#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014684.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_2014684 loop_ _publ_author_name ' Ch\;eci\'nska, Lilianna ' ' Ma\/lecka, Magdalena ' ' Aranowska, Katarzyna' ' Ochocki, Justyn ' _publ_section_title ; Ethyl (2-pyridylmethyl)phosphonate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o4 _journal_page_last o6 _journal_paper_doi 10.1107/S0108270104029221 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C8 H12 N O3 P' _chemical_formula_moiety 'C8 H12 N O3 P' _chemical_formula_sum 'C8 H12 N O3 P' _chemical_formula_weight 201.16 _chemical_name_systematic ; Ethyl (2-pyridylmethyl)phosphonate ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.534(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.7169(5) _cell_length_b 11.2997(5) _cell_length_c 9.7940(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 37.16 _cell_measurement_theta_min 33.08 _cell_volume 933.82(8) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989) ; _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Rigaku AFC-5S' _diffrn_measurement_method '\w scan' _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 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 1849 _diffrn_reflns_theta_full 69.95 _diffrn_reflns_theta_max 69.95 _diffrn_reflns_theta_min 5.24 _diffrn_standards_decay_% 1.9 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.438 _exptl_absorpt_correction_T_max 0.7021 _exptl_absorpt_correction_T_min 0.5353 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(de Meulenaer & Tompa, 1965)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.356 _refine_diff_density_min -0.405 _refine_ls_extinction_coef 0.025(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 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 1743 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0455 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1258 _refine_ls_wR_factor_ref 0.1338 _reflns_number_gt 1268 _reflns_number_total 1743 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ga1090.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Analytical' changed to 'analytical' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2014684 _cod_database_fobs_code 2014684 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 0.68878(8) 0.34585(6) 0.46363(8) 0.0373(3) Uani d . 1 . . P O1 0.6125(2) 0.40058(17) 0.5687(2) 0.0437(5) Uani d . 1 . . O O2 0.6834(2) 0.20714(17) 0.4955(2) 0.0465(6) Uani d . 1 . . O C7 0.7761(4) 0.1250(3) 0.4418(4) 0.0540(8) Uani d . 1 . . C H7A 0.8837 0.1543 0.4565 0.065 Uiso calc R 1 . . H H7B 0.7321 0.1143 0.3413 0.065 Uiso calc R 1 . . H C8 0.7765(4) 0.0070(3) 0.5185(3) 0.0649(10) Uani d . 1 . . C H8A 0.8182 0.0187 0.6181 0.097 Uiso calc R 1 . . H H8B 0.8414 -0.0489 0.4848 0.097 Uiso calc R 1 . . H H8C 0.6701 -0.0227 0.5009 0.097 Uiso calc R 1 . . H O3 0.8466(2) 0.3873(2) 0.4569(2) 0.0528(6) Uani d . 1 . . O C1 0.5555(3) 0.3642(2) 0.2890(3) 0.0414(7) Uani d . 1 . . C H11 0.5527 0.4474 0.2640 0.050 Uiso calc R 1 . . H H12 0.5990 0.3214 0.2215 0.050 Uiso calc R 1 . . H C2 0.3891(3) 0.3228(2) 0.2749(3) 0.0374(6) Uani d . 1 . . C C3 0.3268(3) 0.2197(3) 0.2037(3) 0.0431(7) Uani d . 1 . . C H3 0.3903 0.1708 0.1645 0.052 Uiso calc R 1 . . H C4 0.1700(4) 0.1910(3) 0.1921(3) 0.0527(8) Uani d . 1 . . C H4 0.1266 0.1230 0.1442 0.063 Uiso calc R 1 . . H C5 0.0771(4) 0.2651(3) 0.2528(3) 0.0501(8) Uani d . 