#------------------------------------------------------------------------------ #$Date: 2009-05-13 19:45:18 +0100 (Wed, 13 May 2009) $ #$Revision: 720 $ #$URL: svn://www.crystallography.net/cod/cif/2/2003065.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2003065 _journal_name_full 'Acta Crystallographica, Section B' _journal_year 1999 _journal_volume B55 _journal_page_first 231 _journal_page_last 245 loop_ _publ_author_name ; Fujiko Iwasaki ; _chemical_name_systematic ; 4-(biphenyl-4-yl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl ; _chemical_name_common biPh-TEMPO _chemical_formula_moiety 'C22 H27 N2 O ' _chemical_formula_sum 'C22 H27 N2 O ' _chemical_formula_weight 335.47 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' 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 _cell_length_a 5.9550(10) _cell_length_b 28.488(5) _cell_length_c 11.796(2) _cell_angle_alpha 90 _cell_angle_beta 106.72(2) _cell_angle_gamma 90 _cell_volume 1916.5(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.9 _cell_measurement_theta_max 17.5 _cell_measurement_temperature 296 _exptl_crystal_description 'prism' _exptl_crystal_colour 'Orange' _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.300 _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 724.00 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 296 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w _diffrn_reflns_number 4774 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% -0.72 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 _reflns_number_total 4372 _reflns_number_gt 2488 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1817 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _refine_ls_number_reflns 4372 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.194 _refine_ls_shift/su_mean 0.037 _refine_diff_density_max 0.286 _refine_diff_density_min -0.254 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(2) 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 -0.2026(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)