# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _database_code_CSD 151137 _publ_contact_author_name 'David B. Amabilino' _publ_contact_author_address ; David B. Amabilino Insitut de Ciencia de Materials de Barcelona (CSIC) Campus Universitari E-08193 Bellaterra Spain ; _publ_contact_author_phone '34 3 93 580 1853' _publ_contact_author_fax '34 3 93 580 5729' _publ_contact_author_email amabilino@icmab.es _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 2' _journal_coden_Cambridge 188 _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #========================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Circular Dichroism studies of crystalline chiral and achiral a-nitronyl nitroxide radicals in KBr matrix ; loop_ _publ_author_name _publ_author_address 'David B. Amabilino' ; Insitut de Ciencia de Materials de Barcelona (CSIC) Campus Universitari E-08193 Bellaterra Spain ; 'Maria Minguet' ; Insitut de Ciencia de Materials de Barcelona (CSIC) Campus Universitari E-08193 Bellaterra Spain ; 'Jaume Veciana' ; Insitut de Ciencia de Materials de Barcelona (CSIC) Campus Universitari E-08193 Bellaterra Spain ; 'Wurst, Klaus' ; Institut f\"ur Allgemeine und Anorganische Chemie Universit\"at Innsbruck Innrainstr. 52a A-6020 Innsbruck Austria ; data_amab1 _audit_creation_method SHELXL _chemical_name_systematic ; (R)-methyl[3-(4,4,5,5-tetramethyl-4,5-dihydro-1H- imidazolyl-1-oxy-3-oxide)phenoxy]-2-propionate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H23 N2 O5' _chemical_formula_weight 335.37 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)2(1)2(1) 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' _cell_length_a 10.559(2) _cell_length_b 11.894(2) _cell_length_c 14.016(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1760.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 218(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 5.5 _cell_measurement_theta_max 12.0 _exptl_crystal_description prism _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method ? _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 218(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 'Bruker P4' _diffrn_measurement_method omega-scans _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2694 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 23.00 _reflns_number_total 2066 _reflns_number_observed 1839 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 53 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.4737P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0227(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.78(145) _refine_ls_number_reflns 2013 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_obs 0.0319 _refine_ls_wR_factor_all 0.0775 _refine_ls_wR_factor_obs 0.0722 _refine_ls_goodness_of_fit_all 1.054 _refine_ls_goodness_of_fit_obs 1.074 _refine_ls_restrained_S_all 1.080 _refine_ls_restrained_S_obs 1.074 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 1.0120(2) 0.4995(2) -0.14862(12) 0.0552(6) Uani 1 d . . O2 O 1.0344(2) 0.2091(2) 0.07104(14) 0.0672(7) Uani 1 d . . O3 O 0.8748(2) 0.73434(14) 0.11593(12) 0.0404(5) Uani 