Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_date 2005-03-08 # SUBMISSION DETAILS _publ_contact_author_name 'Dr. J. Siegel' _publ_contact_author_address ; Institute of Organic Chemistry University of Zurich Winterthurerstrasse 190 CH-8057 Zurich Switzerland ; _publ_contact_author_email jss@oci.unizh.ch _publ_contact_author_fax '41 44 635 6812' _publ_contact_author_phone '41 44 635 4228' _publ_requested_category ? _publ_requested_coeditor_name ? # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and stability of exocyclic triazine nucleosides ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_footnote _publ_author_address M.K.Hysell . ; Department of Chemistry University of California San Diego 9500 Gilman Drive La Jolla California 92093-0358 USA ; Y.Tor . ; Department of Chemistry University of California San Diego 9500 Gilman Drive La Jolla California 92093-0358 USA ; J.S.Siegel . ; Institute of Organic Chemistry University of Zurich Winterthurerstrasse 190 CH-8057 Zurich Switzerland ; _publ_section_references ; Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_table_legends ; ? ; _publ_section_figure_captions ; ? ; #========================================================================== data_michb _database_code_depnum_ccdc_archive 'CCDC 266147' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H22 N6 O4' _chemical_formula_weight 302.35 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 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' _cell_length_a 12.9893(12) _cell_length_b 22.218(2) _cell_length_c 5.2165(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1505.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9551 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details semi-empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12910 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3420 _reflns_number_gt 3138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0830P)^2^+0.9378P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(15) _refine_ls_number_reflns 3420 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 N1 N 0.71314(14) 0.77324(8) 0.4807(4) 0.0154(4) Uani 1 1 d . . . N2 N 0.73165(15) 0.67555(9) 0.6168(4) 0.0172(4) Uani 1 1 d . . . N3 N 0.85370(15) 0.65325(9) 0.9468(4) 0.0176(4) Uani 1 1 d . . . N4 N 0.82736(14) 0.75513(9) 0.8140(4) 0.0160(4) Uani 1 1 d . . . N5 N 0.75580(16) 0.57915(10) 0.7564(4) 0.0222(5) Uani 1 1 d . . . N6 N 0.94476(15) 0.73043(10) 1.1256(4) 0.0190(4) Uani 1 1 d . . . O1 O 0.62489(12) 0.85661(7) 0.6444(3) 0.0165(3) Uani 1 1 d . . . O2 O 0.45663(13) 0.93853(8) 0.8257(3) 0.0160(4) Uani 1 1 d . . . O3 O 0.63540(13) 