# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Aakeroy, C.' 'Forbes, Safiyyah' 'Desper, John' _publ_contact_author_name 'Aakeroy, C.' _publ_contact_author_email aakeroy@ksu.edu _publ_section_title ; The effect of water molecules in stabilizing solid forms of co-crystals of a pair of active pharmaceutical ingredients ; # Attachment '- all.cif' data_sf0608m(2A) _database_code_depnum_ccdc_archive 'CCDC 853500' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 242 (3-pyridyl)-CONH-N=CH-(2-pyridyl), hexanoic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C6 H12 O2) (H2 O) ; _chemical_formula_sum 'C18 H24 N4 O4' _chemical_formula_weight 360.41 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 6.6573(13) _cell_length_b 8.1256(14) _cell_length_c 18.128(3) _cell_angle_alpha 95.391(10) _cell_angle_beta 97.999(12) _cell_angle_gamma 104.439(14) _cell_volume 931.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1561 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.05 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 6561 _diffrn_reflns_av_R_equivalents 0.0855 _diffrn_reflns_av_sigmaI/netI 0.1094 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4031 _reflns_number_gt 2060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0950P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4031 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1825 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _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 O1S O 0.4578(3) 0.2957(3) -0.09185(12) 0.0457(6) Uani 1 1 d . . . H1A H 0.557(5) 0.283(4) -0.0645(18) 0.055 Uiso 1 1 d . . . H1B H 0.427(5) 0.225(4) -0.1384(19) 0.055 Uiso 1 1 d . . . N11 N 0.3306(3) 0.0753(3) 0.17737(12) 0.0355(6) Uani 1 1 d . . . C12 C 0.4287(4) 0.1722(4) 0.13107(15) 0.0378(7) Uani 1 1 d . . . H12 H 0.5780 0.1990 0.1382 0.045 Uiso 1 1 calc R . . C13 C 0.3274(4) 0.2358(4) 0.07378(15) 0.0337(7) Uani 1 1 d . . . H13 H 0.4052 0.3050 0.0425 0.040 Uiso 1 1 calc R . . C14 C 0.1080(3) 0.1974(3) 0.06216(13) 0.0261(6) Uani 1 1 d . . . C15 C 0.0056(4) 0.0961(3) 0.11041(14) 0.0311(6) Uani 1 1 d . . . H15 H -0.1436 0.0669 0.1046 0.037 Uiso 1 1 calc R . . C16 C 0.1181(4) 0.0385(3) 0.16594(15) 0.0339(6) Uani 1 1 d . . . H16 H 0.0442 -0.0306 0.1982 0.041 Uiso 1 1 calc R . . C17 C -0.0220(3) 0.2597(3) 0.00357(14) 0.0289(6) Uani 1 1 d . . . N17 N 0.0740(3) 0.3262(3) -0.05161(12) 0.0298(5) Uani 1 1 d . . . H17 H 0.181(4) 0.318(4) -0.0546(15) 0.036 Uiso 1 1 d . . . O17 O -0.2080(2) 0.2490(2) 0.00656(10) 0.0364(5) Uani 1 1 d . . . N21 N 0.0797(3) 0.5862(3) -0.26611(13) 0.0402(6) Uani 1 1 d . . . C22 C -0.0453(4) 0.5118(3) -0.21984(14) 0.0316(6) Uani 1 1 d . . . C23 C -0.2593(4) 0.5019(4) -0.22902(15) 0.0343(6) Uani 1 1 d . . . H23 H -0.3446 0.4440 -0.1965 0.041 Uiso 1 1 calc R . . C24 C -0.3452(4) 0.5770(4) -0.28578(16) 0.0406(7) Uani 1 1 d . . . H24 H -0.4900 0.5748 -0.2924 0.049 Uiso 1 1 calc R . . C25 C -0.2170(5) 0.6558(4) -0.33309(17) 0.0452(7) Uani 1 1 d . . . H25 H -0.2720 0.7079 -0.3732 0.054 Uiso 1 1 calc R . . C26 C -0.0095(4) 0.6573(4) -0.32087(16) 0.0447(8) Uani 1 1 d . . . H26 H 0.0774 0.7125 -0.3535 0.054 Uiso 1 1 calc R . . C27 C 0.0593(4) 0.4421(3) -0.15918(15) 0.0326(6) Uani 1 1 d . . . H27 H 0.2014 0.4392 -0.1581 0.039 Uiso 1 1 calc R . . N27 N -0.0390(3) 0.3848(3) -0.10734(11) 0.0296(5) Uani 1 1 d . . . C31 C 0.6487(4) -0.0855(4) 0.29397(16) 0.0358(7) Uani 1 1 d . . . O31 O 0.5061(3) -0.0037(3) 0.30090(12) 0.0497(6) Uani 1 1 d . . . H31 H 0.444(5) 0.022(4) 0.2487(19) 0.060 Uiso 1 1 d . . . O32 O 0.7011(3) -0.1215(3) 0.23454(11) 0.0498(6) Uani 1 1 d . . . C32 C 0.7384(4) -0.1367(4) 0.36614(16) 0.0419(7) Uani 1 1 d . . . H32A H 0.6483 -0.2491 0.3731 0.050 Uiso 1 1 calc R . . H32B H 0.7336 -0.0518 0.4083 0.050 Uiso 1 1 calc R . . C33 C 0.9619(4) -0.1494(4) 0.36985(16) 0.0399(7) Uani 1 1 d . . . H33A H 0.9706 -0.2227 0.3242 0.048 Uiso 1 1 calc R . . H33B H 1.0550 -0.0336 0.3696 0.048 Uiso 1 1 calc R . . C34 C 1.0416(4) -0.2217(4) 0.43801(16) 0.0397(7) Uani 1 1 d . . . H34A H 0.9548 -0.3405 0.4368 0.048 Uiso 1 1 calc R . . H34B H 1.0256 -0.1528 0.4838 0.048 Uiso 1 1 calc R . . C35 C 1.2701(4) -0.2225(4) 0.44234(17) 0.0440(8) Uani 1 1 d . . . H35A H 1.2864 -0.2848 0.3949 0.053 Uiso 1 1 calc R . . H35B H 1.3565 -0.1027 0.4462 0.053 Uiso 1 1 calc R . . C36 C 1.3553(5) -0.3031(4) 0.50715(18) 0.0540(9) Uani 1 1 d . . . H36A H 1.5039 -0.2965 0.5062 0.081 Uiso 1 1 calc R . . H36B H 1.2754 -0.4236 0.5027 0.081 Uiso 1 1 calc R . . H36C H 1.3419 -0.2417 0.5546 0.081 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 O1S 0.0186(8) 0.0826(17) 0.0387(12) 0.0124(11) 0.0044(8) 0.0170(10) N11 0.0260(10) 0.0480(15) 0.0353(13) 0.0139(11) 0.0046(9) 0.0120(10) C12 0.0194(11) 0.0580(19) 0.0367(16) 0.0125(14) 0.0051(11) 0.0092(12) C13 0.0186(11) 0.0496(18) 0.0334(15) 0.0140(13) 0.0085(10) 0.0049(11) C14 0.0166(10) 0.0332(14) 0.0272(14) 0.0053(11) 0.0034(10) 0.0039(10) C15 0.0198(11) 0.0343(15) 0.0377(16) 0.0084(13) 0.0080(11) 0.0015(11) C16 0.0255(12) 0.0402(16) 0.0358(15) 0.0126(13) 0.0075(11) 0.0046(12) C17 0.0200(11) 0.0327(15) 0.0327(15) 0.0053(12) 0.0043(10) 0.0044(11) N17 0.0156(9) 0.0416(14) 0.0344(13) 0.0139(11) 0.0058(9) 0.0076(10) O17 0.0143(7) 0.0534(12) 0.0432(11) 0.0177(9) 0.0066(7) 0.0074(8) N21 0.0314(11) 0.0504(15) 0.0422(14) 0.0203(12) 0.0129(10) 0.0084(11) C22 0.0276(12) 0.0336(15) 0.0323(15) 0.0089(12) 0.0058(11) 0.0036(11) C23 0.0248(12) 0.0390(16) 0.0369(16) 0.0090(13) 0.0033(11) 0.0038(12) C24 0.0305(13) 0.0434(18) 0.0452(18) 0.0077(14) 0.0014(13) 0.0070(13) C25 0.0450(16) 0.0485(19) 0.0398(18) 0.0148(15) -0.0024(13) 0.0103(14) C26 0.0442(16) 0.0518(19) 0.0400(17) 0.0228(15) 0.0115(14) 0.0082(15) C27 0.0223(11) 0.0391(16) 0.0354(15) 0.0095(13) 0.0055(11) 0.0047(11) N27 0.0197(9) 0.0367(13) 0.0312(12) 0.0106(10) 0.0023(9) 0.0042(9) C31 0.0217(12) 0.0465(18) 0.0370(16) 0.0113(14) 0.0042(11) 0.0031(12) O31 0.0432(11) 0.0791(16) 0.0387(12) 0.0212(11) 0.0094(9) 0.0319(11) O32 0.0274(9) 0.0866(18) 0.0357(12) 0.0088(11) 0.0044(9) 0.0159(11) C32 0.0288(13) 0.062(2) 0.0387(17) 0.0173(15) 0.0066(12) 0.0143(14) C33 0.0252(12) 0.0524(18) 0.0428(17) 0.0155(14) 0.0047(12) 0.0087(13) C34 0.0292(13) 0.0485(18) 0.0433(17) 0.0152(14) 0.0073(12) 0.0100(13) C35 0.0296(13) 0.060(2) 0.0458(18) 0.0153(15) 0.0056(13) 0.0150(14) C36 0.0399(16) 0.074(2) 0.057(2) 0.0254(18) 0.0093(15) 0.0253(16) _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 O1S H1A 0.80(3) . ? O1S H1B 0.94(3) . ? N11 C12 1.331(3) . ? N11 C16 1.353(3) . ? C12 C13 1.371(4) . ? C12 H12 0.9500 . ? C13 C14 1.396(3) . ? C13 H13 0.9500 . ? C14 C15 1.389(3) . ? C14 C17 1.482(3) . ? C15 C16 1.359(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.229(3) . ? C17 N17 1.345(3) . ? N17 N27 1.367(3) . ? N17 H17 0.74(3) . ? N21 C26 1.336(4) . ? N21 C22 1.342(3) . ? C22 C23 1.392(3) . ? C22 C27 1.454(4) . ? C23 C24 1.374(4) . ? C23 H23 0.9500 . ? C24 C25 1.381(4) . ? C24 H24 0.9500 . ? C25 C26 1.366(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.276(3) . ? C27 H27 0.9500 . ? C31 O32 1.210(3) . ? C31 O31 1.301(3) . ? C31 C32 1.500(4) . ? O31 H31 1.04(4) . ? C32 C33 1.510(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.504(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.514(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.509(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? 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 H1A O1S H1B 113(3) . . ? C12 N11 C16 116.8(2) . . ? N11 C12 C13 124.0(2) . . ? N11 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 119.0(2) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 117.1(2) . . ? C15 C14 C17 118.0(2) . . ? C13 C14 C17 124.9(2) . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? N11 C16 C15 122.9(2) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? O17 C17 N17 123.0(2) . . ? O17 C17 C14 120.3(2) . . ? N17 C17 C14 116.69(19) . . ? C17 N17 N27 119.10(19) . . ? C17 N17 H17 119(2) . . ? N27 N17 H17 121(2) . . ? C26 N21 C22 116.7(2) . . ? N21 C22 C23 122.6(2) . . ? N21 C22 C27 115.0(2) . . ? C23 C22 C27 122.3(2) . . ? C24 C23 C22 119.0(2) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C23 C24 C25 118.7(3) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C26 C25 C24 118.5(3) . . ? C26 C25 H25 120.8 . . ? C24 C25 H25 120.8 . . ? N21 C26 C25 124.4(3) . . ? N21 C26 H26 117.8 . . ? C25 C26 H26 117.8 . . ? N27 C27 C22 120.3(2) . . ? N27 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? C27 N27 N17 116.13(19) . . ? O32 C31 O31 123.4(3) . . ? O32 C31 C32 122.7(3) . . ? O31 C31 C32 113.9(2) . . ? C31 O31 H31 110.4(17) . . ? C31 C32 C33 114.2(2) . . ? C31 C32 H32A 108.7 . . ? C33 C32 H32A 108.7 . . ? C31 C32 H32B 108.7 . . ? C33 C32 H32B 108.7 . . ? H32A C32 H32B 107.6 . . ? C34 C33 C32 113.9(2) . . ? C34 C33 H33A 108.8 . . ? C32 C33 H33A 108.8 . . ? C34 C33 H33B 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C35 112.4(2) . . ? C33 C34 H34A 109.1 . . ? C35 C34 H34A 109.1 . . ? C33 C34 H34B 109.1 . . ? C35 C34 H34B 109.1 . . ? H34A C34 H34B 107.9 . . ? C36 C35 C34 114.8(2) . . ? C36 C35 H35A 108.6 . . ? C34 C35 H35A 108.6 . . ? C36 C35 H35B 108.6 . . ? C34 C35 H35B 108.6 . . ? H35A C35 H35B 107.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? 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 C16 N11 C12 C13 0.2(4) . . . . ? N11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C12 C13 C14 C17 178.8(3) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C17 C14 C15 C16 -178.8(2) . . . . ? C12 N11 C16 C15 -0.1(4) . . . . ? C14 C15 C16 N11 0.0(4) . . . . ? C15 C14 C17 O17 13.2(4) . . . . ? C13 C14 C17 O17 -165.4(3) . . . . ? C15 C14 C17 N17 -166.6(2) . . . . ? C13 C14 C17 N17 14.8(4) . . . . ? O17 C17 N17 N27 -0.1(4) . . . . ? C14 C17 N17 N27 179.6(2) . . . . ? C26 N21 C22 C23 2.3(4) . . . . ? C26 N21 C22 C27 -177.6(2) . . . . ? N21 C22 C23 C24 -2.7(4) . . . . ? C27 C22 C23 C24 177.3(3) . . . . ? C22 C23 C24 C25 1.8(4) . . . . ? C23 C24 C25 C26 -0.7(4) . . . . ? C22 N21 C26 C25 -1.2(5) . . . . ? C24 C25 C26 N21 0.4(5) . . . . ? N21 C22 C27 N27 172.6(2) . . . . ? C23 C22 C27 N27 -7.4(4) . . . . ? C22 C27 N27 N17 -178.2(2) . . . . ? C17 N17 N27 C27 -178.1(2) . . . . ? O32 C31 C32 C33 30.4(4) . . . . ? O31 C31 C32 C33 -151.4(3) . . . . ? C31 C32 C33 C34 -172.8(3) . . . . ? C32 C33 C34 C35 -176.5(3) . . . . ? C33 C34 C35 C36 -176.6(3) . . . . ? 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 O1S H1A O17 0.80(3) 1.98(3) 2.778(3) 177(3) 1_655 O1S H1B O32 0.94(3) 1.85(3) 2.760(3) 161(3) 2_655 O31 H31 N11 1.04(4) 1.56(4) 2.590(3) 171(3) . N17 H17 O1S 0.74(3) 2.09(3) 2.815(3) 165(3) . _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.272 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.075 #END data_sf0603m(2B) _database_code_depnum_ccdc_archive 'CCDC 853501' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF241 formylpyridine phenylhydrazone, octanoic acid, hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C8 H16 O2) (H2 O) ; _chemical_formula_sum 'C20 H28 N4 O4' _chemical_formula_weight 388.46 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 6.6610(8) _cell_length_b 8.4541(11) _cell_length_c 19.684(2) _cell_angle_alpha 99.459(8) _cell_angle_beta 94.349(9) _cell_angle_gamma 107.887(8) _cell_volume 1031.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1367 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.20 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 7356 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.1400 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.70 _reflns_number_total 4563 _reflns_number_gt 2145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0900P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4563 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1322 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1858 _refine_ls_wR_factor_gt 0.1609 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _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 O1S O 0.5297(3) -0.2981(3) 0.58385(11) 0.0437(6) Uani 1 1 d . . . H1A H 0.541(5) -0.230(4) 0.6193(17) 0.052 Uiso 1 1 d . . . H1B H 0.408(6) -0.288(4) 0.5571(16) 0.052 Uiso 1 1 d . . . N11 N 0.1369(4) 0.5562(3) 0.25630(12) 0.0409(6) Uani 1 1 d . . . C12 C -0.0027(5) 0.4879(3) 0.29781(14) 0.0324(7) Uani 1 1 d . . . C13 C -0.2126(5) 0.4833(4) 0.29007(14) 0.0353(7) Uani 1 1 d . . . H13 H -0.3071 0.4331 0.3202 0.042 Uiso 1 1 calc R . . C14 C -0.2830(5) 0.5522(4) 0.23814(15) 0.0412(7) Uani 1 1 d . . . H14 H -0.4270 0.5492 0.2315 0.049 Uiso 1 1 calc R . . C15 C -0.1407(6) 0.6255(4) 0.19611(16) 0.0475(8) Uani 1 1 d . . . H15 H -0.1830 0.6771 0.1607 0.057 Uiso 1 1 calc R . . C16 C 0.0644(6) 0.6223(4) 0.20668(16) 0.0485(8) Uani 1 1 d . . . H16 H 0.1606 0.6704 0.1766 0.058 Uiso 1 1 calc R . . C17 C 0.0858(4) 0.4237(3) 0.35312(14) 0.0328(6) Uani 1 1 d . . . H17 H 0.2270 0.4198 0.3542 0.039 Uiso 1 1 calc R . . N17 N -0.0253(4) 0.3724(3) 0.40025(11) 0.0312(5) Uani 1 1 d . . . N21 N 0.2808(4) 0.0968(3) 0.65918(12) 0.0370(6) Uani 1 1 d . . . C22 C 0.3945(5) 0.1899(4) 0.61854(14) 0.0378(7) Uani 1 1 d . . . H22 H 0.5450 0.2178 0.6257 0.045 Uiso 1 1 calc R . . C23 C 0.3047(4) 0.2480(4) 0.56656(14) 0.0348(7) Uani 1 1 d . . . H23 H 0.3916 0.3149 0.5388 0.042 Uiso 1 1 calc R . . C24 C 0.0858(4) 0.2072(3) 0.55564(13) 0.0300(6) Uani 1 1 d . . . C25 C -0.0335(4) 0.1094(3) 0.59809(14) 0.0310(6) Uani 1 1 d . . . H25 H -0.1844 0.0786 0.5921 0.037 Uiso 1 1 calc R . . C26 C 0.0704(5) 0.0583(4) 0.64857(14) 0.0348(7) Uani 1 1 d . . . H26 H -0.0120 -0.0080 0.6775 0.042 Uiso 1 1 calc R . . C27 C -0.0323(4) 0.2636(3) 0.50189(13) 0.0290(6) Uani 1 1 d . . . N27 N 0.0765(4) 0.3204(3) 0.45114(12) 0.0315(6) Uani 1 1 d . . . H27 H 0.197(5) 0.317(4) 0.4481(15) 0.038 Uiso 1 1 d . . . O27 O -0.2181(3) 0.2559(3) 0.50585(10) 0.0381(5) Uani 1 1 d . . . C31 C 0.5739(4) -0.0504(4) 0.76561(15) 0.0352(7) Uani 1 1 d . . . O31 O 0.4277(4) 0.0221(3) 0.77139(11) 0.0497(6) Uani 1 1 d . . . H31 H 0.375(5) 0.052(4) 0.7282(18) 0.060 Uiso 1 1 d . . . O32 O 0.6436(3) -0.0798(3) 0.71137(10) 0.0463(6) Uani 1 1 d . . . C32 C 0.6430(5) -0.0968(4) 0.83094(15) 0.0419(7) Uani 1 1 d . . . H32A H 0.5356 -0.2031 0.8364 0.050 Uiso 1 1 calc R . . H32B H 0.6453 -0.0069 0.8705 0.050 Uiso 1 1 calc R . . C33 C 0.8585(5) -0.1211(4) 0.83503(16) 0.0422(7) Uani 1 1 d . . . H33A H 0.9689 -0.0122 0.8342 0.051 Uiso 1 1 calc R . . H33B H 0.8615 -0.2044 0.7937 0.051 Uiso 1 1 calc R . . C34 C 0.9107(5) -0.1825(4) 0.90010(16) 0.0452(8) Uani 1 1 d . . . H34A H 0.8917 -0.1055 0.9409 0.054 Uiso 1 1 calc R . . H34B H 0.8078 -0.2966 0.8984 0.054 Uiso 1 1 calc R . . C35 C 1.1318(5) -0.1919(4) 0.91019(15) 0.0418(8) Uani 1 1 d . . . H35A H 1.2348 -0.0774 0.9129 0.050 Uiso 1 1 calc R . . H35B H 1.1518 -0.2672 0.8689 0.050 Uiso 1 1 calc R . . C36 C 1.1824(5) -0.2564(4) 0.97437(16) 0.0431(8) Uani 1 1 d . . . H36A H 1.1609 -0.1821 1.0156 0.052 Uiso 1 1 calc R . . H36B H 1.0809 -0.3716 0.9714 0.052 Uiso 1 1 calc R . . C37 C 1.4053(5) -0.2634(4) 0.98448(16) 0.0444(8) Uani 1 1 d . . . H37A H 1.5063 -0.1493 0.9849 0.053 Uiso 1 1 calc R . . H37B H 1.4242 -0.3419 0.9441 0.053 Uiso 1 1 calc R . . C38 C 1.4625(6) -0.3197(4) 1.05006(16) 0.0511(9) Uani 1 1 d . . . H38A H 1.6098 -0.3203 1.0526 0.077 Uiso 1 1 calc R . . H38B H 1.3666 -0.4341 1.0496 0.077 Uiso 1 1 calc R . . H38C H 1.4483 -0.2412 1.0905 0.077 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 O1S 0.0290(12) 0.0693(17) 0.0376(12) 0.0099(11) 0.0045(10) 0.0233(11) N11 0.0387(15) 0.0490(16) 0.0372(14) 0.0179(12) 0.0056(11) 0.0123(12) C12 0.0363(17) 0.0328(16) 0.0304(15) 0.0097(12) 0.0041(12) 0.0129(13) C13 0.0387(18) 0.0368(17) 0.0333(16) 0.0104(13) 0.0048(13) 0.0150(14) C14 0.0418(19) 0.0423(18) 0.0403(17) 0.0084(14) -0.0041(14) 0.0168(15) C15 0.058(2) 0.047(2) 0.0389(17) 0.0179(15) -0.0061(15) 0.0175(17) C16 0.058(2) 0.049(2) 0.0400(18) 0.0194(15) 0.0088(15) 0.0139(17) C17 0.0279(15) 0.0378(17) 0.0370(16) 0.0108(13) 0.0024(12) 0.0157(13) N17 0.0329(14) 0.0348(14) 0.0275(12) 0.0073(10) 0.0011(10) 0.0133(11) N21 0.0383(15) 0.0473(15) 0.0330(13) 0.0142(11) 0.0058(11) 0.0215(12) C22 0.0305(16) 0.055(2) 0.0336(16) 0.0147(14) 0.0063(12) 0.0182(14) C23 0.0276(16) 0.0470(18) 0.0320(15) 0.0128(13) 0.0051(12) 0.0127(13) C24 0.0312(16) 0.0321(15) 0.0291(14) 0.0047(12) 0.0038(12) 0.0144(12) C25 0.0261(15) 0.0330(16) 0.0351(15) 0.0086(12) 0.0063(12) 0.0099(12) C26 0.0348(17) 0.0411(17) 0.0322(15) 0.0144(13) 0.0082(12) 0.0130(13) C27 0.0257(15) 0.0298(15) 0.0326(15) 0.0057(12) 0.0041(11) 0.0107(12) N27 0.0266(13) 0.0432(14) 0.0329(12) 0.0164(11) 0.0071(10) 0.0178(11) O27 0.0256(11) 0.0530(13) 0.0408(11) 0.0187(9) 0.0062(8) 0.0150(9) C31 0.0271(16) 0.0374(17) 0.0395(17) 0.0072(13) 0.0025(12) 0.0089(13) O31 0.0540(15) 0.0758(17) 0.0388(12) 0.0213(11) 0.0091(10) 0.0434(13) O32 0.0385(13) 0.0696(16) 0.0340(11) 0.0078(10) 0.0070(9) 0.0230(11) C32 0.0456(19) 0.054(2) 0.0344(16) 0.0146(14) 0.0059(13) 0.0244(16) C33 0.0358(18) 0.0449(19) 0.0504(19) 0.0171(15) 0.0044(14) 0.0156(14) C34 0.0383(18) 0.055(2) 0.0507(19) 0.0183(16) 0.0067(14) 0.0225(16) C35 0.0354(18) 0.0476(19) 0.0474(18) 0.0157(15) 0.0039(14) 0.0180(15) C36 0.0429(19) 0.0438(19) 0.0485(18) 0.0160(15) 0.0035(14) 0.0196(15) C37 0.047(2) 0.050(2) 0.0429(17) 0.0121(15) 0.0030(14) 0.0246(16) C38 0.057(2) 0.056(2) 0.0498(19) 0.0102(16) 0.0023(16) 0.0331(18) _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 O1S H1A 0.81(3) . ? O1S H1B 0.97(4) . ? N11 C16 1.332(4) . ? N11 C12 1.344(3) . ? C12 C13 1.383(4) . ? C12 C17 1.457(4) . