#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/47/2004732.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_2004732 loop_ _publ_author_name 'Vermeulen, L. A.' 'Robinson, P. D.' _publ_section_title ; A Photochromic Zwitterionic Viologen: 4,4'-Bipyridinium-1,1'-bis(2-ethylsulfonate) Monohydrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 984 _journal_page_last 986 _journal_volume 52 _journal_year 1996 _chemical_formula_iupac 'C14 H16 N2 O6 S2, H2 O1' _chemical_formula_moiety 'C14 H16 N2 O6 S2,H2 O1' _chemical_formula_sum 'C14 H18 N2 O7 S2' _chemical_formula_weight 390.43 _chemical_name_systematic ; 1,1'-bis(2-sulfonatoethyl)-4,4'-bipyridinium monohydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90.0 _cell_angle_beta 98.17(3) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 25.016(6) _cell_length_b 5.881(8) _cell_length_c 11.299(8) _cell_measurement_reflns_used 23 _cell_measurement_temperature 296 _cell_measurement_theta_max 19.8 _cell_measurement_theta_min 19.6 _cell_volume 1645(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN PROCESS (Molecular Structure Corporation, 1985)' _computing_molecular_graphics 'TEXSAN ORTEP (Johnson, 1965)' _computing_publication_material 'TEXSAN FINISH PLATON (Spek, 1990)' _computing_structure_refinement 'TEXSAN LS' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Rigaku AFC-5S' _diffrn_measurement_method '\w scans (rate 6\% min^-1^ in \w, max. 3 repetitions)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source x-ray_tube _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4170 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.37 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_type 'empirical via \y scans (North, Phillips & Mathews, 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.35 _refine_diff_density_min -0.51 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.48 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 1551 _refine_ls_R_factor_obs 0.044 _refine_ls_shift/esd_max 0.0003 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 4F~o~^2^/\s^2^(F~o~^2^)' _refine_ls_wR_factor_obs 0.052 _reflns_number_observed 1551 _reflns_number_total 2087 _reflns_observed_criterion '[I > \s(I)]' _[local]_cod_data_source_file fg1127.cif _[local]_cod_data_source_block default _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 1645(2) _cod_database_code 2004732 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,-z+1/2 -x,-y,-z x,-y,z+1/2 x+1/2,y+1/2,z -x+1/2,y+1/2,-z+1/2 -x+1/2,-y+1/2,-z x+1/2,-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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom S1 .33701(2) .16440(9) .12123(5) .0305(2) Uani ? ? O1 .39465(6) .1998(4) .1512(2) .0577(7) Uani ? ? O2 .32019(7) .1449(3) -.00680(16) .0462(6) Uani ? ? O3 .31750(7) -.0183(3) .18876(18) .0501(7) Uani ? ? N1 .36655(7) .4563(3) .35974(17) .0298(5) Uani ? ? C1 .39609(8) .6373(4) .3384(2) .0376(7) Uani ? ? C2 .44883(8) .6554(4) .3913(2) .0360(7) Uani ? ? C3 .47161(7) .4910(4) .46978(19) .0274(6) Uani ? ? C4 .43941(8) .3049(4) .4906(2) .0362(7) Uani ? ? C5 .38714(8) .2915(4) .4330(2) .0357(7) Uani ? ? C6 .30953(8) .4418(4) .2997(2) .0371(7) Uani ? ? C7 .30544(8) .4144(4) .1663(2) .0304(6) Uani ? ? H1 .3805 .7538 .2863 .0450 Uiso calc C(1) H2 .4698 .7824 .3737 .0432 Uiso calc C(2) H4 .4535 .1882 .5443 .0434 Uiso calc C(4) H5 .3656 .1632 .4457 .0428 Uiso calc C(5) H6a .2927 .3149 .3311 .0445 Uiso calc C(6) H6b .2912 .5771 .3161 .0445 Uiso calc C(6) H7a .3220 .5424 .1352 .0364 Uiso calc C(7) H7b .2683 .4096 .1337 .0364 Uiso calc C(7) O4 .50 .0588(5) .25 .0627(12) Uani ? ? H8 .4731 .1558 .2197 .0751 Uiso ? ? 