# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Zhang, Zhenfeng' _publ_contact_author_email zzf5188@sohu.com _publ_section_title ; N...P and O...P Interactions Rather Than "Directed" Hydrogen Bonding in the Crystal Packing of Ethyl (Z)-2-Cyano-3-[(4-alkoxyphenyl)amino]prop-2-enoates ; loop_ _publ_author_name 'Zhenfeng Zhang' 'Xiaopeng Xuan' 'Yonggang Yang' 'Yanbo Wu' 'Guisheng Zhang' # Attachment '- Incorporation of 1 and 2.cif' data_I _database_code_depnum_ccdc_archive 'CCDC 812825' #TrackingRef '- Incorporation of 1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O3' _chemical_formula_weight 260.29 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 8.4186(10) _cell_length_b 12.5730(15) _cell_length_c 13.2177(15) _cell_angle_alpha 79.947(2) _cell_angle_beta 84.258(2) _cell_angle_gamma 79.707(2) _cell_volume 1352.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 26.23 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9739 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15248 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5218 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0665P)^2^+0.2061P] 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 5218 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C4 C 0.2219(2) 0.38475(15) 1.15963(13) 0.0466(4) Uani 1 1 d . . . C3 C 0.1678(2) 0.47778(15) 1.09201(13) 0.0491(4) Uani 1 1 d . . . H3 H 0.0792 0.5273 1.1119 0.059 Uiso 1 1 calc R . . C2 C 0.2451(2) 0.49805(15) 0.99429(13) 0.0484(4) Uani 1 1 d . . . H2 H 0.2084 0.5613 0.9493 0.058 Uiso 1 1 calc R . . C1 C 0.3754(2) 0.42513(15) 0.96375(13) 0.0462(4) Uani 1 1 d . . . C6 C 0.4316(2) 0.33259(16) 1.03174(14) 0.0562(5) Uani 1 1 d . . . H6 H 0.5210 0.2836 1.0120 0.067 Uiso 1 1 calc R . . C5 C 0.3550(2) 0.31245(16) 1.12955(14) 0.0559(5) Uani 1 1 d . . . H5 H 0.3934 0.2501 1.1750 0.067 Uiso 1 1 calc R . . C13 C 0.0009(2) 0.41699(17) 1.28514(15) 0.0600(5) Uani 1 1 d . . . H13A H -0.0756 0.4151 1.2355 0.072 Uiso 1 1 calc R . . H13B H 0.0087 0.4929 1.2861 0.072 Uiso 1 1 calc R . . C14 C -0.0548(3) 0.36429(19) 1.38941(16) 0.0749(7) Uani 1 1 d . . . H14A H -0.0722(4) 0.2920(10) 1.38622(16) 0.112 Uiso 1 1 calc R . . H14B H -0.1536(14) 0.4064(6) 1.4124(4) 0.112 Uiso 1 1 calc R . . H14C H 0.0258(11) 0.3607(2) 1.4365(7) 0.112 Uiso 1 1 calc R . . C7 C 0.5659(2) 0.39020(15) 0.81596(13) 0.0487(4) Uani 1 1 d . . . H7 H 0.6076 0.3222 0.8519 0.058 Uiso 1 1 calc R . . C8 C 0.6334(2) 0.41979(15) 0.71728(13) 0.0469(4) Uani 1 1 d . . . C10 C 0.7615(2) 0.34496(16) 0.67778(13) 0.0529(5) Uani 1 1 d . . . C9 C 0.5763(2) 0.52493(15) 0.65596(13) 0.0473(4) Uani 