Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Bottle, Steven E.' 'Bott, Raymond C.' 'Micallef, Aaron S.' 'Smith, Craig D.' 'Smith, Graham' _publ_contact_author_name 'Dr Steven E Bottle' _publ_contact_author_address ; CIDC, School of Physical and Chemical Sciences Queensland University of Technology GPO Box 2434 Brisbane Q4001 AUSTRALIA ; _publ_contact_author_email 'S.BOTTLE@QUT.EDU.AU' _publ_section_title ; New isoindoline nitroxide based polyradicals for spin probes and meolecular magnetic materials ; data_BOTL6.CIF #(COMPOUND 3) _database_code_CSD 176995 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1-bis(1',1',3',3'-tetramethylisoindolin-2'-yloxyl-5'-yl)ethane ; _chemical_name_common ? _chemical_melting_point 491 _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34 N2 O2' _chemical_formula_weight 406.55 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 nn2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 12.6113(17) _cell_length_b 16.164(2) _cell_length_c 5.8952(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1201.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic' _exptl_crystal_colour ' yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.124 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.071 _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 0.71069 _diffrn_radiation_type ' MoK\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type ' Rigaku AFC7R' _diffrn_measurement_method ' \w--2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.5 _diffrn_reflns_number 1174 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1174 _reflns_number_gt 904 _reflns_threshold_expression ' I >2\s(I)' _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON for Windows (Spek, 1999)' _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^)+(0.1000P)^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 noref _refine_ls_extinction_method SHELXL-97 (Sheldrick, 1997) _refine_ls_extinction_coef 0.015(8) _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 -1(5) _refine_ls_number_reflns 1174 _refine_ls_number_parameters 142 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1824 _refine_ls_wR_factor_gt 0.1723 _refine_ls_goodness_of_fit_ref 1.425 _refine_ls_restrained_S_all 1.424 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.002 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 O2 O 0.1430(3) 0.2640(2) 0.3674(8) 0.0813(13) Uani 1 1 d . . . N2 N 0.1941(3) 0.20624(19) 0.2681(7) 0.0509(9) Uani 1 1 d . . . C1 C 0.2897(3) 0.2238(2) 0.1269(8) 0.0482(11) Uani 1 1 d . . . C3 C 0.1540(3) 0.1203(2) 0.2624(8) 0.0421(10) Uani 1 1 d . . . C4 C 0.2487(3) -0.0022(2) 