#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012160.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_2012160 loop_ _publ_author_name 'McWilliam, Susan A.' 'Skakle, Janet M.S.' 'Low, John N.' 'Wardell, James L.' 'Garden, Simon J.' 'Pinto, Angelo C.' 'Torres, Jose C.' 'Glidewell, Christopher' _publ_section_title ; Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro···I interactions and aromatic \p--\p-stacking interactions ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 942 _journal_page_last 945 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C6 H5 I N2 O2' _chemical_formula_sum 'C6 H5 I N2 O2' _chemical_formula_weight 264.02 _chemical_name_systematic ; 2-Iodo-4-nitroaniline ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 7.4215(5) _cell_length_b 12.6755(9) _cell_length_c 16.4638(11) _cell_measurement_reflns_used 2339 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 31.14 _cell_measurement_theta_min 2.47 _cell_volume 1548.77(18) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .935 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD detector' _diffrn_measurement_method \f-\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0886 _diffrn_reflns_av_sigmaI/netI .0695 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12391 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 31.14 _diffrn_reflns_theta_min 2.47 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 4.084 _exptl_absorpt_correction_T_max .887 _exptl_absorpt_correction_T_min .495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 992 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .03 _refine_diff_density_max '2.20 (0.91 \%A from I2)' _refine_diff_density_min '-1.21 (0.90 \%A from I2)' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .961 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 2339 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .961 _refine_ls_R_factor_all .1376 _refine_ls_R_factor_gt .0631 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0943P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1798 _reflns_number_gt 1109 _reflns_number_total 2339 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1480.cif _[local]_cod_data_source_block Ib _cod_database_code 2012160 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, 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 .5827(11) .4747(7) .3056(5) .0464(19) Uani d . 1 . . C N1 .5512(11) .4240(6) .3743(5) .062(2) Uani d . 1 . . N C2 .6364(10) .5828(7) .3030(4) .0427(19) Uani d . 1 . . C I2 .66772(8) .66835(5) .41043(3) .0531(3) Uani d . 1 . . I C3 .6636(11) .6331(6) .2307(5) .0426(17) Uani d . 1 . . C C4 .6401(11) .5789(7) .1593(5) .0438(19) Uani d . 1 . . C N4 .6642(10) .6332(7) .0834(4) .0529(18) Uani d . 1 . . N O1 .6825(10) .7298(6) .0850(4) .0669(19) Uani d . 1 . . O O2 .6703(9) .5836(6) .0201(4) .075(2) Uani d . 1 . . O C5 .5885(12) .4739(8) .1586(6) .056(2) Uani d . 1 . . C C6 .5595(11) .4233(7) .2307(6) .050(2) Uani d . 1 . . C H11 .5164 .3593 .3734 .075 Uiso calc R 1 . . H H12 .5655 .4557 .4201 .075 Uiso calc R 1 . . H H3 .6979 .7036 .2299 .051 Uiso calc R 1 . . H H5 .5737 .4383 .1096 .067 Uiso calc R 1 . . H H6 .5234 .3530 .2302 .060 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 .039(5) .049(5) .052(4) .002(4) -.003(4) .005(4) N1 .057(5) .067(5) .062(4) -.007(4) -.010(4) .025(4) C2 .027(4) .062(5) .039(4) .009(3) -.003(3) -.003(4) I2 .0436(3) .0690(5) .0468(3) .0027(3) .0007(3) -.0096(3) C3 .031(4) .046(4) .051(4) .000(4) .001(4) .001(3) C4 .031(4) .057(5) .043(4) .008(4) -.001(3) -.003(4) N4 .036(4) .079(6) .044(4) .000(4) .005(3) .005(4) O1 .076(5) .069(5) .056(4) .002(4) .008(3) .014(3) O2 .076(5) .107(6) .043(3) -.001(4) .011(3) -.012(4) C5 .047(5) .063(6) .058(5) -.002(4) -.004(4) -.014(4) C6 .041(5) .043(5) .067(5) -.003(4) -.006(4) .003(4) 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 N1 . 1.323(10) no C1 C6 . 1.404(11) no C1 C2 . 1.428(12) no N1 H11 . .8600 no N1 H12 . .8600 no C2 C3 . 1.365(11) no C2 I2 . 2.087(8) no C3 C4 . 1.373(11) no C3 H3 . .9300 no C4 C5 . 1.384(12) no C4 N4 . 1.439(10) no N4 O2 . 1.218(9) no N4 O1 . 1.231(12) no C5 C6 . 1.368(12) no C5 H5 . .9300 no C6 H6 . .9300 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 N1 C1 C6 120.2(8) no N1 C1 C2 122.7(8) no C6 C1 C2 117.0(7) no C1 N1 H11 120.0 no C1 N1 H12 120.0 no H11 N1 H12 120.0 no C3 C2 C1 121.0(7) no C3 C2 I2 118.7(6) no C1 C2 I2 120.3(6) no C2 C3 C4 119.6(8) no C2 C3 H3 120.2 no C4 C3 H3 120.2 no C3 C4 C5 121.6(8) no C3 C4 N4 119.3(8) no C5 C4 N4 119.1(8) no O2 N4 O1 121.9(7) no O2 N4 C4 120.0(9) no O1 N4 C4 118.1(7) no C6 C5 C4 119.1(8) no C6 C5 H5 120.4 no C4 C5 H5 120.4 no C5 C6 C1 121.7(8) no C5 C6 H6 119.2 no C1 C6 H6 119.2 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 N1 H11 O1 3_645 .86 2.31 3.085(11) 150 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 O1 -9.2(12) no C5 C4 N4 O1 169.0(8) no C3 C4 N4 O2 169.1(8) no C5 C4 N4 O2 -12.7(12) no