1 1 d . . . C11 C 0.6048(3) 0.64595(16) 0.49959(14) 0.0591(5) Uani 1 1 d . . . H11A H 0.6170 0.7052 0.5348 0.071 Uiso 1 1 calc R . . H11B H 0.4919 0.6534 0.4860 0.071 Uiso 1 1 calc R . . C12 C 0.7085(3) 0.65010(18) 0.40101(15) 0.0666(6) Uani 1 1 d . . . H12A H 0.8213(15) 0.6407(2) 0.4157(2) 0.100 Uiso 1 1 calc R . . H12B H 0.6789(5) 0.7204(9) 0.3579(6) 0.100 Uiso 1 1 calc R . . H12C H 0.6928(3) 0.5919(8) 0.3654(5) 0.100 Uiso 1 1 calc R . . N1 N 0.44759(18) 0.45088(12) 0.86254(11) 0.0502(4) Uani 1 1 d . . . H1 H 0.4095 0.5132 0.8280 0.060 Uiso 1 1 calc R . . N2 N 0.8644(2) 0.28356(15) 0.64759(14) 0.0783(6) Uani 1 1 d . . . O3 O 0.15520(15) 0.35825(11) 1.25738(9) 0.0573(4) Uani 1 1 d . . . O1 O 0.46561(16) 0.59182(11) 0.68483(10) 0.0621(4) Uani 1 1 d . . . O2 O 0.65604(15) 0.54111(10) 0.56279(9) 0.0522(3) Uani 1 1 d . . . O4 O 1.08241(19) -0.20070(12) 0.84972(11) 0.0725(4) Uani 1 1 d . . . O5 O 0.90739(15) -0.14131(10) 0.97546(9) 0.0532(3) Uani 1 1 d . . . O6 O 1.41873(16) 0.05320(10) 0.28446(9) 0.0595(4) Uani 1 1 d . . . N4 N 0.7399(2) 0.12946(15) 0.89939(14) 0.0737(5) Uani 1 1 d . . . N3 N 1.11804(19) -0.05215(13) 0.67523(12) 0.0557(4) Uani 1 1 d . . . H3A H 1.1475 -0.1178 0.7062 0.067 Uiso 1 1 calc R . . C18 C 1.3479(2) 0.02194(15) 0.38001(13) 0.0488(4) Uani 1 1 d . . . C17 C 1.3777(2) -0.08074(16) 0.43799(15) 0.0606(5) Uani 1 1 d . . . H17 H 1.4505 -0.1357 0.4116 0.073 Uiso 1 1 calc R . . C16 C 1.3010(3) -0.10324(16) 0.53474(15) 0.0612(5) Uani 1 1 d . . . H16 H 1.3236 -0.1729 0.5731 0.073 Uiso 1 1 calc R . . C15 C 1.1921(2) -0.02403(16) 0.57476(13) 0.0500(4) Uani 1 1 d . . . C20 C 1.1605(2) 0.07938(16) 0.51703(15) 0.0581(5) Uani 1 1 d . . . H20 H 1.0871 0.1340 0.5435 0.070 Uiso 1 1 calc R . . C19 C 1.2378(2) 0.10195(16) 0.41999(15) 0.0571(5) Uani 1 1 d . . . H19 H 1.2153 0.1715 0.3815 0.069 Uiso 1 1 calc R . . C27 C 1.5307(2) -0.02593(16) 0.23801(14) 0.0547(5) Uani 1 1 d . . . H27A H 1.4795 -0.0874 0.2314 0.066 Uiso 1 1 calc R . . H27B H 1.6225 -0.0529 0.2796 0.066 Uiso 1 1 calc R . . C28 C 1.5849(3) 0.02967(19) 0.13405(15) 0.0744(7) Uani 1 1 d . . . H28A H 1.4937(12) 0.0571(4) 0.0947(6) 0.112 Uiso 1 1 calc R . . H28B H 1.6584(10) -0.0213(7) 0.0998(5) 0.112 Uiso 1 1 calc R . . H28C H 1.6371(8) 0.0885(8) 0.14168(17) 0.112 Uiso 1 1 calc R . . C21 C 1.0100(2) 0.01119(16) 0.72535(14) 0.0531(5) Uani 1 1 d . . . H21 H 0.9756 0.0820 0.6923 0.064 Uiso 1 1 calc R . . C22 C 0.9427(2) -0.01889(15) 0.82401(13) 0.0503(5) Uani 1 1 d . . . C24 C 0.8297(2) 0.06221(16) 0.86701(14) 0.0525(3) Uani 1 1 d . . . C25 C 0.9463(3) -0.24796(15) 1.03776(15) 0.0582(5) Uani 1 1 d . . . H25A H 1.0605 -0.2634 1.0499 0.070 Uiso 1 1 calc R . . H25B H 0.9222 -0.3043 1.0028 0.070 Uiso 1 1 calc R . . C26 C 0.8455(3) -0.24608(17) 1.13806(16) 0.0733(7) Uani 1 1 d . . . H26A H 0.8734(5) -0.1927(7) 1.1729(5) 0.110 Uiso 1 1 calc R . . H26B H 0.8654(4) -0.3161(9) 1.1797(6) 0.110 Uiso 1 1 calc R . . H26C H 0.7341(15) -0.2282(3) 1.1250(2) 0.110 Uiso 1 1 calc R . . C23 C 0.9860(2) -0.12849(16) 0.88209(14) 0.0525(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 C4 0.0503(10) 0.0500(10) 0.0353(9) -0.0040(8) 0.0072(8) -0.0052(8) C3 0.0481(10) 0.0516(11) 0.0414(10) -0.0055(8) 0.0074(8) 0.0007(8) C2 0.0518(10) 0.0476(10) 0.0404(10) -0.0005(8) 0.0030(8) -0.0032(8) C1 0.0507(10) 0.0505(10) 0.0353(9) -0.0044(8) 0.0055(8) -0.0097(8) C6 0.0553(11) 0.0550(11) 0.0485(11) -0.0069(9) 0.0135(9) 0.0062(9) C5 0.0596(12) 0.0519(11) 0.0431(10) 0.0033(8) 0.0122(9) 0.0062(9) C13 0.0526(11) 0.0666(13) 0.0495(11) -0.0051(9) 0.0137(9) 0.0066(9) C14 0.0651(13) 0.0817(16) 0.0580(13) 0.0062(11) 0.0221(10) 0.0091(11) C7 0.0484(10) 0.0524(11) 0.0421(10) -0.0060(8) 0.0032(8) -0.0049(8) C8 0.0505(10) 0.0513(11) 0.0349(9) -0.0025(8) 0.0039(8) -0.0057(8) C10 0.0602(12) 0.0546(11) 0.0350(9) 0.0035(8) 0.0090(8) -0.0033(10) C9 0.0474(10) 0.0554(11) 0.0367(9) -0.0085(8) 0.0065(8) -0.0061(9) C11 0.0720(13) 0.0487(11) 0.0470(11) 0.0030(9) 0.0054(9) 0.0002(9) C12 0.0774(14) 0.0620(13) 0.0494(12) 0.0058(10) 0.0097(10) -0.0047(11) N1 0.0530(9) 0.0500(9) 0.0393(8) 0.0001(7) 0.0076(7) 0.0006(7) N2 0.0868(14) 0.0662(12) 0.0601(11) 0.0039(9) 0.0229(10) 0.0163(10) O3 0.0563(8) 0.0630(8) 0.0383(7) 0.0018(6) 0.0151(6) 0.0087(6) O1 0.0632(9) 0.0640(9) 0.0466(8) -0.0018(6) 0.0112(6) 0.0076(7) O2 0.0597(8) 0.0502(7) 0.0388(7) -0.0007(5) 0.0099(6) -0.0011(6) O4 0.0863(10) 0.0563(9) 0.0644(9) -0.0112(7) 0.0266(8) -0.0003(8) O5 0.0651(8) 0.0450(7) 0.0432(7) -0.0014(5) 0.0121(6) -0.0067(6) O6 0.0688(9) 0.0538(8) 0.0429(7) 0.0005(6) 0.0190(6) 0.0041(6) N4 0.0834(13) 0.0603(11) 0.0637(11) 0.0007(9) 0.0172(10) 0.0019(10) N3 0.0624(10) 0.0512(9) 0.0482(9) -0.0040(7) 0.0090(8) -0.0063(8) C18 0.0514(10) 0.0539(11) 0.0370(9) -0.0031(8) 0.0050(8) -0.0057(9) C17 0.0674(13) 0.0524(11) 0.0515(12) -0.0026(9) 0.0175(10) 0.0008(10) C16 0.0722(14) 0.0498(11) 0.0517(12) 0.0024(9) 0.0144(10) -0.0044(10) C15 0.0517(11) 0.0577(12) 0.0394(10) -0.0037(8) 0.0049(8) -0.0142(9) C20 0.0593(12) 0.0585(12) 0.0515(12) -0.0145(10) 0.0095(9) 0.0012(10) C19 0.0641(12) 0.0537(12) 0.0453(11) -0.0017(9) 0.0083(9) -0.0004(10) C27 0.0567(11) 0.0553(11) 0.0452(10) -0.0073(9) 0.0093(9) 0.0014(9) C28 0.0853(16) 0.0719(15) 0.0505(13) -0.0042(11) 