#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202220.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_2202220 loop_ _publ_author_name 'Shang Shan' 'Duan-Jun Xu' 'Wei-Xiao Hu' _publ_section_title ; Isobutyraldehyde 2,4-dinitrophenylhydrazone ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o838 _journal_page_last o840 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C10 H12 N4 O4' _chemical_formula_moiety 'C10 H12 N4 O4' _chemical_formula_sum 'C10 H12 N4 O4' _chemical_formula_weight 252.24 _chemical_melting_point 459.6(5) _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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.372(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.0514(10) _cell_length_b 7.3862(12) _cell_length_c 23.6459(16) _cell_measurement_reflns_used 6730 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.4 _cell_measurement_theta_min 1.8 _cell_volume 1230.5(3) _computing_cell_refinement PROCESS--AUTO _computing_data_collection 'PROCESS--AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku, 2002)' _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_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _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 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 11248 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.72 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.36 _refine_diff_density_min -0.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2820 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.103 _refine_ls_R_factor_gt 0.067 _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^)+(0.059P)^2^+0.539P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.143 _refine_ls_wR_factor_ref 0.159 _reflns_number_gt 1899 _reflns_number_total 2820 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6159.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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: '_chemical_melting_point' value '186-187 \%C' was changed to '459.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '186-187 \%C' was changed to '459.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. '_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_database_code 2202220 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 0.0950(2) 0.9175(3) 0.45718(7) 0.0621(5) Uani d . 1 . . O O2 0.2090(3) 0.8964(3) 0.37445(7) 0.0790(7) Uani d . 1 . . O O3 0.8037(3) 0.6397(3) 0.34322(8) 0.0821(7) Uani d . 1 . . O O4 0.9771(3) 0.5301(3) 0.41206(8) 0.0728(6) Uani d . 1 . . O N1 0.2230(3) 0.8747(3) 0.42553(8) 0.0495(5) Uani d . 1 . . N N2 0.8348(3) 0.6090(3) 0.39334(9) 0.0568(5) Uani d . 1 . . N N3 0.3009(3) 0.8305(3) 0.54811(7) 0.0463(5) Uani d . 1 . . N H3 0.1907 0.8703 0.5373 0.056 Uiso calc R 1 . . H N4 0.3519(3) 0.8173(3) 0.60526(8) 0.0546(5) Uani d . 1 . . N C1 0.4268(3) 0.7801(3) 0.50982(8) 0.0404(5) Uani d . 1 . . C C2 0.3952(3) 0.7962(3) 0.45034(8) 0.0409(5) Uani d . 1 . . C C3 0.5280(3) 0.7400(3) 0.41259(9) 0.0440(5) Uani d . 1 . . C H3A 0.5036 0.7509 0.3738 0.053 Uiso calc R 1 . . H C4 0.6952(3) 0.6685(3) 0.43314(9) 0.0463(5) Uani d . 1 . . C C5 0.7346(3) 0.6518(3) 0.49129(9) 0.0486(6) Uani d . 1 . . C H5 0.8496 0.6030 0.5046 0.058 Uiso calc R 1 . . H C6 0.6047(3) 0.7071(3) 0.52833(9) 0.0474(5) Uani d . 1 . . C H6 0.6331 0.6969 0.5670 0.057 Uiso calc R 1 . . H C7 0.2288(4) 0.8699(4) 0.63867(10) 0.0636(7) Uani d . 1 . . C H7 0.1126 0.9110 0.6237 0.076 Uiso calc R 1 . . H C8 0.2621(5) 0.8688(5) 0.70176(11) 0.0871(10) Uani d . 1 . . C H8 0.2619 0.9960 0.7135 0.104 Uiso calc R 1 . . H C9 0.0978(7) 0.7834(7) 0.72861(14) 0.1354(18) Uani d . 1 . . C H9A 0.1186 0.7841 0.7690 0.203 Uiso calc R 1 . . H H9B 0.0841 0.6608 0.7156 0.203 Uiso calc R 1 . . H H9C -0.0155 0.8501 0.7186 0.203 Uiso calc R 1 . . H C10 0.4528(6) 0.7967(7) 0.71953(13) 0.1278(17) Uani d . 