data_shelxl _audit_update_record ; 2005-12-06 Received for J. Org. Chem. manuscript jo052506b Minor syntax errors corrected (JOC/pH) ; _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., 1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 N5 O3' _chemical_formula_weight 267.30 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_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 9.9344(11) _cell_length_b 13.5019(15) _cell_length_c 10.2111(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.034(3) _cell_angle_gamma 90.00 _cell_volume 1339.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'multi-scans' _exptl_absorpt_correction_method 'symmetry-related measurements' _exptl_absorpt_correction_T_min 0.8130 _exptl_absorpt_correction_T_max 1.0000 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' # # DUPLICATE DATA ITEM COMMENTED OUT # #_diffrn_measurement_device_type 'Rigaku Mercury' # _diffrn_measurement_method 'phi rotations' _diffrn_reflns_number 7176 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2400 _reflns_number_gt 2168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999) ' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0556P)^2^+0.4224P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2400 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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_symetry_multiplicity _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.15243(14) 0.52260(10) 0.38411(13) 0.0238(3) Uani 1 1 d . . . H1A H 0.0619 0.5191 0.4055 0.032 Uiso 1 1 calc R . . H1B H 0.1508 0.4908 0.2986 0.032 Uiso 1 1 calc R . . C2 C 0.20630(14) 0.62887(10) 0.38772(14) 0.0252(3) Uani 1 1 d . . . H2 H 0.1571 0.6787 0.3260 0.034 Uiso 1 1 calc R . . C3 C 0.36206(15) 0.61052(11) 0.39646(15) 0.0314(3) Uani 1 1 d . . . H3A H 0.3833 0.5630 0.3324 0.042 Uiso 1 1 calc R . . H3B H 0.4175 0.6700 0.4005 0.042 Uiso 1 1 calc R . . C4 C 0.35254(13) 0.56646(10) 0.53418(14) 0.0256(3) Uani 1 1 d . . . H4 H 0.4352 0.5594 0.6052 0.034 Uiso 1 1 calc R . . C5 C 0.24819(14) 0.65107(10) 0.53947(14) 0.0253(3) Uani 1 1 d . . . H5 H 0.2947 0.7152 0.5560 0.034 Uiso 1 1 calc R . . C6 C 0.23005(13) 0.40938(9) 0.57381(13) 0.0209(3) Uani 1 1 d . . . C7 C 0.31279(15) 0.33467(11) 0.79645(13) 0.0271(3) Uani 1 1 d . . . C8 C 0.43440(18) 0.36519(14) 0.90497(17) 0.0459(4) Uani 1 1 d . . . H8A H 0.5180 0.3567 0.8731 0.069 Uiso 1 1 calc R . . H8B H 0.4374 0.3248 0.9829 0.069 Uiso 1 1 calc R . . H8C H 0.4248 0.4335 0.9277 0.069 Uiso 1 1 calc R . . C9 C 0.32702(19) 0.22876(12) 0.75229(16) 0.0408(4) Uani 1 1 d . . . H9A H 0.2514 0.2128 0.6803 0.061 Uiso 1 1 calc R . . H9B H 0.3268 0.1848 0.8262 0.061 Uiso 1 1 calc R . . H9C H 0.4119 0.2215 0.7224 0.061 Uiso 1 1 calc R . . C10 C 0.17822(16) 0.35204(12) 0.84042(16) 0.0366(4) Uani 1 1 d . . . H10A H 0.1692 0.4212 0.8589 0.055 Uiso 1 1 calc R . . H10B H 0.1772 0.3142 0.9198 0.055 Uiso 1 1 calc R . . H10C H 0.1030 0.3317 0.7704 0.055 Uiso 1 1 calc R . . C11 C 0.18678(15) 0.63507(10) 0.75420(14) 0.0266(3) Uani 1 1 d . . . N1 N 0.26094(11) 0.48116(8) 0.49246(11) 0.0230(3) Uani 1 1 d . . . N2 N 0.14645(11) 0.63890(8) 0.62105(11) 