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C14 C15 1.376(4) . ? C14 H14 0.9500 . ? C15 C16 1.375(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N17 1.279(3) . ? C17 H17 0.9500 . ? N17 N27 1.372(3) . ? N21 C26 1.329(4) . ? N21 C22 1.329(4) . ? C22 C23 1.378(4) . ? C22 H22 0.9500 . ? C23 C24 1.382(4) . ? C23 H23 0.9500 . ? C24 C25 1.392(4) . ? C24 C27 1.496(4) . ? C25 C26 1.369(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O27 1.228(3) . ? C27 N27 1.344(3) . ? N27 H27 0.82(3) . ? C31 O32 1.215(3) . ? C31 O31 1.303(3) . ? C31 C32 1.485(4) . ? O31 H31 1.00(4) . ? C32 C33 1.510(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.514(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.499(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.510(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.503(4) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.509(4) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? 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 H1A O1S H1B 101(3) . . ? C16 N11 C12 116.7(3) . . ? N11 C12 C13 122.8(3) . . ? N11 C12 C17 114.8(3) . . ? C13 C12 C17 122.4(3) . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 118.7(3) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C16 C15 C14 118.4(3) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? N11 C16 C15 124.3(3) . . ? N11 C16 H16 117.9 . . ? C15 C16 H16 117.9 . . ? N17 C17 C12 120.5(3) . . ? N17 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C17 N17 N27 115.5(2) . . ? C26 N21 C22 117.8(2) . . ? N21 C22 C23 123.2(3) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C22 C23 C24 118.7(3) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C25 118.2(3) . . ? C23 C24 C27 124.4(3) . . ? C25 C24 C27 117.4(3) . . ? C26 C25 C24 118.8(3) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? N21 C26 C25 123.3(3) . . ? N21 C26 H26 118.3 . . ? C25 C26 H26 118.3 . . ? O27 C27 N27 124.1(3) . . ? O27 C27 C24 119.8(2) . . ? N27 C27 C24 116.1(2) . . ? C27 N27 N17 118.4(2) . . ? C27 N27 H27 122(2) . . ? N17 N27 H27 120(2) . . ? O32 C31 O31 122.8(3) . . ? O32 C31 C32 123.5(3) . . ? O31 C31 C32 113.7(2) . . ? C31 O31 H31 116.0(19) . . ? C31 C32 C33 115.2(2) . . ? C31 C32 H32A 108.5 . . ? C33 C32 H32A 108.5 . . ? C31 C32 H32B 108.5 . . ? C33 C32 H32B 108.5 . . ? H32A C32 H32B 107.5 . . ? C32 C33 C34 112.3(2) . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33B 109.1 . . ? C34 C33 H33B 109.1 . . ? H33A C33 H33B 107.9 . . ? C35 C34 C33 114.4(3) . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 114.3(3) . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35B 108.7 . . ? C36 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C37 C36 C35 113.9(3) . . ? C37 C36 H36A 108.8 . . ? C35 C36 H36A 108.8 . . ? C37 C36 H36B 108.8 . . ? C35 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? C36 C37 C38 114.8(3) . . ? C36 C37 H37A 108.6 . . ? C38 C37 H37A 108.6 . . ? C36 C37 H37B 108.6 . . ? C38 C37 H37B 108.6 . . ? H37A C37 H37B 107.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? 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 C16 N11 C12 C13 0.7(4) . . . . ? C16 N11 C12 C17 -177.5(3) . . . . ? N11 C12 C13 C14 -0.5(4) . . . . ? C17 C12 C13 C14 177.6(3) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C13 C14 C15 C16 1.8(4) . . . . ? C12 N11 C16 C15 0.4(5) . . . . ? C14 C15 C16 N11 -1.7(5) . . . . ? N11 C12 C17 N17 172.6(2) . . . . ? C13 C12 C17 N17 -5.6(4) . . . . ? C12 C17 N17 N27 -177.7(2) . . . . ? C26 N21 C22 C23 0.2(4) . . . . ? N21 C22 C23 C24 -0.4(4) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C22 C23 C24 C27 179.1(2) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? C27 C24 C25 C26 -178.9(2) . . . . ? C22 N21 C26 C25 0.2(4) . . . . ? C24 C25 C26 N21 -0.3(4) . . . . ? C23 C24 C27 O27 -163.2(3) . . . . ? C25 C24 C27 O27 15.6(4) . . . . ? C23 C24 C27 N27 17.0(4) . . . . ? C25 C24 C27 N27 -164.1(2) . . . . ? O27 C27 N27 N17 -0.3(4) . . . . ? C24 C27 N27 N17 179.5(2) . . . . ? C17 N17 N27 C27 -179.5(2) . . . . ? O32 C31 C32 C33 22.3(4) . . . . ? O31 C31 C32 C33 -158.9(3) . . . . ? C31 C32 C33 C34 -175.1(3) . . . . ? C32 C33 C34 C35 -174.1(3) . . . . ? C33 C34 C35 C36 -178.9(3) . . . . ? C34 C35 C36 C37 -179.3(3) . . . . ? C35 C36 C37 C38 177.3(3) . . . . ? 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 O31 H31 N21 1.00(4) 1.60(4) 2.597(3) 178(3) . N27 H27 O1S 0.82(3) 2.01(3) 2.815(3) 166(3) 2_656 O1S H1A O32 0.81(3) 1.97(3) 2.758(3) 164(3) . O1S H1B O27 0.97(4) 1.81(4) 2.767(3) 168(3) 2_556 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.70 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.290 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.064 #END data_sf0607m(2D) _database_code_depnum_ccdc_archive 'CCDC 853502' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF363 [4-pyridyl-CONH-N=CH-2-pyridyl] adipic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O)2 (C6 H10 O4) (H2 O)2 ; _chemical_formula_sum 'C30 H34 N8 O8' _chemical_formula_weight 634.65 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 6.6047(8) _cell_length_b 8.0678(9) _cell_length_c 15.3573(18) _cell_angle_alpha 98.182(6) _cell_angle_beta 101.688(8) _cell_angle_gamma 104.436(9) _cell_volume 759.84(15) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2308 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 9931 _diffrn_reflns_av_R_equivalents 0.1503 _diffrn_reflns_av_sigmaI/netI 0.0988 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3529 _reflns_number_gt 2518 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0900P)^2^+0.0500P] 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 3529 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1713 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 O1S O -0.0591(2) 0.1378(2) 0.38649(9) 0.0386(4) Uani 1 1 d . . . H1A H -0.152(4) 0.159(3) 0.4094(16) 0.046 Uiso 1 1 d . . . H1B H -0.085(3) 0.170(3) 0.3338(17) 0.046 Uiso 1 1 d . . . N11 N 0.3890(2) 0.5661(2) 0.71378(10) 0.0292(3) Uani 1 1 d . . . C12 C 0.2323(3) 0.4332(3) 0.65860(12) 0.0319(4) Uani 1 1 d . . . H12 H 0.0906 0.4134 0.6674 0.038 Uiso 1 1 calc R . . C13 C 0.2664(3) 0.3225(2) 0.58906(12) 0.0292(4) Uani 1 1 d . . . H13 H 0.1511 0.2278 0.5516 0.035 Uiso 1 1 calc R . . C14 C 0.4727(2) 0.3530(2) 0.57523(11) 0.0226(4) Uani 1 1 d . . . C15 C 0.6341(3) 0.4907(2) 0.63196(11) 0.0252(4) Uani 1 1 d . . . H15 H 0.7768 0.5146 0.6241 0.030 Uiso 1 1 calc R . . C16 C 0.5879(3) 0.5940(2) 0.70047(12) 0.0276(4) Uani 1 1 d . . . H16 H 0.7011 0.6882 0.7396 0.033 Uiso 1 1 calc R . . C17 C 0.5336(2) 0.2426(2) 0.50328(11) 0.0230(4) Uani 1 1 d . . . N17 N 0.3698(2) 0.13320(18) 0.43725(9) 0.0249(3) Uani 1 1 d . . . H17 H 0.240(3) 0.134(3) 0.4296(14) 0.030 Uiso 1 1 d . . . O17 O 0.72404(18) 0.25548(16) 0.50725(8) 0.0316(3) Uani 1 1 d . . . N21 N 0.1090(2) -0.30588(19) 0.18324(10) 0.0310(4) Uani 1 1 d . . . C22 C 0.2898(3) -0.1878(2) 0.23455(11) 0.0260(4) Uani 1 1 d . . . C23 C 0.4936(3) -0.1793(2) 0.22097(12) 0.0290(4) Uani 1 1 d . . . H23 H 0.6174 -0.0919 0.2583 0.035 Uiso 1 1 calc R . . C24 C 0.5127(3) -0.3003(2) 0.15220(12) 0.0336(4) Uani 1 1 d . . . H24 H 0.6499 -0.2980 0.1414 0.040 Uiso 1 1 calc R . . C25 C 0.3284(3) -0.4247(2) 0.09949(13) 0.0363(4) Uani 1 1 d . . . H25 H 0.3361 -0.5102 0.0519 0.044 Uiso 1 1 calc R . . C26 C 0.1320(3) -0.4222(2) 0.11743(12) 0.0334(4) Uani 1 1 d . . . H26 H 0.0060 -0.5083 0.0808 0.040 Uiso 1 1 calc R . . C27 C 0.2571(3) -0.0688(2) 0.30863(12) 0.0283(4) Uani 1 1 d . . . H27 H 0.1151 -0.0668 0.3110 0.034 Uiso 1 1 calc R . . N27 N 0.4178(2) 0.03121(18) 0.36945(9) 0.0258(3) Uani 1 1 d . . . C31 C 0.2153(3) 0.8186(2) 0.86089(12) 0.0269(4) Uani 1 1 d . . . O31 O 0.3688(2) 0.74237(19) 0.86596(9) 0.0407(4) Uani 1 1 d . . . H31 H 0.367(4) 0.674(3) 0.8053(17) 0.049 Uiso 1 1 d . . . O32 O 0.09009(19) 0.81454(18) 0.79060(8) 0.0379(4) Uani 1 1 d . . . C32 C 0.2097(3) 0.9144(2) 0.95135(12) 0.0288(4) Uani 1 1 d . . . H32A H 0.3259 1.0264 0.9686 0.035 Uiso 1 1 calc R . . H32B H 0.2406 0.8441 0.9975 0.035 Uiso 1 1 calc R . . C33 C -0.0022(3) 0.9522(2) 0.95338(11) 0.0291(4) Uani 1 1 d . . . H33A H -0.1195 0.8409 0.9363 0.035 Uiso 1 1 calc R . . H33B H -0.0334 1.0243 0.9081 0.035 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 O1S 0.0269(7) 0.0656(10) 0.0271(7) 0.0042(7) 0.0098(6) 0.0204(7) N11 0.0313(7) 0.0321(8) 0.0256(8) 0.0001(6) 0.0095(6) 0.0130(6) C12 0.0259(8) 0.0435(11) 0.0274(9) 0.0008(8) 0.0094(7) 0.0133(8) C13 0.0225(8) 0.0356(9) 0.0261(9) -0.0001(7) 0.0060(7) 0.0059(7) C14 0.0251(8) 0.0243(8) 0.0212(8) 0.0047(6) 0.0085(6) 0.0096(6) C15 0.0230(8) 0.0265(8) 0.0270(8) 0.0040(7) 0.0084(6) 0.0078(6) C16 0.0285(8) 0.0247(8) 0.0276(9) 0.0011(7) 0.0062(7) 0.0069(7) C17 0.0243(8) 0.0234(8) 0.0220(8) 0.0032(6) 0.0077(6) 0.0076(6) N17 0.0222(7) 0.0265(7) 0.0256(7) -0.0005(6) 0.0077(6) 0.0080(6) O17 0.0230(6) 0.0383(7) 0.0302(7) -0.0040(5) 0.0090(5) 0.0068(5) N21 0.0312(7) 0.0305(8) 0.0262(8) 0.0003(6) 0.0052(6) 0.0046(6) C22 0.0298(8) 0.0246(8) 0.0226(8) 0.0031(6) 0.0060(7) 0.0071(7) C23 0.0306(9) 0.0270(9) 0.0277(9) 0.0030(7) 0.0076(7) 0.0064(7) C24 0.0360(9) 0.0376(10) 0.0298(9) 0.0041(8) 0.0134(8) 0.0126(8) C25 0.0514(11) 0.0313(10) 0.0272(9) 0.0002(7) 0.0136(8) 0.0137(9) C26 0.0389(10) 0.0297(9) 0.0237(9) -0.0019(7) 0.0040(7) 0.0032(7) C27 0.0277(8) 0.0272(9) 0.0300(9) 0.0023(7) 0.0084(7) 0.0089(7) N27 0.0283(7) 0.0258(7) 0.0235(7) 0.0010(6) 0.0082(6) 0.0092(6) C31 0.0233(8) 0.0301(9) 0.0247(9) 0.0002(7) 0.0080(7) 0.0042(7) O31 0.0398(7) 0.0550(9) 0.0291(7) -0.0071(6) 0.0075(6) 0.0264(7) O32 0.0336(7) 0.0560(9) 0.0247(7) 0.0024(6) 0.0083(5) 0.0162(6) C32 0.0281(8) 0.0324(9) 0.0253(9) -0.0006(7) 0.0068(7) 0.0113(7) C33 0.0269(8) 0.0344(9) 0.0253(9) -0.0015(7) 0.0076(7) 0.0110(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 O1S H1A 0.81(2) . ? O1S H1B 0.88(3) . ? N11 C12 1.331(2) . ? N11 C16 1.339(2) . ? C12 C13 1.384(2) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.374(2) . ? C14 C17 1.502(2) . ? C15 C16 1.379(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.2241(19) . ? C17 N17 1.342(2) . ? N17 N27 1.3719(18) . ? N17 H17 0.84(2) . ? N21 C26 1.338(2) . ? N21 C22 1.339(2) . ? C22 C23 1.390(2) . ? C22 C27 1.468(2) . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C24 H24 0.9500 . ? C25 C26 1.383(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.268(2) . ? C27 H27 0.9500 . ? C31 O32 1.210(2) . ? C31 O31 1.306(2) . ? C31 C32 1.503(2) . ? O31 H31 1.01(3) . ? C32 C33 1.510(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C33 1.518(3) 2_577 ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? 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 H1A O1S H1B 104(2) . . ? C12 N11 C16 118.13(14) . . ? N11 C12 C13 123.00(15) . . ? N11 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C12 C13 C14 118.56(16) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 118.39(14) . . ? C15 C14 C17 117.27(13) . . ? C13 C14 C17 124.33(15) . . ? C14 C15 C16 119.62(14) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? N11 C16 C15 122.30(15) . . ? N11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O17 C17 N17 123.85(15) . . ? O17 C17 C14 119.87(14) . . ? N17 C17 C14 116.28(13) . . ? C17 N17 N27 118.33(13) . . ? C17 N17 H17 124.4(14) . . ? N27 N17 H17 116.5(14) . . ? C26 N21 C22 116.65(15) . . ? N21 C22 C23 123.39(16) . . ? N21 C22 C27 114.52(14) . . ? C23 C22 C27 122.07(15) . . ? C24 C23 C22 118.77(16) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C25 C24 C23 118.64(16) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 118.61(16) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? N21 C26 C25 123.94(17) . . ? N21 C26 H26 118.0 . . ? C25 C26 H26 118.0 . . ? N27 C27 C22 120.16(15) . . ? N27 C27 H27 119.9 . . ? C22 C27 H27 119.9 . . ? C27 N27 N17 115.65(13) . . ? O32 C31 O31 123.85(15) . . ? O32 C31 C32 122.80(15) . . ? O31 C31 C32 113.35(15) . . ? C31 O31 H31 112.6(13) . . ? C31 C32 C33 114.30(14) . . ? C31 C32 H32A 108.7 . . ? C33 C32 H32A 108.7 . . ? C31 C32 H32B 108.7 . . ? C33 C32 H32B 108.7 . . ? H32A C32 H32B 107.6 . . ? C32 C33 C33 111.66(18) . 2_577 ? C32 C33 H33A 109.3 . . ? C33 C33 H33A 109.3 2_577 . ? C32 C33 H33B 109.3 . . ? C33 C33 H33B 109.3 2_577 . ? H33A C33 H33B 107.9 . . ? 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 C16 N11 C12 C13 0.6(3) . . . . ? N11 C12 C13 C14 -1.0(3) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C12 C13 C14 C17 179.21(15) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C17 C14 C15 C16 -178.60(15) . . . . ? C12 N11 C16 C15 0.2(3) . . . . ? C14 C15 C16 N11 -0.5(3) . . . . ? C15 C14 C17 O17 13.6(2) . . . . ? C13 C14 C17 O17 -164.92(17) . . . . ? C15 C14 C17 N17 -166.49(15) . . . . ? C13 C14 C17 N17 15.0(2) . . . . ? O17 C17 N17 N27 -0.9(3) . . . . ? C14 C17 N17 N27 179.23(13) . . . . ? C26 N21 C22 C23 1.5(3) . . . . ? C26 N21 C22 C27 -177.04(15) . . . . ? N21 C22 C23 C24 -1.2(3) . . . . ? C27 C22 C23 C24 177.30(15) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C22 N21 C26 C25 -0.9(3) . . . . ? C24 C25 C26 N21 0.0(3) . . . . ? N21 C22 C27 N27 169.72(16) . . . . ? C23 C22 C27 N27 -8.9(3) . . . . ? C22 C27 N27 N17 -177.99(14) . . . . ? C17 N17 N27 C27 -179.61(15) . . . . ? O32 C31 C32 C33 19.6(3) . . . . ? O31 C31 C32 C33 -160.92(16) . . . . ? C31 C32 C33 C33 179.57(18) . . . 2_577 ? 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 O31 H31 N11 1.01(3) 1.60(3) 2.6035(19) 174(2) . O1S H1A O17 0.81(2) 2.00(2) 2.7649(17) 157(2) 1_455 O1S H1B O32 0.88(3) 1.93(3) 2.7744(19) 161(2) 2_566 N17 H17 O1S 0.84(2) 1.96(2) 2.7928(19) 168(2) . _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.385 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.071 #END data_sf0609m(2E) _database_code_depnum_ccdc_archive 'CCDC 853503' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF357 [(3-pyridyl)-CONH-N=CH-(2-pyridyl)]2, octanedioic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O)2 (C8 H14 O4) (H2 O)2 ; _chemical_formula_sum 'C32 H38 N8 O8' _chemical_formula_weight 662.70 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 6.6074(6) _cell_length_b 8.1545(7) _cell_length_c 15.8735(14) _cell_angle_alpha 81.488(6) _cell_angle_beta 83.679(6) _cell_angle_gamma 75.024(7) _cell_volume 814.80(12) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2675 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 350 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 10732 _diffrn_reflns_av_R_equivalents 0.1070 _diffrn_reflns_av_sigmaI/netI 0.0944 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3801 _reflns_number_gt 2162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0800P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3801 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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 O1S O 1.0223(3) 0.3558(2) 0.39196(10) 0.0411(4) Uani 1 1 d . . . H1A H 0.900(4) 0.332(3) 0.4192(16) 0.049 Uiso 1 1 d . . . H1B H 1.047(4) 0.307(3) 0.3451(17) 0.049 Uiso 1 1 d . . . N11 N 0.2238(3) -0.0196(2) 0.69635(11) 0.0317(4) Uani 1 1 d . . . C12 C 0.1094(3) 0.1050(3) 0.64458(13) 0.0344(5) Uani 1 1 d . . . H12A H -0.0393 0.1275 0.6526 0.041 Uiso 1 1 calc R . . C13 C 0.1976(3) 0.2025(3) 0.57994(13) 0.0301(5) Uani 1 1 d . . . H13A H 0.1112 0.2918 0.5448 0.036 Uiso 1 1 calc R . . C14 C 0.4139(3) 0.1685(2) 0.56698(12) 0.0251(4) Uani 1 1 d . . . C15 C 0.5323(3) 0.0382(2) 0.62062(13) 0.0280(5) Uani 1 1 d . . . H15A H 0.6815 0.0115 0.6137 0.034 Uiso 1 1 calc R . . C16 C 0.4314(3) -0.0516(3) 0.68387(13) 0.0313(5) Uani 1 1 d . . . H16A H 0.5138 -0.1409 0.7204 0.038 Uiso 1 1 calc R . . C17 C 0.5307(3) 0.2649(2) 0.49972(12) 0.0258(5) Uani 1 1 d . . . N17 N 0.4179(3) 0.3606(2) 0.43640(10) 0.0260(4) Uani 1 1 d . . . H17 H 0.294(3) 0.357(3) 0.4319(14) 0.031 Uiso 1 1 d . . . O17 O 0.7165(2) 0.25469(18) 0.50455(9) 0.0343(4) Uani 1 1 d . . . N21 N 0.3497(3) 0.7489(2) 0.19454(11) 0.0363(5) Uani 1 1 d . . . C22 C 0.4913(3) 0.6460(2) 0.24587(13) 0.0289(5) Uani 1 1 d . . . C23 C 0.7015(3) 0.6441(3) 0.23600(13) 0.0313(5) Uani 1 1 d . . . H23A H 0.7970 0.5673 0.2729 0.038 Uiso 1 1 calc R . . C24 C 0.7720(4) 0.7543(3) 0.17228(14) 0.0364(5) Uani 1 1 d . . . H24A H 0.9162 0.7557 0.1644 0.044 Uiso 1 1 calc R . . C25 C 0.6269(4) 0.8626(3) 0.12022(14) 0.0416(6) Uani 1 1 d . . . H25A H 0.6692 0.9416 0.0759 0.050 Uiso 1 1 calc R . . C26 C 0.4223(4) 0.8547(3) 0.13316(14) 0.0416(6) Uani 1 1 d . . . H26A H 0.3249 0.9293 0.0962 0.050 Uiso 1 1 calc R . . C27 C 0.4035(3) 0.5390(2) 0.31452(13) 0.0303(5) Uani 1 1 d . . . H27A H 0.2614 0.5337 0.3152 0.036 Uiso 1 1 calc R . . N27 N 0.5168(3) 0.4526(2) 0.37363(10) 0.0272(4) Uani 1 1 d . . . C31 C -0.0617(3) -0.2458(2) 0.83058(13) 0.0286(5) Uani 1 1 d . . . O31 O 0.0854(3) -0.1710(2) 0.83800(10) 0.0445(5) Uani 1 1 d . . . H31 H 0.138(4) -0.125(3) 0.7873(17) 0.053 Uiso 1 1 d . . . O32 O -0.1370(2) -0.2411(2) 0.76387(9) 0.0421(4) Uani 1 1 d . . . C32 C -0.1264(3) -0.3430(3) 0.91227(13) 0.0310(5) Uani 1 1 d . . . H32A H -0.1182 -0.2804 0.9602 0.037 Uiso 1 1 calc R . . H32B H -0.0246 -0.4558 0.9204 0.037 Uiso 1 1 calc R . . C33 C -0.3441(3) -0.3711(3) 0.91666(13) 0.0328(5) Uani 1 1 d . . . H33A H -0.3601 -0.4192 0.8648 0.039 Uiso 1 1 calc R . . H33B H -0.4486 -0.2596 0.9177 0.039 Uiso 1 1 calc R . . C34 