1 . . C H10A 0.5490 0.8631 0.7008 0.192 Uiso calc R 1 . . H H10B 0.4602 0.6710 0.7095 0.192 Uiso calc R 1 . . H H10C 0.4721 0.8095 0.7598 0.192 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 0.0475(9) 0.0875(14) 0.0515(9) 0.0158(9) 0.0029(8) -0.0060(9) O2 0.0671(12) 0.1269(19) 0.0427(9) 0.0267(12) -0.0032(8) 0.0078(10) O3 0.0791(14) 0.1139(18) 0.0545(11) 0.0270(12) 0.0190(10) 0.0046(11) O4 0.0550(10) 0.0827(14) 0.0813(13) 0.0209(10) 0.0109(9) -0.0031(11) N1 0.0456(10) 0.0580(13) 0.0445(10) 0.0024(9) -0.0022(9) -0.0009(9) N2 0.0532(12) 0.0589(14) 0.0589(12) 0.0048(10) 0.0113(10) -0.0029(10) N3 0.0443(10) 0.0566(12) 0.0381(9) 0.0032(9) 0.0025(8) 0.0012(8) N4 0.0592(12) 0.0647(14) 0.0400(10) 0.0041(10) 0.0031(9) 0.0007(9) C1 0.0441(11) 0.0359(12) 0.0413(10) -0.0072(9) 0.0031(9) 0.0000(9) C2 0.0399(11) 0.0398(12) 0.0429(11) -0.0020(9) 0.0006(9) 0.0009(9) C3 0.0477(12) 0.0431(13) 0.0414(11) -0.0044(10) 0.0032(9) -0.0007(9) C4 0.0452(12) 0.0446(13) 0.0495(12) -0.0006(10) 0.0089(10) 0.0000(10) C5 0.0431(12) 0.0473(14) 0.0553(13) 0.0037(10) -0.0012(10) 0.0036(10) C6 0.0490(12) 0.0508(14) 0.0419(11) -0.0018(11) -0.0029(10) 0.0032(10) C7 0.0700(17) 0.076(2) 0.0448(13) 0.0132(14) 0.0061(12) 0.0041(13) C8 0.105(2) 0.112(3) 0.0452(14) 0.024(2) 0.0097(16) 0.0015(16) C9 0.178(4) 0.162(4) 0.070(2) 0.025(4) 0.058(3) 0.019(2) C10 0.147(4) 0.181(5) 0.0531(18) 0.041(3) -0.023(2) 0.007(2) 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 . 1.238(2) ? O2 N1 . 1.218(2) ? O3 N2 . 1.218(3) ? O4 N2 . 1.227(3) ? N1 C2 . 1.447(3) ? N2 C4 . 1.458(3) ? N3 C1 . 1.346(3) y N3 N4 . 1.387(2) y N3 H3 . 0.860 ? N4 C7 . 1.259(3) y C1 C6 . 1.418(3) y C1 C2 . 1.420(3) y C2 C3 . 1.384(3) y C3 C4 . 1.363(3) y C3 H3A . 0.930 ? C4 C5 . 1.397(3) y C5 C6 . 1.356(3) y C5 H5 . 0.930 ? C6 H6 . 0.930 ? C7 C8 . 1.501(3) y C7 H7 . 0.930 ? C8 C9 . 1.485(5) y C8 C10 . 1.490(5) y C8 H8 . 0.980 ? C9 H9A . 0.960 ? C9 H9B . 0.960 ? C9 H9C . 0.960 ? C10 H10A . 0.960 ? C10 H10B . 0.960 ? C10 H10C . 0.960 ? 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 O2 N1 O1 122.3(2) O2 N1 C2 119.15(19) O1 N1 C2 118.56(17) O3 N2 O4 123.5(2) O3 N2 C4 118.2(2) O4 N2 C4 118.3(2) C1 N3 N4 118.97(18) C1 N3 H3 120.5 N4 N3 H3 120.5 C7 N4 N3 115.6(2) N3 C1 C6 119.80(19) N3 C1 C2 124.22(19) C6 C1 C2 115.97(19) C3 C2 C1 122.1(2) C3 C2 N1 115.93(19) C1 C2 N1 121.96(18) C4 C3 C2 119.0(2) C4 C3 H3A 120.5 C2 C3 H3A 120.5 C3 C4 C5 121.3(2) C3 C4 N2 118.9(2) C5 C4 N2 119.8(2) C6 C5 C4 119.8(2) C6 C5 H5 120.1 C4 C5 H5 120.1 C5 C6 C1 121.9(2) C5 C6 H6 119.1 C1 C6 H6 119.1 N4 C7 C8 122.6(3) N4 C7 H7 118.7 C8 C7 H7 118.7 C9 C8 C10 116.0(3) C9 C8 C7 109.5(3) C10 C8 C7 112.6(3) C9 C8 H8 106.0 C10 C8 H8 106.0 C7 C8 H8 106.0 C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C8 C10 H10A 109.5 C8 C10 H10B 109.5 H10A C10 H10B 109.5 C8 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 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 H3 O1 . 0.86 2.02 2.624(2) 127 yes N3 H3 O1 3_576 0.86 2.56 3.353(3) 154 yes C5 H5 O4 3_766 0.93 2.48 3.283(3) 145 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 178.7(2) N4 N3 C1 C6 2.9(3) N4 N3 C1 C2 -176.6(2) N3 C1 C2 C3 -179.1(2) C6 C1 C2 C3 1.5(3) N3 C1 C2 N1 1.8(3) C6 C1 C2 N1 -177.6(2) O2 N1 C2 C3 -4.1(3) O1 N1 C2 C3 175.9(2) O2 N1 C2 C1 175.0(2) O1 N1 C2 C1 -5.0(3) C1 C2 C3 C4 -0.6(3) N1 C2 C3 C4 178.6(2) C2 C3 C4 C5 -0.3(3) C2 C3 C4 N2 179.9(2) O3 N2 C4 C3 6.2(3) O4 N2 C4 C3 -173.5(2) O3 N2 C4 C5 -173.7(2) O4 N2 C4 C5 6.6(3) C3 C4 C5 C6 0.1(4) N2 C4 C5 C6 -180.0(2) C4 C5 C6 C1 0.9(4) N3 C1 C6 C5 178.9(2) C2 C1 C6 C5 -1.6(3) N3 N4 C7 C8 -178.6(3) N4 C7 C8 C9 -131.7(3) N4 C7 C8 C10 -1.0(5)