#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013150.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_2013150 loop_ _publ_author_name 'Shang Shan' 'Duan-Jun Xu' 'Chen-Hsiung Hung' 'Jing-Yun Wu' 'Michael Y. Chiang' _publ_section_title ; Benzaldehyde 2,4-dinitrophenylhydrazone ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o135 _journal_page_last o136 _journal_paper_doi 10.1107/S0108270103002464 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C13 H10 N4 O4' _chemical_formula_moiety 'C13 H10 N4 O4' _chemical_formula_sum 'C13 H10 N4 O4' _chemical_formula_weight 286.25 _chemical_name_systematic ; ? ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 92.596(15) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.290(3) _cell_length_b 6.825(3) _cell_length_c 14.3316(18) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 10.8 _cell_measurement_theta_min 4.9 _cell_volume 1298.6(7) _computing_cell_refinement MSC/AFC _computing_data_collection 'MSC/AFC (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 'SIR-92 (Altomare et al., 1993)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.71069 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2677 _diffrn_reflns_theta_full 26.0 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 2.8 _diffrn_standards_decay_% 0.2 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.18 _refine_diff_density_min -0.16 _refine_ls_extinction_coef 0.016(2) _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 1.002 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2564 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.112 _refine_ls_R_factor_gt 0.040 _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^)+(0.0715P)^2^+0.0073P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.111 _refine_ls_wR_factor_ref 0.141 _reflns_number_gt 1258 _reflns_number_total 2564 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1407.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_sg_symbol_H-M 'P 21/c' _cod_database_code 2013150 _cod_database_fobs_code 2013150 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 O1 1.01944(13) 0.1347(4) 0.25135(15) 0.1147(10) Uani d . 1 . . O O2 1.03126(14) 0.1295(4) 0.39982(15) 0.1215(10) Uani d . 1 . . O O3 0.74168(12) 0.0892(3) 0.57597(9) 0.0638(5) Uani d . 1 . . O O4 0.59199(10) 0.0913(2) 0.51373(10) 0.0560(4) Uani d . 1 . . O N1 0.98211(15) 0.1281(4) 0.32660(17) 0.0754(7) Uani d . 1 . . N N2 0.68439(12) 0.0935(3) 0.50696(10) 0.0409(4) Uani d . 1 . . N N3 0.56126(12) 0.0945(2) 0.33133(11) 0.0405(4) Uani d . 1 . . N H3A 0.5301 0.0856 0.3824 0.049 Uiso calc R 1 . . H N4 0.50861(12) 0.0994(2) 0.24659(11) 0.0415(4) Uani d . 1 . . N C1 0.66282(13) 0.1039(3) 0.33295(13) 0.0368(5) Uani d . 