#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008357.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_2008357 loop_ _publ_author_name 'Hoong-Kun Fun' 'Kandasamy Chinnakali' 'Ibrahim Abdul Razak' 'Zhong-Lin Lu' 'Bei-Sheng Kang' _publ_section_title ; p-Hydroxybenzaldehyde nicotinoylhydrazone monohydrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 574 _journal_page_last 576 _journal_paper_doi 10.1107/S0108270198015893 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C13 H11 N3 O2,H2 O' _chemical_formula_sum 'C13 H13 N3 O3' _chemical_formula_weight 259.26 _chemical_name_systematic ; p-Hydroxybenzaldehyde nicotinoylhydrazone monohydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.1260(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 27.7745(12) _cell_length_b 7.3270(3) _cell_length_c 11.9575(5) _cell_measurement_reflns_used 3324 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.00 _cell_measurement_theta_min 3.34 _cell_volume 2432.93(18) _computing_cell_refinement 'SAINT (Siemens, 1996a)' _computing_data_collection 'SMART (Siemens, 1996b)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device ; Siemens SMART CCD area-detector diffractometer ; _diffrn_measurement_method '\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 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8816 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 3.34 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.285 _refine_diff_density_min -0.210 _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_method 'SHELXTL (Sheldrick, 1996)' _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3479 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.1211 _refine_ls_R_factor_gt 0.0639 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0345P)^2^+3.0789P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1460 _reflns_number_gt 2101 _reflns_number_total 3479 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1156.cif _cod_data_source_block lg004m _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0345P)^2^+3.0789P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0345P)^2^+3.0789P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2008357 _cod_database_fobs_code 2008357 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z+1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.43270(5) 0.3560(3) 0.63103(12) 0.0479(5) Uani d . 1 . . O O2 0.73755(6) 0.0810(3) 0.62309(15) 0.0498(5) Uani d . 1 . . O N1 0.30241(6) 0.4364(3) 0.47540(16) 0.0393(5) Uani d . 1 . . N N2 0.47055(6) 0.2783(3) 0.47257(15) 0.0330(4) Uani d . 1 . . N N3 0.51378(6) 0.2480(3) 0.52988(14) 0.0326(4) Uani d . 1 . . N C1 0.29703(8) 0.3908(4) 0.3676(2) 0.0411(6) Uani d . 1 . . C C2 0.33377(8) 0.3261(4) 0.30387(19) 0.0389(6) Uani d . 1 . . C C3 0.37912(7) 0.3058(3) 0.35192(18) 0.0344(5) Uani d . 