#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/52/2205256.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_2205256
loop_
_publ_author_name
'Vadivelu Manivannan'
'Nagarajan Vembu'
'Maruthai Nallu'
'Kandasamy Sivakumar'
'Frank R. Fronczek'
_publ_section_title
;
 1-Napthyl 4-toluenesulfonate: supramolecular aggregation through weak
 C---H···O and C---H···π
 interactions
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o528
_journal_page_last               o530
_journal_paper_doi               10.1107/S160053680500276X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H14 O3 S'
_chemical_formula_moiety         'C17 H14 O3 S'
_chemical_formula_sum            'C17 H14 O3 S'
_chemical_formula_weight         298.34
_chemical_melting_point          396.5(5)
_chemical_name_common            'α-naphthyl p-toluenesulfonate'
_chemical_name_systematic
;
1-naphthyl 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                70.446(4)
_cell_angle_beta                 71.335(4)
_cell_angle_gamma                81.831(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8693(10)
_cell_length_b                   9.3982(10)
_cell_length_c                   9.7112(10)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_cell_volume                     722.12(14)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
'KappaCCD (with an Oxford Cryosystems  Cryostream coller)'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12785
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            tan
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.433
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0371P)²+0.2951P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                3618
_reflns_number_total             4173
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6137.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '396-397' was changed to '396.5(5)' -
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 '396-397' was changed to '396.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205256
_cod_database_fobs_code          2205256
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_occupancy
_atom_site_type_symbol
S1 0.27616(3) 0.69621(3) 0.84693(3) 0.01878(8) Uani d 1 S
O1 0.44043(11) 0.64780(11) 0.81136(11) 0.0262(2) Uani d 1 O
O2 0.21933(12) 0.81989(10) 0.74096(10) 0.0278(2) Uani d 1 O
O3 0.17074(10) 0.55929(9) 0.87136(10) 0.01995(18) Uani d 1 O
C1 0.21628(14) 0.72478(13) 1.02625(13) 0.0169(2) Uani d 1 C
C2 0.07282(14) 0.80386(13) 1.06793(14) 0.0191(2) Uani d 1 C
C3 0.02221(15) 0.82293(15) 1.21147(15) 0.0226(2) Uani d 1 C
C4 0.11336(16) 0.76464(15) 1.31332(14) 0.0238(3) Uani d 1 C
C5 0.25789(16) 0.68812(15) 1.26721(14) 0.0236(2) Uani d 1 C
C6 0.31085(15) 0.66675(14) 1.12429(14) 0.0207(2) Uani d 1 C
C7 0.0554(2) 0.7846(2) 1.46938(19) 0.0420(4) Uani d 1 C
C8 0.22678(13) 0.40893(13) 0.92523(13) 0.0177(2) Uani d 1 C
C9 0.20123(15) 0.33882(15) 1.07827(14) 0.0219(2) Uani d 1 C
C10 0.24750(16) 0.18480(15) 1.12931(15) 0.0248(3) Uani d 1 C
C11 0.31563(15) 0.10623(14) 1.02734(15) 0.0226(2) Uani d 1 C
C12 0.41305(15) 0.09891(14) 0.75945(16) 0.0241(3) Uani d 1 C
C13 0.43480(16) 0.17064(15) 0.60671(16) 0.0274(3) Uani d 1 C
C14 0.38663(17) 0.32404(16) 0.55448(15) 0.0268(3) Uani d 1 C
C15 0.31966(15) 0.40423(14) 0.65588(14) 0.0214(2) Uani d 1 C
C16 0.29733(13) 0.33325(13) 0.81436(13) 0.0175(2) Uani d 1 C
C17 0.34306(14) 0.17783(13) 0.86778(14) 0.0191(2) Uani d 1 C
H2 0.0069(19) 0.8441(18) 0.9993(19) 0.027(4) Uiso d 1 H
H3 -0.077(2) 0.8780(18) 1.2415(18) 0.029(4) Uiso d 1 H
H5 0.326(2) 0.6496(19) 1.3372(19) 0.033(4) Uiso d 1 H
H6 0.4121(19) 0.6113(18) 1.0922(18) 0.028(4) Uiso d 1 H
H7A 0.141(3) 0.802(3) 1.502(3) 0.069(7) Uiso d 1 H
H7B -0.020(3) 0.864(3) 1.475(3) 0.082(8) Uiso d 1 H
H7C 0.011(3) 0.694(3) 1.540(3) 0.082(8) Uiso d 1 H
H9 0.1505(19) 0.3958(19) 1.1459(19) 0.028(4) Uiso d 1 H
H10 0.230(2) 0.134(2) 1.238(2) 0.036(5) Uiso d 1 H
H11 0.345(2) 0.001(2) 1.060(2) 0.034(4) Uiso d 1 H
H12 0.4413(19) -0.0079(19) 0.7957(18) 0.027(4) Uiso d 1 H
H13 0.486(2) 0.116(2) 0.538(2) 0.034(4) Uiso d 1 H
H14 0.401(2) 0.376(2) 0.446(2) 0.038(5) Uiso d 1 H
H15 0.285(2) 0.5090(19) 0.6218(19) 0.032(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'
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
O2 S1 O1 120.59(6) y
O2 S1 O3 103.28(5) y
O1 S1 O3 108.74(5) y
O2 S1 C1 109.69(6) y
O1 S1 C1 109.43(6) y
O3 S1 C1 103.66(5) y
C8 O3 S1 119.57(7) y
C2 C1 C6 121.59(11) ?