0.0231(11) 0.0075(12) C21 0.0545(11) 0.0545(11) 0.0480(11) -0.0068(9) 0.0048(9) -0.0088(9) C22 0.0564(11) 0.0543(11) 0.0389(10) -0.0019(8) 0.0057(8) -0.0163(9) C24 0.0574(8) 0.0541(8) 0.0427(8) -0.0038(6) 0.0105(6) -0.0120(7) C25 0.0752(13) 0.0413(10) 0.0521(11) -0.0017(8) 0.0090(10) -0.0065(9) C26 0.1075(19) 0.0518(12) 0.0504(12) 0.0015(10) 0.0145(12) -0.0064(12) C23 0.0574(8) 0.0541(8) 0.0427(8) -0.0038(6) 0.0105(6) -0.0120(7) _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 C4 O3 1.366(2) . ? C4 C3 1.378(2) . ? C4 C5 1.383(2) . ? C3 C2 1.390(2) . ? C3 H3 0.9300 . ? C2 C1 1.374(2) . ? C2 H2 0.9300 . ? C1 C6 1.381(3) . ? C1 N1 1.421(2) . ? C6 C5 1.389(2) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C13 O3 1.423(2) . ? C13 C14 1.490(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9554 . ? C14 H14B 0.9554 . ? C14 H14C 0.9554 . ? C7 N1 1.313(2) . ? C7 C8 1.386(2) . ? C7 H7 0.9300 . ? C8 C10 1.420(3) . ? C8 C9 1.454(2) . ? C10 N2 1.143(2) . ? C9 O1 1.217(2) . ? C9 O2 1.344(2) . ? C11 O2 1.451(2) . ? C11 C12 1.493(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9707 . ? C12 H12B 0.9707 . ? C12 H12C 0.9707 . ? N1 H1 0.8600 . ? O4 C23 1.212(2) . ? O5 C23 1.339(2) . ? O5 C25 1.447(2) . ? O6 C18 1.365(2) . ? O6 C27 1.420(2) . ? N4 C24 1.142(2) . ? N3 C21 1.306(2) . ? N3 C15 1.424(2) . ? N3 H3A 0.8600 . ? C18 C17 1.376(3) . ? C18 C19 1.380(2) . ? C17 C16 1.381(3) . ? C17 H17 0.9300 . ? C16 C15 1.368(3) . ? C16 H16 0.9300 . ? C15 C20 1.383(3) . ? C20 C19 1.386(3) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? C27 C28 1.496(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9499 . ? C28 H28B 0.9499 . ? C28 H28C 0.9499 . ? C21 C22 1.386(2) . ? C21 H21 0.9300 . ? C22 C24 1.420(3) . ? C22 C23 1.459(3) . ? C25 C26 1.502(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9505 . ? C26 H26B 0.9505 . ? C26 H26C 0.9505 . ? 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 O3 C4 C3 124.70(16) . . ? O3 C4 C5 116.05(16) . . ? C3 C4 C5 119.23(16) . . ? C4 C3 C2 120.37(16) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C1 C2 C3 120.36(17) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C1 C6 119.51(16) . . ? C2 C1 N1 117.22(16) . . ? C6 C1 N1 123.26(16) . . ? C1 C6 C5 120.19(17) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C4 C5 C6 120.31(17) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? O3 C13 C14 108.02(16) . . ? O3 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? O3 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C7 C8 124.97(17) . . ? N1 C7 H7 117.5 . . ? C8 C7 H7 117.5 . . ? C7 C8 C10 118.19(16) . . ? C7 C8 C9 121.12(16) . . ? C10 C8 C9 120.69(15) . . ? N2 C10 C8 178.8(2) . . ? O1 C9 O2 122.74(16) . . ? O1 C9 C8 123.82(16) . . ? O2 C9 C8 113.44(15) . . ? O2 C11 C12 107.68(16) . . ? O2 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? O2 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? 