# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Lemmerer, Andreas' 'Bernstein, Joel' 'Kahlenberg, Volker' _publ_contact_author_name 'Lemmerer, Andreas' _publ_contact_author_email andreas.lemmerer@wits.ac.za _publ_section_title ; Covalent assistance in supramolecular synthesis: In-situ modification and masking of the hydrogen bonding functionality of the supramolecular reagent isoniazid in co-crystals ; _publ_requested_category FO # Attachment '- 4-12.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-03-20 at 07:32:37 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 9vnp362_p excalibur4 data_4 _database_code_depnum_ccdc_archive 'CCDC 810551' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-03-20T07:32:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(cyclopentylidene)isonicotinohydrazide) .(3-hydroxybenzoic acid) ; _chemical_formula_moiety 'C11 H13 N3 O, C7 H6 O3' _chemical_formula_sum 'C18 H19 N3 O4' _chemical_formula_weight 341.36 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 19.7268(4) _cell_length_b 8.3772(2) _cell_length_c 10.1372(2) _cell_angle_alpha 90 _cell_angle_beta 98.644(2) _cell_angle_gamma 90 _cell_volume 1656.20(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4911 _cell_measurement_theta_min 3.162 _cell_measurement_theta_max 28.5863 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9524 _exptl_absorpt_correction_T_max 0.9902 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_unetI/netI 0.0333 _diffrn_reflns_number 10130 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3073 _reflns_number_gt 2285 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0515P)^2^] 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_number_reflns 3073 _refine_ls_number_parameters 245 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.195 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.29469(6) 0.66684(15) 0.35701(14) 0.0236(3) Uani 1 1 d . . . C2 C 0.25320(6) 0.55452(15) 0.40687(13) 0.0222(3) Uani 1 1 d . . . H2A H 0.2685 0.5035 0.4897 0.027 Uiso 1 1 calc R . . C3 C 0.18948(6) 0.51689(15) 0.33578(14) 0.0225(3) Uani 1 1 d . . . C4 C 0.16853(7) 0.58852(16) 0.21351(14) 0.0278(3) Uani 1 1 d . . . H4 H 0.1255 0.5613 0.1634 0.033 Uiso 1 1 calc R . . C5 C 0.20993(7) 0.69937(17) 0.16404(15) 0.0315(4) Uani 1 1 d . . . H5 H 0.1951 0.7477 0.0799 0.038 Uiso 1 1 calc R . . C6 C 0.27266(7) 0.74075(16) 0.23559(14) 0.0284(3) Uani 1 1 d . . . H6 H 0.3004 0.819 0.202 0.034 Uiso 1 1 calc R . . C7 C 0.36427(7) 0.70320(16) 0.43135(14) 0.0262(3) Uani 1 1 d . . . O1 O 0.38539(5) 0.59885(11) 0.52548(10) 0.0315(3) Uani 1 1 d . . . H1 H 0.4344(9) 0.6210(19) 0.5642(17) 0.047 Uiso 1 1 d . . . O2 O 0.39799(5) 0.81727(12) 0.40576(12) 0.0432(3) Uani 1 1 d . . . O3 O 0.14651(5) 0.40916(12) 0.38080(10) 0.0288(3) Uani 1 1 d . . . H3 H 0.1636(8) 0.3812(19) 0.4619(19) 0.043 Uiso 1 1 d . . . C8 C 0.64515(6) 0.70734(15) 0.76370(13) 0.0208(3) Uani 1 1 d . . . C9 C 0.61549(6) 0.80314(16) 0.65949(14) 0.0241(3) Uani 1 1 d . . . H9 H 0.6398 0.8914 0.631 0.029 Uiso 1 1 calc R . . C10 C 0.55000(6) 0.76813(16) 0.59774(14) 0.0264(3) Uani 1 1 d . . . H10 H 0.53 0.8342 0.5262 0.032 Uiso 1 1 calc R . . C11 C 0.54278(7) 0.55380(17) 0.73367(15) 0.0303(4) Uani 1 1 d . . . H11 H 0.5174 0.4657 0.7594 0.036 Uiso 1 1 calc R . . C12 C 0.60748(7) 0.57941(16) 0.80112(14) 0.0260(3) Uani 1 1 d . . . H12 H 0.6262 0.511 0.8721 0.031 Uiso 1 1 calc R . . C13 C 0.71462(6) 0.73897(15) 0.84181(13) 0.0212(3) Uani 1 1 d . . . C14 C 0.86615(6) 0.92428(16) 0.78291(14) 0.0251(3) Uani 1 1 d DU A . C15 C 0.85812(7) 0.98720(17) 0.64280(14) 0.0285(3) Uani 1 1 d DU A . H15A H 0.8246 1.0759 0.6304 0.034 Uiso 1 1 calc R . . H15B H 0.8427 0.9019 0.5775 0.034 Uiso 1 1 calc R . . C16 C 0.92968(8) 1.0454(3) 0.62722(17) 0.0528(5) Uani 1 1 d DU . . H16A H 0.9553 0.9613 0.5871 0.063 Uiso 0.810(11) 1 calc PR A 1 H16B H 0.9271 1.1416 0.5699 0.063 Uiso 0.810(11) 1 calc PR A 1 H16C H 0.9432 0.9948 0.5468 0.063 Uiso 0.190(11) 1 d PR A 2 H16D H 0.9277 1.1621 0.6117 0.063 Uiso 0.190(11) 1 d PR A 2 C17A C 0.96375(18) 1.0837(5) 0.7664(2) 0.0373(8) Uani 0.810(11) 1 d PDU A 1 H17A H 0.9514 1.1926 0.7924 0.045 Uiso 0.810(11) 1 calc PR A 1 H17B H 1.0142 1.0767 0.7729 0.045 Uiso 0.810(11) 1 calc PR A 1 C17B C 0.9786(4) 1.019(3) 0.7503(9) 0.049(3) Uani 0.190(11) 1 d PDU A 2 H17C H 1.0023 1.1203 0.7798 0.059 Uiso 0.190(11) 1 calc PR A 2 H17D H 1.0135 0.9393 0.7349 0.059 Uiso 0.190(11) 1 calc PR A 2 C18 C 0.93731(7) 0.96053(19) 0.85403(16) 0.0358(4) Uani 1 1 d DU . . H18A H 0.9357 1.0036 0.9445 0.043 Uiso 0.810(11) 1 calc PR A 1 H18B H 0.9664 0.8637 0.8616 0.043 Uiso 0.810(11) 1 calc PR A 1 H18C H 0.9586 0.8651 0.9006 0.043 Uiso 0.190(11) 1 d PR A 2 H18D H 0.9365 1.048 0.9194 0.043 Uiso 0.190(11) 1 d PR A 2 N1 N 0.51354(5) 0.64620(14) 0.63368(12) 0.0273(3) Uani 1 1 d . . . N2 N 0.75844(5) 0.82170(13) 0.77641(12) 0.0225(3) Uani 1 1 d . A . H2 H 0.7509(7) 0.8316(16) 0.6923(16) 0.027 Uiso 1 1 d . . . N3 N 0.82314(5) 0.85431(13) 0.84578(11) 0.0241(3) Uani 1 1 d . . . O4 O 0.72915(5) 0.69647(11) 0.95837(9) 0.0275(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 C1 0.0249(7) 0.0207(7) 0.0258(8) -0.0025(6) 0.0061(6) 0.0038(6) C2 0.0235(7) 0.0243(7) 0.0182(7) -0.0013(6) 0.0015(6) 0.0022(6) C3 0.0235(7) 0.0237(7) 0.0211(8) -0.0024(6) 0.0062(6) 0.0013(6) C4 0.0250(7) 0.0338(8) 0.0228(8) -0.0009(6) -0.0019(6) 0.0010(6) C5 0.0368(8) 0.0339(8) 0.0225(8) 0.0055(6) 0.0004(7) 0.0042(7) C6 0.0331(8) 0.0241(7) 0.0288(9) 0.0024(6) 0.0071(6) 0.0004(6) C7 0.0257(7) 0.0237(7) 0.0297(9) -0.0023(6) 0.0057(6) 0.0006(6) O1 0.0224(5) 0.0370(6) 0.0331(6) 0.0070(5) -0.0021(4) -0.0056(4) O2 0.0356(6) 0.0323(6) 0.0588(8) 0.0101(5) -0.0022(5) -0.0108(5) O3 0.0241(5) 0.0401(6) 0.0212(6) 0.0031(4) 0.0000(4) -0.0073(4) C8 0.0207(7) 0.0221(7) 0.0204(7) -0.0036(6) 0.0058(6) 0.0013(5) C9 0.0214(7) 0.0241(7) 0.0271(8) 0.0008(6) 0.0050(6) -0.0017(6) C10 0.0241(7) 0.0293(7) 0.0253(8) 0.0019(6) 0.0025(6) 0.0018(6) C11 0.0280(7) 0.0307(8) 0.0327(9) 0.0023(7) 0.0061(7) -0.0078(6) C12 0.0278(7) 0.0256(7) 0.0245(8) 0.0035(6) 0.0041(6) -0.0001(6) C13 0.0223(7) 0.0192(7) 0.0221(8) -0.0027(5) 0.0034(6) 0.0023(5) C14 0.0207(7) 0.0314(8) 0.0227(8) -0.0049(6) 0.0021(6) -0.0001(6) C15 0.0240(7) 0.0367(8) 0.0241(8) 0.0000(6) 0.0016(6) -0.0056(6) C16 0.0343(9) 0.0899(14) 0.0336(10) 0.0062(9) 0.0034(7) -0.0240(9) C17A 0.0138(13) 0.0512(17) 0.0450(13) 0.0050(11) -0.0013(9) -0.0038(11) C17B 0.008(3) 0.071(8) 0.068(6) 0.035(6) 0.005(3) 0.017(4) C18 0.0206(7) 0.0573(10) 0.0283(9) -0.0033(7) 0.0003(6) -0.0052(7) N1 0.0227(6) 0.0327(7) 0.0267(7) -0.0025(5) 0.0044(5) -0.0036(5) N2 0.0189(6) 0.0313(6) 0.0163(6) -0.0010(5) -0.0007(5) -0.0026(5) N3 0.0172(6) 0.0325(6) 0.0215(7) -0.0040(5) -0.0006(5) -0.0014(5) O4 0.0259(5) 0.0343(5) 0.0220(6) 0.0037(4) 0.0020(4) 0.0005(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3879(19) . ? C1 C2 1.3911(19) . ? C1 C7 1.4946(18) . ? C2 C3 1.3881(17) . ? C2 H2A 0.95 . ? C3 O3 1.3630(16) . ? C3 C4 1.3832(19) . ? C4 C5 1.380(2) . ? C4 H4 0.95 . ? C5 C6 1.3812(19) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2144(16) . ? C7 O1 1.3148(16) . ? O1 H1 1.004(17) . ? O3 H3 0.873(18) . ? C8 C9 1.3843(18) . ? C8 C12 1.3890(19) . ? C8 C13 1.4997(17) . ? C9 C10 1.3798(18) . ? C9 H9 0.95 . ? C10 N1 1.3312(17) . ? C10 H10 0.95 . ? C11 N1 1.3356(18) . ? C11 C12 1.3711(18) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2261(15) . ? C13 N2 1.3562(17) . ? C14 N3 1.2775(18) . ? C14 C15 1.5009(19) . ? C14 C18 1.5093(18) . ? C15 C16 1.524(2) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17B 1.474(7) . ? C16 C17A 1.503(3) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C16 H16C 0.99 . ? C16 H16D 0.99 . ? C17A C18 1.506(3) . ? C17A H17A 0.99 . ? C17A H17B 0.99 . ? C17B C18 1.507(7) . ? C17B H17C 0.99 . ? C17B H17D 0.99 . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C18 H18C 0.99 . ? C18 H18D 0.99 . ? N2 N3 1.3888(14) . ? N2 H2 0.847(16) . ? 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 C6 C1 C2 120.07(12) . . ? C6 C1 C7 119.85(12) . . ? C2 C1 C7 120.03(12) . . ? C3 C2 C1 120.09(12) . . ? C3 C2 H2A 120 . . ? C1 C2 H2A 120 . . ? O3 C3 C4 118.05(11) . . ? O3 C3 C2 122.47(12) . . ? C4 C3 C2 119.48(12) . . ? C5 C4 C3 120.27(12) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.70(13) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 119.36(13) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O2 C7 O1 123.66(12) . . ? O2 C7 C1 122.93(12) . . ? O1 C7 C1 113.40(12) . . ? C7 O1 H1 110.0(9) . . ? C3 O3 H3 108.8(10) . . ? C9 C8 C12 118.27(12) . . ? C9 C8 C13 123.25(12) . . ? C12 C8 C13 118.43(12) . . ? C10 C9 C8 118.85(13) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N1 C10 C9 123.12(12) . . ? N1 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? N1 C11 C12 123.45(13) . . ? N1 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C8 118.73(13) . . ? C11 C12 H12 120.6 . . ? C8 C12 H12 120.6 . . ? O4 C13 N2 123.06(11) . . ? O4 C13 C8 121.35(12) . . ? N2 C13 C8 115.54(11) . . ? N3 C14 C15 130.51(11) . . ? N3 C14 C18 119.59(12) . . ? C15 C14 C18 109.86(12) . . ? C14 C15 C16 104.05(11) . . ? C14 C15 H15A 110.9 . . ? C16 C15 H15A 110.9 . . ? C14 C15 H15B 110.9 . . ? C16 C15 H15B 110.9 . . ? H15A C15 H15B 109 . . ? C17B C16 C15 111.3(3) . . ? C17A C16 C15 105.17(17) . . ? C17A C16 H16A 110.7 . . ? C15 C16 H16A 110.7 . . ? C17B C16 H16B 125.9 . . ? C17A C16 H16B 110.7 . . ? C15 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C17B C16 H16C 114.3 . . ? C17A C16 H16C 136.6 . . ? C15 C16 H16C 108.4 . . ? C17B C16 H16D 106.6 . . ? C15 C16 H16D 108.5 . . ? H16A C16 H16D 130.4 . . ? H16C C16 H16D 107.5 . . ? C16 C17A C18 105.17(17) . . ? C16 C17A H17A 110.7 . . ? C18 C17A H17A 110.7 . . ? C16 C17A H17B 110.7 . . ? C18 C17A H17B 110.7 . . ? H17A C17A H17B 108.8 . . ? C16 C17B C18 106.6(5) . . ? C16 C17B H17C 110.4 . . ? C18 C17B H17C 110.4 . . ? C16 C17B H17D 110.4 . . ? C18 C17B H17D 110.4 . . ? H17C C17B H17D 108.6 . . ? C17A C18 C14 103.64(15) . . ? C17B C18 C14 107.1(3) . . ? C17A C18 H18A 111 . . ? C17B C18 H18A 128.5 . . ? C14 C18 H18A 111 . . ? C17A C18 H18B 111 . . ? C14 C18 H18B 111 . . ? H18A C18 H18B 109 . . ? C17B C18 H18C 111.2 . . ? C14 C18 H18C 111.3 . . ? C17A C18 H18D 86 . . ? C17B C18 H18D 106.8 . . ? C14 C18 H18D 111.2 . . ? H18C C18 H18D 109.1 . . ? C10 N1 C11 117.58(11) . . ? C13 N2 N3 117.25(11) . . ? C13 N2 H2 120.9(10) . . ? N3 N2 H2 120.0(10) . . ? C14 N3 N2 117.81(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(2) . . . . ? C7 C1 C2 C3 -177.93(12) . . . . ? C1 C2 C3 O3 -179.23(12) . . . . ? C1 C2 C3 C4 1.8(2) . . . . ? O3 C3 C4 C5 179.46(12) . . . . ? C2 C3 C4 C5 -1.5(2) . . . . ? C3 C4 C5 C6 -0.1(2) . . . . ? C4 C5 C6 C1 1.5(2) . . . . ? C2 C1 C6 C5 -1.2(2) . . . . ? C7 C1 C6 C5 176.25(13) . . . . ? C6 C1 C7 O2 15.2(2) . . . . ? C2 C1 C7 O2 -167.30(14) . . . . ? C6 C1 C7 O1 -164.04(12) . . . . ? C2 C1 C7 O1 13.45(19) . . . . ? C12 C8 C9 C10 0.2(2) . . . . ? C13 C8 C9 C10 -177.08(12) . . . . ? C8 C9 C10 N1 0.1(2) . . . . ? N1 C11 C12 C8 -0.4(2) . . . . ? C9 C8 C12 C11 -0.1(2) . . . . ? C13 C8 C12 C11 177.32(12) . . . . ? C9 C8 C13 O4 151.77(13) . . . . ? C12 C8 C13 O4 -25.53(19) . . . . ? C9 C8 C13 N2 -25.97(18) . . . . ? C12 C8 C13 N2 156.73(12) . . . . ? N3 C14 C15 C16 -176.07(16) . . . . ? C18 C14 C15 C16 6.36(17) . . . . ? C14 C15 C16 C17B 0.1(10) . . . . ? C14 C15 C16 C17A -25.5(2) . . . . ? C17B C16 C17A C18 -72.5(9) . . . . ? C15 C16 C17A C18 35.6(3) . . . . ? C17A C16 C17B C18 73.6(9) . . . . ? C15 C16 C17B C18 -6.4(15) . . . . ? C16 C17A C18 C17B 70.5(9) . . . . ? C16 C17A C18 C14 -30.8(3) . . . . ? C16 C17B C18 C17A -75.4(9) . . . . ? C16 C17B C18 C14 10.1(15) . . . . ? N3 C14 C18 C17A -162.9(2) . . . . ? C15 C14 C18 C17A 15.0(2) . . . . ? N3 C14 C18 C17B 171.7(9) . . . . ? C15 C14 C18 C17B -10.4(9) . . . . ? C9 C10 N1 C11 -0.6(2) . . . . ? C12 C11 N1 C10 0.7(2) . . . . ? O4 C13 N2 N3 1.87(18) . . . . ? C8 C13 N2 N3 179.57(10) . . . . ? C15 C14 N3 N2 3.2(2) . . . . ? C18 C14 N3 N2 -179.39(12) . . . . ? C13 N2 N3 C14 176.16(12) . . . . ? 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 O1 H1 N1 1.004(17) 1.628(17) 2.6302(14) 176.0(15) . C10 H10 O2 0.95 2.71 3.3459(16) 125.1 . O3 H3 N3 0.873(18) 1.940(19) 2.7845(15) 162.3(16) 2_646 O3 H3 O4 0.873(18) 2.647(16) 3.2630(13) 128.5(14) 2_646 N2 H2 O4 0.847(16) 2.357(16) 3.1924(15) 168.6(13) 4_575 ###END data_5 _database_code_depnum_ccdc_archive 'CCDC 810552' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-03-31T11:16:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(cyclooctylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) ; _chemical_formula_moiety 'C14 H19 N3 O, C7 H6 O3' _chemical_formula_sum 'C21 H25 N3 O4' _chemical_formula_weight 383.44 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 21.3902(15) _cell_length_b 7.8621(5) _cell_length_c 11.2995(7) _cell_angle_alpha 90 _cell_angle_beta 97.986(3) _cell_angle_gamma 90 _cell_volume 1881.