C2 C1 S1 118.60(9) ?
C6 C1 S1 119.80(9) ?
C3 C2 C1 118.96(11) ?
C3 C2 H2 119.6(10) ?
C1 C2 H2 121.4(10) ?
C2 C3 C4 120.91(11) ?
C2 C3 H3 119.6(10) ?
C4 C3 H3 119.5(10) ?
C5 C4 C3 118.76(11) ?
C5 C4 C7 121.08(13) ?
C3 C4 C7 120.15(13) ?
C6 C5 C4 121.43(11) ?
C6 C5 H5 119.0(10) ?
C4 C5 H5 119.6(10) ?
C5 C6 C1 118.33(11) ?
C5 C6 H6 121.5(9) ?
C1 C6 H6 120.1(9) ?
C4 C7 H7A 112.0(14) ?
C4 C7 H7B 112.9(16) ?
H7A C7 H7B 108(2) ?
C4 C7 H7C 107.9(16) ?
H7A C7 H7C 106(2) ?
H7B C7 H7C 110(2) ?
C9 C8 O3 120.41(10) ?
C9 C8 C16 122.80(11) ?
O3 C8 C16 116.58(10) ?
C8 C9 C10 119.05(11) ?
C8 C9 H9 118.1(10) ?
C10 C9 H9 122.8(10) ?
C11 C10 C9 120.58(12) ?
C11 C10 H10 119.6(11) ?
C9 C10 H10 119.9(11) ?
C10 C11 C17 120.96(11) ?
C10 C11 H11 121.6(10) ?
C17 C11 H11 117.4(10) ?
C13 C12 C17 120.62(12) ?
C13 C12 H12 120.4(9) ?
C17 C12 H12 118.9(10) ?
C12 C13 C14 120.52(12) ?
C12 C13 H13 118.2(11) ?
C14 C13 H13 121.2(11) ?
C15 C14 C13 120.45(12) ?
C15 C14 H14 118.6(11) ?
C13 C14 H14 120.9(11) ?
C14 C15 C16 120.20(12) ?
C14 C15 H15 121.3(10) ?
C16 C15 H15 118.5(10) ?
C15 C16 C8 123.02(11) ?
C15 C16 C17 119.52(11) ?
C8 C16 C17 117.44(11) ?
C12 C17 C11 122.15(11) ?
C12 C17 C16 118.68(11) ?
C11 C17 C16 119.17(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.4244(9) y
S1 O1 1.4296(9) y
S1 O3 1.6068(9) y
S1 C1 1.7513(11) y
O3 C8 1.4105(14) y
C1 C2 1.3922(16) ?
C1 C6 1.3932(16) ?
C2 C3 1.3858(17) ?
C2 H2 0.973(16) ?
C3 C4 1.3983(18) ?
C3 H3 0.968(17) ?
C4 C5 1.3954(18) ?
C4 C7 1.5036(19) ?
C5 C6 1.3892(17) ?
C5 H5 0.998(17) ?
C6 H6 0.986(16) ?
C7 H7A 0.96(3) ?
C7 H7B 0.94(3) ?
C7 H7C 0.94(3) ?
C8 C9 1.3659(17) ?
