#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012159.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_2012159 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 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 67.905(3) _cell_angle_beta 86.956(3) _cell_angle_gamma 65.744(2) _cell_formula_units_Z 2 _cell_length_a 7.1647(4) _cell_length_b 7.9572(4) _cell_length_c 8.0489(5) _cell_measurement_reflns_used 1728 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 3.05 _cell_volume 384.84(4) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _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 150(2) _diffrn_measured_fraction_theta_full .988 _diffrn_measured_fraction_theta_max .972 _diffrn_measurement_device_type Kappa-CCD _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 .71073 _diffrn_reflns_av_R_equivalents .047 _diffrn_reflns_av_sigmaI/netI .0493 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4602 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.05 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 4.109 _exptl_absorpt_correction_T_max .887 _exptl_absorpt_correction_T_min .393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 248 _exptl_crystal_size_max .28 _exptl_crystal_size_mid .08 _exptl_crystal_size_min .03 _refine_diff_density_max '2.77 (0.96 \%A from I2)' _refine_diff_density_min '-2.14 (0.83 \%A from I2)' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1728 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all .0535 _refine_ls_R_factor_gt .0460 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+1.2313P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1200 _reflns_number_gt 1556 _reflns_number_total 1728 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1480.cif _[local]_cod_data_source_block Ia _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012159 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 N1 .5600(9) 1.1211(8) .1092(7) .0313(11) Uani d . 1 . . N C1 .5549(9) .9692(8) .2561(7) .0235(11) Uani d . 1 . . C C2 .3716(9) .9557(8) .3118(7) .0236(11) Uani d . 1 . . C I2 .08930(6) 1.17350(5) .15765(5) .03361(19) Uani d . 1 . . I C3 .3701(9) .8046(8) .4684(8) .0244(11) Uani d . 1 . . C C4 .5571(9) .6618(8) .5699(7) .0223(11) Uani d . 1 . . C O1 .3910(7) .5031(6) .7809(6) .0339(10) Uani d . 1 . . O O2 .7239(7) .3786(6) .8240(6) .0350(10) Uani d . 1 . . O N4 .5571(8) .5051(7) .7357(6) .0253(10) Uani d . 1 . . N C5 .7436(9) .6646(8) .5181(7) .0237(11) Uani d . 1 . . C C6 .7417(9) .8177(8) .3609(8) .0259(11) Uani d . 1 . . C H11 .4444 1.2177 .0434 .038 Uiso calc R 1 . . H H12 .6790 1.1237 .0790 .038 Uiso calc R 1 . . H H3 .2441 .7986 .5057 .029 Uiso calc R 1 . . H H5 .8699 .5637 .5889 .028 Uiso calc R 1 . . H H6 .8686 .8208 .3229 .031 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 N1 .044(3) .026(2) .025(2) -.020(2) .003(2) -.004(2) C1 .036(3) .018(2) .016(2) -.011(2) .002(2) -.006(2) C2 .028(3) .014(2) .022(3) -.004(2) -.003(2) -.004(2) I2 .0321(3) .0226(2) .0316(3) -.00509(18) -.00796(17) -.00137(18) C3 .027(3) .018(2) .023(3) -.005(2) -.001(2) -.007(2) C4 .035(3) .015(2) .012(2) -.009(2) .002(2) -.0015(19) O1 .034(2) .025(2) .031(2) -.0097(18) .0073(18) -.0022(18) O2 .034(2) .024(2) .028(2) -.0086(18) -.0084(18) .0064(17) N4 .033(3) .018(2) .020(2) -.010(2) .0020(19) -.0043(19) C5 .024(3) .020(2) .022(3) -.005(2) -.001(2) -.008(2) C6 .026(3) .021(3) .030(3) -.011(2) .005(2) -.008(2) 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 N1 C1 . 1.348(7) no N1 H11 . .8800 no N1 H12 . .8800 no C1 C2 . 1.399(8) no C1 C6 . 1.409(8) no C2 C3 . 1.380(8) no C2 I2 . 2.098(5) no C3 C4 . 1.386(8) no C3 H3 . .9500 no C4 C5 . 1.385(8) no C4 N4 . 1.444(7) no O1 N4 . 1.230(7) no O2 N4 . 1.229(6) no C5 C6 . 1.384(8) no C5 H5 . .9500 no C6 H6 . .9500 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' 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' I I -.4742 1.8119 '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 C1 N1 H11 120.0 no C1 N1 H12 120.0 no H11 N1 H12 120.0 no N1 C1 C2 123.0(5) no N1 C1 C6 119.0(5) no C2 C1 C6 118.0(5) no C3 C2 C1 121.8(5) no C3 C2 I2 118.6(4) no C1 C2 I2 119.6(4) no C2 C3 C4 118.3(5) no C2 C3 H3 120.9 no C4 C3 H3 120.9 no C5 C4 C3 122.3(5) no C5 C4 N4 119.0(5) no C3 C4 N4 118.7(5) no O2 N4 O1 123.2(5) no O2 N4 C4 118.1(5) no O1 N4 C4 118.7(5) no C6 C5 C4 118.5(5) no C6 C5 H5 120.7 no C4 C5 H5 120.7 no C5 C6 C1 121.1(5) no C5 C6 H6 119.4 no C1 C6 H6 119.4 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 1_564 .88 2.35 2.994(7) 130 y N1 H12 O2 1_564 .88 2.40 3.000(8) 126 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 .3(8) no C5 C4 N4 O1 -179.9(6) no C3 C4 N4 O2 179.6(6) no C5 C4 N4 O2 -.6(8) no