# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_01 _database_code_CSD 161012 _journal_coden_Cambridge 188 # 1. SUBMISSION DETAILS _publ_contact_author ; Itzia I. Padilla-Mart/'inez Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 M/'exico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'J. Chem Soc., Perkin Trans. 2' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Further Insight into Three Center Hydrogen Bonding. Participation in Tautomeric Equilibria of Heterocyclic Amides. ; loop_ _publ_author_name _publ_author_address 'Itzia I. Padilla-Martinez' ; Departamento de Quimica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. Mexico D. F. ; 'Francisco J. Martinez-Martinez' ; Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. Mexico D. F. ; 'Efr/'en V. Garcia-Baez' ; Departamento de Quimica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. Mexico D. F. ; 'Susana Rojas-Lima' ; Centro de Investigaciones Quimicas Universidad Autonoma del Estado de Hidalgo Carretera-Tulancingo Pachuca Km. 3. Pachuca-Hidalgo, Mexico. ; 'Mart/'in Torres-Valencia' ; Centro de Investigaciones Quimicas Universidad Autonoma del Estado de Hidalgo Carretera Tulancingo Pachuca Km. 3. Pachuca-Hidalgo, M/'exico. ; 'Herbert Hopfl' ; Centro de Investigaciones Quimicas Universidad Autonoma del Estado de Morelos Cuernavaca-Morelos, Mexico. ; _publ_manuscript_creation 'RTF-File by CIFRTF (H.Schwenk 1996)' _audit_creation_method 'SHELXL-CIF-file updated by CIFRTF' _chemical_name_systematic ; N-(3-hydroxypyridine)-N'-(2-nitrophenyl)oxamide ; _chemical_name_common ? _chemical_formula_moiety 'C16 H17 N5 O6' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H17 N5 O6' _chemical_formula_weight 375.35 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)/c 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 7.2193(4) _cell_length_b 14.6988(7) _cell_length_c 16.6931(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.3250(1) _cell_angle_gamma 90.00 _cell_volume 1770.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needles' _exptl_crystal_colour colorless _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Diffractometer operator Susana Rojas scanspeed_seconds/frame 10 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in glass fiber ; _diffrn_ambient_temperature 293(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 'Bruker SMART 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 11207 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3467 _reflns_number_observed 1720 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Ver. 2.00)' _computing_cell_refinement 'XSCANS (Ver. 2.00)' _computing_data_reduction 'XSCANS (Ver. 2.00)' _computing_structure_solution 'SHELXS (Sheldrick 1997)' _computing_structure_refinement 'SHELXL (Sheldrick 1997)' _computing_molecular_graphics 'XPMA (Zsolnai 