#------------------------------------------------------------------------------ #$Date: 2011-03-05 23:31:02 +0200 (Sat, 05 Mar 2011) $ #$Revision: 12744 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/8102005.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8102005 loop_ _publ_author_name 'X.-S. Tai' 'F.-Y. Kong' _publ_section_title ; Crystal structure of 2'-hydroxyacetophenone nicotinoyl- hydrazone monohydrate, C14H15N3O3 · H2O ; _journal_issue 3 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 341 _journal_volume 221 _journal_year 2006 _chemical_formula_structural 'C14H15N3O3 · H2O' _chemical_formula_sum 'C14 H15 N3 O3' _chemical_formula_weight 273.29 _chemical_name_systematic ; 2'-hydroxyacetophenone nicotinoylhydrazone monohydrate ; _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 SHELXL-97 _cell_angle_alpha 81.28(3) _cell_angle_beta 86.26(3) _cell_angle_gamma 70.48(3) _cell_formula_units_Z 2 _cell_length_a 8.6795(17) _cell_length_b 8.8771(18) _cell_length_c 9.2728(19) _cell_measurement_reflns_used 389 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 25.1 _cell_measurement_theta_min 2 _cell_volume 665.5(3) _computing_cell_refinement raxis _computing_data_collection raxis _computing_data_reduction raxis _computing_molecular_graphics texsan _computing_publication_material texsan _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 291(2) _diffrn_detector_area_resol_mean 0 _diffrn_measured_fraction_theta_full 0.828 _diffrn_measured_fraction_theta_max 0.828 _diffrn_measurement_device_type 'Rigaku R-AXIS IV' _diffrn_measurement_method omega _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 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 1937 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.22 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_correction_T_min 0.9806 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.265 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.055 _refine_ls_extinction_coef 0.046(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 1937 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0642 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1027P)^2^+0.1228P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1625 _refine_ls_wR_factor_ref 0.1769 _reflns_number_gt 1420 _reflns_number_total 1937 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file 1267-1820.cff _[local]_cod_data_source_block p-1 _[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_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_original_cell_volume 665.5(2) _cod_database_code 8102005 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_Wyckoff_symbol _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5665(3) 0.7665(3) 0.5528(3) 0.0514(7) Uani 1 2 i d . . . N2 N 0.5104(3) 0.7310(3) 0.4293(3) 0.0526(7) Uani 1 2 i d . . . H2E H 0.582(4) 0.687(4) 0.359(3) 0.059(9) Uiso 1 2 i d . . . N3 N 0.1055(3) 0.5624(3) 0.2302(3) 0.0609(7) Uani 1 2 i d . . . O1 O 0.5124(3) 0.8071(4) 0.8202(3) 0.0764(8) Uani 1 2 i d . . . O2 O 0.2787(3) 0.7294(3) 0.5547(2) 0.0650(7) Uani 