#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015310.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_2015310 loop_ _publ_author_name 'Lemmerer, Andreas' 'Billing, David G.' _publ_section_title ; Hydrogen bonding in isomorphous 2-methyl-4-nitroanilinium bromide and iodide ; _journal_coeditor_code GD3015 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o271 _journal_page_last o273 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C7 H9 N2 O2 + , I -' _chemical_formula_moiety 'C7 H9 N2 O2 + , I -' _chemical_formula_sum 'C7 H9 I N2 O2' _chemical_formula_weight 280.06 _chemical_name_systematic ; 2-methyl-4-nitroanilinium iodide ; _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' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 93.782(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.671(4) _cell_length_b 9.830(3) _cell_length_c 6.875(2) _cell_measurement_reflns_used 576 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19.71 _cell_measurement_theta_min 3.471 _cell_volume 989.3(5) _computing_cell_refinement 'SAINT-Plus (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2003) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5499 _diffrn_reflns_theta_full 25.49 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_min 1.39 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 3.202 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_correction_T_min 0.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.88 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _refine_diff_density_max 4.269 _refine_diff_density_min -0.853 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 99 _refine_ls_number_reflns 1846 _refine_ls_number_restraints 92 _refine_ls_restrained_S_all 0.925 _refine_ls_R_factor_gt 0.0701 _refine_ls_shift/su_max 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1138P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1865 _reflns_number_gt 1047 _reflns_number_total 1846 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd3015.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_original_cell_volume 989.4(5) _cod_database_code 2015310 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_type_symbol _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 C C1 0.7037(4) 0.4315(6) 0.7801(11) 0.040(2) Uani d GU 1 C C2 0.7928(5) 0.4796(5) 0.8032(12) 0.047(2) Uani d GU 1 C C3 0.8655(4) 0.3886(8) 0.8163(12) 0.054(3) Uani d GU 1 H H3 0.9251 0.4209 0.8318 0.065 Uiso calc R 1 C C4 0.8490(4) 0.2495(7) 0.8062(12) 0.054(2) Uani d GU 1 C C5 0.7599(5) 0.2013(5) 0.7830(11) 0.049(2) Uani d GU 1 H H5 0.7489 0.1082 0.7762 0.059 Uiso calc R 1 C C6 0.6872(4) 0.2923(7) 0.7699(11) 0.048(2) Uani d GU 1 H H6 0.6276 0.2601 0.7544 0.058 Uiso calc R 1 C C7 0.8118(10) 0.6313(13) 0.822(3) 0.078(5) Uani d U 1 H H7A 0.8758 0.6477 0.8107 0.117 Uiso calc R 1 H H7B 0.7944 0.6629 0.9459 0.117 Uiso calc R 1 H H7C 0.7772 0.679 0.7196 0.117 Uiso calc R 1 N N1 0.9243(10) 0.1569(15) 0.825(2) 0.077(3) Uani d U 1 N N2 0.6273(6) 0.5232(11) 0.7665(12) 0.048(2) Uani d U 1 H H2A 0.5756 0.4757 0.7561 0.071 Uiso calc R 1 H H2B 0.6307 0.5759 0.6619 0.071 Uiso calc R 1 H H2C 0.6283 0.5748 0.8729 0.071 Uiso calc R 1 O O1 0.9969(8) 0.1965(14) 0.896(2) 0.123(5) Uani d U 1 O O2 0.9106(9) 0.0396(14) 0.7834(18) 0.111(4) Uani d U 1 I I1 0.59475(6) 0.60749(8) 0.26188(11) 0.0490(4) Uani d . 1 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 0.042(4) 0.048(4) 0.033(6) 0.001(3) 0.011(5) 0.001(5) C2 0.046(4) 0.048(4) 0.047(6) -0.004(3) 0.007(5) 0.006(5) C3 0.042(5) 0.063(4) 0.058(7) 0.001(4) 0.014(6) 0.001(6) C4 0.059(4) 0.056(4) 0.047(6) 0.010(4) 0.010(6) 0.004(6) C5 0.068(5) 0.044(5) 0.036(6) 0.001(3) 0.011(6) 0.006(5) C6 0.051(5) 0.050(4) 0.044(6) -0.008(3) 0.009(5) -0.002(5) C7 0.061(9) 0.054(5) 0.119(13) -0.009(5) 0.004(9) 0.000(8) N1 0.078(5) 0.083(6) 0.072(8) 0.033(5) 0.019(6) 0.018(6) N2 0.045(5) 0.058(6) 0.040(6) 0.004(4) 0.006(5) 0.011(5) O1 0.066(6) 0.135(10) 0.168(14) 0.029(6) 0.008(7) 0.023(9) O2 0.133(10) 0.084(6) 0.115(10) 0.061(6) -0.003(8) -0.006(7) I1 0.0580(6) 0.0466(5) 0.0425(5) -0.0084(4) 0.0053(4) 0.0000(4) 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 C2 C1 C6 120 C2 C1 N2 121.2(6) C6 C1 N2 118.8(6) C1 C2 C3 120 C1 C2 C7 120.6(7) C3 C2 C7 119.4(7) C4 C3 C2 120 C4 C3 H3 120 C2 C3 H3 120 C3 C4 C5 120 C3 C4 N1 119.4(8) C5 C4 N1 120.6(8) C4 C5 C6 120 C4 C5 H5 120 C6 C5 H5 120 C5 C6 C1 120 C5 C6 H6 120 C1 C6 H6 120 C2 C7 H7A 109.5 C2 C7 H7B 109.5 H7A C7 H7B 109.5 C2 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 O2 N1 O1 122.4(14) O2 N1 C4 118.2(14) O1 N1 C4 119.1(14) C1 N2 H2A 109.5 C1 N2 H2B 109.5 H2A N2 H2B 109.5 C1 N2 H2C 109.5 H2A N2 H2C 109.5 H2B N2 H2C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.39 C1 C6 1.39 C1 N2 1.436(10) C2 C3 1.39 C2 C7 1.521(13) C3 C4 1.39 C3 H3 0.93 C4 C5 1.39 C4 N1 1.431(13) C5 C6 1.39 C5 H5 0.93 C6 H6 0.93 C7 H7A 0.96 C7 H7B 0.96 C7 H7C 0.96 N1 O2 1.202(19) N1 O1 1.207(17) N2 H2A 0.89 N2 H2B 0.89 N2 H2C 0.89 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 N2 H2A I1 3_666 0.89 2.62 3.495(10) 166 N2 H2C I1 1_556 0.89 2.77 3.568(9) 150 N2 H2B I1 . 0.89 2.78 3.568(8) 148 N2 H2B I1 4_576 0.89 3.24 3.662(10) 112 N2 H2C I1 4_576 0.89 3.24 3.662(10) 112 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 C6 C1 C2 C3 0 N2 C1 C2 C3 179.9(8) C6 C1 C2 C7 -177.9(10) N2 C1 C2 C7 2.0(11) C1 C2 C3 C4 0 C7 C2 C3 C4 177.9(10) C2 C3 C4 C5 0 C2 C3 C4 N1 -178.4(9) C3 C4 C5 C6 0 N1 C4 C5 C6 178.3(9) C4 C5 C6 C1 0 C2 C1 C6 C5 0 N2 C1 C6 C5 -179.9(8) C3 C4 N1 O2 -167.6(11) C5 C4 N1 O2 14.0(16) C3 C4 N1 O1 18.3(17) C5 C4 N1 O1 -160.0(12) _journal_paper_doi 10.1107/S0108270106011358