0.0630(9) 0.0492(11) Uani 1 1 d . . . C5 C 0.3330(4) -0.0277(3) -0.0720(9) 0.0560(12) Uani 1 1 d . . . C6 C 0.4085(3) 0.0297(3) -0.1533(7) 0.0496(11) Uani 1 1 d . . . C7 C 0.3979(3) 0.1116(3) -0.0898(8) 0.0450(10) Uani 1 1 d . . . C8 C 0.3134(3) 0.1365(2) 0.0451(6) 0.0389(9) Uani 1 1 d . . . C9 C 0.2395(3) 0.0806(2) 0.1197(7) 0.0366(9) Uani 1 1 d . . . C11 C 0.2599(4) 0.2826(3) -0.0645(12) 0.0704(15) Uani 1 1 d . . . C12 C 0.3771(4) 0.2583(4) 0.2741(13) 0.0824(18) Uani 1 1 d . . . C31 C 0.1461(4) 0.0852(3) 0.4996(9) 0.0664(14) Uani 1 1 d . . . C32 C 0.0466(3) 0.1203(3) 0.1453(11) 0.0649(14) Uani 1 1 d . . . C61 C 0.5000 0.0000 -0.2980(12) 0.080(3) Uani 1 2 d S . . C62 C 0.5153(8) 0.0404(6) -0.5016(18) 0.066(3) Uani 0.50 1 d P . . H4 H 0.1964 -0.0413 0.1121 0.061 Uiso 1 1 d . . . H5 H 0.3406 -0.0852 -0.1130 0.073 Uiso 1 1 d . . . H7 H 0.4487 0.1520 -0.1412 0.057 Uiso 1 1 d . . . H111 H 0.2378 0.3341 -0.0061 0.092 Uiso 1 1 d . . . H112 H 0.3217 0.2916 -0.1593 0.092 Uiso 1 1 d . . . H113 H 0.2058 0.2594 -0.1562 0.092 Uiso 1 1 d . . . H121 H 0.3616 0.2499 0.4305 0.104 Uiso 1 1 d . . . H122 H 0.4428 0.2288 0.2415 0.104 Uiso 1 1 d . . . H123 H 0.3883 0.3148 0.2453 0.104 Uiso 1 1 d . . . H311 H 0.1545 0.1281 0.6079 0.085 Uiso 1 1 d . . . H312 H 0.0792 0.0594 0.5188 0.085 Uiso 1 1 d . . . H313 H 0.2009 0.0450 0.5206 0.085 Uiso 1 1 d . . . H321 H -0.0088 0.1201 0.2561 0.083 Uiso 1 1 d . . . H322 H 0.0385 0.1672 0.0503 0.083 Uiso 1 1 d . . . H323 H 0.0394 0.0712 0.0544 0.083 Uiso 1 1 d . . . H621 H 0.5481 0.0915 -0.4722 0.050 Uiso 0.50 1 d P . . H622 H 0.5695 -0.0037 -0.5933 0.050 Uiso 0.50 1 d P . . 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 O2 0.087(2) 0.0573(18) 0.100(3) -0.019(2) 0.033(2) 0.0169(18) N2 0.0529(19) 0.0402(18) 0.060(2) -0.0158(17) 0.0153(19) 0.0048(15) C1 0.0451(19) 0.042(2) 0.058(3) -0.009(2) 0.006(2) -0.0064(16) C3 0.0410(19) 0.042(2) 0.044(2) -0.0024(17) 0.0017(19) 0.0023(16) C4 0.048(2) 0.042(2) 0.058(3) 0.001(2) 0.001(2) 0.0065(17) C5 0.064(3) 0.047(2) 0.057(3) -0.007(2) -0.001(3) 0.019(2) C6 0.046(2) 0.065(3) 0.038(2) 0.002(2) -0.0056(18) 0.025(2) C7 0.0299(17) 0.060(2) 0.045(2) 0.001(2) -0.001(2) 0.0065(16) C8 0.0376(17) 0.0389(19) 0.040(2) -0.0021(17) -0.0053(17) 0.0040(15) C9 0.0325(17) 0.0383(18) 0.039(2) 0.0030(17) -0.0047(18) 0.0038(14) C11 0.092(4) 0.042(2) 0.077(3) 0.000(3) 0.011(3) 0.012(2) C12 0.071(3) 0.080(4) 0.096(4) -0.038(3) 0.007(4) -0.026(3) C31 0.068(3) 0.075(3) 0.056(3) 0.010(3) 0.011(3) 0.004(2) C32 0.040(2) 0.073(3) 0.082(4) -0.011(3) -0.002(3) 0.010(2) C61 0.070(5) 0.130(7) 0.039(4) 0.000 0.000 0.065(5) C62 0.062(6) 0.086(6) 0.051(5) 0.008(5) 