# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_email 'andreas.lemmerer@wits.ac.za ' _publ_contact_author_name 'Andreas Lemmerer' _publ_author_name A.Lemmerer data_1 _database_code_depnum_ccdc_archive 'CCDC 847197' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-08-16T14:44:15-00:00 _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 ; Isonicotinic acid hydrazide ; _chemical_formula_moiety 'C6 H7 N3 O' _chemical_formula_sum 'C6 H7 N3 O' _chemical_formula_weight 137.15 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.78720(10) _cell_length_b 11.2948(4) _cell_length_c 14.6870(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 628.25(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3435 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.32 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.45 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9834 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_number 5027 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 916 _reflns_number_gt 876 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0410P)^2^+0.1881P] 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 916 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.204 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # 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 0.4782(4) 0.45975(13) 0.59146(10) 0.0184(3) Uani 1 1 d . . . C2 C 0.4022(5) 0.53059(13) 0.66617(10) 0.0245(4) Uani 1 1 d . . . H2 H 0.4442 0.6135 0.664 0.029 Uiso 1 1 calc R . . C3 C 0.2644(5) 0.47881(14) 0.74387(10) 0.0278(4) Uani 1 1 d . . . H3 H 0.212 0.5283 0.7944 0.033 Uiso 1 1 calc R . . C4 C 0.2753(5) 0.29539(14) 0.67930(11) 0.0261(4) Uani 1 1 d . . . H4 H 0.2298 0.2128 0.6833 0.031 Uiso 1 1 calc R . . C5 C 0.4147(5) 0.33890(13) 0.59882(11) 0.0225(3) Uani 1 1 d . . . H5 H 0.4659 0.2872 0.5496 0.027 Uiso 1 1 calc R . . C6 C 0.6333(4) 0.50518(12) 0.50406(9) 0.0181(3) Uani 1 1 d . . . N1 N 0.6049(4) 0.62263(11) 0.49105(8) 0.0200(3) Uani 1 1 d . . . H1 H 0.493(6) 0.6728(16) 0.5287(13) 0.03 Uiso 1 1 d . . . N2 N 0.2011(4) 0.36255(13) 0.75157(9) 0.0265(3) Uani 1 1 d . . . N3 N 0.7750(4) 0.67764(11) 0.41585(8) 0.0198(3) Uani 1 1 d . . . H3A H 0.635(6) 0.6734(17) 0.3651(13) 0.03 Uiso 1 1 d . . . H3B H 0.955(6) 0.6291(18) 0.4034(14) 0.03 Uiso 1 1 d . . . O1 O 0.7806(4) 0.43999(9) 0.44959(7) 0.0278(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 0.0182(7) 0.0216(6) 0.0155(6) 0.0017(5) -0.0024(6) 0.0013(6) C2 0.0324(9) 0.0219(7) 0.0193(7) 0.0010(5) 0.0008(7) 0.0034(7) C3 0.0347(9) 0.0311(8) 0.0176(7) 0.0005(6) 0.0016(7) 0.0051(8) C4 0.0282(8) 0.0249(7) 0.0253(7) 0.0052(6) -0.0025(7) -0.0038(8) C5 0.0245(8) 0.0223(7) 0.0207(7) -0.0001(6) -0.0004(7) -0.0015(7) C6 0.0195(7) 0.0187(6) 0.0160(6) -0.0009(5) -0.0005(6) -0.0006(6) N1 0.0272(7) 0.0177(6) 0.0152(6) -0.0001(5) 0.0046(6) 0.0003(6) N2 0.0269(8) 0.0331(7) 0.0196(6) 0.0066(5) 0.0008(6) 0.0000(6) N3 0.0245(7) 0.0205(5) 0.0143(6) 0.0008(5) 0.0008(6) -0.0024(6) O1 0.0397(7) 0.0208(5) 0.0229(5) -0.0024(4) 0.0083(6) 0.0039(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 1.388(2) . ? C1 C5 1.3902(19) . ? C1 C6 1.5021(19) . ? C2 C3 1.384(2) . ? C2 H2 0.95 . ? C3 N2 1.340(2) . ? C3 H3 0.95 . ? C4 N2 1.335(2) . ? C4 C5 1.385(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2219(18) . ? C6 N1 1.3446(18) . ? N1 N3 1.4215(18) . ? N1 H1 0.90(2) . ? N3 H3A 0.92(2) . ? N3 H3B 0.89(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C5 117.95(14) . . ? C2 C1 C6 124.03(13) . . ? C5 C1 C6 118.00(13) . . ? C3 C2 C1 119.10(14) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? N2 C3 C2 123.44(14) . . ? N2 C3 H3 118.3 . . ? C2 C3 H3 118.3 . . ? N2 C4 C5 123.89(14) . . ? N2 C4 H4 118.1 . . ? C5 C4 H4 118.1 . . ? C4 C5 C1 118.73(14) . . ? C4 C5 H5 120.6 . . ? C1 C5 H5 120.6 . . ? O1 C6 N1 122.55(14) . . ? O1 C6 C1 122.15(13) . . ? N1 C6 C1 115.29(12) . . ? C6 N1 N3 120.35(13) . . ? C6 N1 H1 125.0(12) . . ? N3 N1 H1 114.6(12) . . ? C4 N2 C3 116.89(13) . . ? N1 N3 H3A 110.3(14) . . ? N1 N3 H3B 103.7(13) . . ? H3A N3 H3B 104.0(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 C5 C1 C2 C3 -0.6(3) . . . . ? C6 C1 C2 C3 -179.01(16) . . . . ? C1 C2 C3 N2 0.4(3) . . . . ? N2 C4 C5 C1 -0.9(3) . . . . ? C2 C1 C5 C4 0.8(3) . . . . ? C6 C1 C5 C4 179.30(15) . . . . ? C2 C1 C6 O1 160.56(16) . . . . ? C5 C1 C6 O1 -17.8(2) . . . . ? C2 C1 C6 N1 -18.1(2) . . . . ? C5 C1 C6 N1 163.48(15) . . . . ? O1 C6 N1 N3 -5.5(2) . . . . ? C1 C6 N1 N3 173.15(13) . . . . ? C5 C4 N2 C3 0.6(3) . . . . ? C2 C3 N2 C4 -0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.90(2) 2.05(2) 2.919(2) 163(2) 4_466 N3 H3A N2 0.92(2) 2.14(2) 3.046(2) 172(2) 2_564 N3 H3B N2 0.89(2) 2.58(2) 3.157(2) 123(2) 2_664 ###END data_2 _database_code_depnum_ccdc_archive 'CCDC 847198' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-08-16T15:22:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N?-(propan-2-ylidene)isonicotinohydrazide ; _chemical_formula_moiety 'C9 H11 N3 O' _chemical_formula_sum 'C9 H11 N3 O' _chemical_formula_weight 177.21 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pccn _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 12.9790(5) _cell_length_b 17.6437(3) _cell_length_c 7.9695(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1825.00(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5601 _cell_measurement_theta_min 3.4008 _cell_measurement_theta_max 67.3561 #----------------------------------------------------------------------------# # 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 1.29 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_special_details ; Absorption corrections were made using the program Crysalis ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.719 _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 0.55401 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # 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 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_unetI/netI 0.0212 _diffrn_reflns_number 10141 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 67.51 _diffrn_reflns_theta_full 67.51 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1642 _reflns_number_gt 1408 _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^)+(0.0894P)^2^+0.1731P] 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 1642 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1202 _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_diff_density_max 0.175 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # 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 0.14761(10) 0.42539(8) 0.43199(16) 0.0277(3) Uani 1 1 d . . . C2 C 0.10735(11) 0.44609(9) 0.58660(18) 0.0342(4) Uani 1 1 d . . . H2 H 0.0984 0.498 0.6149 0.041 Uiso 1 1 calc R . . C3 C 0.08047(13) 0.38960(9) 0.6989(2) 0.0421(4) Uani 1 1 d . . . H3 H 0.0526 0.4044 0.8041 0.051 Uiso 1 1 calc R . . C4 C 0.12876(11) 0.29690(9) 0.5185(2) 0.0373(4) Uani 1 1 d . . . H4 H 0.1367 0.2446 0.4935 0.045 Uiso 1 1 calc R . . C5 C 0.15699(11) 0.34877(8) 0.39681(18) 0.0331(4) Uani 1 1 d . . . H5 H 0.1823 0.3322 0.2911 0.04 Uiso 1 1 calc R . . C6 C 0.17730(10) 0.48266(8) 0.30202(17) 0.0277(3) Uani 1 1 d . . . C7 C 0.41685(11) 0.62566(8) 0.42049(18) 0.0332(4) Uani 1 1 d . . . H7A H 0.3775 0.62 0.5247 0.05 Uiso 1 1 calc R . . H7B H 0.4622 0.6699 0.4294 0.05 Uiso 1 1 calc R . . H7C H 0.4585 0.5801 0.4016 0.05 Uiso 1 1 calc R . . C8 C 0.34414(10) 0.63634(8) 0.27671(17) 0.0279(3) Uani 1 1 d . . . C9 C 0.36806(12) 0.69783(10) 0.1536(2) 0.0420(4) Uani 1 1 d . . . H9A H 0.318 0.6963 0.0616 0.063 Uiso 1 1 calc R . . H9B H 0.4376 0.6903 0.1086 0.063 Uiso 1 1 calc R . . H9C H 0.3643 0.7471 0.2098 0.063 Uiso 1 1 calc R . . N1 N 0.23943(9) 0.53871(7) 0.35773(14) 0.0285(3) Uani 1 1 d . . . H1 H 0.2678(14) 0.5359(10) 0.458(3) 0.043 Uiso 1 1 d . . . N2 N 0.09125(10) 0.31555(8) 0.66837(17) 0.0416(4) Uani 1 1 d . . . N3 N 0.26394(9) 0.59644(7) 0.24498(13) 0.0296(3) Uani 1 1 d . . . O1 O 0.14718(8) 0.47714(6) 0.15615(12) 0.0371(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 0.0253(6) 0.0335(7) 0.0243(7) 0.0026(5) -0.0011(5) -0.0053(5) C2 0.0399(8) 0.0326(7) 0.0301(7) 0.0003(6) 0.0071(6) -0.0042(6) C3 0.0492(9) 0.0465(9) 0.0307(8) 0.0050(7) 0.0091(6) -0.0081(7) C4 0.0347(8) 0.0309(7) 0.0464(9) 0.0049(6) -0.0030(6) -0.0038(6) C5 0.0317(7) 0.0339(8) 0.0336(8) -0.0017(6) 0.0019(6) -0.0032(6) C6 0.0277(7) 0.0326(7) 0.0228(6) 0.0023(5) 0.0001(5) -0.0042(5) C7 0.0291(7) 0.0369(8) 0.0337(8) 0.0000(6) -0.0031(5) -0.0051(5) C8 0.0266(7) 0.0289(7) 0.0281(7) 0.0012(5) 0.0033(5) 0.0004(5) C9 0.0356(8) 0.0439(9) 0.0466(9) 0.0161(7) 0.0010(6) -0.0075(6) N1 0.0340(6) 0.0324(7) 0.0190(6) 0.0062(5) -0.0023(4) -0.0083(5) N2 0.0434(8) 0.0415(8) 0.0398(7) 0.0129(6) -0.0008(6) -0.0085(6) N3 0.0311(6) 0.0331(6) 0.0245(6) 0.0079(4) -0.0004(4) -0.0053(5) O1 0.0413(6) 0.0464(6) 0.0237(5) 0.0034(4) -0.0050(4) -0.0128(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 C5 1.386(2) . ? C1 C2 1.387(2) . ? C1 C6 1.4975(18) . ? C2 C3 1.384(2) . ? C2 H2 0.95 . ? C3 N2 1.336(2) . ? C3 H3 0.95 . ? C4 N2 1.331(2) . ? C4 C5 1.383(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2303(17) . ? C6 N1 1.3510(17) . ? C7 C8 1.4964(19) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 N3 1.2818(18) . ? C8 C9 1.4956(19) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? N1 N3 1.3950(15) . ? N1 H1 0.88(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C2 118.00(13) . . ? C5 C1 C6 119.71(13) . . ? C2 C1 C6 122.25(13) . . ? C3 C2 C1 118.65(14) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? N2 C3 C2 124.07(15) . . ? N2 C3 H3 118 . . ? C2 C3 H3 118 . . ? N2 C4 C5 124.24(14) . . ? N2 C4 H4 117.9 . . ? C5 C4 H4 117.9 . . ? C4 C5 C1 118.71(14) . . ? C4 C5 H5 120.6 . . ? C1 C5 H5 120.6 . . ? O1 C6 N1 123.92(12) . . ? O1 C6 C1 121.23(12) . . ? N1 C6 C1 114.84(12) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 115.95(12) . . ? N3 C8 C7 126.44(12) . . ? C9 C8 C7 117.58(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 N1 N3 117.32(11) . . ? C6 N1 H1 120.4(11) . . ? N3 N1 H1 122.1(11) . . ? C4 N2 C3 116.30(13) . . ? C8 N3 N1 117.34(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 C5 C1 C2 C3 1.2(2) . . . . ? C6 C1 C2 C3 179.08(13) . . . . ? C1 C2 C3 N2 0.3(3) . . . . ? N2 C4 C5 C1 1.0(2) . . . . ? C2 C1 C5 C4 -1.8(2) . . . . ? C6 C1 C5 C4 -179.77(13) . . . . ? C5 C1 C6 O1 48.0(2) . . . . ? C2 C1 C6 O1 -129.89(16) . . . . ? C5 C1 C6 N1 -131.26(14) . . . . ? C2 C1 C6 N1 50.90(19) . . . . ? O1 C6 N1 N3 5.0(2) . . . . ? C1 C6 N1 N3 -175.80(12) . . . . ? C5 C4 N2 C3 0.5(2) . . . . ? C2 C3 N2 C4 -1.2(2) . . . . ? C9 C8 N3 N1 -179.87(13) . . . . ? C7 C8 N3 N1 2.2(2) . . . . ? C6 N1 N3 C8 -159.82(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 N1 H1 O1 0.88(2) 2.19(2) 3.000(2) 153(2) 8_656 ###END _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_4 _database_code_depnum_ccdc_archive 'CCDC 847200' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-06-30T08:00:29-00:00 _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).bis(N?-(propan-2-ylidene)isonicotinohydrazide) ; _chemical_formula_moiety 'C9 H11 N3 O, 0.5(C4 H6 O4)' _chemical_formula_sum 'C11 H14 N3 O3' _chemical_formula_weight 236.