# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_BAntQNN300K _database_code_depnum_ccdc_archive 'CCDC 923567' #TrackingRef 'AntQNN.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl ; _chemical_name_common ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazole-3-oxide- ; _chemical_melting_point 481 _chemical_formula_moiety 'C21 H19 N2 O4' _chemical_formula_sum 'C21 H19 N2 O4' _chemical_formula_weight 363.38 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.3230(5) _cell_length_b 21.4026(17) _cell_length_c 22.3514(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3503.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2507 _cell_measurement_theta_min 2.635 _cell_measurement_theta_max 20.032 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6224 _exptl_absorpt_correction_T_max 0.7449 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker APEX II' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 24088 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 23.32 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.32 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 2534 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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 'calc w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+1.2058P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2534 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.173 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.039 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 C1 C 0.3408(3) 0.13577(11) 0.23054(10) 0.0400(6) Uani 1 1 d . . . O1 O 0.2182(3) 0.26406(9) 0.25256(9) 0.0720(7) Uani 1 1 d . . . N1 N 0.2940(3) 0.24746(10) 0.20338(9) 0.0465(6) Uani 1 1 d . . . O2 O 0.4884(3) 0.14146(8) 0.10778(8) 0.0536(5) Uani 1 1 d . . . N2 N 0.4210(3) 0.18901(9) 0.13458(8) 0.0399(5) Uani 1 1 d . . . C2 C 0.3628(3) 0.14309(11) 0.29197(11) 0.0406(6) Uani 1 1 d . . . H2 H 0.3972 0.1817 0.3074 0.049 Uiso 1 1 calc R . . C3 C 0.3334(3) 0.09277(11) 0.33056(10) 0.0389(6) Uani 1 1 d . . . O4 O 0.4400(3) 0.14800(8) 0.41544(8) 0.0592(6) Uani 1 1 d . . . C4 C 0.3633(4) 0.10146(12) 0.39621(11) 0.0439(6) Uani 1 1 d . . . C5 C 0.3043(3) 0.04992(11) 0.43651(11) 0.0447(6) Uani 1 1 d . . . C6 C 0.3136(4) 0.05846(13) 0.49827(12) 0.0571(8) Uani 1 1 d . . . H6 H 0.3543 0.0963 0.5137 0.069 Uiso 1 1 calc R . . C7 C 0.2626(4) 0.01097(15) 0.53656(14) 0.0675(9) Uani 1 1 d . . . H7 H 0.2677 0.0171 0.5777 0.081 Uiso 1 1 calc R . . C8 C 0.2040(4) -0.04573(15) 0.51395(14) 0.0664(9) Uani 1 1 d . . . H8 H 0.1711 -0.0778 0.5399 0.080 Uiso 1 1 calc R . . C9 C 0.1943(4) -0.05471(13) 0.45293(14) 0.0587(8) Uani 1 1 d . . . H9 H 0.1549 -0.0929 0.4379 0.070 Uiso 1 1 calc R . . C10 C 0.2434(3) -0.00680(12) 0.41357(12) 0.0480(7) Uani 1 1 d . . . O11 O 0.1772(4) -0.06702(10) 0.32767(10) 0.0913(8) Uani 1 1 d . . . C11 C 0.2299(4) -0.01730(12) 0.34794(13) 0.0528(7) Uani 1 1 d . . . C12 C 0.2781(3) 0.03534(11) 0.30750(11) 0.0434(6) Uani 1 1 d . . . C13 C 0.2629(4) 0.02749(12) 0.24593(12) 0.0506(7) Uani 1 1 d . . . H13 H 0.2306 -0.0113 0.2304 0.061 Uiso 1 1 calc R . . C14 C 0.2955(4) 0.07687(11) 0.20762(11) 0.0486(7) Uani 1 1 d . . . H14 H 0.2873 0.0710 0.1665 0.058 Uiso 1 1 calc R . . C15 C 0.3550(3) 0.18974(11) 0.19091(10) 0.0387(6) Uani 1 1 d . . . C16 C 0.3030(4) 0.29144(11) 0.15102(11) 0.0448(6) Uani 1 1 d . . . C17 C 0.4219(3) 0.25278(11) 0.10597(10) 0.0421(6) Uani 1 1 d . . . C18 C 0.3859(5) 0.35260(13) 0.17235(13) 0.0668(9) Uani 1 1 d . . . H18A H 0.3035 0.3727 0.1997 0.100 Uiso 1 1 calc R . . H18B H 0.4071 0.3794 0.1386 0.100 Uiso 1 1 calc R . . H18C H 0.4996 0.3443 0.1922 0.100 Uiso 1 1 calc R . . C19 C 0.1056(4) 0.30122(15) 0.13104(14) 0.0683(9) Uani 1 1 d . . . H19A H 0.0414 0.3250 0.1608 0.102 Uiso 1 1 calc R . . H19B H 0.0472 0.2614 0.1261 0.102 Uiso 1 1 calc R . . H19C H 0.1040 0.3234 0.0937 0.102 Uiso 1 1 calc R . . C20 C 0.6206(4) 0.27304(13) 0.10246(12) 0.0569(8) Uani 1 1 d . . . H20A H 0.6840 0.2474 0.0740 0.085 Uiso 1 1 calc R . . H20B H 0.6765 0.2686 0.1411 0.085 Uiso 1 1 calc R . . H20C H 0.6269 0.3159 0.0901 0.085 Uiso 1 1 calc R . . C21 C 0.3425(4) 0.24576(14) 0.04322(11) 0.0611(8) Uani 1 1 d . . . H21A H 0.4245 0.2216 0.0190 0.092 Uiso 1 1 calc R . . H21B H 0.3263 0.2863 0.0257 0.092 Uiso 1 1 calc R . . H21C H 0.2266 0.2249 0.0455 0.092 Uiso 1 1 calc R . . 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 C1 0.0422(15) 0.0439(14) 0.0340(14) 0.0012(11) 0.0029(11) 0.0024(12) O1 0.1054(18) 0.0683(13) 0.0423(11) 0.0018(10) 0.0286(11) 0.0229(12) N1 0.0579(14) 0.0503(13) 0.0313(12) 0.0022(10) 0.0087(10) 0.0058(11) O2 0.0641(12) 0.0561(12) 0.0407(10) -0.0110(9) 0.0066(9) 0.0060(10) N2 0.0447(12) 0.0459(12) 0.0292(11) -0.0020(9) 0.0000(9) 0.0011(10) C2 0.0417(14) 0.0430(14) 0.0373(14) -0.0024(11) 0.0017(11) -0.0019(11) C3 0.0380(14) 0.0420(14) 0.0367(14) 0.0057(11) 0.0019(11) 0.0020(11) O4 0.0803(15) 0.0556(12) 0.0418(11) 0.0033(9) -0.0083(10) -0.0156(10) C4 0.0444(15) 0.0447(15) 0.0427(15) 0.0045(12) -0.0011(12) 0.0002(13) C5 0.0446(15) 0.0497(16) 0.0399(15) 0.0103(12) 0.0006(12) 0.0031(12) C6 0.067(2) 0.0608(18) 0.0437(16) 0.0089(14) 0.0001(14) 0.0010(15) C7 0.074(2) 0.078(2) 0.0506(18) 0.0225(16) 0.0061(16) 0.0049(17) C8 0.068(2) 0.070(2) 0.061(2) 0.0312(17) 0.0073(16) -0.0015(16) C9 0.0565(18) 0.0524(17) 0.067(2) 0.0148(15) 0.0020(15) -0.0017(14) C10 0.0457(16) 0.0470(15) 0.0513(17) 0.0140(13) 0.0043(13) 0.0001(12) O11 0.147(2) 0.0556(13) 0.0710(15) 0.0040(11) -0.0063(15) -0.0340(14) C11 0.0588(18) 0.0414(16) 0.0581(18) 0.0042(13) -0.0005(14) -0.0067(13) C12 0.0449(15) 0.0411(14) 0.0442(16) 0.0020(12) -0.0001(12) 0.0006(11) C13 0.0606(17) 0.0426(14) 0.0486(16) -0.0060(13) -0.0015(13) -0.0044(13) C14 0.0565(17) 0.0506(16) 0.0386(15) -0.0045(12) -0.0003(13) 0.0026(13) C15 0.0419(14) 0.0445(15) 0.0299(13) -0.0003(11) 0.0002(11) 0.0022(11) C16 0.0521(16) 0.0458(14) 0.0364(14) 0.0086(11) -0.0001(12) -0.0001(12) C17 0.0510(16) 0.0491(15) 0.0263(13) 0.0038(11) -0.0032(11) -0.0006(12) C18 0.090(2) 0.0528(18) 0.0572(19) -0.0002(14) 0.0076(17) -0.0053(16) C19 0.059(2) 0.079(2) 0.066(2) 0.0134(17) -0.0002(16) 0.0152(16) C20 0.0546(18) 0.0716(19) 0.0446(16) 0.0050(14) 0.0038(14) -0.0088(14) C21 0.076(2) 0.0749(19) 0.0318(15) 0.0025(14) -0.0103(14) 0.0006(16) _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 C1 C2 1.391(3) . ? C1 C14 1.401(3) . ? C1 C15 1.459(3) . ? O1 N1 1.282(3) . ? N1 C15 1.343(3) . ? N1 C16 1.503(3) . ? O2 N2 1.280(2) . ? N2 C15 1.349(3) . ? N2 C17 1.507(3) . ? C2 C3 1.396(3) . ? C2 H2 0.9300 . ? C3 C12 1.393(3) . ? C3 C4 1.495(3) . ? O4 C4 1.222(3) . ? C4 C5 1.488(3) . ? C5 C10 1.391(4) . ? C5 C6 1.394(4) . ? C6 C7 