#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/30/2003060.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003060 loop_ _publ_author_name ; Fujiko Iwasaki ; _publ_section_title ; TEMPO radicals showing magnetic interactions. I. 4-(4-Halobenzylideneamino)TEMPO and related compounds ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 231 _journal_page_last 245 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C15 H22 N3 O' _chemical_formula_weight 260.36 _chemical_name_common 4-Py-TEMPO _chemical_name_systematic ' 4-(4-pyridyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 125.95(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.977(6) _cell_length_b 20.158(7) _cell_length_c 11.383(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 17.3 _cell_measurement_theta_min 14.3 _cell_volume 1482(2) _computing_cell_refinement 'Rigaku/AFC Diffractometer Control' _computing_data_collection 'Rigaku/AFC Diffractometer Control' _computing_data_reduction teXsan _computing_molecular_graphics 'ORTEP II' _computing_publication_material teXsan _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution SAPI91 _diffrn_ambient_temperature 295 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3631 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.02 _diffrn_standards_decay_% -0.08 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 564.00 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.148 _refine_diff_density_min -0.190 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 260 _refine_ls_number_reflns 3400 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.2298P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref 0.1204 _reflns_number_gt 2464 _reflns_number_total 3400 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file oa0019.cif _[local]_cod_data_source_block 6 _[local]_cod_cif_authors_sg_H-M 'P 21/c ' _[local]_cod_chemical_formula_sum_orig 'C15 H22 N3 O ' _cod_original_cell_volume 1481.0(10) _cod_database_code 2003060 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -2 -2 1 -1 -2 -1 -4 -1 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' O O 0.0106 0.0060 '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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.66692(17) 0.20588(5) 0.68638(10) 0.0614(3) Uani d . 1 . . O N1 0.57579(17) 0.18079(5) 0.55966(10) 0.0426(2) Uani d . 1 . . N N2 0.32248(19) 0.08646(6) 0.15827(12) 0.0556(3) Uani d . 1 . . N N14 0.1225(2) -0.02359(7) -0.30557(13) 0.0618(3) Uani d . 1 . . N C2 0.5925(2) 0.21876(6) 0.45395(13) 0.0449(3) Uani d . 1 . . C C3 0.5402(2) 0.17283(7) 0.32952(14) 0.0486(3) Uani d . 1 . . C C4 0.3435(2) 0.13250(7) 0.26638(14) 0.0494(3) Uani d . 1 . . C C5 0.3671(3) 0.09152(7) 0.38637(17) 0.0533(3) Uani d . 1 . . C C6 0.4072(2) 0.13205(6) 0.51462(14) 0.0476(3) Uani d . 1 . . C C7 0.1824(2) 0.09644(8) 0.02753(16) 0.0546(3) Uani d . 1 . . C C11 0.1579(2) 0.05324(7) -0.08720(14) 0.0500(3) Uani d . 1 . . C C12 0.0459(2) 0.07502(8) -0.22893(16) 0.0596(4) Uani d . 1 . . C C13 0.0340(3) 0.03546(9) -0.33276(16) 0.0623(4) Uani d . 1 . . C C15 0.2279(3) -0.04471(9) -0.16901(17) 0.0645(4) Uani d . 1 . . C C16 0.2495(2) -0.00854(8) -0.05737(16) 0.0594(4) Uani d . 1 . . C C21 0.8150(3) 0.24249(10) 0.5323(2) 0.0655(4) Uani d . 1 . . C C22 0.4489(3) 0.27924(8) 0.40051(19) 0.0627(4) Uani d . 1 . . C C61 0.2127(3) 0.16838(9) 0.4769(2) 0.0613(4) Uani d . 