C -0.3884(3) -0.4914(3) 0.99506(13) 0.0300(5) Uani 1 1 d . . . H34A H -0.2920 -0.6058 0.9913 0.036 Uiso 1 1 calc R . . H34B H -0.3589 -0.4488 1.0465 0.036 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 O1S 0.0328(9) 0.0629(11) 0.0299(9) 0.0008(8) -0.0010(7) -0.0199(8) N11 0.0386(11) 0.0311(9) 0.0259(9) 0.0059(7) -0.0017(8) -0.0150(8) C12 0.0331(12) 0.0405(13) 0.0300(12) 0.0024(10) -0.0011(9) -0.0139(10) C13 0.0302(11) 0.0329(11) 0.0248(11) 0.0047(9) -0.0023(9) -0.0077(9) C14 0.0330(11) 0.0214(10) 0.0209(10) -0.0001(8) -0.0006(8) -0.0089(8) C15 0.0296(11) 0.0242(10) 0.0288(11) 0.0002(9) -0.0021(9) -0.0060(8) C16 0.0385(13) 0.0250(10) 0.0293(11) 0.0032(9) -0.0052(9) -0.0081(9) C17 0.0299(11) 0.0218(10) 0.0248(10) -0.0006(8) 0.0004(8) -0.0070(8) N17 0.0277(9) 0.0257(8) 0.0244(9) 0.0050(7) -0.0017(7) -0.0110(7) O17 0.0288(8) 0.0387(9) 0.0315(8) 0.0086(7) -0.0017(6) -0.0092(6) N21 0.0440(11) 0.0303(10) 0.0298(10) 0.0069(8) -0.0048(8) -0.0059(8) C22 0.0379(12) 0.0220(10) 0.0250(11) 0.0014(8) -0.0022(9) -0.0068(9) C23 0.0406(13) 0.0271(11) 0.0258(11) -0.0010(9) -0.0014(9) -0.0096(9) C24 0.0475(14) 0.0317(12) 0.0313(12) -0.0029(10) 0.0054(10) -0.0157(10) C25 0.0616(17) 0.0300(12) 0.0299(12) 0.0033(10) 0.0091(11) -0.0144(11) C26 0.0561(16) 0.0318(12) 0.0293(12) 0.0077(10) -0.0015(11) -0.0045(11) C27 0.0338(12) 0.0275(11) 0.0297(11) 0.0007(9) -0.0015(9) -0.0105(9) N27 0.0328(10) 0.0241(9) 0.0238(9) 0.0024(7) 0.0002(7) -0.0091(7) C31 0.0278(11) 0.0281(11) 0.0269(11) 0.0028(9) 0.0006(9) -0.0062(9) O31 0.0539(11) 0.0588(11) 0.0275(8) 0.0141(8) -0.0059(8) -0.0353(9) O32 0.0441(10) 0.0609(11) 0.0236(8) 0.0035(7) -0.0052(7) -0.0209(8) C32 0.0320(12) 0.0326(11) 0.0271(11) 0.0062(9) -0.0019(9) -0.0113(9) C33 0.0333(12) 0.0331(11) 0.0315(12) 0.0084(9) -0.0037(9) -0.0139(9) C34 0.0299(11) 0.0294(11) 0.0301(11) 0.0038(9) -0.0022(9) -0.0107(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 O1S H1A 0.93(3) . ? O1S H1B 0.88(3) . ? N11 C16 1.326(3) . ? N11 C12 1.331(3) . ? C12 C13 1.375(3) . ? C12 H12A 0.9500 . ? C13 C14 1.382(3) . ? C13 H13A 0.9500 . ? C14 C15 1.384(3) . ? C14 C17 1.496(3) . ? C15 C16 1.370(3) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 O17 1.219(2) . ? C17 N17 1.344(3) . ? N17 N27 1.368(2) . ? N17 H17 0.84(2) . ? N21 C26 1.337(3) . ? N21 C22 1.343(3) . ? C22 C23 1.377(3) . ? C22 C27 1.458(3) . ? C23 C24 1.375(3) . ? C23 H23A 0.9500 . ? C24 C25 1.380(3) . ? C24 H24A 0.9500 . ? C25 C26 1.362(3) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 N27 1.274(3) . ? C27 H27A 0.9500 . ? C31 O32 1.210(2) . ? C31 O31 1.297(2) . ? C31 C32 1.497(3) . ? O31 H31 0.91(3) . ? C32 C33 1.507(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.518(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C34 1.506(4) 2_447 ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? 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 H1A O1S H1B 107(2) . . ? C16 N11 C12 118.19(17) . . ? N11 C12 C13 122.8(2) . . ? N11 C12 H12A 118.6 . . ? C13 C12 H12A 118.6 . . ? C12 C13 C14 118.90(19) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C13 C14 C15 118.19(17) . . ? C13 C14 C17 124.63(18) . . ? C15 C14 C17 117.18(18) . . ? C16 C15 C14 119.02(19) . . ? C16 C15 H15A 120.5 . . ? C14 C15 H15A 120.5 . . ? N11 C16 C15 122.9(2) . . ? N11 C16 H16A 118.5 . . ? C15 C16 H16A 118.5 . . ? O17 C17 N17 123.90(18) . . ? O17 C17 C14 120.21(18) . . ? N17 C17 C14 115.89(18) . . ? C17 N17 N27 118.24(17) . . ? C17 N17 H17 121.6(15) . . ? N27 N17 H17 119.8(15) . . ? C26 N21 C22 116.4(2) . . ? N21 C22 C23 122.97(18) . . ? N21 C22 C27 114.49(19) . . ? C23 C22 C27 122.53(19) . . ? C24 C23 C22 119.5(2) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C23 C24 C25 117.9(2) . . ? C23 C24 H24A 121.0 . . ? C25 C24 H24A 121.0 . . ? C26 C25 C24 119.1(2) . . ? C26 C25 H25A 120.5 . . ? C24 C25 H25A 120.5 . . ? N21 C26 C25 124.2(2) . . ? N21 C26 H26A 117.9 . . ? C25 C26 H26A 117.9 . . ? N27 C27 C22 120.2(2) . . ? N27 C27 H27A 119.9 . . ? C22 C27 H27A 119.9 . . ? C27 N27 N17 115.64(17) . . ? O32 C31 O31 123.59(19) . . ? O32 C31 C32 122.84(19) . . ? O31 C31 C32 113.56(18) . . ? C31 O31 H31 113.6(17) . . ? C31 C32 C33 114.79(18) . . ? C31 C32 H32A 108.6 . . ? C33 C32 H32A 108.6 . . ? C31 C32 H32B 108.6 . . ? C33 C32 H32B 108.6 . . ? H32A C32 H32B 107.5 . . ? C32 C33 C34 112.15(18) . . ? C32 C33 H33A 109.2 . . ? C34 C33 H33A 109.2 . . ? C32 C33 H33B 109.2 . . ? C34 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? C34 C34 C33 113.0(2) 2_447 . ? C34 C34 H34A 109.0 2_447 . ? C33 C34 H34A 109.0 . . ? C34 C34 H34B 109.0 2_447 . ? C33 C34 H34B 109.0 . . ? H34A C34 H34B 107.8 . . ? 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 C16 N11 C12 C13 -0.9(3) . . . . ? N11 C12 C13 C14 1.1(3) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C12 C13 C14 C17 -179.49(19) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C17 C14 C15 C16 179.08(19) . . . . ? C12 N11 C16 C15 0.4(3) . . . . ? C14 C15 C16 N11 0.0(3) . . . . ? C13 C14 C17 O17 163.0(2) . . . . ? C15 C14 C17 O17 -15.9(3) . . . . ? C13 C14 C17 N17 -16.6(3) . . . . ? C15 C14 C17 N17 164.54(17) . . . . ? O17 C17 N17 N27 -0.1(3) . . . . ? C14 C17 N17 N27 179.45(16) . . . . ? C26 N21 C22 C23 -1.5(3) . . . . ? C26 N21 C22 C27 177.02(18) . . . . ? N21 C22 C23 C24 1.5(3) . . . . ? C27 C22 C23 C24 -176.89(19) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C22 N21 C26 C25 0.3(3) . . . . ? C24 C25 C26 N21 0.8(4) . . . . ? N21 C22 C27 N27 -170.97(19) . . . . ? C23 C22 C27 N27 7.6(3) . . . . ? C22 C27 N27 N17 178.03(16) . . . . ? C17 N17 N27 C27 178.97(18) . . . . ? O32 C31 C32 C33 -24.7(3) . . . . ? O31 C31 C32 C33 156.79(19) . . . . ? C31 C32 C33 C34 171.76(18) . . . . ? C32 C33 C34 C34 174.7(2) . . . 2_447 ? 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 O31 H31 N11 0.91(3) 1.69(3) 2.594(2) 174(2) . O1S H1A O17 0.93(3) 1.87(3) 2.754(2) 160(2) . O1S H1B O32 0.88(3) 1.88(3) 2.734(2) 166(2) 2_656 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.260 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.062 #END data_sf0703m(2F) _database_code_depnum_ccdc_archive 'CCDC 853504' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF 356 (4-pyridyl)-CONH-N=CH-(2-pyridyl), decanedioic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O)2 (C10 H18 O4) (H2 O)2 ; _chemical_formula_sum 'C34 H42 N8 O8' _chemical_formula_weight 690.76 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 6.5516(4) _cell_length_b 8.1666(5) _cell_length_c 33.7458(19) _cell_angle_alpha 94.293(3) _cell_angle_beta 93.041(3) _cell_angle_gamma 105.225(3) _cell_volume 1732.32(18) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 9872 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 32.91 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9763 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 75728 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 32.58 _reflns_number_total 12391 _reflns_number_gt 7114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0630P)^2^+0.1500P] 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 12391 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 O1S O 1.17709(16) -0.02449(14) 0.58823(3) 0.0332(2) Uani 1 1 d . . . H1A H 1.083(3) 0.030(2) 0.5835(5) 0.040 Uiso 1 1 d . . . H1B H 1.111(3) -0.129(2) 0.5893(5) 0.040 Uiso 1 1 d . . . O2S O -0.02871(16) 1.29527(14) -0.05117(3) 0.0301(2) Uani 1 1 d . . . H2A H 0.082(3) 1.285(2) -0.0387(5) 0.036 Uiso 1 1 d . . . H2B H -0.039(3) 1.245(2) -0.0736(5) 0.036 Uiso 1 1 d . . . C31 C 1.1357(2) 0.46653(16) 0.38700(4) 0.0236(3) Uani 1 1 d . . . O31 O 1.33876(16) 0.49877(13) 0.39785(3) 0.0325(2) Uani 1 1 d . . . H31 H 1.358(3) 0.440(2) 0.4183(5) 0.039 Uiso 1 1 d . . . C32 C 1.0934(2) 0.55716(16) 0.35164(4) 0.0229(3) Uani 1 1 d . . . H32A H 1.1243 0.4947 0.3274 0.027 Uiso 1 1 calc R . . H32B H 1.1939 0.6722 0.3543 0.027 Uiso 1 1 calc R . . O32 O 0.99826(16) 0.37011(13) 0.40359(3) 0.0343(2) Uani 1 1 d . . . C33 C 0.8702(2) 0.57655(19) 0.34553(4) 0.0284(3) Uani 1 1 d . . . H33A H 0.8485 0.6613 0.3663 0.034 Uiso 1 1 calc R . . H33B H 0.7664 0.4662 0.3483 0.034 Uiso 1 1 calc R . . C34 C 0.8326(2) 0.63396(18) 0.30447(4) 0.0264(3) Uani 1 1 d . . . H34A H 0.9498 0.7348 0.3005 0.032 Uiso 1 1 calc R . . H34B H 0.8371 0.5418 0.2840 0.032 Uiso 1 1 calc R . . C35 C 0.6227(2) 0.67905(18) 0.29796(4) 0.0276(3) Uani 1 1 d . . . H35A H 0.6248 0.7804 0.3162 0.033 Uiso 1 1 calc R . . H35B H 0.5063 0.5834 0.3049 0.033 Uiso 1 1 calc R . . C36 C 0.5772(2) 0.71600(18) 0.25518(4) 0.0266(3) Uani 1 1 d . . . H36A H 0.6875 0.8175 0.2490 0.032 Uiso 1 1 calc R . . H36B H 0.5866 0.6183 0.2368 0.032 Uiso 1 1 calc R . . C37 C 0.3605(2) 0.74735(18) 0.24773(4) 0.0266(3) Uani 1 1 d . . . H37A H 0.3503 0.8435 0.2665 0.032 Uiso 1 1 calc R . . H37B H 0.2504 0.6450 0.2535 0.032 Uiso 1 1 calc R . . C38 C 0.3139(2) 0.78763(18) 0.20546(4) 0.0264(3) Uani 1 1 d . . . H38A H 0.3182 0.6902 0.1865 0.032 Uiso 1 1 calc R . . H38B H 0.4249 0.8885 0.1992 0.032 Uiso 1 1 calc R . . C39 C 0.0977(2) 0.82288(17) 0.20017(4) 0.0239(3) Uani 1 1 d . . . H39A H -0.0124 0.7195 0.2054 0.029 Uiso 1 1 calc R . . H39B H 0.0919 0.9153 0.2205 0.029 Uiso 1 1 calc R . . C40 C 0.0445(2) 0.87298(16) 0.15972(4) 0.0223(3) Uani 1 1 d . . . O40 O -0.10102(16) 0.95665(14) 0.15995(3) 0.0336(3) Uani 1 1 d . . . H40 H -0.132(3) 0.986(2) 0.1351(5) 0.040 Uiso 1 1 d . . . O41 O 0.12770(15) 0.83900(13) 0.12996(3) 0.0298(2) Uani 1 1 d . . . N11_1 N 1.44505(19) 0.34422(14) 0.45854(3) 0.0256(2) Uani 1 1 d . . . C12_1 C 1.3248(2) 0.24853(17) 0.48322(4) 0.0257(3) Uani 1 1 d . . . H12_1 H 1.1750 0.2228 0.4785 0.031 Uiso 1 1 calc R . . C13_1 C 1.4069(2) 0.18416(16) 0.51563(4) 0.0231(3) Uani 1 1 d . . . H13_1 H 1.3155 0.1177 0.5328 0.028 Uiso 1 1 calc R . . C14_1 C 1.62570(19) 0.21941(15) 0.52225(4) 0.0193(2) Uani 1 1 d . . . C15_1 C 1.7511(2) 0.31875(17) 0.49639(4) 0.0262(3) Uani 1 1 d . . . H15_1 H 1.9014 0.3451 0.5001 0.031 Uiso 1 1 calc R . . C16_1 C 1.6553(2) 0.37885(18) 0.46525(4) 0.0285(3) Uani 1 1 d . . . H16_1 H 1.7426 0.4477 0.4479 0.034 Uiso 1 1 calc R . . C17_1 C 1.74004(19) 0.15458(15) 0.55484(4) 0.0207(3) Uani 1 1 d . . . N17_1 N 1.61945(18) 0.06712(14) 0.58171(3) 0.0211(2) Uani 1 1 d . . . H17_1 H 1.479(2) 0.0444(18) 0.5822(4) 0.025 Uiso 1 1 d . . . O17_1 O 1.93314(14) 0.18031(13) 0.55610(3) 0.0311(2) Uani 1 1 d . . . N21_1 N 1.57959(19) -0.19775(15) 0.69861(3) 0.0296(3) Uani 1 1 d . . . C22_1 C 1.7139(2) -0.12333(16) 0.67227(4) 0.0237(3) Uani 1 1 d . . . C23_1 C 1.9320(2) -0.10096(17) 0.67689(4) 0.0259(3) Uani 1 1 d . . . H23_1 H 2.0213 -0.0465 0.6578 0.031 Uiso 1 1 calc R . . C24_1 C 2.0171(2) -0.15915(18) 0.70975(4) 0.0307(3) Uani 1 1 d . . . H24_1 H 2.1654 -0.1464 0.7135 0.037 Uiso 1 1 calc R . . C25_1 C 1.8806(3) -0.23649(18) 0.73698(4) 0.0319(3) Uani 1 1 d . . . H25_1 H 1.9334 -0.2774 0.7599 0.038 Uiso 1 1 calc R . . C26_1 C 1.6662(3) -0.25283(19) 0.73002(4) 0.0331(3) Uani 1 1 d . . . H26_1 H 1.5741 -0.3068 0.7488 0.040 Uiso 1 1 calc R . . C27_1 C 1.6106(2) -0.06521(17) 0.63835(4) 0.0244(3) Uani 1 1 d . . . H27_1 H 1.4609 -0.0840 0.6360 0.029 Uiso 1 1 calc R . . N27_1 N 1.72427(17) 0.01086(13) 0.61210(3) 0.0219(2) Uani 1 1 d . . . N11_2 N -0.22519(17) 1.05181(14) 0.09252(3) 0.0234(2) Uani 1 1 d . . . C12_2 C -0.1082(2) 1.15664(17) 0.06875(4) 0.0245(3) Uani 1 1 d . . . H12_2 H 0.0419 1.1828 0.0728 0.029 Uiso 1 1 calc R . . C13_2 C -0.1957(2) 1.22904(17) 0.03849(4) 0.0216(3) Uani 1 1 d . . . H13_2 H -0.1073 1.3036 0.0223 0.026 Uiso 1 1 calc R . . C14_2 C -0.41534(18) 1.19013(15) 0.03236(3) 0.0170(2) Uani 1 1 d . . . C15_2 C -0.53720(19) 1.08078(15) 0.05702(4) 0.0194(2) Uani 1 1 d . . . H15_2 H -0.6877 1.0513 0.0536 0.023 Uiso 1 1 calc R . . C16_2 C -0.4367(2) 1.01565(16) 0.08654(4) 0.0217(3) Uani 1 1 d . . . H16_2 H -0.5212 0.9418 0.1034 0.026 Uiso 1 1 calc R . . C17_2 C -0.53260(19) 1.26024(15) 0.00114(3) 0.0173(2) Uani 1 1 d . . . N17_2 N -0.41650(17) 1.33264(13) -0.02794(3) 0.0188(2) Uani 1 1 d . . . H17_2 H -0.290(2) 1.3262(18) -0.0317(4) 0.023 Uiso 1 1 d . . . O17_2 O -0.72183(13) 1.25012(12) 0.00304(3) 0.0240(2) Uani 1 1 d . . . N21_2 N -0.34253(17) 1.63402(14) -0.13870(3) 0.0234(2) Uani 1 1 d . . . C22_2 C -0.48760(19) 1.54291(15) -0.11639(4) 0.0191(2) Uani 1 1 d . . . C23_2 C -0.7038(2) 1.52944(16) -0.12201(4) 0.0213(3) Uani 1 1 d . . . H23_2 H -0.8013 1.4628 -0.1058 0.026 Uiso 1 1 calc R . . C24_2 C -0.7741(2) 1.61476(17) -0.15156(4) 0.0251(3) Uani 1 1 d . . . H24_2 H -0.9207 1.6074 -0.1561 0.030 Uiso 1 1 calc R . . C25_2 C -0.6258(2) 1.71122(17) -0.17436(4) 0.0271(3) Uani 1 1 d . . . H25_2 H -0.6683 1.7724 -0.1947 0.032 Uiso 1 1 calc R . . C26_2 C -0.4142(2) 1.71634(17) -0.16677(4) 0.0258(3) Uani 1 1 d . . . H26_2 H -0.3137 1.7826 -0.1825 0.031 Uiso 1 1 calc R . . C27_2 C -0.3997(2) 1.46351(15) -0.08440(4) 0.0209(3) Uani 1 1 d . . . H27_2 H -0.2555 1.4608 -0.0838 0.025 Uiso 1 1 calc R . . N27_2 N -0.51624(16) 1.39802(13) -0.05738(3) 0.0189(2) 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 O1S 0.0229(5) 0.0346(6) 0.0466(7) 0.0181(5) 0.0082(4) 0.0106(4) O2S 0.0202(5) 0.0550(7) 0.0196(5) 0.0039(5) 0.0001(4) 0.0182(5) C31 0.0300(7) 0.0224(6) 0.0209(6) 0.0025(5) 0.0015(5) 0.0114(5) O31 0.0291(5) 0.0415(6) 0.0297(5) 0.0174(5) -0.0043(4) 0.0115(5) C32 0.0248(6) 0.0238(6) 0.0202(6) 0.0050(5) -0.0012(5) 0.0064(5) O32 0.0356(6) 0.0355(6) 0.0361(6) 0.0165(5) 0.0112(5) 0.0118(5) C33 0.0270(7) 0.0365(8) 0.0238(7) 0.0068(6) -0.0011(5) 0.0118(6) C34 0.0240(7) 0.0321(7) 0.0246(7) 0.0063(5) -0.0016(5) 0.0097(6) C35 0.0275(7) 0.0330(7) 0.0245(7) 0.0060(6) -0.0016(5) 0.0119(6) C36 0.0238(7) 0.0326(7) 0.0261(7) 0.0083(6) -0.0001(5) 0.0112(6) C37 0.0263(7) 0.0322(7) 0.0241(7) 0.0062(6) -0.0009(5) 0.0123(6) C38 0.0263(7) 0.0340(7) 0.0224(6) 0.0086(5) 0.0015(5) 0.0128(6) C39 0.0274(7) 0.0286(7) 0.0193(6) 0.0061(5) 0.0022(5) 0.0125(5) C40 0.0207(6) 0.0248(6) 0.0209(6) 0.0045(5) -0.0006(5) 0.0051(5) O40 0.0370(6) 0.0513(7) 0.0232(5) 0.0128(5) 0.0031(4) 0.0280(5) O41 0.0278(5) 0.0426(6) 0.0210(5) 0.0039(4) 0.0022(4) 0.0129(4) N11_1 0.0341(6) 0.0283(6) 0.0194(5) 0.0045(4) 0.0001(5) 0.0170(5) C12_1 0.0242(7) 0.0295(7) 0.0253(7) 0.0036(5) -0.0030(5) 0.0112(6) C13_1 0.0232(6) 0.0249(6) 0.0226(6) 0.0061(5) 0.0022(5) 0.0079(5) C14_1 0.0216(6) 0.0193(6) 0.0198(6) 0.0037(5) 0.0008(5) 0.0098(5) C15_1 0.0227(6) 0.0306(7) 0.0294(7) 0.0121(6) 0.0048(5) 0.0113(6) C16_1 0.0330(7) 0.0329(7) 0.0268(7) 0.0140(6) 0.0087(6) 0.0171(6) C17_1 0.0202(6) 0.0213(6) 0.0225(6) 0.0056(5) 0.0004(5) 0.0080(5) N17_1 0.0203(5) 0.0250(5) 0.0204(5) 0.0087(4) 0.0012(4) 0.0085(4) O17_1 0.0191(5) 0.0407(6) 0.0365(6) 0.0193(5) 0.0017(4) 0.0087(4) N21_1 0.0353(7) 0.0329(6) 0.0200(6) 0.0067(5) 0.0038(5) 0.0064(5) C22_1 0.0306(7) 0.0209(6) 0.0195(6) 0.0032(5) 0.0018(5) 0.0066(5) C23_1 0.0318(7) 0.0259(7) 0.0215(6) 0.0056(5) 0.0021(5) 0.0096(6) C24_1 0.0353(8) 0.0322(7) 0.0261(7) 0.0042(6) -0.0031(6) 0.0124(6) C25_1 0.0464(9) 0.0305(7) 0.0192(6) 0.0052(6) -0.0038(6) 0.0117(6) C26_1 0.0452(9) 0.0334(8) 0.0184(7) 0.0065(6) 0.0040(6) 0.0048(7) C27_1 0.0254(7) 0.0270(7) 0.0221(6) 0.0051(5) 0.0018(5) 0.0085(5) N27_1 0.0245(5) 0.0217(5) 0.0207(5) 0.0053(4) -0.0011(4) 0.0083(4) N11_2 0.0261(6) 0.0280(6) 0.0197(5) 0.0052(4) 0.0007(4) 0.0131(5) C12_2 0.0187(6) 0.0362(7) 0.0212(6) 0.0062(5) 0.0010(5) 0.0113(5) C13_2 0.0190(6) 0.0289(6) 0.0186(6) 0.0069(5) 0.0028(5) 0.0078(5) C14_2 0.0174(6) 0.0195(6) 0.0155(5) 0.0022(4) 0.0008(4) 0.0075(5) C15_2 0.0178(6) 0.0211(6) 0.0202(6) 0.0028(5) 0.0024(5) 0.0062(5) C16_2 0.0250(6) 0.0211(6) 0.0209(6) 0.0059(5) 0.0036(5) 0.0078(5) C17_2 0.0179(6) 0.0183(5) 0.0162(6) 0.0021(4) -0.0005(4) 0.0057(5) N17_2 0.0171(5) 0.0244(5) 0.0180(5) 0.0072(4) 0.0013(4) 0.0095(4) O17_2 0.0159(4) 0.0345(5) 0.0239(5) 0.0100(4) 0.0023(3) 0.0088(4) N21_2 0.0246(6) 0.0282(6) 0.0186(5) 0.0070(4) 0.0043(4) 0.0074(5) C22_2 0.0222(6) 0.0189(6) 0.0169(6) 0.0032(5) 0.0019(5) 0.0065(5) C23_2 0.0207(6) 0.0228(6) 0.0200(6) 0.0042(5) 0.0015(5) 0.0049(5) C24_2 0.0241(6) 0.0289(7) 0.0234(7) 0.0032(5) -0.0018(5) 0.0094(5) C25_2 0.0348(8) 0.0285(7) 0.0196(6) 0.0082(5) -0.0021(5) 0.0106(6) C26_2 0.0301(7) 0.0276(7) 0.0199(6) 0.0086(5) 0.0047(5) 0.0060(6) C27_2 0.0196(6) 0.0241(6) 0.0213(6) 0.0060(5) 0.0015(5) 0.0085(5) N27_2 0.0203(5) 0.0208(5) 0.0174(5) 0.0045(4) -0.0007(4) 0.0086(4) _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 O1S H1A 0.866(17) . ? O1S H1B 0.856(18) . ? O2S H2A 0.846(18) . ? O2S H2B 0.824(17) . ? C31 O32 1.2211(16) . ? C31 O31 1.3130(16) . ? C31 C32 1.5011(17) . ? O31 H31 0.894(17) . ? C32 C33 1.5167(18) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.5239(18) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.5233(18) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.5269(18) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.5184(18) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.5212(18) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.5214(18) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.5035(17) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O41 1.2158(15) . ? C40 O40 1.3110(15) . ? O40 H40 0.918(17) . ? N11_1 C12_1 1.3301(17) . ? N11_1 C16_1 1.3344(18) . ? C12_1 C13_1 1.3906(17) . ? C12_1 H12_1 0.9500 . ? C13_1 C14_1 1.3883(17) . ? C13_1 H13_1 0.9500 . ? C14_1 C15_1 1.3880(17) . ? C14_1 C17_1 1.5030(16) . ? C15_1 C16_1 1.3816(18) . ? C15_1 H15_1 0.9500 . ? C16_1 H16_1 0.9500 . ? C17_1 O17_1 1.2247(14) . ? C17_1 N17_1 1.3541(16) . ? N17_1 N27_1 1.3769(14) . ? N17_1 H17_1 0.893(15) . ? N21_1 C26_1 1.3379(17) . ? N21_1 C22_1 1.3477(17) . ? C22_1 C23_1 1.3910(19) . ? C22_1 C27_1 1.4700(17) . ? C23_1 C24_1 1.3853(18) . ? C23_1 H23_1 0.9500 . ? C24_1 C25_1 1.386(2) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.381(2) . ? C25_1 H25_1 0.9500 . ? C26_1 H26_1 0.9500 . ? C27_1 N27_1 1.2784(16) . ? C27_1 H27_1 0.9500 . ? N11_2 C12_2 1.3369(16) . ? N11_2 C16_2 1.3395(16) . ? C12_2 C13_2 1.3881(17) . ? C12_2 H12_2 0.9500 . ? C13_2 C14_2 1.3903(17) . ? C13_2 H13_2 0.9500 . ? C14_2 C15_2 1.3907(16) . ? C14_2 C17_2 1.5046(16) . ? C15_2 C16_2 1.3795(17) . ? C15_2 H15_2 0.9500 . ? C16_2 H16_2 0.9500 . ? C17_2 O17_2 1.2261(14) . ? C17_2 N17_2 1.3493(15) . ? N17_2 N27_2 1.3759(13) . ? N17_2 H17_2 0.863(14) . ? N21_2 C26_2 1.3354(16) . ? N21_2 C22_2 1.3462(15) . ? C22_2 C23_2 1.3929(17) . ? C22_2 C27_2 1.4671(16) . ? C23_2 C24_2 1.3844(17) . ? C23_2 H23_2 0.9500 . ? C24_2 C25_2 1.3874(18) . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.3857(19) . ? C25_2 H25_2 0.9500 . ? C26_2 H26_2 0.9500 . ? C27_2 N27_2 1.2779(15) . ? C27_2 H27_2 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 H1A O1S H1B 107.5(16) . . ? H2A O2S H2B 108.3(16) . . ? O32 C31 O31 123.04(12) . . ? O32 C31 C32 124.35(12) . . ? O31 C31 C32 112.59(11) . . ? C31 O31 H31 110.1(11) . . ? C31 C32 C33 115.87(11) . . ? C31 C32 H32A 108.3 . . ? C33 C32 H32A 108.3 . . ? C31 C32 H32B 108.3 . . ? C33 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C32 C33 C34 110.88(11) . . ? C32 C33 H33A 109.5 . . ? C34 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C34 C33 H33B 109.5 . . ? H33A C33 H33B 108.1 . . ? C35 C34 C33 114.19(11) . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 113.09(11) . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35B 109.0 . . ? C36 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? C37 C36 C35 113.29(11) . . ? C37 C36 H36A 108.9 . . ? C35 C36 H36A 108.9 . . ? C37 C36 H36B 108.9 . . ? C35 C36 H36B 108.9 . . ? H36A C36 H36B 107.7 . . ? C36 C37 C38 114.06(11) . . ? C36 C37 H37A 108.7 . . ? C38 C37 H37A 108.7 . . ? C36 C37 H37B 108.7 . . ? C38 C37 H37B 108.7 . . ? H37A C37 H37B 107.6 . . ? C37 C38 C39 111.61(11) . . ? C37 C38 H38A 109.3 . . ? C39 C38 H38A 109.3 . . ? C37 C38 H38B 109.3 . . ? C39 C38 H38B 109.3 . . ? H38A C38 H38B 108.0 . . ? C40 C39 C38 114.88(10) . . ? C40 C39 H39A 108.5 . . ? C38 C39 H39A 108.5 . . ? C40 C39 H39B 108.5 . . ? C38 C39 H39B 108.5 . . ? H39A C39 H39B 107.5 . . ? O41 C40 O40 123.68(12) . . ? O41 C40 C39 123.42(11) . . ? O40 C40 C39 112.90(11) . . ? C40 O40 H40 112.1(10) . . ? C12_1 N11_1 C16_1 117.96(11) . . ? N11_1 C12_1 C13_1 123.40(12) . . ? N11_1 C12_1 H12_1 118.3 . . ? C13_1 C12_1 H12_1 118.3 . . ? C14_1 C13_1 C12_1 118.36(12) . . ? C14_1 C13_1 H13_1 120.8 . . ? C12_1 C13_1 H13_1 120.8 . . ? C15_1 C14_1 C13_1 118.21(11) . . ? C15_1 C14_1 C17_1 116.58(11) . . ? C13_1 C14_1 C17_1 125.19(11) . . ? C16_1 C15_1 C14_1 119.34(12) . . ? C16_1 C15_1 H15_1 120.3 . . ? C14_1 C15_1 H15_1 120.3 . . ? N11_1 C16_1 C15_1 122.72(12) . . ? N11_1 C16_1 H16_1 118.6 . . ? C15_1 C16_1 H16_1 118.6 . . ? O17_1 C17_1 N17_1 122.91(11) . . ? O17_1 C17_1 C14_1 120.24(11) . . ? N17_1 C17_1 C14_1 116.85(11) . . ? C17_1 N17_1 N27_1 116.95(10) . . ? C17_1 N17_1 H17_1 126.7(9) . . ? N27_1 N17_1 H17_1 116.4(9) . . ? C26_1 N21_1 C22_1 116.47(12) . . ? N21_1 C22_1 C23_1 123.13(12) . . ? N21_1 C22_1 C27_1 114.27(12) . . ? C23_1 C22_1 C27_1 122.59(12) . . ? C24_1 C23_1 C22_1 119.07(12) . . ? C24_1 C23_1 H23_1 120.5 . . ? C22_1 C23_1 H23_1 120.5 . . ? C23_1 C24_1 C25_1 118.36(14) . . ? C23_1 C24_1 H24_1 120.8 . . ? C25_1 C24_1 H24_1 120.8 . . ? C26_1 C25_1 C24_1 118.57(13) . . ? C26_1 C25_1 H25_1 120.7 . . ? C24_1 C25_1 H25_1 120.7 . . ? N21_1 C26_1 C25_1 124.39(13) . . ? N21_1 C26_1 H26_1 117.8 . . ? C25_1 C26_1 H26_1 117.8 . . ? N27_1 C27_1 C22_1 119.34(12) . . ? N27_1 C27_1 H27_1 120.3 . . ? C22_1 C27_1 H27_1 120.3 . . ? C27_1 N27_1 N17_1 116.70(11) . . ? C12_2 N11_2 C16_2 117.87(11) . . ? N11_2 C12_2 C13_2 123.14(12) . . ? N11_2 C12_2 H12_2 118.4 . . ? C13_2 C12_2 H12_2 118.4 . . ? C12_2 C13_2 C14_2 118.60(11) . . ? C12_2 C13_2 H13_2 120.7 . . ? C14_2 C13_2 H13_2 120.7 . . ? C13_2 C14_2 C15_2 118.32(11) . . ? C13_2 C14_2 C17_2 124.62(10) . . ? C15_2 C14_2 C17_2 117.05(10) . . ? C16_2 C15_2 C14_2 119.13(11) . . ? C16_2 C15_2 H15_2 120.4 . . ? C14_2 C15_2 H15_2 120.4 . . ? N11_2 C16_2 C15_2 122.93(11) . . ? N11_2 C16_2 H16_2 118.5 . . ? C15_2 C16_2 H16_2 118.5 . . ? O17_2 C17_2 N17_2 123.86(11) . . ? O17_2 C17_2 C14_2 120.32(10) . . ? N17_2 C17_2 C14_2 115.82(10) . . ? C17_2 N17_2 N27_2 118.22(10) . . ? C17_2 N17_2 H17_2 124.5(9) . . ? N27_2 N17_2 H17_2 116.5(9) . . ? C26_2 N21_2 C22_2 116.82(11) . . ? N21_2 C22_2 C23_2 123.08(11) . . ? N21_2 C22_2 C27_2 114.73(11) . . ? C23_2 C22_2 C27_2 122.15(11) . . ? C24_2 C23_2 C22_2 118.96(11) . . ? C24_2 C23_2 H23_2 120.5 . . ? C22_2 C23_2 H23_2 120.5 . . ? C23_2 C24_2 C25_2 118.51(12) . . ? C23_2 C24_2 H24_2 120.7 . . ? C25_2 C24_2 H24_2 120.7 . . ? C26_2 C25_2 C24_2 118.48(12) . . ? C26_2 C25_2 H25_2 120.8 . . ? C24_2 C25_2 H25_2 120.8 . . ? N21_2 C26_2 C25_2 124.14(12) . . ? N21_2 C26_2 H26_2 117.9 . . ? C25_2 C26_2 H26_2 117.9 . . ? N27_2 C27_2 C22_2 120.27(11) . . ? N27_2 C27_2 H27_2 119.9 . . ? C22_2 C27_2 H27_2 119.9 . . ? C27_2 N27_2 N17_2 115.68(10) . . ? 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 O32 C31 C32 C33 21.26(19) . . . . ? O31 C31 C32 C33 -160.28(12) . . . . ? C31 C32 C33 C34 -167.53(11) . . . . ? C32 C33 C34 C35 -172.35(12) . . . . ? C33 C34 C35 C36 -173.28(12) . . . . ? C34 C35 C36 C37 175.47(12) . . . . ? C35 C36 C37 C38 178.93(12) . . . . ? C36 C37 C38 C39 -178.32(12) . . . . ? C37 C38 C39 C40 176.89(11) . . . . ? C38 C39 C40 O41 22.11(19) . . . . ? C38 C39 C40 O40 -158.04(12) . . . . ? C16_1 N11_1 C12_1 C13_1 0.4(2) . . . . ? N11_1 C12_1 C13_1 C14_1 -1.0(2) . . . . ? C12_1 C13_1 C14_1 C15_1 0.69(19) . . . . ? C12_1 C13_1 C14_1 C17_1 -177.60(12) . . . . ? C13_1 C14_1 C15_1 C16_1 0.1(2) . . . . ? C17_1 C14_1 C15_1 C16_1 178.50(12) . . . . ? C12_1 N11_1 C16_1 C15_1 0.4(2) . . . . ? C14_1 C15_1 C16_1 N11_1 -0.6(2) . . . . ? C15_1 C14_1 C17_1 O17_1 -4.81(18) . . . . ? C13_1 C14_1 C17_1 O17_1 173.51(13) . . . . ? C15_1 C14_1 C17_1 N17_1 175.77(12) . . . . ? C13_1 C14_1 C17_1 N17_1 -5.91(19) . . . . ? O17_1 C17_1 N17_1 N27_1 1.99(19) . . . . ? C14_1 C17_1 N17_1 N27_1 -178.60(10) . . . . ? C26_1 N21_1 C22_1 C23_1 -0.8(2) . . . . ? C26_1 N21_1 C22_1 C27_1 179.98(12) . . . . ? N21_1 C22_1 C23_1 C24_1 0.8(2) . . . . ? C27_1 C22_1 C23_1 C24_1 179.90(12) . . . . ? C22_1 C23_1 C24_1 C25_1 -0.5(2) . . . . ? C23_1 C24_1 C25_1 C26_1 0.4(2) . . . . ? C22_1 N21_1 C26_1 C25_1 0.7(2) . . . . ? C24_1 C25_1 C26_1 N21_1 -0.5(2) . . . . ? N21_1 C22_1 C27_1 N27_1 178.33(12) . . . . ? C23_1 C22_1 C27_1 N27_1 -0.9(2) . . . . ? C22_1 C27_1 N27_1 N17_1 -178.00(11) . . . . ? C17_1 N17_1 N27_1 C27_1 177.08(12) . . . . ? C16_2 N11_2 C12_2 C13_2 0.10(19) . . . . ? N11_2 C12_2 C13_2 C14_2 -0.4(2) . . . . ? C12_2 C13_2 C14_2 C15_2 0.25(18) . . . . ? C12_2 C13_2 C14_2 C17_2 179.25(11) . . . . ? C13_2 C14_2 C15_2 C16_2 0.20(18) . . . . ? C17_2 C14_2 C15_2 C16_2 -178.88(11) . . . . ? C12_2 N11_2 C16_2 C15_2 0.39(19) . . . . ? C14_2 C15_2 C16_2 N11_2 -0.54(19) . . . . ? C13_2 C14_2 C17_2 O17_2 -164.17(12) . . . . ? C15_2 C14_2 C17_2 O17_2 14.85(17) . . . . ? C13_2 C14_2 C17_2 N17_2 15.71(17) . . . . ? C15_2 C14_2 C17_2 N17_2 -165.27(11) . . . . ? O17_2 C17_2 N17_2 N27_2 -0.47(18) . . . . ? C14_2 C17_2 N17_2 N27_2 179.66(10) . . . . ? C26_2 N21_2 C22_2 C23_2 1.30(18) . . . . ? C26_2 N21_2 C22_2 C27_2 -176.42(11) . . . . ? N21_2 C22_2 C23_2 C24_2 -0.74(19) . . . . ? C27_2 C22_2 C23_2 C24_2 176.82(12) . . . . ? C22_2 C23_2 C24_2 C25_2 -0.27(19) . . . . ? C23_2 C24_2 C25_2 C26_2 0.6(2) . . . . ? C22_2 N21_2 C26_2 C25_2 -0.9(2) . . . . ? C24_2 C25_2 C26_2 N21_2 -0.1(2) . . . . ? N21_2 C22_2 C27_2 N27_2 168.47(11) . . . . ? C23_2 C22_2 C27_2 N27_2 -9.28(19) . . . . ? C22_2 C27_2 N27_2 N17_2 -177.62(11) . . . . ? C17_2 N17_2 N27_2 C27_2 -179.30(11) . . . . ? 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 N17_1 H17_1 O1S 0.893(15) 1.934(15) 2.8216(15) 172.6(14) . N17_2 H17_2 O2S 0.863(14) 1.932(15) 2.7831(14) 168.4(13) . O1S H1A O17_1 0.866(17) 2.007(18) 2.8318(14) 158.9(15) 1_455 O1S H1B O32 0.856(18) 1.946(18) 2.7946(15) 170.8(16) 2_756 O2S H2A O17_2 0.846(18) 1.943(18) 2.7612(13) 162.3(15) 1_655 O2S H2B O41 0.824(17) 1.975(18) 2.7749(14) 163.2(16) 2_575 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.508 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.053 #END data_sf0722m(2G) _database_code_depnum_ccdc_archive 'CCDC 853505' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; C20 (4-pyridyl)-CONH-N=CH-(2-pyridyl), 4-aminobenzoic acid hydrate ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C7 H7 N O2) (H2 O) ; _chemical_formula_sum 'C19 H19 N5 O4' _chemical_formula_weight 381.39 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 8.8995(2) _cell_length_b 14.6202(4) _cell_length_c 14.0267(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.198(2) _cell_angle_gamma 90.00 _cell_volume 1822.21(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4782 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 26.40 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 23993 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.12 _reflns_number_total 4009 _reflns_number_gt 2884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0520P)^2^+0.3500P] 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 4009 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 O1S O 0.14240(15) 0.41177(9) 0.49878(9) 0.0376(3) Uani 1 1 d . . . H1A H 0.186(2) 0.4237(14) 0.5578(15) 0.045 Uiso 1 1 d . . . H1B H 0.067(2) 0.3631(14) 0.5126(13) 0.045 Uiso 1 1 d . . . N11 N 0.56425(15) 0.16271(9) 0.37152(9) 0.0266(3) Uani 1 1 d . . . C12 C 0.44733(18) 0.20021(11) 0.41241(11) 0.0276(4) Uani 1 1 d . . . H12 H 0.3764 0.1607 0.4395 0.033 Uiso 1 1 calc R . . C13 C 0.42388(18) 0.29334(11) 0.41747(11) 0.0258(3) Uani 1 1 d . . . H13 H 0.3391 0.3171 0.4474 0.031 Uiso 1 1 calc R . . C14 C 0.52673(17) 0.35176(10) 0.37788(10) 0.0227(3) Uani 1 1 d . . . C15 C 0.64925(19) 0.31333(11) 0.33642(11) 0.0282(4) Uani 1 1 d . . . H15 H 0.7230 0.3512 0.3099 0.034 Uiso 1 1 calc R . . C16 C 0.66302(19) 0.21912(11) 0.33400(11) 0.0293(4) Uani 1 1 d . . . H16 H 0.7466 0.1934 0.3043 0.035 Uiso 1 1 calc R . . C17 C 0.51644(18) 0.45465(10) 0.37804(10) 0.0244(3) Uani 1 1 d . . . N17 N 0.38133(15) 0.48963(9) 0.39773(9) 0.0246(3) Uani 1 1 d . . . H17 H 0.303(2) 0.4538(12) 0.4142(11) 0.029 Uiso 1 1 d . . . O17 O 0.62584(13) 0.50122(7) 0.36034(8) 0.0333(3) Uani 1 1 d . . . N21 N 0.06758(16) 0.72835(9) 0.46854(9) 0.0301(3) Uani 1 1 d . . . C22 C 0.19874(18) 0.70742(11) 0.42995(10) 0.0256(4) Uani 1 1 d . . . C23 C 0.29663(19) 0.77357(11) 0.40010(11) 0.0285(4) Uani 1 1 d . . . H23 H 0.3874 0.7564 0.3723 0.034 Uiso 1 1 calc R . . C24 C 0.2612(2) 0.86516(12) 0.41114(12) 0.0334(4) Uani 1 1 d . . . H24 H 0.3269 0.9117 0.3911 0.040 Uiso 1 1 calc R . . C25 C 0.1285(2) 0.88718(12) 0.45176(12) 0.0349(4) Uani 1 1 d . . . H25 H 0.1011 0.9492 0.4609 0.042 Uiso 1 1 calc R . . C26 C 0.0362(2) 0.81705(12) 0.47880(12) 0.0345(4) Uani 1 1 d . . . H26 H -0.0554 0.8328 0.5064 0.041 Uiso 1 1 calc R . . C27 C 0.23111(19) 0.60929(11) 0.42243(11) 0.0268(4) Uani 1 1 d . . . H27 H 0.1552 0.5655 0.4335 0.032 Uiso 1 1 calc R . . N27 N 0.36223(15) 0.58304(9) 0.40082(9) 0.0263(3) Uani 1 1 d . . . C31 C 0.78136(17) -0.12617(10) 0.29908(10) 0.0231(3) Uani 1 1 d . . . C37 C 0.75563(17) -0.02861(11) 0.31921(11) 0.0249(3) Uani 1 1 d . . . O31 O 0.62644(13) -0.01286(8) 0.35800(9) 0.0350(3) Uani 1 1 d . . . H31 H 0.609(2) 0.0479(14) 0.3623(13) 0.042 Uiso 1 1 d . . . O32 O 0.84383(13) 0.03212(8) 0.30095(8) 0.0328(3) Uani 1 1 d . . . C32 C 0.68550(17) -0.19334(10) 0.33149(11) 0.0241(3) Uani 1 1 d . . . H32 H 0.6031 -0.1756 0.3676 0.029 Uiso 1 1 calc R . . C33 C 0.70694(18) -0.28464(11) 0.31269(11) 0.0269(4) Uani 1 1 d . . . H33 H 0.6402 -0.3291 0.3359 0.032 Uiso 1 1 calc R . . C34 C 0.82779(18) -0.31199(11) 0.25906(11) 0.0281(4) Uani 1 1 d . . . N34 N 0.84691(19) -0.40280(11) 0.23698(13) 0.0429(4) Uani 1 1 d . . . H34A H 0.789(2) -0.4430(15) 0.2662(15) 0.051 Uiso 1 1 d . . . H34B H 0.931(3) -0.4205(15) 0.2204(15) 0.051 Uiso 1 1 d . . . C35 C 0.92368(19) -0.24467(11) 0.22574(12) 0.0291(4) Uani 1 1 d . . . H35 H 1.0052 -0.2620 0.1887 0.035 Uiso 1 1 calc R . . C36 C 0.90151(18) -0.15378(11) 0.24582(11) 0.0262(4) Uani 1 1 d . . . H36 H 0.9686 -0.1092 0.2232 0.031 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 O1S 0.0349(8) 0.0351(7) 0.0438(7) 0.0029(6) 0.0108(6) -0.0033(6) N11 0.0249(7) 0.0225(7) 0.0323(7) -0.0016(5) 0.0013(6) 0.0011(6) C12 0.0248(9) 0.0251(8) 0.0330(8) -0.0002(6) 0.0034(7) -0.0007(7) C13 0.0223(8) 0.0243(8) 0.0312(8) -0.0025(6) 0.0040(7) 0.0016(7) C14 0.0214(8) 0.0227(8) 0.0238(7) -0.0024(6) -0.0012(6) 0.0004(6) C15 0.0264(9) 0.0245(8) 0.0342(8) -0.0011(7) 0.0057(7) -0.0005(7) C16 0.0259(9) 0.0272(9) 0.0354(9) -0.0037(7) 0.0059(7) 0.0026(7) C17 0.0267(9) 0.0231(8) 0.0235(7) -0.0015(6) 0.0028(6) -0.0009(7) N17 0.0252(7) 0.0175(7) 0.0313(7) -0.0008(5) 0.0043(6) -0.0002(6) O17 0.0297(7) 0.0235(6) 0.0481(7) -0.0007(5) 0.0131(5) -0.0027(5) N21 0.0269(8) 0.0307(8) 0.0331(7) 0.0020(6) 0.0052(6) 0.0040(6) C22 0.0253(9) 0.0272(8) 0.0243(7) -0.0001(6) 0.0006(6) 0.0016(7) C23 0.0235(9) 0.0276(9) 0.0344(8) -0.0005(7) 0.0032(7) 0.0017(7) C24 0.0322(10) 0.0272(9) 0.0406(9) 0.0011(7) -0.0002(8) -0.0013(8) C25 0.0397(11) 0.0265(9) 0.0381(9) -0.0033(7) -0.0016(8) 0.0076(8) C26 0.0329(10) 0.0363(10) 0.0346(9) 0.0016(7) 0.0054(8) 0.0122(8) C27 0.0253(9) 0.0245(8) 0.0308(8) 0.0002(6) 0.0026(7) -0.0004(7) N27 0.0297(8) 0.0197(7) 0.0295(7) -0.0018(5) 0.0025(6) 0.0016(6) C31 0.0193(8) 0.0241(8) 0.0257(7) 0.0013(6) 0.0001(6) 0.0007(7) C37 0.0219(8) 0.0252(8) 0.0276(7) 0.0017(6) 0.0021(6) 0.0000(7) O31 0.0310(7) 0.0205(6) 0.0552(8) -0.0024(5) 0.0179(6) -0.0001(5) O32 0.0269(6) 0.0239(6) 0.0483(7) 0.0003(5) 0.0074(5) -0.0050(5) C32 0.0191(8) 0.0240(8) 0.0295(8) 0.0021(6) 0.0036(6) 0.0014(6) C33 0.0225(8) 0.0230(8) 0.0355(8) 0.0051(6) 0.0047(7) 0.0011(7) C34 0.0237(9) 0.0244(8) 0.0360(8) -0.0005(7) 0.0006(7) 0.0028(7) N34 0.0329(9) 0.0256(8) 0.0721(12) -0.0043(7) 0.0202(8) 0.0040(7) C35 0.0208(9) 0.0318(9) 0.0352(8) -0.0011(7) 0.0070(7) 0.0038(7) C36 0.0203(8) 0.0282(9) 0.0303(8) 0.0019(6) 0.0035(6) -0.0009(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 O1S H1A 0.91(2) . ? O1S H1B 1.01(2) . ? N11 C12 1.334(2) . ? N11 C16 1.335(2) . ? C12 C13 1.380(2) . ? C12 H12 0.9500 . ? C13 C14 1.390(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 C17 1.507(2) . ? C15 C16 1.383(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.2248(18) . ? C17 N17 1.349(2) . ? N17 N27 1.3772(18) . ? N17 H17 0.915(18) . ? N21 C26 1.336(2) . ? N21 C22 1.349(2) . ? C22 C23 1.382(2) . ? C22 C27 1.468(2) . ? C23 C24 1.386(2) . ? C23 H23 0.9500 . ? C24 C25 1.378(2) . ? C24 H24 0.9500 . ? C25 C26 1.380(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.281(2) . ? C27 H27 0.9500 . ? C31 C32 1.394(2) . ? C31 C36 1.398(2) . ? C31 C37 1.474(2) . ? C37 O32 1.2217(18) . ? C37 O31 1.3194(18) . ? O31 H31 0.90(2) . ? C32 C33 1.376(2) . ? C32 H32 0.9500 . ? C33 C34 1.405(2) . ? C33 H33 0.9500 . ? C34 N34 1.376(2) . ? C34 C35 1.400(2) . ? N34 H34A 0.89(2) . ? N34 H34B 0.84(2) . ? C35 C36 1.375(2) . ? C35 H35 0.9500 . ? C36 H36 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 H1A O1S H1B 102.6(16) . . ? C12 N11 C16 117.54(13) . . ? N11 C12 C13 123.48(15) . . ? N11 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C12 C13 C14 118.74(14) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 118.05(14) . . ? C15 C14 C17 117.10(13) . . ? C13 C14 C17 124.84(13) . . ? C16 C15 C14 119.19(14) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? N11 C16 C15 122.98(14) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? O17 C17 N17 123.94(14) . . ? O17 C17 C14 120.36(14) . . ? N17 C17 C14 115.69(13) . . ? C17 N17 N27 119.69(13) . . ? C17 N17 H17 122.6(11) . . ? N27 N17 H17 117.5(11) . . ? C26 N21 C22 117.02(14) . . ? N21 C22 C23 122.48(15) . . ? N21 C22 C27 115.35(14) . . ? C23 C22 C27 122.17(14) . . ? C22 C23 C24 119.39(15) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 118.52(16) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 118.50(16) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? N21 C26 C25 124.07(16) . . ? N21 C26 H26 118.0 . . ? C25 C26 H26 118.0 . . ? N27 C27 C22 119.66(15) . . ? N27 C27 H27 120.2 . . ? C22 C27 H27 120.2 . . ? C27 N27 N17 114.85(13) . . ? C32 C31 C36 118.12(14) . . ? C32 C31 C37 120.99(13) . . ? C36 C31 C37 120.89(14) . . ? O32 C37 O31 122.98(15) . . ? O32 C37 C31 123.68(14) . . ? O31 C37 C31 113.33(13) . . ? C37 O31 H31 110.9(12) . . ? C33 C32 C31 121.81(14) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.1 . . ? C32 C33 C34 119.82(14) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? N34 C34 C35 121.18(15) . . ? N34 C34 C33 120.21(15) . . ? C35 C34 C33 118.55(14) . . ? C34 N34 H34A 116.7(13) . . ? C34 N34 H34B 118.9(15) . . ? H34A N34 H34B 118(2) . . ? C36 C35 C34 120.92(14) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C31 120.77(14) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? 