# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Andreas Lemmerer' _publ_contact_author_email ANDREAS.LEMMERER@GMAIL.COM _publ_section_title ; Simultaneous covalent and supramolecular synthesis of pharmaceutical co-crystals using the API isoniazid: an ideal supramolecular reagent. ; _publ_requested_category FO loop_ _publ_author_name 'Andreas Lemmerer' 'Joel Bernstein' 'Volker Kahlenberg' # Attachment 'Lemmerer_and_Bernstein_1-9.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-04-03 at 13:57:58 # 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 : 8anp159_p excalibur data_1 _database_code_depnum_ccdc_archive 'CCDC 746444' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-09-04T10:12:20-00:00 _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 ; (malonic acid).(isonicotinic acid hydrazide)2 ; _chemical_formula_moiety '2(C6 H7 N3 O), C3 H4 O4' _chemical_formula_sum 'C15 H18 N6 O6' _chemical_formula_weight 378.35 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 7.7489(15) _cell_length_b 28.027(6) _cell_length_c 3.8702(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 840.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2654 _cell_measurement_theta_min 2.9961 _cell_measurement_theta_max 28.3729 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.118 _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 0.95 _exptl_absorpt_correction_T_max 0.97 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_number 5103 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 3 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 979 _reflns_number_gt 878 _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^)+(0.0582P)^2^+0.0092P] 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 979 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 593 friedel pairs' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.224 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 '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 0.6506(3) 0.34739(8) 0.5344(6) 0.0180(5) Uani 1 1 d . . . C2 C 0.7020(3) 0.39327(8) 0.6235(7) 0.0288(6) Uani 1 1 d . . . H2A H 0.8178 0.4032 0.5882 0.035 Uiso 1 1 calc R . . C3 C 0.5832(3) 0.42393(8) 0.7628(7) 0.0321(6) Uani 1 1 d . . . H3 H 0.6193 0.4552 0.824 0.039 Uiso 1 1 calc R . . C5 C 0.3690(3) 0.36742(8) 0.7351(7) 0.0246(6) Uani 1 1 d . . . H5 H 0.2526 0.3584 0.7754 0.029 Uiso 1 1 calc R . . C6 C 0.4812(3) 0.33453(8) 0.5949(7) 0.0219(5) Uani 1 1 d . . . H6 H 0.4423 0.3033 0.5403 0.026 Uiso 1 1 calc R . . C7 C 0.7747(3) 0.31076(8) 0.3926(6) 0.0194(5) Uani 1 1 d . . . N1 N 0.9168(3) 0.32784(7) 0.2449(5) 0.0224(5) Uani 1 1 d . . . N2 N 0.4195(3) 0.41176(6) 0.8161(5) 0.0219(5) Uani 1 1 d . . . N3 N 1.0448(3) 0.29855(7) 0.0935(7) 0.0312(5) Uani 1 1 d . . . O1 O 0.7439(2) 0.26797(5) 0.4169(5) 0.0345(5) Uani 1 1 d . . . H1 H 0.934(4) 0.3583(11) 0.212(9) 0.052 Uiso 1 1 d . . . H3A H 0.989(4) 0.2784(11) -0.054(9) 0.052 Uiso 1 1 d . . . H3B H 1.093(4) 0.2796(11) 0.283(9) 0.052 Uiso 1 1 d . . . C8 C 0.0957(3) 0.46356(7) 1.2143(6) 0.0161(5) Uani 1 1 d . . . C9 C 0 0.5 1.4323(8) 0.0177(7) Uani 1 2 d S . . H9A H 0.0836 0.5168 1.5829 0.021 Uiso 0.5 1 calc PR . . H9B H -0.0836 0.4832 1.5829 0.021 Uiso 0.5 1 calc PR . . O2 O 0.2480(2) 0.47635(5) 1.1215(5) 0.0254(4) Uani 1 1 d . . . H2 H 0.2988 0.4531 1.029 0.038 Uiso 1 1 calc R . . O3 O 0.0294(2) 0.42523(5) 1.1356(5) 0.0264(4) 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 0.0202(12) 0.0137(11) 0.0203(12) 0.0024(9) 0.0004(9) 0.0016(9) C2 0.0197(13) 0.0216(12) 0.0450(15) -0.0074(11) 0.0113(13) -0.0047(10) C3 0.0286(15) 0.0180(11) 0.0497(16) -0.0073(12) 0.0125(13) -0.0038(11) C5 0.0176(12) 0.0241(12) 0.0320(14) 0.0015(11) 0.0038(11) -0.0019(10) C6 0.0211(12) 0.0147(11) 0.0298(13) -0.0002(9) 0.0015(11) -0.0016(10) C7 0.0209(12) 0.0155(11) 0.0217(11) -0.0003(9) -0.0016(11) 0.0009(9) N1 0.0211(11) 0.0129(9) 0.0332(11) 0.0008(8) 0.0089(10) 0.0029(8) N2 0.0205(11) 0.0191(10) 0.0260(10) 0.0014(8) 0.0036(9) 0.0027(8) N3 0.0298(12) 0.0221(11) 0.0417(13) 0.0051(9) 0.0136(12) 0.0102(9) O1 0.0350(11) 0.0136(8) 0.0548(12) -0.0005(8) 0.0173(11) 0.0006(8) C8 0.0178(12) 0.0140(10) 0.0163(10) 0.0036(9) -0.0017(10) 0.0023(9) C9 0.0167(17) 0.0179(15) 0.0184(16) 0 0 0.0019(13) O2 0.0205(9) 0.0178(8) 0.0380(10) -0.0036(7) 0.0081(9) 0.0017(7) O3 0.0280(10) 0.0157(8) 0.0353(9) -0.0050(7) 0.0065(9) -0.0048(7) #----------------------------------------------------------------------------# # 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 1.381(3) . ? C1 C2 1.389(3) . ? C1 C7 1.510(3) . ? C2 C3 1.370(3) . ? C2 H2A 0.95 . ? C3 N2 1.330(3) . ? C3 H3 0.95 . ? C5 N2 1.340(3) . ? C5 C6 1.378(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.226(3) . ? C7 N1 1.330(3) . ? N1 N3 1.415(3) . ? N1 H1 0.87(3) . ? N3 H3A 0.91(3) . ? N3 H3B 0.98(3) . ? C8 O3 1.229(3) . ? C8 O2 1.285(3) . ? C8 C9 1.518(3) . ? C9 C8 1.518(3) 2_565 ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? O2 H2 0.84 . ? 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 118.1(2) . . ? C6 C1 C7 119.3(2) . . ? C2 C1 C7 122.5(2) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? N2 C3 C2 122.8(2) . . ? N2 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? N2 C5 C6 121.9(2) . . ? N2 C5 H5 119 . . ? C6 C5 H5 119 . . ? C5 C6 C1 119.4(2) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O1 C7 N1 123.1(2) . . ? O1 C7 C1 120.9(2) . . ? N1 C7 C1 116.03(19) . . ? C7 N1 N3 123.36(19) . . ? C7 N1 H1 123(2) . . ? N3 N1 H1 113(2) . . ? C3 N2 C5 118.7(2) . . ? N1 N3 H3A 107(2) . . ? N1 N3 H3B 105.7(19) . . ? H3A N3 H3B 108(3) . . ? O3 C8 O2 124.0(2) . . ? O3 C8 C9 121.43(18) . . ? O2 C8 C9 114.60(17) . . ? C8 C9 C8 112.5(3) . 2_565 ? C8 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 2_565 . ? C8 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 2_565 . ? H9A C9 H9B 107.8 . . ? C8 O2 H2 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(4) . . . . ? C7 C1 C2 C3 -177.5(2) . . . . ? C1 C2 C3 N2 -0.2(4) . . . . ? N2 C5 C6 C1 -0.2(4) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? C7 C1 C6 C5 177.8(2) . . . . ? C6 C1 C7 O1 -19.8(3) . . . . ? C2 C1 C7 O1 156.9(2) . . . . ? C6 C1 C7 N1 160.6(2) . . . . ? C2 C1 C7 N1 -22.7(3) . . . . ? O1 C7 N1 N3 1.6(4) . . . . ? C1 C7 N1 N3 -178.8(2) . . . . ? C2 C3 N2 C5 1.0(4) . . . . ? C6 C5 N2 C3 -0.8(4) . . . . ? O3 C8 C9 C8 -93.4(2) . . . 2_565 ? O2 C8 C9 C8 86.34(18) . . . 2_565 ? 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 O2 H2 N2 0.84 1.7 2.538(2) 172 . C5 H5 O3 0.95 2.91 3.458(3) 118 . N1 H1 O3 0.87(3) 2.04(3) 2.897(3) 168(3) 1_654 N3 H3B O1 0.98(3) 2.12(3) 3.073(3) 164(3) 4_556 _chemical_name_common '(malonic acid).(isonicotinic acid hydrazide)2' ###END data_2 _database_code_depnum_ccdc_archive 'CCDC 746445' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-03T17:00:37-00:00 _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 ; (succinic acid).(isonicotinic acid hydrazide)2 ; _chemical_formula_moiety 'C6 H7 N3 O, 0.5(C4 H6 O4)' _chemical_formula_sum 'C8 H10 N3 O3' _chemical_formula_weight 196.19 #----------------------------------------------------------------------------# # 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 6.9976(4) _cell_length_b 19.5601(10) _cell_length_c 7.1495(5) _cell_angle_alpha 90 _cell_angle_beta 114.892(8) _cell_angle_gamma 90 _cell_volume 887.7(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3252 _cell_measurement_theta_min 3.1162 _cell_measurement_theta_max 28.3578 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.115 _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 0.95 _exptl_absorpt_correction_T_max 0.96 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_number 5573 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.31 _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 1659 _reflns_number_gt 1386 _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, 1997)' _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^)+(0.0529P)^2^+0.1050P] 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 1659 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.169 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # 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 0.70146(18) 0.32425(7) 0.53890(19) 0.0181(3) Uani 1 1 d . . . C2 C 0.51522(19) 0.31490(7) 0.5612(2) 0.0209(3) Uani 1 1 d . . . H2A H 0.4419 0.3522 0.5783 0.025 Uiso 1 1 calc R . . C3 C 0.44083(19) 0.24932(7) 0.5577(2) 0.0213(3) Uani 1 1 d . . . H3 H 0.3162 0.2434 0.5727 0.026 Uiso 1 1 calc R . . C5 C 0.71799(19) 0.20283(7) 0.5102(2) 0.0230(3) Uani 1 1 d . . . H5 H 0.7872 0.1646 0.4916 0.028 Uiso 1 1 calc R . . C6 C 0.80330(19) 0.26675(7) 0.5125(2) 0.0213(3) Uani 1 1 d . . . H6 H 0.9279 0.2711 0.4964 0.026 Uiso 1 1 calc R . . C7 C 0.80573(19) 0.39288(7) 0.5557(2) 0.0189(3) Uani 1 1 d . . . N1 N 0.68082(17) 0.44700(6) 0.53134(18) 0.0214(3) Uani 1 1 d . . . H1 H 0.548(3) 0.4426(8) 0.500(2) 0.032 Uiso 1 1 d . . . N2 N 0.54003(16) 