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 18.0455(3) _cell_length_b 8.2643(3) _cell_length_c 7.7750(6) _cell_angle_alpha 90 _cell_angle_beta 94.445(2) _cell_angle_gamma 90 _cell_volume 1156.02(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9943 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.16 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9373 _exptl_absorpt_correction_T_max 0.99 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0152 _diffrn_reflns_number 20671 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2782 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0603P)^2^+0.7986P] 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 2782 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.283 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # 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 0.25558(8) 0.43833(19) 0.36898(19) 0.0229(3) Uani 1 1 d . . . C2 C 0.21151(8) 0.33356(19) 0.26545(19) 0.0245(3) Uani 1 1 d . . . H2A H 0.2153 0.2197 0.2805 0.029 Uiso 1 1 calc R . . C3 C 0.16172(9) 0.3997(2) 0.1394(2) 0.0279(3) Uani 1 1 d . . . H3 H 0.1313 0.3281 0.0694 0.033 Uiso 1 1 calc R . . C4 C 0.19669(10) 0.6584(2) 0.2122(2) 0.0312(4) Uani 1 1 d . . . H4 H 0.192 0.7716 0.1936 0.037 Uiso 1 1 calc R . . C5 C 0.24704(9) 0.6036(2) 0.3426(2) 0.0291(4) Uani 1 1 d . . . H5 H 0.2754 0.6783 0.4133 0.035 Uiso 1 1 calc R . . C6 C 0.30930(9) 0.3824(2) 0.51433(19) 0.0249(3) Uani 1 1 d . . . C7 C 0.38055(13) -0.0925(2) 0.5180(2) 0.0423(5) Uani 1 1 d . . . H7A H 0.4126 -0.109 0.4234 0.063 Uiso 1 1 calc R . . H7B H 0.3305 -0.0628 0.4706 0.063 Uiso 1 1 calc R . . H7V H 0.3781 -0.1927 0.5848 0.063 Uiso 1 1 calc R . . C8 C 0.41159(9) 0.0397(2) 0.6323(2) 0.0271(3) Uani 1 1 d . . . C9 C 0.46639(11) -0.0075(3) 0.7792(3) 0.0396(4) Uani 1 1 d . . . H9A H 0.4415 -0.0751 0.8609 0.059 Uiso 1 1 calc R . . H9B H 0.486 0.0901 0.838 0.059 Uiso 1 1 calc R . . H9C H 0.5074 -0.0684 0.7344 0.059 Uiso 1 1 calc R . . N1 N 0.34128(7) 0.23698(17) 0.49350(16) 0.0245(3) Uani 1 1 d . . . H1 H 0.3385(11) 0.192(3) 0.389(3) 0.037 Uiso 1 1 d . . . N2 N 0.15430(8) 0.55828(19) 0.11125(18) 0.0296(3) Uani 1 1 d . . . N3 N 0.39384(7) 0.18851(18) 0.62513(16) 0.0274(3) Uani 1 1 d . . . O1 O 0.32054(7) 0.46478(16) 0.64474(16) 0.0353(3) Uani 1 1 d . . . C10 C 0.05673(9) 0.53606(19) -0.2837(2) 0.0277(3) Uani 1 1 d . . . C11 C -0.00783(9) 0.5420(2) -0.4172(2) 0.0313(4) Uani 1 1 d . . . H11A H -0.0206 0.6565 -0.4426 0.038 Uiso 1 1 calc R . . H11B H -0.0514 0.4905 -0.3699 0.038 Uiso 1 1 calc R . . O2 O 0.04432(8) 0.61693(18) -0.14120(17) 0.0399(3) Uani 1 1 d . . . H2 H 0.0820(16) 0.604(3) -0.062(4) 0.06 Uiso 1 1 d . . . O3 O 0.11464(8) 0.46844(18) -0.3035(2) 0.0443(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 0.0240(7) 0.0268(7) 0.0180(6) -0.0012(6) 0.0013(5) 0.0000(6) C2 0.0270(7) 0.0236(7) 0.0228(7) -0.0015(6) 0.0008(6) -0.0002(6) C3 0.0267(7) 0.0334(8) 0.0229(7) -0.0045(6) -0.0022(6) 0.0005(6) C4 0.0353(8) 0.0259(8) 0.0322(8) 0.0006(7) 0.0013(7) 0.0043(6) C5 0.0332(8) 0.0255(8) 0.0280(8) -0.0054(6) -0.0018(6) -0.0014(6) C6 0.0269(7) 0.0284(8) 0.0189(7) -0.0005(6) -0.0011(5) -0.0043(6) C7 0.0662(13) 0.0293(9) 0.0299(9) 0.0016(7) -0.0054(8) -0.0018(9) C8 0.0282(7) 0.0320(8) 0.0208(7) 0.0048(6) 0.0004(6) -0.0010(6) C9 0.0389(9) 0.0412(10) 0.0368(10) 0.0096(8) -0.0104(8) 0.0026(8) N1 0.0296(7) 0.0275(7) 0.0155(6) 0.0013(5) -0.0035(5) -0.0007(5) N2 0.0286(7) 0.0353(8) 0.0245(7) 0.0005(6) -0.0006(5) 0.0053(6) N3 0.0291(7) 0.0325(7) 0.0192(6) 0.0033(5) -0.0068(5) -0.0026(5) O1 0.0437(7) 0.0367(7) 0.0239(6) -0.0081(5) -0.0072(5) 0.0008(5) C10 0.0289(8) 0.0232(7) 0.0301(8) 0.0027(6) -0.0021(6) 0.0012(6) C11 0.0256(8) 0.0375(9) 0.0304(9) 0.0014(7) -0.0010(6) 0.0057(7) O2 0.0379(7) 0.0519(8) 0.0288(6) -0.0033(6) -0.0049(5) 0.0151(6) O3 0.0357(7) 0.0453(8) 0.0494(8) -0.0140(6) -0.0124(6) 0.0150(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 C5 1.388(2) . ? C1 C2 1.390(2) . ? C1 C6 1.504(2) . ? C2 C3 1.389(2) . ? C2 H2A 0.95 . ? C3 N2 1.333(2) . ? C3 H3 0.95 . ? C4 N2 1.339(2) . ? C4 C5 1.384(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2252(19) . ? C6 N1 1.348(2) . ? C7 C8 1.490(2) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7V 0.98 . ? C8 N3 1.271(2) . ? C8 C9 1.503(2) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? N1 N3 1.3989(17) . ? N1 H1 0.89(2) . ? C10 O3 1.205(2) . ? C10 O2 1.328(2) . ? C10 C11 1.500(2) . ? C11 C11 1.509(3) 3_564 ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? O2 H2 0.89(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 C5 C1 C2 118.40(14) . . ? C5 C1 C6 118.13(14) . . ? C2 C1 C6 123.39(14) . . ? C3 C2 C1 118.23(15) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? N2 C3 C2 123.63(15) . . ? N2 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? N2 C4 C5 122.72(16) . . ? N2 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C4 C5 C1 119.28(15) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? O1 C6 N1 123.36(15) . . ? O1 C6 C1 120.44(15) . . ? N1 C6 C1 116.16(13) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7V 109.5 . . ? H7A C7 H7V 109.5 . . ? H7B C7 H7V 109.5 . . ? N3 C8 C7 126.98(15) . . ? N3 C8 C9 115.67(15) . . ? C7 C8 C9 117.24(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 N1 N3 116.08(13) . . ? C6 N1 H1 119.1(14) . . ? N3 N1 H1 122.4(14) . . ? C3 N2 C4 117.72(14) . . ? C8 N3 N1 117.61(14) . . ? O3 C10 O2 122.93(16) . . ? O3 C10 C11 124.19(16) . . ? O2 C10 C11 112.87(14) . . ? C10 C11 C11 112.87(17) . 3_564 ? C10 C11 H11A 109 . . ? C11 C11 H11A 109 3_564 . ? C10 C11 H11B 109 . . ? C11 C11 H11B 109 3_564 . ? H11A C11 H11B 107.8 . . ? C10 O2 H2 110.4(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 C5 C1 C2 C3 0.7(2) . . . . ? C6 C1 C2 C3 177.45(14) . . . . ? C1 C2 C3 N2 0.6(2) . . . . ? N2 C4 C5 C1 1.3(3) . . . . ? C2 C1 C5 C4 -1.6(2) . . . . ? C6 C1 C5 C4 -178.52(15) . . . . ? C5 C1 C6 O1 30.6(2) . . . . ? C2 C1 C6 O1 -146.11(16) . . . . ? C5 C1 C6 N1 -151.43(15) . . . . ? C2 C1 C6 N1 31.9(2) . . . . ? O1 C6 N1 N3 -5.0(2) . . . . ? C1 C6 N1 N3 177.10(13) . . . . ? C2 C3 N2 C4 -0.9(3) . . . . ? C5 C4 N2 C3 0.0(3) . . . . ? C7 C8 N3 N1 -2.1(3) . . . . ? C9 C8 N3 N1 -178.12(14) . . . . ? C6 N1 N3 C8 163.26(15) . . . . ? O3 C10 C11 C11 -1.7(3) . . . 3_564 ? O2 C10 C11 C11 176.83(19) . . . 3_564 ? 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 N1 H1 O1 0.89(2) 2.30(2) 3.1805(19) 168.9(19) 4_565 O2 H2 N2 0.89(3) 1.84(3) 2.7244(19) 173(3) . ###END data_5 _database_code_depnum_ccdc_archive 'CCDC 847201' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-06-30T08:22:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (succinic acid).((Z)-N?-(butan-2-ylidene)isonicotinohydrazide) ; _chemical_formula_moiety 'C10 H13 N3 O, 0.5(C4 H6 O4)' _chemical_formula_sum 'C12 H16 N3 O3' _chemical_formula_weight 250.28 #----------------------------------------------------------------------------# # 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 5.0602(3) _cell_length_b 31.8299(17) _cell_length_c 8.0552(5) _cell_angle_alpha 90 _cell_angle_beta 98.780(3) _cell_angle_gamma 90 _cell_volume 1282.21(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7503 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.94 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9541 _exptl_absorpt_correction_T_max 0.9924 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_unetI/netI 0.0257 _diffrn_reflns_number 20982 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3092 _reflns_number_gt 2520 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0779P)^2^+0.4717P] 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 3092 _refine_ls_number_parameters 198 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.069 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.145 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.332 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # 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 0.7545(3) 0.22530(4) 0.52488(18) 0.0264(3) Uani 1 1 d . . . C2 C 0.5204(3) 0.21691(5) 0.4158(2) 0.0331(4) Uani 1 1 d . . . H2C H 0.4246 0.2389 0.3533 0.04 Uiso 1 1 calc R . . C3 C 0.4297(4) 0.17597(6) 0.4002(2) 0.0425(4) Uani 1 1 d . . . H3 H 0.2701 0.1704 0.3248 0.051 Uiso 1 1 calc R . . C4 C 0.7781(5) 0.15222(6) 0.5900(3) 0.0524(5) Uani 1 1 d . . . H4 H 0.8679 0.1297 0.6521 0.063 Uiso 1 1 calc R . . C5 C 0.8853(4) 0.19206(5) 0.6122(2) 0.0423(4) Uani 1 1 d . . . H5 H 1.0472 0.1966 0.6867 0.051 Uiso 1 1 calc R . . C6 C 0.8767(3) 0.26831(4) 0.54902(18) 0.0253(3) Uani 1 1 d . . . C7 C 0.3696(4) 0.36714(7) 0.4422(4) 0.0694(8) Uani 1 1 d . . . H7A H 0.381 0.3523 0.3369 0.104 Uiso 1 1 calc R . . H7B H 0.2943 0.3952 0.4172 0.104 Uiso 1 1 calc R . . H7C H 0.2544 0.3513 0.5072 0.104 Uiso 1 1 calc R . . C8 C 0.6406(3) 0.37104(5) 0.5410(3) 0.0400(4) Uani 1 1 d . . . C9 C 0.7415(5) 0.41385(5) 0.5982(3) 0.0563(6) Uani 1 1 d . . . H9A H 0.9255 0.4111 0.6598 0.068 Uiso 1 1 calc R . . H9B H 0.6277 0.4251 0.6775 0.068 Uiso 1 1 calc R . . C10 C 0.7432(5) 0.44527(6) 0.4539(4) 0.0646(7) Uani 1 1 d . . . H10A H 0.858 0.4346 0.3758 0.097 Uiso 1 1 calc R . . H10B H 0.812 0.4724 0.4994 0.097 Uiso 1 1 calc R . . H10C H 0.5607 0.4489 0.3945 0.097 Uiso 1 1 calc R . . N1 N 0.7011(3) 0.30030(4) 0.53908(17) 0.0288(3) Uani 1 1 d . . . H1 H 0.528(5) 0.2942(6) 0.535(3) 0.043 Uiso 1 1 d . . . N2 N 0.5539(4) 0.14401(5) 0.4849(2) 0.0463(4) Uani 1 1 d . . . N3 N 0.8008(3) 0.34031(4) 0.58402(18) 0.0317(3) Uani 1 1 d . . . O1 O 1.1194(2) 0.27275(3) 0.57509(16) 0.0345(3) Uani 1 1 d . . . C11 C 0.2049(4) 0.05106(5) 0.5058(2) 0.0391(4) Uani 1 1 d DU . . C12A C 0.128(2) 0.0058(2) 0.4627(18) 0.041(2) Uani 0.462(17) 1 d PDU . 1 H12A H 0.2762 -0.0132 0.5092 0.049 Uiso 0.462(17) 1 calc PR . 1 H12B H 0.0948 0.0022 0.3392 0.049 Uiso 0.462(17) 1 calc PR . 1 O2A O 0.3083(19) 0.0726(2) 0.3916(6) 0.0453(15) Uani 0.462(17) 1 d PDU . 1 H2A H 0.3667 0.0957 0.4327 0.068 Uiso 0.462(17) 1 calc PR . 1 O3A O 0.205(2) 0.0647(2) 0.6427(6) 0.0478(17) Uani 0.462(17) 1 d PDU . 1 C12B C 0.057(2) 0.0120(2) 0.4360(12) 0.0385(17) Uani 0.538(17) 1 d PDU . 2 H12C H -0.0892 0.0203 0.3458 0.046 Uiso 0.538(17) 1 calc PR . 2 H12D H 0.1814 -0.0062 0.3853 0.046 Uiso 0.538(17) 1 calc PR . 2 O2B O 0.4135(19) 0.0617(2) 0.4307(12) 0.0598(19) Uani 0.538(17) 1 d PDU . 2 H2B H 0.4622 0.0863 0.4588 0.09 Uiso 0.538(17) 1 calc PR . 2 O3B O 0.1147(18) 0.0713(2) 0.6083(12) 0.0618(19) Uani 0.538(17) 1 d PDU . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0256(7) 0.0295(7) 0.0245(7) 0.0000(5) 0.0056(5) -0.0046(5) C2 0.0285(8) 0.0402(8) 0.0300(8) -0.0068(6) 0.0024(6) -0.0021(6) C3 0.0393(10) 0.0491(10) 0.0398(9) -0.0147(7) 0.0080(7) -0.0153(8) C4 0.0778(15) 0.0338(9) 0.0428(10) 0.0098(7) 0.0007(10) -0.0109(9) C5 0.0464(10) 0.0356(8) 0.0404(9) 0.0081(7) -0.0080(7) -0.0074(7) C6 0.0217(7) 0.0287(7) 0.0250(6) 0.0025(5) 0.0022(5) -0.0023(5) C7 0.0283(10) 0.0561(12) 0.124(2) 0.0509(14) 0.0141(11) 0.0060(8) C8 0.0332(9) 0.0342(8) 0.0582(11) 0.0138(7) 0.0252(8) 0.0039(6) C9 0.0710(15) 0.0298(9) 0.0778(15) 0.0038(9) 0.0429(12) 0.0063(9) C10 0.0683(15) 0.0347(9) 0.0972(19) 0.0175(11) 0.0334(13) -0.0015(9) N1 0.0195(6) 0.0291(6) 0.0382(7) 0.0030(5) 0.0052(5) -0.0020(5) N2 0.0639(11) 0.0392(8) 0.0392(8) -0.0067(6) 0.0189(7) -0.0244(7) N3 0.0282(7) 0.0276(6) 0.0412(7) 0.0008(5) 0.0107(5) -0.0018(5) O1 0.0191(6) 0.0313(6) 0.0521(7) 0.0000(5) 0.0021(5) -0.0012(4) C11 0.0583(11) 0.0256(7) 0.0344(8) -0.0019(6) 0.0100(7) -0.0104(7) C12A 0.045(4) 0.025(2) 0.055(5) -0.009(3) 0.016(3) -0.009(2) O2A 0.075(4) 0.030(2) 0.0327(17) -0.0051(13) 0.017(2) -0.019(2) O3A 0.073(5) 0.041(2) 0.0328(18) -0.0086(15) 0.016(2) -0.021(3) C12B 0.059(5) 0.026(2) 0.031(3) -0.0043(18) 0.010(3) -0.010(2) O2B 0.080(4) 0.034(2) 0.075(4) -0.018(2) 0.044(3) -0.026(2) O3B 0.061(4) 0.038(2) 0.093(4) -0.034(3) 0.034(3) -0.018(2) #----------------------------------------------------------------------------# # 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 C5 1.382(2) . ? C1 C2 1.389(2) . ? C1 C6 1.5022(19) . ? C2 C3 1.381(2) . ? C2 H2C 0.95 . ? C3 N2 1.329(3) . ? C3 H3 0.95 . ? C4 N2 1.333(3) . ? C4 C5 1.380(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2223(18) . ? C6 N1 1.3456(19) . ? C7 C8 1.482(3) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 N3 1.284(2) . ? C8 C9 1.503(3) . ? C9 C10 1.534(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? N1 N3 1.3971(17) . ? N1 H1 0.89(2) . ? C11 O3A 1.185(5) . ? C11 O3B 1.191(5) . ? C11 O2A 1.319(4) . ? C11 O2B 1.338(4) . ? C11 C12B 1.513(5) . ? C11 C12A 1.520(6) . ? C12A C12A 1.55(3) 3_556 ? C12A H12A 0.99 . ? C12A H12B 0.99 . ? O2A H2A 0.84 . ? C12B C12B 1.47(2) 3_556 ? C12B H12C 0.99 . ? C12B H12D 0.99 . ? O2B H2B 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 C5 C1 C2 118.07(14) . . ? C5 C1 C6 118.43(14) . . ? C2 C1 C6 123.48(14) . . ? C3 C2 C1 118.62(16) . . ? C3 C2 H2C 120.7 . . ? C1 C2 H2C 120.7 . . ? N2 C3 C2 123.43(17) . . ? N2 C3 H3 118.3 . . ? C2 C3 H3 118.3 . . ? N2 C4 C5 122.80(18) . . ? N2 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C4 C5 C1 119.29(17) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? O1 C6 N1 124.03(13) . . ? O1 C6 C1 120.70(13) . . ? N1 C6 C1 115.28(13) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C7 125.15(18) . . ? N3 C8 C9 115.93(18) . . ? C7 C8 C9 118.92(17) . . ? C8 C9 C10 113.6(2) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 N1 N3 117.74(13) . . ? C6 N1 H1 118.2(13) . . ? N3 N1 H1 121.4(13) . . ? C3 N2 C4 117.78(15) . . ? C8 N3 N1 115.88(15) . . ? O3A C11 O2A 120.9(5) . . ? O3B C11 O2A 115.9(4) . . ? O3A C11 O2B 116.0(4) . . ? O3B C11 O2B 126.0(4) . . ? O3A C11 C12B 125.2(6) . . ? O3B C11 C12B 118.8(6) . . ? O2A C11 C12B 113.2(5) . . ? O2B C11 C12B 114.8(5) . . ? O3A C11 C12A 121.6(7) . . ? O3B C11 C12A 124.0(7) . . ? O2A C11 C12A 116.7(7) . . ? O2B C11 C12A 109.2(6) . . ? C11 C12A C12A 109.6(9) . 3_556 ? C11 C12A H12A 109.8 . . ? C12A C12A H12A 109.8 3_556 . ? C11 C12A H12B 109.8 . . ? C12A C12A H12B 109.8 3_556 . ? H12A C12A H12B 108.2 . . ? C11 O2A H2A 109.5 . . ? C12B C12B C11 113.0(8) 3_556 . ? C12B C12B H12C 109 3_556 . ? C11 C12B H12C 109 . . ? C12B C12B H12D 109 3_556 . ? C11 C12B H12D 109 . . ? H12C C12B H12D 107.8 . . ? C11 O2B H2B 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 C5 C1 C2 C3 0.1(2) . . . . ? C6 C1 C2 C3 178.31(14) . . . . ? C1 C2 C3 N2 0.4(3) . . . . ? N2 C4 C5 C1 1.1(3) . . . . ? C2 C1 C5 C4 -0.8(3) . . . . ? C6 C1 C5 C4 -179.13(17) . . . . ? C5 C1 C6 O1 33.2(2) . . . . ? C2 C1 C6 O1 -144.95(16) . . . . ? C5 C1 C6 N1 -146.99(16) . . . . ? C2 C1 C6 N1 34.8(2) . . . . ? N3 C8 C9 C10 123.1(2) . . . . ? C7 C8 C9 C10 -57.3(3) . . . . ? O1 C6 N1 N3 -9.2(2) . . . . ? C1 C6 N1 N3 171.05(12) . . . . ? C2 C3 N2 C4 -0.2(3) . . . . ? C5 C4 N2 C3 -0.6(3) . . . . ? C7 C8 N3 N1 -3.1(3) . . . . ? C9 C8 N3 N1 176.48(14) . . . . ? C6 N1 N3 C8 166.20(14) . . . . ? O3A C11 C12A C12A 45.0(18) . . . 