#------------------------------------------------------------------------------ #$Date: 2013-12-28 14:58:47 +0100 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/01/2100141.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_2100141 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-(3-Iodophenyl)-4-nitrophthalimide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 97.960(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.9592(9) _cell_length_b 6.5708(7) _cell_length_c 25.648(3) _cell_measurement_reflns_used 4808 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 32.59 _cell_measurement_theta_min 2.58 _cell_volume 1328.4(3) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 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 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0855 _diffrn_reflns_av_sigmaI/netI 0.1574 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 13842 _diffrn_reflns_theta_full 32.59 _diffrn_reflns_theta_max 32.59 _diffrn_reflns_theta_min 2.58 _diffrn_standards_decay_% nil _exptl_absorpt_coefficient_mu 2.428 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_correction_T_min 0.539 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.971 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.700 _refine_diff_density_min -0.347 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.766 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 4808 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.766 _refine_ls_R_factor_all 0.2007 _refine_ls_R_factor_gt 0.0488 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.0974 _reflns_number_gt 1564 _reflns_number_total 4808 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm5022.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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 2100141 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, 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 0.2572(4) 0.3057(5) 0.23850(13) 0.0359(8) Uani d . 1 . . N C1 0.3679(6) 0.3800(7) 0.28155(19) 0.0469(12) Uani d . 1 . . C O1 0.4498(4) 0.5353(6) 0.28135(13) 0.0664(10) Uani d . 1 . . O C2 0.1811(5) 0.1229(7) 0.25127(18) 0.0392(11) Uani d . 1 . . C O2 0.0761(4) 0.0303(5) 0.22220(12) 0.0498(8) Uani d . 1 . . O C3 0.2518(5) 0.0768(7) 0.30601(17) 0.0418(11) Uani d . 1 . . C C4 0.2227(6) -0.0859(7) 0.3380(2) 0.0492(12) Uani d . 1 . . C C5 0.3031(6) -0.0746(8) 0.3891(2) 0.0519(13) Uani d . 1 . . C N5 0.2700(6) -0.2417(8) 0.4253(2) 0.0704(14) Uani d . 1 . . N O51 0.3144(5) -0.2137(7) 0.47317(17) 0.1032(15) Uani d . 