#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012908.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_2012908 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 'C8 H5 I2 N O4' _chemical_formula_sum 'C8 H5 I2 N O4' _chemical_formula_weight 432.93 _chemical_name_systematic ; 2,6-Diiodo-4-nitrophenyl acetate ; _space_group_IT_number 62 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.0608(9) _cell_length_b 12.4501(14) _cell_length_c 11.6790(13) _cell_measurement_reflns_used 2206 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 32.58 _cell_measurement_theta_min 2.39 _cell_volume 1172.1(2) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _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 292(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _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 0.044 _diffrn_reflns_av_sigmaI/netI 0.024 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11456 _diffrn_reflns_theta_full 32.58 _diffrn_reflns_theta_max 32.58 _diffrn_reflns_theta_min 2.39 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 5.360 _exptl_absorpt_correction_T_max 0.528 _exptl_absorpt_correction_T_min 0.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.453 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _refine_diff_density_max 1.20 _refine_diff_density_min -0.41 _refine_ls_extinction_coef 0.0321(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 81 _refine_ls_number_reflns 2206 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.057 _refine_ls_R_factor_gt 0.041 _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^)+(0.0513P)^2^+0.8851P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.103 _refine_ls_wR_factor_ref 0.112 _reflns_number_gt 1555 _reflns_number_total 2206 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tr1033.cif _cod_data_source_block II _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 2012908 _cod_database_fobs_code 2012908 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x+1/2, y, -z+1/2' '-x+1/2, y+1/2, z+1/2' 'x, -y+1/2, 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 0.1503(5) 0.2500 0.1689(3) 0.0376(7) Uani d S 1 . . C O1 0.1962(3) 0.2500 0.0539(2) 0.0406(6) Uani d S 1 . . O C11 0.0705(6) 0.2500 -0.0268(3) 0.0447(9) Uani d S 1 . . C O12 -0.0711(5) 0.2500 0.0010(3) 0.0801(14) Uani d S 1 . . O C12 0.1402(6) 0.2500 -0.1442(3) 0.0548(12) Uani d S 1 . . C C2 0.1341(3) 0.3471(2) 0.2269(2) 0.0407(6) Uani d . 1 . . C I2 0.16877(4) 0.49229(2) 0.14194(2) 0.06767(17) Uani d . 1 . . I C3 0.1006(4) 0.3473(3) 0.3440(2) 0.0444(6) Uani d . 1 . . C C4 0.0833(5) 0.2500 0.3985(3) 0.0436(9) Uani d S 1 . . C N4 0.0485(5) 0.2500 0.5223(3) 0.0540(10) Uani d S 1 . . N O4 0.0328(4) 0.3362(3) 0.5705(2) 0.0765(9) Uani d . 1 . . O H12A 0.0605 0.2202 -0.1963 0.082 Uiso calc PR 0.50 . . H H12B 0.2395 0.2075 -0.1457 0.082 Uiso calc PR 0.50 . . H H12C 0.1657 0.3223 -0.1666 0.082 Uiso calc PR 0.50 . . H H3 0.0903 0.4114 0.3842 0.053 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 0.0379(18) 0.048(2) 0.0274(15) 0.000 0.0006(13) 0.000 O1 0.0390(14) 0.0558(17) 0.0270(12) 0.000 0.0029(10) 0.000 C11 0.052(2) 0.051(2) 0.0312(17) 0.000 0.0005(16) 0.000 O12 0.0437(18) 0.150(5) 0.0464(19) 0.000 -0.0016(15) 0.000 C12 0.064(3) 0.072(3) 0.0288(18) 0.000 -0.0013(17) 0.000 C2 0.0430(14) 0.0448(14) 0.0344(12) 0.0022(11) -0.0010(10) 0.0007(10) I2 0.1028(3) 0.04586(18) 0.0543(2) 0.00141(11) 0.00652(12) 0.00583(9) C3 0.0461(14) 0.0547(17) 0.0323(12) 0.0030(13) -0.0015(11) -0.0046(11) C4 0.0371(19) 0.068(3) 0.0255(15) 0.000 -0.0045(14) 0.000 N4 0.0471(19) 0.089(3) 0.0262(15) 0.000 -0.0035(13) 0.000 O4 0.088(2) 0.103(2) 0.0381(12) -0.0214(16) 0.0074(12) -0.0237(14) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C2 8_555 . 120.6(3) no C2 C1 O1 8_555 . 119.58(17) no C2 C1 O1 . . 119.58(17) no C11 O1 C1 . . 117.5(3) no O12 C11 O1 . . 121.2(4) no O12 C11 C12 . . 128.2(4) no O1 C11 C12 . . 110.6(4) no C11 C12 H12A . . 109.5 no C11 C12 H12B . . 109.5 no H12A C12 H12B . . 109.5 no C11 C12 H12C . . 109.5 no H12A C12 H12C . . 109.5 no H12B C12 H12C . . 109.5 no C1 C2 C3 . . 119.7(3) no C1 C2 I2 . . 120.7(2) no C3 C2 I2 . . 119.5(2) no C4 C3 C2 . . 118.2(3) no C4 C3 H3 . . 120.9 no C2 C3 H3 . . 120.9 no C3 C4 C3 8_555 . 123.4(4) no C3 C4 N4 8_555 . 118.27(18) no C3 C4 N4 . . 118.27(18) no O4 N4 O4 . 8_555 123.5(4) no O4 N4 C4 . . 118.2(2) no O4 N4 C4 8_555 . 118.2(2) 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 8_555 1.392(3) no C1 C2 . 1.392(3) no C1 O1 . 1.393(4) no O1 C11 . 1.385(5) no C11 O12 . 1.186(6) no C11 C12 . 1.481(6) no C12 H12A . 0.9600 no C12 H12B . 0.9600 no C12 H12C . 0.9600 no C2 C3 . 1.394(4) no C2 I2 . 2.080(3) no C3 C4 . 1.375(4) no C3 H3 . 0.9300 no C4 C3 8_555 1.375(4) no C4 N4 . 1.474(5) no N4 O4 . 1.218(3) no N4 O4 8_555 1.218(3) 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 C1 O1 C11 8_555 . 92.6(3) no C1 O1 C11 O12 . . 0.0 no C1 O1 C11 C12 . . 180.0 no C2 C1 C2 C3 8_555 . -0.3(5) no O1 C1 C2 C3 . . -175.1(3) no C2 C1 C2 I2 8_555 . 177.22(18) no O1 C1 C2 I2 . . 2.4(4) no C1 C2 C3 C4 . . -0.5(5) no I2 C2 C3 C4 . . -178.0(3) no C2 C3 C4 C3 . 8_555 1.4(6) no C2 C3 C4 N4 . . 179.8(3) no C3 C4 N4 O4 8_555 . -179.9(4) no C3 C4 N4 O4 . . 1.6(6) y C3 C4 N4 O4 8_555 8_555 -1.6(6) no C3 C4 N4 O4 . 8_555 179.9(4) y C2 C1 O1 C11 . . -92.6(3) y