1.380(4) . ? C6 H6 0.9300 . ? C7 C8 1.383(4) . ? C7 H7 0.9300 . ? C8 C9 1.379(4) . ? C8 H8 0.9300 . ? C9 C10 1.398(3) . ? C9 H9 0.9300 . ? C10 C11 1.487(4) . ? O11 C11 1.219(3) . ? C11 C12 1.487(3) . ? C12 C13 1.391(4) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C16 C18 1.520(4) . ? C16 C19 1.527(4) . ? C16 C17 1.568(3) . ? C17 C20 1.521(4) . ? C17 C21 1.526(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C2 C1 C14 119.3(2) . . ? C2 C1 C15 120.1(2) . . ? C14 C1 C15 120.5(2) . . ? O1 N1 C15 125.3(2) . . ? O1 N1 C16 120.85(19) . . ? C15 N1 C16 113.58(19) . . ? O2 N2 C15 125.8(2) . . ? O2 N2 C17 121.32(18) . . ? C15 N2 C17 112.77(19) . . ? C1 C2 C3 120.3(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C12 C3 C2 119.8(2) . . ? C12 C3 C4 121.0(2) . . ? C2 C3 C4 119.2(2) . . ? O4 C4 C5 121.7(2) . . ? O4 C4 C3 120.9(2) . . ? C5 C4 C3 117.3(2) . . ? C10 C5 C6 119.7(2) . . ? C10 C5 C4 121.1(2) . . ? C6 C5 C4 119.2(2) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.2(3) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C5 C10 C9 119.4(3) . . ? C5 C10 C11 121.1(2) . . ? C9 C10 C11 119.5(2) . . ? O11 C11 C12 120.7(3) . . ? O11 C11 C10 121.3(2) . . ? C12 C11 C10 118.0(2) . . ? C13 C12 C3 119.7(2) . . ? C13 C12 C11 119.4(2) . . ? C3 C12 C11 120.8(2) . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C1 120.2(2) . . ? C13 C14 H14 119.9 . . ? C1 C14 H14 119.9 . . ? N1 C15 N2 108.9(2) . . ? N1 C15 C1 125.3(2) . . ? N2 C15 C1 125.7(2) . . ? N1 C16 C18 108.2(2) . . ? N1 C16 C19 105.8(2) . . ? C18 C16 C19 110.6(2) . . ? N1 C16 C17 101.17(18) . . ? C18 C16 C17 115.7(2) . . ? C19 C16 C17 114.2(2) . . ? N2 C17 C20 106.5(2) . . ? N2 C17 C21 107.4(2) . . ? C20 C17 C21 110.2(2) . . ? N2 C17 C16 101.72(18) . . ? C20 C17 C16 114.5(2) . . ? C21 C17 C16 115.5(2) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C14 C1 C2 C3 -2.3(4) . . . . ? C15 C1 C2 C3 174.3(2) . . . . ? C1 C2 C3 C12 -1.4(4) . . . . ? C1 C2 C3 C4 178.2(2) . . . . ? C12 C3 C4 O4 167.8(2) . . . . ? C2 C3 C4 O4 -11.8(4) . . . . ? C12 C3 C4 C5 -9.3(3) . . . . ? C2 C3 C4 C5 171.1(2) . . . . ? O4 C4 C5 C10 -169.9(2) . . . . ? C3 C4 C5 C10 7.2(4) . . . . ? O4 C4 C5 C6 9.0(4) . . . . ? C3 C4 C5 C6 -174.0(2) . . . . ? C10 C5 C6 C7 0.0(4) . . . . ? C4 C5 C6 C7 -178.9(3) . . . . ? C5 C6 C7 C8 0.8(5) . . . . ? C6 C7 C8 C9 -0.8(5) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C6 C5 C10 C9 -0.8(4) . . . . ? C4 C5 C10 C9 178.1(2) . . . . ? C6 C5 C10 C11 179.3(2) . . . . ? C4 C5 C10 C11 -1.8(4) . . . . ? C8 C9 C10 C5 0.8(4) . . . . ? C8 C9 C10 C11 -179.3(3) . . . . ? C5 C10 C11 O11 179.7(3) . . . . ? C9 C10 C11 O11 -0.2(4) . . . . ? C5 C10 C11 C12 -1.9(4) . . . . ? C9 C10 C11 C12 178.3(2) . . . . ? C2 C3 C12 C13 3.8(4) . . . . ? C4 C3 C12 C13 -175.8(2) . . . . ? C2 C3 C12 C11 -174.5(2) . . . . ? C4 C3 C12 C11 5.9(4) . . . . ? O11 C11 C12 C13 -0.1(4) . . . . ? C10 C11 C12 C13 -178.5(2) . . . . ? O11 C11 C12 C3 178.2(3) . . . . ? C10 C11 C12 C3 -0.3(4) . . . . ? C3 C12 C13 C14 -2.5(4) . . . . ? C11 C12 C13 C14 175.8(2) . . . . ? C12 C13 C14 C1 -1.2(4) . . . . ? C2 C1 C14 C13 3.7(4) . . . . ? C15 C1 C14 C13 -173.0(2) . . . . ? O1 N1 C15 N2 178.1(2) . . . . ? C16 N1 C15 N2 4.5(3) . . . . ? O1 N1 C15 C1 1.9(4) . . . . ? C16 N1 C15 C1 -171.7(2) . . . . ? O2 N2 C15 N1 -179.2(2) . . . . ? C17 N2 C15 N1 5.2(3) . . . . ? O2 N2 C15 C1 -3.0(4) . . . . ? C17 N2 C15 C1 -178.6(2) . . . . ? C2 C1 C15 N1 -37.5(4) . . . . ? C14 C1 C15 N1 139.1(3) . . . . ? C2 C1 C15 N2 146.9(2) . . . . ? C14 C1 C15 N2 -36.5(4) . . . . ? O1 N1 C16 C18 52.6(3) . . . . ? C15 N1 C16 C18 -133.5(2) . . . . ? O1 N1 C16 C19 -66.0(3) . . . . ? C15 N1 C16 C19 107.9(2) . . . . ? O1 N1 C16 C17 174.7(2) . . . . ? C15 N1 C16 C17 -11.4(3) . . . . ? O2 N2 C17 C20 -67.5(3) . . . . ? C15 N2 C17 C20 108.3(2) . . . . ? O2 N2 C17 C21 50.6(3) . . . . ? C15 N2 C17 C21 -133.6(2) . . . . ? O2 N2 C17 C16 172.4(2) . . . . ? C15 N2 C17 C16 -11.9(2) . . . . ? N1 C16 C17 N2 12.8(2) . . . . ? C18 C16 C17 N2 129.4(2) . . . . ? C19 C16 C17 N2 -100.4(2) . . . . ? N1 C16 C17 C20 -101.6(2) . . . . ? C18 C16 C17 C20 15.0(3) . . . . ? C19 C16 C17 C20 145.2(2) . . . . ? N1 C16 C17 C21 128.7(2) . . . . ? C18 C16 C17 C21 -114.6(3) . . . . ? C19 C16 C17 C21 15.6(3) . . . . ? data_BAntQNN199K _database_code_depnum_ccdc_archive 'CCDC 923568' #TrackingRef 'AntQNN.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl ; _chemical_name_common ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazole-3-oxide- ; _chemical_melting_point 481 _chemical_formula_moiety 'C21 H19 N2 O4' _chemical_formula_sum 'C21 H19 N2 O4' _chemical_formula_weight 363.38 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.2592(5) _cell_length_b 21.3199(14) _cell_length_c 22.2954(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3450.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 199(2) _cell_measurement_reflns_used 3133 _cell_measurement_theta_min 2.644 _cell_measurement_theta_max 21.358 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6062 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 199(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 '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 27343 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.81 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.81 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 2974 _reflns_number_gt 2176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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 'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+1.6872P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2974 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.215 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.045 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 C1 C 0.3470(3) 0.13583(10) 0.23084(9) 0.0289(5) Uani 1 1 d . . . O1 O 0.2236(3) 0.26495(7) 0.25278(7) 0.0494(5) Uani 1 1 d . . . N1 N 0.3008(3) 0.24797(8) 0.20366(8) 0.0326(4) Uani 1 1 d . . . O2 O 0.4956(2) 0.14119(7) 0.10761(7) 0.0365(4) Uani 1 1 d . . . N2 N 0.4278(2) 0.18907(8) 0.13443(7) 0.0284(4) Uani 1 1 d . . . C2 C 0.3692(3) 0.14354(10) 0.29255(9) 0.0288(5) Uani 1 1 d . . . H2 H 0.4049 0.1831 0.3083 0.035 Uiso 1 1 calc R . . C3 C 0.3387(3) 0.09290(10) 0.33114(9) 0.0290(5) Uani 1 1 d . . . O4 O 0.4466(2) 0.14837(7) 0.41628(7) 0.0408(4) Uani 1 1 d . . . C4 C 0.3684(3) 0.10185(10) 0.39698(10) 0.0311(5) Uani 1 1 d . . . C5 C 0.3071(3) 0.05032(10) 0.43747(10) 0.0320(5) Uani 1 1 d . . . C6 C 0.3167(3) 0.05898(11) 0.49953(10) 0.0387(6) Uani 1 1 d . . . H6 H 0.3600 0.0976 0.5154 0.046 Uiso 1 1 calc R . . C7 C 0.2632(3) 0.01133(11) 0.53798(11) 0.0449(6) Uani 1 1 d . . . H7 H 