Supplementary Material (ESI) for Green Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Ferdinando Pizzo' _publ_contact_author_address ; Dipartimento di Chimica Universita di Perugia Perugia 06123 ITALY ; _publ_contact_author_email PIZZO@UNIPG.IT _publ_section_title ; Catalyst- and Solvent-Free Conditions as an environmetally benign approach to 4-Aryl-3-cyano-hexahydro- 4H-1,2-benzoxazine-2-oxides ; _publ_section_references ; R.H. Blessing, acta cryst. a51, 33-38, (1995). Sir97: c. Giacovazzo, J. Appl. Cryst. 32, 115-119 (1999). SHELXL-97: G.M. Sheldrick ,University of Goettingen, Germany, 1997. Wingx: L.J. Farrugia, J. Appl. Cryst 32, 837-838 (1999). ; _publ_section_acknowledgements ; This work was supported by grants from the Ministero dell'Istruzione, della Universita e della Ricerca (MIUR, Rome, Italy) and the Universita degli Studi di Perugia (within the funding projects: COFIN, COFINLAB and FIRB 2001). ; loop_ _publ_author_name 'Ferdinando Pizzo' 'Gianfranco Bellachioma' 'Luca Castrica' 'Francesco Fringuelli' 'L. Vaccaro' data_11a _database_code_depnum_ccdc_archive 'CCDC 623145' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N2 O3 Si' _chemical_formula_sum 'C18 H24 N2 O3 Si' _chemical_formula_weight 344.48 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.893(2) _cell_length_b 10.366(2) _cell_length_c 10.379(2) _cell_angle_alpha 102.062(17) _cell_angle_beta 105.681(17) _cell_angle_gamma 103.638(17) _cell_volume 952.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details r.h.blessing,actacryst.(1995),a5 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 14614 _diffrn_reflns_av_R_equivalents 0.0960 _diffrn_reflns_av_sigmaI/netI 0.2823 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 29.47 _reflns_number_total 5292 _reflns_number_gt 3156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XCALIBUR (Kuma4CCD) diffractometer' _computing_cell_refinement 'CRYSALIS (CCD 171) software' _computing_data_reduction 'CRYSALIS (CCD 171) software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0207P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5292 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2485 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0550 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _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 C1' C 0.0868(3) 0.3802(3) 0.8611(3) 0.0448(7) Uani 1 1 d . . . C2' C 0.0018(3) 0.3284(3) 0.7220(4) 0.0626(9) Uani 1 1 d . . . H2' H -0.0283 0.2334 0.6788 0.067(4) Uiso 1 1 calc R . . C3 C 0.0454(3) 0.1423(3) 0.8901(2) 0.044 Uani 1 1 d . . . C3' C -0.0400(3) 0.4160(5) 0.6447(4) 0.0838(10) Uani 1 1 d . . . H3' H -0.0981 0.3797 0.5507 0.067(4) Uiso 1 1 calc R . . C4' C 0.0055(3) 0.5568(4) 0.7086(4) 0.0822(11) Uani 1 1 d . . . H4' H -0.0219 0.6162 0.6580 0.067(4) Uiso 1 1 calc R . . C4 C 0.1313(3) 0.2925(2) 