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5790 _cell_measurement_theta_min 3.9498 _cell_measurement_theta_max 67.2544 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.7472 _exptl_absorpt_correction_T_max 0.8606 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_number 11997 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 67.4 _diffrn_reflns_theta_full 67.4 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3383 _reflns_number_gt 2940 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^+0.3434P] 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_number_reflns 3383 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.242 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.32821(7) 0.67004(18) 0.38709(13) 0.0186(3) Uani 1 1 d . . . C2 C 0.28325(7) 0.57109(17) 0.43360(12) 0.0179(3) Uani 1 1 d . . . H2A H 0.2915 0.531 0.5135 0.021 Uiso 1 1 calc R . . C3 C 0.22649(7) 0.53086(17) 0.36372(12) 0.0176(3) Uani 1 1 d . . . C4 C 0.21545(7) 0.58752(18) 0.24587(13) 0.0208(3) Uani 1 1 d . . . H4 H 0.1771 0.5593 0.197 0.025 Uiso 1 1 calc R . . C5 C 0.26054(7) 0.68545(19) 0.19950(13) 0.0219(3) Uani 1 1 d . . . H5 H 0.2529 0.722 0.1187 0.026 Uiso 1 1 calc R . . C6 C 0.31656(7) 0.73037(18) 0.26981(13) 0.0214(3) Uani 1 1 d . . . H6 H 0.3465 0.8009 0.2387 0.026 Uiso 1 1 calc R . . C7 C 0.39028(7) 0.70724(19) 0.46051(13) 0.0209(3) Uani 1 1 d . . . O1 O 0.40283(5) 0.60546(14) 0.55413(9) 0.0243(3) Uani 1 1 d . . . H1 H 0.4498(10) 0.625(3) 0.5998(18) 0.037 Uiso 1 1 d . . . O2 O 0.42578(5) 0.81845(15) 0.43542(11) 0.0311(3) Uani 1 1 d . . . O3 O 0.18071(5) 0.43583(13) 0.40429(9) 0.0215(3) Uani 1 1 d . . . H3 H 0.1933(10) 0.406(3) 0.479(2) 0.032 Uiso 1 1 d . . . C8 C 0.64097(7) 0.70626(17) 0.77575(12) 0.0180(3) Uani 1 1 d . . . C9 C 0.61890(7) 0.7776(2) 0.66539(14) 0.0259(4) Uani 1 1 d . . . H9 H 0.6452 0.8501 0.6265 0.031 Uiso 1 1 calc R . . C10 C 0.55793(7) 0.7413(2) 0.61298(14) 0.0271(4) Uani 1 1 d . . . H10 H 0.5435 0.7884 0.5366 0.032 Uiso 1 1 calc R . . C11 C 0.53985(8) 0.5745(2) 0.77105(15) 0.0267(4) Uani 1 1 d . . . H11 H 0.5122 0.5042 0.8085 0.032 Uiso 1 1 calc R . . C12 C 0.60026(7) 0.6014(2) 0.82860(14) 0.0241(3) Uani 1 1 d . . . H12 H 0.6139 0.5489 0.9034 0.029 Uiso 1 1 calc R . . C13 C 0.70480(7) 0.74321(17) 0.84419(12) 0.0177(3) Uani 1 1 d . . . C14 C 0.83816(7) 0.96824(17) 0.77846(12) 0.0171(3) Uani 1 1 d . . . C15 C 0.81902(7) 1.00804(18) 0.64772(12) 0.0187(3) Uani 1 1 d . . . H15A H 0.7811 1.0816 0.6408 0.022 Uiso 1 1 calc R . . H15B H 0.8063 0.9001 0.6062 0.022 Uiso 1 1 calc R . . C16 C 0.86752(7) 1.09449(18) 0.58022(12) 0.0198(3) Uani 1 1 d . . . H16A H 0.845 1.1651 0.5153 0.024 Uiso 1 1 calc R . . H16B H 0.8941 1.1713 0.6357 0.024 Uiso 1 1 calc R . . C17 C 0.91017(7) 0.9690(2) 0.52649(13) 0.0229(3) Uani 1 1 d . . . H17A H 0.884 0.9016 0.4642 0.027 Uiso 1 1 calc R . . H17B H 0.941 1.0342 0.4868 0.027 Uiso 1 1 calc R . . C18 C 0.94628(7) 0.84694(19) 0.61608(13) 0.0213(3) Uani 1 1 d . . . H18A H 0.9743 0.7758 0.5738 0.026 Uiso 1 1 calc R . . H18B H 0.9157 0.7703 0.6473 0.026 Uiso 1 1 calc R . . C19 C 0.98632(7) 0.93464(18) 0.72201(12) 0.0198(3) Uani 1 1 d . . . H19A H 1.0286 0.8812 0.7344 0.024 Uiso 1 1 calc R . . H19B H 0.9919 1.0555 0.7013 0.024 Uiso 1 1 calc R . . C20 C 0.95842(7) 0.92652(19) 0.83920(12) 0.0204(3) Uani 1 1 d . . . H20A H 0.9916 0.9624 0.9044 0.024 Uiso 1 1 calc R . . H20B H 0.9484 0.8061 0.8541 0.024 Uiso 1 1 calc R . . C21 C 0.89892(7) 1.03274(18) 0.84894(12) 0.0189(3) Uani 1 1 d . . . H21A H 0.8931 1.039 0.9342 0.023 Uiso 1 1 calc R . . H21B H 0.9064 1.15 0.8221 0.023 Uiso 1 1 calc R . . N1 N 0.51842(6) 0.64327(16) 0.66462(11) 0.0229(3) Uani 1 1 d . . . N2 N 0.74479(6) 0.83045(15) 0.78276(11) 0.0184(3) Uani 1 1 d . . . H2 H 0.7348(9) 0.849(2) 0.7103(18) 0.022 Uiso 1 1 d . . . N3 N 0.80232(5) 0.88581(15) 0.84146(10) 0.0176(3) Uani 1 1 d . . . O4 O 0.71845(5) 0.70232(13) 0.94933(9) 0.0214(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 C1 0.0197(7) 0.0171(6) 0.0203(7) -0.0033(5) 0.0074(6) 0.0013(5) C2 0.0212(7) 0.0166(7) 0.0172(7) -0.0012(5) 0.0076(6) 0.0010(5) C3 0.0192(7) 0.0153(7) 0.0199(7) -0.0016(5) 0.0081(6) -0.0003(5) C4 0.0241(7) 0.0210(7) 0.0174(7) -0.0019(5) 0.0037(6) 0.0011(6) C5 0.0287(8) 0.0228(7) 0.0154(7) 0.0004(5) 0.0069(6) 0.0013(6) C6 0.0254(8) 0.0187(7) 0.0225(7) -0.0005(5) 0.0122(6) 0.0009(6) C7 0.0208(7) 0.0202(7) 0.0237(7) -0.0023(5) 0.0096(6) -0.0002(6) O1 0.0199(5) 0.0301(6) 0.0234(5) 0.0029(4) 0.0045(4) -0.0042(4) O2 0.0246(6) 0.0303(6) 0.0385(7) 0.0060(5) 0.0052(5) -0.0091(5) O3 0.0209(5) 0.0251(5) 0.0192(5) 0.0017(4) 0.0047(4) -0.0058(4) C8 0.0185(7) 0.0167(7) 0.0204(7) -0.0026(5) 0.0086(6) 0.0003(5) C9 0.0212(8) 0.0325(8) 0.0249(8) 0.0059(6) 0.0062(6) -0.0042(6) C10 0.0215(8) 0.0358(9) 0.0244(8) 0.0041(6) 0.0051(6) -0.0025(6) C11 0.0225(8) 0.0289(8) 0.0297(8) 0.0027(6) 0.0075(6) -0.0060(6) C12 0.0244(8) 0.0261(8) 0.0228(7) 0.0023(6) 0.0064(6) -0.0038(6) C13 0.0191(7) 0.0153(7) 0.0200(7) -0.0011(5) 0.0077(5) 0.0014(5) C14 0.0182(7) 0.0164(7) 0.0179(7) -0.0020(5) 0.0075(5) 0.0019(5) C15 0.0183(7) 0.0203(7) 0.0180(7) -0.0016(5) 0.0045(5) 0.0005(5) C16 0.0211(7) 0.0221(7) 0.0170(7) 0.0020(5) 0.0050(6) -0.0005(6) C17 0.0219(8) 0.0303(8) 0.0180(7) -0.0006(6) 0.0082(6) 0.0010(6) C18 0.0219(7) 0.0237(7) 0.0197(7) -0.0026(6) 0.0073(6) 0.0013(6) C19 0.0183(7) 0.0217(7) 0.0206(7) -0.0006(5) 0.0068(6) -0.0005(5) C20 0.0198(7) 0.0243(7) 0.0175(7) 0.0004(5) 0.0037(6) -0.0022(6) C21 0.0192(7) 0.0231(7) 0.0156(6) -0.0032(5) 0.0065(5) -0.0037(6) N1 0.0190(6) 0.0257(7) 0.0251(7) -0.0030(5) 0.0071(5) -0.0018(5) N2 0.0161(6) 0.0225(6) 0.0171(6) 0.0004(5) 0.0038(5) -0.0025(5) N3 0.0155(6) 0.0189(6) 0.0192(6) -0.0026(4) 0.0046(5) -0.0016(4) O4 0.0223(5) 0.0227(5) 0.0199(5) 0.0018(4) 0.0058(4) -0.0003(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.395(2) . ? C1 C6 1.397(2) . ? C1 C7 1.493(2) . ? C2 C3 1.390(2) . ? C2 H2A 0.95 . ? C3 O3 1.3609(17) . ? C3 C4 1.393(2) . ? C4 C5 1.392(2) . ? C4 H4 0.95 . ? C5 C6 1.388(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2170(19) . ? C7 O1 1.3238(19) . ? O1 H1 1.08(2) . ? O3 H3 0.88(2) . ? C8 C9 1.389(2) . ? C8 C12 1.393(2) . ? C8 C13 1.501(2) . ? C9 C10 1.385(2) . ? C9 H9 0.95 . ? C10 N1 1.337(2) . ? C10 H10 0.95 . ? C11 N1 1.340(2) . ? C11 C12 1.380(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2262(17) . ? C13 N2 1.3599(18) . ? C14 N3 1.2908(19) . ? C14 C15 1.5100(19) . ? C14 C21 1.5143(19) . ? C15 C16 1.5296(19) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.526(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.525(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.535(2) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 C20 1.5275(19) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C21 1.539(2) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? N2 N3 1.3845(17) . ? N2 H2 0.83(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 C2 C1 C6 120.34(14) . . ? C2 C1 C7 120.40(13) . . ? C6 C1 C7 119.21(13) . . ? C3 C2 C1 120.43(13) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? O3 C3 C2 123.11(12) . . ? O3 C3 C4 117.60(13) . . ? C2 C3 C4 119.28(13) . . ? C5 C4 C3 120.16(14) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.89(13) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.85(13) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? O2 C7 O1 123.82(14) . . ? O2 C7 C1 123.13(14) . . ? O1 C7 C1 113.04(12) . . ? C7 O1 H1 111.6(11) . . ? C3 O3 H3 109.3(13) . . ? C9 C8 C12 117.99(14) . . ? C9 C8 C13 123.77(13) . . ? C12 C8 C13 118.16(13) . . ? C10 C9 C8 118.89(14) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N1 C10 C9 123.17(14) . . ? N1 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? N1 C11 C12 122.86(14) . . ? N1 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C11 C12 C8 119.27(14) . . ? C11 C12 H12 120.4 . . ? C8 C12 H12 120.4 . . ? O4 C13 N2 123.01(13) . . ? O4 C13 C8 121.71(13) . . ? N2 C13 C8 115.23(12) . . ? N3 C14 C15 122.86(13) . . ? N3 C14 C21 114.22(12) . . ? C15 C14 C21 122.78(12) . . ? C14 C15 C16 118.00(12) . . ? C14 C15 H15A 107.8 . . ? C16 C15 H15A 107.8 . . ? C14 C15 H15B 107.8 . . ? C16 C15 H15B 107.8 . . ? H15A C15 H15B 107.1 . . ? C17 C16 C15 113.31(12) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 114.74(12) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 114.27(12) . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 114.47(12) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 117.77(12) . . ? C19 C20 H20A 107.9 . . ? C21 C20 H20A 107.9 . . ? C19 C20 H20B 107.9 . . ? C21 C20 H20B 107.9 . . ? H20A C20 H20B 107.2 . . ? C14 C21 C20 116.01(11) . . ? C14 C21 H21A 108.3 . . ? C20 C21 H21A 108.3 . . ? C14 C21 H21B 108.3 . . ? C20 C21 H21B 108.3 . . ? H21A C21 H21B 107.4 . . ? C10 N1 C11 117.79(13) . . ? C13 N2 N3 119.62(12) . . ? C13 N2 H2 119.9(13) . . ? N3 N2 H2 120.5(13) . . ? C14 N3 N2 116.75(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(2) . . . . ? C7 C1 C2 C3 -177.47(12) . . . . ? C1 C2 C3 O3 -179.59(12) . . . . ? C1 C2 C3 C4 1.3(2) . . . . ? O3 C3 C4 C5 179.90(13) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C4 C5 C6 C1 2.5(2) . . . . ? C2 C1 C6 C5 -2.1(2) . . . . ? C7 C1 C6 C5 175.63(13) . . . . ? C2 C1 C7 O2 -164.71(14) . . . . ? C6 C1 C7 O2 17.6(2) . . . . ? C2 C1 C7 O1 16.19(19) . . . . ? C6 C1 C7 O1 -161.55(13) . . . . ? C12 C8 C9 C10 -0.1(2) . . . . ? C13 C8 C9 C10 -176.70(14) . . . . ? C8 C9 C10 N1 1.5(3) . . . . ? N1 C11 C12 C8 1.0(2) . . . . ? C9 C8 C12 C11 -1.0(2) . . . . ? C13 C8 C12 C11 175.74(13) . . . . ? C9 C8 C13 O4 167.01(14) . . . . ? C12 C8 C13 O4 -9.5(2) . . . . ? C9 C8 C13 N2 -10.4(2) . . . . ? C12 C8 C13 N2 173.00(12) . . . . ? N3 C14 C15 C16 -175.39(13) . . . . ? C21 C14 C15 C16 9.2(2) . . . . ? C14 C15 C16 C17 88.15(15) . . . . ? C15 C16 C17 C18 -56.51(17) . . . . ? C16 C17 C18 C19 -55.16(17) . . . . ? C17 C18 C19 C20 104.56(14) . . . . ? C18 C19 C20 C21 -70.35(16) . . . . ? N3 C14 C21 C20 100.37(14) . . . . ? C15 C14 C21 C20 -83.89(16) . . . . ? C19 C20 C21 C14 72.73(16) . . . . ? C9 C10 N1 C11 -1.5(2) . . . . ? C12 C11 N1 C10 0.2(2) . . . . ? O4 C13 N2 N3 -4.0(2) . . . . ? C8 C13 N2 N3 173.45(11) . . . . ? C15 C14 N3 N2 1.43(19) . . . . ? C21 C14 N3 N2 177.16(11) . . . . ? C13 N2 N3 C14 -179.85(12) . . . . ? 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 O1 H1 N1 1.08(2) 1.55(2) 2.6272(16) 176.9(19) . C10 H10 O2 0.95 2.63 3.2876(19) 126.9 . O3 H3 N3 0.88(2) 2.02(2) 2.8723(16) 161.0(19) 2_646 O3 H3 O4 0.88(2) 2.52(2) 3.1253(15) 126.4(16) 2_646 N2 H2 O4 0.83(2) 2.95(2) 3.7402(16) 160.4(16) 4_575 ###END data_6 _database_code_depnum_ccdc_archive 'CCDC 810553' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-03-31T11:42:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(1-p-tolylethylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) ; _chemical_formula_moiety ' C15 H15 N3 O, C7 H6 O3' _chemical_formula_sum 'C22 H21 N3 O4' _chemical_formula_weight 391.42 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 24.4670(16) _cell_length_b 7.3712(5) _cell_length_c 10.8211(6) _cell_angle_alpha 90 _cell_angle_beta 99.666(6) _cell_angle_gamma 90 _cell_volume 1923.