#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012697.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012697 loop_ _publ_author_name 'Bakir, Mohammed' 'Green, Orville' _publ_section_title ; Di-2-pyridyl ketone p-aminobenzoylhydrazone hydrate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o263 _journal_page_last o265 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C18 H15 N5 O , H2 O' _chemical_formula_sum 'C18 H17 N5 O2' _chemical_formula_weight 335.37 _chemical_melting_point 400 _chemical_name_common 'Di-2-pyridyl ketone p-aminobenzoylhydrazone hydrate' _chemical_name_systematic ; 4-Amino-2'-(di-2-pyridylmethylene)benzohydrazide hydrate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 91.083(9) _cell_angle_beta 109.199(5) _cell_angle_gamma 109.571(10) _cell_formula_units_Z 2 _cell_length_a 8.6648(10) _cell_length_b 9.9630(16) _cell_length_c 11.1996(11) _cell_measurement_reflns_used 46 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12.44 _cell_measurement_theta_min 3.90 _cell_volume 851.2(2) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 1996)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.077 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7103 _diffrn_reflns_theta_full 32.50 _diffrn_reflns_theta_max 32.50 _diffrn_reflns_theta_min 1.95 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'via \y-scans (XSCANS; Bruker, 1996)' _exptl_crystal_colour yellow-brown _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description octahedral _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.19 _refine_diff_density_min -0.18 _refine_ls_extinction_coef 0.0156(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 6067 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.947 _refine_ls_R_factor_all 0.172 _refine_ls_R_factor_gt 0.050 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.02P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.094 _refine_ls_wR_factor_ref 0.124 _reflns_number_gt 1820 _reflns_number_total 6067 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1194.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 851.21(19) _cod_database_code 2012697 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N1 0.5842(2) 0.30151(16) 0.32922(14) 0.0743(5) Uani d . 1 N C11 0.4877(3) 0.1993(2) 0.3790(2) 0.0963(9) Uani d . 1 C H11A 0.4935 0.2220 0.4617 0.116 Uiso calc R 1 H C12 0.3817(3) 0.0645(2) 0.3159(2) 0.0887(8) Uani d . 1 C H12A 0.3155 -0.0020 0.3539 0.106 Uiso calc R 1 H C13 0.3755(3) 0.0300(2) 0.19650(19) 0.0810(7) Uani d . 