1 d . . O4 O 0.6387(2) 0.6511(2) 0.04408(15) 0.0607(6) Uani 1 d . . O5 O 0.7292(2) 0.6641(2) -0.09984(13) 0.0451(5) Uani 1 d . . N1 N 1.0165(2) 0.4011(2) -0.11097(15) 0.0360(5) Uani 1 d . . N2 N 1.0312(2) 0.2639(2) -0.0077(2) 0.0420(6) Uani 1 d . . C1 C 1.0232(2) 0.3769(2) -0.0165(2) 0.0324(6) Uani 1 d . . C2 C 1.0007(3) 0.2982(2) -0.1713(2) 0.0405(7) Uani 1 d . . C3 C 1.0463(3) 0.2063(2) -0.1019(2) 0.0445(7) Uani 1 d . . C4 C 1.0194(2) 0.4583(2) 0.0615(2) 0.0320(6) Uani 1 d . . C5 C 0.9507(2) 0.5579(2) 0.0483(2) 0.0331(6) Uani 1 d . . H5 H 0.9097 0.5719 -0.0100 0.040 Uiso 1 calc . . C6 C 0.9437(2) 0.6355(2) 0.1216(2) 0.0334(6) Uani 1 d . . C7 C 1.0080(3) 0.6177(2) 0.2069(2) 0.0384(7) Uani 1 d . . H7 H 1.0042 0.6715 0.2560 0.046 Uiso 1 calc . . C8 C 1.0771(3) 0.5206(2) 0.2190(2) 0.0411(7) Uani 1 d . . H8 H 1.1218 0.5093 0.2762 0.049 Uiso 1 calc . . C9 C 1.0820(3) 0.4388(2) 0.1478(2) 0.0384(7) Uani 1 d . . H9 H 1.1269 0.3715 0.1577 0.046 Uiso 1 calc . . C10 C 0.8273(3) 0.7652(2) 0.0236(2) 0.0365(7) Uani 1 d . . H10 H 0.8967 0.7625 -0.0238 0.044 Uiso 1 calc . . C11 C 0.7774(3) 0.8841(2) 0.0319(2) 0.0494(8) Uani 1 d . . H11A H 0.7431(16) 0.9077(6) -0.0291(4) 0.074 Uiso 1 calc R . H11B H 0.8459(5) 0.9341(3) 0.0501(13) 0.074 Uiso 1 calc R . H11C H 0.7114(12) 0.8868(4) 0.0799(10) 0.074 Uiso 1 calc R . C12 C 0.7206(3) 0.6866(2) -0.0070(2) 0.0370(7) Uani 1 d . . C13 C 0.6356(3) 0.5885(3) -0.1395(2) 0.0528(8) Uani 1 d . . H13A H 0.6538(11) 0.5759(13) -0.2065(4) 0.079 Uiso 1 calc R . H13B H 0.5521(3) 0.6216(8) -0.1331(12) 0.079 Uiso 1 calc R . H13C H 0.6382(13) 0.5175(6) -0.1056(9) 0.079 Uiso 1 calc R . C21 C 1.0720(3) 0.3075(3) -0.2642(2) 0.0614(9) Uani 1 d . . H21A H 1.0663(17) 0.2368(7) -0.2984(7) 0.092 Uiso 1 calc R . H21B H 1.1601(5) 0.3246(17) -0.2513(2) 0.092 Uiso 1 calc R . H21C H 1.0353(13) 0.3670(12) -0.3026(7) 0.092 Uiso 1 calc R . C22 C 0.8572(3) 0.2928(3) -0.1933(2) 0.0629(9) Uani 1 d . . H22A H 0.8399(4) 0.2281(11) -0.2334(13) 0.094 Uiso 1 calc R . H22B H 0.8315(5) 0.3608(9) -0.2263(13) 0.094 Uiso 1 calc R . H22C H 0.8102(3) 0.2860(18) -0.1341(3) 0.094 Uiso 1 calc R . C31 C 1.1864(4) 0.1799(4) -0.1099(3) 0.0928(14) Uani 1 d . . H31A H 1.2027(5) 0.1415(21) -0.1697(9) 0.139 Uiso 1 calc R . H31B H 1.2117(7) 0.1321(19) -0.0571(11) 0.139 Uiso 1 calc R . H31C H 1.2346(4) 0.2493(4) -0.1079(20) 0.139 Uiso 1 calc R . C32 C 0.9675(4) 0.0982(3) -0.1039(3) 0.0862(13) Uani 1 d . . H32A H 1.0023(17) 0.0447(9) -0.0587(15) 0.129 Uiso 1 calc R . H32B H 0.9697(22) 0.0662(13) -0.1675(6) 0.129 Uiso 1 calc R . H32C H 0.8807(7) 0.1153(5) -0.0867(19) 0.129 Uiso 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 0.095(2) 0.0340(10) 0.0365(10) 0.0055(9) -0.0028(12) -0.0007(12) O2 0.119(2) 0.0441(12) 0.0384(12) 0.0117(10) -0.0022(13) 0.0095(12) O3 0.0471(11) 0.0404(11) 0.0337(11) -0.0041(9) -0.0015(10) 0.0061(9) O4 0.0529(13) 0.076(2) 0.0529(13) -0.0065(11) 0.0213(12) -0.0187(12) O5 0.0380(11) 0.0591(12) 0.0381(11) -0.0022(10) -0.0005(9) -0.0111(10) N1 0.0468(14) 0.0296(11) 0.0316(12) 0.0009(10) -0.0008(12) 0.0013(10) N2 0.058(2) 0.0372(13) 0.0312(13) 0.0075(11) 0.0034(12) 