#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012539.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_2012539 loop_ _publ_author_name 'Chruszcz, Maksymilian' 'Lewinski, Krzysztof' 'sodium 2-hydroxy-5-nitrobenzylsulfonate monohydrate' _publ_section_title ; The sodium salt of 2-hydroxy-5-nitrobenzylsulfonic acid ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m150 _journal_page_last m151 _journal_paper_doi 10.1107/S0108270102000069 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'Na (C7 H6 N O6 S) , H2 O' _chemical_formula_moiety 'C7 H6 N O6 S - , Na + , H2 O' _chemical_formula_sum 'C7 H8 N Na O7 S' _chemical_formula_weight 273.19 _chemical_name_systematic 'sodium 2-hydroxy-5-nitrobenzylsulfonate monohydrate' _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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 105.2640(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.49400(10) _cell_length_b 12.0800(3) _cell_length_c 7.1600(3) _cell_measurement_reflns_used 2893 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.03 _cell_measurement_theta_min 1.02 _cell_volume 1042.52(5) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor 1997)' _computing_data_collection 'COLLECT (Nonius, 1997-2000)' _computing_data_reduction 'HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full .953 _diffrn_measured_fraction_theta_max .953 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .015 _diffrn_reflns_av_sigmaI/netI .032 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 5291 _diffrn_reflns_theta_full 30.02 _diffrn_reflns_theta_max 30.02 _diffrn_reflns_theta_min 2.39 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu .376 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 560 _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _refine_diff_density_max .30 _refine_diff_density_min -.44 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 3026 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all .042 _refine_ls_R_factor_gt .035 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.6053P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .090 _refine_ls_wR_factor_ref .094 _reflns_number_gt 2606 _reflns_number_total 3026 _reflns_threshold_expression I>2\s(I) _cod_data_source_file av1096.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.6053P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.6053P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012539 _cod_database_fobs_code 2012539 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 Na .51268(6) .68316(5) -.25367(9) .02991(16) Uani d . 1 . . Na S .63218(3) .57656(3) .22544(5) .02100(10) Uani d . 1 . . S O1 .58125(11) .66148(10) .08673(16) .0334(3) Uani d . 1 . . O O2 .55192(10) .50288(10) .27538(19) .0344(3) Uani d . 1 . . O O3 .70769(10) .62568(11) .39595(15) .0339(3) Uani d . 1 . . O C7 .71423(13) .49101(13) .1142(2) .0241(3) Uani d . 