0.006(5) 0.029(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 N2 1.277(4) . ? N2 C3 1.479(5) . ? N2 C1 1.492(5) . ? C1 C12 1.510(7) . ? C1 C8 1.521(5) . ? C1 C11 1.522(8) . ? C3 C9 1.510(5) . ? C3 C31 1.512(7) . ? C3 C32 1.519(6) . ? C4 C9 1.383(6) . ? C4 C5 1.392(6) . ? C4 H4 0.96 . ? C5 C6 1.412(6) . ? C5 H5 0.97 . ? C6 C7 1.382(6) . ? C6 C61 1.513(6) . ? C61 C62 1.380(13) . ? C7 C8 1.389(5) . ? C7 H7 0.97 . ? C8 C9 1.371(5) . ? C11 H111 0.94 . ? C11 H112 0.97 . ? C11 H113 0.95 . ? C12 H121 0.95 . ? C12 H122 0.98 . ? C12 H123 0.94 . ? C31 H311 0.95 . ? C31 H312 0.95 . ? C31 H313 0.96 . ? C32 H321 0.96 . ? C32 H322 0.95 . ? C32 H323 0.96 . ? C61 C62 1.380(13) 2_655 ? C61 C62 1.380(13) . ? C61 C6 1.513(6) 2_655 ? C62 C62 1.36(2) 2_655 ? C62 H621 0.94 . ? C62 H622 1.13 . ? 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 O2 N2 C3 121.7(3) . . ? O2 N2 C1 121.6(3) . . ? C3 N2 C1 116.3(3) . . ? N2 C1 C12 109.9(4) . . ? N2 C1 C8 99.2(3) . . ? C12 C1 C8 112.4(4) . . ? N2 C1 C11 109.5(4) . . ? C12 C1 C11 112.0(4) . . ? C8 C1 C11 113.2(4) . . ? N2 C3 C9 99.6(3) . . ? N2 C3 C31 110.7(4) . . ? C9 C3 C31 113.7(3) . . ? N2 C3 C32 108.4(3) . . ? C9 C3 C32 112.5(4) . . ? C31 C3 C32 111.2(4) . . ? C9 C4 C5 119.2(4) . . ? C9 C4 H4 121 . . ? C5 C4 H4 121 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5 120 . . ? C6 C5 H5 119 . . ? C7 C6 C5 118.1(4) . . ? C7 C6 C61 122.0(4) . . ? C5 C6 C61 119.8(4) . . ? C6 C7 C8 120.5(4) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 C1 112.1(3) . . ? C7 C8 C1 127.0(3) . . ? C8 C9 C4 120.2(3) . . ? C8 C9 C3 112.6(3) . . ? C4 C9 C3 127.2(3) . . ? C1 C11 H111 111 . . ? C1 C11 H112 109 . . ? H111 C11 H112 108 . . ? C1 C11 H113 110 . . ? H111 C11 H113 110 . . ? H112 C11 H113 108 . . ? C1 C12 H121 111 . . ? C1 C12 H122 109 . . ? H121 C12 H122 107 . . ? C1 C12 H123 111 . . ? H121 C12 H123 110 . . ? H122 C12 H123 108 . . ? C3 C31 H311 110 . . ? C3 C31 H312 110 . . ? H311 C31 H312 110 . . ? C3 C31 H313 109 . . ? H311 C31 H313 109 . . ? H312 C31 H313 109 . . ? C3 C32 H321 110 . . ? C3 C32 H322 111 . . ? H321 C32 H322 109 . . ? C3 C32 H323 110 . . ? H321 C32 H323 108 . . ? H322 C32 H323 109 . . ? C62 C61 C6 116.5(4) 2_655 2_655 ? C62 C61 C6 122.3(5) . 2_655 ? C62 C61 C6 122.3(5) 2_655 . ? C62 C61 C6 116.5(4) . . ? C6 C61 C6 111.4(5) 2_655 . ? C61 C62 H621 108.4(10) . . ? C61 C62 H622 101.7(7) . . ? H621 C62 H622 112.1(10) . . ? 