##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-01-30
_journal_date_accepted     2012-02-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1074
_journal_page_last     o1075
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812005454
_journal_coeditor_code     LH5413
_publ_contact_author_name     'Professor Fun, Hoong-Kun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
_publ_contact_author_email     hkfun@usm.my
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
S-Phenyl 4-methoxybenzothioate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'El-Azab, Adel S.' ?
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
PO Box 2457
Riyadh 11451
Saudi Arabia
and Department of Organic Chemistry
Faculty of Pharmacy
Al-Azhar University
Cairo 11884
Egypt
;
    'Abdel-Aziz, Alaa A.-M.' ?
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
PO Box 2457
Riyadh 11451
Saudi Arabia
and Department of Medicinal Chemistry
Faculty of Pharmacy
University of Mansoura
Mansoura 35516
Egypt
;
    'El-Subbagh, Hussein I.' ?
;
Department of Pharmaceutical Chemistry
Faculty of Pharmaceutical Sciences and Pharmaceutical Industries
Future University
Cairo 12311
Egypt
;
    'Suchada Chantrapromma'
;
Thomson Reuters ResearcherID: A-5085-2009.
;
;
Crystal Materials Research Unit
Department of Chemistry
Faculty of Science
Prince of Songkla University
Hat-Yai, Songkhla 90112
Thailand
;
    'Hoong-Kun Fun'
;
Alternative address: College of Pharmacy (Visiting Professor), King Saud
University, PO Box 2457, Riyadh 11451, Saudi Arabia.
Thomson Reuters ResearcherID: A-3561-2009.
;
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
S-Phenyl 4-methoxybenzothioate
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C14 H12 O2 S'
_chemical_formula_sum     'C14 H12 O2 S'
_chemical_formula_iupac     'C14 H12 O2 S'
_chemical_formula_weight     244.31
_chemical_melting_point_gt     366
_chemical_melting_point_lt     367
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_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'
_cell_length_a     5.4478(2)
_cell_length_b     8.2149(3)
_cell_length_c     27.3841(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1225.52(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2144
_cell_measurement_theta_min     3.23
_cell_measurement_theta_max     69.39
_cell_measurement_temperature     296(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.58
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     2.234
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.3574
_exptl_absorpt_correction_T_max     0.6986
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     7810
_diffrn_reflns_av_R_equivalents     0.0502
_diffrn_reflns_av_sigmaI/netI     0.0558
_diffrn_reflns_theta_min     3.23
_diffrn_reflns_theta_max     69.39
_diffrn_reflns_theta_full     69.39
_diffrn_measured_fraction_theta_max     0.972
_diffrn_measured_fraction_theta_full     0.971
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     29
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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     2144
_reflns_number_gt     1479
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0998
_refine_ls_R_factor_gt     0.0561
_refine_ls_wR_factor_gt     0.1604
_refine_ls_wR_factor_ref     0.1986
_refine_ls_goodness_of_fit_ref     1.221
_refine_ls_restrained_S_all     1.221
_refine_ls_number_reflns     2144
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0897P)²+0.2372P] 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     0.001
_refine_diff_density_max     0.316
_refine_diff_density_min     -0.281
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.025(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), with 1811 Friedel pairs'
_refine_ls_abs_structure_Flack     0.07(5)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.2447(3) 0.2241(2) 0.88540(4) 0.0866(6) Uani d . 1 1 . .
    O O1 -0.1014(8) 0.0079(5) 0.87109(10) 0.0848(13) Uani d . 1 1 . .
    O O2 -0.0150(7) -0.0916(5) 1.10026(10) 0.0712(10) Uani d . 1 1 . .
    C C1 0.0101(8) 0.0386(6) 0.95439(14) 0.0579(11) Uani d . 1 1 . .
    C C2 -0.1770(8) -0.0607(6) 0.97065(16) 0.0641(12) Uani d . 1 1 . .
    H H2A -0.2939 -0.0981 0.9486 0.077 Uiso calc R 1 1 . .
    C C3 -0.1940(8) -0.1055(7) 1.01918(14) 0.0657(13) Uani d . 1 1 . .
    H H3A -0.3225 -0.1713 1.0297 0.079 Uiso calc R 1 1 . .
    C C4 -0.0204(8) -0.0527(6) 1.05180(14) 0.0596(11) Uani d . 1 1 . .
    C C5 0.1682(8) 0.0475(6) 1.03636(15) 0.0637(12) Uani d . 1 1 . .
    H H5A 0.2841 0.0853 1.0585 0.076 Uiso calc R 1 1 . .
    C C6 0.1830(8) 0.0911(7) 0.98763(15) 0.0625(12) Uani d . 1 1 . .
    H H6A 0.3117 0.1568 0.9771 0.075 Uiso calc R 1 1 . .
    C C7 0.0229(9) 0.0742(7) 0.90125(15) 0.0653(13) Uani d . 1 1 . .
    C C8 0.2346(9) 0.2180(7) 0.82059(16) 0.0684(13) Uani d . 1 1 . .
    C C9 0.4109(10) 0.1329(7) 0.79629(16) 0.0773(15) Uani d . 1 1 . .
    H H9A 0.5299 0.0757 0.8136 0.093 Uiso calc R 1 1 . .
    C C10 0.4122(11) 0.1319(8) 0.74530(17) 0.0827(17) Uani d . 1 1 . .
    H H10A 0.5297 0.0722 0.7284 0.099 Uiso calc R 1 1 . .
    C C11 0.2390(10) 0.2194(7) 0.72047(17) 0.0779(14) Uani d . 1 1 . .
    H H11A 0.2402 0.2198 0.6865 0.094 Uiso calc R 1 1 . .
    C C12 0.0654(11) 0.3056(9) 0.74480(18) 0.0860(18) Uani d . 1 1 . .
