##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2013
_chemical_name_systematic
;
4-Chloronaphthalen-1-yl 4-methylbenzenesulfonate
;
_chemical_name_common
;
4-Chloronaphthalen-1-yl tosylate
;
_chemical_formula_moiety     'C17 H13 Cl O3 S'
_chemical_formula_sum     'C17 H13 Cl O3 S'
_chemical_formula_iupac     'C17 H13 Cl O3 S'
_chemical_formula_weight     332.78
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.1301(3)
_cell_length_b     11.9592(2)
_cell_length_c     10.3738(3)
_cell_angle_alpha     90
_cell_angle_beta     112.041(3)
_cell_angle_gamma     90
_cell_volume     1509.90(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10121
_cell_measurement_theta_min     3.348
_cell_measurement_theta_max     25.995
_cell_measurement_temperature     100
_exptl_crystal_description     'irregular'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.5
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.4
_exptl_crystal_density_diffrn     1.464
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.400
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     100.00(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     '1024 x 1024 with blocks 2 x 2'
_diffrn_reflns_number     10121
_diffrn_reflns_av_R_equivalents     0.0171
_diffrn_reflns_theta_min     3.348
_diffrn_reflns_theta_max     25.995
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     2950
_reflns_number_gt     2515
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0326
_refine_ls_R_factor_gt     0.0262
_refine_ls_wR_factor_gt     0.0703
_refine_ls_wR_factor_ref     0.0716
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     2950
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0373P)²+0.4347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.396
_refine_diff_density_min     -0.340
_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
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_cell_refinement
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.03474(3) 0.34571(3) 0.29668(4) 0.01694(11) Uani d 1 . .
    Cl Cl1 0.44738(3) 0.56968(3) 0.12070(4) 0.02886(12) Uani d 1 . .
    O O1 0.13270(8) 0.29057(8) 0.26065(11) 0.0190(2) Uani d 1 . .
    O O2 -0.04014(9) 0.39892(9) 0.17485(11) 0.0238(3) Uani d 1 . .
    O O3 -0.00103(9) 0.25441(9) 0.35695(11) 0.0234(3) Uani d 1 . .
    C C1 0.20522(12) 0.36011(12) 0.22530(15) 0.0175(3) Uani d 1 . .
    C C2 0.16998(13) 0.42354(13) 0.10778(15) 0.0213(3) Uani d 1 . .
    H H2 0.0963 0.4236 0.0490 0.026 Uiso calc 1 . .
    C C3 0.24673(13) 0.48882(13) 0.07683(15) 0.0226(3) Uani d 1 . .
    H H3 0.2236 0.5340 -0.0019 0.027 Uiso calc 1 . .
    C C4 0.35509(13) 0.48629(13) 0.16182(16) 0.0204(3) Uani d 1 . .
    C C5 0.50724(12) 0.41223(12) 0.37265(16) 0.0199(3) Uani d 1 . .
    H H5 0.5592 0.4534 0.3518 0.024 Uiso calc 1 . .
    C C6 0.53989(13) 0.34678(13) 0.48863(17) 0.0227(3) Uani d 1 . .
    H H6 0.6138 0.3436 0.5461 0.027 Uiso calc 1 . .
    C C7 0.46217(13) 0.28373(13) 0.52221(17) 0.0232(3) Uani d 1 . .
    H H7 0.4852 0.2399 0.6021 0.028 Uiso calc 1 . .
    C C8 0.35365(13) 0.28673(12) 0.43820(16) 0.0199(3) Uani d 1 . .
    H H8 0.3033 0.2444 0.4608 0.024 Uiso calc 1 . .
    C C9 0.31700(12) 0.35393(12) 0.31654(15) 0.0162(3) Uani d 1 . .
    C C10 0.39536(12) 0.41840(12) 0.28356(15) 0.0169(3) Uani d 1 . .
    C C11 0.10147(11) 0.44694(12) 0.42155(14) 0.0144(3) Uani d 1 . .
    C C12 0.09851(12) 0.55841(12) 0.38264(15) 0.0178(3) Uani d 1 . .
    H H12 0.0603 0.5802 0.2910 0.021 Uiso calc 1 . .
    C C13 0.15371(12) 0.63630(12) 0.48313(16) 0.0195(3) Uani d 1 . .
    H H13 0.1521 0.7112 0.4584 0.023 Uiso calc 1 . .
    C C14 0.21162(11) 0.60499(13) 0.62050(15) 0.0174(3) Uani d 1 . .
