#------------------------------------------------------------------------------ #$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/57/2005702.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_2005702 loop_ _publ_author_name 'Tahir, M. N.' '\"Ulk\"u, D.' 'Yilmaz, H.' 'Nazir, H.' _publ_section_title ; Ethyl {[N-(2-Hydroxyethyl)amino](2-hydroxy-1-naphthyl)methyl}phosphonate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 3133 _journal_page_last 3135 _journal_paper_doi 10.1107/S0108270196009304 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C15 H20 N O5 P' _chemical_formula_sum 'C15 H20 N O5 P' _chemical_formula_weight 325.30 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90.00 _cell_angle_beta 92.47(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.990(3) _cell_length_b 13.887(4) _cell_length_c 16.389(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294 _cell_measurement_theta_max 18.14 _cell_measurement_theta_min 10.13 _cell_volume 1589.4(9) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1993)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'MolEN version of ORTEPII (Johnson, 1976)' _computing_publication_material MolEN _computing_structure_refinement 'LSFM MolEN' _computing_structure_solution 'SIMPEL MolEN' _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 2932 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.68 _diffrn_standards_decay_% -0.28 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.19 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_type 'empirical via \y scans (MolEN; Fair, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas ? _exptl_crystal_description prismatic _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.283 _refine_diff_density_min -0.326 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.24 _refine_ls_number_parameters 199 _refine_ls_number_reflns 2036 _refine_ls_R_factor_obs 0.049 _refine_ls_shift/esd_max 0.0004 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme unit _refine_ls_wR_factor_obs 0.054 _reflns_number_observed 2036 _reflns_number_total 2680 _reflns_observed_criterion I>3\s(I) _cod_data_source_file ab1384.cif _cod_data_source_block hashmz2 _cod_depositor_comments ; 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'Unit weight' was changed to 'unit'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1589.4(8) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2005702 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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 _atom_site_aniso_type_symbol P1 0.0254(4) 0.0345(4) 0.0326(4) 0.0014(4) -0.0046(4) 0.0014(5) P O1 0.0280(10) 0.064(2) 0.0420(10) 0.0110(10) 0.0050(10) 0.0130(10) O O2 0.052(2) 0.054(2) 0.099(2) -0.006(2) 0.021(2) 0.004(2) O O3 0.0480(10) 0.0420(10) 0.0360(10) -0.0020(10) -0.0140(10) 0.0040(10) O O4 0.0330(10) 0.054(2) 0.051(2) -0.0020(10) 0.0020(10) 0.0020(10) O O5 0.0400(10) 