0.2682 0.0177 0.5801 0.054 Uiso 1 1 calc R . . C8 C 0.2023(3) -0.04573(12) 0.51524(11) 0.0439(6) Uani 1 1 d . . . H8 H 0.1676 -0.0785 0.5418 0.053 Uiso 1 1 calc R . . C9 C 0.1924(3) -0.05463(11) 0.45395(11) 0.0401(6) Uani 1 1 d . . . H9 H 0.1505 -0.0936 0.4385 0.048 Uiso 1 1 calc R . . C10 C 0.2436(3) -0.00675(10) 0.41449(10) 0.0336(5) Uani 1 1 d . . . O11 O 0.1739(3) -0.06707(8) 0.32839(8) 0.0603(6) Uani 1 1 d . . . C11 C 0.2296(3) -0.01724(10) 0.34856(11) 0.0373(6) Uani 1 1 d . . . C12 C 0.2814(3) 0.03519(10) 0.30813(10) 0.0315(5) Uani 1 1 d . . . C13 C 0.2666(3) 0.02744(10) 0.24620(10) 0.0351(5) Uani 1 1 d . . . H13 H 0.2328 -0.0123 0.2303 0.042 Uiso 1 1 calc R . . C14 C 0.3006(3) 0.07673(10) 0.20771(10) 0.0338(5) Uani 1 1 d . . . H14 H 0.2925 0.0707 0.1656 0.041 Uiso 1 1 calc R . . C15 C 0.3619(3) 0.19010(9) 0.19103(9) 0.0270(5) Uani 1 1 d . . . C16 C 0.3094(3) 0.29198(10) 0.15082(9) 0.0318(5) Uani 1 1 d . . . C17 C 0.4290(3) 0.25285(10) 0.10577(9) 0.0296(5) Uani 1 1 d . . . C18 C 0.3934(4) 0.35366(11) 0.17192(11) 0.0460(6) Uani 1 1 d . . . H18A H 0.3088 0.3743 0.1999 0.069 Uiso 1 1 calc R . . H18B H 0.4145 0.3810 0.1373 0.069 Uiso 1 1 calc R . . H18C H 0.5108 0.3453 0.1921 0.069 Uiso 1 1 calc R . . C19 C 0.1106(3) 0.30200(12) 0.13069(11) 0.0467(6) Uani 1 1 d . . . H19A H 0.0445 0.3264 0.1611 0.070 Uiso 1 1 calc R . . H19B H 0.0502 0.2612 0.1255 0.070 Uiso 1 1 calc R . . H19C H 0.1094 0.3248 0.0925 0.070 Uiso 1 1 calc R . . C20 C 0.6300(3) 0.27330(11) 0.10227(10) 0.0389(6) Uani 1 1 d . . . H20A H 0.6953 0.2470 0.0731 0.058 Uiso 1 1 calc R . . H20B H 0.6875 0.2687 0.1418 0.058 Uiso 1 1 calc R . . H20C H 0.6363 0.3173 0.0896 0.058 Uiso 1 1 calc R . . C21 C 0.3492(4) 0.24592(12) 0.04283(10) 0.0412(6) Uani 1 1 d . . . H21A H 0.4337 0.2211 0.0180 0.062 Uiso 1 1 calc R . . H21B H 0.3329 0.2875 0.0249 0.062 Uiso 1 1 calc R . . H21C H 0.2298 0.2246 0.0451 0.062 Uiso 1 1 calc R . . 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 C1 0.0267(11) 0.0342(12) 0.0259(11) 0.0012(9) 0.0011(9) 0.0012(9) O1 0.0709(12) 0.0494(10) 0.0280(9) 0.0013(8) 0.0183(8) 0.0153(9) N1 0.0385(10) 0.0367(10) 0.0226(9) 0.0014(8) 0.0059(8) 0.0038(8) O2 0.0417(9) 0.0394(9) 0.0284(8) -0.0086(7) 0.0025(7) 0.0041(7) N2 0.0316(10) 0.0320(10) 0.0217(9) -0.0017(7) -0.0002(7) 0.0012(8) C2 0.0291(11) 0.0303(11) 0.0272(11) -0.0001(9) 0.0005(9) 0.0002(9) C3 0.0273(11) 0.0318(11) 0.0278(12) 0.0030(9) 0.0002(9) 0.0021(9) O4 0.0530(11) 0.0406(9) 0.0289(9) 0.0014(7) -0.0050(7) -0.0097(8) C4 0.0309(12) 0.0320(12) 0.0303(12) 0.0012(10) -0.0011(9) 0.0013(10) C5 0.0306(12) 0.0364(12) 0.0289(11) 0.0048(9) 0.0009(9) 0.0048(10) C6 0.0430(14) 0.0413(13) 0.0317(12) 0.0043(10) 0.0026(10) 0.0047(11) C7 0.0469(15) 0.0537(16) 0.0340(13) 0.0131(12) 0.0049(11) 0.0044(12) C8 0.0406(14) 0.0494(15) 0.0416(15) 0.0203(12) 0.0043(11) 0.0025(11) C9 0.0358(13) 0.0375(13) 0.0469(15) 0.0104(11) 0.0018(11) -0.0004(10) C10 0.0285(11) 0.0346(12) 0.0377(13) 0.0097(10) 0.0018(10) 0.0018(9) O11 0.0931(16) 0.0381(10) 0.0495(11) 0.0027(8) -0.0049(10) -0.0207(10) C11 0.0400(13) 0.0309(12) 0.0410(14) 0.0019(10) -0.0003(11) -0.0031(10) C12 0.0298(12) 0.0318(11) 0.0330(12) -0.0003(9) 0.0009(9) 0.0007(9) C13 0.0411(13) 0.0302(11) 0.0340(12) -0.0055(10) -0.0004(10) -0.0019(10) C14 0.0357(13) 0.0376(12) 0.0281(12) -0.0029(10) -0.0001(10) -0.0002(10) C15 0.0289(11) 0.0310(11) 0.0211(11) 0.0008(9) -0.0006(9) 0.0004(9) C16 0.0375(13) 0.0343(11) 0.0236(11) 0.0060(9) 0.0011(9) 0.0014(10) C17 0.0338(12) 0.0359(12) 0.0190(10) 0.0034(9) -0.0018(9) -0.0022(9) C18 0.0617(17) 0.0368(13) 0.0394(14) 0.0003(11) 0.0032(12) -0.0039(12) C19 0.0402(14) 0.0554(16) 0.0445(15) 0.0082(12) 0.0012(11) 0.0093(12) C20 0.0374(13) 0.0500(14) 0.0293(12) 0.0025(11) 0.0036(10) -0.0040(11) C21 0.0510(15) 0.0511(14) 0.0216(11) 0.0031(10) -0.0070(10) -0.0011(12) _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 C1 C2 1.395(3) . ? C1 C14 1.403(3) . ? C1 C15 1.462(3) . ? O1 N1 1.282(2) . ? N1 C15 1.341(3) . ? N1 C16 1.507(3) . ? O2 N2 1.281(2) . ? N2 C15 1.350(3) . ? N2 C17 1.503(3) . ? C2 C3 1.398(3) . ? C2 H2 0.9500 . ? C3 C12 1.397(3) . ? C3 C4 1.496(3) . ? O4 C4 1.221(3) . ? C4 C5 1.490(3) . ? C5 C6 1.398(3) . ? C5 C10 1.398(3) . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(4) . ? C7 H7 0.9500 . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 C10 1.398(3) . ? C9 H9 0.9500 . ? C10 C11 1.491(3) . ? O11 C11 1.222(3) . ? C11 C12 1.484(3) . ? C12 C13 1.395(3) . ? C13 C14 1.379(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C18 1.524(3) . ? C16 C19 1.526(3) . ? C16 C17 1.568(3) . ? C17 C20 1.525(3) . ? C17 C21 1.525(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C2 C1 C14 119.75(19) . . ? C2 C1 C15 119.80(19) . . ? C14 C1 C15 120.35(18) . . ? O1 N1 C15 125.71(17) . . ? O1 N1 C16 120.65(16) . . ? C15 N1 C16 113.25(16) . . ? O2 N2 C15 125.84(17) . . ? O2 N2 C17 121.36(16) . . ? C15 N2 C17 112.63(16) . . ? C1 C2 C3 119.85(19) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C12 C3 C2 120.09(19) . . ? C12 C3 C4 121.05(18) . . ? C2 C3 C4 118.86(19) . . ? O4 C4 C5 121.62(19) . . ? O4 C4 C3 121.08(19) . . ? C5 C4 C3 117.22(18) . . ? C6 C5 C10 119.6(2) . . ? C6 C5 C4 119.2(2) . . ? C10 C5 C4 121.21(19) . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.4(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.6(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C5 119.5(2) . . ? C9 C10 C11 119.5(2) . . ? C5 C10 C11 120.95(19) . . ? O11 C11 C12 121.0(2) . . ? O11 C11 C10 121.0(2) . . ? C12 C11 C10 117.95(19) . . ? C13 C12 C3 119.40(19) . . ? C13 C12 C11 119.51(19) . . ? C3 C12 C11 121.06(19) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C1 119.9(2) . . ? C13 C14 H14 120.0 . . ? C1 C14 H14 120.0 . . ? N1 C15 N2 109.19(17) . . ? N1 C15 C1 125.16(18) . . ? N2 C15 C1 125.51(18) . . ? N1 C16 C18 108.20(17) . . ? N1 C16 C19 106.14(17) . . ? C18 C16 C19 110.39(19) . . ? N1 C16 C17 101.09(15) . . ? C18 C16 C17 115.80(19) . . ? C19 C16 C17 114.19(18) . . ? N2 C17 C20 106.62(17) . . ? N2 C17 C21 107.53(17) . . ? C20 C17 C21 110.12(18) . . ? N2 C17 C16 101.89(15) . . ? C20 C17 C16 114.24(18) . . ? C21 C17 C16 115.50(18) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C14 C1 C2 C3 -2.2(3) . . . . ? C15 C1 C2 C3 174.27(19) . . . . ? C1 C2 C3 C12 -1.7(3) . . . . ? C1 C2 C3 C4 178.33(19) . . . . ? C12 C3 C4 O4 167.8(2) . . . . ? C2 C3 C4 O4 -12.2(3) . . . . ? C12 C3 C4 C5 -9.2(3) . . . . ? C2 C3 C4 C5 170.77(19) . . . . ? O4 C4 C5 C6 8.8(3) . . . . ? C3 C4 C5 C6 -174.2(2) . . . . ? O4 C4 C5 C10 -170.1(2) . . . . ? C3 C4 C5 C10 6.9(3) . . . . ? C10 C5 C6 C7 -0.1(3) . . . . ? C4 C5 C6 C7 -179.0(2) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? C7 