1 . . C C62 0.4821(4) 0.08522(8) 0.6422(2) 0.0661(4) Uani d . 1 . . C H4 0.220(2) 0.1627(7) 0.2193(15) 0.051(4) Uiso d . 1 . . H H7 0.082(3) 0.1336(9) -0.0051(18) 0.076(5) Uiso d . 1 . . H H12 -0.022(3) 0.1174(9) -0.2521(19) 0.078(5) Uiso d . 1 . . H H13 -0.049(3) 0.0500(8) -0.436(2) 0.077(5) Uiso d . 1 . . H H15 0.294(3) -0.0890(10) -0.1486(19) 0.084(6) Uiso d . 1 . . H H16 0.330(3) -0.0255(8) 0.036(2) 0.073(5) Uiso d . 1 . . H H21 0.907(3) 0.2050(10) 0.574(2) 0.082(6) Uiso d . 1 . . H H22 0.831(3) 0.2648(10) 0.463(2) 0.094(6) Uiso d . 1 . . H H23 0.846(3) 0.2743(9) 0.608(2) 0.078(5) Uiso d . 1 . . H H24 0.297(3) 0.2678(10) 0.335(2) 0.085(6) Uiso d . 1 . . H H25 0.475(3) 0.3036(9) 0.482(2) 0.082(5) Uiso d . 1 . . H H26 0.478(3) 0.3088(10) 0.348(2) 0.099(7) Uiso d . 1 . . H H31 0.660(2) 0.1408(8) 0.3669(16) 0.059(4) Uiso d . 1 . . H H32 0.530(2) 0.2005(8) 0.2524(17) 0.063(4) Uiso d . 1 . . H H51 0.244(3) 0.0638(8) 0.3487(17) 0.066(5) Uiso d . 1 . . H H52 0.490(2) 0.0604(7) 0.4235(16) 0.055(4) Uiso d . 1 . . H H61 0.112(3) 0.1383(10) 0.4606(19) 0.082(6) Uiso d . 1 . . H H62 0.248(3) 0.1981(9) 0.5561(19) 0.075(5) Uiso d . 1 . . H H63 0.145(3) 0.1973(9) 0.386(2) 0.076(5) Uiso d . 1 . . H H64 0.615(3) 0.0634(10) 0.675(2) 0.089(6) Uiso d . 1 . . H H65 0.375(3) 0.0500(10) 0.611(2) 0.090(6) Uiso d . 1 . . H H66 0.511(3) 0.1101(10) 0.726(2) 0.085(6) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0810(7) 0.0637(6) 0.0419(5) -0.0090(5) 0.0375(5) -0.0116(4) N1 0.0540(6) 0.0399(5) 0.0381(5) 0.0006(4) 0.0294(5) -0.0023(4) N2 0.0587(7) 0.0626(7) 0.0485(6) -0.0005(6) 0.0332(6) -0.0140(5) N14 0.0656(8) 0.0754(9) 0.0488(7) -0.0134(7) 0.0361(6) -0.0173(6) C2 0.0550(7) 0.0429(6) 0.0400(6) -0.0044(5) 0.0297(6) -0.0001(5) C3 0.0601(8) 0.0519(7) 0.0423(7) -0.0035(6) 0.0348(6) -0.0024(6) C4 0.0516(7) 0.0529(7) 0.0450(7) 0.0010(6) 0.0290(6) -0.0111(6) C5 0.0662(9) 0.0463(7) 0.0653(9) -0.0117(7) 0.0486(8) -0.0157(6) C6 0.0621(8) 0.0416(6) 0.0556(7) -0.0041(6) 0.0438(7) -0.0066(5) C7 0.0555(8) 0.0576(8) 0.0510(8) 0.0013(7) 0.0314(7) -0.0074(6) C11 0.0479(7) 0.0574(8) 0.0447(7) -0.0061(6) 0.0272(6) -0.0097(6) C12 0.0639(9) 0.0591(9) 0.0498(8) -0.0024(7) 0.0301(7) -0.0019(7) C13 0.0665(9) 0.0752(11) 0.0428(7) -0.0142(8) 0.0308(7) -0.0050(7) C15 0.0693(10) 0.0658(10) 0.0545(8) 0.0035(8) 0.0342(8) -0.0109(7) C16 0.0629(9) 0.0661(9) 0.0417(7) 0.0036(7) 0.0266(7) -0.0041(6) C21 0.0656(10) 0.0730(11) 0.0593(9) -0.0208(9) 0.0374(8) -0.0073(8) C22 0.0844(12) 0.0420(7) 0.0576(9) 0.0055(7) 0.0395(9) 0.0052(7) C61 0.0641(9) 0.0651(9) 0.0730(10) -0.0033(8) 0.0505(9) -0.0136(8) C62 0.1050(14) 0.0474(8) 0.0774(11) 0.0006(9) 0.0711(11) 0.0036(8) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O1 N1 C6 116.67(11) yes O1 N1 C2 116.42(11) yes C6 N1 C2 123.23(11) yes C7 N2 C4 118.66(13) yes C13 N14 C15 116.42(13) no N1 C2 C21 108.24(13) no N1 C2 C3 109.28(11) yes C21 C2 C3 108.84(13) no N1 C2 C22 109.12(12) yes C21 C2 C22 108.97(14) no C3 C2 C22 112.30(13) no C4 C3 C2 113.93(12) yes C4 C3 H31 108.1(9) no C2 C3 H31 108.5(9) no C4 C3 H32 110.7(9) no C2 C3 H32 108.2(9) no H31 C3 H32 107.2(12) no N2 C4 C5 107.70(12) yes N2 C4 C3 108.19(12) yes C5 C4 C3 108.57(13) yes N2 C4 H4 110.0(8) no C5 C4 H4 112.2(8) no C3 C4 H4 110.1(8) no C4 C5 C6 114.53(12) yes C4 C5 H51 110.7(9) no C6 C5 H51 108.5(9) no C4 C5 H52 106.7(8) no C6 C5 H52 108.7(8) no H51 C5 H52 107.4(13) no N1 C6 C62 108.00(14) no N1 