0.9541(2) 0.0422(7) Uani 1 1 d . . . H4 H 0.1029 0.3226 1.0361 0.028(4) Uiso 1 1 calc R . . C5' C 0.0909(3) 0.6086(3) 0.8462(4) 0.072 Uani 1 1 d . . . H5' H 0.1230 0.7038 0.8888 0.067(4) Uiso 1 1 calc R . . C4A C 0.2959(3) 0.3112(2) 1.0119(2) 0.0411(7) Uani 1 1 d . . . H4A H 0.3491 0.4058 1.0171 0.028(4) Uiso 1 1 calc R . . C6' C 0.1297(3) 0.5226(3) 0.9222(3) 0.057 Uani 1 1 d . . . H6' H 0.1859 0.5599 1.0166 0.067(4) Uiso 1 1 calc R . . C5 C 0.3401(3) 0.2979(3) 1.1600(2) 0.059 Uani 1 1 d . . . H5B H 0.3210 0.3707 1.2212 0.077(3) Uiso 1 1 calc R . . H5A H 0.2796 0.2094 1.1601 0.077(3) Uiso 1 1 calc R . . C6 C 0.5024(3) 0.3078(3) 1.2167(3) 0.076 Uani 1 1 d . . . H6A H 0.5636 0.3992 1.2247 0.077(3) Uiso 1 1 calc R . . H6B H 0.5247 0.2950 1.3092 0.077(3) Uiso 1 1 calc R . . C7 C 0.5364(3) 0.1983(3) 1.1202(3) 0.0685(9) Uani 1 1 d . . . H7B H 0.4795 0.1068 1.1167 0.077(3) Uiso 1 1 calc R . . H7A H 0.6404 0.2069 1.1561 0.077(3) Uiso 1 1 calc R . . C8 C 0.4983(3) 0.2155(3) 0.9729(3) 0.0568(8) Uani 1 1 d . . . H8B H 0.5635 0.3029 0.9757 0.077(3) Uiso 1 1 calc R . . H8A H 0.5154 0.1415 0.9113 0.077(3) Uiso 1 1 calc R . . C8A C 0.3396(3) 0.2128(3) 0.9139(3) 0.0444(7) Uani 1 1 d . . . C9 C -0.1126(3) 0.0950(3) 0.8524(3) 0.058 Uani 1 1 d . . . C16 C 0.2199(4) 0.2308(4) 0.5080(3) 0.1261(14) Uani 1 1 d . . . H16A H 0.2397 0.3296 0.5374 0.178(5) Uiso 1 1 calc R . . H16B H 0.1191 0.1854 0.4967 0.178(5) Uiso 1 1 calc R . . H16C H 0.2363 0.2043 0.4206 0.178(5) Uiso 1 1 calc R . . C14 C 0.3136(3) -0.0093(3) 0.5960(3) 0.1114(13) Uani 1 1 d . . . H14C H 0.3802 -0.0294 0.6697 0.178(5) Uiso 1 1 calc R . . H14B H 0.3318 -0.0397 0.5101 0.178(5) Uiso 1 1 calc R . . H14A H 0.2137 -0.0570 0.5853 0.178(5) Uiso 1 1 calc R . . C15 C 0.5375(3) 0.2718(3) 0.6644(3) 0.1015(11) Uani 1 1 d . . . H15B H 0.6026 0.2447 0.7330 0.178(5) Uiso 1 1 calc R . . H15C H 0.5555 0.3701 0.6955 0.178(5) Uiso 1 1 calc R . . H15A H 0.5548 0.2479 0.5771 0.178(5) Uiso 1 1 calc R . . N2 N 0.1030(2) 0.0407(2) 0.86870(19) 0.052 Uani 1 1 d . . . N10 N -0.2376(3) 0.0650(2) 0.8238(2) 0.0831(8) Uani 1 1 d . . . O1 O 0.25598(18) 0.06954(17) 0.90058(15) 0.0520(5) Uani 1 1 d . . . O11 O 0.03570(18) -0.08641(16) 0.82280(18) 0.070 Uani 1 1 d . . . O12 O 0.30424(16) 0.23577(16) 0.78445(16) 0.0525(5) Uani 1 1 d . . . Si13 Si 0.34287(10) 0.17995(9) 0.64018(8) 0.0648(3) Uani 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 C1' 0.0481(19) 0.0378(19) 0.0581(19) 0.0164(17) 0.0271(17) 0.0179(16) C2' 0.074(2) 0.058(2) 0.068(2) 0.027(2) 0.029(2) 0.028(2) C3 0.047 0.041 0.049 0.018 0.017 0.019 C3' 0.091(3) 0.105(3) 0.077(2) 0.048(3) 0.031(2) 0.047(3) C4' 0.101(3) 0.086(3) 0.125(3) 0.081(3) 0.067(3) 0.070(2) C4 0.054(2) 0.0335(17) 0.0468(17) 0.0132(15) 0.0272(16) 0.0152(16) C5' 0.075 0.061 0.112 0.037 0.061 0.033 C4A 0.0488(19) 0.0317(17) 0.0424(17) 0.0123(13) 0.0162(15) 