1 . . C C2 0.72528(14) 0.1011(3) 0.41597(12) 0.0363(5) Uani d . 1 . . C C3 0.82919(14) 0.1075(3) 0.41344(14) 0.0440(5) Uani d . 1 . . C H3 0.8688 0.1041 0.4686 0.053 Uiso calc R 1 . . H C4 0.87289(15) 0.1188(3) 0.32939(15) 0.0482(6) Uani d . 1 . . C C5 0.81507(15) 0.1264(3) 0.24646(14) 0.0499(6) Uani d . 1 . . C H5 0.8460 0.1362 0.1897 0.060 Uiso calc R 1 . . H C6 0.71319(15) 0.1193(3) 0.24841(14) 0.0456(5) Uani d . 1 . . C H6 0.6752 0.1247 0.1923 0.055 Uiso calc R 1 . . H C7 0.41286(14) 0.0933(3) 0.24870(13) 0.0403(5) Uani d . 1 . . C H7 0.3826 0.0849 0.3058 0.048 Uiso calc R 1 . . H C8 0.35017(14) 0.0992(3) 0.16234(13) 0.0385(5) Uani d . 1 . . C C9 0.24624(15) 0.1026(3) 0.16693(15) 0.0461(5) Uani d . 1 . . C H9 0.2171 0.0995 0.2247 0.055 Uiso calc R 1 . . H C10 0.18576(17) 0.1104(3) 0.08584(17) 0.0559(6) Uani d . 1 . . C H10 0.1160 0.1125 0.0891 0.067 Uiso calc R 1 . . H C11 0.22892(19) 0.1150(3) 0.00054(17) 0.0591(6) Uani d . 1 . . C H11 0.1882 0.1208 -0.0539 0.071 Uiso calc R 1 . . H C12 0.33218(18) 0.1110(3) -0.00477(15) 0.0540(6) Uani d . 1 . . C H12 0.3609 0.1132 -0.0627 0.065 Uiso calc R 1 . . H C13 0.39282(15) 0.1038(3) 0.07551(14) 0.0452(5) Uani d . 1 . . C H13 0.4625 0.1020 0.0717 0.054 Uiso calc R 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 0.0510(12) 0.211(3) 0.0847(14) -0.0010(15) 0.0302(11) 0.0121(16) O2 0.0442(10) 0.235(3) 0.0837(14) -0.0131(15) -0.0099(10) 0.0204(17) O3 0.0552(9) 0.1038(14) 0.0318(7) -0.0042(10) -0.0064(6) -0.0062(9) O4 0.0403(8) 0.0852(12) 0.0430(8) -0.0009(9) 0.0077(6) -0.0002(8) N1 0.0392(11) 0.117(2) 0.0709(14) -0.0012(12) 0.0078(10) 0.0095(15) N2 0.0443(10) 0.0467(10) 0.0318(8) -0.0002(8) 0.0015(7) -0.0033(8) N3 0.0378(9) 0.0525(11) 0.0310(8) -0.0024(9) 0.0002(6) 0.0025(8) N4 0.0400(9) 0.0468(11) 0.0374(8) -0.0007(9) -0.0028(7) 0.0016(9) C1 0.0365(10) 0.0374(11) 0.0363(10) 0.0000(10) -0.0004(8) 0.0001(10) C2 0.0383(10) 0.0383(11) 0.0325(10) -0.0012(10) 0.0030(8) -0.0003(9) C3 0.0408(11) 0.0507(13) 0.0399(11) -0.0012(11) -0.0042(8) -0.0004(11) C4 0.0350(10) 0.0584(15) 0.0515(12) -0.0007(11) 0.0054(9) 0.0035(12) C5 0.0439(12) 0.0664(16) 0.0401(11) 0.0005(11) 0.0109(9) 0.0034(11) C6 0.0475(12) 0.0572(15) 0.0318(10) -0.0013(11) -0.0012(8) 0.0008(10) C7 0.0396(11) 0.0437(12) 0.0377(10) -0.0013(10) 0.0035(8) 0.0030(10) C8 0.0384(10) 0.0350(11) 0.0417(11) 0.0001(10) -0.0021(8) -0.0001(10) C9 0.0405(11) 0.0482(13) 0.0495(12) 0.0008(11) 0.0008(9) -0.0016(11) C10 0.0414(11) 0.0544(15) 0.0708(16) 0.0027(12) -0.0106(11) -0.0028(13) C11 0.0663(15) 0.0547(15) 0.0539(13) 0.0056(13) -0.0237(11) -0.0007(12) C12 0.0647(15) 0.0546(15) 0.0420(12) -0.0004(13) -0.0042(10) -0.0020(12) C13 0.0412(11) 0.0495(13) 0.0448(11) 0.0010(11) 0.0004(9) 0.0011(11) 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 