# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Fedor Mushenok' _publ_contact_author_email MUSHENOKF@YANDEX.RU _publ_section_title ; Thermally induced paramagnetism of spiropyrane iodides ; loop_ _publ_author_name 'Fedor Mushenok' 'Sergey M Aldoshin' 'Roman B Morgunov' 'Nataliya Sanina' "E. Yur'eva" # Attachment 'Sp2I.cif' data_0 _database_code_depnum_ccdc_archive 'CCDC 721088' _audit_creation_method SHELXTL7 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H23 I N2 O' _chemical_formula_sum 'C23 H23 I N2 O' _chemical_formula_weight 470.33 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9250(16) _cell_length_b 11.338(2) _cell_length_c 23.147(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.14(3) _cell_angle_gamma 90.00 _cell_volume 2058.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 5 _cell_measurement_theta_max 15 _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max .36 _exptl_crystal_size_mid .34 _exptl_crystal_size_min .31 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.570 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min none _exptl_absorpt_correction_T_max none _exptl_absorpt_process_details none _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 ? _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 3944 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3659 _reflns_number_gt 2021 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _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^)+(0.0778P)^2^+0.0000P] 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 none _refine_ls_extinction_method SHELXTL _refine_ls_extinction_coef 0.0010(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3659 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.000 _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 I1 I 0.77342(6) 0.29233(3) 0.01253(2) 0.0796(2) Uani 1 1 d . . . O2 O 0.4081(5) -0.1159(3) 0.21499(15) 0.0564(9) Uani 1 1 d . . . C4 C 0.4895(6) -0.1439(4) 0.1689(2) 0.0476(12) Uani 1 1 d . . . C5 C 0.5371(6) -0.0637(4) 0.1313(2) 0.0446(12) Uani 1 1 d . . . C6 C 0.6548(6) -0.2231(4) 0.0786(2) 0.0447(12) Uani 1 1 d . . . C7 C 0.5266(8) -0.2650(4) 0.1633(2) 0.0536(14) Uani 1 1 d . . . H7 H 0.4954 -0.3187 0.1902 0.064 Uiso 1 1 calc R . . N8 N 0.7359(6) -0.2601(4) 0.0333(2) 0.0529(11) Uani 1 1 d . . . C9 C 0.6800(7) -0.0247(5) 0.0443(2) 0.0548(14) Uani 1 1 d . . . H8 H 0.6588 0.0558 0.0465 0.066 Uiso 1 1 calc R . . C10 C 0.6063(7) -0.3031(4) 0.1194(2) 0.0551(13) Uani 1 1 d . . . H10 H 0.6296 -0.3831 0.1161 0.066 Uiso 1 1 calc R . . C11 C 0.5001(7) 0.0608(4) 0.1427(2) 0.0545(14) Uani 1 1 d . . . H11 H 0.5435 0.1199 0.1211 0.065 Uiso 1 1 calc R . . C12 C 0.6240(6) -0.1016(4) 0.0855(2) 0.0476(12) Uani 1 1 d . . . N13 N 0.3307(7) 0.0274(4) 0.2777(2) 0.0640(13) Uani 1 1 d . . . C14 C 0.1955(8) -0.0289(5) 