3_556 ? O3B C11 C12A C12A 14(2) . . . 3_556 ? O2A C11 C12A C12A -144.6(14) . . . 3_556 ? O2B C11 C12A C12A -175.4(15) . . . 3_556 ? C12B C11 C12A C12A -63(3) . . . 3_556 ? O3A C11 C12B C12B -9.1(18) . . . 3_556 ? O3B C11 C12B C12B -39.2(17) . . . 3_556 ? O2A C11 C12B C12B 179.7(13) . . . 3_556 ? O2B C11 C12B C12B 147.6(14) . . . 3_556 ? C12A C11 C12B C12B 74(3) . . . 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 N1 H1 O1 0.89(2) 2.25(2) 3.1271(17) 168(2) 1_455 O2A H2A N2 0.84 1.82 2.643(5) 165 . O2B H2B N2 0.84 1.9 2.732(5) 171 . ###END _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 847203' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-06-30T09:16:09-00:00 _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).bis(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)/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 11.0130(4) _cell_length_b 13.1213(4) _cell_length_c 11.9425(4) _cell_angle_alpha 90 _cell_angle_beta 114.128(2) _cell_angle_gamma 90 _cell_volume 1574.98(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8824 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.29 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.33 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9903 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_unetI/netI 0.0172 _diffrn_reflns_number 24789 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3813 _reflns_number_gt 3153 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0588P)^2^+0.4418P] 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 3813 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.371 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 0.78812(11) 0.33628(8) 0.41026(10) 0.0233(2) Uani 1 1 d . . . C2 C 0.69567(12) 0.37210(10) 0.29886(11) 0.0301(3) Uani 1 1 d . . . H2A H 0.7229 0.4135 0.248 0.036 Uiso 1 1 calc R . . C3 C 0.56290(12) 0.34665(11) 0.26284(12) 0.0342(3) Uani 1 1 d . . . H3 H 0.5001 0.3724 0.1869 0.041 Uiso 1 1 calc R . . C4 C 0.60845(13) 0.25216(10) 0.43551(12) 0.0327(3) Uani 1 1 d . . . H4A H 0.5786 0.2092 0.4831 0.039 Uiso 1 1 calc R . . C5 C 0.74275(12) 0.27476(10) 0.47949(11) 0.0308(3) Uani 1 1 d . . . H5 H 0.8031 0.2484 0.5562 0.037 Uiso 1 1 calc R . . C6 C 0.93462(11) 0.35910(9) 0.46234(11) 0.0242(2) Uani 1 1 d . . . C7 C 1.06509(16) 0.48578(12) 0.21792(14) 0.0439(3) Uani 1 1 d . . . H7A H 1.0087 0.4263 0.182 0.066 Uiso 1 1 calc R . . H7B H 1.12 0.4999 0.1726 0.066 Uiso 1 1 calc R . . H7C H 1.0089 0.545 0.213 0.066 Uiso 1 1 calc R . . C8 C 1.15342(12) 0.46444(9) 0.34980(13) 0.0315(3) Uani 1 1 d . . . C9 C 1.29888(14) 0.48772(11) 0.39416(16) 0.0434(4) Uani 1 1 d . . . H9A H 1.3439 0.4711 0.4816 0.065 Uiso 1 1 calc R . . H9B H 1.3107 0.5603 0.382 0.065 Uiso 1 1 calc R . . H9C H 1.3371 0.4469 0.3478 0.065 Uiso 1 1 calc R . . N1 N 0.97991(10) 0.40704(8) 0.38785(10) 0.0277(2) Uani 1 1 d . . . H1 H 0.9263(17) 0.4263(13) 0.3174(16) 0.042 Uiso 1 1 d . . . N2 N 0.51897(10) 0.28807(9) 0.32922(10) 0.0312(2) Uani 1 1 d . . . N3 N 1.11515(10) 0.42791(8) 0.42959(10) 0.0299(2) Uani 1 1 d . . . O1 O 1.00561(8) 0.33294(7) 0.56743(8) 0.0349(2) Uani 1 1 d . . . C10 C 0.10151(11) 0.17277(9) 0.32598(10) 0.0245(2) Uani 1 1 d . . . C11 C -0.00014(12) 0.19646(9) 0.21257(11) 0.0275(2) Uani 1 1 d . . . H11 H 0.0209 0.2291 0.1517 0.033 Uiso 1 1 calc R . . C12 C -0.13121(11) 0.17310(9) 0.18746(11) 0.0272(2) Uani 1 1 d . . . H12 H -0.1998 0.1902 0.1102 0.033 Uiso 1 1 calc R . . C13 C -0.16197(11) 0.12462(8) 0.27584(10) 0.0242(2) Uani 1 1 d . . . C14 C -0.06146(12) 0.10136(10) 0.38980(11) 0.0290(3) Uani 1 1 d . . . H14 H -0.0827 0.069 0.4507 0.035 Uiso 1 1 calc R . . C15 C 0.06920(11) 0.12537(10) 0.41427(11) 0.0285(3) Uani 1 1 d . . . H15 H 0.1375 0.1093 0.4921 0.034 Uiso 1 1 calc R . . C16 C 0.24338(11) 0.19683(9) 0.35616(11) 0.0271(2) Uani 1 1 d . . . O2 O 0.26209(9) 0.24425(8) 0.26617(8) 0.0346(2) Uani 1 1 d . . . H2 H 0.354(2) 0.2569(14) 0.2933(17) 0.052 Uiso 1 1 d . . . O3 O 0.33380(8) 0.17483(8) 0.45320(8) 0.0374(2) Uani 1 1 d . . . O4 O -0.28824(8) 0.09784(7) 0.25643(9) 0.0301(2) Uani 1 1 d . . . H4 H -0.3459(17) 0.1212(13) 0.1843(16) 0.045 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 0.0182(5) 0.0241(5) 0.0276(5) -0.0050(4) 0.0095(4) -0.0013(4) C2 0.0221(5) 0.0315(6) 0.0336(6) 0.0045(5) 0.0084(5) -0.0042(5) C3 0.0207(6) 0.0398(7) 0.0354(6) 0.0037(5) 0.0046(5) -0.0030(5) C4 0.0276(6) 0.0424(7) 0.0330(6) -0.0026(5) 0.0175(5) -0.0060(5) C5 0.0241(6) 0.0412(7) 0.0277(6) 0.0009(5) 0.0112(5) -0.0022(5) C6 0.0187(5) 0.0225(5) 0.0301(6) -0.0026(4) 0.0087(4) -0.0002(4) C7 0.0440(8) 0.0482(8) 0.0484(8) 0.0056(7) 0.0281(7) -0.0027(6) C8 0.0276(6) 0.0247(6) 0.0480(7) -0.0018(5) 0.0212(5) 0.0000(5) C9 0.0301(7) 0.0381(7) 0.0704(10) -0.0013(7) 0.0292(7) -0.0042(6) N1 0.0173(5) 0.0353(5) 0.0300(5) 0.0017(4) 0.0090(4) -0.0010(4) N2 0.0206(5) 0.0380(6) 0.0360(5) -0.0072(4) 0.0127(4) -0.0056(4) N3 0.0179(5) 0.0308(5) 0.0410(6) 0.0001(4) 0.0120(4) -0.0018(4) O1 0.0223(4) 0.0415(5) 0.0341(5) 0.0071(4) 0.0045(4) -0.0051(4) C10 0.0189(5) 0.0269(6) 0.0270(5) -0.0049(4) 0.0087(4) -0.0018(4) C11 0.0244(6) 0.0320(6) 0.0265(6) 0.0001(5) 0.0107(5) -0.0028(5) C12 0.0209(5) 0.0323(6) 0.0245(5) 0.0005(4) 0.0055(4) -0.0002(4) C13 0.0189(5) 0.0227(5) 0.0303(6) -0.0016(4) 0.0092(4) -0.0003(4) C14 0.0244(6) 0.0339(6) 0.0286(6) 0.0059(5) 0.0108(5) 0.0000(5) C15 0.0217(5) 0.0342(6) 0.0256(5) 0.0020(5) 0.0057(4) 0.0012(5) C16 0.0216(5) 0.0309(6) 0.0287(6) -0.0082(5) 0.0102(4) -0.0031(4) O2 0.0211(4) 0.0490(6) 0.0335(5) -0.0006(4) 0.0109(4) -0.0081(4) O3 0.0202(4) 0.0559(6) 0.0321(5) -0.0019(4) 0.0065(4) -0.0028(4) O4 0.0181(4) 0.0346(5) 0.0361(5) 0.0037(4) 0.0096(3) -0.0014(3) #----------------------------------------------------------------------------# # 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 1.3856(16) . ? C1 C5 1.3866(17) . ? C1 C6 1.5031(15) . ? C2 C3 1.3858(16) . ? C2 H2A 0.95 . ? C3 N2 1.3292(17) . ? C3 H3 0.95 . ? C4 N2 1.3348(17) . ? C4 C5 1.3843(17) . ? C4 H4A 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2255(14) . ? C6 N1 1.3412(16) . ? C7 C8 1.501(2) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 N3 1.2820(17) . ? C8 C9 1.4988(18) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? N1 N3 1.3910(13) . ? N1 H1 0.845(17) . ? C10 C15 1.3900(17) . ? C10 C11 1.3945(16) . ? C10 C16 1.4866(15) . ? C11 C12 1.3834(16) . ? C11 H11 0.95 . ? C12 C13 1.3876(16) . ? C12 H12 0.95 . ? C13 O4 1.3593(14) . ? C13 C14 1.3925(16) . ? C14 C15 1.3825(16) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 O3 1.2143(15) . ? C16 O2 1.3289(15) . ? O2 H2 0.94(2) . ? O4 H4 0.890(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 C5 117.88(10) . . ? C2 C1 C6 124.95(11) . . ? C5 C1 C6 117.17(10) . . ? C1 C2 C3 118.96(11) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? N2 C3 C2 123.32(12) . . ? N2 C3 H3 118.3 . . ? C2 C3 H3 118.3 . . ? N2 C4 C5 122.97(12) . . ? N2 C4 H4A 118.5 . . ? C5 C4 H4A 118.5 . . ? C4 C5 C1 119.20(11) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? O1 C6 N1 123.79(10) . . ? O1 C6 C1 119.70(11) . . ? N1 C6 C1 116.50(10) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 116.24(12) . . ? N3 C8 C7 125.50(12) . . ? C9 C8 C7 118.26(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 N1 N3 119.25(10) . . ? C6 N1 H1 120.2(11) . . ? N3 N1 H1 120.5(11) . . ? C3 N2 C4 117.65(10) . . ? C8 N3 N1 115.88(11) . . ? C15 C10 C11 118.92(10) . . ? C15 C10 C16 118.73(10) . . ? C11 C10 C16 122.34(11) . . ? C12 C11 C10 120.89(11) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.62(11) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? O4 C13 C12 122.66(10) . . ? O4 C13 C14 117.33(10) . . ? C12 C13 C14 120.01(10) . . ? C15 C14 C13 119.97(11) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C10 120.58(11) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O3 C16 O2 123.05(11) . . ? O3 C16 C10 123.47(11) . . ? O2 C16 C10 113.48(10) . . ? C16 O2 H2 107.7(11) . . ? C13 O4 H4 110.6(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 C5 C1 C2 C3 1.14(18) . . . . ? C6 C1 C2 C3 -178.81(11) . . . . ? C1 C2 C3 N2 -0.9(2) . . . . ? N2 C4 C5 C1 -0.9(2) . . . . ? C2 C1 C5 C4 -0.31(18) . . . . ? C6 C1 C5 C4 179.64(11) . . . . ? C2 C1 C6 O1 172.06(12) . . . . ? C5 C1 C6 O1 -7.88(17) . . . . ? C2 C1 C6 N1 -8.66(17) . . . . ? C5 C1 C6 N1 171.39(11) . . . . ? O1 C6 N1 N3 0.91(18) . . . . ? C1 C6 N1 N3 -178.33(10) . . . . ? C2 C3 N2 C4 -0.3(2) . . . . ? C5 C4 N2 C3 1.2(2) . . . . ? C9 C8 N3 N1 179.66(11) . . . . ? C7 C8 N3 N1 0.00(19) . . . . ? C6 N1 N3 C8 173.21(11) . . . . ? C15 C10 C11 C12 -0.22(18) . . . . ? C16 C10 C11 C12 -179.94(11) . . . . ? C10 C11 C12 C13 -0.59(18) . . . . ? C11 C12 C13 O4 -178.78(11) . . . . ? C11 C12 C13 C14 1.13(18) . . . . ? O4 C13 C14 C15 179.05(11) . . . . ? C12 C13 C14 C15 -0.87(19) . . . . ? C13 C14 C15 C10 0.05(19) . . . . ? C11 C10 C15 C14 0.49(18) . . . . ? C16 C10 C15 C14 -179.78(11) . . . . ? C15 C10 C16 O3 2.03(18) . . . . ? C11 C10 C16 O3 -178.25(12) . . . . ? C15 C10 C16 O2 -178.43(10) . . . . ? C11 C10 C16 O2 1.30(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.85(2) 2.66(2) 3.274(1) 131(1) 2 O2 H2 N2 0.94(2) 1.74(2) 2.676(1) 174(2) . O4 H4 O1 0.89(2) 1.77(2) 2.624(1) 161(2) 4_465 C4 H4A O3 0.95 2.61 3.278(2) 128 . ###END data_8 _database_code_depnum_ccdc_archive 'CCDC 847204' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-06-30T10:16:52-00:00 _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 ; (salicyclic 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)/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 11.2793(5) _cell_length_b 3.7452(2) _cell_length_c 29.8282(15) _cell_angle_alpha 90 _cell_angle_beta 93.567(4) _cell_angle_gamma 90 _cell_volume 1257.60(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2041 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.07 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_T_max 0.9945 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_unetI/netI 0.0461 _diffrn_reflns_number 8409 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 2987 _reflns_number_gt 2208 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0410P)^2^+0.5076P] 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 2987 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.113 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.278 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # 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 0.73688(13) 0.5865(4) 0.62374(5) 0.0212(3) Uani 1 1 d . . . C2 C 0.65168(14) 0.6389(4) 0.58862(5) 0.0241(3) Uani 1 1 d . . . H2A H 0.5758 0.734 0.5941 0.029 Uiso 1 1 calc R . . C3 C 0.67968(15) 0.5497(5) 0.54547(5) 0.0285(4) Uani 1 1 d . . . H3 H 0.6216 0.5863 0.5215 0.034 Uiso 1 1 calc R . . C4 C 0.86673(14) 0.3646(5) 0.57012(5) 0.0270(4) Uani 1 1 d . . . H4A H 0.9418 0.2691 0.5637 0.032 Uiso 1 1 calc R . . C5 C 0.84607(14) 0.4471(4) 0.61408(5) 0.0244(4) Uani 1 1 d . . . H5 H 0.906 0.4086 0.6374 0.029 Uiso 1 1 calc R . . C6 C 0.71770(14) 0.6862(4) 0.67169(5) 0.0225(3) Uani 1 1 d . . . N1 N 0.60725(12) 0.6442(4) 0.68426(4) 0.0265(3) Uani 1 1 d . . . H1 H 0.5509(18) 0.545(6) 0.6648(7) 0.04 Uiso 1 1 d . . . N2 N 0.78487(12) 0.4144(4) 0.53624(4) 0.0277(3) Uani 1 1 d . . . N3 N 0.57398(14) 0.7171(5) 0.72830(5) 0.0321(4) Uani 1 1 d . . . H3A H 0.5813(19) 0.953(7) 0.7334(7) 0.048 Uiso 1 1 d . . . H3B H 0.6319(19) 0.620(6) 0.7479(7) 0.048 Uiso 1 1 d . . . O1 O 0.80028(10) 0.7936(4) 0.69670(4) 0.0346(3) Uani 1 1 d . . . C7 C 0.76960(13) -0.0117(4) 0.38580(5) 0.0201(3) Uani 1 1 d . . . C8 C 0.87864(13) 0.0667(4) 0.36824(5) 0.0223(3) Uani 1 1 d . . . H8 H 0.9389 0.1819 0.3866 0.027 Uiso 1 1 calc R . . C9 C 0.89978(14) -0.0213(4) 0.32449(5) 0.0246(4) Uani 1 1 d . . . H9 H 0.9743 0.0313 0.3129 0.03 Uiso 1 1 calc R . . C10 C 0.81127(14) -0.1869(4) 0.29772(5) 0.0244(3) Uani 1 1 d . . . H10 H 0.826 -0.25 0.2677 0.029 Uiso 1 1 calc R . . C11 C 0.70204(14) -0.2615(4) 0.31391(5) 0.0232(3) Uani 1 1 d . . . H11 H 0.6414 -0.3699 0.295 0.028 Uiso 1 1 calc R . . C12 C 0.68145(13) -0.1768(4) 0.35816(5) 0.0207(3) Uani 1 1 d . . . C13 C 0.74590(14) 0.0836(4) 0.43251(5) 0.0229(3) Uani 1 1 d . . . O2 O 0.83334(10) 0.2381(3) 0.45547(4) 0.0321(3) Uani 1 1 d . . . H2 H 0.8087(18) 0.299(6) 0.4842(7) 0.048 Uiso 1 1 d . . . O3 O 0.64897(10) 0.0195(4) 0.44823(4) 0.0314(3) Uani 1 1 d . . . O4 O 0.57376(9) -0.2624(3) 0.37375(4) 