C8 C9 C10 0.1(4) . . . . ? C8 C9 C10 C5 0.7(3) . . . . ? C8 C9 C10 C11 -179.3(2) . . . . ? C6 C5 C10 C9 -0.7(3) . . . . ? C4 C5 C10 C9 178.1(2) . . . . ? C6 C5 C10 C11 179.3(2) . . . . ? C4 C5 C10 C11 -1.9(3) . . . . ? C9 C10 C11 O11 0.1(4) . . . . ? C5 C10 C11 O11 -179.9(2) . . . . ? C9 C10 C11 C12 178.7(2) . . . . ? C5 C10 C11 C12 -1.3(3) . . . . ? C2 C3 C12 C13 4.2(3) . . . . ? C4 C3 C12 C13 -175.9(2) . . . . ? C2 C3 C12 C11 -173.6(2) . . . . ? C4 C3 C12 C11 6.3(3) . . . . ? O11 C11 C12 C13 -0.2(3) . . . . ? C10 C11 C12 C13 -178.8(2) . . . . ? O11 C11 C12 C3 177.6(2) . . . . ? C10 C11 C12 C3 -1.0(3) . . . . ? C3 C12 C13 C14 -2.7(3) . . . . ? C11 C12 C13 C14 175.2(2) . . . . ? C12 C13 C14 C1 -1.3(3) . . . . ? C2 C1 C14 C13 3.7(3) . . . . ? C15 C1 C14 C13 -172.7(2) . . . . ? O1 N1 C15 N2 177.4(2) . . . . ? C16 N1 C15 N2 4.6(2) . . . . ? O1 N1 C15 C1 1.5(3) . . . . ? C16 N1 C15 C1 -171.38(19) . . . . ? O2 N2 C15 N1 -179.43(18) . . . . ? C17 N2 C15 N1 5.3(2) . . . . ? O2 N2 C15 C1 -3.5(3) . . . . ? C17 N2 C15 C1 -178.73(18) . . . . ? C2 C1 C15 N1 -37.4(3) . . . . ? C14 C1 C15 N1 139.1(2) . . . . ? C2 C1 C15 N2 147.3(2) . . . . ? C14 C1 C15 N2 -36.2(3) . . . . ? O1 N1 C16 C18 53.0(3) . . . . ? C15 N1 C16 C18 -133.7(2) . . . . ? O1 N1 C16 C19 -65.5(3) . . . . ? C15 N1 C16 C19 107.8(2) . . . . ? O1 N1 C16 C17 175.11(19) . . . . ? C15 N1 C16 C17 -11.6(2) . . . . ? O2 N2 C17 C20 -67.5(2) . . . . ? C15 N2 C17 C20 107.9(2) . . . . ? O2 N2 C17 C21 50.5(2) . . . . ? C15 N2 C17 C21 -133.99(19) . . . . ? O2 N2 C17 C16 172.41(17) . . . . ? C15 N2 C17 C16 -12.1(2) . . . . ? N1 C16 C17 N2 13.03(19) . . . . ? C18 C16 C17 N2 129.67(19) . . . . ? C19 C16 C17 N2 -100.45(19) . . . . ? N1 C16 C17 C20 -101.51(19) . . . . ? C18 C16 C17 C20 15.1(3) . . . . ? C19 C16 C17 C20 145.0(2) . . . . ? N1 C16 C17 C21 129.23(19) . . . . ? C18 C16 C17 C21 -114.1(2) . . . . ? C19 C16 C17 C21 15.7(3) . . . . ? data_BAntQNN99K _database_code_depnum_ccdc_archive 'CCDC 923569' #TrackingRef 'AntQNN.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl ; _chemical_name_common ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazole-3-oxide- ; _chemical_melting_point 481 _chemical_formula_moiety 'C21 H19 N2 O4' _chemical_formula_sum 'C21 H19 N2 O4' _chemical_formula_weight 363.38 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.2081(4) _cell_length_b 21.2504(13) _cell_length_c 22.2459(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3407.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 99(2) _cell_measurement_reflns_used 3551 _cell_measurement_theta_min 2.651 _cell_measurement_theta_max 25.641 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6146 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 99(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 '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 30866 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.40 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 3482 _reflns_number_gt 2568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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 'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+2.0352P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3482 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.317 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.053 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 C1 C 0.3521(2) 0.13595(8) 0.23107(8) 0.0183(4) Uani 1 1 d . . . O1 O 0.2292(2) 0.26579(6) 0.25311(6) 0.0289(4) Uani 1 1 d . . . N1 N 0.3070(2) 0.24872(7) 0.20376(7) 0.0197(4) Uani 1 1 d . . . O2 O 0.50216(19) 0.14096(6) 0.10726(6) 0.0218(3) Uani 1 1 d . . . N2 N 0.4337(2) 0.18907(7) 0.13437(7) 0.0171(3) Uani 1 1 d . . . C2 C 0.3744(3) 0.14396(8) 0.29307(8) 0.0179(4) Uani 1 1 d . . . H2 H 0.4108 0.1836 0.3089 0.021 Uiso 1 1 calc R . . C3 C 0.3426(2) 0.09323(9) 0.33146(8) 0.0179(4) Uani 1 1 d . . . O4 O 0.4529(2) 0.14863(6) 0.41692(6) 0.0236(3) Uani 1 1 d . . . C4 C 0.3729(3) 0.10207(8) 0.39774(8) 0.0186(4) Uani 1 1 d . . . C5 C 0.3092(3) 0.05066(9) 0.43823(8) 0.0195(4) Uani 1 1 d . . . C6 C 0.3191(3) 0.05945(9) 0.50061(9) 0.0232(4) Uani 1 1 d . . . H6 H 0.3635 0.0981 0.5165 0.028 Uiso 1 1 calc R . . C7 C 0.2642(3) 0.01180(9) 0.53911(9) 0.0257(5) Uani 1 1 d . . . H7 H 0.2699 0.0182 0.5813 0.031 Uiso 1 1 calc R . . C8 C 0.2004(3) -0.04556(9) 0.51647(9) 0.0256(5) Uani 1 1 d . . . H8 H 0.1638 -0.0782 0.5431 0.031 Uiso 1 1 calc R . . C9 C 0.1910(3) -0.05442(9) 0.45478(9) 0.0236(4) Uani 1 1 d . . . H9 H 0.1481 -0.0934 0.4392 0.028 Uiso 1 1 calc R . . C10 C 0.2439(3) -0.00658(9) 0.41529(9) 0.0205(4) Uani 1 1 d . . . O11 O 0.1714(2) -0.06700(7) 0.32887(7) 0.0336(4) Uani 1 1 d . . . C11 C 0.2294(3) -0.01736(9) 0.34916(9) 0.0216(4) Uani 1 1 d . . . C12 C 0.2841(3) 0.03525(8) 0.30849(9) 0.0194(4) Uani 1 1 d . . . C13 C 0.2697(3) 0.02713(9) 0.24634(9) 0.0211(4) Uani 1 1 d . . . H13 H 0.2350 -0.0127 0.2305 0.025 Uiso 1 1 calc R . . C14 C 0.3055(3) 0.07670(9) 0.20763(8) 0.0206(4) Uani 1 1 d . . . H14 H 0.2984 0.0706 0.1654 0.025 Uiso 1 1 calc R . . C15 C 0.3675(3) 0.19044(8) 0.19100(8) 0.0170(4) Uani 1 1 d . . . C16 C 0.3157(3) 0.29257(9) 0.15071(8) 0.0196(4) Uani 1 1 d . . . C17 C 0.4356(3) 0.25319(8) 0.10543(8) 0.0182(4) Uani 1 1 d . . . C18 C 0.4004(3) 0.35463(9) 0.17148(9) 0.0264(5) Uani 1 1 d . . . H18A H 0.3156 0.3754 0.1996 0.040 Uiso 1 1 calc R . . H18B H 0.4210 0.3820 0.1366 0.040 Uiso 1 1 calc R . . H18C H 0.5190 0.3464 0.1915 0.040 Uiso 1 1 calc R . . C19 C 0.1150(3) 0.30266(10) 0.13051(9) 0.0269(5) Uani 1 1 d . . . H19A H 0.0485 0.3272 0.1610 0.040 Uiso 1 1 calc R . . H19B H 0.0542 0.2618 0.1253 0.040 Uiso 1 1 calc R . . H19C H 0.1137 0.3255 0.0922 0.040 Uiso 1 1 calc R . . C20 C 0.6386(3) 0.27355(9) 0.10214(9) 0.0230(4) Uani 1 1 d . . . H20A H 0.7044 0.2472 0.0729 0.035 Uiso 1 1 calc R . . H20B H 0.6962 0.2688 0.1418 0.035 Uiso 1 1 calc R . . H20C H 0.6455 0.3177 0.0896 0.035 Uiso 1 1 calc R . . C21 C 0.3551(3) 0.24617(10) 0.04232(8) 0.0239(4) Uani 1 1 d . . . H21A H 0.4401 0.2213 0.0175 0.036 Uiso 1 1 calc R . . H21B H 0.3386 0.2879 0.0243 0.036 Uiso 1 1 calc R . . H21C H 0.2347 0.2248 0.0446 0.036 Uiso 1 1 calc R . . 