# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/315 data_1 _publ_author_name 'D. M. Loakes, D. M. Brown and S. A. Salisbury' _audit_creation_method SHELXL _chemical_name_systematic ;3-methyl-6-(2-chloroethyl)-8-(2-deoxy-beta-D-ribofuranosyl)-1,2,4,- triazolo[1,5-c]pyrimidin-5-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H17 Cl N4 O4' _chemical_formula_weight 328.76 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.911(4) _cell_length_b 16.391(5) _cell_length_c 9.146(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.44(4) _cell_angle_gamma 90.00 _cell_volume 730.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method ? _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1472 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1317 _reflns_number_observed 1189 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.0923P] 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 ? _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 0.09(12) _refine_ls_number_reflns 1317 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_obs 0.0370 _refine_ls_wR_factor_all 0.1028 _refine_ls_wR_factor_obs 0.0966 _refine_ls_goodness_of_fit_all 0.937 _refine_ls_goodness_of_fit_obs 0.934 _refine_ls_restrained_S_all 0.937 _refine_ls_restrained_S_obs 0.934 _refine_ls_shift/esd_max -0.004 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O5' O 0.2100(7) 0.7590(2) 0.1150(4) 0.0635(8) Uani 1 d . . H5' H 0.2290(70) 0.7109(11) 0.0934(52) 0.095 Uiso 1 calc R . C5' C 0.4305(8) 0.7831(2) 0.2219(5) 0.0522(10) Uani 1 d . . H5'1 H 0.6037(8) 0.7756(2) 0.1833(5) 0.063 Uiso 1 calc R . H5'2 H 0.4328(8) 0.7499(2) 0.3098(5) 0.063 Uiso 1 calc R . C4' C 0.3934(7) 0.8714(2) 0.2591(4) 0.0406(8) Uani 1 d . . H4' H 0.5400(7) 0.8870(2) 0.3371(4) 0.049 Uiso 1 calc R . O4' O 0.4119(5) 0.9225(2) 0.1314(3) 0.0432(6) Uani 1 d . . C3' C 0.1204(7) 0.8943(2) 0.3073(3) 0.0397(8) Uani 1 d . . H3'1 H -0.0242(7) 0.8668(2) 0.2413(3) 0.048 Uiso 1 calc R . O3' O 0.0888(6) 0.8722(2) 0.4535(3) 0.0543(7) Uani 1 d . . H3' H 0.1910(87) 0.9002(24) 0.5112(3) 0.081 Uiso 1 calc R . C2' C 0.1051(8) 0.9842(2) 0.2720(4) 0.0423(8) Uani 1 d . . H2'1 H -0.0830(8) 1.0037(2) 0.2597(4) 0.051 Uiso 1 calc R . H2'2 H 0.2134(8) 1.0161(2) 0.3478(4) 0.051 Uiso 1 calc R . C1' C 0.2254(7) 0.9867(2) 0.1290(4) 0.0393(8) Uani 1 d . . H1' H 0.3215(7) 1.0386(2) 0.1211(4) 0.047 Uiso 1 calc R . N8 N 0.0065(7) 0.9775(2) 0.0008(3) 0.0394(6) Uani 1 d . . C9 C -0.1521(8) 1.0458(2) -0.0300(4) 0.0433(8) Uani 1 d . . O9 O -0.1168(6) 1.1097(2) 0.0351(3) 0.0572(7) Uani 1 d . . N1 N -0.3624(7) 1.0330(2) -0.1440(3) 0.0440(7) Uani 1 d . . N2 N -0.5469(7) 1.0930(2) -0.1901(3) 0.0502(8) Uani 1 d . . C3 C -0.6989(8) 1.0565(3) -0.3006(4) 0.0497(9) Uani 1 d . . C31 C -0.9340(7) 1.09842(14) -0.3864(4) 0.0661(13) Uani 1 d . . H31A H -0.8774(5) 1.1209(2) -0.4746(6) 0.099 Uiso 1 calc R . H31B H -0.9969(13) 1.1415(3) -0.3281(6) 0.099 Uiso 1 calc R . H31C H -1.0802(4) 1.0601(2) -0.4121(2) 0.099 Uiso 1 calc R . N4 N -0.6242(4) 0.97752(11) -0.3283(2) 0.0503(8) Uani 1 d R . C4 C -0.4111(4) 0.96460(11) -0.2258(2) 0.0412(8) Uani 1 d R . C6 C -0.2393(4) 0.89591(11) -0.1906(2) 0.0417(8) Uani 1 d R . C61 C -0.2793(4) 0.81716(11) -0.2765(2) 0.0545(10) Uani 1 d R . H61A H -0.3516(4) 0.82992(12) -0.3777(2) 0.065 Uiso 1 calc R . H61B H -0.1016(4) 0.79153(12) -0.2776(2) 0.065 Uiso 1 calc R . C62 C -0.4594(19) 0.7599(4) -0.2200(8) 0.110(3) Uani 1 d . . H62A H -0.6291(19) 0.7875(4) -0.2068(8) 0.132 Uiso 1 calc R . H62B H -0.3754(19) 0.7416(4) -0.1237(8) 0.132 Uiso 1 calc R . Cl1 Cl -0.5388(3) 0.67352(7) -0.3328(2) 0.0774(4) Uani 1 d . . C7 C -0.0378(8) 0.9054(2) -0.0764(4) 0.0410(8) Uani 1 d . . H7 H 0.0763 0.8613 -0.0485 0.049 Uiso 1 calc . . 