data_nci97a # compound 4b in NO-amide paper _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 N4 O3' _chemical_formula_sum 'C20 H18 N4 O3' _chemical_formula_weight 362.38 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.3109(19) _cell_length_b 10.8087(9) _cell_length_c 20.0132(16) _cell_angle_alpha 90.00 _cell_angle_beta 109.785(4) _cell_angle_gamma 90.00 _cell_volume 3727.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2383 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.17 _exptl_crystal_description 'rod' _exptl_crystal_colour 'colourless' _exptl_crystal_size_min 0.082 _exptl_crystal_size_mid 0.101 _exptl_crystal_size_max 0.375 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.090 ############################################################################## # # # 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 0.9671 _exptl_absorpt_correction_T_max 0.9927 _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 20155 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.33 _reflns_number_total 4639 _reflns_number_gt 2667 _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^)+(0.0788P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4639 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 0.839 _refine_ls_restrained_S_all 0.839 _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 O1 O 0.31214(7) 0.59536(13) 0.18133(7) 0.0301(3) Uani 1 1 d . . . N1 N 0.25438(9) 0.59314(13) 0.12478(8) 0.0193(3) Uani 1 1 d . . . O2 O 0.18126(7) 0.60057(12) 0.18979(7) 0.0247(3) Uani 1 1 d . . . N2 N 0.18326(9) 0.59518(14) 0.12038(8) 0.0229(4) Uani 1 1 d . . . C3 C 0.10012(11) 0.6070(2) 0.18426(11) 0.0336(5) Uani 1 1 d . . . H3A H 0.0754 0.5247 0.1725 0.040 Uiso 1 1 calc R . . H3B H 0.0718 0.6662 0.1466 0.040 Uiso 1 1 calc R . . N3 N 0.26732(9) 0.60012(13) 0.05960(8) 0.0213(3) Uani 1 1 d . . . C4 C 0.09876(10) 0.64971(18) 0.25512(10) 0.0265(4) Uani 1 1 d . . . C5 C 0.10133(11) 0.77574(19) 0.27007(11) 0.0303(5) Uani 1 1 d . . . H5A H 0.1043 0.8338 0.2354 0.036 Uiso 1 1 calc R . . C6 C 0.09965(11) 0.8174(2) 0.33510(11) 0.0351(5) Uani 1 1 d . . . H6A H 0.1015 0.9035 0.3449 0.042 Uiso 1 1 calc R . . C7 C 0.09535(12) 0.7336(2) 0.38539(11) 0.0369(5) Uani 1 1 d . . . H7A H 0.0940 0.7620 0.4299 0.044 Uiso 1 1 calc R . . C8 C 0.09294(11) 0.6090(2) 0.37137(11) 0.0360(5) Uani 1 1 d . . . H8A H 0.0901 0.5515 0.4063 0.043 Uiso 1 1 calc R . . C9 C 0.09462(11) 0.56689(19) 0.30680(11) 0.0309(5) Uani 1 1 d . . . H9A H 0.0929 0.4805 0.2976 0.037 Uiso 1 1 calc R . . O10 O 0.23572(8) 0.39117(11) 0.04589(7) 0.0268(3) Uani 1 1 d . . . C10 C 0.25618(10) 0.49088(15) 0.02693(9) 0.0185(4) Uani 1 1 d . . . C11 C 0.27293(9) 0.49571(15) -0.04153(9) 0.0175(4) Uani 1 1 d . . . C12 C 0.28416(10) 0.38458(16) -0.07104(9) 0.0179(4) Uani 1 1 d . . . H12A H 0.2816 0.3091 -0.0476 0.021 Uiso 1 1 calc R . . N13 N 0.29864(8) 0.38223(13) -0.13266(8) 0.0182(3) Uani 1 1 d . . . C14 C 0.29961(10) 0.48678(16) -0.16890(9) 0.0218(4) Uani 1 1 d . . . H14A H 0.3084 0.4830 -0.2130 0.026 Uiso 1 1 calc R . . C15 C 0.28777(11) 0.59898(16) -0.14193(10) 0.0245(4) Uani 1 1 d . . . H15A H 0.2880 0.6728 -0.1676 0.029 Uiso 1 1 calc R . . C16 C 0.27553(10) 0.60467(16) -0.07745(10) 0.0215(4) Uani 1 1 d . . . H16A H 0.2690 0.6823 -0.0580 0.026 Uiso 1 1 calc R . . C17 C 0.31840(10) 0.26239(15) -0.15992(10) 0.0204(4) Uani 1 1 d . . . H17A H 0.3018 0.2648 -0.2124 0.025 Uiso 1 1 calc R . . H17B H 0.2907 0.1936 -0.1461 0.025 Uiso 1 1 calc R . . C18 C 