data_nci102 # compound 4b on NO-amide paper _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N3 O3' _chemical_formula_sum 'C16 H17 N3 O3' _chemical_formula_weight 299.33 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 5.429(4) _cell_length_b 8.743(5) _cell_length_c 16.342(11) _cell_angle_alpha 96.30(3) _cell_angle_beta 96.60(3) _cell_angle_gamma 92.33(3) _cell_volume 764.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 181 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 17.50 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_min 0.011 _exptl_crystal_size_mid 0.047 _exptl_crystal_size_max 0.256 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.092 ############################################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # # # ############################################################################## _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000c)' _exptl_absorpt_correction_T_min 0.9769 _exptl_absorpt_correction_T_max 0.9990 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) # APEX 2 parameters _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 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2961 _diffrn_reflns_av_R_equivalents 0.2410 _diffrn_reflns_av_sigmaI/netI 0.3679 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 23.30 _reflns_number_total 2034 _reflns_number_gt 574 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001)' _computing_data_reduction ; Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _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^)+(0.1000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2034 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2446 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.2435 _refine_ls_wR_factor_gt 0.1677 _refine_ls_goodness_of_fit_ref 0.703 _refine_ls_restrained_S_all 0.703 _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 0.4969(14) 0.3291(8) 0.3858(4) 0.039(2) Uani 1 1 d . . . O2 O 0.3625(10) 0.5475(7) 0.3665(3) 0.0409(17) Uani 1 1 d . . . N3 N 0.4537(14) 0.1638(8) 0.3777(5) 0.046(2) Uani 1 1 d . . . C4 C 0.1360(15) 0.6200(10) 0.3405(5) 0.039(2) Uani 1 1 d . . . H4A H 0.1354 0.7221 0.3733 0.047 Uiso 1 1 calc R . . H4B H -0.0078 0.5564 0.3524 0.047 Uiso 1 1 calc R . . O1 O 0.7062(11) 0.3843(7) 0.4148(4) 0.0498(19) Uani 1 1 d . . . N2 N 0.3064(13) 0.3905(8) 0.3546(4) 0.038(2) Uani 1 1 d . . . C5 C 0.1067(15) 0.6405(10) 0.2492(6) 0.035(2) Uani 1 1 d . . . C6 C 0.2545(15) 0.5754(11) 0.1935(6) 0.045(3) Uani 1 1 d . . . H6A H 0.3850 0.5131 0.2114 0.054 Uiso 1 1 calc R . . C7 C 0.2118(16) 0.6011(11) 0.1112(6) 0.051(3) Uani 1 1 d . . . H7A H 0.3216 0.5612 0.0739 0.061 Uiso 1 1 calc R . . C8 C 0.0174(16) 0.6816(11) 0.0818(6) 0.047(3) Uani 1 1 d . . . H8A H -0.0149 0.6924 0.0244 0.057 Uiso 1 1 calc R . . C9 C -0.1305(17) 0.7469(11) 0.1374(6) 0.053(3) Uani 1 1 d . . . H9A H -0.2612 0.8086 0.1190 0.063 Uiso 1 1 calc R . . C10 C -0.0895(15) 0.7227(11) 0.2201(6) 0.046(3) Uani 1 1 d . . . H10A H -0.1986 0.7635 0.2574 0.055 Uiso 1 1 calc R . . C11 C 