1 C H13A 0.3052 -0.0613 0.1511 0.097 Uiso calc R 1 H C14 0.4738(3) 0.13115(19) 0.14301(17) 0.0666(6) Uani d . 1 C H14A 0.4711 0.1083 0.0612 0.080 Uiso calc R 1 H C15 0.5769(2) 0.26686(17) 0.21077(16) 0.0531(5) Uani d . 1 C C1 0.6862(2) 0.37739(17) 0.15655(15) 0.0489(4) Uani d . 1 C N2 0.4948(2) 0.32413(15) -0.06348(13) 0.0577(4) Uani d . 1 N C21 0.4712(3) 0.31476(19) -0.18867(17) 0.0658(5) Uani d . 1 C H21A 0.3584 0.2944 -0.2470 0.079 Uiso calc R 1 H C22 0.6033(3) 0.3335(2) -0.23497(18) 0.0698(6) Uani d . 1 C H22A 0.5806 0.3278 -0.3224 0.084 Uiso calc R 1 H C23 0.7696(3) 0.3607(2) -0.15089(18) 0.0682(6) Uani d . 1 C H23A 0.8616 0.3722 -0.1799 0.082 Uiso calc R 1 H C24 0.7971(3) 0.37061(18) -0.02213(17) 0.0576(5) Uani d . 1 C H24A 0.9085 0.3880 0.0372 0.069 Uiso calc R 1 H C25 0.6590(2) 0.35461(16) 0.01796(15) 0.0484(4) Uani d . 1 C N3 0.80950(19) 0.49946(14) 0.21342(12) 0.0500(4) Uani d . 1 N N4 0.84465(19) 0.54217(13) 0.33902(12) 0.0511(4) Uani d . 1 N H4A 0.7931 0.4862 0.3828 0.061 Uiso calc R 1 H C2 0.9646(2) 0.67696(18) 0.39298(15) 0.0501(4) Uani d . 1 C O2 1.05071(18) 0.75088(13) 0.33431(11) 0.0727(4) Uani d . 1 O C31 0.9784(2) 0.72869(17) 0.52141(14) 0.0462(4) Uani d . 1 C C32 1.0880(3) 0.86984(18) 0.57435(16) 0.0611(5) Uani d . 1 C H32A 1.1512 0.9263 0.5288 0.073 Uiso calc R 1 H C33 1.1049(3) 0.92749(19) 0.69182(16) 0.0650(6) Uani d . 1 C H33A 1.1790 1.0223 0.7244 0.078 Uiso calc R 1 H C34 1.0138(3) 0.84741(18) 0.76295(15) 0.0556(5) Uani d . 1 C C35 0.9039(3) 0.70589(18) 0.71144(15) 0.0597(5) Uani d . 1 C H35A 0.8414 0.6494 0.7574 0.072 Uiso calc R 1 H C36 0.8871(2) 0.64892(18) 0.59283(16) 0.0571(5) Uani d . 1 C H36A 0.8124 0.5543 0.5598 0.068 Uiso calc R 1 H N5 1.0333(2) 0.90457(17) 0.88126(13) 0.0776(6) Uani d . 1 N H5A 1.1032 0.9917 0.9126 0.093 Uiso calc R 1 H H5B 0.9758 0.8534 0.9244 0.093 Uiso calc R 1 H O1 0.8545(3) 0.76604(18) 1.05729(18) 0.0799(5) Uani d . 1 O H1 0.738(4) 0.728(3) 1.038(2) 0.126(11) Uiso d . 1 H H2 0.899(4) 0.738(3) 1.124(3) 0.144(13) Uiso d . 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0835(13) 0.0663(10) 0.0572(9) -0.0013(9) 0.0348(9) -0.0001(8) C11 0.112(2) 0.0878(16) 0.0662(13) -0.0082(15) 0.0481(14) 0.0050(12) C12 0.0872(18) 0.0733(14) 0.0783(15) -0.0070(13) 0.0317(14) 0.0157(12) C13 0.0945(18) 0.0521(11) 0.0692(14) 0.0049(12) 0.0171(13) 0.0112(10) C14 0.0813(15) 0.0472(10) 0.0579(11) 0.0094(10) 0.0224(11) 0.0045(9) C15 0.0573(12) 0.0476(9) 0.0484(10) 0.0125(9) 0.0181(9) 0.0036(8) C1 0.0532(11) 0.0435(9) 0.0465(9) 0.0135(9) 0.0177(9) 0.0018(7) N2 0.0586(11) 