#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/30/2003065.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_2003065 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_paper_doi 10.1107/S0108768198012786 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C22 H27 N2 O ' _chemical_formula_sum 'C22 H27 N2 O' _chemical_formula_weight 335.47 _chemical_name_common biPh-TEMPO _chemical_name_systematic ' 4-(biphenyl-4-yl)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' _cell_angle_alpha 90 _cell_angle_beta 106.72(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.9550(10) _cell_length_b 28.488(5) _cell_length_c 11.796(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.5 _cell_measurement_theta_min 13.9 _cell_volume 1916.5(6) _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_collection 'MSC/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 SIR88 _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w _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 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4774 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.80 _diffrn_standards_decay_% -0.72 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_crystal_colour Orange _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 724.00 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.286 _refine_diff_density_min -0.254 _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 335 _refine_ls_number_reflns 4372 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.981 _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0624 _refine_ls_shift/su_max 0.194 _refine_ls_shift/su_mean 0.037 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1817 _reflns_number_gt 2488 _reflns_number_total 4372 _reflns_threshold_expression >2sigma(I) _cod_data_source_file oa0019.cif _cod_data_source_block 5 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c ' _cod_original_formula_sum 'C22 H27 N2 O ' _cod_database_code 2003065 _cod_database_fobs_code 2003065 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_ _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 -0.2026(3) 0.22330(7) 0.61910(15) 0.0714(6) Uani d . 1 . . O N1 -0.0943(3) 0.20482(7) 0.55047(15) 0.0492(5) Uani d . 1 . . N N2 0.1857(4) 0.13859(8) 0.30386(17) 0.0607(6) Uani d . 1 . . N C2 -0.0380(4) 0.23685(8) 0.46225(19) 0.0526(6) Uani d . 1 . . C C3 0.0168(5) 0.20741(9) 0.3655(2) 0.0536(6) Uani d . 1 . . C C4 0.1819(4) 0.16641(8) 0.4082(2) 0.0516(6) Uani d . 1 . . C C5 0.0833(5) 0.13554(9) 0.4874(2) 0.0569(6) Uani d . 1 . . C C6 0.0346(4) 0.16040(8) 0.59225(19) 0.0522(6) Uani d . 1 . . C C7 0.3585(5) 0.13943(9) 0.2654(2) 0.0568(6) Uani d . 1 . . C C11 0.3634(4) 0.11384(8) 0.1576(2) 0.0518(6) Uani d . 1 . . C C12 0.1862(6) 0.08486(13) 0.1029(3) 0.0941(12) Uani d . 1 . . C C13 0.1850(7) 0.06131(14) 0.0009(3) 0.1019(13) Uani d . 1 . . C C14 0.3603(4) 0.06534(8) -0.05117(19) 0.0517(6) Uani d . 1 . . C C15 0.5345(6) 0.09551(16) 0.0024(3) 0.1100(15) Uani d . 