0.2991(2) 0.0553(14) Uani 1 1 d . . . C15 C 0.3202(7) -0.0025(4) 0.2166(2) 0.0546(14) Uani 1 1 d . . . C16 C 0.7614(9) -0.3886(6) 0.0241(3) 0.0737(18) Uani 1 1 d . . . H16A H 0.7173 -0.4316 0.0520 0.110 Uiso 1 1 d . . . H16B H 0.8795 -0.4120 0.0231 0.110 Uiso 1 1 d . . . H16C H 0.6998 -0.4070 -0.0152 0.110 Uiso 1 1 d . . . C17 C 0.7634(8) -0.0657(6) 0.0019(3) 0.0635(16) Uani 1 1 d . . . H17 H 0.8049 -0.0132 -0.0235 0.076 Uiso 1 1 calc R . . C18 C 0.0698(7) -0.0595(5) 0.2538(2) 0.0541(14) Uani 1 1 d . . . C19 C 0.7877(8) -0.1841(5) -0.0042(2) 0.0613(15) Uani 1 1 d . . . H19 H 0.8411 -0.2117 -0.0348 0.074 Uiso 1 1 calc R . . C20 C 0.1266(7) -0.0224(5) 0.1974(2) 0.0571(14) Uani 1 1 d . . . C21 C 0.4072(8) 0.0886(4) 0.1827(3) 0.0595(15) Uani 1 1 d . . . H21 H 0.3934 0.1680 0.1910 0.071 Uiso 1 1 calc R . . C22 C 0.0296(12) -0.1033(6) 0.3678(3) 0.085(2) Uani 1 1 d . . . H22 H 0.0152 -0.1196 0.4062 0.102 Uiso 1 1 calc R . . C23 C -0.0774(8) -0.1107(6) 0.2653(3) 0.0739(18) Uani 1 1 d . . . H23 H -0.1623 -0.1308 0.2350 0.089 Uiso 1 1 calc R . . C24 C -0.0995(10) -0.1326(6) 0.3230(4) 0.082(2) Uani 1 1 d . . . H24 H -0.1999 -0.1667 0.3315 0.098 Uiso 1 1 calc R . . C25 C 0.0887(9) -0.1155(6) 0.1492(3) 0.0807(19) Uani 1 1 d . . . H25A H 0.1270 -0.0874 0.1142 0.121 Uiso 1 1 calc R . . H25B H -0.0318 -0.1300 0.1419 0.121 Uiso 1 1 calc R . . H25C H 0.1472 -0.1874 0.1614 0.121 Uiso 1 1 calc R . . C26 C 0.0350(9) 0.0934(6) 0.1761(3) 0.088(2) Uani 1 1 d . . . H26A H 0.0708 0.1173 0.1399 0.132 Uiso 1 1 calc R . . H26B H 0.0633 0.1540 0.2048 0.132 Uiso 1 1 calc R . . H26C H -0.0861 0.0809 0.1703 0.132 Uiso 1 1 calc R . . C27 C 0.1767(10) -0.0512(5) 0.3569(3) 0.0735(19) Uani 1 1 d . . . H27 H 0.2620 -0.0312 0.3871 0.088 Uiso 1 1 calc R . . C28 C 0.4947(10) 0.0460(7) 0.3127(3) 0.094(2) Uani 1 1 d . . . H28A H 0.5688 0.0865 0.2900 0.142 Uiso 1 1 calc R . . H28B H 0.5438 -0.0288 0.3251 0.142 Uiso 1 1 calc R . . H28C H 0.4802 0.0925 0.3463 0.142 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 I1 0.0774(3) 0.0524(3) 0.1136(4) 0.0041(2) 0.0294(2) 0.0000(2) O2 0.072(2) 0.0483(19) 0.054(2) 0.0024(17) 0.0265(19) -0.0014(19) C4 0.051(3) 0.049(3) 0.045(3) 0.000(2) 0.015(2) -0.009(2) C5 0.046(3) 0.035(2) 0.054(3) 0.002(2) 0.010(3) -0.002(2) C6 0.044(3) 0.049(3) 0.042(3) 0.002(2) 0.007(2) 0.000(2) C7 0.074(4) 0.036(3) 0.055(3) 0.005(2) 0.026(3) -0.010(3) N8 0.052(2) 0.050(2) 0.058(3) -0.004(2) 0.012(2) -0.001(2) C9 0.050(3) 0.050(3) 0.064(4) 0.019(3) 0.009(3) -0.004(3) C10 0.061(3) 0.036(2) 0.070(4) -0.004(3) 0.015(3) -0.004(3) C11 0.064(3) 0.044(3) 0.060(4) 0.007(3) 0.027(3) -0.008(3) C12 0.046(3) 0.041(3) 0.056(3) 0.004(2) 0.009(2) -0.003(2) N13 0.075(3) 0.062(3) 0.056(3) -0.013(2) 0.009(3) 0.001(3) C14 0.069(4) 0.045(3) 0.054(4) -0.005(3) 0.018(3) 0.015(3) C15 0.065(4) 