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 O2 N2 C1 C12 64.7(6) . . . . ? C3 N2 C1 C12 -123.0(4) . . . . ? O2 N2 C1 C8 -177.4(4) . . . . ? C3 N2 C1 C8 -5.1(5) . . . . ? O2 N2 C1 C11 -58.8(6) . . . . ? C3 N2 C1 C11 113.6(4) . . . . ? O2 N2 C3 C9 177.5(4) . . . . ? C1 N2 C3 C9 5.2(5) . . . . ? O2 N2 C3 C31 -62.5(6) . . . . ? C1 N2 C3 C31 125.2(4) . . . . ? O2 N2 C3 C32 59.7(6) . . . . ? C1 N2 C3 C32 -112.6(4) . . . . ? C9 C4 C5 C6 -0.6(7) . . . . ? C4 C5 C6 C7 1.7(7) . . . . ? C4 C5 C6 C61 179.4(5) . . . . ? C5 C6 C7 C8 -1.7(6) . . . . ? C61 C6 C7 C8 -179.3(4) . . . . ? C6 C7 C8 C9 0.6(6) . . . . ? C6 C7 C8 C1 -179.2(4) . . . . ? N2 C1 C8 C9 2.8(4) . . . . ? C12 C1 C8 C9 118.8(5) . . . . ? C11 C1 C8 C9 -113.1(4) . . . . ? N2 C1 C8 C7 -177.5(4) . . . . ? C12 C1 C8 C7 -61.5(6) . . . . ? C11 C1 C8 C7 66.7(5) . . . . ? C7 C8 C9 C4 0.6(6) . . . . ? C1 C8 C9 C4 -179.6(4) . . . . ? C7 C8 C9 C3 -179.6(3) . . . . ? C1 C8 C9 C3 0.2(5) . . . . ? C5 C4 C9 C8 -0.6(6) . . . . ? C5 C4 C9 C3 179.7(4) . . . . ? N2 C3 C9 C8 -3.1(4) . . . . ? C31 C3 C9 C8 -120.9(4) . . . . ? C32 C3 C9 C8 111.5(4) . . . . ? N2 C3 C9 C4 176.7(4) . . . . ? C31 C3 C9 C4 58.9(6) . . . . ? C32 C3 C9 C4 -68.7(5) . . . . ? C7 C6 C61 C62 -123.1(6) . . . 2_655 ? C5 C6 C61 C62 59.3(8) . . . 2_655 ? C7 C6 C61 C62 -54.5(8) . . . . ? C5 C6 C61 C62 127.9(7) . . . . ? C7 C6 C61 C6 92.3(4) . . . 2_655 ? C5 C6 C61 C6 -85.3(4) . . . 2_655 ? C6 C61 C62 C62 103.8(8) 2_655 . . 2_655 ? C6 C61 C62 C62 -113.4(7) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.260 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.048 ############################################################# data_366gs38 #BOTTLE7.CIF COMPOUND (15). _database_code_CSD 176996 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2,3,5,6,7-hexahydro-1,1,3,3,5,5,7,7-octamethylbenzo[1,2-c:4,5-c']- dipyrrol-2,6-diyloxyl ; _chemical_name_common ? _chemical_melting_point 503 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 N2 O2' _chemical_formula_weight 302.41 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 '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 6.332(2) _cell_length_b 13.4029(17) _cell_length_c 11.2087(17) _cell_angle_alpha 90.00 _cell_angle_beta 92.007(19) _cell_angle_gamma 90.00 _cell_volume 950.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.056 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.069 _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 0.71069 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method '\w--2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 1833 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1676 _reflns_number_gt 509 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON for Windows (Spek, 1999)' _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^)+(0.1000P)^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 noref _refine_ls_extinction_method 'SHELXL-97 (Sheldrick, 1997)' _refine_ls_extinction_coef 0.017(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1676 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2415 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2581 _refine_ls_wR_factor_gt 0.2023 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 O2 O 0.2878(7) 0.7671(3) 0.2474(3) 0.1293(19) Uani 1 1 d . . . N2 N 0.2076(8) 0.8309(3) 0.3160(3) 0.0992(17) Uani 1 1 d . . . C1 C 0.2201(10) 0.9392(3) 0.2930(4) 0.093(2) Uani 1 1 d . . . C3 C 0.1060(11) 0.8012(3) 0.4282(4) 0.105(2) Uani 1 1 d . . . C4 C 0.0423(8) 0.9026(3) 0.4727(4) 0.0808(17) Uani 1 1 d . . . C5 C 0.1069(9) 0.9780(3) 0.3989(3) 0.0832(18) Uani 1 1 d . . . C6 C 0.0649(9) 1.0773(3) 0.4245(4) 0.0862(19) Uani 1 1 d . . . C11 C 0.0956(13) 0.9630(4) 0.1727(4) 0.136(3) Uani 1 1 d . . . C12 C 0.4529(12) 0.9715(4) 0.2940(6) 0.135(3) Uani 1 1 d . . . C31 C -0.0976(14) 0.7345(4) 0.3936(6) 0.160(4) Uani 1 1 d . . . C32 C 0.2758(16) 0.7532(5) 0.5124(6) 0.190(5) Uani 1 1 d . . . H6 H 0.0892 1.1362 0.3580 0.058 Uiso 1 1 d . . . H111 H -0.0453 0.9891 0.1882 0.169 Uiso 1 1 d . . . H112 H 0.1653 1.0101 0.1261 0.169 Uiso 1 1 d . . . H113 H 0.0716 0.9031 0.1256 0.169 Uiso 1 1 d . . . H121 H 0.5076 0.9776 0.3749 0.171 Uiso 1 1 d . . . H122 H 0.5373 0.9233 0.2544 0.171 Uiso 1 1 d . . . H123 H 0.4684 1.0343 0.2555 0.171 Uiso 1 1 d . . . H311 H -0.1641 0.7124 0.4649 0.200 Uiso 1 1 d . . . H312 H -0.1950 0.7706 0.3460 0.200 Uiso 1 1 d . . . H313 H -0.0555 0.6754 0.3511 0.200 Uiso 1 1 d . . . H321 H 0.2363 0.7617 0.5942 0.237 Uiso 1 1 d . . . H322 H 0.2822 0.6824 0.4977 0.237 Uiso 1 1 d . . . H323 H 0.4089 0.7815 0.5022 0.237 Uiso 1 1 d . . . 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 O2 0.201(5) 0.078(2) 0.113(3) -0.027(2) 0.077(3) 0.020(2) N2 0.165(5) 0.057(2) 0.079(3) -0.014(2) 0.057(3) 0.014(3) C1 0.152(6) 0.052(3) 0.080(4) -0.008(2) 0.061(4) 0.005(3) C3 0.178(7) 0.056(3) 0.083(3) -0.001(3) 0.064(4) 0.018(4) C4 0.127(5) 0.046(3) 0.073(3) 0.001(2) 0.041(3) 0.006(3) C5 0.134(5) 0.059(3) 0.060(3) 0.001(2) 0.037(3) 0.005(3) C6 0.146(5) 0.046(3) 0.070(3) 0.007(2) 0.050(3) 0.008(3) C11 0.264(9) 0.095(4) 0.053(3) 0.005(3) 0.048(4) 0.026(5) C12 0.165(7) 0.099(5) 0.149(6) -0.025(4) 0.101(5) -0.015(4) C31 0.242(9) 0.061(4) 0.184(6) -0.048(4) 0.124(6) -0.042(5) C32 0.331(12) 0.127(6) 0.117(5) 0.057(4) 0.089(6) 0.152(7) _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 N2 1.267(4) . ? N2 C1 1.477(6) . ? N2 C3 1.487(5) . ? C1 C5 1.501(5) . ? C1 C12 1.536(9) . ? C1 C11 1.570(9) . ? C3 C4 1.507(6) . ? C3 C32 1.546(9) . ? C3 C31 1.606(9) . ? C4 C5 1.377(5) . ? C4 C6 1.384(5) 3_576 ? C5 C6 1.389(5) . ? C6 C4 1.384(5) 3_576 ? C6 H6 1.10 . ? C11 H111 0.98 . ? C11 H112 0.94 . ? C11 H113 0.97 . ? C12 H121 0.96 . ? C12 H122 0.96 . ? C12 H123 0.95 . ? C31 H311 0.96 . ? C31 H312 0.94 . ? C31 H313 0.97 . ? C32 H321 0.97 . ? C32 H322 0.97 . ? C32 H323 0.94 . ? 