#------------------------------------------------------------------------------ #$Date: 2014-04-19 22:43:05 +0300 (Sat, 19 Apr 2014) $ #$Revision: 110685 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/94/2239402.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_2239402 loop_ _publ_author_name 'Reuter, Hans' 'Reichelt, Martin' _publ_section_title ; Methylphosphonic acid, CH~3~PO(OH)~2~ ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o353 _journal_paper_doi 10.1107/S1600536814003572 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C H5 O3 P' _chemical_formula_moiety 'C H5 O3 P' _chemical_formula_sum 'C H5 O3 P' _chemical_formula_weight 96.02 _chemical_name_systematic ; Methylphosphonic acid ; _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 108.262(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.1015(8) _cell_length_b 5.7704(3) _cell_length_c 9.9549(6) _cell_measurement_reflns_used 9876 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 28.66 _cell_measurement_theta_min 2.84 _cell_volume 823.79(8) _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2008) ; _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _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 0.0753 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 58588 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.84 _exptl_absorpt_coefficient_mu 0.507 _exptl_absorpt_correction_T_max 0.9417 _exptl_absorpt_correction_T_min 0.8047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rhomboidal plate' _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.333 _refine_diff_density_min -0.345 _refine_ls_extinction_coef 0.0089(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 97 _refine_ls_number_reflns 1989 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0280 _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^)+(0.0446P)^2^+0.3474P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.0870 _reflns_number_gt 1763 _reflns_number_total 1989 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL HR600_0ma in P2(1)/c CELL 0.71073 15.1015 5.7704 9.9549 90.000 108.262 90.000 ZERR 8.00 0.0008 0.0003 0.0006 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H P O UNIT 8 40 8 24 OMIT -3 56 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 HTAB SIZE 0.120 0.263 0.448 HTAB O11 O13_$1 HTAB O12 O13_$2 HTAB O21 O23_$3 HTAB O22 O23_$4 EQIV $1 [ -x+1, y+1/2, -z+3/2 ] EQIV $2 [ -x+1, -y+1, -z+1 ] EQIV $3 [ -x, y+1/2, -z+3/2 ] EQIV $4 [ -x, -y+2, -z+1 ] TEMP -273 WGHT 0.0447 0.3461 EXTI 0.008880 FVAR 0.25147 0.08363 0.06923 0.06974 MOLE 1 P1 3 0.410343 0.359243 0.609081 11.00000 0.03007 0.02541 = 0.02766 -0.00150 0.01342 -0.00282 O11 4 0.402972 0.424491 0.755629 11.00000 0.05634 0.04862 = 0.03819 -0.01723 0.02838 -0.02190 AFIX 3 H11 2 0.443322 0.544974 0.806603 11.00000 41.00000 AFIX 0 O12 4 0.381517 0.572425 0.511265 11.00000 0.03843 0.04568 = 0.06350 0.02443 0.02695 0.01458 AFIX 3 H12 2 0.425095 0.636312 0.469077 11.00000 41.00000 AFIX 0 O13 4 0.505910 0.277937 0.615647 11.00000 0.03453 0.03813 = 0.04051 0.01574 0.01718 0.00818 C1 1 0.324693 0.143812 0.548615 11.00000 0.04871 0.04566 = 0.05500 -0.02218 0.02387 -0.01940 AFIX 137 H111 2 0.321211 0.098112 0.452279 11.00000 21.00000 H112 2 0.264116 0.204597 0.548703 11.00000 21.00000 H113 2 0.341023 0.008676 0.611167 11.00000 21.00000 AFIX 0 P2 3 0.090291 0.866354 0.694828 11.00000 0.03047 0.02675 = 0.02232 0.00254 0.00533 0.00449 O21 4 0.095036 0.919012 0.849397 11.00000 0.06061 0.05085 = 0.02461 0.00005 0.01085 0.02242 AFIX 3 H21 2 0.049520 1.029834 0.856802 11.00000 41.00000 AFIX 0 O22 4 0.113149 1.093548 0.629334 11.00000 0.03695 0.03612 = 0.04133 0.01110 -0.00191 -0.00757 AFIX 3 H22 2 0.071233 1.144035 0.540429 11.00000 41.00000 AFIX 0 O23 4 -0.002277 0.770985 0.607976 11.00000 0.03447 0.04115 = 0.03288 0.01350 0.00381 -0.00649 C2 1 0.182649 0.670323 0.712553 11.00000 0.04489 0.04199 = 0.03915 -0.00325 0.00651 0.01693 AFIX 137 H211 2 0.170015 0.526076 0.755217 