#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013126.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_2013126 loop_ _publ_author_name 'Merz, Klaus' _publ_section_title ; Secondary interactions in 1-iodo-3-nitrobenzene and 1-iodo-3,5-dinitrobenzene ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o65 _journal_page_last o67 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C6 H3 I1 N2 O4' _chemical_formula_sum 'C6 H3 I N2 O4' _chemical_formula_weight 294.00 _chemical_name_common 3-Iodo-5-dinitro-benzene _chemical_name_systematic ; 3-iodo-1,5-dinitro-benzene ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 101.766(12) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.842(9) _cell_length_b 8.164(5) _cell_length_c 15.288(9) _cell_measurement_reflns_used 53 _cell_measurement_temperature 213(2) _cell_measurement_theta_max 17.6 _cell_measurement_theta_min 3.4 _cell_volume 1691.3(18) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL and ORTEPIII (Farrugia, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Siemens, 1996)' _diffrn_ambient_temperature 213(2) _diffrn_measured_fraction_theta_full 0.970 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.061 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 6318 _diffrn_reflns_theta_full 30.01 _diffrn_reflns_theta_max 30.01 _diffrn_reflns_theta_min 2.91 _diffrn_standards_decay_% 0.1 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.770 _exptl_absorpt_correction_T_max 0.470 _exptl_absorpt_correction_T_min 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '[SADABS (Sheldrick, 1996; Blessing, 1995)]' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.309 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.93 _refine_diff_density_min -0.99 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 2404 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.052 _refine_ls_R_factor_gt 0.037 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0103P)^2^+2.3695P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.080 _refine_ls_wR_factor_ref 0.084 _reflns_number_gt 1927 _reflns_number_total 2404 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file dn1017.cif _[local]_cod_data_source_block III _[local]_cod_cif_authors_sg_H-M 'C 2/c' _[local]_cod_chemical_formula_sum_orig 'C6 H3 I1 N2 O4' _cod_original_cell_volume 1691.2(18) _cod_database_code 2013126 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' '-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_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 I1 0.100566(19) 0.80925(3) 0.380331(14) 0.03627(11) Uani d . 1 . . I O1 0.1019(3) 0.6800(4) 0.80264(19) 0.0559(9) Uani d . 1 . . O C1 0.1186(3) 0.6743(4) 0.6559(2) 0.0287(7) Uani d . 1 . . C C2 0.1089(3) 0.7634(4) 0.5773(2) 0.0270(7) Uani d . 1 . . C H2A 0.0980 0.8771 0.5763 0.032 Uiso calc R 1 . . H C3 0.1158(3) 0.6784(4) 0.5002(2) 0.0259(7) Uani d . 1 . . C N1 0.1096(3) 0.7627(5) 0.7376(2) 0.0435(9) Uani d . 1 . . N C6 0.1357(3) 0.5090(5) 0.6610(2) 0.0304(8) Uani d . 1 . . C H6A 0.1422 0.4513 0.7151 0.036 Uiso calc R 1 . . H O3 0.1861(3) 0.1901(4) 0.6581(3) 0.0648(11) Uani d . 1 . . O C4 0.1326(3) 0.5120(5) 0.5017(2) 0.0295(7) Uani d . 1 . . C H4A 0.1370 0.4547 0.4493 0.035 Uiso calc R 1 . . H O2 0.1094(4) 0.9105(5) 0.7352(2) 0.0717(12) Uani d . 1 . . O N2 0.1617(3) 0.2547(5) 0.5853(3) 0.0412(8) Uani d . 1 . . N C5 0.1427(3) 0.4324(4) 0.5828(2) 0.0294(7) Uani d . 1 . . C O4 0.1494(4) 0.1813(4) 0.5149(3) 0.0734(13) Uani d . 1 . . O 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 I1 0.04522(17) 0.04186(17) 0.02156(12) -0.00267(12) 0.00645(10) 0.00836(9) O1 0.070(2) 0.077(3) 0.0245(13) 0.0093(19) 0.0184(14) 0.0080(13) C1 0.0337(18) 0.035(2) 0.0190(14) -0.0019(16) 0.0084(13) -0.0003(12) C2 0.0361(19) 0.0202(16) 0.0265(15) -0.0005(15) 0.0110(14) 0.0029(12) C3 0.0287(16) 0.0291(18) 0.0202(14) -0.0019(15) 0.0057(12) 0.0030(12) N1 0.060(2) 0.052(2) 0.0208(14) 0.001(2) 0.0134(15) -0.0031(14) C6 0.0321(18) 0.0319(19) 0.0276(16) -0.0008(16) 0.0069(14) 0.0098(13) O3 0.083(3) 0.0376(19) 0.070(2) 0.0053(19) 0.006(2) 0.0210(15) C4 0.0335(18) 0.0285(18) 0.0272(16) -0.0010(16) 0.0078(13) -0.0034(13) O2 0.133(4) 0.044(2) 0.0466(18) -0.009(2) 0.040(2) -0.0178(15) N2 0.0399(19) 0.0253(16) 0.058(2) 0.0007(16) 0.0086(16) 0.0019(16) C5 0.0307(17) 0.0238(17) 0.0325(17) -0.0018(16) 0.0038(13) 0.0058(13) O4 0.118(4) 0.0310(18) 0.069(3) 0.008(2) 0.014(2) -0.0094(15) 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 I1 C3 . 2.094(3) yes O1 N1 . 1.225(5) yes C1 C6 . 1.370(5) ? C1 C2 . 1.388(5) ? C1 N1 . 1.470(5) yes C2 C3 . 1.388(5) ? C2 H2A . 0.9400 ? C3 C4 . 1.377(5) ? N1 O2 . 1.207(6) yes C6 C5 . 1.370(5) ? C6 H6A . 0.9400 ? O3 N2 . 1.215(5) yes C4 C5 . 1.383(5) ? C4 H4A . 0.9400 ? N2 O4 . 1.213(5) yes N2 C5 . 1.473(5) yes 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' 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' I I -0.4742 1.8119 '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 C6 C1 C2 123.5(3) ? C6 C1 N1 118.6(3) yes C2 C1 N1 117.9(3) yes C1 C2 C3 117.5(3) ? C1 C2 H2A 121.3 ? C3 C2 H2A 121.3 ? C4 C3 C2 121.3(3) ? C4 C3 I1 120.3(2) yes C2 C3 I1 118.4(3) yes O2 N1 O1 125.1(4) yes O2 N1 C1 117.8(3) yes O1 N1 C1 117.1(4) yes C1 C6 C5 116.2(3) ? C1 C6 H6A 121.9 ? C5 C6 H6A 121.9 ? C3 C4 C5 117.7(3) ? C3 C4 H4A 121.2 ? C5 C4 H4A 121.2 ? O4 N2 O3 124.1(4) yes O4 N2 C5 118.1(4) yes O3 N2 C5 117.7(4) yes C6 C5 C4 123.8(3) ? C6 C5 N2 118.1(3) yes C4 C5 N2 118.1(3) yes _cod_database_fobs_code 2013126