#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012402.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_2012402 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1462 _journal_page_last 1464 _publ_section_title ; 4-Nitro-9,10-dihydrophenanthrene and a polymorphic form of 4-nitrophenanthrene ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Sekine, Akiko' 'Uekusa, Hidehiro' 'Ohashi, Yuji' 'Yoshimura, Kimihiro' 'Yagi, Mikio' 'Higuchi, Jiro' _chemical_formula_moiety 'C14 H9 N O2' _chemical_formula_sum 'C14 H9 N O2' _chemical_formula_iupac 'C14 H9 N O2' _chemical_formula_weight 223.22 _symmetry_cell_setting monoclinic 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' _cell_length_a 15.934(7) _cell_length_b 12.471(5) _cell_length_c 11.436(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.48(5) _cell_angle_gamma 90.00 _cell_volume 2129.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _exptl_crystal_density_diffrn 1.393 _diffrn_ambient_temperature 296(2) _refine_ls_R_factor_obs .0539 _refine_ls_wR_factor_obs .1395 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 N1 .6026(2) .3115(2) 1.0396(2) .0552(6) Uani d . 1 . N O1 .65477(15) .2549(2) 1.1180(2) .0719(7) Uani d . 1 . O O2 .6251(2) .3922(2) .9962(2) .0805(7) Uani d . 1 . O C1 .3289(2) .2457(3) .9488(3) .0589(8) Uani d . 1 . C H1 .2685 .2322 .9328 .071 Uiso calc R 1 . H C2 .3664(2) .3368(3) 1.0105(3) .0652(9) Uani d . 1 . C H2 .3316 .3854 1.0352 .078 Uiso calc R 1 . H C3 .4567(2) .3571(3) 1.0365(3) .0596(8) Uani d . 1 . C H3 .4830 .4184 1.0804 .072 Uiso calc R 1 . H C4 .5067(2) .2858(2) .9970(2) .0467(6) Uani d . 1 . C C4a .4712(2) .1907(2) .9282(2) .0417(6) Uani d . 1 . C C4b .5204(2) .1149(2) .8791(2) .0422(6) Uani d . 1 . C C5 .6061(2) .1335(2) .8722(2) .0494(7) Uani d . 1 . C H5 .6341 .1990 .8989 .059 Uiso calc R 1 . H C6 .6487(2) .0574(3) .8270(3) .0592(8) Uani d . 1 . C H6 .7048 .0721 .8227 .071 Uiso calc R 1 . H C7 .6090(2) -.0417(3) .7875(3) .0619(8) Uani d . 1 . C H7 .6394 -.0942 .7604 .074 Uiso calc R 1 . H C8 .5256(2) -.0614(2) .7887(3) .0583(8) Uani d . 1 . C H8 .4991 -.1277 .7614 .070 Uiso calc R 1 . H C8a .4779(2) .0159(2) .8303(2) .0464(6) Uani d . 1 . C C9 .3874(2) -.0020(2) .8184(3) .0562(7) Uani d . 1 . C H9 .3604 -.0669 .7863 .067 Uiso calc R 1 . H C10 .3398(2) .0726(2) .8523(3) .0557(7) Uani d . 1 . C H10 .2797 .0601 .8391 .067 Uiso calc R 1 . H C10a .3801(2) .1710(2) .9086(2) .0477(7) Uani d . 1 . C N11 .8639(2) .3028(2) .9130(3) .0639(7) Uani d . 1 . N O11 .8352(2) .3760(2) .8385(3) .1024(10) Uani d . 1 . O O12 .8162(2) .2440(2) .9473(3) .0859(8) Uani d . 1 . O C11 1.1404(2) .2669(3) 1.0986(3) .0620(8) Uani d . 1 . C H11 1.2011 .2598 1.1446 .074 Uiso calc R 1 . H C12 1.0952(2) .3554(3) 1.1156(3) .0694(9) Uani d . 1 . C H12 1.1254 .4091 1.1708 .083 Uiso calc R 1 . H C13 1.0047(2) .3643(2) 1.0506(3) .0630(8) Uani d . 1 . C H13 .9731 .4230 1.0637 .076 Uiso calc R 1 . H C14 .9615(2) .2871(2) .9669(3) .0493(7) Uani d . 1 . C C14a 1.0042(2) .1953(2) .9402(2) .0433(6) Uani d . 1 . C C14b .9618(2) .1122(2) .8481(2) .0423(6) Uani d . 1 . C C15 .8750(2) .1185(2) .7578(3) .0529(7) Uani d . 1 . C H15 .8420 .1811 .7516 .064 Uiso calc R 1 . H C16 .8379(2) .0348(3) .6789(3) .0617(8) Uani d . 1 . C H16 .7804 .0413 .6203 .074 Uiso calc R 1 . H C17 .8856(2) -.0598(3) .6857(3) .0637(8) Uani d . 1 . C H17 .8592 -.1178 .6351 .076 Uiso calc R 1 . H C18 .9710(2) -.0669(2) .7668(3) .0565(8) Uani d . 1 . C H18 1.0034 -.1293 .7691 .068 Uiso calc R 1 . H C18a 1.0118(2) .0184(2) .8480(2) .0466(6) Uani d . 