#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/27/2202774.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_2202774
loop_
_publ_author_name
'Nagarajan Vembu'
'Maruthai Nallu'
'Jered Garrison'
'Wiley J. Youngs'
_publ_section_title
;
 2,4-Dichlorophenyl 4-toluenesulfonate: supramolecular aggregation
 through C---H···O,
 C---H···Cl, C---H···π and
 π···π interactions
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o939
_journal_page_last               o941
_journal_paper_doi               10.1107/S160053680301208X
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C13 H10 Cl2 O3 S'
_chemical_formula_sum            'C13 H10 Cl2 O3 S'
_chemical_formula_weight         317.17
_chemical_melting_point          374.0(10)
_chemical_name_common            '2,4-dichlorophenyl p-toluenesulfonate'
_chemical_name_systematic
;
2,4-dichlorophenyl 4-toluenesulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.079(2)
_cell_angle_beta                 96.119(2)
_cell_angle_gamma                103.134(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7314(11)
_cell_length_b                   8.3724(11)
_cell_length_c                   10.7055(15)
_cell_measurement_reflns_used    7298
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.54
_cell_volume                     659.04(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8295
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.7811
_exptl_absorpt_correction_T_min  0.7164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0284
_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/[σ²(Fo²)+(0.0378P)²+0.4025P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                2954
_reflns_number_total             3074
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6251.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '373-375' was changed to '374.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '373-375' was changed to '374.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2202774
_cod_database_fobs_code          2202774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_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_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
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
_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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 191535
