#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012971.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_2012971 loop_ _publ_author_name 'Abdallah Khaoulana Idrissi' 'Mohamed Saadi' 'Mohamed Rafiq' 'Elizabeth M. Holt' _publ_section_title ; 2-Aminoanilinium phosphite ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o604 _journal_page_last o605 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C6 H9 N2 1+, H2 P1 O3 1-' _chemical_formula_moiety 'C6 H9 N2 1+, H2 P1 O3 1-' _chemical_formula_sum 'C6 H11 N2 O3 P' _chemical_formula_weight 190.14 _chemical_name_common 'o-phenylenediamine phosphite' _chemical_name_systematic ; 2-Aminoanilinium phosphite ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 110.16(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.212(8) _cell_length_b 5.992(5) _cell_length_c 13.204(14) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 9.3 _cell_measurement_theta_min 4.1 _cell_volume 832.7(13) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Siemens P4 four-circle ' _diffrn_measurement_method \q-2\q _diffrn_radiation_monochromator 'highly oriented graphite crystal' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2306 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.097 _refine_diff_density_min -0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 111 _refine_ls_number_reflns 1672 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.907 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0585 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1328P)^2^+0.2326P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1535 _refine_ls_wR_factor_ref 0.1668 _reflns_number_gt 1359 _reflns_number_total 1672 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1382.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2012971 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_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 P1 0.67177(7) 0.06825(11) 0.94968(5) 0.0286(3) Uani d . 1 . . P H1 0.7698 0.0370 0.9441 0.050 Uiso d R 1 . . H O1 0.6125(2) -0.1656(3) 0.93233(15) 0.0412(6) Uani d . 1 . . O H11 0.6178 -0.2240 0.9924 0.050 Uiso d R 1 . . H O2 0.6888(2) 0.1537(3) 1.05738(16) 0.0414(6) Uani d . 1 . . O O3 0.5969(2) 0.2060(4) 0.85740(16) 0.0396(6) Uani d . 1 . . O N1 0.6391(2) 0.5146(4) 0.72571(18) 0.0308(5) Uani d . 1 . . N H1A 0.6478 0.4141 0.7784 0.050 Uiso d R 1 . . H H1B 0.5636 0.5767 0.7189 0.050 Uiso d R 1 . . H H1C 0.6404 0.4548 0.6636 0.050 Uiso d R 1 . . H N2 0.6415(2) 0.9039(4) 0.61449(19) 0.0329(6) Uani d . 1 . . N H2A 0.6494 1.0469 0.5968 0.050 Uiso d R 1 . . H H2B 0.5647 0.8894 0.6212 0.050 Uiso d R 1 . . H C1 0.7447(3) 0.6618(5) 0.7634(2) 0.0293(6) Uani d . 1 . . C C2 0.7437(3) 0.8527(5) 0.7061(2) 0.0316(6) Uani d . 1 . . C C3 0.8496(3) 0.9842(5) 0.7394(3) 0.0411(7) Uani d . 1 . . C H3 0.8514 1.1153 0.7022 0.050 Uiso calc R 1 . . H C4 0.9519(3) 0.9269(6) 0.8255(3) 0.0479(8) Uani d . 1 . . C H4 1.0238 1.0169 0.8458 0.050 Uiso calc R 1 . . H C5 0.9505(3) 0.7397(6) 0.8823(3) 0.0496(9) Uani d . 