0.3166(15) 0.1031(12) 0.4355(6) 0.041(3) Uani 1 1 d . . . O11 O 0.2849(11) -0.0368(7) 0.4294(4) 0.056(2) Uani 1 1 d . . . C12 C 0.2175(15) 0.2120(11) 0.4988(5) 0.050(3) Uani 1 1 d . . . H12A H 0.1516 0.1542 0.5403 0.075 Uiso 1 1 calc R . . H12B H 0.0845 0.2681 0.4718 0.075 Uiso 1 1 calc R . . H12C H 0.3512 0.2853 0.5259 0.075 Uiso 1 1 calc R . . C13 C 0.6139(16) 0.0759(11) 0.3262(6) 0.050(3) Uani 1 1 d . . . H13A H 0.5701 -0.0354 0.3248 0.061 Uiso 1 1 calc R . . H13B H 0.7886 0.0951 0.3514 0.061 Uiso 1 1 calc R . . C14 C 0.5903(16) 0.1183(11) 0.2382(6) 0.042(2) Uani 1 1 d . . . C15 C 0.3880(16) 0.0573(11) 0.1837(6) 0.051(3) Uani 1 1 d . . . H15A H 0.2688 -0.0111 0.2009 0.061 Uiso 1 1 calc R . . C16 C 0.3620(16) 0.0968(11) 0.1046(7) 0.053(3) Uani 1 1 d . . . H16A H 0.2245 0.0540 0.0666 0.064 Uiso 1 1 calc R . . C17 C 0.5327(18) 0.1986(12) 0.0783(6) 0.059(3) Uani 1 1 d . . . H17A H 0.5127 0.2244 0.0230 0.070 Uiso 1 1 calc R . . C18 C 0.7304(16) 0.2611(12) 0.1337(6) 0.056(3) Uani 1 1 d . . . H18A H 0.8469 0.3324 0.1174 0.067 Uiso 1 1 calc R . . C19 C 0.7580(16) 0.2189(11) 0.2136(6) 0.051(3) Uani 1 1 d . . . H19A H 0.8958 0.2607 0.2517 0.061 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 N1 0.038(5) 0.042(6) 0.039(5) 0.005(4) 0.011(4) 0.012(4) O2 0.050(4) 0.025(4) 0.046(4) 0.002(3) 0.003(3) -0.001(3) N3 0.065(6) 0.022(5) 0.054(6) 0.006(5) 0.016(4) 0.009(4) C4 0.037(6) 0.023(5) 0.057(7) -0.004(5) 0.014(4) 0.007(4) O1 0.036(4) 0.057(5) 0.057(5) 0.021(4) -0.004(3) -0.007(3) N2 0.043(5) 0.017(5) 0.051(5) -0.008(4) 0.008(4) 0.001(3) C5 0.027(5) 0.026(6) 0.049(7) -0.001(5) 0.005(4) -0.005(4) C6 0.034(6) 0.046(7) 0.056(8) 0.013(6) 0.006(5) -0.003(4) C7 0.037(6) 0.058(7) 0.061(8) 0.002(6) 0.023(5) 0.003(5) C8 0.039(6) 0.053(7) 0.049(7) 0.004(6) 0.002(5) 0.002(5) C9 0.046(6) 0.063(8) 0.051(8) 0.008(6) 0.008(5) 0.018(5) C10 0.036(6) 0.047(7) 0.051(7) -0.011(6) 0.011(5) 0.003(5) C11 0.032(6) 0.036(7) 0.053(7) 0.000(6) -0.005(5) 0.006(4) O11 0.062(5) 0.031(4) 0.075(5) -0.004(4) 0.014(3) -0.009(3) C12 0.039(6) 0.066(7) 0.042(7) -0.006(6) 0.010(4) -0.001(5) C13 0.056(6) 0.036(6) 0.064(8) 0.009(6) 0.019(5) 0.016(5) C14 0.040(6) 0.048(6) 0.038(7) 0.007(5) 0.002(5) 0.008(5) C15 0.036(6) 0.058(7) 0.057(8) 0.005(6) 0.004(5) -0.006(5) C16 0.038(6) 0.060(8) 0.055(8) -0.009(6) -0.004(5) -0.006(5) C17 0.062(7) 0.076(9) 0.040(7) 0.013(6) 0.009(5) -0.005(6) C18 0.046(7) 0.072(8) 0.053(8) 0.010(7) 0.019(5) -0.013(5) C19 0.041(6) 0.063(8) 0.046(7) -0.002(6) 0.012(5) -0.009(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 N1 O1 1.237(7) . ? N1 N2 1.266(8) . ? N1 N3 1.444(10) . ? O2 N2 1.381(8) . ? O2 C4 1.448(9) . ? N3 C11 1.403(12) . ? N3 C13 1.462(11) . ? C4 C5 1.513(12) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.374(12) . ? C5 C10 1.378(11) . ? C6 C7 1.383(12) . ? C6 H6A 0.9500 . ? C7 C8 1.364(12) . ? C7 H7A 0.9500 . ? C8 C9 1.373(12) . ? C8 H8A 0.9500 . ? C9 C10 1.386(12) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 O11 1.220(10) . ? C11 C12 