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 C1 0.0167(9) 0.0220(9) 0.0163(9) 0.0021(7) 0.0012(7) 0.0017(7) O1 0.0397(9) 0.0319(8) 0.0152(7) -0.0016(6) 0.0105(6) 0.0064(7) N1 0.0232(8) 0.0233(8) 0.0128(8) 0.0008(6) 0.0029(6) 0.0009(7) O2 0.0238(7) 0.0235(7) 0.0182(7) -0.0052(5) 0.0018(6) 0.0027(6) N2 0.0179(8) 0.0204(8) 0.0129(7) -0.0007(6) 0.0007(6) 0.0000(6) C2 0.0166(9) 0.0206(9) 0.0164(9) -0.0014(7) -0.0009(7) 0.0006(7) C3 0.0141(9) 0.0226(9) 0.0170(9) 0.0019(7) 0.0005(7) 0.0022(7) O4 0.0289(8) 0.0242(7) 0.0177(7) 0.0005(5) -0.0029(6) -0.0034(6) C4 0.0181(9) 0.0193(9) 0.0182(9) -0.0003(7) 0.0009(7) 0.0014(7) C5 0.0168(9) 0.0243(10) 0.0174(9) 0.0026(8) 0.0002(7) 0.0025(8) C6 0.0237(10) 0.0262(10) 0.0197(10) 0.0024(8) 0.0004(8) 0.0026(8) C7 0.0248(11) 0.0339(11) 0.0184(10) 0.0067(9) 0.0005(8) 0.0036(9) C8 0.0221(10) 0.0301(11) 0.0245(11) 0.0117(8) 0.0014(8) 0.0011(8) C9 0.0206(10) 0.0222(10) 0.0280(11) 0.0053(8) -0.0009(8) 0.0005(8) C10 0.0180(9) 0.0231(10) 0.0206(10) 0.0041(8) 0.0005(8) 0.0016(8) O11 0.0475(10) 0.0254(8) 0.0279(8) 0.0000(6) -0.0015(7) -0.0106(7) C11 0.0215(10) 0.0196(9) 0.0237(10) 0.0005(8) 0.0006(8) -0.0008(8) C12 0.0162(9) 0.0210(9) 0.0211(10) 0.0010(8) -0.0009(8) 0.0018(7) C13 0.0229(10) 0.0197(9) 0.0207(10) -0.0032(8) -0.0001(8) -0.0006(8) C14 0.0206(10) 0.0247(10) 0.0164(9) -0.0022(8) 0.0003(7) 0.0002(8) C15 0.0186(9) 0.0207(9) 0.0117(8) -0.0005(7) -0.0005(7) -0.0014(7) C16 0.0235(10) 0.0217(9) 0.0137(9) 0.0029(7) 0.0010(7) 0.0014(8) C17 0.0223(10) 0.0213(9) 0.0110(9) 0.0007(7) -0.0002(7) -0.0001(8) C18 0.0330(12) 0.0229(10) 0.0233(10) 0.0006(8) 0.0020(9) -0.0019(9) C19 0.0235(11) 0.0320(11) 0.0253(11) 0.0045(9) -0.0003(8) 0.0051(9) C20 0.0234(10) 0.0298(10) 0.0159(9) 0.0018(8) 0.0015(8) -0.0029(8) C21 0.0284(11) 0.0304(10) 0.0128(9) 0.0016(8) -0.0034(8) -0.0008(9) _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 C1 C2 1.399(3) . ? C1 C14 1.404(3) . ? C1 C15 1.465(2) . ? O1 N1 1.285(2) . ? N1 C15 1.343(2) . ? N1 C16 1.505(2) . ? O2 N2 1.2854(19) . ? N2 C15 1.347(2) . ? N2 C17 1.507(2) . ? C2 C3 1.394(3) . ? C2 H2 0.9500 . ? C3 C12 1.399(3) . ? C3 C4 1.502(3) . ? O4 C4 1.222(2) . ? C4 C5 1.488(3) . ? C5 C10 1.401(3) . ? C5 C6 1.402(3) . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.397(3) . ? C7 H7 0.9500 . ? C8 C9 1.387(3) . ? C8 H8 0.9500 . ? C9 C10 1.397(3) . ? C9 H9 0.9500 . ? C10 C11 1.492(3) . ? O11 C11 1.221(2) . ? C11 C12 1.491(3) . ? C12 C13 1.397(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C18 1.525(3) . ? C16 C19 1.530(3) . ? C16 C17 1.569(3) . ? C17 C21 1.527(2) . ? C17 C20 1.528(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C2 C1 C14 120.19(17) . . ? C2 C1 C15 119.66(16) . . ? C14 C1 C15 120.07(16) . . ? O1 N1 C15 125.62(15) . . ? O1 N1 C16 120.88(14) . . ? C15 N1 C16 113.05(15) . . ? O2 N2 C15 126.29(15) . . ? O2 N2 C17 121.00(14) . . ? C15 N2 C17 112.52(14) . . ? C3 C2 C1 119.40(17) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C12 120.45(17) . . ? C2 C3 C4 118.72(16) . . ? C12 C3 C4 120.83(16) . . ? O4 C4 C5 121.91(17) . . ? O4 C4 C3 120.83(16) . . ? C5 C4 C3 117.21(16) . . ? C10 C5 C6 119.56(17) . . ? C10 C5 C4 121.38(17) . . ? C6 C5 C4 119.04(17) . . ? C7 C6 C5 120.03(19) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.62(19) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.44(18) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.68(18) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C5 119.65(18) . . ? C9 C10 C11 119.30(17) . . ? C5 C10 C11 121.05(17) . . ? O11 C11 C12 120.93(18) . . ? O11 C11 C10 121.38(17) . . ? C12 C11 C10 117.68(16) . . ? C13 C12 C3 119.52(17) . . ? C13 C12 C11 119.21(16) . . ? C3 C12 C11 121.22(17) . . ? C14 C13 C12 120.50(17) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C1 119.73(17) . . ? C13 C14 H14 120.1 . . ? C1 C14 H14 120.1 . . ? N1 C15 N2 109.42(15) . . ? N1 C15 C1 125.13(16) . . ? N2 C15 C1 125.33(16) . . ? N1 C16 C18 108.33(15) . . ? N1 C16 C19 106.13(15) . . ? C18 C16 C19 110.27(16) . . ? N1 C16 C17 101.31(14) . . ? C18 C16 C17 115.80(16) . . ? C19 C16 C17 114.01(16) . . ? N2 C17 C21 107.53(14) . . ? N2 C17 C20 106.57(15) . . ? C21 C17 C20 110.36(16) . . ? N2 C17 C16 101.71(13) . . ? C21 C17 C16 115.66(16) . . ? C20 C17 C16 114.03(15) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C14 C1 C2 C3 -2.5(3) . . . . ? C15 C1 C2 C3 174.05(17) . . . . ? C1 C2 C3 C12 -1.7(3) . . . . ? C1 C2 C3 C4 178.10(17) . . . . ? C2 C3 C4 O4 -12.2(3) . . . . ? C12 C3 C4 O4 167.61(18) . . . . ? C2 C3 C4 C5 170.43(16) . . . . ? C12 C3 C4 C5 -9.7(3) . . . . ? O4 C4 C5 C10 -169.99(18) . . . . ? C3 C4 C5 C10 7.3(3) . . . . ? O4 C4 C5 C6 8.5(3) . . . . ? C3 C4 C5 C6 -174.18(17) . . . . ? C10 C5 C6 C7 -0.2(3) . . . . ? C4 C5 C6 C7 -178.67(18) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C5 0.7(3) . . . . ? C8 C9 C10 C11 -179.11(18) . . . . ? C6 C5 C10 C9 -0.5(3) . . . . ? C4 C5 C10 C9 177.93(17) . . . . ? C6 C5 C10 C11 179.31(18) . . . . ? C4 C5 C10 C11 -2.2(3) . . . . ? C9 C10 C11 O11 0.4(3) . . . . ? C5 C10 C11 O11 -179.48(19) . . . . ? C9 C10 C11 C12 178.95(17) . . . . ? C5 C10 C11 C12 -0.9(3) . . . . ? C2 C3 C12 C13 4.3(3) . . . . ? C4 C3 C12 C13 -175.51(17) . . . . ? C2 C3 C12 C11 -173.19(17) . . . . ? C4 C3 C12 C11 7.0(3) . . . . ? O11 C11 C12 C13 -0.5(3) . . . . ? C10 C11 C12 C13 -179.05(17) . . . . ? O11 C11 C12 C3 177.03(18) . . . . ? C10 C11 C12 C3 -1.6(3) . . . . ? C3 C12 C13 C14 -2.6(3) . . . . ? C11 C12 C13 C14 174.90(17) . . . . ? C12 C13 C14 C1 -1.6(3) . . . . ? C2 C1 C14 C13 4.2(3) . . . . ? C15 C1 C14 C13 -172.38(17) . . . . ? O1 N1 C15 N2 177.25(17) . . . . ? C16 N1 C15 N2 4.8(2) . . . . ? O1 N1 C15 C1 1.1(3) . . . . ? C16 N1 C15 C1 -171.34(16) . . . . ? O2 N2 C15 N1 -179.79(16) . . . . ? C17 N2 C15 N1 5.1(2) . . . . ? O2 N2 C15 C1 -3.6(3) . . . . ? C17 N2 C15 C1 -178.69(16) . . . . ? C2 C1 C15 N1 -37.0(3) . . . . ? C14 C1 C15 N1 139.63(19) . . . . ? C2 C1 C15 N2 147.46(19) . . . . ? C14 C1 C15 N2 -36.0(3) . . . . ? O1 N1 C16 C18 53.1(2) . . . . ? C15 N1 C16 C18 -134.13(17) . . . . ? O1 N1 C16 C19 -65.3(2) . . . . ? C15 N1 C16 C19 107.47(18) . . . . ? O1 N1 C16 C17 175.32(16) . . . . ? C15 N1 C16 C17 -11.86(19) . . . . ? O2 N2 C17 C21 50.6(2) . . . . ? C15 N2 C17 C21 -134.00(16) . . . . ? O2 N2 C17 C20 -67.7(2) . . . . ? C15 N2 C17 C20 107.66(17) . . . . ? O2 N2 C17 C16 172.58(15) . . . . ? C15 N2 C17 C16 -12.04(19) . . . . ? N1 C16 C17 N2 13.15(16) . . . . ? C18 C16 C17 N2 130.08(16) . . . . ? C19 C16 C17 N2 -100.38(17) . . . . ? N1 C16 C17 C21 129.31(16) . . . . ? C18 C16 C17 C21 -113.76(19) . . . . ? C19 C16 C17 C21 15.8(2) . . . . ? N1 C16 C17 C20 -101.13(17) . . . . ? C18 C16 C17 C20 15.8(2) . . . . ? C19 C16 C17 C20 145.34(17) . . . . ? data_BAntQNN10K _database_code_depnum_ccdc_archive 'CCDC 923570' #TrackingRef 'AntQNN.cif' #=========================================================================== # # The submitted manuscript has been created by UChicago Argonne, LLC, # Operator of Argonne National Laboratory ("Argonne"). Argonne, a U.S. # Department of Energy Office of Science laboratory, is operated under # Contract No. DE-AC02-06CH11357. The U.S. Government retains for itself, # and others acting on its behalf, a paid-up nonexclusive, irrevocable # worldwide license in said article to reproduce, prepare derivative works, # distribute copies to the public, and perform publicly and display # publicly, by or on behalf of the Government. #=========================================================================== _audit_creation_method 'manual editing of SHELXL-97 cif file' _chemical_name_systematic ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl ; _chemical_name_common ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazole-3-oxide- ; _chemical_melting_point 481 _chemical_formula_moiety 'C21 H19 N2 O4' _chemical_formula_sum 'C21 H19 N2 O4' _chemical_formula_weight 363.38 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.1778(4) _cell_length_b 21.2070(12) _cell_length_c 22.1861(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3377.