#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014744.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_2014744 loop_ _publ_author_name 'Garden, Simon J.' 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; 2-Iodo-6-methoxy-4-nitroaniline: tripartite ribbons built from N---H···O hydrogen bonds and iodo--nitro interactions are \p-stacked into sheets ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o145 _journal_page_last o147 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C7 H7 I N2 O3' _chemical_formula_moiety 'C7 H7 I N2 O3' _chemical_formula_sum 'C7 H7 I N2 O3' _chemical_formula_weight 294.05 _chemical_name_systematic ; 2-Iodo-6-methoxy-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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 112.616(2) _cell_angle_beta 115.060(3) _cell_angle_gamma 93.810(3) _cell_formula_units_Z 2 _cell_length_a 8.0671(3) _cell_length_b 8.0739(4) _cell_length_c 8.6212(5) _cell_measurement_reflns_used 2061 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.51 _cell_measurement_theta_min 3.70 _cell_volume 451.55(4) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker-Nonius FR91 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 8665 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 3.70 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 3.522 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_correction_T_min 0.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.163 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _refine_diff_density_max 1.271 _refine_diff_density_min -0.771 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2061 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0251 _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^)+(0.0279P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.0530 _reflns_number_gt 1845 _reflns_number_total 2061 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1806.cif _[local]_cod_data_source_block I _cod_database_code 2014744 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_type_symbol I2 0.21628(2) 0.90838(2) 0.66781(3) 0.02135(8) Uani d . 1 I O1 0.7476(3) 0.6384(3) 1.0752(3) 0.0265(5) Uani d . 1 O O2 0.7049(3) 0.3445(3) 0.9016(3) 0.0256(5) Uani d . 1 O O6 0.1721(3) 0.1987(3) 0.2458(3) 0.0194(4) Uani d . 1 O N1 0.0624(3) 0.5013(4) 0.2886(3) 0.0235(6) Uani d . 1 N N4 0.6613(3) 0.4922(3) 0.9212(3) 0.0190(5) Uani d . 1 N C1 0.2056(4) 0.5048(4) 0.4476(4) 0.0151(6) Uani d . 1 C C2 0.2989(4) 0.6607(4) 0.6293(4) 0.0149(6) Uani d . 1 C C3 0.4480(4) 0.6571(4) 0.7856(4) 0.0169(6) Uani d . 1 C C4 0.5038(4) 0.4954(4) 0.7597(4) 0.0151(6) Uani d . 1 C C5 0.4153(4) 0.3347(4) 0.5824(4) 0.0156(6) Uani d . 1 C C6 0.2686(4) 0.3417(4) 0.4282(4) 0.0162(6) Uani d . 1 C C61 0.2159(4) 0.0240(4) 0.2147(4) 0.0224(6) Uani d . 