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4773 _cell_measurement_theta_min 3.662 _cell_measurement_theta_max 67.3859 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.775 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.7678 _exptl_absorpt_correction_T_max 0.9265 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0283 _diffrn_reflns_number 11105 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 67.49 _diffrn_reflns_theta_full 67.49 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3452 _reflns_number_gt 2909 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.2000P)^2^] 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_number_reflns 3452 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 0.722 _refine_ls_restrained_S_all 0.722 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.255 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.078 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34361(6) 0.61920(18) 0.30172(12) 0.0279(3) Uani 1 1 d . . . C2 C 0.31094(6) 0.54609(19) 0.19547(12) 0.0272(3) Uani 1 1 d . . . H2A H 0.328 0.4939 0.1313 0.033 Uiso 1 1 calc R . . C3 C 0.25354(6) 0.54929(19) 0.18315(13) 0.0285(3) Uani 1 1 d . . . C4 C 0.22875(6) 0.6308(2) 0.27588(14) 0.0357(4) Uani 1 1 d . . . H4 H 0.1895 0.6351 0.2677 0.043 Uiso 1 1 calc R . . C5 C 0.26165(7) 0.7056(2) 0.38022(15) 0.0389(4) Uani 1 1 d . . . H5 H 0.2446 0.7625 0.4427 0.047 Uiso 1 1 calc R . . C6 C 0.31896(7) 0.69903(19) 0.39511(13) 0.0338(4) Uani 1 1 d . . . H6 H 0.3411 0.7482 0.4679 0.041 Uiso 1 1 calc R . . C7 C 0.40539(6) 0.6153(2) 0.31524(13) 0.0308(3) Uani 1 1 d . . . O1 O 0.42318(4) 0.55752(17) 0.21407(10) 0.0398(3) Uani 1 1 d . . . H1 H 0.4675(10) 0.564(3) 0.221(2) 0.06 Uiso 1 1 d . . . O2 O 0.43592(5) 0.66171(18) 0.41074(10) 0.0460(3) Uani 1 1 d . . . O3 O 0.21964(4) 0.47570(16) 0.08225(9) 0.0351(3) Uani 1 1 d . . . H3 H 0.2401(9) 0.428(3) 0.033(2) 0.053 Uiso 1 1 d . . . C8 C 0.63959(6) 0.63065(18) 0.17889(12) 0.0271(3) Uani 1 1 d . . . C9 C 0.62671(6) 0.5634(2) 0.29003(13) 0.0315(3) Uani 1 1 d . . . H9 H 0.6554 0.5321 0.3572 0.038 Uiso 1 1 calc R . . C10 C 0.57178(6) 0.5421(2) 0.30246(14) 0.0339(4) Uani 1 1 d . . . H10 H 0.5635 0.4932 0.3784 0.041 Uiso 1 1 calc R . . C11 C 0.54202(6) 0.6532(2) 0.10430(15) 0.0371(4) Uani 1 1 d . . . H11 H 0.5125 0.686 0.0394 0.044 Uiso 1 1 calc R . . C12 C 0.59591(6) 0.6747(2) 0.08405(14) 0.0339(3) Uani 1 1 d . . . H12 H 0.6031 0.7192 0.0059 0.041 Uiso 1 1 calc R . . C13 C 0.69706(6) 0.65307(18) 0.15035(12) 0.0275(3) Uani 1 1 d . . . C14 C 0.83119(6) 0.58793(19) 0.31550(14) 0.0291(3) Uani 1 1 d . . . C15 C 0.82178(7) 0.5316(2) 0.44342(15) 0.0409(4) Uani 1 1 d . . . H15A H 0.7909 0.4454 0.4354 0.061 Uiso 1 1 calc R . . H15B H 0.8129 0.6387 0.49 0.061 Uiso 1 1 calc R . . H15C H 0.8554 0.474 0.4885 0.061 Uiso 1 1 calc R . . C16 C 0.88864(6) 0.59456(19) 0.28911(13) 0.0284(3) Uani 1 1 d . . . C17 C 0.89989(6) 0.5737(2) 0.16745(14) 0.0327(4) Uani 1 1 d . . . H17 H 0.8703 0.5556 0.0997 0.039 Uiso 1 1 calc R . . C18 C 0.95404(6) 0.5794(2) 0.14520(14) 0.0339(4) Uani 1 1 d . . . H18 H 0.9609 0.5643 0.062 0.041 Uiso 1 1 calc R . . C19 C 0.99876(6) 0.6068(2) 0.24194(15) 0.0325(3) Uani 1 1 d . . . C20 C 0.98738(6) 0.6290(2) 0.36181(14) 0.0344(4) Uani 1 1 d . . . H20 H 1.017 0.6502 0.4291 0.041 Uiso 1 1 calc R . . C21 C 0.93345(6) 0.6210(2) 0.38572(14) 0.0330(4) Uani 1 1 d . . . H21 H 0.9269 0.6337 0.4694 0.04 Uiso 1 1 calc R . . C22 C 1.05760(6) 0.6094(2) 0.21783(17) 0.0408(4) Uani 1 1 d . . . H22A H 1.0583 0.6571 0.1336 0.061 Uiso 1 1 calc R . . H22B H 1.0726 0.4858 0.2241 0.061 Uiso 1 1 calc R . . H22C H 1.0802 0.6869 0.2801 0.061 Uiso 1 1 calc R . . N1 N 0.52975(5) 0.58792(18) 0.21163(12) 0.0349(3) Uani 1 1 d . . . N2 N 0.73905(5) 0.61981(17) 0.24551(12) 0.0294(3) Uani 1 1 d . . . H2 H 0.7332(7) 0.592(2) 0.3182(18) 0.035 Uiso 1 1 d . . . N3 N 0.79284(5) 0.62835(16) 0.22297(11) 0.0289(3) Uani 1 1 d . . . O4 O 0.70487(4) 0.69506(15) 0.04474(9) 0.0344(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 C1 0.0343(7) 0.0246(7) 0.0262(7) 0.0030(5) 0.0088(6) -0.0028(5) C2 0.0301(7) 0.0280(7) 0.0255(7) 0.0027(5) 0.0102(6) -0.0005(5) C3 0.0291(7) 0.0278(7) 0.0304(7) 0.0068(5) 0.0105(6) -0.0009(5) C4 0.0354(8) 0.0324(8) 0.0438(9) 0.0048(6) 0.0201(7) 0.0006(6) C5 0.0520(9) 0.0303(8) 0.0412(9) -0.0021(6) 0.0274(7) -0.0014(7) C6 0.0479(9) 0.0257(7) 0.0305(7) -0.0015(6) 0.0143(6) -0.0057(6) C7 0.0354(8) 0.0287(7) 0.0278(7) 0.0022(5) 0.0038(6) -0.0042(6) O1 0.0287(6) 0.0562(7) 0.0354(6) -0.0083(5) 0.0078(5) -0.0034(5) O2 0.0427(7) 0.0583(8) 0.0342(6) -0.0058(5) -0.0023(5) -0.0104(6) O3 0.0269(5) 0.0468(6) 0.0321(6) 0.0008(5) 0.0067(4) -0.0030(4) C8 0.0281(7) 0.0239(7) 0.0294(7) -0.0064(5) 0.0052(6) 0.0008(5) C9 0.0294(7) 0.0372(8) 0.0270(7) -0.0026(6) 0.0026(6) 0.0016(6) C10 0.0319(7) 0.0396(8) 0.0311(7) -0.0039(6) 0.0083(6) -0.0031(6) C11 0.0287(8) 0.0426(9) 0.0381(8) 0.0007(7) 0.0002(6) 0.0015(6) C12 0.0313(7) 0.0371(8) 0.0326(7) 0.0035(6) 0.0037(6) 0.0019(6) C13 0.0294(7) 0.0233(7) 0.0296(7) -0.0052(5) 0.0046(6) 0.0022(5) C14 0.0282(7) 0.0263(7) 0.0329(7) 0.0018(5) 0.0057(6) 0.0013(5) C15 0.0322(8) 0.0528(10) 0.0392(8) 0.0143(7) 0.0098(6) 0.0038(7) C16 0.0270(7) 0.0258(7) 0.0328(7) 0.0039(5) 0.0058(6) 0.0018(5) C17 0.0304(7) 0.0367(8) 0.0304(7) 0.0024(6) 0.0035(6) 0.0025(6) C18 0.0333(8) 0.0386(8) 0.0311(7) 0.0030(6) 0.0092(6) 0.0029(6) C19 0.0292(7) 0.0272(7) 0.0417(8) 0.0027(6) 0.0077(6) 0.0013(6) C20 0.0304(8) 0.0345(8) 0.0367(8) 0.0004(6) 0.0015(6) -0.0014(6) C21 0.0331(8) 0.0347(8) 0.0309(7) -0.0001(6) 0.0049(6) 0.0003(6) C22 0.0306(8) 0.0413(9) 0.0517(9) -0.0021(7) 0.0106(7) -0.0002(6) N1 0.0288(6) 0.0380(7) 0.0382(7) -0.0056(5) 0.0065(5) -0.0008(5) N2 0.0254(6) 0.0348(7) 0.0287(6) -0.0002(5) 0.0064(5) 0.0004(5) N3 0.0241(6) 0.0303(6) 0.0325(6) -0.0025(5) 0.0057(5) 0.0006(5) O4 0.0312(5) 0.0443(6) 0.0282(5) -0.0009(4) 0.0066(4) 0.0010(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.391(2) . ? C1 C2 1.394(2) . ? C1 C7 1.494(2) . ? C2 C3 1.3884(19) . ? C2 H2A 0.95 . ? C3 O3 1.3676(18) . ? C3 C4 1.393(2) . ? C4 C5 1.386(2) . ? C4 H4 0.95 . ? C5 C6 1.385(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2181(18) . ? C7 O1 1.3150(18) . ? O1 H1 1.08(2) . ? O3 H3 0.87(2) . ? C8 C9 1.385(2) . ? C8 C12 1.390(2) . ? C8 C13 1.4987(19) . ? C9 C10 1.382(2) . ? C9 H9 0.95 . ? C10 N1 1.341(2) . ? C10 H10 0.95 . ? C11 N1 1.337(2) . ? C11 C12 1.381(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2295(16) . ? C13 N2 1.3492(18) . ? C14 N3 1.2870(19) . ? C14 C16 1.4815(19) . ? C14 C15 1.499(2) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 C21 1.396(2) . ? C16 C17 1.398(2) . ? C17 C18 1.386(2) . ? C17 H17 0.95 . ? C18 C19 1.396(2) . ? C18 H18 0.95 . ? C19 C20 1.381(2) . ? C19 C22 1.506(2) . ? C20 C21 1.388(2) . ? C20 H20 0.95 . ? C21 H21 0.95 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? N2 N3 1.3797(16) . ? N2 H2 0.848(19) . ? 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 C6 C1 C2 120.28(14) . . ? C6 C1 C7 119.45(13) . . ? C2 C1 C7 120.26(12) . . ? C3 C2 C1 120.22(12) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? O3 C3 C2 122.55(12) . . ? O3 C3 C4 117.85(12) . . ? C2 C3 C4 119.60(13) . . ? C5 C4 C3 119.66(14) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 121.25(13) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 118.95(14) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O2 C7 O1 123.76(14) . . ? O2 C7 C1 122.95(13) . . ? O1 C7 C1 113.29(12) . . ? C7 O1 H1 113.2(12) . . ? C3 O3 H3 108.6(14) . . ? C9 C8 C12 117.76(13) . . ? C9 C8 C13 125.20(13) . . ? C12 C8 C13 116.99(12) . . ? C10 C9 C8 119.46(13) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N1 C10 C9 122.60(13) . . ? N1 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? N1 C11 C12 122.59(14) . . ? N1 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C11 C12 C8 119.47(13) . . ? C11 C12 H12 120.3 . . ? C8 C12 H12 120.3 . . ? O4 C13 N2 122.55(13) . . ? O4 C13 C8 121.13(12) . . ? N2 C13 C8 116.30(12) . . ? N3 C14 C16 115.71(12) . . ? N3 C14 C15 125.27(13) . . ? C16 C14 C15 119.00(13) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 117.81(13) . . ? C21 C16 C14 120.77(13) . . ? C17 C16 C14 121.41(13) . . ? C18 C17 C16 120.35(14) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 121.71(13) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C20 C19 C18 117.72(13) . . ? C20 C19 C22 120.69(14) . . ? C18 C19 C22 121.58(14) . . ? C19 C20 C21 121.18(14) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 121.21(13) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C11 N1 C10 118.09(12) . . ? C13 N2 N3 118.91(12) . . ? C13 N2 H2 121.7(12) . . ? N3 N2 H2 119.4(12) . . ? C14 N3 N2 116.39(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.2(2) . . . . ? C7 C1 C2 C3 179.81(12) . . . . ? C1 C2 C3 O3 -178.44(12) . . . . ? C1 C2 C3 C4 1.9(2) . . . . ? O3 C3 C4 C5 179.44(13) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C4 C5 C6 C1 1.5(2) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? C7 C1 C6 C5 178.52(12) . . . . ? C6 C1 C7 O2 8.0(2) . . . . ? C2 C1 C7 O2 -173.01(14) . . . . ? C6 C1 C7 O1 -171.78(13) . . . . ? C2 C1 C7 O1 7.19(18) . . . . ? C12 C8 C9 C10 0.2(2) . . . . ? C13 C8 C9 C10 -177.19(13) . . . . ? C8 C9 C10 N1 -1.5(2) . . . . ? N1 C11 C12 C8 -1.3(2) . . . . ? C9 C8 C12 C11 1.1(2) . . . . ? C13 C8 C12 C11 178.70(13) . . . . ? C9 C8 C13 O4 171.98(14) . . . . ? C12 C8 C13 O4 -5.4(2) . . . . ? C9 C8 C13 N2 -6.3(2) . . . . ? C12 C8 C13 N2 176.33(12) . . . . ? N3 C14 C16 C21 155.94(14) . . . . ? C15 C14 C16 C21 -25.57(19) . . . . ? N3 C14 C16 C17 -24.41(19) . . . . ? C15 C14 C16 C17 154.08(15) . . . . ? C21 C16 C17 C18 0.0(2) . . . . ? C14 C16 C17 C18 -179.63(13) . . . . ? C16 C17 C18 C19 -0.3(2) . . . . ? C17 C18 C19 C20 -0.3(2) . . . . ? C17 C18 C19 C22 178.84(14) . . . . ? C18 C19 C20 C21 1.2(2) . . . . ? C22 C19 C20 C21 -177.91(14) . . . . ? C19 C20 C21 C16 -1.6(2) . . . . ? C17 C16 C21 C20 0.9(2) . . . . ? C14 C16 C21 C20 -179.42(13) . . . . ? C12 C11 N1 C10 0.0(2) . . . . ? C9 C10 N1 C11 1.4(2) . . . . ? O4 C13 N2 N3 -1.8(2) . . . . ? C8 C13 N2 N3 176.42(11) . . . . ? C16 C14 N3 N2 178.94(11) . . . . ? C15 C14 N3 N2 0.6(2) . . . . ? C13 N2 N3 C14 -177.13(12) . . . . ? 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 O1 H1 N1 1.08(2) 1.55(2) 2.6218(16) 171(2) . O3 H3 O4 0.87(2) 1.93(2) 2.7815(15) 168(2) 3_665 N2 H2 O4 0.848(19) 3.084(18) 3.7356(16) 135.4(15) 4_576 ###END data_7 _database_code_depnum_ccdc_archive 'CCDC 810554' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-04-08T09:24:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; bis(N'-(diphenylmethylene)isonicotinohydrazide) . (3-hydroxybenzoic acid) ; _chemical_formula_moiety '2(C19 H15 N3 O), C7 H6 O3' _chemical_formula_sum 'C45 H36 N6 O5' _chemical_formula_weight 740.8 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8338(9) _cell_length_b 10.2475(9) _cell_length_c 10.8863(10) _cell_angle_alpha 104.295(8) _cell_angle_beta 112.784(8) _cell_angle_gamma 103.370(8) _cell_volume 912.17(18) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3220 _cell_measurement_theta_min 4.7429 _cell_measurement_theta_max 62.4606 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.87 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_unetI/netI 0.0181 _diffrn_reflns_number 4365 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 62.65 _diffrn_reflns_theta_full 62.65 _diffrn_measured_fraction_theta_full 0.955 _diffrn_measured_fraction_theta_max 0.955 _reflns_number_total 2793 _reflns_number_gt 2516 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0896P)^2^+0.3716P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.011(2) _refine_ls_number_reflns 2793 _refine_ls_number_parameters 314 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1618 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.209 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.4263(3) 0.4632(2) 0.4412(3) 0.0682(8) Uani 1 1 d D . 1 H2A H 1.4153 0.4428 0.3471 0.082 Uiso 0.5 1 calc PR . 1 C4 C 1.2801(13) 0.4386(7) 0.5832(11) 0.067(4) Uani 0.5 1 d PD A 1 H4 H 1.1894 0.4089 0.5963 0.08 Uiso 0.5 1 calc PR A 1 C5 C 1.4356(5) 0.5149(4) 0.6854(5) 0.0429(9) Uani 0.5 1 d PD A 1 H5 H 1.4532 0.5408 0.7818 0.052 Uiso 0.5 1 calc PR A 1 C6 C 1.5718(4) 0.5605(4) 0.6714(4) 0.0412(8) Uani 0.5 1 d PD . 1 H6 H 1.6697 0.6139 0.7568 0.049 Uiso 0.5 1 calc PR . 