#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006652.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2006652 _journal_name_full 'Acta Crystallographica' _journal_year 1997 _journal_volume C53 _journal_page_first 1647 _journal_page_last 1648 _publ_section_title ; 2-Nitro-4'-(N,N-diethylamino)azobenzene, C~16~H~18~N~4~O~2~ ; loop_ _publ_author_name 'De-Chun Zhang' 'Zheng-Hao Fei' 'Tian-Zhu Zhang' 'Yan-Qiu Zhang' 'Kai-Bei Yu' _chemical_formula_sum 'C16 H18 N4 O2' _chemical_formula_structural 'C6H4NO2NNC6H4N(C2H5)2' _chemical_formula_weight 298.34 _chemical_melting_point .378E-305 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.366(3) _cell_length_b 8.196(2) _cell_length_c 20.999(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2988.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _exptl_crystal_density_diffrn 1.326 _diffrn_ambient_temperature 291(2) _refine_ls_R_factor_obs .0334 _refine_ls_wR_factor_obs .0694 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .14512(11) .2480(2) .77972(9) .0718(6) Uani d . 1 . O O2 .18483(9) .1372(2) .69308(8) .0631(5) Uani d . 1 . O N1 .15280(10) .1300(3) .74511(9) .0468(5) Uani d . 1 . N N2 .02542(10) .1017(2) .83292(8) .0450(5) Uani d . 1 . N N3 .01142(10) .0995(2) .89220(8) .0417(5) Uani d . 1 . N N4 -.16169(10) .6094(2) .99597(8) .0441(5) Uani d . 1 . N C1 .12420(12) -.0287(3) .76636(9) .0372(6) Uani d . 1 . C C2 .15914(14) -.1649(3) .74143(11) .0426(6) Uani d . 1 . C C3 .13673(14) -.3174(4) .76144(11) .0491(7) Uani d . 1 . C C4 .07897(15) -.3322(3) .80658(11) .0497(7) Uani d . 1 . C C5 .04417(14) -.1953(3) .83114(11) .0456(6) Uani d . 1 . C C6 .06596(12) -.0394(3) .81224(9) .0381(6) Uani d . 1 . C C7 -.03219(12) .2328(2) .91454(9) .0362(6) Uani d . 1 . C C8 -.04541(13) .2377(3) .97953(10) .0406(6) Uani d . 1 . C C9 -.08743(13) .3617(3) 1.00651(11) .0401(6) Uani d . 1 . C C10 -.11888(12) .4876(3) .96965(10) .0362(5) Uani d . 1 . C C11 -.10452(14) .4796(3) .90359(10) .0427(6) Uani d . 1 . C C12 -.06237(13) .3569(3) .87702(11) .0423(6) Uani d . 1 . C C13 -.16515(14) .6346(3) 1.06465(11) .0433(6) Uani d . 1 . C C14 -.2336(2) .5544(4) 1.09579(15) .0638(8) Uani d . 1 . C C15 -.20296(15) .7297(3) .95741(13) .0512(7) Uani d . 1 . C C16 -.1553(2) .8789(4) .9433(2) .0683(9) Uani d . 1 . C H2 .2002(11) -.150(2) .7101(9) .040(6) Uiso d . 1 . H H3 .1636(12) -.412(3) .7462(9) .047(7) Uiso d . 1 . H H4 .0615(12) -.441(3) .8224(9) .053(7) Uiso d . 1 . H H5 .0059(13) -.202(3) .8660(11) .066(8) Uiso d . 1 . H H8 -.0224(11) .155(2) 1.0064(9) .038(6) Uiso d . 1 . H H9 -.0951(10) .361(2) 1.0517(9) .038(6) Uiso d . 