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 C16 N11 C12 C13 0.1(2) . . . . ? N11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C15 -0.9(2) . . . . ? C12 C13 C14 C17 -179.87(15) . . . . ? C13 C14 C15 C16 1.4(2) . . . . ? C17 C14 C15 C16 -179.57(14) . . . . ? C12 N11 C16 C15 0.4(2) . . . . ? C14 C15 C16 N11 -1.2(3) . . . . ? C15 C14 C17 O17 -14.5(2) . . . . ? C13 C14 C17 O17 164.48(15) . . . . ? C15 C14 C17 N17 164.98(14) . . . . ? C13 C14 C17 N17 -16.1(2) . . . . ? O17 C17 N17 N27 -1.5(2) . . . . ? C14 C17 N17 N27 179.03(12) . . . . ? C26 N21 C22 C23 -1.2(2) . . . . ? C26 N21 C22 C27 178.31(14) . . . . ? N21 C22 C23 C24 1.0(2) . . . . ? C27 C22 C23 C24 -178.53(15) . . . . ? C22 C23 C24 C25 0.0(2) . . . . ? C23 C24 C25 C26 -0.6(2) . . . . ? C22 N21 C26 C25 0.6(2) . . . . ? C24 C25 C26 N21 0.3(3) . . . . ? N21 C22 C27 N27 -169.16(14) . . . . ? C23 C22 C27 N27 10.4(2) . . . . ? C22 C27 N27 N17 178.66(13) . . . . ? C17 N17 N27 C27 -178.32(14) . . . . ? C32 C31 C37 O32 172.44(15) . . . . ? C36 C31 C37 O32 -8.4(2) . . . . ? C32 C31 C37 O31 -8.4(2) . . . . ? C36 C31 C37 O31 170.75(14) . . . . ? C36 C31 C32 C33 0.3(2) . . . . ? C37 C31 C32 C33 179.42(15) . . . . ? C31 C32 C33 C34 -0.3(2) . . . . ? C32 C33 C34 N34 -177.64(16) . . . . ? C32 C33 C34 C35 -0.2(2) . . . . ? N34 C34 C35 C36 178.18(17) . . . . ? C33 C34 C35 C36 0.7(3) . . . . ? C34 C35 C36 C31 -0.8(3) . . . . ? C32 C31 C36 C35 0.3(2) . . . . ? C37 C31 C36 C35 -178.85(15) . . . . ? 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 O31 H31 N11 0.90(2) 1.73(2) 2.6349(17) 176.7(18) . N17 H17 O1S 0.915(18) 2.001(18) 2.8570(18) 155.1(15) . O1S H1A O17 0.91(2) 2.26(2) 3.0533(19) 145.2(17) 3_666 O1S H1B N21 1.01(2) 1.82(2) 2.8274(19) 176.8(17) 3_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.228 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.045 #END data_sf0606m(2H) _database_code_depnum_ccdc_archive 'CCDC 853506' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF228 (3-pyridyl)-CONH-N=CH-(2-pyridyl), 3-fluorobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C7 H5 F O2) (H2 O) ; _chemical_formula_sum 'C19 H17 F N4 O4' _chemical_formula_weight 384.37 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' F F 0.0171 0.0103 '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 6.6065(14) _cell_length_b 7.2295(17) _cell_length_c 21.354(4) _cell_angle_alpha 92.457(13) _cell_angle_beta 97.668(14) _cell_angle_gamma 116.706(15) _cell_volume 896.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 596 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 22.05 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 6657 _diffrn_reflns_av_R_equivalents 0.1136 _diffrn_reflns_av_sigmaI/netI 0.1703 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3951 _reflns_number_gt 1507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0800P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3951 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1947 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _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 O1S O 0.8138(4) 0.3037(5) 0.62504(12) 0.0452(8) Uani 1 1 d . . . H1A H 0.916(6) 0.425(6) 0.6523(18) 0.054 Uiso 1 1 d . . . H1B H 0.894(7) 0.272(6) 0.6057(18) 0.057 Uiso 1 1 d . . . N11 N 0.5074(5) 0.2554(5) 0.36659(13) 0.0370(8) Uani 1 1 d . . . C12 C 0.6307(6) 0.2633(7) 0.42214(17) 0.0471(11) Uani 1 1 d . . . H12 H 0.7803 0.2758 0.4224 0.056 Uiso 1 1 calc R . . C13 C 0.5539(6) 0.2542(6) 0.47898(16) 0.0377(9) Uani 1 1 d . . . H13 H 0.6485 0.2604 0.5175 0.045 Uiso 1 1 calc R . . C14 C 0.3374(5) 0.2360(5) 0.47955(15) 0.0284(8) Uani 1 1 d . . . C15 C 0.2118(6) 0.2305(6) 0.42203(16) 0.0405(10) Uani 1 1 d . . . H15 H 0.0625 0.2199 0.4204 0.049 Uiso 1 1 calc R . . C16 C 0.3000(6) 0.2402(6) 0.36715(17) 0.0408(9) Uani 1 1 d . . . H16 H 0.2095 0.2359 0.3281 0.049 Uiso 1 1 calc R . . C17 C 0.2309(6) 0.2294(5) 0.53742(16) 0.0314(8) Uani 1 1 d . . . N17 N 0.3517(5) 0.2275(5) 0.59331(13) 0.0344(7) Uani 1 1 d . . . H17 H 0.508(6) 0.259(5) 0.5976(15) 0.041 Uiso 1 1 d . . . O17 O 0.0419(4) 0.2253(4) 0.53279(11) 0.0389(7) Uani 1 1 d . . . N21 N 0.4309(5) 0.2328(5) 0.81079(14) 0.0439(8) Uani 1 1 d . . . C22 C 0.2817(6) 0.2099(6) 0.75860(16) 0.0353(9) Uani 1 1 d . . . C23 C 0.0601(6) 0.1782(6) 0.76001(17) 0.0384(9) Uani 1 1 d . . . H23 H -0.0411 0.1629 0.7219 0.046 Uiso 1 1 calc R . . C24 C -0.0105(6) 0.1695(6) 0.81855(17) 0.0441(10) Uani 1 1 d . . . H24 H -0.1617 0.1481 0.8213 0.053 Uiso 1 1 calc R . . C25 C 0.1397(7) 0.1920(6) 0.87195(18) 0.0488(10) Uani 1 1 d . . . H25 H 0.0955 0.1880 0.9126 0.059 Uiso 1 1 calc R . . C26 C 0.3559(7) 0.2206(6) 0.86622(17) 0.0489(11) Uani 1 1 d . . . H26 H 0.4579 0.2323 0.9038 0.059 Uiso 1 1 calc R . . C27 C 0.3719(6) 0.2216(6) 0.69931(17) 0.0384(9) Uani 1 1 d . . . H27 H 0.5202 0.2310 0.6999 0.046 Uiso 1 1 calc R . . N27 N 0.2542(5) 0.2194(5) 0.64725(13) 0.0338(7) Uani 1 1 d . . . C31 C 0.7934(6) 0.2990(6) 0.17144(17) 0.0383(9) Uani 1 1 d . B . C37 C 0.7784(7) 0.3055(6) 0.24042(18) 0.0408(9) Uani 1 1 d . . . O31 O 0.5739(4) 0.2551(5) 0.25160(12) 0.0508(8) Uani 1 1 d . . . H31 H 0.583(6) 0.283(6) 0.3022(19) 0.061 Uiso 1 1 d . . . O32 O 0.9463(4) 0.3551(4) 0.28166(12) 0.0523(8) Uani 1 1 d . . . C32 C 0.6012(7) 0.2506(6) 0.12670(17) 0.0463(10) Uani 1 1 d . . . H32 H 0.4578 0.2194 0.1393 0.056 Uiso 1 1 calc R A 1 C33A C 0.6205(8) 0.2482(7) 0.0634(2) 0.0589(12) Uani 0.785(4) 1 d P B 1 F33 F 0.4404(6) 0.2060(6) 0.02069(14) 0.0857(12) Uani 0.785(4) 1 d P B 1 C33B C 0.6205(8) 0.2482(7) 0.0634(2) 0.0589(12) Uani 0.215(4) 1 d P B 2 H33 H 0.4885 0.2171 0.0326 0.071 Uiso 0.215(4) 1 calc PR B 2 C34 C 0.8206(9) 0.2885(8) 0.0434(2) 0.0676(14) Uani 1 1 d . . . H34 H 0.8299 0.2841 -0.0007 0.081 Uiso 1 1 calc R B 1 C35A C 1.0097(9) 0.3360(8) 0.0889(2) 0.0653(13) Uani 0.785(4) 1 d P B 1 H35 H 1.1518 0.3642 0.0758 0.078 Uiso 0.785(4) 1 calc PR B 1 C35B C 1.0097(9) 0.3360(8) 0.0889(2) 0.0653(13) Uani 0.215(4) 1 d P B 2 F35 F 1.167(2) 0.346(2) 0.0590(5) 0.0857(12) Uani 0.215(4) 1 d P B 2 C36 C 0.9997(7) 0.3439(6) 0.1521(2) 0.0503(11) Uani 1 1 d . . . H36 H 1.1339 0.3801 0.1826 0.060 Uiso 1 1 calc R B 1 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 O1S 0.0368(16) 0.070(2) 0.0389(16) -0.0043(14) 0.0058(12) 0.0339(15) N11 0.0442(18) 0.047(2) 0.0316(17) 0.0068(15) 0.0115(14) 0.0296(16) C12 0.041(2) 0.075(3) 0.040(2) 0.010(2) 0.0121(18) 0.038(2) C13 0.038(2) 0.059(3) 0.0268(19) 0.0103(18) 0.0074(16) 0.030(2) C14 0.0299(18) 0.030(2) 0.0290(19) 0.0031(16) 0.0075(15) 0.0162(16) C15 0.033(2) 0.060(3) 0.035(2) 0.0109(19) 0.0056(17) 0.026(2) C16 0.045(2) 0.055(3) 0.031(2) 0.0088(19) 0.0072(17) 0.030(2) C17 0.0325(19) 0.030(2) 0.033(2) 0.0010(17) 0.0068(16) 0.0148(17) N17 0.0288(16) 0.050(2) 0.0273(16) 0.0061(14) 0.0082(13) 0.0194(15) O17 0.0331(14) 0.0538(18) 0.0391(15) 0.0055(13) 0.0102(11) 0.0269(13) N21 0.0486(19) 0.055(2) 0.0313(18) 0.0086(16) 0.0062(15) 0.0266(17) C22 0.041(2) 0.037(2) 0.029(2) 0.0039(17) 0.0069(16) 0.0182(18) C23 0.042(2) 0.043(2) 0.034(2) 0.0053(18) 0.0101(17) 0.0219(19) C24 0.045(2) 0.047(3) 0.044(2) 0.012(2) 0.0191(19) 0.020(2) C25 0.067(3) 0.052(3) 0.034(2) 0.007(2) 0.018(2) 0.030(2) C26 0.067(3) 0.052(3) 0.027(2) 0.0101(19) 0.0057(19) 0.027(2) C27 0.036(2) 0.047(3) 0.036(2) 0.0043(19) 0.0074(17) 0.0223(19) N27 0.0377(17) 0.0406(19) 0.0279(16) 0.0044(14) 0.0114(13) 0.0207(15) C31 0.046(2) 0.033(2) 0.037(2) 0.0041(18) 0.0137(18) 0.0179(19) C37 0.045(2) 0.042(2) 0.041(2) 0.0034(19) 0.0105(19) 0.024(2) O31 0.0451(16) 0.078(2) 0.0335(15) 0.0050(14) 0.0118(12) 0.0305(15) O32 0.0504(17) 0.065(2) 0.0462(16) -0.0054(15) -0.0043(14) 0.0350(15) C32 0.056(3) 0.051(3) 0.033(2) 0.008(2) 0.016(2) 0.024(2) C33A 0.076(3) 0.061(3) 0.040(3) 0.011(2) 0.015(2) 0.030(3) F33 0.092(3) 0.126(3) 0.0331(17) 0.0079(19) -0.0038(17) 0.049(2) C33B 0.076(3) 0.061(3) 0.040(3) 0.011(2) 0.015(2) 0.030(3) C34 0.102(4) 0.073(4) 0.046(3) 0.023(3) 0.036(3) 0.048(3) C35A 0.086(4) 0.071(3) 0.064(3) 0.021(3) 0.046(3) 0.047(3) C35B 0.086(4) 0.071(3) 0.064(3) 0.021(3) 0.046(3) 0.047(3) F35 0.092(3) 0.126(3) 0.0331(17) 0.0079(19) -0.0038(17) 0.049(2) C36 0.051(3) 0.045(3) 0.060(3) 0.009(2) 0.022(2) 0.023(2) _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 O1S H1A 0.94(4) . ? O1S H1B 0.81(4) . ? N11 C16 1.326(4) . ? N11 C12 1.330(4) . ? N11 H31 1.51(4) . ? C12 C13 1.370(4) . ? C12 H12 0.9500 . ? C13 C14 1.378(4) . ? C13 H13 0.9500 . ? C14 C15 1.376(4) . ? C14 C17 1.494(4) . ? C15 C16 1.368(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.226(4) . ? C17 N17 1.349(4) . ? N17 N27 1.384(4) . ? N17 H17 0.94(3) . ? N21 C26 1.334(4) . ? N21 C22 1.336(4) . ? C22 C23 1.381(5) . ? C22 C27 1.460(5) . ? C23 C24 1.386(5) . ? C23 H23 0.9500 . ? C24 C25 1.359(5) . ? C24 H24 0.9500 . ? C25 C26 1.372(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.264(4) . ? C27 H27 0.9500 . ? C31 C32 1.377(5) . ? C31 C36 1.378(5) . ? C31 C37 1.490(5) . ? C37 O32 1.220(4) . ? C37 O31 1.291(4) . ? O31 H31 1.08(4) . ? C32 C33A 1.374(5) . ? C32 H32 0.9500 . ? C33A F33 1.304(5) . ? C33A C34 1.354(6) . ? C34 C35A 1.373(6) . ? C34 H34 0.9500 . ? C35A C36 1.360(5) . ? C35A H35 0.9500 . ? C36 H36 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 H1A O1S H1B 106(4) . . ? C16 N11 C12 117.4(3) . . ? C16 N11 H31 114.4(14) . . ? C12 N11 H31 127.9(14) . . ? N11 C12 C13 123.6(3) . . ? N11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 117.1(3) . . ? C15 C14 C17 117.2(3) . . ? C13 C14 C17 125.6(3) . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N11 C16 C15 122.3(3) . . ? N11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O17 C17 N17 123.0(3) . . ? O17 C17 C14 120.1(3) . . ? N17 C17 C14 116.9(3) . . ? C17 N17 N27 117.5(3) . . ? C17 N17 H17 122(2) . . ? N27 N17 H17 120(2) . . ? C26 N21 C22 116.9(3) . . ? N21 C22 C23 123.3(3) . . ? N21 C22 C27 114.5(3) . . ? C23 C22 C27 122.2(3) . . ? C22 C23 C24 118.2(3) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? C25 C24 C23 119.0(4) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 119.0(4) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? N21 C26 C25 123.6(4) . . ? N21 C26 H26 118.2 . . ? C25 C26 H26 118.2 . . ? N27 C27 C22 120.5(3) . . ? N27 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C27 N27 N17 116.5(3) . . ? C32 C31 C36 119.7(4) . . ? C32 C31 C37 120.0(3) . . ? C36 C31 C37 120.3(4) . . ? O32 C37 O31 124.2(3) . . ? O32 C37 C31 122.1(3) . . ? O31 C37 C31 113.7(3) . . ? C37 O31 H31 108.7(19) . . ? C33A C32 C31 118.8(4) . . ? C33A C32 H32 120.6 . . ? C31 C32 H32 120.6 . . ? F33 C33A C34 118.2(4) . . ? F33 C33A C32 119.3(4) . . ? C34 C33A C32 122.5(4) . . ? C33A C34 C35A 117.6(4) . . ? C33A C34 H34 121.2 . . ? C35A C34 H34 121.2 . . ? C36 C35A C34 122.0(4) . . ? C36 C35A H35 119.0 . . ? C34 C35A H35 119.0 . . ? C35A C36 C31 119.5(4) . . ? C35A C36 H36 120.3 . . ? C31 C36 H36 120.3 . . ? 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 C16 N11 C12 C13 0.7(6) . . . . ? N11 C12 C13 C14 0.0(6) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C12 C13 C14 C17 -178.4(4) . . . . ? C13 C14 C15 C16 0.8(6) . . . . ? C17 C14 C15 C16 178.7(4) . . . . ? C12 N11 C16 C15 -0.7(6) . . . . ? C14 C15 C16 N11 -0.1(6) . . . . ? C15 C14 C17 O17 -2.0(5) . . . . ? C13 C14 C17 O17 175.6(3) . . . . ? C15 C14 C17 N17 177.8(3) . . . . ? C13 C14 C17 N17 -4.6(5) . . . . ? O17 C17 N17 N27 0.4(5) . . . . ? C14 C17 N17 N27 -179.4(3) . . . . ? C26 N21 C22 C23 1.0(6) . . . . ? C26 N21 C22 C27 -179.2(3) . . . . ? N21 C22 C23 C24 -0.1(6) . . . . ? C27 C22 C23 C24 -179.9(3) . . . . ? C22 C23 C24 C25 -0.1(6) . . . . ? C23 C24 C25 C26 -0.7(6) . . . . ? C22 N21 C26 C25 -1.8(6) . . . . ? C24 C25 C26 N21 1.7(6) . . . . ? N21 C22 C27 N27 -174.2(3) . . . . ? C23 C22 C27 N27 5.6(6) . . . . ? C22 C27 N27 N17 -178.9(3) . . . . ? C17 N17 N27 C27 -178.8(3) . . . . ? C32 C31 C37 O32 -177.3(4) . . . . ? C36 C31 C37 O32 1.9(6) . . . . ? C32 C31 C37 O31 2.5(5) . . . . ? C36 C31 C37 O31 -178.4(3) . . . . ? C36 C31 C32 C33A 0.1(6) . . . . ? C37 C31 C32 C33A 179.2(4) . . . . ? C31 C32 C33A F33 -178.9(4) . . . . ? C31 C32 C33A C34 1.1(7) . . . . ? F33 C33A C34 C35A 179.0(4) . . . . ? C32 C33A C34 C35A -0.9(7) . . . . ? C33A C34 C35A C36 -0.3(7) . . . . ? C34 C35A C36 C31 1.4(7) . . . . ? C32 C31 C36 C35A -1.2(6) . . . . ? C37 C31 C36 C35A 179.6(4) . . . . ? 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 N17 H17 O1S 0.94(3) 1.90(3) 2.826(4) 167(3) . O1S H1A O32 0.94(4) 1.87(4) 2.791(4) 165(3) 2_766 O1S H1B O17 0.81(4) 2.04(4) 2.817(3) 161(4) 1_655 O31 H31 N11 1.08(4) 1.51(4) 2.552(4) 159(3) . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.285 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.068 #END data_sf0702m(2I) _database_code_depnum_ccdc_archive 'CCDC 853507' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF355 4-pyridyl-CONH-N=CH-2-pyridyl, 2,4-difluorobenzoic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C7 H4 O2 F2) (H2 O) (O0.1) ; _chemical_formula_sum 'C19 H16 F2 N4 O4.10' _chemical_formula_weight 403.96 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 7.4376(2) _cell_length_b 12.3798(4) _cell_length_c 39.3480(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.396(2) _cell_angle_gamma 90.00 _cell_volume 3616.64(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 33.15 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1670 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 34501 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_limit_l_max 56 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5339 _reflns_number_gt 4155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0800P)^2^+3.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5339 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 O1S O 0.29973(19) 0.56376(9) 0.28366(3) 0.0263(3) Uani 1 1 d . . . H1A H 0.300(3) 0.5101(18) 0.2707(6) 0.032 Uiso 1 1 d . . . H1B H 0.395(3) 0.5605(17) 0.2951(6) 0.032 Uiso 1 1 d . . . O2S O 0.0000 0.5517(10) 0.2500 0.060(3) Uiso 0.20 2 d SP . . N11 N 0.49377(18) 0.26159(10) 0.11473(3) 0.0196(3) Uani 1 1 d . . . C12 C 0.4943(2) 0.18973(12) 0.14024(3) 0.0204(3) Uani 1 1 d . . . H12 H 0.5337 0.1182 0.1361 0.024 Uiso 1 1 calc R . . C13 C 0.4400(2) 0.21498(11) 0.17245(3) 0.0195(3) Uani 1 1 d . . . H13 H 0.4397 0.1615 0.1898 0.023 Uiso 1 1 calc R . . C14 C 0.3860(2) 0.32035(11) 0.17883(3) 0.0167(3) Uani 1 1 d . . . C15 C 0.3885(2) 0.39574(11) 0.15269(3) 0.0181(3) Uani 1 1 d . . . H15 H 0.3544 0.4686 0.1564 0.022 Uiso 1 1 calc R . . C16 C 0.4416(2) 0.36284(12) 0.12108(3) 0.0198(3) Uani 1 1 d . . . H16 H 0.4410 0.4143 0.1032 0.024 Uiso 1 1 calc R . . C17 C 0.3299(2) 0.35886(11) 0.21289(3) 0.0180(3) Uani 1 1 d . . . N17 N 0.27701(18) 0.28072(10) 0.23424(3) 0.0171(2) Uani 1 1 d . . . H17 H 0.255(3) 0.2133(16) 0.2283(5) 0.021 Uiso 1 1 d . . . O17 O 0.33393(19) 0.45507(8) 0.22008(3) 0.0279(3) Uani 1 1 d . . . N21 N 0.05204(19) 0.17094(10) 0.33496(3) 0.0217(3) Uani 1 1 d . . . C22 C 0.1132(2) 0.25835(11) 0.31889(3) 0.0170(3) Uani 1 1 d . . . C23 C 0.1239(2) 0.36046(11) 0.33372(3) 0.0182(3) Uani 1 1 d . . . H23 H 0.1659 0.4207 0.3215 0.022 Uiso 1 1 calc R . . C24 C 0.0714(2) 0.37176(12) 0.36682(3) 0.0207(3) Uani 1 1 d . . . H24 H 0.0780 0.4402 0.3778 0.025 Uiso 1 1 calc R . . C25 C 0.0093(2) 0.28229(13) 0.38368(3) 0.0215(3) Uani 1 1 d . . . H25 H -0.0269 0.2881 0.4064 0.026 Uiso 1 1 calc R . . C26 C 0.0012(2) 0.18425(12) 0.36682(3) 0.0229(3) Uani 1 1 d . . . H26 H -0.0426 0.1232 0.3784 0.027 Uiso 1 1 calc R . . C27 C 0.1693(2) 0.23586(11) 0.28439(3) 0.0188(3) Uani 1 1 d . . . H27 H 0.1624 0.1643 0.2757 0.023 Uiso 1 1 calc R . . N27 N 0.22745(17) 0.31224(9) 0.26590(3) 0.0171(2) Uani 1 1 d . . . C31 C 0.69908(19) 0.04478(11) 0.02403(3) 0.0161(3) Uani 1 1 d . . . C37 C 0.6448(2) 0.08890(12) 0.05734(3) 0.0185(3) Uani 1 1 d . A . O31 O 0.59232(17) 0.19056(9) 0.05554(3) 0.0256(3) Uani 1 1 d . . . H31 H 0.555(3) 0.2144(17) 0.0814(5) 0.031 Uiso 1 1 d . . . O32 O 0.65007(19) 0.03530(10) 0.08329(3) 0.0290(3) Uani 1 1 d . . . C32A C 0.7643(2) -0.06009(12) 0.02137(4) 0.0217(3) Uani 0.702(3) 1 d P A 1 F32 F 0.7708(2) -0.13046(10) 0.04666(3) 0.0286(4) Uani 0.702(3) 1 d P A 1 C32B C 0.7643(2) -0.06009(12) 0.02137(4) 0.0217(3) Uani 0.298(3) 1 d P A 2 H32 H 0.7734 -0.1040 0.0412 0.026 Uiso 0.298(3) 1 calc PR A 2 C33 C 0.8164(2) -0.10288(13) -0.00895(4) 0.0287(4) Uani 1 1 d . . . H33 H 0.8606 -0.1747 -0.0102 0.034 Uiso 1 1 calc R A 1 C34 C 0.8020(3) -0.03785(15) -0.03717(4) 0.0297(4) Uani 1 1 d . A . F34 F 0.8529(2) -0.07827(12) -0.06705(3) 0.0526(4) Uani 1 1 d . . . C35 C 0.7376(2) 0.06564(15) -0.03664(4) 0.0284(4) Uani 1 1 d . . . H35 H 0.7289 0.1086 -0.0567 0.034 Uiso 1 1 calc R A 1 C36A C 0.6858(2) 0.10536(12) -0.00589(4) 0.0217(3) Uani 0.702(3) 1 d P A 1 H36 H 0.6393 0.1767 -0.0051 0.026 Uiso 0.702(3) 1 calc PR A 1 C36B C 0.6858(2) 0.10536(12) -0.00589(4) 0.0217(3) Uani 0.298(3) 1 d P A 2 F36 F 0.5957(5) 0.1925(2) -0.01224(8) 0.0246(9) Uani 0.298(3) 1 d P A 2 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 O1S 0.0435(8) 0.0181(5) 0.0186(5) -0.0030(4) 0.0137(5) 0.0007(5) N11 0.0234(7) 0.0267(6) 0.0094(5) -0.0052(4) 0.0068(4) -0.0027(5) C12 0.0269(8) 0.0219(6) 0.0134(6) -0.0054(5) 0.0099(5) -0.0029(5) C13 0.0276(8) 0.0204(6) 0.0113(6) -0.0019(5) 0.0090(5) -0.0032(5) C14 0.0213(7) 0.0207(6) 0.0087(5) -0.0034(4) 0.0059(5) -0.0032(5) C15 0.0252(8) 