#------------------------------------------------------------------------------ #$Date: 2010-01-30 14:59:17 +0100 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2100144.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_2100144 _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 ; 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.80700(10) _cell_length_b 13.0955(2) _cell_length_c 14.8369(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1322.58(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.979 _diffrn_ambient_temperature 120(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 0.5570(3) 0.13693(17) 0.58404(14) 0.0144(5) Uani d . 1 . . N C1 0.6474(4) 0.1513(2) 0.50008(17) 0.0174(6) Uani d . 1 . . C O1 0.8043(3) 0.19132(16) 0.48780(13) 0.0233(5) Uani d . 1 . . O C2 0.3702(4) 0.09199(19) 0.57525(17) 0.0144(5) Uani d . 1 . . C O2 0.2569(3) 0.08007(16) 0.63623(13) 0.0201(4) Uani d . 1 . . O C3 0.3482(4) 0.0670(2) 0.47684(17) 0.0152(5) Uani d . 1 . . C C4 0.2020(4) 0.0220(2) 0.42612(19) 0.0176(6) Uani d . 1 . . C N4 0.0316(4) -0.0274(2) 0.46738(17) 0.0225(5) Uani d . 1 . . N O41 -0.1217(3) -0.03007(18) 0.42526(16) 0.0340(5) Uani d . 1 . . O O42 0.0534(3) -0.0655(2) 0.54257(15) 0.0336(6) Uani d . 1 . . O C5 0.2171(4) 0.0179(2) 0.33249(18) 0.0190(6) Uani d . 1 . . C C6 0.3815(5) 0.0576(2) 0.29069(17) 0.0238(6) Uani d . 1 . . C C7 0.5332(5) 0.1009(2) 0.34014(19) 0.0219(6) Uani d . 1 . . C C8 0.5115(4) 0.1059(2) 0.43312(19) 0.0161(6) Uani d . 1 . . C C11 0.6306(4) 0.17250(19) 0.66836(16) 0.0149(5) Uani d . 1 . . C C12 0.5089(4) 0.2277(2) 0.72450(18) 0.0169(6) Uani d . 1 . . C C13 0.5787(4) 0.2572(2) 0.80854(17) 0.0180(6) Uani d . 1 . . C I13 0.38491(3) 0.335227(15) 0.894736(12) 0.02576(7) Uani d . 1 . . I C14 0.7692(4) 0.2355(2) 0.83518(19) 0.0210(6) Uani d . 1 . . C C15 0.8903(4) 0.1817(2) 0.77675(19) 0.0227(6) Uani d . 1 . . C C16 0.8229(4) 0.1495(2) 0.69295(18) 0.0189(6) Uani d . 1 . . C H5 0.1150 -0.0119 0.2977 0.023 Uiso calc R 1 . . H H6 0.3909 0.0552 0.2268 0.029 Uiso calc R 1 . . H H7 0.6480 0.1262 0.3114 0.026 Uiso calc R 1 . . H H12 0.3796 0.2452 0.7060 0.020 Uiso calc R 1 . . H H14 0.8161 0.2571 0.8924 0.025 Uiso calc R 1 . . H H15 1.0214 0.1667 0.7943 0.027 Uiso calc R 1 . . H H16 0.9064 0.1126 0.6533 0.023 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 0.0140(10) 0.0168(12) 0.0124(10) -0.0009(9) 0.0017(9) 0.0002(8) C1 0.0216(14) 0.0145(14) 0.0160(12) -0.0013(12) 0.0017(11) -0.0013(10) O1 0.0240(10) 0.0242(12) 0.0215(10) -0.0120(9) 0.0070(9) -0.0029(8) C2 0.0150(12) 0.0122(12) 0.0160(11) 0.0031(11) -0.0025(12) 0.0025(9) O2 0.0162(9) 0.0275(12) 0.0167(9) -0.0015(8) 0.0045(8) 0.0019(8) C3 0.0172(14) 0.0139(13) 0.0145(12) 0.0023(11) 0.0012(11) 0.0016(9) C4 0.0160(12) 0.0143(14) 0.0225(13) 0.0034(11) 0.0011(11) -0.0008(11) N4 0.0153(11) 0.0235(14) 0.0288(13) -0.0008(10) -0.0008(11) -0.0121(11) O41 0.0179(10) 0.0396(13) 0.0445(12) -0.0004(10) -0.0084(10) -0.0153(10) O42 0.0314(12) 0.0431(14) 0.0264(11) -0.0153(11) 0.0022(10) 0.0026(10) C5 0.0245(15) 0.0173(15) 0.0151(13) 0.0026(12) -0.0036(12) -0.0027(11) C6 0.0376(17) 0.0211(15) 0.0127(12) 0.0020(15) -0.0002(14) -0.0016(10) C7 0.0305(16) 0.0185(15) 0.0166(13) -0.0016(13) 0.0045(12) 0.0006(11) C8 0.0185(13) 0.0134(14) 0.0165(13) 0.0001(11) -0.0005(11) 0.0014(11) C11 0.0165(12) 0.0145(12) 0.0136(11) -0.0005(13) 0.0032(10) -0.0006(9) C12 0.0178(13) 0.0171(14) 0.0159(13) 0.0025(11) 0.0005(11) 0.0004(11) C13 0.0224(14) 0.0154(13) 0.0163(12) -0.0005(11) 0.0043(12) -0.0020(10) I13 0.03085(11) 0.02628(11) 0.02015(10) -0.00147(9) 0.00725(8) -0.00753(7) C14 0.0263(15) 0.0201(16) 0.0164(13) -0.0029(12) -0.0063(12) 0.0030(11) C15 0.0184(13) 0.0221(15) 0.0275(14) -0.0007(13) -0.0060(12) -0.0006(11) C16 0.0199(13) 0.0191(15) 0.0177(13) 0.0054(11) -0.0018(11) -0.0029(11) 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 . 1.402(3) no N1 C2 . 1.407(4) no N1 C11 . 1.426(3) no C1 O1 . 1.203(3) no C1 C8 . 1.482(4) no C2 O2 . 1.199(3) no C2 C3 . 1.504(4) no C3 C4 . 1.380(4) no C3 C8 . 1.384(4) no C4 C5 . 1.394(4) no C4 N4 . 1.462(4) no N4 O41 . 1.217(3) no N4 O42 . 1.231(3) no C5 C6 . 1.381(4) no C5 H5 . 0.95 no C6 C7 . 1.388(4) no C6 H6 . 0.95 no C7 C8 . 1.389(4) no C7 H7 . 0.95 no C11 C12 . 1.379(4) no C11 C16 . 1.392(4) no C12 C13 . 1.389(4) no C12 H12 . 0.95 no C13 C14 . 1.385(4) no C13 I13 . 2.102(3) no C14 C15 . 1.389(4) no C14 H14 . 0.95 no C15 C16 . 1.391(4) no C15 H15 . 0.95 no C16 H16 . 0.95 no _cod_database_code 2100144