1 C7 C 1.2886(3) 0.4168(3) 0.4604(4) 0.0771(9) Uani 1 1 d D A 1 O1 O 1.1491(3) 0.3552(3) 0.3398(3) 0.0913(8) Uani 1 1 d . A 1 H1 H 1.070(5) 0.333(4) 0.359(4) 0.137 Uiso 1 1 d . B 1 O2 O 1.3146(9) 0.4348(6) 0.5970(6) 0.0529(15) Uani 0.5 1 d P C 2 C8 C 0.6317(2) 0.19644(19) 0.43516(19) 0.0427(5) Uani 1 1 d D . . C9A C 0.7869(8) 0.2712(5) 0.5492(8) 0.0592(18) Uani 0.5 1 d PD D 1 H9A H 0.8022 0.2933 0.6447 0.071 Uiso 0.5 1 calc PR D 1 C10A C 0.9200(11) 0.3146(6) 0.5290(11) 0.070(2) Uani 0.5 1 d PD D 1 H10A H 1.0236 0.3644 0.608 0.084 Uiso 0.5 1 calc PR D 1 C11A C 0.7541(11) 0.2127(7) 0.2824(11) 0.0449(16) Uani 0.5 1 d PD D 1 H11A H 0.742 0.1916 0.188 0.054 Uiso 0.5 1 calc PR D 1 C12A C 0.6200(9) 0.1675(6) 0.2989(7) 0.0410(14) Uani 0.5 1 d PD D 1 H12A H 0.5192 0.1162 0.2163 0.049 Uiso 0.5 1 calc PR D 1 C9B C 0.7757(8) 0.2112(5) 0.5331(7) 0.0534(18) Uani 0.5 1 d PD D 2 H9B H 0.7925 0.1941 0.6187 0.064 Uiso 0.5 1 calc PR D 2 C10B C 0.8963(8) 0.2526(6) 0.5004(8) 0.063(2) Uani 0.5 1 d PD D 2 H10B H 0.9972 0.2611 0.569 0.076 Uiso 0.5 1 calc PR D 2 C11B C 0.7442(12) 0.2628(7) 0.2930(12) 0.055(2) Uani 0.5 1 d PD D 2 H11B H 0.7304 0.2786 0.2073 0.066 Uiso 0.5 1 calc PR D 2 C12B C 0.6118(10) 0.2217(6) 0.3120(7) 0.0517(17) Uani 0.5 1 d PD D 2 H12B H 0.5106 0.2112 0.2424 0.062 Uiso 0.5 1 calc PR D 2 C13 C 0.4847(3) 0.1477(2) 0.4512(2) 0.0442(5) Uani 1 1 d . D . C14 C 0.4322(3) 0.1921(2) 0.7583(2) 0.0477(5) Uani 1 1 d . . . C15 C 0.5979(3) 0.2807(2) 0.8756(2) 0.0498(5) Uani 1 1 d . . . C16 C 0.7136(3) 0.2209(2) 0.9088(2) 0.0568(6) Uani 1 1 d . . . H16 H 0.6881 0.1219 0.8564 0.068 Uiso 1 1 calc R . . C17 C 0.8661(3) 0.3040(3) 1.0178(3) 0.0641(7) Uani 1 1 d . . . H17 H 0.9441 0.2613 1.0403 0.077 Uiso 1 1 calc R . . C18 C 0.9055(3) 0.4469(3) 1.0934(3) 0.0685(7) Uani 1 1 d . . . H18 H 1.0106 0.503 1.1679 0.082 Uiso 1 1 calc R . . C19 C 0.7952(4) 0.5086(3) 1.0622(4) 0.0832(9) Uani 1 1 d . . . H19 H 0.8229 0.6081 1.1145 0.1 Uiso 1 1 calc R . . C20 C 0.6420(3) 0.4266(3) 0.9542(3) 0.0761(8) Uani 1 1 d . . . H20 H 0.5652 0.4708 0.9331 0.091 Uiso 1 1 calc R . . C21 C 0.3032(3) 0.1489(2) 0.7957(2) 0.0474(5) Uani 1 1 d . . . C22 C 0.3373(3) 0.1572(3) 0.9343(2) 0.0597(6) Uani 1 1 d . . . H22 H 0.4444 0.1953 1.0075 0.072 Uiso 1 1 calc R . . C23 C 0.2161(3) 0.1102(3) 0.9667(2) 0.0622(7) Uani 1 1 d . . . H23 H 0.2406 0.1163 1.0618 0.075 Uiso 1 1 calc R . . C24 C 0.0603(3) 0.0548(2) 0.8617(2) 0.0576(6) Uani 1 1 d . . . H24 H -0.0225 0.0216 0.884 0.069 Uiso 1 1 calc R . . C25 C 0.0250(3) 0.0476(3) 0.7238(2) 0.0629(7) Uani 1 1 d . . . H25 H -0.0822 0.0099 0.651 0.075 Uiso 1 1 calc R . . C26 C 0.1465(3) 0.0956(2) 0.6918(2) 0.0588(6) Uani 1 1 d . . . H26 H 0.1215 0.0918 0.5972 0.071 Uiso 1 1 calc R . . N1 N 0.8942(2) 0.2821(2) 0.38980(19) 0.0536(5) Uani 1 1 d D . . N2 N 0.5128(2) 0.18927(18) 0.58988(19) 0.0472(5) Uani 1 1 d . . . H2 H 0.608(3) 0.246(3) 0.662(3) 0.057 Uiso 1 1 d . . . N3 N 0.3920(2) 0.14749(17) 0.62273(18) 0.0490(5) Uani 1 1 d . D . O4 O 0.35456(19) 0.07708(16) 0.34775(16) 0.0576(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0797(15) 0.0446(13) 0.130(3) 0.0452(15) 0.0829(17) 0.0344(12) C4 0.036(4) 0.048(4) 0.116(8) 0.021(4) 0.042(4) 0.014(3) C5 0.049(2) 0.048(2) 0.044(2) 0.0239(19) 0.028(2) 0.021(2) C6 0.046(2) 0.043(2) 0.045(2) 0.0214(17) 0.0258(18) 0.0194(17) C7 0.0598(16) 0.0457(13) 0.161(3) 0.0467(16) 0.075(2) 0.0284(12) O1 0.0791(14) 0.1143(17) 0.155(2) 0.0905(16) 0.0896(16) 0.0552(13) O2 0.041(3) 0.064(3) 0.069(3) 0.018(3) 0.046(3) 0.018(2) C8 0.0703(13) 0.0364(10) 0.0418(10) 0.0208(8) 0.0383(10) 0.0259(9) C9A 0.081(4) 0.058(4) 0.042(3) 0.021(3) 0.038(3) 0.015(3) C10A 0.074(4) 0.071(5) 0.050(3) 0.015(4) 0.034(3) 0.001(4) C11A 0.060(3) 0.047(4) 0.035(3) 0.014(3) 0.030(2) 0.019(3) C12A 0.055(3) 0.039(3) 0.041(2) 0.020(3) 0.031(2) 0.018(3) C9B 0.084(4) 0.062(4) 0.058(4) 0.049(4) 0.049(3) 0.046(4) C10B 0.064(4) 0.096(6) 0.061(5) 0.054(5) 0.036(4) 0.046(5) C11B 0.075(4) 0.060(5) 0.046(4) 0.025(4) 0.041(3) 0.023(4) C12B 0.067(3) 0.053(4) 0.042(3) 0.022(3) 0.034(2) 0.017(4) C13 0.0742(14) 0.0343(10) 0.0457(11) 0.0225(9) 0.0414(11) 0.0245(10) C14 0.0798(15) 0.0429(11) 0.0524(12) 0.0280(9) 0.0492(11) 0.0330(10) C15 0.0781(14) 0.0500(12) 0.0519(12) 0.0264(10) 0.0512(11) 0.0306(11) C16 0.0872(17) 0.0551(13) 0.0517(12) 0.0267(10) 0.0450(12) 0.0367(12) C17 0.0819(17) 0.0719(16) 0.0634(14) 0.0346(13) 0.0484(13) 0.0350(13) C18 0.0804(17) 0.0667(15) 0.0792(17) 0.0294(13) 0.0608(15) 0.0187(13) C19 0.089(2) 0.0515(14) 0.116(2) 0.0140(15) 0.0699(19) 0.0169(14) C20 0.0836(18) 0.0540(14) 0.112(2) 0.0232(14) 0.0684(17) 0.0306(13) C21 0.0749(14) 0.0427(11) 0.0492(11) 0.0246(9) 0.0444(11) 0.0281(10) C22 0.0744(15) 0.0872(17) 0.0568(13) 0.0454(12) 0.0474(12) 0.0463(13) C23 0.0763(16) 0.0915(18) 0.0543(13) 0.0454(13) 0.0474(12) 0.0415(14) C24 0.0756(15) 0.0573(13) 0.0574(13) 0.0271(11) 0.0472(12) 0.0197(11) C25 0.0742(15) 0.0589(14) 0.0447(12) 0.0145(10) 0.0339(11) 0.0009(11) C26 0.0812(16) 0.0516(13) 0.0419(11) 0.0151(10) 0.0383(12) 0.0077(11) N1 0.0679(12) 0.0649(12) 0.0555(11) 0.0332(9) 0.0423(10) 0.0356(10) N2 0.0753(12) 0.0438(9) 0.0462(10) 0.0238(8) 0.0452(9) 0.0249(9) N3 0.0835(13) 0.0403(9) 0.0557(10) 0.0291(8) 0.0529(10) 0.0298(9) O4 0.0745(11) 0.0523(9) 0.0501(9) 0.0185(7) 0.0397(9) 0.0128(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C1 1.374(6) 2_866 ? C1 C7 1.440(3) . ? C1 H2A 0.95 . ? C4 C7 1.338(9) . ? C4 C5 1.374(9) . ? C4 H4 0.95 . ? C5 C6 1.393(5) . ? C5 H5 0.95 . ? C6 C1 1.198(5) 2_866 ? C6 H6 0.95 . ? C7 O1 1.341(4) . ? O1 H1 0.87(5) . ? C8 C9B 1.348(7) . ? C8 C12B 1.376(6) . ? C8 C12A 1.392(6) . ? C8 C9A 1.407(7) . ? C8 C13 1.509(3) . ? C9A C10A 1.401(8) . ? C9A H9A 0.95 . ? C10A N1 1.373(10) . ? C10A H10A 0.95 . ? C11A N1 1.288(10) . ? C11A C12A 1.388(7) . ? C11A H11A 0.95 . ? C12A H12A 0.95 . ? C9B C10B 1.372(7) . ? C9B H9B 0.95 . ? C10B N1 1.306(9) . ? C10B H10B 0.95 . ? C11B N1 1.372(11) . ? C11B C12B 1.383(8) . ? C11B H11B 0.95 . ? C12B H12B 0.95 . ? C13 O4 1.218(3) . ? C13 N2 1.357(3) . ? C14 N3 1.294(3) . ? C14 C21 1.483(3) . ? C14 C15 1.497(3) . ? C15 C16 1.384(3) . ? C15 C20 1.392(3) . ? C16 C17 1.384(3) . ? C16 H16 0.95 . ? C17 C18 1.367(4) . ? C17 H17 0.95 . ? C18 C19 1.353(4) . ? C18 H18 0.95 . ? C19 C20 1.383(4) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 C26 1.382(3) . ? C21 C22 1.389(3) . ? C22 C23 1.385(3) . ? C22 H22 0.95 . ? C23 C24 1.377(3) . ? C23 H23 0.95 . ? C24 C25 1.382(3) . ? C24 H24 0.95 . ? C25 C26 1.387(3) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? N2 N3 1.376(2) . ? N2 H2 0.89(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 C1 C1 C7 120.1(4) 2_866 . ? C1 C1 H2A 120 2_866 . ? C7 C1 H2A 120 . . ? C7 C4 C5 102.4(8) . . ? C7 C4 H4 128.8 . . ? C5 C4 H4 128.8 . . ? C4 C5 C6 130.8(6) . . ? C4 C5 H5 114.6 . . ? C6 C5 H5 114.6 . . ? C1 C6 C5 124.3(4) 2_866 . ? C1 C6 H6 117.8 2_866 . ? C5 C6 H6 117.8 . . ? C4 C7 O1 115.5(5) . . ? C4 C7 C1 128.5(6) . . ? O1 C7 C1 115.7(3) . . ? C7 O1 H1 111(3) . . ? C9B C8 C12B 120.7(5) . . ? C12A C8 C9A 114.6(5) . . ? C9B C8 C13 122.6(4) . . ? C12B C8 C13 116.7(4) . . ? C12A C8 C13 120.0(4) . . ? C9A C8 C13 125.4(4) . . ? C10A C9A C8 123.3(7) . . ? C10A C9A H9A 118.3 . . ? C8 C9A H9A 118.3 . . ? N1 C10A C9A 117.0(7) . . ? N1 C10A H10A 121.5 . . ? C9A C10A H10A 121.5 . . ? N1 C11A C12A 122.8(8) . . ? N1 C11A H11A 118.6 . . ? C12A C11A H11A 118.6 . . ? C11A C12A C8 120.7(7) . . ? C11A C12A H12A 119.7 . . ? C8 C12A H12A 119.7 . . ? C8 C9B C10B 115.3(6) . . ? C8 C9B H9B 122.3 . . ? C10B C9B H9B 122.3 . . ? N1 C10B C9B 130.1(6) . . ? N1 C10B H10B 115 . . ? C9B C10B H10B 115 . . ? N1 C11B C12B 124.3(9) . . ? N1 C11B H11B 117.8 . . ? C12B C11B H11B 117.8 . . ? C8 C12B C11B 117.7(8) . . ? C8 C12B H12B 121.1 . . ? C11B C12B H12B 121.1 . . ? O4 C13 N2 124.40(19) . . ? O4 C13 C8 121.99(17) . . ? N2 C13 C8 113.61(19) . . ? N3 C14 C21 116.3(2) . . ? N3 C14 C15 124.15(18) . . ? C21 C14 C15 119.57(17) . . ? C16 C15 C20 117.4(2) . . ? C16 C15 C14 121.19(19) . . ? C20 C15 C14 121.4(2) . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 120.1(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 119.9(3) . . ? C18 C19 H19 120 . . ? C20 C19 H19 120 . . ? C19 C20 C15 121.4(3) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C26 C21 C22 118.7(2) . . ? C26 C21 C14 120.40(18) . . ? C22 C21 C14 120.9(2) . . ? C23 C22 C21 120.5(2) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.6(2) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 119.9(2) . . ? C24 C25 H25 120 . . ? C26 C25 H25 120 . . ? C21 C26 C25 120.9(2) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C10B N1 C11B 111.8(5) . . ? C11A N1 C10A 121.5(6) . . ? C13 N2 N3 120.6(2) . . ? C13 N2 H2 121.7(16) . . ? N3 N2 H2 117.7(16) . . ? C14 N3 N2 115.51(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 C7 C4 C5 C6 -0.1(2) . . . . ? C4 C5 C6 C1 -0.8(4) . . . 2_866 ? C5 C4 C7 O1 -173.9(2) . . . . ? C5 C4 C7 C1 -0.6(3) . . . . ? C1 C1 C7 C4 2.0(3) 2_866 . . . ? C1 C1 C7 O1 175.3(2) 2_866 . . . ? C9B C8 C9A C10A 88.6(16) . . . . ? C12B C8 C9A C10A -25.5(3) . . . . ? C12A C8 C9A C10A 0.5(2) . . . . ? C13 C8 C9A C10A -179.8(2) . . . . ? C8 C9A C10A N1 0.4(2) . . . . ? N1 C11A C12A C8 0.3(7) . . . . ? C9B C8 C12A C11A -26.4(5) . . . . ? C12B C8 C12A C11A 91.0(16) . . . . ? C9A C8 C12A C11A -0.8(5) . . . . ? C13 C8 C12A C11A 179.4(3) . . . . ? C12B C8 C9B C10B 0.2(2) . . . . ? C12A C8 C9B C10B 24.9(3) . . . . ? C9A C8 C9B C10B -77.2(15) . . . . ? C13 C8 C9B C10B 178.3(2) . . . . ? C8 C9B C10B N1 1.1(3) . . . . ? C9B C8 C12B C11B -0.2(5) . . . . ? C12A C8 C12B C11B -73.9(16) . . . . ? C9A C8 C12B C11B 25.0(5) . . . . ? C13 C8 C12B C11B -178.3(3) . . . . ? N1 C11B C12B C8 -1.0(7) . . . . ? C9B C8 C13 O4 -147.9(3) . . . . ? C12B C8 C13 O4 30.2(3) . . . . ? C12A C8 C13 O4 3.4(3) . . . . ? C9A C8 C13 O4 -176.3(3) . . . . ? C9B C8 C13 N2 31.7(3) . . . . ? C12B C8 C13 N2 -150.2(3) . . . . ? C12A C8 C13 N2 -177.0(2) . . . . ? C9A C8 C13 N2 3.3(3) . . . . ? N3 C14 C15 C16 -71.4(3) . . . . ? C21 C14 C15 C16 107.7(2) . . . . ? N3 C14 C15 C20 107.8(2) . . . . ? C21 C14 C15 C20 -73.1(3) . . . . ? C20 C15 C16 C17 1.0(3) . . . . ? C14 C15 C16 C17 -179.84(18) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C17 C18 C19 C20 0.4(4) . . . . ? C18 C19 C20 C15 -0.1(4) . . . . ? C16 C15 C20 C19 -0.6(4) . . . . ? C14 C15 C20 C19 -179.8(2) . . . . ? N3 C14 C21 C26 -15.1(3) . . . . ? C15 C14 C21 C26 165.77(19) . . . . ? N3 C14 C21 C22 163.03(19) . . . . ? C15 C14 C21 C22 -16.1(3) . . . . ? C26 C21 C22 C23 1.2(3) . . . . ? C14 C21 C22 C23 -177.0(2) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C22 C23 C24 C25 -0.7(4) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C22 C21 C26 C25 -1.7(3) . . . . ? C14 C21 C26 C25 176.5(2) . . . . ? C24 C25 C26 C21 0.9(4) . . . . ? C12A C11A N1 C10B 24.2(6) . . . . ? C12A C11A N1 C11B -77.8(18) . . . . ? C12A C11A N1 C10A 0.8(7) . . . . ? C9B C10B N1 C11A -26.4(5) . . . . ? C9B C10B N1 C11B -2.1(5) . . . . ? C9B C10B N1 C10A 99.5(15) . . . . ? C12B C11B N1 C11A 88.6(19) . . . . ? C12B C11B N1 C10B 2.0(6) . . . . ? C12B C11B N1 C10A -24.7(6) . . . . ? C9A C10A N1 C11A -1.1(5) . . . . ? C9A C10A N1 C10B -65.3(14) . . . . ? C9A C10A N1 C11B 23.8(4) . . . . ? O4 C13 N2 N3 2.6(3) . . . . ? C8 C13 N2 N3 -176.95(15) . . . . ? C21 C14 N3 N2 179.60(15) . . . . ? C15 C14 N3 N2 -1.3(3) . . . . ? C13 N2 N3 C14 179.43(16) . . . . ? 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 O1 H1 N1 0.87(5) 1.87(5) 2.744(3) 177(4) . C10A H10A O2 0.95 2.84 3.498(11) 127 . ###END data_8 _database_code_depnum_ccdc_archive 'CCDC 810555' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-03-20T11:16:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(propan-2-ylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) . (H2O) ; _chemical_formula_moiety 'C9 H11 N3 O, C7 H6 O3, H2 O' _chemical_formula_sum 'C16 H19 N3 O5' _chemical_formula_weight 333.34 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3511(6) _cell_length_b 10.5853(8) _cell_length_c 12.8026(12) _cell_angle_alpha 75.694(7) _cell_angle_beta 78.613(8) _cell_angle_gamma 81.087(7) _cell_volume 812.47(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2216 _cell_measurement_theta_min 3.2901 _cell_measurement_theta_max 28.485 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.99295 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_unetI/netI 0.0569 _diffrn_reflns_number 5230 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 2990 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0378P)^2^] 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_number_reflns 2990 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 0.832 _refine_ls_restrained_S_all 0.832 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.134 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.3196(2) -0.02326(14) 0.22633(13) 0.0259(4) Uani 1 1 d . . . C2 C 1.2083(2) -0.11915(14) 0.21193(13) 0.0256(4) Uani 1 1 d . . . H2A H 1.0617 -0.1249 0.2456 0.031 Uiso 1 1 calc R . . C3 C 1.3117(2) -0.20625(14) 0.14842(13) 0.0270(4) Uani 1 1 d . . . C4 C 1.5233(2) -0.19508(15) 0.09697(14) 0.0331(4) Uani 1 1 d . . . H4 H 1.593 -0.2535 0.0519 0.04 Uiso 1 1 calc R . . C5 C 1.6334(3) -0.09934(15) 0.11098(15) 0.0371(4) Uani 1 1 d . . . H5 H 1.7787 -0.0922 0.0755 0.044 Uiso 1 1 calc R . . C6 C 1.5334(2) -0.01417(15) 0.17617(15) 0.0347(4) Uani 1 1 d . . . H6 H 1.6103 0.0505 0.1868 0.042 Uiso 1 1 calc R . . C7 C 1.2146(3) 0.06814(14) 0.29714(14) 0.0307(4) Uani 1 1 d . . . O1 O 1.00833(17) 0.06027(10) 0.33273(10) 0.0400(3) Uani 1 1 d . . . H1 H 0.941(3) 0.1212(17) 0.3829(16) 0.06 Uiso 1 1 d . . . O2 O 1.31432(17) 0.14517(10) 0.31949(10) 0.0432(3) Uani 1 1 d . . . O3 O 1.21384(18) -0.30610(11) 0.13511(11) 0.0403(3) Uani 1 1 d . . . H3 H 1.101(3) -0.3208(18) 0.1869(17) 0.06 Uiso 