0.045(3) 0.057(4) -0.004(3) 0.021(3) -0.001(3) C16 0.094(5) 0.055(3) 0.077(5) -0.007(3) 0.028(4) 0.009(3) C17 0.068(4) 0.069(4) 0.056(4) 0.021(3) 0.017(3) 0.002(3) C18 0.057(3) 0.050(3) 0.056(3) 0.000(3) 0.012(3) 0.012(3) C19 0.070(4) 0.068(4) 0.051(3) 0.003(3) 0.023(3) 0.002(3) C20 0.062(3) 0.064(3) 0.046(3) 0.006(3) 0.009(3) 0.003(3) C21 0.073(4) 0.037(3) 0.070(4) -0.005(3) 0.013(3) -0.004(3) C22 0.129(7) 0.069(4) 0.068(5) 0.010(4) 0.047(5) 0.037(5) C23 0.064(4) 0.071(4) 0.091(5) 0.014(4) 0.024(4) 0.011(3) C24 0.080(5) 0.065(4) 0.110(6) 0.017(4) 0.049(5) 0.020(4) C25 0.077(4) 0.099(5) 0.065(4) -0.014(4) 0.006(3) -0.019(4) C26 0.090(5) 0.104(5) 0.071(5) 0.027(4) 0.013(4) 0.034(5) C27 0.108(6) 0.065(4) 0.051(4) 0.004(3) 0.022(4) 0.023(4) C28 0.096(6) 0.108(6) 0.074(5) -0.023(4) -0.003(4) -0.009(5) _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 O2 C4 1.360(6) . ? O2 C15 1.465(6) . ? C4 C5 1.349(7) . ? C4 C7 1.413(7) . ? C5 C12 1.410(7) . ? C5 C11 1.473(7) . ? C6 N8 1.372(6) . ? C6 C10 1.403(7) . ? C6 C12 1.412(7) . ? C7 C10 1.341(7) . ? N8 C19 1.328(7) . ? N8 C16 1.490(8) . ? C9 C17 1.340(7) . ? C9 C12 1.410(7) . ? C11 C21 1.301(7) . ? N13 C14 1.397(7) . ? N13 C15 1.446(7) . ? N13 C28 1.447(9) . ? C14 C18 1.385(8) . ? C14 C27 1.388(8) . ? C15 C21 1.519(7) . ? C15 C20 1.553(8) . ? C17 C19 1.366(9) . ? C18 C23 1.362(8) . ? C18 C20 1.501(8) . ? C20 C25 1.534(8) . ? C20 C26 1.547(8) . ? C22 C27 1.362(10) . ? C22 C24 1.390(11) . ? C23 C24 1.393(10) . ? 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 C4 O2 C15 120.3(4) . . ? C5 C4 O2 123.7(4) . . ? C5 C4 C7 121.0(5) . . ? O2 C4 C7 115.3(4) . . ? C4 C5 C12 119.4(4) . . ? C4 C5 C11 116.8(5) . . ? C12 C5 C11 123.8(4) . . ? N8 C6 C10 121.3(4) . . ? N8 C6 C12 119.5(4) . . ? C10 C6 C12 119.1(5) . . ? C10 C7 C4 120.6(5) . . ? C19 N8 C6 121.5(5) . . ? C19 N8 C16 118.7(5) . . ? C6 N8 C16 119.7(4) . . ? C17 C9 C12 121.0(5) . . ? C7 C10 C6 120.3(5) . . ? C21 C11 C5 120.4(5) . . ? C9 C12 C5 123.7(5) . . ? C9 C12 C6 116.7(5) . . ? C5 C12 C6 119.5(4) . . ? C14 N13 C15 107.5(5) . . ? C14 N13 C28 122.7(6) . . ? C15 N13 C28 120.3(5) . . ? C18 C14 C27 121.3(6) . . ? C18 C14 N13 110.5(5) . . ? C27 C14 N13 128.1(6) . . ? N13 C15 O2 105.6(4) . . ? N13 C15 C21 112.2(5) . . ? O2 C15 C21 109.4(4) . . ? N13 C15 C20 103.4(4) . . ? O2 C15 C20 108.6(4) . . ? C21 C15 C20 117.0(5) . . ? C9 C17 C19 120.6(5) . . ? C23 C18 C14 120.2(6) . . ? C23 C18 C20 131.3(6) . . ? C14 C18 C20 108.5(5) . . ? N8 C19 C17 120.6(5) . . ? C18 C20 C25 112.8(5) . . ? C18 C20 C26 109.3(5) . . ? C25 C20 C26 108.5(5) . . ? C18 C20 C15 101.4(4) . . ? C25 C20 C15 113.1(5) . . ? C26 C20 C15 111.6(5) . . ? C11 C21 C15 123.1(5) . . ? C27 C22 C24 121.6(7) . . ? C18 C23 C24 119.4(7) . . ? C22 C24 C23 119.5(7) . . ? C22 C27 C14 