#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012783.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_2012783 loop_ _publ_author_name 'Demir, Selcuk' 'Yilmaz, Veysel T.' 'Andac, Omer' 'Harrison, William T. A.' _publ_section_title ; N-(2-Hydroxyethyl)ethylenediammonium hydrogenphosphate monohydrate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o407 _journal_page_last o408 _journal_paper_doi 10.1107/S0108270102009629 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C4 H14 N2 O 2+ , H O4 P 2- , H2 O' _chemical_formula_sum 'C4 H17 N2 O6 P' _chemical_formula_weight 220.17 _chemical_name_systematic ; N-(2-hydroxyethyl)ethylenediammonium hydrogenphosphate monohydrate ; _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 mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary none _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 94.8740(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.0863(3) _cell_length_b 28.4885(11) _cell_length_c 4.8336(2) _cell_measurement_reflns_used 5486 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.47 _cell_measurement_theta_min 2.88 _cell_volume 972.27(7) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 9939 _diffrn_reflns_theta_full 32.51 _diffrn_reflns_theta_max 32.51 _diffrn_reflns_theta_min 2.88 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_T_max 0.947 _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description chunk _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.34 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 162 _refine_ls_number_reflns 3520 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.103 _refine_ls_R_factor_all 0.038 _refine_ls_R_factor_gt 0.032 _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^)+(0.0512P)^2^+0.0694P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.088 _refine_ls_wR_factor_ref 0.091 _reflns_number_gt 3051 _reflns_number_total 3520 _reflns_threshold_expression I>2\s(I) _cod_data_source_file av1110.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012783 _cod_database_fobs_code 2012783 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 0.24386(3) 0.066713(9) 0.53198(5) 0.01795(7) Uani d . 1 . . P O1 0.29299(11) 0.03924(3) 0.79651(15) 0.02687(16) Uani d . 1 . . O O2 0.06383(10) 0.09652(3) 0.54860(15) 0.02467(15) Uani d . 1 . . O O3 0.40488(10) 0.09761(3) 0.44708(16) 0.02603(16) Uani d . 1 . . O O4 0.19514(14) 0.02854(3) 0.29789(17) 0.0344(2) Uani d . 1 . . O H4 0.227(4) 0.0375(10) 0.152(5) 0.090(8) Uiso d . 1 . . H O5 0.32252(15) 0.18549(3) 0.3287(2) 0.0384(2) Uani d . 1 . . O H5 0.346(3) 0.1595(7) 0.351(4) 0.050(5) Uiso d . 1 . . H O1W 0.67791(16) 0.22440(5) 0.4570(2) 0.0462(3) Uani d . 1 . . O H1A 0.572(4) 0.2120(9) 0.435(5) 0.074(7) Uiso d . 1 . . H H1B 0.667(3) 0.2415(8) 0.595(5) 0.069(7) Uiso d . 1 . . H N1 -0.01794(12) 0.13671(3) 0.03106(18) 0.02173(16) Uani d . 1 . . N H111 0.022(2) 0.1264(6) 0.198(3) 0.036(4) Uiso d . 1 . . H H112 0.027(2) 0.1211(6) -0.094(4) 0.038(4) Uiso d . 1 . . H N2 -0.27371(12) 0.05690(4) 0.27835(19) 0.02369(17) Uani d . 1 . . N H211 -0.278(2) 0.0247(6) 0.264(3) 0.038(4) Uiso d . 1 . . H H212 -0.371(2) 0.0689(6) 0.354(4) 0.040(4) Uiso d . 1 . . H H213 -0.167(2) 0.0633(6) 0.385(3) 0.035(4) Uiso d . 1 . . H C1 0.25351(17) 0.19171(5) 0.0471(3) 0.0361(3) Uani d . 1 . . C H11 0.3124 0.1687 -0.0661 0.053(5) Uiso calc R 1 . . H H12 0.2891 0.2227 -0.0138 0.045(5) Uiso calc R 1 . . H C2 0.03989(17) 0.18656(4) 0.0031(3) 0.0328(2) Uani d . 1 . . C H21 -0.0190 0.2055 0.1386 0.049(5) Uiso calc R 1 . . H H22 -0.0038 0.1979 -0.1804 0.050(5) Uiso calc R 1 . . H C3 -0.22630(14) 0.12816(4) -0.0113(2) 0.0261(2) Uani d . 