1 . . C H1 .6606(17) .4555(18) .005(3) .033(5) Uiso d . 1 . . H H2 .7453(19) .4345(19) .208(3) .041(6) Uiso d . 1 . . H O4 .68967(9) .58223(11) -.25615(16) .0295(3) Uani d . 1 . . O H5 .698(2) .601(2) -.369(4) .049(7) Uiso d . 1 . . H C2 .78967(12) .59583(13) -.1285(2) .0229(3) Uani d . 1 . . C C1 .80549(12) .55308(12) .0590(2) .0227(3) Uani d . 1 . . C C6 .90826(13) .56561(13) .1910(2) .0260(3) Uani d . 1 . . C H6 .9210(18) .5351(18) .315(3) .036(5) Uiso d . 1 . . H C5 .99296(13) .61849(13) .1342(2) .0271(3) Uani d . 1 . . C C4 .97869(14) .65959(14) -.0513(3) .0311(3) Uani d . 1 . . C H4 1.0387(19) .689(2) -.085(3) .046(6) Uiso d . 1 . . H C3 .87651(13) .64914(14) -.1826(2) .0293(3) Uani d . 1 . . C H3 .8617(17) .6796(18) -.314(3) .036(5) Uiso d . 1 . . H N1 1.10174(12) .62824(13) .2711(2) .0358(3) Uani d . 1 . . N O5 1.11698(13) .58883(14) .4319(2) .0538(4) Uani d . 1 . . O O6 1.17458(12) .67840(15) .2188(3) .0583(4) Uani d . 1 . . O O7 .41280(12) .82522(12) -.1144(2) .0373(3) Uani d . 1 . . O H7 .346(3) .828(3) -.141(4) .072(9) Uiso d . 1 . . H H8 .430(4) .888(4) -.154(6) .124(15) Uiso d . 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 Na .0338(4) .0292(3) .0269(3) .0001(3) .0083(3) .0027(2) S .02316(18) .02339(18) .01724(16) -.00021(12) .00672(12) .00101(12) O1 .0422(7) .0327(6) .0260(5) .0126(5) .0101(5) .0070(5) O2 .0320(6) .0336(6) .0432(7) -.0068(5) .0200(5) .0000(5) O3 .0387(7) .0440(7) .0190(5) -.0101(5) .0072(5) -.0069(5) C7 .0263(7) .0244(7) .0231(6) .0015(5) .0088(6) .0009(5) O4 .0235(5) .0456(7) .0183(5) -.0036(5) .0037(4) .0023(5) C2 .0207(7) .0263(7) .0213(6) .0018(5) .0048(5) -.0005(5) C1 .0224(7) .0255(7) .0212(6) .0029(5) .0075(5) -.0001(5) C6 .0257(7) .0288(8) .0224(7) .0047(6) .0041(6) .0010(5) C5 .0206(7) .0262(7) .0309(7) .0024(6) .0007(6) -.0027(6) C4 .0250(7) .0310(8) .0378(8) -.0022(6) .0094(7) .0031(6) C3 .0279(8) .0336(8) .0269(7) -.0023(6) .0082(6) .0053(6) N1 .0262(7) .0327(8) .0425(8) .0030(6) -.0015(6) -.0043(6) O5 .0438(8) .0631(10) .0414(8) -.0011(7) -.0121(6) .0073(7) O6 .0259(7) .0713(11) .0701(11) -.0125(7) -.0010(7) .0078(9) O7 .0287(7) .0392(7) .0425(7) .0061(5) .0066(5) .0044(6) 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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na .0362 .0249 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Na O2 . 3_665 89.28(5) yes O1 Na O1 . 4_575 118.95(5) yes O2 Na O1 3_665 4_575 147.37(5) ? O1 Na O7 . . 75.37(5) yes O2 Na O7 3_665 . 118.81(5) ? O1 Na O7 4_575 . 86.15(5) ? O1 Na O4 . . 82.77(4) yes O2 Na O4 3_665 . 80.00(5) ? O1 Na O4 4_575 . 87.28(5) ? O7 Na O4 . . 150.42(5) ? O1 Na O7 . 4_575 168.52(5) yes O2 Na O7 3_665 4_575 80.19(5) ? O1 Na O7 4_575 4_575 72.47(4) ? O7 Na O7 . 4_575 105.67(6) yes O4 Na O7 . 4_575 99.72(5) ? O1 Na S . 4_575 95.66(4) ? O2 Na S 3_665 4_575 169.11(4) ? O1 Na S 4_575 4_575 24.33(3) ? O7 Na S . 