#------------------------------------------------------------------------------ #$Date: 2016-03-26 17:21:16 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180389 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/58/7205884.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7205884 loop_ _publ_author_name 'Zavras, Athanasios' 'Fry, Julie A.' 'Beavers, Christine M.' 'Talbo, Gert H.' 'Richards, Anne F.' _publ_section_title ; 2-Pyridylmethylphosphonic acid: a flexible, multi-dentate ligand for metal phosphonates ; _journal_issue 10 _journal_name_full CrystEngComm _journal_page_first 3551 _journal_paper_doi 10.1039/c0ce00969e _journal_volume 13 _journal_year 2011 _chemical_formula_sum 'C12 H20 Cl2 Fe N2 O16 P2' _chemical_formula_weight 636.99 _chemical_name_common (((2PyHCH2PO3H)Fe(H2O))ClO4)n _chemical_name_systematic ; ? ; _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 97.108(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 13.5170(8) _cell_length_b 8.2636(4) _cell_length_c 10.3910(4) _cell_measurement_reflns_used 3262 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 29.2873 _cell_measurement_theta_min 2.4597 _cell_volume 1151.75(10) _computing_cell_refinement 'CrysAlisPro, V. 171.34.40' _computing_data_collection 'CrysAlisPro, V. 1.171.34.40' _computing_data_reduction 'CrysAlisPro, V. 1.171.34.40' _computing_molecular_graphics Olex2 _computing_publication_material 'XCIF, Bruker SHELXTL v. 6.12' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 10.3281 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 8350 _diffrn_reflns_theta_full 26.25 _diffrn_reflns_theta_max 26.25 _diffrn_reflns_theta_min 2.90 _exptl_absorpt_coefficient_mu 1.107 _exptl_absorpt_correction_type none _exptl_absorpt_process_details 'not measured' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.935 _refine_diff_density_min -1.845 _refine_diff_density_rms 0.193 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2322 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0803 _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^)+(0.1433P)^2^+8.7927P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2291 _refine_ls_wR_factor_ref 0.2536 _reflns_number_gt 1790 _reflns_number_total 2322 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c0ce00969e.txt _cod_data_source_block g:\pych2po\ar140f~1\ar140 _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 1555 2011-01-17 13:19:09Z saulius ; _cod_original_sg_symbol_H-M P21/c _cod_database_code 7205884 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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.0000 0.0000 0.0348(5) Uani 1 2 d SD . . Cl1 Cl -0.32842(12) -0.1169(2) 0.24342(14) 0.0328(5) Uani 1 1 d . . . P1 P -0.06557(11) 0.32196(18) 0.19943(13) 0.0182(4) Uani 1 1 d . . . O1 O -0.0631(3) 0.1478(5) 0.1578(4) 0.0186(9) Uani 1 1 d . . . O2 O 0.0400(4) 0.3935(7) 0.1846(5) 0.0430(15) Uani 1 1 d . . . H2A H 0.0508 0.4745 0.2331 0.064 Uiso 1 1 calc R . . O3 O -0.0935(3) 0.3527(5) 