0.19385(6) 0.53355(17) 0.0211(3) Uani 1 1 d . . . N3 N 0.75793(17) 0.51491(6) 0.5708(2) 0.0223(3) Uani 1 1 d . . . H3A H 0.821(3) 0.5240(8) 0.489(3) 0.034 Uiso 1 1 d . . . H3B H 0.858(3) 0.5155(8) 0.703(3) 0.034 Uiso 1 1 d . . . O1 O 0.99341(13) 0.39756(5) 0.59259(15) 0.0261(3) Uani 1 1 d . . . C8 C 0.20256(19) 0.07076(7) 0.5239(2) 0.0182(3) Uani 1 1 d . . . C9 C 0.10977(19) 0.00025(7) 0.5038(2) 0.0203(3) Uani 1 1 d . . . H9A H 0.2015 -0.0273 0.6197 0.024 Uiso 1 1 calc R . . H9B H 0.1051 -0.0208 0.3791 0.024 Uiso 1 1 calc R . . O2 O 0.39267(13) 0.07046(5) 0.52698(16) 0.0244(3) Uani 1 1 d . . . H2 H 0.439(2) 0.1179(9) 0.535(3) 0.037 Uiso 1 1 d . . . O3 O 0.11386(15) 0.12247(5) 0.53590(18) 0.0358(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 0.0168(6) 0.0199(7) 0.0155(6) 0.0003(5) 0.0048(5) -0.0001(5) C2 0.0203(6) 0.0181(7) 0.0254(7) -0.0007(6) 0.0108(5) 0.0014(5) C3 0.0171(6) 0.0229(7) 0.0259(7) 0.0008(6) 0.0111(5) -0.0005(5) C5 0.0192(6) 0.0200(7) 0.0296(8) -0.0024(6) 0.0101(6) 0.0026(5) C6 0.0162(6) 0.0232(7) 0.0256(7) -0.0006(6) 0.0099(5) -0.0007(5) C7 0.0187(6) 0.0207(7) 0.0174(7) 0.0003(5) 0.0077(5) -0.0008(5) N1 0.0148(5) 0.0168(6) 0.0302(7) -0.0009(5) 0.0072(5) -0.0029(4) N2 0.0184(5) 0.0191(6) 0.0241(6) 0.0009(5) 0.0072(5) -0.0008(4) N3 0.0198(6) 0.0170(6) 0.0310(7) -0.0005(5) 0.0114(5) -0.0043(4) O1 0.0192(5) 0.0225(5) 0.0393(6) 0.0016(4) 0.0150(4) -0.0020(4) C8 0.0168(6) 0.0189(7) 0.0184(7) 0.0017(5) 0.0069(5) 0.0013(5) C9 0.0207(7) 0.0183(7) 0.0227(7) -0.0004(6) 0.0098(5) -0.0005(5) O2 0.0189(5) 0.0170(5) 0.0399(6) -0.0001(4) 0.0150(4) -0.0009(4) O3 0.0279(5) 0.0194(6) 0.0683(8) -0.0003(5) 0.0281(5) 0.0012(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 1.3864(18) . ? C1 C2 1.3902(18) . ? C1 C7 1.5083(18) . ? C2 C3 1.3806(18) . ? C2 H2A 0.93 . ? C3 N2 1.3377(17) . ? C3 H3 0.93 . ? C5 N2 1.3360(17) . ? C5 C6 1.3827(19) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 O1 1.2292(15) . ? C7 N1 1.3367(17) . ? N1 N3 1.4168(15) . ? N1 H1 0.866(17) . ? N3 H3A 0.887(18) . ? N3 H3B 0.910(17) . ? C8 O3 1.2084(16) . ? C8 O2 1.3212(15) . ? C8 C9 1.5054(18) . ? C9 C9 1.514(2) 3_556 ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? O2 H2 0.977(18) . ? 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 118.00(11) . . ? C6 C1 C7 118.27(11) . . ? C2 C1 C7 123.61(11) . . ? C3 C2 C1 118.99(12) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? N2 C3 C2 122.94(11) . . ? N2 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? N2 C5 C6 122.54(12) . . ? N2 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C5 C6 C1 119.41(12) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O1 C7 N1 123.37(11) . . ? O1 C7 C1 121.37(11) . . ? N1 C7 C1 115.24(11) . . ? C7 N1 N3 122.90(10) . . ? C7 N1 H1 121.8(10) . . ? N3 N1 H1 115.1(10) . . ? C5 N2 C3 118.11(11) . . ? N1 N3 H3A 108.1(11) . . ? N1 N3 H3B 106.4(10) . . ? H3A N3 H3B 107.3(15) . . ? O3 C8 O2 123.11(12) . . ? O3 C8 C9 124.05(11) . . ? O2 C8 C9 112.84(10) . . ? C8 C9 C9 113.55(13) . 3_556 ? C8 C9 H9A 108.9 . . ? C9 C9 H9A 108.9 3_556 . ? C8 C9 H9B 108.9 . . ? C9 C9 H9B 108.9 3_556 . ? H9A C9 H9B 107.7 . . ? C8 O2 H2 107.7(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.45(19) . . . . ? C7 C1 C2 C3 -175.42(12) . . . . ? C1 C2 C3 N2 0.0(2) . . . . ? N2 C5 C6 C1 -0.3(2) . . . . ? C2 C1 C6 C5 -0.29(19) . . . . ? C7 C1 C6 C5 175.81(12) . . . . ? C6 C1 C7 O1 -16.50(19) . . . . ? C2 C1 C7 O1 159.36(13) . . . . ? C6 C1 C7 N1 164.66(12) . . . . ? C2 C1 C7 N1 -19.48(18) . . . . ? O1 C7 N1 N3 -8.0(2) . . . . ? C1 C7 N1 N3 170.77(12) . . . . ? C6 C5 N2 C3 0.8(2) . . . . ? C2 C3 N2 C5 -0.61(19) . . . . ? O3 C8 C9 C9 1.0(2) . . . 3_556 ? O2 C8 C9 C9 -178.99(14) . . . 3_556 ? 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 O2 H2 N2 0.98(2) 1.65(2) 2.617(1) 172(2) . C3 H3 O3 0.93 2.71 3.3340(16) 125.0 . N1 H1 N3 0.87(2) 2.15(2) 2.937(2) 151(1) 3_666 N1 H1 N1 0.87(2) 2.64(2) 3.154(2) 119(1) 3_666 N3 H3A O1 0.89(2) 2.24(2) 3.006(2) 145(1) 3_766 N3 H3B O2 0.91(2) 2.26(2) 3.084(2) 151(1) 2_656 _chemical_name_common '(succinic acid).(isonicotinic acid hydrazide)2' ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 746446' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-03T15:07:47-00:00 _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 ; (glutaric acid).(isonicotinic acid hydrazide) ; _chemical_formula_moiety 'C6 H7 N3 O, C5 H8 O4' _chemical_formula_sum 'C11 H15 N3 O5' _chemical_formula_weight 269.26 #----------------------------------------------------------------------------# # 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 5.0641(5) _cell_length_b 8.1495(10) _cell_length_c 16.3114(17) _cell_angle_alpha 76.668(10) _cell_angle_beta 81.845(8) _cell_angle_gamma 73.046(10) _cell_volume 624.54(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2044 _cell_measurement_theta_min 3.1761 _cell_measurement_theta_max 28.5302 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_unetI/netI 0.0542 _diffrn_reflns_number 4020 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 2295 _reflns_number_gt 1717 _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^)+(0.0405P)^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 2295 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.165 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # 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 0.7386(3) 0.9401(2) 0.29921(9) 0.0190(4) Uani 1 1 d . . . C2 C 0.4822(3) 0.9905(2) 0.34329(10) 0.0231(4) Uani 1 1 d . . . H2A H 0.3371 1.0824 0.3173 0.028 Uiso 1 1 calc R . . C3 C 0.4422(3) 0.9045(2) 0.42564(10) 0.0264(4) Uani 1 1 d . . . H3 H 0.2664 0.9394 0.4554 0.032 Uiso 1 1 calc R . . C5 C 0.8863(3) 0.7290(2) 0.42293(10) 0.0288(4) Uani 1 1 d . . . H5 H 1.0289 0.6382 0.4508 0.035 Uiso 1 1 calc R . . C6 C 0.9442(3) 0.8074(2) 0.34064(10) 0.0228(4) Uani 1 1 d . . . H6 H 1.1228 0.771 0.3127 0.027 Uiso 1 1 calc R . . C7 C 0.8026(3) 1.02251(19) 0.20984(10) 0.0187(3) Uani 1 1 d . . . N1 N 0.5873(3) 1.08806(17) 0.16194(8) 0.0222(3) Uani 1 1 d . . . H1 H 0.432(4) 1.066(2) 0.1782(11) 0.033 Uiso 1 1 d . . . N2 N 0.6385(3) 0.77461(18) 0.46549(8) 0.0285(4) Uani 1 1 d . . . N3 N 0.6233(3) 1.1636(2) 0.07511(9) 0.0249(3) Uani 1 1 d . . . H3A H 0.774(4) 1.097(3) 0.0518(12) 0.037 Uiso 1 1 d . . . H3B H 0.661(4) 1.265(3) 0.0737(11) 0.037 Uiso 1 1 d . . . O1 O 1.0407(2) 1.02687(14) 0.18155(7) 0.0254(3) Uani 1 1 d . . . C8 C 0.3043(3) 0.6246(2) 0.65446(10) 0.0221(4) Uani 1 1 d . . . C9 C 0.2766(3) 0.5037(2) 0.73821(10) 0.0227(4) Uani 1 1 d . . . H7A H 0.4198 0.5039 0.7737 0.027 Uiso 1 1 calc R . . H7B H 0.3136 0.3833 0.7285 0.027 Uiso 1 1 calc R . . C10 C -0.0055(3) 0.5512(2) 0.78661(10) 0.0225(4) Uani 1 1 d . . . H12A H -0.1518 0.5704 0.7484 0.027 Uiso 1 1 calc R . . H12B H -0.0298 0.6621 0.8055 0.027 Uiso 1 1 calc R . . C11 C -0.0397(3) 0.4089(2) 0.86341(9) 0.0220(4) Uani 1 1 d . . . H11A H -0.2285 0.4444 0.8912 0.026 Uiso 1 1 calc R . . H11B H -0.0217 0.2993 0.844 0.026 Uiso 1 1 calc R . . C12 C 0.1668(3) 0.3733(2) 0.92696(9) 0.0196(4) Uani 1 1 d . . . O2 O 0.5561(2) 0.57912(17) 0.61629(8) 0.0365(3) Uani 1 1 d . . . H2 H 0.573(4) 0.656(3) 0.5652(14) 0.055 Uiso 1 1 d . . . O3 O 0.1239(2) 0.74847(16) 0.62483(7) 0.0377(3) Uani 1 1 d . . . O4 O 0.2096(2) 0.21376(15) 0.97448(7) 0.0279(3) Uani 1 1 d . . . H4 H 0.337(4) 0.204(2) 1.0081(12) 0.042 Uiso 1 1 d . . . O5 O 0.2826(2) 0.47892(15) 0.93539(6) 0.0260(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 0.0184(8) 0.0199(9) 0.0218(8) -0.0069(7) -0.0025(7) -0.0075(7) C2 0.0198(8) 0.0259(9) 0.0236(9) -0.0063(7) -0.0029(7) -0.0046(7) C3 0.0200(9) 0.0341(10) 0.0259(9) -0.0099(8) 0.0015(7) -0.0070(8) C5 0.0256(9) 0.0297(10) 0.0273(10) -0.0015(8) -0.0037(8) -0.0040(8) C6 0.0185(8) 0.0244(9) 0.0233(9) -0.0039(7) 0.0003(7) -0.0041(7) C7 0.0180(8) 0.0131(8) 0.0253(9) -0.0060(7) -0.0009(7) -0.0034(6) N1 0.0172(7) 0.0267(8) 0.0199(7) 0.0011(6) -0.0011(6) -0.0063(6) N2 0.0288(8) 0.0352(9) 0.0210(7) -0.0039(7) 0.0015(6) -0.0110(7) N3 0.0256(8) 0.0248(9) 0.0205(8) 0.0006(6) -0.0011(6) -0.0056(6) O1 0.0159(6) 0.0328(7) 0.0258(6) -0.0018(5) 0.0001(5) -0.0080(5) C8 0.0212(9) 0.0250(9) 0.0212(9) -0.0072(7) -0.0001(7) -0.0068(7) C9 0.0199(8) 0.0229(9) 0.0237(9) -0.0026(7) -0.0028(7) -0.0044(7) C10 0.0186(8) 0.0236(9) 0.0241(9) -0.0027(7) -0.0026(7) -0.0050(7) C11 0.0189(8) 0.0242(9) 0.0231(9) -0.0034(7) -0.0019(7) -0.0070(7) C12 0.0169(8) 0.0235(9) 0.0170(8) -0.0067(7) 0.0061(6) -0.0046(7) O2 0.0272(7) 0.0408(8) 0.0261(7) 0.0060(6) 0.0066(6) 0.0005(6) O3 0.0272(7) 0.0356(8) 0.0349(7) 0.0093(6) -0.0002(6) 0.0013(6) O4 0.0326(7) 0.0248(7) 0.0265(6) 0.0014(5) -0.0114(5) -0.0089(5) O5 0.0265(6) 0.0300(7) 0.0252(6) -0.0059(5) -0.0025(5) -0.0130(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 C6 1.384(2) . ? C1 C2 1.390(2) . ? C1 C7 1.491(2) . ? C2 C3 1.381(2) . ? C2 H2A 0.95 . ? C3 N2 1.335(2) . ? C3 H3 0.95 . ? C5 N2 1.340(2) . ? C5 C6 