#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/28/2012818.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_2012818 loop_ _publ_author_name 'Wardell, James L.' 'Wardell, Solange M. S. V.' 'Skakle, Janet M. S.' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; N-(2-Iodobenzylidene)-3-nitroaniline: sheets formed by a combination of C---H···O hydrogen bonds and two aromatic \p--\p-stacking interactions ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o428 _journal_page_last o430 _journal_paper_doi 10.1107/S0108270102008624 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C13 H9 I N2 O2' _chemical_formula_sum 'C13 H9 I N2 O2' _chemical_formula_weight 352.12 _chemical_melting_point 346 _chemical_name_systematic ; N-(2-Iodobenzylidene)-3-nitroaniline ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 82.2570(9) _cell_angle_beta 71.5605(8) _cell_angle_gamma 62.7543(10) _cell_formula_units_Z 2 _cell_length_a 7.7405(2) _cell_length_b 8.3297(2) _cell_length_c 11.3317(3) _cell_measurement_reflns_used 2720 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.1 _cell_volume 616.17(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _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 0.064 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8201 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.1 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 2.593 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_correction_T_min 0.464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 340 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.80 _refine_diff_density_min -1.60 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2720 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.030 _refine_ls_R_factor_gt 0.028 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0278P)^2^+0.3610P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.067 _refine_ls_wR_factor_ref 0.068 _reflns_number_gt 2596 _reflns_number_total 2720 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gg1119.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 2012818 _cod_database_fobs_code 2012818 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 C1 0.7422(3) 0.0695(3) 0.3077(2) 0.0164(5) Uani d . 1 . . C N1 0.7310(3) 0.1564(3) 0.1922(2) 0.0183(4) Uani d . 1 . . N C2 0.7499(4) -0.1018(3) 0.3290(2) 0.0165(5) Uani d . 1 . . C C3 0.7636(4) -0.1796(3) 0.4437(2) 0.0172(5) Uani d . 1 . . C N3 0.7716(3) -0.3600(3) 0.4652(2) 0.0225(5) Uani d . 1 . . N O31 0.7780(4) -0.4380(3) 0.3785(2) 0.0371(5) Uani d . 1 . . O O32 0.7710(3) -0.4248(3) 0.5691(2) 0.0322(5) Uani d . 1 . . O C4 0.7705(4) -0.0952(4) 0.5378(2) 0.0214(5) Uani d . 1 . . C C5 0.7635(4) 0.0749(4) 0.5149(3) 0.0235(6) Uani d . 1 . . C C6 0.7519(4) 0.1560(4) 0.4008(3) 0.0201(5) Uani d . 1 . . C C11 0.5803(4) 0.2370(3) 0.0246(2) 0.0163(5) Uani d . 1 . . C C12 0.4086(4) 0.2768(3) -0.0131(2) 0.0153(5) Uani d . 1 . . C I12 0.15723(2) 0.23901(2) 0.102073(14) 0.02085(8) Uani d . 1 . . I C13 0.3940(4) 0.3507(3) -0.1292(2) 0.0185(5) Uani d . 1 . . C C14 0.5492(4) 0.3842(4) -0.2092(3) 0.0201(5) Uani d . 1 . . C C15 0.7211(4) 0.3454(3) -0.1738(3) 0.0205(5) Uani d . 1 . . C C16 0.7343(4) 0.2734(3) -0.0579(3) 0.0196(5) Uani d . 1 . . C C17 0.6006(4) 0.1579(3) 0.1460(2) 0.0168(5) Uani d . 