#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202147.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_2202147 loop_ _publ_author_name 'Shang Shan' 'Duan-Jun Xu' 'Jing-Yun Wu' 'Michael Y. Chiang' _publ_section_title ; Salicylaldehyde 4-nitrophenylhydrazone ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o342 _journal_page_last o343 _journal_paper_doi 10.1107/S1600536803003350 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C13 H11 N3 O3' _chemical_formula_moiety 'C13 H11 N3 O3' _chemical_formula_sum 'C13 H11 N3 O3' _chemical_formula_weight 257.25 _chemical_name_systematic ? _space_group_IT_number 7 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.199(15) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.0052(11) _cell_length_b 9.9004(16) _cell_length_c 12.1749(12) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12.2 _cell_measurement_theta_min 8.6 _cell_volume 602.86(17) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1985)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Rigaku AFC-7S' _diffrn_measurement_method \w/2\q _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 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 1328 _diffrn_reflns_theta_full 26.0 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.06 _diffrn_standards_decay_% 1.9 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.13 _refine_diff_density_min -0.15 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 1190 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.073 _refine_ls_R_factor_gt 0.032 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.0138P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.076 _refine_ls_wR_factor_ref 0.091 _reflns_number_gt 774 _reflns_number_total 1190 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6130.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P c' _cod_database_code 2202147 _cod_database_fobs_code 2202147 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, 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 1.1219(6) 0.0500(3) 0.5900(2) 0.0774(8) Uani d . 1 . . O O2 1.1702(6) -0.1120(3) 0.4758(3) 0.0880(10) Uani d . 1 . . O O3 -0.0249(5) 0.5120(2) 0.3978(2) 0.0635(7) Uani d . 1 . . O N1 1.0663(6) -0.0053(3) 0.5016(3) 0.0576(8) Uani d . 1 . . N N2 0.2966(5) 0.2283(3) 0.2189(2) 0.0479(7) Uani d . 1 . . N H1 0.2781 0.1981 0.1528 0.057 Uiso calc R 1 . . H N3 0.1378(5) 0.3308(2) 0.2531(2) 0.0446(6) Uani d . 1 . . N C1 0.4849(6) 0.1739(3) 0.2897(3) 0.0417(7) Uani d . 1 . . C C2 0.6294(7) 0.0607(3) 0.2557(3) 0.0515(8) Uani d . 1 . . C H2 0.5952 0.0251 0.1859 0.062 Uiso calc R 1 . . H C3 0.8191(6) 0.0024(3) 0.3237(3) 0.0529(9) Uani d . 1 . . C H3 0.9124 -0.0730 0.3006 0.063 Uiso calc R 1 . . H C4 0.8723(7) 0.0565(3) 0.4277(3) 0.0454(7) Uani d . 1 . . C C5 0.7345(6) 0.1688(4) 0.4615(3) 0.0509(8) Uani d . 1 . . C H5 0.7724 0.2051 0.5308 0.061 Uiso calc R 1 . . H C6 0.5424(6) 0.2272(3) 0.3939(3) 0.0481(8) Uani d . 1 . . C H6 0.4500 0.3027 0.4176 0.058 Uiso calc R 1 . . H C7 -0.0384(6) 0.3772(3) 0.1848(3) 0.0475(8) Uani d . 1 . . C H7 -0.0531 0.3402 0.1146 0.057 Uiso calc R 1 . . H C8 -0.2189(6) 0.4873(3) 0.2140(3) 0.0464(8) Uani d . 1 . . C C9 -0.2040(6) 0.5500(3) 0.3169(3) 0.0505(8) Uani d . 1 . . C C10 -0.3793(8) 0.6534(4) 0.3392(4) 0.0656(11) Uani d . 1 . . C H10 -0.3685 0.6961 0.4072 0.079 Uiso calc R 1 . . H C11 -0.5690(7) 0.6935(4) 0.2618(4) 0.0690(11) Uani d . 1 . . C H11 -0.6864 0.7627 0.2784 0.083 Uiso calc R 1 . . H C12 -0.5887(7) 0.6337(4) 0.1604(3) 0.0619(10) Uani d . 1 . . C H12 -0.7185 0.6617 0.1086 0.074 Uiso calc R 1 . . H C13 -0.4131(7) 0.5312(3) 0.1361(3) 0.0555(9) Uani d . 