#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/12/2011250.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_2011250 loop_ _publ_author_name 'Robert A. Burrow' 'David H. Farrar' 'Alan J. Lough' 'M\'arcia R. Siqueira' 'Fatima Squizani' _publ_section_title ; Phenylphosphinic acid ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e357 _journal_page_last e358 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C6 H7 O2 P' _chemical_formula_sum 'C6 H7 O2 P' _chemical_formula_weight 142.09 _chemical_name_systematic ; phenylphosphinic acid ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.6624(6) _cell_length_b 5.5762(4) _cell_length_c 15.2489(11) _cell_measurement_reflns_used 4387 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.67 _cell_volume 651.54(8) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full .997 _diffrn_measured_fraction_theta_max .997 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\y and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .054 _diffrn_reflns_av_sigmaI/netI .0519 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 4387 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.89 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .337 _exptl_absorpt_correction_T_max .918 _exptl_absorpt_correction_T_min .906 _exptl_absorpt_correction_type 'multi-scan (Otwinski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 296 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .26 _refine_diff_density_max .219 _refine_diff_density_min -.228 _refine_ls_abs_structure_details 'Flack (1983), 593 Friedel pairs' _refine_ls_abs_structure_Flack .60(14) _refine_ls_extinction_coef .002(4) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 93 _refine_ls_number_reflns 1364 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all .049 _refine_ls_R_factor_gt .038 _refine_ls_shift/su_max .006 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0474P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .089 _reflns_number_gt 1162 _reflns_number_total 1364 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qa0333.cif _[local]_cod_data_source_block I _cod_database_code 2011250 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' 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 P .40757(8) .43127(10) .33664(5) .0289(2) Uani d . 1 . . P H1 .521(4) .619(5) .3566(18) .030(7) Uiso d . 1 . . H H2 .155(5) .443(5) .371(2) .042(9) Uiso d . 1 . . H O1 .4629(3) .1792(3) .35461(12) .0371(5) Uani d . 1 . . O O2 .2477(3) .5225(3) .38994(12) .0359(5) Uani d . 1 . . O C11 .3604(3) .4705(4) .22256(17) .0242(5) Uani d . 1 . . C C12 .2722(4) .6752(5) .19354(16) .0297(6) Uani d . 1 . . C H12 .2412 .7978 .2339 .036 Uiso calc R 1 . . H C13 .2302(4) .6980(5) .10532(17) .0311(6) Uani d . 1 . . C H13 .1700 .8366 .0855 .037 Uiso calc R 1 . . H C14 .2756(3) .5199(4) .04580(17) .0288(6) Uani d . 1 . . C H14 .2444 .5350 -.0142 .035 Uiso calc R 1 . . H C15 .3674(4) .3184(4) .07481(16) .0271(5) Uani d . 1 . . C H15 .4003 .1975 .0342 .033 Uiso calc R 1 . . H C16 .4105(3) .2942(4) .16248(16) .0253(5) Uani d . 1 . . C H16 .4741 .1579 .1818 .030 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 P .0306(3) .0366(3) .0195(3) -.0083(2) .0000(3) -.0005(3) O1 .0346(10) .0449(10) .0316(12) -.0015(8) .0014(8) .0103(8) O2 .0404(12) .0431(11) .0243(11) -.0074(9) .0034(8) -.0084(8) C11 .0255(13) .0271(11) .0200(10) -.0046(9) .0027(10) .0009(10) C12 .0324(15) .0278(12) .0290(14) -.0016(10) .0064(10) -.0038(11) C13 .0291(15) .0293(13) .0348(15) .0040(11) -.0004(11) .0071(11) C14 .0275(14) .0362(14) .0226(13) -.0031(11) -.0015(10) .0050(10) C15 .0296(14) .0282(12) .0237(12) -.0009(11) .0011(10) -.0045(10) C16 .0255(13) .0223(11) .0281(13) -.0011(9) -.0011(10) .0003(10) 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 P O1 . 1.4933(19) y P O2 . 1.556(2) y P C11 . 1.790(3) n P H1 . 1.40(3) y O2 H2 . .88(4) y C11 C16 . 1.398(4) n C11 C12 . 1.398(4) n C12 C13 . 1.389(4) n C12 H12 . .9500 n C13 C14 . 1.390(4) n C13 H13 . .9500 n C14 C15 . 1.397(4) n C14 H14 . .9500 n C15 C16 . 1.384(4) n C15 H15 . .9500 n C16 H16 . .9500 n loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .1023 .0942 '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_publ_flag O1 P O2 115.82(11) y O1 P C11 110.53(11) n O2 P C11 107.98(12) n O1 P H1 119.3(11) y O2 P H1 97.5(11) y C11 P H1 104.2(11) n P O2 H2 107(2) y C16 C11 C12 120.0(2) n C16 C11 P 119.71(18) n C12 C11 P 120.3(2) n C13 C12 C11 119.6(2) n C13 C12 H12 120.2 n C11 C12 H12 120.2 n C12 C13 C14 120.6(2) n C12 C13 H13 119.7 n C14 C13 H13 119.7 n C13 C14 C15 119.6(2) n C13 C14 H14 120.2 n C15 C14 H14 120.2 n C16 C15 C14 120.3(2) n C16 C15 H15 119.9 n C14 C15 H15 119.9 n C15 C16 C11 120.0(2) n C15 C16 H16 120.0 n C11 C16 H16 120.0 n 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 O2 H2 O1 4_455 .88(4) 1.64(4) 2.513(3) 168(3) C15 H15 O2 3_544 .95 2.66 3.383(3) 133.4 _cod_database_fobs_code 2011250