1 2 i d . . . O3 O 0.2203(3) 0.4627(3) -0.2600(3) 0.0659(7) Uiso 1 2 i d . . . C1 C 0.6527(4) 0.8427(4) 0.8082(3) 0.0558(8) Uani 1 2 i d . . . C2 C 0.7122(5) 0.8682(5) 0.9352(4) 0.0720(10) Uani 1 2 i d . . . H2A H 0.6527 0.8647 1.0220 0.086 Uiso 1 2 i calc R . . C3 C 0.8565(5) 0.8985(5) 0.9341(4) 0.0771(11) Uani 1 2 i d . . . H3A H 0.8943 0.9153 1.0198 0.093 Uiso 1 2 i calc R . . C4 C 0.9457(5) 0.9040(5) 0.8071(4) 0.0759(11) Uani 1 2 i d . . . H4A H 1.0451 0.9225 0.8071 0.091 Uiso 1 2 i calc R . . C5 C 0.8885(4) 0.8823(4) 0.6799(4) 0.0619(9) Uani 1 2 i d . . . H5A H 0.9496 0.8875 0.5942 0.074 Uiso 1 2 i calc R . . C6 C 0.7401(4) 0.8527(3) 0.6763(3) 0.0492(7) Uani 1 2 i d . . . C7 C 0.6832(3) 0.8257(3) 0.5385(3) 0.0473(7) Uani 1 2 i d . . . C8 C 0.7591(4) 0.8705(4) 0.3961(3) 0.0604(9) Uani 1 2 i d . . . H8A H 0.7081 0.8459 0.3180 0.091 Uiso 1 2 i calc R . . H8B H 0.8739 0.8103 0.3962 0.091 Uiso 1 2 i calc R . . H8C H 0.7440 0.9838 0.3827 0.091 Uiso 1 2 i calc R . . C9 C 0.3643(4) 0.7061(3) 0.4437(3) 0.0513(8) Uani 1 2 i d . . . C10 C 0.1737(4) 0.6034(4) 0.3358(3) 0.0559(8) Uani 1 2 i d . . . H10A H 0.1292 0.5952 0.4295 0.067 Uiso 1 2 i calc R . . C11 C 0.3078(3) 0.6578(3) 0.3148(3) 0.0495(7) Uani 1 2 i d . . . C12 C 0.3732(4) 0.6682(4) 0.1751(4) 0.0639(9) Uani 1 2 i d . . . H12A H 0.4624 0.7043 0.1553 0.077 Uiso 1 2 i calc R . . C13 C 0.3045(4) 0.6245(5) 0.0664(4) 0.0699(10) Uani 1 2 i d . . . H13A H 0.3470 0.6302 -0.0281 0.084 Uiso 1 2 i calc R . . C14 C 0.1732(4) 0.5724(4) 0.0976(4) 0.0634(9) Uani 1 2 i d . . . H14A H 0.1288 0.5425 0.0224 0.076 Uiso 1 2 i calc R . . H1E H 0.501(5) 0.782(5) 0.729(5) 0.112(16) Uiso 1 2 i d . . . H3F H 0.088(8) 0.472(8) -0.257(6) 0.19(2) Uiso 1 2 i d . . . H3E H 0.200(5) 0.555(5) -0.306(4) 0.085(12) Uiso 1 2 i 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 N1 0.0438(14) 0.0570(16) 0.0558(14) -0.0081(12) 0.0000(11) -0.0196(12) N2 0.0413(15) 0.0614(17) 0.0580(16) -0.0142(13) 0.0060(12) -0.0193(13) N3 0.0464(15) 0.0652(18) 0.0758(18) -0.0082(14) 0.0001(13) -0.0254(14) O1 0.0641(16) 0.113(2) 0.0597(15) -0.0068(14) 0.0099(12) -0.0440(15) O2 0.0586(14) 0.0785(16) 0.0688(14) -0.0228(12) 0.0184(11) -0.0352(13) C1 0.0500(18) 0.0564(19) 0.0595(19) -0.0015(15) 0.0005(14) -0.0188(16) C2 0.079(3) 0.082(3) 0.055(2) -0.0033(18) 0.0016(17) -0.030(2) C3 0.091(3) 0.089(3) 0.065(2) -0.010(2) -0.015(2) -0.045(2) C4 0.065(2) 0.090(3) 0.084(2) -0.013(2) -0.007(2) -0.040(2) C5 0.056(2) 0.066(2) 0.069(2) -0.0097(17) 0.0051(16) -0.0278(17) C6 0.0481(18) 0.0432(16) 0.0557(17) -0.0059(14) 0.0037(14) -0.0156(14) C7 0.0409(16) 0.0421(16) 0.0585(17) -0.0070(13) 0.0082(13) -0.0144(13) C8 0.062(2) 0.064(2) 0.0631(18) -0.0154(16) 0.0122(15) -0.0302(18) C9 0.0413(17) 0.0503(18) 0.0630(19) -0.0073(15) 0.0051(14) -0.0176(14) C10 0.0441(18) 0.061(2) 0.0646(19) -0.0066(16) 0.0039(15) -0.0222(16) C11 0.0407(16) 0.0467(17) 0.0607(18) -0.0083(14) 0.0054(13) -0.0146(13) C12 0.0527(19) 0.080(2) 0.067(2) -0.0156(18) 0.0101(16) -0.0321(18) C13 0.059(2) 0.094(3) 0.062(2) -0.0193(19) 0.0079(16) -0.029(2) C14 0.0510(19) 