    H H12A -0.0511 0.3651 0.7275 0.103 Uiso calc R 1 1 . .
    C C13 0.0619(11) 0.3049(8) 0.79550(19) 0.0818(16) Uani d . 1 1 . .
    H H13A -0.0574 0.3634 0.8123 0.098 Uiso calc R 1 1 . .
    C C14 -0.2089(11) -0.1900(9) 1.11832(18) 0.096(2) Uani d . 1 1 . .
    H H14A -0.1840 -0.2103 1.1525 0.144 Uiso calc R 1 1 . .
    H H14B -0.2115 -0.2915 1.1010 0.144 Uiso calc R 1 1 . .
    H H14C -0.3624 -0.1347 1.1137 0.144 Uiso calc R 1 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 C8 . 1.776(4) ?
    S1 C7 . 1.779(6) ?
    O1 C7 . 1.199(5) ?
    O2 C4 . 1.366(5) ?
    O2 C14 . 1.419(6) ?
    C1 C6 . 1.379(6) ?
    C1 C2 . 1.380(6) ?
    C1 C7 . 1.486(6) ?
    C2 C3 . 1.382(6) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.371(6) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.383(6) ?
    C5 C6 . 1.384(6) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C8 C9 . 1.362(7) ?
    C8 C13 . 1.366(7) ?
    C9 C10 . 1.397(6) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.367(7) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.356(8) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.389(7) ?
    C12 H12A . 0.9300 ?
    C13 H13A . 0.9300 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 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
    C8 S1 C7 . . 101.7(2) ?
    C4 O2 C14 . . 117.1(4) ?
    C6 C1 C2 . . 118.5(4) ?
    C6 C1 C7 . . 123.6(4) ?
    C2 C1 C7 . . 117.8(4) ?
    C1 C2 C3 . . 121.1(4) ?
    C1 C2 H2A . . 119.4 ?
    C3 C2 H2A . . 119.4 ?
    C4 C3 C2 . . 119.7(4) ?
    C4 C3 H3A . . 120.1 ?
    C2 C3 H3A . . 120.1 ?
    O2 C4 C3 . . 125.0(4) ?
    O2 C4 C5 . . 114.9(4) ?
    C3 C4 C5 . . 120.1(4) ?
    C4 C5 C6 . . 119.5(4) ?
    C4 C5 H5A . . 120.3 ?
    C6 C5 H5A . . 120.3 ?
    C1 C6 C5 . . 121.0(4) ?
    C1 C6 H6A . . 119.5 ?
    C5 C6 H6A . . 119.5 ?
    O1 C7 C1 . . 124.0(5) ?
    O1 C7 S1 . . 122.0(4) ?
    C1 C7 S1 . . 114.0(3) ?
    C9 C8 C13 . . 120.5(5) ?
    C9 C8 S1 . . 118.7(4) ?
    C13 C8 S1 . . 120.6(4) ?
    C8 C9 C10 . . 119.7(5) ?
    C8 C9 H9A . . 120.2 ?
    C10 C9 H9A . . 120.2 ?
    C11 C10 C9 . . 119.4(5) ?
    C11 C10 H10A . . 120.3 ?
    C9 C10 H10A . . 120.3 ?
    C12 C11 C10 . . 120.7(4) ?
    C12 C11 H11A . . 119.6 ?
    C10 C11 H11A . . 119.6 ?
    C11 C12 C13 . . 119.9(5) ?
    C11 C12 H12A . . 120.0 ?
    C13 C12 H12A . . 120.0 ?
    C8 C13 C12 . . 119.7(5) ?
    C8 C13 H13A . . 120.2 ?
    C12 C13 H13A . . 120.2 ?
    O2 C14 H14A . . 109.5 ?
    O2 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O2 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 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
    C6 C1 C2 C3 . . . . 0.8(7) ?
    C7 C1 C2 C3 . . . . 176.9(5) ?
    C1 C2 C3 C4 . . . . -0.9(8) ?
    C14 O2 C4 C3 . . . . -2.2(8) ?
    C14 O2 C4 C5 . . . . 178.1(5) ?
    C2 C3 C4 O2 . . . . -178.6(5) ?
    C2 C3 C4 C5 . . . . 1.2(8) ?
    O2 C4 C5 C6 . . . . 178.4(5) ?
    C3 C4 C5 C6 . . . . -1.3(8) ?
    C2 C1 C6 C5 . . . . -0.9(8) ?
    C7 C1 C6 C5 . . . . -176.8(5) ?
    C4 C5 C6 C1 . . . . 1.2(7) ?
    C6 C1 C7 O1 . . . . 167.1(5) ?
    C2 C1 C7 O1 . . . . -8.8(8) ?
    C6 C1 C7 S1 . . . . -12.0(6) ?
    C2 C1 C7 S1 . . . . 172.1(3) ?
    C8 S1 C7 O1 . . . . -5.6(5) ?
    C8 S1 C7 C1 . . . . 173.6(4) ?
    C7 S1 C8 C9 . . . . -99.8(5) ?
    C7 S1 C8 C13 . . . . 84.1(5) ?
    C13 C8 C9 C10 . . . . -1.3(8) ?
    S1 C8 C9 C10 . . . . -177.4(5) ?
    C8 C9 C10 C11 . . . . 1.4(9) ?
    C9 C10 C11 C12 . . . . -0.6(9) ?
    C10 C11 C12 C13 . . . . -0.3(9) ?
    C9 C8 C13 C12 . . . . 0.4(9) ?
    S1 C8 C13 C12 . . . . 176.5(5) ?
    C11 C12 C13 C8 . . . . 0.4(10) ?
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
    C3 H3A Cg1 3_447 0.93 2.96 3.658(6) 133 y