0.0410(10) 0.047(2) 0.0060(10) -0.0020(10) -0.0010(10) O N1 0.040(2) 0.037(2) 0.0260(10) 0.0020(10) -0.0070(10) 0.0040(10) N C1 0.027(2) 0.036(2) 0.031(2) -0.003(2) -0.0040(10) 0.003(2) C C2 0.030(2) 0.042(2) 0.036(2) -0.005(2) -0.002(2) 0.006(2) C C3 0.028(2) 0.052(2) 0.053(2) -0.002(2) -0.007(2) 0.013(2) C C4 0.048(2) 0.051(2) 0.042(2) -0.008(2) -0.015(2) 0.015(2) C C5 0.049(2) 0.038(2) 0.033(2) -0.016(2) -0.007(2) 0.002(2) C C6 0.068(3) 0.056(3) 0.031(2) -0.014(2) -0.004(2) 0.006(2) C C7 0.082(3) 0.070(3) 0.034(2) -0.013(3) 0.014(2) -0.008(2) C C8 0.056(3) 0.072(3) 0.048(2) -0.003(2) 0.016(2) -0.017(2) C C9 0.042(2) 0.057(3) 0.038(2) -0.002(2) 0.003(2) -0.006(2) C C10 0.034(2) 0.037(2) 0.030(2) -0.012(2) -0.002(2) -0.004(2) C C11 0.027(2) 0.035(2) 0.029(2) 0.003(2) -0.0010(10) 0.000(2) C C12 0.050(2) 0.036(2) 0.040(2) -0.003(2) -0.005(2) -0.004(2) C C13 0.054(2) 0.042(2) 0.053(2) -0.009(2) -0.001(2) 0.004(2) C C14 0.058(2) 0.043(2) 0.069(3) 0.012(2) -0.017(2) 0.008(2) C C15 0.124(4) 0.048(3) 0.104(4) -0.013(3) -0.050(3) 0.019(3) C loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_thermal_displace_type _atom_site_type_symbol P1 0.9730(1) 0.15377(7) 0.92561(6) 2.44(2) Beq P O1 0.4915(3) 0.1428(2) 0.8745(2) 3.49(6) Beq O O2 0.3359(5) -0.0639(2) 0.9130(2) 5.34(8) Beq O O3 0.9978(4) 0.1120(2) 1.0090(2) 3.34(5) Beq O O4 1.1396(4) 0.1839(2) 0.8789(2) 3.64(6) Beq O O5 0.8351(4) 0.2434(2) 0.9341(2) 3.37(6) Beq O N1 0.7249(4) -0.0041(2) 0.9079(2) 2.73(6) Beq N C1 0.7385(5) 0.1062(3) 0.7878(2) 2.45(7) Beq C C2 0.5617(5) 0.1463(3) 0.7990(2) 2.83(7) Beq C C3 0.4556(5) 0.1900(3) 0.7336(3) 3.51(9) Beq C C4 0.5299(6) 0.1940(3) 0.6589(3) 3.76(9) Beq C C5 0.7105(6) 0.1542(3) 0.6437(2) 3.17(8) Beq C C6 0.7866(7) 0.1564(3) 0.5652(2) 4.12(9) Beq C C7 0.9576(7) 0.1165(4) 0.5504(3) 4.9(1) Beq C C8 1.0643(7) 0.0728(4) 0.6141(3) 4.6(1) Beq C C9 0.9979(6) 0.0698(3) 0.6912(3) 3.61(9) Beq C C10 0.8180(5) 0.1090(3) 0.7094(2) 2.68(7) Beq C C11 0.8473(5) 0.0620(3) 0.8603(2) 2.38(7) Beq C C12 0.6394(6) -0.0859(3) 0.8595(2) 3.34(8) Beq C C13 0.4824(6) -0.1326(3) 0.9044(3) 3.92(9) Beq C C14 0.8196(7) 0.3195(3) 0.8737(3) 4.5(1) Beq C C15 0.9289(9) 0.4054(4) 0.9010(4) 7.4(2) Beq C H1 0.381 0.161 0.879 4.6 Beq H H2 0.244 -0.091 0.933 7.0 Beq H H3 0.333 0.216 0.742 4.5 Beq H H4 0.459 0.224 0.615 4.9 Beq H H6 0.715 0.187 0.522 5.3 Beq H H7 1.005 0.118 0.497 6.3 Beq H H8 1.185 0.045 0.604 6.0 Beq H H9 1.074 0.041 0.734 4.7 Beq H H11 0.626 0.028 0.930 3.7 Beq H H11' 0.953 0.021 0.843 3.4 Beq H H12 0.793 -0.029 0.943 3.7 Beq H H121 0.738 -0.132 0.847 4.5 Beq H H122 0.590 -0.060 0.810 4.5 Beq H H131 0.436 -0.187 0.873 5.2 Beq H H132 0.522 -0.158 0.956 5.2 Beq H H141 0.679 0.332 0.859 5.8 Beq H H142 0.906 0.298 0.830 5.8 Beq H H151 0.905 0.453 0.862 9.3 Beq H H152 0.890 0.421 0.954 9.3 Beq H H153 1.066 0.394 0.907 9.3 Beq H 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 121.5(2) yes