#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008593.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_2008593 loop_ _publ_author_name 'S.Shanmuga Sundara Raj' 'Hoong-Kun Fun' 'Zhong-Lin Lu' 'Wen Xiao' 'Ye-Xiang Tong' 'Bei-Sheng Kang' _publ_section_title ; p-Methoxybenzaldehyde isonicotinoylhydrazone monohydrate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 942 _journal_page_last 944 _journal_paper_doi 10.1107/S0108270199002486 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C14 H13 N3 O2, H2 O' _chemical_formula_sum 'C14 H15 N3 O3' _chemical_formula_weight 273.29 _chemical_name_systematic ; p-Methoxybenzaldehyde Isonicotinoyl Hydrazone Monohydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 96.7270(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3875(2) _cell_length_b 12.4718(3) _cell_length_c 14.8382(4) _cell_measurement_reflns_used 6564 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.24 _cell_measurement_theta_min 2.76 _cell_volume 1357.71(6) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _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, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.970 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scan' _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 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12180 _diffrn_reflns_theta_full 33.09 _diffrn_reflns_theta_max 33.09 _diffrn_reflns_theta_min 2.76 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.313 _refine_diff_density_min -0.169 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 5003 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0485 _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^)+(0.0683P)^2^+0.1724P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1413 _reflns_number_gt 3596 _reflns_number_total 5003 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1409.cif _cod_data_source_block lg009m _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008593 _cod_database_fobs_code 2008593 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' 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 N1 .70214(14) .03891(8) .59693(6) .0342(2) Uani d . 1 . . N N2 .66633(14) -.01324(8) .67581(6) .0328(2) Uani d . 1 . . N N3 .63532(18) -.14163(11) .99441(7) .0517(3) Uani d . 1 . . N O1 .92922(13) .09076(7) .19091(5) .0433(2) Uani d . 1 . . O O2 .64948(16) .14341(7) .75398(6) .0500(3) Uani d . 1 . . O C1 .9782(2) .19821(12) .16978(10) .0476(3) Uani d . 1 . . C C2 .88233(15) .07066(9) .27590(7) .0320(2) Uani d . 1 . . C C3 .83699(18) -.03502(10) .29195(8) .0384(3) Uani d . 1 . . C C4 .78607(18) -.06398(9) .37545(8) .0381(2) Uani d . 1 . . C C5 .77676(14) .01178(9) .44435(7) .0308(2) Uani d . 1 . . C C6 .82191(18) .11763(9) .42693(7) .0375(2) Uani d . 1 . . C C7 .87548(18) .14785(9) .34352(7) .0379(2) Uani d . 1 . . C C8 .72587(16) -.02504(9) .53175(7) .0341(2) Uani d . 1 . . C C9 .64831(16) .04478(9) .75097(7) .0333(2) Uani d . 1 . . C C10 .63494(16) -.02158(9) .83496(7) .0323(2) Uani d . 1 . . C C11 .53860(16) -.11701(9) .83567(7) .0349(2) Uani d . 1 . . C C12 .5417(2) -.17403(11) .91635(9) .0433(3) Uani d . 1 . . C C13 .7245(2) -.04824(13) .99378(8) .0524(3) Uani d . 1 . . C C14 .7274(2) .01470(12) .91687(8) .0450(3) Uani d . 1 . . C O1W .62884(18) -.25227(8) 1.15972(7) .0527(3) Uani d . 1 . . O H1A 1.011(3) .1935(15) .1073(13) .065(5) Uiso d . 1 . . H H1B 1.087(3) .2228(16) .2113(13) .069(5) Uiso d . 1 . . H H1C .880(3) .2499(14) .1751(12) .063(5) Uiso d . 1 . . H H3 .839(2) -.0875(15) .2448(11) .058(5) Uiso d . 1 . . H H4 .756(3) -.1393(16) .3873(12) .062(5) Uiso d . 1 . . H H6 .812(2) .1717(13) .4731(11) .053(4) Uiso d . 1 . . H H7 .903(2) .2219(15) .3306(11) .055(4) Uiso d . 1 . . H H8 .711(2) -.1014(14) .5395(11) .047(4) Uiso d . 