0.0576(9) 0.0501(8) 0.0157(8) 0.0167(8) 0.0029(7) C21 0.0698(15) 0.0672(12) 0.0505(11) 0.0211(11) 0.0131(10) 0.0047(9) C22 0.0914(18) 0.0659(12) 0.0477(11) 0.0193(12) 0.0289(12) 0.0002(9) C23 0.0759(16) 0.0656(12) 0.0645(12) 0.0142(11) 0.0388(12) -0.0022(10) C24 0.0553(12) 0.0557(10) 0.0550(11) 0.0112(9) 0.0207(9) -0.0032(8) C25 0.0508(11) 0.0408(9) 0.0475(9) 0.0087(8) 0.0184(9) -0.0021(7) N3 0.0542(10) 0.0496(8) 0.0424(7) 0.0146(7) 0.0170(7) -0.0015(6) N4 0.0598(10) 0.0441(8) 0.0414(7) 0.0083(7) 0.0191(7) -0.0011(6) C2 0.0512(11) 0.0477(9) 0.0469(9) 0.0109(9) 0.0194(9) -0.0002(8) O2 0.0834(11) 0.0608(8) 0.0597(8) -0.0048(7) 0.0402(8) -0.0085(6) C31 0.0474(11) 0.0442(9) 0.0423(9) 0.0112(8) 0.0159(8) 0.0022(7) C32 0.0694(14) 0.0497(10) 0.0551(10) 0.0028(10) 0.0302(10) 0.0008(8) C33 0.0778(15) 0.0487(10) 0.0546(11) 0.0010(10) 0.0290(10) -0.0065(8) C34 0.0659(13) 0.0524(10) 0.0434(9) 0.0145(10) 0.0205(9) 0.0016(8) C35 0.0716(14) 0.0547(10) 0.0495(10) 0.0106(10) 0.0297(10) 0.0081(8) C36 0.0643(13) 0.0430(9) 0.0532(10) 0.0057(9) 0.0217(10) 0.0021(8) N5 0.1009(15) 0.0698(10) 0.0504(9) 0.0089(10) 0.0354(9) -0.0076(7) O1 0.0798(13) 0.0870(11) 0.0781(11) 0.0231(10) 0.0409(10) 0.0291(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C15 N1 C11 117.43(16) yes N1 C11 C12 124.1(2) yes N1 C11 H11A 118.0 no C12 C11 H11A 118.0 no C13 C12 C11 118.2(2) no C13 C12 H12A 120.9 no C11 C12 H12A 120.9 no C12 C13 C14 119.37(19) no C12 C13 H13A 120.3 no C14 C13 H13A 120.3 no C13 C14 C15 119.91(18) no C13 C14 H14A 120.0 no C15 C14 H14A 120.0 no N1 C15 C14 121.02(16) no N1 C15 C1 117.77(15) no C14 C15 C1 121.20(15) no N3 C1 C15 128.82(14) yes N3 C1 C25 111.42(14) yes C15 C1 C25 119.76(14) yes C25 N2 C21 116.57(17) yes N2 C21 C22 123.7(2) yes N2 C21 H21A 118.1 no C22 C21 H21A 118.1 no C21 C22 C23 119.08(18) no C21 C22 H22A 120.5 no C23 C22 H22A 120.5 no C22 C23 C24 118.3(2) no C22 C23 H23A 120.9 no C24 C23 H23A 120.9 no C25 C24 C23 119.58(19) no C25 C24 H24A 120.2 no C23 C24 H24A 120.2 no N2 C25 C24 122.71(16) no N2 C25 C1 116.05(16) no C24 C25 C1 121.17(17) no C1 N3 N4 119.37(14) yes N3 N4 C2 117.83(13) yes N3 N4 H4A 121.1 no C2 N4 H4A 121.1 no O2 C2 N4 120.86(15) yes O2 C2 C31 122.73(15) yes N4 C2 C31 116.37(15) yes C36 C31 C32 117.11(15) no C36 C31 C2 125.10(14) no C32 C31 C2 117.77(15) no C33 C32 C31 121.50(16) no C33 C32 H32A 119.2 no C31 C32 H32A 119.2 no C32 C33 C34 121.22(16) no C32 C33 H33A 119.4 no C34 C33 H33A 119.4 no N5 C34 C33 121.06(16) no N5 C34 C35 120.96(17) no C33 C34 C35 117.98(15) no C36 C35 C34 