0.96332(7) 0.1271(3) 0.0160(3) Uani 1 1 d . . . O4 O 0.5574(3) 0.4451(2) 0.1714(14) 0.153(3) Uani 1 1 d . . . C1 C 0.59450(17) 0.91260(10) 0.5306(4) 0.0135(4) Uani 1 1 d . . . H1A H 0.6332 0.9464 0.6128 0.016 Uiso 1 1 calc R . . C2 C 0.62721(17) 0.90667(10) 0.2509(4) 0.0140(4) Uani 1 1 d . . . H2C H 0.5781 0.8801 0.1561 0.017 Uiso 1 1 calc R . . C3 C 0.73134(18) 0.87553(10) 0.2796(4) 0.0156(5) Uani 1 1 d . . . H3C H 0.7873 0.9055 0.2989 0.019 Uiso 1 1 calc R . . H3B H 0.7462 0.8499 0.1288 0.019 Uiso 1 1 calc R . . C4 C 0.72046(17) 0.83704(10) 0.5239(4) 0.0155(5) Uani 1 1 d . . . H4A H 0.7795 0.8455 0.6415 0.019 Uiso 1 1 calc R . . C5 C 0.75895(16) 0.73321(10) 0.6448(5) 0.0151(4) Uani 1 1 d . . . C6 C 0.78110(18) 0.63770(10) 0.7740(5) 0.0176(5) Uani 1 1 d . . . C7 C 0.87290(17) 0.71276(10) 0.9585(5) 0.0171(5) Uani 1 1 d . . . C8 C 0.48054(17) 0.92181(10) 0.5684(4) 0.0139(4) Uani 1 1 d . . . H8A H 0.4562 0.9537 0.4503 0.017 Uiso 1 1 calc R . . H8B H 0.4437 0.8841 0.5251 0.017 Uiso 1 1 calc R . . C9 C 0.63858(18) 0.75206(11) 0.2904(5) 0.0185(5) Uani 1 1 d . . . H9A H 0.6413 0.7080 0.2802 0.028 Uiso 1 1 calc R . . H9B H 0.6553 0.7693 0.1225 0.028 Uiso 1 1 calc R . . H9C H 0.5692 0.7647 0.3410 0.028 Uiso 1 1 calc R . . C10 C 0.6917(2) 0.55658(12) 0.5504(7) 0.0331(7) Uani 1 1 d . . . H10A H 0.6822 0.5131 0.5707 0.050 Uiso 1 1 calc R . . H10B H 0.7250 0.5648 0.3854 0.050 Uiso 1 1 calc R . . H10C H 0.6246 0.5766 0.5556 0.050 Uiso 1 1 calc R . . C11 C 0.97234(18) 0.79275(12) 1.1701(5) 0.0224(5) Uani 1 1 d . . . H11A H 1.0259 0.7948 1.3020 0.034 Uiso 1 1 calc R . . H11B H 0.9115 0.8151 1.2277 0.034 Uiso 1 1 calc R . . H11C H 0.9982 0.8105 1.0106 0.034 Uiso 1 1 calc R . . H5A H 0.795(3) 0.5513(14) 0.839(7) 0.032(8) Uiso 1 1 d . . . H6A H 0.972(2) 0.7033(14) 1.212(6) 0.015(7) Uiso 1 1 d . . . H3A H 0.585(2) 0.9664(12) 0.019(6) 0.016(7) Uiso 1 1 d . . . H2A H 0.431(3) 0.9149(16) 0.890(7) 0.034(11) 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 N1 0.0170(8) 0.0139(9) 0.0152(9) 0.0007(7) -0.0031(8) 0.0021(7) N2 0.0159(8) 0.0150(9) 0.0207(10) -0.0002(8) -0.0006(8) 0.0031(7) N3 0.0166(9) 0.0182(9) 0.0179(10) 0.0029(8) 0.0008(8) 0.0058(7) N4 0.0154(8) 0.0173(9) 0.0154(10) 0.0013(8) -0.0013(7) 0.0026(7) N5 0.0205(9) 0.0167(10) 0.0293(12) 0.0035(9) -0.0016(9) 0.0034(8) N6 0.0176(9) 0.0192(10) 0.0201(10) 0.0040(8) -0.0033(8) 0.0043(8) O1 0.0180(7) 0.0160(8) 0.0156(8) 0.0031(6) 0.0030(7) 0.0065(6) O2 0.0177(8) 0.0140(8) 0.0164(9) 0.0015(7) 0.0040(7) -0.0028(7) O3 0.0206(8) 0.0149(8) 0.0126(8) 0.0026(6) -0.0015(7) 0.0004(6) O4 0.072(2) 0.135(4) 0.251(7) -0.140(5) 0.047(3) -0.022(2) C1 0.0143(9) 0.0120(10) 