1 . . C C16 0.5377(6) 0.11921(17) 0.1053(3) 0.1160(17) Uani d . 1 . . C C21 0.1670(6) 0.26881(11) 0.5243(3) 0.0734(9) Uani d . 1 . . C C22 -0.2572(7) 0.26630(13) 0.4070(3) 0.0764(9) Uani d . 1 . . C C41 0.3546(5) 0.03879(8) -0.1609(2) 0.0564(6) Uani d . 1 . . C C42 0.1828(7) 0.00671(14) -0.2074(3) 0.1034(13) Uani d . 1 . . C C43 0.1731(9) -0.01843(17) -0.3096(4) 0.1279(18) Uani d . 1 . . C C44 0.3387(8) -0.01204(14) -0.3654(3) 0.0967(12) Uani d . 1 . . C C45 0.5088(8) 0.02003(15) -0.3224(3) 0.0996(12) Uani d . 1 . . C C46 0.5178(6) 0.04565(12) -0.2207(3) 0.0829(9) Uani d . 1 . . C C61 0.2610(6) 0.17127(14) 0.6900(3) 0.0719(8) Uani d . 1 . . C C62 -0.1236(7) 0.12947(12) 0.6428(3) 0.0755(8) Uani d . 1 . . C H4 0.344(4) 0.1780(8) 0.4514(19) 0.050(6) Uiso d . 1 . . H H7 0.495(5) 0.1584(10) 0.306(3) 0.088(9) Uiso d . 1 . . H H12 0.060(7) 0.0831(14) 0.135(3) 0.138(14) Uiso calc . 1 . . H H13 0.070(7) 0.0412(15) -0.023(4) 0.136(15) Uiso calc . 1 . . H H15 0.644(7) 0.1022(14) -0.036(3) 0.132(14) Uiso calc . 1 . . H H16 0.644(7) 0.1408(15) 0.133(4) 0.140(15) Uiso calc . 1 . . H H21 0.322(5) 0.2500(11) 0.553(3) 0.087(10) Uiso d . 1 . . H H22 0.139(5) 0.2830(11) 0.593(3) 0.095(10) Uiso d . 1 . . H H23 0.181(5) 0.2931(11) 0.466(3) 0.090(9) Uiso d . 1 . . H H24 -0.282(5) 0.2879(11) 0.468(3) 0.089(9) Uiso d . 1 . . H H25 -0.406(6) 0.2459(13) 0.374(3) 0.109(12) Uiso d . 1 . . H H26 -0.237(5) 0.2841(11) 0.342(3) 0.098(10) Uiso d . 1 . . H H31 0.082(5) 0.2276(9) 0.316(2) 0.070(8) Uiso d . 1 . . H H32 -0.130(5) 0.1947(9) 0.312(2) 0.067(7) Uiso d . 1 . . H H42 0.072(7) 0.0027(14) -0.174(3) 0.122(14) Uiso calc . 1 . . H H43 0.063(9) -0.0409(17) -0.332(4) 0.17(2) Uiso calc . 1 . . H H44 0.323(7) -0.0274(14) -0.434(4) 0.127(14) Uiso calc . 1 . . H H45 0.634(8) 0.0267(14) -0.361(4) 0.142(15) Uiso calc . 1 . . H H46 0.650(6) 0.0680(13) -0.189(3) 0.115(12) Uiso calc . 1 . . H H51 0.186(5) 0.1099(10) 0.517(2) 0.071(8) Uiso d . 1 . . H H52 -0.065(5) 0.1205(9) 0.435(2) 0.064(7) Uiso d . 1 . . H H61 0.377(5) 0.1892(11) 0.660(3) 0.084(9) Uiso d . 1 . . H H62 0.332(6) 0.1423(12) 0.723(3) 0.101(11) Uiso d . 1 . . H H63 0.225(5) 0.1914(11) 0.753(3) 0.088(9) Uiso d . 1 . . H H64 -0.042(6) 0.0988(12) 0.662(3) 0.095(10) Uiso d . 1 . . H H65 -0.153(6) 0.1435(12) 0.718(3) 0.106(11) Uiso d . 1 . . H H66 -0.278(6) 0.1247(10) 0.581(3) 0.085(10) 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 0.0890(13) 0.0762(12) 0.0653(11) 0.0142(10) 0.0483(10) 0.0033(9) N1 0.0548(11) 0.0544(11) 0.0450(9) 0.0007(9) 0.0245(8) -0.0019(8) N2 0.0610(13) 0.0693(13) 0.0575(12) -0.0088(10) 0.0260(10) -0.0193(10) C2 0.0637(14) 0.0500(13) 0.0513(12) 0.0010(11) 0.0283(11) 0.0037(10) C3 0.0586(14) 0.0618(15) 0.0447(12) -0.0036(12) 0.0217(11) -0.0007(11) C4 0.0516(14) 0.0589(14) 0.0477(12) -0.0056(11) 0.0199(10) -0.0142(10) C5 0.0649(16) 0.0508(14) 0.0585(14) -0.0013(13) 0.0233(13) -0.0046(12) C6 0.0579(14) 0.0545(13) 0.0476(12) 0.0025(11) 0.0208(11) 0.0045(10) C7 0.0524(14) 0.0658(15) 0.0538(13) -0.0028(12) 0.0182(11) -0.0122(12) C11 