1 . . C H13 -0.4241 0.4908 0.0672 0.067 Uiso calc R 1 . . H H9 0.0943 0.4491 0.3658 0.080 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 0.0806(18) 0.100(2) 0.0505(15) 0.0174(17) -0.0127(13) 0.0054(15) O2 0.097(2) 0.0724(18) 0.093(2) 0.0349(18) -0.0158(17) -0.0003(16) O3 0.0676(15) 0.0649(14) 0.0577(13) 0.0085(14) -0.0021(12) -0.0073(13) N1 0.0542(18) 0.0573(19) 0.0612(19) 0.0059(16) 0.0000(16) 0.0135(16) N2 0.0473(14) 0.0471(16) 0.0486(16) 0.0079(14) -0.0065(13) -0.0080(13) N3 0.0436(13) 0.0392(14) 0.0509(14) 0.0009(13) 0.0011(12) 0.0017(12) C1 0.0376(16) 0.0391(16) 0.0485(17) -0.0040(14) 0.0041(14) -0.0024(14) C2 0.0492(18) 0.0512(18) 0.054(2) 0.0034(18) -0.0056(15) -0.0148(17) C3 0.0493(19) 0.0416(17) 0.068(2) 0.0077(16) -0.0002(18) -0.0060(16) C4 0.0427(16) 0.0443(17) 0.0493(17) 0.0020(15) 0.0016(13) 0.0075(16) C5 0.056(2) 0.053(2) 0.0436(18) 0.0015(17) -0.0015(16) -0.0027(16) C6 0.0518(19) 0.0449(17) 0.0473(19) 0.0035(16) -0.0005(16) -0.0034(16) C7 0.0455(17) 0.0481(18) 0.0491(18) -0.0008(17) 0.0037(16) 0.0010(16) C8 0.0416(16) 0.0447(18) 0.0535(18) 0.0000(14) 0.0092(15) 0.0102(15) C9 0.052(2) 0.0454(19) 0.054(2) -0.0012(17) 0.0081(17) 0.0060(17) C10 0.073(3) 0.0493(19) 0.075(2) 0.006(2) 0.016(2) -0.0067(19) C11 0.063(2) 0.056(2) 0.090(3) 0.020(2) 0.025(2) 0.015(2) C12 0.051(2) 0.063(2) 0.072(2) 0.0120(19) 0.0103(18) 0.027(2) C13 0.053(2) 0.057(2) 0.056(2) 0.0059(19) 0.0060(17) 0.0123(18) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 C9 O3 H9 106.8 ? O2 N1 O1 121.7(3) ? O2 N1 C4 119.4(3) ? O1 N1 C4 118.9(3) ? C1 N2 N3 119.9(3) yes C1 N2 H1 120.1 ? N3 N2 H1 120.1 ? C7 N3 N2 117.7(3) yes N2 C1 C6 122.6(3) ? N2 C1 C2 118.7(3) ? C6 C1 C2 118.7(3) ? C3 C2 C1 120.9(3) ? C3 C2 H2 119.6 ? C1 C2 H2 119.6 ? C2 C3 C4 119.6(3) ? C2 C3 H3 120.2 ? C4 C3 H3 120.2 ? C5 C4 C3 120.1(3) ? C5 C4 N1 119.4(3) ? C3 C4 N1 120.5(3) ? C6 C5 C4 120.6(3) ? C6 C5 H5 119.7 ? C4 C5 H5 119.7 ? C5 C6 C1 120.1(3) ? C5 C6 H6 119.9 ? C1 C6 H6 119.9 ? N3 C7 C8 121.8(3) ? N3 C7 H7 119.1 ? C8 C7 H7 119.1 ? C9 C8 C13 118.7(3) ? C9 C8 C7 122.3(3) ? C13 C8 C7 118.9(3) ? O3 C9 C10 118.0(3) ? O3 C9 C8 122.5(3) ? C10 C9 C8 119.5(3) ? C11 C10 C9 120.6(4) ? C11 C10 H10 119.7 ? C9 C10 H10 119.7 ? C12 C11 C10 121.2(4) ? C12 C11 H11 119.4 ? C10 C11 H11 119.4 ? C11 C12 C13 119.1(4) ? C11 C12 H12 120.5 ? C13 C12 H12 120.5 ? C12 C13 C8 120.9(4) ? C12 C13 H13 119.6 ? C8 C13 H13 119.6 ? 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 N1 . 1.229(4) yes O2 N1 . 1.224(4) yes O3 C9 . 1.359(4) yes O3 H9 . 0.956 ? N1 C4 . 1.436(4) yes N2 C1 . 1.364(4) yes N2 N3 . 1.364(3) yes N2 H1 . 0.860 ? N3 C7 . 1.274(4) yes C1 C6 . 1.394(4) ? C1 C2 . 1.404(5) ? C2 C3 . 1.364(5) ? C2 H2 . 0.930 ? C3 C4 . 1.391(5) ? C3 H3 . 0.930 ? C4 C5 . 1.379(5) ? C5 C6 . 1.370(5) ? C5 H5 . 0.930 ? C6 H6 . 0.930 ? C7 C8 . 1.468(4) yes C7 H7 . 0.930 ? C8 C9 . 1.398(4) ? C8 C13 . 1.401(5) ? C9 C10 . 1.382(5) ? C10 C11 . 1.371(5) ? C10 H10 . 0.930 ? C11 C12 . 1.368(6) ? C11 H11 . 0.930 ? C12 C13 . 1.382(5) ? C12 H12 . 0.930 ? C13 H13 . 0.930 ? 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 O3 H9 N3 . 0.956 1.823 2.664(3) 145 yes N2 H1 O2 2_454 0.860 2.360 3.215(4) 173 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 C1 N2 N3 C7 -178.8(3) N3 N2 C1 C6 -6.6(4) N3 N2 C1 C2 174.4(3) N2 C1 C2 C3 -179.8(3) C6 C1 C2 C3 1.1(5) C1 C2 C3 C4 -0.7(5) C2 C3 C4 C5 -0.3(5) C2 C3 C4 N1 178.4(3) O2 N1 C4 C5 173.1(3) O1 N1 C4 C5 -6.2(5) O2 N1 C4 C3 -5.5(5) O1 N1 C4 C3 175.1(3) C3 C4 C5 C6 0.7(5) N1 C4 C5 C6 -177.9(3) C4 C5 C6 C1 -0.3(5) N2 C1 C6 C5 -179.7(3) C2 C1 C6 C5 -0.7(4) N2 N3 C7 C8 179.9(2) N3 C7 C8 C9 1.7(4) N3 C7 C8 C13 -178.3(3) C13 C8 C9 O3 178.8(3) C7 C8 C9 O3 -1.2(5) C13 C8 C9 C10 -0.2(4) C7 C8 C9 C10 179.8(3) O3 C9 C10 C11 -178.3(3) C8 C9 C10 C11 0.8(5) C9 C10 C11 C12 -0.6(6) C10 C11 C12 C13 -0.2(5) C11 C12 C13 C8 0.7(5) C9 C8 C13 C12 -0.5(5) C7 C8 C13 C12 179.4(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 12549131