1 . . C C4 0.38574(7) 0.3519(3) 0.46353(16) 0.0271(4) Uani d . 1 . . C C5 0.34643(7) 0.4160(3) 0.52094(18) 0.0333(5) Uani d . 1 . . C C6 0.43179(7) 0.3308(3) 0.52966(17) 0.0290(4) Uani d . 1 . . C C7 0.54774(7) 0.1918(3) 0.46849(18) 0.0305(5) Uani d . 1 . . C C8 0.59630(7) 0.1566(3) 0.51265(17) 0.0278(4) Uani d . 1 . . C C9 0.61075(7) 0.1980(3) 0.62275(18) 0.0325(5) Uani d . 1 . . C C10 0.65769(7) 0.1705(3) 0.65779(18) 0.0341(5) Uani d . 1 . . C C11 0.69169(7) 0.1017(3) 0.58467(18) 0.0327(5) Uani d . 1 . . C C12 0.67745(7) 0.0577(3) 0.47581(18) 0.0333(5) Uani d . 1 . . C C13 0.63022(7) 0.0847(3) 0.44081(18) 0.0310(5) Uani d . 1 . . C O1W 0.5000 0.0357(5) 0.7500 0.0752(11) Uani d S 1 . . O O2W 0.5000 0.4297(4) 0.2500 0.0459(6) Uani d S 1 . . O H1 0.2649(9) 0.405(3) 0.334(2) 0.050(7) Uiso d . 1 . . H H2 0.3272(8) 0.295(3) 0.226(2) 0.045(7) Uiso d . 1 . . H H3 0.4051(8) 0.257(3) 0.310(2) 0.041(7) Uiso d . 1 . . H H5 0.3495(8) 0.445(3) 0.5977(19) 0.035(6) Uiso d . 1 . . H H7 0.5424(8) 0.167(3) 0.388(2) 0.043(7) Uiso d . 1 . . H H9 0.5888(7) 0.249(3) 0.6723(18) 0.029(6) Uiso d . 1 . . H H10 0.6692(8) 0.199(3) 0.737(2) 0.042(6) Uiso d . 1 . . H H12 0.7015(9) 0.010(3) 0.424(2) 0.044(7) Uiso d . 1 . . H H13 0.6202(8) 0.050(3) 0.3637(19) 0.035(6) Uiso d . 1 . . H H1N2 0.4706(9) 0.276(4) 0.400(2) 0.052(8) Uiso d . 1 . . H H1O2 0.7563(11) 0.039(5) 0.569(3) 0.081(11) Uiso d . 1 . . H H1W1 0.5008(18) 0.107(6) 0.694(3) 0.146(19) Uiso d . 1 . . H H1W2 0.5197(10) 0.506(4) 0.286(2) 0.071(10) 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 O1 0.0303(8) 0.0876(14) 0.0258(8) 0.0040(8) -0.0006(6) -0.0052(8) O2 0.0250(8) 0.0814(14) 0.0427(10) 0.0112(8) -0.0056(7) -0.0091(10) N1 0.0255(9) 0.0523(13) 0.0400(11) 0.0081(8) 0.0003(7) -0.0023(10) N2 0.0204(8) 0.0518(12) 0.0266(9) 0.0055(8) -0.0023(7) 0.0019(9) N3 0.0225(8) 0.0446(11) 0.0306(9) 0.0031(8) -0.0029(7) 0.0022(8) C1 0.0267(10) 0.0548(16) 0.0415(13) 0.0070(10) -0.0075(9) -0.0048(11) C2 0.0338(11) 0.0520(16) 0.0306(11) 0.0047(10) -0.0040(9) -0.0049(11) C3 0.0264(10) 0.0462(14) 0.0307(11) 0.0042(9) 0.0031(8) -0.0034(10) C4 0.0227(9) 0.0312(11) 0.0273(10) 0.0016(8) -0.0004(7) 0.0016(8) C5 0.0280(10) 0.0437(13) 0.0284(11) 0.0032(9) 0.0012(8) -0.0027(10) C6 0.0224(9) 0.0370(12) 0.0277(10) 0.0003(8) -0.0003(7) 0.0032(9) C7 0.0252(9) 0.0367(12) 0.0295(11) 0.0003(9) -0.0005(8) 0.0013(9) C8 0.0210(9) 0.0322(11) 0.0303(10) 0.0018(8) 0.0008(7) 0.0020(9) C9 0.0270(10) 0.0412(13) 0.0296(11) 0.0053(9) 0.0062(8) -0.0044(10) C10 0.0296(10) 0.0449(14) 0.0278(11) 0.0026(9) -0.0014(8) -0.0026(10) C11 0.0229(9) 0.0416(13) 0.0336(11) 0.0031(9) -0.0020(8) 0.0029(10) C12 0.0255(10) 0.0436(14) 0.0311(11) 0.0056(9) 0.0059(8) -0.0029(10) C13 0.0280(10) 0.0376(13) 0.0274(11) 0.0009(9) -0.0016(8) -0.0013(9) O1W 0.124(3) 0.051(2) 0.0496(19) 0.000 -0.0203(19) 0.000 O2W 0.0506(15) 