C8 C16 1.4183(16) ?
C9 C10 1.4109(18) ?
C9 H9 0.948(17) ?
C10 C11 1.3677(19) ?
C10 H10 0.970(18) ?
C11 C17 1.4213(18) ?
C11 H11 0.960(17) ?
C12 C13 1.370(2) ?
C12 C17 1.4197(17) ?
C12 H12 0.971(16) ?
C13 C14 1.4115(19) ?
C13 H13 0.942(18) ?
C14 C15 1.3732(17) ?
C14 H14 0.976(18) ?
C15 C16 1.4171(17) ?
C15 H15 0.966(17) ?
C16 C17 1.4235(16) ?
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
C2 H2 O2 . 0.973(16) 2.670(16) 2.9813(15) 99.0(11) ?
C6 H6 O1 . 0.986(16) 2.565(16) 2.9421(15) 102.6(11) ?
C15 H15 O3 . 0.966(17) 2.487(17) 2.8236(15) 100.3(11) ?
C3 H3 O2 2_577 0.968(17) 2.975(17) 3.7990(16) 143.8(12) y
C6 H6 O1 2_667 0.986(16) 2.621(16) 3.4334(15) 139.8(12) y
C7 H7A O2 1_556 0.96(3) 2.69(3) 3.515(2) 144.1(18) y
C9 H9 O3 2_567 0.948(17) 2.870(16) 3.2285(15) 103.7(11) ?
C12 H12 O2 1_545 0.971(16) 2.988(16) 3.4139(16) 107.9(11) ?
C14 H14 O1 2_666 0.976(18) 2.509(18) 3.3231(16) 140.8(14) y
C2 H2 Cg2 2_565 0.973(16) 2.68 3.36 127 y
C3 H3 Cg3 2_565 0.968(17) 2.83 3.40 119 y
C5 H5 Cg3 2_665 0.998(17) 2.86 3.55 127 y
C6 H6 Cg2 2_665 0.986(16) 3.01 3.62 121 y
C11 H11 Cg1 1_545 0.960(17) 2.78 3.49 132 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
O2 S1 O3 C8 158.11(8) y
O1 S1 O3 C8 28.90(10) y
C1 S1 O3 C8 -87.46(9) y
O2 S1 C1 C2 31.33(11) ?
O1 S1 C1 C2 165.71(9) ?
O3 S1 C1 C2 -78.42(10) ?
O2 S1 C1 C6 -149.58(10) ?
O1 S1 C1 C6 -15.20(12) ?
O3 S1 C1 C6 100.67(10) ?
C6 C1 C2 C3 -1.04(18) ?
S1 C1 C2 C3 178.04(9) ?
C1 C2 C3 C4 0.28(19) ?
C2 C3 C4 C5 0.78(19) ?
C2 C3 C4 C7 -179.17(14) ?
C3 C4 C5 C6 -1.2(2) ?
C7 C4 C5 C6 178.80(14) ?
C4 C5 C6 C1 0.43(19) ?
C2 C1 C6 C5 0.68(18) ?
S1 C1 C6 C5 -178.38(9) ?
S1 O3 C8 C9 84.39(12) ?
S1 O3 C8 C16 -100.68(10) ?
O3 C8 C9 C10 175.02(10) ?
C16 C8 C9 C10 0.42(18) ?
C8 C9 C10 C11 -0.60(19) ?
C9 C10 C11 C17 0.68(19) ?
C17 C12 C13 C14 -0.6(2) ?
C12 C13 C14 C15 1.1(2) ?
C13 C14 C15 C16 -0.4(2) ?
C14 C15 C16 C8 -179.03(12) ?
C14 C15 C16 C17 -0.75(18) ?
C9 C8 C16 C15 178.02(12) ?
O3 C8 C16 C15 3.22(16) ?
C9 C8 C16 C17 -0.30(17) ?
O3 C8 C16 C17 -175.10(10) ?
C13 C12 C17 C11 178.66(12) ?
C13 C12 C17 C16 -0.57(18) ?
C10 C11 C17 C12 -179.79(12) ?
C10 C11 C17 C16 -0.56(18) ?
C15 C16 C17 C12 1.23(17) ?
C8 C16 C17 C12 179.61(10) ?
C15 C16 C17 C11 -178.02(11) ?
C8 C16 C17 C11 0.35(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1407118