0.0096(15) C6' 0.065 0.050 0.078 0.029 0.041 0.029 C5 0.066 0.060 0.046 0.014 0.017 0.019 C6 0.083 0.082 0.050 0.025 0.008 0.017 C7 0.053(2) 0.082(2) 0.074(2) 0.0366(19) 0.0114(17) 0.0279(18) C8 0.053(2) 0.060(2) 0.063(2) 0.0268(17) 0.0160(17) 0.0232(17) C8A 0.0428(19) 0.045(2) 0.0457(18) 0.0147(16) 0.0121(15) 0.0170(16) C9 0.063 0.047 0.064 0.022 0.019 0.015 C16 0.154(3) 0.216(4) 0.062(2) 0.065(3) 0.044(2) 0.126(3) C14 0.161(3) 0.081(3) 0.079(2) 0.001(2) 0.044(2) 0.030(2) C15 0.100(3) 0.127(3) 0.100(3) 0.033(2) 0.063(2) 0.040(2) N2 0.051 0.048 0.050 0.019 0.008 0.011 N10 0.0606(17) 0.0856(19) 0.1033(19) 0.0399(15) 0.0243(16) 0.0158(16) O1 0.0521(12) 0.0404(11) 0.0650(12) 0.0154(9) 0.0173(10) 0.0199(10) O11 0.074 0.029 0.090 0.015 0.010 0.008 O12 0.0631(13) 0.0683(12) 0.0421(12) 0.0237(11) 0.0236(10) 0.0358(11) Si13 0.0786(7) 0.0773(7) 0.0505(5) 0.0186(5) 0.0283(5) 0.0380(6) _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' 1.374(3) . ? C1' C6' 1.389(3) . ? C1' C4 1.509(3) . ? C2' C3' 1.393(4) . ? C3 N2 1.318(2) . ? C3 C9 1.437(3) . ? C3 C4 1.492(3) . ? C3' C4' 1.377(4) . ? C4' C5' 1.362(4) . ? C4 C4A 1.524(3) . ? C5' C6' 1.362(3) . ? C4A C8A 1.509(3) . ? C4A C5 1.525(3) . ? C5 C6 1.523(3) . ? C6 C7 1.514(3) . ? C7 C8 1.531(3) . ? C8 C8A 1.514(3) . ? C8A O12 1.380(2) . ? C8A O1 1.477(3) . ? C9 N10 1.138(3) . ? C16 Si13 1.828(3) . ? C14 Si13 1.851(3) . ? C15 Si13 1.857(3) . ? N2 O11 1.248(2) . ? N2 O1 1.401(2) . ? O12 Si13 1.6657(15) . ? 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' C6' 117.9(3) . . ? C2' C1' C4 124.5(2) . . ? C6' C1' C4 117.5(3) . . ? C1' C2' C3' 121.0(3) . . ? N2 C3 C9 113.4(2) . . ? N2 C3 C4 125.2(2) . . ? C9 C3 C4 121.3(2) . . ? C4' C3' C2' 119.5(3) . . ? C5' C4' C3' 119.6(3) . . ? C3 C4 C1' 112.7(2) . . ? C3 C4 C4A 110.4(2) . . ? C1' C4 C4A 116.5(2) . . ? C6' C5' C4' 120.8(3) . . ? C8A C4A C4 110.8(2) . . ? C8A C4A C5 112.3(2) . . ? C4 C4A C5 111.4(2) . . ? C5' C6' C1' 121.1(3) . . ? C6 C5 C4A 112.3(2) . . ? C7 C6 C5 110.2(2) . . ? C6 C7 C8 110.2(2) . . ? C8A C8 C7 112.6(2) . . ? O12 C8A O1 109.4(2) . . ? O12 C8A C4A 109.3(2) . . ? O1 C8A C4A 108.12(19) . . ? O12 C8A C8 113.9(2) . . ? O1 C8A C8 102.5(2) . . ? C4A C8A C8 113.2(2) . . ? N10 C9 C3 176.2(3) . . ? O11 N2 C3 127.1(2) . . ? O11 N2 O1 112.4(2) . . ? C3 N2 O1 120.4(2) . . ? N2 O1 C8A 116.17(18) . . ? C8A O12 Si13 133.43(15) . . ? O12 Si13 C16 103.64(11) . . ? O12 Si13 C14 111.08(11) . . ? C16 Si13 C14 113.52(15) . . ? O12 Si13 C15 110.18(11) . . ? C16 Si13 C15 109.07(15) . . ? C14 Si13 C15 109.22(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.47 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.151 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.029 # Attachment 'compound_6a.cif' data_19a _database_code_depnum_ccdc_archive 'CCDC 623146' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 N2 O2' _chemical_formula_sum 'C15 H16 N2 O2' _chemical_formula_weight 256.30 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/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 14.092(3) _cell_length_b 8.462(3) _cell_length_c 11.276(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.819(16) _cell_angle_gamma 90.00 _cell_volume 1335.