#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013211.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_2013211 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; 4-Iodo-N-(2-nitrophenylsulfanyl)aniline: \p-stacked sheets generated by a combination of N---H···O and C---H···O hydrogen bonds ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o95 _journal_page_last o97 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C12 H9 I N2 O2 S' _chemical_formula_moiety 'C12 H9 I N2 O2 S' _chemical_formula_sum 'C12 H9 I N2 O2 S' _chemical_formula_weight 372.18 _chemical_name_systematic ; ? ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 7.4171(2) _cell_length_b 22.1145(8) _cell_length_c 15.7093(4) _cell_measurement_reflns_used 2928 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.46 _cell_measurement_theta_min 3.55 _cell_volume 2576.73(13) _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, 2002)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) 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 0.992 _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 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 10802 _diffrn_reflns_theta_full 27.46 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_min 3.55 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 2.642 _exptl_absorpt_correction_T_max 0.817 _exptl_absorpt_correction_T_min 0.458 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.757 _refine_diff_density_min -1.021 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2928 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.974 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0403 _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^)+(0.0249P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.0818 _reflns_number_gt 1867 _reflns_number_total 2928 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1610.cif _[local]_cod_data_source_block I _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 2013211 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 0.5139(5) 0.60187(17) 0.0489(2) 0.0212(9) Uani d . 1 . . C C2 0.4337(5) 0.57878(18) -0.0242(2) 0.0256(10) Uani d . 1 . . C C3 0.5363(6) 0.55240(18) -0.0871(2) 0.0272(10) Uani d . 1 . . C C4 0.7206(6) 0.54941(18) -0.0777(2) 0.0266(10) Uani d . 1 . . C I4 0.87720(5) 0.505572(13) -0.171435(16) 0.03766(13) Uani d . 1 . . I C5 0.8042(6) 0.57209(18) -0.0058(2) 0.0304(10) Uani d . 1 . . C C6 0.6996(5) 0.59855(19) 0.0575(3) 0.0287(10) Uani d . 1 . . C S1 0.46633(13) 0.64314(5) 0.21155(6) 0.0236(2) Uani d . 1 . . S N1 0.4042(4) 0.62927(15) 0.11064(19) 0.0266(8) Uani d . 1 . . N C11 0.5423(5) 0.71901(17) 0.2043(2) 0.0202(9) Uani d . 1 . . C C12 0.5882(5) 0.75438(18) 0.2755(2) 0.0208(9) Uani d . 1 . . C C13 0.6467(5) 0.81364(19) 0.2685(2) 0.0266(10) Uani d . 1 . . C C14 0.6623(6) 0.84010(19) 0.1903(2) 0.0326(11) Uani d . 1 . . C C15 0.6187(6) 0.8060(2) 0.1191(2) 0.0347(11) Uani d . 1 . . C C16 0.5584(5) 0.74744(19) 0.1254(2) 0.0252(10) Uani d . 1 . . C N12 0.5739(4) 0.72846(18) 0.3604(2) 0.0279(8) Uani d . 1 . . N O121 0.5351(4) 0.67415(14) 0.36581(15) 0.0286(7) Uani d . 1 . . O O122 0.6018(5) 0.76111(15) 0.42184(16) 0.0497(9) Uani d . 