#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/22/2102202.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_2102202 loop_ _publ_author_name 'S\/orensen, Henning Osholm' 'Stuhr-Hansen, Nicolai' 'Henriksen, Lars' 'Larsen, Sine' _publ_section_title ; Structural characterization of protonated benzeneseleninic acid, the dihydroxyselenonium ion ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 1029 _journal_page_last 1034 _journal_paper_doi 10.1107/S0108768100010697 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C6 H7 O2 Se1 +,C6 H5 O3 S1 -' _chemical_formula_sum 'C12 H12 O5 S Se' _chemical_formula_weight 347.24 _chemical_name_systematic ; dihydroxy phenylselenonium benzene sulfonate ; _space_group_IT_number 43 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 40.641(5) _cell_length_b 22.268(3) _cell_length_c 5.7881(13) _cell_measurement_reflns_used 20 _cell_measurement_temperature 122.0(5) _cell_measurement_theta_max 40.64 _cell_measurement_theta_min 39.13 _cell_volume 5238.2(15) _computing_cell_refinement 'Enraf-Nonius XPRESS' _computing_data_collection 'Enraf-Nonius XPRESS' _computing_data_reduction 'DREADD (Blessing, 1987)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 122.0(5) _diffrn_measured_fraction_theta_full 0.254 _diffrn_measured_fraction_theta_max 0.254 _diffrn_measurement_device_type 'Enraf Nonius CAD-4' _diffrn_measurement_method '\w - 2\q' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 5592 _diffrn_reflns_theta_full 74.93 _diffrn_reflns_theta_max 74.93 _diffrn_reflns_theta_min 4.35 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 166.7 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu 5.521 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_correction_T_min 0.361 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(DeTitta, 1985)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description needle _exptl_crystal_F_000 2784 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _refine_diff_density_max 1.188 _refine_diff_density_min -1.131 _refine_diff_density_rms 0.149 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 5.839 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2669 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 5.891 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0737 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)] _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.1416 _refine_ls_wR_factor_ref 0.1425 _reflns_number_gt 2552 _reflns_number_total 2669 _reflns_threshold_expression >2sigma(I) _cod_data_source_file os0057.cif _cod_data_source_block BEN _cod_original_cell_volume 5238.4(15) _cod_database_code 2102202 _cod_database_fobs_code 2102202 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se Se 0.00474(2) 0.09172(4) 0.0064(3) 0.0466(3) Uani 1 d . . . O11 O 0.02224(13) 0.1138(2) -0.2518(14) 0.0434(14) Uani 1 d . . . O12 O 0.03535(13) 0.1150(3) 0.1938(11) 0.056(2) Uani 1 d . . . C11 C -0.02233(17) 0.1620(3) 0.0373(17) 0.0313(19) Uani 1 d . . . C12 C -0.02132(17) 0.1957(3) 0.2348(18) 0.0316(17) Uani 1 d . . . H12 H -0.0061 0.1859 0.3535 0.038 Uiso 1 calc . . . C13 C -0.0423(2) 0.2437(3) 0.262(2) 0.0371(19) Uani 1 d . . . H13 H -0.0418 0.2670 0.3996 0.045 Uiso 1 calc . . . C14 C -0.0640(2) 0.2574(3) 0.0854(17) 0.039(2) Uani 1 d . . . H14 H -0.0784 0.2907 0.1010 0.047 Uiso 1 calc . . . C15 C -0.0647(2) 0.2225(3) -0.1168(16) 0.0326(19) Uani 1 d . . . H15 H -0.0798 0.2319 -0.2367 0.039 Uiso 1 calc . . . C16 C -0.04363(19) 0.1752(3) -0.1404(15) 0.0317(19) Uani 1 d . . . H16 H -0.0437 0.1516 -0.2773 0.038 Uiso 1 calc . . . S S -0.05331(5) 0.02257(9) 0.4980(5) 0.0558(8) Uani 1 d D . . O21A O -0.0309(3) 0.0534(5) 0.3456(19) 0.0458(14) Uiso 0.518(8) d PD A 1 O22A O -0.0589(3) -0.0401(3) 0.470(3) 0.0458(14) Uiso 0.518(8) d PD A 1 O23A O -0.0392(3) 0.0195(6) 0.7308(14) 0.0458(14) Uiso 0.518(8) d PD A 1 O21B O -0.0283(3) 0.0660(5) 0.436(2) 0.0458(14) Uiso 0.482(8) d PD A 2 O22B O -0.0659(3) -0.0202(5) 0.327(2) 0.0458(14) Uiso 0.482(8) d PD A 2 O23B O -0.0467(3) -0.0107(6) 0.7049(16) 0.0458(14) Uiso 0.482(8) d PD A 2 C21 C -0.08864(16) 0.0674(3) 0.5451(16) 0.0276(19) Uani 1 d . . . C22 C -0.10690(16) 0.0622(3) 0.7457(17) 0.0292(17) Uani 1 d . . . H22 H -0.1010 0.0337 0.8604 0.035 Uiso 1 calc . . . C23 C -0.13386(17) 0.0989(3) 0.7774(17) 0.0340(19) Uani 1 d . . . H23 H -0.1468 0.0952 0.9135 0.041 Uiso 1 calc . . . C24 C -0.14224(19) 0.1412(4) 0.6122(17) 0.035(2) Uani 1 d . . . H24 H -0.1605 0.1671 0.6369 0.042 Uiso 1 calc . . . C25 C -0.12387(19) 0.1457(4) 0.4095(17) 0.037(2) Uani 1 d . . . H25 H -0.1299 0.1745 0.2960 0.045 Uiso 1 calc . . . C26 C -0.09723(19) 0.1091(4) 0.3716(16) 0.0321(19) Uani 1 d . . . H26 H -0.0849 0.1119 0.2326 0.039 Uiso 1 calc . . . 