0.0287(3) Uani 1 1 d . . . H4 H 0.5857(18) -0.186(6) 0.4032(7) 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 0.0239(8) 0.0191(8) 0.0209(7) 0.0009(6) 0.0033(6) -0.0059(6) C2 0.0232(8) 0.0257(9) 0.0235(7) 0.0021(6) 0.0013(6) -0.0028(7) C3 0.0306(9) 0.0337(10) 0.0206(7) 0.0017(7) -0.0023(6) -0.0045(8) C4 0.0246(8) 0.0293(9) 0.0273(8) -0.0012(7) 0.0037(6) -0.0020(7) C5 0.0248(8) 0.0264(9) 0.0217(7) 0.0014(6) -0.0004(6) -0.0029(7) C6 0.0248(8) 0.0235(8) 0.0191(7) 0.0018(6) 0.0004(6) -0.0020(7) N1 0.0233(7) 0.0388(9) 0.0174(6) -0.0005(6) 0.0016(5) -0.0044(6) N2 0.0320(8) 0.0310(8) 0.0203(6) -0.0022(6) 0.0028(5) -0.0060(6) N3 0.0319(8) 0.0471(10) 0.0179(6) 0.0004(6) 0.0054(5) -0.0017(8) O1 0.0276(6) 0.0525(8) 0.0237(6) -0.0084(5) 0.0010(5) -0.0124(6) C7 0.0224(8) 0.0203(8) 0.0175(7) 0.0017(6) 0.0010(5) 0.0001(6) C8 0.0211(8) 0.0222(8) 0.0233(7) 0.0012(6) -0.0008(6) -0.0016(6) C9 0.0233(8) 0.0266(9) 0.0245(8) 0.0044(6) 0.0062(6) 0.0018(7) C10 0.0311(9) 0.0252(9) 0.0171(7) 0.0015(6) 0.0036(6) 0.0042(7) C11 0.0262(8) 0.0242(9) 0.0186(7) -0.0003(6) -0.0034(6) 0.0000(7) C12 0.0198(7) 0.0207(8) 0.0217(7) 0.0028(6) 0.0017(5) 0.0015(6) C13 0.0257(8) 0.0228(8) 0.0200(7) 0.0011(6) 0.0006(6) 0.0002(7) O2 0.0321(6) 0.0457(8) 0.0186(5) -0.0084(5) 0.0027(5) -0.0089(6) O3 0.0279(6) 0.0441(8) 0.0229(6) -0.0029(5) 0.0074(4) -0.0037(6) O4 0.0213(6) 0.0415(8) 0.0237(6) -0.0048(5) 0.0034(4) -0.0076(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 C5 1.384(2) . ? C1 C2 1.391(2) . ? C1 C6 1.507(2) . ? C2 C3 1.385(2) . ? C2 H2A 0.95 . ? C3 N2 1.335(2) . ? C3 H3 0.95 . ? C4 N2 1.339(2) . ? C4 C5 1.381(2) . ? C4 H4A 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2245(19) . ? C6 N1 1.332(2) . ? N1 N3 1.4150(18) . ? N1 H1 0.91(2) . ? N3 H3A 0.90(2) . ? N3 H3B 0.92(2) . ? C7 C12 1.396(2) . ? C7 C8 1.398(2) . ? C7 C13 1.479(2) . ? C8 C9 1.381(2) . ? C8 H8 0.95 . ? C9 C10 1.386(2) . ? C9 H9 0.95 . ? C10 C11 1.380(2) . ? C10 H10 0.95 . ? C11 C12 1.391(2) . ? C11 H11 0.95 . ? C12 O4 1.3656(18) . ? C13 O3 1.2394(18) . ? C13 O2 1.3010(19) . ? O2 H2 0.94(2) . ? O4 H4 0.92(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 C5 C1 C2 118.59(13) . . ? C5 C1 C6 118.24(14) . . ? C2 C1 C6 123.13(14) . . ? C3 C2 C1 118.61(15) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? N2 C3 C2 122.71(15) . . ? N2 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? N2 C4 C5 122.44(15) . . ? N2 C4 H4A 118.8 . . ? C5 C4 H4A 118.8 . . ? C4 C5 C1 119.13(15) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? O1 C6 N1 123.82(14) . . ? O1 C6 C1 120.72(14) . . ? N1 C6 C1 115.45(13) . . ? C6 N1 N3 123.02(14) . . ? C6 N1 H1 119.8(12) . . ? N3 N1 H1 117.0(12) . . ? C3 N2 C4 118.51(13) . . ? N1 N3 H3A 108.7(14) . . ? N1 N3 H3B 107.0(13) . . ? H3A N3 H3B 103(2) . . ? C12 C7 C8 118.87(13) . . ? C12 C7 C13 119.96(13) . . ? C8 C7 C13 121.16(14) . . ? C9 C8 C7 120.78(14) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.39(14) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 121.07(14) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.43(14) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? O4 C12 C11 118.31(14) . . ? O4 C12 C7 121.25(13) . . ? C11 C12 C7 120.44(14) . . ? O3 C13 O2 123.00(14) . . ? O3 C13 C7 121.68(14) . . ? O2 C13 C7 115.32(13) . . ? C13 O2 H2 109.1(13) . . ? C12 O4 H4 99.9(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C1 C2 C3 0.0(2) . . . . ? C6 C1 C2 C3 177.74(15) . . . . ? C1 C2 C3 N2 0.2(3) . . . . ? N2 C4 C5 C1 0.0(3) . . . . ? C2 C1 C5 C4 -0.1(2) . . . . ? C6 C1 C5 C4 -177.95(15) . . . . ? C5 C1 C6 O1 31.7(2) . . . . ? C2 C1 C6 O1 -146.03(17) . . . . ? C5 C1 C6 N1 -147.40(16) . . . . ? C2 C1 C6 N1 34.8(2) . . . . ? O1 C6 N1 N3 -0.6(3) . . . . ? C1 C6 N1 N3 178.56(15) . . . . ? C2 C3 N2 C4 -0.3(3) . . . . ? C5 C4 N2 C3 0.2(3) . . . . ? C12 C7 C8 C9 -0.8(2) . . . . ? C13 C7 C8 C9 -179.61(15) . . . . ? C7 C8 C9 C10 0.5(2) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C9 C10 C11 C12 -1.5(2) . . . . ? C10 C11 C12 O4 -178.20(14) . . . . ? C10 C11 C12 C7 1.2(2) . . . . ? C8 C7 C12 O4 179.35(14) . . . . ? C13 C7 C12 O4 -1.9(2) . . . . ? C8 C7 C12 C11 0.0(2) . . . . ? C13 C7 C12 C11 178.81(14) . . . . ? C12 C7 C13 O3 0.3(2) . . . . ? C8 C7 C13 O3 179.03(15) . . . . ? C12 C7 C13 O2 -179.63(14) . . . . ? C8 C7 C13 O2 -0.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.91(2) 2.05(2) 2.961(2) 173(2) 3_656 N3 H3A N3 0.90(2) 2.87(2) 3.745(2) 166(2) 1_565 N3 H3B O1 0.92(2) 2.16(2) 3.023(2) 156(2) 2_646 O2 H2 N2 0.94(2) 1.65(2) 2.589(2) 172(2) . O4 H4 O3 0.92(2) 1.67(2) 2.556(2) 159(2) . ###END data_9 _database_code_depnum_ccdc_archive 'CCDC 847205' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-06-30T09:55:53-00:00 _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 ; (salicyclic 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)/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 7.3504(4) _cell_length_b 29.8032(16) _cell_length_c 7.6524(4) _cell_angle_alpha 90 _cell_angle_beta 112.787(3) _cell_angle_gamma 90 _cell_volume 1545.54(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7396 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.32 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9474 _exptl_absorpt_correction_T_max 0.9567 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_number 16272 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3721 _reflns_number_gt 3278 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0549P)^2^+0.5123P] 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 3721 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.112 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.273 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # 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 0.50984(16) 0.19703(4) 0.19272(15) 0.0220(2) Uani 1 1 d . . . C2 C 0.53504(18) 0.21949(4) 0.35986(17) 0.0267(2) Uani 1 1 d . . . H2A H 0.5339 0.2514 0.3635 0.032 Uiso 1 1 calc R . . C3 C 0.56192(19) 0.19456(4) 0.52115(17) 0.0292(3) Uani 1 1 d . . . H3 H 0.5768 0.21 0.6344 0.035 Uiso 1 1 calc R . . C4 C 0.54426(19) 0.12827(4) 0.36261(17) 0.0295(3) Uani 1 1 d . . . H4A H 0.5492 0.0964 0.3635 0.035 Uiso 1 1 calc R . . C5 C 0.51306(18) 0.15058(4) 0.19434(16) 0.0259(2) Uani 1 1 d . . . H5 H 0.4942 0.1343 0.082 0.031 Uiso 1 1 calc R . . C6 C 0.46524(17) 0.22005(4) 0.00604(15) 0.0228(2) Uani 1 1 d . . . C7 C 0.5645(2) 0.35300(5) -0.0038(2) 0.0428(4) Uani 1 1 d . . . H7A H 0.5057 0.3398 0.0795 0.064 Uiso 1 1 calc R . . H7B H 0.5017 0.3819 -0.0519 0.064 Uiso 1 1 calc R . . H7C H 0.7062 0.3575 0.0676 0.064 Uiso 1 1 calc R . . C8 C 0.53412(17) 0.32210(4) -0.16631(18) 0.0290(3) Uani 1 1 d . . . C9 C 0.5059(2) 0.34275(5) -0.3537(2) 0.0443(4) Uani 1 1 d . . . H9A H 0.508 0.3192 -0.4422 0.066 Uiso 1 1 calc R . . H9B H 0.6125 0.3642 -0.3367 0.066 Uiso 1 1 calc R . . H9C H 0.3787 0.3584 -0.4047 0.066 Uiso 1 1 calc R . . N1 N 0.55219(16) 0.25974(3) 0.01197(14) 0.0258(2) Uani 1 1 d . . . H1 H 0.648(2) 0.2697(6) 0.120(2) 0.039 Uiso 1 1 d . . . N2 N 0.56780(16) 0.14969(4) 0.52398(14) 0.0289(2) Uani 1 1 d . . . N3 N 0.52387(16) 0.27946(4) -0.16390(14) 0.0290(2) Uani 1 1 d . . . O1 O 0.34949(14) 0.20255(3) -0.14079(12) 0.0311(2) Uani 1 1 d . . . C10 C 0.71657(16) 0.02374(4) 0.95256(16) 0.0235(2) Uani 1 1 d . . . C11 C 0.75497(18) -0.02156(4) 0.93041(18) 0.0287(3) Uani 1 1 d . . . C12 C 0.8110(2) -0.05004(5) 1.0869(2) 0.0363(3) Uani 1 1 d . . . H12 H 0.8397 -0.0806 1.0737 0.044 Uiso 1 1 calc R . . C13 C 0.8250(2) -0.03406(5) 1.2604(2) 0.0377(3) Uani 1 1 d . . . H13 H 0.8621 -0.0539 1.3657 0.045 Uiso 1 1 calc R . . C14 C 0.7859(2) 0.01056(5) 1.28394(18) 0.0346(3) Uani 1 1 d . . . H14 H 0.7951 0.0213 1.404 0.041 Uiso 1 1 calc R . . C15 C 0.73364(18) 0.03904(4) 1.13079(17) 0.0284(3) Uani 1 1 d . . . H15 H 0.7086 0.0697 1.1466 0.034 Uiso 1 1 calc R . . C16 C 0.65782(18) 0.05426(4) 0.78835(16) 0.0261(2) Uani 1 1 d . . . O2 O 0.63227(15) 0.09650(3) 0.82569(12) 0.0322(2) Uani 1 1 d . . . H2 H 0.604(3) 0.1129(6) 0.721(3) 0.048 Uiso 1 1 d . . . O3 O 0.63492(16) 0.04147(3) 0.62904(12) 0.0380(2) Uani 1 1 d . . . O4 O 0.73949(17) -0.03923(3) 0.76282(15) 0.0414(3) Uani 1 1 d . . . H4 H 0.695(3) -0.0167(7) 0.680(3) 0.062 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 0.0211(5) 0.0219(5) 0.0207(5) 0.0015(4) 0.0057(4) -0.0004(4) C2 0.0334(6) 0.0214(6) 0.0258(6) -0.0009(4) 0.0121(5) -0.0005(5) C3 0.0370(7) 0.0292(6) 0.0240(5) -0.0025(4) 0.0147(5) -0.0026(5) C4 0.0373(7) 0.0224(6) 0.0278(6) 0.0025(4) 0.0115(5) -0.0004(5) C5 0.0316(6) 0.0224(6) 0.0210(5) -0.0008(4) 0.0074(4) -0.0007(4) C6 0.0255(5) 0.0206(5) 0.0195(5) 0.0010(4) 0.0056(4) 0.0036(4) C7 0.0452(8) 0.0228(6) 0.0455(8) 0.0008(6) 0.0011(6) 0.0029(6) C8 0.0219(6) 0.0269(6) 0.0348(6) 0.0086(5) 0.0074(5) 0.0020(4) C9 0.0431(8) 0.0427(8) 0.0495(9) 0.0242(7) 0.0207(7) 0.0094(6) N1 0.0330(5) 0.0215(5) 0.0186(4) 0.0016(4) 0.0052(4) -0.0021(4) N2 0.0342(6) 0.0292(5) 0.0239(5) 0.0040(4) 0.0120(4) -0.0009(4) N3 0.0377(6) 0.0257(5) 0.0224(5) 0.0059(4) 0.0103(4) 0.0032(4) O1 0.0377(5) 0.0247(4) 0.0213(4) -0.0003(3) 0.0008(4) -0.0030(4) C10 0.0226(5) 0.0242(6) 0.0225(5) 0.0017(4) 0.0074(4) -0.0024(4) C11 0.0263(6) 0.0268(6) 0.0306(6) -0.0017(5) 0.0085(5) -0.0026(5) C12 0.0352(7) 0.0253(6) 0.0413(7) 0.0056(5) 0.0072(6) 0.0024(5) C13 0.0368(7) 0.0356(7) 0.0329(7) 0.0144(5) 0.0048(5) 0.0012(6) C14 0.0386(7) 0.0408(7) 0.0227(6) 0.0059(5) 0.0100(5) 0.0009(6) C15 0.0319(6) 0.0285(6) 0.0240(6) 0.0018(4) 0.0102(5) 0.0007(5) C16 0.0296(6) 0.0263(6) 0.0217(5) -0.0001(4) 0.0093(4) -0.0048(5) O2 0.0501(6) 0.0237(4) 0.0214(4) 0.0026(3) 0.0124(4) -0.0014(4) O3 0.0607(6) 0.0319(5) 0.0219(4) -0.0014(3) 0.0166(4) -0.0033(4) O4 0.0575(7) 0.0293(5) 0.0356(5) -0.0062(4) 0.0160(5) 0.0026(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 C5 1.3845(16) . ? C1 C2 1.3910(15) . ? C1 C6 1.5020(15) . ? C2 C3 1.3877(16) . ? C2 H2A 0.95 . ? C3 N2 1.3377(17) . ? C3 H3 0.95 . ? C4 N2 1.3405(16) . ? C4 C5 1.3871(16) . ? C4 H4A 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2320(14) . ? C6 N1 1.3370(15) . ? C7 C8 1.493(2) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 N3 1.2735(17) . ? C8 C9 1.4992(18) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? N1 N3 1.4082(13) . ? N1 H1 0.903(17) . ? C10 C15 1.3969(16) . ? C10 C11 1.4029(17) . ? C10 C16 1.4741(15) . ? C11 O4 1.3498(16) . ? C11 C12 1.3936(18) . ? C12 C13 1.377(2) . ? C12 H12 0.95 . ? C13 C14 1.387(2) . ? C13 H13 0.95 . ? C14 C15 1.3757(17) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 O3 1.2251(14) . ? C16 O2 1.3203(15) . ? O2 H2 0.89(2) . ? O4 H4 0.89(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C2 118.50(10) . . ? C5 C1 C6 117.51(10) . . ? C2 C1 C6 123.85(10) . . ? C3 C2 C1 118.85(11) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? N2 C3 C2 122.84(11) . . ? N2 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? N2 C4 C5 122.88(11) . . ? N2 C4 H4A 118.6 . . ? C5 C4 H4A 118.6 . . ? C1 C5 C4 118.93(11) . . ? C1 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? O1 C6 N1 123.90(10) . . ? O1 C6 C1 119.55(10) . . ? N1 C6 C1 116.52(9) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C7 126.45(12) . . ? N3 C8 C9 115.88(12) . . ? C7 C8 C9 117.64(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 N1 N3 116.42(9) . . ? C6 N1 H1 121.0(11) . . ? N3 N1 H1 120.7(10) . . ? C3 N2 C4 117.99(10) . . ? C8 N3 N1 116.27(10) . . ? C15 C10 C11 119.07(11) . . ? C15 C10 C16 121.12(11) . . ? C11 C10 C16 119.81(10) . . ? O4 C11 C12 117.83(12) . . ? O4 C11 C10 122.91(11) . . ? C12 C11 C10 119.26(12) . . ? C13 C12 C11 120.32(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.00(12) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 118.99(12) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C10 121.35(12) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? O3 C16 O2 122.40(11) . . ? O3 C16 C10 122.57(11) . . ? O2 C16 C10 115.04(10) . . ? C16 O2 H2 109.5(12) . . ? C11 O4 H4 104.6(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 C5 C1 C2 C3 -0.14(17) . . . . ? C6 C1 C2 C3 175.48(11) . . . . ? C1 C2 C3 N2 1.08(19) . . . . ? C2 C1 C5 C4 -1.00(17) . . . . ? C6 C1 C5 C4 -176.89(11) . . . . ? N2 C4 C5 C1 1.34(19) . . . . ? C5 C1 C6 O1 34.00(16) . . . . ? C2 C1 C6 O1 -141.65(12) . . . . ? C5 C1 C6 N1 -147.85(11) . . . . ? C2 C1 C6 N1 36.50(16) . . . . ? O1 C6 N1 N3 -7.21(17) . . . . ? C1 C6 N1 N3 174.73(10) . . . . ? C2 C3 N2 C4 -0.79(19) . . . . ? C5 C4 N2 C3 -0.44(19) . . . . ? C7 C8 N3 N1 -2.76(19) . . . . ? C9 C8 N3 N1 179.38(11) . . . . ? C6 N1 N3 C8 153.02(11) . . . . ? C15 C10 C11 O4 179.12(11) . . . . ? C16 C10 C11 O4 -0.46(18) . . . . ? C15 C10 C11 C12 -0.63(18) . . . . ? C16 C10 C11 C12 179.79(11) . . . . ? O4 C11 C12 C13 -178.60(12) . . . . ? C10 C11 C12 C13 1.2(2) . . . . ? C11 C12 C13 C14 -0.7(2) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C13 C14 C15 C10 0.9(2) . . . . ? C11 C10 C15 C14 -0.42(18) . . . . ? C16 C10 C15 C14 179.15(12) . . . . ? C15 C10 C16 O3 -177.38(12) . . . . ? C11 C10 C16 O3 2.19(18) . . . . ? C15 C10 C16 O2 2.84(17) . . . . ? C11 C10 C16 O2 -177.59(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 N1 H1 O1 0.90(2) 2.03(2) 2.933(1) 175(2) 4_666 O2 H2 N2 0.89(2) 1.80(2) 2.687(1) 174(2) . O4 H4 O3 0.89(2) 1.79(2) 2.610(1) 151(2) . C4 H4A O3 0.95 2.49 3.200(2) 131 . ###END data_10 _database_code_depnum_ccdc_archive 'CCDC 847206' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-06-30T10:42:58-00:00 _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-chloro-4-nitrobenzoic acid).