#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/09/2200940.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_2200940 loop_ _publ_author_name ' Ch\;eci\'nska, Lilianna ' ' Ma\/lecka, Magdalena' ' Aranowska, Katarzyna' ' Ochocki, Justyn ' _publ_section_title ; 3-Pyridylmethylphosphonic acid monohydrate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o235 _journal_page_last o237 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C6 H8 N O3 P, H2 O' _chemical_formula_moiety 'C6 H8 N O3 P, H2 O' _chemical_formula_sum 'C6 H10 N O4 P' _chemical_formula_weight 191.12 _chemical_name_systematic ; 3-pyridylmethylphosphonic acid monohydrate ; _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_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.444(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.0554(7) _cell_length_b 14.0106(13) _cell_length_c 8.5228(15) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 37.77 _cell_measurement_theta_min 19.96 _cell_volume 819.40(19) _computing_cell_refinement ; KM4 Data Collection Program ; _computing_data_collection ; KM-4 Data Collection Program (Kuma, 1998) ; _computing_data_reduction 'DATAPROC (Kuma, 1996)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'PARST97 (Nardelli, 1996b)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .918 _diffrn_measured_fraction_theta_max .919 _diffrn_measurement_device_type 'Kuma KM-4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .0606 _diffrn_reflns_av_sigmaI/netI .0506 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2917 _diffrn_reflns_theta_full 67.12 _diffrn_reflns_theta_max 67.12 _diffrn_reflns_theta_min 6.20 _diffrn_standards_decay_% <3 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.839 _exptl_absorpt_correction_T_max .52679 _exptl_absorpt_correction_T_min .49129 _exptl_absorpt_correction_type cylinder _exptl_absorpt_process_details '(CYCLABS; Nardelli, 1996a)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 400 _exptl_crystal_size_rad .15 _refine_diff_density_max .443 _refine_diff_density_min -.423 _refine_ls_extinction_coef .025(2) _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 1.107 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 124 _refine_ls_number_reflns 1410 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.106 _refine_ls_R_factor_all .0558 _refine_ls_R_factor_gt .0522 _refine_ls_shift/su_max .007 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.3766P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1430 _refine_ls_wR_factor_ref .1464 _reflns_number_gt 1302 _reflns_number_total 1410 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na6137.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 819.40(18) _cod_database_code 2200940 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 .20789(9) .28625(4) .87719(7) .0352(4) Uani d . 1 . . P O1 .0880(3) .21576(12) .7493(2) .0451(6) Uani d . 1 . . O H11 .006(5) .238(3) .691(4) .061(11) Uiso d . 1 . . H O2 .3056(3) .22375(11) 1.0179(2) .0449(6) Uani d . 1 . . O O3 .0871(3) .36656(12) .9132(2) .0505(6) Uani d . 1 . . O C1 .3987(4) .33214(19) .7905(3) .0456(7) Uani d . 1 . . C H101 .4835 .3722 .8697 .055 Uiso calc R 1 . . H H102 .4759 .2790 .7670 .055 Uiso calc R 1 . . H C2 .3281(4) .38905(18) .6388(3) .0369(6) Uani d . 1 . . C C3 .3093(4) .48717(18) .6441(3) .0389(6) Uani d . 1 . . C H3 .3427 .5188 .7426 .047 Uiso calc R 1 . . H N1 .2431(3) .53678(15) .5080(2) .0406(6) Uani d . 