#------------------------------------------------------------------------------ #$Date: 2012-02-03 18:16:24 +0100 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$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/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2100143 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M.S.' 'Wardell, Solange M. S. V.' 'Wardell, James L.' _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 ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 227 _journal_page_last 237 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C14 H7 I N2 O4' _chemical_formula_sum 'C14 H7 I N2 O4' _chemical_formula_weight 394.12 _chemical_name_systematic ; N-(4-Iodophenyl)-3-nitrophthalimide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 107.3824(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.52380(10) _cell_length_b 22.6556(5) _cell_length_c 7.92010(10) _cell_measurement_reflns_used 2918 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.46 _cell_measurement_theta_min 2.98 _cell_volume 1288.38(4) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics ' PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL & SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle 2003) & SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 7971 _diffrn_reflns_theta_full 27.46 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_min 2.98 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 2.504 _exptl_absorpt_correction_T_max 0.602 _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.032 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.448 _refine_diff_density_min -0.684 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2918 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0221 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0071P)^2^+1.5414P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.0518 _reflns_number_gt 2724 _reflns_number_total 2918 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm5022.cif _[local]_cod_data_source_block IV _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2100143 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' 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 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N1 C1 111.49(18) no C2 N1 C11 123.50(18) no C1 N1 C11 125.00(19) no O1 C1 N1 126.1(2) no O1 C1 C8 128.0(2) no N1 C1 C8 105.90(18) no O2 C2 N1 124.8(2) no O2 C2 C3 129.4(2) no N1 C2 C3 105.76(18) no C4 C3 C8 117.9(2) no C4 C3 C2 133.6(2) no C8 C3 C2 108.14(19) no C3 C4 C5 120.6(2) no C3 C4 N4 122.07(19) no C5 C4 N4 117.3(2) no C4 C5 C6 119.9(2) no C4 C5 H5 120.0 no C6 C5 H5 120.0 no C7 C6 C5 120.6(2) no C7 C6 H6 119.7 no C5 C6 H6 119.7 no C8 C7 C6 117.6(2) no C8 C7 H7 121.2 no C6 C7 H7 121.2 no C7 C8 C3 123.4(2) no C7 C8 C1 128.0(2) no C3 C8 C1 108.58(19) no O42 N4 O41 124.8(2) no O42 N4 C4 118.12(19) no O41 N4 C4 117.13(19) no C12 C11 C16 121.2(2) no C12 C11 N1 119.3(2) no C16 C11 N1 119.53(19) no C11 C12 C13 119.3(2) no C11 C12 H12 120.4 no C13 C12 H12 120.4 no C14 C13 C12 119.6(2) no C14 C13 H13 120.2 no C12 C13 H13 120.2 no C13 C14 C15 121.0(2) no C13 C14 I14 118.80(16) no C15 C14 I14 120.14(16) no C16 C15 C14 119.6(2) no C16 C15 H15 120.2 no C14 C15 H15 120.2 no C15 C16 C11 119.2(2) no C15 C16 H16 120.4 no C11 C16 H16 120.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C12 H12 O41 4_555 0.95 2.56 3.487(3) 166 y C16 H16 O1 3_666 0.95 2.54 3.484(3) 170 y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C2 N1 C1 O1 179.8(2) no C11 N1 C1 O1 -0.5(4) no C2 N1 C1 C8 -0.1(2) no C11 N1 C1 C8 179.55(19) no C1 N1 C2 O2 176.2(2) no C11 N1 C2 O2 -3.5(4) no C1 N1 C2 C3 -2.0(2) no C11 N1 C2 C3 178.33(19) no O2 C2 C3 C4 -1.0(4) no N1 C2 C3 C4 177.1(2) no O2 C2 C3 C8 -174.6(2) no N1 C2 C3 C8 3.5(2) no C8 C3 C4 C5 0.2(3) no C2 C3 C4 C5 -172.9(2) no C8 C3 C4 N4 -179.0(2) no C2 C3 C4 N4 7.9(4) no C3 C4 C5 C6 -0.1(4) no N4 C4 C5 C6 179.2(2) no C4 C5 C6 C7 -0.1(4) no C5 C6 C7 C8 0.2(3) no C6 C7 C8 C3 -0.1(3) no C6 C7 C8 C1 177.8(2) no C4 C3 C8 C7 -0.1(3) no C2 C3 C8 C7 174.7(2) no C4 C3 C8 C1 -178.35(19) no C2 C3 C8 C1 -3.6(2) no O1 C1 C8 C7 4.3(4) no N1 C1 C8 C7 -175.8(2) no O1 C1 C8 C3 -177.6(2) no N1 C1 C8 C3 2.4(2) no C3 C4 N4 O42 34.4(3) no C5 C4 N4 O42 -144.8(2) no C3 C4 N4 O41 -146.3(2) no C5 C4 N4 O41 34.4(3) no C2 N1 C11 C12 39.4(3) no C1 N1 C11 C12 -140.2(2) no C2 N1 C11 C16 -140.0(2) no C1 N1 C11 C16 40.3(3) no C16 C11 C12 C13 2.9(3) no N1 C11 C12 C13 -176.58(19) no C11 C12 C13 C14 -1.7(3) no C12 C13 C14 C15 -0.9(3) no C12 C13 C14 I14 178.09(16) no C13 C14 C15 C16 2.5(3) no I14 C14 C15 C16 -176.55(17) no C14 C15 C16 C11 -1.3(3) no C12 C11 C16 C15 -1.4(3) no N1 C11 C16 C15 178.1(2) no