#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013801.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_2013801 loop_ _publ_author_name 'Garden, Simon J.' 'Cunha, Fernando R. da' 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; Three-dimensional aggregation in 2-hydroxy-3-iodo-5-nitrobenzaldehyde involving C---H···O, iodo--nitro and aromatic \p--\p stacking interactions, and isolated dimers in disordered 2,4-diiodo-6-nitroanisole ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o12 _journal_page_last o14 _journal_volume 60 _journal_year 2004 _chemical_formula_moiety 'C7 H5 I2 N O3' _chemical_formula_sum 'C7 H5 I2 N O3' _chemical_formula_weight 404.92 _chemical_name_systematic ; 2,4-Diiodo-6-nitroanisole ; _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 95.225(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 32.999(2) _cell_length_b 4.2305(3) _cell_length_c 14.8328(11) _cell_measurement_reflns_used 3712 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 32.58 _cell_measurement_theta_min 2.48 _cell_volume 2062.1(2) _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, 2003)' _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 0.997 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.066 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 10606 _diffrn_reflns_theta_full 29.50 _diffrn_reflns_theta_max 32.58 _diffrn_reflns_theta_min 2.48 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 6.076 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_correction_T_min 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.609 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1472 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _refine_diff_density_max 1.07 _refine_diff_density_min -1.29 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 3712 _refine_ls_number_restraints 10 _refine_ls_restrained_S_all 0.888 _refine_ls_R_factor_all 0.143 _refine_ls_R_factor_gt 0.053 _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^)+(0.0721P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.124 _refine_ls_wR_factor_ref 0.154 _reflns_number_gt 1520 _reflns_number_total 3712 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gg1198.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_code 2013801 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 C1 0.1408(2) 0.3638(13) 0.5217(3) 0.0539(15) Uani d D 1 . . C I1 0.14846(4) 0.5738(3) 0.64326(6) 0.0692(3) Uani d P 0.50 A -1 I N1 0.1473(4) 0.525(4) 0.6090(6) 0.113(2) Uani d PD 0.50 A -2 N O11 0.1770(3) 0.691(3) 0.6295(7) 0.113(2) Uani d PD 0.50 A -2 O O12 0.1220(3) 0.486(4) 0.6629(8) 0.113(2) Uani d PD 0.50 A -2 O C2 0.10114(19) 0.3350(13) 0.4756(4) 0.0488(14) Uani d . 1 A . C O21 0.06871(13) 0.4760(11) 0.5092(3) 0.0616(12) Uani d . 1 . . O C21 0.0465(2) 0.2755(19) 0.5662(5) 0.077(2) Uani d . 1 A . C C3 0.09815(15) 0.1894(15) 0.3909(4) 0.0518(15) Uani d D 1 . . C N3 0.0590(2) 0.162(4) 0.3371(6) 0.113(2) Uani d PD 0.50 A -1 N O31 0.0584(3) 0.149(4) 0.2548(7) 0.113(2) Uani d PD 0.50 A -1 O O32 0.0272(3) 0.140(4) 0.3726(7) 0.113(2) Uani d PD 0.50 A -1 O I3 0.04405(3) 0.1563(3) 0.31796(6) 0.0732(3) Uani d P 0.50 A -2 I C4 0.1321(2) 0.0604(15) 0.3566(4) 0.0590(17) Uani d . 1 A . C C5 0.17055(19) 0.0899(15) 0.4032(4) 0.0540(15) Uani d . 1 . . C I5 0.221995(15) -0.09284(11) 0.34922(4) 0.0749(2) Uani d . 1 A . I C6 0.1749(2) 0.2420(16) 0.4848(4) 0.0574(16) Uani d . 