    C C15 0.21289(12) 0.49281(13) 0.65634(15) 0.0202(3) Uani d 1 . .
    H H15 0.2511 0.4709 0.7479 0.024 Uiso calc 1 . .
    C C16 0.15807(13) 0.41343(13) 0.55780(15) 0.0196(3) Uani d 1 . .
    H H16 0.1592 0.3386 0.5826 0.023 Uiso calc 1 . .
    C C17 0.26993(13) 0.69201(14) 0.72763(17) 0.0246(4) Uani d 1 . .
    H H17A 0.3185 0.7342 0.6965 0.037 Uiso calc 1 . .
    H H17B 0.3116 0.6560 0.8141 0.037 Uiso calc 1 . .
    H H17C 0.2169 0.7413 0.7406 0.037 Uiso calc 1 . .
_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
    S1 O3 . 1.4226(11) ?
    S1 O2 . 1.4270(11) ?
    S1 O1 . 1.6093(10) ?
    S1 C11 . 1.7491(14) ?
    Cl1 C4 . 1.7415(16) ?
    O1 C1 . 1.4124(17) ?
    C1 C2 . 1.361(2) ?
    C1 C9 . 1.419(2) ?
    C2 C3 . 1.404(2) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.364(2) ?
    C3 H3 . 0.9300 ?
    C4 C10 . 1.426(2) ?
    C5 C6 . 1.363(2) ?
    C5 C10 . 1.414(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.414(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.363(2) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.419(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.426(2) ?
    C11 C16 . 1.386(2) ?
    C11 C12 . 1.389(2) ?
    C12 C13 . 1.383(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.391(2) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.391(2) ?
    C14 C17 . 1.505(2) ?
    C15 C16 . 1.383(2) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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 O2 . . 120.01(7) ?
    O3 S1 O1 . . 102.24(6) ?
    O2 S1 O1 . . 108.79(6) ?
    O3 S1 C11 . . 111.22(7) ?
    O2 S1 C11 . . 109.54(7) ?
    O1 S1 C11 . . 103.51(6) ?
    C1 O1 S1 . . 119.63(9) ?
    C2 C1 O1 . . 121.67(13) ?
    C2 C1 C9 . . 123.06(14) ?
    O1 C1 C9 . . 115.18(13) ?
    C1 C2 C3 . . 118.87(14) ?
    C1 C2 H2 . . 120.6 ?
    C3 C2 H2 . . 120.6 ?
    C4 C3 C2 . . 120.26(14) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C3 C4 C10 . . 122.37(14) ?
    C3 C4 Cl1 . . 118.80(12) ?
    C10 C4 Cl1 . . 118.83(12) ?
    C6 C5 C10 . . 120.84(14) ?
    C6 C5 H5 . . 119.6 ?
    C10 C5 H5 . . 119.6 ?
    C5 C6 C7 . . 120.46(14) ?
    C5 C6 H6 . . 119.8 ?
    C7 C6 H6 . . 119.8 ?
    C8 C7 C6 . . 120.43(14) ?
    C8 C7 H7 . . 119.8 ?
    C6 C7 H7 . . 119.8 ?
    C7 C8 C9 . . 120.50(14) ?
    C7 C8 H8 . . 119.8 ?
    C9 C8 H8 . . 119.8 ?
    C1 C9 C8 . . 122.92(14) ?
    C1 C9 C10 . . 118.07(13) ?
    C8 C9 C10 . . 119.01(13) ?
    C5 C10 C4 . . 123.91(14) ?
    C5 C10 C9 . . 118.76(13) ?
    C4 C10 C9 . . 117.33(13) ?
    C16 C11 C12 . . 121.29(13) ?
    C16 C11 S1 . . 118.87(11) ?
    C12 C11 S1 . . 119.83(11) ?
    C13 C12 C11 . . 118.54(13) ?
    C13 C12 H12 . . 120.7 ?
    C11 C12 H12 . . 120.7 ?
    C12 C13 C14 . . 121.41(14) ?
    C12 C13 H13 . . 119.3 ?
    C14 C13 H13 . . 119.3 ?
    C15 C14 C13 . . 118.72(13) ?
    C15 C14 C17 . . 121.19(14) ?
    C13 C14 C17 . . 120.08(14) ?
    C16 C15 C14 . . 120.93(14) ?
    C16 C15 H15 . . 119.5 ?
    C14 C15 H15 . . 119.5 ?
    C15 C16 C11 . . 119.10(14) ?
    C15 C16 H16 . . 120.4 ?
