#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103861.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_2103861 loop_ _publ_author_name 'Bowes, Katharine F.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _publ_section_title ; Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 248 _journal_page_last 262 _journal_paper_doi 10.1107/S0108768102021237 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C6 H16 N2 2+, 2(C3 H6 O5 P 1-), 2(H2 O)' _chemical_formula_sum 'C12 H32 N2 O12 P2' _chemical_formula_weight 458.34 _chemical_name_systematic ; N,N'-Dimethylpiperazine--phosphonopropionic acid--water (1/2/2) ; _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 111.4092(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.9270(2) _cell_length_b 20.6027(5) _cell_length_c 8.0115(2) _cell_measurement_reflns_used 2415 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.90 _cell_volume 1064.47(5) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type Kappa-CCD _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 0.035 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6838 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.90 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.344 _refine_diff_density_min -0.481 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 135 _refine_ls_number_reflns 2415 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0358 _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^)+(0.0402P)^2^+0.3605P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.0923 _reflns_number_gt 1990 _reflns_number_total 2415 _reflns_threshold_expression >2\s(I) _cod_data_source_file bm0061.cif _cod_data_source_block IV _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2103861 _cod_database_fobs_code 2103861 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_type_symbol P1 0.29332(6) 0.382569(18) 0.06467(5) 0.01690(13) Uani d . 1 P O1 -0.2948(2) 0.22877(6) -0.2716(2) 0.0426(4) Uani d . 1 O O2 -0.03885(19) 0.18412(6) -0.04435(18) 0.0369(3) Uani d . 1 O O3 0.21194(18) 0.42239(5) -0.11368(14) 0.0244(3) Uani d . 1 O O4 0.19661(16) 0.40809(5) 0.19357(14) 0.0216(3) Uani d . 1 O O5 0.52786(16) 0.38202(5) 0.14543(16) 0.0247(3) Uani d . 1 O C1 -0.1178(2) 0.23078(8) -0.1329(2) 0.0247(4) Uani d . 1 C C2 -0.0318(3) 0.29874(8) -0.1004(2) 0.0280(4) Uani d . 1 C C3 0.2023(2) 0.30174(7) -0.0040(2) 0.0228(3) Uani d . 1 C N11 0.45581(19) 0.43241(6) 0.51960(16) 0.0189(3) Uani d . 1 N C12 0.6670(2) 0.45397(8) 0.5346(2) 0.0210(3) Uani d . 1 C C13 0.6520(2) 0.51458(8) 0.4228(2) 0.0218(3) Uani d . 1 C C14 0.4643(3) 0.37154(8) 0.6226(2) 0.0270(4) Uani d . 1 C O6 0.1965(2) 0.54462(7) -0.0611(3) 0.0298(6) Uani d P 0.928(6) O O61 0.154(3) 0.5377(9) -0.161(4) 0.025 Uiso d P 0.072(6) O H1 -0.3442 0.1911 -0.2824 0.064 Uiso calc R 1 H H3 0.2154 0.4622 -0.0898 0.037 Uiso calc R 1 H H2A -0.0985 0.3225 -0.0284 0.034 Uiso calc R 1 H H2B -0.0689 0.3212 -0.2171 0.034 Uiso calc R 1 H H3A 0.2702 0.2849 -0.0846 0.027 Uiso calc R 1 H H3B 0.2426 0.2733 0.1029 0.027 Uiso calc R 1 H H11 0.3803 0.4238 0.3994 0.023 Uiso calc R 1 H H12A 0.7359 0.4189 0.4925 0.025 Uiso calc R 1 H H12B 0.7517 0.4632 0.6616 0.025 Uiso calc R 1 H H13A 0.7930 0.5291 0.4358 0.026 Uiso calc R 1 H H13B 0.5750 0.5045 0.2948 0.026 Uiso calc R 1 H H14A 0.3232 0.3581 0.6075 0.040 Uiso calc R 1 H H14B 0.5443 0.3792 0.7499 0.040 Uiso calc R 1 H H14C 0.5310 0.3373 0.5780 0.040 Uiso calc R 1 H H61 0.0767 0.5599 -0.1065 0.065 Uiso d . 1 H H62 0.2756 0.5670 -0.0951 0.065 Uiso d . 