1 A . C H21A 0.0316 0.1199 0.5296 0.115 Uiso calc R 1 . . H H21B 0.0279 0.4016 0.5971 0.115 Uiso calc R 1 . . H H21C 0.0653 0.1718 0.6098 0.115 Uiso calc R 1 . . H H4 0.1292 -0.0474 0.3017 0.071 Uiso calc R 1 . . H H6 0.2006 0.2642 0.5157 0.069 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 0.070(4) 0.047(4) 0.045(3) 0.002(3) 0.007(3) 0.010(3) I1 0.0891(7) 0.0674(6) 0.0507(5) 0.0001(6) 0.0045(5) -0.0066(4) N1 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4) O11 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4) O12 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4) C2 0.056(4) 0.048(3) 0.044(3) 0.006(3) 0.015(3) 0.007(3) O21 0.060(3) 0.065(3) 0.063(3) 0.015(2) 0.021(2) 0.004(2) C21 0.067(5) 0.093(5) 0.074(5) 0.002(4) 0.033(4) 0.004(4) C3 0.048(3) 0.060(4) 0.048(3) -0.002(3) 0.007(3) 0.000(3) N3 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4) O31 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4) O32 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4) I3 0.0548(6) 0.1124(9) 0.0518(5) 0.0057(6) 0.0013(4) -0.0050(5) C4 0.070(4) 0.057(4) 0.053(4) 0.002(3) 0.025(3) -0.003(3) C5 0.053(4) 0.051(4) 0.062(4) 0.000(3) 0.027(3) 0.013(3) I5 0.0687(3) 0.0625(3) 0.0993(4) 0.0104(2) 0.0396(3) 0.0057(3) C6 0.054(4) 0.061(4) 0.059(4) 0.002(3) 0.013(3) 0.001(3) 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 C6 . 1.394(9) no C1 C2 . 1.427(9) no C1 N1 . 1.4603(10) no C1 I1 . 2.005(5) no N1 O12 . 1.2203(10) no N1 O11 . 1.2205(10) no C2 O21 . 1.359(7) no C2 C3 . 1.394(8) no O21 C21 . 1.443(8) no C21 H21A . 0.96 no C21 H21B . 0.96 no C21 H21C . 0.96 no C3 C4 . 1.383(8) no C3 N3 . 1.4608(10) no C3 I3 . 2.007(5) no N3 O31 . 1.2202(10) no N3 O32 . 1.2204(10) no C4 C5 . 1.395(10) no C4 H4 . 0.93 no C5 C6 . 1.368(9) no C5 I5 . 2.090(6) no C6 H6 . 0.93 no 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 C6 C1 C2 121.3(5) no C6 C1 N1 117.5(8) no C2 C1 N1 121.3(7) no C6 C1 I1 118.5(5) no C2 C1 I1 120.3(4) no O12 N1 O11 119.61(15) no O12 N1 C1 117.7(9) no O11 N1 C1 122.7(9) no O21 C2 C3 122.1(5) no O21 C2 C1 120.4(5) no C3 C2 C1 117.2(5) no C2 O21 C21 114.5(5) no O21 C21 H21A 109.5 no O21 C21 H21B 109.5 no H21A C21 H21B 109.5 no O21 C21 H21C 109.5 no H21A C21 H21C 109.5 no H21B C21 H21C 109.5 no C4 C3 C2 120.8(5) no C4 C3 N3 118.2(7) no C2 C3 N3 120.9(7) no C4 C3 I3 118.9(4) no C2 C3 I3 120.2(4) no O31 N3 O32 119.57(15) no O31 N3 C3 118.8(8) no O32 N3 C3 121.5(8) no C3 C4 C5 120.9(6) no C3 C4 H4 119.6 no C5 C4 H4 119.6 no C6 C5 C4 119.9(6) no C6 C5 I5 119.3(5) no C4 C5 I5 120.8(5) no C5 C6 C1 119.8(6) no C5 C6 H6 120.1 no C1 C6 H6 120.1 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 C6 C1 N1 O12 -142.1(13) no C2 C1 N1 O12 38.5(18) no I1 C1 N1 O12 -21(19) no C6 C1 N1 O11 37.2(19) no C2 C1 N1 O11 -142.2(14) no I1 C1 N1 O11 16E1(2) no C6 C1 C2 O21 -174.9(5) no N1 C1 C2 O21 4.5(11) no I1 C1 C2 O21 6.4(7) no C6 C1 C2 C3 -2.1(8) no N1 C1 C2 C3 177.3(9) no I1 C1 C2 C3 179.3(4) no C3 C2 O21 C21 93.7(7) no C1 C2 O21 C21 -93.8(7) no O21 C2 C3 C4 177.0(6) no C1 C2 C3 C4 4.2(9) no O21 C2 C3 N3 -4.5(11) no C1 C2 C3 N3 -177.2(9) no O21 C2 C3 I3 -4.3(8) no C1 C2 C3 I3 -177.0(4) no C4 C3 N3 O31 -28.8(19) no C2 C3 N3 O31 152.6(13) no I3 C3 N3 O31 14E1(5) no C4 C3 N3 O32 148.1(14) no C2 C3 N3 O32 -30(2) no I3 C3 N3 O32 -5E1(5) no C2 C3 C4 C5 -4.0(10) no N3 C3 C4 C5 177.4(9) no I3 C3 C4 C5 177.2(5) no C3 C4 C5 C6 1.4(9) no C3 C4 C5 I5 -178.1(5) no C4 C5 C6 C1 0.8(9) no I5 C5 C6 C1 -179.7(4) no C2 C1 C6 C5 -0.4(9) no N1 C1 C6 C5 -179.8(9) no I1 C1 C6 C5 178.2(5) no