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 . . ? C7 N1 C1 127.25(16) . . ? C7 N1 H1 116.4 . . ? C1 N1 H1 116.4 . . ? C4 O3 C13 118.15(14) . . ? C9 O2 C11 115.31(14) . . ? C23 O5 C25 115.64(14) . . ? C18 O6 C27 118.58(14) . . ? C21 N3 C15 126.89(17) . . ? C21 N3 H3A 116.6 . . ? C15 N3 H3A 116.6 . . ? O6 C18 C17 125.62(16) . . ? O6 C18 C19 115.77(16) . . ? C17 C18 C19 118.60(17) . . ? C18 C17 C16 120.92(18) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C15 C16 C17 120.63(18) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C15 C20 119.01(17) . . ? C16 C15 N3 117.93(17) . . ? C20 C15 N3 123.06(17) . . ? C15 C20 C19 120.31(18) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C18 C19 C20 120.52(18) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? O6 C27 C28 106.99(15) . . ? O6 C27 H27A 110.3 . . ? C28 C27 H27A 110.3 . . ? O6 C27 H27B 110.3 . . ? C28 C27 H27B 110.3 . . ? H27A C27 H27B 108.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N3 C21 C22 125.09(19) . . ? N3 C21 H21 117.5 . . ? C22 C21 H21 117.5 . . ? C21 C22 C24 117.03(17) . . ? C21 C22 C23 121.94(17) . . ? C24 C22 C23 121.03(16) . . ? N4 C24 C22 178.2(2) . . ? O5 C25 C26 107.49(15) . . ? O5 C25 H25A 110.2 . . ? C26 C25 H25A 110.2 . . ? O5 C25 H25B 110.2 . . ? C26 C25 H25B 110.2 . . ? H25A C25 H25B 108.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O4 C23 O5 123.26(17) . . ? O4 C23 C22 123.96(17) . . ? O5 C23 C22 112.78(16) . . ? 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 O3 C4 C3 C2 179.29(16) . . . . ? C5 C4 C3 C2 0.7(3) . . . . ? C4 C3 C2 C1 0.5(3) . . . . ? C3 C2 C1 C6 -1.5(3) . . . . ? C3 C2 C1 N1 179.57(16) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? N1 C1 C6 C5 -179.92(17) . . . . ? O3 C4 C5 C6 -179.69(17) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C1 C6 C5 C4 0.1(3) . . . . ? N1 C7 C8 C10 179.80(17) . . . . ? N1 C7 C8 C9 0.4(3) . . . . ? C7 C8 C10 N2 -3(12) . . . . ? C9 C8 C10 N2 176(100) . . . . ? C7 C8 C9 O1 -1.7(3) . . . . ? C10 C8 C9 O1 178.88(18) . . . . ? C7 C8 C9 O2 179.19(15) . . . . ? C10 C8 C9 O2 -0.2(2) . . . . ? C8 C7 N1 C1 -179.19(17) . . . . ? C2 C1 N1 C7 -175.65(17) . . . . ? C6 C1 N1 C7 5.4(3) . . . . ? C3 C4 O3 C13 13.7(3) . . . . ? C5 C4 O3 C13 -167.71(17) . . . . ? C14 C13 O3 C4 172.86(17) . . . . ? O1 C9 O2 C11 