#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012907.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_2012907 loop_ _publ_author_name 'Garden, Simon J.' 'da Cunha, Fernanda R. ' 'Wardell, James L.' 'Skakle, Janet M. S.' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; 2,6-Diiodo-4-nitrophenol, 2,6-diiodo-4-nitrophenyl acetate and 2,6-diiodo-4-nitroanisole: interplay of hydrogen bonds, iodo--nitro interactions and aromatic \p--\p-stacking interactions to give supramolecular structures in one, two and three dimensions ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o463 _journal_page_last o466 _journal_paper_doi 10.1107/S0108270102010776 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C6 H3 I2 N O3' _chemical_formula_sum 'C6 H3 I2 N O3' _chemical_formula_weight 390.89 _chemical_name_systematic ; 2,6-Diiodo-4-nitrophenol ; _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 69.3082(18) _cell_angle_beta 66.657(2) _cell_angle_gamma 67.3547(15) _cell_formula_units_Z 2 _cell_length_a 7.9749(2) _cell_length_b 8.0952(3) _cell_length_c 8.1395(3) _cell_measurement_reflns_used 1850 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.42 _cell_measurement_theta_min 2.90 _cell_volume 432.59(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 0.984 _diffrn_measured_fraction_theta_max 0.934 _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 0.091 _diffrn_reflns_av_sigmaI/netI 0.069 _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 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4596 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_min 2.90 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 7.235 _exptl_absorpt_correction_T_max 0.700 _exptl_absorpt_correction_T_min 0.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 3.001 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _refine_diff_density_max 1.35 _refine_diff_density_min -1.57 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 1850 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.169 _refine_ls_R_factor_all 0.035 _refine_ls_R_factor_gt 0.032 _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^)+(0.0584P)^2^+0.3136P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.096 _refine_ls_wR_factor_ref 0.115 _reflns_number_gt 1735 _reflns_number_total 1850 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tr1033.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _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_database_code 2012907 _cod_database_fobs_code 2012907 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 0.4568(7) 0.2563(7) 0.5717(7) 0.0151(10) Uani d . 1 . . C O1 0.5878(5) 0.1050(5) 0.6302(5) 0.0168(7) Uani d . 1 . . O C2 0.4701(7) 0.3379(6) 0.3843(7) 0.0165(9) Uani d . 1 . . C I2 0.69997(5) 0.21823(4) 0.18496(5) 0.01781(17) Uani d . 1 . . I C3 0.3342(7) 0.5005(6) 0.3318(7) 0.0153(9) Uani d . 1 . . C C4 0.1880(7) 0.5757(7) 0.4659(7) 0.0161(10) Uani d . 1 . . C N4 0.0478(6) 0.7482(6) 0.4127(6) 0.0188(9) Uani d . 1 . . N O41 -0.0820(6) 0.8178(5) 0.5346(6) 0.0265(9) Uani d . 1 . . O O42 0.0673(6) 0.8160(5) 0.2483(6) 0.0263(9) Uani d . 1 . . O C5 0.1632(7) 0.4974(6) 0.6545(7) 0.0166(9) Uani d . 1 . . C C6 0.3004(8) 0.3383(7) 0.7039(7) 0.0170(10) Uani d . 1 . . C I6 0.27464(5) 0.22289(4) 0.98238(5) 0.01917(17) Uani d . 1 . . I H1 0.6626 0.0572 0.5414 0.025 Uiso calc R 1 . . H H3 0.3442 0.5567 0.2054 0.018 Uiso calc R 1 . . H H5 0.0564 0.5516 0.7449 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 0.012(2) 0.015(2) 0.018(3) -0.0026(17) -0.005(2) -0.0044(19) O1 0.0129(16) 0.0158(16) 0.0146(18) 0.0056(13) -0.0064(15) -0.0039(14) C2 0.019(2) 0.014(2) 0.014(2) -0.002(2) -0.004(2) -0.0050(19) I2 0.0144(3) 0.0183(2) 0.0159(3) 0.00020(18) -0.00123(19) -0.00785(17) C3 0.011(2) 0.014(2) 0.017(2) -0.0001(17) -0.006(2) -0.0018(18) C4 0.014(2) 0.015(2) 0.019(3) -0.0001(18) -0.009(2) -0.003(2) N4 0.0121(18) 0.0175(18) 0.023(3) 0.0005(16) -0.0037(18) -0.0076(18) O41 0.023(2) 0.0244(19) 0.017(2) 0.0041(16) 0.0031(17) -0.0101(17) O42 0.024(2) 0.0229(19) 0.020(2) 0.0076(16) -0.0129(18) -0.0002(17) C5 0.0074(19) 0.022(2) 0.019(2) -0.0034(17) 0.004(2) -0.0134(19) C6 0.018(2) 0.017(2) 0.015(2) -0.008(2) 0.002(2) -0.0073(19) I6 0.0178(3) 0.0189(2) 0.0137(3) 0.00060(17) -0.00289(19) -0.00438(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 O1 C1 C6 118.3(5) no O1 C1 C2 123.5(5) no C6 C1 C2 118.2(5) no C1 O1 H1 109.5 no C3 C2 C1 120.9(5) no C3 C2 I2 120.1(4) no C1 C2 I2 119.1(4) no C4 C3 C2 118.2(5) no C4 C3 H3 120.9 no C2 C3 H3 120.9 no C3 C4 C5 123.6(4) no C3 C4 N4 118.7(5) no C5 C4 N4 117.7(4) no O42 N4 O41 123.4(5) no O42 N4 C4 118.0(4) no O41 N4 C4 118.5(4) no C6 C5 C4 117.4(5) no C6 C5 H5 121.3 no C4 C5 H5 121.3 no C5 C6 C1 121.7(5) no C5 C6 I6 118.7(4) no C1 C6 I6 119.6(4) 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 O1 . 1.347(6) no C1 C6 . 1.399(7) no C1 C2 . 1.410(7) no O1 H1 . 0.8400 no C2 C3 . 1.400(7) no C2 I2 . 2.078(5) no C3 C4 . 1.355(7) no C3 H3 . 0.9500 no C4 C5 . 1.402(7) no C4 N4 . 1.463(6) no N4 O42 . 1.224(6) no N4 O41 . 1.227(5) no C5 C6 . 1.384(7) no C5 H5 . 0.9500 no C6 I6 . 2.082(5) 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 O1 H1 I2 . 0.84 2.67 3.239(4) 126 no O1 H1 O41 1_645 0.84 2.20 2.808(6) 129 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 C3 C4 N4 O41 -178.5(6) y C3 C4 N4 O42 1.1(8) y C5 C4 N4 O41 1.4(8) no C5 C4 N4 O42 -179.1(6) no