#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2011790.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_2011790 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 295 _journal_page_last 297 _publ_section_title ; 4-(Phenyldiazenyl)naphthalen-1-amine and its hydrochloride ; loop_ _publ_author_name 'Yatsenko, A. V.' 'Chernyshev, V. V.' 'Paseshnichenko, K. A.' 'Schenk, H.' _chemical_name_common 'C.I. Solvent Yellow 4' _chemical_formula_sum 'C16 H13 N3' _chemical_formula_weight 247.29 _chemical_melting_point 396 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 26.120(5) _cell_length_b 18.473(4) _cell_length_c 10.379(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5008(2) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.312 _diffrn_ambient_temperature 293(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 N1 .19711(8) -.11543(10) .07824(18) .0555(5) Uani d . 1 . . N N2 .14729(6) .07504(9) .47727(14) .0442(4) Uani d . 1 . . N N3 .18239(6) .11234(8) .52983(14) .0438(4) Uani d . 1 . . N N4 .16634(14) -.25577(13) .3546(2) .0938(8) Uani d . 1 . . N H4A .1966(8) -.25980(16) .3334(6) .142(17) Uiso calc R 1 . . H H4B .1443(5) -.2808(6) .3195(9) .19(2) Uiso calc R 1 . . H N5 .10966(6) -.06221(9) .74285(17) .0540(5) Uani d . 1 . . N N6 .14443(7) -.02607(10) .79748(17) .0624(5) Uani d . 1 . . N C1 .18467(7) -.06957(10) .17689(18) .0422(5) Uani d . 1 . . C C2 .22244(7) -.02806(11) .2337(2) .0458(5) Uani d . 1 . . C C3 .21107(7) .01979(11) .33204(19) .0449(5) Uani d . 1 . . C C4 .16209(7) .02764(10) .37888(18) .0401(5) Uani d . 1 . . C C5 .07036(8) -.01017(12) .3671(2) .0500(5) Uani d . 1 . . C C6 .03282(8) -.05146(13) .3139(2) .0581(6) Uani d . 1 . . C C7 .04427(8) -.10059(13) .2161(2) .0600(6) Uani d . 1 . . C C8 .09341(8) -.10744(12) .1717(2) .0509(5) Uani d . 1 . . C C9 .13320(7) -.06496(10) .22341(18) .0405(5) Uani d . 1 . . C C10 .12189(7) -.01509(10) .32454(17) .0397(5) Uani d . 1 . . C C11 .16327(7) .15787(10) .63115(18) .0417(5) Uani d . 1 . . C C12 .11381(8) .15559(12) .6772(2) .0512(5) Uani d . 1 . . C C13 .09934(9) .20058(12) .7769(2) .0561(6) Uani d . 1 . . C C14 .13384(9) .24739(13) .8317(2) .0562(6) Uani d . 1 . . C C15 .18267(9) .25047(13) .7866(2) .0606(6) Uani d . 1 . . C C16 .19809(8) .20549(12) .6858(2) .0543(6) Uani d . 1 . . C C21 .15272(10) -.20762(13) .4478(2) .0667(7) Uani d . 1 . . C C22 .18927(10) -.16590(13) .5063(2) .0638(6) Uani d . 1 . . C C23 .17667(9) -.11757(13) .6031(2) .0595(6) Uani d . 1 . . C C24 .12661(8) -.10946(11) .6448(2) .0545(6) Uani d . 1 . . C C25 .03485(9) -.14348(14) .6250(3) .0646(7) Uani d . 1 . . C C26 -.00117(11) -.18438(15) .5662(3) .0747(7) Uani d . 1 . . C C27 .01101(13) -.23589(17) .4715(3) .0902(10) Uani d . 1 . . C C28 .06034(14) -.24409(16) .4349(3) .0818(9) Uani d . 1 . . C C29 .09980(9) -.20238(11) .4886(2) .0549(6) Uani d . 1 . . C C30 .08807(9) -.15150(11) .5868(2) .0569(6) Uani d . 