4_575 71.93(4) ? O4 Na S . 4_575 90.97(3) ? O7 Na S 4_575 4_575 95.50(4) ? O1 Na Na . 4_576 36.55(3) ? O2 Na Na 3_665 4_576 111.50(4) ? O1 Na Na 4_575 4_576 101.12(4) ? O7 Na Na . 4_576 39.49(4) ? O4 Na Na . 4_576 114.48(3) ? O7 Na Na 4_575 4_576 145.06(4) ? S Na Na 4_575 4_576 77.72(2) ? O1 Na Na . 4_575 153.38(4) ? O2 Na Na 3_665 4_575 114.22(4) ? O1 Na Na 4_575 4_575 35.02(3) ? O7 Na Na . 4_575 101.71(4) ? O4 Na Na . 4_575 88.97(3) ? O7 Na Na 4_575 4_575 38.08(3) ? S Na Na 4_575 4_575 59.08(2) ? Na Na Na 4_576 4_575 131.44(4) ? Na O1 Na . 4_576 108.43(5) yes Na O7 Na . 4_576 102.43(5) yes O1 S O2 . . 113.21(8) ? O1 S O3 . . 110.81(8) ? O2 S O3 . . 112.29(7) ? O1 S C7 . . 107.67(7) yes O2 S C7 . . 105.65(7) yes O3 S C7 . . 106.76(8) yes O1 S Na . 4_576 44.34(5) ? O2 S Na . 4_576 100.28(5) ? O3 S Na . 4_576 78.69(6) ? C7 S Na . 4_576 148.59(5) ? S O1 Na . . 138.93(8) ? S O1 Na . 4_576 111.33(6) ? S O2 Na . 3_665 143.72(8) ? C1 C7 S . . 113.17(11) yes C1 C7 H1 . . 114.4(12) ? S C7 H1 . . 104.8(12) ? C1 C7 H2 . . 110.0(14) ? S C7 H2 . . 105.9(14) ? H1 C7 H2 . . 108.1(18) ? C2 O4 Na . . 126.27(10) ? C2 O4 H5 . . 106.5(16) ? Na O4 H5 . . 101.1(17) ? O4 C2 C3 . . 120.97(13) ? O4 C2 C1 . . 118.38(13) ? C3 C2 C1 . . 120.63(14) ? C6 C1 C2 . . 118.93(14) ? C6 C1 C7 . . 120.37(13) ? C2 C1 C7 . . 120.66(13) ? C5 C6 C1 . . 119.43(14) ? C5 C6 H6 . . 120.5(13) ? C1 C6 H6 . . 119.9(13) ? C4 C5 C6 . . 122.11(14) ? C4 C5 N1 . . 118.57(15) ? C6 C5 N1 . . 119.29(14) ? C3 C4 C5 . . 118.94(15) ? C3 C4 H4 . . 121.9(14) ? C5 C4 H4 . . 119.1(14) ? C4 C3 C2 . . 119.95(15) ? C4 C3 H3 . . 121.8(12) ? C2 C3 H3 . . 118.2(12) ? O5 N1 O6 . . 122.54(16) yes O5 N1 C5 . . 119.50(16) yes O6 N1 C5 . . 117.95(16) yes Na O7 H7 . . 122(2) ? Na O7 H7 4_576 . 116(2) ? Na O7 H8 . . 106(3) ? Na O7 H8 4_576 . 105(3) ? H7 O7 H8 . . 103(3) ? 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 Na O1 . 2.3756(13) yes Na O1 4_575 2.4652(13) yes Na O2 3_665 2.3791(14) yes Na O4 . 2.5293(14) yes Na O7 . 2.4804(15) yes Na O7 4_575 2.5573(15) yes Na S 4_575 3.2855(8) no Na Na 4_576 3.9273(6) no Na Na 4_575 3.9273(6) no S C7 . 1.7842(15) yes C7 C1 . 1.502(2) yes S O1 . 1.4529(12) yes S O2 . 1.4541(12) yes S O3 . 1.4582(11) yes S Na 4_576 3.2855(8) no O1 Na 4_576 2.4652(13) no O2 Na 3_665 2.3791(14) no C7 H1 . .98(2) no C7 H2 . .96(2) no O4 C2 . 1.3500(18) no O4 H5 . .87(3) no C2 C3 . 1.401(2) no C2 C1 . 1.403(2) no C1 C6 . 1.388(2) no C6 C5 . 1.386(2) no C6 H6 . .94(2) no C5 C4 . 1.385(2) no N1 C5 . 1.456(2) yes C4 C3 . 1.378(2) no C4 H4 . .92(2) no C3 H3 . .98(2) no N1 O5 . 1.213(2) yes N1 O6 . 1.231(2) yes O7 Na 4_576 2.5573(15) no O7 H7 . .81(3) no O7 H8 . .86(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 O4 H5 O3 1_554 .87(3) 1.74(3) 2.613(2) 174(3) O7 H7 O6 4_475 .81(3) 2.11(3) 2.901(2) 165(3) O7 H8 O2 4_575 .86(5) 2.17(5) 2.946(2) 151(4)