1997)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _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^)+(0.1111P)^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 refxyz _refine_ls_weighting_scheme ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3467 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_obs 0.0490 _refine_ls_wR_factor_all 0.1011 _refine_ls_wR_factor_obs 0.0922 _refine_ls_goodness_of_fit_all 1.181 _refine_ls_goodness_of_fit_obs 1.589 _refine_ls_restrained_S_all 1.181 _refine_ls_restrained_S_obs 1.589 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N10 N 0.4226(3) 0.03790(12) 0.35988(10) 0.0519(6) Uani 1 d . . N7 N 0.2180(3) 0.10271(12) 0.54200(11) 0.0489(5) Uani 1 d . . N1 N 0.0274(3) 0.04700(15) 0.68659(12) 0.0559(6) Uani 1 d . . O16 O 0.5768(3) 0.10015(11) 0.22949(9) 0.0687(6) Uani 1 d . . O9 O 0.2979(3) -0.04639(11) 0.46113(9) 0.0677(6) Uani 1 d . . O8 O 0.3535(3) 0.18807(11) 0.44369(10) 0.0703(6) Uani 1 d . . O1B O 0.0666(3) -0.01450(12) 0.63918(10) 0.0695(6) Uani 1 d . . C8 C 0.3069(3) 0.1159(2) 0.47275(14) 0.0490(7) Uani 1 d . . C9 C 0.3414(3) 0.0256(2) 0.43041(13) 0.0485(6) Uani 1 d . . C3 C 0.2018(4) 0.2594(2) 0.58953(14) 0.0578(7) Uani 1 d . . C2 C 0.1634(3) 0.1672(2) 0.59843(13) 0.0476(6) Uani 1 d . . N12 N 0.4373(3) -0.11366(14) 0.31342(12) 0.0588(6) Uani 1 d . . C11 C 0.4698(3) -0.0264(2) 0.30132(13) 0.0455(6) Uani 1 d . . O1A O -0.0453(2) 0.02953(12) 0.75044(10) 0.0766(6) Uani 1 d . . C16 C 0.5506(3) 0.0088(2) 0.23222(14) 0.0507(7) Uani 1 d . . C1 C 0.0691(3) 0.1416(2) 0.66731(13) 0.0490(7) Uani 1 d . . C4 C 0.1478(4) 0.3225(2) 0.6451(2) 0.0647(8) Uani 1 d . . C15 C 0.5960(4) -0.0512(2) 0.17295(14) 0.0632(8) Uani 1 d . . C6 C 0.0130(4) 0.2053(2) 0.7228(2) 0.0629(8) Uani 1 d . . C14 C 0.5621(4) -0.1422(2) 0.1842(2) 0.0697(8) Uani 1 d . . C13 C 0.4846(4) -0.1708(2) 0.2538(2) 0.0635(8) Uani 1 d . . C5 C 0.0517(4) 0.2956(2) 0.7124(2) 0.0699(9) Uani 1 d . . N2S N 0.2012(3) 0.80148(14) 0.02469(12) 0.0581(6) Uani 1 d . . C3S C 0.1666(4) 0.7219(2) 0.07280(15) 0.0652(8) Uani 1 d . . C2S C 0.1399(5) 0.8881(2) 0.0544(2) 0.0884(10) Uani 1 d . . C1S C 0.2874(4) 0.7961(2) -0.0439(2) 0.0651(8) Uani 1 d . . O1S O 0.3232(3) 0.86306(14) -0.08473(11) 0.0937(7) Uani 1 d . . H6 H -0.0644 0.1776 0.7700 0.050 Uiso 1 d . . H7 H 0.1925 0.0363 0.5604 0.050 Uiso 1 d . . H15 H 0.6559 -0.0272 0.1194 0.050 Uiso 1 d . . H10 H 0.4436 0.1015 0.3410 0.050 Uiso 1 d . . H3SC H 0.0328 0.7189 0.0800 0.050 Uiso 1 d . . H3SB H 0.1841 0.6639 0.0404 0.050 Uiso 1 d . . H4 H 0.1793 0.3978 0.6503 0.050 Uiso 1 d . . H13 H 0.4601 -0.2397 0.2711 0.050 Uiso 1 d . . H3 H 0.2925 0.2795 0.5505 0.050 Uiso 1 d . . H5 H 0.0018 0.3452 0.7500 0.050 Uiso 1 d . . H1S H 0.3234 0.7273 -0.0593 0.050 Uiso 1 d . . H14 H 0.5959 -0.1931 0.1491 0.050 Uiso 1 d . . H3SA H 0.2424 0.7251 0.1304 0.050 Uiso 1 d . . H2SC H 0.0014 0.8821 0.0700 0.050 Uiso 1 d . . H2SA H 0.1589 0.9355 0.0203 0.050 Uiso 1 d . . H16 H 0.5999 0.1193 0.1695 0.050 Uiso 1 d . . H2SE H 0.1754 