#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006524.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_2006524 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 1331 _journal_page_last 1334 _publ_section_title ; 3,5-Dinitro-2-{[R-(-)-1-phenylethyl]amino}pyridine ; _space_group_IT_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _[local]_cod_cif_authors_sg_H-M 'P 21' loop_ _publ_author_name 'Cole, Jacqueline M.' 'Howard, Judith A. K.' 'MacBride, J. A. Hugh' _chemical_formula_sum 'C13 H12 N4 O4' _chemical_formula_weight 288.27 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3890(10) _cell_length_b 8.5800(10) _cell_length_c 8.9340(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.689(2) _cell_angle_gamma 90.00 _cell_volume 641.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_meas None _diffrn_ambient_temperature 100(2) _refine_ls_R_factor_obs .0449 _refine_ls_wR_factor_obs .0971 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 -.1566(3) .9649(4) .7299(3) .0307(7) Uani d . 1 . O O2 -.0182(3) 1.0684(4) .5592(3) .0326(7) Uani d . 1 . O O3 .5153(3) .8907(4) .4943(3) .0295(7) Uani d . 1 . O O4 .6102(3) .6964(4) .6283(3) .0300(7) Uani d . 1 . O N1 -.0816(4) .6743(4) .8228(4) .0244(8) Uani d . 1 . N H1N -.151(5) .739(6) .808(5) .029 Uiso d . 1 . H N2 .1773(3) .6038(4) .7886(3) .0221(8) Uani d . 1 . N N3 -.0391(4) .9658(4) .6528(3) .0252(8) Uani d . 1 . N N4 .4996(4) .7843(4) .5843(3) .0249(8) Uani d . 1 . N C1 -.2451(4) .5561(5) 1.0062(4) .0220(9) Uani d . 1 . C C2 -.3860(4) .4728(5) 1.0004(4) .0236(9) Uani d . 1 . C H2 -.404(5) .397(6) .934(5) .028 Uiso d . 1 . H C3 -.5051(5) .5040(5) 1.0990(4) .0251(9) Uani d . 1 . C H3 -.610(5) .437(5) 1.089(4) .030 Uiso d . 1 . H C4 -.4795(5) .6182(5) 1.2074(4) .0272(9) Uani d . 1 . C H4 -.569(5) .643(5) 1.283(5) .033 Uiso d . 1 . H C5 -.3371(5) .7024(5) 1.2167(4) .0272(9) Uani d . 1 . C H5 -.309(5) .780(6) 1.298(5) .033 Uiso d . 1 . H C6 -.2224(5) .6731(5) 1.1147(4) .0241(9) Uani d . 1 . C H6 -.128(5) .732(5) 1.121(5) .029 Uiso d . 1 . H C7 -.1131(5) .5259(5) .8989(4) .0230(9) Uani d . 1 . C H7 -.015(5) .505(5) .961(4) .028 Uiso d . 1 . H C8 -.1526(5) .3981(5) .7838(4) .0268(9) Uani d . 1 . C H8A -.161(5) .294(6) .846(5) .040 Uiso d . 1 . H H8B -.069(6) .385(6) .713(5) .040 Uiso d . 1 . H H8C -.253(6) .423(6) .720(5) .040 Uiso d . 1 . H C9 .0574(4) .7090(5) .7635(4) .0207(8) Uani d . 1 . C C10 .0824(4) .8462(5) .6760(4) .0200(8) Uani d . 1 . C C11 .2243(4) .8695(5) .6132(4) .0207(9) Uani d . 1 . C H11 .243(5) .969(6) .559(4) .025 Uiso d . 1 . H C12 .3437(4) .7593(5) .6420(4) .0215(9) Uani d . 1 . C C13 .3165(5) .6315(5) .7310(4) .0244(9) Uani d . 1 . C H13 .408(5) .548(5) .752(4) .029 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 .0248(14) .026(2) .042(2) .0051(13) .0112(13) .0047(13) O2 .0319(15) .029(2) .037(2) .0078(13) .0035(12) .0098(14) O3 .0310(14) .029(2) .0290(14) .0003(14) .0071(11) .0033(14) O4 .0188(13) .029(2) .042(2) .0035(13) -.0039(11) -.0009(13) N1 .024(2) .018(2) .031(2) .0012(14) .0029(14) .0042(14) N2 .022(2) .019(2) .025(2) -.0013(15) -.0002(14) .0002(14) N3 .030(2) .020(2) .026(2) -.0001(15) -.0002(14) .0022(15) N4 .027(2) .023(2) .025(2) -.005(2) .0029(13) -.005(2) C1 .025(2) .022(2) .018(2) .002(2) -.0022(14) .004(2) C2 .027(2) .019(2) .024(2) -.007(2) -.0024(15) .000(2) C3 .022(2) .026(3) .027(2) .000(2) -.0010(15) .001(2) C4 .029(2) .023(2) .030(2) .005(2) .005(2) .008(2) C5 .035(2) .025(2) .022(2) .002(2) .002(2) .001(2) C6 .025(2) .019(2) .027(2) -.004(2) .001(2) .001(2) C7 .022(2) .021(2) .025(2) .000(2) -.0003(15) .002(2) C8 .027(2) .028(3) .026(2) .002(2) .001(2) -.001(2) C9 .019(2) .022(2) .022(2) -.002(2) -.0023(14) -.001(2) C10 .020(2) .017(2) .022(2) .003(2) -.0010(14) -.0012(14) C11 .023(2) .018(2) .021(2) -.001(2) -.0022(14) -.002(2) C12 .019(2) .020(2) .025(2) .000(2) -.0007(14) -.005(2) C13 .024(2) .023(2) .026(2) .001(2) .000(2) -.002(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 N3 . 1.238(4) YES O1 H1N . 2.06(5) ? O2 N3 . 1.234(4) YES O3 N4 . 1.229(4) YES O4 N4 . 1.240(4) YES N1 C9 . 1.345(5) YES N1 C7 . 1.476(5) YES N1 H1N . .81(5) ? N2 C13 . 1.327(5) YES N2 C9 . 1.359(5) YES N3 C10 . 1.452(5) YES N4 C12 . 1.452(5) YES C1 C2 . 1.379(5) ? C1 C6 . 1.400(6) ? C1 C7 . 1.532(5) ? C2 C3 . 1.400(6) ? C2 H2 . .89(5) ? C3 C4 . 1.385(6) ? C3 H3 . 1.05(4) ? C4 C5 . 1.394(6) ? C4 H4 . 1.06(4) ? C5 C6 . 1.390(6) ? C5 H5 . 1.00(5) ? C6 H6 . .94(5) ? C7 C8 . 1.525(6) ? C7 H7 . .98(4) ? C8 H8A . 1.06(5) ? C8 H8B . .99(5) ? C8 H8C . 1.01(5) ? C9 C10 . 1.436(5) YES C10 C11 . 1.363(5) YES C11 C12 . 1.388(5) YES C11 H11 . 1.00(5) ? C12 C13 . 1.382(6) YES C13 H13 . 1.06(4) ?