Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name M.J.Miller J.Balzarini 'De Clercq, E.' 'Weiqiang Huang.' _publ_contact_author_name 'Marvin J. Miller' _publ_contact_author_address ; Chemistry and Biochemistry University of Notre Dame 251 Nieuwland Science Hall Notre Dame IN 46556 UNITED STATES OF AMERICA ; _publ_contact_author_email MMILLER1@ND.EDU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Syntheses and Anti-HIV Activities of (+)-Norcarbovir and (+) Norabacavir ; data_mjm202m _database_code_depnum_ccdc_archive 'CCDC 633037' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N6 O' _chemical_formula_weight 272.32 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7926(3) _cell_length_b 10.0685(6) _cell_length_c 12.2947(7) _cell_angle_alpha 65.8730(10) _cell_angle_beta 76.4520(10) _cell_angle_gamma 85.5070(10) _cell_volume 636.09(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4520 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 23.29 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9076 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _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 5993 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3118 _reflns_number_gt 2868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0883P)^2^+0.2948P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment isotropic _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3118 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1491 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.8398(2) 0.31170(15) 0.78947(13) 0.0217(3) Uani 1 1 d . . . H1 H 0.910(3) 0.3656(19) 0.7054(16) 0.016(4) Uiso 1 1 d . . . C2 C 1.0188(2) 0.26157(16) 0.86908(14) 0.0246(3) Uani 1 1 d . . . H2 H 1.147(4) 0.203(2) 0.8505(18) 0.033(5) Uiso 1 1 d . . . C3 C 0.9655(2) 0.30382(16) 0.96086(13) 0.0235(3) Uani 1 1 d . . . H3 H 1.057(4) 0.280(2) 1.0225(18) 0.033(5) Uiso 1 1 d . . . O4 O 0.5646(2) 0.32529(12) 1.07132(10) 0.0273(3) Uani 1 1 d . . . H4 H 0.515(4) 0.232(3) 1.077(2) 0.045(6) Uiso 1 1 d . . . C4 C 0.7428(3) 0.39128(15) 0.96132(13) 0.0231(3) Uani 1 1 d . . . H4A H 0.773(3) 0.485(2) 0.9596(17) 0.026(4) Uiso 1 1 d . . . C5 C 0.6697(3) 0.40662(16) 0.84366(13) 0.0235(3) Uani 1 1 d . . . H5A H 0.684(4) 0.509(3) 0.7846(19) 0.039(5) Uiso 1 1 d . . . H5B H 0.501(4) 0.372(2) 0.8672(18) 0.033(5) Uiso 1 1 d . . . N6 N 0.7204(2) 0.18570(12) 0.79264(10) 0.0204(3) Uani 1 1 d . . . C7 C 0.7229(3) 0.04302(15) 0.87217(13) 0.0227(3) Uani 1 1 d . . . H7 H 0.811(3) 0.012(2) 0.9348(17) 0.023(4) Uiso 1 1 d . . . N8 N 0.5945(2) -0.04425(13) 0.85384(11) 0.0227(3) Uani 1 1 d . . . C9 C 0.4997(2) 0.04745(15) 0.75545(12) 0.0201(3) Uani 1 1 d . . . C10 C 0.3568(2) 0.02246(15) 0.68624(13) 0.0221(3) Uani 1 1 d . . . N11 N 0.2875(2) 0.13753(13) 0.59739(11) 0.0240(3) Uani 1 1 d . . . N12 N 0.2777(3) 0.38384(15) 0.48687(13) 0.0295(3) Uani 1 1 d . . . H12A H 0.330(4) 0.476(3) 0.456(2) 0.045(6) Uiso 1 1 d . . . H12B H 0.212(4) 0.362(3) 0.444(2) 0.044(6) Uiso 1 1 d . . . C12 C 0.3660(2) 0.27252(16) 0.57337(13) 0.0228(3) Uani 1 1 d . . . N13 N 0.5166(2) 0.30818(13) 0.62633(11) 0.0219(3) Uani 1 1 d . . . C14 C 0.5761(2) 0.19003(15) 0.71675(12) 0.0197(3) Uani 1 1 d . . . N15 N 0.2966(2) -0.11309(14) 0.70544(12) 0.0273(3) Uani 1 1 d . . . H15 H 0.344(4) -0.182(3) 0.763(2) 0.038(6) Uiso 1 1 d . . . C16 C 0.1883(3) -0.14515(17) 0.62457(14) 0.0278(3) Uani 1 1 d . . . H16 H 0.243(4) -0.091(2) 