1 . . C H31 -0.2751 0.1413 -0.1882 0.040(4) Uiso calc R 1 . . H H32 -0.2887 0.1438 0.1339 0.052(5) Uiso calc R 1 . . H C4 -0.27073(14) 0.07612(4) -0.0070(2) 0.0252(2) Uani d . 1 . . C H4A -0.3932 0.0708 -0.1076 0.040(4) Uiso calc R 1 . . H H4B -0.1766 0.0593 -0.1026 0.038(4) 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 0.01798(11) 0.02074(13) 0.01533(11) -0.00010(8) 0.00256(7) -0.00059(8) O1 0.0317(4) 0.0298(4) 0.0188(3) 0.0015(3) 0.0009(3) 0.0046(3) O2 0.0181(3) 0.0311(4) 0.0249(3) 0.0035(3) 0.0023(2) -0.0001(3) O3 0.0202(3) 0.0264(4) 0.0324(4) -0.0010(3) 0.0074(3) 0.0029(3) O4 0.0533(5) 0.0300(4) 0.0213(4) -0.0118(4) 0.0108(3) -0.0072(3) O5 0.0470(5) 0.0253(4) 0.0400(5) -0.0064(4) -0.0119(4) 0.0015(3) O1W 0.0382(5) 0.0562(7) 0.0438(6) -0.0040(5) 0.0006(4) -0.0047(5) N1 0.0220(4) 0.0214(4) 0.0215(4) 0.0001(3) 0.0009(3) -0.0001(3) N2 0.0200(4) 0.0274(5) 0.0238(4) -0.0008(3) 0.0027(3) 0.0011(3) C1 0.0363(6) 0.0342(6) 0.0368(6) -0.0120(5) -0.0026(5) 0.0073(5) C2 0.0357(6) 0.0215(5) 0.0397(6) -0.0021(4) -0.0048(5) 0.0045(4) C3 0.0212(4) 0.0288(5) 0.0279(5) 0.0027(4) -0.0001(3) 0.0035(4) C4 0.0247(4) 0.0302(5) 0.0202(4) -0.0049(4) -0.0003(3) -0.0009(3) 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' 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' H H 0.0000 0.0000 '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 O1 P1 O3 113.71(4) O1 P1 O2 111.90(4) O3 P1 O2 109.75(5) O1 P1 O4 105.57(5) O3 P1 O4 109.05(5) O2 P1 O4 106.51(5) P1 O4 H4 110(2) C1 O5 H5 108.1(15) H1A O1W H1B 102(2) C2 N1 C3 114.85(9) C2 N1 H111 109.4(10) C3 N1 H111 107.9(10) C2 N1 H112 108.6(12) C3 N1 H112 104.2(11) H111 N1 H112 111.7(15) C4 N2 H211 107.4(10) C4 N2 H212 108.4(11) H211 N2 H212 113.6(14) C4 N2 H213 112.2(10) H211 N2 H213 105.6(14) H212 N2 H213 109.7(16) O5 C1 C2 112.40(11) O5 C1 H11 109.1 C2 C1 H11 109.1 O5 C1 H12 109.1 C2 C1 H12 109.1 H11 C1 H12 107.9 N1 C2 C1 111.03(10) N1 C2 H21 109.4 C1 C2 H21 109.4 N1 C2 H22 109.4 C1 C2 H22 109.4 H21 C2 H22 108.0 N1 C3 C4 111.21(9) N1 C3 H31 109.4 C4 C3 H31 109.4 N1 C3 H32 109.4 C4 C3 H32 109.4 H31 C3 H32 108.0 N2 C4 C3 113.12(9) N2 C4 H4A 109.0 C3 C4 H4A 109.0 N2 C4 H4B 109.0 C3 C4 H4B 109.0 H4A C4 H4B 107.8 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 O1 . 1.5144(8) yes P1 O2 . 1.5402(7) yes P1 O3 . 1.5247(8) yes P1 O4 . 1.5862(8) yes O4 H4 . 0.80(3) yes O5 C1 . 1.4179(16) yes O5 H5 . 0.77(2) ? O1W H1A . 0.83(3) ? O1W H1B . 0.83(2) ? N1 C2 . 1.4875(15) yes N1 C3 . 1.4933(13) yes N1 H111 . 0.881(16) ? N1 H112 . 0.832(18) ? N2 C4 . 1.4857(13) yes N2 H211 . 0.920(18) ? N2 H212 . 0.876(18) ? N2 H213 . 0.897(16) ? C1 C2 . 1.5178(17) yes C1 H11 . 0.9700 ? C1 H12 . 0.9700 ? C2 H21 . 0.9700 ? C2 H22 . 0.9700 ? C3 C4 . 1.5162(16) yes C3 H31 . 0.9700 ? C3 H32 . 0.9700 ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? 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 O4 H4 O1 1_554 0.80(3) 1.82(3) 2.5947(11) 163(3) yes O5 H5 O3 . 0.77(2) 1.86(2) 2.6228(13) 174(2) yes O1W H1A O5 . 0.83(3) 1.95(3) 2.7731(15) 172(2) yes O1W H1B O1W 4_566 0.83(2) 2.00(2) 2.8227(14) 170(2) yes N1 H111 O2 . 0.881(16) 1.898(17) 2.7674(12) 169(2) yes N1 H112 O2 1_554 0.832(18) 1.905(18) 2.7046(12) 161(2) yes N2 H211 O1 3_556 0.920(18) 1.846(18) 2.7643(13) 175(2) yes N2 H212 O3 1_455 0.876(18) 1.875(18) 2.7412(12) 169(2) yes N2 H213 O2 . 0.897(16) 1.994(17) 2.8584(12) 162(2) yes 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 C3 N1 C2 C1 -179.52(10) yes O5 C1 C2 N1 -71.91(14) yes C2 N1 C3 C4 174.46(9) yes N1 C3 C4 N2 82.13(11) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21134828 2 PubChem 139058599