117.9(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.380 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.101 # Attachment 'SpI.cif' data_db200 _database_code_depnum_ccdc_archive 'CCDC 290280' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C22H27N2OI _chemical_formula_sum 'C22 H27 I N2 O' _chemical_formula_weight 462.36 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' I I -0.4742 1.8119 '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 12.862(3) _cell_length_b 11.025(2) _cell_length_c 16.019(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.00(3) _cell_angle_gamma 90.00 _cell_volume 2106.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 1.71 _cell_measurement_theta_max 26.04 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.533 _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 200(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 'KM-4 Kuma Diffraction' _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4343 _diffrn_reflns_av_R_equivalents 0.1296 _diffrn_reflns_av_sigmaI/netI 0.2005 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.04 _reflns_number_total 4155 _reflns_number_gt 2032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM-4 System, 1994' _computing_cell_refinement 'KM-4 System, 1994' _computing_data_reduction 'KM-4 System, 1994' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.1077P)^2^+21.3853P] 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 4155 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2179 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.2520 _refine_ls_wR_factor_gt 0.2317 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _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 I1 I 0.95786(8) 0.71192(8) 0.11312(6) 0.0357(3) Uani 1 1 d . . . O1 O 1.3324(8) 0.7566(8) 0.6427(6) 0.034(2) Uani 1 1 d . . . C8A C 1.2456(10) 0.7197(13) 0.5722(8) 0.030(3) Uani 1 1 d . . . C5 C 1.7050(11) 0.7937(13) 0.8876(9) 0.037(3) Uani 1 1 d . . . H5A H 1.7779 0.7646 0.9148 0.044 Uiso 1 1 calc R . . N5' N 1.0853(10) 0.7514(9) 0.4398(8) 0.032(3) Uani 1 1 d . . . C4A' C 1.1726(10) 0.7959(12) 0.5085(8) 0.025(2) Uani 1 1 d . . . C3A C 1.4879(10) 0.8741(11) 0.8060(8) 0.027(3) Uani 1 1 d . . . C6' C 1.0648(12) 0.6297(12) 0.4283(9) 0.030(3) Uani 1 1 d . . . N1 N 1.3791(10) 0.9101(10) 0.7504(7) 0.034(3) Uani 1 1 d . . . C4A C 1.5521(11) 0.8562(10) 0.7545(8) 0.026(3) Uani 1 1 d . . . C6 C 1.6451(12) 0.8153(12) 0.9383(9) 0.037(3) Uani 1 1 d . . . H6A H 1.6777 0.8031 1.0001 0.044 Uiso 1 1 calc R . . C13 C 0.9672(12) 0.5815(12) 0.3497(9) 0.033(3) Uani 1 1 d . . . H13A H 0.9767 0.6017 0.2947 0.049 Uiso 1 1 calc R . . H13B H 0.8990 0.6171 0.3495 0.049 Uiso 1 1 calc R . . H13C H 0.9635 0.4950 0.3546 0.049 Uiso 1 1 calc R . . C7 C 1.5326(12) 0.8565(13) 0.8999(9) 0.033(3) Uani 1 1 d . . . H7A H 1.4905 0.8712 