0.8973 0.1204 0.050 Uiso 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 N10 0.0753(15) 0.0356(12) 0.0455(11) 0.0026(10) 0.0185(11) -0.0029(11) N7 0.0662(15) 0.0367(12) 0.0443(12) 0.0029(10) 0.0138(11) -0.0015(10) N1 0.0585(15) 0.058(2) 0.0520(13) 0.0066(12) 0.0133(11) 0.0014(12) O16 0.110(2) 0.0421(11) 0.0550(11) 0.0009(9) 0.0298(10) -0.0032(11) O9 0.104(2) 0.0416(11) 0.0586(11) 0.0057(9) 0.0245(11) -0.0063(10) O8 0.109(2) 0.0404(12) 0.0627(11) 0.0070(9) 0.0327(11) -0.0030(11) O1B 0.0972(15) 0.0481(12) 0.0644(11) -0.0030(10) 0.0279(11) -0.0032(11) C8 0.057(2) 0.044(2) 0.0463(15) 0.0039(13) 0.0091(13) -0.0002(14) C9 0.057(2) 0.046(2) 0.0432(14) 0.0036(13) 0.0056(13) -0.0037(14) C3 0.068(2) 0.044(2) 0.062(2) 0.0018(14) 0.0176(14) -0.0023(15) C2 0.054(2) 0.042(2) 0.0469(14) 0.0004(13) 0.0044(13) 0.0028(13) N12 0.078(2) 0.0373(14) 0.0618(14) -0.0034(11) 0.0060(12) -0.0031(12) C11 0.052(2) 0.038(2) 0.0462(14) -0.0016(12) 0.0006(12) 0.0005(13) O1A 0.0945(15) 0.0720(14) 0.0648(12) 0.0090(11) 0.0362(11) -0.0032(11) C16 0.062(2) 0.040(2) 0.0503(15) -0.0024(13) 0.0095(13) 0.0009(14) C1 0.055(2) 0.043(2) 0.049(2) -0.0004(12) 0.0072(13) -0.0024(13) C4 0.083(2) 0.040(2) 0.071(2) -0.0101(14) 0.006(2) -0.0004(15) C15 0.080(2) 0.057(2) 0.053(2) -0.0098(14) 0.0123(15) 0.004(2) C6 0.071(2) 0.057(2) 0.061(2) -0.0051(15) 0.020(2) 0.001(2) C14 0.089(2) 0.050(2) 0.069(2) -0.022(2) 0.005(2) 0.010(2) C13 0.081(2) 0.041(2) 0.069(2) -0.001(2) 0.000(2) -0.001(2) C5 0.085(2) 0.057(2) 0.069(2) -0.0144(15) 0.020(2) 0.009(2) N2S 0.075(2) 0.0534(15) 0.0467(13) 0.0021(11) 0.0136(12) 0.0061(12) C3S 0.081(2) 0.060(2) 0.055(2) -0.0009(14) 0.013(2) -0.005(2) C2S 0.135(3) 0.066(2) 0.066(2) 0.008(2) 0.036(2) 0.026(2) C1S 0.075(2) 0.069(2) 0.052(2) 0.0018(15) 0.013(2) 0.001(2) O1S 0.134(2) 0.083(2) 0.0659(13) 0.0179(12) 0.0347(13) -0.0078(14) _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 N10 C9 1.340(3) . ? N10 C11 1.407(3) . ? N10 H10 0.999(2) . ? N7 C8 1.349(3) . ? N7 C2 1.399(3) . ? N7 H7 1.041(2) . ? N1 O1A 1.226(2) . ? N1 O1B 1.239(2) . ? N1 C1 1.461(3) . ? O16 C16 1.357(3) . ? O16 H16 1.0572(15) . ? O9 C9 1.220(3) . ? O8 C8 1.217(3) . ? C8 C9 1.527(3) . ? C3 C4 1.375(3) . ? C3 C2 1.392(3) . ? C3 H3 0.980(2) . ? C2 C1 1.401(3) . ? N12 C11 1.320(3) . ? N12 C13 1.352(3) . ? C11 C16 1.403(3) . ? C16 C15 1.371(3) . ? C1 C6 1.384(3) . ? C4 C5 1.391(3) . ? C4 H4 1.132(2) . ? C15 C14 1.373(3) . ? C15 H15 1.062(2) . ? C6 C5 1.369(3) . ? C6 H6 1.058(2) . ? C14 C13 1.368(3) . ? C14 H14 0.985(2) . ? C13 H13 1.069(3) . ? C5 H5 1.032(2) . ? N2S C1S 1.318(3) . ? N2S C2S 1.440(3) . ? N2S C3S 1.444(3) . ? C3S H3SC 0.977(3) . ? C3S H3SB 1.019(3) . ? C3S H3SA 1.096(3) . ? C2S H2SC 1.043(3) . ? C2S H2SA 0.911(3) . ? C2S H2SE 1.134(3) . ? C1S O1S 1.228(3) . ? C1S H1S 1.077(3) . ? 