#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013872.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_2013872 loop_ _publ_author_name 'Turkington, David E.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _publ_section_title ; rac-1-Phenylethylammonium carboxymethylphosphonate(1--): hydrogen-bonded anion sheets with pendent cations ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o183 _journal_page_last o185 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H12 N 1+, C2 H4 O5 P 1-' _chemical_formula_moiety 'C8 H12 N 1+, C2 H4 O5 P 1-' _chemical_formula_sum 'C10 H16 N O5 P' _chemical_formula_weight 261.21 _chemical_name_systematic ; rac-2-Phenylethylammonium carboxymethylphosphonate(1-) ; _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 96.7869(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.2969(3) _cell_length_b 13.6898(3) _cell_length_c 11.0388(4) _cell_measurement_reflns_used 2845 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 2.89 _cell_volume 1245.03(7) _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, 2003)' _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 150.0(10) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10538 _diffrn_reflns_theta_full 27.52 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 2.89 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.297 _refine_diff_density_min -0.325 _refine_ls_extinction_coef 0.0076(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 159 _refine_ls_number_reflns 2845 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0355 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.6945P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.0953 _reflns_number_gt 2394 _reflns_number_total 2845 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1696.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013872 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 0.40173(5) 0.36759(3) 0.44266(3) 0.01881(13) Uani d . 1 . . P O1 0.29772(17) 0.29493(8) 0.15716(11) 0.0320(3) Uani d . 1 . . O O2 0.40129(15) 0.44255(8) 0.13225(10) 0.0278(3) Uani d . 1 . . O O3 0.35709(14) 0.42341(8) 0.55175(9) 0.0234(3) Uani d . 1 . . O O4 0.39058(14) 0.25824(8) 0.45235(9) 0.0250(3) Uani d . 1 . . O O5 0.57737(13) 0.39345(8) 0.41434(10) 0.0233(3) Uani d . 1 . . O C1 0.32976(18) 0.38536(11) 0.19124(13) 0.0205(3) Uani d . 1 . . C C2 0.2695(2) 0.41036(12) 0.31071(14) 0.0249(3) Uani d . 1 . . C N1 0.35240(15) 0.09402(9) 0.30670(11) 0.0202(3) Uani d . 1 . . N C11 0.05149(19) 0.10557(11) 0.29944(15) 0.0249(3) Uani d . 1 . . C C12 -0.0543(2) 0.13605(16) 0.3801(2) 0.0461(5) Uani d . 1 . . C C13 -0.2009(3) 0.18031(18) 0.3377(3) 0.0663(8) Uani d . 1 . . C C14 -0.2423(3) 0.19524(15) 0.2149(3) 0.0636(8) Uani d . 1 . . C C15 -0.1371(3) 0.16794(16) 0.1346(2) 0.0551(7) Uani d . 1 . . C C16 0.0095(2) 0.12237(14) 0.17573(17) 0.0351(4) Uani d . 1 . . C C17 0.20171(19) 0.04885(11) 0.34650(14) 0.0234(3) Uani d . 1 . . C C18 0.1913(2) -0.05743(12) 0.30635(19) 0.0352(4) Uani d . 1 . . C H1 0.3347 0.2842 0.0908 0.048 Uiso calc R 1 . . H H5 0.5956 0.4530 0.4284 0.035 Uiso calc R 1 . . H H2A 0.1605 0.3814 0.3123 0.030 Uiso calc R 1 . . H H2B 0.2583 0.4822 0.3162 0.030 Uiso calc R 1 . . H H1A 0.3682 0.1542 0.3412 0.030 Uiso calc R 1 . . H H1B 0.3405 0.0998 0.2240 0.030 Uiso calc R 1 . . H H1C 0.4395 0.0553 0.3309 0.030 Uiso calc R 1 . . H H12 -0.0263 0.1266 0.4653 0.055 Uiso calc R 1 . . H H13 -0.2729 0.2003 0.3939 0.080 Uiso calc R 1 . . H H14 -0.3435 0.2244 0.1859 0.076 Uiso calc R 1 . . H H15 -0.1642 0.1802 0.0500 0.066 Uiso calc R 1 . . H H16 0.0808 0.1028 0.1190 0.042 Uiso calc R 1 . . H H17 0.2124 0.0503 0.4377 0.028 Uiso calc R 1 . . H H18A 0.1829 -0.0608 0.2172 0.053 Uiso calc R 1 . . H H18B 0.0953 -0.0877 0.3344 0.053 Uiso calc R 1 . . H H18C 0.2889 -0.0922 0.3416 0.053 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 0.0262(2) 0.0155(2) 