2.0(3) . . . . ? C8 C9 O2 C11 -178.96(15) . . . . ? C12 C11 O2 C9 178.71(16) . . . . ? C27 O6 C18 C17 1.4(3) . . . . ? C27 O6 C18 C19 -178.70(17) . . . . ? O6 C18 C17 C16 178.98(18) . . . . ? C19 C18 C17 C16 -0.9(3) . . . . ? C18 C17 C16 C15 0.7(3) . . . . ? C17 C16 C15 C20 -0.4(3) . . . . ? C17 C16 C15 N3 -179.55(18) . . . . ? C21 N3 C15 C16 -178.77(19) . . . . ? C21 N3 C15 C20 2.1(3) . . . . ? C16 C15 C20 C19 0.2(3) . . . . ? N3 C15 C20 C19 179.38(17) . . . . ? O6 C18 C19 C20 -179.13(17) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C15 C20 C19 C18 -0.4(3) . . . . ? C18 O6 C27 C28 178.55(17) . . . . ? C15 N3 C21 C22 -178.88(17) . . . . ? N3 C21 C22 C24 178.45(18) . . . . ? N3 C21 C22 C23 -1.1(3) . . . . ? C21 C22 C24 N4 -8(7) . . . . ? C23 C22 C24 N4 171(7) . . . . ? C23 O5 C25 C26 -179.52(17) . . . . ? C25 O5 C23 O4 0.9(3) . . . . ? C25 O5 C23 C22 -179.28(15) . . . . ? C21 C22 C23 O4 0.1(3) . . . . ? C24 C22 C23 O4 -179.44(19) . . . . ? C21 C22 C23 O5 -179.75(16) . . . . ? C24 C22 C23 O5 0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.316 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.031 data_II _database_code_depnum_ccdc_archive 'CCDC 812826' #TrackingRef '- Incorporation of 1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O3' _chemical_formula_weight 246.26 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 4.4026(14) _cell_length_b 10.667(3) _cell_length_c 13.823(4) _cell_angle_alpha 76.294(4) _cell_angle_beta 86.681(4) _cell_angle_gamma 89.165(4) _cell_volume 629.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4495 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2273 _reflns_number_gt 1402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0686P)^2^+0.0628P] 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 2273 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1430 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C1 C -0.1345(4) -0.06030(19) 0.80337(14) 0.0474(5) Uani 1 1 d . . . C2 C -0.2303(5) -0.0715(2) 0.90071(15) 0.0548(5) Uani 1 1 d . . . H2 H -0.1661 -0.0111 0.9338 0.066 Uiso 1 1 calc R . . C3 C -0.4197(5) -0.1700(2) 0.95107(15) 0.0567(6) Uani 1 1 d . . . H3 H -0.4778 -0.1770 1.0179 0.068 Uiso 1 1 calc R . . C4 C -0.5229(4) -0.25845(19) 0.90210(15) 0.0495(5) Uani 1 1 d . . . C5 C -0.4341(5) -0.2453(2) 0.80262(15) 0.0558(6) Uani 1 1 d . . . H5 H -0.5069 -0.3031 0.7686 0.067 Uiso 1 1 calc R . . C6 C -0.2392(5) -0.1479(2) 0.75293(15) 0.0556(6) Uani 1 1 d . . . H6 H -0.1786 -0.1411 0.6863 0.067 Uiso 1 1 calc R . . C13 C -0.7802(6) -0.3829(3) 1.04922(16) 0.0751(7) Uani 1 1 d . . . H13A H -0.9124 -0.4562 1.0702 0.113 Uiso 1 1 calc R . . H13B H -0.8795 -0.3084 1.0641 0.113 Uiso 1 1 calc R . . H13C H -0.5957 -0.3994 1.0839 0.113 Uiso 1 1 calc R . . C7 C 0.2164(5) 0.06074(19) 0.67062(15) 0.0513(5) Uani 1 1 d . . . H7 H 0.1833 0.0024 0.6319 0.062 Uiso 1 1 calc R . . C8 C 0.4181(5) 0.16045(19) 0.63194(15) 0.0524(4) Uani 1 1 d . . . C9 C 0.4851(5) 0.2554(2) 0.68659(15) 0.0524(4) Uani 1 1 d . . . C11 C 0.7475(7) 0.4483(2) 0.68695(19) 0.0808(8) Uani 1 1 d . . . H11A H 0.5645 0.4813 0.7148 0.097 Uiso 1 1 calc R . . H11B H 0.8767 0.4115 0.7410 0.097 Uiso 1 1 calc R . . C12 C 0.9073(8) 0.5524(3) 0.6151(2) 0.1046(11) Uani 1 1 d . . . H12A H 1.0811 0.5179 0.5850 0.157 Uiso 1 1 calc R . . H12B H 0.9729 0.6155 0.6486 0.157 Uiso 1 1 calc R . . H12C H 0.7729 0.5922 0.5644 0.157 Uiso 1 1 calc R . . C10 C 0.5668(5) 0.16478(19) 0.53726(17) 0.0572(6) Uani 1 1 d . . . N1 N 0.0682(4) 0.04217(16) 0.75786(12) 0.0536(5) Uani 1 1 d . . . H1 H 0.0969 0.0987 0.7916 0.064 Uiso 1 1 calc R . . N2 N 0.6885(5) 0.1655(2) 0.46152(16) 0.0855(7) Uani 1 1 d . . . O3 O -0.7104(3) -0.35995(14) 0.94472(10) 0.0659(5) Uani 1 1 d . . . O2 O 0.6688(4) 0.34977(14) 0.63474(11) 0.0663(5) Uani 1 1 d . . . O1 O 0.3862(4) 0.25087(15) 0.77171(11) 0.0753(5) 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 0.0460(11) 0.0427(11) 0.0538(12) -0.0120(9) -0.0043(9) 0.0010(9) C2 0.0588(13) 0.0567(13) 0.0538(12) -0.0224(10) -0.0042(10) -0.0059(11) C3 0.0600(13) 0.0664(14) 0.0451(11) -0.0168(10) -0.0001(10) -0.0019(11) C4 0.0497(12) 0.0462(12) 0.0520(12) -0.0112(9) -0.0001(9) -0.0012(9) C5 0.0686(14) 0.0484(12) 0.0536(12) -0.0189(10) 0.0018(11) -0.0066(11) C6 0.0666(14) 0.0564(13) 0.0447(11) -0.0156(10) 0.0039(10) -0.0016(11) C13 0.0870(18) 0.0779(17) 0.0546(14) -0.0062(12) 0.0100(12) -0.0177(14) C7 0.0586(13) 0.0497(12) 0.0494(12) -0.0187(9) -0.0065(10) 0.0036(10) C8 0.0622(9) 0.0453(9) 0.0509(9) -0.0137(7) -0.0013(7) -0.0035(7) C9 0.0622(9) 0.0453(9) 0.0509(9) -0.0137(7) -0.0013(7) -0.0035(7) C11 0.109(2) 0.0653(16) 0.0771(16) -0.0380(13) 0.0144(14) -0.0247(14) C12 0.146(3) 0.0695(18) 0.103(2) -0.0359(16) 0.032(2) -0.0435(18) C10 0.0751(15) 0.0428(12) 0.0562(13) -0.0171(10) 0.0026(11) -0.0136(10) N1 0.0611(11) 0.0506(10) 0.0539(10) -0.0221(8) -0.0013(8) -0.0044(9) N2 0.1189(18) 0.0753(15) 0.0698(13) -0.0368(11) 0.0239(13) -0.0341(13) O3 0.0769(11) 0.0615(10) 0.0577(9) -0.0125(8) 0.0060(8) -0.0181(8) O2 0.0906(12) 0.0507(9) 0.0614(9) -0.0238(7) 0.0127(8) -0.0212(8) O1 0.0994(13) 0.0741(11) 0.0585(9) -0.0309(8) 0.0159(9) -0.0268(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 C1 C2 1.365(3) . ? C1 C6 1.390(3) . ? C1 N1 1.423(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9300 . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 O3 1.367(2) . ? C4 C5 1.383(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C13 O3 1.423(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C7 N1 1.311(2) . ? C7 C8 1.382(3) . ? C7 H7 0.9300 . ? C8 C10 1.420(3) . ? C8 C9 1.442(3) . ? C9 O1 1.221(2) . ? C9 O2 1.340(2) . ? C11 C12 1.461(3) . ? C11 O2 1.464(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C10 N2 1.147(3) . ? N1 H1 0.8600 . ? 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 C2 C1 C6 119.12(19) . . ? C2 C1 N1 117.95(17) . . ? C6 C1 N1 122.92(18) . . ? C1 C2 C3 121.60(19) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 119.82(19) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? O3 C4 C3 124.74(18) . . ? O3 C4 C5 116.43(18) . . ? C3 C4 C5 118.84(19) . . ? C6 C5 C4 121.17(19) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 119.41(18) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C7 C8 124.90(18) . . ? N1 C7 H7 117.5 . . ? C8 C7 H7 117.6 . . ? C7 C8 C10 117.89(18) . . ? C7 C8 C9 121.62(18) . . ? C10 C8 C9 120.46(18) . . ? O1 C9 O2 122.91(18) . . ? O1 C9 C8 123.80(19) . . ? O2 C9 C8 113.29(17) . . ? C12 C11 O2 108.0(2) . . ? C12 C11 H11A 110.1 . . ? O2 C11 H11A 110.1 . . ? C12 C11 H11B 110.1 . . ? O2 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? 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 . . ? N2 C10 C8 178.5(2) . . ? C7 N1 C1 127.77(17) . . ? C7 N1 H1 116.1 . . ? C1 N1 H1 116.1 . . ? C4 O3 C13 117.33(17) . . ? C9 O2 C11 115.71(17) . . ? 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 C6 C1 C2 C3 2.3(3) . . . . ? N1 C1 C2 C3 -178.15(18) . . . . ? C1 C2 C3 C4 -1.7(3) . . . . ? C2 C3 C4 O3 179.82(18) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? O3 C4 C5 C6 -178.46(18) . . . . ? C3 C4 C5 C6 1.7(3) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? N1 C1 C6 C5 179.55(18) . . . . ? N1 C7 C8 C10 178.2(2) . . . . ? N1 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 O1 4.6(3) . . . . ? C10 C8 C9 O1 -173.3(2) . . . . ? C7 C8 C9 O2 -175.57(18) . . . . ? C10 C8 C9 O2 6.4(3) . . . . ? C7 C8 C10 N2 -49(9) . . . . ? C9 C8 C10 N2 129(9) . . . . ? C8 C7 N1 C1 -177.84(19) . . . . ? C2 C1 N1 C7 170.65(19) . . . . ? C6 C1 N1 C7 -9.8(3) . . . . ? C3 C4 O3 C13 -6.3(3) . . . . ? C5 C4 O3 C13 173.90(19) . . . . ? O1 C9 O2 C11 0.4(3) . . . . ? C8 C9 O2 C11 -179.35(19) . . . . ? C12 C11 O2 C9 -171.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.145 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.036