(isonicotinic acid hydrazide) ; _chemical_formula_moiety 'C7 H4 Cl N O4, C6 H7 N3 O' _chemical_formula_sum 'C13 H11 Cl N4 O5' _chemical_formula_weight 338.71 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1538(3) _cell_length_b 11.0592(4) _cell_length_c 15.0521(5) _cell_angle_alpha 89.085(2) _cell_angle_beta 72.649(2) _cell_angle_gamma 89.906(2) _cell_volume 1454.25(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4416 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.17 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9113 _exptl_absorpt_correction_T_max 0.957 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_unetI/netI 0.0423 _diffrn_reflns_number 16205 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.955 _diffrn_measured_fraction_theta_max 0.955 _reflns_number_total 6699 _reflns_number_gt 4861 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.1366P)^2^+0.3203P] 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 6699 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2086 _refine_ls_wR_factor_gt 0.1861 _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 1.515 _refine_diff_density_min -0.6 _refine_diff_density_rms 0.108 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C1A C 0.0718(3) -0.0579(2) 0.59161(15) 0.0194(5) Uani 1 1 d . . . C2A C -0.0515(3) 0.0192(2) 0.62563(17) 0.0238(5) Uani 1 1 d . . . H2C H -0.0394 0.1041 0.6159 0.029 Uiso 1 1 calc R . . C3A C -0.1920(3) -0.0299(3) 0.67392(17) 0.0258(5) Uani 1 1 d . . . H3E H -0.2769 0.0228 0.6951 0.031 Uiso 1 1 calc R . . C4A C -0.0939(3) -0.2220(3) 0.66003(18) 0.0296(6) Uani 1 1 d . . . H4A H -0.1083 -0.3062 0.673 0.036 Uiso 1 1 calc R . . C5A C 0.0481(3) -0.1813(2) 0.60944(18) 0.0260(5) Uani 1 1 d . . . H5A H 0.1297 -0.2368 0.5868 0.031 Uiso 1 1 calc R . . C6A C 0.2274(3) -0.0176(2) 0.53267(16) 0.0185(5) Uani 1 1 d . . . N1A N 0.2579(2) 0.1004(2) 0.53216(16) 0.0243(5) Uani 1 1 d . . . H1A H 0.203(4) 0.146(3) 0.554(2) 0.036 Uiso 1 1 d . . . N2A N -0.2136(2) -0.1478(2) 0.69201(15) 0.0289(5) Uani 1 1 d . . . N3A N 0.3945(2) 0.1509(2) 0.47213(18) 0.0264(5) Uani 1 1 d . . . H3A H 0.418(4) 0.120(3) 0.423(3) 0.04 Uiso 1 1 d . . . H3B H 0.465(4) 0.129(3) 0.497(2) 0.04 Uiso 1 1 d . . . O1A O 0.31900(19) -0.09035(16) 0.48628(12) 0.0252(4) Uani 1 1 d . . . C1B C 0.4129(3) 0.5337(2) 0.40759(17) 0.0224(5) Uani 1 1 d . . . C2B C 0.5278(3) 0.4522(2) 0.36748(19) 0.0284(6) Uani 1 1 d . . . H2D H 0.5135 0.368 0.381 0.034 Uiso 1 1 calc R . . C3B C 0.6641(3) 0.4955(3) 0.30735(19) 0.0311(6) Uani 1 1 d . . . H3F H 0.7423 0.4392 0.2798 0.037 Uiso 1 1 calc R . . C4B C 0.5799(3) 0.6912(3) 0.32630(19) 0.0309(6) Uani 1 1 d . . . H4B H 0.5983 0.7749 0.3122 0.037 Uiso 1 1 calc R . . C5B C 0.4410(3) 0.6564(2) 0.38687(18) 0.0273(6) Uani 1 1 d . . . H5B H 0.3656 0.715 0.4141 0.033 Uiso 1 1 calc R . . C6B C 0.2609(3) 0.4998(2) 0.47497(17) 0.0227(5) Uani 1 1 d . . . N1B N 0.2397(2) 0.3836(2) 0.50065(16) 0.0260(5) Uani 1 1 d . . . H1B H 0.306(4) 0.328(3) 0.483(2) 0.039 Uiso 1 1 d . . . N2B N 0.6903(3) 0.6125(2) 0.28642(15) 0.0305(5) Uani 1 1 d . . . N3B N 0.1027(3) 0.3397(2) 0.56503(18) 0.0281(5) Uani 1 1 d . . . H3C H 0.040(4) 0.353(3) 0.541(3) 0.042 Uiso 1 1 d . . . H3D H 0.087(4) 0.378(3) 0.614(3) 0.042 Uiso 1 1 d . . . O1B O 0.1617(2) 0.57645(17) 0.50488(15) 0.0340(5) Uani 1 1 d . . . C7A C -0.5437(3) -0.3382(2) 0.95867(18) 0.0242(5) Uani 1 1 d . . . C8A C -0.5538(3) -0.3278(2) 1.05210(19) 0.0273(6) Uani 1 1 d . . . C9A C -0.6757(3) -0.3809(2) 1.12118(18) 0.0294(6) Uani 1 1 d . . . H9A H -0.6849 -0.3722 1.1853 0.035 Uiso 1 1 calc R . . C10A C -0.7815(3) -0.4459(2) 1.09306(19) 0.0286(6) Uani 1 1 d . . . C11A C -0.7762(3) -0.4596(3) 1.0020(2) 0.0313(6) Uani 1 1 d . . . H11A H -0.851 -0.5058 0.9852 0.038 Uiso 1 1 calc R . . C12A C -0.6577(3) -0.4033(3) 0.9356(2) 0.0314(6) Uani 1 1 d . . . H12A H -0.6532 -0.409 0.8719 0.038 Uiso 1 1 calc R . . C13A C -0.4105(3) -0.2864(2) 0.88176(18) 0.0270(6) Uani 1 1 d . . . N4A N -0.9085(3) -0.5031(2) 1.16696(17) 0.0335(6) Uani 1 1 d . . . O2A O -0.4533(2) -0.2430(2) 0.81211(14) 0.0362(5) Uani 1 1 d . . . H2A H -0.363(5) -0.210(3) 0.774(3) 0.054 Uiso 1 1 d . . . O3A O -0.2811(2) -0.2863(2) 0.88554(14) 0.0364(5) Uani 1 1 d . . . O4A O -1.0029(2) -0.56130(19) 1.14318(16) 0.0418(5) Uani 1 1 d . . . O5A O -0.9136(3) -0.4868(2) 1.24783(15) 0.0445(6) Uani 1 1 d . . . Cl1A Cl -0.42304(9) -0.24701(8) 1.08941(6) 0.0459(2) Uani 1 1 d . . . C7B C 1.0484(3) 0.8423(2) 0.04084(17) 0.0219(5) Uani 1 1 d . . . C8B C 1.1819(3) 0.9105(2) 0.02630(17) 0.0246(5) Uani 1 1 d . . . C9B C 1.2738(3) 0.9393(2) -0.06322(18) 0.0263(6) Uani 1 1 d . . . H9B H 1.3652 0.985 -0.0732 0.032 Uiso 1 1 calc R . . C10B C 1.2278(3) 0.8994(2) -0.13662(17) 0.0244(5) Uani 1 1 d . . . C11B C 1.0953(3) 0.8342(2) -0.12577(18) 0.0264(6) Uani 1 1 d . . . H11B H 1.066 0.8093 -0.1782 0.032 Uiso 1 1 calc R . . C12B C 1.0063(3) 0.8060(2) -0.03624(18) 0.0259(5) Uani 1 1 d . . . H12B H 0.9145 0.761 -0.0271 0.031 Uiso 1 1 calc R . . C13B C 0.9481(3) 0.8056(3) 0.13662(18) 0.0287(6) Uani 1 1 d . . . N4B N 1.3273(3) 0.9261(2) -0.23109(16) 0.0334(6) Uani 1 1 d . . . O2B O 0.9049(2) 0.69207(18) 0.13741(14) 0.0349(5) Uani 1 1 d . . . H2B H 0.851(5) 0.676(4) 0.183(3) 0.052 Uiso 1 1 d . . . O3B O 0.9114(3) 0.8717(2) 0.20220(14) 0.0494(6) Uani 1 1 d . . . O4B O 1.3093(3) 0.8662(3) -0.29494(14) 0.0496(6) Uani 1 1 d . . . O5B O 1.4261(2) 1.0037(2) -0.24107(16) 0.0451(6) Uani 1 1 d . . . Cl1B Cl 1.24423(10) 0.95831(8) 0.11727(5) 0.0452(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0176(11) 0.0217(12) 0.0184(11) 0.0025(9) -0.0046(9) -0.0031(10) C2A 0.0222(12) 0.0242(13) 0.0236(12) 0.0019(10) -0.0048(10) -0.0017(10) C3A 0.0195(12) 0.0356(15) 0.0197(12) 0.0028(10) -0.0020(9) -0.0013(11) C4A 0.0301(14) 0.0274(14) 0.0291(13) 0.0100(11) -0.0057(11) -0.0074(12) C5A 0.0248(13) 0.0237(13) 0.0271(13) 0.0052(10) -0.0044(10) -0.0027(11) C6A 0.0142(11) 0.0198(12) 0.0210(11) 0.0032(9) -0.0047(9) 0.0001(9) N1A 0.0138(10) 0.0181(11) 0.0349(12) -0.0027(9) 0.0019(9) -0.0010(8) N2A 0.0235(11) 0.0382(13) 0.0223(10) 0.0083(9) -0.0032(9) -0.0068(10) N3A 0.0150(10) 0.0234(12) 0.0371(13) -0.0007(9) -0.0019(9) -0.0028(9) O1A 0.0199(9) 0.0209(9) 0.0314(9) -0.0004(7) -0.0023(7) 0.0010(7) C1B 0.0205(12) 0.0213(12) 0.0240(12) 0.0015(9) -0.0046(9) -0.0017(10) C2B 0.0250(13) 0.0233(13) 0.0319(14) 0.0037(11) -0.0009(11) -0.0009(11) C3B 0.0247(13) 0.0305(15) 0.0304(14) 0.0039(11) 0.0030(11) 0.0006(12) C4B 0.0339(15) 0.0268(14) 0.0289(13) 0.0070(11) -0.0052(11) -0.0077(12) C5B 0.0298(14) 0.0208(13) 0.0296(13) 0.0035(10) -0.0067(11) 0.0009(11) C6B 0.0176(11) 0.0213(12) 0.0279(12) -0.0004(10) -0.0049(10) -0.0014(10) N1B 0.0151(10) 0.0193(11) 0.0359(12) 0.0023(9) 0.0041(9) 0.0019(9) N2B 0.0283(12) 0.0322(13) 0.0267(11) 0.0077(9) -0.0022(9) -0.0047(10) N3B 0.0185(11) 0.0247(12) 0.0361(13) 0.0035(10) -0.0006(9) -0.0035(9) O1B 0.0232(9) 0.0207(10) 0.0506(12) -0.0005(8) 0.0002(9) 0.0032(8) C7A 0.0216(12) 0.0220(13) 0.0257(12) 0.0079(10) -0.0025(10) 0.0023(10) C8A 0.0256(13) 0.0235(13) 0.0324(14) 0.0027(10) -0.0083(11) -0.0009(11) C9A 0.0346(15) 0.0275(14) 0.0254(13) 0.0053(10) -0.0081(11) 0.0032(12) C10A 0.0223(12) 0.0230(13) 0.0346(14) 0.0053(11) 0.0003(11) 0.0009(11) C11A 0.0224(12) 0.0322(15) 0.0381(15) 0.0009(12) -0.0074(11) -0.0032(11) C12A 0.0288(14) 0.0312(15) 0.0333(14) 0.0049(11) -0.0082(11) -0.0027(12) C13A 0.0233(13) 0.0244(13) 0.0287(13) 0.0063(10) -0.0010(10) 0.0011(11) N4A 0.0302(12) 0.0256(12) 0.0372(13) 0.0056(10) 0.0009(10) 0.0016(10) O2A 0.0217(9) 0.0522(14) 0.0310(10) 0.0210(9) -0.0032(8) -0.0061(9) O3A 0.0230(10) 0.0440(12) 0.0407(11) 0.0151(9) -0.0078(8) -0.0064(9) O4A 0.0283(10) 0.0325(11) 0.0560(14) 0.0024(10) 0.0004(10) -0.0090(9) O5A 0.0450(13) 0.0476(14) 0.0302(11) 0.0089(9) 0.0047(9) -0.0020(11) Cl1A 0.0417(4) 0.0563(5) 0.0428(4) 0.0017(4) -0.0175(3) -0.0201(4) C7B 0.0234(12) 0.0178(12) 0.0217(12) 0.0032(9) -0.0026(9) 0.0021(10) C8B 0.0261(13) 0.0233(13) 0.0246(12) -0.0004(10) -0.0078(10) 0.0001(10) C9B 0.0235(12) 0.0214(13) 0.0324(13) 0.0041(10) -0.0061(10) -0.0049(10) C10B 0.0237(12) 0.0257(13) 0.0201(12) 0.0054(9) -0.0010(10) 0.0011(10) C11B 0.0261(13) 0.0285(14) 0.0244(12) 0.0018(10) -0.0074(10) -0.0014(11) C12B 0.0237(12) 0.0260(13) 0.0271(13) 0.0033(10) -0.0066(10) -0.0047(11) C13B 0.0262(13) 0.0285(14) 0.0264(13) 0.0078(10) -0.0004(10) 0.0048(11) N4B 0.0260(12) 0.0435(15) 0.0269(12) 0.0109(10) -0.0026(9) 0.0011(11) O2B 0.0337(11) 0.0307(11) 0.0305(10) 0.0081(8) 0.0053(8) -0.0065(9) O3B 0.0681(16) 0.0375(12) 0.0276(11) 0.0000(9) 0.0086(10) 0.0018(11) O4B 0.0377(12) 0.0861(19) 0.0225(10) 0.0010(11) -0.0052(9) -0.0003(12) O5B 0.0318(11) 0.0494(14) 0.0448(13) 0.0189(10) 0.0018(9) -0.0104(10) Cl1B 0.0533(5) 0.0529(5) 0.0335(4) -0.0083(3) -0.0190(3) -0.0087(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 C1A C2A 1.388(4) . ? C1A C5A 1.392(3) . ? C1A C6A 1.500(3) . ? C2A C3A 1.382(3) . ? C2A H2C 0.95 . ? C3A N2A 1.331(4) . ? C3A H3E 0.95 . ? C4A N2A 1.342(4) . ? C4A C5A 1.369(3) . ? C4A H4A 0.95 . ? C5A H5A 0.95 . ? C6A O1A 1.227(3) . ? C6A N1A 1.334(3) . ? N1A N3A 1.416(3) . ? N1A H1A 0.72(3) . ? N3A H3A 0.79(4) . ? N3A H3B 0.87(4) . ? C1B C2B 1.386(4) . ? C1B C5B 1.395(4) . ? C1B C6B 1.500(3) . ? C2B C3B 1.385(4) . ? C2B H2D 0.95 . ? C3B N2B 1.332(4) . ? C3B H3F 0.95 . ? C4B N2B 1.339(4) . ? C4B C5B 1.377(4) . ? C4B H4B 0.95 . ? C5B H5B 0.95 . ? C6B O1B 1.230(3) . ? C6B N1B 1.334(3) . ? N1B N3B 1.418(3) . ? N1B H1B 0.85(4) . ? N3B H3C 0.77(4) . ? N3B H3D 0.83(4) . ? C7A C8A 1.388(4) . ? C7A C12A 1.398(4) . ? C7A C13A 1.514(3) . ? C8A C9A 1.400(4) . ? C8A Cl1A 1.723(3) . ? C9A C10A 1.375(4) . ? C9A H9A 0.95 . ? C10A C11A 1.368(4) . ? C10A N4A 1.482(3) . ? C11A C12A 1.378(4) . ? C11A H11A 0.95 . ? C12A H12A 0.95 . ? C13A O3A 1.203(3) . ? C13A O2A 1.308(3) . ? N4A O4A 1.218(3) . ? N4A O5A 1.221(3) . ? O2A H2A 0.92(4) . ? C7B C12B 1.392(3) . ? C7B C8B 1.396(3) . ? C7B C13B 1.510(3) . ? C8B C9B 1.391(4) . ? C8B Cl1B 1.723(3) . ? C9B C10B 1.373(4) . ? C9B H9B 0.95 . ? C10B C11B 1.378(4) . ? C10B N4B 1.468(3) . ? C11B C12B 1.382(4) . ? C11B H11B 0.95 . ? C12B H12B 0.95 . ? C13B O3B 1.203(3) . ? C13B O2B 1.316(3) . ? N4B O5B 1.223(3) . ? N4B O4B 1.227(3) . ? O2B H2B 0.73(4) . ? 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 C2A C1A C5A 118.1(2) . . ? C2A C1A C6A 124.3(2) . . ? C5A C1A C6A 117.6(2) . . ? C3A C2A C1A 118.8(2) . . ? C3A C2A H2C 120.6 . . ? C1A C2A H2C 120.6 . . ? N2A C3A C2A 122.8(2) . . ? N2A C3A H3E 118.6 . . ? C2A C3A H3E 118.6 . . ? N2A C4A C5A 122.7(2) . . ? N2A C4A H4A 118.6 . . ? C5A C4A H4A 118.6 . . ? C4A C5A C1A 119.3(2) . . ? C4A C5A H5A 120.4 . . ? C1A C5A H5A 120.4 . . ? O1A C6A N1A 122.7(2) . . ? O1A C6A C1A 120.8(2) . . ? N1A C6A C1A 116.5(2) . . ? C6A N1A N3A 121.6(2) . . ? C6A N1A H1A 125(3) . . ? N3A N1A H1A 112(3) . . ? C3A N2A C4A 118.2(2) . . ? N1A N3A H3A 112(3) . . ? N1A N3A H3B 104(2) . . ? H3A N3A H3B 105(3) . . ? C2B C1B C5B 118.3(2) . . ? C2B C1B C6B 124.6(2) . . ? C5B C1B C6B 117.1(2) . . ? C3B C2B C1B 118.8(2) . . ? C3B C2B H2D 120.6 . . ? C1B C2B H2D 120.6 . . ? N2B C3B C2B 123.0(3) . . ? N2B C3B H3F 118.5 . . ? C2B C3B H3F 118.5 . . ? N2B C4B C5B 123.0(2) . . ? N2B C4B H4B 118.5 . . ? C5B C4B H4B 118.5 . . ? C4B C5B C1B 118.9(2) . . ? C4B C5B H5B 120.6 . . ? C1B C5B H5B 120.6 . . ? O1B C6B N1B 122.1(2) . . ? O1B C6B C1B 121.0(2) . . ? N1B C6B C1B 116.9(2) . . ? C6B N1B N3B 122.7(2) . . ? C6B N1B H1B 125(2) . . ? N3B N1B H1B 112(2) . . ? C3B N2B C4B 118.1(2) . . ? N1B N3B H3C 104(3) . . ? N1B N3B H3D 109(2) . . ? H3C N3B H3D 111(4) . . ? C8A C7A C12A 118.3(2) . . ? C8A C7A C13A 122.2(2) . . ? C12A C7A C13A 119.4(2) . . ? C7A C8A C9A 120.6(2) . . ? C7A C8A Cl1A 122.6(2) . . ? C9A C8A Cl1A 116.7(2) . . ? C10A C9A C8A 117.8(2) . . ? C10A C9A H9A 121.1 . . ? C8A C9A H9A 121.1 . . ? C11A C10A C9A 123.9(2) . . ? C11A C10A N4A 119.0(2) . . ? C9A C10A N4A 117.1(2) . . ? C10A C11A C12A 117.1(2) . . ? C10A C11A H11A 121.4 . . ? C12A C11A H11A 121.4 . . ? C11A C12A C7A 122.3(3) . . ? C11A C12A H12A 118.9 . . ? C7A C12A H12A 118.9 . . ? O3A C13A O2A 124.8(2) . . ? O3A C13A C7A 123.0(2) . . ? O2A C13A C7A 112.2(2) . . ? O4A N4A O5A 