1 . . O O52 0.2001(6) -0.3948(7) 0.40603(19) 0.0953(15) Uani d . 1 . . O C6 0.4063(6) 0.0804(9) 0.4095(2) 0.0590(14) Uani d . 1 . . C C7 0.4379(6) 0.2369(8) 0.3764(2) 0.0552(13) Uani d . 1 . . C C8 0.3598(6) 0.2327(7) 0.32509(18) 0.0428(12) Uani d . 1 . . C C11 0.2265(5) 0.3960(7) 0.18761(18) 0.0387(11) Uani d . 1 . . C C12 0.2393(5) 0.2767(7) 0.14373(17) 0.0411(11) Uani d . 1 . . C C13 0.1986(5) 0.3555(7) 0.09433(17) 0.0457(11) Uani d . 1 . . C C14 0.1423(6) 0.5562(8) 0.0878(2) 0.0530(13) Uani d . 1 . . C C15 0.1326(5) 0.6747(8) 0.1317(2) 0.0500(12) Uani d . 1 . . C C16 0.1756(5) 0.5957(7) 0.1812(2) 0.0471(12) Uani d . 1 . . C I13 0.21726(5) 0.16750(6) 0.029415(13) 0.06463(15) Uani d . 1 . . I H4 0.1537 -0.1950 0.3259 0.059 Uiso calc R 1 . . H H6 0.4538 0.0803 0.4447 0.071 Uiso calc R 1 . . H H7 0.5104 0.3429 0.3885 0.066 Uiso calc R 1 . . H H12 0.2758 0.1425 0.1480 0.049 Uiso calc R 1 . . H H14 0.1117 0.6094 0.0543 0.064 Uiso calc R 1 . . H H15 0.0966 0.8092 0.1276 0.060 Uiso calc R 1 . . H H16 0.1704 0.6773 0.2106 0.057 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 0.039(2) 0.033(2) 0.0355(19) -0.0005(18) 0.0049(16) -0.0012(17) C1 0.047(3) 0.044(3) 0.051(3) 0.000(3) 0.011(2) -0.004(2) O1 0.071(2) 0.064(3) 0.061(2) -0.029(2) -0.0007(18) 0.0007(19) C2 0.036(3) 0.036(3) 0.047(3) 0.002(2) 0.012(2) -0.009(2) O2 0.061(2) 0.0348(19) 0.053(2) -0.0075(17) 0.0065(17) -0.0059(16) C3 0.034(3) 0.048(3) 0.045(3) 0.009(2) 0.009(2) 0.005(2) C4 0.043(3) 0.045(3) 0.062(3) 0.007(2) 0.014(3) 0.002(2) C5 0.047(3) 0.061(4) 0.051(3) 0.019(3) 0.018(3) 0.016(3) N5 0.067(3) 0.072(4) 0.074(4) 0.016(3) 0.018(3) 0.031(3) O51 0.125(4) 0.126(4) 0.057(3) 0.001(3) 0.011(3) 0.040(3) O52 0.119(4) 0.069(3) 0.101(4) -0.009(3) 0.024(3) 0.024(3) C6 0.056(3) 0.076(4) 0.045(3) 0.010(3) 0.008(3) -0.002(3) C7 0.050(3) 0.060(3) 0.055(3) 0.000(2) 0.007(3) 0.003(3) C8 0.041(3) 0.050(3) 0.040(3) -0.002(2) 0.015(2) -0.001(2) C11 0.035(3) 0.034(3) 0.048(3) -0.003(2) 0.007(2) 0.001(2) C12 0.047(3) 0.032(3) 0.044(3) 0.003(2) 0.003(2) -0.002(2) C13 0.043(3) 0.048(3) 0.046(3) -0.009(3) 0.006(2) 0.003(2) C14 0.050(3) 0.056(4) 0.052(3) -0.009(3) 0.001(2) 0.018(3) C15 0.050(3) 0.033(3) 0.067(3) 0.002(3) 0.009(2) 0.006(3) C16 0.050(3) 0.035(3) 0.058(3) -0.005(2) 0.013(2) -0.003(2) I13 0.0827(3) 0.0657(3) 0.04511(19) -0.0086(2) 0.00785(16) -0.0063(2) 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(6) ? N1 C2 . 1.404(5) ? N1 C11 . 1.424(5) ? C1 O1 . 1.212(5) ? C1 C8 . 1.486(6) ? C2 O2 . 1.205(5) ? C2 C3 . 1.470(6) ? C3 C8 . 1.382(6) ? C3 C4 . 1.387(6) ? C4 C5 . 