1 1 d . . . C8 C 0.4694(2) 0.32636(13) 0.60208(13) 0.0221(3) Uani 1 1 d . . . C9 C 0.6745(2) 0.36546(14) 0.57327(13) 0.0253(4) Uani 1 1 d . . . H9 H 0.7093 0.4343 0.6002 0.03 Uiso 1 1 calc R . . C10 C 0.8282(2) 0.30329(14) 0.50497(13) 0.0295(4) Uani 1 1 d . . . H10 H 0.9693 0.3302 0.4867 0.035 Uiso 1 1 calc R . . C11 C 0.5896(3) 0.17112(15) 0.49126(15) 0.0337(4) Uani 1 1 d . . . H11 H 0.558 0.1036 0.4617 0.04 Uiso 1 1 calc R . . C12 C 0.4286(2) 0.22568(14) 0.55998(14) 0.0318(4) Uani 1 1 d . . . H12 H 0.2902 0.1949 0.5787 0.038 Uiso 1 1 calc R . . C13 C 0.2866(2) 0.38595(14) 0.67483(13) 0.0246(4) Uani 1 1 d . . . C14 C 0.1735(2) 0.60099(14) 0.84875(13) 0.0263(4) Uani 1 1 d . . . C15 C 0.3824(2) 0.60819(17) 0.88204(15) 0.0404(5) Uani 1 1 d . . . H15A H 0.4815 0.5297 0.8724 0.061 Uiso 1 1 calc R . . H15B H 0.3569 0.6133 0.959 0.061 Uiso 1 1 calc R . . H15C H 0.4463 0.6864 0.8366 0.061 Uiso 1 1 calc R . . C16 C -0.0228(2) 0.67085(16) 0.90411(15) 0.0386(4) Uani 1 1 d . . . H16A H -0.151 0.6564 0.8787 0.058 Uiso 1 1 calc R . . H16B H -0.009 0.765 0.8866 0.058 Uiso 1 1 calc R . . H16C H -0.0372 0.637 0.9834 0.058 Uiso 1 1 calc R . . N1 N 0.7891(2) 0.20745(12) 0.46332(11) 0.0299(3) Uani 1 1 d . . . N2 N 0.3249(2) 0.47785(11) 0.72242(11) 0.0243(3) Uani 1 1 d . . . H2 H 0.451(2) 0.5045(14) 0.7142(13) 0.029 Uiso 1 1 d . . . N3 N 0.14436(18) 0.54067(12) 0.77871(11) 0.0279(3) Uani 1 1 d . . . O4 O 0.10582(15) 0.34965(10) 0.68881(10) 0.0351(3) Uani 1 1 d . . . O1W O 0.74327(17) 0.59111(11) 0.67752(10) 0.0314(3) Uani 1 1 d . . . H1W H 0.862(3) 0.5603(16) 0.7040(15) 0.047 Uiso 1 1 d . . . H2W H 0.726(3) 0.6740(17) 0.6763(15) 0.047 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0287(9) 0.0225(8) 0.0264(10) -0.0064(7) -0.0051(7) -0.0006(7) C2 0.0231(8) 0.0285(8) 0.0241(10) -0.0090(7) -0.0007(7) 0.0011(7) C3 0.0300(9) 0.0268(8) 0.0243(10) -0.0092(8) -0.0009(8) -0.0025(7) C4 0.0345(9) 0.0330(9) 0.0289(11) -0.0115(8) 0.0025(8) 0.0022(7) C5 0.0276(9) 0.0389(10) 0.0405(12) -0.0083(9) 0.0038(8) -0.0040(8) C6 0.0320(10) 0.0302(9) 0.0413(12) -0.0075(9) -0.0025(8) -0.0073(7) C7 0.0361(10) 0.0257(8) 0.0323(11) -0.0077(8) -0.0101(8) -0.0017(8) O1 0.0356(7) 0.0421(7) 0.0484(9) -0.0306(6) 0.0050(6) -0.0047(5) O2 0.0455(7) 0.0345(6) 0.0591(10) -0.0247(6) -0.0135(7) -0.0042(6) O3 0.0407(7) 0.0422(7) 0.0431(9) -0.0274(6) 0.0099(6) -0.0131(6) C8 0.0229(8) 0.0225(8) 0.0209(9) -0.0052(7) -0.0050(7) -0.0005(6) C9 0.0261(8) 0.0257(8) 0.0265(10) -0.0114(8) -0.0024(7) -0.0035(7) C10 0.0271(8) 0.0323(9) 0.0303(11) -0.0117(8) 0.0008(8) -0.0060(7) C11 0.0396(10) 0.0284(9) 0.0400(12) -0.0176(8) -0.0102(9) -0.0038(8) C12 0.0269(9) 0.0321(9) 0.0416(12) -0.0168(9) -0.0064(8) -0.0041(7) C13 0.0228(8) 0.0265(8) 0.0260(10) -0.0072(7) -0.0056(7) -0.0034(7) C14 0.0263(8) 0.0276(8) 0.0244(10) -0.0075(8) -0.0006(7) -0.0032(7) C15 0.0322(9) 0.0573(11) 0.0389(12) -0.0274(10) -0.0021(8) -0.0043(8) C16 0.0325(9) 0.0480(10) 0.0375(12) -0.0229(9) -0.0015(8) 0.0046(8) N1 0.0328(8) 0.0287(7) 0.0291(9) -0.0124(7) -0.0027(7) 0.0010(6) N2 0.0166(6) 0.0297(7) 0.0290(9) -0.0137(6) 0.0003(6) -0.0030(5) N3 0.0220(7) 0.0337(7) 0.0297(9) -0.0155(7) 0.0000(6) 0.0002(6) O4 0.0217(6) 0.0425(7) 0.0470(8) -0.0229(6) 0.0009(5) -0.0092(5) O1W 0.0253(6) 0.0284(6) 0.0446(8) -0.0166(6) -0.0042(5) -0.0034(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3892(19) . ? C1 C6 1.390(2) . ? C1 C7 1.482(2) . ? C2 C3 1.384(2) . ? C2 H2A 0.95 . ? C3 O3 1.3664(17) . ? C3 C4 1.384(2) . ? C4 C5 1.381(2) . ? C4 H4 0.95 . ? C5 C6 1.378(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2227(16) . ? C7 O1 1.3077(18) . ? O1 H1 1.011(19) . ? O3 H3 0.88(2) . ? C8 C9 1.3809(19) . ? C8 C12 1.3851(18) . ? C8 C13 1.500(2) . ? C9 C10 1.378(2) . ? C9 H9 0.95 . ? C10 N1 1.3315(17) . ? C10 H10 0.95 . ? C11 N1 1.3361(19) . ? C11 C12 1.366(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2326(16) . ? C13 N2 1.3423(17) . ? C14 N3 1.2772(18) . ? C14 C15 1.489(2) . ? C14 C16 1.493(2) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? N2 N3 1.3967(16) . ? N2 H2 0.866(14) . ? O1W H1W 0.874(18) . ? O1W H2W 0.864(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.03(13) . . ? C2 C1 C7 120.75(13) . . ? C6 C1 C7 119.21(13) . . ? C3 C2 C1 119.78(13) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? O3 C3 C4 117.63(13) . . ? O3 C3 C2 122.46(13) . . ? C4 C3 C2 119.91(13) . . ? C5 C4 C3 120.23(14) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.26(15) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 119.77(14) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O1 123.05(14) . . ? O2 C7 C1 122.12(14) . . ? O1 C7 C1 114.83(12) . . ? C7 O1 H1 113.6(9) . . ? C3 O3 H3 109.7(11) . . ? C9 C8 C12 117.72(14) . . ? C9 C8 C13 124.74(12) . . ? C12 C8 C13 117.53(12) . . ? C10 C9 C8 119.13(12) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N1 C10 C9 123.38(14) . . ? N1 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N1 C11 C12 123.65(13) . . ? N1 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C8 119.21(14) . . ? C11 C12 H12 120.4 . . ? C8 C12 H12 120.4 . . ? O4 C13 N2 121.98(14) . . ? O4 C13 C8 119.18(12) . . ? N2 C13 C8 118.84(12) . . ? N3 C14 C15 126.99(14) . . ? N3 C14 C16 116.67(12) . . ? C15 C14 C16 116.34(12) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C10 N1 C11 116.90(13) . . ? C13 N2 N3 116.24(11) . . ? C13 N2 H2 123.6(10) . . ? N3 N2 H2 119.8(10) . . ? C14 N3 N2 118.40(11) . . ? H1W O1W H2W 105.6(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.6(2) . . . . ? C7 C1 C2 C3 -177.83(15) . . . . ? C1 C2 C3 O3 177.10(15) . . . . ? C1 C2 C3 C4 -1.9(2) . . . . ? O3 C3 C4 C5 -177.42(16) . . . . ? C2 C3 C4 C5 1.6(2) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C1 -1.2(3) . . . . ? C2 C1 C6 C5 0.9(2) . . . . ? C7 C1 C6 C5 179.40(16) . . . . ? C2 C1 C7 O2 173.00(15) . . . . ? C6 C1 C7 O2 -5.5(2) . . . . ? C2 C1 C7 O1 -7.4(2) . . . . ? C6 C1 C7 O1 174.07(15) . . . . ? C12 C8 C9 C10 -0.2(2) . . . . ? C13 C8 C9 C10 -179.51(15) . . . . ? C8 C9 C10 N1 0.9(2) . . . . ? N1 C11 C12 C8 1.5(3) . . . . ? C9 C8 C12 C11 -1.0(2) . . . . ? C13 C8 C12 C11 178.43(15) . . . . ? C9 C8 C13 O4 174.83(15) . . . . ? C12 C8 C13 O4 -4.5(2) . . . . ? C9 C8 C13 N2 -4.9(2) . . . . ? C12 C8 C13 N2 175.78(15) . . . . ? C9 C10 N1 C11 -0.5(2) . . . . ? C12 C11 N1 C10 -0.7(2) . . . . ? O4 C13 N2 N3 -6.9(2) . . . . ? C8 C13 N2 N3 172.76(13) . . . . ? C15 C14 N3 N2 -2.8(2) . . . . ? C16 C14 N3 N2 177.85(14) . . . . ? C13 N2 N3 C14 161.29(14) . . . . ? 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 O1 H1 N1 1.011(19) 1.620(19) 2.6185(15) 168.7(15) . C10 H10 O2 0.95 3.48 3.9293(19) 111.6 . O3 H3 O4 0.88(2) 1.85(2) 2.7176(17) 170.6(18) 2_656 N2 H2 O1W 0.866(14) 2.118(15) 2.9783(16) 172.2(15) . O1W H1W N3 0.874(18) 2.152(18) 2.9986(16) 163.2(14) 1_655 O1W H1W O4 0.874(18) 2.535(17) 3.1592(16) 129.1(13) 1_655 O1W H2W O2 0.864(17) 1.904(18) 2.7674(15) 177.5(17) 2_766 ###END data_9 _database_code_depnum_ccdc_archive 'CCDC 810556' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-04-04T09:44:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(butan-2-ylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) . (H2O) ; _chemical_formula_moiety 'C10 H13 N3 O, C7 H6 O3, H2 O' _chemical_formula_sum 'C17 H21 N3 O5' _chemical_formula_weight 347.37 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3699(2) _cell_length_b 10.9498(3) _cell_length_c 12.8120(3) _cell_angle_alpha 81.0090(10) _cell_angle_beta 80.5660(10) _cell_angle_gamma 83.8590(10) _cell_volume 867.67(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6704 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 26.63 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.33 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_number 14210 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3232 _reflns_number_gt 2702 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0553P)^2^+0.3286P] 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_number_reflns 3232 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.55 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.3020(3) -0.03677(14) 0.24886(13) 0.0336(4) Uani 1 1 d . . . C2 C 1.2032(2) -0.13875(14) 0.23544(12) 0.0288(3) Uani 1 1 d . . . H2A H 1.0599 -0.1492 0.2679 0.035 Uiso 1 1 calc R . . C3 C 1.3149(3) -0.22587(14) 0.17422(12) 0.0310(3) Uani 1 1 d . . . C4 C 1.5231(3) -0.20875(17) 0.12568(14) 0.0433(4) Uani 1 1 d . . . H4 H 1.5988 -0.2671 0.0826 0.052 Uiso 1 1 calc R . . C5 C 1.6201(3) -0.1071(2) 0.14002(17) 0.0561(5) Uani 1 1 d . . . H5 H 1.7632 -0.0964 0.1073 0.067 Uiso 1 1 calc R . . C6 C 1.5114(3) -0.02066(19) 0.20155(17) 0.0516(5) Uani 1 1 d . . . H6 H 1.5792 0.049 0.2114 0.062 Uiso 1 1 calc R . . C7 C 1.1874(3) 0.05858(15) 0.31419(13) 0.0368(4) Uani 1 1 d . . . O1 O 0.9926(2) 0.03639(12) 0.35786(10) 0.0447(3) Uani 1 1 d . . . H1 H 0.935(4) 0.102(2) 0.3915(19) 0.067 Uiso 1 1 d . . . O2 O 1.2716(2) 0.14946(12) 0.32504(13) 0.0576(4) Uani 1 1 d . . . O3 O 1.2297(2) -0.32990(11) 0.16038(10) 0.0423(3) Uani 1 1 d . . . H3 H 1.118(4) -0.341(2) 0.2055(19) 0.063 Uiso 1 1 d . . . C8 C 0.4590(2) 0.33338(13) 0.59493(11) 0.0267(3) Uani 1 1 d . . . C9 C 0.6634(2) 0.37192(14) 0.56588(12) 0.0294(3) Uani 1 1 d . . . H9 H 0.7007 0.4432 0.5901 0.035 Uiso 1 1 calc R . . C10 C 0.8122(3) 0.30463(15) 0.50093(12) 0.0337(4) Uani 1 1 d . . . H10 H 0.9527 0.3307 0.4823 0.04 Uiso 1 1 calc R . . C11 C 0.5703(3) 0.17023(16) 0.48989(15) 0.0418(4) Uani 1 1 d . . . H11 H 0.536 0.1004 0.4623 0.05 Uiso 1 1 calc R . . C12 C 0.4126(3) 0.23028(16) 0.55548(15) 0.0390(4) Uani 1 1 d . . . H12 H 0.2741 0.2013 0.5733 0.047 Uiso 1 1 calc R . . C13 C 0.2819(2) 0.39572(14) 0.66633(12) 0.0287(3) Uani 1 1 d . . . C14 C 0.1901(3) 0.60045(15) 0.85187(13) 0.0339(4) Uani 1 1 d . . . C15 C 0.3986(3) 0.60365(19) 0.88953(15) 0.0463(5) Uani 1 1 d . . . H15A H 0.4943 0.5318 0.8703 0.069 Uiso 1 1 calc R . . H15B H 0.3753 0.6012 0.9673 0.069 Uiso 1 1 calc R . . H15C H 0.4633 0.6801 0.8557 0.069 Uiso 1 1 calc R . . C16 C 0.0363(3) 0.80644(18) 0.90767(16) 0.0509(5) Uani 1 1 d . . . H16A H 0.1436 0.8117 0.9532 0.076 Uiso 1 1 calc R . . H16B H -0.0979 0.8516 0.9344 0.076 Uiso 1 1 calc R . . H16C H 0.087 0.8433 0.8343 0.076 Uiso 1 1 calc R . . C17 C -0.0007(3) 0.66954(18) 0.90927(15) 0.0458(5) Uani 1 1 d . . . H17A H -0.0303 0.6292 0.9843 0.055 Uiso 1 1 calc R . . H17B H -0.1274 0.6651 0.8748 0.055 Uiso 1 1 calc R . . N1 N 0.7678(2) 0.20513(13) 0.46328(11) 0.0354(3) Uani 1 1 d . . . N2 N 0.3288(2) 0.48447(12) 0.71807(10) 0.0281(3) Uani 1 1 d . . . H2 H 0.452(3) 0.5089(16) 0.7136(14) 0.034 Uiso 1 1 d . . . N3 N 0.1549(2) 0.54635(13) 0.77589(11) 0.0349(3) Uani 1 1 d . . . O4 O 0.10019(17) 0.36222(11) 0.67629(10) 0.0409(3) Uani 1 1 d . . . O1W O 0.74772(19) 0.59530(12) 0.67873(10) 0.0372(3) Uani 1 1 d . . . H1W H 0.859(4) 0.565(2) 0.7085(17) 0.056 Uiso 1 1 d . . . H2W H 0.744(3) 0.674(2) 0.6748(17) 0.056 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0363(9) 0.0308(8) 0.0343(8) -0.0078(6) -0.0043(7) -0.0020(7) C2 0.0274(8) 0.0296(8) 0.0285(7) -0.0058(6) -0.0023(6) 0.0008(6) C3 0.0338(8) 0.0293(8) 0.0293(8) -0.0070(6) -0.0017(6) 0.0003(6) C4 0.0403(10) 0.0452(10) 0.0407(9) -0.0143(8) 0.0103(8) 0.0005(8) C5 0.0399(10) 0.0645(13) 0.0622(12) -0.0226(10) 0.0183(9) -0.0160(9) C6 0.0444(11) 0.0494(11) 0.0625(12) -0.0198(9) 0.0085(9) -0.0186(9) C7 0.0415(10) 0.0306(8) 0.0412(9) -0.0122(7) -0.0091(8) -0.0007(7) O1 0.0456(7) 0.0382(7) 0.0509(7) -0.0245(6) 0.0053(6) 0.0004(5) O2 0.0554(9) 0.0403(7) 0.0858(11) -0.0316(7) -0.0130(7) -0.0059(6) O3 0.0452(7) 0.0357(7) 0.0463(7) -0.0210(5) 0.0093(6) -0.0068(5) C8 0.0262(8) 0.0268(8) 0.0277(7) -0.0068(6) -0.0051(6) 0.0009(6) C9 0.0301(8) 0.0294(8) 0.0297(8) -0.0100(6) -0.0008(6) -0.0036(6) C10 0.0296(8) 0.0376(9) 0.0331(8) -0.0099(7) 0.0019(6) -0.0022(7) C11 0.0435(10) 0.0342(9) 0.0530(10) -0.0235(8) -0.0080(8) 0.0001(7) C12 0.0302(8) 0.0375(9) 0.0538(10) -0.0199(8) -0.0063(7) -0.0042(7) C13 0.0241(8) 0.0293(8) 0.0333(8) -0.0084(6) -0.0029(6) -0.0011(6) C14 0.0341(8) 0.0343(8) 0.0327(8) -0.0112(7) 0.0005(7) 0.0005(7) C15 0.0454(10) 0.0562(11) 0.0414(10) -0.0222(8) -0.0124(8) 0.0091(9) C16 0.0486(11) 0.0521(12) 0.0494(11) -0.0148(9) -0.0001(9) 0.0070(9) C17 0.0368(9) 0.0559(11) 0.0450(10) -0.0241(9) 0.0053(8) 0.0017(8) N1 0.0390(8) 0.0337(7) 0.0336(7) -0.0126(6) -0.0040(6) 0.0055(6) N2 0.0195(6) 0.0321(7) 0.0340(7) -0.0137(5) -0.0002(5) 0.0001(5) N3 0.0253(7) 0.0393(8) 0.0410(8) -0.0187(6) 0.0013(6) 0.0020(6) O4 0.0235(6) 0.0466(7) 0.0566(8) -0.0241(6) 0.0014(5) -0.0079(5) O1W 0.0324(6) 0.0296(6) 0.0516(7) -0.0110(5) -0.0054(5) -0.0061(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.385(2) . ? C1 C6 1.389(2) . ? C1 C7 1.494(2) . ? C2 C3 1.392(2) . ? C2 H2A 0.95 . ? C3 O3 1.3605(19) . ? C3 C4 1.388(2) . ? C4 C5 1.379(3) . ? C4 H4 0.95 . ? C5 C6 1.382(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.216(2) . ? C7 O1 1.306(2) . ? O1 H1 0.91(3) . ? O3 H3 0.85(2) . ? C8 C12 1.384(2) . ? C8 C9 1.386(2) . ? C8 C13 1.506(2) . ? C9 C10 1.385(2) . ? C9 H9 0.95 . ? C10 N1 1.332(2) . ? C10 H10 0.95 . ? C11 N1 1.329(2) . ? C11 C12 1.379(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2324(18) . ? C13 N2 1.342(2) . ? C14 N3 1.276(2) . ? C14 C15 1.491(2) . ? C14 C17 1.508(2) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 C17 1.539(3) . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? N2 N3 1.4006(17) . ? N2 H2 0.846(19) . ? O1W H1W 0.87(2) . ? O1W H2W 0.85(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 C2 C1 C6 120.53(15) . . ? C2 C1 C7 121.24(14) . . ? C6 C1 C7 118.23(15) . . ? C1 C2 C3 119.70(14) . . ? C1 C2 H2A 120.1 . . ? C3 C2 H2A 120.1 . . ? O3 C3 C4 117.54(14) . . ? O3 C3 C2 122.72(14) . . ? C4 C3 C2 119.73(15) . . ? C5 C4 C3 120.02(16) . . ? C5 C4 H4 120 . . ? C3 C4 H4 120 . . ? C4 C5 C6 120.73(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 119.28(17) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O2 C7 O1 123.33(15) . . ? O2 C7 C1 121.72(16) . . ? O1 C7 C1 114.95(14) . . ? C7 O1 H1 107.6(15) . . ? C3 O3 H3 109.4(16) . . ? C12 C8 C9 118.01(14) . . ? C12 C8 C13 117.15(13) . . ? C9 C8 C13 124.84(13) . . ? C10 C9 C8 118.84(14) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N1 C10 C9 123.15(15) . . ? N1 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? N1 C11 C12 123.31(15) . . ? N1 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C8 119.08(15) . . ? C11 C12 H12 120.5 . . ? C8 C12 H12 120.5 . . ? O4 C13 N2 122.46(14) . . ? O4 C13 C8 118.87(13) . . ? N2 C13 C8 118.66(13) . . ? N3 C14 C15 127.28(15) . . ? N3 C14 C17 116.16(15) . . ? C15 C14 C17 116.55(15) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 C16 111.71(15) . . ? C14 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C14 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C11 N1 C10 117.60(14) . . ? C13 N2 N3 116.01(13) . . ? C13 N2 H2 124.8(12) . . ? N3 N2 H2 119.0(12) . . ? C14 N3 N2 118.12(14) . . ? H1W O1W H2W 106(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 C6 C1 C2 C3 0.1(3) . . . . ? C7 C1 C2 C3 -179.87(14) . . . . ? C1 C2 C3 O3 178.04(15) . . . . ? C1 C2 C3 C4 -1.1(2) . . . . ? O3 C3 C4 C5 -177.79(17) . . . . ? C2 C3 C4 C5 1.4(3) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? C7 C1 C6 C5 -179.47(19) . . . . ? C2 C1 C7 O2 -178.81(16) . . . . ? C6 C1 C7 O2 1.2(3) . . . . ? C2 C1 C7 O1 1.2(2) . . . . ? C6 C1 C7 O1 -178.80(17) . . . . ? C12 C8 C9 C10 -1.3(2) . . . . ? C13 C8 C9 C10 178.94(14) . . . . ? C8 C9 C10 N1 1.1(2) . . . . ? N1 C11 C12 C8 1.0(3) . . . . ? C9 C8 C12 C11 0.3(2) . . . . ? C13 C8 C12 C11 -179.91(15) . . . . ? C12 C8 C13 O4 -8.4(2) . . . . ? C9 C8 C13 O4 171.42(15) . . . . ? C12 C8 C13 N2 170.62(15) . . . . ? C9 C8 C13 N2 -9.6(2) . . . . ? N3 C14 C17 C16 -123.95(18) . . . . ? C15 C14 C17 C16 55.6(2) . . . . ? C12 C11 N1 C10 -1.2(3) . . . . ? C9 C10 N1 C11 0.2(2) . . . . ? O4 C13 N2 N3 -6.3(2) . . . . ? C8 C13 N2 N3 174.71(13) . . . . ? C15 C14 N3 N2 -1.6(3) . . . . ? C17 C14 N3 N2 177.95(14) . . . . ? C13 N2 N3 C14 157.82(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 O1 H1 N1 0.91(3) 1.73(3) 2.6208(17) 165(2) . C10 H10 O2 0.95 3.34 3.808(2) 112.5 . O3 H3 O4 0.85(2) 1.88(2) 2.7214(17) 170(2) 2_656 N2 H2 O1W 0.846(19) 2.149(19) 2.9848(18) 169.5(17) . O1W H1W N3 0.87(2) 2.18(2) 3.0196(19) 163(2) 1_655 O1W H1W O4 0.87(2) 2.61(2) 3.2143(18) 127.6(18) 1_655 O1W H2W O2 0.85(2) 1.93(2) 2.7775(18) 177(2) 2_766 ###END data_10 _database_code_depnum_ccdc_archive 'CCDC 810557' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-03-20T12:05:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(cyclohexylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) . (H2O) ; _chemical_formula_moiety 'C12 H15 N3 O, C7 H6 O3, H2 O' _chemical_formula_sum 'C19 H23 N3 O5' _chemical_formula_weight 373.4 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3632(6) _cell_length_b 10.8918(10) _cell_length_c 13.3842(12) _cell_angle_alpha 87.434(7) _cell_angle_beta 80.241(8) _cell_angle_gamma 83.083(8) _cell_volume 907.26(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5021 _cell_measurement_theta_min 3.3606 _cell_measurement_theta_max 67.339 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.829 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.84 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0311 _diffrn_reflns_number 8274 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 67.45 _diffrn_reflns_theta_full 67.45 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 3240 _reflns_number_gt 2666 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1051P)^2^] 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_number_reflns 3240 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.249 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.06 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.3255(2) -0.08335(14) 0.26199(11) 0.0209(3) Uani 1 1 d . . . C2 C 1.2122(2) -0.18165(14) 0.24820(11) 0.0210(3) Uani 1 1 d . . . H2A H 1.0648 -0.1799 0.2768 0.025 Uiso 1 1 calc R . . C3 C 1.3173(3) -0.28233(14) 0.19207(11) 0.0221(3) Uani 1 1 d . . . C4 C 1.5319(3) -0.28229(14) 0.14797(11) 0.0239(4) Uani 1 1 d . . . H4 H 1.6022 -0.3494 0.1075 0.029 Uiso 1 1 calc R . . C5 C 1.6435(3) -0.18458(15) 0.16295(12) 0.0258(4) Uani 1 1 d . . . H5 H 1.7905 -0.1859 0.1337 0.031 Uiso 1 1 calc R . . C6 C 1.5417(3) -0.08511(15) 0.22034(12) 0.0247(4) Uani 1 1 d . . . H6 H 1.6187 -0.0187 0.2311 0.03 Uiso 1 1 calc R . . C7 C 1.2168(2) 0.02598(14) 0.32142(11) 0.0218(3) Uani 1 1 d . . . O1 O 1.01354(18) 0.02023(10) 0.35854(9) 0.0278(3) Uani 1 1 d . . . H1 H 0.938(4) 0.097(2) 0.3990(17) 0.042 Uiso 1 1 d . . . O2 O 1.31277(19) 0.11377(10) 0.33388(9) 0.0284(3) Uani 1 1 d . . . O3 O 1.2169(2) -0.38232(10) 0.17725(9) 0.0285(3) Uani 1 1 d . . . H3 H 1.099(4) -0.387(2) 0.2264(19) 0.043 Uiso 1 1 d . . . C8 C 0.4708(2) 0.34758(13) 0.58574(11) 0.0199(3) Uani 1 1 d . . . C9 C 0.6756(2) 0.38526(14) 0.56002(11) 0.0210(3) Uani 1 1 d . . . H9 H 0.7072 0.4604 0.5844 0.025 Uiso 1 1 calc R . . C10 C 0.8316(3) 0.31055(14) 0.49814(11) 0.0229(3) Uani 1 1 d . . . H10 H 0.9711 0.3361 0.4809 0.027 Uiso 1 1 calc R . . C11 C 0.5976(3) 0.16957(15) 0.48574(12) 0.0247(4) Uani 1 1 d . . . H11 H 0.5699 0.0946 0.4595 0.03 Uiso 1 1 calc R . . C12 C 0.4322(3) 0.23811(15) 0.54708(12) 0.0243(4) Uani 1 1 d . . . H12 H 0.294 0.2105 0.5625 0.029 Uiso 1 1 calc R . . C13 C 0.2865(2) 0.41708(14) 0.65360(11) 0.0201(3) Uani 1 1 d . . . C14 C 0.1594(3) 0.62965(15) 0.84317(13) 0.0266(4) Uani 1 1 d . . . C15 C 0.3538(2) 0.63650(14) 0.89102(11) 0.0227(3) Uani 1 1 d . . . H15A H 0.4817 0.5922 0.8495 0.027 Uiso 1 1 calc R . . H15B H 0.3344 0.597 0.9595 0.027 Uiso 1 1 calc R . . C16 C 0.3856(3) 0.77361(15) 0.89846(12) 0.0259(4) Uani 1 1 d . . . H16A H 0.5042 0.7793 0.9367 0.031 Uiso 1 1 calc R . . H16B H 0.4277 0.8084 0.8294 0.031 Uiso 1 1 calc R . . C17 C 0.1839(3) 0.85045(15) 0.95064(12) 0.0260(4) Uani 1 1 d . . . H17A H 0.1529 0.8234 1.0227 0.031 Uiso 1 1 calc R . . H17B H 0.209 0.9386 0.9484 0.031 Uiso 1 1 calc R . . C18 C -0.0084(3) 0.83737(17) 0.90004(13) 0.0343(4) Uani 1 1 d . . . H18A H 0.015 0.8734 0.8304 0.041 Uiso 1 1 calc R . . H18B H -0.1385 0.8833 0.9385 0.041 Uiso 1 1 calc R . . C19 C -0.0415(3) 0.70115(19) 0.89603(16) 0.0390(5) Uani 1 1 d . . . H19A H -0.0788 0.6671 0.9658 0.047 Uiso 1 1 calc R . . H19B H -0.1617 0.6934 0.8593 0.047 Uiso 1 1 calc R . . N1 N 0.7950(2) 0.20431(12) 0.46165(10) 0.0229(3) Uani 1 1 d . . . N2 N 0.3246(2) 0.51229(12) 0.70589(10) 0.0207(3) Uani 1 1 d . . . H2 H 0.452(3) 0.5385(18) 0.7041(14) 0.025 Uiso 1 1 d . . . N3 N 0.1412(2) 0.57649(13) 0.76178(11) 0.0272(3) Uani 1 1 d . . . O4 O 0.10571(17) 0.38281(10) 0.66133(9) 0.0262(3) Uani 1 1 d . . . O1W O 0.72603(19) 0.62659(11) 0.67878(9) 0.0248(3) Uani 1 1 d . . . H1W H 0.844(4) 0.606(2) 0.7013(17) 0.037 Uiso 1 1 d . . . H2W H 0.724(4) 0.708(2) 0.6713(16) 0.037 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0214(8) 0.0196(8) 0.0209(7) 0.0004(6) -0.0018(6) -0.0018(6) C2 0.0190(8) 0.0218(8) 0.0213(7) -0.0012(6) -0.0011(6) -0.0016(6) C3 0.0251(8) 0.0198(7) 0.0211(7) -0.0004(6) -0.0021(6) -0.0035(6) C4 0.0262(8) 0.0207(8) 0.0220(7) -0.0007(6) 0.0021(6) 0.0002(6) C5 0.0208(8) 0.0270(8) 0.0267(8) 0.0010(6) 0.0030(6) -0.0016(6) C6 0.0232(8) 0.0226(8) 0.0284(8) 0.0004(6) -0.0025(6) -0.0055(6) C7 0.0222(8) 0.0207(8) 0.0226(7) 0.0006(6) -0.0043(6) -0.0029(6) O1 0.0221(6) 0.0250(6) 0.0344(6) -0.0094(5) 0.0031(5) -0.0020(5) O2 0.0277(6) 0.0223(6) 0.0358(6) -0.0064(5) -0.0042(5) -0.0051(5) O3 0.0286(6) 0.0230(6) 0.0326(6) -0.0084(5) 0.0037(5) -0.0066(5) C8 0.0192(8) 0.0203(7) 0.0197(7) -0.0016(6) -0.0029(6) -0.0004(6) C9 0.0221(8) 0.0206(7) 0.0205(7) -0.0021(6) -0.0022(6) -0.0047(6) C10 0.0215(8) 0.0244(8) 0.0227(7) -0.0031(6) -0.0016(6) -0.0042(6) C11 0.0249(8) 0.0218(8) 0.0276(8) -0.0068(6) -0.0040(6) -0.0021(6) C12 0.0202(8) 0.0249(8) 0.0286(8) -0.0037(6) -0.0037(6) -0.0050(6) C13 0.0194(7) 0.0209(7) 0.0206(7) -0.0019(6) -0.0034(6) -0.0033(6) C14 0.0196(8) 0.0279(8) 0.0316(8) -0.0102(7) 0.0012(6) -0.0044(6) C15 0.0202(8) 0.0249(8) 0.0224(7) -0.0042(6) -0.0015(6) -0.0013(6) C16 0.0226(8) 0.0264(8) 0.0286(8) -0.0066(6) -0.0015(6) -0.0043(7) C17 0.0264(8) 0.0231(8) 0.0272(8) -0.0048(6) 0.0003(6) -0.0025(6) C18 0.0288(9) 0.0412(10) 0.0305(9) -0.0134(7) -0.0065(7) 0.0126(8) C19 0.0176(8) 0.0520(12) 0.0483(11) -0.0296(9) -0.0015(7) -0.0022(8) N1 0.0225(7) 0.0227(7) 0.0227(6) -0.0033(5) -0.0023(5) -0.0002(5) N2 0.0144(6) 0.0223(6) 0.0248(6) -0.0070(5) -0.0001(5) -0.0014(5) N3 0.0172(7) 0.0314(8) 0.0326(7) -0.0140(6) -0.0009(5) -0.0011(6) O4 0.0172(6) 0.0287(6) 0.0331(6) -0.0095(5) -0.0005(4) -0.0058(5) O1W 0.0210(6) 0.0207(6) 0.0331(6) -0.0039(4) -0.0035(5) -0.0042(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.392(2) . ? C1 C2 1.396(2) . ? C1 C7 1.493(2) . ? C2 C3 1.393(2) . ? C2 H2A 0.95 . ? C3 O3 1.3653(19) . ? C3 C4 1.393(2) . ? C4 C5 1.388(2) . ? C4 H4 0.95 . ? C5 C6 1.386(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2268(19) . ? C7 O1 1.3122(19) . ? O1 H1 1.04(3) . ? O3 H3 0.92(3) . ? C8 C12 1.385(2) . ? C8 C9 1.396(2) . ? C8 C13 1.503(2) . ? C9 C10 1.386(2) . ? C9 H9 0.95 . ? C10 N1 1.336(2) . ? C10 H10 0.95 . ? C11 N1 1.339(2) . ? C11 C12 1.383(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2383(19) . ? C13 N2 1.344(2) . ? C14 N3 1.285(2) . ? C14 C15 1.497(2) . ? C14 C19 1.498(2) . ? C15 C16 1.541(2) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.525(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.519(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.528(3) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? N2 N3 1.4019(18) . ? N2 H2 0.89(2) . ? O1W H1W 0.86(3) . ? O1W H2W 0.89(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 C6 C1 C2 120.69(14) . . ? C6 C1 C7 118.73(14) . . ? C2 C1 C7 120.58(14) . . ? C3 C2 C1 119.44(14) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? O3 C3 C4 117.86(14) . . ? O3 C3 C2 122.36(14) . . ? C4 C3 C2 119.78(14) . . ? C5 C4 C3 120.25(15) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.42(15) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.38(15) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O2 C7 O1 123.35(14) . . ? O2 C7 C1 121.68(14) . . ? O1 C7 C1 114.96(13) . . ? C7 O1 H1 114.6(13) . . ? C3 O3 H3 110.3(14) . . ? C12 C8 C9 118.47(14) . . ? C12 C8 C13 116.82(14) . . ? C9 C8 C13 124.71(14) . . ? C10 C9 C8 118.49(14) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? N1 C10 C9 123.06(14) . . ? N1 C10 H10 118.5 . . ? C9 C10 H10 118.5 . . ? N1 C11 C12 122.85(15) . . ? N1 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C11 C12 C8 119.06(14) . . ? C11 C12 H12 120.5 . . ? C8 C12 H12 120.5 . . ? O4 C13 N2 122.21(14) . . ? O4 C13 C8 118.88(14) . . ? N2 C13 C8 118.89(13) . . ? N3 C14 C15 129.86(15) . . ? N3 C14 C19 115.53(15) . . ? C15 C14 C19 114.54(14) . . ? C14 C15 C16 108.60(13) . . ? C14 C15 H15A 110 . . ? C16 C15 H15A 110 . . ? C14 C15 H15B 110 . . ? C16 C15 H15B 110 . . ? H15A C15 H15B 108.4 . . ? C17 C16 C15 112.58(13) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 111.51(13) . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108 . . ? C17 C18 C19 110.39(15) . . ? C17 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? C17 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C14 C19 C18 109.86(15) . . ? C14 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? C14 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C10 N1 C11 118.06(14) . . ? C13 N2 N3 114.77(13) . . ? C13 N2 H2 125.2(13) . . ? N3 N2 H2 119.9(13) . . ? C14 N3 N2 118.73(14) . . ? H1W O1W H2W 102(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 C6 C1 C2 C3 0.0(2) . . . . ? C7 C1 C2 C3 179.73(13) . . . . ? C1 C2 C3 O3 178.83(14) . . . . ? C1 C2 C3 C4 -1.8(2) . . . . ? O3 C3 C4 C5 -178.20(14) . . . . ? C2 C3 C4 C5 2.4(2) . . . . ? C3 C4 C5 C6 -1.2(2) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C2 C1 C6 C5 1.3(2) . . . . ? C7 C1 C6 C5 -178.46(14) . . . . ? C6 C1 C7 O2 0.3(2) . . . . ? C2 C1 C7 O2 -179.46(14) . . . . ? C6 C1 C7 O1 -179.68(14) . . . . ? C2 C1 C7 O1 0.6(2) . . . . ? C12 C8 C9 C10 -0.9(2) . . . . ? C13 C8 C9 C10 178.73(14) . . . . ? C8 C9 C10 N1 0.2(2) . . . . ? N1 C11 C12 C8 0.0(2) . . . . ? C9 C8 C12 C11 0.8(2) . . . . ? C13 C8 C12 C11 -178.85(14) . . . . ? C12 C8 C13 O4 -9.0(2) . . . . ? C9 C8 C13 O4 171.40(14) . . . . ? C12 C8 C13 N2 169.30(14) . . . . ? C9 C8 C13 N2 -10.3(2) . . . . ? N3 C14 C15 C16 120.99(19) . . . . ? C19 C14 C15 C16 -55.64(19) . . . . ? C14 C15 C16 C17 52.69(17) . . . . ? C15 C16 C17 C18 -54.39(18) . . . . ? C16 C17 C18 C19 55.19(19) . . . . ? N3 C14 C19 C18 -118.84(17) . . . . ? C15 C14 C19 C18 58.3(2) . . . . ? C17 C18 C19 C14 -56.0(2) . . . . ? C9 C10 N1 C11 0.5(2) . . . . ? C12 C11 N1 C10 -0.6(2) . . . . ? O4 C13 N2 N3 -5.8(2) . . . . ? C8 C13 N2 N3 175.98(12) . . . . ? C15 C14 N3 N2 0.7(3) . . . . ? C19 C14 N3 N2 177.32(15) . . . . ? C13 N2 N3 C14 150.91(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 O1 H1 N1 1.04(3) 1.57(3) 2.6045(17) 172(2) . C10 H10 O2 0.95 3.49 3.919(2) 110.2 . O3 H3 O4 0.92(3) 1.81(3) 2.7165(16) 169(2) 2_656 N2 H2 O1W 0.89(2) 2.06(2) 2.9357(18) 168.0(17) . O1W H1W N3 0.86(3) 2.16(3) 3.0171(19) 173(2) 1_655 O1W H1W O4 0.86(3) 2.79(2) 3.3558(18) 124.5(18) 1_655 O1W H2W O2 0.89(2) 1.93(3) 2.8088(16) 173(2) 2_766 ###END data_11 _database_code_depnum_ccdc_archive 'CCDC 810558' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-03-20T12:16:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(cycloheptylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) . (H2O) ; _chemical_formula_moiety 'C13 H17 N3 O, C7 H6 O3, H2 O' _chemical_formula_sum 'C20 H25 N3 O5' _chemical_formula_weight 387.43 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.3127(4) _cell_length_b 11.4293(6) _cell_length_c 26.1598(15) _cell_angle_alpha 90 _cell_angle_beta 91.109(5) _cell_angle_gamma 90 _cell_volume 1887.07(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5507 _cell_measurement_theta_min 3.3783 _cell_measurement_theta_max 67.2837 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.92 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_number 11880 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 67.36 _diffrn_reflns_theta_full 67.36 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3403 _reflns_number_gt 2858 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1021P)^2^] 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_number_reflns 3403 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.238 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.2172(2) -0.03476(13) 0.38614(5) 0.0180(3) Uani 1 1 d . . . C2 C 1.1401(2) -0.14929(13) 0.38471(6) 0.0181(3) Uani 1 1 d . . . H2A H 1.004 -0.1665 0.3977 0.022 Uiso 1 1 calc R . . C3 C 1.2630(2) -0.23804(13) 0.36428(5) 0.0177(3) Uani 1 1 d . . . C4 C 1.4637(2) -0.21192(14) 0.34558(6) 0.0197(3) Uani 1 1 d . . . H4 H 1.5475 -0.2722 0.3313 0.024 Uiso 1 1 calc R . . C5 C 1.5404(2) -0.09862(14) 0.34780(6) 0.0209(3) Uani 1 1 d . . . H5 H 1.6778 -0.0818 0.3356 0.025 Uiso 1 1 calc R . . C6 C 1.4178(2) -0.00906(13) 0.36782(6) 0.0206(3) Uani 1 1 d . . . H6 H 1.4703 0.0688 0.369 0.025 Uiso 1 1 calc R . . C7 C 1.0883(2) 0.06317(13) 0.40713(6) 0.0198(3) Uani 1 1 d . . . O1 O 0.91297(17) 0.03077(10) 0.42915(4) 0.0267(3) Uani 1 1 d . . . H1 H 0.834(4) 0.109(2) 0.4456(8) 0.04 Uiso 1 1 d . . . O2 O 1.14466(18) 0.16498(10) 0.40353(5) 0.0287(3) Uani 1 1 d . . . O3 O 1.19658(17) -0.35099(9) 0.36121(4) 0.0206(3) Uani 1 1 d . . . H3 H 1.087(3) -0.3587(18) 0.3814(9) 0.031 Uiso 1 1 d . . . C8 C 0.4474(2) 0.33230(13) 0.53584(5) 0.0173(3) Uani 1 1 d . . . C9 C 0.6443(2) 0.37202(13) 0.52053(6) 0.0184(3) Uani 1 1 d . . . H9 H 0.6958 0.4464 0.5312 0.022 Uiso 1 1 calc R . . C10 C 0.7641(2) 0.30057(14) 0.48932(6) 0.0211(3) Uani 1 1 d . . . H10 H 0.899 0.3275 0.479 0.025 Uiso 1 1 calc R . . C11 C 0.5065(2) 0.15869(13) 0.48768(6) 0.0220(3) Uani 1 1 d . . . H11 H 0.458 0.0845 0.4761 0.026 Uiso 1 1 calc R . . C12 C 0.3764(2) 0.22360(13) 0.51868(6) 0.0206(3) Uani 1 1 d . . . H12 H 0.2416 0.1947 0.5281 0.025 Uiso 1 1 calc R . . C13 C 0.3019(2) 0.39931(13) 0.56991(6) 0.0174(3) Uani 1 1 d . . . C14 C 0.3089(2) 0.59166(13) 0.67121(6) 0.0186(3) Uani 1 1 d . . . C15 C 0.5220(2) 0.56322(15) 0.69536(6) 0.0243(4) Uani 1 1 d . . . H15A H 0.6318 0.5746 0.6693 0.029 Uiso 1 1 calc R . . H15B H 0.5229 0.4793 0.7048 0.029 Uiso 1 1 calc R . . C16 C 0.5850(2) 0.63428(14) 0.74261(6) 0.0226(3) Uani 1 1 d . . . H16A H 0.7243 0.6061 0.7556 0.027 Uiso 1 1 calc R . . H16B H 0.4802 0.6197 0.7696 0.027 Uiso 1 1 calc R . . C17 C 0.5990(2) 0.76607(14) 0.73341(6) 0.0237(3) Uani 1 1 d . . . H17A H 0.7035 0.7998 0.758 0.028 Uiso 1 1 calc R . . H17B H 0.6524 0.7796 0.6986 0.028 Uiso 1 1 calc R . . C18 C 0.3889(2) 0.83066(14) 0.73879(6) 0.0241(4) Uani 1 1 d . . . H18A H 0.4164 0.9157 0.7362 0.029 Uiso 1 1 calc R . . H18B H 0.3348 0.8154 0.7734 0.029 Uiso 1 1 calc R . . C19 C 0.2158(2) 0.79852(14) 0.69971(6) 0.0228(3) Uani 1 1 d . . . H19A H 0.2642 0.8213 0.6653 0.027 Uiso 1 1 calc R . . H19B H 0.0881 0.8454 0.707 0.027 Uiso 1 1 calc R . . C20 C 0.1526(2) 0.66853(14) 0.69825(6) 0.0209(3) Uani 1 1 d . . . H20A H 0.138 0.6401 0.7337 0.025 Uiso 1 1 calc R . . H20B H 0.0125 0.6612 0.6809 0.025 Uiso 1 1 calc R . . N1 N 0.6978(2) 0.19530(11) 0.47320(5) 0.0219(3) Uani 1 1 d . . . N2 N 0.38599(19) 0.48234(11) 0.60039(5) 0.0180(3) Uani 1 1 d . . . H2 H 0.533(3) 0.5026(16) 0.6008(7) 0.022 Uiso 1 1 d . . . N3 N 0.24289(18) 0.55120(11) 0.62775(5) 0.0189(3) Uani 1 1 d . . . O4 O 0.11117(16) 0.37336(10) 0.57038(4) 0.0231(3) Uani 1 1 d . . . O1W O 0.80467(18) 0.59397(10) 0.58636(4) 0.0226(3) Uani 1 1 d . . . H1W H 0.930(4) 0.570(2) 0.5955(8) 0.034 Uiso 1 1 d . . . H2W H 0.806(3) 0.671(2) 0.5878(8) 0.034 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0188(7) 0.0177(7) 0.0176(7) -0.0007(5) 0.0001(5) 0.0009(6) C2 0.0165(7) 0.0191(7) 0.0187(7) 0.0004(5) 0.0022(5) 0.0004(5) C3 0.0202(7) 0.0164(7) 0.0165(7) 0.0012(5) 0.0011(5) 0.0000(6) C4 0.0194(7) 0.0216(8) 0.0182(7) 0.0006(5) 0.0022(5) 0.0049(6) C5 0.0172(7) 0.0261(8) 0.0196(7) 0.0033(6) 0.0027(6) -0.0002(6) C6 0.0212(7) 0.0187(7) 0.0219(8) 0.0016(6) -0.0001(6) -0.0026(6) C7 0.0210(7) 0.0177(8) 0.0206(7) -0.0020(6) -0.0023(6) 0.0003(6) O1 0.0256(6) 0.0202(6) 0.0346(7) -0.0053(5) 0.0090(5) 0.0024(4) O2 0.0289(6) 0.0170(6) 0.0403(7) -0.0032(5) 0.0014(5) -0.0006(4) O3 0.0225(5) 0.0150(5) 0.0245(6) -0.0009(4) 0.0058(4) 0.0002(4) C8 0.0181(7) 0.0177(7) 0.0160(7) 0.0010(5) -0.0001(5) 0.0021(5) C9 0.0193(7) 0.0183(7) 0.0176(7) 0.0004(6) 0.0011(6) 0.0003(5) C10 0.0193(7) 0.0222(8) 0.0217(8) -0.0010(6) 0.0022(6) 0.0018(6) C11 0.0251(8) 0.0180(7) 0.0228(8) -0.0016(6) -0.0006(6) 0.0003(6) C12 0.0208(7) 0.0196(7) 0.0214(7) -0.0021(6) 0.0019(6) -0.0014(6) C13 0.0185(7) 0.0165(7) 0.0173(7) 0.0002(5) 0.0008(5) 0.0004(5) C14 0.0188(7) 0.0180(7) 0.0190(7) -0.0011(6) 0.0040(5) -0.0018(6) C15 0.0212(7) 0.0273(8) 0.0244(8) -0.0056(6) -0.0004(6) 0.0043(6) C16 0.0211(7) 0.0275(8) 0.0193(8) -0.0013(6) 0.0001(6) 0.0014(6) C17 0.0199(7) 0.0296(9) 0.0215(8) -0.0003(6) 0.0005(6) -0.0037(6) C18 0.0253(8) 0.0222(8) 0.0250(8) -0.0044(6) 0.0040(6) -0.0020(6) C19 0.0199(7) 0.0230(8) 0.0255(8) -0.0033(6) 0.0035(6) 0.0031(6) C20 0.0171(7) 0.0251(8) 0.0207(8) -0.0047(6) 0.0040(6) 0.0000(6) N1 0.0237(6) 0.0208(6) 0.0212(7) -0.0020(5) 0.0008(5) 0.0055(5) N2 0.0152(6) 0.0203(6) 0.0187(6) -0.0039(5) 0.0028(5) 0.0013(5) N3 0.0184(6) 0.0180(6) 0.0203(6) -0.0037(5) 0.0046(5) 0.0013(5) O4 0.0160(5) 0.0252(6) 0.0284(6) -0.0058(4) 0.0048(4) -0.0038(4) O1W 0.0201(5) 0.0157(6) 0.0319(6) -0.0007(4) -0.0001(4) -0.0003(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.394(2) . ? C1 C2 1.397(2) . ? C1 C7 1.495(2) . ? C2 C3 1.390(2) . ? C2 H2A 0.95 . ? C3 O3 1.3593(18) . ? C3 C4 1.399(2) . ? C4 C5 1.383(2) . ? C4 H4 0.95 . ? C5 C6 1.392(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2210(19) . ? C7 O1 1.3109(19) . ? O1 H1 1.11(2) . ? O3 H3 0.88(2) . ? C8 C9 1.389(2) . ? C8 C12 1.392(2) . ? C8 C13 1.502(2) . ? C9 C10 1.389(2) . ? C9 H9 0.95 . ? C10 N1 1.339(2) . ? C10 H10 0.95 . ? C11 N1 1.339(2) . ? C11 C12 1.381(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2400(18) . ? C13 N2 1.3423(19) . ? C14 N3 1.289(2) . ? C14 C20 1.508(2) . ? C14 C15 1.510(2) . ? C15 C16 1.525(2) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.528(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.527(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.527(2) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 C20 1.539(2) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? N1 H1 1.50(2) . ? N2 N3 1.4045(16) . ? N2 H2 0.954(19) . ? O1W H1W 0.87(2) . ? O1W H2W 0.88(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 C6 C1 C2 120.45(14) . . ? C6 C1 C7 118.25(13) . . ? C2 C1 C7 121.30(13) . . ? C3 C2 C1 119.82(13) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? O3 C3 C2 122.82(13) . . ? O3 C3 C4 117.54(13) . . ? C2 C3 C4 119.64(14) . . ? C5 C4 C3 120.25(14) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.50(14) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.32(14) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O2 C7 O1 123.57(14) . . ? O2 C7 C1 121.58(14) . . ? O1 C7 C1 114.85(13) . . ? C7 O1 H1 109.5(12) . . ? C3 O3 H3 107.7(14) . . ? C9 C8 C12 118.87(13) . . ? C9 C8 C13 124.42(13) . . ? C12 C8 C13 116.71(13) . . ? C10 C9 C8 118.53(14) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N1 C10 C9 122.88(14) . . ? N1 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N1 C11 C12 123.21(14) . . ? N1 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C11 C12 C8 118.51(14) . . ? C11 C12 H12 120.7 . . ? C8 C12 H12 120.7 . . ? O4 C13 N2 122.43(13) . . ? O4 C13 C8 119.27(13) . . ? N2 C13 C8 118.25(12) . . ? N3 C14 C20 114.79(13) . . ? N3 C14 C15 124.19(13) . . ? C20 C14 C15 120.99(13) . . ? C14 C15 C16 116.12(13) . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C15 C16 C17 114.35(13) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 114.14(13) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 115.70(13) . . ? C17 C18 H18A 108.4 . . ? C19 C18 H18A 108.4 . . ? C17 C18 H18B 108.4 . . ? C19 C18 H18B 108.4 . . ? H18A C18 H18B 107.4 . . ? C18 C19 C20 115.53(13) . . ? C18 C19 H19A 108.4 . . ? C20 C19 H19A 108.4 . . ? C18 C19 H19B 108.4 . . ? C20 C19 H19B 108.4 . . ? H19A C19 H19B 107.5 . . ? C14 C20 C19 113.73(12) . . ? C14 C20 H20A 108.8 . . ? C19 C20 H20A 108.8 . . ? C14 C20 H20B 108.8 . . ? C19 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C10 N1 C11 117.99(13) . . ? C10 N1 H1 124.4(9) . . ? C11 N1 H1 117.2(9) . . ? C13 N2 N3 116.60(12) . . ? C13 N2 H2 123.4(11) . . ? N3 N2 H2 119.5(11) . . ? C14 N3 N2 116.75(12) . . ? H1W O1W H2W 107(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 C6 C1 C2 C3 -0.8(2) . . . . ? C7 C1 C2 C3 179.11(13) . . . . ? C1 C2 C3 O3 -179.25(13) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? O3 C3 C4 C5 -179.77(13) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -1.1(2) . . . . ? C4 C5 C6 C1 0.6(2) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? C7 C1 C6 C5 -179.60(13) . . . . ? C6 C1 C7 O2 7.9(2) . . . . ? C2 C1 C7 O2 -172.02(14) . . . . ? C6 C1 C7 O1 -172.24(13) . . . . ? C2 C1 C7 O1 7.8(2) . . . . ? C12 C8 C9 C10 -1.1(2) . . . . ? C13 C8 C9 C10 179.34(13) . . . . ? C8 C9 C10 N1 0.3(2) . . . . ? N1 C11 C12 C8 -0.1(2) . . . . ? C9 C8 C12 C11 1.0(2) . . . . ? C13 C8 C12 C11 -179.37(13) . . . . ? C9 C8 C13 O4 160.55(14) . . . . ? C12 C8 C13 O4 -19.1(2) . . . . ? C9 C8 C13 N2 -22.1(2) . . . . ? C12 C8 C13 N2 158.24(14) . . . . ? N3 C14 C15 C16 170.75(15) . . . . ? C20 C14 C15 C16 -11.4(2) . . . . ? C14 C15 C16 C17 -60.28(19) . . . . ? C15 C16 C17 C18 86.59(16) . . . . ? C16 C17 C18 C19 -64.65(18) . . . . ? C17 C18 C19 C20 58.02(18) . . . . ? N3 C14 C20 C19 -109.60(15) . . . . ? C15 C14 C20 C19 72.32(18) . . . . ? C18 C19 C20 C14 -77.02(17) . . . . ? C9 C10 N1 C11 0.6(2) . . . . ? C12 C11 N1 C10 -0.7(2) . . . . ? O4 C13 N2 N3 -9.1(2) . . . . ? C8 C13 N2 N3 173.66(12) . . . . ? C20 C14 N3 N2 177.92(12) . . . . ? C15 C14 N3 N2 -4.1(2) . . . . ? C13 N2 N3 C14 150.27(14) . . . . ? 