#------------------------------------------------------------------------------ #$Date: 2010-01-30 14:59:17 +0100 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2100142.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_2100142 _journal_name_full 'Acta Crystallographica, Section B' _journal_year 2005 _journal_volume 61 _journal_page_first 227 _journal_page_last 237 _publ_section_title ; Isomeric N-(iodophenyl)-nitrophthalimides: interplay of C-H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic \p...\p stacking interactions ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M.S.' 'Wardell, Solange M. S. V.' 'Wardell, James L.' _chemical_formula_moiety 'C14 H7 I N2 O4' _chemical_formula_sum 'C14 H7 I N2 O4' _chemical_formula_weight 394.12 _symmetry_cell_setting monoclinic 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 13.4591(6) _cell_length_b 7.6018(3) _cell_length_c 14.7086(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.5920(10) _cell_angle_gamma 90.00 _cell_volume 1408.74(11) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _exptl_crystal_density_diffrn 1.858 _diffrn_ambient_temperature 291(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 0.32614(19) 0.8958(3) 0.08810(18) 0.0529(5) Uani d . 1 . . N C11 0.2475(2) 1.0301(4) 0.0551(2) 0.0559(6) Uani d . 1 . . C C12 0.1692(3) 1.0496(5) 0.0946(3) 0.0655(7) Uani d . 1 . . C I12 0.16016(2) 0.87293(4) 0.20105(2) 0.08778(14) Uani d . 1 . . I C13 0.0947(4) 1.1824(6) 0.0614(3) 0.0878(11) Uani d . 1 . . C C14 0.0993(4) 1.2932(6) -0.0105(4) 0.0976(14) Uani d . 1 . . C C15 0.1754(4) 1.2727(5) -0.0520(3) 0.0895(12) Uani d . 1 . . C C16 0.2498(4) 1.1426(4) -0.0200(3) 0.0731(9) Uani d . 1 . . C C1 0.4182(2) 0.9115(4) 0.1710(2) 0.0547(6) Uani d . 1 . . C O1 0.44132(18) 1.0368(3) 0.22369(17) 0.0715(6) Uani d . 1 . . O C2 0.3212(2) 0.7340(4) 0.0415(2) 0.0527(6) Uani d . 1 . . C O2 0.2517(2) 0.6906(3) -0.03262(17) 0.0730(6) Uani d . 1 . . O C8 0.4768(2) 0.7430(4) 0.17745(19) 0.0527(6) Uani d . 1 . . C C3 0.4178(2) 0.6368(4) 0.1007(2) 0.0500(6) Uani d . 1 . . C C4 0.4513(2) 0.4701(4) 0.0880(2) 0.0537(6) Uani d . 1 . . C C5 0.5474(2) 0.4168(4) 0.1560(2) 0.0558(6) Uani d . 1 . . C N5 0.5869(2) 0.2388(4) 0.1454(2) 0.0672(7) Uani d . 1 . . N O51 0.6652(2) 0.1855(5) 0.2106(2) 0.0923(9) Uani d . 1 . . O O52 0.5389(2) 0.1557(3) 0.0722(2) 0.0774(7) Uani d . 1 . . O C6 0.6075(2) 0.5207(5) 0.2319(2) 0.0654(8) Uani d . 1 . . C C7 0.5729(2) 0.6873(5) 0.2439(2) 0.0639(7) Uani d . 1 . . C H13 0.0418 1.1963 0.0879 0.105 Uiso calc R 1 . . H H14 0.0501 1.3838 -0.0316 0.117 Uiso calc R 1 . . H H15 0.1764 1.3471 -0.1019 0.107 Uiso calc R 1 . . H H16 0.3016 1.1287 -0.0477 0.088 Uiso calc R 1 . . H H4 0.4120 0.3979 0.0369 0.064 Uiso calc R 1 . . H H6 0.6716 0.4788 0.2752 0.078 Uiso calc R 1 . . H H7 0.6127 0.7594 0.2948 0.077 Uiso calc R 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 0.0530(12) 0.0535(13) 0.0522(12) -0.0029(9) 0.0185(10) -0.0064(10) C11 0.0596(15) 0.0495(15) 0.0548(15) -0.0058(12) 0.0155(12) -0.0046(12) C12 0.0677(17) 0.0608(18) 0.0683(18) 0.0057(14) 0.0244(15) 0.0015(15) I12 0.0826(2) 0.1008(2) 0.0971(2) 0.01524(12) 0.05306(17) 0.02594(14) C13 0.085(3) 0.082(2) 0.096(3) 0.024(2) 0.032(2) -0.001(2) C14 0.114(3) 0.060(2) 0.102(3) 0.024(2) 0.017(3) 0.006(2) C15 0.124(3) 0.056(2) 0.081(2) 0.004(2) 0.027(2) 0.0078(18) C16 0.093(3) 0.0598(19) 0.069(2) -0.0113(17) 0.0312(19) -0.0011(15) C1 0.0524(14) 0.0623(16) 0.0520(14) -0.0109(12) 0.0216(12) -0.0095(12) O1 0.0714(13) 0.0713(14) 0.0694(13) -0.0103(11) 0.0217(11) -0.0235(11) C2 0.0535(13) 0.0539(15) 0.0486(14) -0.0058(11) 0.0151(12) -0.0050(11) O2 0.0731(14) 0.0615(12) 0.0633(13) 0.0005(11) -0.0023(11) -0.0086(11) C8 0.0486(13) 0.0619(16) 0.0484(13) -0.0112(11) 0.0179(11) -0.0054(12) C3 0.0484(13) 0.0564(15) 0.0450(13) -0.0058(11) 0.0160(10) -0.0027(11) C4 0.0550(14) 0.0590(16) 0.0475(13) -0.0022(12) 0.0183(12) -0.0047(11) C5 0.0488(13) 0.0640(16) 0.0603(16) 0.0006(12) 0.0264(12) 0.0036(13) N5 0.0595(14) 0.0744(18) 0.0753(17) 0.0106(13) 0.0333(14) 0.0085(15) O51 0.0703(16) 0.105(2) 0.099(2) 0.0307(14) 0.0271(16) 0.0109(16) O52 0.0857(17) 0.0681(15) 0.0836(17) 0.0085(12) 0.0363(14) -0.0055(13) C6 0.0447(13) 0.083(2) 0.0644(18) -0.0002(14) 0.0139(13) 0.0050(16) C7 0.0496(14) 0.0754(19) 0.0601(17) -0.0149(13) 0.0110(13) -0.0104(15) 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 C2 . 1.399(4) no N1 C1 . 1.405(4) no N1 C11 . 1.427(4) no C11 C12 . 1.378(5) no C11 C16 . 1.406(5) no C12 C13 . 1.385(5) no C12 I12 . 2.099(4) no C13 C14 . 1.372(7) no C13 H13 . 0.93 no C14 C15 . 1.373(7) no C14 H14 . 0.93 no C15 C16 . 1.367(6) no C15 H15 . 0.93 no C16 H16 . 0.93 no C1 O1 . 1.198(4) no C1 C8 . 1.490(4) no C2 O2 . 1.206(3) no C2 C3 . 1.483(4) no C8 C7 . 1.385(4) no C8 C3 . 1.388(4) no C3 C4 . 1.380(4) no C4 C5 . 1.388(4) no C4 H4 . 0.93 no C5 C6 . 1.375(5) no C5 N5 . 1.482(4) no N5 O51 . 1.218(4) no N5 O52 . 1.220(4) no C6 C7 . 1.382(5) no C6 H6 . 0.93 no C7 H7 . 0.93 no _cod_database_code 2100142