#------------------------------------------------------------------------------ #$Date: 2013-08-29 17:37:19 +0200 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/30/2003061.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_2003061 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_moiety 'C16 H21 Cl2 N2 O ' _chemical_formula_sum 'C16 H21 Cl2 N2 O' _chemical_formula_weight 328.26 _chemical_name_common 3,5-diCl-TEMPO _chemical_name_systematic ' 4-(3,5-dichlorophenyl)methyleneamino-2,2,6,6-tetramethylpiperidin-1-oxyl' _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.035(3) _cell_length_b 22.964(3) _cell_length_c 10.710(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 17.8 _cell_measurement_theta_min 14.1 _cell_volume 3451.8(11) _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 295 _diffrn_measured_fraction_theta_full 0.896 _diffrn_measured_fraction_theta_max 0.896 _diffrn_measurement_device 'Rigaku AFC5R' _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 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 4927 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.90 _diffrn_standards_decay_% -0.42 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_correction_T_min 0.927 _exptl_absorpt_correction_type integration _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1384.00 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.371 _refine_diff_density_min -0.276 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 3959 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.1287 _refine_ls_R_factor_gt 0.0491 _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^)+(0.0369P)^2^+2.0600P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref 0.1233 _reflns_number_gt 2128 _reflns_number_total 3959 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file oa0019.cif _[local]_cod_data_source_block 7 _[local]_cod_chemical_formula_sum_orig 'C16 H21 Cl2 N2 O ' _cod_original_cell_volume 3451.9(9) _cod_database_code 2003061 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,z x,1/2-y,1/2+z 1/2+x,y,1/2-z loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 0 0 4 0 0 0 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' Cl Cl 0.1484 0.1585 '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 Cl1 0.12604(6) -0.04521(4) -0.28124(8) 0.0682(3) Uani d . 1 . . Cl Cl2 0.43007(6) 0.08783(4) -0.37751(9) 0.0791(3) Uani d . 1 . . Cl O1 -0.03302(16) 0.19379(9) 0.49966(17) 0.0579(6) Uani d . 1 . . O N1 0.01245(16) 0.17800(10) 0.40146(19) 0.0418(6) Uani d . 1 . . N N2 0.14398(17) 0.11600(11) 0.0744(2) 0.0487(6) Uani d . 