1.377(7) ? C4 H4 . 0.9300 ? C5 C6 . 1.366(7) ? C5 N5 . 1.486(6) ? N5 O52 . 1.221(6) ? N5 O51 . 1.243(6) ? C6 C7 . 1.378(6) ? C6 H6 . 0.9300 ? C7 C8 . 1.376(6) ? C7 H7 . 0.9300 ? C11 C16 . 1.376(6) ? C11 C12 . 1.387(6) ? C12 C13 . 1.366(6) ? C12 H12 . 0.9300 ? C13 C14 . 1.395(6) ? C13 I13 . 2.095(5) ? C14 C15 . 1.378(6) ? C14 H14 . 0.9300 ? C15 C16 . 1.373(6) ? C15 H15 . 0.9300 ? C16 H16 . 0.9300 ? 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 C1 N1 C2 111.0(4) C1 N1 C11 125.9(4) C2 N1 C11 123.1(3) O1 C1 N1 124.7(4) O1 C1 C8 129.1(5) N1 C1 C8 106.1(4) O2 C2 N1 124.9(4) O2 C2 C3 128.9(4) N1 C2 C3 106.2(4) C8 C3 C4 120.5(4) C8 C3 C2 108.8(4) C4 C3 C2 130.6(5) C5 C4 C3 115.3(5) C5 C4 H4 122.3 C3 C4 H4 122.3 C6 C5 C4 125.5(5) C6 C5 N5 117.4(5) C4 C5 N5 117.1(5) O52 N5 O51 125.0(5) O52 N5 C5 117.8(5) O51 N5 C5 117.3(6) C5 C6 C7 118.2(5) C5 C6 H6 120.9 C7 C6 H6 120.9 C8 C7 C6 118.5(5) C8 C7 H7 120.8 C6 C7 H7 120.8 C7 C8 C3 122.0(4) C7 C8 C1 130.2(5) C3 C8 C1 107.8(4) C16 C11 C12 119.7(4) C16 C11 N1 121.1(4) C12 C11 N1 119.1(4) C13 C12 C11 120.2(4) C13 C12 H12 119.9 C11 C12 H12 119.9 C12 C13 C14 120.0(4) C12 C13 I13 118.7(4) C14 C13 I13 121.3(4) C15 C14 C13 119.4(5) C15 C14 H14 120.3 C13 C14 H14 120.3 C16 C15 C14 120.4(5) C16 C15 H15 119.8 C14 C15 H15 119.8 C15 C16 C11 120.2(5) C15 C16 H16 119.9 C11 C16 H16 119.9 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 C16 H16 O2 1_565 0.93 2.47 3.181(6) 133 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 C2 N1 C1 O1 -179.9(4) C11 N1 C1 O1 1.9(7) C2 N1 C1 C8 -0.5(5) C11 N1 C1 C8 -178.7(4) C1 N1 C2 O2 177.2(4) C11 N1 C2 O2 -4.5(6) C1 N1 C2 C3 -1.2(4) C11 N1 C2 C3 177.1(4) O2 C2 C3 C8 -175.7(4) N1 C2 C3 C8 2.5(5) O2 C2 C3 C4 2.6(8) N1 C2 C3 C4 -179.2(4) C8 C3 C4 C5 2.2(6) C2 C3 C4 C5 -176.0(4) C3 C4 C5 C6 -0.1(7) C3 C4 C5 N5 177.7(4) C6 C5 N5 O52 -169.1(5) C4 C5 N5 O52 12.9(7) C6 C5 N5 O51 11.6(7) C4 C5 N5 O51 -166.4(4) C4 C5 C6 C7 -2.0(7) N5 C5 C6 C7 -179.8(4) C5 C6 C7 C8 2.1(7) C6 C7 C8 C3 -0.2(7) C6 C7 C8 C1 178.9(4) C4 C3 C8 C7 -2.1(7) C2 C3 C8 C7 176.4(4) C4 C3 C8 C1 178.7(4) C2 C3 C8 C1 -2.8(5) O1 C1 C8 C7 2.3(8) N1 C1 C8 C7 -177.1(4) O1 C1 C8 C3 -178.5(5) N1 C1 C8 C3 2.1(5) C1 N1 C11 C16 -54.9(6) C2 N1 C11 C16 127.0(4) C1 N1 C11 C12 128.7(4) C2 N1 C11 C12 -49.4(5) C16 C11 C12 C13 -1.2(6) N1 C11 C12 C13 175.2(4) C11 C12 C13 C14 -0.6(6) C11 C12 C13 I13 -179.2(3) C12 C13 C14 C15 1.6(7) I13 C13 C14 C15 -179.8(3) C13 C14 C15 C16 -0.9(7) C14 C15 C16 C11 -1.0(7) C12 C11 C16 C15 2.0(6) N1 C11 C16 C15 -174.3(4) _journal_paper_doi 10.1107/S0108768105004234