0.9350 0.040 Uiso 1 1 calc R . . C2'2 C 1.3657(12) 0.8858(11) 0.6591(9) 0.034(3) Uani 1 1 d . . . C4' C 1.1954(12) 0.9259(12) 0.5233(9) 0.031(3) Uani 1 1 d . . . H4'A H 1.1485 0.9819 0.4834 0.038 Uiso 1 1 calc R . . C4 C 1.6614(11) 0.8136(11) 0.7950(9) 0.033(3) Uani 1 1 d . . . H4A H 1.7046 0.7987 0.7608 0.039 Uiso 1 1 calc R . . C3' C 1.2819(13) 0.9636(12) 0.5928(10) 0.039(3) Uani 1 1 d . . . H3'A H 1.2911 1.0470 0.6009 0.046 Uiso 1 1 calc R . . C12 C 1.0066(13) 0.8358(13) 0.3721(10) 0.041(4) Uani 1 1 d . . . H12A H 1.0488 0.8987 0.3577 0.062 Uiso 1 1 calc R . . H12B H 0.9562 0.8714 0.3967 0.062 Uiso 1 1 calc R . . H12C H 0.9645 0.7915 0.3185 0.062 Uiso 1 1 calc R . . C8' C 1.2264(13) 0.5955(12) 0.5630(10) 0.040(4) Uani 1 1 d . . . H8'A H 1.2739 0.5423 0.6051 0.048 Uiso 1 1 calc R . . C3 C 1.4868(12) 0.8887(12) 0.6588(9) 0.034(3) Uani 1 1 d . . . C1 C 1.2824(14) 0.9107(13) 0.7742(11) 0.045(4) Uani 1 1 d . . . H1A H 1.2169 0.9203 0.7181 0.054 Uiso 1 1 calc R . . C11 C 1.5052(15) 0.8077(14) 0.5889(10) 0.048(4) Uani 1 1 d . . . H11A H 1.4972 0.7244 0.6028 0.072 Uiso 1 1 calc R . . H11B H 1.5792 0.8209 0.5894 0.072 Uiso 1 1 calc R . . H11C H 1.4507 0.8268 0.5304 0.072 Uiso 1 1 calc R . . C7' C 1.1363(11) 0.5515(11) 0.4909(9) 0.032(3) Uani 1 1 d . . . H7'A H 1.1237 0.4683 0.4845 0.039 Uiso 1 1 calc R . . C9 C 1.2679(14) 0.7894(16) 0.8161(10) 0.049(4) Uani 1 1 d . . . H9A H 1.2824 0.7236 0.7828 0.074 Uiso 1 1 calc R . . H9B H 1.1925 0.7832 0.8142 0.074 Uiso 1 1 calc R . . H9C H 1.3196 0.7857 0.8775 0.074 Uiso 1 1 calc R . . C10 C 1.5186(14) 1.0239(12) 0.6461(10) 0.042(4) Uani 1 1 d . . . H10A H 1.5984 1.0306 0.6641 0.063 Uiso 1 1 calc R . . H10B H 1.4938 1.0767 0.6826 0.063 Uiso 1 1 calc R . . H10C H 1.4829 1.0467 0.5840 0.063 Uiso 1 1 calc R . . C8 C 1.2826(17) 1.0180(18) 0.8338(12) 0.067(6) Uani 1 1 d . . . H8A H 1.2742 1.0918 0.8001 0.101 Uiso 1 1 calc R . . H8B H 1.3522 1.0199 0.8848 0.101 Uiso 1 1 calc R . . H8C H 1.2215 1.0102 0.8541 0.101 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 I1 0.0480(5) 0.0285(4) 0.0279(4) 0.0010(5) 0.0112(3) -0.0010(6) O1 0.040(5) 0.018(4) 0.036(5) 0.000(4) 0.005(4) -0.004(4) C8A 0.027(6) 0.027(7) 0.033(7) 0.001(6) 0.007(5) 0.009(7) C5 0.033(7) 0.027(6) 0.039(7) 0.004(7) 0.000(6) -0.008(7) N5' 0.040(7) 0.025(5) 0.030(6) 0.006(4) 0.013(5) 0.021(5) C4A' 0.033(7) 0.015(5) 0.032(6) 0.005(6) 0.017(5) -0.003(6) C3A 0.027(7) 0.016(6) 0.030(7) -0.008(5) 0.001(6) -0.009(5) C6' 0.040(8) 0.027(6) 0.032(7) 0.001(6) 0.026(6) -0.001(6) N1 0.044(7) 0.030(6) 0.032(6) 0.000(5) 0.019(5) 0.002(5) C4A 0.046(8) 0.013(6) 0.026(6) 0.000(5) 0.019(6) -0.005(5) C6 0.043(8) 0.033(8) 0.030(7) -0.003(6) 0.008(6) -0.007(6) C13 0.037(8) 0.033(7) 0.025(7) -0.005(6) 0.008(6) 0.004(6) C7 0.045(8) 0.041(8) 0.031(8) -0.003(6) 0.034(7) -0.012(7) C2'2 