015 0.060(5) Uiso 0.14(2) 1 calc PR . . C3 C 0.2518(2) 0.35544(12) 0.61889(18) 0.0475(5) Uani 1 1 d . . . H3A H 0.1901 0.3127 0.6545 0.058(4) Uiso 1 1 calc R . . H3B H 0.1581 0.3937 0.5643 0.058(4) Uiso 1 1 calc R . . C4 C 0.3469(2) 0.31039(12) 0.54149(18) 0.0441(4) Uani 1 1 d . . . C5 C 0.4927(3) 0.25126(12) 0.61718(18) 0.0488(5) Uani 1 1 d . . . H5A H 0.5474 0.2220 0.5615 0.055(4) Uiso 1 1 calc R . . H5B H 0.4387 0.2073 0.6564 0.055(4) Uiso 1 1 calc R . . C6 C 0.6412(2) 0.29927(13) 0.71939(18) 0.0486(5) Uani 1 1 d . . . C6A C 0.7623(3) 0.35100(16) 0.6627(2) 0.0672(6) Uani 1 1 d . . . H6A1 H 0.6862 0.3869 0.5949 0.074(4) Uiso 1 1 calc R . . H6A2 H 0.8327 0.3118 0.6299 0.074(4) Uiso 1 1 calc R . . H6A3 H 0.8448 0.3870 0.7273 0.074(4) Uiso 1 1 calc R . . C6B C 0.7577(3) 0.23421(15) 0.8149(2) 0.0681(6) Uani 1 1 d . . . H6B1 H 0.8581 0.2639 0.8767 0.090(5) Uiso 1 1 calc R . . H6B2 H 0.8059 0.1916 0.7715 0.090(5) Uiso 1 1 calc R . . H6B3 H 0.6830 0.2060 0.8572 0.090(5) Uiso 1 1 calc R . . C7 C 0.3122(3) 0.32013(12) 0.41688(18) 0.0479(5) Uani 1 1 d . . . H7 H 0.3822 0.2861 0.3811 0.068(7) Uiso 1 1 calc R . . C8 C 0.1776(2) 0.37773(12) 0.33009(17) 0.0434(4) Uani 1 1 d . . . O8 O 0.0882(2) 0.43324(10) 0.35579(13) 0.0633(4) Uani 1 1 d . . . O9 O 0.1677(2) 0.35998(9) 0.21150(13) 0.0609(4) Uani 1 1 d . . . C9 C 0.0499(3) 0.41343(16) 0.11337(19) 0.0699(7) Uani 1 1 d . . . H9A H -0.0752 0.4074 0.1117 0.076(6) Uiso 0.75(3) 1 calc PR . . H9B H 0.0580 0.3959 0.0327 0.076(6) Uiso 0.75(3) 1 calc PR . . H9C H 0.0875 0.4730 0.1295 0.076(6) Uiso 0.75(3) 1 calc PR . . H9D H 0.1221 0.4435 0.0709 0.076(6) Uiso 0.25(3) 1 calc PR . . H9E H -0.0111 0.4550 0.1499 0.076(6) Uiso 0.25(3) 1 calc PR . . H9F H -0.0407 0.3778 0.0531 0.076(6) Uiso 0.25(3) 1 calc PR . . 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 0.0580(9) 0.0932(12) 0.0558(9) -0.0184(9) -0.0012(7) 0.0092(9) N1 0.0388(8) 0.0507(9) 0.0459(9) -0.0006(7) 0.0076(7) 0.0034(7) C2 0.0427(10) 0.0430(10) 0.0575(12) 0.0043(9) 0.0143(9) 0.0073(8) C2A 0.0667(15) 0.0466(12) 0.0866(17) 0.0065(12) 0.0182(13) -0.0006(11) C2B 0.0612(13) 0.0678(15) 0.0663(14) -0.0059(12) 0.0208(11) 0.0159(11) C3 0.0350(9) 0.0480(11) 0.0561(12) 0.0046(9) 0.0107(8) 0.0020(8) C4 0.0376(9) 0.0401(10) 0.0542(11) -0.0031(8) 0.0147(8) -0.0059(8) C5 0.0474(10) 0.0449(10) 0.0554(12) 0.0016(9) 0.0190(9) 0.0029(9) C6 0.0403(10) 0.0531(11) 0.0536(11) 0.0006(9) 0.0173(9) 0.0029(9) C6A 0.0503(12) 0.0763(16) 0.0804(16) -0.0046(13) 0.0289(12) -0.0097(11) C6B 0.0547(13) 0.0720(15) 0.0718(15) 0.0056(12) 0.0134(11) 0.0210(11) C7 0.0431(10) 0.0450(10) 0.0543(12) -0.0028(9) 0.0145(9) 0.0021(8) C8 0.0386(10) 0.0420(10) 0.0463(11) -0.0038(8) 0.0097(8) -0.0028(8) O8 0.0658(9) 0.0604(9) 0.0605(9) 0.0002(7) 0.0168(7) 0.0180(8) O9 0.0636(9) 0.0651(9) 0.0474(8) -0.0012(7) 0.0097(7) 0.0130(7) C9 0.0735(15) 0.0787(16) 0.0447(12) 0.0041(11) 0.0029(11) 0.0196(13) _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 1.2736(19) . ? N1 C6 1.497(2) . ? N1 C2 1.502(2) . ? C2 C2B 1.512(3) . ? C2 C2A 1.533(3) . ? C2 C3 1.543(3) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C2A H2A3 0.9700 . ? C2A H2A4 0.9700 . ? C2A H2A5 0.9700 . ? C2A H2A6 0.9700 . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C2B H2B3 0.9700 . ? C2B H2B4 0.9700 . ? C2B H2B5 0.9700 . ? C2B H2B6 0.9700 . ? C3 C4 1.492(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C7 1.346(3) . ? C4 C5 1.485(3) . ? C5 C6 1.523(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C6A 1.530(3) . ? C6 C6B 1.532(3) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C6A H6A3 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C6B H6B3 0.9700 . ? C7 C8 1.471(3) . ? C7 H7 0.9400 . ? C8 O8 1.202(2) . ? C8 O9 1.341(2) . ? O9 C9 1.439(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C9 H9D 0.9700 . ? C9 H9E 0.9700 . ? C9 H9F 0.9700 . ? 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 C6 116.12(14) . . ? O1 N1 C2 116.14(15) . . ? C6 N1 C2 124.00(15) . . ? N1 C2 C2B 107.93(16) . . ? N1 C2 C2A 109.53(16) . . ? C2B C2 C2A 110.00(18) . . ? N1 C2 C3 109.67(15) . . ? C2B C2 C3 109.91(17) . . ? C2A C2 C3 109.78(17) . . ? C2 C2A H2A1 109.5 . . ? C2 C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C2 C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C2 C2A H2A4 109.5 . . ? H2A1 C2A H2A4 141.1 . . ? H2A2 C2A H2A4 56.3 . . ? H2A3 C2A H2A4 56.3 . . ? C2 C2A H2A5 109.5 . . ? H2A1 C2A H2A5 56.3 . . ? H2A2 C2A H2A5 141.1 . . ? H2A3 C2A H2A5 56.3 . . ? H2A4 C2A H2A5 109.5 . . ? C2 C2A H2A6 109.5 . . ? H2A1 C2A H2A6 56.3 . . ? H2A2 C2A H2A6 56.3 . . ? H2A3 C2A H2A6 141.1 . . ? H2A4 C2A H2A6 109.5 . . ? H2A5 C2A H2A6 109.5 . . ? C2 C2B H2B1 109.5 . . ? C2 C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C2 C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C2 C2B H2B4 109.5 . . ? H2B1 C2B H2B4 141.1 . . ? H2B2 C2B H2B4 56.3 . . ? H2B3 C2B H2B4 56.3 . . ? C2 C2B H2B5 109.5 . . ? H2B1 C2B H2B5 56.3 . . ? H2B2 C2B H2B5 141.1 . . ? H2B3 C2B H2B5 56.3 . . ? H2B4 C2B H2B5 109.5 . . ? C2 C2B H2B6 109.5 . . ? H2B1 C2B H2B6 56.3 . . ? H2B2 C2B H2B6 56.3 . . ? H2B3 C2B H2B6 141.1 . . ? H2B4 C2B H2B6 109.5 . . ? H2B5 C2B H2B6 109.5 . . ? C4 C3 C2 112.66(15) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C7 C4 C5 121.04(17) . . ? C7 C4 C3 126.24(17) . . ? C5 C4 C3 112.72(16) . . ? C4 C5 C6 111.66(16) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? N1 C6 C5 109.74(14) . . ? N1 C6 C6A 109.87(16) . . ? C5 C6 C6A 110.93(17) . . ? N1 C6 C6B 107.34(16) . . ? C5 C6 C6B 109.08(17) . . ? C6A C6 C6B 109.81(17) . . ? C6 C6A H6A1 109.5 . . ? C6 C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C6 C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? C6 C6B H6B1 109.5 . . ? C6 C6B H6B2 109.5 . . ? H6B1 