0.538(2) 0.038(5) Uiso 1 1 d . . . C17 C -0.0657(3) -0.19754(19) 0.66549(16) 0.0317(4) Uani 1 1 d . . . H17A H -0.151(4) -0.211(3) 0.749(2) 0.048(6) Uiso 1 1 d . . . H17B H -0.169(4) -0.165(2) 0.603(2) 0.040(6) Uiso 1 1 d . . . C18 C 0.1341(3) -0.30173(18) 0.65828(16) 0.0298(3) Uani 1 1 d . . . H18A H 0.166(4) -0.341(3) 0.590(2) 0.046(6) Uiso 1 1 d . . . H18B H 0.171(4) -0.374(3) 0.734(2) 0.040(6) 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 0.0189(6) 0.0207(6) 0.0256(7) -0.0089(5) -0.0054(5) -0.0018(5) C2 0.0178(6) 0.0258(7) 0.0315(7) -0.0118(6) -0.0076(5) 0.0011(5) C3 0.0209(6) 0.0232(6) 0.0273(7) -0.0091(5) -0.0089(5) -0.0002(5) O4 0.0297(6) 0.0225(5) 0.0266(5) -0.0086(4) -0.0032(4) 0.0004(4) C4 0.0232(7) 0.0191(6) 0.0274(7) -0.0091(5) -0.0065(5) -0.0003(5) C5 0.0221(7) 0.0215(6) 0.0287(7) -0.0102(5) -0.0100(5) 0.0028(5) N6 0.0205(5) 0.0190(6) 0.0223(5) -0.0078(4) -0.0071(4) 0.0007(4) C7 0.0244(6) 0.0202(6) 0.0234(6) -0.0073(5) -0.0081(5) 0.0021(5) N8 0.0244(6) 0.0207(6) 0.0230(6) -0.0076(5) -0.0076(4) 0.0015(4) C9 0.0201(6) 0.0190(6) 0.0207(6) -0.0073(5) -0.0047(5) 0.0006(5) C10 0.0205(6) 0.0221(7) 0.0226(6) -0.0077(5) -0.0039(5) -0.0025(5) N11 0.0242(6) 0.0223(6) 0.0244(6) -0.0061(5) -0.0081(5) -0.0038(5) N12 0.0339(7) 0.0228(6) 0.0310(7) -0.0038(5) -0.0174(6) -0.0041(5) C12 0.0215(6) 0.0226(7) 0.0223(6) -0.0063(5) -0.0058(5) -0.0016(5) N13 0.0212(6) 0.0202(6) 0.0232(6) -0.0064(5) -0.0068(4) -0.0015(4) C14 0.0174(6) 0.0209(6) 0.0208(6) -0.0087(5) -0.0037(5) 0.0005(5) N15 0.0331(7) 0.0215(6) 0.0281(6) -0.0064(5) -0.0133(5) -0.0039(5) C16 0.0335(8) 0.0262(7) 0.0248(7) -0.0098(6) -0.0073(6) -0.0045(6) C17 0.0278(8) 0.0369(9) 0.0380(9) -0.0214(7) -0.0094(6) 0.0015(6) C18 0.0288(7) 0.0274(7) 0.0367(8) -0.0154(7) -0.0085(6) -0.0011(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 N6 1.4744(17) . ? C1 C2 1.5090(19) . ? C1 C5 1.547(2) . ? C2 C3 1.326(2) . ? C3 C4 1.5039(19) . ? O4 C4 1.4335(17) . ? C4 C5 1.546(2) . ? N6 C7 1.3694(17) . ? N6 C14 1.3775(17) . ? C7 N8 1.3113(19) . ? N8 C9 1.3912(17) . ? C9 C14 1.3876(19) . ? C9 C10 1.4180(19) . ? C10 N11 1.3397(18) . ? C10 N15 1.3463(19) . ? N11 C12 1.3591(18) . ? N12 C12 1.3563(18) . ? C12 N13 1.3494(18) . ? N13 C14 1.3430(18) . ? N15 C16 1.4395(19) . ? C16 C18 1.496(2) . ? C16 C17 1.502(2) . ? C17 C18 1.512(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 N6 C1 C2 110.50(11) . . ? N6 C1 C5 113.40(11) . . ? C2 C1 C5 103.74(11) . . ? C3 C2 C1 112.23(13) . . ? C2 C3 C4 113.04(13) . . ? O4 C4 C3 112.50(11) . . ? O4 C4 C5 114.49(12) . . ? C3 C4 C5 103.57(11) . . ? C4 C5 C1 106.96(11) . . ? C7 N6 C14 106.08(11) . . ? C7 N6 C1 127.84(12) . . ? C14 N6 C1 126.06(11) . . ? N8 C7 N6 113.76(12) . . ? C7 N8 C9 104.05(12) . . ? C14 C9 N8 110.46(12) . . ? C14 C9 C10 116.27(12) . . ? N8 C9 C10 133.16(13) . . ? N11 C10 N15 119.92(13) . . ? N11 C10 C9 118.43(13) . . ? N15 C10 C9 121.62(13) . . ? C10 N11 C12 118.82(12) . . ? N13 C12 N12 116.87(13) . . ? N13 C12 N11 127.87(13) . . ? N12 C12 N11 115.25(13) . . ? C14 N13 C12 111.08(12) . . ? N13 C14 N6 127.16(13) . . ? N13 C14 C9 127.18(13) . . ? N6 C14 C9 105.64(12) . . ? C10 N15 C16 123.53(13) . . ? N15 C16 C18 117.00(13) . . ? N15 C16 C17 119.76(14) . . ? C18 C16 C17 60.57(11) . . ? C16 C17 C18 59.53(10) . . ? C16 C18 C17 59.90(11) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.669 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.062