#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/34/2003440.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_2003440 loop_ _publ_author_name 'Ould Abdellahi, M.' 'Jouini, T.' _publ_section_title ; o-Anisidinium Dihydrogenmonophosphate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 922 _journal_page_last 923 _journal_paper_doi 10.1107/S0108270194010668 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C7 H10 N1 O1,H2 O4 P' _chemical_formula_structural (1-2,CH~3~O-C~6~H~4~-NH~3~)H~2~PO~4~ _chemical_formula_sum 'C7 H12 N O5 P' _chemical_formula_weight 221.15 _chemical_name_systematic ; o-Anisidinium Dihydrogenomonophosphate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 109.694(10) _cell_angle_beta 103.062(10) _cell_angle_gamma 90.688(10) _cell_formula_units_Z 2 _cell_length_a 5.6560(10) _cell_length_b 9.0660(10) _cell_length_c 10.4200(10) _cell_measurement_reflns_used 22 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16 _cell_measurement_theta_min 14 _cell_volume 487.77(12) _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71200 _diffrn_reflns_av_R_equivalents 0.0111 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1819 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.14 _diffrn_standards_decay_% 0.021 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.506 _exptl_crystal_description prism _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.265 _refine_diff_density_min -0.383 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.253 _refine_ls_goodness_of_fit_obs 0.239 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 1715 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.253 _refine_ls_restrained_S_obs 0.239 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_obs 0.0408 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; w = 1/[\s~2~(F~o~^2^) + (0.4751P)^2^ + 7.8262P] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1644 _refine_ls_wR_factor_obs 0.1449 _reflns_number_observed 1501 _reflns_number_total 1715 _reflns_observed_criterion >2sigma(I) _cod_data_source_file du1096.cif _cod_data_source_block ABD1 _cod_original_cell_volume 487.77(11) _cod_original_formula_sum 'C7 H12 N1 O5 P1' _cod_database_code 2003440 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 P 0.0287(5) -0.0008(3) 0.0069(3) 0.0244(4) 0.0099(3) 0.0345(5) O1 0.0304(10) 0.0006(8) 0.0097(8) 0.0351(11) 0.0068(9) 0.0349(11) O2 0.0613(15) -0.0172(10) -0.0024(11) 0.0380(13) 0.0233(11) 0.0544(14) O3 0.0478(13) 0.0176(11) 0.0073(10) 0.0489(13) 0.0117(9) 0.0341(11) O4 0.0341(11) 0.0028(9) 0.0207(10) 0.0273(11) 0.0036(10) 0.0620(14) O5 0.0507(13) -0.0108(10) 0.0153(11) 0.0478(14) 0.0076(11) 0.0537(14) N1 0.043(2) 0.0010(12) 0.0010(12) 0.0277(13) 0.0109(11) 0.045(2) C1 0.0373(15) 0.0031(11) 0.0027(12) 0.0297(14) 0.0120(12) 0.040(2) C2 0.040(2) 0.0024(12) 0.0088(13) 0.035(2) 0.0111(13) 0.045(2) C3 0.061(2) -0.004(2) 0.002(2) 0.047(2) 0.007(2) 0.049(2) C4 0.069(3) 0.008(2) 0.004(2) 0.068(3) 0.008(2) 0.039(2) C5 0.073(3) 0.005(2) 0.018(2) 0.084(3) 0.028(2) 0.051(2) C6 0.052(2) -0.004(2) 0.012(2) 0.056(2) 0.026(2) 0.058(2) C7 0.058(2) -0.009(2) 0.022(2) 0.052(2) 0.020(2) 0.081(3) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_type_symbol P 1 0.23372(12) 0.81665(7) 0.45225(7) 0.0295(3) Uani d P O1 1 0.2716(3) 