data_2200609 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o1025 _journal_page_last o1026 _publ_section_title ; \p--\p Stacks and C---H...O bonded sheets in 4-[(2-nitrophenyl)hydrazono]-4H-naphthalen-1-one ; loop_ _publ_author_name 'Yatsenko, A. V.' 'Paseshnichenko, K. A.' _chemical_formula_moiety 'C16 H11 N3 O3' _chemical_formula_sum 'C16 H11 N3 O3' _chemical_formula_iupac 'C16 H11 N3 O3' _chemical_formula_weight 293.28 _chemical_melting_point 517 _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/n' 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' _cell_length_a 7.328(2) _cell_length_b 16.366(4) _cell_length_c 11.131(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.33(2) _cell_angle_gamma 90.00 _cell_volume 1317.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.479 _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 O1 .60667(17) .57864(7) .93712(9) .0572(4) Uani d . 1 . . O O2 .23492(18) .27875(7) .44880(11) .0656(4) Uani d . 1 . . O O3 .1408(2) .20724(7) .28875(13) .0759(4) Uani d . 1 . . O N1 .21431(17) .43700(7) .44329(10) .0401(3) Uani d . 1 . . N N2 .23925(16) .51405(7) .48507(10) .0380(3) Uani d . 1 . . N N3 .15886(19) .27320(8) .34107(13) .0498(4) Uani d . 1 . . N C1 .5250(2) .56377(9) .83466(13) .0386(4) Uani d . 1 . . C C2 .5072(2) .48104(9) .78856(14) .0425(4) Uani d . 1 . . C C3 .4199(2) .46339(9) .67641(14) .0426(4) Uani d . 1 . . C C4 .33440(19) .52586(8) .59335(12) .0336(3) Uani d . 1 . . C C5 .2814(2) .67590(9) .55850(14) .0445(4) Uani d . 1 . . C C6 .2949(2) .75520(10) .59902(16) .0517(4) Uani d . 1 . . C C7 .3810(2) .77243(9) .71679(16) .0523(4) Uani d . 1 . . C C8 .4546(2) .71045(10) .79169(15) .0469(4) Uani d . 1 . . C C9 .4430(2) .62964(9) .75147(13) .0366(3) Uani d . 1 . . C C10 .35333(19) .61141(8) .63376(12) .0352(3) Uani d . 1 . . C C11 .11540(19) .42454(8) .32735(12) .0356(3) Uani d . 1 . . C C12 .0890(2) .34606(9) .27546(13) .0390(4) Uani d . 1 . . C C13 -.0090(2) .33540(11) .15852(15) .0478(4) Uani d . 1 . . C C14 -.0833(2) .40066(11) .09289(15) .0523(5) Uani d . 1 . . C C15 -.0601(2) .47837(11) .14233(15) .0491(4) Uani d . 1 . . C C16 .0393(2) .49030(9) .25649(14) .0416(4) Uani d . 1 . . C H2 .555(2) .4411(10) .8370(14) .053(5) Uiso d . 1 . . H H3 .419(2) .4083(11) .6500(16) .069(5) Uiso d . 1 . . H H5 .226(2) .6630(10) .4827(15) .051(5) Uiso d . 1 . . H H6 .241(2) .7953(11) .5459(14) .061(5) Uiso d . 1 . . H H7 .383(2) .8270(10) .7417(13) .055(5) Uiso d . 1 . . H H8 .508(2) .7184(11) .8724(16) .062(5) Uiso d . 1 . . H H13 -.022(3) .2800(12) .1302(16) .072(6) Uiso d . 1 . . H H14 -.153(2) .3925(10) .0167(15) .060(5) Uiso d . 1 . . H H15 -.114(2) .5221(10) .0985(14) .055(5) Uiso d . 1 . . H H16 .054(2) .5419(10) .2910(13) .052(5) Uiso d . 1 . . H H1 .257(2) .3828(10) .4895(13) .047(4) 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 .0728(8) .0503(7) .0403(6) -.0017(6) -.0153(6) -.0015(5) O2 .0868(10) .0455(7) .0558(8) .0033(6) -.0150(7) .0075(6) O3 .0982(11) .0346(6) .0878(10) -.0061(7) -.0059(8) -.0118(6) N1 .0484(8) .0330(6) .0355(7) .0011(6) -.0037(6) -.0011(5) N2 .0417(7) .0341(6) .0367(7) .0005(5) .0020(6) -.0021(5) N3 .0534(8) .0344(7) .0595(9) -.0051(6) .0027(7) .0012(6) C1 .0382(8) .0396(8) .0358(8) -.0017(7) -.0007(6) .0008(6) C2 .0485(10) .0361(8) .0392(9) .0059(7) -.0042(7) .0071(7) C3 .0488(10) .0332(7) .0436(9) .0025(7) .0004(7) -.0009(7) C4 .0345(8) .0338(7) .0314(7) .0002(6) .0017(6) .0000(6) C5 .0506(10) .0373(8) .0409(9) -.0003(7) -.0064(8) .0043(7) C6 .0576(11) .0356(8) .0572(10) .0016(8) -.0048(8) .0092(8) C7 .0586(11) .0305(8) .0637(11) -.0027(8) -.0019(9) -.0037(8) C8 .0507(10) .0406(8) .0454(9) -.0040(7) -.0042(8) -.0055(7) C9 .0349(8) .0368(7) .0365(7) -.0022(6) .0006(6) -.0005(6) C10 .0337(8) .0351(7) .0361(8) -.0004(6) .0030(6) .0028(6) C11 .0334(8) .0387(8) .0333(8) -.0018(6) .0015(6) -.0004(6) C12 .0365(8) .0387(8) .0409(8) -.0037(6) .0036(6) -.0011(6) C13 .0471(10) .0511(10) .0445(9) -.0116(8) .0049(7) -.0095(8) C14 .0491(10) .0681(12) .0359(9) -.0104(9) -.0045(7) -.0030(8) C15 .0465(10) .0566(10) .0417(9) .0030(8) -.0002(8) .0102(8) C16 .0449(9) .0376(8) .0405(9) .0026(7) .0014(7) -.0002(7) 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 C1 . 1.2235(17) yes O2 N3 . 1.2410(16) no O3 N3 . 1.2235(16) no N1 N2 . 1.3462(17) yes N1 C11 . 1.3889(17) no N1 H1 . 1.047(15) no N2 C4 . 1.3053(17) yes N3 C12 . 1.4479(19) no C1 C2 . 1.446(2) yes C1 C9 . 1.483(2) yes C2 C3 . 1.339(2) yes C2 H2 . .884(16) no C3 C4 . 1.451(2) yes C3 H3 . .949(18) no C4 C10 . 1.4703(19) yes C5 C6 . 1.372(2) no C5 C10 . 1.397(2) no C5 H5 . .900(16) no C6 C7 . 1.389(2) no C6 H6 . .929(17) no C7 C8 . 1.367(2) no C7 H7 . .935(16) no C8 C9 . 1.394(2) no C8 H8 . .929(17) no C9 C10 . 1.3995(19) no C11 C16 . 1.396(2) no C11 C12 . 1.409(2) no C12 C13 . 1.392(2) no C13 C14 . 1.357(2) no C13 H13 . .960(19) no C14 C15 . 1.385(2) no C14 H14 . .926(17) no C15 C16 . 1.372(2) no C15 H15 . .918(16) no C16 H16 . .927(16) no