0.068(2) 0.073(2) -0.0160(18) -0.0011(17) -0.0201(17) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 N2 118.8(3) . . ? C9 N2 N1 116.1(2) . . ? C9 N2 H2E 119.1(19) . . ? N1 N2 H2E 120.2(19) . . ? C10 N3 C14 116.8(3) . . ? C1 O1 H1E 104(3) . . ? H3F O3 H3E 92(4) . . ? O1 C1 C2 117.2(3) . . ? O1 C1 C6 123.4(3) . . ? C2 C1 C6 119.5(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C6 C1 117.7(3) . . ? C5 C6 C7 120.4(3) . . ? C1 C6 C7 121.8(3) . . ? N1 C7 C6 115.1(3) . . ? N1 C7 C8 124.9(3) . . ? C6 C7 C8 120.0(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 N2 121.8(3) . . ? O2 C9 C11 121.6(3) . . ? N2 C9 C11 116.5(3) . . ? N3 C10 C11 124.0(3) . . ? N3 C10 H10A 118.0 . . ? C11 C10 H10A 118.0 . . ? C12 C11 C10 117.2(3) . . ? C12 C11 C9 125.6(3) . . ? C10 C11 C9 117.1(3) . . ? C13 C12 C11 118.9(3) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C14 C13 C12 119.7(3) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? N3 C14 C13 123.3(3) . . ? N3 C14 H14A 118.3 . . ? C13 C14 H14A 118.3 . . ? 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 N1 C7 1.280(4) . ? N1 N2 1.390(3) . ? N2 C9 1.354(4) . ? N2 H2E 0.91(3) . ? N3 C10 1.331(4) . ? N3 C14 1.331(4) . ? O1 C1 1.350(4) . ? O1 H1E 0.93(4) . ? O2 C9 1.231(3) . ? O3 H3F 1.12(7) . ? O3 H3E 0.83(4) . ? C1 C2 1.394(4) . ? C1 C6 1.404(4) . ? C2 C3 1.364(5) . ? C2 H2A 0.9300 . ? C3 C4 1.370(5) . ? C3 H3A 0.9300 . ? C4 C5 1.373(4) . ? C4 H4A 0.9300 . ? C5 C6 1.401(4) . ? C5 H5A 0.9300 . ? C6 C7 1.479(4) . ? C7 C8 1.496(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C11 1.492(4) . ? C10 C11 1.395(4) . ? C10 H10A 0.9300 . ? C11 C12 1.382(4) . ? C12 C13 1.369(4) . ? C12 H12A 0.9300 . ? C13 C14 1.366(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? 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 N2 H2E O3 0.91(3) 2.05(3) 2.922(4) 161(3) 2_665 O3 H3F N3 1.12(7) 1.80(7) 2.902(4) 166(5) 2_565 O3 H3E O2 0.83(4) 2.13(4) 2.876(4) 150(4) 1_554 O1 H1E N1 0.93(4) 1.70(5) 2.551(3) 150(4) . 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 C7 N1 N2 C9 -164.7(3) . . . . ? O1 C1 C2 C3 177.4(3) . . . . ? C6 C1 C2 C3 -1.8(5) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 C5 1.3(6) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C4 C5 C6 C1 -1.2(5) . . . . ? C4 C5 C6 C7 -178.5(3) . . . . ? O1 C1 C6 C5 -176.7(3) . . . . ? C2 C1 C6 C5 2.4(5) . . . . ? O1 C1 C6 C7 0.5(5) . . . . ? C2 C1 C6 C7 179.6(3) . . . . ? N2 N1 C7 C6 -177.3(2) . . . . ? N2 N1 C7 C8 4.1(4) . . . . ? C5 C6 C7 N1 165.8(3) . . . . ? C1 C6 C7 N1 -11.4(4) . . . . ? C5 C6 C7 C8 -15.6(4) . . . . ? C1 C6 C7 C8 167.3(3) . . . . ? N1 N2 C9 O2 7.0(4) . . . . ? N1 N2 C9 C11 -176.3(2) . . . . ? C14 N3 C10 C11 1.2(5) . . . . ? N3 C10 C11 C12 -0.4(5) . . . . ? N3 C10 C11 C9 177.2(3) . . . . ? O2 C9 C11 C12 162.7(3) . . . . ? N2 C9 C11 C12 -14.0(5) . . . . ? O2 C9 C11 C10 -14.7(4) . . . . ? N2 C9 C11 C10 168.6(3) . . . . ? C10 C11 C12 C13 -0.3(5) . . . . ? C9 C11 C12 C13 -177.7(3) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? C10 N3 C14 C13 -1.2(5) . . . . ? C12 C13 C14 N3 0.5(6) . . . . ?