1 . . O H2 0.3066 0.5812 -0.0309 0.031 Uiso calc R 1 . . H H3 0.4804 0.5364 -0.1365 0.033 Uiso calc R 1 . . H H5 0.9315 0.5696 0.0003 0.036 Uiso calc R 1 . . H H6 0.7558 0.6145 0.1070 0.034 Uiso calc R 1 . . H H1 0.2947 0.6400 0.0953 0.032 Uiso calc R 1 . . H H13 0.6761 0.8360 0.3183 0.032 Uiso calc R 1 . . H H14 0.7020 0.8808 0.1849 0.039 Uiso calc R 1 . . H H15 0.6309 0.8237 0.0643 0.042 Uiso calc R 1 . . H H16 0.5271 0.7259 0.0752 0.030 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 0.025(2) 0.016(2) 0.022(2) -0.0009(17) 0.0006(19) 0.0003(18) C2 0.024(2) 0.025(2) 0.028(2) -0.0011(18) -0.0095(19) 0.0030(19) C3 0.037(3) 0.026(3) 0.018(2) 0.002(2) -0.003(2) -0.0033(18) C4 0.035(3) 0.021(2) 0.024(2) -0.0022(19) 0.007(2) -0.0006(17) I4 0.0514(2) 0.0369(2) 0.02474(17) 0.00869(15) 0.01215(14) 0.00135(13) C5 0.023(2) 0.031(3) 0.036(2) -0.0057(19) 0.005(2) -0.006(2) C6 0.026(2) 0.033(3) 0.027(2) -0.006(2) -0.004(2) -0.010(2) S1 0.0239(5) 0.0254(6) 0.0215(5) -0.0023(5) 0.0015(5) 0.0012(5) N1 0.0196(18) 0.033(2) 0.0268(18) 0.0024(15) -0.0075(15) -0.0051(16) C11 0.016(2) 0.024(2) 0.021(2) 0.0018(17) 0.0036(18) -0.0015(18) C12 0.021(2) 0.027(2) 0.0145(19) 0.0025(17) 0.0028(17) 0.0003(18) C13 0.027(2) 0.030(3) 0.023(2) 0.0005(19) 0.002(2) -0.0097(19) C14 0.042(3) 0.020(2) 0.035(3) -0.003(2) 0.002(2) 0.006(2) C15 0.044(3) 0.037(3) 0.023(2) -0.001(2) 0.006(2) 0.005(2) C16 0.028(2) 0.030(3) 0.017(2) -0.0004(18) 0.0003(18) 0.0001(18) N12 0.023(2) 0.041(3) 0.0194(18) 0.0032(17) 0.0035(16) 0.0009(18) O121 0.0252(16) 0.038(2) 0.0228(15) 0.0003(14) 0.0022(13) 0.0101(14) O122 0.078(3) 0.056(2) 0.0151(16) -0.0101(18) -0.0001(16) -0.0103(15) 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 . 1.386(5) no C1 C2 . 1.390(5) no C2 C3 . 1.376(5) no C2 H2 . 0.95 no C3 C4 . 1.376(6) no C3 H3 . 0.95 no C4 C5 . 1.383(5) no C4 I4 . 2.111(4) no C5 C6 . 1.390(5) no C5 H5 . 0.95 no C6 H6 . 0.95 no C1 N1 . 1.404(5) y S1 N1 . 1.679(3) y S1 C11 . 1.774(4) y C12 N12 . 1.455(5) y N12 O121 . 1.238(4) y N12 O122 . 1.224(4) y N1 H1 . 0.88 no C11 C12 . 1.407(5) y C12 C13 . 1.385(6) y C13 C14 . 1.365(5) y C14 C15 . 1.388(5) y C15 C16 . 1.374(6) y C16 C11 . 1.394(5) y C13 H13 . 0.95 no C14 H14 . 0.95 no C15 H15 . 0.95 no C16 H16 . 0.95 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' S S 0.1246 0.1234 '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 119.1(4) no C6 C1 N1 122.1(3) no C2 C1 N1 118.8(3) no C3 C2 C1 120.7(4) no C3 C2 H2 119.6 no C1 C2 H2 119.6 no C4 C3 C2 119.5(4) no C4 C3 H3 120.2 no C2 C3 H3 120.2 no C3 C4 C5 121.0(4) no C3 C4 I4 119.6(3) no C5 C4 I4 119.3(3) no C4 C5 C6 119.1(4) no C4 C5 H5 120.5 no C6 C5 H5 120.5 no C1 C6 C5 120.5(4) no C1 C6 H6 119.8 no C5 C6 H6 119.8 no C1 N1 H1 117.5 no S1 N1 H1 117.5 no C1 N1 S1 124.9(3) y N1 S1 C11 101.5(2) y C12 C11 C16 115.8(4) y S1 C11 C12 123.5(3) y S1 C11 C16 120.7(3) y C11 C12 C13 122.6(3) y C11 C12 N12 119.5(4) y C13 C12 N12 118.0(3) y C14 C13 C12 120.3(4) no C14 C13 H13 119.9 no C12 C13 H13 119.9 no C13 C14 C15 118.2(4) no C13 C14 H14 120.9 no C15 C14 H14 120.9 no C16 C15 C14 122.0(4) no C16 C15 H15 119.0 no C14 C15 H15 119.0 no C15 C16 C11 121.2(4) no C15 C16 H16 119.4 no C11 C16 H16 119.4 no O122 N12 O121 123.9(3) no O122 N12 C12 118.6(4) no O121 N12 C12 117.6(3) 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 H1 O121 6_556 0.88 2.16 2.935(4) 147 y C6 H6 O121 6_656 0.95 2.49 3.231(5) 135 y C16 H16 O122 7_575 0.95 2.49 3.220(5) 134 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 C6 C1 C2 C3 0.6(6) no N1 C1 C2 C3 179.0(3) no C1 C2 C3 C4 -0.6(6) no C2 C3 C4 C5 0.5(6) no C2 C3 C4 I4 177.3(3) no C3 C4 C5 C6 -0.4(6) no I4 C4 C5 C6 -177.2(3) no C2 C1 C6 C5 -0.5(6) no N1 C1 C6 C5 -178.8(4) no C4 C5 C6 C1 0.4(6) no C6 C1 N1 S1 -18.3(5) no C1 N1 S1 C11 94.7(3) y C2 C1 N1 S1 163.4(3) y N1 S1 C11 C12 171.7(3) y N1 S1 C11 C16 -7.7(3) no C16 C11 C12 C13 -0.3(6) no S1 C11 C12 C13 -179.8(3) no C16 C11 C12 N12 179.5(3) no S1 C11 C12 N12 0.0(5) no C11 C12 C13 C14 -0.1(6) no N12 C12 C13 C14 -180.0(4) no C12 C13 C14 C15 -0.2(6) no C13 C14 C15 C16 1.0(7) no C14 C15 C16 C11 -1.5(7) no C12 C11 C16 C15 1.1(6) no S1 C11 C16 C15 -179.4(3) no C13 C12 N12 O122 5.0(5) no C11 C12 N12 O122 -174.8(3) no C13 C12 N12 O121 -174.5(3) no C11 C12 N12 O121 5.7(5) y