0.3332(3) 0.0177(9) Uani 1 1 d . . . O4 O 0.1419(4) 0.1633(6) 0.0022(5) 0.0301(11) Uani 1 1 d D . . O6 O -0.4115(5) -0.0201(11) 0.2519(7) 0.080(3) Uani 1 1 d . . . O7 O -0.3204(4) -0.1645(9) 0.1130(5) 0.0527(16) Uani 1 1 d . . . O8 O -0.238(3) -0.034(6) 0.290(3) 0.113(18) Uani 0.33 1 d P . . N1 N -0.2603(4) 0.2327(6) -0.0330(4) 0.0210(11) Uani 1 1 d . . . H1 H -0.2082 0.1995 -0.0686 0.025 Uiso 1 1 calc R . . C1 C -0.2486(5) 0.3578(8) 0.0486(5) 0.0265(14) Uani 1 1 d . . . C2 C -0.3310(8) 0.4117(12) 0.0995(7) 0.055(3) Uani 1 1 d . . . H2 H -0.3258 0.5025 0.1561 0.065 Uiso 1 1 calc R . . C3 C -0.4202(9) 0.337(2) 0.0699(11) 0.093(6) Uani 1 1 d . . . H3 H -0.4767 0.3745 0.1070 0.111 Uiso 1 1 calc R . . C4 C -0.4295(6) 0.209(2) -0.0118(10) 0.089(5) Uani 1 1 d . . . H4 H -0.4919 0.1562 -0.0332 0.107 Uiso 1 1 calc R . . C5 C -0.3456(6) 0.1557(11) -0.0633(7) 0.043(2) Uani 1 1 d . . . H5 H -0.3492 0.0650 -0.1199 0.052 Uiso 1 1 calc R . . C6 C -0.1468(6) 0.4293(8) 0.0772(6) 0.0325(16) Uani 1 1 d . . . H6B H -0.1532 0.5426 0.1060 0.039 Uiso 1 1 calc R . . H6A H -0.1153 0.4316 -0.0039 0.039 Uiso 1 1 calc R . . H4B H 0.187(3) 0.151(8) -0.049(6) 0.049 Uiso 1 1 d D . . H4A H 0.163(4) 0.226(9) 0.066(5) 0.049 Uiso 1 1 d D . . O8B O -0.2411(15) -0.084(2) 0.324(2) 0.028(4) Uiso 0.33 1 d P . . O8A O -0.2537(15) 0.028(2) 0.2506(18) 0.027(4) Uiso 0.33 1 d P . . O5B O -0.3668(10) -0.2735(16) 0.3038(12) 0.052(3) Uiso 0.50 1 d P . . O5A O -0.3024(13) -0.230(2) 0.3342(16) 0.074(4) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0352(9) 0.0454(9) 0.0247(8) 0.0033(6) 0.0071(6) 0.0081(6) Cl1 0.0234(8) 0.0548(11) 0.0191(8) -0.0007(7) -0.0012(6) 0.0035(7) P1 0.0236(8) 0.0247(8) 0.0070(7) -0.0061(5) 0.0044(5) -0.0108(6) O1 0.025(2) 0.024(2) 0.0078(18) -0.0021(14) 0.0025(15) 0.0007(16) O2 0.043(3) 0.066(4) 0.024(2) -0.024(2) 0.023(2) -0.037(3) O3 0.019(2) 0.027(2) 0.0073(18) -0.0042(14) 0.0045(14) -0.0089(16) O4 0.028(3) 0.033(3) 0.030(2) -0.0014(19) 0.0085(19) -0.005(2) O6 0.051(4) 0.141(8) 0.053(4) 0.035(4) 0.030(3) 0.057(5) O7 0.041(3) 0.091(5) 0.028(3) -0.009(3) 0.012(2) -0.007(3) O8 0.08(2) 0.23(5) 0.035(18) -0.04(2) 0.023(15) -0.10(3) N1 0.023(3) 0.027(3) 0.013(2) 0.0016(19) 0.0038(19) 0.004(2) C1 0.042(4) 0.027(3) 0.011(3) 0.010(2) 0.006(2) 0.018(3) C2 0.065(6) 0.075(6) 0.028(4) 0.014(4) 0.024(4) 0.053(5) C3 0.064(8) 0.180(15) 0.042(6) 0.054(8) 0.037(5) 0.080(9) C4 0.016(4) 0.207(16) 0.043(6) 0.070(8) -0.004(4) -0.010(6) C5 0.033(4) 0.072(6) 0.021(3) 0.015(3) -0.011(3) -0.014(4) C6 0.065(5) 0.015(3) 0.015(3) 0.002(2) -0.003(3) -0.006(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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe1 O1 180.0 3 . ? O1 Fe1 O4 86.41(15) 3 . ? O1 Fe1 O4 93.59(15) . . ? O1 Fe1 O4 93.59(15) 3 3 ? O1 Fe1 O4 86.41(15) . 3 ? O4 Fe1 O4 180.0 . 3 ? O1 Fe1 O3 92.17(13) 3 2_545 ? O1 Fe1 O3 87.83(13) . 2_545 ? O4 Fe1 O3 85.76(16) . 2_545 ? O4 Fe1 O3 94.24(16) 3 2_545 ? O1 Fe1 O3 87.83(13) 3 4_565 ? O1 Fe1 O3 92.17(13) . 4_565 ? O4 Fe1 O3 94.24(16) . 