1.378(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.2357(18) . ? C7 N1 1.3396(19) . ? N1 N3 1.4170(19) . ? N1 H1 0.853(18) . ? N3 H3A 0.89(2) . ? N3 H3B 0.900(19) . ? C8 O3 1.2038(19) . ? C8 O2 1.3254(19) . ? C8 C9 1.504(2) . ? C9 C10 1.521(2) . ? C9 H7A 0.99 . ? C9 H7B 0.99 . ? C10 C11 1.526(2) . ? C10 H12A 0.99 . ? C10 H12B 0.99 . ? C11 C12 1.498(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 O5 1.2149(18) . ? C12 O4 1.3252(19) . ? O2 H2 0.93(2) . ? O4 H4 0.878(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 118.21(14) . . ? C6 C1 C7 118.61(14) . . ? C2 C1 C7 123.17(14) . . ? C3 C2 C1 118.81(15) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? N2 C3 C2 123.23(15) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C5 C6 123.15(15) . . ? N2 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C1 119.09(15) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O1 C7 N1 122.28(14) . . ? O1 C7 C1 121.88(13) . . ? N1 C7 C1 115.82(13) . . ? C7 N1 N3 121.17(13) . . ? C7 N1 H1 121.8(11) . . ? N3 N1 H1 115.5(11) . . ? C3 N2 C5 117.50(14) . . ? N1 N3 H3A 109.0(12) . . ? N1 N3 H3B 105.6(11) . . ? H3A N3 H3B 106.2(16) . . ? O3 C8 O2 123.22(15) . . ? O3 C8 C9 125.27(15) . . ? O2 C8 C9 111.51(13) . . ? C8 C9 C10 114.32(13) . . ? C8 C9 H7A 108.7 . . ? C10 C9 H7A 108.7 . . ? C8 C9 H7B 108.7 . . ? C10 C9 H7B 108.7 . . ? H7A C9 H7B 107.6 . . ? C9 C10 C11 112.24(13) . . ? C9 C10 H12A 109.2 . . ? C11 C10 H12A 109.2 . . ? C9 C10 H12B 109.2 . . ? C11 C10 H12B 109.2 . . ? H12A C10 H12B 107.9 . . ? C12 C11 C10 113.57(12) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? O5 C12 O4 122.79(13) . . ? O5 C12 C11 124.16(14) . . ? O4 C12 C11 113.04(13) . . ? C8 O2 H2 111.0(13) . . ? C12 O4 H4 106.5(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 -1.1(2) . . . . ? C7 C1 C2 C3 179.20(13) . . . . ? C1 C2 C3 N2 0.1(2) . . . . ? N2 C5 C6 C1 0.1(2) . . . . ? C2 C1 C6 C5 1.0(2) . . . . ? C7 C1 C6 C5 -179.28(14) . . . . ? C6 C1 C7 O1 -27.0(2) . . . . ? C2 C1 C7 O1 152.71(15) . . . . ? C6 C1 C7 N1 151.72(14) . . . . ? C2 C1 C7 N1 -28.6(2) . . . . ? O1 C7 N1 N3 1.2(2) . . . . ? C1 C7 N1 N3 -177.49(13) . . . . ? C2 C3 N2 C5 1.0(2) . . . . ? C6 C5 N2 C3 -1.1(2) . . . . ? O3 C8 C9 C10 -1.1(2) . . . . ? O2 C8 C9 C10 178.50(13) . . . . ? C8 C9 C10 C11 170.38(12) . . . . ? C9 C10 C11 C12 60.64(18) . . . . ? C10 C11 C12 O5 25.1(2) . . . . ? C10 C11 C12 O4 -155.58(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 O2 H2 N2 0.93(2) 1.73(2) 2.656(2) 172(2) . C3 H3 O3 0.95 2.95 3.546(2) 122.2 . O4 H4 N3 0.88(2) 1.85(2) 2.723(2) 175(2) 1_546 N1 H1 O1 0.85(2) 2.09(2) 2.914(2) 164(2) 1_455 N3 H3A O4 0.89(2) 2.64(2) 3.203(2) 122(1) 2_666 N3 H3B O5 0.90(2) 2.15(2) 3.050(2) 175(2) 2_676 _chemical_name_common '(glutaric acid).(isonicotinic acid hydrazide)' ###END data_4 _database_code_depnum_ccdc_archive 'CCDC 746447' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-10-01T07:46:04-00:00 _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 ; (adipic acid).(isonicotinic acid hydrazide)2 ; _chemical_formula_moiety 'C6 H10 O4, 2(C6 H7 N3 O)' _chemical_formula_sum 'C18 H24 N6 O6' _chemical_formula_weight 420.43 #----------------------------------------------------------------------------# # 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 6.3361(4) _cell_length_b 3.8795(2) _cell_length_c 39.723(2) _cell_angle_alpha 90 _cell_angle_beta 90.122(5) _cell_angle_gamma 90 _cell_volume 976.42(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2805 _cell_measurement_theta_min 3.3356 _cell_measurement_theta_max 67.2154 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.43 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.921 _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 0.82 _exptl_absorpt_correction_T_max 0.89 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_number 4606 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 66.95 _diffrn_reflns_theta_full 66.95 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1733 _reflns_number_gt 1570 _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^)+(0.0792P)^2^+0.1400P] 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 0.0071(11) _refine_ls_number_reflns 1733 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.185 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # 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 0.7555(2) -0.0495(3) 0.16943(3) 0.0230(3) Uani 1 1 d . . . C2 C 0.5520(2) 0.0689(4) 0.16330(3) 0.0292(3) Uani 1 1 d . . . H2A H 0.4449 0.0443 0.1798 0.035 Uiso 1 1 calc R . . C3 C 0.5086(2) 0.2234(4) 0.13264(3) 0.0295(3) Uani 1 1 d . . . H3 H 0.3693 0.304 0.1286 0.035 Uiso 1 1 calc R . . C5 C 0.8470(2) 0.1454(4) 0.11434(3) 0.0312(3) Uani 1 1 d . . . H5 H 0.9505 0.1709 0.0972 0.037 Uiso 1 1 calc R . . C6 C 0.9041(2) -0.0143(4) 0.14427(3) 0.0282(3) Uani 1 1 d . . . H6 H 1.0436 -0.0982 0.1474 0.034 Uiso 1 1 calc R . . C7 C 0.82308(19) -0.2145(3) 0.20207(3) 0.0221(3) Uani 1 1 d . . . N1 N 0.68591(18) -0.1942(3) 0.22761(3) 0.0251(3) Uani 1 1 d . . . N2 N 0.65258(18) 0.2646(3) 0.10859(3) 0.0284(3) Uani 1 1 d . . . N3 N 0.72513(17) -0.3622(3) 0.25879(3) 0.0248(3) Uani 1 1 d . . . O1 O 0.99532(14) -0.3597(2) 0.20489(2) 0.0284(3) Uani 1 1 d . . . H1 H 0.563(3) -0.080(5) 0.2260(4) 0.043 Uiso 1 1 d . . . H3A H 0.811(3) -0.219(5) 0.2717(4) 0.043 Uiso 1 1 d . . . H3B H 0.802(3) -0.555(5) 0.2536(5) 0.043 Uiso 1 1 d . . . C8 C 0.3313(2) 0.6984(3) 0.05345(3) 0.0248(3) Uani 1 1 d . . . C9 C 0.2608(2) 0.8457(3) 0.02016(3) 0.0245(3) Uani 1 1 d . . . H9A H 0.291 0.6744 0.0023 0.029 Uiso 1 1 calc R . . H9B H 0.3466 1.053 0.0153 0.029 Uiso 1 1 calc R . . C10 C 0.0293(2) 0.9442(3) 0.01789(3) 0.0246(3) Uani 1 1 d . . . H10A H 0 1.1352 0.0337 0.03 Uiso 1 1 calc R . . H10B H -0.0588 0.7447 0.0245 0.03 Uiso 1 1 calc R . . O2 O 0.52900(15) 0.5867(3) 0.05194(2) 0.0327(3) Uani 1 1 d . . . O3 O 0.22390(16) 0.6802(3) 0.07848(2) 0.0373(3) Uani 1 1 d . . . H2 H 0.567(3) 0.478(6) 0.0730(5) 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 0.0263(7) 0.0211(6) 0.0216(6) -0.0018(5) -0.0042(5) -0.0007(5) C2 0.0257(7) 0.0379(7) 0.0239(6) 0.0023(5) -0.0008(5) 0.0023(5) C3 0.0266(7) 0.0356(7) 0.0263(6) 0.0014(5) -0.0046(5) 0.0038(6) C5 0.0313(7) 0.0381(7) 0.0241(6) 0.0030(5) 0.0009(5) 0.0034(6) C6 0.0259(7) 0.0319(7) 0.0268(6) 0.0004(5) -0.0025(5) 0.0033(5) C7 0.0238(7) 0.0200(6) 0.0226(6) -0.0020(4) -0.0045(5) -0.0009(5) N1 0.0252(6) 0.0299(6) 0.0203(5) 0.0039(4) -0.0035(4) 0.0029(5) N2 0.0320(6) 0.0306(6) 0.0227(5) 0.0006(4) -0.0041(4) 0.0015(5) N3 0.0267(6) 0.0280(6) 0.0198(5) 0.0027(4) -0.0046(4) -0.0017(4) O1 0.0254(5) 0.0332(5) 0.0266(5) 0.0014(3) -0.0038(4) 0.0056(4) C8 0.0273(7) 0.0233(6) 0.0238(6) -0.0008(5) -0.0030(5) 0.0002(5) C9 0.0267(7) 0.0248(6) 0.0220(6) 0.0021(5) -0.0014(5) 0.0005(5) C10 0.0267(7) 0.0243(6) 0.0229(7) 0.0024(5) -0.0010(5) 0.0007(5) O2 0.0275(5) 0.0467(6) 0.0239(5) 0.0059(4) -0.0024(4) 0.0095(4) O3 0.0338(6) 0.0531(7) 0.0251(5) 0.0084(4) 0.0019(4) 0.0096(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 C6 1.3813(19) . ? C1 C2 1.3898(19) . ? C1 C7 1.5070(16) . ? C2 C3 1.3843(18) . ? C2 H2A 0.95 . ? C3 N2 1.3322(18) . ? C3 H3 0.95 . ? C5 N2 1.3351(18) . ? C5 C6 1.3878(18) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.2330(16) . ? C7 N1 1.3397(17) . ? N1 N3 1.4211(14) . ? N1 H1 0.90(2) . ? N3 H3A 0.93(2) . ? N3 H3B 0.92(2) . ? C8 O3 1.2082(17) . ? C8 O2 1.3267(17) . ? C8 C9 1.5077(16) . ? C9 C10 1.5182(18) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C10 1.531(2) 3_575 ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? O2 H2 0.97(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 118.28(11) . . ? C6 C1 C7 118.15(11) . . ? C2 C1 C7 123.57(12) . . ? C3 C2 C1 118.69(12) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? N2 C3 C2 123.20(12) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C5 C6 122.68(13) . . ? N2 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C1 C6 C5 119.16(12) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? O1 C7 N1 122.25(11) . . ? O1 C7 C1 121.46(11) . . ? N1 C7 C1 116.29(11) . . ? C7 N1 N3 121.37(10) . . ? C7 N1 H1 122.6(11) . . ? N3 N1 H1 116.0(12) . . ? C3 N2 C5 117.96(11) . . ? N1 N3 H3A 107.8(12) . . ? N1 N3 H3B 105.6(12) . . ? H3A N3 H3B 107.3(16) . . ? O3 C8 O2 123.50(11) . . ? O3 C8 C9 125.26(12) . . ? O2 C8 C9 111.23(11) . . ? C8 C9 C10 115.60(10) . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C10 111.00(13) . 3_575 ? C9 C10 H10A 109.4 . . ? C10 C10 H10A 109.4 3_575 . ? C9 C10 H10B 109.4 . . ? C10 C10 H10B 109.4 3_575 . ? H10A C10 H10B 108 . . ? C8 O2 H2 109.5(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 -1.44(19) . . . . ? C7 C1 C2 C3 178.59(12) . . . . ? C1 C2 C3 N2 0.0(2) . . . . ? C2 C1 C6 C5 1.75(19) . . . . ? C7 C1 C6 C5 -178.27(12) . . . . ? N2 C5 C6 C1 -0.7(2) . . . . ? C6 C1 C7 O1 -10.41(17) . . . . ? C2 C1 C7 O1 169.56(12) . . . . ? C6 C1 C7 N1 169.58(11) . . . . ? C2 C1 C7 N1 -10.45(18) . . . . ? O1 C7 N1 N3 -4.78(18) . . . . ? C1 C7 N1 N3 175.23(10) . . . . ? C2 C3 N2 C5 1.1(2) . . . . ? C6 C5 N2 C3 -0.8(2) . . . . ? O3 C8 C9 C10 -6.22(19) . . . . ? O2 C8 C9 C10 173.37(11) . . . . ? C8 C9 C10 C10 -174.29(12) . . . 