#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015387.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_2015387 loop_ _publ_author_name 'Wardell, James L.' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; 2,4-Dinitrophenylhydrazine, redetermined at 120K: a three-dimensional framework built from N---H···O, N---H···(O)~2~, N---H···\p(arene) and C---H···O hydrogen bonds ; _journal_coeditor_code SK3017 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o318 _journal_page_last o320 _journal_paper_doi 10.1107/S0108270106013114 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C6 H6 N4 O4' _chemical_formula_moiety 'C6 H6 N4 O4' _chemical_formula_sum 'C6 H6 N4 O4' _chemical_formula_weight 198.15 _chemical_name_systematic ; 2,4-Dinitrophenylhydrazine ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 98.372(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.7917(2) _cell_length_b 11.5905(6) _cell_length_c 14.0496(5) _cell_measurement_reflns_used 1775 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.56 _cell_measurement_theta_min 2.93 _cell_volume 771.97(6) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker Nonius FR591 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 12045 _diffrn_reflns_theta_full 27.56 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 2.93 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.300 _refine_diff_density_min -0.321 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1775 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0523 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.084P)^2^+0.0429P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1226 _refine_ls_wR_factor_ref 0.1432 _reflns_number_gt 1165 _reflns_number_total 1775 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk3017.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2015387 _cod_database_fobs_code 2015387 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_type_symbol _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 O O21 0.7714(3) 0.38510(13) 0.26608(10) 0.0294(4) Uani d . 1 O O22 0.4354(3) 0.48759(13) 0.31092(11) 0.0312(4) Uani d . 1 O O41 0.0413(3) 0.39687(14) 0.59366(11) 0.0322(4) Uani d . 1 O O42 0.2072(3) 0.25219(14) 0.68243(10) 0.0348(4) Uani d . 1 N N1 0.8872(4) 0.18027(15) 0.33876(11) 0.0223(4) Uani d . 1 N N2 0.5923(4) 0.40231(15) 0.32000(11) 0.0240(5) Uani d . 1 N N4 0.1951(4) 0.31214(16) 0.60898(12) 0.0249(4) Uani d . 1 N N11 1.0180(4) 0.07058(15) 0.34824(12) 0.0268(4) Uani d . 1 C C1 0.7212(4) 0.21498(17) 0.40275(13) 0.0187(4) Uani d . 1 C C2 0.5699(4) 0.32132(17) 0.39589(13) 0.0190(5) Uani d . 1 C C3 0.3937(4) 0.35209(18) 0.46204(13) 0.0213(5) Uani d . 1 C C4 0.3720(4) 0.27957(17) 0.53799(13) 0.0208(5) Uani d . 1 C C5 0.5205(4) 0.17504(18) 0.54867(13) 0.0237(5) Uani d . 1 C C6 0.6891(5) 0.14360(18) 0.48299(14) 0.0237(5) Uani d . 