1 C H3 0.5103 0.7640 0.9079 0.020 Uiso calc R 1 H H5 0.4550 0.2241 0.5686 0.019 Uiso calc R 1 H H11 0.0225 0.6014 0.2957 0.028 Uiso calc R 1 H H12 0.0094 0.3989 0.1783 0.028 Uiso calc R 1 H H61A 0.3503 0.0405 0.2487 0.034 Uiso calc R 1 H H61B 0.1361 -0.0667 0.0789 0.034 Uiso calc R 1 H H61C 0.1914 -0.0217 0.2952 0.034 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 I2 0.02230(12) 0.01713(12) 0.02269(12) 0.01023(8) 0.00859(8) 0.00921(9) O1 0.0306(11) 0.0176(11) 0.0140(11) 0.0105(9) 0.0000(9) 0.0026(9) O2 0.0318(11) 0.0166(11) 0.0202(11) 0.0142(9) 0.0055(9) 0.0077(9) O6 0.0186(9) 0.0146(10) 0.0142(10) 0.0055(8) 0.0014(8) 0.0037(8) N1 0.0224(12) 0.0182(13) 0.0171(13) 0.0084(10) 0.0008(10) 0.0055(11) N4 0.0206(12) 0.0185(13) 0.0141(12) 0.0070(10) 0.0052(10) 0.0073(11) C1 0.0137(13) 0.0180(14) 0.0155(14) 0.0042(11) 0.0066(11) 0.0099(12) C2 0.0170(13) 0.0107(13) 0.0174(14) 0.0061(11) 0.0081(11) 0.0068(11) C3 0.0184(13) 0.0149(14) 0.0149(14) 0.0035(11) 0.0067(11) 0.0062(12) C4 0.0132(12) 0.0187(15) 0.0088(13) 0.0039(11) 0.0018(10) 0.0059(11) C5 0.0169(13) 0.0154(14) 0.0155(14) 0.0053(11) 0.0071(11) 0.0087(12) C6 0.0156(13) 0.0134(14) 0.0127(14) 0.0020(11) 0.0043(11) 0.0028(11) C61 0.0247(15) 0.0134(15) 0.0168(15) 0.0040(12) 0.0045(12) 0.0021(12) 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 N1 C1 C2 124.3(3) no N1 C1 C6 118.0(3) no C2 C1 C6 117.7(2) no C1 N1 H11 120.0 no C1 N1 H12 120.0 no H11 N1 H12 120.0 no C3 C2 C1 121.6(3) no C3 C2 I2 118.6(2) no C1 C2 I2 119.83(19) no C4 C3 C2 118.6(3) no C4 C3 H3 120.7 no C2 C3 H3 120.7 no C3 C4 C5 122.5(2) no C3 C4 N4 118.8(2) no C5 C4 N4 118.7(2) no O2 N4 O1 122.4(2) no O2 N4 C4 119.0(2) no O1 N4 C4 118.6(2) no C6 C5 C4 118.0(3) no C6 C5 H5 121.0 no C4 C5 H5 121.0 no O6 C6 C5 124.9(3) no O6 C6 C1 113.5(2) no C5 C6 C1 121.6(2) no C6 O6 C61 117.7(2) no O6 C61 H61A 109.5 no O6 C61 H61B 109.5 no H61A C61 H61B 109.5 no O6 C61 H61C 109.5 no H61A C61 H61C 109.5 no H61B C61 H61C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 1.356(3) no C1 C2 1.401(4) no C1 C6 1.418(4) no N1 H11 0.88 no N1 H12 0.88 no C2 C3 1.388(4) no C2 I2 2.100(3) no C3 C4 1.377(4) no C3 H3 0.95 no C4 C5 1.399(4) no C4 N4 1.445(3) no N4 O2 1.234(3) no N4 O1 1.242(3) no C5 C6 1.381(4) no C5 H5 0.95 no C6 O6 1.363(3) no O6 C61 1.429(4) no C61 H61A 0.98 no C61 H61B 0.98 no C61 H61C 0.98 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_454 0.88 2.36 3.007(3) 130 y N1 H12 O2 1_454 0.88 2.45 3.028(3) 124 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 N1 C1 C2 C3 -178.3(3) no C6 C1 C2 C3 0.1(4) no N1 C1 C2 I2 0.6(4) no C6 C1 C2 I2 179.0(2) no C1 C2 C3 C4 -0.2(4) no I2 C2 C3 C4 -179.2(2) no C2 C3 C4 C5 -0.4(4) no C2 C3 C4 N4 178.9(2) no C3 C4 N4 O2 175.9(3) no C5 C4 N4 O2 -4.8(4) no C3 C4 N4 O1 -3.8(4) no C5 C4 N4 O1 175.5(3) no C3 C4 C5 C6 1.1(4) no N4 C4 C5 C6 -178.2(3) no C4 C5 C6 O6 178.2(3) no C4 C5 C6 C1 -1.2(4) no N1 C1 C6 O6 -0.3(4) no C2 C1 C6 O6 -178.8(2) no N1 C1 C6 C5 179.1(3) no C2 C1 C6 C5 0.6(4) no C5 C6 O6 C61 5.0(4) no C1 C6 O6 C61 -175.6(2) no