#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013273.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_2013273 loop_ _publ_author_name 'Sakwa, Samuel' 'Wheeler, Kraig A.' _publ_section_title ; Two bis(ammonium) 1,5-naphthalenedisulfonate salts ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o332 _journal_page_last o334 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac '2N H4 1+, C10 H6 O6 S2 2-' _chemical_formula_moiety '2N H4 1+, C10 H6 O6 S2 2-' _chemical_formula_sum 'C10 H14 N2 O6 S2' _chemical_formula_weight 322.36 _chemical_name_common 'Ammonium 1,5-naphthalenedisulfonate' _chemical_name_systematic ; bis(ammonium) naphthalene-1,5-disulfonate ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.431(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 11.3771(7) _cell_length_b 7.3386(4) _cell_length_c 7.9974(7) _cell_measurement_reflns_used 29 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.907 _cell_measurement_theta_min 19.339 _cell_volume 649.46(8) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 1999)' _computing_data_reduction XSCANS _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material X-SEED _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \q/2\q\ _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 2078 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.33 _diffrn_standards_decay_% <3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.438 _exptl_absorpt_correction_T_max 0.96341 _exptl_absorpt_correction_T_min 0.84374 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(SHELXTL; Bruker, 1998)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'Transparent plate' _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.299 _refine_diff_density_min -0.374 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 1495 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0316 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.2958P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0820 _refine_ls_wR_factor_ref 0.0859 _reflns_number_gt 1334 _reflns_number_total 1495 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1418.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013273 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 S 0.19300(3) 0.54277(5) 0.45424(5) 0.02419(14) Uani d . 1 . . S O1 0.12795(11) 0.70256(18) 0.48991(19) 0.0386(3) Uani d . 1 . . O O2 0.18437(11) 0.39108(17) 0.56914(16) 0.0316(3) Uani d . 1 . . O O3 0.15911(11) 0.4867(2) 0.27507(16) 0.0347(3) Uani d . 1 . . O C1 0.34900(13) 0.6017(2) 0.5021(2) 0.0231(3) Uani d . 1 . . C C2 0.38150(15) 0.7680(2) 0.5753(2) 0.0270(3) Uani d . 1 . . C C3 0.50450(15) 0.8166(2) 0.6251(2) 0.0281(3) Uani d . 1 . . C C4 0.59205(14) 0.6991(2) 0.6030(2) 0.0260(3) Uani d . 1 . . C C5 0.56227(13) 0.5257(2) 0.52650(19) 0.0216(3) Uani d . 1 . . C N 0.08994(15) 0.0731(2) 0.3672(2) 0.0319(3) Uani d . 1 . . N H2 0.3212 0.8507 0.5926 0.032 Uiso calc R 1 . . H H3 0.5265 0.9329 0.6747 0.034 Uiso calc R 1 . . H H4 0.6745 0.7336 0.6394 0.031 Uiso calc R 1 . . H H1N 0.114(2) 0.160(4) 0.442(3) 0.049(7) Uiso d . 1 . . H H2N 0.124(2) 0.083(3) 0.279(3) 0.044(6) Uiso d . 1 . . H H3N 0.109(3) -0.038(4) 0.406(4) 0.055(8) Uiso d . 1 . . H H4N 0.007(3) 0.072(4) 0.331(3) 0.058(8) 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 S 0.0182(2) 0.0262(2) 0.0277(2) -0.00048(14) 0.00430(15) 0.00070(15) O1 0.0252(6) 0.0317(7) 0.0596(9) 0.0039(5) 0.0113(6) -0.0044(6) O2 0.0308(6) 0.0323(7) 0.0334(6) -0.0036(5) 0.0112(5) 0.0041(5) O3 0.0253(6) 0.0481(8) 0.0275(6) -0.0013(5) -0.0004(5) -0.0003(6) C1 0.0191(7) 0.0267(8) 0.0230(7) -0.0018(6) 0.0039(6) 0.0008(6) C2 0.0245(7) 0.0266(8) 0.0294(8) 0.0015(6) 0.0054(6) -0.0023(7) C3 0.0299(8) 0.0248(8) 0.0287(8) -0.0050(7) 0.0052(6) -0.0071(6) C4 0.0214(7) 0.0279(8) 0.0277(7) -0.0055(6) 0.0035(6) -0.0044(6) C5 0.0203(7) 0.0239(7) 0.0203(7) -0.0023(6) 0.0040(6) 0.0000(6) N 0.0287(8) 0.0343(9) 0.0325(8) -0.0057(7) 0.0065(6) 0.0002(7) 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 S O1 . 1.4499(13) ? S O3 . 1.4540(13) ? S O2 . 1.4612(13) ? S C1 . 1.7798(15) ? C1 C2 . 1.367(2) ? C1 C5 3_666 1.432(2) ? C2 C3 . 1.409(2) ? C2 H2 . 0.9500 ? C3 C4 . 1.360(2) ? C3 H3 . 0.9500 ? C4 C5 . 1.418(2) ? C4 H4 . 0.9500 ? C5 C1 3_666 1.432(2) ? C5 C5 3_666 1.432(3) ? N H1N . 0.88(3) ? N H2N . 0.88(3) ? N H3N . 0.88(3) ? N H4N . 0.92(3) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle O1 S O3 . . 113.07(8) O1 S O2 . . 112.36(8) O3 S O2 . . 111.30(8) O1 S C1 . . 106.88(8) O3 S C1 . . 107.66(7) O2 S C1 . . 105.02(7) C2 C1 C5 . 3_666 121.35(14) C2 C1 S . . 117.77(12) C5 C1 S 3_666 . 120.79(12) C1 C2 C3 . . 119.95(15) C1 C2 H2 . . 120.0 C3 C2 H2 . . 120.0 C4 C3 C2 . . 120.80(15) C4 C3 H3 . . 119.6 C2 C3 H3 . . 119.6 C3 C4 C5 . . 121.08(14) C3 C4 H4 . . 119.5 C5 C4 H4 . . 119.5 C4 C5 C1 . 3_666 123.19(14) C4 C5 C5 . 3_666 118.99(18) C1 C5 C5 3_666 3_666 117.82(18) H1N N H2N . . 111(2) H1N N H3N . . 115(2) H2N N H3N . . 104(2) H1N N H4N . . 111(2) H2N N H4N . . 110(2) H3N N H4N . . 105(2) 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 N H1N O2 . 0.88(3) 2.04(3) 2.898(2) 166(2) yes N H2N O2 4_565 0.88(3) 1.98(3) 2.846(2) 175(2) yes N H3N O1 1_545 0.88(3) 2.01(3) 2.889(2) 172(3) yes N H4N O3 2_545 0.92(3) 1.98(3) 2.868(2) 160(2) 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion O1 S C1 C2 . . 6.03(15) O3 S C1 C2 . . 127.80(13) O2 S C1 C2 . . -113.51(14) O1 S C1 C5 . 3_666 -177.45(13) O3 S C1 C5 . 3_666 -55.68(15) O2 S C1 C5 . 3_666 63.01(14) C5 C1 C2 C3 3_666 . -0.3(2) S C1 C2 C3 . . 176.20(13) C1 C2 C3 C4 . . -0.7(3) C2 C3 C4 C5 . . 1.2(3) C3 C4 C5 C5 . 3_666 -0.6(3) C3 C4 C5 C1 . 3_666 178.96(15)