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 10(2) _cell_measurement_reflns_used 3504 _cell_measurement_theta_min 2.658 _cell_measurement_theta_max 26.423 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5683 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS, R. Blessing; 1995' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.000 cm. ; _diffrn_radiation_probe x-ray _diffrn_ambient_temperature 10(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 '3-circle goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 35765 _diffrn_reflns_av_R_equivalents 0.0923 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.34 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 4209 _reflns_number_gt 3007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II v.2.2 (Bruker, 2007)' _computing_cell_refinement 'APEX II v.2.2 (Bruker, 2007)' _computing_data_reduction 'APEX II v.2.2 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.1a (Crystal Impact, 2005)' _computing_publication_material 'SHELXTL (Bruker, 2006)' _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 'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+3.0338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4209 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.437 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.065 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 C1 C 0.3553(2) 0.13628(9) 0.23115(8) 0.0128(4) Uani 1 1 d . . . O1 O 0.23338(19) 0.26645(6) 0.25345(6) 0.0166(3) Uani 1 1 d . . . N1 N 0.3110(2) 0.24939(7) 0.20418(7) 0.0124(3) Uani 1 1 d . . . O2 O 0.50532(18) 0.14117(6) 0.10715(6) 0.0143(3) Uani 1 1 d . . . N2 N 0.4375(2) 0.18947(7) 0.13429(6) 0.0112(3) Uani 1 1 d . . . C2 C 0.3777(2) 0.14415(8) 0.29336(8) 0.0117(3) Uani 1 1 d . . . H2 H 0.4148 0.1838 0.3092 0.014 Uiso 1 1 calc R . . C3 C 0.3453(2) 0.09340(9) 0.33187(8) 0.0122(4) Uani 1 1 d . . . O4 O 0.45602(18) 0.14885(6) 0.41776(6) 0.0147(3) Uani 1 1 d . . . C4 C 0.3751(2) 0.10239(8) 0.39821(8) 0.0125(4) Uani 1 1 d . . . C5 C 0.3105(2) 0.05080(9) 0.43883(8) 0.0128(4) Uani 1 1 d . . . C6 C 0.3202(2) 0.05949(9) 0.50133(8) 0.0138(4) Uani 1 1 d . . . H6 H 0.3654 0.0982 0.5173 0.017 Uiso 1 1 calc R . . C7 C 0.2639(3) 0.01180(9) 0.54003(9) 0.0153(4) Uani 1 1 d . . . H7 H 0.2690 0.0182 0.5824 0.018 Uiso 1 1 calc R . . C8 C 0.1999(3) -0.04549(9) 0.51716(8) 0.0145(4) Uani 1 1 d . . . H8 H 0.1632 -0.0783 0.5438 0.017 Uiso 1 1 calc R . . C9 C 0.1900(3) -0.05434(9) 0.45516(8) 0.0140(4) Uani 1 1 d . . . H9 H 0.1460 -0.0933 0.4395 0.017 Uiso 1 1 calc R . . C10 C 0.2441(2) -0.00634(9) 0.41574(8) 0.0131(4) Uani 1 1 d . . . O11 O 0.17043(19) -0.06688(6) 0.32909(6) 0.0178(3) Uani 1 1 d . . . C11 C 0.2297(3) -0.01717(8) 0.34950(8) 0.0131(4) Uani 1 1 d . . . C12 C 0.2859(2) 0.03533(9) 0.30886(8) 0.0128(4) Uani 1 1 d . . . C13 C 0.2716(3) 0.02725(9) 0.24644(8) 0.0137(4) Uani 1 1 d . . . H13 H 0.2365 -0.0126 0.2305 0.016 Uiso 1 1 calc R . . C14 C 0.3085(2) 0.07691(9) 0.20784(8) 0.0133(4) Uani 1 1 d . . . H14 H 0.3020 0.0708 0.1655 0.016 Uiso 1 1 calc R . . C15 C 0.3718(2) 0.19071(8) 0.19117(8) 0.0113(3) Uani 1 1 d . . . C16 C 0.3192(2) 0.29307(8) 0.15067(8) 0.0120(4) Uani 1 1 d . . . C17 C 0.4397(2) 0.25355(8) 0.10532(8) 0.0113(3) Uani 1 1 d . . . C18 C 0.4043(3) 0.35549(9) 0.17127(9) 0.0161(4) Uani 1 1 d . . . H18A H 0.3193 0.3763 0.1995 0.024 Uiso 1 1 calc R . . H18B H 0.4245 0.3828 0.1362 0.024 Uiso 1 1 calc R . . H18C H 0.5236 0.3474 0.1913 0.024 Uiso 1 1 calc R . . C19 C 0.1171(3) 0.30317(9) 0.13055(9) 0.0161(4) Uani 1 1 d . . . H19A H 0.0507 0.3277 0.1612 0.024 Uiso 1 1 calc R . . H19B H 0.0560 0.2622 0.1255 0.024 Uiso 1 1 calc R . . H19C H 0.1155 0.3260 0.0922 0.024 Uiso 1 1 calc R . . C20 C 0.6434(2) 0.27380(9) 0.10181(8) 0.0147(4) Uani 1 1 d . . . H20A H 0.7091 0.2474 0.0725 0.022 Uiso 1 1 calc R . . H20B H 0.7016 0.2690 0.1415 0.022 Uiso 1 1 calc R . . H20C H 0.6505 0.3180 0.0892 0.022 Uiso 1 1 calc R . . C21 C 0.3585(3) 0.24659(9) 0.04211(8) 0.0151(4) Uani 1 1 d . . . H21A H 0.4436 0.2216 0.0171 0.023 Uiso 1 1 calc R . . H21B H 0.3421 0.2884 0.0241 0.023 Uiso 1 1 calc R . . H21C H 0.2376 0.2253 0.0445 0.023 Uiso 1 1 calc R . . 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 C1 0.0088(8) 0.0169(9) 0.0126(8) 0.0011(7) 0.0011(7) 0.0011(7) O1 0.0188(7) 0.0213(7) 0.0098(6) -0.0022(5) 0.0048(5) 0.0023(6) N1 0.0126(7) 0.0155(7) 0.0090(7) 0.0004(6) 0.0011(6) -0.0008(6) O2 0.0142(6) 0.0150(6) 0.0137(6) -0.0040(5) 0.0010(5) 0.0019(5) N2 0.0109(7) 0.0132(7) 0.0094(7) -0.0005(6) -0.0005(6) 0.0002(6) C2 0.0095(8) 0.0135(9) 0.0121(8) -0.0018(7) -0.0002(7) 0.0004(7) C3 0.0076(8) 0.0170(9) 0.0120(8) 0.0008(7) 0.0008(7) 0.0012(7) O4 0.0158(6) 0.0161(7) 0.0121(6) 0.0004(5) -0.0014(5) -0.0010(5) C4 0.0102(8) 0.0129(9) 0.0144(9) -0.0014(7) -0.0001(7) 0.0012(7) C5 0.0104(8) 0.0157(9) 0.0122(8) 0.0004(7) 0.0001(7) 0.0018(7) C6 0.0103(8) 0.0162(9) 0.0148(9) -0.0003(7) 0.0001(7) -0.0003(7) C7 0.0124(9) 0.0214(10) 0.0121(8) 0.0014(7) -0.0003(7) 0.0015(7) C8 0.0123(8) 0.0173(9) 0.0139(9) 0.0057(7) 0.0011(7) 0.0009(7) C9 0.0114(8) 0.0140(9) 0.0165(9) -0.0001(7) -0.0004(7) 0.0000(7) C10 0.0087(8) 0.0169(9) 0.0135(8) 0.0016(7) -0.0004(7) 0.0025(7) O11 0.0211(7) 0.0161(7) 0.0163(7) -0.0004(5) -0.0003(6) -0.0030(5) C11 0.0111(8) 0.0142(9) 0.0139(9) 0.0000(7) -0.0004(7) 0.0010(7) C12 0.0100(8) 0.0152(9) 0.0133(8) 0.0006(7) -0.0006(7) 0.0012(7) C13 0.0122(9) 0.0144(9) 0.0146(9) -0.0032(7) -0.0002(7) -0.0001(7) C14 0.0112(8) 0.0188(9) 0.0097(8) -0.0013(7) 0.0006(7) 0.0003(7) C15 0.0090(8) 0.0156(9) 0.0093(8) -0.0009(7) -0.0009(6) -0.0007(7) C16 0.0129(8) 0.0144(9) 0.0087(8) 0.0016(7) 0.0004(7) -0.0002(7) C17 0.0119(8) 0.0129(8) 0.0092(8) 0.0003(7) 0.0000(6) 0.0007(7) C18 0.0179(9) 0.0151(9) 0.0152(9) 0.0007(7) 0.0014(7) -0.0014(7) C19 0.0134(9) 0.0191(10) 0.0158(9) 0.0017(8) 0.0004(7) 0.0012(7) C20 0.0113(8) 0.0195(9) 0.0133(9) 0.0008(7) 0.0009(7) -0.0004(7) C21 0.0152(9) 0.0209(9) 0.0090(8) 0.0009(7) -0.0019(7) -0.0008(8) _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 C1 C2 1.400(2) . ? C1 C14 1.402(3) . ? C1 C15 1.460(2) . ? O1 N1 1.2794(19) . ? N1 C15 1.350(2) . ? N1 C16 1.507(2) . ? O2 N2 1.2840(19) . ? N2 C15 1.348(2) . ? N2 C17 1.503(2) . ? C2 C3 1.394(2) . ? C2 H2 0.9500 . ? C3 C12 1.399(3) . ? C3 C4 1.500(2) . ? O4 C4 1.223(2) . ? C4 C5 1.491(3) . ? C5 C10 1.399(3) . ? C5 C6 1.401(3) . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C7 C8 1.395(3) . ? C7 H7 0.9500 . ? C8 C9 1.390(3) . ? C8 H8 0.9500 . ? C9 C10 1.397(3) . ? C9 H9 0.9500 . ? C10 C11 1.491(3) . ? O11 C11 1.224(2) . ? C11 C12 1.488(3) . ? C12 C13 1.399(3) . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C18 1.528(3) . ? C16 C19 1.533(2) . ? C16 C17 1.569(2) . ? C17 C21 1.526(2) . ? C17 C20 1.526(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C2 C1 C14 119.89(17) . . ? C2 C1 C15 119.69(16) . . ? C14 C1 C15 120.35(16) . . ? O1 N1 C15 125.74(15) . . ? O1 N1 C16 121.08(14) . . ? C15 N1 C16 112.69(14) . . ? O2 N2 C15 125.97(15) . . ? O2 N2 C17 121.11(14) . . ? C15 N2 C17 112.74(14) . . ? C3 C2 C1 119.55(17) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C12 120.46(16) . . ? C2 C3 C4 118.66(16) . . ? C12 C3 C4 120.89(16) . . ? O4 C4 C5 121.62(16) . . ? O4 C4 C3 121.21(16) . . ? C5 C4 C3 117.09(15) . . ? C10 C5 C6 119.56(17) . . ? C10 C5 C4 121.33(16) . . ? C6 C5 C4 119.10(16) . . ? C7 C6 C5 120.17(17) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.40(17) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.64(17) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.45(17) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 119.77(17) . . ? C9 C10 C11 119.05(17) . . ? C5 C10 C11 121.18(16) . . ? O11 C11 C12 120.96(17) . . ? O11 C11 C10 121.43(17) . . ? C12 C11 C10 117.59(16) . . ? C13 C12 C3 119.41(17) . . ? C13 C12 C11 119.22(16) . . ? C3 C12 C11 121.31(16) . . ? C14 C13 C12 120.38(17) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C1 120.09(16) . . ? C13 C14 H14 120.0 . . ? C1 C14 H14 120.0 . . ? N2 C15 N1 109.34(15) . . ? N2 C15 C1 125.57(16) . . ? N1 C15 C1 124.94(16) . . ? N1 C16 C18 108.22(14) . . ? N1 C16 C19 106.16(14) . . ? C18 C16 C19 110.14(15) . . ? N1 C16 C17 101.44(13) . . ? C18 C16 C17 115.75(15) . . ? C19 C16 C17 114.16(15) . . ? N2 C17 C21 107.55(14) . . ? N2 C17 C20 106.64(14) . . ? C21 C17 C20 110.27(15) . . ? N2 C17 C16 101.70(13) . . ? C21 C17 C16 115.50(15) . . ? C20 C17 C16 114.22(15) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C14 C1 C2 C3 -2.8(3) . . . . ? C15 C1 C2 C3 174.18(16) . . . . ? C1 C2 C3 C12 -1.7(3) . . . . ? C1 C2 C3 C4 178.37(16) . . . . ? C2 C3 C4 O4 -12.5(3) . . . . ? C12 C3 C4 O4 167.51(17) . . . . ? C2 C3 C4 C5 170.49(16) . . . . ? C12 C3 C4 C5 -9.5(2) . . . . ? O4 C4 C5 C10 -170.05(17) . . . . ? C3 C4 C5 C10 6.9(2) . . . . ? O4 C4 C5 C6 8.7(3) . . . . ? C3 C4 C5 C6 -174.35(16) . . . . ? C10 C5 C6 C7 -0.2(3) . . . . ? C4 C5 C6 C7 -178.90(16) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C5 0.6(3) . . . . ? C8 C9 C10 C11 -179.33(17) . . . . ? C6 C5 C10 C9 -0.6(3) . . . . ? C4 C5 C10 C9 178.10(16) . . . . ? C6 C5 C10 C11 179.31(17) . . . . ? C4 C5 C10 C11 -2.0(3) . . . . ? C9 C10 C11 O11 0.5(3) . . . . ? C5 C10 C11 O11 -179.42(17) . . . . ? C9 C10 C11 C12 179.09(16) . . . . ? C5 C10 C11 C12 -0.8(3) . . . . ? C2 C3 C12 C13 4.4(3) . . . . ? C4 C3 C12 C13 -175.67(17) . . . . ? C2 C3 C12 C11 -172.93(16) . . . . ? C4 C3 C12 C11 7.0(3) . . . . ? O11 C11 C12 C13 -0.4(3) . . . . ? C10 C11 C12 C13 -179.04(17) . . . . ? O11 C11 C12 C3 176.84(17) . . . . ? C10 C11 C12 C3 -1.8(3) . . . . ? C3 C12 C13 C14 -2.6(3) . . . . ? C11 C12 C13 C14 174.73(16) . . . . ? C12 C13 C14 C1 -1.8(3) . . . . ? C2 C1 C14 C13 4.5(3) . . . . ? C15 C1 C14 C13 -172.41(17) . . . . ? O2 N2 C15 N1 -179.70(15) . . . . ? C17 N2 C15 N1 5.3(2) . . . . ? O2 N2 C15 C1 -4.0(3) . . . . ? C17 N2 C15 C1 -179.04(16) . . . . ? O1 N1 C15 N2 177.02(15) . . . . ? C16 N1 C15 N2 5.0(2) . . . . ? O1 N1 C15 C1 1.3(3) . . . . ? C16 N1 C15 C1 -170.75(16) . . . . ? C2 C1 C15 N2 147.76(18) . . . . ? C14 C1 C15 N2 -35.3(3) . . . . ? C2 C1 C15 N1 -37.2(3) . . . . ? C14 C1 C15 N1 139.74(18) . . . . ? O1 N1 C16 C18 53.1(2) . . . . ? C15 N1 C16 C18 -134.39(16) . . . . ? O1 N1 C16 C19 -65.1(2) . . . . ? C15 N1 C16 C19 107.40(17) . . . . ? O1 N1 C16 C17 175.37(15) . . . . ? C15 N1 C16 C17 -12.17(18) . . . . ? O2 N2 C17 C21 50.5(2) . . . . ? C15 N2 C17 C21 -134.15(15) . . . . ? O2 N2 C17 C20 -67.74(19) . . . . ? C15 N2 C17 C20 107.58(16) . . . . ? O2 N2 C17 C16 172.31(14) . . . . ? C15 N2 C17 C16 -12.37(18) . . . . ? N1 C16 C17 N2 13.53(16) . . . . ? C18 C16 C17 N2 130.38(15) . . . . ? C19 C16 C17 N2 -100.18(16) . . . . ? N1 C16 C17 C21 129.63(15) . . . . ? C18 C16 C17 C21 -113.51(18) . . . . ? C19 C16 C17 C21 15.9(2) . . . . ? N1 C16 C17 C20 -100.91(16) . . . . ? C18 C16 C17 C20 15.9(2) . . . . ? C19 C16 C17 C20 145.38(16) . . . . ? #END data_antqnn_alpha_293K _database_code_depnum_ccdc_archive 'CCDC 923571' _audit_update_record ; 2012-10-24 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl- 4,5-dihydro-1H-imidazole-3-oxide-1-oxyl ; _chemical_name_common ; 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazole-3-oxide-1-oxyl ; _chemical_melting_point 207-209 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N2 O4' _chemical_formula_weight 363.38 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 8.2851(17) _cell_length_b 18.895(4) _cell_length_c 11.832(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.70(3) _cell_angle_gamma 90.00 _cell_volume 1764.