0.0055(12) C1 0.0338(15) 0.0321(14) 0.0314(15) 0.0025(12) -0.0009(13) 0.0022(12) C2 0.052(2) 0.0337(15) 0.035(2) -0.0045(12) 0.0011(14) 0.0019(14) C3 0.059(2) 0.0368(15) 0.038(2) -0.0039(12) 0.0004(15) 0.0097(14) C4 0.0307(14) 0.0352(14) 0.0302(14) 0.0026(12) 0.0027(13) -0.0027(13) C5 0.0316(14) 0.0388(15) 0.0288(14) -0.0005(12) -0.0032(12) -0.0002(12) C6 0.0333(14) 0.0341(14) 0.0329(15) 0.0004(12) 0.0030(13) -0.0003(12) C7 0.047(2) 0.039(2) 0.0294(15) -0.0021(12) 0.0018(14) -0.0057(15) C8 0.046(2) 0.050(2) 0.0274(15) 0.0059(14) -0.0062(13) -0.0038(15) C9 0.038(2) 0.040(2) 0.037(2) 0.0092(13) 0.0012(13) 0.0006(13) C10 0.035(2) 0.039(2) 0.035(2) 0.0003(13) -0.0001(13) -0.0013(13) C11 0.050(2) 0.039(2) 0.059(2) 0.0017(15) -0.010(2) 0.0026(15) C12 0.032(2) 0.041(2) 0.039(2) 0.0010(15) 0.0048(14) 0.0061(14) C13 0.042(2) 0.064(2) 0.053(2) -0.011(2) -0.003(2) -0.010(2) C21 0.084(3) 0.061(2) 0.039(2) -0.006(2) 0.015(2) 0.003(2) C22 0.063(2) 0.064(2) 0.062(2) -0.006(2) -0.011(2) -0.006(2) C31 0.091(3) 0.127(3) 0.061(2) -0.007(3) 0.003(2) 0.065(3) C32 0.148(4) 0.047(2) 0.064(2) 0.003(2) -0.012(3) -0.012(2) _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 N1 1.284(3) . ? O2 N2 1.282(3) . ? O3 C6 1.384(3) . ? O3 C10 1.435(3) . ? O4 C12 1.199(3) . ? O5 C12 1.331(3) . ? O5 C13 1.447(3) . ? N1 C1 1.357(3) . ? N1 C2 1.497(3) . ? N2 C1 1.352(3) . ? N2 C3 1.496(4) . ? C1 C4 1.461(3) . ? C2 C21 1.508(4) . ? C2 C3 1.541(4) . ? C2 C22 1.548(4) . ? C3 C31 1.516(4) . ? C3 C32 1.531(4) . ? C4 C9 1.398(4) . ? C4 C5 1.402(3) . ? C5 C6 1.383(4) . ? C6 C7 1.392(4) . ? C7 C8 1.376(4) . ? C8 C9 1.394(4) . ? C10 C11 1.514(4) . ? C10 C12 1.526(4) . ? 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 C6 O3 C10 116.9(2) . . ? C12 O5 C13 117.0(2) . . ? O1 N1 C1 126.6(2) . . ? O1 N1 C2 120.6(2) . . ? C1 N1 C2 112.5(2) . . ? O2 N2 C1 125.8(2) . . ? O2 N2 C3 121.6(2) . . ? C1 N2 C3 112.4(2) . . ? N2 C1 N1 107.7(2) . . ? N2 C1 C4 126.3(2) . . ? N1 C1 C4 126.0(2) . . ? N1 C2 C21 111.8(2) . . ? N1 C2 C3 100.9(2) . . ? C21 C2 C3 116.2(2) . . ? N1 C2 C22 104.9(2) . . ? C21 C2 C22 108.6(2) . . ? C3 C2 C22 113.7(2) . . ? N2 C3 C31 105.3(3) . . ? N2 C3 C32 110.0(2) . . ? C31 C3 C32 110.8(3) . . ? N2 C3 C2 101.5(2) . . ? C31 C3 C2 113.9(3) . . ? C32 C3 C2 114.5(3) . . ? C9 C4 C5 119.9(2) . . ? C9 C4 C1 121.7(2) . . ? C5 C4 C1 118.4(2) . . ? C6 C5 C4 119.6(2) . . ? C5 C6 O3 123.5(2) . . ? C5 C6 C7 120.7(2) . . ? O3 C6 C7 115.8(2) . . ? C8 C7 C6 119.5(2) . . ? C7 C8 C9 121.2(2) . . ? C8 C9 C4 119.1(2) . . ? O3 C10 C11 107.0(2) . . ? O3 C10 C12 110.8(2) . . ? C11 C10 C12 109.7(2) . . ? O4 C12 O5 124.2(3) . . ? O4 C12 C10 125.4(2) . . ? O5 C12 C10 110.3(2) . . ? 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 N1 C2 C3 N2 21.0(3) . . . . ? N2 C3 C2 N1 21.0(3) . . . . ? N1 C1 C4 C5 30.1(4) . . . . ? C5 C4 C1 N1 30.1(4) . . . . ? N2 C1 C4 C9 31.7(4) . . . . ? C9 C4 C1 N2 31.7(4) . . . . ? _refine_diff_density_max 0.123 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.027 #============================================================================ _eof # End of Crystallographic Information File