0.0480(16) 0.0387(14) 0.000 -0.0084(11) 0.000 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 C11 O2 H1O2 111(2) C5 N1 C1 116.66(19) C6 N2 N3 119.28(18) C6 N2 H1N2 121.9(17) N3 N2 H1N2 118.3(17) C7 N3 N2 114.18(17) N1 C1 C2 123.5(2) N1 C1 H1 116.7(15) C2 C1 H1 119.8(15) C1 C2 C3 119.3(2) C1 C2 H2 119.0(14) C3 C2 H2 121.7(14) C2 C3 C4 118.5(2) C2 C3 H3 120.7(14) C4 C3 H3 120.8(14) C5 C4 C3 118.02(18) C5 C4 C6 116.55(18) C3 C4 C6 125.37(18) N1 C5 C4 124.1(2) N1 C5 H5 115.9(13) C4 C5 H5 120.0(13) O1 C6 N2 123.03(18) O1 C6 C4 120.46(18) N2 C6 C4 116.48(18) N3 C7 C8 122.46(19) N3 C7 H7 121.5(14) C8 C7 H7 116.0(14) C13 C8 C9 118.50(18) C13 C8 C7 118.37(18) C9 C8 C7 123.09(18) C10 C9 C8 120.39(19) C10 C9 H9 119.4(13) C8 C9 H9 120.2(13) C9 C10 C11 120.76(19) C9 C10 H10 122.2(13) C11 C10 H10 117.0(13) O2 C11 C12 122.68(19) O2 C11 C10 118.17(19) C12 C11 C10 119.15(18) C13 C12 C11 120.04(19) C13 C12 H12 120.6(14) C11 C12 H12 119.4(14) C12 C13 C8 121.13(19) C12 C13 H13 119.4(13) C8 C13 H13 119.5(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 . 1.226(2) yes O2 C11 . 1.354(2) yes O2 H1O2 . 0.89(3) ? N1 C5 . 1.337(3) yes N1 C1 . 1.338(3) yes N2 C6 . 1.342(3) yes N2 N3 . 1.389(2) yes N2 H1N2 . 0.86(3) ? N3 C7 . 1.275(3) yes C1 C2 . 1.370(3) ? C1 H1 . 0.98(2) ? C2 C3 . 1.382(3) ? C2 H2 . 0.97(2) ? C3 C4 . 1.385(3) ? C3 H3 . 0.96(2) ? C4 C5 . 1.383(3) ? C4 C6 . 1.499(3) ? C5 H5 . 0.94(2) ? C7 C8 . 1.462(3) ? C7 H7 . 0.98(2) ? C8 C13 . 1.391(3) ? C8 C9 . 1.402(3) ? C9 C10 . 1.377(3) ? C9 H9 . 0.94(2) ? C10 C11 . 1.394(3) ? C10 H10 . 1.01(2) ? C11 C12 . 1.391(3) ? C12 C13 . 1.383(3) ? C12 H12 . 0.99(2) ? C13 H13 . 0.99(2) ? O1W H1W1 . 0.85(4) ? O2W H1W2 . 0.89(3) ? 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 _geom_hbond_publ_flag N2 H1N2 O2W 1_555 0.87(2) 2.28(3) 3.011(2) 142(2) yes O1W H1W1 N3 1_555 0.85(4) 2.25(4) 3.088(3) 167(4) yes O2 H1O2 N1 5_545 0.89(3) 1.87(3) 2.759(3) 170(3) yes O2W H1W2 O1 3_666 0.89(3) 1.92(3) 2.807(2) 173(3) yes C7 H7 O1W 3_656 0.99(2) 2.50(2) 3.351(3) 144(2) yes 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_publ_flag C6 N2 N3 C7 177.4(2) yes C5 N1 C1 C2 -0.1(4) ? N1 C1 C2 C3 0.0(4) ? C1 C2 C3 C4 0.0(4) ? C2 C3 C4 C5 0.0(3) ? C2 C3 C4 C6 177.2(2) ? C1 N1 C5 C4 0.1(4) ? C3 C4 C5 N1 0.0(4) ? C6 C4 C5 N1 -177.5(2) ? N3 N2 C6 O1 0.9(3) ? N3 N2 C6 C4 -177.01(18) yes C5 C4 C6 O1 5.6(3) yes C3 C4 C6 O1 -171.7(2) yes C5 C4 C6 N2 -176.5(2) ? C3 C4 C6 N2 6.3(3) ? N2 N3 C7 C8 178.41(19) yes N3 C7 C8 C13 176.0(2) yes N3 C7 C8 C9 -6.4(3) yes C13 C8 C9 C10 1.0(3) ? C7 C8 C9 C10 -176.6(2) ? C8 C9 C10 C11 0.2(4) ? C9 C10 C11 O2 178.6(2) ? C9 C10 C11 C12 -1.2(4) ? O2 C11 C12 C13 -178.9(2) ? C10 C11 C12 C13 0.9(3) ? C11 C12 C13 C8 0.4(4) ? C9 C8 C13 C12 -1.3(3) ? C7 C8 C13 C12 176.4(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105683 2 PubChem 139056516