0.9614(2) 0.5815(2) 0.0346(5) Uani d O O2 1 0.1615(5) 0.6660(3) 0.4670(3) 0.0524(7) Uani d O O3 1 0.0428(4) 0.8423(3) 0.3292(2) 0.0446(6) Uani d O O4 1 0.4719(4) 0.7920(2) 0.3988(2) 0.0428(6) Uani d O O5 1 0.6702(5) 0.7056(3) 0.7232(3) 0.0531(6) Uani d O N1 1 0.2948(6) 0.4899(3) 0.6323(3) 0.0410(6) Uani d N C1 1 0.3633(5) 0.5880(3) 0.7802(3) 0.0368(7) Uani d C C2 1 0.5581(6) 0.7015(4) 0.8243(3) 0.0413(7) Uani d C C3 1 0.6217(8) 0.7995(5) 0.9639(4) 0.0569(9) Uani d C C4 1 0.4911(8) 0.7815(5) 1.0545(4) 0.0629(10) Uani d C C5 1 0.2996(9) 0.6677(6) 1.0104(4) 0.0673(11) Uani d C C6 1 0.2349(7) 0.5696(5) 0.8716(4) 0.0539(9) Uani d C C7 1 0.8464(9) 0.8348(5) 0.7549(6) 0.0636(11) Uani d C H1 1 0.288(8) 0.549(5) 0.581(4) 0.06(1) Uiso d H H2 1 0.144(8) 0.439(5) 0.616(4) 0.05(1) Uiso d H H3 1 0.398(11) 0.423(7) 0.617(5) 0.09(2) Uiso d H H4 1 0.762(9) 0.877(6) 0.988(5) 0.08(1) Uiso d H H5 1 0.552(9) 0.842(6) 1.154(5) 0.08(1) Uiso d H H6 1 0.210(11) 0.653(7) 1.075(6) 0.10(2) Uiso d H H7 1 0.104(8) 0.493(5) 0.837(4) 0.05(1) Uiso d H H8 1 0.961(12) 0.836(7) 0.836(7) 0.10(2) Uiso d H H9 1 0.767(9) 0.919(6) 0.774(5) 0.08(2) Uiso d H H10 1 0.891(1) 0.822(6) 0.673(6) 0.09(2) Uiso d H H11 1 -0.052(10) 0.912(6) 0.358(5) 0.08(1) Uiso d H H12 1 0.558(8) 0.875(6) 0.405(4) 0.06(1) Uiso d H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag P P 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1023 0.094 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003 C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 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 P O1 116.40(10) yes O2 P O4 106.30(10) yes O1 P O4 110.20(10) yes O2 P O3 109.40(10) yes O1 P O3 109.50(10) yes O4 P O3 104.20(10) yes P O3 H11 113(3) no P O4 H12 117(3) no C2 O5 C7 118.3(3) yes C1 N1 H1 109(3) no C1 N1 H2 107.1(2) no H1 N1 H2 110.3(4) no C1 N1 H3 108(4) no H1 N1 H3 112(5) no H2 N1 H3 109(5) no C6 C1 C2 121.5(3) yes C6 C1 N1 120.7(3) yes C2 C1 N1 117.8(3) yes O5 C2 C1 115.3(3) yes O5 C2 C3 126.0(3) yes C1 C2 C3 118.7(3) yes C4 C3 C2 119.5(4) yes C4 C3 H4 126(3) no C2 C3 H4 114(3) no C5 C4 C3 121.5(4) yes C5 C4 H5 120(3) no C3 C4 H5 118(3) no C4 C5 C6 119.5(4) yes C4 C5 H6 121(3) no C6 C5 H6 119(3) no C1 C6 C5 119.3(4) yes C1 C6 H7 119(2) no C5 C6 H7 122(2) no O5 C7 H8 105(4) no O5 C7 H9 106(3) no H8 C7 H9 110(5) no O5 C7 H10 106(3) no H8 C7 H10 121(5) no H9 C7 H10 108(5) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P O2 1.487(2) yes P O1 1.501(2) yes P O4 1.561(2) yes P O3 1.564(2) yes O3 H11 0.86(6) no O4 H12 0.86(5) no O5 C2 1.357(4) yes O5 C7 1.427(5) yes N1 C1 1.454(4) yes N1 H1 0.87(5) no N1 H2 0.92(5) no N1 H3 0.85(6) no C1 C6 1.370(5) yes C1 C2 1.382(4) yes C2 C3 1.386(5) yes C3 C4 1.371(6) yes C3 H4 0.98(5) no C4 C5 1.370(7) yes C4 H5 0.97(5) no C5 C6 1.379(6) yes C5 H6 0.97(6) no C6 H7 0.93(4) no C7 H8 0.94(7) no C7 H9 0.88(5) no C7 H10 0.91(6) no 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 C7 O5 C2 C1 170.1(3) yes C7 O5 C2 C3 -9.8(6) yes C6 C1 C2 O5 179.3(3) ? N1 C1 C2 O5 -1.9(4) ? C6 C1 C2 C3 -0.8(5) ? N1 C1 C2 C3 178.1(3) ? O5 C2 C3 C4 -180.0(3) ? C1 C2 C3 C4 0.1(6) ? C2 C3 C4 C5 0.5(7) ? C3 C4 C5 C6 -0.5(7) ? C2 C1 C6 C5 0.8(6) ? N1 C1 C6 C5 -178.0(3) ? C4 C5 C6 C1 -0.2(7) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21138989 2 PubChem 139054266