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 C9 N10 C11 129.6(2) . . ? C9 N10 H10 118.4(2) . . ? C11 N10 H10 111.6(2) . . ? C8 N7 C2 128.8(2) . . ? C8 N7 H7 118.6(2) . . ? C2 N7 H7 112.5(2) . . ? O1A N1 O1B 120.8(2) . . ? O1A N1 C1 119.0(2) . . ? O1B N1 C1 120.2(2) . . ? C16 O16 H16 108.7(2) . . ? O8 C8 N7 127.5(2) . . ? O8 C8 C9 121.6(2) . . ? N7 C8 C9 110.9(2) . . ? O9 C9 N10 127.5(2) . . ? O9 C9 C8 120.9(2) . . ? N10 C9 C8 111.6(2) . . ? C4 C3 C2 121.7(2) . . ? C4 C3 H3 116.7(3) . . ? C2 C3 H3 120.2(2) . . ? C3 C2 N7 121.9(2) . . ? C3 C2 C1 116.8(2) . . ? N7 C2 C1 121.4(2) . . ? C11 N12 C13 116.2(2) . . ? N12 C11 C16 124.2(2) . . ? N12 C11 N10 120.0(2) . . ? C16 C11 N10 115.8(2) . . ? O16 C16 C15 125.2(2) . . ? O16 C16 C11 116.9(2) . . ? C15 C16 C11 117.9(2) . . ? C6 C1 C2 121.6(2) . . ? C6 C1 N1 115.5(2) . . ? C2 C1 N1 122.9(2) . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 130.7(3) . . ? C5 C4 H4 108.6(2) . . ? C16 C15 C14 118.8(2) . . ? C16 C15 H15 120.2(3) . . ? C14 C15 H15 121.0(2) . . ? C5 C6 C1 120.4(2) . . ? C5 C6 H6 125.5(2) . . ? C1 C6 H6 114.0(3) . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14 112.6(3) . . ? C15 C14 H14 127.7(3) . . ? N12 C13 C14 123.3(2) . . ? N12 C13 H13 110.1(2) . . ? C14 C13 H13 126.4(3) . . ? C6 C5 C4 119.1(2) . . ? C6 C5 H5 122.2(3) . . ? C4 C5 H5 118.5(3) . . ? C1S N2S C2S 120.4(2) . . ? C1S N2S C3S 121.7(2) . . ? C2S N2S C3S 117.8(2) . . ? N2S C3S H3SC 106.8(2) . . ? N2S C3S H3SB 110.9(2) . . ? H3SC C3S H3SB 99.3(2) . . ? N2S C3S H3SA 111.3(2) . . ? H3SC C3S H3SA 111.7(2) . . ? H3SB C3S H3SA 115.8(3) . . ? N2S C2S H2SC 108.3(3) . . ? N2S C2S H2SA 114.2(2) . . ? H2SC C2S H2SA 112.3(3) . . ? N2S C2S H2SE 112.0(2) . . ? H2SC C2S H2SE 87.9(2) . . ? H2SA C2S H2SE 118.8(3) . . ? O1S C1S N2S 123.0(3) . . ? O1S C1S H1S 124.4(3) . . ? N2S C1S H1S 112.6(3) . . ? _refine_diff_density_max 0.195 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.037 #===END data_a61 _database_code_CSD 161013 _journal_coden_Cambridge 188 # 1. SUBMISSION DETAILS _publ_contact_author 'Itzia I. Padilla-Martinez' _publ_contact_author_address ; Itzia I. Padilla-Martinez Departamento de Quimica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P 07340 Mexico, D. F. ; _publ_contact_author_phone '525 729 6000 EXT 56324' _publ_contact_author_fax '525 729 6000 EXT 56325' _publ_contact_author_email ipadilla@acei.upibi.ipn.mx _publ_requested_journal 'J. Chem Soc., Perkin Trans. 2' _publ_requested_category 'LC' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Further Insight into Three Center Hydrogen Bonding. Participation in Tautomeric Equilibria of Heterocyclic Amides. ; loop_ _publ_author_name _publ_author_address 'Itzia I. Padilla- Martinez' ; Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. Mexico D. F. ; 'Francisco J. Martinez-Martinez' ; Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. Mexico D. F. ; 'Efren V. Garcia-Baez' ; Departamento de Qu/'imica UPIBI-IPN Av. Acueducto s/n, Col. Barrio la Laguna Ticoman C.P. 07340. Mexico D. F. ; 'Susana