120.42(17) no C36 C35 H35A 119.8 no C34 C35 H35A 119.8 no C35 C36 C31 121.78(15) no C35 C36 H36A 119.1 no C31 C36 H36A 119.1 no C34 N5 H5A 120.0 no C34 N5 H5B 120.0 no H5A N5 H5B 120.0 no H1 O1 H2 106(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C15 1.340(2) no N1 C11 1.344(2) no C11 C12 1.363(3) no C11 H11A 0.9300 no C12 C13 1.354(3) no C12 H12A 0.9300 no C13 C14 1.372(2) no C13 H13A 0.9300 no C14 C15 1.381(2) no C14 H14A 0.9300 no C15 C1 1.478(2) yes C1 N3 1.2957(19) yes C1 C25 1.492(2) yes N2 C25 1.340(2) no N2 C21 1.345(2) no C21 C22 1.366(3) no C21 H21A 0.9300 no C22 C23 1.368(3) no C22 H22A 0.9300 no C23 C24 1.378(2) no C23 H23A 0.9300 no C24 C25 1.374(2) no C24 H24A 0.9300 no N3 N4 1.3643(16) yes N4 C2 1.3675(19) yes N4 H4A 0.8600 no C2 O2 1.2260(18) yes C2 C31 1.472(2) yes C31 C36 1.384(2) no C31 C32 1.391(2) no C32 C33 1.368(2) no C32 H32A 0.9300 no C33 C34 1.382(2) no C33 H33A 0.9300 no C34 N5 1.3668(19) yes C34 C35 1.391(2) no C35 C36 1.377(2) no C35 H35A 0.9300 no C36 H36A 0.9300 no N5 H5A 0.8600 no N5 H5B 0.8600 no O1 H1 0.90(3) yes O1 H2 0.83(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N4 H4A N1 . 0.86 2.01 2.656(2) 131 N5 H5B O1 . 0.86 2.13 2.979(2) 168 C14 H14A N2 . 0.93 2.57 3.048(2) 112 N5 H5A O1 2_777 0.86 2.32 3.086(2) 149 O1 H1 N2 2_666 0.90(3) 2.03(3) 2.880(3) 158(2) O1 H2 O2 1_556 0.83(3) 2.26(3) 3.043(2) 158(3) O1 H2 N3 1_556 0.83(3) 2.57(3) 3.193(2) 133(3) C23 H23A O2 2_765 0.93 2.55 3.325(2) 142 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 C15 N1 C11 C12 -1.0(4) N1 C11 C12 C13 1.3(4) C11 C12 C13 C14 -0.5(4) C12 C13 C14 C15 -0.4(3) C11 N1 C15 C14 0.0(3) C11 N1 C15 C1 -178.45(19) C13 C14 C15 N1 0.7(3) C13 C14 C15 C1 179.12(19) N1 C15 C1 N3 10.7(3) C14 C15 C1 N3 -167.73(19) N1 C15 C1 C25 -168.84(18) C14 C15 C1 C25 12.7(3) C25 N2 C21 C22 0.4(3) N2 C21 C22 C23 1.3(3) C21 C22 C23 C24 -1.1(3) C22 C23 C24 C25 -0.7(3) C21 N2 C25 C24 -2.4(2) C21 N2 C25 C1 174.85(14) C23 C24 C25 N2 2.5(3) C23 C24 C25 C1 -174.55(15) N3 C1 C25 N2 -126.34(17) C15 C1 C25 N2 53.3(2) N3 C1 C25 C24 50.9(2) C15 C1 C25 C24 -129.45(19) C15 C1 N3 N4 -3.7(3) C25 C1 N3 N4 175.92(14) C1 N3 N4 C2 -174.31(16) N3 N4 C2 O2 -7.4(3) N3 N4 C2 C31 170.29(15) O2 C2 C31 C36 -178.64(18) N4 C2 C31 C36 3.7(3) O2 C2 C31 C32 3.1(3) N4 C2 C31 C32 -174.54(16) C36 C31 C32 C33 0.0(3) C2 C31 C32 C33 178.35(18) C31 C32 C33 C34 0.2(3) C32 C33 C34 N5 178.85(19) C32 C33 C34 C35 0.0(3) N5 C34 C35 C36 -179.14(18) C33 C34 C35 C36 -0.3(3) C34 C35 C36 C31 0.4(3) C32 C31 C36 C35 -0.3(3) C2 C31 C36 C35 -178.52(18)