3_575 ? 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 O2 H2 N2 0.96(2) 1.73(2) 2.689(1) 175(2) . C3 H3 O3 0.95 2.63 3.3178(16) 129 . N1 H1 N3 0.89(2) 2.11(2) 2.956(2) 159(2) 2_655 N3 H3A O1 0.93(2) 2.08(2) 3.001(1) 173(2) 2_755 N3 H3B O1 0.91(2) 2.40(2) 2.989(1) 122(1) 2_745 _chemical_name_common '(adipic acid).(isonicotinic acid hydrazide)2' ###END data_5 _database_code_depnum_ccdc_archive 'CCDC 746448' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-03T17:17:50-00:00 _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 ; (pimelic acid).(isonicotinic acid hydrazide) ; _chemical_formula_moiety 'C7 H12 O4, C6 H7 N3 O' _chemical_formula_sum 'C13 H19 N3 O5' _chemical_formula_weight 297.31 #----------------------------------------------------------------------------# # 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 5.1055(5) _cell_length_b 7.4175(6) _cell_length_c 19.3653(15) _cell_angle_alpha 94.328(6) _cell_angle_beta 93.120(6) _cell_angle_gamma 103.660(7) _cell_volume 708.61(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2673 _cell_measurement_theta_min 2.9351 _cell_measurement_theta_max 28.394 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.108 _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 0.94 _exptl_absorpt_correction_T_max 0.97 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_unetI/netI 0.0385 _diffrn_reflns_number 4574 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 2616 _reflns_number_gt 2063 _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^)+(0.0471P)^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 2616 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.168 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # 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 0.4665(3) 0.22611(19) 0.31781(7) 0.0170(3) Uani 1 1 d . . . C2 C 0.7145(3) 0.3298(2) 0.34769(7) 0.0200(3) Uani 1 1 d . . . H2A H 0.8506 0.388 0.3195 0.024 Uiso 1 1 calc R . . C3 C 0.7604(3) 0.3471(2) 0.41890(7) 0.0247(4) Uani 1 1 d . . . H3 H 0.9295 0.4204 0.439 0.03 Uiso 1 1 calc R . . C5 C 0.3422(3) 0.1630(2) 0.43193(7) 0.0238(3) Uani 1 1 d . . . H5 H 0.2129 0.1023 0.4614 0.029 Uiso 1 1 calc R . . C6 C 0.2762(3) 0.1406(2) 0.36130(7) 0.0202(3) Uani 1 1 d . . . H6 H 0.1043 0.0682 0.3427 0.024 Uiso 1 1 calc R . . C7 C 0.3913(3) 0.20768(19) 0.24111(7) 0.0163(3) Uani 1 1 d . . . N1 N 0.5920(2) 0.20361(17) 0.19992(6) 0.0195(3) Uani 1 1 d . . . H1 H 0.757(4) 0.208(2) 0.2169(8) 0.029 Uiso 1 1 d . . . N2 N 0.5792(2) 0.26589(17) 0.46107(6) 0.0242(3) Uani 1 1 d . . . N3 N 0.5526(2) 0.1979(2) 0.12653(6) 0.0209(3) Uani 1 1 d . . . H3A H 0.437(3) 0.263(2) 0.1181(8) 0.031 Uiso 1 1 d . . . H3B H 0.465(3) 0.080(3) 0.1097(8) 0.031 Uiso 1 1 d . . . O1 O 0.15924(18) 0.20017(15) 0.21781(5) 0.0244(3) Uani 1 1 d . . . C8 C 0.4919(3) 0.2505(2) 0.63429(7) 0.0195(3) Uani 1 1 d . . . C9 C 0.5649(3) 0.2890(2) 0.71118(7) 0.0197(3) Uani 1 1 d . . . H9A H 0.6644 0.421 0.7213 0.024 Uiso 1 1 calc R . . H9B H 0.6877 0.2107 0.7251 0.024 Uiso 1 1 calc R . . C10 C 0.3228(3) 0.2515(2) 0.75453(7) 0.0214(3) Uani 1 1 d . . . H10A H 0.2217 0.12 0.744 0.026 Uiso 1 1 calc R . . H10B H 0.2012 0.3312 0.7412 0.026 Uiso 1 1 calc R . . C11 C 0.3981(3) 0.2880(2) 0.83219(7) 0.0197(3) Uani 1 1 d . . . H11A H 0.5198 0.2087 0.8458 0.024 Uiso 1 1 calc R . . H11B H 0.4976 0.4198 0.8431 0.024 Uiso 1 1 calc R . . C12 C 0.1516(3) 0.2483(2) 0.87416(7) 0.0237(3) Uani 1 1 d . . . H12A H 0.0554 0.1156 0.8641 0.028 Uiso 1 1 calc R . . H12B H 0.0274 0.3246 0.8592 0.028 Uiso 1 1 calc R . . C13 C 0.2201(3) 0.2892(2) 0.95201(7) 0.0209(3) Uani 1 1 d . . . H13A H 0.3582 0.2227 0.9662 0.025 Uiso 1 1 calc R . . H13B H 0.2996 0.4244 0.9626 0.025 Uiso 1 1 calc R . . C14 C -0.0192(3) 0.2327(2) 0.99356(7) 0.0180(3) Uani 1 1 d . . . O2 O 0.68688(19) 0.33633(15) 0.59769(5) 0.0294(3) Uani 1 1 d . . . H2 H 0.642(3) 0.303(3) 0.5514(10) 0.044 Uiso 1 1 d . . . O3 O 0.2815(2) 0.15126(16) 0.60863(5) 0.0311(3) Uani 1 1 d . . . O4 O 0.0246(2) 0.31020(15) 1.05888(5) 0.0253(3) Uani 1 1 d . . . H4 H -0.124(4) 0.274(2) 1.0807(9) 0.038 Uiso 1 1 d . . . O5 O -0.23054(18) 0.12669(15) 0.97196(5) 0.0252(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 0.0167(7) 0.0180(7) 0.0174(7) 0.0005(6) 0.0026(5) 0.0066(6) C2 0.0174(7) 0.0239(8) 0.0169(7) 0.0034(6) 0.0043(5) 0.0004(6) C3 0.0193(7) 0.0311(9) 0.0196(7) -0.0001(6) 0.0003(6) -0.0009(7) C5 0.0228(8) 0.0279(9) 0.0204(8) 0.0056(6) 0.0086(6) 0.0031(6) C6 0.0164(7) 0.0223(8) 0.0208(7) 0.0009(6) 0.0027(5) 0.0024(6) C7 0.0140(7) 0.0147(7) 0.0190(7) 0.0001(5) 0.0006(5) 0.0018(5) N1 0.0149(6) 0.0316(7) 0.0124(6) 0.0011(5) 0.0008(4) 0.0068(5) N2 0.0237(7) 0.0303(8) 0.0168(6) 0.0025(5) 0.0026(5) 0.0027(6) N3 0.0226(7) 0.0275(8) 0.0125(6) 0.0000(5) 0.0010(5) 0.0068(6) O1 0.0145(5) 0.0382(7) 0.0201(5) 0.0006(4) -0.0005(4) 0.0064(4) C8 0.0178(7) 0.0211(8) 0.0196(7) 0.0027(6) 0.0036(6) 0.0042(6) C9 0.0183(7) 0.0216(8) 0.0180(7) 0.0009(6) 0.0014(5) 0.0028(6) C10 0.0181(7) 0.0277(8) 0.0180(7) 0.0038(6) 0.0016(5) 0.0043(6) C11 0.0186(7) 0.0205(8) 0.0188(7) 0.0011(6) 0.0021(5) 0.0024(6) C12 0.0188(7) 0.0337(9) 0.0169(7) 0.0007(6) 0.0020(5) 0.0036(6) C13 0.0165(7) 0.0271(8) 0.0178(7) 0.0004(6) 0.0016(5) 0.0034(6) C14 0.0192(8) 0.0218(8) 0.0152(7) 0.0026(6) -0.0004(5) 0.0091(6) O2 0.0247(6) 0.0413(7) 0.0151(5) 0.0015(5) 0.0053(4) -0.0068(5) O3 0.0227(6) 0.0417(7) 0.0214(6) 0.0006(5) 0.0012(4) -0.0062(5) O4 0.0220(6) 0.0368(7) 0.0144(5) -0.0019(4) 0.0048(4) 0.0022(5) O5 0.0182(5) 0.0331(6) 0.0206(5) -0.0018(5) 0.0026(4) -0.0001(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 1.3864(19) . ? C1 C6 1.3906(18) . ? C1 C7 1.5017(18) . ? C2 C3 1.3774(19) . ? C2 H2A 0.95 . ? C3 N2 1.3335(17) . ? C3 H3 0.95 . ? C5 N2 1.3378(18) . ? C5 C6 1.379(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.2319(16) . ? C7 N1 1.3366(18) . ? N1 N3 1.4206(16) . ? N1 H1 0.880(17) . ? N3 H3A 0.863(18) . ? N3 H3B 0.912(19) . ? C8 O3 1.2066(16) . ? C8 O2 1.3208(16) . ? C8 C9 1.5041(18) . ? C9 C10 1.5152(18) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.5197(18) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.5178(18) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C13 1.5202(18) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.4939(19) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 O5 1.2074(16) . ? C14 O4 1.3339(17) . ? O2 H2 0.914(19) . ? O4 H4 0.885(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 C2 C1 C6 118.27(12) . . ? C2 C1 C7 122.98(11) . . ? C6 C1 C7 118.72(12) . . ? C3 C2 C1 118.95(12) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? N2 C3 C2 123.26(13) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C5 C6 123.26(12) . . ? N2 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C1 118.66(13) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? O1 C7 N1 122.22(12) . . ? O1 C7 C1 121.75(12) . . ? N1 C7 C1 116.02(11) . . ? C7 N1 N3 121.88(12) . . ? C7 N1 H1 121.8(10) . . ? N3 N1 H1 116.3(10) . . ? C3 N2 C5 117.59(12) . . ? N1 N3 H3A 106.6(11) . . ? N1 N3 H3B 108.5(9) . . ? H3A N3 H3B 104.3(15) . . ? O3 C8 O2 123.57(12) . . ? O3 C8 C9 124.30(11) . . ? O2 C8 C9 112.13(12) . . ? C8 C9 C10 113.64(11) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 113.39(11) . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C10 112.12(11) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 113.31(11) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 113.21(11) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? O5 C14 O4 122.36(12) . . ? O5 C14 C13 124.88(13) . . ? O4 C14 C13 112.76(12) . . ? C8 O2 H2 109.9(11) . . ? C14 O4 H4 108.9(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 -1.3(2) . . . . ? C7 C1 C2 C3 176.53(13) . . . . ? C1 C2 C3 N2 1.3(2) . . . . ? N2 C5 C6 C1 1.2(2) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? C7 C1 C6 C5 -177.79(13) . . . . ? C2 C1 C7 O1 -144.03(15) . . . . ? C6 C1 C7 O1 33.8(2) . . . . ? C2 C1 C7 N1 34.7(2) . . . . ? C6 C1 C7 N1 -147.45(13) . . . . ? O1 C7 N1 N3 2.6(2) . . . . ? C1 C7 N1 N3 -176.14(12) . . . . ? C2 C3 N2 C5 0.1(2) . . . . ? C6 C5 N2 C3 -1.3(2) . . . . ? O3 C8 C9 C10 -20.7(2) . . . . ? O2 C8 C9 C10 160.18(12) . . . . ? C8 C9 C10 C11 179.18(12) . . . . ? C9 C10 C11 C12 -179.70(13) . . . . ? C10 C11 C12 C13 -178.25(12) . . . . ? C11 C12 C13 C14 -174.39(13) . . . . ? C12 C13 C14 O5 17.1(2) . . . . ? C12 C13 C14 O4 -163.80(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 O2 H2 N2 0.91(2) 1.75(2) 2.659(2) 173(2) . C5 H5 O3 0.95 2.84 3.4583(17) 123.7 . O4 H4 N3 0.89(2) 1.90(2) 2.789(2) 179(2) 1_456 N1 H1 O1 0.88(2) 2.07(2) 2.904(2) 159(2) 1_655 N3 H3A O4 0.86(2) 2.45(2) 3.243(2) 153(2) 1_554 N3 H3B O5 0.91(2) 2.20(2) 3.039(2) 153(2) 2_556 _chemical_name_common '(pimelic acid).