Rojas-Lima' ; Centro de Investigaciones Qu/'imicas Universidad Autonoma del Estado de Hidalgo Carretera Tulancingo Pachuca Km. 3. Pachuca Hidalgo, Mexico. ; 'Martin Torres-Valencia' ; Centro de Investigaciones Quimicas Universidad Aut/'onoma del Estado de Hidalgo Carretera Tulancingo Pachuca Km. 3. Pachuca Hidalgo, Mexico. ; 'Herbert Hopfl' ; Centro de Investigaciones Quimicas Universidad Autonoma del Estado de Morelos Cuernavaca-Morelos, Mexico. ; _publ_manuscript_creation 'RTF-File by CIFRTF (H.Schwenk 1996)' _audit_creation_method 'SHELXL-CIF-file updated by CIFRTF' _chemical_name_systematic ; N-(3-hydroxypyridine)-N'-(2-methoxyphenyl)oxamide ; _chemical_name_common ? _chemical_formula_moiety 'C14 H15 N3 O5' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H15 N3 O5' _chemical_formula_weight 305.29 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)/c 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 12.825(3) _cell_length_b 15.110(3) _cell_length_c 7.3410(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.02(3) _cell_angle_gamma 90.00 _cell_volume 1396.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .48 _exptl_crystal_size_mid .224 _exptl_crystal_size_min .112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method ? _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Diffractometer operator MARCO A. LEYVA scanwidth_degrees 0.7 low_scanspeed_degrees/min 16.1 high_scanspeed_degrees/min 60 Background measurement : Moving crystal and moving counter at the beginning and end of scan, each for 25% of total scan area. Crystal mounted on a glass fiber. ; _diffrn_ambient_temperature 293(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 Enraf-Nonius _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2825 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 26.29 _reflns_number_total 2825 _reflns_number_observed 1892 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 software (Enraf-Nonius, 1989)' _computing_data_reduction 'JANA98 (Petricek Vaclav, 1998)' _computing_structure_solution 'SHELXS-97(Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'XPMA (Zsolnai 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.3217P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometrically _refine_ls_hydrogen_treatment 'Riding model, fixed isotropic U' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2824 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_obs 0.0399 _refine_ls_wR_factor_all 0.1248 _refine_ls_wR_factor_obs 0.1118 _refine_ls_goodness_of_fit_all 1.014 _refine_ls_goodness_of_fit_obs 1.141 _refine_ls_restrained_S_all 1.024 _refine_ls_restrained_S_obs 1.141 _refine_ls_shift/esd_max -1.755 _refine_ls_shift/esd_mean 0.011 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N15 N 0.83756(12) 0.40295(10) 0.1178(2) 0.0369(4) Uani 1 d . . N14 N 1.01219(12) 0.38527(10) 0.2878(2) 0.0370(4) Uani 1 d . . O19 O 0.84357(11) 0.25823(9) 0.2105(2) 