##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,4-dichlorophenyl 4-toluenesulfonate
;
_chemical_name_common     '2,4-dichlorophenyl p-toluenesulfonate'
_chemical_formula_moiety     'C13 H10 Cl2 O3 S'
_chemical_formula_sum     'C13 H10 Cl2 O3 S'
_chemical_formula_weight     317.17
_chemical_melting_point     '373-375'
_symmetry_cell_setting     'Triclinic'
_symmetry_space_group_name_H-M     'P-1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.7314(11)
_cell_length_b     8.3724(11)
_cell_length_c     10.7055(15)
_cell_angle_alpha     99.079(2)
_cell_angle_beta     96.119(2)
_cell_angle_gamma     103.134(2)
_cell_volume     659.04(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7298
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     28.38
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.40
_exptl_crystal_density_diffrn     1.598
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     324
_exptl_absorpt_coefficient_mu     0.650
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.7164
_exptl_absorpt_correction_T_max     0.7811
_exptl_special_details
;
The Tmin and Tmax values obtained from the SIZE instruction are listed
above. The absorption correction was applied using SADABS and it gives
0.901603 ratio of min/max transmission"
;
_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     'CCD area detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8295
_diffrn_reflns_av_R_equivalents     0.0153
_diffrn_reflns_av_sigmaI/netI     0.0169
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     28.38
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.926
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3074
_reflns_number_gt     2954
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0296
_refine_ls_R_factor_gt     0.0284
_refine_ls_wR_factor_gt     0.0761
_refine_ls_wR_factor_ref     0.0769
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_restrained_S_all     1.076
_refine_ls_number_reflns     3074
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0378P)²+0.4025P] 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     0.394
_refine_diff_density_min     -0.322
_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'
    '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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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 0.35514(5) 0.00280(4) 0.23813(3) 0.01748(10) Uani d . 1 . . S
    Cl1 0.45681(5) 0.49434(4) 0.31856(3) 0.02440(10) Uani d . 1 . . Cl
    Cl2 0.14177(5) 0.52405(5) -0.14652(4) 0.02600(10) Uani d . 1 . . Cl
    O1 0.47889(15) -0.04614(14) 0.32349(11) 0.0250(2) Uani d . 1 . . O
    O2 0.25961(15) -0.11069(13) 0.12540(11) 0.0236(2) Uani d . 1 . . O
    O3 0.48113(13) 0.16079(12) 0.19492(10) 0.0174(2) Uani d . 1 . . O
    C1 -0.1690(2) 0.3051(2) 0.51223(18) 0.0267(3) Uani d . 1 . . C
    C2 -0.03703(19) 0.23010(17) 0.44474(15) 0.0193(3) Uani d . 1 . . C
    C3 0.1225(2) 0.21731(19) 0.51221(14) 0.0205(3) Uani d . 1 . . C