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 Se 0.0278(4) 0.0292(4) 0.0829(7) 0.0188(6) 0.0167(6) 0.0071(4) O11 0.040(3) 0.043(3) 0.048(4) -0.003(4) 0.012(4) 0.006(3) O12 0.021(3) 0.112(6) 0.035(4) 0.025(4) 0.003(3) 0.008(3) C11 0.027(3) 0.014(3) 0.054(6) 0.015(4) -0.005(4) -0.001(3) C12 0.028(3) 0.030(4) 0.037(5) 0.000(4) -0.002(4) -0.006(3) C13 0.048(5) 0.031(4) 0.032(4) 0.008(4) 0.012(5) -0.006(3) C14 0.044(5) 0.025(4) 0.049(6) 0.001(4) 0.007(4) 0.004(4) C15 0.032(4) 0.029(4) 0.037(5) 0.004(4) -0.007(4) 0.002(3) C16 0.036(4) 0.022(4) 0.037(5) 0.000(4) -0.004(4) -0.003(3) S 0.0322(10) 0.0295(10) 0.106(2) 0.0197(16) 0.0327(15) 0.0074(8) C21 0.016(3) 0.023(3) 0.044(6) -0.001(4) 0.000(4) -0.003(3) C22 0.024(3) 0.027(3) 0.037(5) 0.007(4) -0.007(4) -0.005(3) C23 0.025(4) 0.036(4) 0.041(5) -0.006(5) 0.014(4) -0.002(3) C24 0.029(4) 0.026(4) 0.049(6) 0.000(4) -0.001(4) 0.006(3) C25 0.021(4) 0.046(5) 0.045(6) 0.013(4) -0.004(4) 0.003(3) C26 0.027(4) 0.032(4) 0.037(5) -0.003(4) 0.002(4) -0.004(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 '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 O11 Se O12 99.3(3) yes O11 Se C11 94.8(3) yes O12 Se C11 96.2(3) yes C12 C11 C16 121.8(7) yes C12 C11 Se 120.5(6) yes C16 C11 Se 117.6(6) yes C11 C12 C13 120.2(9) yes C12 C13 C14 118.7(10) yes C13 C14 C15 120.5(8) yes C16 C15 C14 119.8(8) yes C15 C16 C11 119.0(8) yes O22A S O23B 67.5(8) yes O22A S O21A 119.8(7) yes O23B S O21A 129.6(8) yes O22A S O21B 137.5(8) yes O23B S O21B 114.9(8) yes O21A S O21B 24.1(7) yes O22A S O22B 39.7(7) yes O23B S O22B 107.0(7) yes O21A S O22B 96.7(7) yes O21B S O22B 120.7(8) yes O22A S O23A 96.9(8) yes O23B S O23A 30.1(6) yes O21A S O23A 109.7(7) yes O21B S O23A 89.1(8) yes O22B S O23A 136.6(8) yes O22A S C21 116.2(5) yes O23B S C21 108.4(7) yes O21A S C21 109.8(6) yes O21B S C21 103.4(6) yes O22B S C21 100.8(6) yes O23A S C21 101.7(6) yes C22 C21 C26 121.3(7) yes C22 C21 S 121.2(6) yes C26 C21 S 117.5(6) yes C23 C22 C21 119.2(8) yes C22 C23 C24 120.4(8) yes C23 C24 C25 119.9(7) yes C26 C25 C24 120.9(8) yes C25 C26 C21 118.2(8) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Se O11 1.727(7) yes Se O12 1.730(6) yes Se C11 1.922(7) yes C11 C12 1.368(13) yes C11 C16 1.376(11) yes C12 C13 1.376(11) yes C13 C14 1.384(14) yes C14 C15 1.405(11) yes C15 C16 1.366(10) yes S O22A 1.424(6) yes S O23B 1.434(6) yes S O21A 1.443(6) yes S O21B 1.447(6) yes S O22B 1.465(6) yes S O23A 1.466(6) yes S C21 1.769(7) yes C21 C22 1.383(11) yes C21 C26 1.412(12) yes C22 C23 1.380(9) yes C23 C24 1.384(12) yes C24 C25 1.394(13) yes C25 C26 1.372(11) 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 O11 Se C11 C12 -126.6(6) yes O12 Se C11 C12 -26.7(6) yes O11 Se C11 C16 56.5(6) no O12 Se C11 C16 156.4(6) no C16 C11 C12 C13 1.0(12) no Se C11 C12 C13 -175.8(6) yes C11 C12 C13 C14 -0.7(12) no C12 C13 C14 C15 0.6(13) no C13 C14 C15 C16 -0.7(13) no C14 C15 C16 C11 1.0(13) no C12 C11 C16 C15 -1.1(12) no Se C11 C16 C15 175.7(6) yes O21A S C21 C22 -153.0(8) yes O22A S C21 C22 67.0(10) yes O23A S C21 C22 -36.8(8) yes O21B S C21 C22 -128.7(8) yes O22B S C21 C22 105.8(8) yes O23B S C21 C22 -6.4(9) yes O21A S C21 C26 26.2(9) no O22A S C21 C26 -113.8(9) no O23A S C21 C26 142.3(8) no O21B S C21 C26 50.4(9) no O22B S C21 C26 -75.0(8) no O23B S C21 C26 172.7(8) no C26 C21 C22 C23 -0.5(11) no S C21 C22 C23 178.6(6) yes C21 C22 C23 C24 -1.1(12) no C22 C23 C24 C25 1.7(12) no C23 C24 C25 C26 -0.7(13) no C24 C25 C26 C21 -0.9(12) no C22 C21 C26 C25 1.5(11) no S C21 C26 C25 -177.7(6) no