0.0515(13) 0.0572(14) 0.0495(12) 0.0005(11) 0.0189(10) -0.0064(10) C12 0.096(2) 0.121(3) 0.088(2) -0.050(2) 0.0635(19) -0.050(2) C13 0.102(3) 0.126(3) 0.097(2) -0.061(2) 0.061(2) -0.060(2) C14 0.0609(14) 0.0493(13) 0.0487(12) 0.0047(11) 0.0217(11) -0.0012(10) C15 0.078(2) 0.170(4) 0.103(2) -0.049(2) 0.059(2) -0.075(3) C16 0.076(2) 0.183(4) 0.107(3) -0.056(3) 0.054(2) -0.089(3) C21 0.096(2) 0.0610(17) 0.0746(19) -0.0215(16) 0.0427(18) -0.0146(15) C22 0.092(2) 0.074(2) 0.0728(19) 0.0284(18) 0.0391(18) 0.0184(17) C41 0.0725(16) 0.0516(14) 0.0494(13) 0.0076(12) 0.0243(12) -0.0011(10) C42 0.118(3) 0.109(3) 0.106(3) -0.044(2) 0.067(2) -0.057(2) C43 0.153(4) 0.128(3) 0.127(3) -0.057(3) 0.079(3) -0.078(3) C44 0.143(3) 0.093(3) 0.0661(19) -0.003(2) 0.049(2) -0.0252(18) C45 0.132(3) 0.114(3) 0.072(2) -0.013(3) 0.061(2) -0.017(2) C46 0.098(2) 0.098(2) 0.0647(18) -0.017(2) 0.0430(17) -0.0184(16) C61 0.0723(19) 0.089(2) 0.0514(15) 0.0098(17) 0.0124(14) 0.0033(15) C62 0.089(2) 0.069(2) 0.081(2) 0.0013(17) 0.0435(19) 0.0168(16) 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 1 -2 0 12 3 0 -9 6 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 116.39(17) yes O1 N1 C2 116.32(18) yes C6 N1 C2 123.52(17) yes C7 N2 C4 120.7(2) yes N1 C2 C3 108.95(18) yes N1 C2 C21 109.8(2) no C3 C2 C21 111.9(2) no N1 C2 C22 107.2(2) no C3 C2 C22 108.8(2) no C21 C2 C22 110.0(3) no C4 C3 C2 115.67(19) yes C4 C3 H31 108.6(15) no C2 C3 H31 109.2(15) no C4 C3 H32 107.5(15) no C2 C3 H32 109.9(15) no H31 C3 H32 105(2) no N2 C4 C3 107.59(19) yes N2 C4 C5 107.72(19) yes C3 C4 C5 108.8(2) yes N2 C4 H4 110.9(12) no C3 C4 H4 110.5(12) no C5 C4 H4 111.2(12) no C4 C5 C6 115.3(2) yes C4 C5 H51 110.6(16) no C6 C5 H51 107.9(16) no C4 C5 H52 106.9(14) no C6 C5 H52 110.8(14) no H51 C5 H52 105(2) no N1 C6 C5 109.08(18) yes N1 C6 C62 107.6(2) no C5 C6 C62 109.3(2) no N1 C6 C61 109.6(2) no C5 C6 C61 111.9(2) no C62 C6 C61 109.3(2) no N2 C7 C11 122.1(2) yes N2 C7 H7 119.7(17) no C11 C7 H7 118.1(17) no C12 C11 C16 116.5(2) no C12 C11 C7 120.6(2) no C16 C11 C7 122.9(2) no C11 C12 C13 121.6(3) no C11 C12 H12 117(2) no C13 C12 H12 122(2) no C14 C13 C12 122.8(3) no C14 C13 H13 123(3) no C12 C13 H13 114(3) no C15 C14 C13 115.3(2) no C15 C14 C41 123.3(2) no C13 C14 C41 121.4(2) no C14 C15 C16 122.2(3) no C14 C15 H15 118(3) no C16 C15 H15 120(3) no C11 C16 C15 121.5(3) no C11 C16 H16 118(3) no C15 C16 H16 120(3) no C2 C21 H21 111.2(17) no C2 C21 H22 110.2(19) no H21 C21 H22 107(3) no C2 C21 H23 107.2(18) no H21 C21 H23 110(2) no H22 C21 H23 111(2) no C2 C22 H24 108.6(18) no C2 C22 H25 112.6(19) no H24 C22 H25 109(3) no C2 C22 H26 110.0(19) no H24 C22 H26 109(3) no H25 C22 H26 107(3) no C42 C41 C46 116.7(3) no C42 C41 C14 121.1(2) no C46 C41 C14 122.2(2) no C41 C42 C43 122.2(3) no C41 C42 H42 119(3) no C43 C42 H42 119(3) no C44 C43 C42 120.1(4) no C44 C43 H43 122(3) no C42 C43 H43 118(3) no C43 C44 C45 118.9(3) no C43 C44 H44 118(3) no C45 C44 H44 122(3) no C44 C45 C46 121.2(3) no C44 C45 H45 122(2) no C46 C45 H45 