1 . . N C2 0.09738(19) 0.14025(13) 0.4217(2) 0.0463(7) Uani d . 1 . . C C3 0.1249(3) 0.11150(15) 0.2979(3) 0.0499(8) Uani d . 1 . . C C4 0.1265(2) 0.15156(13) 0.1858(3) 0.0454(7) Uani d . 1 . . C C5 0.0294(2) 0.17977(14) 0.1728(3) 0.0428(7) Uani d . 1 . . C C6 -0.00257(19) 0.21422(12) 0.2875(2) 0.0416(7) Uani d . 1 . . C C7 0.2145(2) 0.12751(13) 0.0064(3) 0.0435(7) Uani d . 1 . . C C11 0.23550(18) 0.09205(12) -0.1052(2) 0.0386(6) Uani d . 1 . . C C12 0.1775(2) 0.04533(12) -0.1372(3) 0.0402(6) Uani d . 1 . . C C13 0.19897(19) 0.01287(12) -0.2410(2) 0.0417(6) Uani d . 1 . . C C14 0.2769(2) 0.02516(13) -0.3152(3) 0.0446(7) Uani d . 1 . . C C15 0.3332(2) 0.07152(13) -0.2828(3) 0.0457(7) Uani d . 1 . . C C16 0.3141(2) 0.10468(14) -0.1787(3) 0.0454(7) Uani d . 1 . . C C21 0.0687(3) 0.09282(18) 0.5143(3) 0.0652(10) Uani d . 1 . . C C22 0.1794(3) 0.1764(2) 0.4747(4) 0.0669(11) Uani d . 1 . . C C61 -0.1084(2) 0.22702(19) 0.2764(4) 0.0610(9) Uani d . 1 . . C C62 0.0523(3) 0.27139(15) 0.2998(3) 0.0580(9) Uani d . 1 . . C H4 0.1743(18) 0.1801(11) 0.195(2) 0.036(7) Uiso d . 1 . . H H7 0.2581(19) 0.1604(12) 0.025(2) 0.047(8) Uiso d . 1 . . H H12 0.1245(17) 0.0365(10) -0.091(2) 0.032(7) Uiso d . 1 . . H H14 0.2890(18) 0.0029(12) -0.385(3) 0.052(8) Uiso d . 1 . . H H16 0.3517(16) 0.1326(10) -0.155(2) 0.025(7) Uiso d . 1 . . H H21 0.120(3) 0.0632(16) 0.516(3) 0.093(13) Uiso calc . 1 . . H H22 0.008(3) 0.0688(18) 0.484(4) 0.118(16) Uiso calc . 1 . . H H23 0.062(2) 0.1064(14) 0.592(3) 0.068(11) Uiso d . 1 . . H H24 0.209(2) 0.2080(14) 0.414(3) 0.075(11) Uiso d . 1 . . H H25 0.228(3) 0.1512(16) 0.498(3) 0.093(14) Uiso calc . 1 . . H H26 0.160(3) 0.1998(16) 0.546(3) 0.093(13) Uiso calc . 1 . . H H31 0.083(2) 0.0818(12) 0.282(3) 0.050(9) Uiso d . 1 . . H H32 0.185(2) 0.0932(12) 0.309(3) 0.051(8) Uiso d . 1 . . H H51 -0.0175(18) 0.1498(11) 0.155(2) 0.041(7) Uiso d . 1 . . H H52 0.0280(18) 0.2053(12) 0.103(3) 0.045(8) Uiso d . 1 . . H H61 -0.146(2) 0.1907(14) 0.281(3) 0.059(9) Uiso d . 1 . . H H62 -0.119(2) 0.2485(14) 0.199(3) 0.062(9) Uiso d . 1 . . H H63 -0.132(2) 0.2504(16) 0.344(3) 0.085(12) Uiso calc . 1 . . H H64 0.125(2) 0.2689(14) 0.297(3) 0.076(11) Uiso d . 1 . . H H65 0.036(2) 0.2972(13) 0.236(3) 0.062(10) Uiso d . 