124.1(2) . . ? O4A N4A C10A 117.9(2) . . ? O5A N4A C10A 117.9(2) . . ? C13A O2A H2A 102(2) . . ? C12B C7B C8B 118.7(2) . . ? C12B C7B C13B 118.5(2) . . ? C8B C7B C13B 122.8(2) . . ? C9B C8B C7B 121.0(2) . . ? C9B C8B Cl1B 116.96(19) . . ? C7B C8B Cl1B 121.99(19) . . ? C10B C9B C8B 117.8(2) . . ? C10B C9B H9B 121.1 . . ? C8B C9B H9B 121.1 . . ? C9B C10B C11B 123.3(2) . . ? C9B C10B N4B 117.8(2) . . ? C11B C10B N4B 118.8(2) . . ? C10B C11B C12B 117.9(2) . . ? C10B C11B H11B 121.1 . . ? C12B C11B H11B 121.1 . . ? C11B C12B C7B 121.3(2) . . ? C11B C12B H12B 119.3 . . ? C7B C12B H12B 119.3 . . ? O3B C13B O2B 125.1(2) . . ? O3B C13B C7B 124.5(3) . . ? O2B C13B C7B 110.3(2) . . ? O5B N4B O4B 124.0(2) . . ? O5B N4B C10B 118.2(2) . . ? O4B N4B C10B 117.8(2) . . ? C13B O2B H2B 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A C1A C2A C3A -1.2(3) . . . . ? C6A C1A C2A C3A 175.6(2) . . . . ? C1A C2A C3A N2A 2.3(4) . . . . ? N2A C4A C5A C1A 1.4(4) . . . . ? C2A C1A C5A C4A -0.6(4) . . . . ? C6A C1A C5A C4A -177.6(2) . . . . ? C2A C1A C6A O1A -161.9(2) . . . . ? C5A C1A C6A O1A 14.9(3) . . . . ? C2A C1A C6A N1A 16.7(3) . . . . ? C5A C1A C6A N1A -166.5(2) . . . . ? O1A C6A N1A N3A 5.0(4) . . . . ? C1A C6A N1A N3A -173.5(2) . . . . ? C2A C3A N2A C4A -1.5(4) . . . . ? C5A C4A N2A C3A -0.4(4) . . . . ? C5B C1B C2B C3B -1.3(4) . . . . ? C6B C1B C2B C3B -179.0(2) . . . . ? C1B C2B C3B N2B 0.3(4) . . . . ? N2B C4B C5B C1B -0.3(4) . . . . ? C2B C1B C5B C4B 1.3(4) . . . . ? C6B C1B C5B C4B 179.1(2) . . . . ? C2B C1B C6B O1B -176.9(3) . . . . ? C5B C1B C6B O1B 5.4(4) . . . . ? C2B C1B C6B N1B 3.3(4) . . . . ? C5B C1B C6B N1B -174.4(2) . . . . ? O1B C6B N1B N3B -0.9(4) . . . . ? C1B C6B N1B N3B 178.9(2) . . . . ? C2B C3B N2B C4B 0.6(4) . . . . ? C5B C4B N2B C3B -0.6(4) . . . . ? C12A C7A C8A C9A -0.3(4) . . . . ? C13A C7A C8A C9A -177.5(2) . . . . ? C12A C7A C8A Cl1A -178.5(2) . . . . ? C13A C7A C8A Cl1A 4.3(4) . . . . ? C7A C8A C9A C10A 1.8(4) . . . . ? Cl1A C8A C9A C10A -180.0(2) . . . . ? C8A C9A C10A C11A -1.4(4) . . . . ? C8A C9A C10A N4A 179.1(2) . . . . ? C9A C10A C11A C12A -0.5(4) . . . . ? N4A C10A C11A C12A 179.0(3) . . . . ? C10A C11A C12A C7A 2.1(4) . . . . ? C8A C7A C12A C11A -1.7(4) . . . . ? C13A C7A C12A C11A 175.6(3) . . . . ? C8A C7A C13A O3A 36.6(4) . . . . ? C12A C7A C13A O3A -140.6(3) . . . . ? C8A C7A C13A O2A -143.5(3) . . . . ? C12A C7A C13A O2A 39.3(3) . . . . ? C11A C10A N4A O4A 0.7(4) . . . . ? C9A C10A N4A O4A -179.8(3) . . . . ? C11A C10A N4A O5A -177.9(3) . . . . ? C9A C10A N4A O5A 1.7(4) . . . . ? C12B C7B C8B C9B -1.7(4) . . . . ? C13B C7B C8B C9B 178.0(2) . . . . ? C12B C7B C8B Cl1B -179.4(2) . . . . ? C13B C7B C8B Cl1B 0.3(4) . . . . ? C7B C8B C9B C10B 0.6(4) . . . . ? Cl1B C8B C9B C10B 178.4(2) . . . . ? C8B C9B C10B C11B 0.9(4) . . . . ? C8B C9B C10B N4B -177.9(2) . . . . ? C9B C10B C11B C12B -1.2(4) . . . . ? N4B C10B C11B C12B 177.5(2) . . . . ? C10B C11B C12B C7B 0.1(4) . . . . ? C8B C7B C12B C11B 1.3(4) . . . . ? C13B C7B C12B C11B -178.4(3) . . . . ? C12B C7B C13B O3B -136.1(3) . . . . ? C8B C7B C13B O3B 44.3(4) . . . . ? C12B C7B C13B O2B 42.8(3) . . . . ? C8B C7B C13B O2B -136.8(3) . . . . ? C9B C10B N4B O5B -16.1(4) . . . . ? C11B C10B N4B O5B 165.1(3) . . . . ? C9B C10B N4B O4B 161.6(3) . . . . ? C11B C10B N4B O4B -17.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1A N3B 0.72(3) 2.32(4) 2.980(3) 153(3) . N3A H3A O5B 0.79(4) 3.03(4) 3.807(3) 168(3) 2_765 N3A H3B O1A 0.87(4) 2.11(4) 2.946(3) 161(3) 2_656 N1B H1B N3A 0.85(4) 2.11(4) 2.911(3) 157(3) . N3B H3C O1B 0.77(4) 2.29(4) 3.050(3) 168(4) 2_566 N3B H3D O5A 0.83(4) 2.53(4) 3.287(3) 152(3) 2_457 O2A H2A N2A 0.92(4) 1.69(4) 2.602(3) 171(4) . O2B H2B N2B 0.73(4) 1.92(4) 2.642(3) 167(4) . ###END data_11 _database_code_depnum_ccdc_archive 'CCDC 847207' #TrackingRef '- Combined cif.cif' _audit_creation_date 2011-07-16T09:21:24-00:00 _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 ; ? ; _chemical_formula_moiety 'C9 H12 N3 O, 3(C9 H11 N3 O), 3(C7 H4 Cl N O4), C7 H3 Cl N O4' _chemical_formula_sum 'C64 H60 Cl4 N16 O20' _chemical_formula_weight 1515.08 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8490(2) _cell_length_b 38.7853(12) _cell_length_c 12.7324(4) _cell_angle_alpha 90 _cell_angle_beta 98.265(2) _cell_angle_gamma 90 _cell_volume 3347.11(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9915 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 28.34 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8676 _exptl_absorpt_correction_T_max 0.9127 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_number 42752 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 51 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 14216 _reflns_number_gt 13432 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0474P)^2^+3.3600P] 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 14216 _refine_ls_number_parameters 949 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 6122 Friedel Pairs' _refine_ls_abs_structure_Flack 0.26(4) _refine_diff_density_max 1.156 _refine_diff_density_min -0.71 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C1A C 1.2905(4) 0.47851(8) 0.1122(2) 0.0250(6) Uani 1 1 d . . . C2A C 1.2496(5) 0.44686(8) 0.0636(3) 0.0313(7) Uani 1 1 d . . . H2A1 H 1.2289 0.4451 -0.0116 0.038 Uiso 1 1 calc R . . C3A C 1.2393(5) 0.41796(8) 0.1256(3) 0.0320(7) Uani 1 1 d . . . H3A H 1.2086 0.3965 0.0913 0.038 Uiso 1 1 calc R . . C4A C 1.3101(5) 0.44960(8) 0.2800(3) 0.0289(6) Uani 1 1 d . . . H4A H 1.3321 0.4506 0.3553 0.035 Uiso 1 1 calc R . . C5A C 1.3196(4) 0.47967(8) 0.2229(3) 0.0275(6) Uani 1 1 d . . . H5A H 1.3459 0.501 0.2587 0.033 Uiso 1 1 calc R . . C6A C 1.3100(5) 0.51029(8) 0.0468(3) 0.0276(6) Uani 1 1 d . . . C7A C 1.1648(6) 0.59415(10) 0.2091(3) 0.0452(9) Uani 1 1 d . . . H7A1 H 1.0368 0.5825 0.2031 0.068 Uiso 1 1 calc R . . H7A2 H 1.1532 0.6173 0.2385 0.068 Uiso 1 1 calc R . . H7A3 H 1.263 0.5809 0.2562 0.068 Uiso 1 1 calc R . . C8A C 1.2277(5) 0.59689(8) 0.1018(3) 0.0299(6) Uani 1 1 d . . . C9A C 1.2527(6) 0.63190(8) 0.0579(3) 0.0365(7) Uani 1 1 d . . . H9A1 H 1.2971 0.6299 -0.0117 0.055 Uiso 1 1 calc R . . H9A2 H 1.351 0.6447 0.1062 0.055 Uiso 1 1 calc R . . H9A3 H 1.1264 0.6442 0.0501 0.055 Uiso 1 1 calc R . . N1A N 1.2409(4) 0.53881(7) 0.0890(2) 0.0295(6) Uani 1 1 d . . . H1A H 1.164(6) 0.5362(11) 0.140(3) 0.044 Uiso 1 1 d . . . N2A N 1.2704(4) 0.41871(7) 0.2317(2) 0.0298(6) Uani 1 1 d . . . N3A N 1.2663(4) 0.57106(7) 0.0449(2) 0.0295(6) Uani 1 1 d . . . O1A O 1.3904(4) 0.50924(6) -0.0331(2) 0.0387(6) Uani 1 1 d . . . C1B C 0.8111(4) 0.47794(5) 0.3511(2) 0.0396(8) Uani 1 1 d GU . . C2B C 0.7905(4) 0.47739(6) 0.4581(2) 0.0607(13) Uani 1 1 d GU . . H2B1 H 0.7808 0.4984 0.4953 0.073 Uiso 1 1 calc R . . C3B C 0.7842(5) 0.44609(9) 0.5107(2) 0.092(2) Uani 1 1 d GU . . H3B H 0.7702 0.4457 0.5838 0.111 Uiso 1 1 calc R . . N2B N 0.7985(5) 0.41534(6) 0.4562(3) 0.0973(17) Uiso 1 1 d GU . . H2B H 0.7945 0.3955 0.4895 0.146 Uiso 1 1 calc R . . C4B C 0.8190(4) 0.41589(5) 0.3492(3) 0.105(3) Uani 1 1 d GU . . H4B H 0.8287 0.3949 0.312 0.126 Uiso 1 1 calc R . . C5B C 0.8253(4) 0.44719(7) 0.2966(2) 0.0733(17) Uani 1 1 d GU . . H5B H 0.8394 0.4476 0.2235 0.088 Uiso 1 1 calc R . . C6B C 0.8174(5) 0.51220(8) 0.2924(3) 0.0317(7) Uani 1 1 d . . . C7B C 0.7619(6) 0.59438(11) 0.4694(3) 0.0478(9) Uani 1 1 d . . . H7B1 H 0.6398 0.5899 0.4988 0.072 Uiso 1 1 calc R . . H7B2 H 0.8186 0.6163 0.4971 0.072 Uiso 1 1 calc R . . H7B3 H 0.8563 0.5757 0.4898 0.072 Uiso 1 1 calc R . . C8B C 0.7175(5) 0.59627(8) 0.3505(3) 0.0323(7) Uani 1 1 d . . . C9B C 0.6872(6) 0.63101(10) 0.3028(4) 0.0479(9) Uani 1 1 d . . . H9B1 H 0.6711 0.6291 0.2253 0.072 Uiso 1 1 calc R . . H9B2 H 0.8019 0.6455 0.3273 0.072 Uiso 1 1 calc R . . H9B3 H 0.5687 0.6414 0.3243 0.072 Uiso 1 1 calc R . . N1B N 0.7326(4) 0.53831(7) 0.3392(2) 0.0296(6) Uani 1 1 d . . . H1B H 0.639(6) 0.5329(11) 0.377(3) 0.044 Uiso 1 1 d . . . N3B N 0.7095(4) 0.57054(7) 0.2885(2) 0.0338(6) Uani 1 1 d . . . O1B O 0.8971(4) 0.51573(7) 0.2135(2) 0.0472(7) Uani 1 1 d . . . C1C C 0.3066(4) 0.56190(8) 0.6178(2) 0.0258(6) Uani 1 1 d . . . C2C C 0.3062(4) 0.56118(8) 0.7270(2) 0.0266(6) Uani 1 1 d . . . H2C1 H 0.3174 0.5399 0.7644 0.032 Uiso 1 1 calc R . . C3C C 0.2892(4) 0.59185(8) 0.7804(2) 0.0277(6) Uani 1 1 d . . . H3C H 0.2892 0.5912 0.855 0.033 Uiso 1 1 calc R . . C4C C 0.2738(5) 0.62310(8) 0.6265(3) 0.0345(7) Uani 1 1 d . . . H4C H 0.2636 0.6448 0.5916 0.041 Uiso 1 1 calc R . . C5C C 0.2895(5) 0.59346(9) 0.5670(3) 0.0331(7) Uani 1 1 d . . . H5C H 0.2883 0.5949 0.4924 0.04 Uiso 1 1 calc R . . C6C C 0.3338(4) 0.52983(8) 0.5550(2) 0.0274(6) Uani 1 1 d . . . C7C C 0.2216(7) 0.44617(10) 0.7238(3) 0.0450(9) Uani 1 1 d . . . H7C1 H 0.3062 0.4634 0.7641 0.067 Uiso 1 1 calc R . . H7C2 H 0.2418 0.4237 0.7591 0.067 Uiso 1 1 calc R . . H7C3 H 0.0831 0.453 0.7205 0.067 Uiso 1 1 calc R . . C8C C 0.2732(5) 0.44361(8) 0.6132(3) 0.0320(7) Uani 1 1 d . . . C9C C 0.3044(6) 0.40817(9) 0.5716(3) 0.0398(8) Uani 1 1 d . . . H9C1 H 0.3557 0.41 0.5038 0.06 Uiso 1 1 calc R . . H9C2 H 0.1787 0.3957 0.561 0.06 Uiso 1 1 calc R . . H9C3 H 0.3993 0.3957 0.6228 0.06 Uiso 1 1 calc R . . N1C N 0.2657(4) 0.50124(7) 0.5968(2) 0.0313(6) Uani 1 1 d . . . H1C H 0.181(6) 0.5033(12) 0.641(3) 0.047 Uiso 1 1 d . . . N2C N 0.2728(4) 0.62202(7) 0.7313(2) 0.0306(6) Uani 1 1 d . . . N3C N 0.2976(4) 0.46902(7) 0.5536(2) 0.0326(6) Uani 1 1 d . . . O1C O 0.4151(4) 0.53083(6) 0.47483(19) 0.0388(6) Uani 1 1 d . . . C1D C -0.2069(4) 0.56047(8) 0.8359(3) 0.0272(6) Uani 1 1 d . . . C2D C -0.2396(5) 0.56688(9) 0.9394(3) 0.0321(7) Uani 1 1 d . . . H2D1 H -0.2465 0.5485 0.988 0.039 Uiso 1 1 calc R . . C3D C -0.2619(5) 0.60069(9) 0.9699(3) 0.0355(7) Uani 1 1 d . . . H3D H -0.2841 0.6052 1.0405 0.043 Uiso 1 1 calc R . . C4D C -0.2228(5) 0.62124(9) 0.8052(3) 0.0362(7) Uani 1 1 d . . . H4D H -0.2182 0.6401 0.758 0.043 Uiso 1 1 calc R . . C5D C -0.1973(5) 0.58841(9) 0.7689(3) 0.0334(7) Uani 1 1 d . . . H5D H -0.1732 0.5849 0.698 0.04 Uiso 1 1 calc R . . C6D C -0.1775(4) 0.52515(8) 0.7908(3) 0.0296(6) Uani 1 1 d . . . C7D C -0.2805(7) 0.44318(10) 0.9734(3) 0.0464(9) Uani 1 1 d . . . H7D1 H -0.1828 0.4593 1.0093 0.07 Uiso 1 1 calc R . . H7D2 H -0.2606 0.4204 1.0064 0.07 Uiso 1 1 calc R . . H7D3 H -0.4135 0.4514 0.9797 0.07 Uiso 1 1 calc R . . C8D C -0.2569(5) 0.44075(8) 0.8589(3) 0.0316(7) Uani 1 1 d . . . C9D C -0.2477(7) 0.40566(10) 0.8123(3) 0.0488(10) Uani 1 1 d . . . H9D1 H -0.2364 0.4076 0.7367 0.073 Uiso 1 1 calc R . . H9D2 H -0.368 0.3929 0.8207 0.073 Uiso 1 1 calc R . . H9D3 H -0.1326 0.3933 0.8488 0.073 Uiso 1 1 calc R . . N1D N -0.2530(4) 0.49892(7) 0.8397(2) 0.0328(6) Uani 1 1 d . . . H1D H -0.321(6) 0.5045(11) 0.898(3) 0.049 Uiso 1 1 d . . . N2D N -0.2535(4) 0.62745(7) 0.9040(2) 0.0342(6) Uani 1 1 d . . . N3D N -0.2413(5) 0.46607(7) 0.7965(2) 0.0386(7) Uani 1 1 d . . . O1D O -0.0895(4) 0.52187(6) 0.7139(2) 0.0409(6) Uani 1 1 d . . . C10A C 1.1884(4) 0.30185(7) 0.3314(2) 0.0212(5) Uani 1 1 d . . . C11A C 1.2805(4) 0.29358(7) 0.4344(2) 0.0228(6) Uani 1 1 d . . . C12A C 1.3110(4) 0.25957(7) 0.4656(2) 0.0220(5) Uani 1 1 d . . . H12A H 1.3805 0.254 0.5336 0.026 Uiso 1 1 calc R . . C13A C 1.2374(4) 0.23374(7) 0.3954(2) 0.0240(6) Uani 1 1 d . . . C14A C 1.1362(4) 0.24025(7) 0.2965(2) 0.0250(6) Uani 1 1 d . . . H14A H 1.0829 0.2221 0.251 0.03 Uiso 1 1 calc R . . C15A C 1.1148(4) 0.27476(7) 0.2656(2) 0.0236(5) Uani 1 1 d . . . H15A H 1.0474 0.28 0.1969 0.028 Uiso 1 1 calc R . . C16A C 1.1674(4) 0.33748(7) 0.2823(2) 0.0244(6) Uani 1 1 d . . . N4A N 1.2672(4) 0.19771(7) 0.4316(2) 0.0282(5) Uani 1 1 d . . . O2A O 1.2760(4) 0.36087(6) 0.33305(19) 0.0361(5) Uani 1 1 d . . . H2A H 1.251(6) 0.3850(11) 0.290(4) 0.054 Uiso 1 1 d . . . O3A O 1.0633(4) 0.34179(6) 0.19807(18) 0.0409(6) Uani 1 1 d . . . O4A O 1.3963(4) 0.19171(6) 0.50579(19) 0.0375(5) Uani 1 1 d . . . O5A O 1.1565(4) 0.17609(6) 0.3848(2) 0.0395(5) Uani 1 1 d . . . Cl1A Cl 1.34455(11) 0.324186(17) 0.53124(5) 0.02775(15) Uani 1 1 d . . . C10B C 0.8166(4) 0.29854(8) 0.5657(2) 0.0248(6) Uani 1 1 d . . . C11B C 0.7901(4) 0.28857(7) 0.6687(2) 0.0233(6) Uani 1 1 d . . . C12B C 0.7853(4) 0.25416(8) 0.6966(2) 0.0237(6) Uani 1 1 d . . . H12B H 0.7671 0.2476 0.7664 0.028 Uiso 1 1 calc R . . C13B C 0.8073(4) 0.22953(7) 0.6211(2) 0.0245(6) Uani 1 1 d . . . C14B C 0.8306(4) 0.23781(9) 0.5178(2) 0.0294(6) Uani 1 1 d . . . H14B H 0.8418 0.2204 0.4666 0.035 Uiso 1 1 calc R . . C15B C 0.8367(4) 0.27214(9) 0.4923(2) 0.0300(7) Uani 1 1 d . . . H15B H 0.8554 0.2783 0.4223 0.036 Uiso 1 1 calc R . . C16B C 0.8225(5) 0.33475(10) 0.5241(4) 0.0470(10) Uani 1 1 d . . . N4B N 0.8036(4) 0.19287(7) 0.6516(2) 0.0330(6) Uani 1 1 d . . . O2B O 0.8228(5) 0.35966(7) 0.5871(3) 0.0558(8) Uani 1 1 d . . . O3B O 0.8221(5) 0.33846(8) 0.4268(2) 0.0577(8) Uani 1 1 d . . . O4B O 0.7547(5) 0.18575(7) 