data_rlm4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N6 O2' _chemical_formula_weight 326.36 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 6.4306(13) _cell_length_b 10.050(2) _cell_length_c 11.980(2) _cell_angle_alpha 84.052(4) _cell_angle_beta 84.765(3) _cell_angle_gamma 88.383(4) _cell_volume 766.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9873 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details 'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 1998)' _diffrn_ambient_temperature 173(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 'SMART CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 5277 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3445 _reflns_number_gt 2572 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Bruker SMART v5.624 (Bruker 1998)' _computing_cell_refinement 'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)' _computing_data_reduction 'Bruker SHELXTL v6.14 (Bruker 2000)' _computing_structure_solution 'Bruker SHELXTL v6.14' _computing_structure_refinement 'Bruker SHELXTL v6.14' _computing_molecular_graphics 'Bruker SHELXTL v6.14' _computing_publication_material 'Bruker SHELXTL v6.14' _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. The two protons on N10 were obtained from a Difference Fourier map and refined without any constraints. ; _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^)+(0.0592P)^2^] 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 3445 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O15 O 0.40017(15) 0.19677(10) 0.47439(9) 0.0356(3) Uani 1 1 d . . . O16 O 0.71233(14) 0.22844(9) 0.37668(8) 0.0290(2) Uani 1 1 d . . . N1 N 0.23983(16) 0.82795(11) 0.31100(9) 0.0230(3) Uani 1 1 d . . . N3 N 0.57789(16) 0.73314(10) 0.24665(9) 0.0226(3) Uani 1 1 d . . . N7 N 0.29723(16) 0.46853(10) 0.41280(9) 0.0224(3) Uani 1 1 d . . . N9 N 0.61207(16) 0.49858(10) 0.31399(9) 0.0214(2) Uani 1 1 d . . . N10 N -0.01351(18) 0.70681(13) 0.42147(11) 0.0275(3) Uani 1 1 d . . . H10B H -0.064(3) 0.6370(18) 0.4660(14) 0.048(5) Uiso 1 1 d . . . H10A H -0.098(2) 0.7796(17) 0.4186(13) 0.037(4) Uiso 1 1 d . . . N11 N 0.49043(18) 0.95629(11) 0.20506(10) 0.0291(3) Uani 1 1 d . . . C2 C 0.4351(2) 0.83368(13) 0.25604(11) 0.0225(3) Uani 1 1 d . . . C4 C 0.50745(19) 0.61940(12) 0.30421(10) 0.0205(3) Uani 1 1 d . . . C5 C 0.31479(19) 0.59898(12) 0.36522(11) 0.0207(3) Uani 1 1 d . . . C6 C 0.17673(19) 0.71141(13) 0.36673(10) 0.0208(3) Uani 1 1 d . . . C8 C 0.47719(19) 0.41119(13) 0.38079(11) 0.0220(3) Uani 1 1 d . . . C12 C 0.3382(2) 1.06664(14) 0.20168(14) 0.0350(4) Uani 1 1 d . . . H12A H 0.2901 1.0847 0.2787 0.052 Uiso 1 1 calc R . . H12B H 0.2189 1.0426 0.1630 0.052 Uiso 1 1 calc R . . H12C H 0.4033 1.1467 0.1611 0.052 Uiso 1 1 calc R . . C13 C 0.6931(2) 0.97812(15) 0.14361(13) 0.0352(4) Uani 1 1 d . . . H13A H 0.7948 0.9133 0.1748 0.053 Uiso 1 1 