1 . H H11 -.1233(12) .564(3) .8793(9) .046(7) Uiso d . 1 . H H12 -.0556(11) .355(2) .8331(9) .036(5) Uiso d . 1 . H H13A -.1671(11) .755(3) 1.0697(8) .036(6) Uiso d . 1 . H H13B -.1142(13) .596(2) 1.0837(9) .051(7) Uiso d . 1 . H H14A -.2282(15) .429(4) 1.0903(11) .088(10) Uiso d . 1 . H H14B -.2324(13) .583(3) 1.1389(11) .069(8) Uiso d . 1 . H H14C -.2824(17) .585(3) 1.0738(12) .098(11) Uiso d . 1 . H H15A -.2209(11) .680(3) .9159(9) .050(7) Uiso d . 1 . H H15B -.2510(13) .763(3) .9824(9) .061(7) Uiso d . 1 . H H16A -.1083(16) .850(3) .9196(12) .086(9) Uiso d . 1 . H H16B -.1384(15) .933(3) .9854(13) .098(11) Uiso d . 1 . H H16C -.188(2) .958(4) .9190(15) .145(15) 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 .0927(15) .0465(12) .0764(13) -.0132(11) .0131(11) -.0204(10) O2 .0688(12) .0682(13) .0522(11) -.0088(10) .0129(9) .0035(9) N1 .0444(12) .047(2) .0488(13) .0004(11) -.0023(10) -.0050(11) N2 .0456(12) .0456(13) .0438(11) .0074(10) .0010(9) -.0063(10) N3 .0408(11) .0430(13) .0414(11) -.0015(10) .0014(9) -.0067(9) N4 .0500(12) .0401(13) .0424(11) .0112(10) .0013(9) -.0007(10) C1 .0398(13) .035(2) .0370(12) .0022(12) -.0052(11) -.0047(11) C2 .0421(15) .045(2) .0401(14) .0066(13) .0006(12) -.0008(13) C3 .057(2) .043(2) .048(2) .0155(15) -.0023(13) -.0076(13) C4 .059(2) .040(2) .0499(15) .0004(15) -.0014(13) .0009(13) C5 .049(2) .048(2) .0407(14) .0032(14) .0014(12) -.0022(13) C6 .0391(13) .040(2) .0352(12) .0074(12) -.0053(11) -.0050(11) C7 .0368(12) .0302(14) .0416(14) .0003(11) .0007(11) -.0061(11) C8 .0415(14) .039(2) .0409(14) .0019(12) -.0028(11) -.0007(12) C9 .0457(14) .0406(15) .0340(13) .0008(12) .0021(11) -.0027(12) C10 .0345(12) .0315(14) .0427(13) -.0017(11) -.0024(10) -.0013(11) C11 .0511(15) .038(2) .0390(13) .0047(13) -.0017(12) .0015(12) C12 .0494(14) .042(2) .0351(13) -.0026(12) .0024(11) -.0039(12) C13 .047(2) .035(2) .0478(15) .0013(13) .0022(12) -.0087(12) C14 .063(2) .073(3) .055(2) -.016(2) .009(2) -.008(2) C15 .047(2) .050(2) .056(2) .0096(14) .0038(14) -.0012(14) C16 .071(2) .051(2) .083(2) .003(2) .020(2) .006(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 . 1.217(2) yes O2 N1 . 1.227(2) yes N1 C1 . 1.462(3) yes N2 N3 . 1.268(2) yes N2 C6 . 1.422(2) yes N3 C7 . 1.410(2) yes N4 C10 . 1.362(2) yes N4 C13 . 1.458(3) yes N4 C15 . 1.463(3) yes C1 C2 . 1.374(3) ? C1 C6 . 1.399(3) ? C2 C3 . 1.375(3) ? C3 C4 . 1.385(3) ? C4 C5 . 1.375(3) ? C5 C6 . 1.390(3) ? C7 C8 . 1.384(3) ? C7 C12 . 1.389(3) ? C8 C9 . 1.373(3) ? C9 C10 . 1.401(3) ? C10 C11 . 1.411(3) ? C11 C12 . 1.363(3) ? C13 C14 . 1.508(3) ? C15 C16 . 1.506(4) ?