    C11 C16 H16 . . 120.4 ?
    C14 C17 H17A . . 109.5 ?
    C14 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C14 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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 O1 C1 . . . . -166.82(10) ?
    O2 S1 O1 C1 . . . . 65.27(11) ?
    C11 S1 O1 C1 . . . . -51.16(11) ?
    S1 O1 C1 C2 . . . . -65.00(16) ?
    S1 O1 C1 C9 . . . . 118.30(12) ?
    O1 C1 C2 C3 . . . . -178.46(12) ?
    C9 C1 C2 C3 . . . . -2.0(2) ?
    C1 C2 C3 C4 . . . . 1.5(2) ?
    C2 C3 C4 C10 . . . . 0.3(2) ?
    C2 C3 C4 Cl1 . . . . -179.32(11) ?
    C10 C5 C6 C7 . . . . -0.1(2) ?
    C5 C6 C7 C8 . . . . 0.7(2) ?
    C6 C7 C8 C9 . . . . -0.6(2) ?
    C2 C1 C9 C8 . . . . -179.28(13) ?
    O1 C1 C9 C8 . . . . -2.6(2) ?
    C2 C1 C9 C10 . . . . 0.7(2) ?
    O1 C1 C9 C10 . . . . 177.35(11) ?
    C7 C8 C9 C1 . . . . 179.90(14) ?
    C7 C8 C9 C10 . . . . -0.1(2) ?
    C6 C5 C10 C4 . . . . 179.00(14) ?
    C6 C5 C10 C9 . . . . -0.6(2) ?
    C3 C4 C10 C5 . . . . 178.87(15) ?
    Cl1 C4 C10 C5 . . . . -1.5(2) ?
    C3 C4 C10 C9 . . . . -1.6(2) ?
    Cl1 C4 C10 C9 . . . . 178.03(10) ?
    C1 C9 C10 C5 . . . . -179.34(13) ?
    C8 C9 C10 C5 . . . . 0.6(2) ?
    C1 C9 C10 C4 . . . . 1.07(19) ?
    C8 C9 C10 C4 . . . . -178.95(13) ?
    O3 S1 C11 C16 . . . . 30.20(14) ?
    O2 S1 C11 C16 . . . . 165.20(12) ?
    O1 S1 C11 C16 . . . . -78.90(13) ?
    O3 S1 C11 C12 . . . . -150.85(12) ?
    O2 S1 C11 C12 . . . . -15.85(14) ?
    O1 S1 C11 C12 . . . . 100.05(12) ?
    C16 C11 C12 C13 . . . . 0.1(2) ?
    S1 C11 C12 C13 . . . . -178.83(11) ?
    C11 C12 C13 C14 . . . . 0.2(2) ?
    C12 C13 C14 C15 . . . . -0.4(2) ?
    C12 C13 C14 C17 . . . . -179.41(14) ?
    C13 C14 C15 C16 . . . . 0.2(2) ?
    C17 C14 C15 C16 . . . . 179.22(14) ?
    C14 C15 C16 C11 . . . . 0.1(2) ?
    C12 C11 C16 C15 . . . . -0.3(2) ?
    S1 C11 C16 C15 . . . . 178.66(11) ?
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
    C3 H3 O2 3_565 0.93 2.53 3.2651(19) 135.7
    C12 H12 O3 2 0.93 2.53 3.3050(18) 140.8
    C16 H16 O1 4_566 0.93 2.53 3.3192(18) 142.9
_shelxl_version_number         .2013
data_global
_journal_date_recd_electronic     2018-06-12
_journal_date_accepted     2018-06-18
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue      6
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618008891
_journal_coeditor_code     SJ4183
_publ_contact_author_name     'Bartosz Zarychta'
_publ_contact_author_address
; Faculty of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
_publ_contact_author_email     bzarychta@uni.opole.pl
_publ_contact_author_fax      48774527101
_publ_contact_author_phone      48774527161
_publ_section_title
;
4-Chloronaphthalen-1-yl 4-methylbenzenesulfonate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Aleksandra Piontek' ?
; Faculty of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
    'Dawid Siodłak' ?
; Faculty of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
    'Bartosz Zarychta' ?
; Faculty of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
_publ_section_synopsis
;
The structure of a chloronaphthalene tosylate dericative is reported. The
naphthalene ring system and the benzene ring of the tosylate substituent are
inclined to one another by 55.32(5)°. The crystal structure features
C---H...O hydrogen bonds and a weak Cl...Cl halogen bond.
;