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 O2 N2 C1 122.1(3) . . ? O2 N2 C3 121.8(4) . . ? C1 N2 C3 116.0(3) . . ? N2 C1 C5 99.9(3) . . ? N2 C1 C12 109.4(5) . . ? C5 C1 C12 112.4(5) . . ? N2 C1 C11 108.7(4) . . ? C5 C1 C11 111.7(5) . . ? C12 C1 C11 113.7(5) . . ? N2 C3 C4 99.7(3) . . ? N2 C3 C32 108.4(5) . . ? C4 C3 C32 111.2(5) . . ? N2 C3 C31 108.2(5) . . ? C4 C3 C31 111.1(5) . . ? C32 C3 C31 116.8(5) . . ? C5 C4 C6 121.4(3) . 3_576 ? C5 C4 C3 112.0(4) . . ? C6 C4 C3 126.6(4) 3_576 . ? C4 C5 C6 121.1(3) . . ? C4 C5 C1 112.4(4) . . ? C6 C5 C1 126.5(4) . . ? C4 C6 C5 117.5(3) 3_576 . ? C4 C6 H6 120.5(4) 3_576 . ? C5 C6 H6 121 . . ? C1 C11 H111 111 . . ? C1 C11 H112 113 . . ? H111 C11 H112 108 . . ? C1 C11 H113 111 . . ? H111 C11 H113 105 . . ? H112 C11 H113 109 . . ? C1 C12 H121 110 . . ? C1 C12 H122 111 . . ? H121 C12 H122 108 . . ? C1 C12 H123 111 . . ? H121 C12 H123 108 . . ? H122 C12 H123 109 . . ? C3 C31 H311 110 . . ? C3 C31 H312 111 . . ? H311 C31 H312 110 . . ? C3 C31 H313 110 . . ? H311 C31 H313 107 . . ? H312 C31 H313 109 . . ? C3 C32 H321 110 . . ? C3 C32 H322 110 . . ? H321 C32 H322 107 . . ? C3 C32 H323 112 . . ? H321 C32 H323 109 . . ? H322 C32 H323 110 . . ? 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 O2 N2 C1 C5 -179.1(5) . . . . ? C3 N2 C1 C5 -2.5(6) . . . . ? O2 N2 C1 C12 -61.0(7) . . . . ? C3 N2 C1 C12 115.6(5) . . . . ? O2 N2 C1 C11 63.7(7) . . . . ? C3 N2 C1 C11 -119.6(5) . . . . ? O2 N2 C3 C4 179.7(6) . . . . ? C1 N2 C3 C4 3.0(7) . . . . ? O2 N2 C3 C32 63.3(7) . . . . ? C1 N2 C3 C32 -113.3(5) . . . . ? O2 N2 C3 C31 -64.2(7) . . . . ? C1 N2 C3 C31 119.2(5) . . . . ? N2 C3 C4 C5 -2.3(7) . . . . ? C32 C3 C4 C5 111.9(5) . . . . ? C31 C3 C4 C5 -116.2(5) . . . . ? N2 C3 C4 C6 178.8(5) . . . 3_576 ? C32 C3 C4 C6 -67.1(8) . . . 3_576 ? C31 C3 C4 C6 64.9(8) . . . 3_576 ? C6 C4 C5 C6 -0.6(9) 3_576 . . . ? C3 C4 C5 C6 -179.6(6) . . . . ? C6 C4 C5 C1 180.0(5) 3_576 . . . ? C3 C4 C5 C1 1.0(7) . . . . ? N2 C1 C5 C4 0.9(6) . . . . ? C12 C1 C5 C4 -115.1(6) . . . . ? C11 C1 C5 C4 115.7(5) . . . . ? N2 C1 C5 C6 -178.5(6) . . . . ? C12 C1 C5 C6 65.6(7) . . . . ? C11 C1 C5 C6 -63.6(7) . . . . ? C4 C5 C6 C4 0.6(9) . . . 3_576 ? C1 C5 C6 C4 179.9(6) . . . 3_576 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.242 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.044 # END OF FILES