calc R . . H13B H 0.7379 1.0691 0.1505 0.053 Uiso 1 1 calc R . . H13C H 0.6839 0.9667 0.0640 0.053 Uiso 1 1 calc R . . C14 C 0.5226(2) 0.26761(13) 0.41610(11) 0.0234(3) Uani 1 1 d . . . C17 C 0.7686(2) 0.08991(13) 0.41082(13) 0.0324(3) Uani 1 1 d . . . H17A H 0.9100 0.0702 0.3781 0.049 Uiso 1 1 calc R . . H17B H 0.6697 0.0305 0.3842 0.049 Uiso 1 1 calc R . . H17C H 0.7640 0.0756 0.4932 0.049 Uiso 1 1 calc R . . C18 C 0.82282(18) 0.47737(13) 0.26062(11) 0.0229(3) Uani 1 1 d . . . H18A H 0.9065 0.4254 0.3160 0.027 Uiso 1 1 calc R . . H18B H 0.8890 0.5654 0.2408 0.027 Uiso 1 1 calc R . . C19 C 0.83044(19) 0.40506(12) 0.15589(11) 0.0211(3) Uani 1 1 d . . . C20 C 0.6579(2) 0.39145(13) 0.09732(11) 0.0254(3) Uani 1 1 d . . . H20A H 0.5252 0.4240 0.1253 0.030 Uiso 1 1 calc R . . C21 C 0.6772(2) 0.33046(14) -0.00230(12) 0.0303(3) Uani 1 1 d . . . H21A H 0.5575 0.3211 -0.0416 0.036 Uiso 1 1 calc R . . C22 C 0.8680(2) 0.28369(14) -0.04416(12) 0.0314(3) Uani 1 1 d . . . H22A H 0.8807 0.2422 -0.1123 0.038 Uiso 1 1 calc R . . C23 C 1.0419(2) 0.29732(15) 0.01351(12) 0.0325(3) Uani 1 1 d . . . H23A H 1.1746 0.2658 -0.0154 0.039 Uiso 1 1 calc R . . C24 C 1.0228(2) 0.35669(14) 0.11319(12) 0.0277(3) Uani 1 1 d . . . H24A H 1.1425 0.3645 0.1529 0.033 Uiso 1 1 calc R . . 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 O15 0.0331(5) 0.0227(5) 0.0466(7) 0.0039(5) 0.0109(5) 0.0006(4) O16 0.0282(5) 0.0232(5) 0.0332(6) 0.0019(4) 0.0037(4) 0.0062(4) N1 0.0229(5) 0.0205(6) 0.0246(6) -0.0003(4) -0.0001(5) 0.0000(4) N3 0.0235(5) 0.0199(6) 0.0233(6) -0.0001(4) 0.0008(5) -0.0005(4) N7 0.0236(5) 0.0193(6) 0.0237(6) -0.0007(4) -0.0012(5) -0.0004(4) N9 0.0220(5) 0.0190(6) 0.0223(6) -0.0005(4) 0.0006(5) -0.0001(4) N10 0.0222(6) 0.0223(6) 0.0359(7) 0.0009(5) 0.0027(5) 0.0020(5) N11 0.0287(6) 0.0200(6) 0.0355(7) 0.0039(5) 0.0051(5) 0.0003(5) C2 0.0255(7) 0.0213(7) 0.0206(6) -0.0009(5) -0.0027(5) -0.0011(5) C4 0.0220(6) 0.0205(7) 0.0190(6) -0.0029(5) -0.0017(5) 0.0012(5) C5 0.0221(6) 0.0188(6) 0.0209(6) -0.0006(5) -0.0010(5) -0.0016(5) C6 0.0211(6) 0.0220(7) 0.0197(6) -0.0028(5) -0.0032(5) -0.0005(5) C8 0.0231(6) 0.0206(7) 0.0220(7) -0.0021(5) -0.0005(5) -0.0008(5) C12 0.0361(8) 0.0215(7) 0.0442(9) 0.0054(6) 0.0027(7) 0.0033(6) C13 0.0370(8) 0.0275(8) 0.0378(8) 0.0018(6) 0.0103(7) -0.0036(6) C14 0.0252(6) 0.0226(7) 0.0222(7) -0.0028(5) -0.0011(5) 0.0004(5) C17 0.0366(8) 0.0228(7) 0.0361(8) -0.0007(6) 0.0002(6) 0.0092(6) C18 0.0181(6) 0.0238(7) 0.0262(7) -0.0021(5) 0.0005(5) 0.0000(5) C19 0.0216(6) 0.0171(6) 0.0232(7) 0.0016(5) 0.0015(5) -0.0015(5) C20 0.0209(6) 0.0262(7) 0.0281(7) -0.0007(6) 0.0004(6) -0.0001(5) C21 0.0326(7) 0.0302(8) 0.0286(8) 0.0004(6) -0.0068(6) -0.0058(6) C22 0.0435(9) 0.0267(8) 0.0232(7) -0.0037(6) 0.0028(6) -0.0030(6) C23 0.0295(7) 0.0332(8) 0.0333(8) -0.0056(6) 0.0057(6) 0.0055(6) C24 0.0226(6) 0.0285(7) 0.0320(8) -0.0035(6) -0.0026(6) 