0.0141(10) 0.0015(8) -0.0008(8) 0.0013(8) C2 0.0169(10) 0.0127(10) 0.0124(10) 0.0017(8) 0.0000(8) 0.0004(8) C3 0.0186(10) 0.0145(10) 0.0138(11) 0.0005(8) 0.0011(9) 0.0021(9) C4 0.0166(10) 0.0163(11) 0.0136(10) -0.0014(8) 0.0001(9) 0.0040(8) C5 0.0134(9) 0.0149(11) 0.0170(11) 0.0005(9) 0.0032(8) 0.0033(8) C6 0.0164(10) 0.0164(11) 0.0198(11) 0.0024(9) 0.0061(9) 0.0047(8) C7 0.0153(10) 0.0208(11) 0.0151(10) 0.0039(9) 0.0055(9) 0.0051(9) C8 0.0157(9) 0.0139(10) 0.0122(11) 0.0005(8) 0.0003(8) -0.0002(8) C9 0.0191(10) 0.0185(11) 0.0178(11) 0.0007(9) -0.0041(9) 0.0001(9) C10 0.0325(13) 0.0181(12) 0.0487(18) -0.0015(12) -0.0085(13) -0.0009(11) C11 0.0182(11) 0.0256(12) 0.0233(13) 0.0005(10) -0.0038(10) 0.0001(9) _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 N1 C5 1.371(3) . ? N1 C4 1.439(3) . ? N1 C9 1.465(3) . ? N2 C5 1.337(3) . ? N2 C6 1.339(3) . ? N3 C7 1.347(3) . ? N3 C6 1.350(3) . ? N4 C7 1.343(3) . ? N4 C5 1.344(3) . ? N5 C6 1.345(3) . ? N5 C10 1.449(4) . ? N6 C7 1.336(3) . ? N6 C11 1.449(3) . ? O1 C1 1.434(3) . ? O1 C4 1.458(3) . ? O2 C8 1.427(3) . ? O3 C2 1.419(3) . ? C1 C8 1.507(3) . ? C1 C2 1.525(3) . ? C2 C3 1.527(3) . ? C3 C4 1.541(3) . ? 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 C5 N1 C4 120.85(19) . . ? C5 N1 C9 120.14(19) . . ? C4 N1 C9 117.82(18) . . ? C5 N2 C6 114.1(2) . . ? C7 N3 C6 114.25(19) . . ? C7 N4 C5 113.9(2) . . ? C6 N5 C10 121.7(2) . . ? C7 N6 C11 123.9(2) . . ? C1 O1 C4 108.34(16) . . ? O1 C1 C8 109.51(18) . . ? O1 C1 C2 104.15(17) . . ? C8 C1 C2 114.24(19) . . ? O3 C2 C1 112.31(18) . . ? O3 C2 C3 112.34(18) . . ? C1 C2 C3 101.08(17) . . ? C2 C3 C4 104.55(18) . . ? N1 C4 O1 107.77(17) . . ? N1 C4 C3 115.04(19) . . ? O1 C4 C3 105.61(17) . . ? N2 C5 N4 126.5(2) . . ? N2 C5 N1 116.0(2) . . ? N4 C5 N1 117.5(2) . . ? N2 C6 N5 116.7(2) . . ? N2 C6 N3 125.7(2) . . ? N5 C6 N3 117.6(2) . . ? N6 C7 N4 117.9(2) . . ? N6 C7 N3 116.6(2) . . ? N4 C7 N3 125.5(2) . . ? O2 C8 C1 111.85(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A O3 0.91(3) 2.16(3) 2.998(3) 152(3) 3_646 N5 H5A O2 0.91(3) 2.74(4) 3.422(3) 133(3) 4_567 N6 H6A O1 0.83(3) 2.50(3) 3.264(3) 153(2) 4_567 N6 H6A O2 0.83(3) 3.16(3) 3.766(3) 131(2) 4_567 N6 H6A N1 0.83(3) 3.55(3) 4.047(3) 121(2) 4_567 O3 H3A O2 0.87(3) 2.04(3) 2.858(2) 156(3) 1_554 O3 H3A O2 0.87(3) 2.40(3) 2.942(2) 121(2) 2_674 O3 H3A O3 0.87(3) 3.31(3) 3.877(3) 126(2) 2_675 O2 H2A N3 0.71(4) 2.00(4) 2.712(3) 177(4) 4_467 O2 H2A N5 0.71(4) 2.93(4) 3.422(3) 129(3) 4_467 O2 H2A N6 0.71(4) 3.24(4) 3.766(3) 135(3) 4_467 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.423 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.065