#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013213.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_2013213 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; (4-Nitrophenylsulfinyl)acetic acid, a three-dimensional hydrogen-bonded framework built from a combination of two-centre O---H···O and C---H···O hydrogen bonds and a three-centre C---H···(O)~2~ hydrogen bond ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o124 _journal_page_last o126 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C8 H7 N O5 S' _chemical_formula_moiety 'C8 H7 N O5 S' _chemical_formula_sum 'C8 H7 N O5 S' _chemical_formula_weight 229.22 _chemical_name_systematic ; (4-Nitrophenylsulfinyl)acetic 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 _cell_angle_alpha 90.00 _cell_angle_beta 93.088(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.7110(7) _cell_length_b 7.3037(3) _cell_length_c 9.3537(4) _cell_measurement_reflns_used 2124 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 3.16 _cell_volume 935.33(7) _computing_cell_refinement 'DENZO--SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO--SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0616 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7061 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.16 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.791 _refine_diff_density_min -0.354 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 2124 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0434 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.33P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.1104 _reflns_number_gt 1588 _reflns_number_total 2124 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1614.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_database_code 2013213 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 S1 0.20558(4) 0.65399(7) 0.71021(6) 0.01954(18) Uani d . 1 . . S O5 0.17742(11) 0.5651(2) 0.84711(16) 0.0220(4) Uani d . 1 . . O C1 0.26862(16) 0.4852(3) 0.6118(2) 0.0183(5) Uani d . 1 . . C C2 0.25576(16) 0.2990(3) 0.6365(2) 0.0205(5) Uani d . 1 . . C C3 0.30936(16) 0.1737(3) 0.5611(2) 0.0195(5) Uani d . 1 . . C C4 0.37325(15) 0.2402(3) 0.4635(2) 0.0186(5) Uani d . 1 . . C N4 0.43007(13) 0.1080(2) 0.3832(2) 0.0208(4) Uani d . 1 . . N O1 0.49132(13) 0.1682(2) 0.30462(18) 0.0303(4) Uani d . 1 . . O O2 0.41335(12) -0.0562(2) 0.39842(18) 0.0263(4) Uani d . 1 . . O C5 0.38575(16) 0.4248(3) 0.4366(2) 0.0206(5) Uani d . 1 . . C C6 0.33308(17) 0.5492(3) 0.5133(2) 0.0216(5) Uani d . 1 . . C C7 0.09633(16) 0.6606(3) 0.5930(2) 0.0205(5) Uani d . 1 . . C C8 0.03000(17) 0.8074(3) 0.6458(3) 0.0238(5) Uani d . 1 . . C O3 0.05419(13) 0.9127(3) 0.74139(19) 0.0369(5) Uani d . 1 . . O O4 -0.05533(12) 0.8082(2) 0.57336(19) 0.0294(4) Uani d . 