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 O1 H1 N1 1.11(2) 1.50(2) 2.6019(16) 168(2) . C10 H10 O2 0.95 3.14 3.6633(19) 116.3 . O3 H3 O4 0.88(2) 1.80(2) 2.6789(15) 172(2) 3_656 N2 H2 O1W 0.954(19) 2.051(19) 2.9641(17) 159.6(16) . N2 H2 O3 0.954(19) 2.616(18) 3.1786(16) 118.0(13) 3_756 O1W H1W N3 0.87(2) 2.14(2) 2.9913(17) 166(2) 1_655 O1W H1W O4 0.87(2) 2.61(2) 3.2105(16) 127.2(18) 1_655 O1W H2W O2 0.88(2) 1.92(2) 2.7855(16) 170(2) 3_766 ###END data_12 _database_code_depnum_ccdc_archive 'CCDC 810559' #TrackingRef '- 4-12.cif' _audit_creation_date 2010-04-07T14:03:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (N'-(4-methylbenzylidene)isonicotinohydrazide) . (3-hydroxybenzoic acid) . (H2O) ; _chemical_formula_moiety 'C14 H13 N3 O, C7 H6 O3, H2 O' _chemical_formula_sum 'C21 H21 N3 O5' _chemical_formula_weight 395.41 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1506(5) _cell_length_b 10.5426(6) _cell_length_c 16.2041(12) _cell_angle_alpha 73.603(6) _cell_angle_beta 90.403(6) _cell_angle_gamma 79.320(6) _cell_volume 988.57(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5030 _cell_measurement_theta_min 2.8459 _cell_measurement_theta_max 67.1772 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.797 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.7205 _exptl_absorpt_correction_T_max 0.8568 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Cu' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_number 9145 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 67.28 _diffrn_reflns_theta_full 67.28 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3545 _reflns_number_gt 2833 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1066P)^2^] 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_number_reflns 3545 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.143 _refine_ls_wR_factor_gt 0.137 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.212 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.2136(2) -0.00291(13) 0.27256(9) 0.0346(3) Uani 1 1 d . . . C2 C 1.0875(2) -0.09412(14) 0.26297(9) 0.0335(3) Uani 1 1 d . . . H2A H 0.9516 -0.0982 0.2901 0.04 Uiso 1 1 calc R . . C3 C 1.1612(2) -0.18024(14) 0.21317(9) 0.0355(3) Uani 1 1 d . . . C4 C 1.3555(3) -0.16933(16) 0.17087(10) 0.0436(4) Uani 1 1 d . . . H4 H 1.4025 -0.2248 0.1347 0.052 Uiso 1 1 calc R . . C5 C 1.4806(3) -0.07803(17) 0.18127(11) 0.0490(4) Uani 1 1 d . . . H5 H 1.6143 -0.072 0.1527 0.059 Uiso 1 1 calc R . . C6 C 1.4128(3) 0.00441(16) 0.23273(11) 0.0442(4) Uani 1 1 d . . . H6 H 1.5009 0.0655 0.2409 0.053 Uiso 1 1 calc R . . C7 C 1.1416(3) 0.08827(14) 0.32687(10) 0.0391(4) Uani 1 1 d . . . O1 O 0.9472(2) 0.07964(12) 0.35795(8) 0.0507(3) Uani 1 1 d . . . H1 H 0.908(4) 0.133(2) 0.3904(15) 0.076 Uiso 1 1 d . . . O2 O 1.2565(2) 0.16310(12) 0.34127(9) 0.0565(4) Uani 1 1 d . . . O3 O 1.0518(2) -0.27706(11) 0.20483(7) 0.0485(3) Uani 1 1 d . . . H3 H 0.948(4) -0.293(2) 0.2477(16) 0.073 Uiso 1 1 d . . . C8 C 0.5194(2) 0.31632(13) 0.57941(9) 0.0309(3) Uani 1 1 d . . . C9 C 0.7121(2) 0.36283(14) 0.55455(9) 0.0337(3) Uani 1 1 d . . . H9 H 0.7562 0.4293 0.5765 0.04 Uiso 1 1 calc R . . C10 C 0.8397(3) 0.31082(15) 0.49705(10) 0.0384(4) Uani 1 1 d . . . H10 H 0.972 0.3429 0.4806 0.046 Uiso 1 1 calc R . . C11 C 0.6001(3) 0.17333(16) 0.48823(10) 0.0432(4) Uani 1 1 d . . . H11 H 0.5597 0.1071 0.465 0.052 Uiso 1 1 calc R . . C12 C 0.4642(3) 0.21794(15) 0.54525(10) 0.0403(4) Uani 1 1 d . . . H12 H 0.3346 0.1824 0.5612 0.048 Uiso 1 1 calc R . . C13 C 0.3640(2) 0.36410(14) 0.63983(9) 0.0333(3) Uani 1 1 d . . . C14 C 0.3362(2) 0.57257(15) 0.77341(9) 0.0371(3) Uani 1 1 d . . . H14 H 0.4761 0.5984 0.764 0.044 Uiso 1 1 calc R . . C15 C 0.1912(3) 0.62158(15) 0.83373(9) 0.0376(4) Uani 1 1 d . . . C16 C 0.2440(3) 0.72157(17) 0.86645(11) 0.0482(4) Uani 1 1 d . . . H16 H 0.3758 0.7549 0.8509 0.058 Uiso 1 1 calc R . . C17 C 0.1059(4) 0.77316(18) 0.92160(11) 0.0561(5) Uani 1 1 d . . . H17 H 0.143 0.8427 0.9424 0.067 Uiso 1 1 calc R . . C18 C -0.0858(3) 0.72448(19) 0.94687(10) 0.0540(5) Uani 1 1 d . . . C19 C -0.1332(3) 0.6223(2) 0.91536(11) 0.0538(5) Uani 1 1 d . . . H19 H -0.2619 0.5865 0.9327 0.065 Uiso 1 1 calc R . . C20 C 0.0003(3) 0.57144(18) 0.85988(10) 0.0449(4) Uani 1 1 d . . . H20 H -0.0376 0.5019 0.8393 0.054 Uiso 1 1 calc R . . C21 C -0.2357(4) 0.7797(3) 1.00688(14) 0.0779(7) Uani 1 1 d . . . H21A H -0.3614 0.7333 1.0173 0.117 Uiso 0.5 1 calc PR . . H21B H -0.2906 0.8765 0.9807 0.117 Uiso 0.5 1 calc PR . . H21C H -0.1528 0.7654 1.0617 0.117 Uiso 0.5 1 calc PR . . H21D H -0.1751 0.8501 1.0225 0.117 Uiso 0.5 1 calc PR . . H21E H -0.2459 0.707 1.0591 0.117 Uiso 0.5 1 calc PR . . H21F H -0.3837 0.8181 0.9781 0.117 Uiso 0.5 1 calc PR . . N1 N 0.7853(2) 0.21758(12) 0.46355(8) 0.0399(3) Uani 1 1 d . . . N2 N 0.4228(2) 0.45253(12) 0.67803(8) 0.0328(3) Uani 1 1 d . . . H2 H 0.549(3) 0.4837(17) 0.6698(10) 0.039 Uiso 1 1 d . . . N3 N 0.2754(2) 0.49503(12) 0.73334(8) 0.0355(3) Uani 1 1 d . . . O4 O 0.18856(18) 0.32332(11) 0.65272(7) 0.0447(3) Uani 1 1 d . . . O1W O 0.80244(19) 0.57361(12) 0.65678(7) 0.0397(3) Uani 1 1 d . . . H1W H 0.930(4) 0.532(2) 0.6803(13) 0.06 Uiso 1 1 d . . . H2W H 0.795(3) 0.658(2) 0.6538(13) 0.06 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0388(8) 0.0297(7) 0.0364(7) -0.0110(6) 0.0036(6) -0.0072(6) C2 0.0343(7) 0.0337(7) 0.0353(7) -0.0139(6) 0.0065(6) -0.0076(6) C3 0.0427(8) 0.0316(7) 0.0356(7) -0.0140(6) 0.0080(6) -0.0094(6) C4 0.0502(9) 0.0406(8) 0.0421(8) -0.0167(7) 0.0173(7) -0.0058(7) C5 0.0430(9) 0.0501(9) 0.0556(10) -0.0158(7) 0.0205(7) -0.0120(7) C6 0.0408(8) 0.0405(8) 0.0553(10) -0.0145(7) 0.0097(7) -0.0163(7) C7 0.0451(9) 0.0318(7) 0.0436(8) -0.0155(6) 0.0007(7) -0.0084(6) O1 0.0582(7) 0.0529(7) 0.0582(7) -0.0387(6) 0.0200(6) -0.0180(6) O2 0.0548(7) 0.0460(7) 0.0818(9) -0.0364(6) -0.0022(6) -0.0143(6) O3 0.0583(7) 0.0507(7) 0.0539(7) -0.0338(5) 0.0205(6) -0.0240(6) C8 0.0325(7) 0.0305(7) 0.0319(7) -0.0118(5) 0.0043(6) -0.0070(5) C9 0.0371(8) 0.0349(7) 0.0353(7) -0.0175(6) 0.0069(6) -0.0105(6) C10 0.0409(8) 0.0398(8) 0.0416(8) -0.0206(6) 0.0108(6) -0.0116(6) C11 0.0512(9) 0.0400(8) 0.0477(9) -0.0255(7) 0.0048(7) -0.0116(7) C12 0.0418(8) 0.0407(8) 0.0465(8) -0.0210(7) 0.0053(7) -0.0152(6) C13 0.0328(7) 0.0355(7) 0.0356(7) -0.0141(6) 0.0052(6) -0.0105(6) C14 0.0351(8) 0.0434(8) 0.0388(8) -0.0184(6) 0.0099(6) -0.0125(6) C15 0.0408(8) 0.0413(8) 0.0332(7) -0.0158(6) 0.0081(6) -0.0059(6) C16 0.0584(10) 0.0474(9) 0.0469(9) -0.0231(7) 0.0133(8) -0.0152(8) C17 0.0786(13) 0.0489(10) 0.0449(9) -0.0268(8) 0.0067(9) -0.0017(9) C18 0.0561(11) 0.0644(11) 0.0341(8) -0.0177(8) 0.0057(8) 0.0125(9) C19 0.0457(9) 0.0782(13) 0.0405(9) -0.0247(9) 0.0128(7) -0.0071(9) C20 0.0439(9) 0.0582(10) 0.0383(8) -0.0216(7) 0.0108(7) -0.0118(7) C21 0.0778(15) 0.0998(17) 0.0512(11) -0.0387(11) 0.0096(10) 0.0212(13) N1 0.0466(8) 0.0382(7) 0.0397(7) -0.0201(5) 0.0070(5) -0.0066(5) N2 0.0309(6) 0.0391(7) 0.0364(6) -0.0201(5) 0.0129(5) -0.0125(5) N3 0.0345(6) 0.0414(7) 0.0368(6) -0.0194(5) 0.0113(5) -0.0098(5) O4 0.0386(6) 0.0570(7) 0.0527(6) -0.0297(5) 0.0148(5) -0.0227(5) O1W 0.0378(6) 0.0376(6) 0.0527(6) -0.0239(5) 0.0076(5) -0.0124(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(2) . ? C1 C6 1.393(2) . ? C1 C7 1.490(2) . ? C2 C3 1.3954(19) . ? C2 H2A 0.95 . ? C3 O3 1.3583(17) . ? C3 C4 1.388(2) . ? C4 C5 1.382(2) . ? C4 H4 0.95 . ? C5 C6 1.380(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2185(19) . ? C7 O1 1.310(2) . ? O1 H1 0.88(3) . ? O3 H3 0.95(3) . ? C8 C9 1.385(2) . ? C8 C12 1.396(2) . ? C8 C13 1.497(2) . ? C9 C10 1.387(2) . ? C9 H9 0.95 . ? C10 N1 1.3392(19) . ? C10 H10 0.95 . ? C11 N1 1.332(2) . ? C11 C12 1.373(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 O4 1.2315(18) . ? C13 N2 1.3532(19) . ? C14 N3 1.280(2) . ? C14 C15 1.464(2) . ? C14 H14 0.95 . ? C15 C16 1.392(2) . ? C15 C20 1.396(2) . ? C16 C17 1.389(2) . ? C16 H16 0.95 . ? C17 C18 1.391(3) . ? C17 H17 0.95 . ? C18 C19 1.389(3) . ? C18 C21 1.506(2) . ? C19 C20 1.374(2) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C21 H21D 0.98 . ? C21 H21E 0.98 . ? C21 H21F 0.98 . ? N2 N3 1.3835(17) . ? N2 H2 0.891(19) . ? O1W H1W 0.85(2) . ? O1W H2W 0.87(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 C2 C1 C6 120.72(13) . . ? C2 C1 C7 120.78(13) . . ? C6 C1 C7 118.49(13) . . ? C1 C2 C3 119.57(13) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? O3 C3 C4 117.76(12) . . ? O3 C3 C2 122.63(13) . . ? C4 C3 C2 119.61(14) . . ? C5 C4 C3 120.20(14) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.54(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 119.27(15) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O2 C7 O1 123.50(14) . . ? O2 C7 C1 122.20(15) . . ? O1 C7 C1 114.30(13) . . ? C7 O1 H1 113.1(16) . . ? C3 O3 H3 110.6(14) . . ? C9 C8 C12 117.79(13) . . ? C9 C8 C13 125.02(13) . . ? C12 C8 C13 117.19(13) . . ? C8 C9 C10 118.98(13) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? N1 C10 C9 123.20(14) . . ? N1 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? N1 C11 C12 123.78(14) . . ? N1 C11 H11 118.1 . . ? C12 C11 H11 118.1 . . ? C11 C12 C8 119.02(14) . . ? C11 C12 H12 120.5 . . ? C8 C12 H12 120.5 . . ? O4 C13 N2 122.42(13) . . ? O4 C13 C8 119.75(13) . . ? N2 C13 C8 117.83(13) . . ? N3 C14 C15 120.29(14) . . ? N3 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C20 118.41(14) . . ? C16 C15 C14 119.36(14) . . ? C20 C15 C14 122.23(14) . . ? C17 C16 C15 120.69(17) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 120.94(17) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C18 C17 117.63(15) . . ? C19 C18 C21 121.2(2) . . ? C17 C18 C21 121.17(19) . . ? C20 C19 C18 122.10(18) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C15 120.19(17) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C21 H21D 109.5 . . ? H21A C21 H21D 141.1 . . ? H21B C21 H21D 56.3 . . ? H21C C21 H21D 56.3 . . ? C18 C21 H21E 109.5 . . ? H21A C21 H21E 56.3 . . ? H21B C21 H21E 141.1 . . ? H21C C21 H21E 56.3 . . ? H21D C21 H21E 109.5 . . ? C18 C21 H21F 109.5 . . ? H21A C21 H21F 56.3 . . ? H21B C21 H21F 56.3 . . ? H21C C21 H21F 141.1 . . ? H21D C21 H21F 109.5 . . ? H21E C21 H21F 109.5 . . ? C11 N1 C10 117.21(13) . . ? C13 N2 N3 116.43(12) . . ? C13 N2 H2 124.3(11) . . ? N3 N2 H2 119.3(11) . . ? C14 N3 N2 116.60(13) . . ? H1W O1W H2W 106.3(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 C6 C1 C2 C3 0.3(2) . . . . ? C7 C1 C2 C3 -178.68(13) . . . . ? C1 C2 C3 O3 176.37(13) . . . . ? C1 C2 C3 C4 -2.7(2) . . . . ? O3 C3 C4 C5 -176.13(14) . . . . ? C2 C3 C4 C5 3.0(2) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 C1 -1.6(3) . . . . ? C2 C1 C6 C5 1.8(2) . . . . ? C7 C1 C6 C5 -179.14(14) . . . . ? C2 C1 C7 O2 174.87(14) . . . . ? C6 C1 C7 O2 -4.1(2) . . . . ? C2 C1 C7 O1 -4.5(2) . . . . ? C6 C1 C7 O1 176.51(14) . . . . ? C12 C8 C9 C10 0.4(2) . . . . ? C13 C8 C9 C10 -179.17(13) . . . . ? C8 C9 C10 N1 0.4(2) . . . . ? N1 C11 C12 C8 0.7(3) . . . . ? C9 C8 C12 C11 -0.9(2) . . . . ? C13 C8 C12 C11 178.71(13) . . . . ? C9 C8 C13 O4 174.61(13) . . . . ? C12 C8 C13 O4 -4.9(2) . . . . ? C9 C8 C13 N2 -4.9(2) . . . . ? C12 C8 C13 N2 175.55(12) . . . . ? N3 C14 C15 C16 -170.17(14) . . . . ? N3 C14 C15 C20 9.8(2) . . . . ? C20 C15 C16 C17 -2.1(3) . . . . ? C14 C15 C16 C17 177.92(15) . . . . ? C15 C16 C17 C18 1.3(3) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C16 C17 C18 C21 179.80(17) . . . . ? C17 C18 C19 C20 -1.2(3) . . . . ? C21 C18 C19 C20 179.34(16) . . . . ? C18 C19 C20 C15 0.4(3) . . . . ? C16 C15 C20 C19 1.2(3) . . . . ? C14 C15 C20 C19 -178.76(15) . . . . ? C12 C11 N1 C10 0.1(2) . . . . ? C9 C10 N1 C11 -0.6(2) . . . . ? O4 C13 N2 N3 0.3(2) . . . . ? C8 C13 N2 N3 179.83(11) . . . . ? C15 C14 N3 N2 -179.54(12) . . . . ? C13 N2 N3 C14 176.09(12) . . . . ? 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 O1 H1 N1 0.88(3) 1.77(3) 2.6317(16) 167(2) . C10 H10 O2 0.95 3.61 4.025 110 . O3 H3 O4 0.95(3) 1.80(3) 2.7260(16) 165(2) 2_656 N2 H2 O1W 0.891(19) 1.955(19) 2.8402(17) 172.0(16) . O1W H1W N3 0.85(2) 2.21(2) 3.0270(17) 160.5(19) 1_655 O1W H1W O4 0.85(2) 2.61(2) 3.2225(17) 129.3(17) 1_655 O1W H2W O2 0.87(2) 1.88(2) 2.7411(16) 171(2) 2_766