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 O5' 0.071(2) 0.0417(15) 0.072(2) -0.0078(14) -0.013(2) -0.0036(14) C5' 0.047(2) 0.046(2) 0.061(3) 0.002(2) -0.003(2) 0.001(2) C4' 0.037(2) 0.042(2) 0.040(2) 0.000(2) -0.0012(14) -0.009(2) O4' 0.0384(12) 0.0469(15) 0.0451(13) 0.0026(12) 0.0083(10) -0.0002(11) C3' 0.039(2) 0.049(2) 0.030(2) 0.0015(15) -0.0004(13) -0.009(2) O3' 0.059(2) 0.067(2) 0.0354(14) 0.0090(13) 0.0026(11) -0.0173(14) C2' 0.045(2) 0.046(2) 0.035(2) -0.004(2) 0.0013(14) 0.000(2) C1' 0.043(2) 0.038(2) 0.036(2) -0.0009(15) -0.0002(14) -0.0042(15) N8 0.0471(15) 0.039(2) 0.0311(14) 0.0001(12) 0.0009(11) -0.0040(13) C9 0.055(2) 0.040(2) 0.033(2) 0.002(2) -0.001(2) -0.003(2) O9 0.078(2) 0.043(2) 0.046(2) -0.0045(13) -0.0117(13) 0.0070(14) N1 0.054(2) 0.041(2) 0.035(2) 0.0029(13) -0.0018(13) 0.0056(14) N2 0.056(2) 0.052(2) 0.041(2) 0.0042(15) 0.0008(14) 0.006(2) C3 0.050(2) 0.060(3) 0.038(2) 0.007(2) 0.005(2) 0.001(2) C31 0.063(2) 0.087(4) 0.047(2) 0.005(2) 0.002(2) 0.020(3) N4 0.053(2) 0.062(2) 0.035(2) 0.003(2) -0.0003(13) -0.004(2) C5 0.050(2) 0.047(2) 0.027(2) 0.0021(14) 0.0049(14) -0.008(2) C6 0.050(2) 0.044(2) 0.032(2) -0.0016(15) 0.0062(14) -0.008(2) C61 0.069(3) 0.055(2) 0.040(2) -0.009(2) 0.010(2) -0.011(2) C62 0.173(7) 0.079(4) 0.093(4) -0.047(3) 0.070(5) -0.066(4) Cl1 0.0902(9) 0.0534(7) 0.0883(9) -0.0183(6) 0.0104(7) -0.0209(6) C7 0.052(2) 0.040(2) 0.032(2) -0.0001(15) 0.0063(15) 0.001(2) _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 O5' C5' 1.418(5) . ? C5' C4' 1.503(6) . ? C4' O4' 1.449(5) . ? C4' C3' 1.512(5) . ? O4' C1' 1.394(5) . ? C3' O3' 1.413(4) . ? C3' C2' 1.509(5) . ? C2' C1' 1.504(5) . ? C1' N8 1.492(5) . ? N8 C9 1.372(5) . ? N8 C7 1.378(5) . ? C9 O9 1.207(5) . ? C9 N1 1.386(5) . ? N1 C5 1.351(4) . ? N1 N2 1.367(5) . ? N2 C3 1.320(5) . ? C3 N4 1.377(5) . ? C3 C31 1.479(4) . ? N4 C5 1.33 . ? C5 C6 1.42 . ? C6 C7 1.352(4) . ? C6 C61 1.51 . ? C61 C62 1.431(6) . ? C62 Cl1 1.765(5) . ? 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 O5' C5' C4' 108.7(3) . . ? O4' C4' C5' 110.6(3) . . ? O4' C4' C3' 104.0(3) . . ? C5' C4' C3' 116.3(3) . . ? C1' O4' C4' 109.9(3) . . ? O3' C3' C2' 116.4(3) . . ? O3' C3' C4' 115.0(3) . . ? C2' C3' C4' 101.7(3) . . ? C1' C2' C3' 101.4(3) . . ? O4' C1' N8 109.9(3) . . ? O4' C1' C2' 107.3(3) . . ? N8 C1' C2' 110.9(3) . . ? C9 N8 C7 123.1(3) . . ? C9 N8 C1' 114.2(3) . . ? C7 N8 C1' 122.6(3) . . ? O9 C9 N8 124.5(3) . . ? O9 C9 N1 123.2(3) . . ? N8 C9 N1 112.3(3) . . ? C5 N1 N2 111.3(3) . . ? C5 N1 C9 127.1(3) . . ? N2 N1 C9 121.5(3) . . ? C3 N2 N1 101.3(3) . . ? N2 C3 N4 115.5(3) . . ? N2 C3 C31 121.3(4) . . ? N4 C3 C31 123.2(3) . . ? C5 N4 C3 102.9(2) . . ? N4 C5 N1 108.98(15) . . ? N4 C5 C6 132.6 . . ? N1 C5 C6 118.38(15) . . ? C7 C6 C5 116.0(2) . . ? C7 C6 C61 122.3(2) . . ? C5 C6 C61 121.8 . . ? C62 C61 C6 114.7(2) . . ? C61 C62 Cl1 114.5(4) . . ? C6 C7 N8 123.1(3) . . ? _refine_diff_density_max 0.164 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.040