#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013800.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_2013800 loop_ _publ_author_name 'Garden, Simon J.' 'da Cunha, Fernando R.' '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 H4 I N O4' _chemical_formula_sum 'C7 H4 I N O4' _chemical_formula_weight 293.01 _chemical_name_systematic ; 2-Hydroxy-3-iodo-5-nitrobenzaldehyde ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 115.496(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2556(3) _cell_length_b 15.3414(8) _cell_length_c 7.2521(4) _cell_measurement_reflns_used 1901 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 3.04 _cell_volume 829.05(7) _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 0.992 _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 0.065 _diffrn_reflns_av_sigmaI/netI 0.053 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 8251 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 3.04 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 3.842 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_correction_T_min 0.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.348 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _refine_diff_density_max 1.13 _refine_diff_density_min -1.08 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 1901 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.033 _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^)+(0.0348P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.069 _refine_ls_wR_factor_ref 0.074 _reflns_number_gt 1482 _reflns_number_total 1901 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gg1198.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013800 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_type_symbol C1 0.2059(6) 0.1453(2) 0.1802(6) 0.0135(8) Uani d . 1 C N1 0.3257(5) 0.0711(2) 0.2125(5) 0.0170(8) Uani d . 1 N O11 0.4865(4) 0.08468(18) 0.2696(5) 0.0236(7) Uani d . 1 O O12 0.2593(4) -0.00229(19) 0.1838(5) 0.0252(8) Uani d . 1 O C2 0.0318(6) 0.1324(3) 0.1491(6) 0.0174(9) Uani d . 1 C C3 -0.0769(6) 0.2043(3) 0.1281(6) 0.0160(9) Uani d . 1 C C4 -0.0087(6) 0.2900(3) 0.1386(6) 0.0159(9) Uani d . 1 C C5 0.1703(6) 0.3002(2) 0.1698(6) 0.0157(9) Uani d . 1 C I5 0.28173(4) 0.424544(16) 0.19310(4) 0.02033(12) Uani d . 1 I C6 0.2773(6) 0.2286(3) 0.1902(5) 0.0153(8) Uani d . 1 C C31 -0.2675(6) 0.1906(3) 0.1045(6) 0.0168(9) Uani d . 1 C O31 -0.3591(4) 0.2513(2) 0.1010(5) 0.0277(7) Uani d . 1 O O41 -0.1079(4) 0.36054(18) 0.1176(5) 0.0231(7) Uani d . 1 O H2 -0.0129 0.0762 0.1421 0.021 Uiso calc R 1 H H31 -0.3130 0.1344 0.0927 0.020 Uiso calc R 1 H H41 -0.2028 0.3466 0.1202 0.035 Uiso calc R 1 H H6 0.3957 0.2357 0.2106 0.018 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 0.017(2) 0.0113(19) 0.0123(19) 0.0047(17) 0.0061(17) -0.0005(15) N1 0.023(2) 0.0131(19) 0.0169(17) -0.0002(16) 0.0102(16) -0.0027(14) O11 0.0198(19) 0.0181(17) 0.0352(18) 0.0013(13) 0.0140(15) -0.0013(13) O12 0.031(2) 0.0124(16) 0.0347(19) -0.0029(13) 0.0168(17) -0.0038(13) C2 0.021(3) 0.015(2) 0.016(2) -0.0040(18) 0.0067(18) -0.0019(16) C3 0.017(2) 0.016(2) 0.0151(19) 0.0010(17) 0.0073(18) 0.0005(16) C4 0.022(2) 0.016(2) 0.0116(18) 0.0022(18) 0.0093(17) 0.0009(16) C5 0.022(3) 0.013(2) 0.0143(19) -0.0019(17) 0.0095(18) -0.0016(15) I5 0.0290(2) 0.01252(17) 0.02228(17) -0.00365(12) 0.01369(13) -0.00179(12) C6 0.021(2) 0.015(2) 0.0128(18) -0.0016(18) 0.0094(17) -0.0011(16) C31 0.030(3) 0.008(2) 0.0111(19) 0.0020(19) 0.0073(18) 0.0020(16) O31 0.0204(18) 0.0314(19) 0.0332(18) 0.0028(15) 0.0133(15) 0.0099(14) O41 0.0223(19) 0.0158(15) 0.0377(18) 0.0059(13) 0.0189(16) 0.0042(13) 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 C2 C1 C6 122.0(4) no C2 C1 N1 120.3(4) no C6 C1 N1 117.6(4) no O11 N1 O12 123.4(4) no O11 N1 C1 118.9(3) no O12 N1 C1 117.7(4) no C1 C2 C3 119.1(4) no C1 C2 H2 120.4 no C3 C2 H2 120.4 no C2 C3 C4 120.4(4) no C2 C3 C31 119.4(4) no C4 C3 C31 120.1(4) no O31 C31 C3 120.7(4) no O31 C31 H31 119.7 no C3 C31 H31 119.7 no O41 C4 C5 118.9(4) no O41 C4 C3 122.6(4) no C5 C4 C3 118.6(4) no C4 O41 H41 109.5 no C6 C5 C4 120.7(4) no C6 C5 I5 118.6(3) no C4 C5 I5 120.7(3) no C5 C6 C1 119.2(4) no C5 C6 H6 120.4 no C1 C6 H6 120.4 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.370(6) no C2 C3 1.389(6) no C3 C4 1.419(5) no C4 C5 1.404(6) no C5 C6 1.376(6) no C6 C1 1.396(6) no C1 N1 1.459(5) no N1 O11 1.226(5) no N1 O12 1.231(4) no C2 H2 0.93 no C3 C31 1.522(6) no C31 O31 1.193(5) no C31 H31 0.93 no C4 O41 1.327(5) no O41 H41 0.82 no C5 I5 2.093(4) no C6 H6 0.93 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 O41 H41 O31 . 0.82 1.92 2.629(5) 145 y C6 H6 O31 1_655 0.93 2.48 3.351(6) 155 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 C2 C1 N1 O11 -169.4(4) no C6 C1 N1 O11 8.2(5) no C2 C1 N1 O12 9.5(5) no C6 C1 N1 O12 -173.0(3) no C6 C1 C2 C3 -0.4(6) no N1 C1 C2 C3 177.0(3) no C1 C2 C3 C4 0.1(6) no C1 C2 C3 C31 -176.9(4) no C2 C3 C31 O31 174.6(4) no C4 C3 C31 O31 -2.4(6) no C2 C3 C4 O41 179.4(4) no C31 C3 C4 O41 -3.7(6) no C2 C3 C4 C5 0.2(6) no C31 C3 C4 C5 177.1(3) no O41 C4 C5 C6 -179.4(3) no C3 C4 C5 C6 -0.1(6) no O41 C4 C5 I5 2.1(5) no C3 C4 C5 I5 -178.7(3) no C4 C5 C6 C1 -0.2(6) no I5 C5 C6 C1 178.4(3) no C2 C1 C6 C5 0.4(6) no N1 C1 C6 C5 -177.1(3) no