#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2208583.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_2208583 loop_ _publ_author_name 'Qian, Heng-Yu' 'Liu, Cheng' 'Yin, Zhi-Gang' _publ_section_title ; 3-(2-Furyl)-1-phenylprop-2-en-1-one 2,4-dinitrophenylhydrazone ; _journal_coeditor_code DN2013 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1623 _journal_page_last o1624 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C19 H14 N4 O5' _chemical_formula_moiety 'C19 H14 N4 O5' _chemical_formula_sum 'C19 H14 N4 O5' _chemical_formula_weight 378.34 _chemical_name_systematic ; Furylideneacetophenone 2,4-dinitrophenylhydrazone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 100.0580(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.1605(5) _cell_length_b 17.7094(11) _cell_length_c 12.8041(8) _cell_measurement_reflns_used 4026 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 27.32 _cell_measurement_theta_min 2.76 _cell_volume 1822.0(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 291(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.76 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_correction_T_min 0.9633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.234 _refine_diff_density_min -0.232 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 4181 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0439 _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^)+(0.0612P)^2^+0.2674P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1176 _refine_ls_wR_factor_ref 0.1348 _reflns_number_gt 2780 _reflns_number_total 4181 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file dn2013.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n ' _[local]_cod_cif_authors_sg_Hall '- P 2yn' _cod_database_code 2208583 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 O1 -0.2015(2) 0.67948(8) 0.72120(17) 0.1226(7) Uani d . 1 O O2 -0.1931(3) 0.79863(9) 0.7206(2) 0.1549(10) Uani d . 1 O O3 0.21815(17) 0.93777(7) 0.58948(11) 0.0759(4) Uani d . 1 O O4 0.40617(16) 0.88133(7) 0.52170(12) 0.0831(4) Uani d . 1 O O5 0.23793(14) 0.26020(6) 0.58043(10) 0.0681(3) Uani d . 1 N N1 -0.1333(2) 0.73854(9) 0.70425(16) 0.0879(6) Uani d . 1 N N2 0.28778(17) 0.88018(7) 0.56792(11) 0.0573(3) Uani d . 1 N N3 0.03351(16) 0.60023(7) 0.66072(11) 0.0564(3) Uani d . 1 H H3 -0.0578 0.5984 0.6855 0.068 Uiso calc R 1 N N4 0.10987(15) 0.53411(7) 0.64051(11) 0.0526(3) Uani d . 1 C C1 0.09817(18) 0.66797(8) 0.64275(12) 0.0487(3) Uani d . 1 C C2 0.0196(2) 0.73669(9) 0.66155(13) 0.0554(4) Uani d . 1 C C3 0.08410(19) 0.80575(8) 0.63923(12) 0.0537(4) Uani d . 1 H H3A 0.0313 0.8503 0.6529 0.064 Uiso calc R 1 C C4 0.22599(18) 0.80770(8) 0.59697(12) 0.0489(3) Uani d . 1 C C5 0.31055(19) 0.74168(9) 0.57968(13) 0.0553(4) Uani d . 