#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100585.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_2100585 loop_ _publ_author_name 'Wardell, James L.' 'Low, John Nicolson' 'Skakle, Janet M.S.' 'Glidewell, Christopher' _publ_section_title ; Isomeric N-(iodophenyl)nitrobenzamides form different three-dimensional framework structures ; _journal_coeditor_code BM5035 _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 931 _journal_page_last 943 _journal_paper_doi 10.1107/S0108768106029053 _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C13 H9 I N2 O3' _chemical_formula_sum 'C13 H9 I N2 O3' _chemical_formula_weight 368.12 _chemical_name_systematic ; N-(3-iodophenyl)-3-nitrobenzamide ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 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 105.2353(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.8494(4) _cell_length_b 10.0495(3) _cell_length_c 9.4203(3) _cell_measurement_reflns_used 2797 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 4.06 _cell_volume 1265.03(7) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'DENZO & COLLECT)' _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_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7022 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 4.06 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 2.536 _exptl_absorpt_correction_T_max 0.666 _exptl_absorpt_correction_T_min 0.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.557 _refine_diff_density_min -1.094 _refine_ls_abs_structure_details 'Flack (1983), 1349 Friedel pairs' _refine_ls_abs_structure_Flack 0.013(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2797 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.244 _refine_ls_R_factor_all 0.0185 _refine_ls_R_factor_gt 0.0180 _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^)+(0.0227P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.0527 _reflns_number_gt 2752 _reflns_number_total 2797 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm5035.cif _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_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_original_sg_symbol_H-M 'C c' _cod_database_code 2100585 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' loop_ _atom_site_type_symbol _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 C C11 0.7797(2) 0.6833(3) 0.7339(3) 0.0116(6) Uani d . 1 C C12 0.8261(2) 0.6561(3) 0.6247(3) 0.0117(5) Uani d . 1 C C13 0.8695(4) 0.7603(3) 0.5672(6) 0.0134(8) Uani d . 1 C C14 0.8706(2) 0.8902(3) 0.6162(3) 0.0176(6) Uani d . 1 C C15 0.8241(2) 0.9169(3) 0.7266(3) 0.0160(6) Uani d . 1 C C16 0.7794(2) 0.8146(3) 0.7857(3) 0.0152(6) Uani d . 1 C C17 0.72916(19) 0.5797(3) 0.8039(3) 0.0125(5) Uani d . 1 O O17 0.71903(16) 0.5977(2) 0.92908(19) 0.0143(4) Uani d . 1 N N1 0.69589(15) 0.4705(2) 0.7215(2) 0.0122(4) Uani d . 1 C C21 0.6521(2) 0.3559(3) 0.7658(3) 0.0131(6) Uani d . 1 C C22 0.6025(2) 0.3578(3) 0.8765(3) 0.0141(6) Uani d . 1 C C23 0.5646(3) 0.2390(2) 0.9152(4) 0.0134(7) Uani d . 1 C C24 0.5712(2) 0.1206(3) 0.8434(3) 0.0172(7) Uani d . 1 C C25 0.6176(2) 0.1212(3) 0.7283(4) 0.0189(7) Uani d . 1 C C26 0.6584(4) 0.2369(3) 0.6902(6) 0.0173(9) Uani d . 1 N N13 0.9173(3) 0.7305(2) 0.4484(4) 0.0178(6) Uani d . 1 O O31 0.91357(17) 0.6161(2) 0.4020(2) 0.0254(5) Uani d . 1 O O32 0.95718(19) 0.8224(2) 0.3990(3) 0.0297(5) Uani d . 1 I I23 0.50081(5) 0.240359(12) 1.09460(7) 0.01576(7) Uani d . 1 H H12 0.8284 0.5679 0.5895 0.014 Uiso calc R 1 H H14 0.9022 0.9588 0.5754 0.021 Uiso calc R 1 H H15 0.8228 1.0052 0.7620 0.019 Uiso calc R 1 H H16 0.7483 0.8335 0.8621 0.018 Uiso calc R 1 H H1 0.7088 0.4646 0.6351 0.015 Uiso d R 1 H H22 0.5946 0.4386 0.9246 0.017 Uiso calc R 1 H H24 0.5449 0.0406 0.8717 0.021 Uiso calc R 1 H H25 0.6211 0.0414 0.6758 0.023 Uiso calc R 1 H H26 0.6907 0.2361 0.6128 0.021 Uiso calc R 1 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 C11 0.0119(14) 0.0093(14) 0.0125(14) 0.0008(11) 0.0011(11) 0.0001(11) C12 0.0131(12) 0.0117(14) 0.0106(12) 0.0015(10) 0.0035(11) 0.0022(10) C13 