O3 P1 O5 105.8(2) yes O3 P1 C11 107.2(2) yes O4 P1 O5 108.5(2) yes O4 P1 C11 105.0(2) yes O5 P1 C11 108.4(2) yes C2 O1 H1 116.4(3) no C13 O2 H2 107.9(4) no P1 O5 C14 122.7(3) yes C11 N1 C12 114.4(3) yes C11 N1 H11 111.5(3) no C11 N1 H12 107.7(3) no C12 N1 H11 107.0(3) no C12 N1 H12 105.6(3) no H11 N1 H12 110.5(3) no C2 C1 C10 119.9(3) yes C2 C1 C11 118.9(3) yes C10 C1 C11 121.2(3) yes O1 C2 C1 118.2(3) yes O1 C2 C3 120.7(4) yes C1 C2 C3 121.1(4) yes C2 C3 C4 119.7(4) yes C2 C3 H3 120.2(4) no C4 C3 H3 120.1(4) no C3 C4 C5 121.8(4) yes C3 C4 H4 119.2(5) no C5 C4 H4 119.0(4) no C4 C5 C6 121.8(4) yes C4 C5 C10 118.9(4) yes C6 C5 C10 119.3(4) yes C5 C6 C7 121.7(4) yes C5 C6 H6 119.1(5) no C7 C6 H6 119.2(5) no C6 C7 C8 119.5(4) yes C6 C7 H7 120.2(5) no C8 C7 H7 120.3(6) no C7 C8 C9 120.9(5) yes C7 C8 H8 119.5(5) no C9 C8 H8 119.6(5) no C8 C9 C10 121.7(4) yes C8 C9 H9 119.2(5) no C10 C9 H9 119.1(4) no C1 C10 C5 118.6(4) yes C1 C10 C9 124.5(4) yes C5 C10 C9 116.9(4) yes P1 C11 N1 112.8(2) yes P1 C11 C1 112.5(3) yes P1 C11 H11' 102.5(3) no N1 C11 C1 112.3(3) yes N1 C11 H11' 104.9(3) no C1 C11 H11' 111.2(3) no N1 C12 C13 110.7(3) yes N1 C12 H121 109.9(4) no N1 C12 H122 107.1(4) no C13 C12 H121 110.8(4) no C13 C12 H122 109.9(4) no H121 C12 H122 108.4(4) no O2 C13 C12 107.8(4) yes O2 C13 H131 110.6(4) no O2 C13 H132 110.5(4) no C12 C13 H131 108.0(4) no C12 C13 H132 114.1(4) no H131 C13 H132 105.7(4) no O5 C14 C15 111.1(4) yes O5 C14 H141 109.2(4) no O5 C14 H142 104.1(4) no C15 C14 H141 114.5(4) no C15 C14 H142 97.7(5) no H141 C14 H142 119.5(5) no C14 C15 H151 106.9(5) no C14 C15 H152 107.4(6) no C14 C15 H153 113.5(5) no H151 C15 H152 114.9(6) no H151 C15 H153 109.2(7) no H152 C15 H153 105.1(6) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P1 O3 1.488(3) yes P1 O4 1.482(3) yes P1 O5 1.584(3) yes P1 C11 1.860(4) yes O1 C2 1.351(4) yes O1 H1 0.819(3) no O2 C13 1.411(5) yes O2 H2 0.830(3) no O5 C14 1.449(5) yes N1 C11 1.497(5) yes N1 C12 1.495(5) yes N1 H11 0.912(3) no N1 H12 0.810(3) no C1 C2 1.375(5) yes C1 C10 1.421(5) yes C1 C11 1.514(5) yes C2 C3 1.415(5) yes C3 C4 1.350(6) yes C3 H3 0.950(4) no C4 C5 1.411(6) yes C4 H4 0.950(4) no C5 C6 1.414(6) yes C5 C10 1.431(5) yes C6 C7 1.349(7) yes C6 H6 0.950(5) no C7 C8 1.396(7) yes C7 H7 0.950(5) no C8 C9 1.365(6) yes C8 H8 0.950(5) no C9 C10 1.415(6) yes C9 H9 0.950(5) no C11 H11' 0.984(4) no C12 C13 1.496(6) yes C12 H121 0.971(4) no C12 H122 0.941(4) no C13 H131 0.964(5) no C13 H132 0.949(5) no C14 C15 1.476(7) yes C14 H141 1.020(5) no C14 H142 0.999(5) no C15 H151 0.930(6) no C15 H152 0.954(7) no C15 H153 0.970(7) 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 O3 P1 O5 C14 161.36(0.29) no O4 P1 O5 C14 29.52(0.34) no C11 P1 O5 C14 -83.97(0.32) no O3 P1 C11 N1 26.99(0.28) no O3 P1 C11 C1 155.22(0.24) no O3 P1 C11 H11' -85.26(0.26) no O4 P1 C11 N1 157.38(0.24) no O4 P1 C11 C1 -74.38(0.27) no O4 P1 C11 H11' 