1 H H5 0.4087 0.7441 0.5523 0.066 Uiso calc R 1 C C6 0.24824(19) 0.67373(8) 0.60324(13) 0.0537(4) Uani d . 1 H H6 0.3063 0.6299 0.5930 0.064 Uiso calc R 1 C C7 0.02837(17) 0.47320(8) 0.65660(12) 0.0463(3) Uani d . 1 C C8 0.09989(18) 0.40185(8) 0.63386(12) 0.0502(4) Uani d . 1 H H8 0.1988 0.4027 0.6072 0.060 Uiso calc R 1 C C9 0.03328(18) 0.33467(8) 0.64856(12) 0.0471(3) Uani d . 1 H H9 -0.0644 0.3347 0.6767 0.056 Uiso calc R 1 C C10 0.09750(18) 0.26246(8) 0.62525(12) 0.0489(3) Uani d . 1 C C11 0.0458(2) 0.19126(8) 0.63888(13) 0.0569(4) Uani d . 1 H H11 -0.0469 0.1773 0.6676 0.068 Uiso calc R 1 C C12 0.1585(2) 0.14190(10) 0.60134(15) 0.0699(5) Uani d . 1 H H12 0.1549 0.0894 0.6005 0.084 Uiso calc R 1 C C13 0.2704(3) 0.18551(11) 0.56768(17) 0.0773(6) Uani d . 1 H H13 0.3599 0.1675 0.5389 0.093 Uiso calc R 1 C C14 -0.13698(17) 0.47572(7) 0.69188(12) 0.0449(3) Uani d . 1 C C15 -0.1521(2) 0.48766(9) 0.79639(13) 0.0579(4) Uani d . 1 H H15 -0.0576 0.4921 0.8484 0.070 Uiso calc R 1 C C16 -0.3102(2) 0.49308(10) 0.82338(15) 0.0670(5) Uani d . 1 H H16 -0.3206 0.5003 0.8939 0.080 Uiso calc R 1 C C17 -0.4499(2) 0.48794(10) 0.74736(16) 0.0665(5) Uani d . 1 H H17 -0.5547 0.4922 0.7659 0.080 Uiso calc R 1 C C18 -0.4345(2) 0.47654(11) 0.64472(16) 0.0730(5) Uani d . 1 H H18 -0.5295 0.4729 0.5929 0.088 Uiso calc R 1 C C19 -0.2795(2) 0.47029(10) 0.61636(13) 0.0607(4) Uani d . 1 H H19 -0.2710 0.4624 0.5457 0.073 Uiso calc R 1 C CG1 -0.2939 0.4819 0.7200 0.010 Uiso d P 0.00 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 0.1093(12) 0.0565(8) 0.235(2) 0.0023(8) 0.1207(14) 0.0107(10) O2 0.1618(17) 0.0542(9) 0.298(3) 0.0153(9) 0.1780(19) 0.0024(12) O3 0.0961(9) 0.0429(6) 0.1003(10) 0.0039(6) 0.0492(8) 0.0009(6) O4 0.0796(9) 0.0614(8) 0.1231(12) -0.0062(6) 0.0582(8) 0.0032(7) O5 0.0601(7) 0.0544(7) 0.0986(9) 0.0070(5) 0.0387(6) -0.0018(6) N1 0.0903(12) 0.0500(9) 0.1441(16) 0.0078(8) 0.0780(12) 0.0049(9) N2 0.0624(8) 0.0469(7) 0.0674(8) -0.0033(6) 0.0248(7) -0.0017(6) N3 0.0497(7) 0.0395(7) 0.0855(10) 0.0003(5) 0.0272(7) -0.0028(6) N4 0.0450(7) 0.0404(7) 0.0752(9) 0.0009(5) 0.0180(6) -0.0038(6) C1 0.0478(8) 0.0406(7) 0.0597(9) -0.0010(6) 0.0152(7) -0.0040(6) C2 0.0558(9) 0.0453(8) 0.0721(10) 0.0028(7) 0.0302(8) -0.0016(7) C3 0.0617(10) 0.0404(8) 0.0641(10) 0.0035(7) 0.0256(8) -0.0029(7) C4 0.0535(9) 0.0413(8) 0.0541(8) -0.0039(6) 0.0153(7) -0.0024(6) C5 0.0464(8) 0.0513(9) 0.0721(10) -0.0026(6) 0.0212(7) -0.0059(7) C6 0.0475(8) 0.0421(8) 0.0745(10) 0.0013(6) 0.0192(7) -0.0074(7) C7 0.0406(7) 0.0422(8) 0.0567(8) 0.0004(6) 0.0102(6) -0.0019(6) C8 0.0398(7) 0.0458(8) 0.0674(10) 0.0021(6) 0.0157(7) -0.0040(7) C9 0.0439(8) 0.0447(8) 0.0544(8) 0.0021(6) 0.0137(6) -0.0029(6) C10 0.0460(8) 0.0470(8) 0.0562(9) 0.0033(6) 0.0160(7) -0.0012(6) C11 0.0644(10) 0.0452(8) 0.0640(10) 0.0008(7) 0.0192(8) -0.0007(7) C12 0.0875(13) 0.0461(9) 0.0791(12) 0.0132(9) 