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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-08-08
_journal_date_accepted     2008-08-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o1798
_journal_page_last     o1798
_journal_paper_category     QO
_journal_coeditor_code     BH2187
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Bis(carboxymethyl)ammonium 4-toluenesulfonate
;
loop_
    _publ_author_name
    _publ_author_address
    "Lo, Kong Mun"
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    "Ng, Seik Weng"
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(carboxymethyl)ammonium 4-toluenesulfonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H8 N O4 +,  C7 H7 O3 S -'
_chemical_formula_sum     'C11 H15 N O7 S'
_chemical_formula_iupac     'C4 H8 N O4 +,  C7 H7 O3 S -'
_chemical_formula_weight     305.30
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     9.9291(2)
_cell_length_b     10.3636(2)
_cell_length_c     25.8862(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2663.72(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4293
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     27.2
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'Triangular block'
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.523
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1280
_exptl_absorpt_coefficient_mu     0.275
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9295
_exptl_absorpt_correction_T_max     0.9295
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20842
_diffrn_reflns_av_R_equivalents     0.0480
_diffrn_reflns_av_sigmaI/netI     0.0300
_diffrn_reflns_theta_min     1.57
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3059
_reflns_number_gt     2560
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0511
_refine_ls_R_factor_gt     0.0377
_refine_ls_wR_factor_gt     0.1032
_refine_ls_wR_factor_ref     0.1189
_refine_ls_goodness_of_fit_ref     1.151
_refine_ls_restrained_S_all     1.150
_refine_ls_number_reflns     3059
_refine_ls_number_parameters     198
_refine_ls_number_restraints     4
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0644P)²+0.8206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.422
_refine_diff_density_min     -0.502
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2008)'
loop_
    _atom_site_type_symbol
    _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
    S S1 0.49041(5) 0.84948(4) 0.358654(17) 0.01248(14) Uani d . 1 . .
    O O1 0.55419(15) 0.74172(13) 0.38508(5) 0.0195(3) Uani d . 1 . .
    O O2 0.56209(14) 0.88382(13) 0.31102(5) 0.0163(3) Uani d . 1 . .
    O O3 0.34727(14) 0.83294(13) 0.35029(5) 0.0190(3) Uani d . 1 . .
    O O4 0.40223(14) 0.52637(13) 0.30853(5) 0.0171(3) Uani d . 1 . .
    O O5 0.51261(16) 0.49339(13) 0.38301(5) 0.0199(3) Uani d D 1 . .
    H H5O 0.510(3) 0.5747(10) 0.3841(10) 0.034(7) Uiso d D 1 . .
    O O6 0.20627(14) 0.17528(13) 0.21695(5) 0.0176(3) Uani d . 1 . .
    O O7 0.29656(14) -0.02406(13) 0.22217(5) 0.0163(3) Uani d D 1 . .
    H H7O 0.229(2) -0.047(3) 0.2048(10) 0.051(9) Uiso d D 1 . .
    N N1 0.37466(17) 0.27383(15) 0.28845(6) 0.0129(3) Uani d D 1 . .
    H H1N1 0.402(3) 0.316(2) 0.2610(7) 0.031(7) Uiso d D 1 . .
    H H1N2 0.2899(11) 0.296(2) 0.2924(8) 0.014(5) Uiso d D 1 . .
    C C1 0.50864(19) 0.98391(18) 0.40013(7) 0.0141(4) Uani d . 1 . .
    C C2 0.3995(2) 1.02980(19) 0.42797(8) 0.0187(4) Uani d . 1 . .
    H H2 0.3146 0.9879 0.4256 0.022 Uiso calc R 1 . .
    C C3 0.4152(2) 1.1376(2) 0.45941(8) 0.0212(4) Uani d . 1 . .
    H H3 0.3404 1.1681 0.4788 0.025 Uiso calc R 1 . .
    C C4 0.5374(2) 1.20164(19) 0.46306(7) 0.0183(4) Uani d . 1 . .
    C C5 0.6471(2) 1.15329(19) 0.43556(8) 0.0191(4) Uani d . 1 . .
    H H5 0.7319 1.1952 0.4380 0.023 Uiso calc R 1 . .
    C C6 0.6335(2) 1.04440(19) 0.40462(7) 0.0171(4) Uani d . 1 . .
    H H6 0.7093 1.0112 0.3866 0.021 Uiso calc R 1 . .
    C C7 0.5517(2) 1.3217(2) 0.49545(8) 0.0247(5) Uani d . 1 . .
    H H7A 0.4636 1.3631 0.4993 0.037 Uiso calc R 1 . .
    H H7B 0.6142 1.3815 0.4785 0.037 Uiso calc R 1 . .
    H H7C 0.5868 1.2985 0.5296 0.037 Uiso calc R 1 . .
    C C8 0.45172(19) 0.45546(18) 0.34029(7) 0.0137(4) Uani d . 1 . .
    C C9 0.45326(19) 0.31071(18) 0.33494(7) 0.0137(4) Uani d . 1 . .
    H H9A 0.5472 0.2798 0.3315 0.016 Uiso calc R 1 . .
    H H9B 0.4132 0.2705 0.3660 0.016 Uiso calc R 1 . .
    C C10 0.3811(2) 0.13288(17) 0.27813(7) 0.0142(4) Uani d . 1 . .
    H H10A 0.3570 0.0845 0.3098 0.017 Uiso calc R 1 . .
    H H10B 0.4738 0.1085 0.2680 0.017 Uiso calc R 1 . .
    C C11 0.28461(19) 0.09925(18) 0.23534(7) 0.0132(4) Uani d . 1 . .