1.489(13) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.517(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.364(12) . ? C14 C15 1.381(11) . ? C15 C16 1.368(12) . ? C15 H15A 0.9500 . ? C16 C17 1.394(12) . ? C16 H16A 0.9500 . ? C17 C18 1.375(12) . ? C17 H17A 0.9500 . ? C18 C19 1.389(11) . ? C18 H18A 0.9500 . ? C19 H19A 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 O1 N1 N2 131.6(8) . . ? O1 N1 N3 118.2(7) . . ? N2 N1 N3 109.9(7) . . ? N2 O2 C4 106.4(6) . . ? C11 N3 N1 117.1(7) . . ? C11 N3 C13 125.0(8) . . ? N1 N3 C13 115.5(7) . . ? O2 C4 C5 112.8(7) . . ? O2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? O2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N1 N2 O2 105.9(6) . . ? C6 C5 C10 118.5(9) . . ? C6 C5 C4 124.1(8) . . ? C10 C5 C4 117.3(9) . . ? C5 C6 C7 119.5(9) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C8 C7 C6 122.2(9) . . ? C8 C7 H7A 118.9 . . ? C6 C7 H7A 118.9 . . ? C7 C8 C9 118.3(10) . . ? C7 C8 H8A 120.9 . . ? C9 C8 H8A 120.9 . . ? C8 C9 C10 120.1(9) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C5 C10 C9 121.2(9) . . ? C5 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? O11 C11 N3 116.8(9) . . ? O11 C11 C12 124.6(10) . . ? N3 C11 C12 118.5(9) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 112.3(8) . . ? N3 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N3 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C19 C14 C15 120.2(9) . . ? C19 C14 C13 121.4(8) . . ? C15 C14 C13 118.3(9) . . ? C16 C15 C14 118.9(9) . . ? C16 C15 H15A 120.5 . . ? C14 C15 H15A 120.5 . . ? C15 C16 C17 121.6(9) . . ? C15 C16 H16A 119.2 . . ? C17 C16 H16A 119.2 . . ? C18 C17 C16 118.9(9) . . ? C18 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? C17 C18 C19 119.4(9) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? C14 C19 C18 121.0(9) . . ? C14 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 N3 C11 104.7(8) . . . . ? N2 N1 N3 C11 -80.1(9) . . . . ? O1 N1 N3 C13 -58.5(10) . . . . ? N2 N1 N3 C13 116.7(8) . . . . ? N2 O2 C4 C5 -88.8(8) . . . . ? O1 N1 N2 O2 -6.8(11) . . . . ? N3 N1 N2 O2 178.9(6) . . . . ? C4 O2 N2 N1 -173.0(7) . . . . ? O2 C4 C5 C6 10.3(11) . . . . ? O2 C4 C5 C10 -173.4(7) . . . . ? C10 C5 C6 C7 3.6(13) . . . . ? C4 C5 C6 C7 179.9(8) . . . . ? C5 C6 C7 C8 -4.1(14) . . . . ? C6 C7 C8 C9 4.1(15) . . . . ? C7 C8 C9 C10 -3.7(14) . . . . ? C6 C5 C10 C9 -3.4(13) . . . . ? C4 C5 C10 C9 -179.9(8) . . . . ? C8 C9 C10 C5 3.5(14) . . . . ? N1 N3 C11 O11 -178.6(7) . . . . ? C13 N3 C11 O11 -17.1(13) . . . . ? N1 N3 C11 C12 2.3(11) . . . . ? C13 N3 C11 C12 163.7(8) . . . . ? C11 N3 C13 C14 139.2(8) . . . . ? N1 N3 C13 C14 -59.1(10) . . . . ? N3 C13 C14 C19 98.5(11) . . . . ? N3 C13 C14 C15 -78.9(11) . . . . ? C19 C14 C15 C16 1.3(15) . . . . ? C13 C14 C15 C16 178.8(10) . . . . ? C14 C15 C16 C17 -0.9(16) . . . . ? C15 C16 C17 C18 -0.4(16) . . . . ? C16 C17 C18 C19 1.4(16) . . . . ? C15 C14 C19 C18 -0.4(15) . . . . ? C13 C14 C19 C18 -177.8(9) . . . . ? C17 C18 C19 C14 -0.9(16) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.272 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.073