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 0.0139(2) 0.0155(2) 0.0197(2) 0.00018(14) 0.00415(15) 0.00017(15) O1 0.0290(7) 0.0225(7) 0.0541(8) -0.0081(5) -0.0114(6) 0.0042(6) O2 0.0297(7) 0.0246(7) 0.0443(8) -0.0030(5) -0.0008(6) 0.0058(6) O3 0.0310(6) 0.0210(6) 0.0209(6) 0.0010(5) 0.0092(5) 0.0017(5) O4 0.0179(5) 0.0264(6) 0.0190(5) 0.0007(5) 0.0049(4) -0.0025(5) O5 0.0141(6) 0.0189(6) 0.0376(7) 0.0002(4) 0.0053(5) 0.0007(5) C1 0.0191(8) 0.0214(8) 0.0300(8) -0.0015(7) 0.0046(7) -0.0001(7) C2 0.0204(8) 0.0198(8) 0.0357(9) -0.0021(6) 0.0007(7) 0.0000(7) C3 0.0194(8) 0.0180(8) 0.0287(8) -0.0004(6) 0.0059(7) -0.0008(7) N11 0.0193(6) 0.0185(6) 0.0168(6) -0.0007(5) 0.0043(5) -0.0008(5) C12 0.0166(7) 0.0212(8) 0.0237(8) 0.0001(6) 0.0054(6) -0.0022(6) C13 0.0204(8) 0.0219(8) 0.0238(8) -0.0006(6) 0.0088(6) -0.0021(6) C14 0.0287(9) 0.0206(8) 0.0283(9) -0.0017(7) 0.0064(7) 0.0045(7) O6 0.0210(7) 0.0211(7) 0.0492(16) 0.0033(5) 0.0152(8) 0.0065(7) 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_site_symmetry_1 _geom_angle _geom_angle_publ_flag O5 P1 O4 . 112.57(6) no O5 P1 O3 . 111.54(7) no O4 P1 O3 . 109.82(6) no O5 P1 C3 . 109.05(7) no O4 P1 C3 . 109.73(7) no O3 P1 C3 . 103.74(7) no C1 O1 H1 . 109.5 no P1 O3 H3 . 109.5 no O2 C1 O1 . 123.67(15) no O2 C1 C2 . 125.13(15) no O1 C1 C2 . 111.20(14) no C1 C2 C3 . 113.98(14) no C1 C2 H2A . 108.8 no C3 C2 H2A . 108.8 no C1 C2 H2B . 108.8 no C3 C2 H2B . 108.8 no H2A C2 H2B . 107.7 no C2 C3 P1 . 112.55(11) no C2 C3 H3A . 109.1 no P1 C3 H3A . 109.1 no C2 C3 H3B . 109.1 no P1 C3 H3B . 109.1 no H3A C3 H3B . 107.8 no C13 N11 C14 3_666 111.63(12) no C13 N11 C12 3_666 110.18(12) no C14 N11 C12 . 111.51(12) no C13 N11 H11 3_666 107.8 no C14 N11 H11 . 107.8 no C12 N11 H11 . 107.8 no N11 C12 C13 . 110.10(12) no N11 C12 H12A . 109.6 no C13 C12 H12A . 109.6 no N11 C12 H12B . 109.6 no C13 C12 H12B . 109.6 no H12A C12 H12B . 108.2 no N11 C13 C12 3_666 110.76(12) no N11 C13 H13A 3_666 109.5 no C12 C13 H13A . 109.5 no N11 C13 H13B 3_666 109.5 no C12 C13 H13B . 109.5 no H13A C13 H13B . 108.1 no N11 C14 H14A . 109.5 no N11 C14 H14B . 109.5 no H14A C14 H14B . 109.5 no N11 C14 H14C . 109.5 no H14A C14 H14C . 109.5 no H14B C14 H14C . 109.5 no O61 O6 H61 . 70.6 no O61 O6 H62 . 79.1 no H61 O6 H62 . 108.5 no O6 O61 H61 . 58.7 no O6 O61 H62 . 53.8 no H61 O61 H62 . 88.6 no 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 O5 . 1.5136(11) no P1 O4 . 1.5154(11) no P1 O3 . 1.5635(11) no P1 C3 . 1.7945(16) no O1 C1 . 1.3212(19) no O1 H1 . 0.84 no O2 C1 . 1.201(2) no O3 H3 . 0.84 no C1 C2 . 1.507(2) no C2 C3 . 1.521(2) no C2 H2A . 0.99 no C2 H2B . 0.99 no C3 H3A . 0.99 no C3 H3B . 0.99 no N11 C13 3_666 1.488(2) no N11 C14 . 1.490(2) no N11 C12 . 1.4911(19) no N11 H11 . 0.93 no C12 C13 . 1.518(2) no C12 H12A . 0.99 no C12 H12B . 0.99 no C13 N11 3_666 1.488(2) no C13 H13A . 0.99 no C13 H13B . 0.99 no C14 H14A . 0.98 no C14 H14B . 0.98 no C14 H14C . 0.98 no O6 O61 . 0.76(3) no O6 H61 . 0.84 no O6 H62 . 0.84 no O61 H61 . 0.92 no O61 H62 . 1.02 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 O5 4_465 0.84 1.74 2.562(2) 167 y O3 H3 O6 . 0.84 1.73 2.562(2) 174 y N11 H11 O4 . 0.93 1.71 2.622(2) 168 y O6 H61 O4 3_565 0.84 1.88 2.717(2) 176 y O6 H62 O5 3_665 0.83 1.88 2.707(2) 174 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 O3 P1 C3 C2 -56.5(2) no O4 P1 C3 C2 60.8(2) no O5 P1 C3 C2 -175.5(2) no P1 C3 C2 C1 -170.4(2) no C3 C2 C1 O1 -154.9(2) no C3 C2 C1 O2 25.9(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063808