(isonicotinic acid hydrazide)' ###END data_6 _database_code_depnum_ccdc_archive 'CCDC 746449' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-03T16:24:46-00:00 _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 ; (4-hydroxybenzoic acid).(isonicotinic acid hydrazide) ; _chemical_formula_moiety 'C6 H7 N3 O, C7 H6 O3' _chemical_formula_sum 'C13 H13 N3 O4' _chemical_formula_weight 275.26 #----------------------------------------------------------------------------# # 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 12.9083(5) _cell_length_b 4.98980(10) _cell_length_c 20.3294(9) _cell_angle_alpha 90 _cell_angle_beta 91.850(4) _cell_angle_gamma 90 _cell_volume 1308.73(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4487 _cell_measurement_theta_min 3.0022 _cell_measurement_theta_max 28.3865 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.106 _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 0.95 _exptl_absorpt_correction_T_max 0.96 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_number 8040 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2417 _reflns_number_gt 2005 _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^)+(0.0399P)^2^+0.1707P] 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 0.021(2) _refine_ls_number_reflns 2417 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.186 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # 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 0.39415(9) 0.8184(2) 0.57605(6) 0.0206(3) Uani 1 1 d . . . C2 C 0.37941(10) 0.6049(3) 0.61799(7) 0.0297(3) Uani 1 1 d . . . H2A H 0.319 0.4969 0.6136 0.036 Uiso 1 1 calc R . . C3 C 0.45404(11) 0.5508(3) 0.66653(7) 0.0361(4) Uani 1 1 d . . . H3 H 0.4425 0.4058 0.6957 0.043 Uiso 1 1 calc R . . C5 C 0.55456(10) 0.8998(3) 0.63430(7) 0.0357(4) Uani 1 1 d . . . H5 H 0.6161 1.003 0.6395 0.043 Uiso 1 1 calc R . . C6 C 0.48304(9) 0.9719(3) 0.58551(6) 0.0281(3) Uani 1 1 d . . . H6 H 0.4945 1.1246 0.5588 0.034 Uiso 1 1 calc R . . C7 C 0.31759(9) 0.8959(2) 0.52229(6) 0.0199(3) Uani 1 1 d . . . N1 N 0.26971(8) 0.6934(2) 0.49127(5) 0.0236(3) Uani 1 1 d . . . H1 H 0.2816(11) 0.525(3) 0.5004(7) 0.035 Uiso 1 1 d . . . N2 N 0.54129(9) 0.6916(2) 0.67454(6) 0.0353(3) Uani 1 1 d . . . N3 N 0.18945(9) 0.7381(2) 0.44314(6) 0.0255(3) Uani 1 1 d . . . H3A H 0.2181(11) 0.757(3) 0.4019(8) 0.038 Uiso 1 1 d . . . H3B H 0.1593(12) 0.899(3) 0.4546(7) 0.038 Uiso 1 1 d . . . O1 O 0.30180(7) 1.13221(17) 0.50779(4) 0.0273(2) Uani 1 1 d . . . C8 C 0.84249(9) 0.3429(3) 0.79888(6) 0.0221(3) Uani 1 1 d . . . C9 C 0.84990(9) 0.5028(3) 0.85491(6) 0.0255(3) Uani 1 1 d . . . H9 H 0.8017 0.6445 0.8602 0.031 Uiso 1 1 calc R . . C10 C 0.92598(9) 0.4591(3) 0.90288(6) 0.0255(3) Uani 1 1 d . . . H10 H 0.9303 0.5705 0.9408 0.031 Uiso 1 1 calc R . . C11 C 0.99634(9) 0.2515(2) 0.89557(6) 0.0212(3) Uani 1 1 d . . . C12 C 0.99095(9) 0.0919(2) 0.83943(6) 0.0243(3) Uani 1 1 d . . . H12 H 1.0399 -0.0478 0.8339 0.029 Uiso 1 1 calc R . . C13 C 0.91422(9) 0.1371(3) 0.79174(6) 0.0244(3) Uani 1 1 d . . . H13 H 0.9103 0.0267 0.7537 0.029 Uiso 1 1 calc R . . C14 C 0.76055(9) 0.3869(3) 0.74763(6) 0.0265(3) Uani 1 1 d . . . O2 O 0.69339(8) 0.5750(2) 0.76292(5) 0.0436(3) Uani 1 1 d . . . H2 H 0.6415(15) 0.604(4) 0.7284(10) 0.065 Uiso 1 1 d . . . O3 O 0.75383(7) 0.2614(2) 0.69615(5) 0.0375(3) Uani 1 1 d . . . O4 O 1.06937(7) 0.21793(19) 0.94457(4) 0.0297(2) Uani 1 1 d . . . H4 H 1.1038(12) 0.067(4) 0.9412(8) 0.044 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 0.0198(6) 0.0201(6) 0.0217(6) -0.0041(5) -0.0035(5) 0.0023(5) C2 0.0327(7) 0.0240(7) 0.0317(8) 0.0031(6) -0.0091(6) -0.0043(6) C3 0.0466(9) 0.0291(8) 0.0316(8) 0.0052(6) -0.0149(7) 0.0015(6) C5 0.0227(7) 0.0505(9) 0.0332(8) -0.0018(7) -0.0075(6) -0.0051(6) C6 0.0248(7) 0.0329(7) 0.0263(7) 0.0019(6) -0.0048(5) -0.0051(6) C7 0.0188(6) 0.0185(6) 0.0221(6) 0.0001(5) -0.0011(5) -0.0002(5) N1 0.0264(6) 0.0164(5) 0.0271(6) 0.0005(5) -0.0127(5) -0.0007(4) N2 0.0323(7) 0.0425(7) 0.0301(6) -0.0018(6) -0.0121(5) 0.0079(5) N3 0.0271(6) 0.0239(6) 0.0248(6) 0.0002(5) -0.0113(5) -0.0017(5) O1 0.0316(5) 0.0163(5) 0.0333(5) 0.0017(4) -0.0110(4) -0.0005(4) C8 0.0193(6) 0.0266(7) 0.0202(7) 0.0037(5) -0.0020(5) -0.0030(5) C9 0.0216(6) 0.0289(7) 0.0257(7) 0.0006(6) -0.0033(5) 0.0065(5) C10 0.0267(7) 0.0276(7) 0.0220(7) -0.0043(5) -0.0032(5) 0.0039(5) C11 0.0186(6) 0.0223(6) 0.0223(6) 0.0031(5) -0.0046(5) -0.0014(5) C12 0.0241(6) 0.0224(7) 0.0262(7) -0.0006(5) -0.0031(5) 0.0040(5) C13 0.0277(7) 0.0248(7) 0.0204(6) -0.0031(5) -0.0021(5) -0.0020(5) C14 0.0223(7) 0.0332(7) 0.0240(7) 0.0044(6) -0.0019(5) -0.0024(6) O2 0.0376(6) 0.0583(7) 0.0337(6) -0.0060(5) -0.0186(5) 0.0210(5) O3 0.0346(6) 0.0516(7) 0.0257(5) -0.0043(5) -0.0103(4) 0.0006(5) O4 0.0292(5) 0.0290(5) 0.0299(5) -0.0050(4) -0.0140(4) 0.0089(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 1.3816(18) . ? C1 C6 1.3879(18) . ? C1 C7 1.5002(17) . ? C2 C3 1.3831(18) . ? C2 H2A 0.95 . ? C3 N2 1.3327(19) . ? C3 H3 0.95 . ? C5 N2 1.3369(19) . ? C5 C6 1.3808(19) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.2310(15) . ? C7 N1 1.3325(16) . ? N1 N3 1.4195(14) . ? N1 H1 0.875(16) . ? N3 H3A 0.932(16) . ? N3 H3B 0.925(17) . ? C8 C9 1.3915(18) . ? C8 C13 1.3932(18) . ? C8 C14 1.4768(17) . ? C9 C10 1.3789(17) . ? C9 H9 0.95 . ? C10 C11 1.3888(17) . ? C10 H10 0.95 . ? C11 O4 1.3594(15) . ? C11 C12 1.3915(18) . ? C12 C13 1.3820(17) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 O3 1.2202(16) . ? C14 O2 1.3216(17) . ? O2 H2 0.97(2) . ? O4 H4 0.876(18) . ? 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 118.02(12) . . ? C2 C1 C7 123.21(11) . . ? C6 C1 C7 118.75(11) . . ? C1 C2 C3 118.95(12) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? N2 C3 C2 123.42(13) . . ? N2 C3 H3 118.3 . . ? C2 C3 H3 118.3 . . ? N2 C5 C6 123.11(12) . . ? N2 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C1 119.09(13) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O1 C7 N1 122.85(11) . . ? O1 C7 C1 121.42(11) . . ? N1 C7 C1 115.72(10) . . ? C7 N1 N3 121.61(11) . . ? C7 N1 H1 123.7(10) . . ? N3 N1 H1 114.6(10) . . ? C3 N2 C5 117.34(11) . . ? N1 N3 H3A 109.5(9) . . ? N1 N3 H3B 105.4(9) . . ? H3A N3 H3B 108.8(13) . . ? C9 C8 C13 118.65(11) . . ? C9 C8 C14 121.39(11) . . ? C13 C8 C14 119.96(11) . . ? C10 C9 C8 121.12(11) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.71(12) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? O4 C11 C10 116.99(11) . . ? O4 C11 C12 123.08(11) . . ? C10 C11 C12 119.93(11) . . ? C13 C12 C11 119.85(11) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C8 120.72(12) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? O3 C14 O2 122.48(12) . . ? O3 C14 C8 123.93(12) . . ? O2 C14 C8 113.58(11) . . ? C14 O2 H2 112.3(11) . . ? C11 O4 H4 113.0(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.08(19) . . . . ? C7 C1 C2 C3 -179.35(12) . . . . ? C1 C2 C3 N2 -1.2(2) . . . . ? N2 C5 C6 C1 -1.9(2) . . . . ? C2 C1 C6 C5 2.53(19) . . . . ? C7 C1 C6 C5 -179.13(12) . . . . ? C2 C1 C7 O1 143.77(13) . . . . ? C6 C1 C7 O1 -34.49(17) . . . . ? C2 C1 C7 N1 -37.10(17) . . . . ? C6 C1 C7 N1 144.65(12) . . . . ? O1 C7 N1 N3 -6.07(19) . . . . ? C1 C7 N1 N3 174.81(10) . . . . ? C2 C3 N2 C5 2.0(2) . . . . ? C6 C5 N2 C3 -0.4(2) . . . . ? C13 C8 C9 C10 -0.41(19) . . . . ? C14 C8 C9 C10 179.38(12) . . . . ? C8 C9 C10 C11 -0.30(19) . . . . ? C9 C10 C11 O4 -179.83(11) . . . . ? C9 C10 C11 C12 1.18(18) . . . . ? O4 C11 C12 C13 179.74(11) . . . . ? C10 C11 C12 C13 -1.34(18) . . . . ? C11 C12 C13 C8 0.62(19) . . . . ? C9 C8 C13 C12 0.26(18) . . . . ? C14 C8 C13 C12 -179.54(11) . . . . ? C9 C8 C14 O3 176.13(12) . . . . ? C13 C8 C14 O3 -4.08(19) . . . . ? C9 C8 C14 O2 -4.55(17) . . . . ? C13 C8 C14 O2 175.23(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 N2 0.97(2) 1.72(2) 2.682(2) 171(2) . O4 H4 N3 0.88(2) 1.88(2) 2.754(1) 172(2) 4_666 O4 H4 N1 0.88(2) 2.68(2) 3.412(1) 142(1) 4_666 N1 H1 O1 0.88(2) 1.98(2) 2.849(1) 172(1) 1_545 N3 H3A O3 0.93(2) 2.04(2) 2.948(2) 164(1) 3_666 N3 H3B O4 0.93(2) 2.24(2) 3.126(2) 160(1) 4_475 _chemical_name_common '(4-hydroxybenzoic acid).(isonicotinic acid hydrazide)' ###END data_7 _database_code_depnum_ccdc_archive 'CCDC 746450' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-03T23:37:16-00:00 _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 ; (2,4-dihydroxybenzoic acid).