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 19274 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.1933 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 29.57 _reflns_number_total 3733 _reflns_number_gt 2040 _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^)+(0.0200P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3733 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1538 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _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 C1' C 0.85093(16) -0.0844(3) 0.8085(2) 0.0318(6) Uani 1 1 d . . . C2' C 0.9193(2) -0.0320(3) 0.7406(3) 0.049 Uani 1 1 d . . . C3 C 0.68002(18) -0.1732(3) 0.7715(2) 0.035 Uani 1 1 d . . . C4 C 0.74753(17) -0.0360(3) 0.7770(2) 0.0310(7) Uani 1 1 d . . . C3' C 1.0156(2) -0.0618(4) 0.7754(3) 0.065 Uani 1 1 d . . . C4A C 0.71581(16) 0.0851(3) 0.8640(2) 0.0296(6) Uani 1 1 d . . . C4' C 1.0429(3) -0.1460(4) 0.8762(3) 0.0627(10) Uani 1 1 d . . . C5 C 0.7610(2) 0.2466(3) 0.8547(3) 0.0423(8) Uani 1 1 d . . . C5' C 0.9762(3) -0.2035(4) 0.9432(3) 0.0587(9) Uani 1 1 d . . . C6 C 0.7238(2) 0.3623(4) 0.9417(3) 0.0506(9) Uani 1 1 d . . . C6' C 0.8794(2) -0.1715(3) 0.9102(3) 0.0466(8) Uani 1 1 d . . . C7 C 0.6151(2) 0.3736(3) 0.9227(3) 0.0500(8) Uani 1 1 d . . . C8 C 0.5701(2) 0.2118(3) 0.9314(3) 0.0427(8) Uani 1 1 d . . . C8A C 0.60802(17) 0.0986(3) 0.8449(2) 0.0346(7) Uani 1 1 d . . . C9 C 0.70533(18) -0.3160(3) 0.7102(2) 0.045 Uani 1 1 d . . . N2 N 0.59894(15) -0.1854(2) 0.81304(17) 0.0455(6) Uani 1 1 d . . . N10 N 0.72799(16) -0.4225(3) 0.65859(18) 0.0676(7) Uani 1 1 d . . . O11 O 0.58126(14) 0.1356(2) 0.72461(16) 0.0448(6) Uani 1 1 d . . . O1 O 0.56522(11) -0.0546(2) 0.86858(14) 0.0459(5) Uani 1 1 d . . . H11 H 0.5274(17) 0.169(3) 0.719(2) 0.060(10) Uiso 1 1 d . . . H2' H 0.8978(15) 0.037(2) 0.6647(19) 0.073(7) Uiso 1 1 d . . . H3' H 1.0572(17) -0.021(2) 0.728(2) 0.081(10) Uiso 1 1 d . . . H4 H 0.7407(11) 0.0093(18) 0.7013(15) 0.010(6) Uiso 1 1 d . . . H4A H 0.7312(11) 0.0382(18) 0.9453(15) 0.008(5) Uiso 1 1 d . . . H4' H 1.111(2) -0.169(3) 0.900(2) 0.083(10) Uiso 1 1 d . . . H5B H 0.8292(15) 0.230(2) 0.8717(17) 0.035(7) Uiso 1 1 d . . . H5A H 0.7467(14) 0.284(2) 0.7724(18) 0.039(7) Uiso 1 1 d . . . H5' H 0.9870(17) -0.268(3) 1.016(2) 0.084(11) Uiso 1 1 d . . . H6A H 0.7442(16) 0.324(2) 1.026(2) 0.059(8) Uiso 1 1 d . . . H6B H 0.7503(15) 0.466(2) 0.9351(19) 0.045(8) Uiso 1 1 d . . . H6' H 0.8313(15) -0.209(2) 0.9573(18) 0.041(8) Uiso 1 1 d . . . H7B H 0.5915(15) 