0.7370(2) 0.0497(7) Uani 1 1 d . . . O5B O 0.8496(5) 0.17154(7) 0.5890(2) 0.0512(7) Uani 1 1 d . . . Cl1B Cl 0.75553(12) 0.317860(19) 0.76655(6) 0.03356(17) Uani 1 1 d . . . C10C C 0.3557(4) 0.73947(7) 0.8317(2) 0.0217(5) Uani 1 1 d . . . C11C C 0.3089(4) 0.74860(7) 0.9315(2) 0.0216(5) Uani 1 1 d . . . C12C C 0.3002(4) 0.78251(8) 0.9618(2) 0.0234(6) Uani 1 1 d . . . H12C H 0.2672 0.7885 1.0294 0.028 Uiso 1 1 calc R . . C13C C 0.3411(4) 0.80788(7) 0.8908(2) 0.0243(6) Uani 1 1 d . . . C14C C 0.3916(4) 0.80037(8) 0.7924(2) 0.0249(6) Uani 1 1 d . . . H14C H 0.4195 0.8181 0.7452 0.03 Uiso 1 1 calc R . . C15C C 0.4000(4) 0.76599(7) 0.7655(2) 0.0234(6) Uani 1 1 d . . . H15C H 0.4375 0.7602 0.6987 0.028 Uiso 1 1 calc R . . C16C C 0.3595(4) 0.70353(7) 0.7860(2) 0.0240(6) Uani 1 1 d . . . N4C N 0.3326(5) 0.84408(7) 0.9232(2) 0.0372(6) Uani 1 1 d . . . O2C O 0.2509(4) 0.68102(6) 0.82653(19) 0.0329(5) Uani 1 1 d . . . H2C H 0.263(6) 0.6608(12) 0.800(4) 0.049 Uiso 1 1 d . . . O3C O 0.4515(4) 0.69790(6) 0.7137(2) 0.0434(6) Uani 1 1 d . . . O4C O 0.2760(6) 0.85041(7) 1.0073(2) 0.0616(9) Uani 1 1 d . . . O5C O 0.3837(5) 0.86620(6) 0.8644(2) 0.0500(7) Uani 1 1 d . . . Cl1C Cl 0.26620(11) 0.718329(18) 1.02582(5) 0.02718(14) Uani 1 1 d . . . C10D C -0.2298(4) 0.73728(8) 1.0795(2) 0.0251(6) Uani 1 1 d . . . C11D C -0.2660(4) 0.74943(8) 1.1775(2) 0.0234(6) Uani 1 1 d . . . C12D C -0.2734(4) 0.78435(8) 1.1979(2) 0.0274(6) Uani 1 1 d . . . H12D H -0.3022 0.7926 1.2642 0.033 Uiso 1 1 calc R . . C13D C -0.2378(4) 0.80704(7) 1.1188(2) 0.0256(6) Uani 1 1 d . . . C14D C -0.1987(4) 0.79631(8) 1.0213(2) 0.0278(6) Uani 1 1 d . . . H14D H -0.1726 0.8125 0.9689 0.033 Uiso 1 1 calc R . . C15D C -0.1984(5) 0.76116(8) 1.0015(2) 0.0272(6) Uani 1 1 d . . . H15D H -0.1765 0.7532 0.9337 0.033 Uiso 1 1 calc R . . C16D C -0.2206(4) 0.69922(8) 1.0535(3) 0.0295(6) Uani 1 1 d . . . N4D N -0.2440(4) 0.84440(7) 1.1410(2) 0.0318(6) Uani 1 1 d . . . O2D O -0.2757(4) 0.69317(6) 0.9524(2) 0.0390(6) Uani 1 1 d . . . H2D H -0.255(7) 0.6705(12) 0.938(4) 0.058 Uiso 1 1 d . . . O3D O -0.1662(5) 0.67797(7) 1.1191(2) 0.0495(7) Uani 1 1 d . . . O4D O -0.2255(5) 0.86422(7) 1.0695(2) 0.0572(8) Uani 1 1 d . . . O5D O -0.2725(5) 0.85308(7) 1.2293(2) 0.0528(7) Uani 1 1 d . . . Cl1D Cl -0.31110(12) 0.72178(2) 1.27745(6) 0.03230(16) 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 C1A 0.0282(14) 0.0172(14) 0.0306(15) 0.0037(11) 0.0081(11) 0.0026(10) C2A 0.0440(17) 0.0213(16) 0.0307(16) -0.0007(13) 0.0127(13) 0.0024(12) C3A 0.0442(17) 0.0186(15) 0.0355(17) -0.0001(13) 0.0133(13) 0.0006(12) C4A 0.0342(15) 0.0237(16) 0.0287(15) 0.0032(12) 0.0040(12) -0.0013(11) C5A 0.0316(15) 0.0171(14) 0.0343(16) -0.0007(12) 0.0061(12) 0.0004(11) C6A 0.0391(16) 0.0177(15) 0.0273(15) 0.0014(11) 0.0089(12) -0.0014(11) C7A 0.064(2) 0.033(2) 0.045(2) -0.0093(16) 0.0284(18) -0.0048(17) C8A 0.0341(15) 0.0235(16) 0.0343(16) 0.0036(13) 0.0120(12) 0.0036(12) C9A 0.054(2) 0.0181(16) 0.0391(18) 0.0037(13) 0.0128(15) 0.0030(13) N1A 0.0443(15) 0.0182(13) 0.0288(13) 0.0034(10) 0.0146(11) 0.0012(10) N2A 0.0356(13) 0.0200(13) 0.0342(14) 0.0055(11) 0.0071(11) 0.0016(10) N3A 0.0456(15) 0.0169(13) 0.0278(13) 0.0050(10) 0.0110(11) 0.0024(10) O1A 0.0606(15) 0.0247(12) 0.0363(13) 0.0056(10) 0.0260(11) 0.0059(10) C1B 0.0245(15) 0.0224(16) 0.071(3) 0.0048(16) 0.0054(15) -0.0008(11) C2B 0.0360(19) 0.065(3) 0.083(3) 0.047(2) 0.0153(19) 0.0080(18) C3B 0.053(3) 0.084(4) 0.141(5) 0.063(4) 0.020(3) 0.006(3) C4B 0.029(2) 0.022(2) 0.250(8) -0.046(3) -0.025(3) 0.0097(15) C5B 0.038(2) 0.030(2) 0.147(5) -0.027(3) -0.005(3) 0.0083(16) C6B 0.0340(16) 0.0239(16) 0.0386(18) -0.0033(13) 0.0103(13) 0.0003(12) C7B 0.063(2) 0.039(2) 0.042(2) -0.0101(17) 0.0101(17) -0.0110(18) C8B 0.0348(16) 0.0224(16) 0.0427(18) 0.0012(14) 0.0156(13) 0.0003(12) C9B 0.063(2) 0.0226(18) 0.061(2) 0.0030(17) 0.0171(19) 0.0060(16) N1B 0.0399(14) 0.0208(13) 0.0308(14) 0.0025(11) 0.0146(11) 0.0001(10) N3B 0.0476(16) 0.0205(14) 0.0355(15) 0.0049(11) 0.0131(12) 0.0018(11) O1B 0.0560(15) 0.0422(15) 0.0490(16) -0.0002(12) 0.0264(13) 0.0085(12) C1C 0.0287(14) 0.0213(15) 0.0282(15) -0.0009(12) 0.0073(11) -0.0008(11) C2C 0.0302(14) 0.0234(15) 0.0267(14) 0.0009(12) 0.0054(11) -0.0036(11) C3C 0.0338(15) 0.0254(16) 0.0250(14) -0.0019(12) 0.0081(11) -0.0053(11) C4C 0.0497(19) 0.0192(16) 0.0366(18) 0.0055(13) 0.0131(14) 0.0028(13) C5C 0.0486(18) 0.0260(17) 0.0259(15) -0.0010(13) 0.0095(13) -0.0008(14) C6C 0.0349(15) 0.0221(15) 0.0261(14) -0.0021(12) 0.0069(12) -0.0015(11) C7C 0.072(3) 0.0250(19) 0.042(2) 0.0005(15) 0.0222(18) 0.0006(16) C8C 0.0448(18) 0.0187(16) 0.0344(17) -0.0033(13) 0.0119(13) -0.0041(12) C9C 0.057(2) 0.0210(16) 0.044(2) -0.0059(14) 0.0182(16) -0.0024(15) N1C 0.0477(16) 0.0149(13) 0.0350(14) -0.0050(11) 0.0189(12) -0.0018(11) N2C 0.0402(14) 0.0208(14) 0.0329(14) -0.0061(11) 0.0123(11) -0.0018(10) N3C 0.0465(15) 0.0190(13) 0.0353(14) -0.0064(11) 0.0159(12) -0.0009(11) O1C 0.0574(14) 0.0276(13) 0.0368(13) -0.0049(10) 0.0252(11) -0.0035(10) C1D 0.0265(14) 0.0211(15) 0.0356(16) -0.0016(12) 0.0096(12) -0.0030(11) C2D 0.0369(16) 0.0242(16) 0.0354(16) -0.0006(13) 0.0062(13) -0.0028(12) C3D 0.0384(17) 0.0359(19) 0.0330(16) -0.0100(14) 0.0076(13) -0.0005(13) C4D 0.0398(17) 0.0258(17) 0.0438(19) 0.0015(14) 0.0091(14) 0.0001(13) C5D 0.0368(16) 0.0274(17) 0.0374(17) 0.0027(13) 0.0102(13) -0.0004(12) C6D 0.0309(14) 0.0256(16) 0.0333(16) -0.0049(13) 0.0086(12) -0.0005(11) C7D 0.069(3) 0.034(2) 0.041(2) 0.0058(16) 0.0237(18) 0.0095(17) C8D 0.0388(16) 0.0230(16) 0.0352(17) 0.0007(13) 0.0130(13) -0.0005(12) C9D 0.083(3) 0.0220(18) 0.045(2) -0.0020(15) 0.024(2) -0.0067(17) N1D 0.0473(16) 0.0177(14) 0.0369(15) -0.0020(11) 0.0186(12) -0.0023(11) N2D 0.0389(14) 0.0219(14) 0.0413(16) -0.0047(11) 0.0042(12) -0.0018(10) N3D 0.0602(19) 0.0191(14) 0.0409(16) -0.0014(12) 0.0223(14) -0.0047(12) O1D 0.0526(14) 0.0302(14) 0.0461(15) -0.0028(11) 0.0278(12) -0.0039(10) C10A 0.0228(12) 0.0200(13) 0.0230(13) 0.0000(10) 0.0103(10) 0.0028(10) C11A 0.0287(14) 0.0189(14) 0.0218(13) -0.0042(11) 0.0071(10) -0.0018(10) C12A 0.0294(14) 0.0218(14) 0.0160(12) -0.0019(11) 0.0071(10) 0.0024(10) C13A 0.0353(15) 0.0142(13) 0.0250(14) 0.0001(11) 0.0131(11) 0.0018(10) C14A 0.0335(14) 0.0192(14) 0.0234(13) -0.0041(11) 0.0074(11) -0.0009(11) C15A 0.0275(13) 0.0226(14) 0.0218(13) 0.0023(11) 0.0075(10) 0.0010(10) C16A 0.0305(14) 0.0190(14) 0.0250(14) 0.0018(11) 0.0089(11) -0.0005(10) N4A 0.0464(15) 0.0165(12) 0.0253(13) 0.0003(10) 0.0171(11) -0.0012(10) O2A 0.0560(15) 0.0167(11) 0.0327(12) 0.0034(9) -0.0033(10) -0.0065(9) O3A 0.0573(15) 0.0285(12) 0.0327(12) 0.0091(10) -0.0074(10) -0.0072(10) O4A 0.0584(15) 0.0202(12) 0.0330(12) 0.0050(9) 0.0035(11) 0.0065(10) O5A 0.0599(15) 0.0176(11) 0.0413(13) -0.0005(10) 0.0087(11) -0.0059(10) Cl1A 0.0419(4) 0.0181(3) 0.0227(3) -0.0048(3) 0.0027(3) 0.0007(3) C10B 0.0223(13) 0.0271(15) 0.0251(14) 0.0078(12) 0.0039(10) -0.0020(11) C11B 0.0252(13) 0.0200(14) 0.0246(14) -0.0029(11) 0.0032(10) 0.0013(10) C12B 0.0280(14) 0.0241(15) 0.0189(13) 0.0054(11) 0.0034(10) 0.0026(11) C13B 0.0242(13) 0.0197(15) 0.0292(14) 0.0008(11) 0.0025(10) -0.0034(10) C14B 0.0293(15) 0.0326(17) 0.0275(15) -0.0063(13) 0.0079(11) -0.0014(12) C15B 0.0290(15) 0.0382(18) 0.0235(14) 0.0037(12) 0.0059(11) -0.0030(12) C16B 0.0310(17) 0.028(2) 0.080(3) 0.0233(19) 0.0029(17) -0.0048(13) N4B 0.0334(14) 0.0243(14) 0.0403(16) 0.0016(12) 0.0020(11) 0.0034(10) O2B 0.081(2) 0.0215(14) 0.072(2) 0.0063(13) 0.0353(16) -0.0027(13) O3B 0.0733(19) 0.0500(17) 0.0462(16) 0.0325(14) -0.0036(13) -0.0172(14) O4B 0.0727(19) 0.0274(14) 0.0523(17) 0.0125(12) 0.0205(14) 0.0047(12) O5B 0.076(2) 0.0255(14) 0.0503(16) -0.0098(12) 0.0040(14) 0.0087(12) Cl1B 0.0455(4) 0.0242(4) 0.0315(4) -0.0069(3) 0.0074(3) 0.0013(3) C10C 0.0213(12) 0.0189(14) 0.0251(13) -0.0002(11) 0.0043(10) 0.0003(10) C11C 0.0254(13) 0.0185(14) 0.0216(13) 0.0025(11) 0.0056(10) -0.0029(10) C12C 0.0293(14) 0.0185(14) 0.0224(13) -0.0024(11) 0.0035(10) 0.0009(10) C13C 0.0321(14) 0.0152(14) 0.0254(14) -0.0017(11) 0.0029(11) -0.0023(10) C14C 0.0277(13) 0.0206(14) 0.0270(14) 0.0035(11) 0.0061(11) -0.0026(10) C15C 0.0269(13) 0.0233(15) 0.0214(13) 0.0000(11) 0.0079(10) -0.0002(10) C16C 0.0287(14) 0.0201(14) 0.0240(13) -0.0017(11) 0.0064(11) 0.0003(10) N4C 0.0568(18) 0.0231(15) 0.0316(14) -0.0025(12) 0.0059(12) -0.0029(12) O2C 0.0476(13) 0.0181(11) 0.0370(13) -0.0050(9) 0.0192(10) -0.0050(9) O3C 0.0652(16) 0.0273(12) 0.0456(14) -0.0131(10) 0.0351(12) -0.0114(11) O4C 0.129(3) 0.0257(14) 0.0353(14) -0.0081(11) 0.0312(16) -0.0002(15) O5C 0.080(2) 0.0163(12) 0.0577(17) 0.0008(11) 0.0250(14) -0.0139(12) Cl1C 0.0405(4) 0.0194(3) 0.0234(3) 0.0024(3) 0.0110(3) -0.0016(3) C10D 0.0235(13) 0.0262(16) 0.0257(14) -0.0018(12) 0.0043(11) 0.0027(11) C11D 0.0249(13) 0.0252(15) 0.0207(13) 0.0019(11) 0.0052(10) -0.0025(10) C12D 0.0321(15) 0.0248(16) 0.0255(14) -0.0021(12) 0.0043(11) 0.0010(11) C13D 0.0277(14) 0.0186(15) 0.0303(15) -0.0004(11) 0.0037(11) -0.0010(10) C14D 0.0307(15) 0.0249(16) 0.0278(15) 0.0044(12) 0.0039(11) -0.0004(11) C15D 0.0338(15) 0.0253(15) 0.0243(14) -0.0011(12) 0.0103(11) 0.0004(11) C16D 0.0297(14) 0.0242(16) 0.0373(17) -0.0015(13) 0.0140(12) 0.0035(12) N4D 0.0425(15) 0.0190(13) 0.0345(14) -0.0002(11) 0.0077(11) -0.0011(10) O2D 0.0554(15) 0.0223(12) 0.0376(13) -0.0069(10) 0.0013(11) 0.0074(10) O3D 0.085(2) 0.0276(13) 0.0401(14) 0.0065(11) 0.0235(13) 0.0196(13) O4D 0.107(3) 0.0237(14) 0.0428(15) 0.0078(12) 0.0181(15) 0.0016(14) O5D 0.098(2) 0.0252(14) 0.0393(15) -0.0088(11) 0.0230(14) -0.0041(13) Cl1D 0.0476(4) 0.0257(4) 0.0257(3) 0.0034(3) 0.0125(3) -0.0007(3) #----------------------------------------------------------------------------# # 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 C1A C2A 1.385(4) . ? C1A C5A 1.395(4) . ? C1A C6A 1.504(4) . ? C2A C3A 1.379(4) . ? C2A H2A1 0.95 . ? C3A N2A 1.337(4) . ? C3A H3A 0.95 . ? C4A N2A 1.356(4) . ? C4A C5A 1.381(4) . ? C4A H4A 0.95 . ? C5A H5A 0.95 . ? C6A O1A 1.226(4) . ? C6A N1A 1.345(4) . ? C7A C8A 1.495(5) . ? C7A H7A1 0.98 . ? C7A H7A2 0.98 . ? C7A H7A3 0.98 . ? C8A N3A 1.286(4) . ? C8A C9A 1.488(4) . ? C9A H9A1 0.98 . ? C9A H9A2 0.98 . ? C9A H9A3 0.98 . ? N1A N3A 1.392(4) . ? N1A H1A 0.89(4) . ? C1B C2B 1.39 . ? C1B C5B 1.39 . ? C1B C6B 1.528(4) . ? C2B C3B 1.39 . ? C2B H2B1 0.95 . ? C3B N2B 1.39 . ? C3B H3B 0.95 . ? N2B C4B 1.39 . ? N2B H2B 0.88 . ? C4B C5B 1.39 . ? C4B H4B 0.95 . ? C5B H5B 0.95 . ? C6B O1B 1.219(4) . ? C6B N1B 1.348(4) . ? C7B C8B 1.503(5) . ? C7B H7B1 0.98 . ? C7B H7B2 0.98 . ? C7B H7B3 0.98 . ? C8B N3B 1.268(4) . ? C8B C9B 1.480(5) . ? C9B H9B1 0.98 . ? C9B H9B2 0.98 . ? C9B H9B3 0.98 . ? N1B N3B 1.405(4) . ? N1B H1B 0.88(4) . ? C1C C5C 1.381(4) . ? C1C C2C 1.392(4) . ? C1C C6C 1.505(4) . ? C2C C3C 1.383(4) . ? C2C H2C1 0.95 . ? C3C N2C 1.324(4) . ? C3C H3C 0.95 . ? C4C N2C 1.336(4) . ? C4C C5C 1.389(5) . ? C4C H4C 0.95 . ? C5C H5C 0.95 . ? C6C O1C 1.232(4) . ? C6C N1C 1.342(4) . ? C7C C8C 1.504(5) . ? C7C H7C1 0.98 . ? C7C H7C2 0.98 . ? C7C H7C3 0.98 . ? C8C N3C 1.270(4) . ? C8C C9C 1.500(4) . ? C9C H9C1 0.98 . ? C9C H9C2 0.98 . ? C9C H9C3 0.98 . ? N1C N3C 1.395(4) . ? N1C H1C 0.87(4) . ? C1D C5D 1.387(4) . ? C1D C2D 1.391(4) . ? C1D C6D 1.510(4) . ? C2D C3D 1.382(5) . ? C2D H2D1 0.95 . ? C3D N2D 1.341(5) . ? C3D H3D 0.95 . ? C4D N2D 1.327(5) . ? C4D C5D 1.374(5) . ? C4D H4D 0.95 . ? C5D H5D 0.95 . ? C6D O1D 1.228(4) . ? C6D N1D 1.335(4) . ? C7D C8D 1.493(5) . ? C7D H7D1 0.98 . ? C7D H7D2 0.98 . ? C7D H7D3 0.98 . ? C8D N3D 1.277(4) . ? C8D C9D 1.490(5) . ? C9D H9D1 0.98 . ? C9D H9D2 0.98 . ? C9D H9D3 0.98 . ? N1D N3D 1.394(4) . ? N1D H1D 0.95(4) . ? C10A C15A 1.393(4) . ? C10A C11A 1.408(4) . ? C10A C16A 1.515(4) . ? C11A C12A 1.385(4) . ? C11A Cl1A 1.722(3) . ? C12A C13A 1.389(4) . ? C12A H12A 0.95 . ? C13A C14A 1.371(4) . ? C13A N4A 1.476(4) . ? C14A C15A 1.397(4) . ? C14A H14A 0.95 . ? C15A H15A 0.95 . ? C16A O3A 1.211(4) . ? C16A O2A 1.287(4) . ? N4A O4A 1.220(4) . ? N4A O5A 1.225(3) . ? O2A H2A 1.08(4) . ? C10B C11B 1.404(4) . ? C10B C15B 1.406(4) . ? C10B C16B 1.504(4) . ? C11B C12B 1.382(4) . ? C11B Cl1B 1.727(3) . ? C12B C13B 1.379(4) . ? C12B H12B 0.95 . ? C13B C14B 1.384(4) . ? C13B N4B 1.475(4) . ? C14B C15B 1.373(5) . ? C14B H14B 0.95 . ? C15B H15B 0.95 . ? C16B O3B 1.246(5) . ? C16B O2B 1.256(5) . ? N4B O4B 1.214(4) . ? N4B O5B 1.221(4) . ? C10C C15C 1.391(4) . ? C10C C11C 1.400(4) . ? C10C C16C 1.512(4) . ? C11C C12C 1.374(4) . ? C11C Cl1C 1.734(3) . ? C12C C13C 1.391(4) . ? C12C H12C 0.95 . ? C13C C14C 1.378(4) . ? C13C N4C 1.467(4) . ? C14C C15C 1.380(4) . ? C14C H14C 0.95 . ? C15C H15C 0.95 . ? C16C O3C 1.208(4) . ? C16C O2C 1.301(4) . ? N4C O4C 1.215(4) . ? N4C O5C 1.223(4) . ? O2C H2C 0.86(5) . ? C10D C11D 1.389(4) . ? C10D C15D 1.397(4) . ? C10D C16D 1.516(4) . ? C11D C12D 1.381(4) . ? C11D Cl1D 1.725(3) . ? C12D C13D 1.385(4) . ? C12D H12D 0.95 . ? C13D C14D 1.372(4) . ? C13D N4D 1.478(4) . ? C14D C15D 1.386(4) . ? C14D H14D 0.95 . ? C15D H15D 0.95 . ? C16D O3D 1.194(4) . ? C16D O2D 1.309(4) . ? N4D O4D 1.212(4) . ? N4D O5D 1.216(4) . ? O2D H2D 0.91(5) . ? 