4_565 ? O4 Fe1 O3 85.76(16) 3 4_565 ? O3 Fe1 O3 180.0 2_545 4_565 ? O5A Cl1 O8B 65.2(11) . . ? O5A Cl1 O6 119.9(8) . . ? O8B Cl1 O6 118.9(9) . . ? O5A Cl1 O7 115.5(8) . . ? O8B Cl1 O7 117.9(8) . . ? O6 Cl1 O7 112.1(4) . . ? O5A Cl1 O8 87(2) . . ? O8B Cl1 O8 22.4(19) . . ? O6 Cl1 O8 111(2) . . ? O7 Cl1 O8 107.1(11) . . ? O5A Cl1 O5B 37.8(8) . . ? O8B Cl1 O5B 102.6(9) . . ? O6 Cl1 O5B 98.1(6) . . ? O7 Cl1 O5B 102.8(5) . . ? O8 Cl1 O5B 125.0(19) . . ? O5A Cl1 O8A 112.9(10) . . ? O8B Cl1 O8A 47.6(11) . . ? O6 Cl1 O8A 94.4(8) . . ? O7 Cl1 O8A 97.6(8) . . ? O8 Cl1 O8A 26(2) . . ? O5B Cl1 O8A 149.8(8) . . ? O1 P1 O3 116.3(2) . . ? O1 P1 O2 106.2(3) . . ? O3 P1 O2 111.2(2) . . ? O1 P1 C6 107.5(3) . . ? O3 P1 C6 111.5(3) . . ? O2 P1 C6 103.1(3) . . ? P1 O1 Fe1 137.6(2) . . ? P1 O2 H2A 109.5 . . ? P1 O3 Fe1 126.4(2) . 2 ? Fe1 O4 H4B 124(2) . . ? Fe1 O4 H4A 123(2) . . ? H4B O4 H4A 111(3) . . ? C5 N1 C1 123.9(6) . . ? C5 N1 H1 118.1 . . ? C1 N1 H1 118.1 . . ? N1 C1 C2 117.4(8) . . ? N1 C1 C6 117.9(6) . . ? C2 C1 C6 124.7(8) . . ? C3 C2 C1 120.5(10) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.7(8) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.2(10) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 C4 119.3(10) . . ? N1 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C1 C6 P1 114.2(4) . . ? C1 C6 H6B 108.7 . . ? P1 C6 H6B 108.7 . . ? C1 C6 H6A 108.7 . . ? P1 C6 H6A 108.7 . . ? H6B C6 H6A 107.6 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O1 2.292(4) 3 ? Fe1 O1 2.292(4) . ? Fe1 O4 2.343(5) . ? Fe1 O4 2.343(5) 3 ? Fe1 O3 2.354(4) 2_545 ? Fe1 O3 2.354(4) 4_565 ? Cl1 O5A 1.344(16) . ? Cl1 O8B 1.39(2) . ? Cl1 O6 1.390(6) . ? Cl1 O7 1.428(6) . ? Cl1 O8 1.44(3) . ? Cl1 O5B 1.555(13) . ? Cl1 O8A 1.56(2) . ? P1 O1 1.504(4) . ? P1 O3 1.507(4) . ? P1 O2 1.570(5) . ? P1 C6 1.805(7) . ? O2 H2A 0.8400 . ? O3 Fe1 2.354(4) 2 ? O4 H4B 0.862(10) . ? O4 H4A 0.867(10) . ? N1 C5 1.320(9) . ? N1 C1 1.334(8) . ? N1 H1 0.8800 . ? C1 C2 1.366(10) . ? C1 C6 1.494(10) . ? C2 C3 1.357(19) . ? C2 H2 0.9500 . ? C3 C4 1.35(2) . ? C3 H3 0.9500 . ? C4 C5 1.383(15) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O2 0.867(10) 2.59(5) 3.122(7) 121(4) . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 P1 O1 Fe1 -163.9(3) . . . . ? O2 P1 O1 Fe1 -39.5(4) . . . . ? C6 P1 O1 Fe1 70.3(4) . . . . ? O1 Fe1 O1 P1 -77(100) 3 . . . ? O4 Fe1 O1 P1 34.7(4) . . . . ? O4 Fe1 O1 P1 -145.3(4) 3 . . . ? O3 Fe1 O1 P1 120.3(4) 2_545 . . . ? O3 Fe1 O1 P1 -59.7(4) 4_565 . . . ? O1 P1 O3 Fe1 125.0(3) . . . 2 ? O2 P1 O3 Fe1 3.2(4) . . . 2 ? C6 P1 O3 Fe1 -111.2(3) . . . 2 ? C5 N1 C1 C2 -2.4(9) . . . . ? C5 N1 C1 C6 177.9(6) . . . . ? N1 C1 C2 C3 1.7(11) . . . . ? C6 C1 C2 C3 -178.6(7) . . . . ? C1 C2 C3 C4 -0.9(14) . . . . ? C2 C3 C4 C5 0.5(15) . . . . ? C1 N1 C5 C4 2.0(10) . . . . ? C3 C4 C5 N1 -1.0(13) . . . . ? N1 C1 C6 P1 -82.1(6) . . . . ? C2 C1 C6 P1 98.3(7) . . . . ? O1 P1 C6 C1 54.4(5) . . . . ? O3 P1 C6 C1 -74.2(5) . . . . ? O2 P1 C6 C1 166.3(5) . . . . ?