1 . . H H11 .470(2) -.1455(12) .7830(10) .045(4) Uiso d . 1 . . H H12 .476(3) -.2422(15) .9163(12) .061(5) Uiso d . 1 . . H H13 .791(3) -.0250(14) 1.0515(13) .066(5) Uiso d . 1 . . H H14 .801(2) .0817(16) .9190(11) .061(5) Uiso d . 1 . . H H1N2 .661(2) -.0867(15) .6768(10) .050(4) Uiso d . 1 . . H H1W1 .632(3) -.2168(18) 1.1068(15) .078(6) Uiso d . 1 . . H H2W1 .541(3) -.2193(18) 1.1842(15) .082(7) 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 .0406(5) .0367(5) .0263(4) .0010(4) .0076(3) .0054(3) N2 .0442(5) .0302(4) .0250(4) .0012(4) .0084(3) .0023(3) N3 .0648(8) .0602(7) .0320(5) .0146(6) .0136(5) .0106(5) O1 .0606(6) .0427(5) .0292(4) -.0025(4) .0155(4) .0030(3) O2 .0781(7) .0306(4) .0448(5) -.0044(4) .0217(5) -.0024(3) C1 .0593(8) .0453(7) .0412(6) .0027(6) .0182(6) .0118(5) C2 .0348(5) .0359(5) .0259(4) .0017(4) .0060(4) .0019(4) C3 .0528(7) .0339(5) .0302(5) -.0025(5) .0116(5) -.0042(4) C4 .0511(7) .0301(5) .0346(5) -.0038(5) .0115(5) -.0004(4) C5 .0329(5) .0342(5) .0256(4) .0016(4) .0053(4) .0027(4) C6 .0522(7) .0328(5) .0282(5) .0007(5) .0081(4) -.0018(4) C7 .0546(7) .0295(5) .0307(5) -.0010(5) .0093(5) .0022(4) C8 .0393(6) .0355(6) .0281(4) .0001(4) .0067(4) .0031(4) C9 .0383(5) .0330(5) .0297(5) .0003(4) .0094(4) .0001(4) C10 .0374(5) .0344(5) .0264(4) .0031(4) .0086(4) -.0015(4) C11 .0398(6) .0356(5) .0306(5) .0021(4) .0089(4) .0004(4) C12 .0516(7) .0409(6) .0402(6) .0062(5) .0167(5) .0082(5) C13 .0641(9) .0657(9) .0267(5) .0072(7) .0024(5) -.0021(5) C14 .0536(8) .0500(7) .0316(5) -.0036(6) .0052(5) -.0073(5) O1W .0818(8) .0391(5) .0403(5) .0098(5) .0196(5) .0075(4) 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 C8 N1 N2 113.59(9) y C9 N2 N1 119.45(9) y C13 N3 C12 117.43(11) ? C2 O1 C1 118.06(10) ? O1 C2 C3 115.10(10) ? O1 C2 C7 124.76(10) ? C3 C2 C7 120.14(10) ? C4 C3 C2 119.86(10) ? C3 C4 C5 121.29(11) ? C6 C5 C4 118.08(10) ? C6 C5 C8 123.56(10) ? C4 C5 C8 118.33(10) ? C5 C6 C7 121.31(10) ? C6 C7 C2 119.30(11) ? N1 C8 C5 123.01(10) ? O2 C9 N2 124.41(10) y O2 C9 C10 121.27(10) y N2 C9 C10 114.27(9) y C11 C10 C14 118.03(11) ? C11 C10 C9 124.06(10) ? C14 C10 C9 117.91(11) ? C10 C11 C12 119.24(11) ? N3 C12 C11 123.03(13) ? N3 C13 C14 123.58(13) ? C13 C14 C10 118.63(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 N1 C8 . 1.281(2) y N1 N2 . 1.3910(10) y N2 C9 . 1.3490(10) y N3 C13 . 1.339(2) ? N3 C12 . 1.3399(19) ? O1 C2 . 1.3700(10) y O1 C1 . 1.432(2) y O2 C9 . 1.2310(10) y C2 C3 . 1.3874(16) ? C2 C7 . 1.3957(15) ? C3 C4 . 1.3842(16) ? C4 C5 . 1.3997(15) ? C5 C6 . 1.3932(16) ? C5 C8 . 1.4660(10) y C6 C7 . 1.3947(15) ? C9 C10 . 1.509(2) y C10 C11 . 1.3874(16) ? C10 C14 . 1.3978(16) ? C11 C12 . 1.3902(16) ? C13 C14 . 1.3873(19) ? 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 O1W H1W1 N3 1_555 0.90(2) 1.92(2) 2.820(2) 179(2) yes N2 H1N2 O1W 4_555 0.92(2) 2.04(2) 2.9450(10) 171.0(10) yes O1W H2W1 O2 3_657 0.88(2) 2.00(2) 2.886(2) 177(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 C8 N1 N2 C9 176.50(10) y C1 O1 C2 C3 -179.81(12) ? C1 O1 C2 C7 1.19(18) ? O1 C2 C3 C4 -179.49(11) ? C7 C2 C3 C4 -0.44(19) ? C2 C3 C4 C5 0.9(2) ? C3 C4 C5 C6 -0.56(18) ? C3 C4 C5 C8 -178.62(12) ? C4 C5 C6 C7 -0.18(19) ? C8 C5 C6 C7 177.77(12) ? C5 C6 C7 C2 0.6(2) ? O1 C2 C7 C6 178.67(12) ? C3 C2 C7 C6 -0.29(19) ? N2 N1 C8 C5 -175.90(10) y C6 C5 C8 N1 6.70(18) ? C4 C5 C8 N1 -175.35(12) ? N1 N2 C9 O2 5.0(2) y N1 N2 C9 C10 -172.20(10) y O2 C9 C10 C11 143.30(13) ? N2 C9 C10 C11 -39.40(16) ? O2 C9 C10 C14 -37.58(17) ? N2 C9 C10 C14 139.72(12) ? C14 C10 C11 C12 -1.83(17) ? C9 C10 C11 C12 177.29(11) ? C13 N3 C12 C11 2.0(2) ? C10 C11 C12 N3 -0.51(19) ? C12 N3 C13 C14 -1.2(2) ? N3 C13 C14 C10 -1.1(2) ? C11 C10 C14 C13 2.56(19) ? C9 C10 C14 C13 -176.62(12) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21180248 2 PubChem 139056626