    C4 0.2440(2) 0.14659(18) 0.45074(14) 0.0194(3) Uani d . 1 . . C
    C5 0.20369(18) 0.08855(17) 0.31954(13) 0.0162(3) Uani d . 1 . . C
    C6 0.04635(19) 0.10076(18) 0.24933(14) 0.0184(3) Uani d . 1 . . C
    C7 -0.07293(19) 0.17108(18) 0.31323(15) 0.0198(3) Uani d . 1 . . C
    C8 0.39860(18) 0.24500(17) 0.11238(13) 0.0157(3) Uani d . 1 . . C
    C9 0.37926(18) 0.40343(17) 0.16049(13) 0.0165(3) Uani d . 1 . . C
    C10 0.30044(18) 0.49065(17) 0.08087(14) 0.0183(3) Uani d . 1 . . C
    C11 0.24333(19) 0.41690(18) -0.04656(14) 0.0187(3) Uani d . 1 . . C
    C12 0.2659(2) 0.26087(18) -0.09650(14) 0.0206(3) Uani d . 1 . . C
    C13 0.34456(19) 0.17467(18) -0.01564(14) 0.0185(3) Uani d . 1 . . C
    H1A -0.202(4) 0.387(4) 0.472(3) 0.069(9) Uiso d . 1 . . H
    H1B -0.273(3) 0.224(3) 0.519(2) 0.048(7) Uiso d . 1 . . H
    H1C -0.126(4) 0.354(4) 0.595(3) 0.066(8) Uiso d . 1 . . H
    H3 0.152(3) 0.256(3) 0.602(2) 0.032(5) Uiso d . 1 . . H
    H4 0.350(3) 0.138(3) 0.499(2) 0.032(5) Uiso d . 1 . . H
    H6 0.022(2) 0.063(2) 0.1578(18) 0.017(4) Uiso d . 1 . . H
    H7 -0.180(3) 0.177(3) 0.268(2) 0.035(5) Uiso d . 1 . . H
    H10 0.286(3) 0.599(2) 0.1125(18) 0.026(5) Uiso d . 1 . . H
    H12 0.231(3) 0.214(3) -0.185(2) 0.029(5) Uiso d . 1 . . H
    H13 0.356(2) 0.064(2) -0.0455(18) 0.021(4) 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 0.01871(17) 0.01458(16) 0.02211(18) 0.00756(13) 0.00526(13) 0.00569(13)
    Cl1 0.0303(2) 0.02017(18) 0.02093(18) 0.00586(14) 0.00299(14) -0.00047(13)
    Cl2 0.02321(19) 0.0284(2) 0.0309(2) 0.01036(15) 0.00224(14) 0.01456(15)
    O1 0.0249(5) 0.0269(6) 0.0314(6) 0.0153(5) 0.0077(5) 0.0142(5)
    O2 0.0281(6) 0.0143(5) 0.0279(6) 0.0052(4) 0.0072(4) 0.0007(4)
    O3 0.0155(4) 0.0170(5) 0.0219(5) 0.0060(4) 0.0036(4) 0.0068(4)
    C1 0.0238(8) 0.0249(8) 0.0340(9) 0.0093(6) 0.0108(7) 0.0042(7)
    C2 0.0177(7) 0.0152(6) 0.0265(7) 0.0040(5) 0.0072(5) 0.0060(5)
    C3 0.0220(7) 0.0214(7) 0.0180(7) 0.0048(6) 0.0037(5) 0.0037(5)
    C4 0.0176(7) 0.0212(7) 0.0208(7) 0.0059(5) 0.0011(5) 0.0074(5)
    C5 0.0158(6) 0.0141(6) 0.0201(7) 0.0046(5) 0.0043(5) 0.0045(5)
    C6 0.0174(6) 0.0182(6) 0.0189(7) 0.0029(5) 0.0015(5) 0.0046(5)
    C7 0.0146(6) 0.0208(7) 0.0252(7) 0.0050(5) 0.0016(5) 0.0076(6)
    C8 0.0134(6) 0.0148(6) 0.0206(7) 0.0048(5) 0.0041(5) 0.0056(5)
    C9 0.0153(6) 0.0158(6) 0.0181(6) 0.0029(5) 0.0049(5) 0.0016(5)
    C10 0.0161(6) 0.0141(6) 0.0265(7) 0.0047(5) 0.0071(5) 0.0049(5)
    C11 0.0144(6) 0.0190(6) 0.0250(7) 0.0048(5) 0.0035(5) 0.0093(6)
    C12 0.0217(7) 0.0203(7) 0.0186(7) 0.0032(6) 0.0023(5) 0.0038(6)
    C13 0.0199(7) 0.0151(6) 0.0214(7) 0.0051(5) 0.0056(5) 0.0029(5)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.4242(11) y
    S O2 . 1.4262(11) y
    S O3 . 1.6174(10) y
    S C5 . 1.7458(14) y
    Cl1 C9 . 1.7239(14) y
    Cl2 C11 . 1.7350(15) y
    O3 C8 . 1.4021(16) y
    C1 C2 . 1.504(2) y
    C1 H1A . 0.93(3) ?
    C1 H1B . 0.94(3) ?
    C1 H1C . 0.91(3) ?
    C2 C7 . 1.392(2) ?
    C2 C3 . 1.396(2) ?
    C3 C4 . 1.388(2) ?
    C3 H3 . 0.95(2) ?