O1 N1 O2 123.1(2) ? O1 N1 C4 118.5(2) ? O2 N1 C4 118.4(2) ? O3 N2 O4 121.42(16) ? O3 N2 C2 119.25(16) ? O4 N2 C2 119.33(15) ? C1 N3 N4 118.85(15) yes C1 N3 H3A 120.6 ? N4 N3 H3A 120.6 ? C7 N4 N3 116.55(16) yes N3 C1 C6 120.01(17) ? N3 C1 C2 124.04(17) ? C6 C1 C2 115.95(17) ? C3 C2 C1 121.59(17) ? C3 C2 N2 116.36(16) ? C1 C2 N2 122.04(16) ? C4 C3 C2 119.39(18) ? C4 C3 H3 120.3 ? C2 C3 H3 120.3 ? C3 C4 C5 121.19(18) ? C3 C4 N1 119.5(2) ? C5 C4 N1 119.3(2) ? C6 C5 C4 119.73(19) ? C6 C5 H5 120.1 ? C4 C5 H5 120.1 ? C5 C6 C1 122.13(19) ? C5 C6 H6 118.9 ? C1 C6 H6 118.9 ? N4 C7 C8 120.70(18) yes N4 C7 H7 119.7 ? C8 C7 H7 119.7 ? C9 C8 C13 119.31(19) ? C9 C8 C7 119.44(18) ? C13 C8 C7 121.25(18) ? C10 C9 C8 120.2(2) ? C10 C9 H9 119.9 ? C8 C9 H9 119.9 ? C11 C10 C9 119.9(2) ? C11 C10 H10 120.1 ? C9 C10 H10 120.1 ? C10 C11 C12 120.4(2) ? C10 C11 H11 119.8 ? C12 C11 H11 119.8 ? C13 C12 C11 120.1(2) ? C13 C12 H12 119.9 ? C11 C12 H12 119.9 ? C12 C13 C8 120.1(2) ? C12 C13 H13 119.9 ? C8 C13 H13 119.9 ? 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 . 1.208(3) ? O2 N1 . 1.211(3) ? O3 N2 . 1.221(2) ? O4 N2 . 1.236(2) ? N1 C4 . 1.455(3) ? N2 C2 . 1.436(2) ? N3 C1 . 1.350(2) yes N3 N4 . 1.374(2) yes N3 H3A . 0.860 ? N4 C7 . 1.275(2) yes C1 C6 . 1.414(3) yes C1 C2 . 1.420(3) yes C2 C3 . 1.384(3) ? C3 C4 . 1.363(3) ? C3 H3 . 0.930 ? C4 C5 . 1.387(3) ? C5 C6 . 1.356(3) ? C5 H5 . 0.930 ? C6 H6 . 0.930 ? C7 C8 . 1.461(3) yes C7 H7 . 0.930 ? C8 C9 . 1.386(3) ? C8 C13 . 1.391(3) ? C9 C10 . 1.384(3) ? C9 H9 . 0.930 ? C10 C11 . 1.374(4) ? C10 H10 . 0.930 ? C11 C12 . 1.378(3) ? C11 H11 . 0.930 ? C12 C13 . 1.375(3) ? 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 N3 H3A O4 . 0.86 2.02 2.628(2) 127 yes N3 H3A O4 3_656 0.86 2.55 3.331(2) 151 yes C9 H9 O1 1_455 0.93 2.68 3.306(3) 125 yes C10 H10 O1 1_455 0.93 2.71 3.319(3) 124 yes C11 H11 O2 4_465 0.93 2.75 3.418(3) 129 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 N3 N4 C7 -178.93(18) N4 N3 C1 C6 0.2(3) N4 N3 C1 C2 179.70(18) N3 C1 C2 C3 178.80(19) C6 C1 C2 C3 -1.7(3) N3 C1 C2 N2 -1.9(3) C6 C1 C2 N2 177.61(18) O3 N2 C2 C3 -1.4(3) O4 N2 C2 C3 178.61(19) O3 N2 C2 C1 179.25(19) O4 N2 C2 C1 -0.8(3) C1 C2 C3 C4 0.7(3) N2 C2 C3 C4 -178.69(19) C2 C3 C4 C5 0.8(4) C2 C3 C4 N1 179.2(2) O1 N1 C4 C3 178.7(3) O2 N1 C4 C3 -1.5(4) O1 N1 C4 C5 -2.8(4) O2 N1 C4 C5 177.0(3) C3 C4 C5 C6 -1.0(4) N1 C4 C5 C6 -179.5(2) C4 C5 C6 C1 -0.1(4) N3 C1 C6 C5 -179.1(2) C2 C1 C6 C5 1.4(3) N3 N4 C7 C8 179.53(17) N4 C7 C8 C9 -176.7(2) N4 C7 C8 C13 2.6(3) C13 C8 C9 C10 0.0(3) C7 C8 C9 C10 179.3(2) C8 C9 C10 C11 0.0(3) C9 C10 C11 C12 0.3(4) C10 C11 C12 C13 -0.5(4) C11 C12 C13 C8 0.4(4) C9 C8 C13 C12 -0.2(3) C7 C8 C13 C12 -179.5(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 7841082