1 . . O H2 0.2111 0.2583 0.7039 0.016(6) Uiso calc R 1 . . H H3 0.3024 0.0458 0.5760 0.026(7) Uiso calc R 1 . . H H5 0.4293 0.4651 0.3675 0.023(6) Uiso calc R 1 . . H H6 0.3409 0.6770 0.4988 0.033(7) Uiso calc R 1 . . H H71 0.1135 0.6878 0.4938 0.040(8) Uiso calc R 1 . . H H72 0.0629 0.5404 0.5934 0.027(7) Uiso calc R 1 . . H H4 -0.0906 0.8914 0.6049 0.080(13) 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 S1 0.0199(3) 0.0199(3) 0.0189(3) 0.0001(2) 0.0027(2) -0.0021(2) O5 0.0233(9) 0.0261(9) 0.0167(8) -0.0001(6) 0.0015(7) 0.0008(6) C1 0.0177(11) 0.0195(11) 0.0174(11) -0.0009(8) -0.0005(9) -0.0038(9) C2 0.0198(11) 0.0242(12) 0.0177(12) -0.0047(9) 0.0034(9) 0.0003(9) C3 0.0244(12) 0.0160(10) 0.0178(11) -0.0026(8) -0.0011(9) 0.0000(9) C4 0.0191(11) 0.0199(11) 0.0167(11) 0.0014(8) -0.0013(9) -0.0032(9) N4 0.0205(10) 0.0221(10) 0.0196(10) 0.0027(8) -0.0003(8) -0.0002(8) O1 0.0337(10) 0.0279(9) 0.0307(10) 0.0043(7) 0.0160(8) 0.0019(7) O2 0.0278(9) 0.0183(9) 0.0327(10) 0.0023(6) -0.0005(7) -0.0015(7) C5 0.0189(11) 0.0228(12) 0.0204(12) -0.0043(9) 0.0038(9) 0.0012(9) C6 0.0225(12) 0.0177(11) 0.0247(13) -0.0013(8) 0.0036(10) 0.0004(9) C7 0.0214(12) 0.0238(12) 0.0163(11) 0.0016(8) 0.0021(9) -0.0004(9) C8 0.0247(13) 0.0261(12) 0.0206(12) 0.0019(9) 0.0019(10) 0.0021(10) O3 0.0361(11) 0.0425(10) 0.0313(10) 0.0134(8) -0.0047(8) -0.0128(9) O4 0.0233(9) 0.0333(10) 0.0310(10) 0.0051(7) -0.0026(8) -0.0009(8) 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 S1 C1 . 1.789(2) y S1 C7 . 1.809(2) y S1 O5 . 1.5045(16) y C8 O3 . 1.212(3) y C8 O4 . 1.320(3) y C1 C6 . 1.392(3) no C1 C2 . 1.392(3) no C2 C3 . 1.390(3) no C2 H2 . 0.95 no C3 C4 . 1.387(3) no C3 H3 . 0.95 no C4 C5 . 1.384(3) no C4 N4 . 1.472(3) no N4 O1 . 1.227(2) no N4 O2 . 1.231(2) no C5 C6 . 1.385(3) no C5 H5 . 0.95 no C6 H6 . 0.95 no C7 C8 . 1.507(3) no C7 H71 . 0.99 no C7 H72 . 0.99 no O4 H4 . 0.84 no 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' S S 0.1246 0.1234 '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 O5 S1 C1 107.08(10) y O5 S1 C7 106.57(10) y C1 S1 C7 96.54(10) y S1 C1 C2 121.26(17) y S1 C1 C6 116.79(16) y C6 C1 C2 121.9(2) no C3 C2 C1 118.9(2) no C3 C2 H2 120.5 no C1 C2 H2 120.5 no C4 C3 C2 118.25(19) no C4 C3 H3 120.9 no C2 C3 H3 120.9 no C5 C4 C3 123.4(2) no C5 C4 N4 118.19(19) no C3 C4 N4 118.46(19) no O1 N4 O2 123.77(18) y O1 N4 C4 117.98(18) no O2 N4 C4 118.25(18) no C4 C5 C6 118.2(2) no C4 C5 H5 120.9 no C6 C5 H5 120.9 no C5 C6 C1 119.4(2) no C5 C6 H6 120.3 no C1 C6 H6 120.3 no C8 C7 S1 108.37(15) no C8 C7 H71 110.0 no S1 C7 H71 110.0 no C8 C7 H72 110.0 no S1 C7 H72 110.0 no H71 C7 H72 108.4 no O3 C8 O4 125.2(2) no O3 C8 C7 123.2(2) no O4 C8 C7 111.6(2) no C8 O4 H4 109.5 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 O4 H4 O5 2_556 0.84 1.81 2.648(2) 173 y C5 H5 O1 2_655 0.95 2.48 3.391(3) 160 y C6 H6 O2 1_565 0.95 2.40 3.286(3) 155 y C7 H71 O3 4_564 0.99 2.56 3.351(3) 137 y C7 H71 O5 4_564 0.99 2.46 3.289(3) 141 y C7 H72 O3 2_546 0.99 2.47 3.206(3) 131 y 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 C1 S1 C7 C8 -175.84(16) y C7 S1 C1 C2 -87.3(2) y C3 C4 N4 O1 -175.0(2) y C5 C4 N4 O1 5.6(3) y S1 C7 C8 O3 7.3(3) y S1 C7 C8 O4 -174.0(2) y O5 S1 C1 C6 -155.66(17) no C7 S1 C1 C6 94.73(19) no O5 S1 C1 C2 22.4(2) no C6 C1 C2 C3 0.4(3) no S1 C1 C2 C3 -177.53(16) no C1 C2 C3 C4 -0.3(3) no C2 C3 C4 C5 -0.5(3) no C2 C3 C4 N4 -179.92(19) no C5 C4 N4 O2 -174.3(2) no C3 C4 N4 O2 5.2(3) no C3 C4 C5 C6 1.3(3) no N4 C4 C5 C6 -179.29(19) no C4 C5 C6 C1 -1.2(3) no C2 C1 C6 C5 0.4(3) no S1 C1 C6 C5 178.41(17) no O5 S1 C7 C8 74.12(17) no _cod_database_fobs_code 2013213 _journal_paper_doi 10.1107/S0108270103001860