    C4 C5 . 1.389(2) ?
    C4 H4 . 0.95(2) ?
    C5 C6 . 1.3932(19) ?
    C6 C7 . 1.385(2) ?
    C6 H6 . 0.965(18) ?
    C7 H7 . 0.93(2) ?
    C8 C13 . 1.382(2) ?
    C8 C9 . 1.3922(19) ?
    C9 C10 . 1.385(2) ?
    C10 C11 . 1.385(2) ?
    C10 H10 . 0.95(2) ?
    C11 C12 . 1.388(2) ?
    C12 C13 . 1.387(2) ?
    C12 H12 . 0.95(2) ?
    C13 H13 . 0.959(19) ?
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 S O2 . . 120.41(7) y
    O1 S O3 . . 102.48(6) y
    O2 S O3 . . 108.04(6) y
    O1 S C5 . . 111.35(7) y
    O2 S C5 . . 109.13(7) y
    O3 S C5 . . 103.91(6) y
    C8 O3 S . . 117.63(8) y
    C2 C1 H1A . . 111.5(18) ?
    C2 C1 H1B . . 112.2(15) ?
    H1A C1 H1B . . 110(2) ?
    C2 C1 H1C . . 113.6(18) ?
    H1A C1 H1C . . 106(2) ?
    H1B C1 H1C . . 103(2) ?
    C7 C2 C3 . . 118.77(13) ?
    C7 C2 C1 . . 120.25(14) ?
    C3 C2 C1 . . 120.97(14) ?
    C4 C3 C2 . . 121.27(14) ?
    C4 C3 H3 . . 117.4(13) ?
    C2 C3 H3 . . 121.3(13) ?
    C3 C4 C5 . . 118.46(13) ?
    C3 C4 H4 . . 119.4(13) ?
    C5 C4 H4 . . 122.2(13) ?
    C4 C5 C6 . . 121.66(13) ?
    C4 C5 S . . 119.87(11) ?
    C6 C5 S . . 118.45(11) ?
    C7 C6 C5 . . 118.66(13) ?
    C7 C6 H6 . . 120.8(11) ?
    C5 C6 H6 . . 120.5(11) ?
    C6 C7 C2 . . 121.18(13) ?
    C6 C7 H7 . . 119.6(14) ?
    C2 C7 H7 . . 119.2(14) ?
    C13 C8 C9 . . 120.71(13) ?
    C13 C8 O3 . . 120.44(12) ?
    C9 C8 O3 . . 118.80(12) ?
    C10 C9 C8 . . 120.13(13) ?
    C10 C9 Cl1 . . 119.45(11) ?
    C8 C9 Cl1 . . 120.41(11) ?
    C9 C10 C11 . . 118.45(13) ?
    C9 C10 H10 . . 120.9(12) ?
    C11 C10 H10 . . 120.6(12) ?
    C10 C11 C12 . . 122.01(13) ?
    C10 C11 Cl2 . . 118.77(11) ?
    C12 C11 Cl2 . . 119.22(12) ?
    C13 C12 C11 . . 118.94(14) ?
    C13 C12 H12 . . 119.9(12) ?
    C11 C12 H12 . . 121.1(12) ?
    C8 C13 C12 . . 119.73(13) ?
    C8 C13 H13 . . 118.9(11) ?
    C12 C13 H13 . . 121.3(11) ?
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
    O1 S O3 C8 . . . . -177.68(10) ?
    O2 S O3 C8 . . . . 54.19(11) ?
    C5 S O3 C8 . . . . -61.64(11) y
    C7 C2 C3 C4 . . . . -0.3(2) ?
    C1 C2 C3 C4 . . . . 179.30(14) ?
    C2 C3 C4 C5 . . . . 0.2(2) ?
    C3 C4 C5 C6 . . . . 0.4(2) ?
    C3 C4 C5 S . . . . 178.64(11) ?
    O1 S C5 C4 . . . . 18.90(14) ?
    O2 S C5 C4 . . . . 154.21(11) ?
    O3 S C5 C4 . . . . -90.73(12) ?
    O1 S C5 C6 . . . . -162.80(11) ?