1 . . C C31 .12692(9) .02105(11) .8972(2) .0531(5) Uani d . 1 . . C C32 .07563(9) .02685(13) .9341(2) .0636(6) Uani d . 1 . . C C33 .06304(11) .07348(15) 1.0318(3) .0724(7) Uani d . 1 . . C C34 .09943(12) .11322(14) 1.0925(2) .0694(7) Uani d . 1 . . C C35 .14975(11) .10847(13) 1.0569(2) .0653(7) Uani d . 1 . . C C36 .16350(10) .06231(13) .9593(2) .0584(6) Uani d . 1 . . C H10 .2301(7) -.1135(10) .0494(18) .051(6) Uiso d . 1 . . H H11 .1733(8) -.1366(11) .033(2) .069(8) Uiso d . 1 . . H H2 .2584(7) -.0316(9) .2029(17) .060(6) Uiso d . 1 . . H H3 .2372(6) .0510(8) .3672(16) .040(5) Uiso d . 1 . . H H5 .0621(7) .0260(10) .4320(18) .052(6) Uiso d . 1 . . H H6 -.0011(8) -.0466(10) .3445(19) .072(7) Uiso d . 1 . . H H7 .0194(7) -.1312(10) .1789(19) .062(6) Uiso d . 1 . . H H8 .1015(7) -.1431(10) .1107(18) .047(6) Uiso d . 1 . . H H12 .0918(7) .1206(10) .643(2) .066(7) Uiso d . 1 . . H H13 .0645(8) .1997(10) .8108(18) .067(7) Uiso d . 1 . . H H14 .1233(8) .2771(11) .899(2) .069(7) Uiso d . 1 . . H H15 .2066(8) .2838(10) .8210(19) .068(7) Uiso d . 1 . . H H16 .2332(7) .2037(9) .6536(18) .058(6) Uiso d . 1 . . H H22 .2238(8) -.1697(11) .484(2) .073(7) Uiso d . 1 . . H H23 .2047(9) -.0847(12) .643(2) .093(8) Uiso d . 1 . . H H25 .0262(9) -.1066(13) .685(2) .092(9) Uiso d . 1 . . H H26 -.0400(10) -.1802(12) .592(2) .105(9) Uiso d . 1 . . H H27 -.0092(9) -.2693(13) .417(2) .101(9) Uiso d . 1 . . H H28 .0707(10) -.2824(14) .376(3) .104(10) Uiso d . 1 . . H H32 .0585(10) -.0173(14) .871(3) .121(9) Uiso d . 1 . . H H33 .0260(10) .0753(12) 1.057(2) .095(8) Uiso d . 1 . . H H34 .0905(8) .1446(12) 1.154(2) .073(8) Uiso d . 1 . . H H35 .1745(7) .1384(11) 1.101(2) .067(7) Uiso d . 1 . . H H36 .1980(8) .0572(10) .9376(18) .060(6) 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 N1 .0499(12) .0659(13) .0507(12) .0034(10) -.0021(10) -.0130(10) N2 .0438(9) .0511(10) .0376(9) .0030(8) -.0019(8) .0007(8) N3 .0454(9) .0497(10) .0362(9) .0042(8) -.0031(8) -.0024(8) N4 .119(2) .0844(17) .0775(16) .0169(16) -.0081(16) -.0253(14) N5 .0533(10) .0587(11) .0501(11) -.0069(9) -.0057(9) -.0025(10) N6 .0625(12) .0675(12) .0572(12) .0004(10) -.0013(10) -.0005(10) C1 .0451(11) .0419(11) .0394(11) .0067(9) -.0022(9) .0007(9) C2 .0375(11) .0521(12) .0477(12) .0028(10) .0018(10) -.0006(10) C3 .0415(11) .0502(12) .0429(12) -.0032(10) -.0048(10) -.0046(10) C4 .0395(11) .0453(11) .0357(10) .0039(9) -.0001(9) .0010(9) C5 .0450(12) .0595(14) .0454(13) -.0001(11) .0032(10) .0046(12) C6 .0371(12) .0747(16) .0626(15) -.0040(12) .0021(12) .0079(14) C7 .0466(13) .0663(15) .0671(16) -.0145(12) -.0126(12) .0059(13) C8 .0534(14) .0494(13) .0498(13) -.0050(11) -.0092(11) .0008(12) C9 .0414(11) .0413(11) .0387(11) .0006(9) -.0065(9) .0056(9) C10 .0366(10) .0450(11) .0376(11) .0018(9) -.0024(9) .0058(9) C11 .0446(11) .0444(11) .0363(11) .0063(9) -.0044(9) .0033(10) C12 .0544(13) .0541(14) .0450(13) -.0021(11) -.0011(11) -.0032(11) C13 .0549(14) .0635(14) .0500(14) .0011(12) .0054(12) -.0072(12) C14 .0613(15) .0613(15) .0459(13) .0101(13) -.0038(12) -.0106(12) C15 .0588(14) .0609(14) .0621(15) .0026(13) -.0145(13) -.0152(12) C16 .0418(12) .0605(13) .0605(15) .0044(11) -.0015(11) -.0073(12) C21 .0892(19) .0554(15) .0554(15) .0073(14) -.0067(14) .0043(12) C22 .0639(16) .0636(15) .0639(16) -.0022(14) -.0094(14) .0018(13) C23 .0553(14) .0652(15) .0580(15) -.0015(13) -.0008(12) .0068(13) C24 .0647(15) .0511(13) .0479(13) -.0023(11) -.0047(11) .0050(11) C25 .0599(15) .0722(17) .0618(16) -.0145(13) -.0040(13) .0151(14) C26 .0712(18) .0825(19) .0703(18) -.0244(15) -.0087(15) .0139(16) C27 .098(2) .081(2) .092(2) -.0350(19) -.030(2) .0264(19) C28 .110(2) .0634(18) .0717(19) -.0235(18) -.0301(18) .0136(15) C29 .0731(16) .0468(12) .0448(13) -.0052(12) -.0117(12) .0084(11) C30 .0708(15) .0509(13) .0490(13) -.0161(11) -.0161(12) .0168(11) C31 .0717(15) .0474(12) .0402(12) .0076(11) -.0019(11) .0013(10) C32 .0676(16) .0637(16) .0596(16) -.0055(13) -.0062(13) .0063(13) C33 .0687(17) .0811(19) .0673(18) .0110(15) .0140(15) .0112(15) C34 .095(2) .0644(17) .0487(16) .0130(16) .0007(15) -.0026(13) C35 .0782(18) .0591(16) .0585(16) .0000(14) -.0142(14) -.0042(13) C36 .0539(14) .0628(15) .0586(15) .0051(12) -.0039(13) .0067(13) 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 N1 C1 . 1.368(2) yes C1 C2 . 1.381(3) yes C2 C3 . 1.383(3) yes C3 C4 . 1.376(2) yes C4 N2 . 1.400(2) yes N2 N3 . 1.270(2) yes N4 C21 . 1.362(3) yes C21 C22 . 1.369(3) yes C22 C23 . 1.384(3) yes C23 C24 . 1.386(3) yes C24 N5 . 1.412(3) yes N5 N6 . 1.262(2) yes N1 H10 . .912(18) no N1 H11 . .87(2) no N3 C11 . 1.436(2) no N4 H4A . .8230 no N4 H4B . .8230 no N6 C31 . 1.427(3) no C1 C9 . 1.431(2) no C2 H2 . .995(18) no C3 H3 . .965(16) no C4 C10 . 1.430(2) no C5 C6 . 1.359(3) no C5 C10 . 1.420(3) no C5 H5 . .973(18) no C6 C7 . 1.394(3) no C6 H6 . .95(2) no C7 C8 . 1.370(3) no C7 H7 . .944(19) no C8 C9 . 1.409(3) no C8 H8 . .938(18) no C9 C10 . 1.427(2) no C11 C12 . 1.378(3) no C11 C16 . 1.386(3) no C12 C13 . 1.380(3) no C12 H12 . .933(19) no C13 C14 . 1.373(3) no C13 H13 . .98(2) no C14 C15 . 1.360(3) no C14 H14 . .93(2) no C15 C16 . 1.396(3) no C15 H15 . .947(19) no C16 H16 . .976(18) no C21 C29 . 1.449(3) no C22 H22 . .93(2) no C23 H23 . 1.04(2) no C24 C30 . 1.407(3) no C25 C26 . 1.352(3) no C25 C30 . 1.453(3) no C25 H25 . .95(2) no C26 C27 . 1.405(4) no C26 H26 . 1.05(2) no C27 C28 . 1.352(4) no C27 H27 . .99(2) no C28 C29 . 1.402(3) no C28 H28 . .97(3) no C29 C30 . 1.420(3) no C31 C36 . 1.382(3) no C31 C32 . 1.398(3) no C32 C33 . 1.370(3) no C32 H32 . 1.14(3) no C33 C34 . 1.356(4) no C33 H33 . 1.00(2) no C34 C35 . 1.368(3) no C34 H34 . .89(2) no C35 C36 . 1.372(3) no C35 H35 . .96(2) no C36 H36 . .933(19) no _cod_database_code 2011790