0.0252(3) Uani 1 1 d . . . H2A H 0.0606 0.6342 0.5841 0.034 Uiso 1 1 calc R . . N3 N 0.06812(13) 0.62634(10) 0.81498(12) 0.0330(3) Uani 1 1 d . . . N4 N 0.10157(15) 0.61585(10) 0.93856(14) 0.0394(4) Uani 1 1 d . . . N5 N 0.1220(2) 0.60516(14) 1.04987(17) 0.0623(5) Uani 1 1 d . . . O1 O 0.12956(10) 0.35518(7) 0.54339(9) 0.0256(2) Uani 1 1 d . . . O2 O 0.32605(9) 0.40375(7) 0.68693(9) 0.0271(2) Uani 1 1 d . . . O3 O 0.30374(11) 0.63868(8) 0.81827(10) 0.0364(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 0.0257(7) 0.0234(7) 0.0214(7) 0.0039(5) 0.0027(5) 0.0019(5) C2 0.0247(7) 0.0233(7) 0.0281(8) 0.0072(5) 0.0064(5) 0.0025(5) C3 0.0272(8) 0.0312(8) 0.0381(9) 0.0096(6) 0.0122(6) 0.0013(6) C4 0.0189(7) 0.0261(7) 0.0313(8) 0.0049(5) 0.0042(5) -0.0005(5) C5 0.0220(7) 0.0217(7) 0.0315(8) 0.0018(5) 0.0040(5) -0.0032(5) C6 0.0205(7) 0.0210(7) 0.0215(7) 0.0007(5) 0.0049(5) 0.0047(5) C7 0.0286(7) 0.0295(7) 0.0227(7) 0.0094(6) 0.0044(5) 0.0024(6) C8 0.0412(10) 0.0600(11) 0.0311(9) 0.0142(8) -0.0050(7) -0.0039(8) C9 0.0548(10) 0.0323(9) 0.0366(9) 0.0105(7) 0.0126(7) 0.0102(7) C10 0.0371(9) 0.0430(9) 0.0325(8) 0.0094(6) 0.0134(7) 0.0065(7) C11 0.0288(8) 0.0196(7) 0.0304(8) -0.0053(5) 0.0037(6) -0.0001(6) N1 0.0229(6) 0.0218(6) 0.0233(6) 0.0041(4) 0.0027(4) 0.0007(4) N2 0.0197(6) 0.0289(6) 0.0259(7) -0.0028(5) 0.0024(5) -0.0013(5) N3 0.0355(7) 0.0372(7) 0.0266(8) -0.0054(5) 0.0073(5) -0.0032(5) N4 0.0469(8) 0.0391(8) 0.0338(10) -0.0086(6) 0.0121(6) -0.0070(6) N5 0.0791(13) 0.0785(13) 0.0316(10) -0.0043(8) 0.0169(8) -0.0117(10) O1 0.0257(5) 0.0237(5) 0.0257(5) 0.0026(4) 0.0016(4) -0.0023(4) O2 0.0236(5) 0.0314(5) 0.0242(5) 0.0102(4) 0.0004(4) -0.0027(4) O3 0.0309(6) 0.0420(6) 0.0323(6) -0.0058(4) -0.0026(4) -0.0006(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 C1 N1 1.4839(16) . ? C1 C2 1.5291(19) . ? C2 C5 1.548(2) . ? C2 C3 1.551(2) . ? C3 C4 1.5478(19) . ? C4 N1 1.4746(17) . ? C4 C5 1.5511(19) . ? C5 N2 1.4469(18) . ? C6 O1 1.2245(16) . ? C6 O2 1.3380(16) . ? C6 N1 1.3527(17) . ? C7 O2 1.4831(16) . ? C7 C10 1.515(2) . ? C7 C8 1.516(2) . ? C7 C9 1.515(2) . ? C11 O3 1.2097(18) . ? C11 N2 1.3359(19) . ? C11 N3 1.447(2) . ? N3 N4 1.244(2) . ? N4 N5 1.121(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 N1 C1 C2 98.03(10) . . ? C1 C2 C5 103.03(10) . . ? C1 C2 C3 101.04(11) . . ? C5 C2 C3 85.21(10) . . ? C4 C3 C2 82.22(10) . . ? N1 C4 C3 100.87(11) . . ? N1 C4 C5 102.04(10) . . ? C3 C4 C5 85.21(10) . . ? N2 C5 C2 118.69(11) . . ? N2 C5 C4 119.25(11) . . ? C2 C5 C4 82.22(10) . . ? O1 C6 O2 125.58(12) . . ? O1 C6 N1 123.35(12) . . ? O2 C6 N1 111.02(11) . . ? O2 C7 C10 110.42(11) . . ? O2 C7 C8 101.40(11) . . ? C10 C7 C8 111.06(13) . . ? O2 C7 C9 109.92(11) . . ? C10 C7 C9 112.17(13) . . ? C8 C7 C9 111.38(13) . . ? O3 C11 N2 126.82(14) . . ? O3 C11 N3 123.22(13) . . ? N2 C11 N3 109.96(12) . . ? C6 N1 C4 125.98(11) . . ? C6 N1 C1 120.36(11) . . ? C4 N1 C1 103.27(10) . . ? C11 N2 C5 119.54(12) . . ? N4 N3 C11 112.03(12) . . ? N5 N4 N3 175.00(17) . . ? C6 O2 C7 121.82(10) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.191 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.038