(isonicotinic acid hydrazide) ; _chemical_formula_moiety 'C6 H7 N3 O, C7 H6 O4' _chemical_formula_sum 'C13 H13 N3 O5' _chemical_formula_weight 291.26 #----------------------------------------------------------------------------# # 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 8.1931(4) _cell_length_b 5.0698(2) _cell_length_c 30.2815(13) _cell_angle_alpha 90 _cell_angle_beta 94.923(4) _cell_angle_gamma 90 _cell_volume 1253.17(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3900 _cell_measurement_theta_min 3.0677 _cell_measurement_theta_max 28.3803 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.121 _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 0.91 _exptl_absorpt_correction_T_max 0.98 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_number 7598 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2321 _reflns_number_gt 1894 _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^)+(0.0489P)^2^+0.1009P] 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 2321 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.047 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0863 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.168 _refine_diff_density_min -0.262 _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 0.0033 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 0.61085(16) 0.8520(3) 0.12798(4) 0.0142(3) Uani 1 1 d . . . C2 C 0.69204(17) 0.6418(3) 0.14936(4) 0.0182(3) Uani 1 1 d . . . H2A H 0.7568 0.5253 0.1336 0.022 Uiso 1 1 calc R . . C3 C 0.67720(18) 0.6047(3) 0.19404(5) 0.0206(3) Uani 1 1 d . . . H3 H 0.7333 0.4604 0.2085 0.025 Uiso 1 1 calc R . . C5 C 0.51103(18) 0.9668(3) 0.19727(5) 0.0204(3) Uani 1 1 d . . . H5A H 0.448 1.0812 0.2139 0.024 Uiso 1 1 calc R . . C6 C 0.51974(17) 1.0183(3) 0.15279(4) 0.0173(3) Uani 1 1 d . . . H6 H 0.4641 1.1659 0.1393 0.021 Uiso 1 1 calc R . . C7 C 0.61748(17) 0.9106(3) 0.07961(4) 0.0154(3) Uani 1 1 d . . . N1 N 0.63993(15) 0.7037(3) 0.05357(4) 0.0181(3) Uani 1 1 d . . . H1 H 0.644(2) 0.545(4) 0.0626(5) 0.027 Uiso 1 1 d . . . N2 N 0.58768(14) 0.7621(2) 0.21801(4) 0.0200(3) Uani 1 1 d . . . N3 N 0.66315(18) 0.7342(3) 0.00791(4) 0.0217(3) Uani 1 1 d . . . H3A H 0.721(2) 0.878(4) 0.0060(5) 0.033 Uiso 1 1 d . . . H3B H 0.561(2) 0.767(3) -0.0081(6) 0.033 Uiso 1 1 d . . . O1 O 0.60267(13) 1.13808(18) 0.06497(3) 0.0215(3) Uani 1 1 d . . . C8 C 0.40787(17) 0.3721(3) 0.35203(4) 0.0163(3) Uani 1 1 d . . . C9 C 0.47583(17) 0.5273(3) 0.38728(4) 0.0189(3) Uani 1 1 d . . . H9 H 0.5429 0.6732 0.381 0.023 Uiso 1 1 calc R . . C10 C 0.44866(18) 0.4754(3) 0.43060(5) 0.0212(3) Uani 1 1 d . . . H10 H 0.4961 0.5835 0.4539 0.025 Uiso 1 1 calc R . . C11 C 0.34991(17) 0.2607(3) 0.43972(4) 0.0184(3) Uani 1 1 d . . . C12 C 0.28127(17) 0.1015(3) 0.40588(4) 0.0179(3) Uani 1 1 d . . . H12 H 0.2149 -0.0446 0.4125 0.021 Uiso 1 1 calc R . . C13 C 0.30977(17) 0.1562(3) 0.36209(5) 0.0164(3) Uani 1 1 d . . . C14 C 0.43408(17) 0.4353(3) 0.30589(5) 0.0183(3) Uani 1 1 d . . . O2 O 0.53575(13) 0.6321(2) 0.30074(3) 0.0248(3) Uani 1 1 d . . . H2 H 0.545(2) 0.674(4) 0.2710(6) 0.037 Uiso 1 1 d . . . O3 O 0.36556(13) 0.3134(2) 0.27423(3) 0.0257(3) Uani 1 1 d . . . O4 O 0.32273(14) 0.2217(2) 0.48307(3) 0.0270(3) Uani 1 1 d . . . H4 H 0.276(2) 0.081(4) 0.4857(6) 0.04 Uiso 1 1 d . . . O5 O 0.23779(12) -0.0044(2) 0.33045(3) 0.0224(3) Uani 1 1 d . . . H5 H 0.265(2) 0.056(3) 0.3046(6) 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 0.0147(7) 0.0133(7) 0.0146(7) -0.0008(6) 0.0016(5) -0.0038(5) C2 0.0191(8) 0.0172(8) 0.0182(7) -0.0017(6) 0.0016(6) 0.0018(6) C3 0.0240(8) 0.0188(8) 0.0182(7) 0.0030(6) -0.0016(6) 0.0010(6) C5 0.0220(8) 0.0204(8) 0.0195(7) -0.0036(6) 0.0060(6) -0.0013(6) C6 0.0197(8) 0.0133(7) 0.0190(7) 0.0002(6) 0.0022(6) 0.0009(6) C7 0.0152(7) 0.0147(7) 0.0162(7) 0.0000(6) 0.0014(5) -0.0006(6) N1 0.0308(7) 0.0119(6) 0.0120(6) 0.0010(5) 0.0044(5) 0.0008(5) N2 0.0221(7) 0.0230(7) 0.0150(6) -0.0011(5) 0.0015(5) -0.0051(5) N3 0.0348(8) 0.0189(7) 0.0118(6) 0.0005(5) 0.0036(5) 0.0021(6) O1 0.0358(7) 0.0129(5) 0.0160(5) 0.0018(4) 0.0037(4) 0.0028(4) C8 0.0157(7) 0.0163(7) 0.0173(7) 0.0015(6) 0.0028(6) 0.0027(6) C9 0.0183(8) 0.0179(8) 0.0208(7) 0.0023(6) 0.0031(6) -0.0023(6) C10 0.0242(8) 0.0219(8) 0.0171(7) -0.0016(6) 0.0001(6) -0.0025(6) C11 0.0222(8) 0.0189(8) 0.0143(7) 0.0022(6) 0.0030(6) 0.0030(6) C12 0.0192(8) 0.0145(7) 0.0202(7) 0.0026(6) 0.0034(6) -0.0010(6) C13 0.0161(7) 0.0158(7) 0.0173(7) -0.0004(6) 0.0005(5) 0.0039(6) C14 0.0181(8) 0.0174(8) 0.0198(7) -0.0003(6) 0.0045(6) 0.0020(6) O2 0.0296(6) 0.0308(6) 0.0147(5) 0.0042(5) 0.0055(4) -0.0104(5) O3 0.0338(6) 0.0271(6) 0.0166(5) -0.0029(5) 0.0052(4) -0.0051(5) O4 0.0440(7) 0.0236(6) 0.0141(5) 0.0009(5) 0.0065(5) -0.0114(5) O5 0.0309(6) 0.0211(6) 0.0153(5) -0.0015(4) 0.0028(4) -0.0060(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 1.387(2) . ? C1 C6 1.3889(19) . ? C1 C7 1.5003(18) . ? C2 C3 1.3816(19) . ? C2 H2A 0.95 . ? C3 N2 1.3391(19) . ? C3 H3 0.95 . ? C5 N2 1.3407(19) . ? C5 C6 1.3798(19) . ? C5 H5A 0.95 . ? C6 H6 0.95 . ? C7 O1 1.2379(16) . ? C7 N1 1.3344(18) . ? N1 N3 1.4200(16) . ? N1 H1 0.848(17) . ? N3 H3A 0.877(19) . ? N3 H3B 0.946(18) . ? C8 C9 1.402(2) . ? C8 C13 1.407(2) . ? C8 C14 1.4672(19) . ? C9 C10 1.3744(19) . ? C9 H9 0.95 . ? C10 C11 1.398(2) . ? C10 H10 0.95 . ? C11 O4 1.3647(17) . ? C11 C12 1.385(2) . ? C12 C13 1.3938(19) . ? C12 H12 0.95 . ? C13 O5 1.3530(17) . ? C14 O3 1.2345(17) . ? C14 O2 1.3173(17) . ? O2 H2 0.935(19) . ? O4 H4 0.82(2) . ? O5 H5 0.886(18) . ? 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 118.21(12) . . ? C2 C1 C7 123.49(12) . . ? C6 C1 C7 118.30(12) . . ? C3 C2 C1 118.86(13) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? N2 C3 C2 123.23(13) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C5 C6 122.85(13) . . ? N2 C5 H5A 118.6 . . ? C6 C5 H5A 118.6 . . ? C5 C6 C1 119.22(13) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O1 C7 N1 122.35(12) . . ? O1 C7 C1 121.56(12) . . ? N1 C7 C1 116.09(12) . . ? C7 N1 N3 121.77(12) . . ? C7 N1 H1 123.9(11) . . ? N3 N1 H1 114.3(11) . . ? C3 N2 C5 117.62(12) . . ? N1 N3 H3A 105.8(11) . . ? N1 N3 H3B 109.3(10) . . ? H3A N3 H3B 106.4(15) . . ? C9 C8 C13 117.95(12) . . ? C9 C8 C14 121.42(12) . . ? C13 C8 C14 120.61(12) . . ? C10 C9 C8 122.19(13) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 118.78(13) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? O4 C11 C12 122.53(13) . . ? O4 C11 C10 116.61(12) . . ? C12 C11 C10 120.84(13) . . ? C11 C12 C13 119.83(13) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? O5 C13 C12 117.10(12) . . ? O5 C13 C8 122.49(12) . . ? C12 C13 C8 120.41(13) . . ? O3 C14 O2 122.50(12) . . ? O3 C14 C8 122.42(13) . . ? O2 C14 C8 115.08(12) . . ? C14 O2 H2 113.1(11) . . ? C11 O4 H4 109.7(13) . . ? C13 O5 H5 106.9(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 0.9(2) . . . . ? C7 C1 C2 C3 -179.71(13) . . . . ? C1 C2 C3 N2 0.1(2) . . . . ? N2 C5 C6 C1 0.3(2) . . . . ? C2 C1 C6 C5 -1.0(2) . . . . ? C7 C1 C6 C5 179.51(12) . . . . ? C2 C1 C7 O1 -151.19(14) . . . . ? C6 C1 C7 O1 28.2(2) . . . . ? C2 C1 C7 N1 28.9(2) . . . . ? C6 C1 C7 N1 -151.68(13) . . . . ? O1 C7 N1 N3 5.8(2) . . . . ? C1 C7 N1 N3 -174.26(12) . . . . ? C2 C3 N2 C5 -0.8(2) . . . . ? C6 C5 N2 C3 0.6(2) . . . . ? C13 C8 C9 C10 -0.4(2) . . . . ? C14 C8 C9 C10 178.08(13) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C9 C10 C11 O4 -178.18(13) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? O4 C11 C12 C13 178.10(13) . . . . ? C10 C11 C12 C13 -0.4(2) . . . . ? C11 C12 C13 O5 -179.20(12) . . . . ? C11 C12 C13 C8 0.0(2) . . . . ? C9 C8 C13 O5 179.53(12) . . . . ? C14 C8 C13 O5 1.1(2) . . . . ? C9 C8 C13 C12 0.4(2) . . . . ? C14 C8 C13 C12 -178.09(13) . . . . ? C9 C8 C14 O3 -174.45(14) . . . . ? C13 C8 C14 O3 4.0(2) . . . . ? C9 C8 C14 O2 5.41(19) . . . . ? C13 C8 C14 O2 -176.19(13) . . . . ? 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 O2 H2 N2 0.94(2) 1.73(2) 2.660(2) 173(2) . O4 H4 N3 0.82(2) 1.99(2) 2.790(2) 166(2) 4_566 O5 H5 O3 0.89(2) 1.83(2) 2.626(2) 148(2) . N1 H1 O1 0.85(2) 2.09(2) 2.907(2) 161(2) 1_545 N3 H3A O4 0.88(2) 2.32(2) 3.171(2) 163(2) 4_675 N3 H3B O1 0.95(2) 2.14(2) 3.035(2) 156(1) 3_675 _chemical_name_common '(2,4-dihydroxybenzoic acid).(isonicotinic acid hydrazide)' ###END data_8 _database_code_depnum_ccdc_archive 'CCDC 746451' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-05T18:41:51-00:00 _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 ; (3-hydroxybenzoic acid).