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 C2A C1A C5A 118.1(3) . . ? C2A C1A C6A 120.5(3) . . ? C5A C1A C6A 121.4(3) . . ? C3A C2A C1A 119.2(3) . . ? C3A C2A H2A1 120.4 . . ? C1A C2A H2A1 120.4 . . ? N2A C3A C2A 123.2(3) . . ? N2A C3A H3A 118.4 . . ? C2A C3A H3A 118.4 . . ? N2A C4A C5A 122.0(3) . . ? N2A C4A H4A 119 . . ? C5A C4A H4A 119 . . ? C4A C5A C1A 119.6(3) . . ? C4A C5A H5A 120.2 . . ? C1A C5A H5A 120.2 . . ? O1A C6A N1A 125.8(3) . . ? O1A C6A C1A 121.3(3) . . ? N1A C6A C1A 112.9(3) . . ? C8A C7A H7A1 109.5 . . ? C8A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C8A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? N3A C8A C9A 117.1(3) . . ? N3A C8A C7A 124.7(3) . . ? C9A C8A C7A 118.2(3) . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C6A N1A N3A 120.4(3) . . ? C6A N1A H1A 118(3) . . ? N3A N1A H1A 121(3) . . ? C3A N2A C4A 118.0(3) . . ? C8A N3A N1A 115.1(3) . . ? C2B C1B C5B 120 . . ? C2B C1B C6B 120.4(2) . . ? C5B C1B C6B 119.6(2) . . ? C1B C2B C3B 120 . . ? C1B C2B H2B1 120 . . ? C3B C2B H2B1 120 . . ? C2B C3B N2B 120 . . ? C2B C3B H3B 120 . . ? N2B C3B H3B 120 . . ? C4B N2B C3B 120 . . ? C4B N2B H2B 120 . . ? C3B N2B H2B 120 . . ? C5B C4B N2B 120 . . ? C5B C4B H4B 120 . . ? N2B C4B H4B 120 . . ? C4B C5B C1B 120 . . ? C4B C5B H5B 120 . . ? C1B C5B H5B 120 . . ? O1B C6B N1B 123.5(3) . . ? O1B C6B C1B 123.3(3) . . ? N1B C6B C1B 113.2(3) . . ? C8B C7B H7B1 109.5 . . ? C8B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C8B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? N3B C8B C9B 118.1(3) . . ? N3B C8B C7B 124.9(3) . . ? C9B C8B C7B 117.0(3) . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C6B N1B N3B 119.5(3) . . ? C6B N1B H1B 117(3) . . ? N3B N1B H1B 115(3) . . ? C8B N3B N1B 115.0(3) . . ? C5C C1C C2C 118.2(3) . . ? C5C C1C C6C 119.5(3) . . ? C2C C1C C6C 122.2(3) . . ? C3C C2C C1C 119.1(3) . . ? C3C C2C H2C1 120.4 . . ? C1C C2C H2C1 120.4 . . ? N2C C3C C2C 122.3(3) . . ? N2C C3C H3C 118.8 . . ? C2C C3C H3C 118.8 . . ? N2C C4C C5C 122.0(3) . . ? N2C C4C H4C 119 . . ? C5C C4C H4C 119 . . ? C1C C5C C4C 119.1(3) . . ? C1C C5C H5C 120.5 . . ? C4C C5C H5C 120.5 . . ? O1C C6C N1C 125.4(3) . . ? O1C C6C C1C 121.3(3) . . ? N1C C6C C1C 113.4(3) . . ? C8C C7C H7C1 109.5 . . ? C8C C7C H7C2 109.5 . . ? H7C1 C7C H7C2 109.5 . . ? C8C C7C H7C3 109.5 . . ? H7C1 C7C H7C3 109.5 . . ? H7C2 C7C H7C3 109.5 . . ? N3C C8C C9C 117.5(3) . . ? N3C C8C C7C 125.3(3) . . ? C9C C8C C7C 117.1(3) . . ? C8C C9C H9C1 109.5 . . ? C8C C9C H9C2 109.5 . . ? H9C1 C9C H9C2 109.5 . . ? C8C C9C H9C3 109.5 . . ? H9C1 C9C H9C3 109.5 . . ? H9C2 C9C H9C3 109.5 . . ? C6C N1C N3C 120.1(3) . . ? C6C N1C H1C 119(3) . . ? N3C N1C H1C 120(3) . . ? C3C N2C C4C 119.2(3) . . ? C8C N3C N1C 114.7(3) . . ? C5D C1D C2D 118.1(3) . . ? C5D C1D C6D 117.0(3) . . ? C2D C1D C6D 124.8(3) . . ? C3D C2D C1D 118.4(3) . . ? C3D C2D H2D1 120.8 . . ? C1D C2D H2D1 120.8 . . ? N2D C3D C2D 122.8(3) . . ? N2D C3D H3D 118.6 . . ? C2D C3D H3D 118.6 . . ? N2D C4D C5D 122.2(3) . . ? N2D C4D H4D 118.9 . . ? C5D C4D H4D 118.9 . . ? C4D C5D C1D 119.9(3) . . ? C4D C5D H5D 120.1 . . ? C1D C5D H5D 120.1 . . ? O1D C6D N1D 124.1(3) . . ? O1D C6D C1D 120.3(3) . . ? N1D C6D C1D 115.6(3) . . ? C8D C7D H7D1 109.5 . . ? C8D C7D H7D2 109.5 . . ? H7D1 C7D H7D2 109.5 . . ? C8D C7D H7D3 109.5 . . ? H7D1 C7D H7D3 109.5 . . ? H7D2 C7D H7D3 109.5 . . ? N3D C8D C9D 116.3(3) . . ? N3D C8D C7D 126.1(3) . . ? C9D C8D C7D 117.6(3) . . ? C8D C9D H9D1 109.5 . . ? C8D C9D H9D2 109.5 . . ? H9D1 C9D H9D2 109.5 . . ? C8D C9D H9D3 109.5 . . ? H9D1 C9D H9D3 109.5 . . ? H9D2 C9D H9D3 109.5 . . ? C6D N1D N3D 117.7(3) . . ? C6D N1D H1D 117(3) . . ? N3D N1D H1D 125(3) . . ? C4D N2D C3D 118.6(3) . . ? C8D N3D N1D 116.3(3) . . ? C15A C10A C11A 117.6(3) . . ? C15A C10A C16A 115.8(2) . . ? C11A C10A C16A 126.5(3) . . ? C12A C11A C10A 120.9(3) . . ? C12A C11A Cl1A 116.0(2) . . ? C10A C11A Cl1A 122.9(2) . . ? C11A C12A C13A 118.4(3) . . ? C11A C12A H12A 120.8 . . ? C13A C12A H12A 120.8 . . ? C14A C13A C12A 123.2(3) . . ? C14A C13A N4A 119.3(3) . . ? C12A C13A N4A 117.4(3) . . ? C13A C14A C15A 117.0(3) . . ? C13A C14A H14A 121.5 . . ? C15A C14A H14A 121.5 . . ? C10A C15A C14A 122.6(3) . . ? C10A C15A H15A 118.7 . . ? C14A C15A H15A 118.7 . . ? O3A C16A O2A 124.9(3) . . ? O3A C16A C10A 120.0(3) . . ? O2A C16A C10A 115.0(2) . . ? O4A N4A O5A 125.1(3) . . ? O4A N4A C13A 118.3(3) . . ? O5A N4A C13A 116.6(3) . . ? C16A O2A H2A 109(2) . . ? C11B C10B C15B 117.3(3) . . ? C11B C10B C16B 126.9(3) . . ? C15B C10B C16B 115.8(3) . . ? C12B C11B C10B 121.1(3) . . ? C12B C11B Cl1B 116.1(2) . . ? C10B C11B Cl1B 122.8(2) . . ? C13B C12B C11B 118.8(3) . . ? C13B C12B H12B 120.6 . . ? C11B C12B H12B 120.6 . . ? C12B C13B C14B 122.7(3) . . ? C12B C13B N4B 118.4(3) . . ? C14B C13B N4B 118.9(3) . . ? C15B C14B C13B 117.5(3) . . ? C15B C14B H14B 121.3 . . ? C13B C14B H14B 121.3 . . ? C14B C15B C10B 122.7(3) . . ? C14B C15B H15B 118.7 . . ? C10B C15B H15B 118.7 . . ? O3B C16B O2B 123.0(3) . . ? O3B C16B C10B 117.5(4) . . ? O2B C16B C10B 119.4(4) . . ? O4B N4B O5B 124.1(3) . . ? O4B N4B C13B 118.2(3) . . ? O5B N4B C13B 117.7(3) . . ? C15C C10C C11C 117.5(3) . . ? C15C C10C C16C 115.5(2) . . ? C11C C10C C16C 127.0(2) . . ? C12C C11C C10C 121.5(3) . . ? C12C C11C Cl1C 115.8(2) . . ? C10C C11C Cl1C 122.7(2) . . ? C11C C12C C13C 118.3(3) . . ? C11C C12C H12C 120.9 . . ? C13C C12C H12C 120.9 . . ? C14C C13C C12C 122.8(3) . . ? C14C C13C N4C 118.9(3) . . ? C12C C13C N4C 118.3(3) . . ? C13C C14C C15C 117.1(3) . . ? C13C C14C H14C 121.5 . . ? C15C C14C H14C 121.5 . . ? C14C C15C C10C 122.9(3) . . ? C14C C15C H15C 118.5 . . ? C10C C15C H15C 118.5 . . ? O3C C16C O2C 124.8(3) . . ? O3C C16C C10C 120.0(3) . . ? O2C C16C C10C 115.1(2) . . ? O4C N4C O5C 123.6(3) . . ? O4C N4C C13C 118.2(3) . . ? O5C N4C C13C 118.2(3) . . ? C16C O2C H2C 111(3) . . ? C11D C10D C15D 118.6(3) . . ? C11D C10D C16D 123.0(3) . . ? C15D C10D C16D 118.3(3) . . ? C12D C11D C10D 121.1(3) . . ? C12D C11D Cl1D 117.1(2) . . ? C10D C11D Cl1D 121.7(2) . . ? C11D C12D C13D 118.1(3) . . ? C11D C12D H12D 120.9 . . ? C13D C12D H12D 120.9 . . ? C14D C13D C12D 122.9(3) . . ? C14D C13D N4D 119.0(3) . . ? C12D C13D N4D 118.1(3) . . ? C13D C14D C15D 117.9(3) . . ? C13D C14D H14D 121 . . ? C15D C14D H14D 121 . . ? C14D C15D C10D 121.2(3) . . ? C14D C15D H15D 119.4 . . ? C10D C15D H15D 119.4 . . ? O3D C16D O2D 125.5(3) . . ? O3D C16D C10D 122.5(3) . . ? O2D C16D C10D 112.0(3) . . ? O4D N4D O5D 124.5(3) . . ? O4D N4D C13D 118.0(3) . . ? O5D N4D C13D 117.5(3) . . ? C16D O2D H2D 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A C1A C2A C3A 0.0(5) . . . . ? C6A C1A C2A C3A 177.8(3) . . . . ? C1A C2A C3A N2A -1.2(5) . . . . ? N2A C4A C5A C1A -0.9(5) . . . . ? C2A C1A C5A C4A 1.0(4) . . . . ? C6A C1A C5A C4A -176.7(3) . . . . ? C2A C1A C6A O1A -38.3(5) . . . . ? C5A C1A C6A O1A 139.3(3) . . . . ? C2A C1A C6A N1A 145.0(3) . . . . ? C5A C1A C6A N1A -37.4(4) . . . . ? O1A C6A N1A N3A -3.3(5) . . . . ? C1A C6A N1A N3A 173.2(3) . . . . ? C2A C3A N2A C4A 1.3(5) . . . . ? C5A C4A N2A C3A -0.2(5) . . . . ? C9A C8A N3A N1A 180.0(3) . . . . ? C7A C8A N3A N1A 1.6(5) . . . . ? C6A N1A N3A C8A -167.9(3) . . . . ? C5B C1B C2B C3B 0 . . . . ? C6B C1B C2B C3B 179.8(3) . . . . ? C1B C2B C3B N2B 0 . . . . ? C2B C3B N2B C4B 0 . . . . ? C3B N2B C4B C5B 0 . . . . ? N2B C4B C5B C1B 0 . . . . ? C2B C1B C5B C4B 0 . . . . ? C6B C1B C5B C4B -179.8(2) . . . . ? C2B C1B C6B O1B 155.0(3) . . . . ? C5B C1B C6B O1B -25.3(4) . . . . ? C2B C1B C6B N1B -22.7(4) . . . . ? C5B C1B C6B N1B 157.1(2) . . . . ? O1B C6B N1B N3B 8.8(5) . . . . ? C1B C6B N1B N3B -173.6(3) . . . . ? C9B C8B N3B N1B -177.8(3) . . . . ? C7B C8B N3B N1B 4.2(5) . . . . ? C6B N1B N3B C8B -148.8(3) . . . . ? C5C C1C C2C C3C -0.2(4) . . . . ? C6C C1C C2C C3C 177.2(3) . . . . ? C1C C2C C3C N2C 0.1(4) . . . . ? C2C C1C C5C C4C 0.4(5) . . . . ? C6C C1C C5C C4C -177.0(3) . . . . ? N2C C4C C5C C1C -0.7(5) . . . . ? C5C C1C C6C O1C 28.5(4) . . . . ? C2C C1C C6C O1C -148.8(3) . . . . ? C5C C1C C6C N1C -152.9(3) . . . . ? C2C C1C C6C N1C 29.8(4) . . . . ? O1C C6C N1C N3C 4.8(5) . . . . ? C1C C6C N1C N3C -173.7(3) . . . . ? C2C C3C N2C C4C -0.4(5) . . . . ? C5C C4C N2C C3C 0.7(5) . . . . ? C9C C8C N3C N1C 179.8(3) . . . . ? C7C C8C N3C N1C -2.3(5) . . . . ? C6C N1C N3C C8C 163.0(3) . . . . ? C5D C1D C2D C3D 0.3(4) . . . . ? C6D C1D C2D C3D 179.3(3) . . . . ? C1D C2D C3D N2D 0.1(5) . . . . ? N2D C4D C5D C1D 1.1(5) . . . . ? C2D C1D C5D C4D -0.9(5) . . . . ? C6D C1D C5D C4D -180.0(3) . . . . ? C5D C1D C6D O1D 22.4(4) . . . . ? C2D C1D C6D O1D -156.6(3) . . . . ? C5D C1D C6D N1D -157.4(3) . . . . ? C2D C1D C6D N1D 23.6(4) . . . . ? O1D C6D N1D N3D -4.1(5) . . . . ? C1D C6D N1D N3D 175.7(3) . . . . ? C5D C4D N2D C3D -0.7(5) . . . . ? C2D C3D N2D C4D 0.1(5) . . . . ? C9D C8D N3D N1D 179.1(3) . . . . ? C7D C8D N3D N1D -1.8(5) . . . . ? C6D N1D N3D C8D 159.3(3) . . . . ? C15A C10A C11A C12A 5.2(4) . . . . ? C16A C10A C11A C12A -172.2(3) . . . . ? C15A C10A C11A Cl1A -169.7(2) . . . . ? C16A C10A C11A Cl1A 12.8(4) . . . . ? C10A C11A C12A C13A -4.0(4) . . . . ? Cl1A C11A C12A C13A 171.3(2) . . . . ? C11A C12A C13A C14A 0.0(4) . . . . ? C11A C12A C13A N4A -178.4(3) . . . . ? C12A C13A C14A C15A 2.5(4) . . . . ? N4A C13A C14A C15A -179.1(2) . . . . ? C11A C10A C15A C14A -2.6(4) . . . . ? C16A C10A C15A C14A 175.1(3) . . . . ? C13A C14A C15A C10A -1.1(4) . . . . ? C15A C10A C16A O3A 11.9(4) . . . . ? C11A C10A C16A O3A -170.6(3) . . . . ? C15A C10A C16A O2A -163.8(3) . . . . ? C11A C10A C16A O2A 13.7(4) . . . . ? C14A C13A N4A O4A 161.7(3) . . . . ? C12A C13A N4A O4A -19.8(4) . . . . ? C14A C13A N4A O5A -19.3(4) . . . . ? C12A C13A N4A O5A 159.2(3) . . . . ? C15B C10B C11B C12B 0.4(4) . . . . ? C16B C10B C11B C12B 179.2(3) . . . . ? C15B C10B C11B Cl1B -178.0(2) . . . . ? C16B C10B C11B Cl1B 0.9(4) . . . . ? C10B C11B C12B C13B 0.1(4) . . . . ? Cl1B C11B C12B C13B 178.5(2) . . . . ? C11B C12B C13B C14B -1.2(4) . . . . ? C11B C12B C13B N4B 179.5(2) . . . . ? C12B C13B C14B C15B 1.8(4) . . . . ? N4B C13B C14B C15B -178.9(3) . . . . ? C13B C14B C15B C10B -1.3(4) . . . . ? C11B C10B C15B C14B 0.3(4) . . . . ? C16B C10B C15B C14B -178.7(3) . . . . ? C11B C10B C16B O3B -171.0(3) . . . . ? C15B C10B C16B O3B 7.9(4) . . . . ? C11B C10B C16B O2B 7.3(5) . . . . ? C15B C10B C16B O2B -173.8(3) . . . . ? C12B C13B N4B O4B 9.9(4) . . . . ? C14B C13B N4B O4B -169.4(3) . . . . ? C12B C13B N4B O5B -170.3(3) . . . . ? C14B C13B N4B O5B 10.3(4) . . . . ? C15C C10C C11C C12C 2.1(4) . . . . ? C16C C10C C11C C12C -176.4(3) . . . . ? C15C C10C C11C Cl1C -175.7(2) . . . . ? C16C C10C C11C Cl1C 5.7(4) . . . . ? C10C C11C C12C C13C -0.5(4) . . . . ? Cl1C C11C C12C C13C 177.5(2) . . . . ? C11C C12C C13C C14C -0.7(4) . . . . ? C11C C12C C13C N4C -179.8(3) . . . . ? C12C C13C C14C C15C 0.3(4) . . . . ? N4C C13C C14C C15C 179.3(3) . . . . ? C13C C14C C15C C10C 1.5(4) . . . . ? C11C C10C C15C C14C -2.7(4) . . . . ? C16C C10C C15C C14C 176.0(3) . . . . ? C15C C10C C16C O3C 21.6(4) . . . . ? C11C C10C C16C O3C -159.8(3) . . . . ? C15C C10C C16C O2C -155.0(3) . . . . ? C11C C10C C16C O2C 23.5(4) . . . . ? C14C C13C N4C O4C 175.5(3) . . . . ? C12C C13C N4C O4C -5.4(5) . . . . ? C14C C13C N4C O5C -4.8(5) . . . . ? C12C C13C N4C O5C 174.3(3) . . . . ? C15D C10D C11D C12D 0.7(4) . . . . ? C16D C10D C11D C12D -179.9(3) . . . . ? C15D C10D C11D Cl1D 178.7(2) . . . . ? C16D C10D C11D Cl1D -1.9(4) . . . . ? C10D C11D C12D C13D -1.9(4) . . . . ? Cl1D C11D C12D C13D -180.0(2) . . . . ? C11D C12D C13D C14D 1.0(4) . . . . ? C11D C12D C13D N4D -179.5(3) . . . . ? C12D C13D C14D C15D 1.1(5) . . . . ? N4D C13D C14D C15D -178.5(3) . . . . ? C13D C14D C15D C10D -2.3(5) . . . . ? C11D C10D C15D C14D 1.4(5) . . . . ? C16D C10D C15D C14D -178.0(3) . . . . ? C11D C10D C16D O3D -30.5(5) . . . . ? C15D C10D C16D O3D 148.8(3) . . . . ? C11D C10D C16D O2D 150.5(3) . . . . ? C15D C10D C16D O2D -30.2(4) . . . . ? C14D C13D N4D O4D 4.2(5) . . . . ? C12D C13D N4D O4D -175.3(3) . . . . ? C14D C13D N4D O5D -177.6(3) . . . . ? C12D C13D N4D O5D 2.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1A O1B 0.89(4) 2.31(4) 3.151(4) 156(4) . N2B H2B O2B 0.88 1.86 2.718(4) 166 . N2B H2B O3B 0.88 2.37 3.012(4) 130 . C4B H4B O3B 0.95 2.64 3.161(4) 115 . N1B H1B O1C 0.88(4) 2.11(4) 2.979(3) 168(4) . N1C H1C O1D 0.87(4) 2.30(4) 3.135(4) 160(4) . N1D H1D O1A 0.95(4) 2.28(4) 3.145(4) 150(4) 1_356 O2A H2A N2A 1.08(4) 1.52(4) 2.585(3) 166(4) . O2C H2C N2C 0.86(5) 1.74(5) 2.605(3) 173(4) . O2D H2D N2D 0.91(5) 1.72(5) 2.632(4) 171(4) . ###END