1 . C C19 1.1037(2) .0108(2) .9271(3) .0531(7) Uani d . 1 . C H19 1.1357 -.0514 .9265 .064 Uiso calc R 1 . H C20 1.1441(2) .0922(2) 1.0019(3) .0543(7) Uani d . 1 . C H20 1.2049 .0872 1.0484 .065 Uiso calc R 1 . H C20a 1.0963(2) .1861(2) 1.0122(2) .0475(7) Uani d . 1 . C 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 .0584(15) .0468(14) .0546(14) -.0048(12) .0124(12) -.0069(12) O1 .0659(14) .0654(14) .0665(14) .0039(12) .0007(11) .0058(12) O2 .074(2) .0576(15) .100(2) -.0172(12) .0173(13) .0143(13) C1 .052(2) .065(2) .066(2) .0067(15) .0286(15) .010(2) C2 .076(2) .062(2) .068(2) .016(2) .038(2) .002(2) C3 .074(2) .049(2) .054(2) .0055(15) .0216(15) -.0040(13) C4 .054(2) .0433(15) .0440(14) .0008(12) .0183(12) .0017(12) C4a .0440(14) .0396(14) .0413(13) -.0016(11) .0147(11) .0040(11) C4b .0476(15) .0399(14) .0377(13) .0002(11) .0131(11) .0035(11) C5 .047(2) .049(2) .052(2) -.0009(13) .0175(13) .0006(13) C6 .051(2) .071(2) .058(2) .0119(15) .0210(14) .005(2) C7 .069(2) .064(2) .053(2) .022(2) .0207(15) .0009(15) C8 .079(2) .044(2) .047(2) .0067(15) .0167(14) -.0028(13) C8a .057(2) .0426(15) .0365(13) -.0007(13) .0122(12) .0038(11) C9 .061(2) .050(2) .053(2) -.0164(15) .0144(14) -.0005(13) C10 .044(2) .063(2) .058(2) -.0081(14) .0159(13) .0047(15) C10a .0469(15) .052(2) .0451(14) .0013(13) .0172(12) .0093(13) N11 .061(2) .0495(15) .089(2) .0058(14) .0363(15) -.0079(14) O11 .081(2) .067(2) .143(3) .0188(14) .018(2) .029(2) O12 .070(2) .082(2) .126(2) -.0068(13) .060(2) -.009(2) C11 .061(2) .074(2) .050(2) -.010(2) .0180(15) .003(2) C12 .083(2) .069(2) .061(2) -.020(2) .032(2) -.017(2) C13 .080(2) .050(2) .070(2) -.006(2) .040(2) -.010(2) C14 .055(2) .045(2) .055(2) -.0003(13) .0291(13) .0023(13) C14a .0487(15) .0406(14) .0477(14) -.0005(12) .0257(12) .0062(12) C15 .049(2) .056(2) .057(2) .0036(13) .0227(13) .0009(14) C16 .052(2) .076(2) .057(2) -.010(2) .0206(14) -.010(2) C17 .075(2) .063(2) .060(2) -.018(2) .032(2) -.013(2) C18 .077(2) .042(2) .063(2) -.0006(14) .040(2) .0003(14) C18a .056(2) .0423(15) .052(2) .0015(12) .0314(13) .0036(12) C14b .0416(14) .0443(15) .0464(14) .0019(11) .0222(11) .0063(12) C19 .053(2) .051(2) .064(2) .0134(14) .0313(14) .0138(14) C20 .043(2) .061(2) .059(2) .0070(14) .0184(13) .0161(15) C20a .048(2) .051(2) .0471(15) -.0034(13) .0213(12) .0069(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 O1 . 1.213(3) y N1 O2 . 1.230(3) y N1 C4 . 1.468(4) y C4 C3 . 1.371(4) y C4 C4a . 1.427(4) y C3 C2 . 1.386(4) ? C2 C1 . 1.360(4) ? C1 C10a . 1.418(4) ? C10a C4a . 1.411(4) ? C10a C10 . 1.430(4) ? C10 C9 . 1.339(4) ? C9 C8a . 1.419(4) ? C8a C8 . 1.409(4) ? C8a C4b . 1.424(4) ? C8 C7 . 1.357(4) ? C7 C6 . 1.390(4) ? C6 C5 . 1.370(4) ? C5 C4b . 1.414(4) ? C4a C4b . 1.460(4) y N11 O11 . 1.223(4) y N11 O12 . 1.217(3) y N11 C14 . 1.471(4) y C14 C13 . 1.363(4) y C14 C14a . 1.418(4) y C13 C12 . 1.376(5) ? C12 C11 . 1.369(5) ? C11 C20a . 1.413(4) ? C20a C14a . 1.414(4) ? C20a C20 . 1.424(4) ? C20 C19 . 1.339(4) ? C19 C18a . 1.429(4) ? C18a C18 . 1.412(4) ? C18a C14b . 1.416(4) ? C18 C17 . 1.355(4) ? C17 C16 . 1.391(4) ? C16 C15 . 1.372(4) ? C15 C14b . 1.409(4) ? C14b C14a . 1.464(4) y C13 H13 . .93 ? C12 H12 . .93 ? C11 H11 . .93 ? C20 H20 . .93 ? C19 H19 . .93 ? C18 H18 . .93 ? C17 H17 . .93 ? C16 H16 . .93 ? C15 H15 . .93 ? C3 H3 . .93 ? C2 H2 . .93 ? C1 H1 . .93 ? C10 H10 . .93 ? C9 H9 . .93 ? C8 H8 . .93 ? C7 H7 . .93 ? C6 H6 . .93 ? C5 H5 . .93 ? _cod_database_code 2012402