Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' _audit_creation_method maXus loop_ _publ_author_name 'Patrick S. Taylor' 'Paul R. Serwinski' 'Paul M. Lahti' _publ_contact_author_name 'Paul M. Lahti' _publ_contact_author_address ; Chemistry University of Massachusetts Lederle GRT Room 701 Amherst MA 01003 UNITED STATES OF AMERICA ; _publ_contact_author_email 'lahti@chem.umass.edu ' _publ_section_title ; Molecular recognition for stable organic radicals 6-uradinyl-4,4,5,5-tetramethyl- 4,5-dihydro-1H-imidazole-1-oxyl ; _publ_section_abstract ; We present the crystal and molecular structure of 6-uradinyl-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; data_compound _database_code_CSD 207264 _chemical_compound_source 'Local laboratory' _exptl_crystal_description Cube _exptl_crystal_colour reddish _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment noref # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 loop_ _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X==UH _diffrn_orient_matrix_UB_11 -0.04521 _diffrn_orient_matrix_UB_12 0.05316 _diffrn_orient_matrix_UB_13 -0.03791 _diffrn_orient_matrix_UB_21 0.03423 _diffrn_orient_matrix_UB_22 -0.01589 _diffrn_orient_matrix_UB_23 -0.06310 _diffrn_orient_matrix_UB_31 -0.05834 _diffrn_orient_matrix_UB_32 -0.03118 _diffrn_orient_matrix_UB_33 -0.02379 _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_special_details ; solvent == 1 to 1 chloroform to water, slow evaporation ; _chemical_formula_weight 251.266 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X+ 1/2,-Y+ 1/2,-Z' '+X+ 1/2,+Y+ 1/2,+Z' '-X,+Y,-Z+ 1/2' '+X,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C11 H15 N4 O3 ' _chemical_formula_sum 'C11 H15 N4 O3 ' _chemical_name_systematic ; 6-uradinyl-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl ; _diffrn_radiation_wavelength 0.71073 _diffrn_ambient_temperature 298 _exptl_crystal_F_000 1064 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _diffrn_reflns_av_R_equivalents 0.0249 _refine_diff_density_max 0.397 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.046 _cell_length_a 13.3744(9) _cell_length_b 13.6012(9) _cell_length_c 15.1086(13) _cell_angle_alpha 90.00 _cell_angle_beta 109.701(3) _cell_angle_gamma 90.00 _cell_volume 2587.5(3) _diffrn_reflns_number 4041 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_full 25.05 _cell_measurement_reflns_used 2209 _cell_measurement_theta_min 4.076 _cell_measurement_theta_max 25.028 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.096 _reflns_number_total 2244 _reflns_number_gt 1643 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1340P)^2^+2.2453P] where P==(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2244 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2667 _refine_ls_wR_factor_gt 0.2416 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 O1 O 0.5472(2) 0.4106(2) 0.58440(18) 0.0917(9) Uani 1 1 d . . . O2 O 0.1992(2) 0.4827(3) 0.4392(2) 0.1200(12) Uani 1 1 d . . . O3 O 0.1227(2) 0.2218(3) 0.6269(2) 0.1178(12) Uani 1 1 d . . . N1 N 0.3725(2) 0.4485(2) 0.5145(2) 0.0817(9) Uani 1 1 d . . . N2 N 0.2428(3) 0.3638(3) 0.5602(3) 0.0999(11) Uani 1 1 d . . . N3 N 0.2105(2) 0.2097(2) 0.6921(2) 0.0818(9) Uani 1 1 d . . . N4 N 0.3850(2) 0.2197(2) 0.76811(19) 0.0758(8) Uani 1 1 d . . . C1 C 0.3216(3) 0.3147(2) 0.6243(2) 0.0666(8) Uani 1 1 d . . . C2 C 0.4247(2) 0.3304(2) 0.63038(19) 0.0553(7) Uani 1 1 d . . . C3 C 0.4542(3) 0.3967(3) 0.5767(2) 0.0752(10) Uani 1 1 d . . . C4 C 0.2662(3) 0.4351(3) 0.4992(3) 0.0837(10) Uani 1 1 d . . . C5 C 0.3078(3) 0.2472(3) 0.6953(2) 0.0691(9) Uani 1 1 d . . . C6 C 0.2224(3) 0.1631(4) 0.7848(3) 0.0933(12) Uani 1 1 d . . . C7 C 0.3437(3) 0.1478(3) 