1 . . H H66 0.034(2) 0.2916(14) 0.376(3) 0.069(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 Cl1 0.0633(5) 0.0636(5) 0.0778(6) -0.0187(4) 0.0007(5) -0.0197(4) Cl2 0.0710(6) 0.0875(7) 0.0786(6) -0.0172(5) 0.0406(5) -0.0182(5) O1 0.0683(14) 0.0695(14) 0.0361(10) 0.0107(12) 0.0172(10) 0.0025(11) N1 0.0454(13) 0.0500(14) 0.0301(12) 0.0030(11) 0.0071(10) 0.0029(10) N2 0.0529(15) 0.0549(15) 0.0382(13) -0.0006(12) 0.0070(12) -0.0105(12) C2 0.0466(16) 0.0575(18) 0.0346(14) 0.0077(14) -0.0014(13) -0.0007(14) C3 0.0510(18) 0.055(2) 0.0433(17) 0.0117(18) -0.0012(15) -0.0015(15) C4 0.0446(16) 0.0531(18) 0.0385(15) -0.0040(15) 0.0074(13) -0.0129(14) C5 0.0499(17) 0.0504(18) 0.0279(14) -0.0007(16) 0.0022(13) 0.0000(14) C6 0.0458(15) 0.0468(16) 0.0321(14) 0.0038(13) 0.0038(13) 0.0049(13) C7 0.0460(16) 0.0477(18) 0.0367(15) 0.0003(15) 0.0000(13) -0.0056(14) C11 0.0394(14) 0.0424(15) 0.0341(14) 0.0043(13) 0.0010(12) -0.0002(12) C12 0.0366(15) 0.0463(17) 0.0377(15) 0.0019(13) 0.0005(13) 0.0035(13) C13 0.0405(14) 0.0445(16) 0.0400(15) -0.0002(13) -0.0042(13) -0.0036(13) C14 0.0492(17) 0.0497(18) 0.0348(15) 0.0034(15) 0.0033(13) -0.0081(14) C15 0.0428(15) 0.0513(17) 0.0429(16) -0.0012(14) 0.0093(13) -0.0017(14) C16 0.0429(16) 0.0492(19) 0.0442(16) -0.0044(15) 0.0005(14) -0.0063(14) C21 0.087(3) 0.067(2) 0.0413(19) 0.018(2) 0.001(2) 0.0121(18) C22 0.056(2) 0.094(3) 0.050(2) 0.001(2) -0.0081(18) -0.010(2) C61 0.055(2) 0.073(3) 0.055(2) 0.0192(19) 0.0059(18) 0.014(2) C62 0.081(3) 0.049(2) 0.0446(19) -0.0023(18) 0.0118(19) 0.0000(17) 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 C2 116.3(2) yes O1 N1 C6 116.3(2) yes C2 N1 C6 123.8(2) yes C7 N2 C4 119.1(3) yes N1 C2 C21 107.4(3) no N1 C2 C22 109.9(3) no C21 C2 C22 110.2(3) no N1 C2 C3 109.1(2) yes C21 C2 C3 108.7(3) no C22 C2 C3 111.5(3) no C4 C3 C2 115.4(2) yes C4 C3 H31 108.5(18) no C2 C3 H31 108.4(18) no C4 C3 H32 110.9(17) no C2 C3 H32 107.6(17) no H31 C3 H32 106(2) no N2 C4 C3 108.0(2) yes N2 C4 C5 108.3(2) yes C3 C4 C5 108.7(2) yes N2 C4 H4 110.5(15) no C3 C4 H4 110.6(15) no C5 C4 H4 110.7(15) no C4 C5 C6 114.3(2) yes C4 C5 H51 108.9(15) no C6 C5 H51 109.1(15) no C4 C5 H52 110.7(16) no C6 C5 H52 108.1(16) no H51 C5 H52 105(2) no N1 C6 C61 108.0(2) no N1 C6 C62 109.7(2) no C61 C6 C62 109.5(3) no N1 C6 C5 109.1(2) yes C61 C6 C5 108.9(3) no C62 C6 C5 111.5(2) no N2 C7 C11 120.7(3) yes N2 C7 H7 122.0(15) no C11 C7 H7 117.4(15) no C16 C11 C12 119.2(3) no C16 C11 C7 120.2(3) no C12 C11 C7 120.6(2) no C13 C12 C11 119.4(3) no C13 C12 H12 119.9(15) no C11 C12 H12 120.7(15) no C12 C13 C14 121.9(3) no C12 C13 Cl1 119.3(2) no C14 C13 Cl1 118.8(2) no C15 C14 C13 118.1(3) no C15 C14 H14 121.9(17) no C13 C14 H14 120.0(17) no C14 C15 C16 121.4(3) no C14 C15 Cl2 118.1(2) no C16 C15 Cl2 120.4(2) no C15 C16 C11 120.0(3) no C15 C16 H16 121.5(15) no C11 C16 H16 118.4(15) no C2 C21 H21 108(2) no C2 C21 H22 113(2) no H21 C21 H22 103(3) no C2 C21 H23 113(2) no