data_2013803 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2004 _journal_volume 60 _journal_page_first o24 _journal_page_last o27 _publ_section_title ; A three-dimensional hydrogen-bonded framework in N-(3-nitrophenyl)phthalimide and hydrogen bonded chains of rings in N-(3,5-dinitrophenyl)phthalimide, linked into sheets by dipolar interactions ; loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _chemical_formula_moiety 'C14 H7 N3 O6' _chemical_formula_sum 'C14 H7 N3 O6' _chemical_formula_weight 313.23 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/n' _symmetry_space_group_name_Hall '-P 2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x+1/2, -y, z+1/2' _cell_length_a 5.0936(7) _cell_length_b 12.6297(18) _cell_length_c 10.366(2) _cell_angle_alpha 90 _cell_angle_beta 101.335(6) _cell_angle_gamma 90 _cell_volume 653.84(18) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.591 _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 0.2500 0.37629(17) 0.7500 0.0226(6) Uani d S 1 . . N C1 0.0390(4) 0.31442(16) 0.68110(19) 0.0235(5) Uani d . 1 . . C O1 -0.1659(3) 0.34953(10) 0.61631(14) 0.0274(4) Uani d . 1 . . O C2 0.1267(4) 0.20282(15) 0.7077(2) 0.0245(5) Uani d . 1 . . C C3 -0.0026(4) 0.10993(18) 0.6631(2) 0.0326(5) Uani d . 1 . . C C4 0.1276(4) 0.01564(18) 0.7072(3) 0.0413(6) Uani d . 1 . . C C11 0.2500 0.4893(2) 0.7500 0.0210(6) Uani d S 1 . . C C12 0.0935(4) 0.54315(16) 0.82428(19) 0.0232(5) Uani d . 1 . . C C13 0.0997(4) 0.65247(15) 0.82276(18) 0.0224(5) Uani d . 1 . . C N13 -0.0639(3) 0.71134(14) 0.90124(16) 0.0269(4) Uani d . 1 . . N O31 -0.2117(3) 0.66002(11) 0.95792(14) 0.0305(4) Uani d . 1 . . O O32 -0.0481(3) 0.80857(12) 0.90361(15) 0.0398(5) Uani d . 1 . . O C14 0.2500 0.7098(2) 0.7500 0.0238(6) Uani d S 1 . . C H3 -0.1721 0.1102 0.6051 0.039 Uiso calc R 1 . . H H4 0.0459 -0.0500 0.6778 0.050 Uiso calc R 1 . . H H12 -0.0141 0.5060 0.8744 0.028 Uiso calc R 1 . . H H14 0.2500 0.7850 0.7500 0.029 Uiso calc SR 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 0.0237(13) 0.0198(13) 0.0236(14) 0.000 0.0030(10) 0.000 C1 0.0248(11) 0.0285(12) 0.0180(11) -0.0014(8) 0.0060(8) -0.0027(9) O1 0.0240(7) 0.0294(8) 0.0277(9) 0.0014(6) 0.0028(6) 0.0005(6) C2 0.0255(10) 0.0248(12) 0.0237(12) -0.0004(8) 0.0056(8) -0.0008(9) C3 0.0299(12) 0.0313(13) 0.0353(13) -0.0014(9) 0.0033(10) -0.0028(10) C4 0.0426(14) 0.0242(13) 0.0537(17) -0.0043(10) 0.0013(11) -0.0031(11) C11 0.0216(15) 0.0201(16) 0.0206(16) 0.000 0.0020(11) 0.000 C12 0.0211(11) 0.0287(12) 0.0186(11) -0.0008(8) 0.0014(8) 0.0010(8) C13 0.0239(10) 0.0243(12) 0.0173(11) 0.0030(8) 0.0002(8) -0.0010(8) N13 0.0264(10) 0.0302(11) 0.0226(10) 0.0043(7) 0.0012(7) -0.0017(8) O31 0.0240(8) 0.0400(10) 0.0287(9) -0.0011(6) 0.0078(6) -0.0016(7) O32 0.0549(10) 0.0251(10) 0.0422(11) 0.0088(7) 0.0164(8) -0.0008(7) C14 0.0228(15) 0.0228(16) 0.0234(16) 0.000 -0.0014(11) 0.000 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 . 1.405(2) no N1 C1 2_556 1.405(2) no N1 C11 . 1.428(3) no C1 O1 . 1.209(2) no C1 C2 . 1.488(3) no C2 C3 . 1.380(3) no C2 C2 2_556 1.383(4) no C3 C4 . 1.396(3) no C3 H3 . 0.95 no C4 C4 2_556 1.381(5) no C4 H4 . 0.95 no C11 C12 . 1.390(2) no C11 C12 2_556 1.390(2) no C12 C13 . 1.381(3) no C12 H12 . 0.95 no C13 C14 . 1.381(2) no C13 N13 . 1.475(2) no N13 O31 . 1.227(2) no N13 O32 . 1.231(2) no C14 C13 2_556 1.381(2) no C14 H14 . 0.95 no