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 0.0313(3) 0.0284(3) 0.0303(3) 0.0061(2) -0.00030(18) -0.0021(2) O1 0.0302(8) 0.0787(14) 0.0627(13) 0.0076(9) 0.0019(8) -0.0231(12) O2 0.0576(10) 0.0481(10) 0.0307(10) 0.0113(9) -0.0010(7) -0.0044(9) O3 0.0664(12) 0.0305(9) 0.0534(12) 0.0085(8) 0.0088(10) 0.0110(9) N1 0.0258(8) 0.0318(10) 0.0311(10) 0.0000(7) 0.0012(7) -0.0082(9) C1 0.0363(10) 0.0274(11) 0.0456(14) 0.0014(9) -0.0058(9) 0.0057(11) C2 0.0315(10) 0.0270(10) 0.0471(14) -0.0025(9) -0.0022(9) 0.0058(12) C3 0.0285(10) 0.0257(10) 0.0273(11) -0.0007(8) 0.0019(8) -0.0015(9) C4 0.0352(11) 0.0311(11) 0.0405(13) -0.0038(9) -0.0010(9) 0.0085(11) C5 0.0341(10) 0.0332(12) 0.0393(13) -0.0074(9) 0.0040(9) 0.0008(11) C6 0.0245(10) 0.0429(13) 0.0429(14) 0.0011(9) 0.0009(9) -0.0115(12) C7 0.0278(9) 0.0252(10) 0.0361(12) 0.0023(8) -0.0024(8) -0.0014(10) O4 0.0448(14) 0.0416(15) 0.101(3) 0.0 0.0088(14) 0.0 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 International_Tables_Vol_IV_Table_2.3.1 H 0 0 International_Tables_Vol_IV_Table_2.3.1 O .008 .006 International_Tables_Vol_IV_Table_2.3.1 N .004 .003 International_Tables_Vol_IV_Table_2.3.1 S .110 .124 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -1 -2 4 0 -2 -2 0 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 S1 O2 . 112.44(12) yes O1 S1 O3 . 112.58(12) yes O1 S1 C7 . 106.40(11) yes O2 S1 O3 . 113.33(11) yes O2 S1 C7 . 105.84(11) yes O3 S1 C7 . 105.49(11) yes C1 N1 C5 . 121.15(19) no C1 N1 C6 . 118.72(18) yes C5 N1 C6 . 120.13(18) yes N1 C1 C2 . 120.3(2) no C1 C2 C3 . 120.6(2) no C2 C3 C3 3_666 121.7(2) no C2 C3 C4 . 117.48(18) no C4 C3 C3 3_666 120.8(2) no C3 C4 C5 . 119.7(2) no N1 C5 C4 . 120.7(2) no N1 C6 C7 . 112.70(17) yes S1 C7 C6 . 113.94(16) yes H8 O4 H8 2_655 102.4 yes O4 H8 O1 . 148.1 no 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 O1 . 1.448(2) yes S1 O2 . 1.453(2) yes S1 O3 . 1.443(2) yes S1 C7 . 1.777(3) yes N1 C1 . 1.337(3) no N1 C5 . 1.330(3) no N1 C6 . 1.493(3) yes C1 C2 . 1.373(3) no C2 C3 . 1.379(3) no C3 C3 3_666 1.490(4) no C3 C4 . 1.399(3) no C4 C5 . 1.378(3) no C6 C7 . 1.504(3) yes O4 H8 . 0.91 no O4 O1 . 2.836(4) no H8 O1 . 2.02 no 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_site_symmetry_1 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag S1 C7 C6 N1 . . . 60.6(2) no O1 S1 C7 C6 . . . -70.86(18) no O2 S1 C7 C6 . . . 169.33(16) no O3 S1 C7 C6 . . . 48.94(18) no N1 C1 C2 C3 . . . -1.9(4) no N1 C5 C4 C3 . . . -1.5(4) no C1 N1 C5 C4 . . . 1.1(3) no C1 N1 C6 C7 . . . 66.7(3) no C1 C2 C3 C4 . . . 1.5(3) no C2 C1 N1 C5 . . . 0.6(4) no C2 C1 N1 C6 . . . -179.5(2) no C2 C3 C4 C5 . . . 0.2(3) no C4 C5 N1 C6 . . . -178.8(2) no C5 N1 C6 C7 . . . -113.4(2) no C3 C3 C4 C5 3_666 . . 179.6(2) no C1 C2 C3 C3 . . 3_666 -178.8(3) no C4 C3 C3 C2 . 3_666 3_666 -0.2(3) no C2 C3 C3 C2 . 3_666 3_666 -180.0(10) no C4 C3 C3 C4 . 3_666 3_666 180.0(8) no C2 C3 C3 C4 . 3_666 3_666 0.2(4) no