H21 C21 H23 108(3) no H22 C21 H23 112(3) no C2 C22 H24 116.3(17) no C2 C22 H25 108(2) no H24 C22 H25 108(3) no C2 C22 H26 112(2) no H24 C22 H26 102(3) no H25 C22 H26 110(3) no C6 C61 H61 110.6(17) no C6 C61 H62 108.4(17) no H61 C61 H62 113(3) no C6 C61 H63 113(2) no H61 C61 H63 105(3) no H62 C61 H63 108(3) no C6 C62 H64 116.9(18) no C6 C62 H65 111.2(19) no H64 C62 H65 105(3) no C6 C62 H66 110.6(18) no H64 C62 H66 108(3) no H65 C62 H66 104(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C13 1.736(3) yes Cl2 C15 1.736(3) yes O1 N1 1.283(3) yes N1 C2 1.490(3) yes N1 C6 1.492(3) yes N2 C7 1.257(3) yes N2 C4 1.467(3) yes C2 C21 1.527(5) no C2 C22 1.528(5) no C2 C3 1.531(4) yes C3 C4 1.513(4) yes C3 H31 .92(3) no C3 H32 .95(3) no C4 C5 1.515(4) yes C4 H4 .94(2) no C5 C6 1.528(4) yes C5 H51 .97(3) no C5 H52 .95(3) no C6 C61 1.519(4) no C6 C62 1.528(4) no C7 C11 1.476(4) yes C7 H7 .99(3) no C11 C16 1.386(4) no C11 C12 1.389(4) no C12 C13 1.372(4) no C12 H12 .92(2) no C13 C14 1.381(4) no C14 C15 1.371(4) no C14 H14 .92(3) no C15 C16 1.377(4) no C16 H16 .87(2) no C21 H21 .99(4) no C21 H22 1.06(4) no C21 H23 .89(3) no C22 H24 1.06(3) no C22 H25 .93(4) no C22 H26 .97(4) no C61 H61 .99(3) no C61 H62 .98(3) no C61 H63 .96(4) no C62 H64 1.03(3) no C62 H65 .93(3) no C62 H66 .97(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 5.945(2) 1_555 7_555 yes O1 O1 7.477(2) 1_555 2_556 yes O1 C5 3.554(4) 1_555 7_555 yes O1 C62 3.522(5) 1_555 7_555 yes O1 H65 2.72(3) 1_555 7_555 yes O1 H52 2.71(3) 1_555 7_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 46.0(3) no C6 N1 C2 C21 -156.2(3) no O1 N1 C2 C22 -73.8(3) no C6 N1 C2 C22 84.0(3) no O1 N1 C2 C3 163.7(2) yes C6 N1 C2 C3 -38.5(4) yes N1 C2 C3 C4 45.5(4) yes C21 C2 C3 C4 162.3(3) no C22 C2 C3 C4 -76.0(4) no C7 N2 C4 C3 -122.6(3) yes C7 N2 C4 C5 119.8(3) yes C2 C3 C4 N2 -174.1(3) yes C2 C3 C4 C5 -56.8(4) yes N2 C4 C5 C6 175.0(2) yes C3 C4 C5 C6 57.9(3) yes O1 N1 C6 C61 -43.9(3) no C2 N1 C6 C61 158.3(3) no O1 N1 C6 C62 75.4(3) no C2 N1 C6 C62 -82.4(3) no O1 N1 C6 C5 -162.2(2) yes C2 N1 C6 C5 40.0(3) yes C4 C5 C6 N1 -48.1(3) yes C4 C5 C6 C61 -165.8(3) no C4 C5 C6 C62 73.3(3) no C4 N2 C7 C11 178.9(2) yes N2 C7 C11 C16 -179.2(3) yes N2 C7 C11 C12 .0(4) yes C16 C11 C12 C13 -.3(4) no C7 C11 C12 C13 -179.6(2) no C11 C12 C13 C14 .1(4) no C11 C12 C13 Cl1 -179.6(2) no C12 C13 C14 C15 -.3(4) no Cl1 C13 C14 C15 179.4(2) no C13 C14 C15 C16 .8(4) no C13 C14 C15 Cl2 -178.9(2) no C14 C15 C16 C11 -1.1(4) no Cl2 C15 C16 C11 178.6(2) no C12 C11 C16 C15 .8(4) no C7 C11 C16 C15 -179.9(3) no _cod_database_fobs_code 2003061