0.40508(11) 0.24117(16) -0.12924(10) 0.0213(4) Uani 1 1 d . . . C19 C 0.43639(11) 0.17553(17) -0.06651(10) 0.0256(4) Uani 1 1 d . . . H19A H 0.4030 0.1394 -0.0445 0.031 Uiso 1 1 calc R . . C20 C 0.51594(12) 0.16230(19) -0.03584(11) 0.0339(5) Uani 1 1 d . . . H20A H 0.5370 0.1168 0.0070 0.041 Uiso 1 1 calc R . . C21 C 0.56475(12) 0.2150(2) -0.06729(13) 0.0394(6) Uani 1 1 d . . . H21A H 0.6194 0.2075 -0.0456 0.047 Uiso 1 1 calc R . . C22 C 0.53418(13) 0.2786(2) -0.13025(14) 0.0446(6) Uani 1 1 d . . . H22A H 0.5677 0.3138 -0.1524 0.053 Uiso 1 1 calc R . . C23 C 0.45436(12) 0.29122(19) -0.16142(12) 0.0344(5) Uani 1 1 d . . . H23A H 0.4335 0.3345 -0.2051 0.041 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 O1 0.0239(7) 0.0486(9) 0.0171(7) 0.0002(6) 0.0059(6) -0.0005(6) N1 0.0272(8) 0.0172(8) 0.0155(8) -0.0006(6) 0.0098(7) -0.0003(6) O2 0.0236(7) 0.0358(8) 0.0180(7) -0.0015(5) 0.0113(5) 0.0012(5) N2 0.0278(9) 0.0267(9) 0.0166(8) -0.0008(6) 0.0106(7) 0.0015(6) C3 0.0226(10) 0.0508(13) 0.0307(12) -0.0116(10) 0.0132(9) -0.0028(9) N3 0.0333(9) 0.0184(8) 0.0171(8) -0.0025(6) 0.0149(7) -0.0032(6) C4 0.0172(9) 0.0375(11) 0.0264(11) -0.0045(9) 0.0093(8) -0.0012(8) C5 0.0276(11) 0.0364(12) 0.0307(12) 0.0005(9) 0.0148(9) -0.0041(9) C6 0.0306(11) 0.0391(12) 0.0377(13) -0.0125(10) 0.0140(10) -0.0045(9) C7 0.0288(11) 0.0606(15) 0.0225(11) -0.0066(10) 0.0101(9) -0.0046(10) C8 0.0252(11) 0.0553(15) 0.0279(12) 0.0095(10) 0.0094(9) 0.0000(10) C9 0.0238(10) 0.0336(11) 0.0356(12) 0.0013(9) 0.0105(9) 0.0005(8) O10 0.0451(8) 0.0166(6) 0.0253(7) -0.0002(5) 0.0207(6) -0.0042(6) C10 0.0203(9) 0.0194(9) 0.0172(9) 0.0022(7) 0.0082(7) 0.0025(7) C11 0.0203(9) 0.0171(8) 0.0154(9) -0.0013(7) 0.0063(7) -0.0005(7) C12 0.0202(9) 0.0184(9) 0.0157(9) 0.0023(7) 0.0071(7) -0.0003(7) N13 0.0214(8) 0.0176(7) 0.0162(8) -0.0009(6) 0.0072(6) -0.0002(6) C14 0.0303(10) 0.0225(9) 0.0147(9) 0.0011(7) 0.0106(8) -0.0025(8) C15 0.0358(11) 0.0192(9) 0.0213(10) 0.0025(7) 0.0134(9) 0.0000(8) C16 0.0295(10) 0.0171(9) 0.0193(10) 0.0002(7) 0.0101(8) 0.0002(7) C17 0.0277(10) 0.0174(9) 0.0184(9) -0.0035(7) 0.0107(8) 0.0002(7) C18 0.0246(10) 0.0198(9) 0.0216(10) -0.0022(7) 0.0104(8) 0.0004(7) C19 0.0304(11) 0.0239(10) 0.0243(11) -0.0016(8) 0.0115(9) 0.0003(8) C20 0.0332(12) 0.0341(12) 0.0299(12) -0.0011(9) 0.0047(10) 0.0062(9) C21 0.0245(11) 0.0404(13) 0.0501(15) -0.0047(11) 0.0085(10) 0.0037(9) C22 0.0312(12) 0.0486(14) 0.0627(18) 0.0054(12) 0.0273(12) -0.0002(10) C23 0.0337(12) 0.0393(12) 0.0363(13) 0.0080(10) 0.0197(10) 0.0045(9) _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 O1 N1 1.2608(18) . ? N1 N2 1.276(2) . ? N1 N3 1.404(2) . ? O2 N2 1.4030(19) . ? O2 C3 1.454(2) . ? C3 C4 1.499(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N3 C10 1.332(2) . ? C4 C9 1.389(3) . ? C4 C5 1.392(3) . ? C5 C6 1.387(3) . ? C5 H5A 0.9500 . ? C6 C7 1.376(3) . ? C6 H6A 0.9500 . ? C7 C8 1.374(3) . ? C7 H7A 0.9500 . ? C8 C9 1.380(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? O10 C10 1.2417(19) . ? C10 C11 1.503(2) . ? C11 C12 1.384(2) . ? C11 C16 1.389(2) . ? C12 N13 1.346(2) . ? C12 H12A 0.9500 . ? N13 C14 1.346(2) . ? N13 C17 1.497(2) . ? C14 C15 1.374(2) . ? C14 H14A 0.9500 . ? C15 C16 1.384(2) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C18 1.513(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C23 1.384(3) . ? C18 C19 1.386(3) . ? C19 C20 1.383(3) . ? C19 H19A 0.9500 . ? C20 C21 1.379(3) . ? C20 H20A 0.9500 . ? C21 C22 1.377(3) . ? C21 H21A 0.9500 . ? C22 C23 1.388(3) . ? C22 H22A 0.9500 . ? C23 H23A 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 126.03(15) . . ? O1 N1 N3 118.60(14) . . ? N2 N1 N3 115.11(14) . . ? N2 O2 C3 107.16(13) . . ? N1 N2 O2 107.50(13) . . ? O2 C3 C4 106.66(15) . . ? O2 C3 H3A 110.4 . . ? C4 C3 H3A 110.4 . . ? O2 C3 H3B 110.4 . . ? C4 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? C10 N3 N1 111.24(13) . . ? C9 C4 C5 118.49(19) . . ? C9 C4 C3 121.91(19) . . ? C5 C4 C3 119.60(19) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C7 C6 C5 119.9(2) . . ? C7 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C8 C7 C6 120.1(2) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C9 120.4(2) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C4 C9 C8 120.6(2) . . ? C4 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? O10 C10 N3 129.16(16) . . ? O10 C10 C11 118.98(15) . . ? N3 C10 C11 111.85(14) . . ? C12 C11 C16 118.61(16) . . ? C12 C11 C10 117.67(15) . . ? C16 C11 C10 123.69(15) . . ? N13 C12 C11 120.72(15) . . ? N13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C14 N13 C12 121.35(15) . . ? C14 N13 C17 118.76(15) . . ? C12 N13 C17 119.80(14) . . ? N13 C14 C15 119.78(17) . . ? N13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? C14 C15 C16 120.15(17) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C11 119.32(16) . . ? C15 C16 H16A 120.3 . . ? C11 C16 H16A 120.3 . . ? N13 C17 C18 109.45(14) . . ? N13 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? N13 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? C23 C18 C19 119.12(18) . . ? C23 C18 C17 120.77(17) . . ? C19 C18 C17 120.06(16) . . ? C20 C19 C18 120.37(18) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C22 C21 C20 119.9(2) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C18 C23 C22 120.4(2) . . ? C18 C23 H23A 119.8 . . ? C22 C23 H23A 119.8 . . ? 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 N2 O2 0.1(2) . . . . ? N3 N1 N2 O2 -173.95(12) . . . . ? C3 O2 N2 N1 178.14(14) . . . . ? N2 O2 C3 C4 -163.76(15) . . . . ? O1 N1 N3 C10 106.09(17) . . . . ? N2 N1 N3 C10 -79.39(18) . . . . ? O2 C3 C4 C9 -95.1(2) . . . . ? O2 C3 C4 C5 85.2(2) . . . . ? C9 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 C6 179.60(17) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C5 C4 C9 C8 0.1(3) . . . . ? C3 C4 C9 C8 -179.57(17) . . . . ? C7 C8 C9 C4 0.0(3) . . . . ? N1 N3 C10 O10 1.3(3) . . . . ? N1 N3 C10 C11 -177.71(13) . . . . ? O10 C10 C11 C12 -16.2(2) . . . . ? N3 C10 C11 C12 162.97(15) . . . . ? O10 C10 C11 C16 161.94(16) . . . . ? N3 C10 C11 C16 -18.9(2) . . . . ? C16 C11 C12 N13 1.1(3) . . . . ? C10 C11 C12 N13 179.35(15) . . . . ? C11 C12 N13 C14 -2.7(3) . . . . ? C11 C12 N13 C17 173.93(15) . . . . ? C12 N13 C14 C15 1.8(3) . . . . ? C17 N13 C14 C15 -174.81(16) . . . . ? N13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C11 -2.0(3) . . . . ? C12 C11 C16 C15 1.2(3) . . . . ? C10 C11 C16 C15 -176.93(16) . . . . ? C14 N13 C17 C18 88.78(18) . . . . ? C12 N13 C17 C18 -87.91(18) . . . . ? N13 C17 C18 C23 -85.6(2) . . . . ? N13 C17 C18 C19 91.62(19) . . . . ? C23 C18 C19 C20 1.2(3) . . . . ? C17 C18 C19 C20 -176.00(16) . . . . ? C18 C19 C20 C21 0.4(3) . . . . ? C19 C20 C21 C22 -1.5(3) . . . . ? C20 C21 C22 C23 1.0(3) . . . . ? C19 C18 C23 C22 -1.7(3) . . . . ? C17 C18 C23 C22 175.51(18) . . . . ? C21 C22 C23 C18 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.575 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.055