1 . . C H5 -0.0293 0.2478 0.2440 0.060 Uiso calc R 1 . . H C6 0.1429(3) 0.3618(3) 0.3241(3) 0.0473(8) Uani d . 1 . . C H6 0.0832 0.4097 0.3684 0.057 Uiso calc R 1 . . H N1 0.2954(3) 0.3896(2) 0.3317(2) 0.0400(6) Uani d . 1 . . N H1 0.3338 0.4533 0.3751 0.048 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 0.0308(4) 0.0392(4) 0.0411(4) 0.0013(3) 0.0075(3) -0.0005(3) O1 0.0449(11) 0.0441(12) 0.0432(11) 0.0049(9) 0.0130(9) -0.0059(9) O2 0.0500(12) 0.0348(12) 0.0574(13) 0.0080(9) 0.0186(10) 0.0018(9) C7 0.063(2) 0.0477(19) 0.0524(19) 0.0142(15) 0.0171(16) -0.0023(15) C8 0.078(2) 0.0426(19) 0.072(2) 0.0155(17) 0.0139(19) 0.0029(17) O3 0.0281(10) 0.0626(14) 0.0659(15) -0.0045(9) 0.0087(9) 0.0011(11) C1 0.0344(14) 0.0480(17) 0.0431(15) -0.0037(12) 0.0119(12) 0.0007(13) C2 0.0328(13) 0.0405(16) 0.0372(14) 0.0023(11) 0.0055(11) 0.0025(12) C3 0.0446(16) 0.0426(17) 0.0408(16) 0.0021(13) 0.0081(12) -0.0025(13) C4 0.0486(18) 0.0537(19) 0.0508(19) -0.0102(15) 0.0032(14) -0.0021(15) C5 0.0353(15) 0.065(2) 0.0484(18) -0.0083(14) 0.0066(13) 0.0027(15) C6 0.0335(14) 0.060(2) 0.0482(17) 0.0069(14) 0.0094(13) 0.0028(14) N1 0.0342(12) 0.0436(13) 0.0407(13) 0.0024(10) 0.0063(10) -0.0039(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 -1 1 2 1 1 2 -1 -1 2 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 O1 118.85(13) yes O3 P1 O2 113.22(12) yes O1 P1 O2 103.37(11) yes O3 P1 C1 107.73(13) yes O1 P1 C1 108.12(12) yes O2 P1 C1 104.58(12) yes C7 O2 P1 121.44(19) no O2 C7 C8 108.6(3) no O2 C7 H7A 110.0 no C8 C7 H7A 110.0 no O2 C7 H7B 110.0 no C8 C7 H7B 110.0 no H7A C7 H7B 108.3 no C7 C8 H8A 109.5 no C7 C8 H8B 109.5 no H8A C8 H8B 109.5 no C7 C8 H8C 109.5 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no C2 C1 P1 115.16(19) yes C2 C1 H11 108.5 no P1 C1 H11 108.5 no C2 C1 H12 108.5 no P1 C1 H12 108.5 no H11 C1 H12 107.5 no N1 C2 C3 118.6(3) no N1 C2 C1 117.8(2) no C3 C2 C1 123.6(3) no C4 C3 C2 119.3(3) no C4 C3 H3 120.3 no C2 C3 H3 120.3 no C3 C4 C5 119.5(3) no C3 C4 H4 120.3 no C5 C4 H4 120.3 no C6 C5 C4 119.3(3) no C6 C5 H5 120.3 no C4 C5 H5 120.3 no C5 C6 N1 120.2(3) no C5 C6 H6 119.9 no N1 C6 H6 119.9 no C2 N1 C6 123.0(3) no C2 N1 H1 118.5 no C6 N1 H1 118.5 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 O3 . 1.4702(19) yes P1 O1 . 1.4925(19) yes P1 O2 . 1.601(2) yes P1 C1 . 1.822(3) yes O2 C7 . 1.416(3) no C7 C8 . 1.530(4) no C7 H7A . 0.9700 no C7 H7B . 0.9700 no C8 H8A . 0.9600 no C8 H8B . 0.9600 no C8 H8C . 0.9600 no C1 C2 . 1.498(4) yes C1 H11 . 0.9700 no C1 H12 . 0.9700 no C2 N1 . 1.332(3) no C2 C3 . 1.396(4) no C3 C4 . 1.382(4) no C3 H3 . 0.9300 no C4 C5 . 1.398(4) no C4 H4 . 0.9300 no C5 C6 . 1.345(4) no C5 H5 . 0.9300 no C6 N1 . 1.349(3) no C6 H6 . 0.9300 no N1 H1 . 0.8600 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 N1 H1 O1 3_666 0.86 1.77 2.612(3) 168 yes C6 H6 O3 1_455 0.93 2.44 3.183(3) 137 yes C3 H3 O1 4_565 0.93 2.49 3.384(3) 161 yes C1 H12 O2 4_565 0.97 2.52 3.430(3) 156 yes C8 H8B Cg 2_645 0.96 2.96 3.663(3) 131 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 O2 C7 -35.1(3) no O1 P1 O2 C7 -165.1(2) no C1 P1 O2 C7 81.9(2) no P1 O2 C7 C8 166.3(2) no O3 P1 C1 C2 178.3(2) no O1 P1 C1 C2 -52.1(2) no O2 P1 C1 C2 57.5(2) no P1 C1 C2 N1 74.7(3) no P1 C1 C2 C3 -106.6(3) no N1 C2 C3 C4 1.1(4) no C1 C2 C3 C4 -177.7(3) no C2 C3 C4 C5 -0.6(4) no C3 C4 C5 C6 -1.4(5) no C4 C5 C6 N1 2.8(5) no C3 C2 N1 C6 0.4(4) no C1 C2 N1 C6 179.2(3) no C5 C6 N1 C2 -2.4(4) no