C6 C61 109.98(12) no C62 C6 C61 109.19(14) no N1 C6 C5 108.64(11) yes C62 C6 C5 108.78(13) no C61 C6 C5 112.15(14) no N2 C7 C11 121.26(15) yes N2 C7 H7 121.9(10) no C11 C7 H7 116.8(10) no C12 C11 C16 117.42(13) no C12 C11 C7 120.20(14) no C16 C11 C7 122.36(14) no C11 C12 C13 119.28(16) no C11 C12 H12 118.6(11) no C13 C12 H12 122.2(11) no N14 C13 C12 123.99(15) no N14 C13 H13 115.8(10) no C12 C13 H13 120.2(10) no N14 C15 C16 123.81(17) no N14 C15 H15 116.4(11) no C16 C15 H15 119.7(11) no C11 C16 C15 119.07(15) no C11 C16 H16 121.6(11) no C15 C16 H16 119.2(11) no C2 C21 H21 109.3(11) no C2 C21 H22 109.2(12) no H21 C21 H22 110.0(17) no C2 C21 H23 109.1(11) no H21 C21 H23 110.5(15) no H22 C21 H23 108.8(16) no C2 C22 H24 113.9(11) no C2 C22 H25 109.5(11) no H24 C22 H25 108.2(16) no C2 C22 H26 110.1(13) no H24 C22 H26 108.1(16) no H25 C22 H26 106.7(16) no C6 C61 H61 110.9(12) no C6 C61 H62 110.0(10) no H61 C61 H62 109.0(16) no C6 C61 H63 113.7(10) no H61 C61 H63 106.7(15) no H62 C61 H63 106.4(14) no C6 C62 H64 111.3(12) no C6 C62 H65 108.7(12) no H64 C62 H65 108.4(16) no C6 C62 H66 110.4(11) no H64 C62 H66 106.0(16) no H65 C62 H66 112.1(16) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 1.2782(17) yes N1 C6 1.4926(19) yes N1 C2 1.4963(17) yes N2 C7 1.246(2) yes N2 C4 1.4701(17) yes N14 C13 1.325(2) no N14 C15 1.330(2) no C2 C21 1.522(3) no C2 C3 1.5308(19) yes C2 C22 1.533(2) no C3 C4 1.521(2) yes C3 H31 1.014(16) no C3 H32 1.003(15) no C4 C5 1.510(2) yes C4 H4 1.003(15) no C5 C6 1.534(2) yes C5 H51 .981(17) no C5 H52 1.026(16) no C6 C62 1.529(2) no C6 C61 1.531(2) no C7 C11 1.484(2) yes C7 H7 .996(18) no C11 C12 1.379(2) no C11 C16 1.381(2) no C12 C13 1.382(2) no C12 H12 .961(18) no C13 H13 .992(18) no C15 C16 1.385(2) no C15 H15 .993(19) no C16 H16 .930(18) no C21 H21 .96(2) no C21 H22 .98(2) no C21 H23 .980(19) no C22 H24 1.01(2) no C22 H25 .961(19) no C22 H26 .96(2) no C61 H61 .94(2) no C61 H62 .977(18) no C61 H63 1.024(18) no C62 H64 1.00(2) no C62 H65 1.00(2) no C62 H66 .98(2) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O1 7.977(6) 1_555 1_455 yes O1 O1 5.963(4) 1_555 4_555 yes O1 O1 6.774(7) 1_555 4_655 yes O1 C22 3.746(3) 1_555 4_555 no O1 C3 3.404(2) 1_555 4_555 yes O1 C21 3.539(4) 1_555 4_555 yes O1 H22 2.67(2) 1_555 4_555 yes O1 H32 2.51(2) 1_555 4_555 yes 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_publ_flag O1 N1 C2 C21 43.19(16) no C6 N1 C2 C21 -159.17(13) no O1 N1 C2 C3 161.59(11) yes C6 N1 C2 C3 -40.77(16) yes O1 N1 C2 C22 -75.26(16) no C6 N1 C2 C22 82.38(15) no N1 C2 C3 C4 47.67(16) yes C21 C2 C3 C4 165.68(13) no C22 C2 C3 C4 -73.57(17) no C7 N2 C4 C5 133.09(15) yes C7 N2 C4 C3 -109.73(17) yes C2 C3 C4 N2 -174.81(11) yes C2 C3 C4 C5 -58.19(16) yes N2 C4 C5 C6 175.69(12) yes C3 C4 C5 C6 58.76(16) yes O1 N1 C6 C62 -43.88(15) no C2 N1 C6 C62 158.53(12) no O1 N1 C6 C61 75.19(15) no C2 N1 C6 C61 -82.40(15) no O1 N1 C6 C5 -161.72(11) yes C2 N1 C6 C5 40.69(16) yes C4 C5 C6 N1 -48.31(17) yes C4 C5 C6 C62 -165.65(14) no C4 C5 C6 C61 73.46(16) no C4 N2 C7 C11 177.72(12) yes N2 C7 C11 C12 -161.08(15) yes N2 C7 C11 C16 16.8(2) yes C16 C11 C12 C13 -1.4(2) no C7 C11 C12 C13 176.66(14) no C15 N14 C13 C12 .1(2) no C11 C12 C13 N14 .8(2) no C13 N14 C15 C16 -.5(2) no C12 C11 C16 C15 1.1(2) no C7 C11 C16 C15 -176.92(14) no N14 C15 C16 C11 -.1(3) no _cod_database_fobs_code 2003060 _journal_paper_doi 10.1107/S0108768198012786