((Z)-N'-(butan-2-ylidene)isonicotinohydrazide) ; _chemical_formula_moiety 'C10 H13 N3 O, C7 H6 O3' _chemical_formula_sum 'C17 H19 N3 O4' _chemical_formula_weight 329.35 #----------------------------------------------------------------------------# # 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 19.8053(8) _cell_length_b 8.4686(4) _cell_length_c 10.0248(4) _cell_angle_alpha 90 _cell_angle_beta 99.567(4) _cell_angle_gamma 90 _cell_volume 1658.01(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4885 _cell_measurement_theta_min 4.4574 _cell_measurement_theta_max 67.2712 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.79 _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 0.89 _exptl_absorpt_correction_T_max 0.91 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_unetI/netI 0.0443 _diffrn_reflns_number 9383 _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 -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.53 _diffrn_reflns_theta_max 67.34 _diffrn_reflns_theta_full 67.34 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2954 _reflns_number_gt 2482 _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, 1997)' _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^)+(0.1809P)^2^+0.4767P] 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 0.023(2) _refine_ls_number_reflns 2954 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.08 _refine_ls_wR_factor_ref 0.1981 _refine_ls_wR_factor_gt 0.1874 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.575 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.155 #----------------------------------------------------------------------------# # 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 0.35489(9) 0.7906(2) 0.23453(18) 0.0208(5) Uani 1 1 d . . . C2 C 0.38581(9) 0.6946(2) 0.3390(2) 0.0249(5) Uani 1 1 d . . . H2A H 0.3624 0.6055 0.3666 0.03 Uiso 1 1 calc R . . C3 C 0.45161(10) 0.7311(3) 0.4026(2) 0.0269(5) Uani 1 1 d . . . H3 H 0.4727 0.6653 0.4743 0.032 Uiso 1 1 calc R . . C5 C 0.45618(10) 0.9473(3) 0.2666(2) 0.0312(5) Uani 1 1 d . . . H5 H 0.4806 1.0362 0.2417 0.037 Uiso 1 1 calc R . . C6 C 0.39083(10) 0.9194(3) 0.1971(2) 0.0271(5) Uani 1 1 d . . . H6 H 0.371 0.987 0.1255 0.033 Uiso 1 1 calc R . . C7 C 0.28514(9) 0.7565(2) 0.15455(19) 0.0208(5) Uani 1 1 d . . . C15 C 0.14920(11) 0.5179(3) 0.3613(2) 0.0360(6) Uani 1 1 d . . . H15A H 0.1963 0.478 0.3806 0.054 Uiso 1 1 calc R . . H15B H 0.1173 0.4327 0.3734 0.054 Uiso 1 1 calc R . . H15C H 0.1438 0.6047 0.4233 0.054 Uiso 1 1 calc R . . C16 C 0.13425(10) 0.5766(3) 0.2181(2) 0.0266(5) Uani 1 1 d . . . C17 C 0.06272(10) 0.5541(3) 0.1420(2) 0.0357(6) Uani 1 1 d . . . H17A H 0.0488 0.4426 0.1493 0.043 Uiso 1 1 calc R . . H17B H 0.0618 0.5783 0.0451 0.043 Uiso 1 1 calc R . . C18 C 0.01254(13) 0.6612(6) 0.1983(4) 0.0725(11) Uani 1 1 d . . . H18A H 0.0143 0.6391 0.2948 0.109 Uiso 1 1 calc R . . H18B H -0.0339 0.6417 0.1499 0.109 Uiso 1 1 calc R . . H18C H 0.0249 0.7718 0.1865 0.109 Uiso 1 1 calc R . . N1 N 0.24175(8) 0.6781(2) 0.22253(17) 0.0226(4) Uani 1 1 d . . . H1 H 0.2498(13) 0.660(3) 0.308(3) 0.034 Uiso 1 1 d . . . N2 N 0.48667(8) 0.8549(2) 0.36724(17) 0.0280(5) Uani 1 1 d . . . N3 N 0.17619(8) 0.6459(2) 0.15331(16) 0.0235(4) Uani 1 1 d . . . O1 O 0.27051(7) 0.79430(18) 0.03547(13) 0.0271(4) Uani 1 1 d . . . C8 C 0.70690(9) 0.8301(2) 0.6491(2) 0.0241(5) Uani 1 1 d . . . C9 C 0.74759(9) 0.9435(2) 0.60108(19) 0.0225(5) Uani 1 1 d . . . H9 H 0.731 0.9988 0.5198 0.027 Uiso 1 1 calc R . . C10 C 0.81283(9) 0.9760(2) 0.67231(18) 0.0229(5) Uani 1 1 d . . . C11 C 0.83580(10) 0.8984(3) 0.7934(2) 0.0282(5) Uani 1 1 d . . . H11 H 0.8797 0.9222 0.8435 0.034 Uiso 1 1 calc R . . C12 C 0.79458(11) 0.7861(3) 0.8413(2) 0.0313(5) Uani 1 1 d . . . H12 H 0.8106 0.7329 0.9239 0.038 Uiso 1 1 calc R . . C13 C 0.73014(11) 0.7508(3) 0.7695(2) 0.0293(5) Uani 1 1 d . . . H13 H 0.7023 0.6735 0.8023 0.035 Uiso 1 1 calc R . . C14 C 0.63659(10) 0.7966(2) 0.5732(2) 0.0268(5) Uani 1 1 d . . . O2 O 0.61519(7) 0.90202(19) 0.47933(15) 0.0318(4) Uani 1 1 d . . . H2 H 0.5657(15) 0.875(4) 0.440(3) 0.048 Uiso 1 1 d . . . O3 O 0.60290(8) 0.6835(2) 0.59708(19) 0.0439(5) Uani 1 1 d . . . O4 O 0.85490(7) 1.08426(18) 0.62832(15) 0.0288(4) Uani 1 1 d . . . H4 H 0.8350(14) 1.112(4) 0.544(3) 0.043 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 0.0185(9) 0.0237(10) 0.0210(10) -0.0032(7) 0.0058(7) 0.0004(7) C2 0.0205(9) 0.0266(10) 0.0282(10) 0.0005(8) 0.0062(7) -0.0017(7) C3 0.0203(9) 0.0324(11) 0.0276(10) 0.0007(8) 0.0034(7) 0.0009(8) C5 0.0257(10) 0.0346(12) 0.0334(11) 0.0015(9) 0.0054(8) -0.0095(8) C6 0.0257(10) 0.0289(11) 0.0270(10) 0.0024(8) 0.0052(8) -0.0024(8) C7 0.0191(9) 0.0206(9) 0.0233(10) -0.0012(7) 0.0049(7) 0.0019(7) C15 0.0368(11) 0.0432(13) 0.0282(11) 0.0002(9) 0.0059(8) -0.0163(10) C16 0.0224(10) 0.0321(11) 0.0255(10) -0.0056(8) 0.0048(8) -0.0060(8) C17 0.0222(10) 0.0514(14) 0.0337(12) -0.0070(10) 0.0054(8) -0.0105(9) C18 0.0228(12) 0.104(3) 0.090(2) -0.039(2) 0.0080(13) -0.0005(14) N1 0.0164(8) 0.0302(9) 0.0199(8) -0.0008(6) -0.0004(6) -0.0028(6) N2 0.0214(8) 0.0331(10) 0.0298(9) -0.0025(7) 0.0052(7) -0.0040(7) N3 0.0158(8) 0.0308(9) 0.0230(8) -0.0043(7) 0.0006(6) -0.0019(6) O1 0.0232(7) 0.0347(8) 0.0232(8) 0.0028(6) 0.0027(5) -0.0009(6) C8 0.0224(9) 0.0224(10) 0.0276(10) -0.0037(8) 0.0047(7) 0.0009(7) C9 0.0226(9) 0.0246(10) 0.0204(9) -0.0015(7) 0.0040(7) 0.0009(7) C10 0.0206(9) 0.0260(10) 0.0226(9) -0.0036(7) 0.0049(7) 0.0010(7) C11 0.0244(9) 0.0350(12) 0.0245(10) -0.0013(8) 0.0018(8) 0.0007(8) C12 0.0342(11) 0.0343(12) 0.0246(11) 0.0052(8) 0.0023(8) 0.0020(9) C13 0.0301(10) 0.0275(11) 0.0316(11) 0.0028(8) 0.0089(8) -0.0006(8) C14 0.0249(10) 0.0252(10) 0.0309(11) -0.0010(8) 0.0060(8) -0.0009(8) O2 0.0213(7) 0.0370(9) 0.0351(9) 0.0066(6) -0.0008(6) -0.0051(6) O3 0.0322(8) 0.0329(9) 0.0631(11) 0.0097(8) -0.0020(7) -0.0113(7) O4 0.0224(7) 0.0384(9) 0.0250(8) 0.0033(6) 0.0018(6) -0.0069(6) #----------------------------------------------------------------------------# # 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 1.386(3) . ? C1 C6 1.388(3) . ? C1 C7 1.506(2) . ? C2 C3 1.387(3) . ? C2 H2A 0.95 . ? C3 N2 1.337(3) . ? C3 H3 0.95 . ? C5 N2 1.338(3) . ? C5 C6 1.384(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.223(2) . ? C7 N1 1.356(3) . ? C15 C16 1.501(3) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 N3 1.279(3) . ? C16 C17 1.505(3) . ? C17 C18 1.521(4) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? N1 N3 1.394(2) . ? N1 H1 0.86(3) . ? C8 C9 1.390(3) . ? C8 C13 1.391(3) . ? C8 C14 1.499(3) . ? C9 C10 1.396(3) . ? C9 H9 0.95 . ? C10 O4 1.361(2) . ? C10 C11 1.389(3) . ? C11 C12 1.390(3) . ? C11 H11 0.95 . ? C12 C13 1.389(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 O3 1.213(3) . ? C14 O2 1.316(3) . ? O2 H2 1.02(3) . ? O4 H4 0.90(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.93(17) . . ? C2 C1 C7 122.75(17) . . ? C6 C1 C7 118.25(17) . . ? C1 C2 C3 118.64(19) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? N2 C3 C2 122.89(19) . . ? N2 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? N2 C5 C6 123.15(19) . . ? N2 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C1 118.44(19) . . ? C5 C6 H6 120.8 . . ? C1 C6 H6 120.8 . . ? O1 C7 N1 123.46(17) . . ? O1 C7 C1 121.15(16) . . ? N1 C7 C1 115.36(16) . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C15 126.59(17) . . ? N3 C16 C17 115.89(18) . . ? C15 C16 C17 117.52(17) . . ? C16 C17 C18 110.77(19) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 N1 N3 117.48(16) . . ? C7 N1 H1 124.1(17) . . ? N3 N1 H1 117.7(17) . . ? C3 N2 C5 117.94(17) . . ? C16 N3 N1 117.83(16) . . ? C9 C8 C13 120.44(17) . . ? C9 C8 C14 119.89(17) . . ? C13 C8 C14 119.64(18) . . ? C8 C9 C10 119.98(18) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? O4 C10 C11 118.21(16) . . ? O4 C10 C9 122.12(17) . . ? C11 C10 C9 119.66(18) . . ? C10 C11 C12 119.98(18) . . ? C10 C11 H11 120 . . ? C12 C11 H11 120 . . ? C13 C12 C11 120.65(19) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 119.26(19) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? O3 C14 O2 123.67(18) . . ? O3 C14 C8 122.99(19) . . ? O2 C14 C8 113.33(17) . . ? C14 O2 H2 107.6(18) . . ? C10 O4 H4 106.6(18) . . ? 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 176.83(17) . . . . ? C1 C2 C3 N2 -0.1(3) . . . . ? N2 C5 C6 C1 0.7(3) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? C7 C1 C6 C5 -177.25(17) . . . . ? C2 C1 C7 O1 -148.63(19) . . . . ? C6 C1 C7 O1 28.1(3) . . . . ? C2 C1 C7 N1 29.4(3) . . . . ? C6 C1 C7 N1 -153.82(17) . . . . ? N3 C16 C17 C18 -109.4(3) . . . . ? C15 C16 C17 C18 70.0(3) . . . . ? O1 C7 N1 N3 -2.9(3) . . . . ? C1 C7 N1 N3 179.07(15) . . . . ? C2 C3 N2 C5 0.5(3) . . . . ? C6 C5 N2 C3 -0.8(3) . . . . ? C15 C16 N3 N1 -3.3(3) . . . . ? C17 C16 N3 N1 176.04(17) . . . . ? C7 N1 N3 C16 -177.76(17) . . . . ? C13 C8 C9 C10 1.4(3) . . . . ? C14 C8 C9 C10 179.37(17) . . . . ? C8 C9 C10 O4 179.03(17) . . . . ? C8 C9 C10 C11 -2.2(3) . . . . ? O4 C10 C11 C12 -179.48(18) . . . . ? C9 C10 C11 C12 1.7(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C8 -0.4(3) . . . . ? C9 C8 C13 C12 -0.1(3) . . . . ? C14 C8 C13 C12 -178.08(19) . . . . ? C9 C8 C14 O3 168.1(2) . . . . ? C13 C8 C14 O3 -13.9(3) . . . . ? C9 C8 C14 O2 -12.3(3) . . . . ? C13 C8 C14 O2 165.72(18) . . . . ? 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 O2 H2 N2 1.02(3) 1.62(3) 2.636(2) 173(3) . C3 H3 O3 0.95 2.67 3.317(2) 125.8 . O4 H4 N3 0.90(3) 1.98(3) 2.836(2) 159(3) 2_655 N1 H1 O1 0.86(3) 2.29(3) 3.103(2) 160(3) 4_576 _chemical_name_common ;(3-hydroxybenzoic acid).((Z)-N'-(butan-2- ylidene)isonicotinohydrazide) ; ##END data_9 _database_code_depnum_ccdc_archive 'CCDC 746452' #TrackingRef 'Lemmerer_and_Bernstein_1-9.cif' _audit_creation_date 2009-04-06T18:57:05-00:00 _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 ; (3-hydroxybenzoic acid).