0.0153(2) -0.00028(14) 0.00470(14) -0.00098(14) O1 0.0533(8) 0.0220(6) 0.0230(6) -0.0106(5) 0.0142(5) -0.0046(5) O2 0.0374(7) 0.0238(6) 0.0217(6) -0.0075(5) 0.0010(5) 0.0024(4) O3 0.0335(6) 0.0200(5) 0.0183(5) -0.0026(4) 0.0091(4) -0.0027(4) O4 0.0398(7) 0.0161(5) 0.0194(5) -0.0020(4) 0.0051(5) -0.0003(4) O5 0.0259(6) 0.0214(5) 0.0234(5) -0.0004(4) 0.0064(4) -0.0037(4) C1 0.0223(7) 0.0202(7) 0.0182(7) 0.0014(6) -0.0014(6) 0.0007(6) C2 0.0284(8) 0.0248(8) 0.0216(7) 0.0066(6) 0.0037(6) -0.0019(6) N1 0.0238(7) 0.0173(6) 0.0195(6) -0.0004(5) 0.0026(5) -0.0009(5) C11 0.0236(8) 0.0192(7) 0.0316(8) -0.0021(6) 0.0022(6) -0.0012(6) C12 0.0321(10) 0.0553(13) 0.0513(12) 0.0009(9) 0.0063(9) -0.0264(10) C13 0.0289(11) 0.0528(14) 0.117(2) 0.0046(9) 0.0087(13) -0.0476(16) C14 0.0276(11) 0.0228(9) 0.134(3) 0.0009(8) -0.0152(14) 0.0002(12) C15 0.0353(11) 0.0455(12) 0.0782(16) -0.0146(9) -0.0201(11) 0.0343(12) C16 0.0278(9) 0.0392(10) 0.0368(10) -0.0087(7) -0.0021(7) 0.0147(8) C17 0.0255(8) 0.0253(8) 0.0196(7) -0.0019(6) 0.0042(6) 0.0033(6) C18 0.0308(9) 0.0213(8) 0.0539(12) -0.0016(7) 0.0070(8) 0.0045(8) 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 O3 . 1.5088(11) y P1 O4 . 1.5043(11) y P1 O5 . 1.5667(11) y P1 C2 . 1.8137(16) y C1 O1 . 1.3120(18) y C1 O2 . 1.2167(19) y O1 H1 . 0.84 no O5 H5 . 0.84 no C1 C2 . 1.504(2) no C2 H2A . 0.99 no C2 H2B . 0.99 no N1 C17 . 1.5062(19) no N1 H1A . 0.91 no N1 H1B . 0.91 no N1 H1C . 0.91 no C11 C12 . 1.386(3) no C11 C16 . 1.388(2) no C11 C17 . 1.508(2) no C12 C13 . 1.390(3) no C12 H12 . 0.95 no C13 C14 . 1.374(4) no C13 H13 . 0.95 no C14 C15 . 1.367(4) no C14 H14 . 0.95 no C15 C16 . 1.394(3) no C15 H15 . 0.95 no C16 H16 . 0.95 no C17 C18 . 1.520(2) no C17 H17 . 1.00 no C18 H18A . 0.98 no C18 H18B . 0.98 no C18 H18C . 0.98 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 O3 P1 O4 115.10(6) y O4 P1 O5 107.79(6) y O5 P1 O3 111.51(6) y O3 P1 C2 107.18(7) y O4 P1 C2 109.99(7) y O5 P1 C2 104.79(7) y C1 O1 H1 109.5 no P1 O5 H5 109.5 no O2 C1 O1 123.29(14) no O2 C1 C2 123.81(14) no O1 C1 C2 112.90(13) no C1 C2 P1 113.50(11) no C1 C2 H2A 108.9 no P1 C2 H2A 108.9 no C1 C2 H2B 108.9 no P1 C2 H2B 108.9 no H2A C2 H2B 107.7 no C17 N1 H1A 109.5 no C17 N1 H1B 109.5 no H1A N1 H1B 109.5 no C17 N1 H1C 109.5 no H1A N1 H1C 109.5 no H1B N1 H1C 109.5 no C12 C11 C16 118.55(18) no C12 C11 C17 119.59(17) no C16 C11 C17 121.69(16) no C11 C12 C13 120.7(2) no C11 C12 H12 119.7 no C13 C12 H12 119.7 no C14 C13 C12 120.2(2) no C14 C13 H13 119.9 no C12 C13 H13 119.9 no C15 C14 C13 119.6(2) no C15 C14 H14 120.2 no C13 C14 H14 120.2 no C14 C15 C16 120.7(2) no C14 C15 H15 119.6 no C16 C15 H15 119.6 no C11 C16 C15 120.1(2) no C11 C16 H16 119.9 no C15 C16 H16 119.9 no N1 C17 C11 111.65(12) no N1 C17 C18 109.18(13) no C11 C17 C18 112.09(14) no N1 C17 H17 107.9 no C11 C17 H17 107.9 no C18 C17 H17 107.9 no C17 C18 H18A 109.5 no C17 C18 H18B 109.5 no H18A C18 H18B 109.5 no C17 C18 H18C 109.5 no H18A C18 H18C 109.5 no H18B C18 H18C 109.5 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 O1 H1 O4 4_565 0.84 1.75 2.5781(15) 169 y O5 H5 O3 3_666 0.84 1.75 2.5834(15) 176 y N1 H1A O4 . 0.91 1.88 2.7603(16) 164 y N1 H1B O3 4_565 0.91 1.95 2.8293(16) 162 y N1 H1C O2 2_645 0.91 2.04 2.9334(17) 166 y C2 H2B Cg1 2_555 0.99 2.75 3.6417(19) 150 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 O2 C1 C2 P1 -99.72(16) no O1 C1 C2 P1 80.00(16) no O4 P1 C2 C1 -71.68(13) no O3 P1 C2 C1 162.51(11) no O5 P1 C2 C1 43.93(13) no C16 C11 C12 C13 1.5(3) no C17 C11 C12 C13 -173.91(19) no C11 C12 C13 C14 -0.6(3) no C12 C13 C14 C15 -1.2(3) no C13 C14 C15 C16 2.0(3) no C12 C11 C16 C15 -0.7(3) no C17 C11 C16 C15 174.61(16) no C14 C15 C16 C11 -1.0(3) no C12 C11 C17 N1 -127.50(16) no C16 C11 C17 N1 57.2(2) no C12 C11 C17 C18 109.65(18) no C16 C11 C17 C18 -65.7(2) no _cod_database_fobs_code 2013872 _journal_paper_doi 10.1107/S0108270104000939