1 . . N H1 .239(5) .600(3) .519(4) .056(9) Uiso d . 1 . . H C4 .1930(4) .4961(2) .3627(3) .0444(7) Uani d . 1 . . C H4 .1458 .5331 .2713 .053 Uiso calc R 1 . . H C5 .2117(4) .3996(2) .3496(3) .0463(7) Uani d . 1 . . C H5 .1799 .3703 .2490 .056 Uiso calc R 1 . . H C6 .2785(4) .34601(18) .4876(3) .0427(7) Uani d . 1 . . C H6 .2904 .2802 .4793 .051 Uiso calc R 1 . . H O4 .2249(4) .55319(19) .9842(3) .0759(8) Uani d D 1 . . O H401 .117(6) .587(3) 1.013(6) .114 Uiso d D 1 . . H H402 .190(7) .487(2) .978(6) .114 Uiso d 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 .0428(6) .0281(5) .0314(5) .0006(2) .0016(3) .0014(2) O1 .0513(13) .0342(11) .0417(11) -.0025(8) -.0057(9) -.0005(7) O2 .0562(13) .0340(9) .0367(10) -.0037(8) -.0053(9) .0066(7) O3 .0627(14) .0397(10) .0495(11) .0107(8) .0138(9) -.0029(7) C1 .0408(15) .0431(14) .0490(15) .0009(12) .0026(11) .0070(11) C2 .0340(13) .0356(12) .0421(13) -.0006(10) .0110(9) .0026(10) C3 .0440(15) .0348(13) .0403(13) -.0029(10) .0145(10) -.0033(10) N1 .0473(14) .0318(12) .0452(12) .0004(9) .0160(9) .0032(8) C4 .0485(17) .0458(15) .0393(13) -.0001(11) .0113(11) .0062(10) C5 .0545(18) .0467(15) .0380(13) -.0050(12) .0115(11) -.0063(11) C6 .0456(16) .0345(12) .0492(15) -.0004(11) .0137(11) -.0040(10) O4 .0752(18) .0786(17) .0845(17) -.0270(14) .0403(13) -.0273(14) 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 . 1.4860(18) yes P1 O2 . 1.5150(17) yes P1 O1 . 1.5655(18) yes P1 C1 . 1.799(3) yes O1 H11 . .74(3) no C1 C2 . 1.502(3) yes C1 H101 . .9700 no C1 H102 . .9700 no C2 C3 . 1.383(4) yes C2 C6 . 1.392(3) yes C3 N1 . 1.340(3) yes C3 H3 . .9300 no N1 C4 . 1.334(3) yes N1 H1 . .89(3) no C4 C5 . 1.366(4) yes C4 H4 . .9300 no C5 C6 . 1.383(4) yes C5 H5 . .9300 no C6 H6 . .9300 no O4 H401 . .97(3) no O4 H402 . .95(3) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .2955 .4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 0 0 1 -6 0 1 1 5 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 O2 116.84(11) yes O3 P1 O1 112.23(12) yes O2 P1 O1 105.03(10) yes O3 P1 C1 109.52(12) yes O2 P1 C1 106.60(12) yes O1 P1 C1 105.92(12) yes P1 O1 H11 115(3) no C2 C1 P1 114.42(17) yes C2 C1 H101 108.7 no P1 C1 H101 108.7 no C2 C1 H102 108.7 no P1 C1 H102 108.7 no H101 C1 H102 107.6 no C3 C2 C6 117.1(2) no C3 C2 C1 121.0(2) no C6 C2 C1 121.9(2) no N1 C3 C2 120.2(2) no N1 C3 H3 119.9 no C2 C3 H3 119.9 no C4 N1 C3 123.1(2) no C4 N1 H1 121(2) no C3 N1 H1 116(2) no N1 C4 C5 119.3(2) no N1 C4 H4 120.4 no C5 C4 H4 120.4 no C4 C5 C6 119.2(2) no C4 C5 H5 120.4 no C6 C5 H5 120.4 no C5 C6 C2 121.0(2) no C5 C6 H6 119.5 no C2 C6 H6 119.5 no H401 O4 H402 106(4) 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 H11 O2 4_565 .74(3) 1.87(3) 2.598(3) 170(4) yes N1 H1 O2 2_556 .89(3) 1.78(3) 2.644(3) 163(3) yes O4 H401 O3 3_567 .97(3) 1.82(4) 2.787(4) 171(4) yes O4 H402 O3 1_555 .95(3) 1.87(3) 2.806(3) 166(3) yes C3 H3 O4 1_555 .93 2.44 3.227(4) 142 yes C1 H101 O4 3_667 .97 2.38 3.309(4) 159 yes C4 H4 O3 3_566 .93 2.44 3.313(3) 156 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 O3 P1 C1 C2 -58.1(2) yes O2 P1 C1 C2 174.66(18) yes O1 P1 C1 C2 63.2(2) yes P1 C1 C2 C3 93.1(3) yes P1 C1 C2 C6 -86.7(3) yes C6 C2 C3 N1 .9(4) no C1 C2 C3 N1 -178.9(2) no C2 C3 N1 C4 -.2(4) no C3 N1 C4 C5 -1.0(4) no N1 C4 C5 C6 1.3(4) no C4 C5 C6 C2 -.5(4) no C3 C2 C6 C5 -.6(4) no C1 C2 C6 C5 179.3(2) no _journal_paper_doi 10.1107/S1600536802002155