11.00000 31.00000 H212 2 0.240892 0.738568 0.773202 11.00000 31.00000 H213 2 0.188431 0.637245 0.619103 11.00000 31.00000 HKLF 4 REM HR600_0ma in P2(1)/c REM R1 = 0.0280 for 1763 Fo > 4sig(Fo) and 0.0323 for all 1989 data REM 97 parameters refined using 0 restraints END WGHT 0.0447 0.3461 REM Highest difference peak 0.333, deepest hole -0.346, 1-sigma level 0.052 Q1 1 0.3677 0.2438 0.5787 11.00000 0.05 0.33 Q2 1 0.1388 0.7567 0.6977 11.00000 0.05 0.32 Q3 1 0.3820 0.5227 0.7047 11.00000 0.05 0.29 Q4 1 0.0348 0.8332 0.6538 11.00000 0.05 0.28 Q5 1 0.1206 1.0297 0.8367 11.00000 0.05 0.27 ; _[local]_cod_data_source_file hg5383sup1.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2239402 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_type_symbol _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_symmetry_multiplicity P P1 0.41034(3) 0.35924(6) 0.60908(4) 0.02670(13) Uani d . 1 1 O O11 0.40297(9) 0.4245(2) 0.75562(13) 0.0446(3) Uani d . 1 1 H H11 0.4433 0.5450 0.8066 0.070(4) Uiso d R 1 1 O O12 0.38152(8) 0.5724(2) 0.51127(14) 0.0466(3) Uani d . 1 1 H H12 0.4251 0.6363 0.4691 0.070(4) Uiso d R 1 1 O O13 0.50590(7) 0.2779(2) 0.61564(12) 0.0365(3) Uani d . 1 1 C C1 0.32469(13) 0.1438(3) 0.5486(2) 0.0480(5) Uani d . 1 1 H H111 0.3212 0.0982 0.4522 0.083(5) Uiso calc R 1 1 H H112 0.2641 0.2045 0.5488 0.083(5) Uiso calc R 1 1 H H113 0.3411 0.0086 0.6111 0.083(5) Uiso calc R 1 1 P P2 0.09029(3) 0.86636(6) 0.69483(4) 0.02720(13) Uani d . 1 1 O O21 0.09504(9) 0.9190(2) 0.84939(12) 0.0459(3) Uani d . 1 1 H H21 0.0495 1.0299 0.8568 0.070(4) Uiso d R 1 1 O O22 0.11315(8) 1.0935(2) 0.62934(12) 0.0414(3) Uani d . 1 1 H H22 0.0712 1.1440 0.5404 0.070(4) Uiso d R 1 1 O O23 -0.00227(7) 0.7710(2) 0.60798(11) 0.0377(3) Uani d . 1 1 C C2 0.18264(13) 0.6703(3) 0.71256(18) 0.0436(4) Uani d . 1 1 H H211 0.1700 0.5260 0.7551 0.069(4) Uiso calc R 1 1 H H212 0.2409 0.7385 0.7733 0.069(4) Uiso calc R 1 1 H H213 0.1885 0.6373 0.6191 0.069(4) Uiso calc R 1 1 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 0.0301(2) 0.0254(2) 0.0277(2) -0.00282(13) 0.01342(15) -0.00150(13) O11 0.0563(7) 0.0486(7) 0.0382(6) -0.0219(6) 0.0283(6) -0.0172(5) O12 0.0384(6) 0.0457(7) 0.0635(8) 0.0146(5) 0.0269(6) 0.0244(6) O13 0.0345(6) 0.0381(6) 0.0405(6) 0.0082(5) 0.0172(5) 0.0157(5) C1 0.0487(10) 0.0457(10) 0.0550(11) -0.0194(8) 0.0239(9) -0.0222(8) P2 0.0305(2) 0.0268(2) 0.0223(2) 0.00449(13) 0.00533(15) 0.00254(12) O21 0.0605(8) 0.0509(7) 0.0246(5) 0.0224(6) 0.0108(5) 0.0001(5) O22 0.0369(6) 0.0361(6) 0.0413(6) -0.0076(5) -0.0019(5) 0.0111(5) O23 0.0345(6) 0.0411(6) 0.0329(5) -0.0065(5) 0.0038(4) 0.0135(5) C2 0.0449(9) 0.0420(9) 0.0392(9) 0.0169(8) 0.0065(7) -0.0033(7) 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' P P 0.1023 0.0942 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O13 P1 O11 112.86(7) O13 P1 O12 110.73(6) O11 P1 O12 108.17(8) O13 P1 C1 112.85(8) O11 P1 C1 103.46(8) O12 P1 C1 108.39(9) P1 O11 H11 117.1 P1 O12 H12 119.1 P1 C1 H111 109.5 P1 C1 H112 109.5 H111 C1 H112 109.5 P1 C1 H113 109.5 H111 C1 H113 109.5 H112 C1 H113 109.5 O23 P2 O21 112.94(7) O23 P2 O22 110.99(6) O21 P2 O22 107.75(7) O23 P2 C2 112.83(8) O21 P2 C2 103.76(7) O22 P2 C2 108.15(9) P2 O21 H21 113.4 P2 O22 H22 118.4 P2 C2 H211 109.5 P2 C2 H212 109.5 H211 C2 H212 109.5 P2 C2 H213 109.5 H211 C2 H213 109.5 H212 C2 H213 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P1 O13 1.4993(11) y P1 O11 1.5441(11) y P1 O12 1.5443(12) y P1 C1 1.7586(17) y O11 H11 0.9583 ? O12 H12 0.9584 ? C1 H111 0.9800 ? C1 H112 0.9800 ? C1 H113 0.9800 ? P2 O23 1.4989(11) y P2 O21 1.5478(11) y P2 O22 1.5504(12) y P2 C2 1.7612(17) y O21 H21 0.9584 ? O22 H22 0.9580 ? C2 H211 0.9800 ? C2 H212 0.9800 ? C2 H213 0.9800 ? 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 O22 H22 O23 3_576 0.96 1.59 2.5528(15) 179.5 O21 H21 O23 2_556 0.96 1.65 2.5768(16) 161.2 O12 H12 O13 3_666 0.96 1.61 2.5649(15) 173.5 O11 H11 O13 2_656 0.96 1.62 2.5671(16) 169.3 _cod_database_fobs_code 2239402