1 H H1 0.9143 0.2259 0.2909 0.027 Uiso calc R 1 H H3 0.2900 0.4222 0.4549 0.026 Uiso calc R 1 H H5 0.5036 0.1261 0.6018 0.028 Uiso calc R 1 H H6 0.7876 0.0723 0.4909 0.028 Uiso calc R 1 H H11A 0.9208 0.0275 0.2950 0.032 Uiso d R 1 H H11B 1.2186 0.0905 0.3511 0.032 Uiso d R 1 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 C1 0.0172(10) 0.0211(11) 0.0176(9) -0.0039(8) 0.0019(8) -0.0033(7) N1 0.0257(10) 0.0223(9) 0.0201(8) 0.0001(8) 0.0069(7) -0.0004(7) N11 0.0268(10) 0.0270(10) 0.0267(9) 0.0036(8) 0.0044(7) -0.0042(7) C2 0.0206(11) 0.0203(10) 0.0158(9) -0.0019(9) 0.0018(8) 0.0002(7) N2 0.0251(10) 0.0238(10) 0.0231(9) -0.0041(8) 0.0031(8) 0.0000(7) O21 0.0355(9) 0.0293(9) 0.0265(8) -0.0033(7) 0.0147(7) 0.0014(6) O22 0.0330(9) 0.0267(9) 0.0333(9) 0.0042(7) 0.0025(7) 0.0063(7) C3 0.0176(11) 0.0227(11) 0.0227(10) -0.0007(8) -0.0002(8) -0.0025(8) C4 0.0196(11) 0.0241(11) 0.0197(10) -0.0017(9) 0.0063(8) -0.0035(8) N4 0.0220(10) 0.0307(10) 0.0228(9) -0.0007(8) 0.0058(7) -0.0047(7) O41 0.0250(9) 0.0380(10) 0.0350(9) 0.0077(7) 0.0083(7) -0.0059(7) O42 0.0382(10) 0.0446(10) 0.0250(8) 0.0038(8) 0.0159(7) 0.0036(7) C5 0.0286(12) 0.0237(11) 0.0194(10) -0.0026(9) 0.0052(9) 0.0002(8) C6 0.0277(12) 0.0207(11) 0.0233(10) 0.0022(9) 0.0060(9) 0.0005(8) 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 N1 C1 C6 119.84(18) no N1 C1 C2 123.87(17) no C6 C1 C2 116.28(18) no C1 N1 N11 120.17(16) no C1 N1 H1 119.9 no N11 N1 H1 119.9 no N1 N11 H11A 103.6 no N1 N11 H11B 102.1 no H11A N11 H11B 120.9 no C3 C2 C1 121.93(18) no C3 C2 N2 116.55(18) no C1 C2 N2 121.52(17) no O22 N2 O21 121.96(16) no O22 N2 C2 119.27(16) no O21 N2 C2 118.76(17) no C4 C3 C2 118.97(19) no C4 C3 H3 120.5 no C2 C3 H3 120.5 no C3 C4 C5 121.13(18) no C3 C4 N4 119.53(18) no C5 C4 N4 119.33(17) no O41 N4 O42 123.30(17) no O41 N4 C4 118.93(17) no O42 N4 C4 117.78(17) no C6 C5 C4 120.05(19) no C6 C5 H5 120.0 no C4 C5 H5 120.0 no C5 C6 C1 121.61(19) no C5 C6 H6 119.2 no C1 C6 H6 119.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.426(3) y C2 C3 1.390(3) y C3 C4 1.374(3) y C4 C5 1.402(3) y C5 C6 1.361(3) y C6 C1 1.425(3) y C1 N1 1.346(2) y C2 N2 1.436(2) y N2 O21 1.241(2) y N2 O22 1.237(2) y C4 N4 1.450(2) y N4 O41 1.228(2) y N4 O42 1.238(2) y N1 N11 1.415(2) y N1 H1 0.88 no N11 H11A 0.96 no N11 H11B 0.98 no C3 H3 0.95 no C5 H5 0.95 no C6 H6 0.95 no 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 N1 H1 O21 . 0.88 1.98 2.612(2) 127 y N1 H1 O42 4_654 0.88 2.23 2.961(2) 140 y N11 H11A O21 2_745 0.96 2.45 2.948(2) 112 y N11 H11A O22 2_645 0.96 2.15 3.038(2) 154 y N11 H11B Cg1 1_655 0.98 2.80 3.509(2) 129 y C5 H5 O21 4_555 0.95 2.48 3.193(2) 132 y 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 C6 C1 N1 N11 3.2(3) no C2 C1 N1 N11 -176.64(18) y N1 C1 C2 C3 177.92(18) no C6 C1 C2 C3 -2.0(3) no N1 C1 C2 N2 -2.1(3) no C6 C1 C2 N2 177.98(17) no C3 C2 N2 O22 -7.6(3) no C1 C2 N2 O22 172.50(17) no C3 C2 N2 O21 171.62(17) no C1 C2 N2 O21 -8.3(3) y C1 C2 C3 C4 2.1(3) no N2 C2 C3 C4 -177.81(18) no C2 C3 C4 C5 -1.0(3) no C2 C3 C4 N4 178.29(17) no C3 C4 N4 O41 8.9(3) y C5 C4 N4 O41 -171.84(18) no C3 C4 N4 O42 -171.26(18) no C5 C4 N4 O42 8.0(3) no C3 C4 C5 C6 -0.3(3) no N4 C4 C5 C6 -179.54(18) no C4 C5 C6 C1 0.4(3) no N1 C1 C6 C5 -179.21(19) no C2 C1 C6 C5 0.7(3) no