1 . . C H5 1.0202 0.7030 0.9426 0.050 Uiso calc R 1 . . H C6 0.8473(3) 0.6070(5) 0.8507(2) 0.0400(7) Uani d . 1 . . C H6 0.8463 0.4770 0.8889 0.050 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 P1 0.0320(4) 0.0198(4) 0.0303(4) 0.0012(3) 0.0061(3) 0.0014(3) O1 0.0592(14) 0.0223(11) 0.0342(10) -0.0069(10) 0.0060(9) -0.0009(8) O2 0.0623(14) 0.0206(10) 0.0370(11) -0.0002(10) 0.0116(10) -0.0017(8) O3 0.0435(12) 0.0291(11) 0.0387(11) -0.0012(9) 0.0044(9) 0.0116(8) N1 0.0378(13) 0.0207(11) 0.0300(11) 0.0003(10) 0.0065(10) 0.0041(9) N2 0.0412(13) 0.0178(11) 0.0349(12) -0.0007(9) 0.0070(10) 0.0028(9) C1 0.0336(14) 0.0204(13) 0.0327(13) -0.0009(11) 0.0098(11) -0.0016(10) C2 0.0376(15) 0.0231(13) 0.0318(13) 0.0024(11) 0.0089(12) -0.0019(11) C3 0.0442(17) 0.0287(15) 0.0500(17) -0.0059(13) 0.0156(14) -0.0006(13) C4 0.0351(16) 0.047(2) 0.055(2) -0.0106(14) 0.0066(14) -0.0064(15) C5 0.0377(16) 0.050(2) 0.0494(18) 0.0050(15) -0.0006(14) 0.0041(16) C6 0.0411(16) 0.0344(16) 0.0370(15) 0.0069(13) 0.0039(13) 0.0076(13) 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 P1 O2 . 1.461(3) yes P1 O3 . 1.471(2) yes P1 O1 . 1.534(2) yes P1 H1 . 1.1421 no O1 H11 . 0.8500 no N1 C1 . 1.422(4) yes N1 H1A . 0.90 no N1 H1B . 0.90 no N1 H1C . 0.90 no N2 C2 . 1.384(4) yes N2 H2A . 0.90 no N2 H2B . 0.90 no C1 C6 . 1.359(4) yes C1 C2 . 1.370(4) yes C2 C3 . 1.365(4) yes C3 C4 . 1.352(5) yes C3 H3 . 0.93 no C4 C5 . 1.352(5) yes C4 H4 . 0.93 no C5 C6 . 1.346(5) yes C5 H5 . 0.93 no C6 H6 . 0.93 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' 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' P P 0.1023 0.0942 '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 O2 P1 O3 117.08(14) yes O2 P1 O1 111.72(12) yes O3 P1 O1 107.12(13) yes O2 P1 H1 108.3 no O3 P1 H1 109.0 no O1 P1 H1 102.6 no P1 O1 H11 110.4 no C1 N1 H1A 106.8 no C1 N1 H1B 114.8 no H1A N1 H1B 101.6 no C1 N1 H1C 107.0 no H1A N1 H1C 114.0 no H1B N1 H1C 112.6 no C2 N2 H2A 108.1 no C2 N2 H2B 115.1 no H2A N2 H2B 107.5 no C6 C1 C2 120.9(3) yes C6 C1 N1 120.4(3) yes C2 C1 N1 118.5(3) yes C3 C2 C1 117.6(3) yes C3 C2 N2 121.3(3) yes C1 C2 N2 121.0(3) yes C4 C3 C2 121.0(3) yes C4 C3 H3 119.5 no C2 C3 H3 119.5 no C3 C4 C5 120.6(3) yes C3 C4 H4 119.7 no C5 C4 H4 119.7 no C4 C5 C6 119.4(3) yes C4 C5 H5 120.3 no C6 C5 H5 120.3 no C1 C6 C5 120.4(3) yes C1 C6 H6 119.8 no C5 C6 H6 119.8 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 N1 H1A O3 . 0.90 1.84 2.690(3) 157 N1 H1B O3 2_656 0.90 1.90 2.741(4) 155 N1 H1C O2 4_565 0.90 1.79 2.669(4) 164 N2 H2B O3 2_656 0.90 2.22 3.061(4) 156 N2 H2A O2 4_575 0.90 1.96 2.855(4) 172 O1 H11 N2 4_566 0.85 1.88 2.719(4) 168 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 0.5(4) no N1 C1 C2 C3 -175.6(3) no C6 C1 C2 N2 177.2(3) no N1 C1 C2 N2 1.1(4) no C1 C2 C3 C4 0.4(5) no N2 C2 C3 C4 -176.4(3) no C2 C3 C4 C5 -1.5(6) no C3 C4 C5 C6 1.7(6) no C2 C1 C6 C5 -0.2(5) no N1 C1 C6 C5 175.8(3) no C4 C5 C6 C1 -0.9(5) no _cod_database_fobs_code 2012971