0.0211(6) 0.0084(5) -0.0018(4) 0.0056(5) 0.0009(5) C16 0.0260(8) 0.0265(7) 0.0073(5) -0.0011(5) 0.0046(5) 0.0000(5) C17 0.0264(8) 0.0203(6) 0.0082(5) -0.0018(4) 0.0076(5) -0.0025(5) N17 0.0278(7) 0.0176(5) 0.0069(5) -0.0026(4) 0.0091(4) -0.0029(4) O17 0.0538(8) 0.0191(5) 0.0127(5) -0.0043(4) 0.0169(5) -0.0060(5) N21 0.0337(8) 0.0226(6) 0.0098(5) 0.0007(4) 0.0110(5) -0.0025(5) C22 0.0224(7) 0.0210(6) 0.0082(5) 0.0008(4) 0.0062(5) 0.0008(5) C23 0.0256(8) 0.0208(6) 0.0087(5) 0.0004(4) 0.0061(5) 0.0012(5) C24 0.0292(8) 0.0240(7) 0.0093(6) -0.0019(5) 0.0051(5) 0.0038(5) C25 0.0260(8) 0.0311(7) 0.0082(5) 0.0002(5) 0.0068(5) 0.0036(6) C26 0.0320(9) 0.0279(7) 0.0099(6) 0.0019(5) 0.0102(5) -0.0027(6) C27 0.0262(8) 0.0218(6) 0.0093(5) -0.0019(5) 0.0078(5) -0.0019(5) N27 0.0245(7) 0.0217(5) 0.0059(4) -0.0023(4) 0.0074(4) -0.0009(4) C31 0.0200(7) 0.0194(6) 0.0094(5) -0.0029(4) 0.0056(5) -0.0018(5) C37 0.0221(7) 0.0232(6) 0.0110(5) -0.0038(5) 0.0064(5) -0.0022(5) O31 0.0428(7) 0.0216(5) 0.0139(5) -0.0050(4) 0.0138(4) 0.0012(4) O32 0.0456(8) 0.0315(6) 0.0110(5) 0.0001(4) 0.0113(4) 0.0062(5) C32A 0.0273(8) 0.0216(6) 0.0173(6) 0.0025(5) 0.0093(5) 0.0015(5) F32 0.0504(10) 0.0229(7) 0.0131(6) 0.0055(5) 0.0067(5) 0.0065(6) C32B 0.0273(8) 0.0216(6) 0.0173(6) 0.0025(5) 0.0093(5) 0.0015(5) C33 0.0342(10) 0.0209(7) 0.0330(8) -0.0085(6) 0.0190(7) -0.0009(6) C34 0.0338(10) 0.0417(9) 0.0153(7) -0.0157(6) 0.0156(6) -0.0105(7) F34 0.0671(9) 0.0674(8) 0.0267(6) -0.0272(6) 0.0321(6) -0.0144(7) C35 0.0307(9) 0.0453(9) 0.0098(6) 0.0034(6) 0.0071(6) -0.0028(7) C36A 0.0247(8) 0.0250(7) 0.0163(6) 0.0030(5) 0.0085(5) 0.0022(5) C36B 0.0247(8) 0.0250(7) 0.0163(6) 0.0030(5) 0.0085(5) 0.0022(5) F36 0.032(2) 0.0254(16) 0.0172(14) 0.0005(11) 0.0049(12) 0.0056(12) _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 O1S H1A 0.84(2) . ? O1S H1B 0.82(2) . ? N11 C16 1.3399(19) . ? N11 C12 1.3410(18) . ? C12 C13 1.3886(18) . ? C12 H12 0.9500 . ? C13 C14 1.3921(19) . ? C13 H13 0.9500 . ? C14 C15 1.3899(19) . ? C14 C17 1.5045(18) . ? C15 C16 1.3884(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.2242(17) . ? C17 N17 1.3547(17) . ? N17 N27 1.3766(15) . ? N17 H17 0.88(2) . ? N21 C26 1.3408(17) . ? N21 C22 1.3459(18) . ? C22 C23 1.3925(19) . ? C22 C27 1.4703(18) . ? C23 C24 1.3885(18) . ? C23 H23 0.9500 . ? C24 C25 1.384(2) . ? C24 H24 0.9500 . ? C25 C26 1.383(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.2836(18) . ? C27 H27 0.9500 . ? C31 C32A 1.392(2) . ? C31 C36A 1.3945(19) . ? C31 C37 1.4975(18) . ? C37 O32 1.2163(17) . ? C37 O31 1.3183(18) . ? O31 H31 1.11(2) . ? C32A F32 1.3212(18) . ? C32A C33 1.382(2) . ? C33 C34 1.370(3) . ? C33 H33 0.9500 . ? C34 F34 1.3526(17) . ? C34 C35 1.368(3) . ? C35 C36A 1.382(2) . ? C35 H35 0.9500 . ? C36A H36 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 H1A O1S H1B 105(2) . . ? C16 N11 C12 117.98(12) . . ? N11 C12 C13 123.08(13) . . ? N11 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C12 C13 C14 118.57(13) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 118.62(12) . . ? C15 C14 C17 117.58(12) . . ? C13 C14 C17 123.77(12) . . ? C16 C15 C14 118.89(13) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N11 C16 C15 122.84(13) . . ? N11 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? O17 C17 N17 123.75(12) . . ? O17 C17 C14 120.66(12) . . ? N17 C17 C14 115.60(12) . . ? C17 N17 N27 117.51(11) . . ? C17 N17 H17 124.7(13) . . ? N27 N17 H17 117.0(13) . . ? C26 N21 C22 117.53(13) . . ? N21 C22 C23 123.06(12) . . ? N21 C22 C27 113.81(12) . . ? C23 C22 C27 123.12(12) . . ? C24 C23 C22 118.18(13) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C25 C24 C23 119.28(13) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C26 C25 C24 118.60(13) . . ? C26 C25 H25 120.7 . . ? C24 C25 H25 120.7 . . ? N21 C26 C25 123.35(13) . . ? N21 C26 H26 118.3 . . ? C25 C26 H26 118.3 . . ? N27 C27 C22 120.49(13) . . ? N27 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? C27 N27 N17 114.92(12) . . ? C32A C31 C36A 116.47(13) . . ? C32A C31 C37 121.28(12) . . ? C36A C31 C37 122.25(13) . . ? O32 C37 O31 124.10(13) . . ? O32 C37 C31 122.60(13) . . ? O31 C37 C31 113.30(12) . . ? C37 O31 H31 107.1(11) . . ? F32 C32A C33 113.45(14) . . ? F32 C32A C31 123.76(14) . . ? C33 C32A C31 122.63(14) . . ? C34 C33 C32A 117.50(15) . . ? C34 C33 H33 121.2 . . ? C32A C33 H33 121.2 . . ? F34 C34 C35 118.42(16) . . ? F34 C34 C33 118.33(16) . . ? C35 C34 C33 123.25(14) . . ? C34 C35 C36A 117.56(14) . . ? C34 C35 H35 121.2 . . ? C36A C35 H35 121.2 . . ? C35 C36A C31 122.56(14) . . ? C35 C36A H36 118.7 . . ? C31 C36A H36 118.7 . . ? 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 C16 N11 C12 C13 1.4(2) . . . . ? N11 C12 C13 C14 -1.4(2) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C12 C13 C14 C17 -177.99(14) . . . . ? C13 C14 C15 C16 1.1(2) . . . . ? C17 C14 C15 C16 179.29(14) . . . . ? C12 N11 C16 C15 -0.1(2) . . . . ? C14 C15 C16 N11 -1.1(2) . . . . ? C15 C14 C17 O17 -19.3(2) . . . . ? C13 C14 C17 O17 158.78(16) . . . . ? C15 C14 C17 N17 160.92(14) . . . . ? C13 C14 C17 N17 -21.0(2) . . . . ? O17 C17 N17 N27 -0.8(2) . . . . ? C14 C17 N17 N27 178.92(12) . . . . ? C26 N21 C22 C23 -0.6(2) . . . . ? C26 N21 C22 C27 178.81(14) . . . . ? N21 C22 C23 C24 1.0(2) . . . . ? C27 C22 C23 C24 -178.37(14) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C23 C24 C25 C26 -0.2(2) . . . . ? C22 N21 C26 C25 -0.2(2) . . . . ? C24 C25 C26 N21 0.6(3) . . . . ? N21 C22 C27 N27 178.76(15) . . . . ? C23 C22 C27 N27 -1.8(2) . . . . ? C22 C27 N27 N17 179.52(13) . . . . ? C17 N17 N27 C27 176.39(14) . . . . ? C32A C31 C37 O32 -2.0(2) . . . . ? C36A C31 C37 O32 177.35(15) . . . . ? C32A C31 C37 O31 177.68(14) . . . . ? C36A C31 C37 O31 -2.9(2) . . . . ? C36A C31 C32A F32 -174.14(16) . . . . ? C37 C31 C32A F32 5.3(2) . . . . ? C36A C31 C32A C33 0.9(2) . . . . ? C37 C31 C32A C33 -179.63(15) . . . . ? F32 C32A C33 C34 175.55(16) . . . . ? C31 C32A C33 C34 0.0(3) . . . . ? C32A C33 C34 F34 179.80(16) . . . . ? C32A C33 C34 C35 -0.6(3) . . . . ? F34 C34 C35 C36A 179.81(16) . . . . ? C33 C34 C35 C36A 0.2(3) . . . . ? C34 C35 C36A C31 0.8(3) . . . . ? C32A C31 C36A C35 -1.4(2) . . . . ? C37 C31 C36A C35 179.21(15) . . . . ? 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 O1S H1A O17 0.84(2) 2.13(2) 2.8653(15) 146(2) . O1S H1B N21 0.82(2) 2.34(2) 2.9844(19) 136(2) 3 O31 H31 N11 1.11(2) 1.53(2) 2.6337(15) 172.1(18) . N17 H17 O1S 0.88(2) 1.95(2) 2.8264(16) 178(2) 4_545 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.570 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.084 #END data_sf0604m(2J) _database_code_depnum_ccdc_archive 'CCDC 853508' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF229 (3-pyridyl)-CONH-N=CH-(2-pyridyl), 4-nitrobenzoic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C7 H5 N O4) (H2 O) ; _chemical_formula_sum 'C19 H17 N5 O6' _chemical_formula_weight 411.38 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5983(13) _cell_length_b 7.2343(14) _cell_length_c 19.755(4) _cell_angle_alpha 81.922(11) _cell_angle_beta 84.772(14) _cell_angle_gamma 80.711(16) _cell_volume 919.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 844 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.20 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 6545 _diffrn_reflns_av_R_equivalents 0.0969 _diffrn_reflns_av_sigmaI/netI 0.1119 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.04 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3966 _reflns_number_gt 2090 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1500P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3966 _refine_ls_number_parameters 306 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.2475 _refine_ls_wR_factor_gt 0.2181 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.923 _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 O1S O 0.9826(3) 0.2033(4) 0.49819(11) 0.0433(7) Uani 1 1 d D . . H1A H 0.868(2) 0.223(5) 0.5148(17) 0.052 Uiso 1 1 d D . . H1B H 1.039(6) 0.102(3) 0.511(3) 0.052 Uiso 0.50 1 d PD . . H1C H 1.043(5) 0.286(5) 0.503(3) 0.052 Uiso 0.50 1 d PD . . N11 N 0.0101(4) 0.4752(4) 0.74502(13) 0.0362(7) Uani 1 1 d . . . C12 C -0.0489(5) 0.4616(5) 0.68393(17) 0.0385(8) Uani 1 1 d . . . H12 H -0.1919 0.4860 0.6772 0.046 Uiso 1 1 calc R . . C13 C 0.0863(5) 0.4138(5) 0.62961(17) 0.0368(8) Uani 1 1 d . . . H13 H 0.0376 0.4091 0.5862 0.044 Uiso 1 1 calc R . . C14 C 0.2948(4) 0.3726(5) 0.63955(16) 0.0302(7) Uani 1 1 d . . . C15 C 0.3568(4) 0.3856(5) 0.70276(16) 0.0348(8) Uani 1 1 d . . . H15 H 0.4987 0.3593 0.7112 0.042 Uiso 1 1 calc R . . C16 C 0.2109(5) 0.4374(5) 0.75429(16) 0.0360(8) Uani 1 1 d . . . H16 H 0.2556 0.4464 0.7979 0.043 Uiso 1 1 calc R . . C17 C 0.4560(4) 0.3197(4) 0.58389(15) 0.0295(7) Uani 1 1 d . . . N17 N 0.3869(3) 0.2762(4) 0.52730(12) 0.0301(6) Uani 1 1 d . A . H17 H 0.2548 0.2755 0.5243 0.036 Uiso 1 1 calc R . . O17 O 0.6389(3) 0.3169(4) 0.59131(11) 0.0404(6) Uani 1 1 d . . . N21A N 0.792(3) 0.146(3) 0.3711(8) 0.032(2) Uani 0.32(3) 1 d PD A 1 C22A C 0.587(3) 0.14(3) 0.363(4) 0.031(7) Uani 0.32(3) 1 d PD A 1 C23A C 0.512(3) 0.119(9) 0.3025(15) 0.042(3) Uani 0.32(3) 1 d PD A 1 H23A H 0.3684 0.1315 0.2971 0.050 Uiso 0.32(3) 1 calc PR A 1 C24A C 0.6571(17) 0.076(2) 0.2502(7) 0.0369(19) Uani 0.32(3) 1 d PD A 1 H24A H 0.6122 0.0572 0.2077 0.044 Uiso 0.32(3) 1 calc PR A 1 C25A C 0.8609(18) 0.0600(15) 0.2571(5) 0.0354(18) Uani 0.32(3) 1 d PD A 1 H25A H 0.9571 0.0268 0.2204 0.042 Uiso 0.32(3) 1 calc PR A 1 C26A C 0.9287(15) 0.0921(18) 0.3180(6) 0.0335(17) Uani 0.32(3) 1 d PD A 1 H26A H 1.0723 0.0767 0.3233 0.040 Uiso 0.32(3) 1 calc PR A 1 C27A C 0.4546(4) 0.1965(5) 0.42120(16) 0.0329(7) Uani 0.32(3) 1 d P A 1 H27A H 0.3097 0.2058 0.4199 0.040 Uiso 0.32(3) 1 calc PR A 1 N21B N 0.471(2) 0.142(8) 0.3073(13) 0.042(3) Uani 0.39(4) 1 d P A 2 C22B C 0.589(3) 0.15(3) 0.360(3) 0.031(7) Uani 0.39(4) 1 d P A 2 C23B C 0.801(3) 0.106(3) 0.3576(8) 0.032(2) Uani 0.39(4) 1 d P A 2 H23B H 0.8775 0.1003 0.3966 0.039 Uiso 0.39(4) 1 calc PR A 2 C24B C 0.8927(15) 0.0676(16) 0.2941(5) 0.0335(17) Uani 0.39(4) 1 d P A 2 H24B H 1.0387 0.0434 0.2885 0.040 Uiso 0.39(4) 1 calc PR A 2 C25B C 0.7823(17) 0.0627(14) 0.2387(5) 0.0354(18) Uani 0.39(4) 1 d P A 2 H25B H 0.8503 0.0369 0.1958 0.042 Uiso 0.39(4) 1 calc PR A 2 C26B C 0.5724(14) 0.096(2) 0.2471(6) 0.0369(19) Uani 0.39(4) 1 d P A 2 H26B H 0.4945 0.0866 0.2099 0.044 Uiso 0.39(4) 1 calc PR A 2 C27B C 0.4546(4) 0.1965(5) 0.42120(16) 0.0329(7) Uani 0.39(4) 1 d P A 2 H27B H 0.3106 0.1967 0.4211 0.040 Uiso 0.39(4) 1 calc PR A 2 N21C N 0.801(3) 0.106(3) 0.3576(8) 0.032(2) Uani 0.13(3) 1 d PD A 3 C22C C 0.589(3) 0.15(3) 0.360(3) 0.031(7) Uani 0.13(3) 1 d PD A 3 C23C C 0.471(2) 0.142(8) 0.3073(13) 0.042(3) Uani 0.13(3) 1 d PD A 3 H23C H 0.3248 0.1646 0.3126 0.050 Uiso 0.13(3) 1 calc PR A 3 C24C C 0.5724(14) 0.096(2) 0.2471(6) 0.0369(19) Uani 0.13(3) 1 d PD A 3 H24C H 0.4945 0.0866 0.2099 0.044 Uiso 0.13(3) 1 calc PR A 3 C25C C 0.7823(17) 0.0627(14) 0.2387(5) 0.0354(18) Uani 0.13(3) 1 d PD A 3 H25C H 0.8503 0.0369 0.1958 0.042 Uiso 0.13(3) 1 calc PR A 3 C26C C 0.8927(15) 0.0676(16) 0.2941(5) 0.0335(17) Uani 0.13(3) 1 d PD A 3 H26C H 1.0387 0.0434 0.2885 0.040 Uiso 0.13(3) 1 calc PR A 3 C27C C 0.4546(4) 0.1965(5) 0.42120(16) 0.0329(7) Uani 0.13(3) 1 d P A 3 H27C H 0.3106 0.1967 0.4211 0.040 Uiso 0.13(3) 1 calc PR A 3 N21D N 0.512(3) 0.119(9) 0.3025(15) 0.042(3) Uani 0.16(3) 1 d P A 4 C22D C 0.587(3) 0.14(3) 0.363(4) 0.031(7) Uani 0.16(3) 1 d P A 4 C23D C 0.792(3) 0.146(3) 0.3711(8) 0.032(2) Uani 0.16(3) 1 d P A 4 H23D H 0.8357 0.1839 0.4109 0.039 Uiso 0.16(3) 1 calc PR A 4 C24D C 0.9287(15) 0.0921(18) 0.3180(6) 0.0335(17) Uani 0.16(3) 1 d P A 4 H24D H 1.0723 0.0767 0.3233 0.040 Uiso 0.16(3) 1 calc PR A 4 C25D C 0.8609(18) 0.0600(15) 0.2571(5) 0.0354(18) Uani 0.16(3) 1 d P A 4 H25D H 0.9571 0.0268 0.2204 0.042 Uiso 0.16(3) 1 calc PR A 4 C26D C 0.6571(17) 0.076(2) 0.2502(7) 0.0369(19) Uani 0.16(3) 1 d P A 4 H26D H 0.6122 0.0572 0.2077 0.044 Uiso 0.16(3) 1 calc PR A 4 C27D C 0.4546(4) 0.1965(5) 0.42120(16) 0.0329(7) Uani 0.16(3) 1 d P A 4 H27D H 0.3097 0.2058 0.4199 0.040 Uiso 0.16(3) 1 calc PR A 4 N27 N 0.5277(4) 0.2327(4) 0.47418(13) 0.0310(6) Uani 1 1 d . . . C31 C -0.3466(4) 0.6870(4) 0.94775(15) 0.0279(7) Uani 1 1 d . . . C37 C -0.1922(4) 0.6247(5) 0.89269(16) 0.0323(7) Uani 1 1 d . . . O31 O -0.2710(3) 0.5765(4) 0.84101(12) 0.0405(6) Uani 1 1 d . . . H31 H -0.164(7) 0.549(7) 0.808(2) 0.092(16) Uiso 1 1 d . . . O32 O -0.0089(3) 0.6179(4) 0.89708(12) 0.0500(7) Uani 1 1 d . . . C32 C -0.2795(4) 0.7134(5) 1.00933(16) 0.0333(8) Uani 1 1 d . . . H32 H -0.1362 0.6900 1.0157 0.040 Uiso 1 1 calc R . . C33 C -0.4155(4) 0.7728(5) 1.06155(15) 0.0307(7) Uani 1 1 d . . . H33 H -0.3690 0.7914 1.1039 0.037 Uiso 1 1 calc R . . C34 C -0.6234(4) 0.8047(4) 1.05022(15) 0.0295(7) Uani 1 1 d . . . N34 N -0.7707(4) 0.8644(4) 1.10629(13) 0.0356(7) Uani 1 1 d . . . O33 O -0.7053(4) 0.8909(4) 1.15867(12) 0.0520(7) Uani 1 1 d . . . O34 O -0.9549(3) 0.8839(4) 1.09722(13) 0.0537(8) Uani 1 1 d . . . C35 C -0.6960(4) 0.7808(5) 0.98963(16) 0.0320(7) Uani 1 1 d . . . H35 H -0.8394 0.8057 0.9834 0.038 Uiso 1 1 calc R . . C36 C -0.5571(4) 0.7199(4) 0.93787(15) 0.0300(7) Uani 1 1 d . . . H36 H -0.6043 0.7005 0.8958 0.036 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 O1S 0.0264(11) 0.0637(18) 0.0390(14) -0.0100(13) 0.0061(10) -0.0061(11) N11 0.0357(14) 0.0443(17) 0.0301(15) -0.0100(13) 0.0074(11) -0.0114(12) C12 0.0285(15) 0.047(2) 0.042(2) -0.0177(17) 0.0033(14) -0.0062(14) C13 0.0273(14) 0.052(2) 0.0345(18) -0.0159(16) -0.0001(13) -0.0066(14) C14 0.0302(15) 0.0334(18) 0.0283(16) -0.0063(14) 0.0032(12) -0.0094(13) C15 0.0268(14) 0.046(2) 0.0326(18) -0.0021(15) -0.0013(13) -0.0097(13) C16 0.0386(16) 0.045(2) 0.0247(16) -0.0034(15) -0.0004(13) -0.0101(15) C17 0.0240(14) 0.0362(19) 0.0290(17) -0.0041(14) 0.0011(12) -0.0078(12) N17 0.0230(11) 0.0401(16) 0.0276(14) -0.0074(12) 0.0044(10) -0.0070(11) O17 0.0244(10) 0.0620(17) 0.0386(13) -0.0182(12) 0.0012(9) -0.0099(10) N21A 0.030(2) 0.026(7) 0.037(5) -0.014(3) 0.018(3) 0.004(4) C22A 0.0328(16) 0.033(18) 0.027(5) -0.003(9) 0.0058(14) -0.007(2) C23A 0.058(6) 0.046(11) 0.024(3) -0.011(3) 0.004(4) -0.014(9) C24A 0.044(6) 0.045(4) 0.025(2) -0.007(2) -0.003(5) -0.012(6) C25A 0.052(6) 0.046(3) 0.012(4) -0.012(3) 0.003(3) -0.014(4) C26A 0.030(4) 0.048(4) 0.026(6) -0.013(4) 0.001(3) -0.010(3) C27A 0.0306(15) 0.0385(19) 0.0293(17) -0.0031(14) 0.0029(13) -0.0077(13) N21B 0.058(6) 0.046(11) 0.024(3) -0.011(3) 0.004(4) -0.014(9) C22B 0.0328(16) 0.033(18) 0.027(5) -0.003(9) 0.0058(14) -0.007(2) C23B 0.030(2) 0.026(7) 0.037(5) -0.014(3) 0.018(3) 0.004(4) C24B 0.030(4) 0.048(4) 0.026(6) -0.013(4) 0.001(3) -0.010(3) C25B 0.052(6) 0.046(3) 0.012(4) -0.012(3) 0.003(3) -0.014(4) C26B 0.044(6) 0.045(4) 0.025(2) -0.007(2) -0.003(5) -0.012(6) C27B 0.0306(15) 0.0385(19) 0.0293(17) -0.0031(14) 0.0029(13) -0.0077(13) N21C 0.030(2) 0.026(7) 0.037(5) -0.014(3) 0.018(3) 0.004(4) C22C 0.0328(16) 0.033(18) 0.027(5) -0.003(9) 0.0058(14) -0.007(2) C23C 0.058(6) 0.046(11) 0.024(3) -0.011(3) 0.004(4) -0.014(9) C24C 0.044(6) 0.045(4) 0.025(2) -0.007(2) -0.003(5) -0.012(6) C25C 0.052(6) 0.046(3) 0.012(4) -0.012(3) 0.003(3) -0.014(4) C26C 0.030(4) 0.048(4) 0.026(6) -0.013(4) 0.001(3) -0.010(3) C27C 0.0306(15) 0.0385(19) 0.0293(17) -0.0031(14) 0.0029(13) -0.0077(13) N21D 0.058(6) 0.046(11) 0.024(3) -0.011(3) 0.004(4) -0.014(9) C22D 0.0328(16) 0.033(18) 0.027(5) -0.003(9) 0.0058(14) -0.007(2) C23D 0.030(2) 0.026(7) 0.037(5) -0.014(3) 0.018(3) 0.004(4) C24D 0.030(4) 0.048(4) 0.026(6) -0.013(4) 0.001(3) -0.010(3) C25D 0.052(6) 0.046(3) 0.012(4) -0.012(3) 0.003(3) -0.014(4) C26D 0.044(6) 0.045(4) 0.025(2) -0.007(2) -0.003(5) -0.012(6) C27D 0.0306(15) 0.0385(19) 0.0293(17) -0.0031(14) 0.0029(13) -0.0077(13) N27 0.0272(12) 0.0391(16) 0.0264(14) -0.0062(12) 0.0047(10) -0.0063(11) C31 0.0260(14) 0.0302(17) 0.0285(16) -0.0028(13) 0.0030(12) -0.0102(12) C37 0.0307(15) 0.0381(19) 0.0276(17) -0.0030(14) -0.0013(13) -0.0052(13) O31 0.0320(11) 0.0624(17) 0.0304(13) -0.0179(12) 0.0068(10) -0.0112(11) O32 0.0255(11) 0.082(2) 0.0427(15) -0.0167(13) 0.0011(10) -0.0043(12) C32 0.0248(14) 0.045(2) 0.0299(17) -0.0027(15) -0.0025(12) -0.0071(13) C33 0.0324(15) 0.0392(19) 0.0228(16) -0.0031(14) -0.0051(12) -0.0110(13) C34 0.0281(14) 0.0335(18) 0.0270(16) -0.0066(13) 0.0056(12) -0.0072(12) N34 0.0378(14) 0.0433(18) 0.0279(15) -0.0110(13) 0.0052(11) -0.0114(12) O33 0.0503(14) 0.084(2) 0.0283(13) -0.0254(13) 0.0040(11) -0.0193(14) O34 0.0285(12) 0.087(2) 0.0472(15) -0.0257(14) 0.0053(10) -0.0024(12) C35 0.0250(14) 0.0396(19) 0.0325(17) -0.0048(14) -0.0027(12) -0.0075(13) C36 0.0321(15) 0.0369(19) 0.0225(16) -0.0043(14) -0.0012(12) -0.0094(13) _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 O1S H1A 0.796(10) . ? O1S H1B 0.786(10) . ? O1S H1C 0.792(10) . ? N11 C12 1.323(4) . ? N11 C16 1.333(4) . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 C15 1.369(4) . ? C14 C17 1.504(4) . ? C15 C16 1.384(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.225(3) . ? C17 N17 1.340(4) . ? N17 N27 1.373(3) . ? N17 H17 0.8800 . ? N21A C26A 1.376(11) . ? N21A C22A 1.39(3) . ? C22A C23A 1.369(11) . ? C22A C27A 1.45(2) . ? C23A C24A 1.377(12) . ? C23A H23A 0.9500 . ? C24A C25A 1.348(10) . ? C24A H24A 0.9500 . ? C25A C26A 1.383(9) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? C27A N27 1.267(4) . ? C27A H27A 0.9500 . ? N21B C26B 1.366(11) . ? N21B C22B 1.368(10) . ? C22B C23B 1.39(3) . ? C23B C24B 1.388(11) . ? C23B H23B 0.9500 . ? C24B C25B 1.376(9) . ? C24B H24B 0.9500 . ? C25B C26B 1.366(9) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? C31 C32 1.380(4) . ? C31 C36 1.398(4) . ? C31 C37 1.487(4) . ? C37 O32 1.213(4) . ? C37 O31 1.300(4) . ? O31 H31 0.94(5) . ? C32 C33 1.373(4) . ? C32 H32 0.9500 . ? C33 C34 1.387(4) . ? C33 H33 0.9500 . ? C34 C35 1.372(4) . ? C34 N34 1.470(4) . ? N34 O33 1.207(3) . ? N34 O34 1.228(3) . ? C35 C36 1.380(4) . ? C35 H35 0.9500 . ? C36 H36 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 H1A O1S H1B 112(2) . . ? H1A O1S H1C 110(2) . . ? H1B O1S H1C 115(2) . . ? C12 N11 C16 117.8(3) . . ? N11 C12 C13 123.4(3) . . ? N11 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C12 C13 C14 118.7(3) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 118.2(3) . . ? C15 C14 C17 118.6(3) . . ? C13 C14 C17 123.2(3) . . ? C14 C15 C16 119.4(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N11 C16 C15 122.5(3) . . ? N11 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? O17 C17 N17 123.2(3) . . ? O17 C17 C14 120.7(3) . . ? N17 C17 C14 116.1(2) . . ? C17 N17 N27 118.2(2) . . ? C17 N17 H17 120.9 . . ? N27 N17 H17 120.9 . . ? C26A N21A C22A 115.6(15) . . ? C23A C22A N21A 125(2) . . ? C23A C22A C27A 122.7(16) . . ? N21A C22A C27A 112(3) . . ? C22A C23A C24A 115.9(14) . . ? C22A C23A H23A 122.1 . . ? C24A C23A H23A 122.1 . . ? C25A C24A C23A 122.5(11) . . ? C25A C24A H24A 118.8 . . ? C23A C24A H24A 118.8 . . ? C24A C25A C26A 119.5(9) . . ? C24A C25A H25A 120.3 . . ? C26A C25A H25A 120.3 . . ? N21A C26A C25A 121.3(10) . . ? N21A C26A H26A 119.4 . . ? C25A C26A H26A 119.4 . . ? N27 C27A C22A 121.5(12) . . ? N27 C27A H27A 119.3 . . ? C22A C27A H27A 119.3 . . ? C26B N21B C22B 117.1(12) . . ? N21B C22B C23B 125(2) . . ? C22B C23B C24B 114.3(14) . . ? C22B C23B H23B 122.8 . . ? C24B C23B H23B 122.8 . . ? C25B C24B C23B 123.2(10) . . ? C25B C24B H24B 118.4 . . ? C23B C24B H24B 118.4 . . ? C26B C25B C24B 118.2(8) . . ? C26B C25B H25B 120.9 . . ? C24B C25B H25B 120.9 . . ? C25B C26B N21B 122.1(10) . . ? C25B C26B H26B 118.9 . . ? N21B C26B H26B 118.9 . . ? C27A N27 N17 115.9(2) . . ? C32 C31 C36 119.8(3) . . ? C32 C31 C37 119.0(3) . . ? C36 C31 C37 121.1(3) . . ? O32 C37 O31 123.9(3) . . ? O32 C37 C31 121.9(3) . . ? O31 C37 C31 114.2(3) . . ? C37 O31 H31 108(3) . . ? C33 C32 C31 121.3(3) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C32 C33 C34 117.5(3) . . ? C32 C33 H33 121.2 . . ? C34 C33 H33 121.2 . . ? C35 C34 C33 122.9(3) . . ? C35 C34 N34 119.2(3) . . ? C33 C34 N34 118.0(3) . . ? O33 N34 O34 123.4(3) . . ? O33 N34 C34 118.8(3) . . ? O34 N34 C34 117.8(3) . . ? C34 C35 C36 118.8(3) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? C35 C36 C31 119.6(3) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? 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 C16 N11 C12 C13 -1.2(5) . . . . ? N11 C12 C13 C14 1.8(5) . . . . ? C12 C13 C14 C15 -1.4(5) . . . . ? C12 C13 C14 C17 -179.7(3) . . . . ? C13 C14 C15 C16 0.5(5) . . . . ? C17 C14 C15 C16 178.8(3) . . . . ? C12 N11 C16 C15 0.1(5) . . . . ? C14 C15 C16 N11 0.2(5) . . . . ? C15 C14 C17 O17 -11.1(5) . . . . ? C13 C14 C17 O17 167.2(3) . . . . ? C15 C14 C17 N17 168.5(3) . . . . ? C13 C14 C17 N17 -13.2(5) . . . . ? O17 C17 N17 N27 -2.4(5) . . . . ? C14 C17 N17 N27 178.0(3) . . . . ? C26A N21A C22A C23A -11(22) . . . . ? C26A N21A C22A C27A 179(9) . . . . ? N21A C22A C23A C24A 8(22) . . . . ? C27A C22A C23A C24A 177(12) . . . . ? C22A C23A C24A C25A -1(12) . . . . ? C23A C24A C25A C26A -2(4) . . . . ? C22A N21A C26A C25A 8(10) . . . . ? C24A C25A C26A N21A -2(2) . . . . ? C23A C22A C27A N27 -174(11) . . . . ? N21A C22A C27A N27 -4(18) . . . . ? C26B N21B C22B C23B -6(21) . . . . ? N21B C22B C23B C24B 8(20) . . . . ? C22B C23B C24B C25B -5(9) . . . . ? C23B C24B C25B C26B -1(2) . . . . ? C24B C25B C26B N21B 3(3) . . . . ? C22B N21B C26B C25B 0(11) . . . . ? C22A C27A N27 N17 -178(10) . . . . ? C17 N17 N27 C27A -178.5(3) . . . . ? C32 C31 C37 O32 -8.9(5) . . . . ? C36 C31 C37 O32 170.7(3) . . . . ? C32 C31 C37 O31 170.1(3) . . . . ? C36 C31 C37 O31 -10.2(5) . . . . ? C36 C31 C32 C33 -0.4(5) . . . . ? C37 C31 C32 C33 179.3(3) . . . . ? C31 C32 C33 C34 0.3(5) . . . . ? C32 C33 C34 C35 -0.5(5) . . . . ? C32 C33 C34 N34 178.7(3) . . . . ? C35 C34 N34 O33 -177.7(3) . . . . ? C33 C34 N34 O33 3.1(5) . . . . ? C35 C34 N34 O34 2.6(5) . . . . ? C33 C34 N34 O34 -176.7(3) . . . . ? C33 C34 C35 C36 0.9(5) . . . . ? N34 C34 C35 C36 -178.3(3) . . . . ? C34 C35 C36 C31 -1.0(5) . . . . ? C32 C31 C36 C35 0.8(5) . . . . ? C37 C31 C36 C35 -178.9(3) . . . . ? 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 O1S H1A O17 0.796(10) 2.138(18) 2.875(3) 154(3) . O1S H1B O1S 0.786(10) 2.27(4) 2.904(6) 139(5) 2_756 O31 H31 N11 0.94(5) 1.69(5) 2.624(3) 172(4) . _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.784 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.120 #END data_sf0706m(4C) _database_code_depnum_ccdc_archive 'CCDC 853509' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF41 4-pyridyl-CONH-N=CH-4-pyridyl, succinic acid dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C4 H6 O4) (H2 O)2 ; _chemical_formula_sum 'C16 H20 N4 O7' _chemical_formula_weight 380.36 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 4.8122(3) _cell_length_b 8.8128(5) _cell_length_c 11.0772(6) _cell_angle_alpha 75.874(3) _cell_angle_beta 80.095(3) _cell_angle_gamma 76.225(3) _cell_volume 439.22(4) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7222 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 33.10 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 14803 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 32.57 _reflns_number_total 3150 _reflns_number_gt 2646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3150 _refine_ls_number_parameters 142 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1659 _refine_ls_wR_factor_gt 0.1586 _refine_ls_goodness_of_fit_ref 1.318 _refine_ls_restrained_S_all 1.317 _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 O1S O -0.1808(3) 1.09522(14) 0.08439(9) 0.0551(3) Uani 1 1 d D . . H1A H -0.098(4) 1.068(2) 0.1465(13) 0.066 Uiso 1 1 d D . . H1B H -0.313(6) 1.048(4) 0.098(3) 0.066 Uiso 0.50 1 d PD A 1 H1C H -0.110(7) 1.037(4) 0.037(2) 0.066 Uiso 0.50 1 d PD B 2 N11 N 0.43616(16) 0.63928(9) 0.31168(7) 0.01951(18) Uani 1 1 d . C . C12 C 0.5740(2) 0.73425(11) 0.21914(9) 0.0224(2) Uani 1 1 d . . . H12 H 0.4911 0.8451 0.1983 0.027 Uiso 1 1 calc R . . C13 C 0.8333(2) 0.67589(12) 0.15289(9) 0.0225(2) Uani 1 1 d . C . H13 H 0.9263 0.7459 0.0880 0.027 Uiso 1 1 calc R . . C14 C 0.95625(18) 0.51287(11) 0.18272(8) 0.01825(19) Uani 1 1 d . . . C15 C 0.81082(19) 0.41441(11) 0.27787(8) 0.01909(19) Uani 1 1 d . C . H15 H 0.8866 0.3028 0.2998 0.023 Uiso 1 1 calc R . . C16 C 0.55271(19) 0.48273(11) 0.34008(8) 0.0197(2) Uani 1 1 d . . . H16 H 0.4548 0.4157 0.4055 0.024 Uiso 1 1 calc R C . C17A C 1.23187(18) 0.43895(11) 0.11671(8) 0.01869(19) Uani 0.50 1 d P C 1 O17 O 1.3171(3) 0.29502(17) 0.14358(14) 0.0253(3) Uani 0.50 1 d P C 1 C17B C 1.23187(18) 0.43895(11) 0.11671(8) 0.01869(19) Uani 0.50 1 d P C 2 H17A H 1.3043 0.3268 0.1358 0.022 Uiso 0.50 1 calc PR C 2 N17 N 1.37318(15) 0.53561(10) 0.02995(7) 0.01958(19) Uani 1 1 d . . . H17 H 1.306(6) 0.641(3) 0.009(3) 0.023 Uiso 0.50 1 d P . . C21 C -0.15872(19) 0.87334(10) 0.42564(8) 0.01882(19) Uani 1 1 d . . . O21 O -0.04211(14) 0.72047(8) 0.44822(7) 0.02318(18) Uani 1 1 d . . . H21 H 0.133(3) 0.7027(16) 0.3861(13) 0.028 Uiso 1 1 d . . . O22 O -0.05441(17) 0.97377(9) 0.34485(7) 0.0292(2) Uani 1 1 d . . . C22 C -0.43488(19) 0.91165(10) 0.50995(9) 0.0199(2) Uani 1 1 d . . . H22A H -0.3968 0.8712 0.5984 0.024 Uiso 1 1 calc R . . H22B H -0.5761 0.8550 0.4949 0.024 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 O1S 0.0831(9) 0.0609(7) 0.0278(5) -0.0086(4) 0.0119(5) -0.0416(6) N11 0.0174(3) 0.0209(4) 0.0209(4) -0.0087(3) 0.0049(3) -0.0062(3) C12 0.0229(4) 0.0196(4) 0.0249(4) -0.0087(3) 0.0071(3) -0.0074(3) C13 0.0228(4) 0.0222(4) 0.0231(4) -0.0082(3) 0.0083(3) -0.0102(3) C14 0.0157(4) 0.0241(4) 0.0172(4) -0.0095(3) 0.0043(3) -0.0077(3) C15 0.0172(4) 0.0216(4) 0.0174(4) -0.0057(3) 0.0032(3) -0.0042(3) C16 0.0180(4) 0.0221(4) 0.0184(4) -0.0061(3) 0.0052(3) -0.0061(3) C17A 0.0164(4) 0.0235(4) 0.0172(4) -0.0089(3) 0.0043(3) -0.0060(3) O17 0.0216(6) 0.0223(6) 0.0276(7) -0.0066(5) 0.0088(5) -0.0033(5) C17B 0.0164(4) 0.0235(4) 0.0172(4) -0.0089(3) 0.0043(3) -0.0060(3) N17 0.0148(3) 0.0260(4) 0.0194(4) -0.0115(3) 0.0053(3) -0.0054(3) C21 0.0170(4) 0.0201(4) 0.0196(4) -0.0063(3) 0.0028(3) -0.0056(3) O21 0.0195(3) 0.0198(3) 0.0251(3) -0.0048(3) 0.0072(2) -0.0011(2) O22 0.0282(4) 0.0218(3) 0.0308(4) -0.0033(3) 0.0119(3) -0.0056(3) C22 0.0159(4) 0.0179(4) 0.0234(4) -0.0048(3) 0.0053(3) -0.0033(3) _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 O1S H1A 0.811(9) . ? O1S H1B 0.814(10) . ? O1S H1C 0.800(10) . ? N11 C16 1.3407(11) . ? N11 C12 1.3427(11) . ? C12 C13 1.3869(13) . ? C12 H12 0.9500 . ? C13 C14 1.3979(13) . ? C13 H13 0.9500 . ? C14 C15 1.3938(12) . ? C14 C17A 1.4852(12) . ? C15 C16 1.3899(12) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17A O17 1.2147(17) . ? C17A N17 1.3278(11) . ? N17 N17 1.3725(14) 2_865 ? N17 H17 0.89(3) . ? C21 O22 1.2275(10) . ? C21 O21 1.3100(10) . ? C21 C22 1.5051(12) . ? O21 H21 0.999(15) . ? C22 C22 1.5106(17) 2_476 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 H1A O1S H1B 107.0(16) . . ? H1A O1S H1C 110.1(17) . . ? H1B O1S H1C 85(4) . . ? C16 N11 C12 118.71(7) . . ? N11 C12 C13 122.18(8) . . ? N11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C12 C13 C14 119.26(8) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 118.37(8) . . ? C15 C14 C17A 118.36(8) . . ? C13 C14 C17A 123.25(8) . . ? C16 C15 C14 118.70(8) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N11 C16 C15 122.77(8) . . ? N11 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? O17 C17A N17 123.21(10) . . ? O17 C17A C14 119.33(10) . . ? N17 C17A C14 117.46(8) . . ? C17A N17 N17 116.35(10) . 2_865 ? C17A N17 H17 122.6(17) . . ? N17 N17 H17 121.0(18) 2_865 . ? O22 C21 O21 123.77(8) . . ? O22 C21 C22 123.90(8) . . ? O21 C21 C22 112.33(7) . . ? C21 O21 H21 108.1(8) . . ? C21 C22 C22 113.21(9) . 2_476 ? C21 C22 H22A 108.9 . . ? C22 C22 H22A 108.9 2_476 . ? C21 C22 H22B 108.9 . . ? C22 C22 H22B 108.9 2_476 . ? H22A C22 H22B 107.7 . . ? 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 C16 N11 C12 C13 -0.50(14) . . . . ? N11 C12 C13 C14 0.14(15) . . . . ? C12 C13 C14 C15 0.59(14) . . . . ? C12 C13 C14 C17A 179.59(8) . . . . ? C13 C14 C15 C16 -0.95(14) . . . . ? C17A C14 C15 C16 180.00(8) . . . . ? C12 N11 C16 C15 0.12(14) . . . . ? C14 C15 C16 N11 0.62(14) . . . . ? C15 C14 C17A O17 2.90(16) . . . . ? C13 C14 C17A O17 -176.11(12) . . . . ? C15 C14 C17A N17 -177.27(8) . . . . ? C13 C14 C17A N17 3.72(14) . . . . ? O17 C17A N17 N17 0.00(18) . . . 2_865 ? C14 C17A N17 N17 -179.82(8) . . . 2_865 ? O22 C21 C22 C22 -2.97(16) . . . 2_476 ? O21 C21 C22 C22 177.05(10) . . . 2_476 ? 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 O1S H1A O22 0.811(9) 2.178(12) 2.9370(14) 155.8(18) . O1S H1B O17 0.814(10) 2.56(4) 2.7130(19) 92(3) 1_365 O1S H1C O1S 0.800(10) 2.115(15) 2.892(2) 164(4) 2_575 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 32.57 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.514 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.066 #END data_sf0709m(4D) _database_code_depnum_ccdc_archive 'CCDC 853510' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF807 [(4-pyridyl)-CONH-N=CH-(4-pyridyl)], hexanedioic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C6 H10 O4) (H2 O) ; _chemical_formula_sum 'C18 H22 N4 O6' _chemical_formula_weight 390.40 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 6.8908(3) _cell_length_b 11.3841(6) _cell_length_c 12.6504(6) _cell_angle_alpha 66.395(2) _cell_angle_beta 89.086(2) _cell_angle_gamma 84.907(2) _cell_volume 905.54(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5095 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 30.35 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 15411 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.50 _reflns_number_total 5258 _reflns_number_gt 3710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0700P)^2^+0.2000P] 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 5258 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 O1S O 0.14428(17) 0.27124(13) -0.03878(12) 0.0335(3) Uani 1 1 d . . . H1A H 0.119(3) 0.305(2) -0.113(2) 0.040 Uiso 1 1 d . . . H1B H 0.039(3) 0.277(2) -0.0161(19) 0.040 Uiso 1 1 d . . . N11 N 0.28655(19) 0.51489(14) 0.25052(12) 0.0267(3) Uani 1 1 d . A . C12 C 0.2060(2) 0.44806(17) 0.20039(15) 0.0286(4) Uani 1 1 d . . . H12 H 0.0686 0.4450 0.2036 0.034 Uiso 1 1 calc R . . C13 C 0.3113(2) 0.38284(16) 0.14384(14) 0.0269(3) Uani 1 1 d . A . H13 H 0.2477 0.3363 0.1089 0.032 Uiso 1 1 calc R . . C14 C 0.5114(2) 0.38651(15) 0.13897(13) 0.0225(3) Uani 1 1 d . . . C15 C 0.5952(2) 0.45625(16) 0.19069(14) 0.0263(3) Uani 1 1 d . A . H15 H 0.7322 0.4613 0.1887 0.032 Uiso 1 1 calc R . . C16 C 0.4792(2) 0.51827(16) 0.24514(14) 0.0271(3) Uani 1 1 d . . . H16 H 0.5391 0.5657 0.2806 0.033 Uiso 1 1 calc R A . C17A C 0.6443(2) 0.31973(15) 0.08180(13) 0.0241(3) Uani 0.978(3) 1 d P A 1 O17 O 0.82038(15) 0.31972(12) 0.08793(11) 0.0308(4) Uani 0.978(3) 1 d P A 1 C17B C 0.6443(2) 0.31973(15) 0.08180(13) 0.0241(3) Uani 0.022(3) 1 d P A 2 H17B H 0.7821 0.3188 0.0855 0.029 Uiso 0.022(3) 1 calc PR A 2 N17 N 0.55559(19) 0.26100(13) 0.02466(12) 0.0257(3) Uani 1 1 d . . . H17 H 0.432(3) 0.2718(18) 0.0111(16) 0.031 Uiso 1 1 d . . . N21 N 0.87114(18) -0.06458(14) -0.25653(12) 0.0266(3) Uani 1 1 d . A . C22 C 0.9718(2) -0.01251(16) -0.19951(14) 0.0271(3) Uani 1 1 d . . . H22 H 1.1100 -0.0257 -0.1976 0.032 Uiso 1 1 calc R . . C23 C 0.8849(2) 0.05936(16) -0.14342(14) 0.0261(3) Uani 1 1 d . A . H23 H 0.9615 0.0958 -0.1046 0.031 Uiso 1 1 calc R . . C24 C 0.6831(2) 0.07749(15) -0.14484(13) 0.0235(3) Uani 1 1 d . . . C25 C 0.5793(2) 0.02306(16) -0.20368(14) 0.0263(3) Uani 1 1 d . A . H25 H 0.4409 0.0334 -0.2061 0.032 Uiso 1 1 calc R . . C26 C 0.6780(2) -0.04608(16) -0.25862(14) 0.0268(3) Uani 1 1 d . . . H26 H 0.6051 -0.0820 -0.2996 0.032 Uiso 1 1 calc R A . C27A C 0.5772(2) 0.14927(16) -0.08603(14) 0.0266(3) Uani 0.978(3) 1 d P A 1 H27A H 0.4389 0.1611 -0.0910 0.032 Uiso 0.978(3) 1 calc PR A 1 C27B C 0.5772(2) 0.14927(16) -0.08603(14) 0.0266(3) Uani 0.022(3) 1 d P A 2 O27 O 0.399(5) 0.145(4) -0.093(3) 0.007(10) Uiso 0.022(3) 1 d P A 2 N27 N 0.66933(18) 0.19633(13) -0.02788(11) 0.0254(3) Uani 1 1 d . A . C31 C -0.0727(2) 0.65868(17) 0.35838(14) 0.0276(3) Uani 1 1 d . . . O31 O 0.11098(16) 0.61854(13) 0.38245(11) 0.0357(3) Uani 1 1 d . . . H31 H 0.157(3) 0.588(2) 0.333(2) 0.043 Uiso 1 1 d . . . O32 O -0.15843(16) 0.65351(15) 0.27773(11) 0.0424(4) Uani 1 1 d . . . C32 C -0.1645(2) 0.71513(18) 0.43725(15) 0.0290(4) Uani 1 1 d . . . H32A H -0.1390 0.8069 0.4081 0.035 Uiso 1 1 calc R . . H32B H -0.1012 0.6706 0.5145 0.035 Uiso 1 1 calc R . . C33 C -0.3824(2) 0.70597(16) 0.44957(14) 0.0255(3) Uani 1 1 d . . . H33A H -0.4084 0.6145 0.4893 0.031 Uiso 1 1 calc R . . H33B H -0.4454 0.7404 0.3720 0.031 Uiso 1 1 calc R . . C34 C -0.4701(2) 0.78077(16) 0.51768(14) 0.0251(3) Uani 1 1 d . . . H34A H -0.4075 0.7461 0.5954 0.030 Uiso 1 1 calc R . . H34B H -0.4436 0.8722 0.4781 0.030 Uiso 1 1 calc R . . C35 C -0.6880(2) 0.77225(17) 0.52965(14) 0.0257(3) Uani 1 1 d . . . H35A H -0.7507 0.8143 0.4520 0.031 Uiso 1 1 calc R . . H35B H -0.7140 0.6804 0.5614 0.031 Uiso 1 1 calc R . . C36 C -0.7796(2) 0.83327(16) 0.60541(14) 0.0254(3) Uani 1 1 d . . . O36 O -0.96310(16) 0.81027(14) 0.62591(12) 0.0367(3) Uani 1 1 d . . . H36 H -1.017(3) 0.857(2) 0.6675(19) 0.044 Uiso 1 1 d . . . O37 O -0.69697(16) 0.89642(12) 0.64472(11) 0.0343(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 O1S 0.0246(5) 0.0483(8) 0.0345(7) -0.0236(6) 0.0049(5) -0.0050(5) N11 0.0267(6) 0.0301(7) 0.0296(7) -0.0185(6) 0.0042(5) -0.0029(5) C12 0.0217(7) 0.0354(9) 0.0356(9) -0.0213(8) 0.0032(6) -0.0039(6) C13 0.0246(7) 0.0316(9) 0.0321(8) -0.0204(7) 0.0023(6) -0.0038(6) C14 0.0228(6) 0.0237(8) 0.0237(8) -0.0123(6) 0.0031(6) -0.0021(6) C15 0.0218(6) 0.0319(9) 0.0300(8) -0.0169(7) 0.0029(6) -0.0048(6) C16 0.0273(7) 0.0309(9) 0.0305(8) -0.0192(7) 0.0041(6) -0.0070(6) C17A 0.0250(7) 0.0257(8) 0.0244(8) -0.0131(6) 0.0032(6) -0.0013(6) O17 0.0217(5) 0.0411(8) 0.0370(7) -0.0235(6) 0.0042(5) -0.0026(5) C17B 0.0250(7) 0.0257(8) 0.0244(8) -0.0131(6) 0.0032(6) -0.0013(6) N17 0.0233(6) 0.0308(8) 0.0305(7) -0.0208(6) 0.0035(5) -0.0001(5) N21 0.0251(6) 0.0310(7) 0.0303(7) -0.0190(6) 0.0028(5) -0.0040(5) C22 0.0211(6) 0.0338(9) 0.0337(9) -0.0211(7) 0.0024(6) -0.0033(6) C23 0.0256(7) 0.0297(9) 0.0299(8) -0.0186(7) 0.0000(6) -0.0048(6) C24 0.0242(7) 0.0249(8) 0.0249(8) -0.0136(6) 0.0030(6) -0.0020(6) C25 0.0217(6) 0.0303(9) 0.0319(9) -0.0173(7) 0.0023(6) -0.0045(6) C26 0.0256(7) 0.0303(9) 0.0307(8) -0.0184(7) 0.0008(6) -0.0046(6) C27A 0.0253(7) 0.0288(9) 0.0297(8) -0.0162(7) 0.0031(6) -0.0015(6) C27B 0.0253(7) 0.0288(9) 0.0297(8) -0.0162(7) 0.0031(6) -0.0015(6) N27 0.0273(6) 0.0256(7) 0.0272(7) -0.0153(6) 0.0057(5) -0.0004(5) C31 0.0247(7) 0.0372(9) 0.0302(8) -0.0219(7) 0.0054(6) -0.0096(6) O31 0.0262(5) 0.0542(9) 0.0423(7) -0.0367(7) 0.0010(5) 0.0023(5) O32 0.0270(6) 0.0791(11) 0.0400(7) -0.0426(7) 0.0058(5) -0.0116(6) C32 0.0235(7) 0.0404(10) 0.0333(9) -0.0252(8) 0.0033(6) -0.0042(7) C33 0.0226(6) 0.0315(9) 0.0283(8) -0.0182(7) 0.0029(6) -0.0028(6) C34 0.0220(6) 0.0301(9) 0.0290(8) -0.0178(7) 0.0023(6) -0.0027(6) C35 0.0230(6) 0.0326(9) 0.0282(8) -0.0193(7) 0.0028(6) -0.0028(6) C36 0.0219(6) 0.0309(9) 0.0288(8) -0.0171(7) 0.0014(6) -0.0041(6) O36 0.0236(5) 0.0556(8) 0.0528(8) -0.0435(7) 0.0106(5) -0.0114(5) O37 0.0262(5) 0.0454(8) 0.0474(7) -0.0342(6) 0.0056(5) -0.0093(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 O1S H1A 0.87(2) . ? O1S H1B 0.78(2) . ? N11 C12 1.327(2) . ? N11 C16 1.3316(19) . ? C12 C13 1.380(2) . ? C12 H12 0.9500 . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 C15 1.379(2) . ? C14 C17A 1.495(2) . ? C15 C16 1.372(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17A O17 1.2170(18) . ? C17A N17 1.348(2) . ? N17 N27 1.3678(17) . ? N17 H17 0.860(19) . ? N21 C26 1.3279(19) . ? N21 C22 1.336(2) . ? C22 C23 1.377(2) . ? C22 H22 0.9500 . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 C25 1.384(2) . ? C24 C27A 1.455(2) . ? C25 C26 1.376(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27A N27 1.274(2) . ? C27A H27A 0.9500 . ? C31 O32 1.2112(19) . ? C31 O31 1.3044(19) . ? C31 C32 1.493(2) . ? O31 H31 0.87(2) . ? C32 C33 1.516(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.521(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.515(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.495(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 O37 1.2070(18) . ? C36 O36 1.3146(18) . ? O36 H36 0.94(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 H1A O1S H1B 100(2) . . ? C12 N11 C16 117.52(13) . . ? N11 C12 C13 123.42(14) . . ? N11 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C12 C13 C14 118.68(14) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 117.95(13) . . ? C15 C14 C17A 117.41(13) . . ? C13 C14 C17A 124.65(13) . . ? C16 C15 C14 119.50(13) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N11 C16 C15 122.93(14) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? O17 C17A N17 123.49(14) . . ? O17 C17A C14 120.98(14) . . ? N17 C17A C14 115.53(12) . . ? C17A N17 N27 118.35(12) . . ? C17A N17 H17 122.8(12) . . ? N27 N17 H17 118.2(12) . . ? C26 N21 C22 118.10(13) . . ? N21 C22 C23 123.18(13) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C22 C23 C24 118.59(14) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? C25 C24 C23 118.07(13) . . ? C25 C24 C27A 119.06(13) . . ? C23 C24 C27A 122.86(14) . . ? C26 C25 C24 119.53(14) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? N21 C26 C25 122.53(14) . . ? N21 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? N27 C27A C24 120.21(14) . . ? N27 C27A H27A 119.9 . . ? C24 C27A H27A 119.9 . . ? C27A N27 N17 115.39(13) . . ? O32 C31 O31 122.90(14) . . ? O32 C31 C32 123.48(14) . . ? O31 C31 C32 113.59(14) . . ? C31 O31 H31 109.6(14) . . ? C31 C32 C33 114.30(13) . . ? C31 C32 H32A 108.7 . . ? C33 C32 H32A 108.7 . . ? C31 C32 H32B 108.7 . . ? C33 C32 H32B 108.7 . . ? H32A C32 H32B 107.6 . . ? C32 C33 C34 111.38(13) . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33B 109.4 . . ? C34 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 C34 C33 111.47(13) . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34B 109.3 . . ? C33 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C36 C35 C34 113.93(13) . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35B 108.8 . . ? C34 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? O37 C36 O36 122.75(14) . . ? O37 C36 C35 124.79(13) . . ? O36 C36 C35 112.46(13) . . ? C36 O36 H36 108.9(13) . . ? 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 C16 N11 C12 C13 0.0(3) . . . . ? N11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C12 C13 C14 C17A 179.42(15) . . . . ? C13 C14 C15 C16 0.4(2) . . . . ? C17A C14 C15 C16 -179.43(15) . . . . ? C12 N11 C16 C15 0.0(3) . . . . ? C14 C15 C16 N11 -0.2(3) . . . . ? C15 C14 C17A O17 5.0(2) . . . . ? C13 C14 C17A O17 -174.75(16) . . . . ? C15 C14 C17A N17 -175.06(15) . . . . ? C13 C14 C17A N17 5.1(2) . . . . ? O17 C17A N17 N27 1.0(2) . . . . ? C14 C17A N17 N27 -178.92(13) . . . . ? C26 N21 C22 C23 -0.2(3) . . . . ? N21 C22 C23 C24 0.8(3) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C22 C23 C24 C27A 178.54(16) . . . . ? C23 C24 C25 C26 -0.2(2) . . . . ? C27A C24 C25 C26 -179.36(16) . . . . ? C22 N21 C26 C25 -0.7(2) . . . . ? C24 C25 C26 N21 0.9(3) . . . . ? C25 C24 C27A N27 177.49(15) . . . . ? C23 C24 C27A N27 -1.6(3) . . . . ? C24 C27A N27 N17 -179.46(14) . . . . ? C17A N17 N27 C27A -176.09(15) . . . . ? O32 C31 C32 C33 28.5(3) . . . . ? O31 C31 C32 C33 -153.35(15) . . . . ? C31 C32 C33 C34 -172.33(15) . . . . ? C32 C33 C34 C35 179.75(14) . . . . ? C33 C34 C35 C36 174.42(14) . . . . ? C34 C35 C36 O37 7.8(2) . . . . ? C34 C35 C36 O36 -171.91(15) . . . . ? 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 N17 H17 O1S 0.860(19) 2.09(2) 2.9376(18) 167.9(17) . O31 H31 N11 0.87(2) 1.77(2) 2.6269(17) 170(2) . O36 H36 N21 0.94(2) 1.69(2) 2.6269(17) 175.6(19) 1_366 O1S H1A O32 0.87(2) 1.97(2) 2.7950(19) 158.6(19) 2_565 O1S H1B O17 0.78(2) 2.13(2) 2.8689(16) 156(2) 1_455 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.307 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.058 #END data_sf0721m(4E) _database_code_depnum_ccdc_archive 'CCDC 853511' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SF40 4-pyridyl-CONH-N=CH-4-pyridyl, octanedioic acid hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C12 H10 N4 O) (C8 H14 O4) (H2 O) ; _chemical_formula_sum 'C20 H26 N4 O6' _chemical_formula_weight 418.45 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 6.918(2) _cell_length_b 11.800(4) _cell_length_c 13.910(5) _cell_angle_alpha 67.522(16) _cell_angle_beta 79.851(16) _cell_angle_gamma 84.973(16) _cell_volume 1032.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6027 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 28.90 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 23107 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 29.57 _reflns_number_total 5306 _reflns_number_gt 2997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0950P)^2^+0.3500P] 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 5306 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.2042 _refine_ls_wR_factor_gt 0.1621 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1S O 1.1346(3) 0.23918(17) 0.53482(17) 0.0556(5) Uani 1 1 d . . . H1A H 1.031(5) 0.269(3) 0.508(2) 0.067 Uiso 1 1 d . . . H1B H 1.102(4) 0.209(3) 0.603(3) 0.067 Uiso 1 1 d . . . N11 N 0.3421(3) 0.71848(17) 0.27345(16) 0.0446(5) Uani 1 1 d . . . C12 C 0.5311(3) 0.7179(2) 0.28214(19) 0.0450(6) Uani 1 1 d . . . H12 H 0.5969 0.7937 0.2539 0.054 Uiso 1 1 calc R . . C13 C 0.6357(3) 0.6113(2) 0.33066(19) 0.0429(6) Uani 1 1 d . . . H13 H 0.7703 0.6148 0.3352 0.052 Uiso 1 1 calc R . . C14 C 0.5420(3) 0.49935(19) 0.37260(17) 0.0361(5) Uani 1 1 d . . . C15 C 0.3455(3) 0.4998(2) 0.3634(2) 0.0461(6) Uani 1 1 d . . . H15 H 0.2757 0.4254 0.3908 0.055 Uiso 1 1 calc R . . C16 C 0.2526(3) 0.6109(2) 0.3134(2) 0.0492(7) Uani 1 1 d . . . H16 H 0.1181 0.6103 0.3073 0.059 Uiso 1 1 calc R . . C17 C 0.6619(3) 0.3857(2) 0.42435(18) 0.0390(5) Uani 1 1 d . . . N17 N 0.5598(3) 0.28046(16) 0.47647(15) 0.0415(5) Uani 1 1 d . . . H17 H 0.434(4) 0.283(2) 0.4861(19) 0.050 Uiso 1 1 d . . . O17 O 0.8398(2) 0.39077(15) 0.41946(14) 0.0518(5) Uani 1 1 d . . . N21 N 0.8021(3) -0.27445(17) 0.73490(16) 0.0442(5) Uani 1 1 d . . . C22 C 0.9187(3) -0.1769(2) 0.6824(2) 0.0440(6) Uani 1 1 d . . . H22 H 1.0566 -0.1892 0.6810 0.053 Uiso 1 1 calc R . . C23 C 0.8473(3) -0.05972(19) 0.63030(18) 0.0409(6) Uani 1 1 d . . . H23 H 0.9343 0.0066 0.5947 0.049 Uiso 1 1 calc R . . C24 C 0.6452(3) -0.04105(19) 0.63118(18) 0.0378(5) Uani 1 1 d . . . C25 C 0.5251(3) -0.1420(2) 0.68536(19) 0.0418(6) Uani 1 1 d . . . H25 H 0.3868 -0.1328 0.6874 0.050 Uiso 1 1 calc R . . C26 C 0.6091(3) -0.2561(2) 0.73641(19) 0.0440(6) Uani 1 1 d . . . H26 H 0.5253 -0.3238 0.7739 0.053 Uiso 1 1 calc R . . C27 C 0.5541(3) 0.0795(2) 0.57743(18) 0.0420(6) Uani 1 1 d . . . H27 H 0.4152 0.0878 0.5821 0.050 Uiso 1 1 calc R . . N27 N 0.6612(3) 0.17325(16) 0.52448(15) 0.0417(5) Uani 1 1 d . . . C31 C 0.0114(3) 0.9536(2) 0.17729(19) 0.0447(6) Uani 1 1 d . . . O31 O 0.1998(2) 0.93469(16) 0.16095(15) 0.0573(6) Uani 1 1 d . . . H31 H 0.236(4) 0.861(3) 0.210(2) 0.069 Uiso 1 1 d . . . O32 O -0.0981(3) 0.87981(18) 0.24648(16) 0.0787(8) Uani 1 1 d . . . C32 C -0.0572(3) 1.0763(2) 0.1048(2) 0.0449(6) Uani 1 1 d . . . H32A H 0.0270 1.0974 0.0352 0.054 Uiso 1 1 calc R . . H32B H -0.0372 1.1390 0.1330 0.054 Uiso 1 1 calc R . . C33 C -0.2711(3) 1.0843(2) 0.08861(19) 0.0418(6) Uani 1 1 d . . . H33A H -0.3564 1.0540 0.1580 0.050 Uiso 1 1 calc R . . H33B H -0.2890 1.0312 0.0505 0.050 Uiso 1 1 calc R . . C34 C -0.3320(3) 1.2164(2) 0.0258(2) 0.0435(6) Uani 1 1 d . . . H34A H -0.3114 1.2691 0.0639 0.052 Uiso 1 1 calc R . . H34B H -0.2460 1.2459 -0.0434 0.052 Uiso 1 1 calc R . . C35 C -0.5452(3) 1.2301(2) 0.00804(19) 0.0422(6) Uani 1 1 d . . . H35A H -0.6311 1.1964 0.0770 0.051 Uiso 1 1 calc R . . H35B H -0.5641 1.1814 -0.0337 0.051 Uiso 1 1 calc R . . C36 C -0.6074(3) 1.3639(2) -0.0494(2) 0.0432(6) Uani 1 1 d . . . H36A H -0.5916 1.4126 -0.0072 0.052 Uiso 1 1 calc R . . H36B H -0.5207 1.3984 -0.1181 0.052 Uiso 1 1 calc R . . C37 C -0.8203(3) 1.3745(2) -0.06783(19) 0.0428(6) Uani 1 1 d . . . H37A H -0.8386 1.3168 -0.1016 0.051 Uiso 1 1 calc R . . H37B H -0.9065 1.3484 0.0014 0.051 Uiso 1 1 calc R . . C38 C -0.8863(3) 1.5017(2) -0.13551(19) 0.0418(6) Uani 1 1 d . . . O38 O -1.0667(2) 1.50227(15) -0.15445(16) 0.0600(6) Uani 1 1 d . . . H38 H -1.101(4) 1.582(3) -0.197(2) 0.072 Uiso 1 1 d . . . O39 O -0.7872(2) 1.59222(14) -0.17037(15) 0.0573(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 O1S 0.0440(9) 0.0484(11) 0.0609(11) -0.0038(9) -0.0109(8) -0.0038(8) N11 0.0477(10) 0.0280(9) 0.0508(11) -0.0063(9) -0.0084(8) -0.0002(8) C12 0.0505(13) 0.0260(10) 0.0516(14) -0.0055(10) -0.0080(10) -0.0072(9) C13 0.0397(11) 0.0296(11) 0.0531(14) -0.0071(10) -0.0075(10) -0.0061(9) C14 0.0400(11) 0.0254(10) 0.0384(11) -0.0073(9) -0.0047(8) -0.0013(8) C15 0.0426(12) 0.0267(10) 0.0600(15) -0.0043(11) -0.0100(10) -0.0057(9) C16 0.0415(12) 0.0310(11) 0.0656(16) -0.0054(11) -0.0131(11) -0.0019(9) C17 0.0424(12) 0.0292(11) 0.0402(12) -0.0073(9) -0.0068(9) 0.0007(9) N17 0.0404(10) 0.0254(9) 0.0500(11) -0.0042(8) -0.0087(8) 0.0016(7) O17 0.0423(9) 0.0369(9) 0.0654(11) -0.0058(8) -0.0119(8) -0.0003(7) N21 0.0473(11) 0.0258(9) 0.0532(12) -0.0063(9) -0.0094(9) -0.0045(7) C22 0.0397(11) 0.0282(11) 0.0575(14) -0.0080(10) -0.0073(10) -0.0042(8) C23 0.0427(11) 0.0246(10) 0.0488(13) -0.0062(10) -0.0043(9) -0.0074(8) C24 0.0430(11) 0.0253(10) 0.0415(11) -0.0083(9) -0.0067(9) -0.0011(8) C25 0.0370(11) 0.0331(11) 0.0504(13) -0.0099(10) -0.0057(9) -0.0051(8) C26 0.0480(12) 0.0263(10) 0.0506(13) -0.0056(10) -0.0056(10) -0.0098(9) C27 0.0427(11) 0.0291(11) 0.0495(13) -0.0093(10) -0.0088(10) 0.0010(9) N27 0.0445(10) 0.0259(9) 0.0479(11) -0.0060(8) -0.0088(8) 0.0016(7) C31 0.0454(12) 0.0312(11) 0.0493(13) -0.0017(10) -0.0127(10) -0.0107(9) O31 0.0493(10) 0.0312(9) 0.0672(12) 0.0056(8) -0.0048(8) 0.0029(7) O32 0.0506(10) 0.0607(12) 0.0794(14) 0.0299(11) -0.0160(9) -0.0179(9) C32 0.0452(12) 0.0275(10) 0.0517(14) -0.0016(10) -0.0088(10) -0.0068(9) C33 0.0401(11) 0.0289(11) 0.0496(13) -0.0056(10) -0.0086(10) -0.0038(9) C34 0.0429(12) 0.0292(11) 0.0516(13) -0.0064(10) -0.0082(10) -0.0041(9) C35 0.0420(11) 0.0274(10) 0.0503(13) -0.0056(10) -0.0096(10) -0.0020(8) C36 0.0423(12) 0.0285(11) 0.0532(14) -0.0073(10) -0.0092(10) -0.0054(9) C37 0.0420(11) 0.0263(10) 0.0500(13) -0.0024(10) -0.0072(10) -0.0048(8) C38 0.0401(11) 0.0289(11) 0.0489(13) -0.0065(10) -0.0049(9) -0.0043(8) O38 0.0481(10) 0.0275(8) 0.0865(14) 0.0049(9) -0.0218(9) -0.0072(7) O39 0.0518(10) 0.0277(8) 0.0784(13) -0.0004(8) -0.0144(9) -0.0115(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 O1S H1A 0.86(3) . ? O1S H1B 0.87(3) . ? N11 C12 1.333(3) . ? N11 C16 1.335(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(3) . ? C14 C17 1.511(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O17 1.227(3) . ? C17 N17 1.361(3) . ? N17 N27 1.379(2) . ? N17 H17 0.86(3) . ? N21 C26 1.331(3) . ? N21 C22 1.350(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 C24 1.395(3) . ? C23 H23 0.9500 . ? C24 C25 1.394(3) . ? C24 C27 1.475(3) . ? C25 C26 1.390(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N27 1.282(3) . ? C27 H27 0.9500 . ? C31 O32 1.215(3) . ? C31 O31 1.297(3) . ? C31 C32 1.506(3) . ? O31 H31 0.93(3) . ? C32 C33 1.525(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.531(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.523(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.534(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.525(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.516(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O39 1.208(3) . ? C38 O38 1.319(3) . ? O38 H38 0.94(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 H1A O1S H1B 108(3) . . ? C12 N11 C16 117.58(19) . . ? N11 C12 C13 122.8(2) . . ? N11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C12 C13 C14 119.5(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 117.73(19) . . ? C15 C14 C17 124.62(19) . . ? C13 C14 C17 117.65(19) . . ? C14 C15 C16 118.8(2) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N11 C16 C15 123.5(2) . . ? N11 C16 H16 118.2 . . ? C15 C16 H16 118.2 . . ? O17 C17 N17 123.30(19) . . ? O17 C17 C14 120.81(19) . . ? N17 C17 C14 115.88(18) . . ? C17 N17 N27 118.67(19) . . ? C17 N17 H17 120.1(17) . . ? N27 N17 H17 120.8(17) . . ? C26 N21 C22 117.84(18) . . ? N21 C22 C23 123.2(2) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C22 C23 C24 118.79(19) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C25 C24 C23 117.88(18) . . ? C25 C24 C27 118.94(19) . . ? C23 C24 C27 123.18(19) . . ? C26 C25 C24 119.5(2) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? N21 C26 C25 122.75(19) . . ? N21 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? N27 C27 C24 120.3(2) . . ? N27 C27 H27 119.8 . . ? C24 C27 H27 119.8 . . ? C27 N27 N17 115.11(19) . . ? O32 C31 O31 122.7(2) . . ? O32 C31 C32 123.5(2) . . ? O31 C31 C32 113.85(18) . . ? C31 O31 H31 110.9(18) . . ? C31 C32 C33 115.66(18) . . ? C31 C32 H32A 108.4 . . ? C33 C32 H32A 108.4 . . ? C31 C32 H32B 108.4 . . ? C33 C32 H32B 108.4 . . ? H32A C32 H32B 107.4 . . ? C32 C33 C34 111.08(18) . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33B 109.4 . . ? C34 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 C34 C33 113.41(18) . . ? C35 C34 H34A 108.9 . . ? C33 C34 H34A 108.9 . . ? C35 C34 H34B 108.9 . . ? C33 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? C34 C35 C36 112.83(19) . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35B 109.0 . . ? C36 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? C37 C36 C35 111.62(18) . . ? C37 C36 H36A 109.3 . . ? C35 C36 H36A 109.3 . . ? C37 C36 H36B 109.3 . . ? C35 C36 H36B 109.3 . . ? H36A C36 H36B 108.0 . . ? C38 C37 C36 114.94(18) . . ? C38 C37 H37A 108.5 . . ? C36 C37 H37A 108.5 . . ? C38 C37 H37B 108.5 . . ? C36 C37 H37B 108.5 . . ? H37A C37 H37B 107.5 . . ? O39 C38 O38 123.1(2) . . ? O39 C38 C37 125.2(2) . . ? O38 C38 C37 111.64(19) . . ? C38 O38 H38 108.8(19) . . ? 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 C16 N11 C12 C13 -0.2(4) . . . . ? N11 C12 C13 C14 -0.1(4) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C12 C13 C14 C17 179.8(2) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C17 C14 C15 C16 -179.7(2) . . . . ? C12 N11 C16 C15 0.3(4) . . . . ? C14 C15 C16 N11 -0.2(4) . . . . ? C15 C14 C17 O17 172.0(3) . . . . ? C13 C14 C17 O17 -7.6(4) . . . . ? C15 C14 C17 N17 -8.8(4) . . . . ? C13 C14 C17 N17 171.7(2) . . . . ? O17 C17 N17 N27 -1.5(4) . . . . ? C14 C17 N17 N27 179.3(2) . . . . ? C26 N21 C22 C23 -0.1(4) . . . . ? N21 C22 C23 C24 -0.5(4) . . . . ? C22 C23 C24 C25 0.4(4) . . . . ? C22 C23 C24 C27 -179.4(2) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C27 C24 C25 C26 -180.0(2) . . . . ? C22 N21 C26 C25 0.9(4) . . . . ? C24 C25 C26 N21 -1.0(4) . . . . ? C25 C24 C27 N27 -178.0(2) . . . . ? C23 C24 C27 N27 1.7(4) . . . . ? C24 C27 N27 N17 179.1(2) . . . . ? C17 N17 N27 C27 175.9(2) . . . . ? O32 C31 C32 C33 -25.3(4) . . . . ? O31 C31 C32 C33 156.3(2) . . . . ? C31 C32 C33 C34 172.5(2) . . . . ? C32 C33 C34 C35 -179.5(2) . . . . ? C33 C34 C35 C36 176.7(2) . . . . ? C34 C35 C36 C37 179.0(2) . . . . ? C35 C36 C37 C38 -173.1(2) . . . . ? C36 C37 C38 O39 -3.2(4) . . . . ? C36 C37 C38 O38 175.4(2) . . . . ? 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 O31 H31 N11 0.93(3) 1.74(3) 2.641(3) 166(3) . O38 H38 N21 0.94(3) 1.74(3) 2.666(3) 172(3) 1_374 O1S H1A O17 0.86(3) 2.05(3) 2.873(3) 161(3) . O1S H1B O32 0.87(3) 1.95(3) 2.795(3) 165(3) 2_666 N17 H17 O1S 0.86(3) 2.11(3) 2.942(3) 165(2) 1_455 _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.373 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.069 #END