0.0023(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 O15 C14 1.2009(15) . ? O16 C14 1.3317(15) . ? O16 C17 1.4550(16) . ? N1 C6 1.3407(16) . ? N1 C2 1.3635(16) . ? N3 C4 1.3402(16) . ? N3 C2 1.3524(16) . ? N7 C8 1.3212(16) . ? N7 C5 1.3778(16) . ? N9 C4 1.3710(16) . ? N9 C8 1.3910(15) . ? N9 C18 1.4645(15) . ? N10 C6 1.3339(17) . ? N10 H10B 0.886(18) . ? N10 H10A 0.897(16) . ? N11 C2 1.3590(17) . ? N11 C13 1.4480(17) . ? N11 C12 1.4582(17) . ? C4 C5 1.3890(17) . ? C5 C6 1.4177(18) . ? C8 C14 1.4895(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.5101(18) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.3830(18) . ? C19 C24 1.3892(17) . ? C20 C21 1.391(2) . ? C20 H20A 0.9500 . ? C21 C22 1.3717(19) . ? C21 H21A 0.9500 . ? C22 C23 1.384(2) . ? C22 H22A 0.9500 . ? C23 C24 1.383(2) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? 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 C14 O16 C17 115.23(10) . . ? C6 N1 C2 118.56(11) . . ? C4 N3 C2 110.96(11) . . ? C8 N7 C5 104.23(10) . . ? C4 N9 C8 105.77(10) . . ? C4 N9 C18 123.17(10) . . ? C8 N9 C18 131.07(10) . . ? C6 N10 H10B 124.7(10) . . ? C6 N10 H10A 120.2(10) . . ? H10B N10 H10A 115.0(14) . . ? C2 N11 C13 121.45(11) . . ? C2 N11 C12 120.24(12) . . ? C13 N11 C12 118.05(11) . . ? N3 C2 N11 116.96(12) . . ? N3 C2 N1 127.98(12) . . ? N11 C2 N1 115.06(11) . . ? N3 C4 N9 126.57(11) . . ? N3 C4 C5 127.49(12) . . ? N9 C4 C5 105.94(11) . . ? N7 C5 C4 111.09(11) . . ? N7 C5 C6 132.66(12) . . ? C4 C5 C6 116.25(11) . . ? N10 C6 N1 118.30(12) . . ? N10 C6 C5 122.98(12) . . ? N1 C6 C5 118.72(11) . . ? N7 C8 N9 112.97(11) . . ? N7 C8 C14 121.27(11) . . ? N9 C8 C14 125.76(11) . . ? N11 C12 H12A 109.5 . . ? N11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N11 C13 H13A 109.5 . . ? N11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O15 C14 O16 124.58(12) . . ? O15 C14 C8 122.91(12) . . ? O16 C14 C8 112.50(11) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N9 C18 C19 114.39(10) . . ? N9 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? N9 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C24 118.65(13) . . ? C20 C19 C18 123.17(11) . . ? C24 C19 C18 118.08(11) . . ? C19 C20 C21 120.50(12) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C22 C21 C20 120.44(13) . . ? C22 C21 H21A 119.8 . . ? C20 C21 H21A 119.8 . . ? C21 C22 C23 119.55(13) . . ? C21 C22 H22A 120.2 . . ? C23 C22 H22A 120.2 . . ? C24 C23 C22 120.14(13) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C19 120.72(13) . . ? C23 C24 H24A 119.6 . . ? C19 C24 H24A 119.6 . . ? 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 N10 H10B N7 0.886(18) 2.204(17) 3.0284(17) 154.5(14) 2_566 N10 H10A O15 0.897(16) 2.251(15) 2.8682(15) 125.6(12) 2_566 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.200 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.044 # Formatted by publCIF