0.0596(5) Uani 1 d . . O3 O 0.63459(11) 0.06433(9) -0.1300(2) 0.0477(4) Uani 1 d . . O20 O 0.86228(11) 0.57754(9) 0.1082(2) 0.0502(4) Uani 1 d . . N16 N 0.65099(12) 0.22919(10) -0.0005(2) 0.0380(4) Uani 1 d . . O7 O 0.64650(12) 0.37448(9) -0.0868(2) 0.0579(5) Uani 1 d . . O1 O 0.93060(12) 0.72975(9) -0.0042(2) 0.0522(4) Uani 1 d . . C2 C 0.54987(14) 0.19890(12) -0.0943(2) 0.0359(4) Uani 1 d . . C9 C 0.93558(14) 0.43857(12) 0.2042(2) 0.0321(4) Uani 1 d . . C7 C 0.68913(14) 0.31113(12) -0.0016(3) 0.0350(4) Uani 1 d . . C12 C 1.1252(2) 0.51151(14) 0.3572(3) 0.0446(5) Uani 1 d . . C11 C 1.0440(2) 0.56687(12) 0.2718(3) 0.0403(5) Uani 1 d . . C8 C 0.80013(14) 0.32017(11) 0.1223(3) 0.0346(4) Uani 1 d . . C10 C 0.94732(15) 0.53042(12) 0.1943(2) 0.0355(4) Uani 1 d . . C1 C 0.54171(15) 0.11130(13) -0.1581(3) 0.0382(4) Uani 1 d . . C13 C 1.10605(15) 0.42265(13) 0.3634(3) 0.0431(5) Uani 1 d . . C6 C 0.4434(2) 0.07864(14) -0.2433(3) 0.0467(5) Uani 1 d . . C4 C 0.3630(2) 0.2184(2) -0.2053(3) 0.0551(6) Uani 1 d . . C5 C 0.3550(2) 0.1329(2) -0.2673(3) 0.0535(6) Uani 1 d . . C3 C 0.4607(2) 0.25212(14) -0.1173(3) 0.0463(5) Uani 1 d . . C14 C 0.6303(2) -0.02301(14) -0.2065(3) 0.0544(6) Uani 1 d . . H15 H 0.7839 0.4400 0.0451 0.050 Uiso 1 d . . H12 H 1.1961 0.5404 0.4045 0.050 Uiso 1 d . . H6 H 0.4357 0.0171 -0.2856 0.050 Uiso 1 d . . H5 H 0.2875 0.0972 -0.3236 0.050 Uiso 1 d . . H11 H 1.0608 0.6429 0.2673 0.050 Uiso 1 d . . H20 H 0.8815 0.6409 0.0850 0.050 Uiso 1 d . . H13 H 1.1638 0.3803 0.4268 0.050 Uiso 1 d . . H16 H 0.6965 0.1800 0.0610 0.050 Uiso 1 d . . H3 H 0.4713 0.3200 -0.0740 0.050 Uiso 1 d . . H4 H 0.3014 0.2569 -0.2303 0.050 Uiso 1 d . . H1A H 0.9777 0.7602 0.0631 0.050 Uiso 1 d . . H14C H 0.5846 -0.0614 -0.1591 0.050 Uiso 1 d . . H14B H 0.7033 -0.0426 -0.1914 0.050 Uiso 1 d . . H14A H 0.6032 -0.0216 -0.3366 0.050 Uiso 1 d . . H1B H 0.9816 0.7189 -0.1047 0.050 Uiso 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 N15 0.0333(8) 0.0299(8) 0.0434(9) 0.0011(6) -0.0030(7) -0.0036(6) N14 0.0339(8) 0.0339(8) 0.0413(9) -0.0008(7) 0.0027(7) -0.0020(7) O19 0.0430(8) 0.0363(8) 0.0877(12) 0.0114(8) -0.0175(8) -0.0039(6) O3 0.0442(8) 0.0389(8) 0.0543(9) -0.0098(6) -0.0047(6) -0.0009(6) O20 0.0438(8) 0.0331(7) 0.0676(10) 0.0071(6) -0.0046(7) -0.0023(6) N16 0.0329(8) 0.0332(8) 0.0440(9) -0.0020(7) -0.0030(7) -0.0028(7) O7 0.0492(9) 0.0412(8) 0.0716(11) 0.0143(7) -0.0177(7) -0.0052(7) O1 0.0628(10) 0.0381(8) 0.0551(9) -0.0070(7) 0.0096(7) -0.0054(7) C2 0.0308(9) 0.0397(10) 0.0353(10) -0.0015(8) 0.0013(7) -0.0075(8) C9 0.0318(9) 0.0337(9) 0.0306(9) -0.0041(7) 0.0051(7) -0.0049(7) C7 0.0343(10) 0.0331(10) 0.0359(10) -0.0024(8) 0.0023(8) -0.0013(8) C12 0.0374(10) 0.0465(12) 0.0466(12) -0.0007(9) -0.0004(9) -0.0120(9) C11 0.0427(11) 0.0349(10) 0.0411(11) -0.0026(8) 0.0026(8) -0.0090(8) C8 0.0317(10) 0.0314(9) 0.0388(10) -0.0026(8) 0.0018(8) 0.0006(7) C10 0.0371(10) 0.0335(10) 0.0354(10) -0.0009(7) 