0.447(2) 0.9827(19) 0.049(8) Uiso 1 1 d . . . H7A H 0.5917(14) 0.420(2) 0.8404(19) 0.052(8) Uiso 1 1 d . . . H8A H 0.5863(14) 0.166(2) 1.0104(18) 0.048(8) Uiso 1 1 d . . . H8B H 0.5002(16) 0.213(2) 0.9152(18) 0.046(8) 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 C1' 0.0234(15) 0.0332(15) 0.0389(16) -0.0015(13) 0.0043(14) -0.0019(12) C2' 0.032 0.052 0.062 0.005 0.008 0.003 C3 0.035 0.035 0.034 -0.001 0.002 -0.001 C4 0.0300(17) 0.0314(15) 0.0315(17) 0.0060(14) 0.0027(13) -0.0010(13) C3' 0.045 0.069 0.083 -0.003 0.021 -0.003 C4A 0.0254(16) 0.0361(17) 0.0271(16) 0.0076(13) 0.0022(13) 0.0020(13) C4' 0.036(2) 0.061(2) 0.089(3) -0.0165(19) -0.002(2) 0.0088(19) C5 0.030(2) 0.0436(18) 0.053(2) -0.0005(16) 0.0033(18) 0.0001(15) C5' 0.052(3) 0.057(2) 0.063(3) 0.0010(19) -0.009(2) 0.0137(19) C6 0.054(2) 0.040(2) 0.057(2) -0.0088(18) 0.0005(18) -0.0002(17) C6' 0.037(2) 0.0510(19) 0.052(2) 0.0052(16) 0.0061(18) 0.0015(16) C7 0.050(2) 0.051(2) 0.049(2) -0.0053(18) 0.0060(18) 0.0110(17) C8 0.036(2) 0.055(2) 0.038(2) -0.0005(16) 0.0089(18) 0.0056(16) C8A 0.0324(17) 0.0394(17) 0.0326(17) 0.0025(14) 0.0059(14) 0.0014(14) C9 0.040 0.050 0.045 -0.001 0.003 -0.010 N2 0.0387(15) 0.0453(15) 0.0529(15) -0.0033(12) 0.0073(12) -0.0064(12) N10 0.0764(18) 0.0614(16) 0.0652(17) -0.0138(14) 0.0097(13) -0.0022(14) O11 0.0335(13) 0.0634(13) 0.0364(12) 0.0007(9) 0.0002(10) 0.0112(11) O1 0.0342(11) 0.0479(12) 0.0585(12) -0.0039(10) 0.0175(9) -0.0081(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' C2' 1.373(3) . ? C1' C6' 1.382(3) . ? C1' C4 1.515(3) . ? C2' C3' 1.390(3) . ? C3 N2 1.290(3) . ? C3 C9 1.457(3) . ? C3 C4 1.497(3) . ? C4 C4A 1.522(3) . ? C3' C4' 1.358(4) . ? C4A C8A 1.513(3) . ? C4A C5 1.516(3) . ? C4' C5' 1.364(4) . ? C5 C6 1.523(4) . ? C5' C6' 1.397(4) . ? C6 C7 1.523(4) . ? C7 C8 1.518(4) . ? C8 C8A 1.509(3) . ? C8A O11 1.400(2) . ? C8A O1 1.468(2) . ? C9 N10 1.139(3) . ? N2 O1 1.383(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 C2' C1' C6' 118.8(3) . . ? C2' C1' C4 120.1(2) . . ? C6' C1' C4 121.0(2) . . ? C1' C2' C3' 120.6(3) . . ? N2 C3 C9 112.5(2) . . ? N2 C3 C4 129.3(2) . . ? C9 C3 C4 118.2(2) . . ? C3 C4 C1' 112.9(2) . . ? C3 C4 C4A 108.4(2) . . ? C1' C4 C4A 112.3(2) . . ? C4' C3' C2' 120.1(4) . . ? C8A C4A C5 110.2(2) . . ? C8A C4A C4 109.0(2) . . ? C5 C4A C4 113.9(2) . . ? C3' C4' C5' 120.4(3) . . ? C4A C5 C6 110.8(3) . . ? C4' C5' C6' 119.9(3) . . ? C5 C6 C7 111.5(3) . . ? C1' C6' C5' 120.2(3) . . ? C8 C7 C6 110.8(3) . . ? C8A C8 C7 110.4(3) . . ? O11 C8A O1 107.71(18) . . ? O11 C8A C8 114.2(2) . . ? O1 C8A C8 105.0(2) . . ? O11 C8A C4A 107.7(2) . . ? O1 C8A C4A 109.55(19) . . ? C8 C8A C4A 112.5(2) . . ? N10 C9 C3 176.2(3) . . ? C3 N2 O1 117.9(2) . . ? N2 O1 C8A 117.00(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.114 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.033