    O2 S C5 C6 . . . . -27.49(13) ?
    O3 S C5 C6 . . . . 87.57(12) ?
    C4 C5 C6 C7 . . . . -0.7(2) ?
    S C5 C6 C7 . . . . -179.01(11) ?
    C5 C6 C7 C2 . . . . 0.6(2) ?
    C3 C2 C7 C6 . . . . 0.0(2) ?
    C1 C2 C7 C6 . . . . -179.66(14) ?
    S O3 C8 C13 . . . . -74.50(15) ?
    S O3 C8 C9 . . . . 108.25(12) ?
    C13 C8 C9 C10 . . . . 1.9(2) ?
    O3 C8 C9 C10 . . . . 179.14(12) ?
    C13 C8 C9 Cl1 . . . . -176.87(11) ?
    O3 C8 C9 Cl1 . . . . 0.37(18) ?
    C8 C9 C10 C11 . . . . -0.4(2) ?
    Cl1 C9 C10 C11 . . . . 178.35(10) ?
    C9 C10 C11 C12 . . . . -1.2(2) ?
    C9 C10 C11 Cl2 . . . . 179.16(10) ?
    C10 C11 C12 C13 . . . . 1.4(2) ?
    Cl2 C11 C12 C13 . . . . -178.96(11) ?
    C9 C8 C13 C12 . . . . -1.7(2) ?
    O3 C8 C13 C12 . . . . -178.89(12) ?
    C11 C12 C13 C8 . . . . 0.0(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
    C13 H13 O3 2_655 0.959(19) 2.871(19) 3.7361(18) 150.5(14) y
    C10 H10 O2 1_565 0.95(2) 2.47(2) 3.3876(18) 162.0(16) y
    C7 H7 O3 1_455 0.93(2) 2.62(2) 3.5211(18) 163.8(18) y
    C7 H7 O1 1_455 0.93(2) 3.04(2) 3.5505(19) 116.3(16) y
    C7 H7 Cl2 2_565 0.93(2) 2.97(2) 3.4404(15) 112.9(16) y
    C4 H4 O1 2_656 0.95(2) 2.52(2) 3.3907(18) 153.6(17) y
    C1 H1B O1 2_556 0.94(3) 2.81(3) 3.644(2) 147.7(19) y
    C1 H1B O1 1_455 0.94(3) 2.97(3) 3.668(2) 131.7(18) y
    C4 H4 O1 . 0.95(2) 2.66(2) 2.9874(19) 100.7(14) y
    C6 H6 O2 . 0.965(18) 2.605(18) 2.9436(18) 100.9(12) y
    C13 H13 O2 . 0.959(19) 2.583(19) 3.0093(18) 107.2(13) y
    C6 H6 Cg2 . 0.97(2) 3.388 3.778 106.6 y
data_global
_journal_date_recd_electronic     2003-05-20
_journal_date_accepted     2003-06-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue      7
_journal_page_first     o939
_journal_page_last     o941
_journal_paper_category     EO
_publ_contact_author
;
     Maruthai Nallu
     Department of Chemistry
     Bharathidasan University
     Tiruchirappalli - 620 024
     Tamil Nadu, India
;
_publ_contact_author_email     'mnalv2003@yahoo.com'
_publ_contact_author_phone     '0091-431-2407053'
_publ_section_title
;
2,4-Dichlorophenyl 4-toluenesulfonate: Supramolecular aggregation through
C-H...O, C-H...Cl, C-H...π and π...π interactions
;
loop_
    _publ_author_name
    _publ_author_address
    'Nagarajan Vembu'
;     Department of Chemistry
      Bharathidasan University
      Tiruchirappalli 620 024, INDIA
;
    'Maruthai Nallu'
;     Department of Chemistry
      Bharathidasan University
      Tiruchirappalli 620 024, INDIA
;
    'Jered Garrison'
;     Department of Chemistry
      University of Akron
      190, East Buchtel Commons
      Akron, Ohio 44325-3601, USA
;
    'Wiley J. Youngs'
;     Department of Chemistry
      University of Akron
      190, East Buchtel Commons
      Akron, Ohio 44325-3601, USA
;