0.0057(8) -0.0014(8) C1 0.0381(10) 0.0426(11) 0.0326(10) -0.0009(8) 0.0031(8) -0.0082(8) C13 0.0352(10) 0.0444(11) 0.0465(11) 0.0007(9) 0.0001(9) -0.0030(8) C6 0.0460(12) 0.0513(12) 0.0406(11) -0.0050(9) 0.0029(9) -0.0183(10) C4 0.0317(11) 0.074(2) 0.0571(14) 0.0008(12) 0.0025(9) 0.0012(10) C5 0.0355(11) 0.074(2) 0.0473(12) -0.0025(11) -0.0006(9) -0.0189(11) C3 0.0369(11) 0.0512(12) 0.0493(12) -0.0036(9) 0.0048(9) -0.0009(9) C14 0.068(2) 0.0375(11) 0.0551(14) -0.0094(10) 0.0047(11) -0.0022(10) _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 N15 C8 1.343(2) . ? N15 C9 1.403(2) . ? N15 H15 0.9652(15) . ? N14 C9 1.326(2) . ? N14 C13 1.349(2) . ? O19 C8 1.211(2) . ? O3 C1 1.368(2) . ? O3 C14 1.431(2) . ? O20 C10 1.354(2) . ? O20 H20 1.0111(13) . ? N16 C7 1.332(2) . ? N16 C2 1.423(2) . ? N16 H16 0.998(2) . ? O7 C7 1.215(2) . ? O1 H1A 0.8406(14) . ? O1 H1B 1.088(2) . ? C2 C3 1.382(3) . ? C2 C1 1.401(3) . ? C9 C10 1.399(2) . ? C7 C8 1.542(3) . ? C12 C13 1.367(3) . ? C12 C11 1.388(3) . ? C12 H12 1.009(2) . ? C11 C10 1.377(3) . ? C11 H11 1.170(2) . ? C1 C6 1.387(3) . ? C13 H13 1.021(2) . ? C6 C5 1.383(3) . ? C6 H6 0.979(2) . ? C4 C5 1.367(3) . ? C4 C3 1.391(3) . ? C4 H4 0.970(2) . ? C5 H5 1.037(2) . ? C3 H3 1.075(2) . ? C14 H14C 0.937(2) . ? C14 H14B 0.968(2) . ? C14 H14A 0.952(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 C8 N15 C9 129.8(2) . . ? C8 N15 H15 109.48(14) . . ? C9 N15 H15 120.68(15) . . ? C9 N14 C13 117.4(2) . . ? C1 O3 C14 116.9(2) . . ? C10 O20 H20 112.09(14) . . ? C7 N16 C2 126.7(2) . . ? C7 N16 H16 120.8(2) . . ? C2 N16 H16 112.31(15) . . ? H1A O1 H1B 91.34(13) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 N16 121.9(2) . . ? C1 C2 N16 117.9(2) . . ? N14 C9 C10 123.3(2) . . ? N14 C9 N15 119.8(2) . . ? C10 C9 N15 116.9(2) . . ? O7 C7 N16 127.3(2) . . ? O7 C7 C8 120.5(2) . . ? N16 C7 C8 112.2(2) . . ? C13 C12 C11 118.9(2) . . ? C13 C12 H12 124.7(2) . . ? C11 C12 H12 116.3(2) . . ? C10 C11 C12 119.0(2) . . ? C10 C11 H11 122.5(2) . . ? C12 C11 H11 118.6(2) . . ? O19 C8 N15 127.1(2) . . ? O19 C8 C7 121.7(2) . . ? N15 C8 C7 111.23(15) . . ? O20 C10 C11 124.4(2) . . ? O20 C10 C9 117.4(2) . . ? C11 C10 C9 118.2(2) . . ? O3 C1 C6 125.0(2) . . ? O3 C1 C2 115.6(2) . . ? C6 C1 C2 119.4(2) . . ? N14 C13 C12 123.3(2) . . ? N14 C13 H13 116.0(2) . . ? C12 C13 H13 120.7(2) . . ? C5 C6 C1 119.9(2) . . ? C5 C6 H6 119.5(2) . . ? C1 C6 H6 120.6(2) . . ? C5 C4 C3 120.3(2) . . ? C5 C4 H4 119.8(2) . . ? C3 C4 H4 119.8(2) . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 129.0(2) . . ? C6 C5 H5 110.1(2) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 117.6(2) . . ? C4 C3 H3 122.6(2) . . ? O3 C14 H14C 113.9(2) . . ? O3 C14 H14B 105.8(2) . . ? H14C C14 H14B 115.3(2) . . ? O3 C14 H14A 110.6(2) . . ? H14C C14 H14A 104.6(2) . . ? H14B C14 H14A 106.3(2) . . ? _refine_diff_density_max 0.233 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.045 #===END