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 O3 . 1.4478(14) ?
    S1 O1 . 1.4547(14) ?
    S1 O2 . 1.4675(13) ?
    S1 C1 . 1.768(2) ?
    O4 C8 . 1.207(2) ?
    O5 C8 . 1.320(2) ?
    O5 H5o . 0.840(10)
                     ?
    O6 C11 . 1.205(2) ?
    O7 C11 . 1.328(2) ?
    O7 H7o . 0.840(10)
                     ?
    N1 C9 . 1.484(2) ?
    N1 C10 . 1.486(2) ?
    N1 H1n1 . 0.880(10)
                      ?
    N1 H1n2 . 0.880(10)
                      ?
    C1 C2 . 1.385(3) ?
    C1 C6 . 1.394(3) ?
    C2 C3 . 1.391(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.386(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.394(3) ?
    C4 C7 . 1.507(3) ?
    C5 C6 . 1.390(3) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 C9 . 1.507(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.505(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
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
    O3 S1 O1 . . 114.00(9) ?
    O3 S1 O2 . . 112.28(8) ?
    O1 S1 O2 . . 111.72(8) ?
    O3 S1 C1 . . 106.53(9) ?
    O1 S1 C1 . . 105.95(9) ?
    O2 S1 C1 . . 105.63(8) ?
    C8 O5 H5O . . 108.2(18) ?
    C11 O7 H7O . . 110(2) ?
    C9 N1 C10 . . 112.10(14) ?
    C9 N1 H1N1 . . 111.7(17) ?
    C10 N1 H1N1 . . 109.4(16) ?
    C9 N1 H1N2 . . 110.2(14) ?
    C10 N1 H1N2 . . 108.3(15) ?
    H1N1 N1 H1N2 . . 105(2) ?
    C2 C1 C6 . . 119.85(18) ?
    C2 C1 S1 . . 120.41(15) ?
    C6 C1 S1 . . 119.73(15) ?
    C1 C2 C3 . . 119.53(19) ?
    C1 C2 H2 . . 120.2 ?
    C3 C2 H2 . . 120.2 ?
    C4 C3 C2 . . 121.46(18) ?
    C4 C3 H3 . . 119.3 ?
    C2 C3 H3 . . 119.3 ?
    C3 C4 C5 . . 118.49(18) ?
    C3 C4 C7 . . 121.06(19) ?
    C5 C4 C7 . . 120.4(2) ?
    C6 C5 C4 . . 120.68(19) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C1 . . 119.93(18) ?
    C5 C6 H6 . . 120.0 ?
    C1 C6 H6 . . 120.0 ?
    C4 C7 H7A . . 109.5 ?
    C4 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C4 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O4 C8 O5 . . 125.13(18) ?
    O4 C8 C9 . . 123.20(17) ?
    O5 C8 C9 . . 111.66(15) ?
    N1 C9 C8 . . 109.01(15) ?
    N1 C9 H9A . . 109.9 ?
    C8 C9 H9A . . 109.9 ?
    N1 C9 H9B . . 109.9 ?
    C8 C9 H9B . . 109.9 ?
    H9A C9 H9B . . 108.3 ?
    N1 C10 C11 . . 109.43(15) ?
    N1 C10 H10A . . 109.8 ?
    C11 C10 H10A . . 109.8 ?
    N1 C10 H10B . . 109.8 ?
    C11 C10 H10B . . 109.8 ?
    H10A C10 H10B . . 108.2 ?
    O6 C11 O7 . . 125.83(17) ?
    O6 C11 C10 . . 123.36(17) ?
    O7 C11 C10 . . 110.79(16) ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O3 S1 C1 C2 . . . . 16.35(19) ?
    O1 S1 C1 C2 . . . . -105.40(17) ?
    O2 S1 C1 C2 . . . . 135.94(16) ?
    O3 S1 C1 C6 . . . . -163.36(15) ?
    O1 S1 C1 C6 . . . . 74.89(17) ?
    O2 S1 C1 C6 . . . . -43.77(18) ?
    C6 C1 C2 C3 . . . . 1.3(3) ?
    S1 C1 C2 C3 . . . . -178.42(15) ?
    C1 C2 C3 C4 . . . . 0.9(3) ?
    C2 C3 C4 C5 . . . . -1.9(3) ?
    C2 C3 C4 C7 . . . . 177.37(19) ?
    C3 C4 C5 C6 . . . . 0.9(3) ?
    C7 C4 C5 C6 . . . . -178.42(18) ?
    C4 C5 C6 C1 . . . . 1.2(3) ?
    C2 C1 C6 C5 . . . . -2.3(3) ?
    S1 C1 C6 C5 . . . . 177.39(15) ?
    C10 N1 C9 C8 . . . . 175.26(15) ?
    O4 C8 C9 N1 . . . . -5.4(3) ?
    O5 C8 C9 N1 . . . . 175.76(15) ?
    C9 N1 C10 C11 . . . . 172.17(15) ?
    N1 C10 C11 O6 . . . . -6.8(3) ?
    N1 C10 C11 O7 . . . . 174.56(14) ?
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
    N1 H1N1 O2 3_645 0.880(10)
                             2.020(10)
                                     2.885(2) 167(2) yes
    N1 H1N2 O3 8_655 0.880(10)
                             2.06(2) 2.792(2) 140(2) yes
    O5 H5O O1 . 0.840(10)
                        1.790(10)
                                2.607(2) 164(3) yes
    O7 H7O O2 6_546 0.840(10)
                            1.850(10)
                                    2.659(2) 160(3) yes