1 . . C H2 0.7458 -0.1640 0.2662 0.020 Uiso calc R 1 . . H H4 0.7798 -0.1519 0.6156 0.026 Uiso calc R 1 . . H H5 0.7666 0.1367 0.5782 0.028 Uiso calc R 1 . . H H6 0.7505 0.2715 0.3860 0.024 Uiso calc R 1 . . H H13 0.2767 0.3780 -0.1534 0.022 Uiso calc R 1 . . H H14 0.5393 0.4339 -0.2887 0.024 Uiso calc R 1 . . H H15 0.8285 0.3684 -0.2289 0.025 Uiso calc R 1 . . H H16 0.8513 0.2482 -0.0341 0.023 Uiso calc R 1 . . H H17 0.5131 0.1058 0.1918 0.020 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 C1 0.0097(10) 0.0194(12) 0.0192(12) -0.0061(9) -0.0044(9) 0.0025(9) N1 0.0185(10) 0.0161(11) 0.0204(11) -0.0074(8) -0.0073(9) 0.0038(8) C2 0.0144(11) 0.0187(12) 0.0176(12) -0.0071(9) -0.0068(9) 0.0007(10) C3 0.0117(11) 0.0199(12) 0.0205(13) -0.0080(9) -0.0045(9) 0.0022(10) N3 0.0178(10) 0.0233(12) 0.0257(12) -0.0092(9) -0.0090(9) 0.0093(10) O31 0.0610(15) 0.0246(11) 0.0399(13) -0.0245(10) -0.0278(12) 0.0093(10) O32 0.0323(11) 0.0358(12) 0.0282(11) -0.0182(9) -0.0104(9) 0.0176(9) C4 0.0148(11) 0.0306(14) 0.0165(12) -0.0081(10) -0.0059(10) 0.0031(10) C5 0.0180(12) 0.0295(15) 0.0226(14) -0.0077(11) -0.0071(11) -0.0058(11) C6 0.0153(12) 0.0203(13) 0.0268(14) -0.0076(10) -0.0079(11) -0.0031(11) C11 0.0151(11) 0.0127(12) 0.0196(13) -0.0046(9) -0.0056(10) -0.0007(9) C12 0.0138(11) 0.0138(12) 0.0174(12) -0.0053(9) -0.0041(9) -0.0003(9) I12 0.01522(11) 0.02461(13) 0.02394(13) -0.01003(8) -0.00601(8) 0.00203(8) C13 0.0193(12) 0.0161(12) 0.0208(13) -0.0052(10) -0.0098(10) -0.0015(10) C14 0.0233(13) 0.0183(13) 0.0158(12) -0.0067(10) -0.0060(10) 0.0007(10) C15 0.0187(12) 0.0202(13) 0.0200(13) -0.0083(10) -0.0028(10) 0.0004(10) C16 0.0159(11) 0.0201(13) 0.0227(13) -0.0079(10) -0.0065(10) 0.0025(10) C17 0.0153(11) 0.0142(12) 0.0193(12) -0.0056(9) -0.0049(9) 0.0014(9) 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 C1 C6 119.4(2) no C2 C1 N1 121.6(2) no C6 C1 N1 119.0(2) no C17 N1 C1 117.4(2) no C3 C2 C1 118.4(2) no C3 C2 H2 120.8 no C1 C2 H2 120.8 no C4 C3 C2 123.0(2) no C4 C3 N3 118.9(2) no C2 C3 N3 118.0(2) no O31 N3 O32 123.5(2) no O31 N3 C3 118.3(2) no O32 N3 C3 118.2(2) no C3 C4 C5 117.8(2) no C3 C4 H4 121.1 no C5 C4 H4 121.1 no C4 C5 C6 120.8(2) no C4 C5 H5 119.6 no C6 C5 H5 119.6 no C5 C6 C1 120.6(3) no C5 C6 H6 119.7 no C1 C6 H6 119.7 no C16 C11 C12 117.9(2) no C12 C11 C17 122.0(2) y C16 C11 C17 120.2(2) y C11 C12 I12 122.97(18) y C13 C12 I12 116.26(17) y C13 C12 C11 120.7(2) no C14 C13 C12 120.1(2) no C14 C13 H13 120.0 no C12 C13 H13 120.0 no C13 C14 C15 120.1(2) no C13 C14 H14 119.9 no C15 C14 H14 119.9 no C16 C15 C14 119.6(2) no C16 C15 H15 120.2 no C14 C15 H15 120.2 no C15 C16 C11 121.6(2) no C15 C16 H16 119.2 no C11 C16 H16 119.2 no N1 C17 C11 122.4(2) no N1 C17 H17 118.8 no C11 C17 H17 118.8 no 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 C1 C2 . 1.392(4) no C1 C6 . 1.394(4) no C1 N1 . 1.415(3) no N1 C17 . 1.270(3) no C2 C3 . 1.385(4) no C2 H2 . 0.9500 no C3 C4 . 1.381(4) no C3 N3 . 1.466(3) no N3 O31 . 1.224(3) no N3 O32 . 1.227(3) no C4 C5 . 1.384(4) no C4 H4 . 0.9500 no C5 C6 . 1.385(4) no C5 H5 . 0.9500 no C6 H6 . 0.9500 no C11 C16 . 1.392(4) no C11 C12 . 1.406(3) no C11 C17 . 1.467(4) no C12 C13 . 1.391(4) no C12 I12 . 2.105(2) no C13 C14 . 1.376(4) no C13 H13 . 0.9500 no C14 C15 . 1.394(4) no C14 H14 . 0.9500 no C15 C16 . 1.382(4) no C15 H15 . 0.9500 no C16 H16 . 0.9500 no C17 H17 . 0.9500 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 C6 H6 O31 1_565 0.95 2.51 3.450(4) 169 y C17 H17 I12 . 0.95 2.92 3.369(2) 110 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 C1 N1 C17 C11 -177.4(2) y N1 C17 C11 C12 -164.7(2) y C17 N1 C1 C2 47.9(4) y C2 C3 N3 O31 4.3(4) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 91182385