0.8225(3) 0.0837(11) Uani 1 1 d . . . C8 C 0.1558(4) 0.0696(5) 0.7670(4) 0.137(2) Uani 1 1 d . . . C9 C 0.1834(5) 0.2395(6) 0.8386(4) 0.149(2) Uani 1 1 d . . . C10 C 0.3792(4) 0.0470(4) 0.8000(4) 0.1122(15) Uani 1 1 d . . . C11 C 0.3966(4) 0.1676(4) 0.9272(3) 0.1230(19) Uani 1 1 d . . . H1 H 0.3894 0.4935 0.4820 0.098 Uiso 1 1 calc R . . H2 H 0.1780 0.3526 0.5555 0.120 Uiso 1 1 calc R . . H2' H 0.4775 0.2936 0.6736 0.066 Uiso 1 1 calc R . . H8A H 0.0818 0.0864 0.7425 0.205 Uiso 1 1 calc R . . H8B H 0.1701 0.0341 0.8249 0.205 Uiso 1 1 calc R . . H8C H 0.1735 0.0292 0.7223 0.205 Uiso 1 1 calc R . . H9A H 0.1076 0.2454 0.8115 0.223 Uiso 1 1 calc R . . H9B H 0.2157 0.3018 0.8353 0.223 Uiso 1 1 calc R . . H9C H 0.2021 0.2196 0.9031 0.223 Uiso 1 1 calc R . . H10A H 0.4552 0.0424 0.8262 0.168 Uiso 1 1 calc R . . H10B H 0.3571 0.0386 0.7331 0.168 Uiso 1 1 calc R . . H10C H 0.3477 -0.0033 0.8266 0.168 Uiso 1 1 calc R . . H11A H 0.4717 0.1569 0.9445 0.185 Uiso 1 1 calc R . . H11B H 0.3678 0.1239 0.9624 0.185 Uiso 1 1 calc R . . H11C H 0.3835 0.2344 0.9407 0.185 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 O1 0.0786(17) 0.105(2) 0.0977(18) 0.0282(15) 0.0379(14) 0.0087(14) O2 0.102(2) 0.153(3) 0.104(2) 0.045(2) 0.0324(18) 0.041(2) O3 0.0756(19) 0.128(3) 0.133(3) 0.013(2) 0.0133(18) -0.0128(17) N1 0.089(2) 0.089(2) 0.0742(18) 0.0135(15) 0.0360(15) 0.0161(16) N2 0.094(2) 0.108(3) 0.098(2) -0.009(2) 0.0329(19) 0.0090(19) N3 0.0615(17) 0.090(2) 0.090(2) -0.0006(16) 0.0198(15) -0.0086(14) N4 0.0736(18) 0.088(2) 0.0690(17) 0.0001(14) 0.0287(15) -0.0105(14) C1 0.072(2) 0.0658(19) 0.0610(17) -0.0071(14) 0.0202(15) 0.0069(15) C2 0.0524(15) 0.0637(17) 0.0535(15) 0.0086(12) 0.0228(12) 0.0079(12) C3 0.079(2) 0.080(2) 0.070(2) 0.0050(16) 0.0292(17) 0.0128(17) C4 0.088(3) 0.096(3) 0.069(2) 0.0117(19) 0.0308(19) 0.019(2) C5 0.0663(19) 0.073(2) 0.0699(19) -0.0102(16) 0.0255(16) -0.0024(15) C6 0.077(2) 0.115(3) 0.094(3) 0.006(2) 0.037(2) -0.017(2) C7 0.080(2) 0.098(3) 0.078(2) 0.0067(19) 0.0342(18) -0.0162(19) C8 0.093(3) 0.146(5) 0.156(5) 0.043(4) 0.022(3) -0.044(3) C9 0.133(4) 0.205(7) 0.134(4) -0.012(4) 0.080(4) 0.032(4) C10 0.119(3) 0.100(3) 0.128(4) 0.027(3) 0.055(3) 0.000(3) C11 0.117(3) 0.171(5) 0.079(3) 0.020(3) 0.031(2) -0.053(3) _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 O1 C3 1.225(4) . ? O2 C4 1.223(4) . ? O3 N3 1.263(4) . ? N1 C3 1.372(4) . ? N1 C4 1.374(5) . ? N2 C1 1.344(5) . ? N2 C4 1.442(5) . ? N3 C5 1.384(4) . ? N3 C6 1.495(5) . ? N4 C5 1.285(4) . ? N4 C7 1.498(4) . ? C1 C2 1.368(4) . ? C1 C5 1.469(5) . ? C2 C3 1.358(4) . ? C6 C9 1.516(7) . ? C6 C8 1.525(7) . ? C6 C7 1.541(6) . ? C7 C11 1.524(6) . ? C7 C10 1.526(6) . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? C2 H2 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 C3 N1 C4 125.9(3) . . ? C1 N2 C4 120.6(3) . . ? O3 N3 C5 126.5(3) . . ? O3 N3 C6 124.3(3) . . ? C5 N3 C6 108.7(3) . . ? C5 N4 C7 108.7(3) . . ? N2 C1 C2 119.8(3) . . ? N2 C1 C5 125.2(3) . . ? C2 C1 C5 114.8(3) . . ? C3 C2 C1 123.6(3) . . ? O1 C3 C2 122.5(3) . . ? O1 C3 N1 122.3(3) . . ? C2 C3 N1 115.2(3) . . ? O2 C4 N1 120.8(4) . . ? O2 C4 N2 124.6(4) . . ? N1 C4 N2 114.6(3) . . ? N4 C5 N3 113.4(3) . . ? N4 C5 C1 123.0(3) . . ? N3 C5 C1 123.5(3) . . ? N3 C6 C9 105.3(4) . . ? N3 C6 C8 108.5(4) . . ? C9 C6 C8 112.3(4) . . ? N3 C6 C7 99.8(3) . . ? C9 C6 C7 113.8(4) . . ? C8 C6 C7 115.6(4) . . ? N4 C7 C11 109.0(3) . . ? N4 C7 C10 105.3(3) . . ? C11 C7 C10 108.6(4) . . ? N4 C7 C6 104.2(3) . . ? C11 C7 C6 115.0(4) . . ? C10 C7 C6 114.0(4) . . ? C3 N1 H1 117.0 . . ? C4 N1 H1 117.0 . . ? C1 N2 H2 119.7 . . ? C4 N2 H2 119.7 . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_measured_fraction_theta_full 0.977