#------------------------------------------------------------------------------ #$Date: 2011-09-28 16:24:46 +0200 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/01/2100143.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_2100143 _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 7.52380(10) _cell_length_b 22.6556(5) _cell_length_c 7.92010(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.3824(16) _cell_angle_gamma 90.00 _cell_volume 1288.38(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 2.032 _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 0.7013(3) 0.41402(8) 0.7885(2) 0.0127(4) Uani d . 1 . . N C1 0.6825(3) 0.42127(10) 0.6070(3) 0.0126(4) Uani d . 1 . . C O1 0.6930(2) 0.46729(7) 0.5338(2) 0.0156(3) Uani d . 1 . . O C2 0.6808(3) 0.35442(10) 0.8304(3) 0.0143(4) Uani d . 1 . . C O2 0.6996(3) 0.33590(7) 0.9774(2) 0.0198(4) Uani d . 1 . . O C3 0.6392(3) 0.32144(10) 0.6588(3) 0.0120(4) Uani d . 1 . . C C4 0.6124(3) 0.26236(10) 0.6137(3) 0.0138(4) Uani d . 1 . . C C5 0.5953(3) 0.24378(11) 0.4426(3) 0.0175(5) Uani d . 1 . . C C6 0.6048(3) 0.28490(11) 0.3142(3) 0.0174(5) Uani d . 1 . . C C7 0.6310(3) 0.34455(11) 0.3560(3) 0.0154(5) Uani d . 1 . . C C8 0.6477(3) 0.36109(10) 0.5278(3) 0.0123(4) Uani d . 1 . . C N4 0.5986(3) 0.21700(9) 0.7425(3) 0.0171(4) Uani d . 1 . . N O41 0.6615(3) 0.16801(8) 0.7276(2) 0.0270(4) Uani d . 1 . . O O42 0.5241(3) 0.23050(8) 0.8548(2) 0.0257(4) Uani d . 1 . . O C11 0.7376(3) 0.46076(10) 0.9164(3) 0.0122(4) Uani d . 1 . . C C12 0.8596(3) 0.45087(10) 1.0842(3) 0.0133(4) Uani d . 1 . . C C13 0.8872(3) 0.49513(10) 1.2114(3) 0.0134(4) Uani d . 1 . . C C14 0.7969(3) 0.54861(10) 1.1675(3) 0.0127(4) Uani d . 1 . . C I14 0.83436(2) 0.613750(6) 1.364074(18) 0.01529(6) Uani d . 1 . . I C15 0.6807(3) 0.55929(10) 0.9972(3) 0.0140(4) Uani d . 1 . . C C16 0.6491(3) 0.51487(10) 0.8710(3) 0.0142(4) Uani d . 1 . . C H5 0.5772 0.2031 0.4129 0.021 Uiso calc R 1 . . H H6 0.5932 0.2720 0.1972 0.021 Uiso calc R 1 . . H H7 0.6372 0.3729 0.2695 0.018 Uiso calc R 1 . . H H12 0.9235 0.4143 1.1119 0.016 Uiso calc R 1 . . H H13 0.9677 0.4886 1.3276 0.016 Uiso calc R 1 . . H H15 0.6233 0.5968 0.9675 0.017 Uiso calc R 1 . . H H16 0.5680 0.5214 0.7550 0.017 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 0.0155(9) 0.0123(9) 0.0100(9) -0.0010(8) 0.0034(7) 0.0004(7) C1 0.0096(10) 0.0172(11) 0.0100(10) 0.0008(9) 0.0016(8) -0.0005(9) O1 0.0189(8) 0.0150(8) 0.0129(8) 0.0005(7) 0.0048(6) 0.0028(6) C2 0.0149(11) 0.0142(11) 0.0146(11) -0.0002(9) 0.0057(9) -0.0011(9) O2 0.0321(10) 0.0161(8) 0.0116(8) -0.0039(7) 0.0072(7) 0.0011(6) C3 0.0107(10) 0.0150(11) 0.0101(10) -0.0003(9) 0.0028(8) -0.0002(8) C4 0.0119(10) 0.0159(11) 0.0134(11) -0.0023(9) 0.0037(8) 0.0024(9) C5 0.0182(12) 0.0170(12) 0.0179(12) -0.0026(9) 0.0062(9) -0.0037(9) C6 0.0189(11) 0.0216(12) 0.0114(11) -0.0004(10) 0.0039(9) -0.0024(9) C7 0.0134(11) 0.0200(11) 0.0130(11) -0.0001(9) 0.0042(8) 0.0007(9) C8 0.0099(10) 0.0145(11) 0.0118(10) 0.0006(9) 0.0021(8) 0.0010(8) N4 0.0182(10) 0.0160(10) 0.0152(10) -0.0039(8) 0.0021(8) 0.0011(8) O41 0.0338(11) 0.0142(9) 0.0325(10) 0.0007(8) 0.0092(8) 0.0026(7) O42 0.0385(11) 0.0228(9) 0.0206(9) -0.0095(8) 0.0161(8) -0.0015(7) C11 0.0119(10) 0.0142(10) 0.0114(10) -0.0030(9) 0.0049(8) -0.0017(8) C12 0.0128(10) 0.0124(10) 0.0149(11) 0.0010(9) 0.0046(8) 0.0019(8) C13 0.0130(10) 0.0151(11) 0.0115(10) -0.0004(9) 0.0028(8) 0.0006(8) C14 0.0129(10) 0.0131(10) 0.0129(10) -0.0025(9) 0.0050(8) -0.0029(8) I14 0.01668(9) 0.01404(9) 0.01426(9) 0.00134(5) 0.00328(6) -0.00308(5) C15 0.0136(10) 0.0123(10) 0.0153(11) 0.0035(9) 0.0030(9) 0.0023(9) C16 0.0151(11) 0.0157(11) 0.0108(10) 0.0011(9) 0.0024(8) 0.0022(8) 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 . 1.410(3) no N1 C1 . 1.411(3) no N1 C11 . 1.434(3) no C1 O1 . 1.207(3) no C1 C8 . 1.491(3) no C2 O2 . 1.205(3) no C2 C3 . 1.500(3) no C3 C4 . 1.384(3) no C3 C8 . 1.388(3) no C4 C5 . 1.388(3) no C4 N4 . 1.473(3) no C5 C6 . 1.397(3) no C5 H5 . 0.95 no C6 C7 . 1.391(3) no C6 H6 . 0.95 no C7 C8 . 1.380(3) no C7 H7 . 0.95 no N4 O42 . 1.224(3) no N4 O41 . 1.226(3) no C11 C12 . 1.389(3) no C11 C16 . 1.390(3) no C12 C13 . 1.392(3) no C12 H12 . 0.95 no C13 C14 . 1.382(3) no C13 H13 . 0.95 no C14 C15 . 1.392(3) no C14 I14 . 2.102(2) no C15 C16 . 1.388(3) no C15 H15 . 0.95 no C16 H16 . 0.95 no _cod_database_code 2100143