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3775 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 293(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 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7057 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.52 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 4036 _reflns_number_gt 3031 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 'calc w=1/[\s^2^(Fo^2^)+(0.1640P)^2^+0.4895P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4036 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1951 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 0.822 _refine_ls_restrained_S_all 0.822 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.397 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.130 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 C1 C 0.2344(2) 0.54047(9) 1.29583(14) 0.0380(4) Uani 1 1 d . . . O1 O 0.3348(2) 0.69100(7) 1.28245(12) 0.0627(4) Uani 1 1 d . . . N1 N 0.3390(2) 0.65987(8) 1.37927(12) 0.0421(4) Uani 1 1 d . . . O2 O 0.2911(3) 0.52175(8) 1.55388(13) 0.0793(6) Uani 1 1 d . . . N2 N 0.3114(2) 0.58062(8) 1.50681(13) 0.0462(4) Uani 1 1 d . . . C2 C 0.2772(2) 0.54724(8) 1.19069(14) 0.0366(4) Uani 1 1 d . . . H2 H 0.3367 0.5868 1.1785 0.044 Uiso 1 1 calc R . . C3 C 0.23031(19) 0.49460(8) 1.10412(13) 0.0333(3) Uani 1 1 d . . . O4 O 0.3440(2) 0.55665(7) 0.97248(12) 0.0577(4) Uani 1 1 d . . . C4 C 0.2762(2) 0.50309(8) 0.99211(14) 0.0371(4) Uani 1 1 d . . . C5 C 0.2325(2) 0.44398(9) 0.90480(14) 0.0376(4) Uani 1 1 d . . . C6 C 0.2733(3) 0.44989(10) 0.79924(16) 0.0499(4) Uani 1 1 d . . . H6 H 0.3279 0.4902 0.7843 0.060 Uiso 1 1 calc R . . C7 C 0.2324(3) 0.39572(11) 0.71672(18) 0.0571(5) Uani 1 1 d . . . H7 H 0.2593 0.4000 0.6462 0.069 Uiso 1 1 calc R . . C8 C 0.1523(3) 0.33554(11) 0.73788(17) 0.0539(5) Uani 1 1 d . . . H8 H 0.1271 0.2991 0.6823 0.065 Uiso 1 1 calc R . . C9 C 0.1095(2) 0.32916(9) 0.84124(17) 0.0463(4) Uani 1 1 d . . . H9 H 0.0532 0.2889 0.8544 0.056 Uiso 1 1 calc R . . C10 C 0.1505(2) 0.38303(8) 0.92647(14) 0.0374(4) Uani 1 1 d . . . O11 O 0.0512(2) 0.31883(8) 1.06301(14) 0.0677(5) Uani 1 1 d . . . C11 C 0.1071(2) 0.37447(9) 1.03791(15) 0.0410(4) Uani 1 1 d . . . C12 C 0.14220(19) 0.43501(8) 1.12283(14) 0.0354(4) Uani 1 1 d . . . C13 C 0.0921(2) 0.43046(10) 1.22470(16) 0.0433(4) Uani 1 1 d . . . H13 H 0.0280 0.3920 1.2352 0.052 Uiso 1 1 calc R . . C14 C 0.1368(2) 0.48252(10) 1.31003(15) 0.0437(4) Uani 1 1 d . . . H14 H 0.1020 0.4792 1.3775 0.052 Uiso 1 1 calc R . . C15 C 0.2922(2) 0.59267(9) 1.39092(14) 0.0393(4) Uani 1 1 d . . . C16 C 0.4202(2) 0.69387(9) 1.49828(15) 0.0426(4) Uani 1 1 d . . . C17 C 0.3448(2) 0.64804(9) 1.57762(14) 0.0411(4) Uani 1 1 d . . . C18 C 0.3776(3) 0.77198(10) 1.49471(19) 0.0631(6) Uani 1 1 d . . . H18A H 0.2575 0.7777 1.4785 0.095 Uiso 1 1 calc R . . H18B H 0.4128 0.7946 1.4335 0.095 Uiso 1 1 calc R . . H18C H 0.4354 0.7931 1.5699 0.095 Uiso 1 1 calc R . . C19 C 0.6113(3) 0.68299(13) 1.5235(2) 0.0624(6) Uani 1 1 d . . . H19D H 0.6356 0.6333 1.5252 0.094 Uiso 1 1 calc R . . H19E H 0.6705 0.7036 1.5989 0.094 Uiso 1 1 calc R . . H19F H 0.6473 0.7053 1.4624 0.094 Uiso 1 1 calc R . . C20 C 0.1737(3) 0.67339(13) 1.5849(2) 0.0599(5) Uani 1 1 d . . . H20D H 0.0995 0.6822 1.5064 0.090 Uiso 1 1 calc R . . H20E H 0.1888 0.7162 1.6306 0.090 Uiso 1 1 calc R . . H20F H 0.1251 0.6377 1.6223 0.090 Uiso 1 1 calc R . . C21 C 0.4625(3) 0.63413(12) 1.70183(16) 0.0571(5) Uani 1 1 d . . . H21A H 0.5702 0.6181 1.6971 0.086 Uiso 1 1 calc R . . H21B H 0.4139 0.5985 1.7394 0.086 Uiso 1 1 calc R . . H21C H 0.4777 0.6770 1.7474 0.086 Uiso 1 1 calc R . . 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 C1 0.0467(8) 0.0362(8) 0.0305(8) -0.0005(6) 0.0106(6) 0.0037(6) O1 0.1136(13) 0.0416(8) 0.0353(7) 0.0041(5) 0.0265(7) -0.0100(7) N1 0.0640(9) 0.0349(7) 0.0288(7) 0.0012(5) 0.0161(6) 0.0008(6) O2 0.1536(18) 0.0446(8) 0.0384(8) 0.0064(6) 0.0273(9) -0.0213(9) N2 0.0728(10) 0.0361(8) 0.0304(7) 0.0010(6) 0.0165(6) -0.0011(7) C2 0.0446(8) 0.0313(8) 0.0338(8) 0.0003(6) 0.0118(6) -0.0006(6) C3 0.0380(8) 0.0312(7) 0.0293(7) 0.0005(6) 0.0080(6) 0.0032(6) O4 0.0916(10) 0.0420(8) 0.0485(8) -0.0054(6) 0.0350(7) -0.0179(7) C4 0.0467(9) 0.0318(8) 0.0332(8) 0.0004(6) 0.0128(6) -0.0010(6) C5 0.0438(8) 0.0358(8) 0.0324(8) -0.0014(6) 0.0103(6) 0.0031(6) C6 0.0712(12) 0.0431(10) 0.0409(9) -0.0043(8) 0.0253(8) -0.0017(8) C7 0.0835(13) 0.0529(11) 0.0410(10) -0.0087(8) 0.0280(9) 0.0025(10) C8 0.0694(12) 0.0451(10) 0.0436(10) -0.0143(8) 0.0119(9) 0.0052(9) C9 0.0522(10) 0.0371(9) 0.0461(10) -0.0083(7) 0.0099(8) -0.0007(7) C10 0.0391(8) 0.0351(8) 0.0353(8) -0.0023(6) 0.0072(6) 0.0029(6) O11 0.1059(12) 0.0454(8) 0.0600(9) -0.0090(7) 0.0374(9) -0.0299(8) C11 0.0455(9) 0.0350(8) 0.0405(9) -0.0028(7) 0.0102(7) -0.0054(6) C12 0.0372(7) 0.0337(8) 0.0334(8) 0.0002(6) 0.0081(6) 0.0000(6) C13 0.0480(9) 0.0438(9) 0.0406(9) -0.0001(7) 0.0173(7) -0.0080(7) C14 0.0523(10) 0.0458(10) 0.0372(9) -0.0008(7) 0.0197(7) -0.0032(7) C15 0.0545(9) 0.0343(8) 0.0290(7) 0.0001(6) 0.0124(6) 0.0020(7) C16 0.0593(10) 0.0362(9) 0.0337(8) -0.0060(6) 0.0165(7) -0.0013(7) C17 0.0582(10) 0.0367(8) 0.0290(8) -0.0028(6) 0.0142(7) 0.0030(7) C18 0.1069(17) 0.0355(10) 0.0528(12) -0.0029(8) 0.0330(11) 0.0013(10) C19 0.0612(12) 0.0715(15) 0.0577(12) -0.0151(10) 0.0229(10) -0.0109(10) C20 0.0613(11) 0.0701(14) 0.0528(11) -0.0088(10) 0.0243(9) 0.0036(10) C21 0.0769(13) 0.0580(12) 0.0316(9) -0.0001(8) 0.0092(8) 0.0036(10) _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 C1 C14 1.401(2) . ? C1 C15 1.463(2) . ? N1 O1 1.2790(19) . ? N1 C15 1.347(2) . ? N1 C16 1.507(2) . ? N2 O2 1.278(2) . ? C2 C1 1.399(2) . ? C3 C2 1.396(2) . ? C3 C12 1.396(2) . ? O4 C4 1.214(2) . ? C4 C5 1.489(2) . ? C4 C3 1.495(2) . ? C5 C6 1.394(2) . ? C5 C10 1.400(2) . ? C6 C7 1.384(3) . ? C7 C8 1.377(3) . ? C9 C8 1.378(3) . ? C10 C9 1.400(2) . ? C10 C11 1.477(2) . ? O11 C11 1.222(2) . ? C12 C13 1.392(2) . ? C12 C11 1.492(2) . ? C14 C13 1.377(3) . ? C15 N2 1.351(2) . ? C16 C18 1.515(3) . ? C16 C19 1.533(3) . ? C17 N2 1.504(2) . ? C17 C21 1.519(2) . ? C17 C20 1.523(3) . ? C17 C16 1.542(3) . ? 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 C2 C1 C14 119.31(15) . . ? C2 C1 C15 120.66(15) . . ? C14 C1 C15 120.02(15) . . ? O1 N1 C15 126.52(14) . . ? O1 N1 C16 121.57(14) . . ? C15 N1 C16 111.52(13) . . ? O2 N2 C15 126.78(15) . . ? O2 N2 C17 121.41(14) . . ? C15 N2 C17 111.57(14) . . ? C3 C2 C1 119.89(15) . . ? C2 C3 C12 120.05(15) . . ? C2 C3 C4 119.03(14) . . ? C12 C3 C4 120.91(14) . . ? O4 C4 C5 121.46(15) . . ? O4 C4 C3 121.10(14) . . ? C5 C4 C3 117.43(14) . . ? C6 C5 C10 119.56(15) . . ? C6 C5 C4 119.16(15) . . ? C10 C5 C4 121.28(14) . . ? C7 C6 C5 119.95(18) . . ? C8 C7 C6 120.69(18) . . ? C7 C8 C9 120.12(17) . . ? C8 C9 C10 120.27(18) . . ? C5 C10 C9 119.41(16) . . ? C5 C10 C11 121.12(14) . . ? C9 C10 C11 119.47(15) . . ? O11 C11 C10 121.63(16) . . ? O11 C11 C12 120.45(16) . . ? C10 C11 C12 117.85(14) . . ? C13 C12 C3 119.69(15) . . ? C13 C12 C11 119.20(15) . . ? C3 C12 C11 121.06(15) . . ? C14 C13 C12 120.41(16) . . ? C13 C14 C1 120.43(16) . . ? N1 C15 N2 108.31(14) . . ? N1 C15 C1 126.44(14) . . ? N2 C15 C1 125.24(15) . . ? N1 C16 C18 110.79(16) . . ? N1 C16 C19 105.46(15) . . ? C18 C16 C19 110.75(18) . . ? N1 C16 C17 100.42(13) . . ? C18 C16 C17 115.44(16) . . ? C19 C16 C17 113.05(16) . . ? N2 C17 C21 110.35(14) . . ? N2 C17 C20 106.32(15) . . ? C21 C17 C20 109.53(16) . . ? N2 C17 C16 100.17(13) . . ? C21 C17 C16 115.23(16) . . ? C20 C17 C16 114.47(16) . . ? # END ===== NEXT FILE