0.052(9) 0.015(6) 0.030(7) 0.001(5) 0.011(6) -0.004(6) C4' 0.040(8) 0.019(6) 0.040(8) 0.008(6) 0.020(7) 0.015(6) C4 0.032(7) 0.023(7) 0.039(7) -0.002(5) 0.009(6) -0.008(5) C3' 0.055(10) 0.022(7) 0.039(8) -0.004(6) 0.017(8) 0.002(7) C12 0.053(10) 0.029(7) 0.033(8) 0.016(6) 0.007(7) 0.013(7) C8' 0.056(10) 0.017(7) 0.039(8) 0.010(6) 0.010(7) 0.013(6) C3 0.042(8) 0.027(7) 0.036(7) 0.003(6) 0.016(6) -0.001(6) C1 0.059(11) 0.030(8) 0.051(9) 0.009(7) 0.026(8) 0.001(7) C11 0.079(11) 0.045(10) 0.032(7) -0.006(7) 0.034(8) 0.009(8) C7' 0.037(8) 0.017(6) 0.038(8) -0.006(6) 0.008(6) 0.006(6) C9 0.054(9) 0.045(8) 0.046(8) 0.012(8) 0.015(7) -0.013(9) C10 0.061(10) 0.026(7) 0.040(8) 0.011(6) 0.020(8) -0.003(7) C8 0.088(14) 0.072(13) 0.064(11) 0.011(10) 0.055(11) 0.046(11) _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 C8A 1.320(15) . ? O1 C2'2 1.482(15) . ? C8A C4A' 1.382(17) . ? C8A C8' 1.389(19) . ? C5 C6 1.33(2) . ? C5 C4 1.393(19) . ? N5' C4A' 1.336(17) . ? N5' C6' 1.367(18) . ? N5' C12 1.499(16) . ? C4A' C4' 1.465(18) . ? C3A C4A 1.383(18) . ? C3A N1 1.404(17) . ? C3A C7 1.407(17) . ? C6' C7' 1.379(19) . ? C6' C13 1.504(19) . ? N1 C1 1.431(19) . ? N1 C2'2 1.433(17) . ? C4A C4 1.391(19) . ? C4A C3 1.490(18) . ? C6 C7 1.42(2) . ? C2'2 C3' 1.47(2) . ? C2'2 C3 1.56(2) . ? C4' C3' 1.31(2) . ? C8' C7' 1.38(2) . ? C3 C11 1.517(19) . ? C3 C10 1.579(18) . ? C1 C8 1.52(2) . ? C1 C9 1.54(2) . ? 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 C8A O1 C2'2 123.0(10) . . ? O1 C8A C4A' 124.6(12) . . ? O1 C8A C8' 117.0(12) . . ? C4A' C8A C8' 118.4(12) . . ? C6 C5 C4 121.7(14) . . ? C4A' N5' C6' 122.1(11) . . ? C4A' N5' C12 120.0(11) . . ? C6' N5' C12 117.9(12) . . ? N5' C4A' C8A 120.9(12) . . ? N5' C4A' C4' 123.2(12) . . ? C8A C4A' C4' 115.8(12) . . ? C4A C3A N1 109.8(11) . . ? C4A C3A C7 121.4(12) . . ? N1 C3A C7 128.9(13) . . ? N5' C6' C7' 118.2(12) . . ? N5' C6' C13 121.2(12) . . ? C7' C6' C13 120.6(12) . . ? C3A N1 C1 126.3(12) . . ? C3A N1 C2'2 107.7(11) . . ? C1 N1 C2'2 119.2(12) . . ? C3A C4A C4 119.7(12) . . ? C3A C4A C3 110.3(12) . . ? C4 C4A C3 129.9(12) . . ? C5 C6 C7 121.4(13) . . ? C3A C7 C6 116.8(11) . . ? N1 C2'2 C3' 113.8(12) . . ? N1 C2'2 O1 106.1(10) . . ? C3' C2'2 O1 110.3(11) . . ? N1 C2'2 C3 105.1(11) . . ? C3' C2'2 C3 116.6(12) . . ? O1 C2'2 C3 104.0(11) . . ? C3' C4' C4A' 120.1(12) . . ? C4A C4 C5 118.9(13) . . ? C4' C3' C2'2 125.9(13) . . ? C7' C8' C8A 119.7(12) . . ? C4A C3 C11 115.7(12) . . ? C4A C3 C2'2 99.8(11) . . ? C11 C3 C2'2 115.0(12) . . ? C4A C3 C10 106.6(11) . . ? C11 C3 C10 110.0(12) . . ? C2'2 C3 C10 109.1(11) . . ? N1 C1 C8 111.9(14) . . ? N1 C1 C9 111.8(13) . . ? C8 C1 C9 112.0(14) . . ? C6' C7' C8' 120.7(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.382 _refine_diff_density_min -1.724 _refine_diff_density_rms 0.217