0.014(2) 0.0163(18) 0.012(2) 0.0029(10) 0.0072(18) 0.0003(11) C14 0.0189(15) 0.0138(14) 0.0204(14) -0.0044(11) 0.0057(12) 0.0035(11) C15 0.0221(15) 0.0087(14) 0.0181(14) -0.0047(12) 0.0068(12) -0.0010(11) C16 0.0191(15) 0.0123(15) 0.0145(15) 0.0001(12) 0.0048(13) -0.0024(12) C17 0.0134(12) 0.0105(13) 0.0124(12) 0.0026(10) 0.0013(10) 0.0021(11) O17 0.0228(10) 0.0140(11) 0.0081(8) -0.0029(8) 0.0077(8) 0.0014(7) N1 0.0174(12) 0.0123(11) 0.0087(10) -0.0031(9) 0.0067(9) 0.0001(8) C21 0.0151(15) 0.0123(14) 0.0109(13) 0.0007(11) 0.0017(11) 0.0020(10) C22 0.0156(15) 0.0125(14) 0.0144(15) 0.0005(11) 0.0041(12) 0.0008(11) C23 0.0116(18) 0.0179(17) 0.0123(18) -0.0014(10) 0.0061(14) 0.0008(9) C24 0.0196(18) 0.0134(15) 0.0202(16) -0.0027(12) 0.0077(14) 0.0024(13) C25 0.0214(17) 0.0140(15) 0.0231(16) -0.0017(12) 0.0088(13) -0.0031(13) C26 0.028(3) 0.0145(17) 0.012(2) -0.0006(12) 0.0097(19) 0.0016(12) N13 0.0184(16) 0.0208(14) 0.0174(16) 0.0051(11) 0.0102(13) 0.0042(11) O31 0.0309(13) 0.0216(13) 0.0295(13) -0.0015(10) 0.0181(11) -0.0044(11) O32 0.0404(14) 0.0252(13) 0.0339(13) 0.0011(11) 0.0279(12) 0.0093(11) I23 0.01521(11) 0.01944(10) 0.01474(11) -0.00027(18) 0.00768(7) 0.00355(17) 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 C12 C11 C16 119.3(3) no C12 C11 C17 123.7(2) no C16 C11 C17 117.1(2) no C11 C12 C13 118.6(3) no C11 C12 H12 120.7 no C13 C12 H12 120.7 no C14 C13 C12 123.4(4) no C14 C13 N13 118.5(3) no C12 C13 N13 118.1(3) no C13 C14 C15 117.8(3) no C13 C14 H14 121.1 no C15 C14 H14 121.1 no C14 C15 C16 120.1(3) no C14 C15 H15 120.0 no C16 C15 H15 120.0 no C15 C16 C11 120.9(3) no C15 C16 H16 119.6 no C11 C16 H16 119.6 no O17 C17 N1 124.0(2) no O17 C17 C11 120.0(2) no N1 C17 C11 116.0(2) no C17 N1 C21 126.7(2) no C17 N1 H1 117.7 no C21 N1 H1 115.2 no C22 C21 C26 120.0(3) no C22 C21 N1 123.0(3) no C26 C21 N1 117.0(3) no C23 C22 C21 118.6(3) no C23 C22 H22 120.7 no C21 C22 H22 120.7 no C24 C23 C22 122.2(4) no C24 C23 I23 119.6(2) no C22 C23 I23 118.2(2) no C23 C24 C25 118.6(3) no C23 C24 H24 120.7 no C25 C24 H24 120.7 no C26 C25 C24 120.5(3) no C26 C25 H25 119.7 no C24 C25 H25 119.7 no C25 C26 C21 120.0(4) no C25 C26 H26 120.0 no C21 C26 H26 120.0 no O31 N13 O32 123.4(3) no O31 N13 C13 118.4(3) no O32 N13 C13 118.1(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C11 C12 1.377(4) no C11 C16 1.407(5) no C11 C17 1.500(4) no C12 C13 1.386(4) no C12 H12 0.95 no C13 C14 1.383(4) no C13 N13 1.473(6) no C14 C15 1.386(4) no C14 H14 0.95 no C15 C16 1.390(4) no C15 H15 0.95 no C16 H16 0.95 no C17 O17 1.237(3) no C17 N1 1.353(3) no N1 C21 1.415(3) no N1 H1 0.88 no C21 C22 1.392(4) no C21 C26 1.406(4) no C22 C23 1.391(4) no C22 H22 0.95 no C23 C24 1.384(4) no C23 I23 2.103(4) no C24 C25 1.397(5) no C24 H24 0.95 no C25 C26 1.381(4) no C25 H25 0.95 no C26 H26 0.95 no N13 O31 1.226(3) no N13 O32 1.228(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 N1 H1 O17 2_564 0.88 2.08 2.937(2) 165 no C12 H12 O17 2_564 0.95 2.48 3.266(4) 140 no C24 H24 O31 4_455 0.95 2.48 3.371(4) 157 no C26 H26 O17 2_564 0.95 2.51 3.256(5) 136 no 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 C16 C11 C12 C13 -1.3(4) no C17 C11 C12 C13 179.4(3) no C11 C12 C13 C14 1.5(6) no C11 C12 C13 N13 -178.8(3) no C12 C13 C14 C15 -1.2(6) no N13 C13 C14 C15 179.1(3) no C13 C14 C15 C16 0.7(4) no C14 C15 C16 C11 -0.6(4) no C12 C11 C16 C15 0.9(4) no C17 C11 C16 C15 -179.7(3) no C12 C11 C17 O17 155.7(3) no C16 C11 C17 O17 -23.7(4) no C12 C11 C17 N1 -25.2(4) no C16 C11 C17 N1 155.5(2) no O17 C17 N1 C21 -5.4(4) no C11 C17 N1 C21 175.5(2) no C17 N1 C21 C22 25.7(4) no C17 N1 C21 C26 -155.9(3) no C26 C21 C22 C23 3.5(5) no N1 C21 C22 C23 -178.1(3) no C21 C22 C23 C24 -2.7(5) no C21 C22 C23 I23 174.8(2) no C22 C23 C24 C25 0.0(5) no I23 C23 C24 C25 -177.4(2) no C23 C24 C25 C26 1.8(5) no C24 C25 C26 C21 -1.0(6) no C22 C21 C26 C25 -1.7(6) no N1 C21 C26 C25 179.7(4) no C14 C13 N13 O31 -177.8(4) no C12 C13 N13 O31 2.5(6) no C14 C13 N13 O32 0.8(6) no C12 C13 N13 O32 -178.8(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2348236 2 PubChem 3092325