C6B H6B2 109.5 . . ? C6 C6B H6B3 109.5 . . ? H6B1 C6B H6B3 109.5 . . ? H6B2 C6B H6B3 109.5 . . ? C4 C7 C8 127.63(18) . . ? C4 C7 H7 116.2 . . ? C8 C7 H7 116.2 . . ? O8 C8 O9 122.87(17) . . ? O8 C8 C7 128.00(18) . . ? O9 C8 C7 109.12(16) . . ? C8 O9 C9 117.14(16) . . ? O9 C9 H9A 109.5 . . ? O9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O9 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O9 C9 H9D 109.5 . . ? H9A C9 H9D 141.1 . . ? H9B C9 H9D 56.3 . . ? H9C C9 H9D 56.3 . . ? O9 C9 H9E 109.5 . . ? H9A C9 H9E 56.3 . . ? H9B C9 H9E 141.1 . . ? H9C C9 H9E 56.3 . . ? H9D C9 H9E 109.5 . . ? O9 C9 H9F 109.5 . . ? H9A C9 H9F 56.3 . . ? H9B C9 H9F 56.3 . . ? H9C C9 H9F 141.1 . . ? H9D C9 H9F 109.5 . . ? H9E C9 H9F 109.5 . . ? 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 N1 C2 C2B -47.4(2) . . . . ? C6 N1 C2 C2B 155.33(17) . . . . ? O1 N1 C2 C2A 72.4(2) . . . . ? C6 N1 C2 C2A -84.9(2) . . . . ? O1 N1 C2 C3 -167.09(16) . . . . ? C6 N1 C2 C3 35.6(2) . . . . ? N1 C2 C3 C4 -42.5(2) . . . . ? C2B C2 C3 C4 -160.97(17) . . . . ? C2A C2 C3 C4 77.9(2) . . . . ? C2 C3 C4 C7 -121.0(2) . . . . ? C2 C3 C4 C5 58.3(2) . . . . ? C7 C4 C5 C6 118.40(19) . . . . ? C3 C4 C5 C6 -60.9(2) . . . . ? O1 N1 C6 C5 164.37(17) . . . . ? C2 N1 C6 C5 -38.3(2) . . . . ? O1 N1 C6 C6A -73.4(2) . . . . ? C2 N1 C6 C6A 83.9(2) . . . . ? O1 N1 C6 C6B 45.9(2) . . . . ? C2 N1 C6 C6B -156.75(17) . . . . ? C4 C5 C6 N1 47.6(2) . . . . ? C4 C5 C6 C6A -74.0(2) . . . . ? C4 C5 C6 C6B 164.92(17) . . . . ? C5 C4 C7 C8 -177.88(17) . . . . ? C3 C4 C7 C8 1.4(3) . . . . ? C4 C7 C8 O8 8.9(3) . . . . ? C4 C7 C8 O9 -171.64(18) . . . . ? O8 C8 O9 C9 2.9(3) . . . . ? C7 C8 O9 C9 -176.56(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.034 _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.1280062 _diffrn_orient_matrix_UB_12 -0.0106648 _diffrn_orient_matrix_UB_13 0.0570333 _diffrn_orient_matrix_UB_21 -0.0466372 _diffrn_orient_matrix_UB_22 -0.0408026 _diffrn_orient_matrix_UB_23 0.0508362 _diffrn_orient_matrix_UB_31 0.0110672 _diffrn_orient_matrix_UB_32 -0.0486115 _diffrn_orient_matrix_UB_33 -0.0551647 _symmetry_space_group_name_Hall '-P 2ybc' _exptl_crystal_id 'UMBC/Kao piperidine-1-oxyl-4-methylene acetic acid methyl ester' _diffrn_measurement_frame_width-CCD -0.30 _diffrn_measurement_details 610,610,610 _diffrn_measurement_total_frames-CCD 1830 _diffrn_measurement_frame_time-CCD 45 _diffrn_measurement_total_time-CCD 25.9 _diffrn_source_voltage 50.00 _diffrn_source_current 30.00 _diffrn_detector_distance-CCD 5.800 _diffrn_measurement_frame_size-CCD 512 _diffrn_measurement_specimen_support 'glass capillary' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' #_______________________________________________________________________________ # _publ_section_references ; Bruker (2005). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst., A46, C-34. ;