0.0225(10) -0.0019(8) C13 0.0774(12) 0.0616(11) 0.1007(15) 0.0213(9) 0.0371(11) -0.0057(10) C14 0.0452(8) 0.0361(7) 0.0554(8) 0.0014(5) 0.0144(6) -0.0004(6) C15 0.0630(10) 0.0547(9) 0.0570(9) 0.0000(7) 0.0132(8) -0.0045(7) C16 0.0878(13) 0.0575(10) 0.0647(11) 0.0011(9) 0.0380(10) -0.0020(8) C17 0.0548(10) 0.0625(10) 0.0898(13) 0.0036(8) 0.0338(10) 0.0085(9) C18 0.0454(9) 0.0975(15) 0.0772(12) -0.0002(9) 0.0137(8) 0.0064(10) C19 0.0475(9) 0.0779(12) 0.0584(10) 0.0004(8) 0.0138(7) -0.0019(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_ _diffrn_reflns_number 15658 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C13 O5 C10 105.82(13) O2 N1 O1 120.97(16) O2 N1 C2 119.20(15) O1 N1 C2 119.81(14) O4 N2 O3 122.36(13) O4 N2 C4 118.68(13) O3 N2 C4 118.96(12) C1 N3 N4 121.58(12) C1 N3 H3 119.2 N4 N3 H3 119.2 C7 N4 N3 114.56(12) N3 C1 C6 121.16(13) N3 C1 C2 122.30(13) C6 C1 C2 116.54(13) C3 C2 C1 121.74(14) C3 C2 N1 116.29(13) C1 C2 N1 121.97(13) C4 C3 C2 119.07(13) C4 C3 H3A 120.5 C2 C3 H3A 120.5 C3 C4 C5 121.37(13) C3 C4 N2 118.81(13) C5 C4 N2 119.81(13) C6 C5 C4 119.46(14) C6 C5 H5 120.3 C4 C5 H5 120.3 C5 C6 C1 121.73(14) C5 C6 H6 119.1 C1 C6 H6 119.1 N4 C7 C8 117.24(13) N4 C7 C14 122.36(12) C8 C7 C14 120.33(12) C9 C8 C7 124.27(13) C9 C8 H8 117.9 C7 C8 H8 117.9 C8 C9 C10 126.38(13) C8 C9 H9 116.8 C10 C9 H9 116.8 C11 C10 O5 109.29(13) C11 C10 C9 132.24(14) O5 C10 C9 118.47(13) C10 C11 C12 107.26(15) C10 C11 H11 126.4 C12 C11 H11 126.4 C13 C12 C11 106.08(16) C13 C12 H12 127.0 C11 C12 H12 127.0 C12 C13 O5 111.55(15) C12 C13 H13 124.2 O5 C13 H13 124.2 C19 C14 C15 118.84(14) C19 C14 C7 118.71(13) C15 C14 C7 122.34(14) C14 C15 C16 119.55(16) C14 C15 H15 120.2 C16 C15 H15 120.2 C17 C16 C15 120.73(16) C17 C16 H16 119.6 C15 C16 H16 119.6 C18 C17 C16 119.56(16) C18 C17 H17 120.2 C16 C17 H17 120.2 C17 C18 C19 120.71(18) C17 C18 H18 119.6 C19 C18 H18 119.6 C14 C19 C18 120.61(16) C14 C19 H19 119.7 C18 C19 H19 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N1 1.2218(19) O2 N1 1.204(2) O3 N2 1.2223(16) O4 N2 1.2181(17) O5 C13 1.364(2) O5 C10 1.3690(18) N1 C2 1.448(2) N2 C4 1.4511(18) N3 C1 1.3464(18) N3 N4 1.3722(16) N3 H3 0.8600 N4 C7 1.3024(18) C1 C6 1.408(2) C1 C2 1.4156(19) C2 C3 1.381(2) C3 C4 1.361(2) C3 H3A 0.9300 C4 C5 1.395(2) C5 C6 1.361(2) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.4426(19) C7 C14 1.4965(19) C8 C9 1.3348(19) C8 H8 0.9300 C9 C10 1.4332(19) C9 H9 0.9300 C10 C11 1.351(2) C11 C12 1.413(2) C11 H11 0.9300 C12 C13 1.324(3) C12 H12 0.9300 C13 H13 0.9300 C14 C19 1.380(2) C14 C15 1.381(2) C15 C16 1.396(2) C15 H15 0.9300 C16 C17 1.366(3) C16 H16 0.9300 C17 C18 1.357(3) C17 H17 0.9300 C18 C19 1.380(2) C18 H18 0.9300 C19 H19 0.9300 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 N3 H3 O1 . 0.86 1.96 2.6014(18) 131 C13 H13 O4 3_666 0.93 2.35 3.276(2) 176