(N'-(propan-2-ylidene)isonicotinohydrazide) ; _chemical_formula_moiety 'C9 H11 N3 O, C7 H6 O3' _chemical_formula_sum 'C16 H17 N3 O4' _chemical_formula_weight 315.33 #----------------------------------------------------------------------------# # 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 8.6520(3) _cell_length_b 20.8180(8) _cell_length_c 8.7850(4) _cell_angle_alpha 90 _cell_angle_beta 101.679(4) _cell_angle_gamma 90 _cell_volume 1549.57(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3304 _cell_measurement_theta_min 3.0629 _cell_measurement_theta_max 28.3889 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _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 0.96 _exptl_absorpt_correction_T_max 0.98 #----------------------------------------------------------------------------# # 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 ult' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_unetI/netI 0.0514 _diffrn_reflns_number 8294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 2864 _reflns_number_gt 2078 _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^)+(0.0462P)^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 2864 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 0.95 _refine_ls_restrained_S_all 0.95 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.149 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # 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 0.18408(17) 0.32362(7) 0.63747(18) 0.0200(3) Uani 1 1 d . . . C2 C 0.29141(17) 0.30036(7) 0.55367(19) 0.0227(4) Uani 1 1 d . . . H2A H 0.314 0.2557 0.5531 0.027 Uiso 1 1 calc R . . C3 C 0.36509(18) 0.34279(7) 0.47091(19) 0.0250(4) Uani 1 1 d . . . H3 H 0.44 0.3263 0.4155 0.03 Uiso 1 1 calc R . . C5 C 0.23369(19) 0.42797(7) 0.5477(2) 0.0285(4) Uani 1 1 d . . . H5 H 0.2127 0.4728 0.5456 0.034 Uiso 1 1 calc R . . C6 C 0.15696(19) 0.38929(7) 0.6360(2) 0.0270(4) Uani 1 1 d . . . H6 H 0.0868 0.4073 0.6948 0.032 Uiso 1 1 calc R . . C7 C 0.09905(17) 0.28164(7) 0.73169(19) 0.0207(4) Uani 1 1 d . . . C15 C 0.0485(2) 0.09083(8) 0.6069(2) 0.0352(4) Uani 1 1 d . . . H15A H 0.1498 0.1123 0.6095 0.053 Uiso 1 1 calc R . . H15B H -0.0151 0.0926 0.5011 0.053 Uiso 1 1 calc R . . H15C H 0.0673 0.0459 0.6386 0.053 Uiso 1 1 calc R . . C16 C -0.03750(18) 0.12392(7) 0.71588(19) 0.0262(4) Uani 1 1 d . . . C17 C -0.1418(2) 0.08333(9) 0.7929(2) 0.0404(5) Uani 1 1 d . . . H17A H -0.1893 0.11 0.8631 0.061 Uiso 1 1 calc R . . H17B H -0.0792 0.0491 0.8523 0.061 Uiso 1 1 calc R . . H17C H -0.2253 0.0643 0.7136 0.061 Uiso 1 1 calc R . . N1 N 0.06453(15) 0.22193(6) 0.67554(16) 0.0228(3) Uani 1 1 d . . . H1 H 0.0720(19) 0.2134(8) 0.578(2) 0.034 Uiso 1 1 d . . . N2 N 0.33632(14) 0.40578(6) 0.46486(16) 0.0250(3) Uani 1 1 d . . . N3 N -0.03035(15) 0.18389(6) 0.75113(16) 0.0254(3) Uani 1 1 d . . . O1 O 0.06597(13) 0.30165(5) 0.85294(13) 0.0284(3) Uani 1 1 d . . . C8 C 0.37489(17) 0.60104(7) 0.17632(19) 0.0229(4) Uani 1 1 d . . . C9 C 0.29680(17) 0.65974(7) 0.17793(19) 0.0241(4) Uani 1 1 d . . . H9 H 0.2311 0.667 0.2508 0.029 Uiso 1 1 calc R . . C10 C 0.31536(17) 0.70737(7) 0.07297(19) 0.0235(4) Uani 1 1 d . . . C11 C 0.41024(18) 0.69585(8) -0.0343(2) 0.0275(4) Uani 1 1 d . . . H11 H 0.4201 0.7278 -0.1091 0.033 Uiso 1 1 calc R . . C12 C 0.48993(19) 0.63859(8) -0.0331(2) 0.0313(4) Uani 1 1 d . . . H12 H 0.5564 0.6317 -0.1054 0.038 Uiso 1 1 calc R . . C13 C 0.47405(18) 0.59084(8) 0.0728(2) 0.0283(4) Uani 1 1 d . . . H13 H 0.5304 0.5516 0.0744 0.034 Uiso 1 1 calc R . . C14 C 0.3403(2) 0.54912(7) 0.2815(2) 0.0274(4) Uani 1 1 d . . . O2 O 0.43005(13) 0.49752(5) 0.28404(14) 0.0319(3) Uani 1 1 d . . . H2 H 0.398(2) 0.4650(9) 0.352(2) 0.048 Uiso 1 1 d . . . O3 O 0.23573(16) 0.55368(6) 0.35419(17) 0.0471(4) Uani 1 1 d . . . O4 O 0.24476(14) 0.76613(5) 0.06627(15) 0.0322(3) Uani 1 1 d . . . H4 H 0.176(2) 0.7700(9) 0.124(2) 0.048 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 0.0232(8) 0.0209(8) 0.0147(9) 0.0005(7) 0.0011(7) -0.0012(6) C2 0.0234(8) 0.0179(8) 0.0265(10) -0.0009(7) 0.0045(7) 0.0012(7) C3 0.0240(8) 0.0241(9) 0.0285(10) -0.0003(7) 0.0093(7) 0.0008(7) C5 0.0420(10) 0.0164(8) 0.0293(10) -0.0004(7) 0.0122(8) 0.0020(7) C6 0.0357(9) 0.0219(9) 0.0265(10) -0.0019(7) 0.0134(8) 0.0025(7) C7 0.0234(8) 0.0215(8) 0.0172(9) 0.0027(7) 0.0042(7) 0.0056(7) C15 0.0442(10) 0.0233(9) 0.0369(12) 0.0043(8) 0.0052(9) 0.0010(8) C16 0.0281(9) 0.0255(9) 0.0217(10) 0.0079(7) -0.0026(7) -0.0035(7) C17 0.0411(10) 0.0358(10) 0.0430(13) 0.0118(9) 0.0057(9) -0.0112(9) N1 0.0315(7) 0.0220(7) 0.0170(8) 0.0020(6) 0.0098(6) -0.0034(6) N2 0.0297(7) 0.0212(7) 0.0253(9) 0.0006(6) 0.0087(6) -0.0014(6) N3 0.0283(7) 0.0273(8) 0.0211(8) 0.0057(6) 0.0058(6) -0.0055(6) O1 0.0407(7) 0.0263(6) 0.0206(7) 0.0001(5) 0.0121(5) 0.0030(5) C8 0.0225(8) 0.0231(9) 0.0223(10) -0.0002(7) 0.0025(7) -0.0047(7) C9 0.0242(8) 0.0267(9) 0.0223(10) -0.0016(7) 0.0069(7) -0.0041(7) C10 0.0228(8) 0.0218(8) 0.0242(10) 0.0009(7) 0.0005(7) -0.0025(7) C11 0.0267(8) 0.0298(9) 0.0267(11) 0.0056(7) 0.0070(7) -0.0056(7) C12 0.0293(9) 0.0360(10) 0.0321(12) 0.0009(8) 0.0146(8) -0.0045(8) C13 0.0283(9) 0.0255(9) 0.0327(11) -0.0002(7) 0.0099(8) 0.0001(7) C14 0.0319(9) 0.0220(9) 0.0296(11) 0.0001(7) 0.0092(8) -0.0022(8) O2 0.0373(7) 0.0215(6) 0.0408(8) 0.0057(5) 0.0172(6) 0.0010(5) O3 0.0603(8) 0.0340(7) 0.0593(10) 0.0170(6) 0.0408(8) 0.0131(6) O4 0.0368(7) 0.0273(6) 0.0361(8) 0.0074(5) 0.0157(6) 0.0031(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 1.384(2) . ? C1 C6 1.387(2) . ? C1 C7 1.496(2) . ? C2 C3 1.379(2) . ? C2 H2A 0.95 . ? C3 N2 1.3338(19) . ? C3 H3 0.95 . ? C5 N2 1.3394(19) . ? C5 C6 1.378(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.2303(18) . ? C7 N1 1.348(2) . ? C15 C16 1.495(2) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 N3 1.2846(19) . ? C16 C17 1.494(2) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 N3 1.4010(17) . ? N1 H1 0.889(18) . ? C8 C13 1.387(2) . ? C8 C9 1.398(2) . ? C8 C14 1.491(2) . ? C9 C10 1.385(2) . ? C9 H9 0.95 . ? C10 O4 1.3633(19) . ? C10 C11 1.390(2) . ? C11 C12 1.376(2) . ? C11 H11 0.95 . ? C12 C13 1.387(2) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 O3 1.2122(19) . ? C14 O2 1.3230(19) . ? O2 H2 0.98(2) . ? O4 H4 0.86(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 118.08(14) . . ? C2 C1 C7 123.23(13) . . ? C6 C1 C7 118.68(14) . . ? C3 C2 C1 119.19(14) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? N2 C3 C2 123.24(14) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C5 C6 123.52(14) . . ? N2 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C5 C6 C1 118.77(15) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? O1 C7 N1 123.77(14) . . ? O1 C7 C1 120.53(13) . . ? N1 C7 C1 115.70(13) . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C17 116.39(16) . . ? N3 C16 C15 126.62(14) . . ? C17 C16 C15 116.99(15) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 N1 N3 117.09(13) . . ? C7 N1 H1 118.9(11) . . ? N3 N1 H1 120.4(11) . . ? C3 N2 C5 117.15(13) . . ? C16 N3 N1 116.05(13) . . ? C13 C8 C9 120.32(15) . . ? C13 C8 C14 121.58(14) . . ? C9 C8 C14 117.99(14) . . ? C10 C9 C8 119.84(15) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? O4 C10 C9 124.04(15) . . ? O4 C10 C11 116.51(14) . . ? C9 C10 C11 119.45(15) . . ? C12 C11 C10 120.52(15) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.57(15) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C8 C13 C12 119.24(15) . . ? C8 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? O3 C14 O2 123.55(15) . . ? O3 C14 C8 122.32(15) . . ? O2 C14 C8 114.10(14) . . ? C14 O2 H2 109.6(10) . . ? C10 O4 H4 114.5(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(2) . . . . ? C7 C1 C2 C3 -179.54(14) . . . . ? C1 C2 C3 N2 -1.2(2) . . . . ? N2 C5 C6 C1 -1.4(3) . . . . ? C2 C1 C6 C5 2.1(2) . . . . ? C7 C1 C6 C5 -179.20(15) . . . . ? C2 C1 C7 O1 146.29(15) . . . . ? C6 C1 C7 O1 -32.4(2) . . . . ? C2 C1 C7 N1 -33.0(2) . . . . ? C6 C1 C7 N1 148.34(15) . . . . ? O1 C7 N1 N3 7.7(2) . . . . ? C1 C7 N1 N3 -173.01(12) . . . . ? C2 C3 N2 C5 1.9(2) . . . . ? C6 C5 N2 C3 -0.6(2) . . . . ? C17 C16 N3 N1 -178.45(13) . . . . ? C15 C16 N3 N1 2.0(2) . . . . ? C7 N1 N3 C16 -167.32(14) . . . . ? C13 C8 C9 C10 1.7(2) . . . . ? C14 C8 C9 C10 -174.61(15) . . . . ? C8 C9 C10 O4 -179.65(14) . . . . ? C8 C9 C10 C11 0.8(2) . . . . ? O4 C10 C11 C12 178.04(15) . . . . ? C9 C10 C11 C12 -2.4(2) . . . . ? C10 C11 C12 C13 1.5(3) . . . . ? C9 C8 C13 C12 -2.5(2) . . . . ? C14 C8 C13 C12 173.61(15) . . . . ? C11 C12 C13 C8 0.9(3) . . . . ? C13 C8 C14 O3 -167.97(17) . . . . ? C9 C8 C14 O3 8.2(3) . . . . ? C13 C8 C14 O2 10.0(2) . . . . ? C9 C8 C14 O2 -173.75(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 O2 H2 N2 0.98(2) 1.73(2) 2.711(2) 178(2) . C5 H5 O3 0.95 2.42 3.1229(19) 131.0 . N1 H1 O1 0.89(2) 1.99(2) 2.879(2) 174(2) 4_565 O4 H4 N3 0.86(2) 2.07(2) 2.881(2) 158(2) 3_566 _chemical_name_common ;(3-hydroxybenzoic acid).(N'-(propan-2- ylidene)isonicotinohydrazide) ;