45.14(0.28) no O5 P1 C11 N1 -86.79(0.26) no O5 P1 C11 C1 41.45(0.28) no O5 P1 C11 H11' 160.97(0.23) no H1 O1 C2 C1 -172.46(0.34) no H1 O1 C2 C3 7.55(0.55) no H2 O2 C13 C12 174.00(0.36) no H2 O2 C13 H131 56.09(0.52) no H2 O2 C13 H132 -60.65(0.50) no P1 O5 C14 C15 -101.68(0.41) no P1 O5 C14 H141 131.14(0.32) no P1 O5 C14 H142 2.43(0.49) no C12 N1 C11 P1 -173.27(0.25) no C12 N1 C11 C1 58.36(0.39) no C12 N1 C11 H11' -62.46(0.38) no H11 N1 C11 P1 65.13(0.33) no H11 N1 C11 C1 -63.24(0.38) no H11 N1 C11 H11' 175.94(0.28) no H12 N1 C11 P1 -56.24(0.36) no H12 N1 C11 C1 175.39(0.30) no H12 N1 C11 H11' 54.56(0.39) no C11 N1 C12 C13 -165.45(0.31) no C11 N1 C12 H121 71.88(0.41) no C11 N1 C12 H122 -45.63(0.44) no H11 N1 C12 C13 -41.42(0.41) no H11 N1 C12 H121 -164.09(0.32) no H11 N1 C12 H122 78.40(0.40) no H12 N1 C12 C13 76.31(0.40) no H12 N1 C12 H121 -46.36(0.44) no H12 N1 C12 H122 -163.87(0.34) no C10 C1 C2 O1 -179.50(0.33) no C10 C1 C2 C3 0.49(0.58) no C11 C1 C2 O1 -1.14(0.53) no C11 C1 C2 C3 178.85(0.35) no C2 C1 C10 C5 0.07(0.57) no C2 C1 C10 C9 -179.76(0.39) no C11 C1 C10 C5 -178.25(0.34) no C11 C1 C10 C9 1.91(0.59) no C2 C1 C11 P1 -80.43(0.38) no C2 C1 C11 N1 48.06(0.45) no C2 C1 C11 H11' 165.19(0.34) no C10 C1 C11 P1 97.91(0.36) no C10 C1 C11 N1 -133.60(0.35) no C10 C1 C11 H11' -16.47(0.50) no O1 C2 C3 C4 178.96(0.38) no O1 C2 C3 H3 -1.24(0.64) no C1 C2 C3 C4 -1.03(0.62) no C1 C2 C3 H3 178.76(0.39) no C2 C3 C4 C5 1.00(0.64) no C2 C3 C4 H4 -178.95(0.40) no H3 C3 C4 C5 -178.79(0.40) no H3 C3 C4 H4 1.26(0.71) no C3 C4 C5 C6 178.58(0.42) no C3 C4 C5 C10 -0.44(0.63) no H4 C4 C5 C6 -1.47(0.67) no H4 C4 C5 C10 179.51(0.39) no C4 C5 C6 C7 -178.57(0.45) no C4 C5 C6 H6 1.23(0.70) no C10 C5 C6 C7 0.45(0.67) no C10 C5 C6 H6 -179.75(0.42) no C4 C5 C10 C1 -0.10(0.57) no C4 C5 C10 C9 179.74(0.38) no C6 C5 C10 C1 -179.15(0.38) no C6 C5 C10 C9 0.69(0.57) no C5 C6 C7 C8 -0.86(0.74) no C5 C6 C7 H7 179.18(0.46) no H6 C6 C7 C8 179.33(0.47) no H6 C6 C7 H7 -0.63(0.82) no C6 C7 C8 C9 0.09(0.76) no C6 C7 C8 H8 -179.76(0.49) no H7 C7 C8 C9 -179.94(0.45) no H7 C7 C8 H8 0.20(0.85) no C7 C8 C9 C10 1.10(0.72) no C7 C8 C9 H9 -178.97(0.45) no H8 C8 C9 C10 -179.04(0.44) no H8 C8 C9 H9 0.89(0.77) no C8 C9 C10 C1 178.37(0.42) no C8 C9 C10 C5 -1.46(0.62) no H9 C9 C10 C1 -1.56(0.67) no H9 C9 C10 C5 178.61(0.40) no N1 C12 C13 O2 63.38(0.42) no N1 C12 C13 H131 -177.02(0.34) no N1 C12 C13 H132 -59.79(0.49) no H121 C12 C13 O2 -174.51(0.35) no H121 C12 C13 H131 -54.91(0.50) no H121 C12 C13 H132 62.33(0.53) no H122 C12 C13 O2 -54.70(0.47) no H122 C12 C13 H131 64.90(0.49) no H122 C12 C13 H132 -177.86(0.39) no O5 C14 C15 H151 -175.47(0.45) no O5 C14 C15 H152 -51.69(0.60) no O5 C14 C15 H153 64.03(0.64) no H141 C14 C15 H151 -51.21(0.69) no H141 C14 C15 H152 72.57(0.63) no H141 C14 C15 H153 -171.71(0.49) no H142 C14 C15 H151 76.17(0.57) no H142 C14 C15 H152 -160.05(0.48) no H142 C14 C15 H153 -44.33(0.63) no