117(2) no C41 C46 C45 120.8(3) no C41 C46 H46 120(2) no C45 C46 H46 119(2) no C6 C61 H61 112.8(17) no C6 C61 H62 109(2) no H61 C61 H62 108(3) no C6 C61 H63 109.8(17) no H61 C61 H63 106(2) no H62 C61 H63 111(2) no C6 C62 H64 106.4(18) no C6 C62 H65 112.8(19) no H64 C62 H65 109(2) no C6 C62 H66 109.5(17) no H64 C62 H66 109(3) no H65 C62 H66 109(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 1.284(2) yes N1 C6 1.489(3) yes N1 C2 1.493(3) yes N2 C7 1.238(3) yes N2 C4 1.470(3) yes C2 C3 1.525(3) yes C2 C21 1.530(4) no C2 C22 1.531(4) no C3 C4 1.516(3) yes C3 H31 .97(3) no C3 H32 .99(3) no C4 C5 1.519(3) yes C4 H4 1.01(2) no C5 C6 1.524(3) yes C5 H51 .95(3) no C5 H52 1.02(3) no C6 C62 1.531(4) no C6 C61 1.533(4) no C7 C11 1.474(3) yes C7 H7 .98(3) no C11 C12 1.349(4) no C11 C16 1.360(4) no C12 C13 1.375(4) no C12 H12 .94(4) no C13 C14 1.360(4) no C13 H13 .87(4) no C14 C15 1.355(4) no C14 C41 1.491(3) no C15 C16 1.384(4) no C15 H15 .91(4) no C16 H16 .88(4) no C21 H21 1.04(3) no C21 H22 .96(3) no C21 H23 1.00(3) no C22 H24 .99(3) no C22 H25 1.04(4) no C22 H26 .96(3) no C41 C42 1.364(4) no C41 C46 1.370(4) no C42 C43 1.389(5) no C42 H42 .87(4) no C43 C44 1.346(5) no C43 H43 .90(5) no C44 C45 1.350(5) no C44 H44 .91(4) no C45 C46 1.392(4) no C45 H45 1.00(4) no C46 H46 1.00(4) no C61 H61 1.00(3) no C61 H62 .96(3) no C61 H63 1.00(3) no C62 H64 1.00(3) no C62 H65 1.03(3) no C62 H66 1.01(3) 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 5.9550(10) 1_555 1_455 yes O1 O1 6.0910(13) 1_555 4_555 yes O1 C22 3.516(4) 1_555 4_555 yes O1 C3 3.445(3) 1_555 4_555 yes O1 H61 2.85(3) 1_555 1_455 yes O1 H21 2.81(3) 1_555 1_455 yes O1 H26 2.70(3) 1_555 4_555 yes O1 H31 2.83(3) 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 C3 -162.3(2) yes C6 N1 C2 C3 40.4(3) yes O1 N1 C2 C21 74.9(3) no C6 N1 C2 C21 -82.4(3) no O1 N1 C2 C22 -44.7(3) no C6 N1 C2 C22 158.1(2) no N1 C2 C3 C4 -46.4(3) yes C21 C2 C3 C4 75.2(3) no C22 C2 C3 C4 -163.0(2) no C7 N2 C4 C3 106.8(3) yes C7 N2 C4 C5 -136.1(3) yes C2 C3 C4 N2 171.8(2) yes C2 C3 C4 C5 55.4(3) yes N2 C4 C5 C6 -172.0(2) yes C3 C4 C5 C6 -55.7(3) yes O1 N1 C6 C5 161.9(2) yes C2 N1 C6 C5 -40.9(3) yes O1 N1 C6 C62 43.4(3) no C2 N1 C6 C62 -159.4(2) no O1 N1 C6 C61 -75.3(3) no C2 N1 C6 C61 82.0(3) no C4 C5 C6 N1 47.1(3) yes C4 C5 C6 C62 164.4(2) no C4 C5 C6 C61 -74.4(3) no C4 N2 C7 C11 -176.9(2) yes N2 C7 C11 C12 -6.2(4) yes N2 C7 C11 C16 171.1(3) yes C16 C11 C12 C13 1.3(6) no C7 C11 C12 C13 178.7(4) no C11 C12 C13 C14 .2(7) no C12 C13 C14 C15 -2.0(6) no C12 C13 C14 C41 179.2(3) no C13 C14 C15 C16 2.3(6) no C41 C14 C15 C16 -179.0(4) no C12 C11 C16 C15 -1.0(6) no C7 C11 C16 C15 -178.4(4) no C14 C15 C16 C11 -.8(8) no C15 C14 C41 C42 176.0(4) no C13 C14 C41 C42 -5.3(5) no C15 C14 C41 C46 -4.9(5) no C13 C14 C41 C46 173.8(3) no C46 C41 C42 C43 .7(6) no C14 C41 C42 C43 179.9(4) no C41 C42 C43 C44 1.0(8) no C42 C43 C44 C45 -1.9(8) no C43 C44 C45 C46 1.3(7) no C42 C41 C46 C45 -1.4(5) no C14 C41 C46 C45 179.5(3) no C44 C45 C46 C41 .4(6) no